Protocatechuic acid

  • GreenMolBD CID : 510
  • Molecular Formula : C7H6O4
  • Molecular Weight : 154.121
  • Exact Molecular Mass : 154.027
  • IUPAC Name : 3,4-dihydroxybenzoic acid
  • InChI : InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
  • InChI Key : YQUVCSBJEUQKSH-UHFFFAOYSA-N
  • Canonical SMILES : C1=CC(=C(C=C1C(=O)O)O)O
  • Isomeric SMILES : c1cc(c(cc1C(=O)O)O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

1.3. Alternative Parent

Benzoic acids; Catechols; Benzoyl derivatives; 1-hydroxy-4-unsubstituted benzenoids; 1-hydroxy-2-unsubstituted benzenoids; Monocarboxylic acids and derivatives; Carboxylic acids; Organooxygen compounds; Organic oxides; Hydrocarbon derivatives;

1.4. Molecular Framework

Aromatic homomonocyclic compounds

1.5. Substituents

Dihydroxybenzoic acid; Hydroxybenzoic acid; Benzoic acid; Benzoyl; Catechol; 1-hydroxy-4-unsubstituted benzenoid; 1-hydroxy-2-unsubstituted benzenoid; Phenol; Carboxylic acid derivative; Carboxylic acid; Monocarboxylic acid or derivatives; Organic oxygen compound; Hydrocarbon derivative; Organooxygen compound; Organic oxide; Aromatic homomonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
0.796 77.76 3 4 11 1 6 6 3.67309 180.045 151.237 0.856016

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-154.753104 2.08 -4.807 -9.09706 -0.51758 4.29

4. Compound Reactivity

DLP nRFG nLMR
0 0 2

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Toxic 1.67778 1572.25 0.366421 None Strong Moderate Degradable 0.23728 29.808

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes No Yes Yes No Yes

7. Synonyms

Name
3,4-DIHYDROXYBENZOIC ACID
protocatechuic acid
99-50-3
4-Carboxy-1,2-dihydroxybenzene
Protocatehuic acid
Benzoic acid, 3,4-dihydroxy-
protocatechuate
4,5-Dihydroxybenzoic acid
3,4-Dihydroxybenzoicacid
UNII-36R5QJ8L4B
CCRIS 6291
EINECS 202-760-0
NSC 16631
BRN 1448841
3,4-Dihydroxy Benzoic Acid
CHEMBL37537
MLS000737807
CHEBI:36062
YQUVCSBJEUQKSH-UHFFFAOYSA-N
MFCD00002509
1ykp
3,4-dihydroxybenzoic acid (protocatechuic acid)
Protocatechuic acid polymer
Catechol-4-carboxylic Acid
3, 4-Dihydroxybenzoic acid
NSC16631
3,4-dihydroxybenzoes
Benzoic acid, 3,4-dihydroxy- (9CI)
DB03946
SMR000528167
C00230
D-3487
b-Resorcylate
beta-Resorcylate
4fht
Protacatechuic Acid
cid_72
ACMC-209scu
AC1Q5TRL
DSSTox_CID_1212
Protocatechuic acid (M1)
bmse000328
3,4-dihydroxy-benzoic acid
DSSTox_RID_76012
DSSTox_GSID_21212
SCHEMBL39435
KSC486M3D
3,4-Dihydroxybenzoate, VIII
Pyrocatechol-4-carboxylic Acid
36R5QJ8L4B
AC1L18F1
AC1Q732Z
DTXSID4021212
CTK3I6631
KS-00000COI
ZINC13246
3,4-DIACETOXY-BENZOICACID
MolPort-000-881-444
BB_NC-2256
HMS2270A17
KUC104409N
ACN-S002778
ACT07872
HY-N0294
Tox21_200167
ANW-41020
BBL012232
BDBM50100861
CP0105
NSC-16631
SBB061371
STL163570
AKOS000119632
AC-9617
CCG-207950
CS-6092
KSC-10-128
LS-7685
MCULE-8964889860
RP21802
RTR-032902
TRA0078616
CAS-99-50-3
Oxidative polymer of protocatechuic acid
3,4-Dihydroxybenzoic acid, 97% 25g
NCGC00246757-01
NCGC00246757-02
NCGC00257721-01
AJ-08357
AK-47644
BR-47644
BT000176
KB-28323
OR021858
OR382759
SC-46684
AB0008267
AB1002236
DB-021903
KB-234038
ST2417248
TR-032902
AM20060767
FT-0600028
N2466
ST50824448
3,4-Dihydroxybenzoic acid, >=97.0% (T)
3,4-Dihydroxybenzoic acid, analytical standard
M-3133
002D509
AE-562/40524392
I01-2896
976C8CCE-B25D-4E0A-9A6F-3CEEA7A6964F
3,4-Dihydroxybenzoic acid, Vetec(TM) reagent grade, 97%
Protocatechuic acid, primary pharmaceutical reference standard
Protocatechuic acid, United States Pharmacopeia (USP) Reference Standard
InChI=1/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11
AS-10808
BG00600769
BG01499737

