NP-MRD: Showing NP-Card for stipitatic acid (NP0040481)

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Record Information

Version

2.0

Created at

2021-06-20 22:37:59 UTC

Updated at

2021-06-30 00:14:25 UTC

NP-MRD ID

NP0040481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

stipitatic acid

Provided By

JEOL Database JEOL Logo

Description

Stipitatic acid, also known as stipitatate, belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. stipitatic acid is found in Penicillium sp. FKI-4410 and Talaromyces stipitatus. stipitatic acid was first documented in 2011 (PMID: 21063422). Based on a literature review very few articles have been published on stipitatic acid (PMID: 26926531) (PMID: 24863423) (PMID: 23870699) (PMID: 22508998).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100383D          

 19 19  0  0  0  0            999 V2000
   -2.8276    0.7512   -0.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7661    1.1319   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529    1.4103   -1.8532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082    1.4041    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7522    1.8828    1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427    2.2502    2.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5498    2.7071    3.6736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3760    2.2329    2.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2832    1.7952    1.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4855    1.8689    1.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913    1.2523    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9441    0.8872   -0.8028 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6372    1.1170   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.2123   -2.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8175    1.9999    1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5169    2.6272    3.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774    2.5637    3.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556    1.0871   -0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5659    0.7128   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  4  1  0  0  0  0
  5  4  2  0  0  0  0
  8  6  2  0  0  0  0
  9 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6  7  1  0  0  0  0
  9 11  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  2  0  0  0  0
  8  9  1  0  0  0  0
  2  3  1  0  0  0  0
  8 17  1  0  0  0  0
 13 19  1  0  0  0  0
  5 15  1  0  0  0  0
 12 18  1  0  0  0  0
  7 16  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040481

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O5/c9-5-1-4(8(12)13)2-6(10)7(11)3-5/h1-3,9H,(H,10,11)(H,12,13)

> <INCHI_KEY>
ANEBWDNUQVPSJT-UHFFFAOYSA-N

> <FORMULA>
C8H6O5

> <MOLECULAR_WEIGHT>
182.131

> <EXACT_MASS>
182.021523293

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
16.043820169635474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,6-dihydroxy-5-oxocyclohepta-1,3,6-triene-1-carboxylic acid

> <ALOGPS_LOGP>
-0.52

> <JCHEM_LOGP>
-0.2233964475994931

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.710563967277967

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8941814409188282

> <JCHEM_PKA_STRONGEST_BASIC>
2.9167176424949663

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
46.0105

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stipitatic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.828   0.751  -0.076  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.766   1.132  -0.541  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.653   1.410  -1.853  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.508   1.404   0.236  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.752   1.883   1.472  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.043   2.250   2.491  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.550   2.707   3.674  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.376   2.233   2.518  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.283   1.795   1.399  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.486   1.869   1.593  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.891   1.252   0.029  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.944   0.887  -0.803  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.637   1.117  -0.404  0.00  0.00           C+0
HETATM   14  H   UNK     0      -2.540   1.212  -2.219  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.817   2.000   1.696  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.517   2.627   3.617  0.00  0.00           H+0
HETATM   17  H   UNK     0       1.877   2.564   3.424  0.00  0.00           H+0
HETATM   18  H   UNK     0       3.756   1.087  -0.286  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.566   0.713  -1.417  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    1    3                                                  
CONECT    3    2   14                                                       
CONECT    4   13    5    2                                                  
CONECT    5    4    6   15                                                  
CONECT    6    8    7    5                                                  
CONECT    7    6   16                                                       
CONECT    8    6    9   17                                                  
CONECT    9   10   11    8                                                  
CONECT   10    9                                                            
CONECT   11   12   13    9                                                  
CONECT   12   11   18                                                       
CONECT   13    4   11   19                                                  
CONECT   14    3                                                            
CONECT   15    5                                                            
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
Stipitatate	ChEBI
3,6-Dihydroxy-5-oxo-1,3,6-cycloheptatriene-1-carboxylic acid	Kegg
3,6-Dihydroxy-5-oxo-1,3,6-cycloheptatriene-1-carboxylate	Generator

