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P-hydroxybenzoic acid
- Family: Plantae - Solanaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Benzoic Acid Derivative
| Canonical Smiles | OC(=O)Cc1c[nH]c2c1cccc2 |
|---|---|
| InChI | InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13) |
| InChIKey | SEOVTRFCIGRIMH-UHFFFAOYSA-N |
| Formula | C10H9NO2 |
| HBA | 1 |
| HBD | 2 |
| MW | 175.19 |
| Rotatable Bonds | 2 |
| TPSA | 53.09 |
| LogP | 1.79 |
| Number Rings | 2 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.1 |
| Exact Mass | 175.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bassia indica | Chenopodiaceae | Plantae | 267517 |
| 2 | Solanum nigrum | Solanaceae | Plantae | 4112 |
Showing of synonyms
P-hydroxybenzoic acid
Indole-3-acetic acid
87-51-4
3-Indoleacetic acid
Indoleacetic acid
Heteroauxin
1H-Indole-3-acetic acid
1H-indol-3-ylacetic acid
2-(1H-Indol-3-yl)acetic acid
Rhizopin
Rhizopon A
3-Indolylacetic acid
Indol-3-ylacetic acid
Hexteroauxin
3-(Carboxymethyl)indole
3-Iaa
Beta-Indoleacetic acid
Acetic acid, indolyl-
Heteroauxinhexteroauxiniaa
Beta-Indolylacetic acid
Indolylacetic acid
Indolyl-3-acetic acid
Indole acetic acid
Omega-Skatole carboxylic acid
Kyselina 3-indolyloctova
Indoleacetic acid (VAN)
(1H-Indol-3-yl)-acetic acid
CCRIS 1014
EPA Pesticide Chemical Code 128915
Kyselina 3-indolyloctova [Czech]
3-Indolylessigsaeure
2-(3-Indolyl)acetic acid
NSC 3787
AI3-24131
3-Indole-Acetic acid
2-(indol-3-yl)ethanoic acid
Indolylacetate
B-Indoleacetate
B-Indolylacetate
(indol-3-yl)acetic acid
3-Indolylacetate
Beta-Indoleacetate
Beta-Indolylacetate
EINECS 201-748-2
Skatole carboxylate
Indol-3-ylacetate
Indolyl-3-acetate
B-Indoleacetic acid
B-Indolylacetic acid
DTXSID5020738
CHEBI:16411
1H-Indole-3-acetate
Skatole carboxylic acid
6U1S09C61L
1H-Indole-3-acetic acid (9CI)
2-(3-Indolyl)acetate
NSC-3787
Beta-Indole-3-acetic acid
(1H-Indol-3-yl)-acetate
Alpha-Indol-3-yl-acetic acid
DTXCID70738
Indole-3-acetic acid (8CI)
INDOLEACETIC ACID [MI]
IES cpd
3Indoleacetic acid
Indole3acetic acid
Indol3ylacetic acid
BetaIndoleacetic acid
Acetic acid, indolyl
1HIndole3acetic acid
BetaIndolylacetic acid
3(Carboxymethyl)indole
Kyselina 3indolyloctova
OmegaSkatole carboxylic acid
3Indolylmethylcarboxylic acid
1HIndole3acetic acid (9CI)
INDOLE ACETIC ACID [INCI]
Inchi=1/c10h9no2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11h,5h2,(h,12,13
Auxin
IAA
Indoleacetate
(indol-3-yl)acetate
MFCD00005636
(1H-Indol-3-yl)acetic acid
.alpha.-IAA
.beta.-IAA
3-indole acetic acid
.beta.-Indoleacetic acid
.beta.-Indolylacetic acid
.beta.-Indole-3-acetic acid
CHEMBL82411
.omega.-Skatole carboxylic acid
.alpha.-Indol-3-yl-acetic acid
NSC3787
3-indoleacetate
(1H-indol-3-yl)acetate
CAS-87-51-4
IES
SMR000471855
Indole 3-acetic acid
3-indolyl acetic acid
UNII-6U1S09C61L
Alpha-IAA
Beta-IAA
IAC
Indole-3acetic acid
Indole-3-acetic-acid
3-indolyl-acetic acid
Acid, 6
Indole-3-acetic-t acid
1H-indol-3-acetic acid
Maybridge1_006755
Indole, 3-carboxymethyl-
1H-Indole 3-acetic acid
Bmse000177
3-Indoleacetic acid, 98%
3-Indoleacetic acid, 99%
Oprea1_602123
SCHEMBL26344
MLS001066408
MLS001331664
MLS001332399
MLS001332400
3-Indolylmethylcarboxylic acid
WLN: T56 BMJ D1VQ
[3H]-IAA
3-Indolyl acetic acid 100 microg/mL in Acetonitrile
Acetic acid, 2-(3-indolyl)-
HMS560L01
2-(1H-indol-3-yl)-acetic acid
HMS2269G24
HMS3604M04
BCP26623
MSK24053
Tox21_202284
Tox21_302731
BBL009348
BDBM50201883
CCG-51070
S4799
STK397461
AKOS000119890
1H-Indole-3-acetic-a-t acid (9CI)
AC-2974
CG-0522
CS-6287
DB07950
FI09866
SDCCGMLS-0066204.P001
3-Indoleacetic acid, >=98.0% (T)
NCGC00247039-01
NCGC00247039-02
NCGC00247039-07
NCGC00256391-01
NCGC00259833-01
HY-18569
SY003464
DB-011566
EU-0099905
I0022
NS00014849
3-Indoleacetic acid, technical, >=95% (T)
EN300-17303
C00954
Q411208
SR-01000596909
3-Indoleacetic acid, SAJ special grade, >=98.5%
IS_INDOLE-2,4,5,6,7-D5-3-ACETIC ACID
SR-01000596909-1
SR-01000596909-2
Z56913182
2-(3-Indolyl)acetic acid 3-(Carboxymethyl)-1H-indole
3-Indoleacetic acid, PESTANAL(R), analytical standard
F0722-8837
0A0524AE-D755-4E91-A73A-2AD867FE676A
3-Indoleacetic acid, plant cell culture tested, crystalline
- Othman A, Amen Y, et al. (2021). A novel acylated flavanol tetraglycoside and rare oleanane saponins with a unique acetal-linked dicarboxylic acid substituent from the xero-halophyte Bassia indica. Fitoterapia, 2021, 152, 104907. [View] [PubMed]
- El-Hawary S.S, Sayed A.M, et al. (2017). Secondary metabolites from fungal endophytes of Solanum nigrum. Natural product research, 2017, 31(21), 2568-2571. [View] [PubMed]
Pubchem:
802
Cas:
87-51-4
Gnps:
CCMSLIB00005744973
Zinc:
ZINC000000083860
Kegg Ligand:
C00954
Chebi:
16411
Nmrshiftdb2:
20097589
Metabolights:
MTBLC16411
Chembl:
CHEMBL82411
Comptox:
DTXSID5020738
Drugbank:
DB07950
Pdb Ligand:
IAC
Bindingdb:
50201883
CPRiL:
9814
SMILES: c1c[nH]c(c12)cccc2
Level: 0
Mol. Weight: 175.19 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.15
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.22
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.27
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.69
- Plasma Protein Binding
- 26.75
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- 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
- 7.28
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.05
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.36
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.92
- 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
- 1.79
- Rat (Acute)
- 2.04
- Rat (Chronic Oral)
- 2.54
- Fathead Minnow
- 3.89
- 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
- 330.57
- Hydration Free Energy
- -9.86
- Log(D) at pH=7.4
- -1.37
- Log(P)
