Chloromaloside A

Details

• Internal ID: 4e3bf8a8-86a1-4ec9-872a-c23d05aca75a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,18S)-16-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(C(=O)CC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(CO9)O)O)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)C)C)C)OC1
• SMILES (Isomeric): C[C@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(C(=O)C[C@H]5[C@H]4CC[C@@H]6[C@@]5(CCC(C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)OC9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)OC1
• InChI: InChI=1S/C50H80O23/c1-19-7-10-50(65-17-19)20(2)32-27(73-50)12-25-23-6-5-21-11-22(8-9-48(21,3)24(23)13-31(55)49(25,32)4)66-45-40(63)37(60)41(30(16-53)69-45)70-47-43(72-46-39(62)36(59)34(57)28(14-51)67-46)42(35(58)29(15-52)68-47)71-44-38(61)33(56)26(54)18-64-44/h19-30,32-47,51-54,56-63H,5-18H2,1-4H3/t19-,20-,21-,22?,23+,24-,25-,26+,27-,28+,29+,30+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44?,45+,46-,47-,48-,49+,50+/m0/s1
• InChI Key: IXUNZKARBRITGN-DRYZWBPLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₀O₂₃
• Molecular Weight: 1049.20 g/mol
• Exact Mass: 1048.50903879 g/mol
• Topological Polar Surface Area (TPSA): 352.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -3.09
• H-Bond Acceptor: 23
• H-Bond Donor: 12
• Rotatable Bonds: 11

Synonyms

• 133024-11-0
• Neo-hecogenin 3-O-glucopyranosyl-1-2-(xylopyranosyl-1-3)glucopyranosyl-1-4-galactopyranoside
• Spirostan-12-one, 3-((O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranosyl)oxy)-, (3beta,5alpha,25S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5734	57.34%
Caco-2	-	0.8791	87.91%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7299	72.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8785	87.85%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7468	74.68%
P-glycoprotein inhibitior	+	0.7392	73.92%
P-glycoprotein substrate	+	0.5391	53.91%
CYP3A4 substrate	+	0.7467	74.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8483	84.83%
CYP3A4 inhibition	-	0.9265	92.65%
CYP2C9 inhibition	-	0.9261	92.61%
CYP2C19 inhibition	-	0.9124	91.24%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	-	0.9264	92.64%
CYP2C8 inhibition	+	0.6548	65.48%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6417	64.17%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9054	90.54%
Skin irritation	-	0.6168	61.68%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.7654	76.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8029	80.29%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9422	94.22%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7660	76.60%
Acute Oral Toxicity (c)	I	0.7641	76.41%
Estrogen receptor binding	+	0.8513	85.13%
Androgen receptor binding	+	0.7280	72.80%
Thyroid receptor binding	-	0.5163	51.63%
Glucocorticoid receptor binding	+	0.6379	63.79%
Aromatase binding	+	0.6377	63.77%
PPAR gamma	+	0.7711	77.11%
Honey bee toxicity	-	0.5512	55.12%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8173	81.73%

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	98.08%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.06%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.99%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.63%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.64%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	89.03%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.56%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.60%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.56%	92.94%
CHEMBL237	P41145	Kappa opioid receptor	85.36%	98.10%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.12%	95.50%
CHEMBL233	P35372	Mu opioid receptor	83.42%	97.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.29%	93.04%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.91%	96.77%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.61%	97.29%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.59%	97.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.48%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.30%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.23%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.87%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.72%	94.75%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.62%	95.83%
CHEMBL325	Q13547	Histone deacetylase 1	80.08%	95.92%

Plants that contains it

• Chlorophytum malayense
• Diuranthera major

Cross-Links

• PubChem: 151156
• LOTUS: LTS0235534
• wikiData: Q105122485