Natural Product: ENC001008

NPs Basic Information

Download MOL File
Name
Beta-Sitosterol
Molecular Formula C29H50O
IUPAC Name*
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-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](CC[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/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChIKey
KZJWDPNRJALLNS-VJSFXXLFSA-N
Synonyms
BETA-SITOSTEROL; 83-46-5; Sitosterol; Cupreol; Azuprostat; 22,23-Dihydrostigmasterol; Quebrachol; Triastonal; Cinchol; Harzol; Rhamnol; beta-Sitosterin; Nimbosterol; B-Sitosterol; (-)-beta-Sitosterol; alpha-Dihydrofucosterol; Prostasal; Sito-Lande; 24alpha-Ethylcholesterol; (24R)-Ethylcholest-5-en-3beta-ol; (3beta)-Stigmast-5-en-3-ol; Betaprost; Sobatum; beta Sitosterol; alpha-Phytosterol; (24R)-Stigmast-5-en-3beta-ol; Angelicin (steroid); SKF 14463; Beta-sistosterol; Stigmast-5-en-3beta-ol; a-Dihydrofucosterol; Phytosterol; CHEBI:27693; NSC8096; SITOSTEROL, BETA; Stigmast-5-en-3-ol, (3beta)-; .alpha.-Dihydrofucosterol; CHEMBL221542; S347WMO6M4; .beta.-Sitosterol; NSC-8096; NSC49083; .alpha.-Phytosterol; Sitosterol, .beta.; NSC 18173; NSC-18173; NSC-49083; Stigmasterol,23-dihydro-; Stigmasterol, 22,23-dihydro-; sitosterin; .beta.-Sitosterin; NSC 8096; SITOSTEROL, BETA-; Stigmast-5-en-3-ol, (3.beta.)-; (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; 24.alpha.-Ethylcholesterol; Stigmast-5-en-3-ol, (3b)-; Stigmast-5-en-3.beta.-ol; SR-05000002307; 24-alpha-Ethylcholesterol; Stigmast-5-en-3-beta-ol; UNII-S347WMO6M4; delta5-Stigmasten-3-beta-ol; Sitosterol beta; a-Phytosterol; b-Sitosterin; beta-Phytosterol; CCRIS 5529; ss--Sitosterol; .beta.Sitosterin; .beta.Sitosterol; beta -Sitosterol; (3-beta)-Stigmast-5-en-3-ol; CAS-83-46-5; NCGC00095716-01; (3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-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-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; EINECS 201-480-6; (-)-b-Sitosterol; Harzol (TN); MFCD00003631; 24a-Ethylcholesterol; alpha.Dihydrofucosterol; D5-Stigmasten-3b-ol; Stigmast-5-en-3b-ol; AI3-26020; Prestwick0_000985; Prestwick1_000985; Prestwick2_000985; Prestwick3_000985; Delta5-Stigmasten-3b-ol; stigmast-5-ene-3beta-ol; DSSTox_CID_2481; beta-Sitosterol, >=70%; Beta-sitosterol [WHO-DD]; SITOSTEROL [MART.]; beta-Sitosterol (Synthetic); DSSTox_RID_76601; BIDD:PXR0121; DSSTox_GSID_22481; SCHEMBL16105; 22,23-dihydro-Stigmasterol; BSPBio_001049; BIDD:ER0636; SPBio_002950; BETA-SITOSTEROL [INCI]; BPBio1_001155; MEGxp0_001710; BETA SITOSTEROL [VANDF]; .BETA.-SITOSTEROL [MI]; DTXSID5022481; (24R)-Stigmast-5-en-3b-ol; ACon1_000287; BETA-SITOSTEROL [USP-RS]; CHEBI:176889; HMS1571E11; HMS2098E11; (24R)-Ethylcholest-5-en-3b-ol; 24-Ethylcholest-5-en-3.beta.-ol; NSC18173; ZINC4095717; beta-Sitosterol, analytical standard; Tox21_111514; BDBM50218197; beta-Sitosterol, synthetic, >=95%; LMST01040129; NSC821067; s2273; AKOS005267194; CCG-208334; DB14038; NSC-821067; beta-Sitosterol, from soybean, >=96%; SMP1_000274; NCGC00142598-02; NCGC00142598-03; (3.BETA.)-STIGMAST-5-EN-3-OL; 14-((1S,4R)-4-ethyl-1,5-dimethylhexyl)(1S,5S,10S,11S,2R,14R,15R)-2,15-dimethyl tetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol; AC-24183; NCI60_041777; AB00513984; S0040; .DELTA.(SUP 5)-STIGMASTEN-3.BETA.-OL; C01753; D08518; A840577; alpha-Dihydrofucosterol, 22,23-Dihydrostigmasterol; Q-200712; SR-05000002307-2; SR-05000002307-3; Q63409374; .BETA.-SITOSTEROL (CONSTITUENT OF PYGEUM) [DSC]; BETA-SITOSTEROL (CONSTITUENT OF SAW PALMETTO) [DSC]; beta-Sitosterol, analytical standard, from soybean, >=40%; beta-Sitosterol, primary pharmaceutical reference standard; 24.BETA.-ETHYL-.DELTA.(SUP 5)-CHOLESTEN-3.BETA.-OL; BETA-SITOSTEROL (CONSTITUENT OF STINGING NETTLE) [DSC]; Beta-sitosterol, European Pharmacopoeia (EP) Reference Standard; beta-Sitosterol, United States Pharmacopeia (USP) Reference Standard; beta-Sitosterol, certified reference material, 100 mug/mL in chloroform; (3S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-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; 17-(5-ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; 76772-70-8
CAS 83-46-5
PubChem CID 222284
ChEMBL ID CHEMBL221542
*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: 414.7 ALogp: 9.3
HBD: 1 HBA: 1
Rotatable Bonds: 6 Lipinski's rule of five: Rejected
Polar Surface Area: 20.2 Aromatic Rings: 4
Heavy Atoms: 30 QED Weighted: 0.416

