Withanolide B

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	63e76ad1-8c17-4c48-a4e9-02d31d919478
Taxonomy	Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name	(1S,2S,4S,5R,10R,11S,14R,15R,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
SMILES (Canonical)	CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)C
SMILES (Isomeric)	CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3[C@H]5[C@H](O5)[C@@]6([C@@]4(C(=O)C=CC6)C)O)C)C
InChI	InChI=1S/C28H38O5/c1-14-13-20(32-25(30)15(14)2)16(3)17-8-9-18-22-19(10-12-26(17,18)4)27(5)21(29)7-6-11-28(27,31)24-23(22)33-24/h6-7,16-20,22-24,31H,8-13H2,1-5H3/t16-,17+,18-,19-,20+,22-,23-,24-,26+,27-,28-/m0/s1
InChI Key	ZTEVDTFJUUJBLP-MBMSZCMESA-N
Popularity	12 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₈H₃₈O₅
Molecular Weight	454.60 g/mol
Exact Mass	454.27192431 g/mol
Topological Polar Surface Area (TPSA)	76.10 Å²
XlogP	4.70
Atomic LogP (AlogP)	4.38
H-Bond Acceptor	5
H-Bond Donor	1
Rotatable Bonds	2

Synonyms

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56973-41-2

Lycium substance B

UNII-9YU877VU8K

9YU877VU8K

WITHANOLIDE B(P)(NEW)

(1S,2S,4S,5R,10R,11S,14R,15R,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

(5alpha,6alpha,7alpha,22R)-5-Hydroxy-6,7:22,26-diepoxyergosta-2,24-diene-1,26-dione

15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

Ergosta-2,24-dien-26-oic acid, 6,7-epoxy-5,22-dihydroxy-1-oxo-, delta-lactone, (5alpha,6alpha,7alpha,22R)-

DTXSID20205575

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9586	95.86%
Caco-2	-	0.5605	56.05%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6784	67.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8801	88.01%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6521	65.21%
BSEP inhibitior	+	0.9648	96.48%
P-glycoprotein inhibitior	+	0.7494	74.94%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7149	71.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9069	90.69%
CYP3A4 inhibition	-	0.7687	76.87%
CYP2C9 inhibition	-	0.9034	90.34%
CYP2C19 inhibition	-	0.9138	91.38%
CYP2D6 inhibition	-	0.9541	95.41%
CYP1A2 inhibition	-	0.6899	68.99%
CYP2C8 inhibition	-	0.6269	62.69%
CYP inhibitory promiscuity	-	0.9787	97.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5543	55.43%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9601	96.01%
Skin irritation	+	0.5955	59.55%
Skin corrosion	-	0.8920	89.20%
Ames mutagenesis	-	0.6397	63.97%
Human Ether-a-go-go-Related Gene inhibition	+	0.7780	77.80%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6665	66.65%
skin sensitisation	-	0.8123	81.23%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.5866	58.66%
Acute Oral Toxicity (c)	I	0.3632	36.32%
Estrogen receptor binding	+	0.8576	85.76%
Androgen receptor binding	+	0.7424	74.24%
Thyroid receptor binding	+	0.6666	66.66%
Glucocorticoid receptor binding	+	0.7226	72.26%
Aromatase binding	+	0.6743	67.43%
PPAR gamma	+	0.6990	69.90%
Honey bee toxicity	-	0.8281	82.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9731	97.31%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.81%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.66%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.51%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.13%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.31%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.53%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.47%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.51%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.23%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.95%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.77%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.50%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.62%	95.89%
CHEMBL230	P35354	Cyclooxygenase-2	84.01%	89.63%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.55%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.55%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	82.83%	90.17%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.39%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.37%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	81.62%	94.75%
CHEMBL220	P22303	Acetylcholinesterase	81.20%	94.45%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.82%	90.08%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.50%	90.71%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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