4-Methylene-5beta-hydroxyovatodiolide

Details

• Internal ID: 4904dd78-7bec-4df4-8942-7963e90c0ed4
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1R,3E,5S,9R,13R)-13-hydroxy-3-methyl-8,12-dimethylidene-6,18-dioxatricyclo[14.2.1.05,9]nonadeca-3,16(19)-diene-7,17-dione
• SMILES (Canonical): CC1=CC2C(CCC(=C)C(CCC3=CC(C1)OC3=O)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@H]2[C@H](CCC(=C)[C@@H](CCC3=C[C@@H](C1)OC3=O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C20H24O5/c1-11-8-15-10-14(20(23)24-15)5-7-17(21)12(2)4-6-16-13(3)19(22)25-18(16)9-11/h9-10,15-18,21H,2-8H2,1H3/b11-9+/t15-,16-,17-,18+/m1/s1
• InChI Key: VOJUAGSYDJPMCX-JUXQZVFASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.76
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 4-Methylene-5beta-hydroxyovatodiolide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9850	98.50%
Caco-2	-	0.5530	55.30%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8292	82.92%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8956	89.56%
OATP1B3 inhibitior	+	0.9318	93.18%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	-	0.7623	76.23%
P-glycoprotein inhibitior	-	0.6257	62.57%
P-glycoprotein substrate	-	0.8459	84.59%
CYP3A4 substrate	+	0.5863	58.63%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8640	86.40%
CYP3A4 inhibition	-	0.9113	91.13%
CYP2C9 inhibition	-	0.8844	88.44%
CYP2C19 inhibition	-	0.8710	87.10%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.6151	61.51%
CYP2C8 inhibition	-	0.7141	71.41%
CYP inhibitory promiscuity	-	0.9745	97.45%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5263	52.63%
Eye corrosion	-	0.9459	94.59%
Eye irritation	-	0.7091	70.91%
Skin irritation	-	0.6202	62.02%
Skin corrosion	-	0.9202	92.02%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4807	48.07%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6067	60.67%
skin sensitisation	-	0.7702	77.02%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4416	44.16%
Estrogen receptor binding	+	0.6920	69.20%
Androgen receptor binding	+	0.5691	56.91%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8096	80.96%
Aromatase binding	-	0.5053	50.53%
PPAR gamma	+	0.5657	56.57%
Honey bee toxicity	-	0.8099	80.99%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9735	97.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.51%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.55%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.04%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.09%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.92%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.39%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.15%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.15%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.09%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.04%	93.56%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.78%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.24%	95.89%

Plants that contains it

• Anisomeles indica

Cross-Links

• PubChem: 24970921
• NPASS: NPC295312
• ChEMBL: CHEMBL460462