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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:17:40 UTC

Update Date

2021-09-23 18:17:40 UTC

HMDB ID

HMDB0302506

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Deoxy-2,3-dihydromycosinol

Description

4-deoxy-2,3-dihydromycosinol is a member of the class of compounds known as ketals. Ketals are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. 4-deoxy-2,3-dihydromycosinol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4-deoxy-2,3-dihydromycosinol can be found in roman camomile, which makes 4-deoxy-2,3-dihydromycosinol a potential biomarker for the consumption of this food product.

Structure

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

  Mrv0541 02241221252D          

 15 16  0  0  0  0            999 V2000
   -3.0348   -0.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7022   -0.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4473   -1.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6223   -1.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -0.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -0.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125   -1.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -1.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0325   -0.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479   -0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479    0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771    0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021    0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271    0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521    0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  3  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 12 13  1  0  0  0  0
 13 14  3  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302506

> <DATABASE_NAME>
hmdb

> <SMILES>
CC#CC#CC=C1OC2(CCCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O2/c1-2-3-4-5-7-12-8-10-13(15-12)9-6-11-14-13/h7-8,10H,6,9,11H2,1H3

> <INCHI_KEY>
WTRXKCNFPMTAJV-UHFFFAOYSA-N

> <FORMULA>
C13H12O2

> <MOLECULAR_WEIGHT>
200.2332

> <EXACT_MASS>
200.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.536113485717877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(hexa-2,4-diyn-1-ylidene)-1,6-dioxaspiro[4.4]non-3-ene

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
2.725074503666666

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.272706731532557

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
62.46520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hexa-2,4-diyn-1-ylidene)-1,6-dioxaspiro[4.4]non-3-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -5.665  -0.285   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.911  -1.190   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.435  -2.655   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.895  -2.655   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.419  -1.190   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.173  -0.285   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.943  -2.655   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.403  -2.655   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.927  -1.190   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.463  -0.714   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.463   0.826   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.077   0.826   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.617   0.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.157   0.826   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.697   0.826   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    6    7                                             
CONECT    6    5    9                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0302506
HETATM    1  C1  UNL     1       7.127  -0.458  -0.021  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.711  -0.228   0.326  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.552  -0.031   0.598  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.193   0.205   0.900  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.031   0.419   1.151  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.666   0.689   1.452  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.272   0.191   0.665  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.081  -0.633  -0.519  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.293  -0.915  -1.010  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.304  -0.290  -0.168  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.175   0.712  -0.910  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.224   0.943   0.188  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.358  -0.475   0.701  1.00  0.00           C  
HETATM   14  O1  UNL     1      -3.211  -1.149   0.386  1.00  0.00           O  
HETATM   15  O2  UNL     1      -1.626   0.387   0.860  1.00  0.00           O  
HETATM   16  H1  UNL     1       7.197  -1.214  -0.844  1.00  0.00           H  
HETATM   17  H2  UNL     1       7.674  -0.822   0.857  1.00  0.00           H  
HETATM   18  H3  UNL     1       7.572   0.500  -0.366  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.458   1.292   2.315  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.882  -0.944  -0.907  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.470  -1.506  -1.880  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.650   1.623  -1.182  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.693   0.194  -1.723  1.00  0.00           H  
HETATM   24  H9  UNL     1      -5.152   1.351  -0.214  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.740   1.598   0.949  1.00  0.00           H  
HETATM   26  H11 UNL     1      -5.188  -0.933   0.085  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.628  -0.508   1.780  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    3
CONECT    3    4
CONECT    4    5    5    5
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8   15
CONECT    8    9    9   20
CONECT    9   10   21
CONECT   10   11   14   15
CONECT   11   12   22   23
CONECT   12   13   24   25
CONECT   13   14   26   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₂O₂

Average Molecular Weight

200.2332

Monoisotopic Molecular Weight

200.083729628

IUPAC Name

2-(hexa-2,4-diyn-1-ylidene)-1,6-dioxaspiro[4.4]non-3-ene

Traditional Name

2-(hexa-2,4-diyn-1-ylidene)-1,6-dioxaspiro[4.4]non-3-ene

CAS Registry Number

Not Available

SMILES

CC#CC#CC=C1OC2(CCCO2)C=C1

InChI Identifier

InChI=1S/C13H12O2/c1-2-3-4-5-7-12-8-10-13(15-12)9-6-11-14-13/h7-8,10H,6,9,11H2,1H3

InChI Key

WTRXKCNFPMTAJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Tetrahydrofuran
Dihydrofuran
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302506)

Food

Herb and spice

Herb

Roman camomile (FooDB: FOOD00046)

Process

Not Available

Role

Biological role

Industrial application

Agriculture

Pesticide (HMDB: HMDB0302506)

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
logP	3.3	ALOGPS
logP	2.73	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.47 m³·mol⁻¹	ChemAxon
Polarizability	22.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	145.705	32859911
AllCCS	[M+H-H2O]+	141.344	32859911
AllCCS	[M+Na]+	150.94	32859911
AllCCS	[M+NH4]+	149.768	32859911
AllCCS	[M-H]-	149.047	32859911
AllCCS	[M+Na-2H]-	149.227	32859911
AllCCS	[M+HCOO]-	149.535	32859911
DeepCCS	[M+H]+	137.572	30932474
DeepCCS	[M-H]-	134.699	30932474
DeepCCS	[M-2H]-	170.786	30932474
DeepCCS	[M+Na]+	145.93	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 10V, Positive-QTOF	splash10-0udi-4490000000-5109fad91a805d26bee4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 20V, Positive-QTOF	splash10-0udj-9530000000-ad38155547a61f6610df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 40V, Positive-QTOF	splash10-0fbd-9200000000-324a7155ec1e2223367b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 10V, Negative-QTOF	splash10-0002-3900000000-f030aa25f5e0e4b2ce13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 20V, Negative-QTOF	splash10-0005-4900000000-895ff31176094d93bbd3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 40V, Negative-QTOF	splash10-01ox-9400000000-cd3c6594dcdf9e7ddcd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 10V, Positive-QTOF	splash10-0udi-2490000000-d43aaa315966c34d268e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 20V, Positive-QTOF	splash10-0l4l-6910000000-1f2bc8af947241775762	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 40V, Positive-QTOF	splash10-00b9-9400000000-9190cd9efac177489412	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 10V, Negative-QTOF	splash10-0002-0900000000-9a55e37b93cc8d2eb060	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 20V, Negative-QTOF	splash10-0002-8900000000-4951d7c3614229795a8f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxy-2,3-dihydromycosinol 40V, Negative-QTOF	splash10-044r-9400000000-715e4c0f7814f3af25dd	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB021847

KNApSAcK ID

Not Available

Chemspider ID

93083

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

103031

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

Not Available

Showing metabocard for 4-Deoxy-2,3-dihydromycosinol (HMDB0302506)

MOL for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

3D MOL for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

3D SDF for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

3D-SDF for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

PDB for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

3D PDB for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

SMILES for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

INCHI for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

Structure for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

3D Structure for HMDB0302506 (4-Deoxy-2,3-dihydromycosinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra