(2S,9R,11S,13S,17S)-11,16-dihydroxy-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-4-ene-3,15-dione

Details

• Internal ID: caae26b9-dc38-44a5-9342-b501a554a7d3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (2S,9R,11S,13S,17S)-11,16-dihydroxy-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-4-ene-3,15-dione
• SMILES (Canonical): CC1C=C(C(=O)C2(C1CC3C4(C2C(C(=O)C(C4CC(O3)O)C)O)C)C)OC
• SMILES (Isomeric): CC1C=C(C(=O)[C@]2(C1C[C@@H]3[C@@]4(C2C(C(=O)C([C@@H]4C[C@H](O3)O)C)O)C)C)OC
• InChI: InChI=1S/C21H30O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9-12,14-15,17-18,22,24H,7-8H2,1-5H3/t9?,10?,11?,12-,14+,15-,17?,18?,20+,21-/m0/s1
• InChI Key: ZXEXAUWPQPJYJZ-CRPYTBJPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.20423867 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.69
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• NSC-627442
• NCI60_008736

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9486	94.86%
Caco-2	-	0.6018	60.18%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6840	68.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8726	87.26%
OATP1B3 inhibitior	+	0.9504	95.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7744	77.44%
P-glycoprotein inhibitior	-	0.7144	71.44%
P-glycoprotein substrate	-	0.6648	66.48%
CYP3A4 substrate	+	0.6406	64.06%
CYP2C9 substrate	-	0.7887	78.87%
CYP2D6 substrate	-	0.8630	86.30%
CYP3A4 inhibition	-	0.8921	89.21%
CYP2C9 inhibition	-	0.9681	96.81%
CYP2C19 inhibition	-	0.9378	93.78%
CYP2D6 inhibition	-	0.9010	90.10%
CYP1A2 inhibition	-	0.8588	85.88%
CYP2C8 inhibition	-	0.7686	76.86%
CYP inhibitory promiscuity	-	0.9404	94.04%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5952	59.52%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9456	94.56%
Skin irritation	-	0.6048	60.48%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5356	53.56%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6088	60.88%
skin sensitisation	-	0.8173	81.73%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5865	58.65%
Acute Oral Toxicity (c)	III	0.5335	53.35%
Estrogen receptor binding	+	0.7005	70.05%
Androgen receptor binding	+	0.5725	57.25%
Thyroid receptor binding	+	0.5260	52.60%
Glucocorticoid receptor binding	+	0.6401	64.01%
Aromatase binding	+	0.6098	60.98%
PPAR gamma	-	0.4909	49.09%
Honey bee toxicity	-	0.6593	65.93%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.8582	85.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.44%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.03%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.90%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.79%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.32%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.25%	97.09%
CHEMBL2581	P07339	Cathepsin D	83.62%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.54%	100.00%
CHEMBL4208	P20618	Proteasome component C5	82.37%	90.00%

Plants that contains it

• Ailanthus altissima
• Picrasma quassioides

Cross-Links

• PubChem: 6711452
• NPASS: NPC69202