Isocucurbitacin B

Details

• Internal ID: 74ba5e39-6b68-4117-aecc-aa856b18bc15
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: [(E,6R)-6-[(3S,8S,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,11-dioxo-3,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
• SMILES (Canonical): CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(=O)C(C4(C)C)O)C)C)C)O)O
• SMILES (Isomeric): CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3CC(=O)[C@H](C4(C)C)O)C)C)C)O)O
• InChI: InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19,21-22,25-26,35,38-39H,11,14-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,26-,29+,30-,31+,32+/m1/s1
• InChI Key: WTBZNVRBNJWSPF-DZEACCAPSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₆O₈
• Molecular Weight: 558.70 g/mol
• Exact Mass: 558.31926842 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 17278-28-3
• [(E,6R)-6-[(3S,8S,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,11-dioxo-3,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
• NSC106400
• 2-EPICUCURBITICIN B
• CUCURBITCIN B,2-EPI-
• SCHEMBL10307348
• DTXSID101316518
• HY-N4189
• AKOS040760471
• NSC-106400
• CS-0032382

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	-	0.7409	74.09%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8019	80.19%
OATP2B1 inhibitior	-	0.7183	71.83%
OATP1B1 inhibitior	+	0.8739	87.39%
OATP1B3 inhibitior	-	0.2636	26.36%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9018	90.18%
P-glycoprotein inhibitior	+	0.6817	68.17%
P-glycoprotein substrate	-	0.5280	52.80%
CYP3A4 substrate	+	0.7066	70.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9083	90.83%
CYP3A4 inhibition	-	0.7546	75.46%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.8767	87.67%
CYP2D6 inhibition	-	0.9532	95.32%
CYP1A2 inhibition	-	0.8799	87.99%
CYP2C8 inhibition	+	0.5312	53.12%
CYP inhibitory promiscuity	-	0.9106	91.06%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6091	60.91%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9176	91.76%
Skin irritation	+	0.5669	56.69%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5067	50.67%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7653	76.53%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5359	53.59%
Acute Oral Toxicity (c)	I	0.6895	68.95%
Estrogen receptor binding	+	0.7550	75.50%
Androgen receptor binding	+	0.7352	73.52%
Thyroid receptor binding	+	0.6278	62.78%
Glucocorticoid receptor binding	+	0.7667	76.67%
Aromatase binding	+	0.7749	77.49%
PPAR gamma	+	0.6292	62.92%
Honey bee toxicity	-	0.6984	69.84%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9973	99.73%

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	97.37%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.16%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.21%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.46%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.45%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.12%	86.33%
CHEMBL1902	P62942	FK506-binding protein 1A	90.55%	97.05%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.22%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.67%	96.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.66%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.36%	91.07%
CHEMBL1937	Q92769	Histone deacetylase 2	86.41%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	84.28%	91.19%
CHEMBL217	P14416	Dopamine D2 receptor	84.08%	95.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.82%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.86%	89.34%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.90%	96.39%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.38%	97.09%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.71%	91.03%

Plants that contains it

• Cucurbita foetidissima
• Helicteres isora
• Hemsleya ellipsoidea
• Ipomopsis aggregata
• Luffa operculata
• Nernstia mexicana
• Trichosanthes kirilowii
• Trichosanthes tricuspidata

Cross-Links

• PubChem: 5352014
• LOTUS: LTS0142421
• wikiData: Q104394482