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Showing metabocard for 2-Benzofurancarboxaldehyde (HMDB0033183)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:54:14 UTC
Update Date2023-02-21 17:23:13 UTC
HMDB IDHMDB0033183
Secondary Accession Numbers
  • HMDB33183
Metabolite Identification
Common Name2-Benzofurancarboxaldehyde
Description2-Benzofurancarboxaldehyde belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 2-Benzofurancarboxaldehyde is an almond and bitter tasting compound. Based on a literature review very few articles have been published on 2-Benzofurancarboxaldehyde.
Structure
Data?1677000193
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033183 (2-Benzofurancarboxaldehyde)


  Mrv0541 05061306582D          

 11 12  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
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3D MOL for HMDB0033183 (2-Benzofurancarboxaldehyde)

HMDB0033183
     RDKit          3D
2-Benzofurancarboxaldehyde
 17 18  0  0  0  0  0  0  0  0999 V2000
    3.1277    2.3750    1.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819    1.5067    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003    0.8403    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    1.0752    0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.2476    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847    0.0437    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -0.8841   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8395   -1.6181   -1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.4057   -1.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711   -0.4754   -0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184   -0.0966   -0.6681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807    1.2983   -0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683    1.7764    1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018    0.6497    1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -1.0011    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4404   -2.3473   -1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342   -1.9843   -2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  3  1  0
 10  5  1  0
  2 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0033183 (2-Benzofurancarboxaldehyde)


  Mrv0541 05061306582D          

 11 12  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033183

> <DATABASE_NAME>
hmdb

> <SMILES>
O=CC1=CC2=CC=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C9H6O2/c10-6-8-5-7-3-1-2-4-9(7)11-8/h1-6H

> <INCHI_KEY>
ADDZHRRCUWNSCS-UHFFFAOYSA-N

> <FORMULA>
C9H6O2

> <MOLECULAR_WEIGHT>
146.1427

> <EXACT_MASS>
146.036779436

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.738332936698649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-benzofuran-2-carbaldehyde

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.7648726849999998

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.431124770588955

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
41.3606

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-benzofuran-2-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0033183 (2-Benzofurancarboxaldehyde)

HMDB0033183
     RDKit          3D
2-Benzofurancarboxaldehyde
 17 18  0  0  0  0  0  0  0  0999 V2000
    3.1277    2.3750    1.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819    1.5067    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003    0.8403    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    1.0752    0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.2476    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847    0.0437    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -0.8841   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8395   -1.6181   -1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.4057   -1.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711   -0.4754   -0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184   -0.0966   -0.6681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807    1.2983   -0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683    1.7764    1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018    0.6497    1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860   -1.0011    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4404   -2.3473   -1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342   -1.9843   -2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  3  1  0
 10  5  1  0
  2 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0033183 (2-Benzofurancarboxaldehyde)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.090   1.509   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    7    8                                                       
CONECT    6    8   10                                                       
CONECT    7    3    5    9                                                  
CONECT    8    5    6   11                                                  
CONECT    9    4    7   11                                                  
CONECT   10    6                                                            
CONECT   11    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0033183 (2-Benzofurancarboxaldehyde)

COMPND    HMDB0033183
HETATM    1  O1  UNL     1       3.128   2.375   1.343  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.082   1.507   0.443  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.800   0.840   0.217  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.633   1.075   0.900  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.346   0.248   0.391  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.685   0.044   0.674  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.440  -0.884  -0.024  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.839  -1.618  -1.024  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.508  -1.406  -1.296  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.271  -0.475  -0.603  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.518  -0.097  -0.668  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.981   1.298  -0.112  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.468   1.776   1.702  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.102   0.650   1.470  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.486  -1.001   0.242  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.440  -2.347  -1.570  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.034  -1.984  -2.084  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   11
CONECT    4    5   13
CONECT    5    6    6   10
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   11
END
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SMILES for HMDB0033183 (2-Benzofurancarboxaldehyde)

O=CC1=CC2=CC=CC=C2O1
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INCHI for HMDB0033183 (2-Benzofurancarboxaldehyde)

InChI=1S/C9H6O2/c10-6-8-5-7-3-1-2-4-9(7)11-8/h1-6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Benzofuran-2-carbaldehydeHMDB
2-BenzofurancarbaldehydeHMDB
2-FormylbenzofuranHMDB
benzo(b)-2-FurfuralHMDB
Benzofuran-2-aldehydeHMDB
Benzofuran-2-carbaldehydeHMDB
Benzofuran-2-carboxaldehydeHMDB
CoumarilaldehydeHMDB
FEMA 3128HMDB
Nchem.328-comp4cHMDB
Chemical FormulaC9H6O2
Average Molecular Weight146.1427
Monoisotopic Molecular Weight146.036779436
IUPAC Name1-benzofuran-2-carbaldehyde
Traditional Name1-benzofuran-2-carbaldehyde
CAS Registry Number4265-16-1
SMILES
O=CC1=CC2=CC=CC=C2O1
InChI Identifier
InChI=1S/C9H6O2/c10-6-8-5-7-3-1-2-4-9(7)11-8/h1-6H
InChI KeyADDZHRRCUWNSCS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • Aryl-aldehyde
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point195.00 to 198.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point130.00 to 131.00 °C. @ 13.00 mm HgThe Good Scents Company Information System
Water Solubility1520 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.665 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.49 g/LALOGPS
logP1.85ALOGPS
logP1.76ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.21 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.36 m³·mol⁻¹ChemAxon
Polarizability14.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.05631661259
DarkChem[M-H]-126.86431661259
DeepCCS[M+H]+129.16430932474
DeepCCS[M-H]-125.80430932474
DeepCCS[M-2H]-163.00830932474
DeepCCS[M+Na]+138.13530932474
AllCCS[M+H]+128.932859911
AllCCS[M+H-H2O]+124.132859911
AllCCS[M+NH4]+133.432859911
AllCCS[M+Na]+134.732859911
AllCCS[M-H]-126.632859911
AllCCS[M+Na-2H]-127.332859911
AllCCS[M+HCOO]-128.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.91 minutes32390414
Predicted by Siyang on May 30, 202214.4057 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.08 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1655.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid568.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid215.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid373.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid294.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid504.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid609.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)214.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1189.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid450.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1221.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid386.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid441.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate544.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA483.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water95.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-BenzofurancarboxaldehydeO=CC1=CC2=CC=CC=C2O12312.3Standard polar33892256
2-BenzofurancarboxaldehydeO=CC1=CC2=CC=CC=C2O11332.7Standard non polar33892256
2-BenzofurancarboxaldehydeO=CC1=CC2=CC=CC=C2O11345.2Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011194
KNApSAcK IDNot Available
Chemspider ID55277
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61341
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1011591
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .