(3R,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2S)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-3,16-dihydroxy-4,4,9,13,14-pentamethyl-3,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-2,11-dione

Details

• Internal ID: c44fb5b2-e1ff-4ca0-a862-7ad944548650
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (3R,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2S)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-3,16-dihydroxy-4,4,9,13,14-pentamethyl-3,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-2,11-dione
• SMILES (Canonical): CC1(C(C(=O)CC2C1=CCC3C2(C(=O)CC4(C3(CC(C4C(C)(C(=O)C=CC(C)(C)O)O)O)C)C)C)O)C
• SMILES (Isomeric): C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3CC(=O)[C@@H](C4(C)C)O)C)C)[C@@](C)(C(=O)/C=C/C(C)(C)O)O)O
• InChI: InChI=1S/C30H44O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-12,17,19-20,23-24,32,35-37H,10,13-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,24+,27+,28-,29+,30-/m1/s1
• InChI Key: ALPSEMFPAVSKJO-LFFXLFLLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₄O₇
• Molecular Weight: 516.70 g/mol
• Exact Mass: 516.30870374 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.93
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	-	0.6689	66.89%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7661	76.61%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8716	87.16%
OATP1B3 inhibitior	+	0.8772	87.72%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8314	83.14%
BSEP inhibitior	+	0.8832	88.32%
P-glycoprotein inhibitior	-	0.4633	46.33%
P-glycoprotein substrate	-	0.5755	57.55%
CYP3A4 substrate	+	0.6818	68.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8818	88.18%
CYP3A4 inhibition	-	0.7613	76.13%
CYP2C9 inhibition	-	0.8918	89.18%
CYP2C19 inhibition	-	0.8605	86.05%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.9256	92.56%
CYP2C8 inhibition	+	0.4863	48.63%
CYP inhibitory promiscuity	-	0.8932	89.32%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5949	59.49%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9170	91.70%
Skin irritation	+	0.5673	56.73%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6424	64.24%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5092	50.92%
skin sensitisation	-	0.7334	73.34%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5770	57.70%
Acute Oral Toxicity (c)	I	0.7424	74.24%
Estrogen receptor binding	+	0.7341	73.41%
Androgen receptor binding	+	0.7304	73.04%
Thyroid receptor binding	+	0.6580	65.80%
Glucocorticoid receptor binding	+	0.7521	75.21%
Aromatase binding	+	0.7528	75.28%
PPAR gamma	+	0.5420	54.20%
Honey bee toxicity	-	0.7659	76.59%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9948	99.48%

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	95.76%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.29%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.41%	97.25%
CHEMBL1902	P62942	FK506-binding protein 1A	91.23%	97.05%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.80%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.88%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.54%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.20%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.55%	85.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.65%	89.34%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.50%	91.07%
CHEMBL4208	P20618	Proteasome component C5	83.85%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.94%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.53%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	81.57%	90.17%
CHEMBL1937	Q92769	Histone deacetylase 2	80.56%	94.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.43%	96.95%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.39%	98.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.00%	89.00%

Plants that contains it

• Aquilaria sinensis
• Salvia miltiorrhiza

Cross-Links

• PubChem: 10649544
• NPASS: NPC34052