3,4-Dihydroxyphenylacetic acid

Details

• Internal ID: a2d79a53-b65a-4716-a5cc-97f793224041
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 2-(3,4-dihydroxyphenyl)acetic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CC(=O)O)O)O
• InChI: InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
• InChI Key: CFFZDZCDUFSOFZ-UHFFFAOYSA-N
• Popularity: 8,195 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15 g/mol
• Exact Mass: 168.04225873 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 102-32-9
• Dopac
• 2-(3,4-DIHYDROXYPHENYL)ACETIC ACID
• Homoprotocatechuic acid
• Dopacetic acid
• 3,4-Dihydroxybenzeneacetic acid
• Benzeneacetic acid, 3,4-dihydroxy-
• Dihydroxyphenylacetic acid
• (3,4-DIHYDROXYPHENYL)ACETIC ACID
• 3,4-dihydroxyphenylacetate
• Homoprotocatechuate
• Acetic acid, (3,4-dihydroxyphenyl)-
• 3,4-Dihydroxy-phenylacetic acid
• BA 2773
• 3,4-DIHYDROXYPHENYLACETICACID
• MFCD00004338
• CCRIS 3765
• EINECS 203-024-1
• Lopac-D-9128
• NSC 73191
• UNII-KEX5N0R4N5
• BRN 2211017
• KEX5N0R4N5
• 3,4-DHPOP
• AI3-52339
• MLS001056737
• 3,4-dihydroxyphenyl acetic acid
• CHEBI:41941
• NSC-73191
• 3,4-DIHYDROXYPHENYLCAETIC ACID
• SMR000326727
• 4-Carboxymethylcatechol
• DHY
• 3,4-Dihydroxyphenylacetate, XV
• Benzene-2,3,6-d3-acetic-a,a-d2 acid, 4,5-dihydroxy-
• 2-(3,4-dihydroxyphenyl)acetate
• Dopacetate
• 3pcn
• Dihydroxyphenylacetate
• 1ai4
• Catechol-4-acetic Acid
• cid_547
• 4-Carboxymethylpyrocatechol
• bmse000329
• D04UPU
• Pyrocatechol-4-acetic Acid
• 3,4-Dihydroxybenzeneacetate
• CHEMBL1284
• NCIOpen2_000518
• Lopac0_000414
• SCHEMBL36348
• 3,4-dihydroxyphenyleddikesyre
• Benzeneacetic acid,4-dihydroxy-
• DTXSID9074430
• Acetic acid,4-dihydroxyphenyl)-
• BDBM52946
• HMDB01336
• 3,4-dihydroxy-Benzeneacetic acid
• 3,4-dihydroxyl phenylacetic acid
• HMS2233I20
• HMS3261C10
• HMS3373A01
• KUC106695N
• KUC106697N
• (3,4-dihydroxyphenyl)-Acetic acid
• NSC73191
• Tox21_500414
• s5639
• 3,4-Dihydroxyphenylacetic acid, 98%
• AKOS015890264
• AC-5292
• CCG-204506
• CS-W001080
• DB01702
• Dopac/(3,4-dihydroxyphenyl)-aceticaci
• HY-W001080
• LP00414
• RS-1018
• SDCCGSBI-0050399.P002
• Acetic acid, (3,4-dihydroxyphenyl)-,
• NCGC00015381-01
• NCGC00015381-02
• NCGC00015381-03
• NCGC00015381-04
• NCGC00015381-05
• NCGC00015381-06
• NCGC00093838-01
• NCGC00093838-02
• NCGC00093838-03
• NCGC00261099-01
• HAA
• KSC-11-207-5
• KSC-11-207-8
• SY015718
• 2-[3,4-bis(oxidanyl)phenyl]ethanoic acid
• AM20020093
• D1283
• EU-0100414
• FT-0614331
• C01161
• D 9128
• EN300-111909
• A800559
• SR-01000075841
• 3,4-Dihydroxyphenylacetic acid, analytical standard
• J-000672
• Q4634071
• SR-01000075841-1
• Z1255438427
• 47115C80-8C82-419A-BC51-B10A2CB7FE8F
• InChI=1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9073	90.73%
Caco-2	+	0.6587	65.87%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8378	83.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9608	96.08%
OATP1B3 inhibitior	+	0.9623	96.23%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9613	96.13%
P-glycoprotein inhibitior	-	0.9879	98.79%
P-glycoprotein substrate	-	0.9880	98.80%
CYP3A4 substrate	-	0.7847	78.47%
CYP2C9 substrate	+	0.8012	80.12%
CYP2D6 substrate	-	0.8218	82.18%
CYP3A4 inhibition	-	0.9383	93.83%
CYP2C9 inhibition	-	0.9649	96.49%
CYP2C19 inhibition	-	0.9743	97.43%
CYP2D6 inhibition	-	0.9257	92.57%
CYP1A2 inhibition	-	0.9513	95.13%
CYP2C8 inhibition	-	0.9088	90.88%
CYP inhibitory promiscuity	-	0.9593	95.93%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7900	79.00%
Carcinogenicity (trinary)	Non-required	0.6842	68.42%
Eye corrosion	-	0.8875	88.75%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.7875	78.75%
Skin corrosion	-	0.7449	74.49%
Ames mutagenesis	+	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8557	85.57%
Micronuclear	+	0.7077	70.77%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	+	0.8281	82.81%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.8194	81.94%
Acute Oral Toxicity (c)	III	0.7203	72.03%
Estrogen receptor binding	-	0.7853	78.53%
Androgen receptor binding	+	0.5275	52.75%
Thyroid receptor binding	-	0.7692	76.92%
Glucocorticoid receptor binding	-	0.6374	63.74%
Aromatase binding	-	0.7807	78.07%
PPAR gamma	+	0.5217	52.17%
Honey bee toxicity	-	0.9406	94.06%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.8595	85.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	39810.7 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	6309.6 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	7943.3 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	7943.3 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	501.2 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	3548.1 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	25118.9 nM; 15848.9 nM; 14125.4 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	1412.5 nM; 1412.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	23934.1 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	3548.1 nM	Potency	via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	22387.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.82%	91.11%
CHEMBL2216739	Q92523	Carnitine O-palmitoyltransferase 1, muscle isoform	93.78%	88.33%
CHEMBL2581	P07339	Cathepsin D	93.04%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.54%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.92%	99.15%
CHEMBL4208	P20618	Proteasome component C5	83.28%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.80%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.78%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.70%	94.45%
CHEMBL3194	P02766	Transthyretin	82.56%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.73%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	80.39%	90.17%

Plants that contains it

• Aloe africana
• Aloe ferox
• Aloe spicata
• Aloe vera
• Olea europaea
• Secamone afzelii
• Tragopogon pratensis
• Vanilla planifolia

Cross-Links

• PubChem: 547
• NPASS: NPC4665
• ChEMBL: CHEMBL1284
• LOTUS: LTS0139020
• wikiData: Q4634071