NP-MRD: Showing NP-Card for Penicillic acid (NP0006402)

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Record Information

Version

2.0

Created at

2020-12-09 03:25:40 UTC

Updated at

2021-07-15 16:54:42 UTC

NP-MRD ID

NP0006402

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penicillic acid

Provided By

NPAtlas

Description

Penicillic acid is found in Penicillium puberulum, Pseudopenicillium megasporum and Purpureocillium lilacinum. Penicillic acid was first documented in 1936 (PMID: 16746037). Based on a literature review very few articles have been published on (2Z)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid (PMID: 33140404) (PMID: 32978257) (PMID: 32969130) (PMID: 32875235).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 22 21  0  0  0  0            999 V2000
   -3.0196    1.2015   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9955    0.3267   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009   -0.9779   -0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7580    0.7702    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7295    1.9840    0.8420 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5069    0.0998    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704   -1.1248    0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1094   -1.7247    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259   -1.0490    0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4129   -2.9987   -0.1448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5902    0.7628    1.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1956    1.8962    0.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9222    2.1933    0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9983    0.9713   -0.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2393   -1.8408   -0.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3941   -0.9855   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410   -1.2098   -1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0442   -1.7406   -0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2919   -3.2142   -0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147    2.2006    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6508    1.7218   -0.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856    2.7377    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  3 15  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  7 18  1  0  0  0  0
 10 19  1  0  0  0  0
 12 20  1  0  0  0  0
 12 21  1  0  0  0  0
 12 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006402

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/OC([H])([H])[H])C(=O)C(=C([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4-

> <INCHI_KEY>
VOUGEZYPVGAPBB-XQRVVYSFSA-N

> <FORMULA>
C8H10O4

> <MOLECULAR_WEIGHT>
170.164

> <EXACT_MASS>
170.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.72667570249424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.0347243956666672

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6046990837275223

> <JCHEM_PKA_STRONGEST_BASIC>
-4.951997988463538

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
43.8815

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
penicillic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.020   1.202  -0.179  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.996   0.327  -0.205  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.301  -0.978  -0.813  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.758   0.770   0.355  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.730   1.984   0.842  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.507   0.100   0.484  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770  -1.125   0.083  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.109  -1.725   0.263  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.026  -1.049   0.815  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.413  -2.999  -0.145  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.590   0.763   1.082  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.196   1.896   0.518  0.00  0.00           C+0
HETATM   13  H   UNK     0      -2.922   2.193   0.242  0.00  0.00           H+0
HETATM   14  H   UNK     0      -3.998   0.971  -0.573  0.00  0.00           H+0
HETATM   15  H   UNK     0      -2.239  -1.841  -0.133  0.00  0.00           H+0
HETATM   16  H   UNK     0      -3.394  -0.986  -1.143  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.741  -1.210  -1.737  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.044  -1.741  -0.386  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.292  -3.214  -0.590  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.015   2.201   1.202  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.651   1.722  -0.468  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.486   2.738   0.484  0.00  0.00           H+0
CONECT    1    2   13   14                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   15   16   17                                             
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   19                                                       
CONECT   11    6   12                                                       
CONECT   12   11   20   21   22                                             
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    3                                                            
CONECT   16    3                                                            
CONECT   17    3                                                            
CONECT   18    7                                                            
CONECT   19   10                                                            
CONECT   20   12                                                            
CONECT   21   12                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2Z)-3-Methoxy-5-methyl-4-oxohexa-2,5-dienoate	Generator
Acid, penicillic	MeSH
Penicillic acid	MeSH
Penicillate	Generator

