Chantriolide B

Details

• Internal ID: 04d374c9-5430-4a79-aba7-1f0c29312e84
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(1S,2S,4S,5R,7S,9S,10R,11S,12S,14S,15S,16R,17S,19S)-10-acetyloxy-5,17-dihydroxy-11,15-dimethyl-16-[(1S)-1-[(2R)-4-methyl-6-oxo-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-2-yl]ethyl]-3,8-dioxahexacyclo[10.7.0.02,4.05,11.07,9.015,19]nonadecan-14-yl] acetate
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)C2C(CC3C2(C(CC4C3C5C(O5)C6(C4(C(C7C(C6)O7)OC(=O)C)C)O)OC(=O)C)C)O)COC8C(C(C(C(O8)CO)O)O)O
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2[C@H](C[C@@H]3[C@@]2([C@H](C[C@H]4[C@H]3[C@H]5[C@H](O5)[C@@]6([C@@]4([C@H]([C@@H]7[C@H](C6)O7)OC(=O)C)C)O)OC(=O)C)C)O)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C38H54O16/c1-13-7-21(52-34(46)17(13)12-48-35-29(45)28(44)27(43)23(11-39)53-35)14(2)26-20(42)8-18-25-19(9-24(36(18,26)5)49-15(3)40)37(6)32(50-16(4)41)30-22(51-30)10-38(37,47)33-31(25)54-33/h14,18-33,35,39,42-45,47H,7-12H2,1-6H3/t14-,18+,19+,20+,21-,22+,23-,24+,25+,26+,27-,28+,29-,30+,31+,32+,33+,35-,36-,37+,38+/m1/s1
• InChI Key: MAUWXIXDBHEPFC-UWOHKWSVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₄O₁₆
• Molecular Weight: 766.80 g/mol
• Exact Mass: 766.34118563 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.74
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• [(1S,2S,4S,5R,7S,9S,10R,11S,12S,14S,15S,16R,17S,19S)-10-Acetyloxy-5,17-dihydroxy-11,15-dimethyl-16-[(1S)-1-[(2R)-4-methyl-6-oxo-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-2-yl]ethyl]-3,8-dioxahexacyclo[10.7.0.02,4.05,11.07,9.015,19]nonadecan-14-yl] acetate
• 558470-60-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7259	72.59%
Caco-2	-	0.8821	88.21%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6636	66.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8334	83.34%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4618	46.18%
P-glycoprotein inhibitior	+	0.7392	73.92%
P-glycoprotein substrate	+	0.6566	65.66%
CYP3A4 substrate	+	0.7294	72.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8978	89.78%
CYP3A4 inhibition	-	0.8081	80.81%
CYP2C9 inhibition	-	0.8377	83.77%
CYP2C19 inhibition	-	0.8866	88.66%
CYP2D6 inhibition	-	0.9417	94.17%
CYP1A2 inhibition	-	0.8894	88.94%
CYP2C8 inhibition	+	0.6754	67.54%
CYP inhibitory promiscuity	-	0.9580	95.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6946	69.46%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9148	91.48%
Skin irritation	-	0.6238	62.38%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.5191	51.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.6842	68.42%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.7644	76.44%
skin sensitisation	-	0.8777	87.77%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7968	79.68%
Acute Oral Toxicity (c)	I	0.7441	74.41%
Estrogen receptor binding	+	0.7702	77.02%
Androgen receptor binding	+	0.7111	71.11%
Thyroid receptor binding	-	0.5888	58.88%
Glucocorticoid receptor binding	+	0.6773	67.73%
Aromatase binding	+	0.6576	65.76%
PPAR gamma	+	0.7332	73.32%
Honey bee toxicity	-	0.5965	59.65%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9649	96.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.82%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.87%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.88%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.11%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.74%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	92.11%	97.79%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.74%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.90%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.61%	95.56%
CHEMBL299	P17252	Protein kinase C alpha	88.65%	98.03%
CHEMBL5103	Q969S8	Histone deacetylase 10	88.06%	90.08%
CHEMBL220	P22303	Acetylcholinesterase	88.02%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.80%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.05%	99.23%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.00%	82.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.49%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.46%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.34%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.05%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.50%	97.25%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.95%	91.24%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.46%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.82%	96.47%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.63%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.51%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	81.79%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.10%	93.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.89%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.68%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.65%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.52%	91.19%

Plants that contains it

• Tacca chantrieri

Cross-Links

• PubChem: 11125583
• NPASS: NPC306379
• LOTUS: LTS0030565
• wikiData: Q105160545