(6R)-6-[(1R,3R,6S,8R,11S,12S,14S,15R,16R,18R)-6,18-dihydroxy-7,7,12,16-tetramethyl-14-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methylheptan-3-one

Details

• Internal ID: ead7f8e5-2537-47cb-8da0-1ffffe6b19d1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (6R)-6-[(1R,3R,6S,8R,11S,12S,14S,15R,16R,18R)-6,18-dihydroxy-7,7,12,16-tetramethyl-14-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methylheptan-3-one
• SMILES (Canonical): CC(C)C(=O)CCC(C)C1C(CC2(C1(CC(C34C2CCC5C3(C4)CCC(C5(C)C)O)O)C)C)OC6C(C(C(CO6)O)O)O
• SMILES (Isomeric): C[C@H](CCC(=O)C(C)C)[C@H]1[C@H](C[C@@]2([C@@]1(C[C@H]([C@]34[C@H]2CC[C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)O)O)C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O)O
• InChI: InChI=1S/C35H58O8/c1-18(2)20(36)9-8-19(3)27-22(43-30-29(41)28(40)21(37)16-42-30)14-32(6)24-11-10-23-31(4,5)25(38)12-13-34(23)17-35(24,34)26(39)15-33(27,32)7/h18-19,21-30,37-41H,8-17H2,1-7H3/t19-,21+,22+,23+,24+,25+,26-,27+,28+,29-,30+,32+,33-,34-,35+/m1/s1
• InChI Key: DMOJARJGPBYTOF-UONXQXKBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₈O₈
• Molecular Weight: 606.80 g/mol
• Exact Mass: 606.41316880 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.83
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7852	78.52%
Caco-2	-	0.8124	81.24%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7471	74.71%
OATP2B1 inhibitior	-	0.7163	71.63%
OATP1B1 inhibitior	+	0.8668	86.68%
OATP1B3 inhibitior	+	0.9197	91.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8292	82.92%
BSEP inhibitior	+	0.5956	59.56%
P-glycoprotein inhibitior	+	0.6502	65.02%
P-glycoprotein substrate	+	0.5083	50.83%
CYP3A4 substrate	+	0.7200	72.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8431	84.31%
CYP3A4 inhibition	-	0.8727	87.27%
CYP2C9 inhibition	-	0.7008	70.08%
CYP2C19 inhibition	-	0.8198	81.98%
CYP2D6 inhibition	-	0.9534	95.34%
CYP1A2 inhibition	-	0.8024	80.24%
CYP2C8 inhibition	+	0.5177	51.77%
CYP inhibitory promiscuity	-	0.9534	95.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7400	74.00%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9169	91.69%
Skin irritation	-	0.6440	64.40%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.6615	66.15%
Human Ether-a-go-go-Related Gene inhibition	+	0.7507	75.07%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8218	82.18%
skin sensitisation	-	0.8959	89.59%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8839	88.39%
Acute Oral Toxicity (c)	I	0.3892	38.92%
Estrogen receptor binding	+	0.5456	54.56%
Androgen receptor binding	+	0.7467	74.67%
Thyroid receptor binding	-	0.5289	52.89%
Glucocorticoid receptor binding	+	0.6530	65.30%
Aromatase binding	+	0.7098	70.98%
PPAR gamma	+	0.6340	63.40%
Honey bee toxicity	-	0.6458	64.58%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9417	94.17%

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	98.85%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.34%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.98%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.82%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.35%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.67%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.33%	95.17%
CHEMBL4302	P08183	P-glycoprotein 1	94.12%	92.98%
CHEMBL2581	P07339	Cathepsin D	92.95%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.20%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.60%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	87.84%	91.19%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.98%	96.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.86%	96.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.49%	96.47%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.41%	91.24%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.26%	95.89%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	84.83%	92.78%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.68%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.40%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.05%	95.89%
CHEMBL3837	P07711	Cathepsin L	83.24%	96.61%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.76%	92.88%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.50%	96.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.47%	95.50%
CHEMBL1075317	P61964	WD repeat-containing protein 5	81.81%	96.33%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.41%	89.05%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	80.51%	99.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.22%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.14%	89.00%

Plants that contains it

• Beilschmiedia erithrophloia
• Curculigo orchioides

Cross-Links

• PubChem: 101618895
• NPASS: NPC206756
• LOTUS: LTS0066203
• wikiData: Q105200995