(1S,3R,8S,9S,10R,11R,13S,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-1,3,11-trihydroxy-10-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid

Details

• Internal ID: 39c08d2b-d1a4-4a3e-963e-f00024606a0b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Ergostane steroids > Ergosterols and derivatives
• IUPAC Name: (1S,3R,8S,9S,10R,11R,13S,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-1,3,11-trihydroxy-10-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid
• SMILES (Canonical): CC(C)C(C)CCC(C)C1CCC2C1(CC(C3C2CC=C4C3(C(CC(C4)O)O)C)O)C(=O)O
• SMILES (Isomeric): C[C@H](CC[C@@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(C[C@H]([C@H]3[C@H]2CC=C4[C@@]3([C@H](C[C@@H](C4)O)O)C)O)C(=O)O
• InChI: InChI=1S/C28H46O5/c1-15(2)16(3)6-7-17(4)21-10-11-22-20-9-8-18-12-19(29)13-24(31)27(18,5)25(20)23(30)14-28(21,22)26(32)33/h8,15-17,19-25,29-31H,6-7,9-14H2,1-5H3,(H,32,33)/t16-,17-,19-,20+,21-,22+,23-,24+,25-,27-,28+/m1/s1
• InChI Key: KUYWDBVHKFAEJK-HTZWKTINSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₆O₅
• Molecular Weight: 462.70 g/mol
• Exact Mass: 462.33452456 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.64
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9910	99.10%
Caco-2	-	0.7006	70.06%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7730	77.30%
OATP2B1 inhibitior	-	0.5792	57.92%
OATP1B1 inhibitior	+	0.8501	85.01%
OATP1B3 inhibitior	-	0.3917	39.17%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6299	62.99%
P-glycoprotein inhibitior	-	0.5844	58.44%
P-glycoprotein substrate	+	0.6797	67.97%
CYP3A4 substrate	+	0.7025	70.25%
CYP2C9 substrate	-	0.8404	84.04%
CYP2D6 substrate	-	0.8509	85.09%
CYP3A4 inhibition	-	0.8753	87.53%
CYP2C9 inhibition	-	0.8844	88.44%
CYP2C19 inhibition	-	0.9055	90.55%
CYP2D6 inhibition	-	0.9612	96.12%
CYP1A2 inhibition	-	0.9222	92.22%
CYP2C8 inhibition	-	0.5734	57.34%
CYP inhibitory promiscuity	-	0.8392	83.92%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6629	66.29%
Eye corrosion	-	0.9946	99.46%
Eye irritation	-	0.9550	95.50%
Skin irritation	+	0.6866	68.66%
Skin corrosion	-	0.9471	94.71%
Ames mutagenesis	-	0.6859	68.59%
Human Ether-a-go-go-Related Gene inhibition	-	0.5511	55.11%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7321	73.21%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7000	70.00%
Acute Oral Toxicity (c)	I	0.8187	81.87%
Estrogen receptor binding	+	0.8048	80.48%
Androgen receptor binding	+	0.7859	78.59%
Thyroid receptor binding	+	0.5579	55.79%
Glucocorticoid receptor binding	+	0.7150	71.50%
Aromatase binding	-	0.5150	51.50%
PPAR gamma	-	0.5235	52.35%
Honey bee toxicity	-	0.7911	79.11%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9955	99.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.86%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.11%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.40%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.56%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.58%	93.56%
CHEMBL2581	P07339	Cathepsin D	89.33%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.31%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.25%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.77%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	88.32%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.25%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	85.02%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.56%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.94%	86.33%
CHEMBL5028	O14672	ADAM10	81.45%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.26%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.57%	93.00%

Plants that contains it

• Adenocaulon himalaicum
• Cunila spicata
• Phlomis armeniaca
• Pluchea indica
• Saussurea cordifolia
• Viburnum orientale
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 162988419
• LOTUS: LTS0238517
• wikiData: Q105178298