Coagulin L

Details

• Internal ID: dccd6eeb-3d0a-4d8e-8a9c-0f1c0f8c2192
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (2R)-2-[(1S)-1-[(3R,8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC=C5C4(C(=O)CC(C5)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)O)O)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@@]2(CC[C@@]3([C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(C(=O)C[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)O)O)C
• InChI: InChI=1S/C34H50O12/c1-16-12-24(46-28(40)17(16)2)32(5,41)34(43)11-10-33(42)21-7-6-18-13-19(44-29-27(39)26(38)25(37)22(15-35)45-29)14-23(36)31(18,4)20(21)8-9-30(33,34)3/h6,19-22,24-27,29,35,37-39,41-43H,7-15H2,1-5H3/t19-,20+,21-,22-,24-,25-,26+,27-,29-,30+,31+,32+,33-,34+/m1/s1
• InChI Key: SYYXVJIFABSJBU-MJJWKRKWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₀O₁₂
• Molecular Weight: 650.80 g/mol
• Exact Mass: 650.33022703 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.56
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• 42EZK9ND5H
• UNII-42EZK9ND5H
• 216164-64-6
• Ergosta-5,24-dien-26-oic acid, 3-(beta-D-glucopyranosyloxy)-14,17,20,22-tetrahydroxy-1-oxo-, .delata.-lactone, (3beta,17alpha,22R)-
• (2R)-2-((1S)-1-((3R,8R,9S,10R,13S,14R,17S)-14,17-DIHYDROXY-10,13-DIMETHYL-1-OXO-3-((2R,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXY-2,3,4,7,8,9,11,12,15,16-DECAHYDROCYCLOPENTA(A)PHENANTHREN-17-YL)-1-HYDROXYETHYL)-4,5-DIMETHYL-2,3-DIHYDROPYRAN-6-ONE
• CHEMBL501881
• ERGOSTA-5,24-DIEN-26-OIC ACID, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-14,17,20,22-TETRAHYDROXY-1-OXO-, .DELATA.-LACTONE, (3.BETA.,17.ALPHA.,22R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8239	82.39%
Caco-2	-	0.8585	85.85%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8445	84.45%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8765	87.65%
OATP1B3 inhibitior	+	0.8514	85.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5829	58.29%
BSEP inhibitior	-	0.4820	48.20%
P-glycoprotein inhibitior	+	0.7286	72.86%
P-glycoprotein substrate	+	0.5087	50.87%
CYP3A4 substrate	+	0.7282	72.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9041	90.41%
CYP3A4 inhibition	-	0.8290	82.90%
CYP2C9 inhibition	-	0.9128	91.28%
CYP2C19 inhibition	-	0.9527	95.27%
CYP2D6 inhibition	-	0.9553	95.53%
CYP1A2 inhibition	-	0.9165	91.65%
CYP2C8 inhibition	+	0.6371	63.71%
CYP inhibitory promiscuity	-	0.9563	95.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5956	59.56%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9227	92.27%
Skin irritation	+	0.6280	62.80%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8041	80.41%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9377	93.77%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6744	67.44%
Acute Oral Toxicity (c)	III	0.5077	50.77%
Estrogen receptor binding	+	0.7393	73.93%
Androgen receptor binding	+	0.7674	76.74%
Thyroid receptor binding	-	0.5857	58.57%
Glucocorticoid receptor binding	+	0.6944	69.44%
Aromatase binding	+	0.6958	69.58%
PPAR gamma	+	0.6538	65.38%
Honey bee toxicity	-	0.7417	74.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9601	96.01%

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	99.30%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.19%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	93.63%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.60%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.78%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.65%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.21%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.13%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.85%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	88.48%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.44%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.31%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.96%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.49%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.35%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.13%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.40%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	84.81%	94.75%
CHEMBL2581	P07339	Cathepsin D	83.67%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.13%	97.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.16%	90.08%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.14%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.84%	92.50%
CHEMBL5028	O14672	ADAM10	80.05%	97.50%

Plants that contains it

• Withania coagulans

Cross-Links

• PubChem: 10508451
• LOTUS: LTS0177802
• wikiData: Q105263882