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

Details

• Internal ID: d5a431f7-9e25-44e4-a407-722156dd6dc2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (2S,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,16-dihydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
• SMILES (Canonical): CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2CC(C1=O)O)CO)C)C(C)(C(=O)CCC(C)(C)O)O)O)C)C
• SMILES (Isomeric): C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)CO)C)[C@](C)(C(=O)CCC(C)(C)O)O)O
• InChI: InChI=1S/C30H46O8/c1-25(2,37)11-10-21(34)29(7,38)23-19(33)13-27(5)20-9-8-16-17(12-18(32)24(36)26(16,3)4)30(20,15-31)22(35)14-28(23,27)6/h8,17-20,23,31-33,37-38H,9-15H2,1-7H3/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1
• InChI Key: AGWNREQWNPJWPL-VOKXYEOFSA-N
• Popularity: 1 reference 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: 1.50
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9878	98.78%
Caco-2	-	0.6588	65.88%
Blood Brain Barrier	+	0.9129	91.29%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8426	84.26%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.8609	86.09%
OATP1B3 inhibitior	+	0.9099	90.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5550	55.50%
BSEP inhibitior	+	0.7906	79.06%
P-glycoprotein inhibitior	-	0.4904	49.04%
P-glycoprotein substrate	-	0.5178	51.78%
CYP3A4 substrate	+	0.6743	67.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8211	82.11%
CYP3A4 inhibition	-	0.8588	85.88%
CYP2C9 inhibition	-	0.8359	83.59%
CYP2C19 inhibition	-	0.9090	90.90%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9469	94.69%
CYP2C8 inhibition	+	0.4795	47.95%
CYP inhibitory promiscuity	-	0.8914	89.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7363	73.63%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9235	92.35%
Skin irritation	+	0.6036	60.36%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6830	68.30%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6217	62.17%
skin sensitisation	-	0.9125	91.25%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4503	45.03%
Acute Oral Toxicity (c)	III	0.8028	80.28%
Estrogen receptor binding	+	0.6979	69.79%
Androgen receptor binding	+	0.7536	75.36%
Thyroid receptor binding	+	0.6343	63.43%
Glucocorticoid receptor binding	+	0.7888	78.88%
Aromatase binding	+	0.7484	74.84%
PPAR gamma	-	0.4867	48.67%
Honey bee toxicity	-	0.7772	77.72%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9834	98.34%

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	97.83%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.02%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.00%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	94.03%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.46%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.39%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.98%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.59%	96.77%
CHEMBL299	P17252	Protein kinase C alpha	86.39%	98.03%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.91%	96.61%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.79%	96.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.22%	82.69%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	84.13%	87.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.24%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.44%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.83%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.06%	99.23%

Plants that contains it

• Cucumis melo

Cross-Links

• PubChem: 44139485
• NPASS: NPC121288
• LOTUS: LTS0155199
• wikiData: Q104912071