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Protocatechuic acid
Acacia nilotica (L.) Wild. 11
Anisomeles indica (L.) Kuntze. Whole Plant 5 , 12
Areca catechu L. Nut 11 , 2 , 13
Coix lachryma Linn. Seed 2
Coriandrum sativum Linn. 38
Crocus sativus L. Petal; Pollen 12 , 18
Curcuma amada Rhizome 13
Cyperus rotundus L Aerial 7 , 24
Ichnocarpus frutescens Leaf 8
Impatiens balsamina L.  Flower 5
Jasminum graniflorum Aerial 13 , 20
Juglans regia Pericarp; Fruit 8 , 17 , 19
Lepidium sativum Seed 3 , 7
Litchi chinensis Seed 2
Mangifera indica Stem Bark 1
Phaseolus vulgaris Seed 1

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
747 3-dehydroquinate synthase Escherichia coli 44000 11412967
747 3-dehydroquinate synthase Escherichia coli 65000 11412967
427 Alpha-(1,3)-fucosyltransferase VII 137000 10.1016/j.abb.2004.02.039 15081893
662 Alpha-glucosidase MAL12 Saccharomyces cerevisiae 8.51E+4 10.1111/cbdd.12205 23957301
662 Alpha-glucosidase MAL12 Saccharomyces cerevisiae >3.00e+5 10.3109/14756366.2012.719503 23009660
431 Carbonic anhydrase Dicentrarchus labrax 3210 10.1016/j.bmcl.2011.05.071 21669522
7 carbonic anhydrase 1 CA1 Homo sapiens 1.08 568362
8 carbonic anhydrase 12 CA12 Homo sapiens 4.09 568365
129 carbonic anhydrase 14 CA14 Homo sapiens 0.69 729533
9 carbonic anhydrase 2 CA2 Homo sapiens 0.47 568363
10 carbonic anhydrase 4 CA4 Homo sapiens 2.45 667535
22 carbonic anhydrase 6 CA6 Homo sapiens 4.72 607496
22 carbonic anhydrase 6 CA6 Homo sapiens 4.72 667536
98 Carbonic anhydrase 6 (CA VI) Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 4720 10.1016/j.bmcl.2011.05.071 21669522
98 Carbonic anhydrase 6 (CA VI) Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 4720 10.1016/j.ejmech.2012.05.025 22687439
130 carbonic anhydrase 7 CA7 Homo sapiens 7.87 729536
131 carbonic anhydrase 9 CA9 Homo sapiens 4.45 568364
99 Carbonic Anhydrase I Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 1080 10.1016/j.bmc.2011.01.016 21282059
100 Carbonic Anhydrase II Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 470 10.1016/j.bmc.2011.01.016 21282059
101 Carbonic Anhydrase IV Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 2450 10.1016/j.ejmech.2012.05.025 22687439
132 Carbonic Anhydrase IX Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 4450 10.1016/j.bmc.2011.01.016 21282059
133 Carbonic Anhydrase VII Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 7870 10.1016/j.bmc.2012.05.019 22668600
134 Carbonic Anhydrase XII Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 4090 10.1016/j.bmc.2011.01.016 21282059
135 Carbonic Anhydrase XIV Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 690 10.1016/j.bmc.2012.05.019 22668600
561 Cathepsin L1 Homo sapiens 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX >59642 2196
11 DNA polymerase beta POLB Homo sapiens 25.1189 485314
65 DNA polymerase iota POLI Homo sapiens 79.4328 588590
84 geminin, DNA replication inhibitor GMNN Homo sapiens 0.7308 624297
26 GLI family zinc finger 3 GLI3 Homo sapiens 30.6067 1259369
14 glucosidase alpha, acid GAA Homo sapiens 5.0119 2100
43 glutaminase GLS Homo sapiens 3.9811 624170
92 histone H2AX LOC100757539 Cricetulus griseus 112.935 1224845
123 L3MBTL1, histone methyl-lysine binding protein L3MBTL1 Homo sapiens 39.8107 485360
610 M18 aspartyl aminopeptidase Plasmodium falciparum (isolate 3D7) 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 479.4 2195
610 M18 aspartyl aminopeptidase PfM18AAP Plasmodium falciparum 3D7 0.4794 2195
16 microtubule associated protein tau MAPT Homo sapiens 2.8184 1460
446 Procollagen-proline,2-oxoglutarate-4-dioxygenase Gallus gallus 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX 5000 3011801
185 Rap guanine nucleotide exchange factor 3 RAPGEF3 Homo sapiens 125.893 720707
54 retinoid X receptor alpha RXRA Homo sapiens 24.5202 1159527
47 thyroid hormone receptor beta Thrb Rattus norvegicus 4.8508 743065
47 thyroid hormone receptor beta Thrb Rattus norvegicus 18.2313 743067
527 Xanthine dehydrogenase/oxidase (XO) Bos taurus 1B4U,1EOB,1N8Q,1PHH,1YKL,1YKN,1YKP,2BSL,2BUV,2BV0,3DX5,3HKP,3LMX,3MV6,3O5U,3PCA,3WRC,4EYK,4FHT,4J0I,4PAF,4RGX,5FAN 5.80E+3 10.1111/cbdd.12205 23957301

