(1S,4R,5R,7S,8R,11R,13S,16S,17S,18S,19R)-4,5,8,16,17-pentahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-9-one

Details

• Internal ID: 3601aa64-ab1c-48f8-a30f-bc051816bd02
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1S,4R,5R,7S,8R,11R,13S,16S,17S,18S,19R)-4,5,8,16,17-pentahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-9-one
• SMILES (Canonical): CC1=CC(C(C2(C1CC3C45C2C(C(C(=C)C4C(C(=O)O3)O)O)(OC5)O)C)O)O
• SMILES (Isomeric): CC1=C[C@@H]([C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@]([C@@H](C(=C)[C@@H]4[C@H](C(=O)O3)O)O)(OC5)O)C)O)O
• InChI: InChI=1S/C20H26O8/c1-7-4-10(21)15(24)18(3)9(7)5-11-19-6-27-20(26,17(18)19)14(23)8(2)12(19)13(22)16(25)28-11/h4,9-15,17,21-24,26H,2,5-6H2,1,3H3/t9-,10-,11+,12+,13+,14+,15+,17+,18+,19-,20-/m0/s1
• InChI Key: WDGYMAIGROVEFK-RLLLAKSDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.16276778 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -1.15
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9319	93.19%
Caco-2	-	0.7957	79.57%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7733	77.33%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8693	86.93%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9028	90.28%
P-glycoprotein inhibitior	-	0.7976	79.76%
P-glycoprotein substrate	+	0.6729	67.29%
CYP3A4 substrate	+	0.6703	67.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8526	85.26%
CYP3A4 inhibition	-	0.8088	80.88%
CYP2C9 inhibition	-	0.8786	87.86%
CYP2C19 inhibition	-	0.8256	82.56%
CYP2D6 inhibition	-	0.9289	92.89%
CYP1A2 inhibition	-	0.8095	80.95%
CYP2C8 inhibition	-	0.6989	69.89%
CYP inhibitory promiscuity	-	0.9159	91.59%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5952	59.52%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9245	92.45%
Skin irritation	-	0.5839	58.39%
Skin corrosion	-	0.9049	90.49%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5885	58.85%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8049	80.49%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.8328	83.28%
Acute Oral Toxicity (c)	III	0.4823	48.23%
Estrogen receptor binding	+	0.7327	73.27%
Androgen receptor binding	+	0.6345	63.45%
Thyroid receptor binding	+	0.6339	63.39%
Glucocorticoid receptor binding	+	0.5883	58.83%
Aromatase binding	+	0.5908	59.08%
PPAR gamma	+	0.6107	61.07%
Honey bee toxicity	-	0.6642	66.42%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9788	97.88%

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	91.72%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	91.55%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.37%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.21%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.82%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.92%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.34%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.30%	97.09%

Plants that contains it

• Ailanthus altissima

Cross-Links

• PubChem: 162965785
• LOTUS: LTS0002902
• wikiData: Q105302360