(2R)-2-[(3S,7R,8S,9S,10R,13S,14S,16S,17R)-7-hydroxy-10,13-dimethyl-3,16-bis[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-4-one

Details

• Internal ID: 5eec31d7-b0f0-4913-8107-c00be814c1f9
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2R)-2-[(3S,7R,8S,9S,10R,13S,14S,16S,17R)-7-hydroxy-10,13-dimethyl-3,16-bis[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-4-one
• SMILES (Canonical): CC(C)CC(=O)CC(C)C1C(CC2C1(CCC3C2C(C=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)O)C)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@H](CC(=O)CC(C)C)[C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C39H64O14/c1-17(2)10-20(42)11-18(3)29-25(51-37-35(49)33(47)31(45)27(16-41)53-37)14-23-28-22(7-9-39(23,29)5)38(4)8-6-21(12-19(38)13-24(28)43)50-36-34(48)32(46)30(44)26(15-40)52-36/h13,17-18,21-37,40-41,43-49H,6-12,14-16H2,1-5H3/t18-,21+,22+,23+,24+,25+,26-,27-,28-,29+,30-,31-,32+,33+,34-,35-,36-,37-,38+,39+/m1/s1
• InChI Key: AJUXWMBUYRRTJS-YFAMFGMBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₄O₁₄
• Molecular Weight: 756.90 g/mol
• Exact Mass: 756.42960671 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.16
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7907	79.07%
Caco-2	-	0.8811	88.11%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8651	86.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8458	84.58%
OATP1B3 inhibitior	-	0.4111	41.11%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	-	0.6252	62.52%
P-glycoprotein inhibitior	+	0.7053	70.53%
P-glycoprotein substrate	-	0.5760	57.60%
CYP3A4 substrate	+	0.7303	73.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8581	85.81%
CYP3A4 inhibition	-	0.9642	96.42%
CYP2C9 inhibition	-	0.8723	87.23%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.8907	89.07%
CYP2C8 inhibition	+	0.5237	52.37%
CYP inhibitory promiscuity	-	0.9193	91.93%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6168	61.68%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9216	92.16%
Skin irritation	-	0.5922	59.22%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.6977	69.77%
Human Ether-a-go-go-Related Gene inhibition	+	0.7967	79.67%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7757	77.57%
skin sensitisation	-	0.9044	90.44%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.6815	68.15%
Acute Oral Toxicity (c)	III	0.7126	71.26%
Estrogen receptor binding	+	0.7921	79.21%
Androgen receptor binding	+	0.7037	70.37%
Thyroid receptor binding	-	0.5838	58.38%
Glucocorticoid receptor binding	-	0.4751	47.51%
Aromatase binding	+	0.6337	63.37%
PPAR gamma	+	0.6715	67.15%
Honey bee toxicity	-	0.7012	70.12%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6855	68.55%
Fish aquatic toxicity	+	0.9649	96.49%

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	98.62%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.20%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.92%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.04%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.94%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.78%	95.93%
CHEMBL237	P41145	Kappa opioid receptor	92.72%	98.10%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.87%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.73%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.43%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.94%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.54%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.33%	90.08%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.25%	91.07%
CHEMBL5255	O00206	Toll-like receptor 4	80.60%	92.50%
CHEMBL5028	O14672	ADAM10	80.41%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	80.38%	90.17%
CHEMBL220	P22303	Acetylcholinesterase	80.36%	94.45%

Plants that contains it

• Aframomum zambesiacum
• Alisma plantago-aquatica
• Ambrosia cumanensis
• Angostura granulosa
• Buckiella undulata
• Camassia cusickii
• Chamaecrista dentata
• Clausena anisum-olens
• Clinostemon mahuba
• Dioscorea cirrhosa
• Echinops bannaticus
• Euonymus lucidus
• Euphorbia lamprocarpa
• Ferula transiliensis
• Fraxinus angustifolia
• Genista hystrix
• Helichrysum anomalum
• Heptapleurum bodinieri
• Hippomane mancinella
• Isatis costata
• Kartalinia acaulis
• Machilus thunbergii
• Prunus sibirica
• Rhododendron ponticum
• Senecio roseus
• Seriphidium aucheri
• Speranskia tuberculata
• Veronica hederifolia
• Viguiera dentata
• Yucca gloriosa

Cross-Links

• PubChem: 101620741
• NPASS: NPC126142
• LOTUS: LTS0039819
• wikiData: Q104913407