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
126632645ChemMolSource URLSource Detail30100183Source Record URL
126649125ChemMolSource URLSource Detail44009933Source Record URL
241101289ChemMolSource URLSource Detail99110393Source Record URL
241176625ChemMolSource URLSource Detail99185729Source Record URL
202541251Debye Scientific Co., LtdSource URLSource DetailDB-021903Source Record URL
251897902labseekerSource URLSource DetailSC-46684Source Record URL
3562662191717 CheMall CorporationSource URLSource DetailBG00600769Source Record URL
3566258901717 CheMall CorporationSource URLSource DetailBG01499737Source Record URL
3627691221717 CheMall CorporationSource URLSource DetailBG04454648Source Record URL
3596919381717 CheMall CorporationSource URLSource DetailBG06536117Source Record URL
3603777561717 CheMall CorporationSource URLSource DetailBG07219044Source Record URL
315442414Phion LtdSource URLSource Detail47591148Source Record URL
249837350SyntreeSource URLSource DetailST2417248Source Record URL
318367519CambridgeChemSource URLSource DetailB4712Source Record URL
329970937CambridgeChemSource URLSource DetailP0735Source Record URL
329972163CambridgeChemSource URLSource Detailwkq-00697Source Record URL
171578517Amadis ChemicalSource URLSource Detail205400Source Record URL
162170105AK Scientific, Inc. (AKSCI)Source URLSource Detail565141Source Record URL
136995327ApexmolSource URLSource DetailAM20060767Source Record URL
125326888Vitas-M LaboratorySource URLSource DetailBBL012232Source Record URL
125292635Vitas-M LaboratorySource URLSource DetailSTL163570Source Record URL
368519046AmbinterSource URLSource DetailAmb1960218Source Record URL
275870205BePharm Ltd.Source URLSource DetailB4712Source Record URL
172883520Nanjing KaimuboSource URLSource DetailKB-234038Source Record URL
162135507Nanjing KaimuboSource URLSource DetailKB-28323Source Record URL
85172709ISpharmSource URLSource DetailI01-2896Source Record URL
354325380iChemical Technology USA IncSource URLSource DetailEBD2224170Source Record URL
160808521AnwardSource URLSource DetailANW-41020Source Record URL
318314475Chem-Space.com DatabaseSource URLSource DetailCSC000212155Source Record URL
104293770ABI ChemSource URLSource DetailAC1L18F1Source Record URL
117545550ABI ChemSource URLSource DetailAC1Q5TRLSource Record URL
117607518ABI ChemSource URLSource DetailAC1Q732ZSource Record URL
318468224Angene ChemicalSource URLSource DetailAGN-PC-0WA7ROSource Record URL
316404970abcr GmbHSource URLSource DetailAB133937Source Record URL
136992580Aurum Pharmatech LLCSource URLSource DetailM-3133Source Record URL
277364765Alfa ChemistrySource URLSource Detail58534-64-8Source Record URL
49747291BiosynthSource URLSource DetailD-3487Source Record URL
316897723Hangzhou APIChem TechnologySource URLSource DetailAC-9617Source Record URL
