NP-MRD: Showing NP-Card for (3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid (NP0183615)

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Record Information

Version

2.0

Created at

2022-09-03 22:33:15 UTC

Updated at

2022-09-03 22:33:15 UTC

NP-MRD ID

NP0183615

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid

Description

Pulvilloric acid, also known as pulvillate, belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid is found in Penicillium simplicissimum. Based on a literature review very few articles have been published on Pulvilloric acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -4.6384   -0.4863   -1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7386   -0.2556    0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2401    1.1176    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7996    1.2895    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9257    0.2975    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738    0.4263    0.4804 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2864   -0.6234    1.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090   -0.5696    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6531   -0.9242    1.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652   -0.8712    1.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9758   -1.2082    2.1059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -0.4252   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8557   -0.3863   -0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7375   -0.7255    0.4076 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2208    0.0335   -1.6798 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4828   -0.0741   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    0.3448   -2.1465 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657   -0.1256   -0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900    0.2252   -1.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533    0.1726   -0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8461    0.4494   -1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -1.2656   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984   -0.7947   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178   -1.0213    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8162   -0.2839    0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8977    1.8671    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3414    1.2574    1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740    2.3293    0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895    1.1372   -0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2194   -0.7413    0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835    0.5208    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0715    1.4134    0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175   -1.6160    0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1506   -0.4360    2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3506   -1.2508    2.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2840    1.0157   -1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1176   -0.3697   -2.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3617    0.5570   -2.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  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
 10 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 12 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20  6  1  0
 18  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  0
  7 34  1  0
  9 35  1  0
 15 36  1  0
 17 37  1  0
 19 38  1  0
M  END


  Mrv1652309042200332D          

 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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183615

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H]1CC2=CC(=O)C(C(O)=O)=C(O)C2=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-2-3-4-5-10-6-9-7-12(16)13(15(18)19)14(17)11(9)8-20-10/h7-8,10,17H,2-6H2,1H3,(H,18,19)/t10-/m0/s1

> <INCHI_KEY>
KPYJKXACXGIDBE-JTQLQIEISA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.304

> <EXACT_MASS>
278.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.99296346945913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-8-hydroxy-6-oxo-3-pentyl-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid

> <JCHEM_LOGP>
1.904657440333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.219486061409633

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4723417446045945

> <JCHEM_PKA_STRONGEST_BASIC>
-4.78742795931797

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
74.75179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    8   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    6                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Pulvillate	Generator
Pulvillic acid	Generator

Chemical Formula

C₁₅H₁₈O₅

Average Mass

278.3040 Da

Monoisotopic Mass

278.11542 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCCC[C@H]1CC2=CC(=O)C(C(O)=O)=C(O)C2=CO1

InChI Identifier

InChI=1S/C15H18O5/c1-2-3-4-5-10-6-9-7-12(16)13(15(18)19)14(17)11(9)8-20-10/h7-8,10,17H,2-6H2,1H3,(H,18,19)/t10-/m0/s1

InChI Key

KPYJKXACXGIDBE-JTQLQIEISA-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
Penicillium simplicissimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Vinylogous acid
Cyclic ketone
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.9	ChemAxon
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00053719

Chemspider ID

78442415

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101281386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid (NP0183615)

MOL for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

3D MOL for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

3D SDF for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

3D-SDF for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

PDB for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

3D PDB for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

SMILES for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

INCHI for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

Structure for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)

3D Structure for NP0183615 ((3s)-8-hydroxy-6-oxo-3-pentyl-3,4-dihydro-2-benzopyran-7-carboxylic acid)