(2S,3R,4S,5R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol

Details

• Internal ID: f30cd2c5-6270-4323-aafd-f558bff4a36c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: (2S,3R,4S,5R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(CO5)O)O)O)C)C)C(C)C
• SMILES (Isomeric): CCC(CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)C)C)C(C)C
• InChI: InChI=1S/C34H58O5/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(39-32-31(37)30(36)29(35)19-38-32)14-16-33(23,5)28(25)15-17-34(26,27)6/h10,20-22,24-32,35-37H,7-9,11-19H2,1-6H3/t21-,22?,24+,25+,26-,27+,28+,29-,30+,31-,32+,33+,34-/m1/s1
• InChI Key: CIGIQYRFUVBHMZ-QLCJHUIXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₈O₅
• Molecular Weight: 546.80 g/mol
• Exact Mass: 546.42842495 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 7.80
• Atomic LogP (AlogP): 6.49
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9339	93.39%
Caco-2	-	0.8196	81.96%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7307	73.07%
OATP2B1 inhibitior	-	0.5726	57.26%
OATP1B1 inhibitior	+	0.9179	91.79%
OATP1B3 inhibitior	+	0.8988	89.88%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7542	75.42%
BSEP inhibitior	-	0.5453	54.53%
P-glycoprotein inhibitior	+	0.6243	62.43%
P-glycoprotein substrate	+	0.6956	69.56%
CYP3A4 substrate	+	0.7401	74.01%
CYP2C9 substrate	-	0.8028	80.28%
CYP2D6 substrate	-	0.8179	81.79%
CYP3A4 inhibition	-	0.7882	78.82%
CYP2C9 inhibition	-	0.7842	78.42%
CYP2C19 inhibition	-	0.8378	83.78%
CYP2D6 inhibition	-	0.9139	91.39%
CYP1A2 inhibition	-	0.8526	85.26%
CYP2C8 inhibition	+	0.5851	58.51%
CYP inhibitory promiscuity	-	0.8009	80.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6761	67.61%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9405	94.05%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	-	0.8578	85.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4230	42.30%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6012	60.12%
skin sensitisation	-	0.8820	88.20%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9397	93.97%
Acute Oral Toxicity (c)	III	0.5609	56.09%
Estrogen receptor binding	+	0.6914	69.14%
Androgen receptor binding	+	0.7245	72.45%
Thyroid receptor binding	-	0.5893	58.93%
Glucocorticoid receptor binding	+	0.6012	60.12%
Aromatase binding	-	0.4841	48.41%
PPAR gamma	+	0.5252	52.52%
Honey bee toxicity	-	0.7384	73.84%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5150	51.50%
Fish aquatic toxicity	+	0.9811	98.11%

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	98.17%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.87%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.97%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.17%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.14%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.26%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.39%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.90%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.47%	97.09%
CHEMBL240	Q12809	HERG	89.36%	89.76%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.22%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.11%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.84%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.55%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.89%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.47%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.98%	92.62%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.91%	90.24%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.16%	92.88%

Plants that contains it

• Akebia quinata
• Andrographis paniculata
• Lonicera japonica
• Lycium chinense
• Morus alba
• Papaver somniferum
• Patrinia scabiosifolia
• Periploca sepium
• Pinellia ternata
• Solanum torvum
• Vitex trifolia
• Woodwardia orientalis

Cross-Links

• PubChem: 6326040
• NPASS: NPC153552