yadanziolide A

Details

• Internal ID: 5b23a169-da3c-48ec-b4b3-0a74a3b0b51c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione
• SMILES (Canonical): CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)CO)O)O)C)O
• SMILES (Isomeric): CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@]4([C@H](C(=O)O3)O)O)(OC5)CO)O)O)C)O
• InChI: InChI=1S/C20H26O10/c1-7-3-9(22)13(24)17(2)8(7)4-10-18-6-29-19(5-21,14(25)11(23)12(17)18)20(18,28)15(26)16(27)30-10/h3,8,10-15,21,23-26,28H,4-6H2,1-2H3/t8-,10+,11+,12+,13+,14-,15-,17-,18+,19+,20-/m0/s1
• InChI Key: QXKKRGMRXXMDDP-JVDXBALSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₁₀
• Molecular Weight: 426.40 g/mol
• Exact Mass: 426.15259702 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -2.98
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 1

Synonyms

• 95258-14-3
• (1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-Pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione
• CHEMBL2037039
• HY-N4210
• AKOS040760154
• AC-34985
• MS-27518
• CS-0032442

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6978	69.78%
Caco-2	-	0.8102	81.02%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7808	78.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8371	83.71%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6092	60.92%
P-glycoprotein inhibitior	-	0.7403	74.03%
P-glycoprotein substrate	+	0.7064	70.64%
CYP3A4 substrate	+	0.6636	66.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8936	89.36%
CYP3A4 inhibition	-	0.9416	94.16%
CYP2C9 inhibition	-	0.9117	91.17%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9147	91.47%
CYP2C8 inhibition	-	0.7648	76.48%
CYP inhibitory promiscuity	-	0.9416	94.16%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6274	62.74%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9572	95.72%
Skin irritation	-	0.6539	65.39%
Skin corrosion	-	0.9336	93.36%
Ames mutagenesis	-	0.7318	73.18%
Human Ether-a-go-go-Related Gene inhibition	-	0.5993	59.93%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5618	56.18%
skin sensitisation	-	0.8737	87.37%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7923	79.23%
Acute Oral Toxicity (c)	I	0.4506	45.06%
Estrogen receptor binding	+	0.8841	88.41%
Androgen receptor binding	+	0.7231	72.31%
Thyroid receptor binding	+	0.6045	60.45%
Glucocorticoid receptor binding	+	0.7316	73.16%
Aromatase binding	+	0.6551	65.51%
PPAR gamma	+	0.5513	55.13%
Honey bee toxicity	-	0.7939	79.39%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9579	95.79%

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	97.43%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.30%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.65%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.48%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.36%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.35%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.39%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.76%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.74%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.86%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.44%	86.33%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 10320238
• NPASS: NPC287343
• ChEMBL: CHEMBL2037039
• LOTUS: LTS0115598
• wikiData: Q104400578