255514502ZINCSource URLSource DetailZINC13246Source Record URL
329733105VladaChemSource URLSource DetailVL141944Source Record URL
252216635Race ChemicalSource URLSource DetailRV022505265Source Record URL
316972266ParchemSource URLSource Detail38773Source Record URL
316605239ParchemSource URLSource Detail7342Source Record URL
321937897AcadechemSource URLSource DetailACDS-069212Source Record URL
329978307Acorn PharmaTech Product ListSource URLSource DetailACN-035759Source Record URL
135916823Acorn PharmaTech Product ListSource URLSource DetailACN-S002778Source Record URL
88529433MolPortSource URLSource DetailMolPort-000-881-444Source Record URL
350090282DC ChemicalsSource URLSource DetailDCY-031Source Record URL
312695977TargetMolSource URLSource DetailT0562Source Record URL
160967019Chembase.cnSource URLSource Detail3581Source Record URL
252392772AHH Chemical co.,ltdSource URLSource DetailMT-02673Source Record URL
29204506R&D ChemicalsSource URLSource Detail6050Source Record URL
174478115BerrChemSource URLSource DetailBR-47644Source Record URL
318156852ApexBio TechnologySource URLSource DetailN2466Source Record URL
321904318AbaChemSceneSource URLSource DetailCS-6092Source Record URL
174552888WutechSource URLSource DetailRP21802Source Record URL
252404046MolepediaSource URLSource DetailM90002729PSource Record URL
103126078AAA ChemistrySource URLSource DetailAR-1E9213Source Record URL
312684606BiocoreSource URLSource DetailBIE000136Source Record URL
250171460Green Chempharm IncSource URLSource Detail28-0158Source Record URL
277297030MolCoreSource URLSource DetailCS20259Source Record URL
163819284Oakwood ProductsSource URLSource Detail043464Source Record URL
312336900AvaChem ScientificSource URLSource Detail3289Source Record URL
57319934NovoSeekSource URLSource Detail72Source Record URL
250197472Founder PharmaSource URLSource DetailFD12979Source Record URL
85089012MP BiomedicalsSource URLSource Detail156421Source Record URL
51074286MP BiomedicalsSource URLSource Detail205667Source Record URL
346682901LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00173718Source Record URL
346411436King ScientificSource URLSource DetailKS-00000COISource Record URL
163806955King ScientificSource URLSource DetailKSC486M3DSource Record URL
117689148ABBLIS ChemicalsSource URLSource DetailAB1002236Source Record URL
223377832Assembly Blocks Pvt. Ltd.Source URLSource DetailAB0008267Source Record URL
349519896Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM1038038Source Record URL
347747224Yuhao ChemicalSource URLSource DetailLT6644Source Record URL
162754949ChemTikSource URLSource DetailCTK3I6631Source Record URL
254758472Achemo Scientific LimitedSource URLSource DetailAC-20247Source Record URL
312292878NORRIS PHARMSource URLSource DetailTH-D16707Source Record URL
