NPs Basic Information

Name
surfactin A
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
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
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
InChIKey
PBEDWPIWZYHNPL-RHKAOURMSA-N
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*-]
CAS NA
PubChem CID 70789014
ChEMBL ID NA
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organic acids and derivat
      • Class: Peptidomimetics
        • Subclass: Depsipeptides
          • Direct Parent: Cyclic depsipeptides

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Physi-Chem Properties

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

NPs ADMET Properties*

ADMET: Absorption

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

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.008 Plasma Protein Binding (PPB): 94.03%
Volume Distribution (VD): 0.37 Fu: 4.05%

ADMET: Metabolism

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

ADMET: Excretion

Clearance (CL): 2.081 Half-life (T1/2): 0.802

ADMET: Toxicity

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
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

*Note: the compound similarity was calculated by RDKIT.