NP-MRD: Showing NP-Card for 2,5-bis(hydroxymethyl)furan monoacetate (NP0007940)

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Record Information

Version

2.0

Created at

2020-12-09 05:33:47 UTC

Updated at

2021-07-15 16:58:59 UTC

NP-MRD ID

NP0007940

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-bis(hydroxymethyl)furan monoacetate

Provided By

NPAtlas

Description

2,5-bis(hydroxymethyl)furan monoacetate is found in Streptomyces. 2,5-bis(hydroxymethyl)furan monoacetate was first documented in 2008 (PMID: 18715034). Based on a literature review very few articles have been published on [5-(hydroxymethyl)furan-2-yl]methyl acetate (PMID: 27163966).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106053D          

 22 22  0  0  0  0            999 V2000
   -4.1360   -0.3280    0.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7737    0.1398    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459   -0.2139    1.5063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1586    1.0253   -0.3849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8897    1.5723   -0.2289 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1946    0.5585   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1460   -0.7963   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441   -1.2606   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022   -0.1557    0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6834   -0.0857    0.2760 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3512    0.0882   -0.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4453    0.9006    0.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7546    0.5937   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5738   -0.9890    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0774   -0.8330   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7806    2.1770    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7246    2.2924   -1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -1.3626   -0.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7666   -2.2700   -0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135   -1.0427    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9217    0.7714    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930   -0.7818   -1.3313 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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12  6  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  5 16  1  0  0  0  0
  5 17  1  0  0  0  0
  7 18  1  0  0  0  0
  8 19  1  0  0  0  0
 10 20  1  0  0  0  0
 10 21  1  0  0  0  0
 11 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007940

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])C([H])=C(O1)C([H])([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O4/c1-6(10)11-5-8-3-2-7(4-9)12-8/h2-3,9H,4-5H2,1H3

> <INCHI_KEY>
KUVRLCOEIGGESY-UHFFFAOYSA-N

> <FORMULA>
C8H10O4

> <MOLECULAR_WEIGHT>
170.164

> <EXACT_MASS>
170.057908802

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.0120279370854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[5-(hydroxymethyl)furan-2-yl]methyl acetate

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
-0.14008054066666692

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.718411342588265

> <JCHEM_PKA_STRONGEST_BASIC>
-2.984827420858065

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
41.109700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(hydroxymethyl)furan-2-yl]methyl acetate

> <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  C   UNK     0      -4.136  -0.328   0.130  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.774   0.140   0.481  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.146  -0.214   1.506  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.159   1.025  -0.385  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.890   1.572  -0.229  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.195   0.559  -0.183  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.146  -0.796  -0.350  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.444  -1.261  -0.205  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.202  -0.156   0.041  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.683  -0.086   0.276  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.351   0.088  -0.927  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.445   0.901   0.049  0.00  0.00           O+0
HETATM   13  H   UNK     0      -4.755   0.594  -0.032  0.00  0.00           H+0
HETATM   14  H   UNK     0      -4.574  -0.989   0.898  0.00  0.00           H+0
HETATM   15  H   UNK     0      -4.077  -0.833  -0.842  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.781   2.177   0.712  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.725   2.292  -1.060  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.747  -1.363  -0.554  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.767  -2.270  -0.275  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.013  -1.043   0.734  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.922   0.771   0.940  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.593  -0.782  -1.331  0.00  0.00           H+0
CONECT    1    2   13   14   15                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   16   17                                             
CONECT    6    5    7   12                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11   20   21                                             
CONECT   11   10   22                                                       
CONECT   12    9    6                                                       
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    5                                                            
CONECT   17    5                                                            
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   10                                                            
CONECT   21   10                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
[5-(Hydroxymethyl)furan-2-yl]methyl acetic acid	Generator
25-Bis(hydroxymethyl)furan monoacetate	ChEMBL
25-Bis(hydroxymethyl)furan monoacetic acid	Generator
2,5-Bis(hydroxymethyl)furan monoacetic acid	Generator

Chemical Formula

C₈H₁₀O₄

Average Mass

170.1640 Da

Monoisotopic Mass

170.05791 Da

IUPAC Name

[5-(hydroxymethyl)furan-2-yl]methyl acetate

Traditional Name

[5-(hydroxymethyl)furan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=CC=C(CO)O1

InChI Identifier

InChI=1S/C8H10O4/c1-6(10)11-5-8-3-2-7(4-9)12-8/h2-3,9H,4-5H2,1H3

InChI Key

KUVRLCOEIGGESY-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	NPAtlas	18715034

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as heteroaromatic compounds. These are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Heteroaromatic compound
Furan
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	ALOGPS
logP	-0.14	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	13.72	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.11 m³·mol⁻¹	ChemAxon
Polarizability	17.01 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019867

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10760157

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12711087

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fotso S, Maskey RP, Schroder D, Ferrer AS, Grun-Wollny I, Laatsch H: Furan oligomers and beta-carbolines from terrestrial streptomycetes. J Nat Prod. 2008 Sep;71(9):1630-3. doi: 10.1021/np800248s. Epub 2008 Aug 21. [PubMed:18715034 ]
Phuakjaiphaeo C, Chang CI, Ruangwong O, Kunasakdakul K: Isolation and identification of an antifungal compound from endophytic Streptomyces sp. CEN26 active against Alternaria brassicicola. Lett Appl Microbiol. 2016 Jul;63(1):38-44. doi: 10.1111/lam.12582. Epub 2016 Jun 3. [PubMed:27163966 ]

Showing NP-Card for 2,5-bis(hydroxymethyl)furan monoacetate (NP0007940)

MOL for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

3D MOL for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

3D SDF for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

3D-SDF for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

PDB for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

3D PDB for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

SMILES for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

INCHI for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

Structure for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)

3D Structure for NP0007940 (2,5-bis(hydroxymethyl)furan monoacetate)