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2,4-dihydroxycinnamic acid
- Family: Leguminosae/Fabaceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | OC(=O)/C=C/c1ccc(cc1O)O |
|---|---|
| InChI | InChI=1S/C9H8O4/c10-7-3-1-6(8(11)5-7)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+ |
| InChIKey | HGEFWFBFQKWVMY-DUXPYHPUSA-N |
| Formula | C9H8O4 |
| HBA | 3 |
| HBD | 3 |
| MW | 180.16 |
| Rotatable Bonds | 2 |
| TPSA | 77.76 |
| LogP | 1.2 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.0 |
| Exact Mass | 180.04 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cassia absus | Leguminosae/Fabaceae | Plantae | 592576 |
Showing of synonyms
2,4-dihydroxycinnamic acid
3-(2,4-Dihydroxyphenyl)acrylic acid
Umbellic acid
(2E)-3-(2,4-Dihydroxyphenyl)acrylic acid
(E)-3-(2,4-dihydroxyphenyl)prop-2-enoic acid
(2E)-3-(2,4-dihydroxyphenyl)prop-2-enoic acid
99699-42-0
Trans-2,4-dihydroxycinnamic acid
2,4-DIHYDROXY-TRANS CINNAMIC ACID
(E)-3-(2,4-dihydroxyphenyl)acrylic acid
3-(2,4-Dihydroxyphenyl)-2-propenoic acid
2-Propenoic acid, 3-(2,4-dihydroxyphenyl)-
2-Propenoic acid, 3-(2,4-dihydroxyphenyl)-, (2E)-
693-615-4
614-86-8
U8G3LS2JEX
Umbellsaure
(E)-2,4-Dihydroxycinnamic acid
MFCD00463787
UNII-U8G3LS2JEX
SCHEMBL89187
SCHEMBL471946
CHEMBL1235981
HGEFWFBFQKWVMY-DUXPYHPUSA-N
2,4-Dihydroxycinnamic acid, 97%
3-(2,4-Dihydroxyphenyl)acrylicacid
AKOS002673718
AC-5288
DB01704
FD67899
LS-13596
PD008486
TS-00196
NS00068851
A12691
Q7881241
Pubchem:
446611
Cas:
99699-42-0
Zinc:
ZINC000002043461
Nmrshiftdb2:
60026367
Chembl:
CHEMBL1235981
Drugbank:
DB01704
Pdb Ligand:
SN1
CPRiL:
449206
SMILES: c1ccccc1
Level: 0
Mol. Weight: 78.11 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.94
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.49
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.17
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.66
- Plasma Protein Binding
- 31.24
- 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
- Non-Inhibitor
- CYP 2C9 Substrate
- 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
- 8.35
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.2
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.03
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.76
- 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
- 2.74
- Rat (Acute)
- 2.04
- Rat (Chronic Oral)
- 2.91
- Fathead Minnow
- 4.01
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 352.28
- Hydration Free Energy
- -12.05
- Log(D) at pH=7.4
- -1.37
- Log(P)
- 1.26
- Log S
- -1.71
- Log(Vapor Pressure)
- -5.8
- Melting Point
- 233.15
- pKa Acid
- 5.21
- pKa Basic
- 5.24
| 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 | 0.9299 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9286 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9215 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9204 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9162 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9050 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8786 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8605 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 3 | 0.8559 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8432 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8299 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8277 |
| Cytosolic IMP-GMP specific 5'-nucleotidase | Q5ZZB6 | Q5ZZB6_LEGPH | Legionella pneumophila subsp. pneumophila | 4 | 0.8096 |
| Feruloyl esterase A | O42807 | FAEA_ASPNG | Aspergillus niger | 3 | 0.8096 |
| Caffeic acid 3-O-methyltransferase | P28002 | COMT1_MEDSA | Medicago sativa | 3 | 0.8073 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8065 |
| Adenosylmethionine-8-amino-7-oxononanoate aminotransferase | P12995 | BIOA_ECOLI | Escherichia coli | 3 | 0.7923 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7856 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7798 |
| Isoleucine--tRNA ligase | P56690 | SYI_THET8 | Thermus thermophilus | 3 | 0.7793 |
| Tyrosine 3-monooxygenase | P04177 | TY3H_RAT | Rattus norvegicus | 3 | 0.7782 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7760 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.7724 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.7712 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7623 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7548 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7545 |
| Malate synthase G | P9WK17 | MASZ_MYCTU | Mycobacterium tuberculosis | 3 | 0.7518 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7446 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7423 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 3 | 0.7421 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7411 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.7371 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7331 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7326 |
| diguanylate cyclase | B0RM05 | B0RM05_XANCB | Xanthomonas campestris pv. campestris | 4 | 0.7304 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7293 |
| Eukaryotic translation initiation factor 4E type 3 | Q9DBB5 | IF4E3_MOUSE | Mus musculus | 3 | 0.7272 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7224 |
| Adenosine monophosphate-protein transferase | Q8ZVF7 | Q8ZVF7_PYRAE | Pyrobaculum aerophilum | 3 | 0.7220 |
| Aminopeptidase N | P15145 | AMPN_PIG | Sus scrofa | 2 | 0.7219 |
| Uridine phosphorylase | Q5XA29 | Q5XA29_STRP6 | Streptococcus pyogenes serotype M6 | 3 | 0.7141 |
| Benzoylformate decarboxylase | P20906 | MDLC_PSEPU | Pseudomonas putida | 3 | 0.7136 |
| Orotidine 5'-phosphate decarboxylase | Q5L0U0 | PYRF_GEOKA | Geobacillus kaustophilus | 3 | 0.7121 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7099 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7084 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7081 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7079 |
| Nucleoside permease | Q9KPL5 | Q9KPL5_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7058 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7054 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 2 | 0.7054 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7036 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7030 |
| D-mycarose 3-C-methyltransferase | Q194Q4 | Q194Q4_STRAA | Streptomyces argillaceus | 4 | 0.7029 |