MiMeDB: Showing metabocard for Gibberellin A12 7-aldehyde (MMDBc0053274)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:19:20 UTC

Update Date

2024-04-30 20:47:31 UTC

Metabolite ID

MMDBc0053274

Metabolite Identification

Common Name

Gibberellin A12 7-aldehyde

Description

Gibberellin A12 aldehyde (GA12-aldehyde), also known as gibberellin A12 7-aldehyde, belongs to the class of organic compounds known as C20-gibberellins. These are gibberellins with carboxy groups in positions 7 and 18 and some also in 20, while others have an aldehyde group in the latter position. Thus, gibberellin A12 aldehyde is considered to be an isoprenoid lipid molecule. Gibberellin A12 aldehyde is found in pulses. It is also a constituent of Phaseolus species, Pisum sativum (peas), and other plant species.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023522D          

 23 26  0  0  0  0            999 V2000
   -0.6002    1.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2656    2.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385   -0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6255    0.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296    1.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879    2.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988    1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893    1.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4744    0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    2.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359    0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    1.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232    2.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435    1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465    1.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852    3.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0992    3.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1229    2.6107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
 12  1  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15  6  1  0  0  0  0
 16 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  7  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  3  1  0  0  0  0
 19  8  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  2  0  0  0  0
 22 17  2  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053274

> <DATABASE_NAME>
MIME

> <SMILES>
CC12CCCC(C)(C1C(C=O)C13CC(CCC21)C(=C)C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-12-9-20-10-13(12)5-6-15(20)18(2)7-4-8-19(3,17(22)23)16(18)14(20)11-21/h11,13-16H,1,4-10H2,2-3H3,(H,22,23)

> <INCHI_KEY>
ZCTUNYRXJKLWPY-UHFFFAOYSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.25589305217993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-formyl-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylic acid

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
3.4273903603333338

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.017706011044307

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.61719932603328

> <JCHEM_PKA_STRONGEST_BASIC>
-7.041050560068249

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
88.07709999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-formyl-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylic 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      -1.120   3.304   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.231   0.427   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.096   5.399   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.155   1.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.752  -0.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.345   0.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.768   1.077   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.269   3.282   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.657   3.839   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.051   2.096   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.861   5.585   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.353   2.857   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.886   1.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.174   4.077   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.987   1.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.609   3.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.070   5.252   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.495   1.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.996   4.149   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.073   2.937   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.399   6.068   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.652   6.734   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.563   4.873   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    7    8                                                       
CONECT    5    6   13                                                       
CONECT    6    5   15                                                       
CONECT    7    4   18                                                       
CONECT    8    4   19                                                       
CONECT    9   12   20                                                       
CONECT   10   13   20                                                       
CONECT   11   14   21                                                       
CONECT   12    1    9   13                                                  
CONECT   13    5   10   12                                                  
CONECT   14   11   16   20                                                  
CONECT   15    6   18   20                                                  
CONECT   16   14   18   19                                                  
CONECT   17   19   22   23                                                  
CONECT   18    2    7   15   16                                             
CONECT   19    3    8   16   17                                             
CONECT   20    9   10   14   15                                             
CONECT   21   11                                                            
CONECT   22   17                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

Synonyms

Value	Source
Gibberellin a12 aldehyde	HMDB
Gibberellin-a-12-aldehyde	MeSH

Molecular Formula

C₂₀H₂₈O₃

Average Mass

316.4345

Monoisotopic Mass

316.203844762

IUPAC Name

2-formyl-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylic acid

Traditional Name

2-formyl-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C1C(C=O)C13CC(CCC21)C(=C)C3)C(O)=O

InChI Identifier

InChI=1S/C20H28O3/c1-12-9-20-10-13(12)5-6-15(20)18(2)7-4-8-19(3,17(22)23)16(18)14(20)11-21/h11,13-16H,1,4-10H2,2-3H3,(H,22,23)

InChI Key

ZCTUNYRXJKLWPY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c20-gibberellins. These are gibberellins with carboxy groups in positions 7 and 18 and some also in 20, while others have an aldehyde group in the latter position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C20-gibberellins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.005 g/L	ALOGPS
logP	2.95	ALOGPS
logP	3.43	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.08 m³·mol⁻¹	ChemAxon
Polarizability	35.26 Å³	ChemAxon
Number of Rings	4	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	splash10-0umr-1291000000-349711c661d5dc15dcd6	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5169000000-960a5dfc81fafb4819a6	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0059000000-7dc36be34a2f5195dd29	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-0093000000-d59673302f9027ebdca7	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0597-2090000000-db2a3f7450356a6027e0	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0095000000-5afa7d85c81962c12b57	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00r2-0191000000-af3c20720bf1c2dee967	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-3891000000-1b47b2608d5f11239d6a	2015-04-24	View Spectrum

Biological Properties

Cellular Locations

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	3	Human feces

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

HMDB0039484

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5253705

PDB ID

Not Available

ChEBI ID

15610

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.

Showing metabocard for Gibberellin A12 7-aldehyde (MMDBc0053274)

MOL for #<Metabolite:0x00007fecaec4e378>

3D MOL for #<Metabolite:0x00007fecaec4e378>

3D SDF for #<Metabolite:0x00007fecaec4e378>

3D-SDF for #<Metabolite:0x00007fecaec4e378>

PDB for #<Metabolite:0x00007fecaec4e378>

3D PDB for #<Metabolite:0x00007fecaec4e378>

SMILES for #<Metabolite:0x00007fecaec4e378>

INCHI for #<Metabolite:0x00007fecaec4e378>

Structure for #<Metabolite:0x00007fecaec4e378>

3D Structure for #<Metabolite:0x00007fecaec4e378>