Natural Product: ENC002696

NPs Basic Information

Download MOL File
Name
Verrucarin B
Molecular Formula C27H32O9
IUPAC Name*
(1R,3R,8R,12S,14R,19E,21Z,25R,26S,27S)-5,14,26-trimethylspiro[2,10,13,17,24-pentaoxapentacyclo[23.2.1.03,8.08,26.012,14]octacosa-4,19,21-triene-27,2'-oxirane]-11,18,23-trione
SMILES
CC1=C[C@@H]2[C@@]3(CC1)COC(=O)[C@@H]4[C@](O4)(CCOC(=O)/C=C/C=C\C(=O)O[C@H]5[C@]3([C@]6(CO6)[C@@H](C5)O2)C)C
InChI
InChI=1S/C27H32O9/c1-16-8-9-26-14-32-23(30)22-24(2,36-22)10-11-31-20(28)6-4-5-7-21(29)35-17-13-19(34-18(26)12-16)27(15-33-27)25(17,26)3/h4-7,12,17-19,22H,8-11,13-15H2,1-3H3/b6-4+,7-5-/t17-,18-,19-,22-,24-,25-,26-,27+/m1/s1
InChIKey
WUZWNHCQLPXCLS-HBGYRMRFSA-N
Synonyms
Verrucarin B; PHV68JZ445; 2290-11-1; Verrucarin A, 2'-deoxy-2',3'-epoxy-, (2'S,3'R)-; VERRUCARIN B [MI]; UNII-PHV68JZ445; SCHEMBL258359; CHEMBL1079296; DTXSID701033950; Q27286564; (2'S,3'R)-2'-DEOXY-2',3'-EPOXYVERRUCARIN A
CAS 2290-11-1
PubChem CID 46883075
ChEMBL ID CHEMBL1079296
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Prenol lipids
        • Subclass: Sesquiterpenoids
          • Direct Parent: Trichothecenes

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 500.5 ALogp: 2.1
HBD: 0 HBA: 9
Rotatable Bonds: 0 Lipinski's rule of five: Rejected
Polar Surface Area: 113.0 Aromatic Rings: 6
Heavy Atoms: 36 QED Weighted: 0.214

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.361 MDCK Permeability: 0.00001840
Pgp-inhibitor: 0.072 Pgp-substrate: 0.985
Human Intestinal Absorption (HIA): 0.004 20% Bioavailability (F20%): 0.941
30% Bioavailability (F30%): 0.261

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.905 Plasma Protein Binding (PPB): 69.21%
Volume Distribution (VD): 1.209 Fu: 17.80%

ADMET: Metabolism

CYP1A2-inhibitor: 0.113 CYP1A2-substrate: 0.162
CYP2C19-inhibitor: 0.72 CYP2C19-substrate: 0.552
CYP2C9-inhibitor: 0.766 CYP2C9-substrate: 0.007
CYP2D6-inhibitor: 0.226 CYP2D6-substrate: 0.066
CYP3A4-inhibitor: 0.895 CYP3A4-substrate: 0.512

ADMET: Excretion

Clearance (CL): 4.633 Half-life (T1/2): 0.215

ADMET: Toxicity

hERG Blockers: 0.097 Human Hepatotoxicity (H-HT): 0.65
Drug-inuced Liver Injury (DILI): 0.501 AMES Toxicity: 0.933
Rat Oral Acute Toxicity: 0.675 Maximum Recommended Daily Dose: 0.925
Skin Sensitization: 0.933 Carcinogencity: 0.059
Eye Corrosion: 0.004 Eye Irritation: 0.211
Respiratory Toxicity: 0.245
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC004774 0.779 D0Q4SD 0.242
ENC002240 0.746 D06XHC 0.233
ENC003126 0.619 D0C7JF 0.226
ENC003173 0.609 D0Z4ZT 0.219
ENC004775 0.605 D04GJN 0.216
ENC004446 0.580 D0EP0C 0.213
ENC003943 0.571 D0G8BV 0.213
ENC002026 0.556 D0F1UL 0.213
ENC002050 0.446 D02JNM 0.212
ENC003310 0.407 D09WYX 0.212
*Note: the compound similarity was calculated by RDKIT.