gamma-Oryzanol

Details

• Internal ID: 85ab38c9-a35c-4476-bdca-35dac2a4af11
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cycloartanols and derivatives
• 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 (Canonical): CC(CCC=C(C)C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)OC(=O)C=CC6=CC(=C(C=C6)O)OC)C)C
• SMILES (Isomeric): 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
• InChI Key: FODTZLFLDFKIQH-FSVGXZBPSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₈O₄
• Molecular Weight: 602.90 g/mol
• Exact Mass: 602.43351033 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 12.10
• Atomic LogP (AlogP): 10.15
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

• Cycloartenyl ferulate
• gamma Oryzanol
• Oliver
• Gammariza
• 11042-64-1
• gamma-Orizanol
• HI-Z
• Gamma oryzanol [JAN]
• UNII-SST9XCL51M
• Cycloartenol Trans-Ferulate
• Cycloartenol ferulate
• 3-O-Ferulylcycloartenol
• 3PQR2YON9T
• SST9XCL51M
• Ferulic acid cycloartenol ester
• Oryzanol A
• 21238-33-5
• gamma Oryzanol (JAN)
• DSSTox_CID_1084
• DSSTox_RID_75932
• DSSTox_GSID_21084
• CAS-11042-64-1
• 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
• 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
• s3957
• AKOS016339566
• AKOS040757309
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	-	0.7798	77.98%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8023	80.23%
OATP2B1 inhibitior	-	0.7122	71.22%
OATP1B1 inhibitior	+	0.8106	81.06%
OATP1B3 inhibitior	+	0.8184	81.84%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9859	98.59%
P-glycoprotein inhibitior	+	0.7823	78.23%
P-glycoprotein substrate	+	0.5547	55.47%
CYP3A4 substrate	+	0.6907	69.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8476	84.76%
CYP3A4 inhibition	-	0.6803	68.03%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.5671	56.71%
CYP2D6 inhibition	-	0.9038	90.38%
CYP1A2 inhibition	-	0.5814	58.14%
CYP2C8 inhibition	+	0.7287	72.87%
CYP inhibitory promiscuity	-	0.7296	72.96%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9120	91.20%
Carcinogenicity (trinary)	Non-required	0.6519	65.19%
Eye corrosion	-	0.9942	99.42%
Eye irritation	-	0.9234	92.34%
Skin irritation	-	0.6613	66.13%
Skin corrosion	-	0.9665	96.65%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7804	78.04%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6656	66.56%
skin sensitisation	-	0.8032	80.32%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9201	92.01%
Acute Oral Toxicity (c)	IV	0.6075	60.75%
Estrogen receptor binding	+	0.7654	76.54%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5641	56.41%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.7350	73.50%
PPAR gamma	+	0.6870	68.70%
Honey bee toxicity	-	0.7535	75.35%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.32%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.75%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.60%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.39%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.14%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.07%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.98%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.02%	92.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.93%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.52%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.18%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.67%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.02%	92.94%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.66%	90.71%
CHEMBL2535	P11166	Glucose transporter	84.33%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.78%	97.14%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.66%	89.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.89%	99.17%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.55%	94.78%
CHEMBL4208	P20618	Proteasome component C5	82.42%	90.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.01%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.84%	91.07%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.67%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.05%	100.00%

Plants that contains it

• Krameria bicolor
• Oryza sativa

Cross-Links

• PubChem: 5282164
• LOTUS: LTS0199553
• wikiData: Q27257875