NP-MRD: Showing NP-Card for 6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one (NP0199782)

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Record Information

Version

2.0

Created at

2022-09-04 18:29:12 UTC

Updated at

2022-09-04 18:29:12 UTC

NP-MRD ID

NP0199782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one

Description

Chlamydospordiol belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. 6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one is found in Fusarium tricinctum. 6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one was first documented in 2006 (PMID: 16908037). Based on a literature review very few articles have been published on Chlamydospordiol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    4.4465    0.2838   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2395   -0.4030   -0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722    0.2835   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0132    1.6511    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284    2.3023    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8354    3.5607    0.3771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2299    1.5830    0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193    0.2505    0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.4193    0.7618 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4368    0.6106    1.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254   -0.7573   -0.5473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5134    0.5193   -1.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -1.3996   -0.3098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9089   -0.4810    0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0001   -1.9289    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -2.6859    0.4228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3358    0.9485   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6294    0.9477    0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2958   -0.3961   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402    2.2095   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5019   -1.2765    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4850    0.3801    1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2483    0.5755    2.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1114    1.6010    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6419   -1.3760   -1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1123    1.1631   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1906    0.2154   -2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148    0.9700   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681   -0.7755   -0.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8502   -2.3370    0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -2.1849   -0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146   -3.6345    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  2  0
 14 15  1  0
 15 16  1  0
 14  3  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  9 21  1  1
 10 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  6
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
M  END


  Mrv1652309042220292D          

 16 16  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
    1.4289    0.8250    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   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
   -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  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC(C(C)C(C)O)=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O5/c1-6(7(2)13)11-8(5-12)9(15-3)4-10(14)16-11/h4,6-7,12-13H,5H2,1-3H3

> <INCHI_KEY>
BSXCHPRMOOSCRM-UHFFFAOYSA-N

> <FORMULA>
C11H16O5

> <MOLECULAR_WEIGHT>
228.244

> <EXACT_MASS>
228.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.901231678405356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxy-2H-pyran-2-one

> <JCHEM_LOGP>
-0.4665524896666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.346931853045817

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.718031565243109

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7373427081795256

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
59.8591

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
4-Methoxy-5-hydroxymethyl-6-(3-butan-2-ol)-2H-pyran-2-one	MeSH

Chemical Formula

C₁₁H₁₆O₅

Average Mass

228.2440 Da

Monoisotopic Mass

228.09977 Da

IUPAC Name

6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxy-2H-pyran-2-one

Traditional Name

6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(C(C)C(C)O)=C1CO

InChI Identifier

InChI=1S/C11H16O5/c1-6(7(2)13)11-8(5-12)9(15-3)4-10(14)16-11/h4,6-7,12-13H,5H2,1-3H3

InChI Key

BSXCHPRMOOSCRM-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, 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
Fusarium tricinctum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Alkyl aryl ether
Pyranone
Vinylogous ester
Heteroaromatic compound
Lactone
Secondary alcohol
Ether
Oxacycle
Aromatic alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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
logP	-0.47	ChemAxon
pKa (Strongest Acidic)	14.72	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.86 m³·mol⁻¹	ChemAxon
Polarizability	22.9 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

165795

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

190904

PDB ID

Not Available

ChEBI ID

182459

Good Scents ID

Not Available

References

General References

Uhlig S, Jestoi M, Kristin Knutsen A, Heier BT: Multiple regression analysis as a tool for the identification of relations between semi-quantitative LC-MS data and cytotoxicity of extracts of the fungus Fusarium avenaceum (syn. F. arthrosporioides). Toxicon. 2006 Oct;48(5):567-79. doi: 10.1016/j.toxicon.2006.07.007. Epub 2006 Jul 7. [PubMed:16908037 ]
LOTUS database [Link]

Showing NP-Card for 6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one (NP0199782)

MOL for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

3D MOL for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

3D SDF for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

3D-SDF for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

PDB for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

3D PDB for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

SMILES for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

INCHI for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

Structure for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)

3D Structure for NP0199782 (6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxypyran-2-one)