Np mrd loader

Showing NP-Card for 5-hydroxy-2-furancarboxaldhyde (NP0044216)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2021-12-17 23:36:50 UTC
Updated at2021-12-17 23:45:25 UTC
NP-MRD IDNP0044216
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-2-furancarboxaldhyde
Description5-Hydroxymethyl-2-furancarboxaldehyde, also known as 5-(hydroxymethyl)-2-furfural or HMF, belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. 5-Hydroxymethyl-2-furancarboxaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hydroxymethyl-2-furancarboxaldehyde exists in all living organisms, ranging from bacteria to humans. 5-Hydroxymethyl-2-furancarboxaldehyde is a caramel, cardboard, and fatty tasting compound. Outside of the human body, 5-Hydroxymethyl-2-furancarboxaldehyde has been detected, but not quantified in, garden onions and garden tomato. This could make 5-hydroxymethyl-2-furancarboxaldehyde a potential biomarker for the consumption of these foods. 5-hydroxy-2-furancarboxaldhyde was first documented in 2010 (PMID: 20082406). Aes-103 has been used in trials studying the treatment and prevention of Hypoxia, Anemia, Sickle Cell, and Sickle Cell Disease (PMID: 20420424) (PMID: 21838257) (PMID: 33978488).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044216 (5-hydroxy-2-furancarboxaldhyde)


  Mrv1652309272007392D          

  9  9  0  0  0  0            999 V2000
10001.406610000.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.121410000.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.642510000.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.928510000.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.021010000.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.353610000.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6085 9999.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4335 9999.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.688410000.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  2  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
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  3  1  0  0  0  0
  1  9  1  0  0  0  0
M  END
Download

3D MOL for NP0044216 (5-hydroxy-2-furancarboxaldhyde)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    3.1009   -1.6333    1.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142   -0.5565    0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -0.1723    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2091    1.0079   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1672    1.0121   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6372   -0.1310    0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0751   -0.5302    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191    0.4089   -0.3283 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -0.7707    0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7728    0.0214    0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134    1.7312   -0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7364    1.8061   -1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2726   -1.5037   -0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   -0.6374    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7361   -0.0524   -0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  9  1  0
  3  2  1  0
  2  1  2  0
  9  6  1  0
  8 15  1  0
  7 13  1  0
  7 14  1  0
  5 12  1  0
  4 11  1  0
  2 10  1  0
M  END
Download

3D SDF for NP0044216 (5-hydroxy-2-furancarboxaldhyde)


  Mrv1652309272007392D          

  9  9  0  0  0  0            999 V2000
10001.406610000.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.121410000.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.642510000.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.928510000.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.021010000.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.353610000.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6085 9999.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4335 9999.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.688410000.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  2  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
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  3  1  0  0  0  0
  1  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC=C(O1)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2

> <INCHI_KEY>
NOEGNKMFWQHSLB-UHFFFAOYSA-N

> <FORMULA>
C6H6O3

> <MOLECULAR_WEIGHT>
126.11

> <EXACT_MASS>
126.031694058

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.032772825774567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(hydroxymethyl)furan-2-carbaldehyde

> <ALOGPS_LOGP>
-0.17

> <JCHEM_LOGP>
-0.10135383899999993

> <ALOGPS_LOGS>
-0.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.645732658563311

> <JCHEM_PKA_STRONGEST_BASIC>
-3.080950200023614

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
31.726300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxymethylfurfural

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0044216 (5-hydroxy-2-furancarboxaldhyde)

Download
PDB for NP0044216 (5-hydroxy-2-furancarboxaldhyde)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8669.2928667.649   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8670.6278666.880   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8664.1338667.649   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8662.8008666.880   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8666.7068667.802   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8665.4608666.896   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8665.9368665.432   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.4768665.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.9528666.896   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1                                                            
CONECT    3    4    6                                                       
CONECT    4    3                                                            
CONECT    5    6    9                                                       
CONECT    6    7    5    3                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5    1                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

