Vulpinic Acid

Details

• Internal ID: cce0f870-e8a8-4070-a058-407015cff5a5
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: methyl (2E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate
• InChI: InChI=1S/C19H14O5/c1-23-18(21)15(13-10-6-3-7-11-13)17-16(20)14(19(22)24-17)12-8-4-2-5-9-12/h2-11,20H,1H3/b17-15+
• InChI Key: OMZRMXULWNMRAE-BMRADRMJSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₄O₅
• Molecular Weight: 322.30 g/mol
• Exact Mass: 322.08412354 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 521-52-8
• methyl (2E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate
• DTXSID601027308
• NSC-5897
• RefChem:194707
• DTXCID001511575
• methyl (2E)-(5-hydroxy-3-oxo-4-phenyl-2(3H)-furanylidene)(phenyl)acetate
• 208-314-1
• Benzeneacetic acid, alpha-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester, (alphaE)-
• 13N7RF6M84
• Vulpic acid
• 73622-57-8
• MFCD00075804
• NSC5897
• methyl (E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2(5H)-ylidene)-2-phenylacetate
• BRN 1437166
• NSC 5897
• methyl (Z)-2-(3-hydroxy-5-oxo-4-phenylfuran-2(5H)-ylidene)-2-phenylacetate
• Acetic acid, (3-hydroxy-5-oxo-4-phenyl-2(5H)-furylidene)phenyl-, methyl ester
• SR-05000002200
• Methylpulvinsaure
• 2-(2,5-Dihydro-3-hydroxy-5-oxo-4-phenyl-2-furanylidene)-2-phenylacetic acid methyl ester
• SCHEMBL559924
• SCHEMBL559925
• CHEMBL463212
• orb1303479
• CHEBI:144250
• NLQPTDHMZUGQCX-BMRADRMJSA-N
• OMZRMXULWNMRAE-BMRADRMJSA-N
• BDBM50478424
• WLN: T5VOYJ CUYR&VO1 DQ ER
• 3,4-Dihydroxy-2,5-Diphenyl-2,4-hexadienedioic Acid Methyl Ester 3,6-Lactone
• AKOS030632335
• CCG-208551
• FV28725
• Benzeneacetic acid, .alpha.-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester
• Benzeneacetic acid, methyl ester, (E)-
• NCGC00160145-01
• Acetic acid, 2-(2,5-dihydro-3-hydroxy-5-oxo-4-phenyl-2-furanylidene)-2-phenyl-, methyl ester
• DA-68664
• HY-125919
• CS-0103068
• SR-05000002200-2
• SR-05000002200-3
• .DELTA.2(5H), 3-hydroxy-5-oxo-.alpha.,4-diphenyl-, methyl ester
• .delta.(sup 2(5H), 3-hydroxy-5-oxo-.alpha.,4-diphenyl-, methyl ester
• 2, 3,4-dihydroxy-2,5-diphenyl-, mono-.gamma.-lactone, methyl ester
• methyl (2E)-2-(3-hydroxy-5-oxo-4-phenyl-2-furylidene)-2-phenyl-acetate
• (?E)-?-(3-Hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)benzeneacetic acid methyl ester
• .delta.2(5H),.alpha.-Furanacetic acid, 3-hydroxy-5-oxo-.alpha.,4-diphenyl-, methyl ester
• 2,4-Hexadienedioic acid, 3,4-dihydroxy-2,5-diphenyl-, mono-.gamma.-lactone, methyl ester
• Methyl (2E)-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)(phenyl)ethanoate
• Methyl (2E)-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)(phenyl)ethanoate #
• (alphaE)-alpha-(3-Hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)benzeneacetic Acid Methyl Ester
• .delta.(sup 2(5H),.alpha.)-Furanacetic acid, 3-hydroxy-5-oxo-.alpha.,4-diphenyl-, methyl ester
• Benzeneacetic acid, .alpha.-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9849	98.49%
Caco-2	+	0.7557	75.57%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8019	80.19%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7059	70.59%
P-glycoprotein inhibitior	-	0.4646	46.46%
P-glycoprotein substrate	-	0.9389	93.89%
CYP3A4 substrate	-	0.5562	55.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8913	89.13%
CYP3A4 inhibition	-	0.9182	91.82%
CYP2C9 inhibition	-	0.5400	54.00%
CYP2C19 inhibition	+	0.6160	61.60%
CYP2D6 inhibition	-	0.9393	93.93%
CYP1A2 inhibition	+	0.5822	58.22%
CYP2C8 inhibition	-	0.5773	57.73%
CYP inhibitory promiscuity	+	0.7381	73.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8482	84.82%
Carcinogenicity (trinary)	Danger	0.6507	65.07%
Eye corrosion	-	0.9820	98.20%
Eye irritation	+	0.8443	84.43%
Skin irritation	-	0.7742	77.42%
Skin corrosion	-	0.9674	96.74%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6602	66.02%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.5592	55.92%
skin sensitisation	-	0.8604	86.04%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.7661	76.61%
Acute Oral Toxicity (c)	III	0.5077	50.77%
Estrogen receptor binding	+	0.7179	71.79%
Androgen receptor binding	+	0.6073	60.73%
Thyroid receptor binding	-	0.5362	53.62%
Glucocorticoid receptor binding	+	0.5601	56.01%
Aromatase binding	+	0.5545	55.45%
PPAR gamma	-	0.5140	51.40%
Honey bee toxicity	-	0.9233	92.33%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9861	98.61%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	223.9 nM; 223.9 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.68%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.12%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.70%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.64%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.54%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.04%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.03%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.81%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	83.12%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.52%	85.14%

Plants that contains it

• Zanthoxylum bungeanum
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 54690323
• NPASS: NPC281604
• ChEMBL: CHEMBL463212