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Caftaric acid

Family: Plantae - Rosaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	O=C(O[C@H]([C@H](C(=O)O)O)C(=O)O)/C=C/c1ccc(c(c1)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
InChIKey	SWGKAHCIOQPKFW-JTNORFRNSA-N
Formula	C₁₃H₁₂O₉
HBA	7
HBD	5
MW	312.23
Rotatable Bonds	6
TPSA	161.59
LogP	-0.45
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	312.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Crataegus oxyacantha	Rosaceae	Plantae	510738

Showing of synonyms

Benabderrahmane W, Lores M, et al. (2021). Polyphenolic content and bioactivities of Crataegus oxyacantha L (Rosaceae). Natural product research, 2021, 35(4), 627-632. [View] [PubMed]

Pubchem: 6440397

Cas: 67879-58-7

Zinc: ZINC000002389524

Chebi: 174975

Nmrshiftdb2: 60028370

Chembl: CHEMBL558557

Comptox: DTXSID3036866

CPRiL: 100107

SMILES: c1ccccc1

Level: 0

Mol. Weight: 312.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.32
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.940
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -6.19

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.310
Plasma Protein Binding: 41.58
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.750
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.790
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.810
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.560
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 6.360
Rat (Acute): 2.050
Rat (Chronic Oral): 3.080
Fathead Minnow: 3.930
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 447.170
Hydration Free Energy: -9.330
Log(D) at pH=7.4: -2.280
Log(P): 0.15
Log S: -1.36
Log(Vapor Pressure): -15.05
Melting Point: 222.15
pKa Acid: 3.24
pKa Basic: 6.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9265
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9156
Geranyl diphosphate synthase large subunit	Q9SBR3	Q9SBR3_MENPI	Mentha piperita	3	0.9138
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9120
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9011
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8937
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8856
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	3	0.8686
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8643
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8626
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8415
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8362
Uncharacterized protein	Q8DY32	Q8DY32_STRA5	Streptococcus agalactiae serotype V	5	0.8277
Geranylgeranyl pyrophosphate synthase BTS1	Q12051	GGPPS_YEAST	Saccharomyces cerevisiae	3	0.8271
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8215
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8208
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8164
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	3	0.8154
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8148
Putative choline kinase	Q5CUP2	Q5CUP2_CRYPI	Cryptosporidium parvum	3	0.8145
Farnesyl pyrophosphate synthase	P14324	FPPS_HUMAN	Homo sapiens	3	0.8129
Caffeic acid 3-O-methyltransferase	P28002	COMT1_MEDSA	Medicago sativa	3	0.8111
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.7979
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7966
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7965
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7938
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7936
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7927
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7880
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7877
MutT/nudix family protein	Q5SJY9	Q5SJY9_THET8	Thermus thermophilus	3	0.7858
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7773
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7730
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	3	0.7697
Nucleoside diphosphate kinase	O58429	NDK_PYRHO	Pyrococcus horikoshii	3	0.7689
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7671
Ficolin-2	Q15485	FCN2_HUMAN	Homo sapiens	3	0.7664
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7662
Nucleoside diphosphate kinase	A5J299	A5J299_PENVA	Penaeus vannamei	3	0.7569
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	4	0.7539
non-specific serine/threonine protein kinase	Q6FS46	Q6FS46_CANGA	Candida glabrata	4	0.7530
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7529
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7524
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7517
D-3-phosphoglycerate dehydrogenase	P9WNX3	SERA_MYCTU	Mycobacterium tuberculosis	3	0.7483
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7475
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7466
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7462
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7446
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.7444
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	4	0.7422
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7387
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7386
Serine/threonine-protein kinase PLK	Q4KMI8	Q4KMI8_DANRE	Danio rerio	3	0.7362
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7362
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7358
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7357
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7317
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7306
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7304
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7296
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7291
Glycerol kinase	P0A6F3	GLPK_ECOLI	Escherichia coli	4	0.7244
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7233
Penicillin V acylase	P12256	PAC_LYSSH	Lysinibacillus sphaericus	3	0.7230
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7216
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7213
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7199
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7184
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7181
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7179
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7169
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7169
Eukaryotic translation initiation factor 2 subunit alpha	P20459	IF2A_YEAST	Saccharomyces cerevisiae	3	0.7148
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7147
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7147
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7142
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7141
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7117
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7104
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7099
Mexicain	P84346	MEX1_JACME	Jacaratia mexicana	3	0.7097
Glucose-1-phosphate adenylyltransferase small subunit, chloroplastic/amyloplastic	P23509	GLGS_SOLTU	Solanum tuberosum	3	0.7091
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7090
Eukaryotic translation initiation factor 4E type 2	O60573	IF4E2_HUMAN	Homo sapiens	4	0.7087
MutT/nudix family protein	O33199	O33199_MYCTO	Mycobacterium tuberculosis	3	0.7086
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7085
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase	P12995	BIOA_ECOLI	Escherichia coli	3	0.7078
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7045
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7041
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7039
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7033
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7022
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	4	0.7019
D-mycarose 3-C-methyltransferase	Q194Q4	Q194Q4_STRAA	Streptomyces argillaceus	5	0.7015

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