Sanglifehrin A   Click here for help

GtoPdb Ligand ID: 13322

PDB Ligand
Compound class: Natural product
Comment: Sanglifehrin A is a bacteria-derived polyketide. It has immunosuppressive action that is mediated by inhibition of cyclophilins [4-5]. Interactions with cyclophilin A (peptidylprolyl isomerase A; PPIA) have been documented [1,3], and the human cyclophilin A:Sanglifehrin A crystal structure has been resloved [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 9
Rotatable bonds 15
Topological polar surface area 273.39
Molecular weight 1090.39
XLogP 6.24
No. Lipinski's rules broken 5

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES CC[C@H]1C[C@H](C)[C@@]2([C@@H](C)[C@H]([C@@H](C)[C@H](C[C@@H]([C@@H](C)CC/C=C/C=C(\C)/[C@@H]3C/C=C/C=C/[C@@H]([C@H](C)[C@H]([C@@H](CCC(=O)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC4=CC=CC(=C4)O)C(=O)N5CCC[C@@H](C(=O)O3)N5)O)O)O)O2)O)NC1=O
Isomeric SMILES CC[C@H]1C[C@@H]([C@@]2([C@H]([C@H]([C@H]([C@@H](O2)C[C@@H]([C@@H](C)CC/C=C/C=C(\C)/[C@@H]3C/C=C/C=C/[C@@H]([C@@H]([C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N4CCC[C@H](N4)C(=O)O3)CC5=CC(=CC=C5)O)C(C)C)CCC(=O)C)O)C)O)O)C)O)C)NC1=O)C
InChI InChI=1S/C60H91N5O13/c1-11-43-30-37(6)60(63-55(43)72)41(10)53(70)40(9)51(78-60)33-49(69)35(4)20-14-12-15-21-36(5)50-26-17-13-16-25-48(68)39(8)54(71)45(28-27-38(7)66)56(73)62-52(34(2)3)57(74)61-47(32-42-22-18-23-44(67)31-42)58(75)65-29-19-24-46(64-65)59(76)77-50/h12-13,15-18,21-23,25,31,34-35,37,39-41,43,45-54,64,67-71H,11,14,19-20,24,26-30,32-33H2,1-10H3,(H,61,74)(H,62,73)(H,63,72)/b15-12+,17-13+,25-16+,36-21+/t35-,37-,39-,40-,41-,43-,45+,46-,47-,48-,49-,50-,51-,52-,53-,54+,60+/m0/s1
InChI Key ONJZYZYZIKTIEG-CFBQITSMSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
(3S,6S,9R,10R,11S,12S,13E,15E,18S,21S)-18-[(2E,4E,8S,9S)-10-[(2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-3,5,11-trimethyl-8-oxo-1-oxa-7-azaspiro[5.5]undecan-2-yl]-9-hydroxy-8-methyldeca-2,4-dien-2-yl]-10,12-dihydroxy-3-[(3-hydroxyphenyl)methyl]-11-methyl-9-(3-oxobutyl)-6-propan-2-yl-19-oxa-1,4,7,25-tetrazabicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetrone
Database Links Click here for help
BindingDB Ligand 50218665
CAS Registry No. 187148-13-6 (source: PubChem)
ChEMBL Ligand CHEMBL410807
DrugBank Ligand DB03393
GtoPdb PubChem SID 496703292
PubChem CID 5388925
RCSB PDB Ligand SFA
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