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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:35:29 UTC

Update Date

2023-02-21 17:27:30 UTC

HMDB ID

HMDB0040045

Secondary Accession Numbers

HMDB40045

Metabolite Identification

Common Name

5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol

Description

5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. Based on a literature review very few articles have been published on 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061311352D          

 13 14  0  0  0  0            999 V2000
   -0.0953    2.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596    3.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4822    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053    1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    0.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5078    4.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697    0.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9203    2.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5078    3.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -0.1525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223    4.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753    3.0452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  1  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040045

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=CC=C(O1)\C=C1\CCN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO2/c12-7-10-2-1-9(13-10)5-8-3-4-11-6-8/h1-2,5-6,12H,3-4,7H2/b8-5-

> <INCHI_KEY>
JOWOWIZUAITHGQ-YVMONPNESA-N

> <FORMULA>
C10H11NO2

> <MOLECULAR_WEIGHT>
177.1998

> <EXACT_MASS>
177.078978601

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.10986306931745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{5-[(4Z)-3,4-dihydro-2H-pyrrol-4-ylidenemethyl]furan-2-yl}methanol

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
0.34872319333333335

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.775043905179203

> <JCHEM_PKA_STRONGEST_BASIC>
6.389169431678977

> <JCHEM_POLAR_SURFACE_AREA>
45.730000000000004

> <JCHEM_REFRACTIVITY>
50.7981

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-[(3Z)-4,5-dihydropyrrol-3-ylidenemethyl]furan-2-yl}methanol

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.178   4.220   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.298   5.684   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.767   0.233   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.736  -0.911   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.623   2.974   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.490   1.247   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.948   8.130   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.997   1.567   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.718   4.220   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.948   6.590   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.329  -0.285   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -2.282   8.900   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.194   5.684   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   10                                                       
CONECT    3    4    8                                                       
CONECT    4    3   11                                                       
CONECT    5    8    9                                                       
CONECT    6    8   11                                                       
CONECT    7   10   12                                                       
CONECT    8    3    5    6                                                  
CONECT    9    1    5   13                                                  
CONECT   10    2    7   13                                                  
CONECT   11    4    6                                                       
CONECT   12    7                                                            
CONECT   13    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[5-(Hydroxymethyl)furfurylidene]-1-pyrroline	HMDB

Chemical Formula

C₁₀H₁₁NO₂

Average Molecular Weight

177.1998

Monoisotopic Molecular Weight

177.078978601

IUPAC Name

{5-[(4Z)-3,4-dihydro-2H-pyrrol-4-ylidenemethyl]furan-2-yl}methanol

Traditional Name

{5-[(3Z)-4,5-dihydropyrrol-3-ylidenemethyl]furan-2-yl}methanol

CAS Registry Number

Not Available

SMILES

OCC1=CC=C(O1)\C=C1\CCN=C1

InChI Identifier

InChI=1S/C10H11NO2/c12-7-10-2-1-9(13-10)5-8-3-4-11-6-8/h1-2,5-6,12H,3-4,7H2/b8-5-

InChI Key

JOWOWIZUAITHGQ-YVMONPNESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds 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

Furan
Pyrroline
Heteroaromatic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Oxacycle
Alcohol
Aromatic alcohol
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Imine
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040045)
Cytoplasm (HMDB: HMDB0040045)

Source

Exogenous

Exogenous (HMDB: HMDB0040045)

Food

Food (HMDB: HMDB0040045)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040045)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	1.32	ALOGPS
logP	0.35	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	6.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.73 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.8 m³·mol⁻¹	ChemAxon
Polarizability	19.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.078	31661259
DarkChem	[M-H]-	140.959	31661259
DeepCCS	[M+H]+	137.815	30932474
DeepCCS	[M-H]-	135.173	30932474
DeepCCS	[M-2H]-	170.923	30932474
DeepCCS	[M+Na]+	146.461	30932474
AllCCS	[M+H]+	138.2	32859911
AllCCS	[M+H-H2O]+	133.6	32859911
AllCCS	[M+NH4]+	142.5	32859911
AllCCS	[M+Na]+	143.7	32859911
AllCCS	[M-H]-	140.5	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	2.78 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8925 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.49 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	688.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	307.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	125.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	275.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	381.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	230.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	816.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	280.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	988.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	256.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	431.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	250.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	51.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol	OCC1=CC=C(O1)\C=C1\CCN=C1	2639.0	Standard polar	33892256
5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol	OCC1=CC=C(O1)\C=C1\CCN=C1	1612.5	Standard non polar	33892256
5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol	OCC1=CC=C(O1)\C=C1\CCN=C1	1788.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol,1TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(/C=C2\C=NCC2)O1	1889.0	Semi standard non polar	33892256
5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(/C=C2\C=NCC2)O1	2112.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-016s-1900000000-666dbcd9a9666d630806	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol GC-MS (1 TMS) - 70eV, Positive	splash10-0229-8920000000-147cd736c7a79a5ebdba	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 10V, Positive-QTOF	splash10-004i-1900000000-71522343137948277035	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 20V, Positive-QTOF	splash10-03fs-2900000000-c92696d3bd1f4809e022	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 40V, Positive-QTOF	splash10-0fv0-9100000000-06275e69d85494737a48	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 10V, Negative-QTOF	splash10-004i-0900000000-035830e6a31406b10f6a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 20V, Negative-QTOF	splash10-056s-0900000000-9325a616a38e94ad108f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 40V, Negative-QTOF	splash10-0v0r-9700000000-971509bb21db1f74e868	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 10V, Negative-QTOF	splash10-0002-0900000000-756b5565f003f9643152	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 20V, Negative-QTOF	splash10-0pxu-1900000000-6d7a2683adbb841f0e93	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 40V, Negative-QTOF	splash10-001i-5900000000-efa472316637150b76e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 10V, Positive-QTOF	splash10-004i-0900000000-7dc7fe44084291893a1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 20V, Positive-QTOF	splash10-004j-2900000000-ac3dd43cf5bb83154981	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol 40V, Positive-QTOF	splash10-016v-2900000000-c5d90dff3173c78b4d14	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019732

KNApSAcK ID

Not Available

Chemspider ID

30777402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752775

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol (HMDB0040045)

MOL for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

3D MOL for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

3D SDF for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

3D-SDF for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

PDB for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

3D PDB for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

SMILES for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

INCHI for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

Structure for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

3D Structure for HMDB0040045 (5-[2H-Pyrrol-4-(3H)-ylidenemethyl]-2-furanmethanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra