data_CIR # _chem_comp.id CIR _chem_comp.name CITRULLINE _chem_comp.type 'L-PEPTIDE LINKING' _chem_comp.pdbx_type ATOMP _chem_comp.formula 'C6 H13 N3 O3' _chem_comp.mon_nstd_parent_comp_id ARG _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _chem_comp.pdbx_modified_date 2024-09-27 _chem_comp.pdbx_ambiguous_flag N _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 175.186 _chem_comp.one_letter_code R _chem_comp.three_letter_code CIR _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1KOD _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB _chem_comp.pdbx_pcm Y # loop_ _chem_comp_atom.comp_id _chem_comp_atom.atom_id _chem_comp_atom.alt_atom_id _chem_comp_atom.type_symbol _chem_comp_atom.charge _chem_comp_atom.pdbx_align _chem_comp_atom.pdbx_aromatic_flag _chem_comp_atom.pdbx_leaving_atom_flag _chem_comp_atom.pdbx_stereo_config _chem_comp_atom.pdbx_backbone_atom_flag _chem_comp_atom.pdbx_n_terminal_atom_flag _chem_comp_atom.pdbx_c_terminal_atom_flag _chem_comp_atom.model_Cartn_x _chem_comp_atom.model_Cartn_y _chem_comp_atom.model_Cartn_z _chem_comp_atom.pdbx_model_Cartn_x_ideal _chem_comp_atom.pdbx_model_Cartn_y_ideal _chem_comp_atom.pdbx_model_Cartn_z_ideal _chem_comp_atom.pdbx_component_atom_id _chem_comp_atom.pdbx_component_comp_id _chem_comp_atom.pdbx_ordinal CIR C C1 C 0 1 N N N Y N Y 1.787 4.103 36.211 3.505 0.297 -0.037 C1 CIR 1 CIR O O1 O 0 1 N N N Y N Y 1.108 3.115 36.448 4.165 -0.036 0.919 O1 CIR 2 CIR OXT O2 O 0 1 N Y N Y N Y 2.914 4.278 36.657 3.886 1.346 -0.783 O2 CIR 3 CIR CA C2 C 0 1 N N S Y N N 1.187 5.188 35.295 2.258 -0.469 -0.396 C2 CIR 4 CIR N N2 N 0 1 N N N Y Y N 1.457 6.536 35.882 2.308 -1.801 0.221 N2 CIR 5 CIR C3 C3 C 0 1 N N N N N N 1.802 5.110 33.878 1.030 0.286 0.119 C3 CIR 6 CIR C4 C4 C 0 1 N N N N N N 2.366 3.720 33.614 -0.240 -0.426 -0.352 C4 CIR 7 CIR C5 C5 C 0 1 N N N N N N 1.224 2.732 33.387 -1.467 0.329 0.162 C5 CIR 8 CIR N6 N6 N 0 1 N N N N N N 1.736 1.341 33.591 -2.684 -0.352 -0.289 N6 CIR 9 CIR C7 C7 C 0 1 N N N N N N 0.948 0.312 33.429 -3.894 0.137 0.047 C7 CIR 10 CIR O7 O7 O 0 1 N N N N N N 0.826 -0.531 34.315 -3.976 1.143 0.724 O7 CIR 11 CIR N8 N8 N 0 1 N N N N N N 0.295 0.166 32.313 -5.012 -0.490 -0.368 N8 CIR 12 CIR HXT HO2 H 0 1 N Y N Y N Y 3.159 3.538 37.200 4.695 1.804 -0.516 HO2 CIR 13 CIR HA H2 H 0 1 N N N Y N N 0.102 5.023 35.216 2.194 -0.572 -1.479 H2 CIR 14 CIR H2 HN21 H 0 0 N Y N Y Y N 1.069 7.242 35.290 2.367 -1.733 1.226 HN21 CIR 15 CIR H HN22 H 0 0 N N N Y Y N 1.039 6.595 36.788 1.513 -2.358 -0.057 HN22 CIR 16 CIR H31 H31 H 0 1 N N N N N N 1.021 5.329 33.134 1.050 0.311 1.208 H31 CIR 17 CIR H32 H32 H 0 1 N N N N N N 2.613 5.849 33.797 1.041 1.304 -0.269 H32 CIR 18 CIR H41 H41 H 0 1 N N N N N N 3.005 3.750 32.719 -0.259 -0.452 -1.442 H41 CIR 19 CIR H42 H42 H 0 1 N N N N N N 2.960 3.397 34.481 -0.251 -1.444 0.035 H42 CIR 20 CIR H51 H51 H 0 1 N N N N N N 0.412 2.935 34.101 -1.448 0.354 1.251 H51 CIR 21 CIR H52 H52 H 0 1 N N N N N N 0.842 2.838 32.361 -1.457 1.347 -0.226 H52 CIR 22 CIR HN6 HN6 H 0 1 N N N N N N 2.690 1.198 