NP-MRD: Showing NP-Card for Aspergillusic acid (NP0013445)

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Record Information

Version

2.0

Created at

2021-01-05 22:48:23 UTC

Updated at

2021-07-15 17:14:30 UTC

NP-MRD ID

NP0013445

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspergillusic acid

Provided By

NPAtlas

Description

Aspergillusic acid is found in Aspergillus. Aspergillusic acid was first documented in 2014 (PMID: 25375978). Based on a literature review very few articles have been published on 4-methoxy-3-(3-methylbut-3-en-1-yn-1-yl)benzoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119363D          

 28 28  0  0  0  0            999 V2000
    4.3881    0.1331    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5301   -0.8567    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846   -2.2963    0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -0.5497    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -0.2977    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621   -0.0101    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -0.9891   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7765   -0.7026   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7399   -1.7803   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619   -1.5211   -0.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101   -3.0924   -0.4760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146    0.6007   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540    1.5731    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065    1.2938    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551    2.2779    0.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    3.6115    0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363    1.1437    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4464   -0.0454    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366   -2.7342    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3885   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260   -2.8314   -0.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -2.0128   -0.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8429   -3.8849   -0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755    0.8284   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    2.5889    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6542    3.9693   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4577    4.2372    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316    3.7354    1.2075 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  3  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14  6  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  7 22  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 16 26  1  0  0  0  0
 16 27  1  0  0  0  0
 16 28  1  0  0  0  0
M  END


  Mrv1652306242119363D          

 28 28  0  0  0  0            999 V2000
    4.3881    0.1331    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5301   -0.8567    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846   -2.2963    0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -0.5497    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -0.2977    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621   -0.0101    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -0.9891   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7765   -0.7026   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7399   -1.7803   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9619   -1.5211   -0.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101   -3.0924   -0.4760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146    0.6007   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540    1.5731    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065    1.2938    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551    2.2779    0.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    3.6115    0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363    1.1437    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4464   -0.0454    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366   -2.7342    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3885   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260   -2.8314   -0.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -2.0128   -0.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8429   -3.8849   -0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755    0.8284   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    2.5889    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6542    3.9693   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4577    4.2372    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316    3.7354    1.2075 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  3  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14  6  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  7 22  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 16 26  1  0  0  0  0
 16 27  1  0  0  0  0
 16 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C(OC([H])([H])[H])C(C#CC(=C([H])[H])C([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O3/c1-9(2)4-5-10-8-11(13(14)15)6-7-12(10)16-3/h6-8H,1H2,2-3H3,(H,14,15)

> <INCHI_KEY>
BZUCIVANDDTNAW-UHFFFAOYSA-N

> <FORMULA>
C13H12O3

> <MOLECULAR_WEIGHT>
216.236

> <EXACT_MASS>
216.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.642039036248114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-3-(3-methylbut-3-en-1-yn-1-yl)benzoic acid

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.844364792666666

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.249055473310402

> <JCHEM_PKA_STRONGEST_BASIC>
-4.883180824141334

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
59.377600000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-3-(3-methylbut-3-en-1-yn-1-yl)benzoic 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       4.388   0.133   0.327  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.530  -0.857   0.285  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.985  -2.296   0.294  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.119  -0.550   0.229  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.941  -0.298   0.169  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.462  -0.010   0.094  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.417  -0.989  -0.091  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.777  -0.703  -0.164  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.740  -1.780  -0.360  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.962  -1.521  -0.425  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.310  -3.092  -0.476  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.215   0.601  -0.049  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.254   1.573   0.135  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.907   1.294   0.207  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.055   2.278   0.393  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.386   3.611   0.511  0.00  0.00           C+0
HETATM   17  H   UNK     0       4.036   1.144   0.319  0.00  0.00           H+0
HETATM   18  H   UNK     0       5.446  -0.045   0.369  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.837  -2.734   1.295  0.00  0.00           H+0
HETATM   20  H   UNK     0       5.017  -2.389  -0.052  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.326  -2.831  -0.428  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.100  -2.013  -0.183  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.843  -3.885  -0.170  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.276   0.828  -0.105  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.605   2.589   0.223  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.654   3.969  -0.503  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.458   4.237   0.926  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.232   3.735   1.208  0.00  0.00           H+0
CONECT    1    2   17   18                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   19   20   21                                             
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   23                                                       
CONECT   12    8   13   24                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15    6                                                  
CONECT   15   14   16                                                       
CONECT   16   15   26   27   28                                             
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    7                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   16                                                            
CONECT   27   16                                                            
CONECT   28   16                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-Methoxy-3-(3-methylbut-3-en-1-yn-1-yl)benzoate	Generator
Aspergillusate	Generator

Chemical Formula

C₁₃H₁₂O₃

Average Mass

216.2360 Da

Monoisotopic Mass

216.07864 Da

IUPAC Name

4-methoxy-3-(3-methylbut-3-en-1-yn-1-yl)benzoic acid

Traditional Name

4-methoxy-3-(3-methylbut-3-en-1-yn-1-yl)benzoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C=C(C=C1)C(O)=O)C#CC(C)=C

InChI Identifier

InChI=1S/C13H12O3/c1-9(2)4-5-10-8-11(13(14)15)6-7-12(10)16-3/h6-8H,1H2,2-3H3,(H,14,15)

InChI Key

BZUCIVANDDTNAW-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, 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
Aspergillus	NPAtlas	25375978

Chemical Taxonomy

Classification

Not classified

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	2.49	ALOGPS
logP	2.84	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.38 m³·mol⁻¹	ChemAxon
Polarizability	23.64 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

NPAtlas ID

NPA011245

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434891

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586221

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rukachaisirikul V, Rungsaiwattana N, Klaiklay S, Phongpaichit S, Borwornwiriyapan K, Sakayaroj J: gamma-Butyrolactone, cytochalasin, cyclic carbonate, eutypinic acid, and phenalenone derivatives from the soil fungus Aspergillus sp. PSU-RSPG185. J Nat Prod. 2014 Nov 26;77(11):2375-82. doi: 10.1021/np500324b. Epub 2014 Nov 6. [PubMed:25375978 ]

Showing NP-Card for Aspergillusic acid (NP0013445)

MOL for NP0013445 (Aspergillusic acid)

3D MOL for NP0013445 (Aspergillusic acid)

3D SDF for NP0013445 (Aspergillusic acid)

3D-SDF for NP0013445 (Aspergillusic acid)

PDB for NP0013445 (Aspergillusic acid)

3D PDB for NP0013445 (Aspergillusic acid)

SMILES for NP0013445 (Aspergillusic acid)

INCHI for NP0013445 (Aspergillusic acid)

Structure for NP0013445 (Aspergillusic acid)

3D Structure for NP0013445 (Aspergillusic acid)