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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:06:43 UTC

Update Date

2022-03-07 02:56:16 UTC

HMDB ID

HMDB0039606

Secondary Accession Numbers

HMDB39606

Metabolite Identification

Common Name

Repandiol

Description

Repandiol belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). Repandiol has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make repandiol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Repandiol.

Structure

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


  Mrv0541 05061311162D          

 14 15  0  0  0  0            999 V2000
   -0.4592   -5.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553   -5.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1737   -4.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697   -5.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0967   -7.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8882   -4.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842   -6.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007   -3.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0967   -7.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -2.2710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8112   -8.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132   -4.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5092   -6.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  3  0  0  0  0
  4  2  3  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039606

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC1C#CC#CC1OC1CO

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c11-5-9-7(13-9)3-1-2-4-8-10(6-12)14-8/h7-12H,5-6H2

> <INCHI_KEY>
BQWDCZPSFPXRCB-UHFFFAOYSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.30296735639127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-{4-[3-(hydroxymethyl)oxiran-2-yl]buta-1,3-diyn-1-yl}oxiran-2-yl)methanol

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-0.45892371466666676

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.85751374528855

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.255482903388081

> <JCHEM_PKA_STRONGEST_BASIC>
-2.992723048817595

> <JCHEM_POLAR_SURFACE_AREA>
65.52

> <JCHEM_REFRACTIVITY>
48.5102

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-{4-[3-(hydroxymethyl)oxiran-2-yl]buta-1,3-diyn-1-yl}oxiran-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      -0.857  -9.423   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.477 -10.193   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.191  -8.653   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.810 -10.963   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.295  -5.009   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.914 -14.607   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.525  -7.883   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.144 -11.733   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.295  -6.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.914 -13.067   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.628  -4.239   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.248 -15.377   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.065  -7.883   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.684 -11.733   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    9   11                                                       
CONECT    6   10   12                                                       
CONECT    7    3    9   13                                                  
CONECT    8    4   10   14                                                  
CONECT    9    5    7   13                                                  
CONECT   10    6    8   14                                                  
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    7    9                                                       
CONECT   14    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3,8,9-Diepoxy-4,6-decadiyne-1,10-diol	HMDB, MeSH
Repandiol	MeSH

Chemical Formula

C₁₀H₁₀O₄

Average Molecular Weight

194.184

Monoisotopic Molecular Weight

194.057908808

IUPAC Name

(3-{4-[3-(hydroxymethyl)oxiran-2-yl]buta-1,3-diyn-1-yl}oxiran-2-yl)methanol

Traditional Name

(3-{4-[3-(hydroxymethyl)oxiran-2-yl]buta-1,3-diyn-1-yl}oxiran-2-yl)methanol

CAS Registry Number

147921-90-2

SMILES

OCC1OC1C#CC#CC1OC1CO

InChI Identifier

InChI=1S/C10H10O4/c11-5-9-7(13-9)3-1-2-4-8-10(6-12)14-8/h7-12H,5-6H2

InChI Key

BQWDCZPSFPXRCB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Not Available

Direct Parent

Epoxides

Alternative Parents

Substituents

Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039606)
Cytoplasm (HMDB: HMDB0039606)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039606)

Source

Endogenous

Plant

Plant (HMDB: HMDB0039606)

Exogenous

Food

Food (HMDB: HMDB0039606)

Not Available

Nutrient (HMDB: HMDB0039606)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 - 169 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	17530 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	-0.5	ALOGPS
logP	-0.46	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.26	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	48.51 m³·mol⁻¹	ChemAxon
Polarizability	20.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	145.721	31661259
DarkChem	[M-H]-	144.197	31661259
DeepCCS	[M+H]+	136.599	30932474
DeepCCS	[M-H]-	133.031	30932474
DeepCCS	[M-2H]-	170.37	30932474
DeepCCS	[M+Na]+	145.908	30932474
AllCCS	[M+H]+	144.8	32859911
AllCCS	[M+H-H2O]+	140.5	32859911
AllCCS	[M+NH4]+	148.9	32859911
AllCCS	[M+Na]+	150.0	32859911
AllCCS	[M-H]-	144.8	32859911
AllCCS	[M+Na-2H]-	145.0	32859911
AllCCS	[M+HCOO]-	145.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Repandiol	OCC1OC1C#CC#CC1OC1CO	2998.9	Standard polar	33892256
Repandiol	OCC1OC1C#CC#CC1OC1CO	1649.7	Standard non polar	33892256
Repandiol	OCC1OC1C#CC#CC1OC1CO	1968.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Repandiol,1TMS,isomer #1	C[Si](C)(C)OCC1OC1C#CC#CC1OC1CO	1874.4	Semi standard non polar	33892256
Repandiol,2TMS,isomer #1	C[Si](C)(C)OCC1OC1C#CC#CC1OC1CO[Si](C)(C)C	1948.3	Semi standard non polar	33892256
Repandiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC1C#CC#CC1OC1CO	2085.9	Semi standard non polar	33892256
Repandiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC1C#CC#CC1OC1CO[Si](C)(C)C(C)(C)C	2326.9	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 - Repandiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9700000000-63fdcde31e9569f96a72	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repandiol GC-MS (2 TMS) - 70eV, Positive	splash10-0ukl-9620000000-81df783b92a42fbb3981	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repandiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repandiol 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 - Repandiol 10V, Positive-QTOF	splash10-0002-0900000000-55b2fd4755077bc62f45	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 20V, Positive-QTOF	splash10-0592-3900000000-9b6d11121ba8ce508136	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 40V, Positive-QTOF	splash10-0zfs-9600000000-14aee89cc01c2bbc527d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 10V, Negative-QTOF	splash10-0006-0900000000-3e00f1bdcb31508f2a50	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 20V, Negative-QTOF	splash10-0006-3900000000-0dc8367eab644bbfa65b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 40V, Negative-QTOF	splash10-000x-9600000000-bc21ccdca2bb346bbb36	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 10V, Negative-QTOF	splash10-0006-0900000000-8bd93f9296182d079567	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 20V, Negative-QTOF	splash10-002f-2900000000-1775e3abc7f81c2a3008	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 40V, Negative-QTOF	splash10-0006-7900000000-10e115a0997e1d253d34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 10V, Positive-QTOF	splash10-052b-0900000000-586b6af9aec398be583f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 20V, Positive-QTOF	splash10-0554-5900000000-ff75a8f685b5efb2ecd9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repandiol 40V, Positive-QTOF	splash10-0hk9-9500000000-1ea6d1fd3ee34f7f5318	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart 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

FDB019232

KNApSAcK ID

C00057084

Chemspider ID

112972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127295

PDB ID

Not Available

ChEBI ID

166496

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1878741

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 Repandiol (HMDB0039606)

MOL for HMDB0039606 (Repandiol)

3D MOL for HMDB0039606 (Repandiol)

3D SDF for HMDB0039606 (Repandiol)

3D-SDF for HMDB0039606 (Repandiol)

PDB for HMDB0039606 (Repandiol)

3D PDB for HMDB0039606 (Repandiol)

SMILES for HMDB0039606 (Repandiol)

INCHI for HMDB0039606 (Repandiol)

Structure for HMDB0039606 (Repandiol)

3D Structure for HMDB0039606 (Repandiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra