3-O-(Rhaa1-4(Rhaa1-2)Glcb)-(25R)-spirost-5-en-3beta-ol

Details

• Internal ID: a53893ac-6532-448a-ad82-f71696ae891d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,3S,5R)-2-[(3S,4S,6R)-6-[[(3S,8S,9S,10R,13S,14S,16S,17R)-16-[(2S,5R)-2,5-dimethyloxan-2-yl]oxy-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-(hydroxymethyl)-5-[(2S,3S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CCC1C(CC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)OC6C(C(C(C(O6)C)O)O)O)O)OC7C(C(C(C(O7)C)O)O)O)C)C)OC8(CCC(CO8)C)C
• SMILES (Isomeric): CC[C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5C([C@H]([C@@H](C(O5)CO)O[C@H]6[C@H](C([C@H](C(O6)C)O)O)O)O)O[C@H]7[C@H](C([C@H](C(O7)C)O)O)O)C)C)O[C@]8(CC[C@H](CO8)C)C
• InChI: InChI=1S/C46H76O16/c1-8-27-30(62-46(7)16-11-21(2)20-55-46)18-29-26-10-9-24-17-25(12-14-44(24,5)28(26)13-15-45(27,29)6)58-43-40(61-42-37(53)35(51)33(49)23(4)57-42)38(54)39(31(19-47)59-43)60-41-36(52)34(50)32(48)22(3)56-41/h9,21-23,25-43,47-54H,8,10-20H2,1-7H3/t21-,22?,23?,25+,26-,27+,28+,29+,30+,31?,32+,33+,34?,35?,36+,37+,38+,39-,40?,41+,42+,43-,44+,45-,46+/m1/s1
• InChI Key: LDHFVSYQLJAAAR-FGRIONLZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₇₆O₁₆
• Molecular Weight: 885.10 g/mol
• Exact Mass: 884.51333633 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.02
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

• 3-O-(Rhaa1-4(Rhaa1-2)Glcb)-(25R)-spirost-5-en-3beta-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7246	72.46%
Caco-2	-	0.8884	88.84%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6338	63.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8706	87.06%
OATP1B3 inhibitior	+	0.8877	88.77%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9346	93.46%
P-glycoprotein inhibitior	+	0.7320	73.20%
P-glycoprotein substrate	+	0.6000	60.00%
CYP3A4 substrate	+	0.7469	74.69%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.8967	89.67%
CYP2C9 inhibition	-	0.9230	92.30%
CYP2C19 inhibition	-	0.8935	89.35%
CYP2D6 inhibition	-	0.9273	92.73%
CYP1A2 inhibition	-	0.8690	86.90%
CYP2C8 inhibition	+	0.7583	75.83%
CYP inhibitory promiscuity	-	0.8236	82.36%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5528	55.28%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.5227	52.27%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.8519	85.19%
Human Ether-a-go-go-Related Gene inhibition	+	0.7687	76.87%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.9108	91.08%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8685	86.85%
Acute Oral Toxicity (c)	III	0.6081	60.81%
Estrogen receptor binding	+	0.8540	85.40%
Androgen receptor binding	+	0.7286	72.86%
Thyroid receptor binding	-	0.5625	56.25%
Glucocorticoid receptor binding	+	0.5800	58.00%
Aromatase binding	+	0.6877	68.77%
PPAR gamma	+	0.7481	74.81%
Honey bee toxicity	-	0.5727	57.27%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9459	94.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	99.42%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.66%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.40%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.69%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.01%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.78%	100.00%
CHEMBL2581	P07339	Cathepsin D	93.18%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.78%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.18%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.91%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	87.57%	92.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.59%	91.71%
CHEMBL237	P41145	Kappa opioid receptor	85.03%	98.10%
CHEMBL1937	Q92769	Histone deacetylase 2	84.62%	94.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.51%	95.89%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	84.23%	98.46%
CHEMBL1914	P06276	Butyrylcholinesterase	83.21%	95.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.95%	94.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.74%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.49%	97.36%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.31%	97.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.20%	97.50%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.33%	89.05%
CHEMBL2996	Q05655	Protein kinase C delta	80.17%	97.79%

Plants that contains it

• Asparagus cochinchinensis
• Dioscorea althaeoides
• Dioscorea futschauensis
• Dioscorea gracillima
• Dioscorea japonica
• Dioscorea nipponica
• Dioscorea panthaica
• Dioscorea polystachya
• Dioscorea septemloba
• Dioscorea tokoro
• Dracaena draco
• Paris polyphylla
• Polygonatum zanlanscianense
• Smilax glabra
• Tribulus terrestris

Cross-Links

• PubChem: 52931449
• NPASS: NPC4925