Marsdekoiside A

Details

• Internal ID: 338627e6-2e82-4aed-9263-4f46f08c1477
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: [3-[5-[5-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-8,14,17-trihydroxy-17-(1-hydroxyethyl)-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,15,16-dodecahydrocyclopenta[a]phenanthren-12-yl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(CC2OC)OC3C(OC(CC3OC)OC4CCC5(C(C4)CCC6(C5CC(C7(C6(CCC7(C(C)O)O)O)C)OC(=O)C=CC8=CC=CC=C8)O)C)C)C)O)OC)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(OC(CC2OC)OC3C(OC(CC3OC)OC4CCC5(C(C4)CCC6(C5CC(C7(C6(CCC7(C(C)O)O)O)C)OC(=O)/C=C/C8=CC=CC=C8)O)C)C)C)O)OC)O
• InChI: InChI=1S/C51H78O17/c1-27-41(54)45(61-9)42(55)46(64-27)68-44-29(3)63-40(25-35(44)60-8)67-43-28(2)62-39(24-34(43)59-7)65-33-18-19-47(5)32(23-33)17-20-50(57)36(47)26-37(66-38(53)16-15-31-13-11-10-12-14-31)48(6)49(56,30(4)52)21-22-51(48,50)58/h10-16,27-30,32-37,39-46,52,54-58H,17-26H2,1-9H3/b16-15+
• InChI Key: PHHVCGYLKLDQTE-FOCLMDBBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₇₈O₁₇
• Molecular Weight: 963.20 g/mol
• Exact Mass: 962.52390102 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.54
• H-Bond Acceptor: 17
• H-Bond Donor: 6
• Rotatable Bonds: 13

Synonyms

• 139953-36-9
• [3-[5-[5-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-8,14,17-trihydroxy-17-(1-hydroxyethyl)-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,15,16-dodecahydrocyclopenta[a]phenanthren-12-yl] (E)-3-phenylprop-2-enoate
• 12-O-Cinnamoyl-dihydrosarcostin-3-O-3-O-methyl-6-deoxy-beta-D-allopyranosyl(1-4)-O-beta-D-oleandropyranosyl(1-4)-O-beta-D-cymaropyranoside
• Pregnane-8,12,14,17,20-pentol, 3-((O-6-deoxy-3-O-methyl-beta-D-allopyranosyl-(1-4)-O-2,6-dideoxy-3-O-methyl-beta-D-arabino-hexopyranosyl-(1-4)-2,6-dideoxy-3-O-methyl-beta-D-ribo-hexopyranosyl)oxy)-, 12-(3-phenyl-2-propenoate), (3beta,5alpha,12beta,14beta,17alpha,20S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8398	83.98%
Caco-2	-	0.8701	87.01%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6137	61.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8527	85.27%
OATP1B3 inhibitior	+	0.8342	83.42%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8321	83.21%
BSEP inhibitior	+	0.9792	97.92%
P-glycoprotein inhibitior	+	0.7463	74.63%
P-glycoprotein substrate	+	0.7478	74.78%
CYP3A4 substrate	+	0.7352	73.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8864	88.64%
CYP3A4 inhibition	-	0.8480	84.80%
CYP2C9 inhibition	-	0.9335	93.35%
CYP2C19 inhibition	-	0.9091	90.91%
CYP2D6 inhibition	-	0.9397	93.97%
CYP1A2 inhibition	-	0.8340	83.40%
CYP2C8 inhibition	+	0.6670	66.70%
CYP inhibitory promiscuity	-	0.9667	96.67%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5721	57.21%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9031	90.31%
Skin irritation	-	0.5567	55.67%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.7670	76.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8208	82.08%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6468	64.68%
skin sensitisation	-	0.8829	88.29%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9744	97.44%
Acute Oral Toxicity (c)	II	0.4417	44.17%
Estrogen receptor binding	+	0.8053	80.53%
Androgen receptor binding	+	0.7551	75.51%
Thyroid receptor binding	+	0.6058	60.58%
Glucocorticoid receptor binding	+	0.7515	75.15%
Aromatase binding	+	0.5822	58.22%
PPAR gamma	+	0.8125	81.25%
Honey bee toxicity	-	0.6523	65.23%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.70%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.93%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.91%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.17%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.62%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	95.24%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.64%	89.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	92.56%	94.08%
CHEMBL2581	P07339	Cathepsin D	91.39%	98.95%
CHEMBL5028	O14672	ADAM10	90.73%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.56%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.13%	94.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.94%	95.89%
CHEMBL4302	P08183	P-glycoprotein 1	87.00%	92.98%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.97%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.93%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.79%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.76%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.87%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.37%	97.14%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.79%	89.44%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.17%	89.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.84%	99.23%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	82.76%	91.65%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.52%	93.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.25%	100.00%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.93%	95.00%

Plants that contains it

• Marsdenia koi

Cross-Links

• PubChem: 6444241
• LOTUS: LTS0098448
• wikiData: Q105208966