19-Norlanost-5-en-24-one, 3-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-22,23,25-trihydroxy-9-methyl-, (3beta,9beta,10alpha,22S,23R)-

Details

• Internal ID: b965e13c-705a-44b9-bc7f-3daf53e457b0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (4R,5S,6S)-2,4,5-trihydroxy-2-methyl-6-[(3S,8R,9R,10S,13R,14S,17R)-4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-one
• SMILES (Canonical): CC(C1CCC2(C1(CCC3(C2CC=C4C3CCC(C4(C)C)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)C)C)C)C(C(C(=O)C(C)(C)O)O)O
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@@]3([C@H]2CC=C4[C@H]3CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)C)C)C)[C@@H]([C@H](C(=O)C(C)(C)O)O)O
• InChI: InChI=1S/C42H70O15/c1-19(27(44)32(49)35(52)39(4,5)53)20-13-14-42(8)25-11-9-21-22(40(25,6)15-16-41(20,42)7)10-12-26(38(21,2)3)57-37-34(51)31(48)29(46)24(56-37)18-54-36-33(50)30(47)28(45)23(17-43)55-36/h9,19-20,22-34,36-37,43-51,53H,10-18H2,1-8H3/t19-,20+,22+,23+,24+,25+,26-,27-,28+,29+,30-,31-,32+,33+,34+,36+,37-,40-,41+,42-/m0/s1
• InChI Key: JRCQXODHWLEPSP-BSIAXBLVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₀O₁₅
• Molecular Weight: 815.00 g/mol
• Exact Mass: 814.47147152 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• DTXSID501103024
• 19-Norlanost-5-en-24-one, 3-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-22,23,25-trihydroxy-9-methyl-, (3beta,9beta,10alpha,22S,23R)-
• 333333-19-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7907	79.07%
Caco-2	-	0.8855	88.55%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8651	86.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8301	83.01%
OATP1B3 inhibitior	-	0.4111	41.11%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.6266	62.66%
P-glycoprotein inhibitior	+	0.7471	74.71%
P-glycoprotein substrate	-	0.5342	53.42%
CYP3A4 substrate	+	0.7088	70.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8641	86.41%
CYP3A4 inhibition	-	0.9642	96.42%
CYP2C9 inhibition	-	0.8723	87.23%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.8907	89.07%
CYP2C8 inhibition	+	0.6538	65.38%
CYP inhibitory promiscuity	-	0.9193	91.93%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6168	61.68%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9104	91.04%
Skin irritation	-	0.5922	59.22%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7713	77.13%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7433	74.33%
skin sensitisation	-	0.9044	90.44%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7897	78.97%
Acute Oral Toxicity (c)	III	0.7126	71.26%
Estrogen receptor binding	+	0.7997	79.97%
Androgen receptor binding	+	0.7194	71.94%
Thyroid receptor binding	-	0.5698	56.98%
Glucocorticoid receptor binding	+	0.6933	69.33%
Aromatase binding	+	0.6562	65.62%
PPAR gamma	+	0.7625	76.25%
Honey bee toxicity	-	0.7390	73.90%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.81%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.68%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	98.43%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.12%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.74%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.03%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.66%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.63%	97.36%
CHEMBL5255	O00206	Toll-like receptor 4	88.03%	92.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.61%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.59%	93.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.34%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.09%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.85%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.73%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.91%	89.00%
CHEMBL5028	O14672	ADAM10	83.70%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.86%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.72%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.59%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.95%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.65%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.61%	95.71%
CHEMBL4208	P20618	Proteasome component C5	80.25%	90.00%

Plants that contains it

• Momordica charantia

Cross-Links

• PubChem: 101077719
• LOTUS: LTS0125307
• wikiData: Q105133824