(1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione

Details

• Internal ID: 491af321-ffd9-4de7-ad99-70d19ac7f06c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones > Ginkgolides and bilobalides
• IUPAC Name: (1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
• SMILES (Canonical): CC1C(=O)OC2C1(C34C(=O)OC5C3(C2O)C6(C(C5)C(C)(C)C)C(C(=O)OC6O4)O)O
• SMILES (Isomeric): C[C@@H]1C(=O)O[C@@H]2[C@]1([C@@]34C(=O)O[C@H]5C3(C2O)C6([C@@H](C5)C(C)(C)C)[C@H](O4)OC(=O)C6O)O
• InChI: InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8-,9?,10?,11+,15+,17?,18?,19-,20-/m1/s1
• InChI Key: SQOJOAFXDQDRGF-OOHPMXMZSA-N
• Popularity: 844 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₁₀
• Molecular Weight: 424.40 g/mol
• Exact Mass: 424.13694696 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.37
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 15291-77-7
• BN 52021
• SCHEMBL464784
• GTPL1862
• (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11R,11aR)-3-(1,1-Dimethylethyl)hexahydro-4,7b,11-trihydroxy-8-methyl-9H-1,7a-(epoxymethano)-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione
• GKB
• LMPR0104540002
• C07602
• Q27077804
• (1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8280	82.80%
Caco-2	-	0.7787	77.87%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6210	62.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9347	93.47%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9239	92.39%
P-glycoprotein inhibitior	-	0.6156	61.56%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6463	64.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8438	84.38%
CYP3A4 inhibition	-	0.9335	93.35%
CYP2C9 inhibition	-	0.9341	93.41%
CYP2C19 inhibition	-	0.9528	95.28%
CYP2D6 inhibition	-	0.9449	94.49%
CYP1A2 inhibition	-	0.9307	93.07%
CYP2C8 inhibition	-	0.7435	74.35%
CYP inhibitory promiscuity	-	0.9699	96.99%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5083	50.83%
Eye corrosion	-	0.9714	97.14%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.6697	66.97%
Skin corrosion	-	0.7632	76.32%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5390	53.90%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6427	64.27%
skin sensitisation	-	0.8070	80.70%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6392	63.92%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7453	74.53%
Acute Oral Toxicity (c)	III	0.5020	50.20%
Estrogen receptor binding	+	0.8458	84.58%
Androgen receptor binding	+	0.7355	73.55%
Thyroid receptor binding	+	0.6462	64.62%
Glucocorticoid receptor binding	-	0.5527	55.27%
Aromatase binding	+	0.5356	53.56%
PPAR gamma	+	0.6308	63.08%
Honey bee toxicity	-	0.8081	80.81%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	-	0.3856	38.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.59%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.73%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.50%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.46%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.66%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.15%	90.08%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.12%	96.90%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.34%	89.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.08%	94.66%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.96%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.48%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.80%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.49%	97.28%
CHEMBL2996	Q05655	Protein kinase C delta	80.25%	97.79%

Plants that contains it

• Ginkgo biloba

Cross-Links

• PubChem: 441294
• NPASS: NPC49015