NP-MRD: Showing NP-Card for Phenol A (NP0076965)

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Record Information

Version

2.0

Created at

2022-04-28 22:08:49 UTC

Updated at

2024-09-03 04:19:28 UTC

NP-MRD ID

NP0076965

Natural Product DOI

https://doi.org/10.57994/1767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenol A

Description

CHEMBL444472 belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Phenol A is found in Penicillium citrinum and Penicillium citrinum B-57u. Based on a literature review very few articles have been published on CHEMBL444472.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    1.0169    1.5397    1.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399    0.6996    0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653    0.5345    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    1.1624    1.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8777   -0.2535   -0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029   -0.8872   -1.5234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1490   -1.6728   -2.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -0.7155   -1.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    0.0533   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102    0.1785    0.4344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4541   -0.9996    1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722    0.2442   -0.6101 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4553   -0.8614   -1.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3698    0.5766    0.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7122    1.1485    2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0464    1.5588    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3830    2.5726    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900    1.7527    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137   -0.3504   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -1.7929   -2.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1359   -1.2735   -1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    1.0691    1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7808   -0.9504    2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982   -0.7793    1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547   -1.9297    0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9486    1.1738   -1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3829   -1.8876   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5776   -0.7359   -1.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9954   -0.6841   -2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144    1.5095    0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 12 10  1  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
  2  9  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 12 26  1  6
 14 30  1  0
 10 22  1  1
 11 23  1  0
 11 24  1  0
 11 25  1  0
  8 21  1  0
  7 20  1  0
  5 19  1  0
  4 18  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
M  END


  Mrv1652304292200082D          

 14 14  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  1  0  0  0
  7 11  1  6  0  0  0
  4 12  1  0  0  0  0
  3 13  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@@H](C)C1=CC(O)=CC(O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O3/c1-6(8(3)12)10-4-9(13)5-11(14)7(10)2/h4-6,8,12-14H,1-3H3/t6-,8-/m1/s1

> <INCHI_KEY>
ZYUVGYBAPZYKSA-HTRCEHHLSA-N

> <FORMULA>
C11H16O3

> <MOLECULAR_WEIGHT>
196.246

> <EXACT_MASS>
196.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.29024720845822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2S,3R)-3-hydroxybutan-2-yl]-4-methylbenzene-1,3-diol

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
2.182395850666667

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.985772768325258

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.636149168685039

> <JCHEM_PKA_STRONGEST_BASIC>
-2.732201154213537

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
55.52229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2S,3R)-3-hydroxybutan-2-yl]-4-methylbenzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    4                                                            
CONECT   13    3                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆O₃

Average Mass

196.2460 Da

Monoisotopic Mass

196.10994 Da

IUPAC Name

5-[(2S,3R)-3-hydroxybutan-2-yl]-4-methylbenzene-1,3-diol

Traditional Name

5-[(2S,3R)-3-hydroxybutan-2-yl]-4-methylbenzene-1,3-diol

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@@H](C)C1=CC(O)=CC(O)=C1C

InChI Identifier

InChI=1S/C11H16O3/c1-6(8(3)12)10-4-9(13)5-11(14)7(10)2/h4-6,8,12-14H,1-3H3/t6-,8-/m1/s1

InChI Key

ZYUVGYBAPZYKSA-HTRCEHHLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Penicillium citrinum	LOTUS Database	35616633
Penicillium citrinum B-57u	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Resorcinol
P-cresol
O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	1.36	ALOGPS
logP	2.18	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.52 m³·mol⁻¹	ChemAxon
Polarizability	21.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

9292098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11116966

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1080/10286020.2024.2311140

Showing NP-Card for Phenol A (NP0076965)

MOL for NP0076965 (Phenol A)

3D MOL for NP0076965 (Phenol A)

3D SDF for NP0076965 (Phenol A)

3D-SDF for NP0076965 (Phenol A)

PDB for NP0076965 (Phenol A)

3D PDB for NP0076965 (Phenol A)

SMILES for NP0076965 (Phenol A)

INCHI for NP0076965 (Phenol A)

Structure for NP0076965 (Phenol A)

3D Structure for NP0076965 (Phenol A)