Chemical Formula

C₈H₆O₅

Average Mass

182.1310 Da

Monoisotopic Mass

182.02152 Da

IUPAC Name

3,6-dihydroxy-5-oxocyclohepta-1,3,6-triene-1-carboxylic acid

Traditional Name

stipitatic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C(O[H])=C([H])C(=O)C(O[H])=C1[H]

InChI Identifier

InChI=1S/C8H6O5/c9-5-1-4(8(12)13)2-6(10)7(11)3-5/h1-3,9H,(H,10,11)(H,12,13)

InChI Key

ANEBWDNUQVPSJT-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium viticola	JEOL database	Iwatsuki, M., et al, J.Antibiot. 64, 183 (2011)
Talaromyces stipitatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Tropolones

Direct Parent

Tropolones

Alternative Parents

Substituents

Tropolone
Vinylogous acid
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:15957 )

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	-0.52	ALOGPS
logP	-0.22	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	2.92	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	1	ChemAxon
Refractivity	46.01 m³·mol⁻¹	ChemAxon
Polarizability	16.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

19955692

KEGG Compound ID

C01853

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Stipitatic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15957

Good Scents ID

Not Available

References

General References

Iwatsuki M, Takada S, Mori M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Nonaka K, Masuma R, Otoguro K, Shiomi K, Omura S: In vitro and in vivo antimalarial activity of puberulic acid and its new analogs, viticolins A-C, produced by Penicillium sp. FKI-4410. J Antibiot (Tokyo). 2011 Feb;64(2):183-8. doi: 10.1038/ja.2010.124. Epub 2010 Nov 10. [PubMed:21063422 ]
Yan Y, Ma YT, Yang J, Horsman GP, Luo D, Ji X, Huang SX: Tropolone Ring Construction in the Biosynthesis of Rubrolone B, a Cationic Tropolone Alkaloid from Endophytic Streptomyces. Org Lett. 2016 Mar 18;18(6):1254-7. doi: 10.1021/acs.orglett.6b00074. Epub 2016 Feb 29. [PubMed:26926531 ]
al Fahad A, Abood A, Simpson TJ, Cox RJ: The biosynthesis and catabolism of the maleic anhydride moiety of stipitatonic acid. Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7519-23. doi: 10.1002/anie.201403450. Epub 2014 May 26. [PubMed:24863423 ]
Cox RJ, Al-Fahad A: Chemical mechanisms involved during the biosynthesis of tropolones. Curr Opin Chem Biol. 2013 Aug;17(4):532-6. doi: 10.1016/j.cbpa.2013.06.029. Epub 2013 Jul 16. [PubMed:23870699 ]
Davison J, al Fahad A, Cai M, Song Z, Yehia SY, Lazarus CM, Bailey AM, Simpson TJ, Cox RJ: Genetic, molecular, and biochemical basis of fungal tropolone biosynthesis. Proc Natl Acad Sci U S A. 2012 May 15;109(20):7642-7. doi: 10.1073/pnas.1201469109. Epub 2012 Apr 16. [PubMed:22508998 ]
Iwatsuki, M., et al. (2011). Iwatsuki, M., et al, J.Antibiot. 64, 183 (2011). J. Antibiotics.

Showing NP-Card for stipitatic acid (NP0040481)

MOL for NP0040481 (stipitatic acid)

3D MOL for NP0040481 (stipitatic acid)

3D SDF for NP0040481 (stipitatic acid)

3D-SDF for NP0040481 (stipitatic acid)

PDB for NP0040481 (stipitatic acid)

3D PDB for NP0040481 (stipitatic acid)

SMILES for NP0040481 (stipitatic acid)

INCHI for NP0040481 (stipitatic acid)

Structure for NP0040481 (stipitatic acid)

3D Structure for NP0040481 (stipitatic acid)