Dihydroferulic Acid

Details

• Internal ID: a9cb1dcf-cc24-47f1-98b8-77def9318ad5
• Taxonomy: Phenylpropanoids and polyketides > Phenylpropanoic acids
• IUPAC Name: 3-(4-hydroxy-3-methoxyphenyl)propanoic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)CCC(=O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CCC(=O)O)O
• InChI: InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
• InChI Key: BOLQJTPHPSDZHR-UHFFFAOYSA-N
• Popularity: 73 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.20 g/mol
• Exact Mass: 196.07355886 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.42
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 3-(4-Hydroxy-3-methoxyphenyl)propionic acid
• 3-(4-Hydroxy-3-methoxyphenyl)propanoic acid
• dihydroferulic acid
• Hydroferulic acid
• Dihydroconiferylic acid
• 3-(4-Hydroxymethyl)propionic acid
• Benzenepropanoic acid, 4-hydroxy-3-methoxy-
• UNII-O01RNC700M
• O01RNC700M
• .beta.-(4-Hydroxy-3-methoxyphenyl)propionic acid
• EINECS 214-489-5
• 4-Hydroxy-3-methoxy-benzenepropanoic acid
• 3-(4-hydroxy-3-methoxy-phenyl)propanoic acid
• Hydroferulic
• Dihydro Ferulic Acid
• bmse010023
• SCHEMBL347918
• 3-METHOXYPHLORETIC ACID
• CHEMBL387842
• CHEBI:86612
• AMY3788
• DTXSID90150427
• HY-N7080
• MFCD00016558
• s5135
• STK662207
• AKOS000166726
• CCG-266549
• DS-6102
• Benzenepropanoic acid, 4-hydroxy-3-methoxy
• 3-(3-methoxy-4-hydroxyphenyl)propanoic acid
• CS-0030749
• FT-0613672
• H1180
• 3-(4-hydroxy-3-methoxy-phenyl)propionic acid
• 3-(4-hydroxy-3-methoxyphenyl)-propionic acid
• 3-(4-hydroxy-3-methoxy-phenyl)-propionic acid
• 3-(4-Hydroxy-3-methoxyphenyl)propanoic acid #
• 3-METHOXY-4-HYDROXYPHENYLPROPIONIC ACID
• A50645
• EN300-111281
• (4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID
• HYDROCINNAMIC ACID, 4-HYDROXY-3-METHOXY-
• J-002977
• .BETA.-3-METHOXY-4-HYDROXYPHENYLPROPIONIC ACID
• Q10395564
• F1905-6428
• Z317038020
• 3-(4-Hydroxy-3-methoxyphenyl)propionic acid, >=96.0% (T)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9738	97.38%
Caco-2	+	0.5690	56.90%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.9066	90.66%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.9328	93.28%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8433	84.33%
P-glycoprotein inhibitior	-	0.9919	99.19%
P-glycoprotein substrate	-	0.9182	91.82%
CYP3A4 substrate	-	0.5995	59.95%
CYP2C9 substrate	+	0.5641	56.41%
CYP2D6 substrate	-	0.7778	77.78%
CYP3A4 inhibition	-	0.9721	97.21%
CYP2C9 inhibition	-	0.8741	87.41%
CYP2C19 inhibition	-	0.8206	82.06%
CYP2D6 inhibition	-	0.9630	96.30%
CYP1A2 inhibition	-	0.7839	78.39%
CYP2C8 inhibition	+	0.8132	81.32%
CYP inhibitory promiscuity	-	0.9385	93.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7815	78.15%
Carcinogenicity (trinary)	Non-required	0.7065	70.65%
Eye corrosion	-	0.8919	89.19%
Eye irritation	+	0.9850	98.50%
Skin irritation	+	0.5480	54.80%
Skin corrosion	-	0.8850	88.50%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6019	60.19%
Micronuclear	-	0.6065	60.65%
Hepatotoxicity	-	0.7089	70.89%
skin sensitisation	-	0.7868	78.68%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8831	88.31%
Acute Oral Toxicity (c)	III	0.7724	77.24%
Estrogen receptor binding	-	0.6565	65.65%
Androgen receptor binding	-	0.7090	70.90%
Thyroid receptor binding	-	0.8262	82.62%
Glucocorticoid receptor binding	-	0.7649	76.49%
Aromatase binding	-	0.9130	91.30%
PPAR gamma	-	0.7731	77.31%
Honey bee toxicity	-	0.9646	96.46%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7604	76.04%
Fish aquatic toxicity	-	0.3644	36.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.34%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.31%	91.11%
CHEMBL1255126	O15151	Protein Mdm4	95.59%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.23%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.24%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.42%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.65%	94.45%
CHEMBL2535	P11166	Glucose transporter	86.45%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.67%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.35%	95.50%
CHEMBL4208	P20618	Proteasome component C5	82.95%	90.00%

Plants that contains it

• Achlys triphylla
• Ailanthus altissima
• Albizia procera
• Artemisia giraldii
• Bulbophyllum protractum
• Bulbophyllum vaginatum
• Calystegia pubescens
• Colchicum kotschyi
• Cypripedium calceolus
• Dianthus superbus
• Diospyros japonica
• Hortonia floribunda
• Lactuca sativa
• Lampranthus sociorum
• Melicope semecarpifolia
• Morus alba
• Perymenium mendezii
• Picea glauca
• Pongamia pinnata
• Protium tonkinense
• Prunella vulgaris
• Pseudostellaria heterophylla
• Seriphidium porrectum
• Stellaria dichotoma
• Tarchonanthus camphoratus
• Uncaria rhynchophylla
• Zingiber officinale

Cross-Links

• PubChem: 14340
• NPASS: NPC194416
• LOTUS: LTS0187038
• wikiData: Q10395564