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Name |
surfactin A
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Molecular Formula | C51H89N7O13 | |
IUPAC Name* |
3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-12-propan-2-yl-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-21-yl]propanoic acid
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SMILES |
CC(C)CCCCCCC[C@@H]1CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)O1)CC(C)C)CC(C)C)CC(=O)O)C(C)C)CC(C)C)CC(C)C)CCC(=O)O
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InChI |
InChI=1S/C51H89N7O13/c1-28(2)18-16-14-13-15-17-19-34-26-41(59)52-35(20-21-42(60)61)45(64)53-36(22-29(3)4)46(65)55-38(24-31(7)8)49(68)58-44(33(11)12)50(69)56-39(27-43(62)63)48(67)54-37(23-30(5)6)47(66)57-40(25-32(9)10)51(70)71-34/h28-40,44H,13-27H2,1-12H3,(H,52,59)(H,53,64)(H,54,67)(H,55,65)(H,56,69)(H,57,66)(H,58,68)(H,60,61)(H,62,63)/t34-,35+,36+,37-,38-,39+,40+,44+/m1/s1
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InChIKey |
PBEDWPIWZYHNPL-RHKAOURMSA-N
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Synonyms |
surfactin A; 3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-3,6,15,18-tetraisobutyl-12-isopropyl-25-(8-methylnonyl)-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-21-yl]propanoic acid; CHEBI:71976; J3.607.430B; Q27139838; Cyclo[L-Glu-L-Leu-D-Leu-L-Val-L-Asp-D-Leu-L-Leu-4-(7-methyloctyl)-2-deamino-D-aThr*-]
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CAS | NA | |
PubChem CID | 70789014 | |
ChEMBL ID | NA |
Chemical Classification: |
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Molecular Weight: | 1008.3 | ALogp: | 7.7 |
HBD: | 9 | HBA: | 13 |
Rotatable Bonds: | 22 | Lipinski's rule of five: | Rejected |
Polar Surface Area: | 305.0 | Aromatic Rings: | 1 |
Heavy Atoms: | 71 | QED Weighted: | 0.052 |
Caco-2 Permeability: | -5.971 | MDCK Permeability: | 0.00004830 |
Pgp-inhibitor: | 0.227 | Pgp-substrate: | 0.994 |
Human Intestinal Absorption (HIA): | 0.018 | 20% Bioavailability (F20%): | 0.91 |
30% Bioavailability (F30%): | 0.839 |
Blood-Brain-Barrier Penetration (BBB): | 0.008 | Plasma Protein Binding (PPB): | 94.03% |
Volume Distribution (VD): | 0.37 | Fu: | 4.05% |
CYP1A2-inhibitor: | 0 | CYP1A2-substrate: | 0.002 |
CYP2C19-inhibitor: | 0.048 | CYP2C19-substrate: | 0.036 |
CYP2C9-inhibitor: | 0.151 | CYP2C9-substrate: | 0.998 |
CYP2D6-inhibitor: | 0.024 | CYP2D6-substrate: | 0.025 |
CYP3A4-inhibitor: | 0.213 | CYP3A4-substrate: | 0.047 |
Clearance (CL): | 2.081 | Half-life (T1/2): | 0.802 |
hERG Blockers: | 0.002 | Human Hepatotoxicity (H-HT): | 0.977 |
Drug-inuced Liver Injury (DILI): | 0.294 | AMES Toxicity: | 0.003 |
Rat Oral Acute Toxicity: | 0.069 | Maximum Recommended Daily Dose: | 0.945 |
Skin Sensitization: | 0.158 | Carcinogencity: | 0.08 |
Eye Corrosion: | 0.003 | Eye Irritation: | 0.004 |
Respiratory Toxicity: | 0.024 |