3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-17-(1-hydroxy-5-methylhex-4-enyl)-8,14-dimethyl-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde

Details

• Internal ID: 5cfe7a77-99f1-4f39-b0fc-268b1c671583
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: 3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-17-(1-hydroxy-5-methylhex-4-enyl)-8,14-dimethyl-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC(=CCCC(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C=O)C)C)O)C
• SMILES (Isomeric): CC(=CCCC(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C=O)C)C)O)C
• InChI: InChI=1S/C39H64O13/c1-20(2)6-5-7-25(43)23-12-14-37(3)24(23)8-9-28-38(37,4)13-10-21-16-22(11-15-39(21,28)19-42)49-36-34(32(47)30(45)27(18-41)51-36)52-35-33(48)31(46)29(44)26(17-40)50-35/h6,19,21-36,40-41,43-48H,5,7-18H2,1-4H3/t21?,22?,23?,24?,25?,26-,27-,28?,29-,30-,31+,32+,33-,34-,35+,36-,37?,38?,39?/m1/s1
• InChI Key: GVBDPCPLRGCHQH-QLRGAEDESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₄O₁₃
• Molecular Weight: 740.90 g/mol
• Exact Mass: 740.43469209 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7719	77.19%
Caco-2	-	0.8841	88.41%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8134	81.34%
OATP2B1 inhibitior	-	0.7336	73.36%
OATP1B1 inhibitior	+	0.8646	86.46%
OATP1B3 inhibitior	-	0.2428	24.28%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.7029	70.29%
P-glycoprotein inhibitior	+	0.7192	71.92%
P-glycoprotein substrate	-	0.5917	59.17%
CYP3A4 substrate	+	0.7281	72.81%
CYP2C9 substrate	-	0.8022	80.22%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.9469	94.69%
CYP2C9 inhibition	-	0.8637	86.37%
CYP2C19 inhibition	-	0.9118	91.18%
CYP2D6 inhibition	-	0.9391	93.91%
CYP1A2 inhibition	-	0.9069	90.69%
CYP2C8 inhibition	+	0.5673	56.73%
CYP inhibitory promiscuity	-	0.9514	95.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6516	65.16%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9166	91.66%
Skin irritation	-	0.5512	55.12%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7873	78.73%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7039	70.39%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.7399	73.99%
Acute Oral Toxicity (c)	I	0.4409	44.09%
Estrogen receptor binding	+	0.8122	81.22%
Androgen receptor binding	+	0.7744	77.44%
Thyroid receptor binding	-	0.5975	59.75%
Glucocorticoid receptor binding	+	0.6132	61.32%
Aromatase binding	+	0.6465	64.65%
PPAR gamma	+	0.6803	68.03%
Honey bee toxicity	-	0.5996	59.96%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9413	94.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.39%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.00%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.00%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.74%	96.61%
CHEMBL233	P35372	Mu opioid receptor	93.70%	97.93%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	93.29%	92.86%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.89%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.04%	96.38%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.10%	91.24%
CHEMBL2094135	Q96BI3	Gamma-secretase	90.10%	98.05%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	89.26%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.94%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.67%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.56%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.32%	85.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	88.26%	95.71%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.75%	94.23%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.37%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.82%	97.25%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	86.20%	95.58%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.28%	94.62%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.91%	93.10%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.83%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.22%	94.33%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.70%	97.29%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.53%	100.00%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	81.65%	95.52%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.61%	96.90%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.46%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.77%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.42%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.20%	92.62%

Plants that contains it

• Gymnema sylvestre
• Gynostemma pentaphyllum

Cross-Links

• PubChem: 5317936
• NPASS: NPC18838
• LOTUS: LTS0018764
• wikiData: Q105107418