NP-MRD: Showing NP-Card for Tanzawaic acid A (NP0075821)

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Record Information

Version

2.0

Created at

2022-04-28 21:02:56 UTC

Updated at

2022-04-28 21:02:57 UTC

NP-MRD ID

NP0075821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tanzawaic acid A

Description

CHEMBL3353035, also known as tanzawaic acid a, belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. Tanzawaic acid A is found in Penicillium citrinum, Penicillium dierckxii and Penicillium sizovae. Based on a literature review very few articles have been published on CHEMBL3353035.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    1.5216   -3.2668    1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2830   -2.5023    0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189   -3.1395    0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703   -2.4566    0.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -1.1103    0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442   -0.4495    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905   -1.1246    0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -0.6421    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980    0.2926   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.6169   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1313    1.5635   -1.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5437    1.9135   -1.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8881    2.8375   -2.1205 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5187    1.2837   -0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022    1.0048    0.0792 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5431    1.5261    1.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6714    1.4162   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595    0.6671   -1.1417 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0911    1.6836   -1.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.3197   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2822   -3.0747    0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3319   -4.3522    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9633   -2.9414    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9448   -4.1956    1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0114   -2.9608    0.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5049   -1.1492    0.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812    0.8218   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3433    0.0717    0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    2.0936   -1.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3026    0.6502    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1664    1.4977    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    2.2380    1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4571    2.0632    1.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7635    0.7254    2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    1.2929   -2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8260    2.5247   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629    0.1375   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    1.6812   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7071    2.6861   -1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8889    1.4226   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9005   -1.0974   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    0.0705    0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
 15  6  1  0
  6  5  2  0
  5 20  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  2  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 14  1  0
 12 13  2  0
 20 18  1  0
  7  6  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 18 37  1  6
 17 35  1  0
 17 36  1  0
 15 31  1  6
 16 32  1  0
 16 33  1  0
 16 34  1  0
 20 41  1  0
 20 42  1  0
  4 25  1  0
  3 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
M  END


  Mrv1652304282223022D          

 20 21  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
    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
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
   -0.7145   -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
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   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
  6  7  1  0  0  0  0
  7  8  2  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
  5 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  1  1  0  0  0
 16 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0075821

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O2/c1-12-10-14(3)18-15(11-12)9-8-13(2)16(18)6-4-5-7-17(19)20/h4-9,12,14H,10-11H2,1-3H3,(H,19,20)/b6-4+,7-5+/t12-,14+/m0/s1

> <INCHI_KEY>
GCHCATJQYLAKIS-UFSSINQASA-N

> <FORMULA>
C18H22O2

> <MOLECULAR_WEIGHT>
270.372

> <EXACT_MASS>
270.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.378385017940406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-5-[(6S,8R)-2,6,8-trimethyl-5,6,7,8-tetrahydronaphthalen-1-yl]penta-2,4-dienoic acid

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
5.203015721333333

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9172092519578445

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.99909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-5-[(6S,8R)-2,6,8-trimethyl-5,6,7,8-tetrahydronaphthalen-1-yl]penta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -3.080   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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    5                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17    1   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Tanzawaic acid a	MeSH

Chemical Formula

C₁₈H₂₂O₂

Average Mass

270.3720 Da

Monoisotopic Mass

270.16198 Da

IUPAC Name

(2E,4E)-5-[(6S,8R)-2,6,8-trimethyl-5,6,7,8-tetrahydronaphthalen-1-yl]penta-2,4-dienoic acid

Traditional Name

(2E,4E)-5-[(6S,8R)-2,6,8-trimethyl-5,6,7,8-tetrahydronaphthalen-1-yl]penta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H22O2/c1-12-10-14(3)18-15(11-12)9-8-13(2)16(18)6-4-5-7-17(19)20/h4-9,12,14H,10-11H2,1-3H3,(H,19,20)/b6-4+,7-5+/t12-,14+/m0/s1

InChI Key

GCHCATJQYLAKIS-UFSSINQASA-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 citrinum	Fungi	KNApSAcK
Penicillium dierckxii	LOTUS Database	35616633
Penicillium sizovae	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Medium-chain fatty acid
Styrene
Fatty acyl
Fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.28	ALOGPS
logP	5.2	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85 m³·mol⁻¹	ChemAxon
Polarizability	31.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

8145962

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9970370

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tanzawaic acid A (NP0075821)

MOL for NP0075821 (Tanzawaic acid A)

3D MOL for NP0075821 (Tanzawaic acid A)

3D SDF for NP0075821 (Tanzawaic acid A)

3D-SDF for NP0075821 (Tanzawaic acid A)

PDB for NP0075821 (Tanzawaic acid A)

3D PDB for NP0075821 (Tanzawaic acid A)

SMILES for NP0075821 (Tanzawaic acid A)

INCHI for NP0075821 (Tanzawaic acid A)

Structure for NP0075821 (Tanzawaic acid A)

3D Structure for NP0075821 (Tanzawaic acid A)