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.679 MDCK Permeability: 0.00001070
Pgp-inhibitor: 0.972 Pgp-substrate: 0.092
Human Intestinal Absorption (HIA): 0.002 20% Bioavailability (F20%): 0.889
30% Bioavailability (F30%): 0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.136 Plasma Protein Binding (PPB): 93.38%
Volume Distribution (VD): 1.484 Fu: 1.30%

ADMET: Metabolism

CYP1A2-inhibitor: 0.095 CYP1A2-substrate: 0.526
CYP2C19-inhibitor: 0.143 CYP2C19-substrate: 0.923
CYP2C9-inhibitor: 0.208 CYP2C9-substrate: 0.131
CYP2D6-inhibitor: 0.142 CYP2D6-substrate: 0.344
CYP3A4-inhibitor: 0.538 CYP3A4-substrate: 0.731

ADMET: Excretion

Clearance (CL): 7.21 Half-life (T1/2): 0.049

ADMET: Toxicity

hERG Blockers: 0.875 Human Hepatotoxicity (H-HT): 0.131
Drug-inuced Liver Injury (DILI): 0.551 AMES Toxicity: 0.002
Rat Oral Acute Toxicity: 0.003 Maximum Recommended Daily Dose: 0.214
Skin Sensitization: 0.963 Carcinogencity: 0.12
Eye Corrosion: 0.943 Eye Irritation: 0.869
Respiratory Toxicity: 0.464
*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
ENC001107 1.000 D0Y7LD 1.000
ENC000961 0.852 D0B4RU 0.581
ENC000125 0.809 D0K0EK 0.495
ENC001647 0.794 D0M4WA 0.422
ENC001545 0.729 D0G3SH 0.416
ENC001170 0.708 D03ZTE 0.416
ENC004758 0.698 D02STN 0.398
ENC001558 0.698 D06XMU 0.392
ENC002882 0.694 D0K5WS 0.364
ENC001764 0.694 D07BSQ 0.361
*Note: the compound similarity was calculated by RDKIT.