Chemical Formula

C₈H₁₀O₄

Average Mass

170.1640 Da

Monoisotopic Mass

170.05791 Da

IUPAC Name

(2Z)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid

Traditional Name

penicillic acid

CAS Registry Number

Not Available

SMILES

CO\C(=C/C(O)=O)C(=O)C(C)=C

InChI Identifier

InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4-

InChI Key

VOUGEZYPVGAPBB-XQRVVYSFSA-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
Penicillium puberulum	NPAtlas	16746037
Pseudopenicillium megasporum	LOTUS Database	35616633
Purpureocillium lilacinum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus alliaceus	KNApSAcK Database	22123792
Aspergillus cervinus	KNApSAcK Database	22123792
Aspergillus melleus	KNApSAcK Database	22123792
Aspergillus ochraceus	KNApSAcK Database	22123792
Aspergillus ostianus	KNApSAcK Database	22123792
Aspergillus quercinus	KNApSAcK Database	22123792
Aspergillus sclerotiorum	KNApSAcK Database	22123792
Aspergillus sulfureus	KNApSAcK Database	22123792
Aspergillus wentii	KNApSAcK Database	22123792
Malbranchea aurantiaca	KNApSAcK Database	22123792
Paecilomyces ehrlichii	KNApSAcK Database	22123792
Penicillium aurantio-virens	KNApSAcK Database	22123792
Penicillium baarnense	KNApSAcK Database	22123792
Penicillium canescens	KNApSAcK Database	22123792
Penicillium chrysogenurn	KNApSAcK Database	22123792
Penicillium cyclopium	KNApSAcK Database	22123792
Penicillium fenelliae	KNApSAcK Database	22123792
Penicillium griseum	KNApSAcK Database	22123792
Penicillium janthinellum	KNApSAcK Database	22123792
Penicillium lilacinum	KNApSAcK Database	22123792
Penicillium lividum	KNApSAcK Database	22123792
Penicillium madriti	KNApSAcK Database	22123792
Penicillium martensii	KNApSAcK Database	22123792
Penicillium olivino-viride	KNApSAcK Database	22123792
Penicillium palitans	KNApSAcK Database	22123792
Penicillium roqueforti	KNApSAcK Database	22123792
Penicillium simplicissimum	KNApSAcK Database	22123792
Penicillium suavolens	KNApSAcK Database	22123792
Penicillium thomii	KNApSAcK Database	22123792
Penicillium viridicatum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Branched fatty acid
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Unsaturated fatty acid
Acryloyl-group
Enone
Vinylogous ester
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	1.15	ALOGPS
logP	1.03	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.88 m³·mol⁻¹	ChemAxon
Polarizability	16.73 Å³	ChemAxon
Number of Rings	0	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

NPAtlas ID

NPA005768

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024006

Chemspider ID

1064791

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1268111

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Birkinshaw JH, Oxford AE, Raistrick H: Studies in the biochemistry of micro-organisms: Penicillic acid, a metabolic product of Penicillium puberulum Bainier and P. cylopium Westling. Biochem J. 1936 Mar;30(3):394-411. doi: 10.1042/bj0300394. [PubMed:16746037 ]
Guan W, You Y, Li J, Hong J, Wu H, Rao Y: Penicillic acid in fruits: method development, validation by liquid chromatography-tandem mass spectrometry and survey in southern China. J Sci Food Agric. 2021 May;101(7):2779-2787. doi: 10.1002/jsfa.10906. Epub 2020 Nov 20. [PubMed:33140404 ]
Onodera T, Momose I, Adachi H, Yamazaki Y, Sawa R, Ohba SI, Kawada M: Human pancreatic cancer cells under nutrient deprivation are vulnerable to redox system inhibition. J Biol Chem. 2020 Dec 4;295(49):16678-16690. doi: 10.1074/jbc.RA120.013893. Epub 2020 Sep 25. [PubMed:32978257 ]
Luciano-Rosario D, Keller NP, Jurick WM 2nd: Penicillium expansum: biology, omics, and management tools for a global postharvest pathogen causing blue mould of pome fruit. Mol Plant Pathol. 2020 Nov;21(11):1391-1404. doi: 10.1111/mpp.12990. Epub 2020 Sep 23. [PubMed:32969130 ]
Hu HC, Li CY, Tsai YH, Yang DY, Wu YC, Hwang TL, Chen SL, Fulop F, Hunyadi A, Yen CH, Cheng YB, Chang FR: Secondary Metabolites and Bioactivities of Aspergillus ochraceopetaliformis Isolated from Anthurium brownii. ACS Omega. 2020 Aug 14;5(33):20991-20999. doi: 10.1021/acsomega.0c02489. eCollection 2020 Aug 25. [PubMed:32875235 ]

Showing NP-Card for Penicillic acid (NP0006402)

MOL for NP0006402 (Penicillic acid)

3D MOL for NP0006402 (Penicillic acid)

3D SDF for NP0006402 (Penicillic acid)

3D-SDF for NP0006402 (Penicillic acid)

PDB for NP0006402 (Penicillic acid)

3D PDB for NP0006402 (Penicillic acid)

SMILES for NP0006402 (Penicillic acid)

INCHI for NP0006402 (Penicillic acid)

Structure for NP0006402 (Penicillic acid)

3D Structure for NP0006402 (Penicillic acid)