Coumalic acid

Details

• Internal ID: fa0307d4-6169-4334-9b14-7911639518b5
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives
• IUPAC Name: 6-oxopyran-3-carboxylic acid
• SMILES (Canonical): C1=CC(=O)OC=C1C(=O)O
• SMILES (Isomeric): C1=CC(=O)OC=C1C(=O)O
• InChI: InChI=1S/C6H4O4/c7-5-2-1-4(3-10-5)6(8)9/h1-3H,(H,8,9)
• InChI Key: ORGPJDKNYMVLFL-UHFFFAOYSA-N
• Popularity: 39 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₄O₄
• Molecular Weight: 140.09 g/mol
• Exact Mass: 140.01095860 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.34
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 500-05-0
• 2-Oxo-2H-pyran-5-carboxylic acid
• Cumalic acid
• 6-oxopyran-3-carboxylic acid
• 2H-Pyran-5-carboxylic acid, 2-oxo-
• 2-Oxopyran-5-carboxylic acid
• .alpha.-Pyrone-5-carboxylic acid
• 2-Pyrone-5-carboxylic acid
• alpha-Pyrone-5-carboxylic acid
• UNII-OB1JPY343G
• OB1JPY343G
• EINECS 207-899-0
• NSC 22978
• NSC-22978
• 2-Oxo-1,2H-pyran-5-carboxylic acid
• 2-Pentenedioic acid, 4-(hydroxymethylene)-, delta-lactone
• Coumalicacid
• 2-Pentenedioic acid, 4-(hydroxymethylene)-, .delta.-lactone
• Coumalic acid, 97%
• a-Pyrone-5-carboxylic acid
• COUMALIC ACID [MI]
• SCHEMBL258740
• 6-oxo-pyran-3-carboxylic acid
• CHEMBL216734
• DTXSID60870569
• (E)-2-Butenedioicaciddiethylester
• .alpha.-Pyrone-3-carboxylic acid
• CHEBI:180952
• NSC22978
• BBL009090
• MFCD00006644
• STK329418
• 2-Oxo-2H-pyran-5-carboxylic acid #
• 2-Pentenedioic acid, .delta.-lactone
• AKOS000119258
• SB40457
• NCGC00336326-01
• AS-17705
• BP-12397
• HY-32004
• CS-0001427
• FT-0624076
• EN300-19035
• 2-OXO-1(2H)-PYRAN-5-CARBOXYLIC ACID
• AB00990923-01
• AB00990923-03
• A827929
• J-650096
• Q-103227
• Q19903002
• F2170-0001
• Z104472302
• GLUTACONIC ACID, 4-(HYDROXYMETHYLENE)-, .DELTA.-LACTONE
• InChI=1/C6H4O4/c7-5-2-1-4(3-10-5)6(8)9/h1-3H,(H,8,9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9333	93.33%
Caco-2	+	0.7234	72.34%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7847	78.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9619	96.19%
OATP1B3 inhibitior	+	0.9813	98.13%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9745	97.45%
P-glycoprotein inhibitior	-	0.9816	98.16%
P-glycoprotein substrate	-	0.9925	99.25%
CYP3A4 substrate	-	0.8106	81.06%
CYP2C9 substrate	-	0.8164	81.64%
CYP2D6 substrate	-	0.9045	90.45%
CYP3A4 inhibition	-	0.8711	87.11%
CYP2C9 inhibition	-	0.9456	94.56%
CYP2C19 inhibition	-	0.9610	96.10%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.9487	94.87%
CYP2C8 inhibition	-	0.8864	88.64%
CYP inhibitory promiscuity	-	0.9908	99.08%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8147	81.47%
Carcinogenicity (trinary)	Non-required	0.6819	68.19%
Eye corrosion	+	0.5348	53.48%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.8423	84.23%
Skin corrosion	-	0.7314	73.14%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9325	93.25%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	-	0.8510	85.10%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5947	59.47%
Acute Oral Toxicity (c)	III	0.6135	61.35%
Estrogen receptor binding	-	0.9306	93.06%
Androgen receptor binding	-	0.8842	88.42%
Thyroid receptor binding	-	0.9176	91.76%
Glucocorticoid receptor binding	-	0.8981	89.81%
Aromatase binding	-	0.8374	83.74%
PPAR gamma	-	0.9036	90.36%
Honey bee toxicity	-	0.9749	97.49%
Biodegradation	+	0.8000	80.00%
Crustacea aquatic toxicity	-	0.9100	91.00%
Fish aquatic toxicity	+	0.7902	79.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293294	P51151	Ras-related protein Rab-9A	95.73%	87.67%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	92.65%	81.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.79%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.78%	95.56%
CHEMBL3194	P02766	Transthyretin	84.46%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.80%	99.23%
CHEMBL4208	P20618	Proteasome component C5	81.20%	90.00%

Plants that contains it

• Hansenia weberbaueriana

Cross-Links

• PubChem: 68141
• NPASS: NPC51846