4-Allylbenzene-1,2-diol

Details

• Internal ID: 6a7a602d-fb23-4f6c-850f-961bee527f94
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 4-prop-2-enylbenzene-1,2-diol
• SMILES (Canonical): C=CCC1=CC(=C(C=C1)O)O
• SMILES (Isomeric): C=CCC1=CC(=C(C=C1)O)O
• InChI: InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2
• InChI Key: FHEHIXJLCWUPCZ-UHFFFAOYSA-N
• Popularity: 152 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17 g/mol
• Exact Mass: 150.068079557 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 1126-61-0
• Hydroxychavicol
• 4-allylbenzene-1,2-diol
• 4-allylcatechol
• 2-Hydroxychavicol
• 3,4-dihydroxy-allylbenzene
• 4-prop-2-enylbenzene-1,2-diol
• 1,2-Benzenediol, 4-(2-propenyl)-
• Desmethylisoeugenol
• CCRIS 1524
• FG58C4J9BR
• 4-(prop-2-en-1-yl)benzene-1,2-diol
• 4-(2-propenyl)-1,2-benzenediol
• Hydroxychavicol; 4-Allylpyrocatechol
• 4-allylbenzene-1,2-d
• Hydroxy chavicol
• P-ALLYLCATECHOL
• 4-Allyl-1,2-benzenediol
• UNII-FG58C4J9BR
• HYDROXYCHAVICOL, 2-
• HydroxychavicolHydroxychavicol
• SCHEMBL43300
• 1,2-Dihydroxy-4-allylbenzene
• 4-Allyl-1,2-dihydroxybenzene
• CHEMBL111134
• DTXSID20150112
• BCP29736
• HY-N1887
• BBL029399
• BDBM50267733
• MFCD01548379
• STK046904
• AKOS005384863
• CS-7492
• 4-Allylpyrocatechol, analytical standard
• AS-58835
• LS-172194
• A894552
• W-200844
• 4-Allylcatechol; 2-Hydroxychavicol pound>>Hydroxychavicol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	+	0.6928	69.28%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6996	69.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9358	93.58%
OATP1B3 inhibitior	+	0.9660	96.60%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9665	96.65%
P-glycoprotein inhibitior	-	0.9803	98.03%
P-glycoprotein substrate	-	0.9826	98.26%
CYP3A4 substrate	-	0.7554	75.54%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	+	0.3810	38.10%
CYP3A4 inhibition	-	0.7448	74.48%
CYP2C9 inhibition	-	0.6559	65.59%
CYP2C19 inhibition	-	0.7313	73.13%
CYP2D6 inhibition	-	0.8434	84.34%
CYP1A2 inhibition	-	0.6499	64.99%
CYP2C8 inhibition	-	0.7240	72.40%
CYP inhibitory promiscuity	+	0.5751	57.51%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6608	66.08%
Carcinogenicity (trinary)	Non-required	0.5443	54.43%
Eye corrosion	+	0.8122	81.22%
Eye irritation	+	0.9944	99.44%
Skin irritation	+	0.8238	82.38%
Skin corrosion	+	0.8790	87.90%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7444	74.44%
Micronuclear	+	0.5459	54.59%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	+	0.9743	97.43%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6308	63.08%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	-	0.7602	76.02%
Acute Oral Toxicity (c)	III	0.4953	49.53%
Estrogen receptor binding	-	0.5801	58.01%
Androgen receptor binding	-	0.5561	55.61%
Thyroid receptor binding	-	0.7789	77.89%
Glucocorticoid receptor binding	-	0.7461	74.61%
Aromatase binding	-	0.7304	73.04%
PPAR gamma	-	0.5674	56.74%
Honey bee toxicity	-	0.7688	76.88%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9598	95.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.89%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.83%	91.49%
CHEMBL3492	P49721	Proteasome Macropain subunit	89.56%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.12%	94.45%
CHEMBL4208	P20618	Proteasome component C5	85.61%	90.00%
CHEMBL2581	P07339	Cathepsin D	84.92%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.35%	96.09%
CHEMBL3194	P02766	Transthyretin	82.03%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.71%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	80.59%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.30%	95.56%

Plants that contains it

• Alpinia officinarum
• Artemisia pedemontana
• Artemisia sericea
• Benkara malabarica
• Calea cuneifolia
• Chamaecyparis formosensis
• Dracaena cambodiana
• Dracaena draco
• Dracocephalum moldavica
• Eucalyptus rubida
• Eurya japonica
• Hemionitis lemmonii
• Juniperus formosana
• Mucuna urens
• Murdannia triquetra
• Ozothamnus ferrugineus
• Phlomis nissolii
• Piper betle
• Piper marginatum
• Piper retrofractum
• Senecio subsessilis
• Stephania merrillii
• Styrax japonicus
• Tanacetum balsamitoides
• Verbascum spinosum
• Viburnum furcatum

Cross-Links

• PubChem: 70775
• NPASS: NPC109955
• ChEMBL: CHEMBL111134
• LOTUS: LTS0106385
• wikiData: Q72437390