134220988SpecsSource URLSource DetailAE-562/40524392Source Record URL
319457887eNovation ChemicalsSource URLSource DetailD402882Source Record URL
87565255TCI (Tokyo Chemical Industry)Source URLSource DetailC0055Source Record URL
329747840Sigma-AldrichSource URLSource Detail03930590_SIALSource Record URL
329748656Sigma-AldrichSource URLSource Detail08992_SIALSource Record URL
329750856Sigma-AldrichSource URLSource Detail1579310_USPSource Record URL
57649743Sigma-AldrichSource URLSource Detail37580_ALDRICHSource Record URL
329830159Sigma-AldrichSource URLSource DetailV900791_VETECSource Record URL
341832607OChemSource URLSource Detail2438Source Record URL
310271811Glentham Life Sciences Ltd.Source URLSource DetailGK7288Source Record URL
143435374TimTecSource URLSource DetailSBB061371Source Record URL
143857028TimTecSource URLSource DetailST50824448Source Record URL
162300212AchemicaSource URLSource DetailACMC-209scuSource Record URL
204361208TractusSource URLSource DetailRTR-032902Source Record URL
135562539TractusSource URLSource DetailTR-032902Source Record URL
252260326TractusSource URLSource DetailTRA0078616Source Record URL
321904223MedChemexpress MCESource URLSource DetailHY-N0294Source Record URL
374176986AA BLOCKSSource URLSource DetailAA003IEVSource Record URL
255396097OXCHEM CORPORATIONSource URLSource DetailAX8004712Source Record URL
355252318MolMallSource URLSource Detail21496Source Record URL
211536109TripleBondSource URLSource DetailCP0105Source Record URL
313078029ClearsynthSource URLSource DetailCS-O-31060Source Record URL
223519318A&J Pharmtech CO., LTD.Source URLSource DetailAJ-08357Source Record URL
254788177Boc SciencesSource URLSource Detail99-50-3Source Record URL
319434897Hefei Hirisun Pharmatech Co., LtdSource URLSource DetailHR011529Source Record URL
169530257MculeSource URLSource DetailMCULE-8964889860Source Record URL
165238670ACT ChemicalSource URLSource DetailACT07872Source Record URL
322078640Pi ChemicalsSource URLSource DetailPI-20424Source Record URL
322082383Pi ChemicalsSource URLSource DetailPI-24686Source Record URL
104668055AKos Consulting & SolutionsSource URLSource DetailAKOS000119632Source Record URL
342521151Wubei-BiochemSource URLSource DetailWB000149SUSource Record URL
164785208Finetech Industry LimitedSource URLSource DetailFT-0600028Source Record URL
374033178Combi-BlocksSource URLSource DetailQA-4158Source Record URL
274952188ChemFacesSource URLSource DetailCFN97568Source Record URL
354265393Key Organics/BIONETSource URLSource DetailAS-10808Source Record URL
355036708MuseChemSource URLSource DetailI005743Source Record URL
340547283Activate ScientificSource URLSource DetailAS33149Source Record URL
7887016SMIDSource URLSource DetailDHBSource Record URL
252051308Bide Pharmatech Ltd.Source URLSource DetailBD4712Source Record URL