NP-MRD: Showing NP-Card for Prelunularic acid (NP0061364)

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Record Information

Version

2.0

Created at

2022-04-28 06:10:56 UTC

Updated at

2022-04-28 06:10:56 UTC

NP-MRD ID

NP0061364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prelunularic acid

Description

Prelunularic acid, also known as prelunularate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Prelunularic acid is found in Conocephalum conicum, Marchanta polymorpha, Marchantia polymorpha and Plagiochila sciophila. Prelunularic acid was first documented in 1985 (PMID: 16664486). Based on a literature review very few articles have been published on Prelunularic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.6902   -3.4746   -0.1312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8490   -2.5122   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960   -2.8781    0.3907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2645   -1.1631   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4610   -0.1446   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0609   -0.1116    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.4211   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201    0.4187   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    1.5030    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0522    1.4662    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110    0.3390    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1199    0.3296    0.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2946   -0.7579   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -0.7216   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647    1.1952   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3818    1.2243    0.2123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1858    0.5711    1.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3229    0.3590   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6792   -0.9646   -0.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2882   -1.9409   -1.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -3.2532    1.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0682    0.6793    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3671   -1.0475    0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204   -0.2372   -1.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5462    1.4677   -1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    2.3694    0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4729    2.3293    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3278    0.0151    1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8687   -1.6444   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -1.5824   -1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917    1.1411   -1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422    2.0371   -0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7545    2.2486    0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7684    1.1625    2.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4326    0.8625   -1.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2905    0.2942   -0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  5 15  1  0
 15 16  1  0
 14  8  1  0
 17 34  1  0
 16 33  1  1
 18 35  1  0
 18 36  1  0
  3 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
M  END


  Mrv1652304282208102D          

 20 21  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    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    1.2375    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
    1.4289    0.8250    0.0000 C   0  0  2  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
    2.1434    1.2375    0.0000 O   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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  1  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC(=O)C(C(O)=O)=C(CCC2=CC=C(O)C=C2)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c16-11-5-2-9(3-6-11)1-4-10-7-12(17)8-13(18)14(10)15(19)20/h2-3,5-6,12,16-17H,1,4,7-8H2,(H,19,20)/t12-/m0/s1

> <INCHI_KEY>
DWEBKCDBKMCKDE-LBPRGKRZSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.30815699794219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-6-oxocyclohex-1-ene-1-carboxylic acid

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
1.8051870283333333

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.29045528751711

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9448398969907745

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7967060903213117

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
72.4904

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-6-oxocyclohex-1-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14    9                                                       
CONECT   16   14                                                            
CONECT   17   10   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Prelunularate	Generator

Chemical Formula

C₁₅H₁₆O₅

Average Mass

276.2880 Da

Monoisotopic Mass

276.09977 Da

IUPAC Name

(4S)-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-6-oxocyclohex-1-ene-1-carboxylic acid

Traditional Name

(4S)-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-6-oxocyclohex-1-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC(=O)C(C(O)=O)=C(CCC2=CC=C(O)C=C2)C1

InChI Identifier

InChI=1S/C15H16O5/c16-11-5-2-9(3-6-11)1-4-10-7-12(17)8-13(18)14(10)15(19)20/h2-3,5-6,12,16-17H,1,4,7-8H2,(H,19,20)/t12-/m0/s1

InChI Key

DWEBKCDBKMCKDE-LBPRGKRZSA-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, 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
Conocephalum conicum	Plant	KNApSAcK
Marchanta polymorpha	-	KNApSAcK
Marchantia polymorpha	Plant	KNApSAcK
Plagiochila sciophila	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Monocyclic benzene moiety
Ketone
Secondary alcohol
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	1.57	ALOGPS
logP	1.81	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.49 m³·mol⁻¹	ChemAxon
Polarizability	28.31 Å³	ChemAxon
Number of Rings	2	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

C00015851

Chemspider ID

74179147

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100988753

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Imoto SA, Ohta Y: Intracellular Localization of Lunularic Acid and Prelunularic Acid in Suspension Cultured Cells of Marchantia polymorpha. Plant Physiol. 1985 Nov;79(3):751-5. doi: 10.1104/pp.79.3.751. [PubMed:16664486 ]

Showing NP-Card for Prelunularic acid (NP0061364)

MOL for NP0061364 (Prelunularic acid)

3D MOL for NP0061364 (Prelunularic acid)

3D SDF for NP0061364 (Prelunularic acid)

3D-SDF for NP0061364 (Prelunularic acid)

PDB for NP0061364 (Prelunularic acid)

3D PDB for NP0061364 (Prelunularic acid)

SMILES for NP0061364 (Prelunularic acid)

INCHI for NP0061364 (Prelunularic acid)

Structure for NP0061364 (Prelunularic acid)

3D Structure for NP0061364 (Prelunularic acid)