(2R,3R,4R,5S)-2-[[(3R,5S,6S,7R,9R,10R,13R,16R,17R)-7-[(2R,3R,4R,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxy-2-methoxyethyl]oxolan-2-yl]oxy-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy]-5-[(1S)-1-hydroxy-2-methoxyethyl]oxolane-3,4-diol

Details

• Internal ID: a0aa5612-1497-4708-99ef-d90fa01ede78
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: (2R,3R,4R,5S)-2-[[(3R,5S,6S,7R,9R,10R,13R,16R,17R)-7-[(2R,3R,4R,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxy-2-methoxyethyl]oxolan-2-yl]oxy-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy]-5-[(1S)-1-hydroxy-2-methoxyethyl]oxolane-3,4-diol
• SMILES (Canonical): CCC(CCC(C)C1C(CC2=C3C(CCC12C)C4(CCC(CC4C(C3OC5C(C(C(O5)C(COC)O)O)O)O)O)C)OC6C(C(C(O6)C(COC)O)O)O)C(C)C
• SMILES (Isomeric): CCC(CC[C@@H](C)[C@H]1[C@@H](CC2=C3[C@H](CC[C@]12C)[C@]4(CC[C@H](C[C@@H]4[C@@H]([C@@H]3O[C@H]5[C@@H]([C@H]([C@@H](O5)[C@H](COC)O)O)O)O)O)C)O[C@H]6[C@@H]([C@H]([C@@H](O6)[C@H](COC)O)O)O)C(C)C
• InChI: InChI=1S/C43H74O14/c1-9-22(20(2)3)11-10-21(4)31-29(54-40-35(50)33(48)37(55-40)27(45)18-52-7)17-25-30-24(13-15-43(25,31)6)42(5)14-12-23(44)16-26(42)32(47)39(30)57-41-36(51)34(49)38(56-41)28(46)19-53-8/h20-24,26-29,31-41,44-51H,9-19H2,1-8H3/t21-,22?,23-,24+,26-,27+,28+,29-,31+,32+,33-,34-,35-,36-,37+,38+,39-,40-,41+,42-,43+/m1/s1
• InChI Key: MXFMHAVXAGVCGZ-QLDMGMRTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₇₄O₁₄
• Molecular Weight: 815.00 g/mol
• Exact Mass: 814.50785703 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9522	95.22%
Caco-2	-	0.8688	86.88%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6633	66.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8511	85.11%
OATP1B3 inhibitior	+	0.9278	92.78%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5126	51.26%
P-glycoprotein inhibitior	+	0.7150	71.50%
P-glycoprotein substrate	+	0.6463	64.63%
CYP3A4 substrate	+	0.7267	72.67%
CYP2C9 substrate	-	0.8041	80.41%
CYP2D6 substrate	-	0.8262	82.62%
CYP3A4 inhibition	-	0.7478	74.78%
CYP2C9 inhibition	-	0.7763	77.63%
CYP2C19 inhibition	-	0.8308	83.08%
CYP2D6 inhibition	-	0.9167	91.67%
CYP1A2 inhibition	-	0.9001	90.01%
CYP2C8 inhibition	+	0.5843	58.43%
CYP inhibitory promiscuity	-	0.9014	90.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4392	43.92%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9043	90.43%
Skin irritation	-	0.6114	61.14%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.7337	73.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7051	70.51%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6445	64.45%
skin sensitisation	-	0.8656	86.56%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7475	74.75%
Acute Oral Toxicity (c)	III	0.4833	48.33%
Estrogen receptor binding	+	0.7285	72.85%
Androgen receptor binding	+	0.7275	72.75%
Thyroid receptor binding	-	0.5804	58.04%
Glucocorticoid receptor binding	+	0.5627	56.27%
Aromatase binding	+	0.6515	65.15%
PPAR gamma	+	0.6697	66.97%
Honey bee toxicity	-	0.6664	66.64%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9630	96.30%

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	98.59%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	98.38%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.76%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.68%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.04%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.90%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.73%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.32%	97.25%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	89.22%	95.58%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.09%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.34%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.97%	89.05%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.96%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.95%	92.62%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.10%	96.38%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.47%	96.00%
CHEMBL1977	P11473	Vitamin D receptor	82.66%	99.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.55%	86.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.40%	89.50%
CHEMBL4302	P08183	P-glycoprotein 1	81.63%	92.98%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.56%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.51%	95.93%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.41%	96.37%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.24%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	81.19%	98.35%
CHEMBL4581	P52732	Kinesin-like protein 1	80.97%	93.18%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.36%	82.38%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.33%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 46886870
• LOTUS: LTS0227653
• wikiData: Q105174039