- 1.46
- Log S
- -2.32
- Log(Vapor Pressure)
- -6.28
- Melting Point
- 175.74
- pKa Acid
- 4.54
- pKa Basic
- 6.36
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.9760 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9641 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9027 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8864 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.8720 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8714 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8460 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.8405 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.8381 |
| 4-chlorobenzoyl CoA ligase | Q8GN86 | Q8GN86_9BURK | Alcaligenes sp. AL3007 | 3 | 0.8253 |
| Kynurenine--oxoglutarate transaminase 1 | Q16773 | KAT1_HUMAN | Homo sapiens | 3 | 0.8172 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.8162 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8106 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.8085 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.8082 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.8081 |
| 4-chlorobenzoyl CoA ligase | Q8GN86 | Q8GN86_9BURK | Alcaligenes sp. AL3007 | 3 | 0.8035 |
| 4-chlorobenzoyl CoA ligase | Q8GN86 | Q8GN86_9BURK | Alcaligenes sp. AL3007 | 3 | 0.8034 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7934 |
| cAMP-dependent protein kinase catalytic subunit alpha | P17612 | KAPCA_HUMAN | Homo sapiens | 2 | 0.7713 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 2 | 0.7704 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 2 | 0.7633 |
| Cytochrome P450 2A6 | P11509 | CP2A6_HUMAN | Homo sapiens | 3 | 0.7630 |
| Carbonic anhydrase 13 | Q8N1Q1 | CAH13_HUMAN | Homo sapiens | 3 | 0.7628 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 3 | 0.7619 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7618 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 2 | 0.7587 |
| Mandelate racemase | P11444 | MANR_PSEPU | Pseudomonas putida | 2 | 0.7584 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7583 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7570 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7563 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7542 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7522 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7453 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7436 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7411 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7383 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.7345 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7342 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 2 | 0.7339 |
| Cytosol aminopeptidase | P00727 | AMPL_BOVIN | Bos taurus | 2 | 0.7338 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7323 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7320 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7316 |
| Benzoylformate decarboxylase | P20906 | MDLC_PSEPU | Pseudomonas putida | 3 | 0.7314 |
| Purine nucleoside phosphorylase DeoD-type 1 | Q9KPM0 | DEOD1_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7310 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7297 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7293 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7278 |
| Cyclic AMP receptor protein | Q5SID7 | CRP_THET8 | Thermus thermophilus | 2 | 0.7278 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7277 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7256 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7255 |
| Tryptophan synthase alpha chain | P00929 | TRPA_SALTY | Salmonella typhimurium | 3 | 0.7246 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7242 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7220 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7196 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7176 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7169 |
| L-lactate dehydrogenase (cytochrome) | P00175 | CYB2_YEAST | Saccharomyces cerevisiae | 3 | 0.7163 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7154 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7153 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7143 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 2 | 0.7134 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7134 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7125 |
| Prenyltransferase | Q4R2T2 | Q4R2T2_STRC1 | Streptomyces sp | 2 | 0.7124 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7115 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 2 | 0.7108 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7107 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7103 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7094 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7092 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7085 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7064 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7062 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7059 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7053 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7052 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7036 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7028 |
| Thiazole tautomerase | P25053 | TENI_BACSU | Bacillus subtilis | 2 | 0.7022 |
| Ceramide transfer protein | Q9Y5P4 | CERT_HUMAN | Homo sapiens | 2 | 0.7022 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7017 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7017 |
| Tyrosine 3-monooxygenase | P04177 | TY3H_RAT | Rattus norvegicus | 3 | 0.7009 |