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

Details

• Internal ID: 83ad6168-27c1-480b-8c61-640f5f8fddc8
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (2R,9S,13S,14R,16S)-17-[(E,2S)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-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)C)C)C(C)(C(=O)C=CC(C)(C)O)O)O)C)C
• SMILES (Isomeric): C[C@]12C[C@@H](C([C@@]1(CC(=O)[C@]3(C2CC=C4C3C[C@H](C(=O)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/h9,11-12,17-20,23,31-32,36-37H,10,13-15H2,1-8H3/b12-11+/t17?,18-,19+,20?,23?,27-,28+,29-,30-/m1/s1
• InChI Key: SRPHMISUTWFFKJ-NDIGCUPJSA-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: 2.10
• 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	+	0.9914	99.14%
Caco-2	-	0.6509	65.09%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7273	72.73%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8734	87.34%
OATP1B3 inhibitior	+	0.9309	93.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8064	80.64%
BSEP inhibitior	+	0.8560	85.60%
P-glycoprotein inhibitior	+	0.5794	57.94%
P-glycoprotein substrate	-	0.6095	60.95%
CYP3A4 substrate	+	0.6848	68.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8818	88.18%
CYP3A4 inhibition	-	0.7343	73.43%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9461	94.61%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5076	50.76%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5708	57.08%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9204	92.04%
Skin irritation	+	0.6094	60.94%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6551	65.51%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5092	50.92%
skin sensitisation	-	0.7211	72.11%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.4673	46.73%
Acute Oral Toxicity (c)	I	0.8231	82.31%
Estrogen receptor binding	+	0.7306	73.06%
Androgen receptor binding	+	0.7406	74.06%
Thyroid receptor binding	+	0.6478	64.78%
Glucocorticoid receptor binding	+	0.8013	80.13%
Aromatase binding	+	0.7720	77.20%
PPAR gamma	-	0.4879	48.79%
Honey bee toxicity	-	0.7527	75.27%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	95.85%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.43%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.94%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.78%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.57%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.40%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.17%	96.09%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.12%	87.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.15%	85.14%
CHEMBL1902	P62942	FK506-binding protein 1A	84.91%	97.05%
CHEMBL221	P23219	Cyclooxygenase-1	84.41%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.37%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	84.03%	91.19%
CHEMBL4208	P20618	Proteasome component C5	83.72%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.70%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.54%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.45%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.00%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.34%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.30%	99.23%

Plants that contains it

• Aquilaria sinensis
• Bryonia alba

Cross-Links

• PubChem: 17750993
• NPASS: NPC246238