3b,5a,6a-Trihydroxyergosta-7,22-diene 6-O-benzoate

Details

• Internal ID: d21cd42c-53e0-48fd-8c21-7ef76a4a2eed
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Ergostane steroids > Ergosterols and derivatives
• IUPAC Name: [(3S,5R,6S,10R,13R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5-dihydroxy-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-yl] benzoate
• SMILES (Canonical): CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=CC(C4(C3(CCC(C4)O)C)O)OC(=O)C5=CC=CC=C5)C
• SMILES (Isomeric): C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CCC2[C@@]1(CCC3C2=C[C@@H]([C@@]4([C@@]3(CC[C@@H](C4)O)C)O)OC(=O)C5=CC=CC=C5)C
• InChI: InChI=1S/C35H50O4/c1-22(2)23(3)12-13-24(4)28-14-15-29-27-20-31(39-32(37)25-10-8-7-9-11-25)35(38)21-26(36)16-19-34(35,6)30(27)17-18-33(28,29)5/h7-13,20,22-24,26,28-31,36,38H,14-19,21H2,1-6H3/b13-12+/t23-,24+,26-,28+,29?,30?,31-,33+,34+,35-/m0/s1
• InChI Key: QPEMNZQKGBYUMV-LQMRAOCTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₀O₄
• Molecular Weight: 534.80 g/mol
• Exact Mass: 534.37091007 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 7.80
• Atomic LogP (AlogP): 7.36
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• [(3S,5R,6S,10R,13R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5-dihydroxy-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-yl] benzoate
• ((3S,5R,6S,10R,13R,17R)-17-((E,2R,5R)-5,6-dimethylhept-3-en-2-yl)-3,5-dihydroxy-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthren-6-yl) benzoate
• (2R,5S,7R,8S,14R,15R)-14-((2R,3E,5R)-5,6-Dimethylhept-3-en-2-yl)-5,7-dihydroxy-2,15-dimethyltetracyclo(8.7.0.0,.0,)heptadec-9-en-8-yl benzoic acid
• (2R,5S,7R,8S,14R,15R)-14-[(2R,3E,5R)-5,6-Dimethylhept-3-en-2-yl]-5,7-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-9-en-8-yl benzoic acid
• RefChem:95601
• 3b,5a,6a-Trihydroxyergosta-7,22-diene 6-O-benzoic acid
• CHEBI:202310

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	-	0.7491	74.91%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7961	79.61%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.7917	79.17%
OATP1B3 inhibitior	-	0.3690	36.90%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	+	0.9409	94.09%
P-glycoprotein inhibitior	+	0.6963	69.63%
P-glycoprotein substrate	-	0.5188	51.88%
CYP3A4 substrate	+	0.7060	70.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8411	84.11%
CYP3A4 inhibition	-	0.7754	77.54%
CYP2C9 inhibition	-	0.6302	63.02%
CYP2C19 inhibition	-	0.6771	67.71%
CYP2D6 inhibition	-	0.9249	92.49%
CYP1A2 inhibition	-	0.6184	61.84%
CYP2C8 inhibition	+	0.5719	57.19%
CYP inhibitory promiscuity	-	0.8233	82.33%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6124	61.24%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9458	94.58%
Skin irritation	+	0.5914	59.14%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7410	74.10%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6186	61.86%
skin sensitisation	-	0.7924	79.24%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8228	82.28%
Acute Oral Toxicity (c)	I	0.5841	58.41%
Estrogen receptor binding	+	0.8594	85.94%
Androgen receptor binding	+	0.6865	68.65%
Thyroid receptor binding	+	0.6192	61.92%
Glucocorticoid receptor binding	+	0.7956	79.56%
Aromatase binding	+	0.6581	65.81%
PPAR gamma	+	0.6757	67.57%
Honey bee toxicity	-	0.7456	74.56%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
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
CHEMBL221	P23219	Cyclooxygenase-1	98.97%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	97.15%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.47%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.03%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	93.71%	85.31%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.40%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	92.51%	94.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.25%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.46%	95.89%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	89.77%	97.53%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.68%	91.11%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	89.64%	94.97%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.04%	94.08%
CHEMBL2535	P11166	Glucose transporter	87.93%	98.75%
CHEMBL5028	O14672	ADAM10	86.94%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.20%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.65%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.60%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.51%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.51%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.13%	94.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.41%	93.56%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.16%	83.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.38%	95.93%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.05%	96.38%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139584507
• LOTUS: LTS0097731
• wikiData: Q77370571