NP-MRD: Showing NP-Card for [(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid (NP0240791)

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Record Information

Version

2.0

Created at

2022-09-07 00:41:58 UTC

Updated at

2022-09-07 00:41:58 UTC

NP-MRD ID

NP0240791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid

Description

Carlic acid, also known as carlate, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. [(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid is found in Penicillium dierckxii. Based on a literature review very few articles have been published on Carlic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202412D          

 16 17  0  0  1  0            999 V2000
    2.7343    3.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343    2.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    2.1693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    2.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    1.3443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6873    0.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4323    0.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172   -0.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073    0.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224   -0.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974   -0.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -1.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099   -1.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773   -1.3773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    0.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 O   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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
  9 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0240791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C[C@@H]1OC(=O)\C(C1=O)=C1\CCCO1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O6/c11-7(12)4-6-9(13)8(10(14)16-6)5-2-1-3-15-5/h6H,1-4H2,(H,11,12)/b8-5-/t6-/m0/s1

> <INCHI_KEY>
KYLABXGOIXIJHD-HOYUYTIUSA-N

> <FORMULA>
C10H10O6

> <MOLECULAR_WEIGHT>
226.184

> <EXACT_MASS>
226.047738042

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.86594600106889

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(Z,5'S)-2',4'-dioxo-3,4-dihydro-2'H,4'H,5H,5'H-[2,3'-bioxolylidene]-5'-yl]acetic acid

> <JCHEM_LOGP>
0.10106845500000033

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.701479570444809

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.782396955130392

> <JCHEM_PKA_STRONGEST_BASIC>
-4.844672571141798

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
50.99650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(Z,5'S)-2',4'-dioxo-4,5-dihydro-3H,5'H-[2,3'-bioxolylidene]-5'-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       5.104   6.359   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.104   4.819   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.438   4.049   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.770   4.049   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.770   2.509   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.016   1.604   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.540   0.139   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.446  -1.106   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.000   0.139   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.095  -1.106   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.555  -1.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.079  -2.571   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.325  -3.476   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.571  -2.571   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.524   1.604   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.060   2.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    9    5   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Carlate	Generator

Chemical Formula

C₁₀H₁₀O₆

Average Mass

226.1840 Da

Monoisotopic Mass

226.04774 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC(=O)C[C@@H]1OC(=O)\C(C1=O)=C1\CCCO1

InChI Identifier

InChI=1S/C10H10O6/c11-7(12)4-6-9(13)8(10(14)16-6)5-2-1-3-15-5/h6H,1-4H2,(H,11,12)/b8-5-/t6-/m0/s1

InChI Key

KYLABXGOIXIJHD-HOYUYTIUSA-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 dierckxii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102117093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid (NP0240791)

MOL for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

3D MOL for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

3D SDF for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

3D-SDF for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

PDB for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

3D PDB for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

SMILES for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

INCHI for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

Structure for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)

3D Structure for NP0240791 ([(z,5's)-2',4'-dioxo-4,5-dihydro-3h,5'h-[2,3'-bioxolyliden]-5'-yl]acetic acid)