NP-MRD: Showing NP-Card for G2201-C (NP0021828)

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Record Information

Version

2.0

Created at

2021-01-06 07:05:18 UTC

Updated at

2021-07-15 17:37:24 UTC

NP-MRD ID

NP0021828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

G2201-C

Provided By

NPAtlas

Description

G2201-C is found in Streptomyces cattleya. G2201-C was first documented in 1978 (PMID: 627519). Based on a literature review very few articles have been published on 2-Hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105193D          

 16 16  0  0  0  0            999 V2000
    1.3942   -2.0718    0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0011   -0.9309    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796    0.2858    0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115    1.1760   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949    0.6078   -1.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507    1.0166   -2.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2787   -0.5661   -0.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7745   -1.5839   -0.9670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2462   -0.0929    0.8694 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4336    0.3717    0.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    0.4604    1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7006    2.1855   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4409   -1.5223   -1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5008   -0.9087    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    0.7776    1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835    0.7952   -0.5605 H   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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7  2  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021828

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O4/c7-3-6(10)4(8)1-2-5(6)9/h1-2,7,10H,3H2

> <INCHI_KEY>
ASRUSYCVDJKOBU-UHFFFAOYSA-N

> <FORMULA>
C6H6O4

> <MOLECULAR_WEIGHT>
142.11

> <EXACT_MASS>
142.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.137654916992355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-0.5953916669999999

> <ALOGPS_LOGS>
0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.87602814026808

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.613344718754643

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2226271002652407

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
33.004799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione

> <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  O   UNK     0       1.394  -2.072   0.826  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.001  -0.931   0.454  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.780   0.286   0.616  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.312   1.176  -0.239  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.195   0.608  -1.021  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.251   1.017  -2.114  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.279  -0.566  -0.205  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.775  -1.584  -0.967  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.246  -0.093   0.869  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.434   0.372   0.308  0.00  0.00           O+0
HETATM   11  H   UNK     0       2.615   0.460   1.318  0.00  0.00           H+0
HETATM   12  H   UNK     0       1.701   2.186  -0.345  0.00  0.00           H+0
HETATM   13  H   UNK     0      -0.441  -1.522  -1.894  0.00  0.00           H+0
HETATM   14  H   UNK     0      -1.501  -0.909   1.564  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.788   0.778   1.389  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.284   0.795  -0.561  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9    2                                             
CONECT    8    7   13                                                       
CONECT    9    7   10   14   15                                             
CONECT   10    9   16                                                       
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Hydroxy-2-hydroxymethylcyclopent-4-ene-1,3-dione	MeSH

Chemical Formula

C₆H₆O₄

Average Mass

142.1100 Da

Monoisotopic Mass

142.02661 Da

IUPAC Name

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione

Traditional Name

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione

CAS Registry Number

Not Available

SMILES

OCC1(O)C(=O)C=CC1=O

InChI Identifier

InChI=1S/C6H6O4/c7-3-6(10)4(8)1-2-5(6)9/h1-2,7,10H,3H2

InChI Key

ASRUSYCVDJKOBU-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
Streptomyces cattleya	NPAtlas	627519

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Tertiary alcohol
Cyclic ketone
Ketone
1,2-diol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-0.47	ALOGPS
logP	-0.6	ChemAxon
logS	0.27	ALOGPS
pKa (Strongest Acidic)	10.61	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	33 m³·mol⁻¹	ChemAxon
Polarizability	12.14 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

NPAtlas ID

NPA018547

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

113771

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

128335

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Noble M, Noble D, Fletton RA: G2201-C, a new cyclopentenedione antibiotic, isolated from the fermentation broth of Streptomyces cattleya. J Antibiot (Tokyo). 1978 Jan;31(1):15-8. doi: 10.7164/antibiotics.31.15. [PubMed:627519 ]

Showing NP-Card for G2201-C (NP0021828)

MOL for NP0021828 (G2201-C)

3D MOL for NP0021828 (G2201-C)

3D SDF for NP0021828 (G2201-C)

3D-SDF for NP0021828 (G2201-C)

PDB for NP0021828 (G2201-C)

3D PDB for NP0021828 (G2201-C)

SMILES for NP0021828 (G2201-C)

INCHI for NP0021828 (G2201-C)

Structure for NP0021828 (G2201-C)

3D Structure for NP0021828 (G2201-C)