Coagulin O

Details

• Internal ID: f07e0336-27bd-421f-83d4-51aaad870caa
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (2R)-2-[(1R)-1-hydroxy-1-[(3R,8R,9S,10R,13R,14R,17S)-14-hydroxy-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,7,8,9,11,12,15,16,17-decahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2CCC3(C2(CCC4C3CC=C5C4(C(=O)CC(C5)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)O)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[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)C
• InChI: InChI=1S/C34H50O11/c1-16-12-25(45-29(40)17(16)2)33(5,41)23-9-11-34(42)21-7-6-18-13-19(43-30-28(39)27(38)26(37)22(15-35)44-30)14-24(36)32(18,4)20(21)8-10-31(23,34)3/h6,19-23,25-28,30,35,37-39,41-42H,7-15H2,1-5H3/t19-,20+,21-,22-,23+,25-,26-,27+,28-,30-,31-,32+,33-,34-/m1/s1
• InChI Key: ZGFSMKCODQJWHY-DKZVLZAESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₀O₁₁
• Molecular Weight: 634.80 g/mol
• Exact Mass: 634.33531241 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.45
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• (+)-Coagulin O
• E5CU44H2XD
• UNII-E5CU44H2XD
• 220381-52-2
• Ergosta-5,24-dien-26-oic acid, 3-(beta-D-glucopyranosyloxy)-14,20,22-trihydroxy-1-oxo-, delta-lactone, (3beta,22R)-
• (2R)-2-((1R)-1-HYDROXY-1-((3R,8R,9S,10R,13R,14R,17S)-14-HYDROXY-10,13-DIMETHYL-1-OXO-3-((2R,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXY-3,4,7,8,9,11,12,15,16,17-DECAHYDRO-2H-CYCLOPENTA(A)PHENANTHREN-17-YL)ETHYL)-4,5-DIMETHYL-2,3-DIHYDROPYRAN-6-ONE
• ERGOSTA-5,24-DIEN-26-OIC ACID, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-14,20,22-TRIHYDROXY-1-OXO-, .DELTA.-LACTONE, (3.BETA.,22R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8239	82.39%
Caco-2	-	0.8562	85.62%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8445	84.45%
OATP2B1 inhibitior	-	0.5804	58.04%
OATP1B1 inhibitior	+	0.8605	86.05%
OATP1B3 inhibitior	+	0.8514	85.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5829	58.29%
BSEP inhibitior	-	0.5958	59.58%
P-glycoprotein inhibitior	+	0.7223	72.23%
P-glycoprotein substrate	-	0.5481	54.81%
CYP3A4 substrate	+	0.7350	73.50%
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	+	0.6352	63.52%
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	-	0.9265	92.65%
Skin irritation	+	0.6280	62.80%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7904	79.04%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9377	93.77%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5537	55.37%
Acute Oral Toxicity (c)	III	0.5077	50.77%
Estrogen receptor binding	+	0.7520	75.20%
Androgen receptor binding	+	0.7620	76.20%
Thyroid receptor binding	-	0.5972	59.72%
Glucocorticoid receptor binding	+	0.6817	68.17%
Aromatase binding	+	0.6785	67.85%
PPAR gamma	+	0.6506	65.06%
Honey bee toxicity	-	0.7238	72.38%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
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	98.56%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.22%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.68%	85.14%
CHEMBL1937	Q92769	Histone deacetylase 2	93.86%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.10%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.00%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.45%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.22%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.10%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.74%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.67%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.28%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.17%	93.04%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.43%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	85.49%	94.73%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.48%	90.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.65%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.29%	91.07%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.43%	96.61%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.19%	100.00%
CHEMBL220	P22303	Acetylcholinesterase	82.10%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.92%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	80.78%	92.50%
CHEMBL2581	P07339	Cathepsin D	80.11%	98.95%

Plants that contains it

• Withania coagulans

Cross-Links

• PubChem: 10770343
• LOTUS: LTS0229073
• wikiData: Q105375143