NP-MRD: Showing NP-Card for 3-(prop-2-en-1-yl)benzene-1,2-diol (NP0188296)

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Record Information

Version

2.0

Created at

2022-09-04 04:36:28 UTC

Updated at

2022-09-04 04:36:28 UTC

NP-MRD ID

NP0188296

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(prop-2-en-1-yl)benzene-1,2-diol

Description

Allylpyrocatechol belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3-(prop-2-en-1-yl)benzene-1,2-diol is found in Piper betle. 3-(prop-2-en-1-yl)benzene-1,2-diol was first documented in 2020 (PMID: 32801638). Based on a literature review a small amount of articles have been published on Allylpyrocatechol (PMID: 33640995) (PMID: 33513803) (PMID: 32741921) (PMID: 32155466).

Structure

MOL 3D MOL SDF PDB SMILES InChI

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₀O₂

Average Mass

150.1770 Da

Monoisotopic Mass

150.06808 Da

IUPAC Name

3-(prop-2-en-1-yl)benzene-1,2-diol

Traditional Name

3-(prop-2-en-1-yl)benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

OC1=C(O)C(CC=C)=CC=C1

InChI Identifier

InChI=1S/C9H10O2/c1-2-4-7-5-3-6-8(10)9(7)11/h2-3,5-6,10-11H,1,4H2

InChI Key

PARWTEYYJSDGQM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Piper betle	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.46	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.31 m³·mol⁻¹	ChemAxon
Polarizability	15.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

257736

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

292101

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Okonogi S, Phumat P, Khongkhunthian S: Enhancement of aqueous solubility and antibiofilm activity of 4-allylpyrocatechol by polymeric micelles. Bioprocess Biosyst Eng. 2021 Jun;44(6):1289-1300. doi: 10.1007/s00449-020-02501-7. Epub 2021 Feb 27. [PubMed:33640995 ]
Okonogi S, Phumat P, Khongkhunthian S, Chaijareenont P, Rades T, Mullertz A: Development of Self-Nanoemulsifying Drug Delivery Systems Containing 4-Allylpyrocatechol for Treatment of Oral Infections Caused by Candida albicans. Pharmaceutics. 2021 Jan 27;13(2):167. doi: 10.3390/pharmaceutics13020167. [PubMed:33513803 ]
Kurnia D, Hutabarat GS, Windaryanti D, Herlina T, Herdiyati Y, Satari MH: Potential Allylpyrocatechol Derivatives as Antibacterial Agent Against Oral Pathogen of S. sanguinis ATCC 10,556 and as Inhibitor of MurA Enzymes: in vitro and in silico Study. Drug Des Devel Ther. 2020 Jul 27;14:2977-2985. doi: 10.2147/DDDT.S255269. eCollection 2020. [PubMed:32801638 ]
Tamura S, Miyoshi A, Kawano T, Horii T, Itagaki S, Murakami N: Structure-Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from Piper betle. Chem Pharm Bull (Tokyo). 2020;68(8):784-790. doi: 10.1248/cpb.c20-00294. [PubMed:32741921 ]
Phumat P, Khongkhunthian S, Wanachantararak P, Okonogi S: Comparative inhibitory effects of 4-allylpyrocatechol isolated from Piper betle on Streptococcus intermedius, Streptococcus mutans, and Candida albicans. Arch Oral Biol. 2020 May;113:104690. doi: 10.1016/j.archoralbio.2020.104690. Epub 2020 Mar 4. [PubMed:32155466 ]
LOTUS database [Link]

Showing NP-Card for 3-(prop-2-en-1-yl)benzene-1,2-diol (NP0188296)

MOL for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

3D MOL for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

3D SDF for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

3D-SDF for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

PDB for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

3D PDB for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

SMILES for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

INCHI for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

Structure for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)

3D Structure for NP0188296 (3-(prop-2-en-1-yl)benzene-1,2-diol)