(1S,4S,5S,8R,9R,13S,16R)-8-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.01,13.04,12.05,9]nonadec-2-en-16-ol

Details

• Internal ID: b0bc1ebd-cc82-4a00-bab1-f48c291ac4dd
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (1S,4S,5S,8R,9R,13S,16R)-8-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.01,13.04,12.05,9]nonadec-2-en-16-ol
• SMILES (Canonical): CC(CC=CC(C)(C)O)C1CCC2(C1(CCC34C2C=CC5(C3CCC(C5(C)C)O)OC4)C)C
• SMILES (Isomeric): C[C@H](C/C=C/C(C)(C)O)[C@H]1CC[C@@]2([C@@]1(CCC34[C@H]2C=C[C@@]5([C@H]3CC[C@H](C5(C)C)O)OC4)C)C
• InChI: InChI=1S/C30H48O3/c1-20(9-8-14-25(2,3)32)21-12-15-28(7)22-13-16-30-23(10-11-24(31)26(30,4)5)29(22,19-33-30)18-17-27(21,28)6/h8,13-14,16,20-24,31-32H,9-12,15,17-19H2,1-7H3/b14-8+/t20-,21-,22+,23+,24-,27-,28+,29?,30+/m1/s1
• InChI Key: GDWGKJJMMBZZDX-YKEKEUCZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₃
• Molecular Weight: 456.70 g/mol
• Exact Mass: 456.36034539 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 6.29
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	-	0.5783	57.83%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6129	61.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8588	85.88%
OATP1B3 inhibitior	+	0.9613	96.13%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7150	71.50%
BSEP inhibitior	+	0.8853	88.53%
P-glycoprotein inhibitior	-	0.4930	49.30%
P-glycoprotein substrate	+	0.5308	53.08%
CYP3A4 substrate	+	0.6728	67.28%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.7433	74.33%
CYP3A4 inhibition	-	0.8412	84.12%
CYP2C9 inhibition	-	0.7672	76.72%
CYP2C19 inhibition	-	0.7741	77.41%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.8117	81.17%
CYP2C8 inhibition	+	0.4691	46.91%
CYP inhibitory promiscuity	-	0.7696	76.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5966	59.66%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9454	94.54%
Skin irritation	-	0.6873	68.73%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	-	0.6607	66.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.8511	85.11%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7935	79.35%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7465	74.65%
Acute Oral Toxicity (c)	III	0.4402	44.02%
Estrogen receptor binding	+	0.8614	86.14%
Androgen receptor binding	+	0.7274	72.74%
Thyroid receptor binding	+	0.7044	70.44%
Glucocorticoid receptor binding	+	0.7824	78.24%
Aromatase binding	+	0.7140	71.40%
PPAR gamma	+	0.6097	60.97%
Honey bee toxicity	-	0.7448	74.48%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9697	96.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.46%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.54%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.49%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.35%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.24%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.43%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.20%	96.77%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.61%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	88.43%	91.03%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.42%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.03%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.62%	92.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.28%	97.09%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.89%	98.75%
CHEMBL2996	Q05655	Protein kinase C delta	83.51%	97.79%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.97%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.76%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.51%	89.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.77%	89.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.61%	86.33%
CHEMBL5028	O14672	ADAM10	81.05%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.81%	91.07%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.77%	89.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.71%	97.28%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.61%	95.56%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	80.33%	87.16%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.33%	90.24%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.19%	95.00%
CHEMBL5646	Q6L5J4	FML2_HUMAN	80.16%	100.00%

Plants that contains it

• Momordica charantia

Cross-Links

• PubChem: 163189716
• LOTUS: LTS0102049
• wikiData: Q105006999