33.854 -2.618 -1.156 -0.829 HN6 CIR 23 CIR HN81 HN81 H 0 0 N N N N N N -0.300 -0.627 32.182 -4.947 -1.293 -0.908 HN81 CIR 24 CIR HN82 HN82 H 0 0 N Y N N N N 0.388 0.847 31.586 -5.884 -0.138 -0.126 HN82 CIR 25 # loop_ _chem_comp_bond.comp_id _chem_comp_bond.atom_id_1 _chem_comp_bond.atom_id_2 _chem_comp_bond.value_order _chem_comp_bond.pdbx_aromatic_flag _chem_comp_bond.pdbx_stereo_config _chem_comp_bond.pdbx_ordinal CIR C O DOUB N N 1 CIR C OXT SING N N 2 CIR C CA SING N N 3 CIR OXT HXT SING N N 4 CIR CA N SING N N 5 CIR CA C3 SING N N 6 CIR CA HA SING N N 7 CIR N H2 SING N N 8 CIR N H SING N N 9 CIR C3 C4 SING N N 10 CIR C3 H31 SING N N 11 CIR C3 H32 SING N N 12 CIR C4 C5 SING N N 13 CIR C4 H41 SING N N 14 CIR C4 H42 SING N N 15 CIR C5 N6 SING N N 16 CIR C5 H51 SING N N 17 CIR C5 H52 SING N N 18 CIR N6 C7 SING N N 19 CIR N6 HN6 SING N N 20 CIR C7 O7 DOUB N N 21 CIR C7 N8 SING N N 22 CIR N8 HN81 SING N N 23 CIR N8 HN82 SING N N 24 # loop_ _pdbx_chem_comp_descriptor.comp_id _pdbx_chem_comp_descriptor.type _pdbx_chem_comp_descriptor.program _pdbx_chem_comp_descriptor.program_version _pdbx_chem_comp_descriptor.descriptor CIR SMILES ACDLabs 12.01 'O=C(O)C(N)CCCNC(=O)N' CIR SMILES_CANONICAL CACTVS 3.370 'N[C@@H](CCCNC(N)=O)C(O)=O' CIR SMILES CACTVS 3.370 'N[CH](CCCNC(N)=O)C(O)=O' CIR SMILES_CANONICAL 'OpenEye OEToolkits' 1.7.0 'C(C[C@@H](C(=O)O)N)CNC(=O)N' CIR SMILES 'OpenEye OEToolkits' 1.7.0 'C(CC(C(=O)O)N)CNC(=O)N' CIR InChI InChI 1.03 'InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1' CIR InChIKey InChI 1.03 RHGKLRLOHDJJDR-BYPYZUCNSA-N # loop_ _pdbx_chem_comp_identifier.comp_id _pdbx_chem_comp_identifier.type _pdbx_chem_comp_identifier.program _pdbx_chem_comp_identifier.program_version _pdbx_chem_comp_identifier.identifier CIR 'SYSTEMATIC NAME' ACDLabs 12.01 N~5~-carbamoyl-L-ornithine CIR 'SYSTEMATIC NAME' 'OpenEye OEToolkits' 1.7.0 '(2S)-5-(aminocarbonylamino)-2-azanyl-pentanoic acid' # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site CIR 'Create component' 1999-07-08 RCSB CIR 'Modify descriptor' 2011-06-04 RCSB CIR 'Modify backbone' 2023-11-03 PDBE CIR 'Modify PCM' 2024-09-27 PDBE # loop_ _pdbx_chem_comp_pcm.pcm_id _pdbx_chem_comp_pcm.comp_id _pdbx_chem_comp_pcm.modified_residue_id _pdbx_chem_comp_pcm.type _pdbx_chem_comp_pcm.category _pdbx_chem_comp_pcm.position _pdbx_chem_comp_pcm.polypeptide_position _pdbx_chem_comp_pcm.comp_id_linking_atom _pdbx_chem_comp_pcm.modified_residue_id_linking_atom _pdbx_chem_comp_pcm.uniprot_specific_ptm_accession _pdbx_chem_comp_pcm.uniprot_generic_ptm_accession 1 CIR ARG Citrullination 'Named protein modification' 'Amino-acid side chain' 'Any position' ? ? PTM-0092 ? 2 CIR CYS None 'Covalent chemical modification' 'Amino-acid side chain' 'Any position' C7 SG ? ? 