(3S,5S)-3-hydroxy-3-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-(2-methylprop-1-enyl)oxolan-2-one

Details

• Internal ID: bf068d37-3cfd-4ac1-9884-2b734c9a53b0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,5S)-3-hydroxy-3-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-(2-methylprop-1-enyl)oxolan-2-one
• SMILES (Canonical): CC(=CC1CC(C(=O)O1)(C2CCC3(C2CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C)O)C
• SMILES (Isomeric): CC(=C[C@@H]1C[C@@](C(=O)O1)([C@H]2CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)C)O)C
• InChI: InChI=1S/C30H48O4/c1-18(2)16-19-17-30(33,25(32)34-19)21-10-14-28(6)20(21)8-9-23-27(5)13-12-24(31)26(3,4)22(27)11-15-29(23,28)7/h16,19-24,31,33H,8-15,17H2,1-7H3/t19-,20-,21+,22+,23-,24+,27+,28-,29-,30+/m1/s1
• InChI Key: UVWSKJGMKBMOEV-OVFYZRPFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.70 g/mol
• Exact Mass: 472.35526001 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 7.40
• Atomic LogP (AlogP): 6.05
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• BDBM50423985

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9929	99.29%
Caco-2	-	0.6328	63.28%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7566	75.66%
OATP2B1 inhibitior	-	0.7122	71.22%
OATP1B1 inhibitior	+	0.9051	90.51%
OATP1B3 inhibitior	+	0.8626	86.26%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	+	0.8062	80.62%
P-glycoprotein inhibitior	-	0.4872	48.72%
P-glycoprotein substrate	-	0.8038	80.38%
CYP3A4 substrate	+	0.7172	71.72%
CYP2C9 substrate	-	0.7853	78.53%
CYP2D6 substrate	-	0.8231	82.31%
CYP3A4 inhibition	-	0.6803	68.03%
CYP2C9 inhibition	-	0.8439	84.39%
CYP2C19 inhibition	-	0.7825	78.25%
CYP2D6 inhibition	-	0.9511	95.11%
CYP1A2 inhibition	-	0.8025	80.25%
CYP2C8 inhibition	-	0.7447	74.47%
CYP inhibitory promiscuity	-	0.8812	88.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4787	47.87%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9310	93.10%
Skin irritation	+	0.5971	59.71%
Skin corrosion	-	0.9247	92.47%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4428	44.28%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6592	65.92%
skin sensitisation	-	0.7910	79.10%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6913	69.13%
Acute Oral Toxicity (c)	I	0.8231	82.31%
Estrogen receptor binding	+	0.7549	75.49%
Androgen receptor binding	+	0.7614	76.14%
Thyroid receptor binding	+	0.6059	60.59%
Glucocorticoid receptor binding	+	0.7568	75.68%
Aromatase binding	+	0.7546	75.46%
PPAR gamma	+	0.6488	64.88%
Honey bee toxicity	-	0.6576	65.76%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9924	99.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	27800 nM	IC50	PMID: 23177789

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.76%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.43%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.27%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	86.17%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.76%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.32%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.88%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.68%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.55%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.00%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.95%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.78%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.73%	93.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.23%	85.30%
CHEMBL204	P00734	Thrombin	80.02%	96.01%

Plants that contains it

• Coleostephus myconis
• Dahlia pinnata
• Gynostemma pentaphyllum
• Synotis alata

Cross-Links

• PubChem: 60201376
• NPASS: NPC255387
• ChEMBL: CHEMBL2313418