Caftaric acid

Details

• Internal ID: 16bc121e-2b15-41e0-9423-b62e0d28ea72
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (2R,3R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)O)C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)O[C@H]([C@H](C(=O)O)O)C(=O)O)O)O
• InChI: InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1
• InChI Key: SWGKAHCIOQPKFW-JTNORFRNSA-N
• Popularity: 56 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₉
• Molecular Weight: 312.23 g/mol
• Exact Mass: 312.04813196 g/mol
• Topological Polar Surface Area (TPSA): 162.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.45
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 67879-58-7
• trans-caftaric acid
• (2R,3R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid
• CAFFEOYLTARTARICACID
• UNII-WCV7W3174L
• WCV7W3174L
• 1234-09-9
• Butanedioic acid, 2-(3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)-3-hydroxy-, (R-(R*,R*-(E)))-
• Caffeoyltartaric acid
• Butanedioic acid, 2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-3-hydroxy-, (2R,3R)-
• C13H12O9
• Caffeoyl tartaric acid
• monocaffeoyltartaric acid
• BOC,TBU-BETA-ALA-OH
• Caftaric acid , HPLC Grade
• Caftaric acid, >=97.0%
• CHEMBL558557
• CAFTARIC ACID [USP-RS]
• DTXSID3036866
• SCHEMBL16426394
• CHEBI:174975
• Caftaric acid, analytical standard
• HY-N0321
• MFCD02094177
• s3308
• AKOS022175477
• C13-H12-O9
• (2R,3R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxy-butanedioic acid
• AC-34146
• AS-79234
• A835919
• Q-100761
• Q5017207
• Caftaric acid, United States Pharmacopeia (USP) Reference Standard
• (2R,3R)-2-(((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOYL)OXY)-3-HYDROXYSUCCINIC ACID
• (2R,3R)-2-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)-3-hydroxysuccinic acid
• (2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
• (2R,3R)-2-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
• 2-Caffeoyl-L-tartaric acid;2-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-butanedioic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8721	87.21%
Caco-2	-	0.8299	82.99%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6638	66.38%
OATP2B1 inhibitior	-	0.7106	71.06%
OATP1B1 inhibitior	+	0.9561	95.61%
OATP1B3 inhibitior	+	0.9693	96.93%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9338	93.38%
BSEP inhibitior	-	0.7188	71.88%
P-glycoprotein inhibitior	-	0.9250	92.50%
P-glycoprotein substrate	-	0.9405	94.05%
CYP3A4 substrate	-	0.6032	60.32%
CYP2C9 substrate	-	0.5984	59.84%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.8352	83.52%
CYP2C9 inhibition	-	0.7902	79.02%
CYP2C19 inhibition	-	0.9321	93.21%
CYP2D6 inhibition	-	0.9554	95.54%
CYP1A2 inhibition	-	0.8973	89.73%
CYP2C8 inhibition	+	0.4906	49.06%
CYP inhibitory promiscuity	-	0.9126	91.26%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8081	80.81%
Carcinogenicity (trinary)	Non-required	0.6715	67.15%
Eye corrosion	-	0.9524	95.24%
Eye irritation	-	0.5483	54.83%
Skin irritation	+	0.6616	66.16%
Skin corrosion	-	0.8471	84.71%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7690	76.90%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.5979	59.79%
skin sensitisation	+	0.7535	75.35%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8364	83.64%
Acute Oral Toxicity (c)	III	0.7293	72.93%
Estrogen receptor binding	-	0.6229	62.29%
Androgen receptor binding	+	0.7168	71.68%
Thyroid receptor binding	-	0.7215	72.15%
Glucocorticoid receptor binding	-	0.5381	53.81%
Aromatase binding	-	0.7157	71.57%
PPAR gamma	-	0.6799	67.99%
Honey bee toxicity	-	0.8330	83.30%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7056	70.56%
Fish aquatic toxicity	+	0.9825	98.25%

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	98.57%	91.11%
CHEMBL3194	P02766	Transthyretin	96.65%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.69%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	93.41%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.82%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.54%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.90%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.74%	94.45%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	86.87%	97.53%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.93%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.81%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.23%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.78%	98.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.16%	80.78%

Plants that contains it

• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Celmisia petriei
• Cichorium intybus
• Cichorium pumilum
• Cirsium helenioides
• Clusia torresii
• Echinacea angustifolia
• Echinacea pallida
• Echinacea purpurea
• Ferula assa-foetida
• Handroanthus guayacan
• Hydrastis canadensis
• Isodon rubescens
• Lapsana communis
• Orthosiphon aristatus
• Oryza sativa
• Populus tremula
• Primula veris
• Senecio integerrimus
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum
• Ulmus laciniata
• Vitis vinifera

Cross-Links

• PubChem: 6440397
• NPASS: NPC251407
• ChEMBL: CHEMBL558557
• LOTUS: LTS0276394
• wikiData: Q5017207