Mehirugin B

Details

• Internal ID: e7b2f1da-ef09-4099-b332-b347120d0f65
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters
• IUPAC Name: [(3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=C2C(C3C1C(C(=O)O3)C)C(=CC2=O)C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1CC(=C2[C@@H]([C@@H]3[C@@H]1[C@@H](C(=O)O3)C)C(=CC2=O)C)C
• InChI: InChI=1S/C20H24O5/c1-6-9(2)19(22)24-14-8-11(4)15-13(21)7-10(3)16(15)18-17(14)12(5)20(23)25-18/h6-7,12,14,16-18H,8H2,1-5H3/b9-6+/t12-,14-,16-,17+,18+/m0/s1
• InChI Key: KRHKMQZMQZFVBI-HKSHSXCXSA-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): 69.70 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• CHEMBL2087217
• (3S)-4beta-(2-Methylcrotonoyloxy)-3,3abeta,4,5,9abeta,9balpha-hexahydro-3beta,6,9-trimethylazuleno[4,5-b]furan-2,7-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	+	0.8380	83.80%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5430	54.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9076	90.76%
OATP1B3 inhibitior	+	0.9293	92.93%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4504	45.04%
P-glycoprotein inhibitior	-	0.4648	46.48%
P-glycoprotein substrate	-	0.6726	67.26%
CYP3A4 substrate	+	0.5897	58.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9057	90.57%
CYP3A4 inhibition	-	0.7916	79.16%
CYP2C9 inhibition	-	0.8490	84.90%
CYP2C19 inhibition	-	0.8358	83.58%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	-	0.5365	53.65%
CYP2C8 inhibition	-	0.8018	80.18%
CYP inhibitory promiscuity	-	0.7969	79.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.4397	43.97%
Eye corrosion	-	0.9282	92.82%
Eye irritation	-	0.8182	81.82%
Skin irritation	-	0.6633	66.33%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	+	0.5118	51.18%
Human Ether-a-go-go-Related Gene inhibition	+	0.8262	82.62%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.7515	75.15%
skin sensitisation	-	0.7025	70.25%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7206	72.06%
Acute Oral Toxicity (c)	III	0.4159	41.59%
Estrogen receptor binding	+	0.6762	67.62%
Androgen receptor binding	+	0.6395	63.95%
Thyroid receptor binding	-	0.5256	52.56%
Glucocorticoid receptor binding	-	0.5949	59.49%
Aromatase binding	-	0.6795	67.95%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.6986	69.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9492	94.92%

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	91.97%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.28%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.06%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.42%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.35%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.78%	99.23%
CHEMBL2581	P07339	Cathepsin D	85.18%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.54%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.25%	89.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.04%	93.65%

Plants that contains it

• Kandelia candel

Cross-Links

• PubChem: 66553496
• NPASS: NPC107787
• LOTUS: LTS0073800
• wikiData: Q105145010