3 CIR CYS None 'Covalent chemical modification' 'Amino-acid side chain' 'Any position' O7 SG ? ? # _pdbe_chem_comp_drugbank_details.comp_id CIR _pdbe_chem_comp_drugbank_details.drugbank_id DB00155 _pdbe_chem_comp_drugbank_details.type 'small molecule' _pdbe_chem_comp_drugbank_details.name Citrulline _pdbe_chem_comp_drugbank_details.description 'Citrulline is an amino acid. It is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.' _pdbe_chem_comp_drugbank_details.cas_number 372-75-8 _pdbe_chem_comp_drugbank_details.mechanism_of_action "L-citrulline is converted to L-arginine by argininosuccinate synthase. L-arginine is in turn responsible for citrulline's therapeutic affects. Many of L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide or NO. NO is produced by all tissues of the body and plays very important roles in the cardiovascular system, immune system and nervous system. NO is formed from L-arginine via the enzyme nitric oxide synthase or synthetase (NOS), and the effects of NO are mainly mediated by 3',5' -cyclic guanylate or cyclic GMP. NO activates the enzyme guanylate cyclase, which catalyzes the synthesis of cyclic GMP from guanosine triphosphate or GTP. Cyclic GMP is converted to guanylic acid via the enzyme cyclic GMP phosphodiesterase. NOS is a heme-containing enzyme with some sequences similar to cytochrome P-450 reductase. Several isoforms of NOS exist, two of which are constitutive and one of which is inducible by immunological stimuli. The constitutive NOS found in the vascular endothelium is designated eNOS and that present in the brain, spinal cord and peripheral nervous system is designated nNOS. The form of NOS induced by immunological or inflammatory stimuli is known as iNOS. iNOS may be expressed constitutively in select tissues such as lung epithelium. All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen (O2) as cosubstrates, as well as the cofactors FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), tetrahydrobiopterin and heme. Interestingly, ascorbic acid appears to enhance NOS activity by increasing intracellular tetrahydrobiopterin. eNOS and nNOS synthesize NO in response to an increased concentration of calcium ions or in some cases in response to calcium-independent stimuli, such as shear stress. _In vitro_ studies of NOS indicate that the Km of the enzyme for L-arginine is in the micromolar range. The concentration of L-arginine in endothelial cells, as well as in other cells, and in plasma is in the millimolar range. What this means is that, under physiological conditions, NOS is saturated with its L-arginine substrate. In other words, L-arginine would not be expected to be rate-limiting for the enzyme, and it would not appear that supraphysiological levels of L-arginine which could occur with oral supplementation of the amino acid would make any difference with regard to NO production. The reaction would appear to have reached its maximum level. However, _in vivo_ studies have demonstrated that, under certain conditions, e.g. hypercholesterolemia, L-arginine could enhance endothelial-dependent vasodilation and NO production." # loop_ _pdbe_chem_comp_synonyms.comp_id _pdbe_chem_comp_synonyms.name _pdbe_chem_comp_synonyms.provenance _pdbe_chem_comp_synonyms.type CIR '(S)-2-Amino-5-ureidopentanoic acid' DrugBank ? CIR '2-Amino-5-ureidovaleric acid' DrugBank ? CIR 'alpha-amino-delta-Ureidovaleric acid' DrugBank ? CIR Cit DrugBank ? CIR Citrulline DrugBank ? CIR delta-Ureidonorvaline DrugBank ? CIR 'L-2-Amino-5-ureidovaleric acid' DrugBank ? CIR L-Citrulline DrugBank ? CIR N(5)-(Aminocarbonyl)-L-ornithine DrugBank ? CIR N(delta)-Carbamylornithine DrugBank ? CIR N5-(Aminocarbonyl)ornithine DrugBank ? CIR N5-Carbamoyl-L-ornithine DrugBank ? CIR N5-carbamoylornithine DrugBank ? CIR 'α-amino-δ-ureidovaleric acid' DrugBank ? CIR 'δ-ureidonorvaline' DrugBank ? # _pdbe_chem_comp_drugbank_classification.comp_id CIR _pdbe_chem_comp_drugbank_classification.drugbank_id DB00155 _pdbe_chem_comp_drugbank_classification.parent 'L-alpha-amino acids' _pdbe_chem_comp_drugbank_classification.kingdom 'Organic compounds' _pdbe_chem_comp_drugbank_classification.class 'Carboxylic acids and derivatives' _pdbe_chem_comp_drugbank_classification.superclass 'Organic acids and derivatives' _pdbe_chem_comp_drugbank_classification.description 'This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.' # loop_ _pdbe_chem_comp_drugbank_targets.comp_id _pdbe_chem_comp_drugbank_targets.drugbank_id _pdbe_chem_comp_drugbank_targets.name _pdbe_chem_comp_drugbank_targets.organism _pdbe_chem_comp_drugbank_targets.uniprot_id _pdbe_chem_comp_drugbank_targets.pharmacologically_active _pdbe_chem_comp_drugbank_targets.ordinal CIR DB00155 'Nitric oxide synthase 3' Humans P29474 unknown 1 CIR DB00155 'Argininosuccinate synthase' Humans P00966 unknown 2 CIR DB00155 'Putative hydrolase DDAH2' Humans O95865 unknown 3 CIR DB00155 'N(G),N(G)-dimethylarginine dimethylaminohydrolase 1' Humans O94760 unknown 4 CIR DB00155 'Ornithine transcarbamylase, mitochondrial' Humans P00480 unknown 5 CIR DB00155 'Nitric oxide synthase 1' Humans P29475 unknown 6 CIR DB00155 'Nitric oxide synthase, inducible' Humans P35228 unknown 7 CIR DB00155 'Protein-arginine deiminase type-4' Humans Q9UM07 unknown 8 CIR DB00155 'Protein-arginine deiminase type-6' Humans Q6TGC4 no 9 CIR DB00155 'Protein-arginine deiminase type-1' Humans Q9ULC6 unknown 10 CIR DB00155 'Protein-arginine deiminase type-3' Humans Q9ULW8 unknown 11 CIR DB00155 'Protein-arginine deiminase type-2' Humans Q9Y2J8 unknown 12 # loop_ _software.name _software.version _software.description rdkit 2023.09.6 'Core functionality.' pdbeccdutils 0.8.6 'Wrapper to provide 2D templates and molecular fragments.' # loop_ _pdbe_chem_comp_atom_depiction.comp_id _pdbe_chem_comp_atom_depiction.atom_id _pdbe_chem_comp_atom_depiction.element _pdbe_chem_comp_atom_depiction.model_Cartn_x _pdbe_chem_comp_atom_depiction.model_Cartn_y _pdbe_chem_comp_atom_depiction.pdbx_ordinal CIR C C 6.404 3.465 1 CIR O O 7.702 2.715 2 CIR OXT O 6.404 4.965 3 CIR CA C 5.104 2.715 4 CIR N N 3.805 3.465 5 CIR C3 C 5.104 1.215 6 CIR C4 C 6.404 0.465 7 CIR C5 C 6.404 -1.035 8 CIR N6 N 7.702 -1.785 9 CIR C7 C 7.702 -3.285 10 CIR O7 O 6.404 -4.035 11 CIR N8 N 9.002 -4.035 12 # loop_ _pdbe_chem_comp_bond_depiction.comp_id _pdbe_chem_comp_bond_depiction.atom_id_1 _pdbe_chem_comp_bond_depiction.atom_id_2 _pdbe_chem_comp_bond_depiction.value_order _pdbe_chem_comp_bond_depiction.bond_dir _pdbe_chem_comp_bond_depiction.pdbx_ordinal CIR C O DOUBLE NONE 1 CIR C OXT SINGLE NONE 2 CIR C CA SINGLE NONE 3 CIR CA N SINGLE BEGINDASH 4 CIR CA C3 SINGLE NONE 5 CIR C3 C4 SINGLE NONE 6 CIR C4 C5 SINGLE NONE 7 CIR C5 N6 SINGLE NONE 8 CIR N6 C7 SINGLE NONE 9 CIR C7 O7 DOUBLE NONE 10 CIR C7 N8 SINGLE NONE 11 # _pdbe_chem_comp_substructure.comp_id CIR _pdbe_chem_comp_substructure.substructure_name peptide _pdbe_chem_comp_substructure.id F1 _pdbe_chem_comp_substructure.substructure_type fragment _pdbe_chem_comp_substructure.substructure_smiles NCC=O _pdbe_chem_comp_substructure.substructure_inchis InChI=1S/C2H5NO/c3-1-2-4/h2H,1,3H2 _pdbe_chem_comp_substructure.substructure_inchikeys LYIIBVSRGJSHAV-UHFFFAOYSA-N # loop_ _pdbe_chem_comp_substructure_mapping.comp_id _pdbe_chem_comp_substructure_mapping.atom_id _pdbe_chem_comp_substructure_mapping.substructure_id _pdbe_chem_comp_substructure_mapping.substructure_ordinal CIR O F1 1 CIR C F1 1 CIR CA F1 1 CIR N F1 1 # _pdbe_chem_comp_rdkit_properties.comp_id CIR _pdbe_chem_comp_rdkit_properties.exactmw 175.096 _pdbe_chem_comp_rdkit_properties.amw 175.188 _pdbe_chem_comp_rdkit_properties.lipinskiHBA 6 _pdbe_chem_comp_rdkit_properties.lipinskiHBD 6 _pdbe_chem_comp_rdkit_properties.NumRotatableBonds 6 _pdbe_chem_comp_rdkit_properties.NumHBD 4 _pdbe_chem_comp_rdkit_properties.NumHBA 4 _pdbe_chem_comp_rdkit_properties.NumHeavyAtoms 12 _pdbe_chem_comp_rdkit_properties.NumAtoms 25 _pdbe_chem_comp_rdkit_properties.NumHeteroatoms 6 _pdbe_chem_comp_rdkit_properties.NumAmideBonds 2 _pdbe_chem_comp_rdkit_properties.FractionCSP3 0.667 _pdbe_chem_comp_rdkit_properties.NumRings 0 _pdbe_chem_comp_rdkit_properties.NumAromaticRings 0 _pdbe_chem_comp_rdkit_properties.NumAliphaticRings 0 _pdbe_chem_comp_rdkit_properties.NumSaturatedRings 0 _pdbe_chem_comp_rdkit_properties.NumHeterocycles 0 _pdbe_chem_comp_rdkit_properties.NumAromaticHeterocycles 0 _pdbe_chem_comp_rdkit_properties.NumSaturatedHeterocycles 0 _pdbe_chem_comp_rdkit_properties.NumAliphaticHeterocycles 0 _pdbe_chem_comp_rdkit_properties.NumSpiroAtoms 0 _pdbe_chem_comp_rdkit_properties.NumBridgeheadAtoms 0 _pdbe_chem_comp_rdkit_properties.NumAtomStereoCenters 1 _pdbe_chem_comp_rdkit_properties.NumUnspecifiedAtomStereoCenters 0 _pdbe_chem_comp_rdkit_properties.labuteASA 88.552 _pdbe_chem_comp_rdkit_properties.tpsa 118.440 _pdbe_chem_comp_rdkit_properties.CrippenClogP -1.153 _pdbe_chem_comp_rdkit_properties.CrippenMR 42.431 _pdbe_chem_comp_rdkit_properties.chi0v 5.566 _pdbe_chem_comp_rdkit_properties.chi1v 2.507 _pdbe_chem_comp_rdkit_properties.chi2v 0.582 _pdbe_chem_comp_rdkit_properties.chi3v 0.582 _pdbe_chem_comp_rdkit_properties.chi4v 0.214 _pdbe_chem_comp_rdkit_properties.chi0n 18.566 _pdbe_chem_comp_rdkit_properties.chi1n 8.651 _pdbe_chem_comp_rdkit_properties.chi2n 0.582 _pdbe_chem_comp_rdkit_properties.chi3n 0.582 _pdbe_chem_comp_rdkit_properties.chi4n 0.214 _pdbe_chem_comp_rdkit_properties.hallKierAlpha -1.300 _pdbe_chem_comp_rdkit_properties.kappa1 1.954 _pdbe_chem_comp_rdkit_properties.kappa2 5.363 _pdbe_chem_comp_rdkit_properties.kappa3 5.482 _pdbe_chem_comp_rdkit_properties.Phi 0.873 # loop_ _pdbe_chem_comp_external_mappings.comp_id _pdbe_chem_comp_external_mappings.source _pdbe_chem_comp_external_mappings.resource _pdbe_chem_comp_external_mappings.resource_id CIR UniChem ChEMBL CHEMBL444814 CIR UniChem DrugBank DB00155 CIR UniChem 'Guide to Pharmacology' 722 CIR UniChem 'KEGG LIGAND' C00327 CIR UniChem ChEBI 16349 CIR UniChem ChEBI 57743 CIR UniChem ZINC ZINC000001532614 CIR UniChem eMolecules 493823 CIR UniChem fdasrs 29VT07BGDA CIR UniChem PharmGKB PA164747225 CIR UniChem HMDB HMDB0000904 CIR UniChem NMRShiftDB 60020828 CIR UniChem ACTor 13594-51-9 CIR UniChem ACTor 627-77-0 CIR UniChem Recon 'citr_L' CIR UniChem Nikkaji J5.711H CIR UniChem BindingDb 92903 CIR UniChem 'EPA CompTox Dashboard' DTXSID80883373 CIR UniChem DrugCentral 3103 CIR UniChem MetaboLights MTBLC16349 CIR UniChem MetaboLights MTBLC57743 CIR UniChem BRENDA 145055 CIR UniChem BRENDA 145969 CIR UniChem BRENDA 153429 CIR UniChem BRENDA 154419 CIR UniChem BRENDA 229570 CIR UniChem BRENDA 24602 CIR UniChem BRENDA 44303 CIR UniChem BRENDA 938 CIR UniChem Rhea 57743 CIR UniChem ChemicalBook CB6423883 CIR UniChem ClinicalTrials CITRULLINE CIR UniChem ClinicalTrials 'CITRULLINE MALATE' CIR UniChem ClinicalTrials L-CITRULLINE CIR UniChem ClinicalTrials STIMOL CIR UniChem rxnorm CITRULLINE CIR UniChem MedChemExpress HY-N0391 CIR UniChem 'Probes And Drugs' PD010197 CIR UniChem CCDC FIFGOQ CIR UniChem PubChem 9750 CIR UniChem SureChEMBL SCHEMBL20588 CIR UniChem 'PubChem TPHARMA' 15195082 CIR UniChem 'PubChem TPHARMA' 15219582 CIR UniChem PubChem 6992098 # loop_ _pdbe_chem_comp_rdkit_conformer.comp_id _pdbe_chem_comp_rdkit_conformer.atom_id _pdbe_chem_comp_rdkit_conformer.Cartn_x_rdkit _pdbe_chem_comp_rdkit_conformer.Cartn_y_rdkit _pdbe_chem_comp_rdkit_conformer.Cartn_z_rdkit _pdbe_chem_comp_rdkit_conformer.rdkit_method _pdbe_chem_comp_rdkit_conformer.rdkit_ordinal CIR C -3.642 -0.315 -0.445 ETKDGv3 1 CIR O -4.121 -1.270 0.225 ETKDGv3 2 CIR OXT -4.217 0.035 -1.662 ETKDGv3 3 CIR CA -2.431 0.427 0.051 ETKDGv3 4 CIR N -2.636 0.837 1.444 ETKDGv3 5 CIR C3 -1.188 -0.477 -0.078 ETKDGv3 6 CIR C4 0.124 0.283 0.169 ETKDGv3 7 CIR C5 1.338 -0.611 -0.105 ETKDGv3 8 CIR N6 2.585 0.112 0.144 ETKDGv3 9 CIR C7 3.861 -0.512 -0.040 ETKDGv3 10 CIR O7 3.935 -1.710 -0.424 ETKDGv3 11 CIR N8 5.058 0.222 0.211 ETKDGv3 12 CIR HXT -5.027 -0.461 -2.016 ETKDGv3 13 CIR HA -2.294 1.332 -0.583 ETKDGv3 14 CIR H2 -3.538 1.365 1.505 ETKDGv3 15 CIR H -1.897 1.530 1.699 ETKDGv3 16 CIR H31 -1.160 -0.901 -1.107 ETKDGv3 17 CIR H32 -1.266 -1.325 0.639 ETKDGv3 18 CIR H41 0.167 0.624 1.226 ETKDGv3 19 CIR H42 0.170 1.173 -0.496 ETKDGv3 20 CIR H51 1.319 -0.948 -1.164 ETKDGv3 21 CIR H52 1.296 -1.504 0.556 ETKDGv3 22 CIR HN6 2.558 1.108 0.463 ETKDGv3 23 CIR HN81 5.016 1.215 0.530 ETKDGv3 24 CIR HN82 5.991 -0.228 0.079 ETKDGv3 25 #