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)-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

Details

• Internal ID: f4150e74-f344-4217-a273-7f7077a4feaf
• 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)-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC(=CCCC(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4(C)C)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(C)C)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/C41H68O13/c1-21(2)8-7-9-24(45)22-12-15-39(5)23(22)10-11-28-40(39,6)16-13-27-38(3,4)29(14-17-41(27,28)20-44)53-37-35(33(49)31(47)26(19-43)52-37)54-36-34(50)32(48)30(46)25(18-42)51-36/h8,20,22-37,42-43,45-50H,7,9-19H2,1-6H3/t22?,23?,24?,25-,26-,27?,28?,29?,30-,31-,32+,33+,34-,35-,36+,37+,39?,40?,41?/m1/s1
• InChI Key: KPWIPFDLQMHSAQ-RVMGFPDHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₈O₁₃
• Molecular Weight: 769.00 g/mol
• Exact Mass: 768.46599222 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 1.97
• 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	-	0.8829	88.29%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8134	81.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8448	84.48%
OATP1B3 inhibitior	-	0.2428	24.28%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.6824	68.24%
P-glycoprotein inhibitior	+	0.7639	76.39%
P-glycoprotein substrate	-	0.6592	65.92%
CYP3A4 substrate	+	0.7220	72.20%
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	+	0.5989	59.89%
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	-	0.9134	91.34%
Skin irritation	-	0.5512	55.12%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7720	77.20%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7577	75.77%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.7011	70.11%
Acute Oral Toxicity (c)	I	0.4409	44.09%
Estrogen receptor binding	+	0.7741	77.41%
Androgen receptor binding	+	0.7726	77.26%
Thyroid receptor binding	-	0.5916	59.16%
Glucocorticoid receptor binding	+	0.6616	66.16%
Aromatase binding	+	0.6531	65.31%
PPAR gamma	+	0.7254	72.54%
Honey bee toxicity	-	0.5721	57.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.33%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.73%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.99%	96.61%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.97%	91.24%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.62%	96.38%
CHEMBL233	P35372	Mu opioid receptor	89.64%	97.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.64%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.20%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.12%	97.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.84%	92.86%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.65%	85.14%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.72%	98.05%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.47%	99.17%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.31%	95.71%
CHEMBL2581	P07339	Cathepsin D	85.15%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.96%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	84.71%	94.75%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.55%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.42%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.24%	94.33%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.97%	95.58%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.56%	92.78%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.44%	97.29%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.20%	97.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.15%	89.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.74%	92.88%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.89%	92.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.89%	97.36%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.86%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.77%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.34%	95.56%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	80.01%	97.47%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 11968578
• NPASS: NPC21258
• LOTUS: LTS0127348
• wikiData: Q105144407