(1R,2S,3S,7S,8R,9S,12R,13R,14S,15R,16R,17S)-3,8,12,13,15,16-hexahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-5-ene-4,11-dione

Details

• Internal ID: 8d9b6607-2aa7-4a6c-b344-cf29e2f2c403
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2S,3S,7S,8R,9S,12R,13R,14S,15R,16R,17S)-3,8,12,13,15,16-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(C(C(C4C2(C1(C(C(=O)O4)O)O)C)O)C(=CC(=O)C3O)C)C)O)O
• SMILES (Isomeric): C[C@H]1[C@H]([C@@H]([C@@H]2[C@@]3([C@@H]([C@H]([C@@H]4[C@]2([C@]1([C@H](C(=O)O4)O)O)C)O)C(=CC(=O)[C@H]3O)C)C)O)O
• InChI: InChI=1S/C20H28O9/c1-6-5-8(21)14(25)18(3)9(6)11(23)16-19(4)13(18)12(24)10(22)7(2)20(19,28)15(26)17(27)29-16/h5,7,9-16,22-26,28H,1-4H3/t7-,9+,10+,11+,12-,13+,14+,15-,16+,18-,19-,20-/m0/s1
• InChI Key: HXMUCWWCZOMGTO-HMOMASBHSA-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: -1.90
• Atomic LogP (AlogP): -2.12
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 0

Synonyms

• (1R)-1beta,2alpha,3abeta,4beta,7alpha,11beta-Hexahydroxy-3alpha,8,11abeta,11cbeta-tetramethyl-1,2,3,3a,4,5,6abeta,7aalpha,10,11,11a,11balpha,11c-tridecahydro-6-oxa-7H-benzo[de]anthracene-5,10-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8394	83.94%
Caco-2	-	0.8252	82.52%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6102	61.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	+	0.9674	96.74%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6882	68.82%
P-glycoprotein inhibitior	-	0.7054	70.54%
P-glycoprotein substrate	+	0.5266	52.66%
CYP3A4 substrate	+	0.5936	59.36%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.9009	90.09%
CYP3A4 inhibition	-	0.8615	86.15%
CYP2C9 inhibition	-	0.9343	93.43%
CYP2C19 inhibition	-	0.9365	93.65%
CYP2D6 inhibition	-	0.9594	95.94%
CYP1A2 inhibition	-	0.9159	91.59%
CYP2C8 inhibition	-	0.8222	82.22%
CYP inhibitory promiscuity	-	0.8736	87.36%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4800	48.00%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9243	92.43%
Skin irritation	+	0.5387	53.87%
Skin corrosion	-	0.9167	91.67%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6350	63.50%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5243	52.43%
skin sensitisation	-	0.7487	74.87%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6456	64.56%
Acute Oral Toxicity (c)	III	0.4540	45.40%
Estrogen receptor binding	+	0.7690	76.90%
Androgen receptor binding	+	0.6686	66.86%
Thyroid receptor binding	+	0.5734	57.34%
Glucocorticoid receptor binding	+	0.5538	55.38%
Aromatase binding	+	0.6090	60.90%
PPAR gamma	+	0.5314	53.14%
Honey bee toxicity	-	0.8398	83.98%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8920	89.20%

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	94.40%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.66%	94.80%
CHEMBL2581	P07339	Cathepsin D	88.75%	98.95%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	87.37%	86.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.41%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.55%	99.23%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.92%	96.90%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.68%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.48%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.67%	90.24%

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: 44614657
• NPASS: NPC7921
• LOTUS: LTS0091295
• wikiData: Q105035079