MiMeDB: Showing metabocard for Dihydrophaseic acid (MMDBc0053089)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:13:59 UTC

Update Date

2024-04-30 20:46:10 UTC

Metabolite ID

MMDBc0053089

Metabolite Identification

Common Name

Dihydrophaseic acid

Description

Dihydrophaseic acid (DPA), also known as 4'-dihydrophaseic acid, belongs to the class of organic compounds known as abscisic acid and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety. Dihydrophaseic acid is found in coconut. Dihydrophaseic acid is isolated from French beans.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023512D          

 23 24  0  0  0  0            999 V2000
    3.7291   -1.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001    2.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -1.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3583   -0.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -0.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -2.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -0.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8045    1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9273   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6118    0.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -2.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    1.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812    0.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424    0.6356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -3.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3236   -1.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6485    1.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8045    0.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133   -1.3177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4457   -0.1550    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634   -2.9494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  2  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14  8  1  0  0  0  0
 15  5  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18 12  1  0  0  0  0
 19 15  1  0  0  0  0
 20  9  1  0  0  0  0
 20 14  1  0  0  0  0
 21  4  1  0  0  0  0
 22  5  1  0  0  0  0
 23  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053089

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1(O)C2(C)COC1(C)CC(O)C2)\C(\C)=C(\[H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-

> <INCHI_KEY>
XIVFQYWMMJWUCD-IGTFLHFFSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.3322

> <EXACT_MASS>
282.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.79493005551389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoic acid

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
0.5024939413333337

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.891974587545853

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.566584044161994

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7397165799455063

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
75.0039

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0       6.961  -2.551   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.240   4.443   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.956  -2.110   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.402  -1.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.905  -0.088   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.030  -4.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.207   2.500   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.207  -0.275   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.502   1.883   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.464  -2.913   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.875   1.113   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.533  -4.753   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.706   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.706  -0.617   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.138   1.113   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.612   1.186   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.098  -6.230   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.471  -3.638   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.944   2.055   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.502   0.343   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       3.011  -2.460   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       6.432  -0.289   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       6.092  -5.506   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5   10   21                                                  
CONECT    5    4   15   22                                                  
CONECT    6   10   12   23                                                  
CONECT    7   11   13                                                       
CONECT    8   11   14                                                       
CONECT    9   13   20                                                       
CONECT   10    1    4    6                                                  
CONECT   11    7    8   16                                                  
CONECT   12    6   17   18                                                  
CONECT   13    2    7    9   15                                             
CONECT   14    3    8   15   20                                             
CONECT   15    5   13   14   19                                             
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   12                                                            
CONECT   19   15                                                            
CONECT   20    9   14                                                       
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    6                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

Synonyms

Value	Source
Dihydrophaseate	Generator
(-)-Dihydrophaseic acid	HMDB
5-(3,8-Dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]oct-8-yl)-3-methyl-2,4-pentadienoic acid, 9ci	HMDB

Molecular Formula

C₁₅H₂₂O₅

Average Mass

282.3322

Monoisotopic Mass

282.146723814

IUPAC Name

(2Z,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoic acid

Traditional Name

(2Z,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1(O)C2(C)COC1(C)CC(O)C2)\C(\C)=C(\[H])C(O)=O

InChI Identifier

InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-

InChI Key

XIVFQYWMMJWUCD-IGTFLHFFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Abscisic acids and derivatives

Alternative Parents

Substituents

Abscisic acid
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Oxepane
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.13 g/L	ALOGPS
logP	0.62	ALOGPS
logP	0.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75 m³·mol⁻¹	ChemAxon
Polarizability	29.79 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-6390000000-15205983f888cc8aae34	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00o0-5302900000-06eb8ff722caa23827b4	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0090000000-39cb65eb76c4015dff61	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0600-0190000000-daee06671fa05492ff10	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v4i-6790000000-f456e9d8a76408cfbc3e	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0190000000-e1034d3cd46d13509eac	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02ar-1190000000-4a1fd8d5a91c0ecc7487	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-2890000000-5341ed0e427da270bdee	2016-08-03	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0038660

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018059

KNApSAcK ID

Not Available

Chemspider ID

24808182

KEGG Compound ID

C15971

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752416

PDB ID

Not Available

ChEBI ID

23758

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
D. C. Walton, B. Dorn, J. Fey (1973). D. C. Walton, B. Dorn, J. Fey, The isolation of an abscisic-acid metabolite, 4'-dihydrophaseic acid, from non-imbibed Phaseolus vulgaris seed, Planta (Berl.) 112, 87-90 (1973) [Isolation]. Planta.

Showing metabocard for Dihydrophaseic acid (MMDBc0053089)

MOL for #<Metabolite:0x00007feca8c47b00>

3D MOL for #<Metabolite:0x00007feca8c47b00>

3D SDF for #<Metabolite:0x00007feca8c47b00>

3D-SDF for #<Metabolite:0x00007feca8c47b00>

PDB for #<Metabolite:0x00007feca8c47b00>

3D PDB for #<Metabolite:0x00007feca8c47b00>

SMILES for #<Metabolite:0x00007feca8c47b00>

INCHI for #<Metabolite:0x00007feca8c47b00>

Structure for #<Metabolite:0x00007feca8c47b00>

3D Structure for #<Metabolite:0x00007feca8c47b00>