Withalongolide H

Details

• Internal ID: 6829868b-a5d4-48b0-a1fa-87fc5a80d8e7
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2R)-5-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3=C(CC(OC3=O)C(C)C4CCC5C4(CCC6C5CC7C8(C6(C(=O)C=CC8O)C)O7)C)C)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OCC3=C(C[C@@H](OC3=O)[C@@H](C)[C@H]4CC[C@@H]5[C@@]4(CC[C@H]6[C@H]5C[C@@H]7[C@]8([C@@]6(C(=O)C=C[C@@H]8O)C)O7)C)C)CO)O)O)O
• InChI: InChI=1S/C40H58O15/c1-16-12-24(17(2)21-6-7-22-19-13-28-40(55-28)27(43)9-8-26(42)39(40,5)23(19)10-11-38(21,22)4)52-35(49)20(16)15-50-36-33(48)31(46)34(25(14-41)53-36)54-37-32(47)30(45)29(44)18(3)51-37/h8-9,17-19,21-25,27-34,36-37,41,43-48H,6-7,10-15H2,1-5H3/t17-,18-,19-,21+,22-,23-,24+,25+,27-,28+,29-,30+,31+,32+,33+,34+,36+,37-,38+,39-,40+/m0/s1
• InChI Key: KWSCHTSFNFDQSG-IPAGGVPOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₈O₁₅
• Molecular Weight: 778.90 g/mol
• Exact Mass: 778.37757114 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.03
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• CHEBI:69112
• 27-O-[alpha-L-rhamnopyranosyl(1->4)]-beta-D-glucopyranosylwithaferin A
• (4beta,5beta,6beta,22R)-4-hydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,24-dien-27-yl 4-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• 27-O-(a-L-Rhamnopyranosyl(1->4))-b-D-glucopyranosylwithaferin a
• 27-O-[a-L-Rhamnopyranosyl(1->4)]-b-D-glucopyranosylwithaferin a
• 27-O-(alpha-L-Rhamnopyranosyl(1->4))-beta-D-glucopyranosylwithaferin a
• 27-O-(alpha-l-rhamnopyranosyl(1-4))-beta-d-glucopyranosylwithaferin A
• 27-O-[alpha-l-rhamnopyranosyl(1-4)]-beta-d-glucopyranosylwithaferin A
• (1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-((1S)-1-((2R)-5-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl)ethyl)-6-hydroxy-2,16-dimethyl-8-oxapentacyclo(9.7.0.02,7.07,9.012,16)octadec-4-en-3-one
• (1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2R)-5-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
• RefChem:194906
• CHEMBL1934460
• Q27137453

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5974	59.74%
Caco-2	-	0.8803	88.03%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7588	75.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8249	82.49%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6271	62.71%
BSEP inhibitior	+	0.9039	90.39%
P-glycoprotein inhibitior	+	0.7404	74.04%
P-glycoprotein substrate	+	0.6849	68.49%
CYP3A4 substrate	+	0.7526	75.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8879	88.79%
CYP3A4 inhibition	-	0.9350	93.50%
CYP2C9 inhibition	-	0.8509	85.09%
CYP2C19 inhibition	-	0.8921	89.21%
CYP2D6 inhibition	-	0.9393	93.93%
CYP1A2 inhibition	-	0.8283	82.83%
CYP2C8 inhibition	+	0.6985	69.85%
CYP inhibitory promiscuity	-	0.9359	93.59%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6538	65.38%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9165	91.65%
Skin irritation	-	0.5804	58.04%
Skin corrosion	-	0.9361	93.61%
Ames mutagenesis	-	0.6686	66.86%
Human Ether-a-go-go-Related Gene inhibition	+	0.7232	72.32%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6697	66.97%
skin sensitisation	-	0.8872	88.72%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6882	68.82%
Acute Oral Toxicity (c)	I	0.7048	70.48%
Estrogen receptor binding	+	0.8101	81.01%
Androgen receptor binding	+	0.7608	76.08%
Thyroid receptor binding	-	0.5610	56.10%
Glucocorticoid receptor binding	+	0.7005	70.05%
Aromatase binding	+	0.6410	64.10%
PPAR gamma	+	0.7746	77.46%
Honey bee toxicity	-	0.5926	59.26%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9617	96.17%

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	96.53%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.74%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.70%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.54%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	93.08%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.99%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.50%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.89%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.12%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	85.39%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.99%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.28%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.21%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.33%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.19%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.37%	97.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.26%	90.08%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.07%	93.56%
CHEMBL1937	Q92769	Histone deacetylase 2	81.71%	94.75%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.37%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.14%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.54%	97.25%

Plants that contains it

• Physalis longifolia

Cross-Links

• PubChem: 56649370
• NPASS: NPC316915
• ChEMBL: CHEMBL1934460
• LOTUS: LTS0181244
• wikiData: Q27137453