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

Details

• Internal ID: 90fb261d-5722-4f75-9d9e-be64254761d8
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (2S,3R,8S,9S,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-2,3,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-7,11-dione
• SMILES (Canonical): CC1(C(C(CC2C1=CC(=O)C3C2(C(=O)CC4(C3(CC(C4C(C)(C(=O)CCC(C)(C)O)O)O)C)C)C)O)O)C
• SMILES (Isomeric): C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2C(=O)C=C4[C@H]3C[C@@H]([C@@H](C4(C)C)O)O)C)C)[C@](C)(C(=O)CCC(C)(C)O)O)O
• InChI: InChI=1S/C30H46O8/c1-25(2,37)10-9-20(34)30(8,38)23-19(33)13-27(5)22-17(31)11-15-16(12-18(32)24(36)26(15,3)4)29(22,7)21(35)14-28(23,27)6/h11,16,18-19,22-24,32-33,36-38H,9-10,12-14H2,1-8H3/t16-,18+,19-,22+,23+,24+,27+,28-,29-,30+/m1/s1
• InChI Key: CEXXNUWIPXZZMB-CASDGZEASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₈
• Molecular Weight: 534.70 g/mol
• Exact Mass: 534.31926842 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9834	98.34%
Caco-2	-	0.6543	65.43%
Blood Brain Barrier	+	0.8388	83.88%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8055	80.55%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.8058	80.58%
OATP1B3 inhibitior	+	0.8748	87.48%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7532	75.32%
BSEP inhibitior	+	0.6135	61.35%
P-glycoprotein inhibitior	-	0.4701	47.01%
P-glycoprotein substrate	+	0.5205	52.05%
CYP3A4 substrate	+	0.6721	67.21%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8060	80.60%
CYP2C9 inhibition	-	0.8389	83.89%
CYP2C19 inhibition	-	0.7834	78.34%
CYP2D6 inhibition	-	0.9541	95.41%
CYP1A2 inhibition	-	0.9254	92.54%
CYP2C8 inhibition	-	0.6020	60.20%
CYP inhibitory promiscuity	-	0.9150	91.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6943	69.43%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9146	91.46%
Skin irritation	+	0.6254	62.54%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7332	73.32%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5914	59.14%
skin sensitisation	-	0.8018	80.18%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7338	73.38%
Acute Oral Toxicity (c)	I	0.5554	55.54%
Estrogen receptor binding	+	0.7294	72.94%
Androgen receptor binding	+	0.7609	76.09%
Thyroid receptor binding	+	0.6436	64.36%
Glucocorticoid receptor binding	+	0.7653	76.53%
Aromatase binding	+	0.7245	72.45%
PPAR gamma	+	0.5347	53.47%
Honey bee toxicity	-	0.7543	75.43%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.66%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.71%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.33%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.58%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.61%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.02%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.53%	95.56%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	87.50%	94.78%
CHEMBL2996	Q05655	Protein kinase C delta	84.72%	97.79%
CHEMBL4208	P20618	Proteasome component C5	84.59%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	84.44%	95.93%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.36%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.62%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.41%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.47%	99.23%

Plants that contains it

• Cayaponia racemosa

Cross-Links

• PubChem: 163017432
• LOTUS: LTS0145459
• wikiData: Q104956192