Natural Product: ENC001582

NPs Basic Information

Download MOL File
Name
gamma-Oryzanol
Molecular Formula C40H58O4
IUPAC Name*
[(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILES
C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)OC(=O)/C=C/C6=CC(=C(C=C6)O)OC)C)C
InChI
InChI=1S/C40H58O4/c1-26(2)10-9-11-27(3)29-18-20-38(7)33-16-15-32-36(4,5)34(19-21-39(32)25-40(33,39)23-22-37(29,38)6)44-35(42)17-13-28-12-14-30(41)31(24-28)43-8/h10,12-14,17,24,27,29,32-34,41H,9,11,15-16,18-23,25H2,1-8H3/b17-13+/t27-,29-,32+,33+,34+,37-,38+,39-,40+/m1/s1
InChIKey
FODTZLFLDFKIQH-FSVGXZBPSA-N
Synonyms
gamma-Oryzanol; Cycloartenyl ferulate; gamma Oryzanol; Oliver; 11042-64-1; Gammariza; gamma-Orizanol; HI-Z; Cycloartenol Trans-Ferulate; Cycloartenol ferulate; Gamma oryzanol [JAN]; 3-O-Ferulylcycloartenol; 3PQR2YON9T; Ferulic acid cycloartenol ester; Oryzanol A; gamma Oryzanol (JAN); DSSTox_CID_1084; 21238-33-5; DSSTox_RID_75932; DSSTox_GSID_21084; CAS-11042-64-1; UNII-SST9XCL51M; Cycloartenol ferulic acid ester; CCRIS 4251; y-Oryzanol; gamma -Oryzanol; NCGC00181756-01; 9,19-CYCLOLANOST-24-EN-3-OL, 3-((2E)-3-(4-HYDROXY-3-METHOXYPHENYL)-2-PROPENOATE), (3.BETA.)-; 9,19-Cyclolanost-24-en-3-ol, 3-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate], (3.beta.)-; gamma-Oryzanol (TN); ORYZANOL A [MI]; UNII-3PQR2YON9T; SST9XCL51M; Hi-Z (TN); Cycloartenol, trans-ferulate; SCHEMBL718726; (3beta)-9,19-Cyclolanost-24-en-3-yl 4-hydroxy-3-methoxycinnamate; CHEMBL388595; CHEBI:32345; CYCLOARTENYL FERULATE [INCI]; EINECS 244-285-1; Tox21_112482; BDBM50483936; MFCD00867548; s3957; ZINC28646872; AKOS016339566; Tox21_112482_1; CCG-270201; OZ; HY-125938; CS-0103198; D01221; E88692; J-002421; Q27257875; 9,19-Cyclo-9beta-lanost-24-en-3beta-ol 4-hydroxy-3-methoxycinamate; 9,19-CYCLO-9.BETA.-LANOST-24-EN-3.BETA.-OL 4-HYDROXY-3-METHOXYCINAMATE; 9,19-CYCLO-9.BETA.-LANOST-24-EN-3.BETA.-OL, 4-HYDROXY-3-METHOXYCINNAMATE; [(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; 286011-27-6; 9,19-CYCLOLANOST-24-EN-3-OL, (2E)-3-(4-HYDROXY-3-METHOXYPHENYL)-2-PROPENOATE, (3.BETA.)-; 9,19-CYCLOLANOST-24-EN-3-OL, 3-(4-HYDROXY-3-METHOXYPHENYL)-2-PROPENOATE, (3.BETA.)-; CINNAMIC ACID, 4-HYDROXY-3-METHOXY-, 9,19-CYCLO-9.BETA.-LANOST-24-EN-3.BETA.-YL ESTER
CAS 11042-64-1
PubChem CID 5282164
ChEMBL ID CHEMBL388595
*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: Cycloartanols and derivat
          • Direct Parent: Cycloartanols and derivat

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Physi-Chem Properties

Molecular Weight: 602.9 ALogp: 12.1
HBD: 1 HBA: 4
Rotatable Bonds: 9 Lipinski's rule of five: Rejected
Polar Surface Area: 55.8 Aromatic Rings: 6
Heavy Atoms: 44 QED Weighted: 0.151

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.044 MDCK Permeability: 0.00001930
Pgp-inhibitor: 0.978 Pgp-substrate: 0.001
Human Intestinal Absorption (HIA): 0.003 20% Bioavailability (F20%): 0.945
30% Bioavailability (F30%): 0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.013 Plasma Protein Binding (PPB): 97.37%
Volume Distribution (VD): 2.409 Fu: 2.72%

ADMET: Metabolism

CYP1A2-inhibitor: 0.045 CYP1A2-substrate: 0.26
CYP2C19-inhibitor: 0.261 CYP2C19-substrate: 0.906
CYP2C9-inhibitor: 0.169 CYP2C9-substrate: 0.907
CYP2D6-inhibitor: 0.568 CYP2D6-substrate: 0.825
CYP3A4-inhibitor: 0.757 CYP3A4-substrate: 0.747

ADMET: Excretion

Clearance (CL): 8.742 Half-life (T1/2): 0.04

ADMET: Toxicity

hERG Blockers: 0.949 Human Hepatotoxicity (H-HT): 0.482
Drug-inuced Liver Injury (DILI): 0.198 AMES Toxicity: 0.002
Rat Oral Acute Toxicity: 0.101 Maximum Recommended Daily Dose: 0.872
Skin Sensitization: 0.969 Carcinogencity: 0.04
Eye Corrosion: 0.014 Eye Irritation: 0.084
Respiratory Toxicity: 0.868
*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.