(1R,2S,3S,7R,9R,12R,13R,14S,15R,16R,17S)-3,7,12,13,15,16-hexahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-5-ene-4,11-dione

Details

• Internal ID: 5397ccef-f37c-4863-af87-d47e4a6dfbb2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2S,3S,7R,9R,12R,13R,14S,15R,16R,17S)-3,7,12,13,15,16-hexahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-5-ene-4,11-dione
• SMILES (Canonical): CC1C(C(C2C3(C1(C(C(=O)OC3CC4(C2(C(C(=O)C=C4C)O)C)O)O)O)C)O)O
• SMILES (Isomeric): C[C@H]1[C@H]([C@@H]([C@H]2[C@@]3([C@]1([C@H](C(=O)O[C@@H]3C[C@@]4([C@@]2([C@@H](C(=O)C=C4C)O)C)O)O)O)C)O)O
• InChI: InChI=1S/C20H28O9/c1-7-5-9(21)14(24)18(4)13-12(23)11(22)8(2)20(28)15(25)16(26)29-10(17(13,20)3)6-19(7,18)27/h5,8,10-15,22-25,27-28H,6H2,1-4H3/t8-,10+,11+,12-,13-,14+,15-,17+,18-,19+,20-/m0/s1
• InChI Key: UJAVIKYBXBAYED-KGDUUCQMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₉
• Molecular Weight: 412.40 g/mol
• Exact Mass: 412.17333247 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -1.97
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8455	84.55%
Caco-2	-	0.8058	80.58%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5385	53.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8614	86.14%
OATP1B3 inhibitior	+	0.9743	97.43%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6896	68.96%
P-glycoprotein inhibitior	-	0.7207	72.07%
P-glycoprotein substrate	-	0.5224	52.24%
CYP3A4 substrate	+	0.6301	63.01%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.8970	89.70%
CYP3A4 inhibition	-	0.8142	81.42%
CYP2C9 inhibition	-	0.9509	95.09%
CYP2C19 inhibition	-	0.9373	93.73%
CYP2D6 inhibition	-	0.9100	91.00%
CYP1A2 inhibition	-	0.9179	91.79%
CYP2C8 inhibition	-	0.8888	88.88%
CYP inhibitory promiscuity	-	0.9528	95.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4884	48.84%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9483	94.83%
Skin irritation	+	0.5148	51.48%
Skin corrosion	-	0.8912	89.12%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5838	58.38%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.5019	50.19%
skin sensitisation	-	0.7738	77.38%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6629	66.29%
Acute Oral Toxicity (c)	III	0.4449	44.49%
Estrogen receptor binding	+	0.7835	78.35%
Androgen receptor binding	+	0.7324	73.24%
Thyroid receptor binding	+	0.5596	55.96%
Glucocorticoid receptor binding	+	0.6377	63.77%
Aromatase binding	+	0.6156	61.56%
PPAR gamma	+	0.5432	54.32%
Honey bee toxicity	-	0.8619	86.19%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8445	84.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.53%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.70%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.06%	94.80%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	87.95%	86.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.60%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.83%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.53%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.61%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.23%	97.09%
CHEMBL2581	P07339	Cathepsin D	81.99%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.78%	86.33%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.44%	90.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.03%	99.23%

Plants that contains it

• Aralidium pinnatifidum
• Bersama swinnyi
• Blainvillea acmella
• Euphorbia resinifera
• Eurycoma longifolia
• Geigeria schinzii
• Goniothalamus undulatus
• Gymnospermium kiangnanensis
• Helichrysum sutherlandii
• Hemionitis marantae
• Lophocereus marginatus
• Nemuaron vieillardii
• Ophryosporus charua
• Oreomecon radicata
• Pachycereus pringlei
• Picea laxa
• Prosopis kuntzei
• Pteris leptophylla
• Stenocereus thurberi
• Vitex negundo

Cross-Links

• PubChem: 118708398
• NPASS: NPC251310
• LOTUS: LTS0120037
• wikiData: Q105273833