NP-MRD: Showing NP-Card for 2-Hydroxymethyl-3-methylcyclopent-2-enon (NP0006574)

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Record Information

Version

2.0

Created at

2020-12-09 03:33:07 UTC

Updated at

2021-07-15 16:55:11 UTC

NP-MRD ID

NP0006574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxymethyl-3-methylcyclopent-2-enon

Provided By

NPAtlas

Description

148694-03-5 Is also known as 2HMMC CPD. 2-Hydroxymethyl-3-methylcyclopent-2-enon is found in Unknown-fungus sp. LRUB20. 2-Hydroxymethyl-3-methylcyclopent-2-enon was first documented in 2006 (PMID: 16989533). Based on a literature review very few articles have been published on 148694-03-5.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118293D          

 19 19  0  0  0  0            999 V2000
   -0.6700    1.9594   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4831    0.4961    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -0.2402   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738    0.3072   -0.7235 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8674    0.0218    0.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3164   -1.6360    0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822   -2.4951    0.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1628   -1.7269    0.0325 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5630   -0.3754    0.5760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7447    2.4051    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0559    2.4297   -0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    2.0995   -0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8106    1.3970   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814   -0.1517   -1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    0.2989    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4158   -1.7505   -1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784   -2.5647    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -0.4202    1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689   -0.0541    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9  2  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  4 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  9 18  1  0  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006574

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H10O2/c1-5-2-3-7(9)6(5)4-8/h8H,2-4H2,1H3

> <INCHI_KEY>
VBOYONXEJMSAAT-UHFFFAOYSA-N

> <FORMULA>
C7H10O2

> <MOLECULAR_WEIGHT>
126.155

> <EXACT_MASS>
126.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.463702497573966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-3-methylcyclopent-2-en-1-one

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
0.39958969366666686

> <ALOGPS_LOGS>
-0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.486472869863274

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.961306891894772

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8157096410460536

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
35.1535

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-3-methylcyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -0.670   1.959  -0.125  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.483   0.496   0.053  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.592  -0.240  -0.194  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.874   0.307  -0.724  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.867   0.022   0.227  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.316  -1.636   0.125  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.182  -2.495   0.402  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.163  -1.727   0.033  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.563  -0.375   0.576  0.00  0.00           C+0
HETATM   10  H   UNK     0      -0.745   2.405   0.890  0.00  0.00           H+0
HETATM   11  H   UNK     0       0.056   2.430  -0.780  0.00  0.00           H+0
HETATM   12  H   UNK     0      -1.697   2.099  -0.573  0.00  0.00           H+0
HETATM   13  H   UNK     0       1.811   1.397  -0.862  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.181  -0.152  -1.664  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.510   0.299   1.121  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.416  -1.751  -1.040  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.578  -2.565   0.608  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.506  -0.420   1.688  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.569  -0.054   0.239  0.00  0.00           H+0
CONECT    1    2   10   11   12                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5   13   14                                             
CONECT    5    4   15                                                       
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16   17                                             
CONECT    9    8    2   18   19                                             
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    4                                                            
CONECT   14    4                                                            
CONECT   15    5                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19    9                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2HMMC CPD	MeSH
2-Hydroxymethyl-3-methylcyclopent-2-enone	MeSH
cis-2-Hydroxymethyl-3-methylcyclopentanone	MeSH

Chemical Formula

C₇H₁₀O₂

Average Mass

126.1550 Da

Monoisotopic Mass

126.06808 Da

IUPAC Name

2-(hydroxymethyl)-3-methylcyclopent-2-en-1-one

Traditional Name

2-(hydroxymethyl)-3-methylcyclopent-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC1=C(CO)C(=O)CC1

InChI Identifier

InChI=1S/C7H10O2/c1-5-2-3-7(9)6(5)4-8/h8H,2-4H2,1H3

InChI Key

VBOYONXEJMSAAT-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
Unknown-fungus sp. LRUB20	NPAtlas	16989533

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
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	-0.18	ALOGPS
logP	0.4	ChemAxon
logS	-0.44	ALOGPS
pKa (Strongest Acidic)	14.96	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.15 m³·mol⁻¹	ChemAxon
Polarizability	13.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA015964

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21378569

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15768146

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chomcheon P, Sriubolmas N, Wiyakrutta S, Ngamrojanavanich N, Chaichit N, Mahidol C, Ruchirawat S, Kittakoop P: Cyclopentenones, scaffolds for organic syntheses produced by the endophytic fungus mitosporic dothideomycete sp. LRUB20. J Nat Prod. 2006 Sep;69(9):1351-3. doi: 10.1021/np060148h. [PubMed:16989533 ]

Showing NP-Card for 2-Hydroxymethyl-3-methylcyclopent-2-enon (NP0006574)

MOL for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

3D MOL for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

3D SDF for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

3D-SDF for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

PDB for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

3D PDB for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

SMILES for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

INCHI for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

Structure for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)

3D Structure for NP0006574 (2-Hydroxymethyl-3-methylcyclopent-2-enon)