Natural Product: ENC001545

NPs Basic Information

Download MOL File
Name
Stigmasterol
Molecular Formula C29H48O
IUPAC Name*
(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
SMILES
CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
InChI
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChIKey
HCXVJBMSMIARIN-PHZDYDNGSA-N
Synonyms
STIGMASTEROL; 83-48-7; Stigmasterin; beta-Stigmasterol; Stigmasta-5,22-dien-3-ol, (3b,22E)-; Stigmasta-5,22-dien-3beta-ol; .beta.-Stigmasterol; (24S)-5,22-Stigmastadien-3beta-ol; Stigmasta-5,22-dien-3-beta-ol; Stigmasta-5,22-dien-3-ol, (3beta,22E)-; (3beta,22E)-Stigmasta-5,22-dien-3-ol; 99WUK5D0Y8; CHEBI:28824; Stigmasta-5,22E-dien-3beta-ol; NSC 8095; NSC-8095; .delta.5,22-Stigmastadien-3.beta.-ol; (3.beta.,22E)-Stigmasta-5,22-dien-3-ol; Stigmasta-5,22-dien-3-ol; MFCD00003630; (3S,8S,9S,10R,13R,14S,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; 3beta-Hydroxy-24-ethyl-5,22-cholestadiene; UNII-99WUK5D0Y8; Serposterol; b-stigmasterol; Stigmasta-5,22-dien-3.beta.-ol; CCRIS 7476; D5-Stigmasterol; HSDB 7683; Delta5-Stigmasterol; EINECS 201-482-7; STIMASTEROL; Stigmasterol, ~95%; Stigmasta-5,22-dien-3-ol, (3beta)-; STIGMASTEROL [MI]; STIGMASTEROL [HSDB]; Wulzen anti-stiffness factor; SCHEMBL23999; .DELTA.5-STIGMASTEROL; STIGMASTEROL [WHO-DD]; stigmasta-5,22t-dien-3b-ol; CHEMBL400247; stigmasta-5,22-dien-3-b-ol; DTXSID801015733; Delta5,22-Stigmastadien-3beta-ol; HY-N0131; ZINC4096712; (24S)-5,22-stigmastadien-3b-ol; BDBM50376364; HB4095; LMST01040123; s2361; STL570256; 24aFH-stigmasta-5,22t-dien-3b-ol; AKOS022168193; CS-7746; (22E)-stigmasta-5,22-dien-3beta-ol; (24S)-Stigmast-5,22-dien-3beta-ol; (24xH)-stigmasta-5,22t-dien-3b-ol; 24-Ethyl-5,22-cholestadien-3beta-ol; 5,22-Cholestadien-24-ethyl-3beta-ol; GUINEA-PIG-ANTI-STIFFNESS FACTOR; (24aFH)-stigmasta-5,22t-dien-3b-ol; (24x)-ethylcholesta-5,22-dien-3b-ol; NCGC00142599-03; (3b,22E)-stigmasta-5,22-dien-3-ol; (3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; 14-((2E)(4S,1R)-4-ethyl-1,5-dimethylhex-2-enyl)(1S,5S,10S,11S,2R,14R,15R)-2,15 -dimethyltetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol; 24x-24-ethylcholest-5,22-dien-3b-ol; AS-15473; 24-Ethyl-5,22-cholestadien-3.beta.-ol; 5,22-Cholestadien-24beta-ethyl-3beta-ol; rac-(24xH)-stigmasta-5,22t-dien-3b-ol; (24S)-24-Ethylcholesta-5,22-dien-3beta-ol; C05442; Q425004; STIGMASTEROL (CONSTITUENT OF PYGEUM) [DSC]; Q-201746; STIGMASTEROL (CONSTITUENT OF SAW PALMETTO) [DSC]; 3.BETA.-HYDROXY-24-ETHYL-.DELTA.(SUP 5,22)-CHOLESTADIENE; Stigmasterol, certified reference material, 10 mg/mL in chloroform; 17-(4-ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS 83-48-7
PubChem CID 5280794
ChEMBL ID CHEMBL400247
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Steroids and steroid deri
        • Subclass: Stigmastanes and derivati
          • Direct Parent: Stigmastanes and derivati

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: 412.7 ALogp: 8.6
HBD: 1 HBA: 1
Rotatable Bonds: 5 Lipinski's rule of five: Rejected
Polar Surface Area: 20.2 Aromatic Rings: 4
Heavy Atoms: 30 QED Weighted: 0.443

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.576 MDCK Permeability: 0.00001440
Pgp-inhibitor: 0.951 Pgp-substrate: 0.936
Human Intestinal Absorption (HIA): 0.009 20% Bioavailability (F20%): 0.992
30% Bioavailability (F30%): 0.552

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.178 Plasma Protein Binding (PPB): 88.12%
Volume Distribution (VD): 1.629 Fu: 1.09%

ADMET: Metabolism

CYP1A2-inhibitor: 0.093 CYP1A2-substrate: 0.651
CYP2C19-inhibitor: 0.17 CYP2C19-substrate: 0.924
CYP2C9-inhibitor: 0.346 CYP2C9-substrate: 0.083
CYP2D6-inhibitor: 0.295 CYP2D6-substrate: 0.59
CYP3A4-inhibitor: 0.832 CYP3A4-substrate: 0.815

ADMET: Excretion

Clearance (CL): 4.515 Half-life (T1/2): 0.036

ADMET: Toxicity

hERG Blockers: 0.31 Human Hepatotoxicity (H-HT): 0.188
Drug-inuced Liver Injury (DILI): 0.237 AMES Toxicity: 0.005
Rat Oral Acute Toxicity: 0.386 Maximum Recommended Daily Dose: 0.973
Skin Sensitization: 0.912 Carcinogencity: 0.1
Eye Corrosion: 0.023 Eye Irritation: 0.08
Respiratory Toxicity: 0.807
*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
ENC004758 0.852 D0Y7LD 0.729
ENC001558 0.852 D0B4RU 0.581
ENC001846 0.794 D0K0EK 0.495
ENC003369 0.794 D0G8OC 0.430
ENC001008 0.729 D02STN 0.398
ENC001107 0.729 D06JPB 0.393
ENC005068 0.717 D06XMU 0.392
ENC000961 0.716 D0G5CF 0.364
ENC002290 0.708 D07BSQ 0.361
ENC003458 0.694 D0G3SH 0.356
*Note: the compound similarity was calculated by RDKIT.