[1,3,3abeta,4,5,6abeta,7,7aalpha,10,11,11a,11balpha-Dodecahydro-1beta,2alpha,3abeta,4beta,11beta-pentahydroxy-3,8,11abeta-trimethyl-5-oxo-2H-3beta,11cbeta-(epoxymethano)phenanthro[10,1-bc]pyran-10alpha-yl]beta-D-glucopyranoside

Details

• Internal ID: fffacec5-b8de-42d4-b673-a242b46f446f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2R,3R,6R,8S,11S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-11-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-4-one
• SMILES (Canonical): CC1=CC(C(C2(C1CC3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)C)O)O)C)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): CC1=C[C@@H]([C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@]4([C@H](C(=O)O3)O)O)(OC5)C)O)O)C)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C26H38O14/c1-8-4-10(38-22-15(30)14(29)13(28)11(6-27)39-22)18(32)23(2)9(8)5-12-25-7-37-24(3,19(33)16(31)17(23)25)26(25,36)20(34)21(35)40-12/h4,9-20,22,27-34,36H,5-7H2,1-3H3/t9-,10-,11+,12+,13+,14-,15+,16+,17+,18+,19-,20-,22+,23-,24+,25+,26+/m0/s1
• InChI Key: GLBAPTKVDVXEGQ-INLJEDTESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₁₄
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.22615588 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: -4.40
• Atomic LogP (AlogP): -4.34
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6926	69.26%
Caco-2	-	0.8658	86.58%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8459	84.59%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6582	65.82%
P-glycoprotein inhibitior	-	0.5644	56.44%
P-glycoprotein substrate	+	0.5203	52.03%
CYP3A4 substrate	+	0.6814	68.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8840	88.40%
CYP3A4 inhibition	-	0.9376	93.76%
CYP2C9 inhibition	-	0.9026	90.26%
CYP2C19 inhibition	-	0.8649	86.49%
CYP2D6 inhibition	-	0.9402	94.02%
CYP1A2 inhibition	-	0.8729	87.29%
CYP2C8 inhibition	-	0.6433	64.33%
CYP inhibitory promiscuity	-	0.8161	81.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6320	63.20%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9290	92.90%
Skin irritation	-	0.6697	66.97%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.6864	68.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4362	43.62%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8680	86.80%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6890	68.90%
Acute Oral Toxicity (c)	III	0.4990	49.90%
Estrogen receptor binding	+	0.7107	71.07%
Androgen receptor binding	+	0.7154	71.54%
Thyroid receptor binding	-	0.5312	53.12%
Glucocorticoid receptor binding	+	0.6061	60.61%
Aromatase binding	+	0.6830	68.30%
PPAR gamma	+	0.6532	65.32%
Honey bee toxicity	-	0.6219	62.19%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9078	90.78%

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	97.71%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.59%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.68%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.15%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.30%	97.25%
CHEMBL2581	P07339	Cathepsin D	89.49%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.22%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.63%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.43%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.26%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	84.76%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.64%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.36%	97.36%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.99%	96.95%
CHEMBL1937	Q92769	Histone deacetylase 2	82.65%	94.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.28%	86.92%
CHEMBL2996	Q05655	Protein kinase C delta	81.51%	97.79%
CHEMBL4208	P20618	Proteasome component C5	81.11%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.66%	96.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.32%	96.21%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 101273517
• NPASS: NPC209936
• LOTUS: LTS0193641
• wikiData: Q105010734