19-Norlanosta-5,23-diene-11,22-dione, 25-(acetyloxy)-3,16,20-trihydroxy-9-(hydroxymethyl)-, (3beta,9beta,10alpha,16alpha,23E)-

Details

• Internal ID: 4adf8c3f-1a17-4e2e-a0be-752093a97ffc
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: [(E)-6-[(3S,10R,16R)-3,16-dihydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[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=C4C3CCC(C4(C)C)O)CO)C)C)O)O
• SMILES (Isomeric): CC(=O)OC(C)(C)/C=C/C(=O)C(C)(C1[C@@H](CC2(C1(CC(=O)C3(C2CC=C4[C@H]3CC[C@@H](C4(C)C)O)CO)C)C)O)O
• InChI: InChI=1S/C32H48O8/c1-18(34)40-27(2,3)14-13-24(37)31(8,39)26-21(35)15-29(6)22-11-9-19-20(10-12-23(36)28(19,4)5)32(22,17-33)25(38)16-30(26,29)7/h9,13-14,20-23,26,33,35-36,39H,10-12,15-17H2,1-8H3/b14-13+/t20-,21-,22?,23+,26?,29?,30?,31?,32?/m1/s1
• InChI Key: DGIGXLXLGBAJJN-IHGCRQHVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₈
• Molecular Weight: 560.70 g/mol
• Exact Mass: 560.33491849 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.29
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• Cucurbitacine (C)
• HSDB 3477
• NSC 94744
• 19-Nor-9-beta,10-alpha-lanosta-5,23-diene-11,22-dione, 3-beta,16-alpha,20,25-tetrahydroxy-9-(hydroxymethyl)-, 25-acetate
• 19-Nor-9beta,10alpha-lanosta-5,23-diene-11,22-dione, 3beta,16alpha,20,25-tetrahydroxy-9-(hydroxymethyl)-, 25-acetate
• 19-Norlanosta-5,23-diene-11,22-dione, 25-(acetyloxy)-3,16,20-trihydroxy-9-(hydroxymethyl)-, (3beta,9beta,10alpha,16alpha,23E)-
• 25-(Acetyloxy)-3,16,20-trihydroxy-9-(hydroxymethyl)-19-norlanosta-5,23-diene-11,22-dione
• LS-97295

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	-	0.7450	74.50%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8797	87.97%
OATP2B1 inhibitior	-	0.7217	72.17%
OATP1B1 inhibitior	+	0.8627	86.27%
OATP1B3 inhibitior	-	0.2372	23.72%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5807	58.07%
BSEP inhibitior	+	0.9596	95.96%
P-glycoprotein inhibitior	+	0.6840	68.40%
P-glycoprotein substrate	+	0.5293	52.93%
CYP3A4 substrate	+	0.7102	71.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9092	90.92%
CYP3A4 inhibition	-	0.8568	85.68%
CYP2C9 inhibition	-	0.7330	73.30%
CYP2C19 inhibition	-	0.9290	92.90%
CYP2D6 inhibition	-	0.9494	94.94%
CYP1A2 inhibition	-	0.9242	92.42%
CYP2C8 inhibition	+	0.5813	58.13%
CYP inhibitory promiscuity	-	0.8757	87.57%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7260	72.60%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9204	92.04%
Skin irritation	+	0.6274	62.74%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4147	41.47%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6098	60.98%
skin sensitisation	-	0.9283	92.83%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4552	45.52%
Acute Oral Toxicity (c)	III	0.7298	72.98%
Estrogen receptor binding	+	0.7388	73.88%
Androgen receptor binding	+	0.7358	73.58%
Thyroid receptor binding	+	0.5939	59.39%
Glucocorticoid receptor binding	+	0.7482	74.82%
Aromatase binding	+	0.7657	76.57%
PPAR gamma	+	0.6082	60.82%
Honey bee toxicity	-	0.7601	76.01%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9915	99.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293277	O15118	Niemann-Pick C1 protein	125.9 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	89.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.75%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.33%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.24%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.39%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.28%	86.33%
CHEMBL1902	P62942	FK506-binding protein 1A	92.45%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.13%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.83%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.97%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.80%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.65%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.62%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.53%	91.07%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.76%	91.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.41%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	82.59%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.56%	99.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.41%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	82.40%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.74%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.77%	93.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.53%	89.34%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.45%	100.00%

Plants that contains it

• Bryonia alba
• Citrullus colocynthis
• Cucumis melo
• Ecballium elaterium
• Luffa aegyptiaca
• Trichosanthes kirilowii

Cross-Links

• PubChem: 6433457
• NPASS: NPC236357