Download
3D PDB for NP0044216 (5-hydroxy-2-furancarboxaldhyde)
Download
SMILES for NP0044216 (5-hydroxy-2-furancarboxaldhyde)
OCC1=CC=C(O1)C=O
Download
INCHI for NP0044216 (5-hydroxy-2-furancarboxaldhyde)
InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
Download
View in JSmol
Synonyms
ValueSource
2-Hydroxymethyl-5-furfuralChEBI
5-(Hydroxymethyl)-2-furaldehydeChEBI
5-(Hydroxymethyl)-2-furancarbonalChEBI
5-(Hydroxymethyl)-2-furancarboxaldehydeChEBI
5-(Hydroxymethyl)-2-furfuralChEBI
5-(Hydroxymethyl)-2-furfuraldehydeChEBI
5-(Hydroxymethyl)furan-2-aldehydeChEBI
5-(Hydroxymethyl)furfuralChEBI
5-(Hydroxymethyl)furfuroleChEBI
5-HMFChEBI
5-Hydroxymethyl-2-formylfuranChEBI
5-Hydroxymethyl-2-furaldehydeChEBI
5-Hydroxymethyl-2-furancarbaldehydeChEBI
5-Hydroxymethyl-2-furfuralChEBI
5-HydroxymethylfuraldehydeChEBI
5-Hydroxymethylfuran-2-aldehydeChEBI
5-HydroxymethylfurfuraldehydeChEBI
5-OxymethylfurfuroleChEBI
HMFChEBI
HydroxymethylfurfuralChEBI
HydroxymethylfurfuralaldehydeChEBI
HydroxymethylfurfuraldehydeChEBI
HydroxymethylfurfuroleChEBI
5-HydroxymethylfurfuralKegg
2-Formyl-5-hydroxymethylfuranHMDB
5-(Hyddroxymethyl)furfuroleHMDB
5-(Hydroxymethyl)-2-formylfuranHMDB
5-(Hydroxymethyl)-2-furfural (HMF)HMDB
5-Hydroxymethyl furaldehydeHMDB
5-Hydroxymethyl-furfuralHMDB
5-HydrxoymethylfurfuralHMDB
5-MethylolfurfuralHMDB
5-HM-2-F CPDMeSH
5-HMF CPDMeSH
Aes-103MeSH
5-Hydroxymethyl furfuralMeSH
5-(Hydroxymethyl)furancarboxaldehydePhytoBank
5-HydroxymethylfurfurolPhytoBank
HydroxymethylfuraldehydePhytoBank
Chemical FormulaC6H6O3
Average Mass126.1100 Da
Monoisotopic Mass126.03169 Da
IUPAC Name5-(hydroxymethyl)furan-2-carbaldehyde
Traditional Namehydroxymethylfurfural
CAS Registry NumberNot Available
SMILES
OCC1=CC=C(O1)C=O
InChI Identifier
InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
InChI KeyNOEGNKMFWQHSLB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2021-12-17View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAryl-aldehydes  
Alternative Parents
Substituents
  • Aryl-aldehyde
    • 

  • Heteroaromatic compound
    • 

  • Furan
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic alcohol
    • 

  • Primary alcohol
    • 

  • Alcohol
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.17ALOGPS
logP-0.1ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)13.65ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity31.73 m³·mol⁻¹ChemAxon
Polarizability12.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034355  
DrugBank IDDB12298  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012717  
KNApSAcK IDC00029547  
Chemspider ID207215  
KEGG Compound IDC11101  
BioCyc IDCPD-11572  
BiGG IDNot Available
Wikipedia LinkHydroxymethylfurfural  
METLIN IDNot Available
PubChem Compound237332  
PDB IDFUX  
ChEBI ID412516  
Good Scents IDNot Available
References
General References
  1. Tong X, Li Y: Efficient and selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by Bronsted-acidic ionic liquids. ChemSusChem. 2010 Mar 22;3(3):350-5. doi: 10.1002/cssc.200900224. [PubMed:20082406  ] 
  2. Mesias-Garcia M, Guerra-Hernandez E, Garcia-Villanova B: Determination of furan precursors and some thermal damage markers in baby foods: ascorbic acid, dehydroascorbic acid, hydroxymethylfurfural and furfural. J Agric Food Chem. 2010 May 26;58(10):6027-32. doi: 10.1021/jf100649z. [PubMed:20420424  ] 
  3. Nikolov PY, Yaylayan VA: Thermal decomposition of 5-(hydroxymethyl)-2-furaldehyde (HMF) and its further transformations in the presence of glycine. J Agric Food Chem. 2011 Sep 28;59(18):10104-13. doi: 10.1021/jf202470u. Epub 2011 Aug 25. [PubMed:21838257  ] 
  4. Boning D, Kuebler WM, Bloch W: The oxygen dissociation curve of blood in COVID-19. Am J Physiol Lung Cell Mol Physiol. 2021 Aug 1;321(2):L349-L357. doi: 10.1152/ajplung.00079.2021. Epub 2021 May 12. [PubMed:33978488  ]