MiMeDB: Showing metabocard for Gibberellin A8 (MMDBc0053294)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:19:55 UTC

Update Date

2022-09-01 02:19:50 UTC

Metabolite ID

MMDBc0053294

Metabolite Identification

Common Name

Gibberellin A8

Description

Gibberellin A8, also known as GA8, belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position. Thus, gibberellin A8 is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on Gibberellin A8.

Structure

MOL SDF PDB SMILES InChI

ChEBI
  Mrv1652304232017252D          

 28 32  0  0  1  0            999 V2000
    6.8825   -5.5933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1679   -5.1809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1679   -4.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8825   -3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7228   -3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -4.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -5.1809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2725   -6.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1731   -6.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880   -4.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7228   -5.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880   -5.1809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0082   -4.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3026   -5.5933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0082   -5.1809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5880   -6.0953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4354   -5.5608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8851   -6.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3050   -6.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0345   -6.8527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5779   -6.8567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7693   -6.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0154   -3.5827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5898   -3.5586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6608   -4.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -4.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4355   -3.9911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3140   -5.2725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 10  1  0  0  0  0
 12 10  1  0  0  0  0
  1 12  1  0  0  0  0
 14 12  1  0  0  0  0
 12 16  1  1  0  0  0
  3  4  1  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  5 13  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 15 11  1  0  0  0  0
 15  9  1  1  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  7 11  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  2 17  1  1  0  0  0
  1 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21 19  1  0  0  0  0
 14 19  1  1  0  0  0
 22  8  2  0  0  0  0
 13 23  1  1  0  0  0
 10 24  1  6  0  0  0
  1 25  1  6  0  0  0
 26 25  2  0  0  0  0
 25 24  1  0  0  0  0
  4 10  1  0  0  0  0
  3 27  1  1  0  0  0
  7 28  1  6  0  0  0
M  END

ChEBI
  Mrv1652304232017252D          

 28 32  0  0  1  0            999 V2000
    6.8825   -5.5933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1679   -5.1809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1679   -4.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8825   -3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7228   -3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -4.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -5.1809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2725   -6.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1731   -6.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880   -4.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7228   -5.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880   -5.1809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0082   -4.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3026   -5.5933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0082   -5.1809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5880   -6.0953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4354   -5.5608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8851   -6.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3050   -6.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0345   -6.8527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5779   -6.8567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7693   -6.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0154   -3.5827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5898   -3.5586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6608   -4.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -4.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4355   -3.9911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3140   -5.2725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 10  1  0  0  0  0
 12 10  1  0  0  0  0
  1 12  1  0  0  0  0
 14 12  1  0  0  0  0
 12 16  1  1  0  0  0
  3  4  1  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  5 13  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 15 11  1  0  0  0  0
 15  9  1  1  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  7 11  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  2 17  1  1  0  0  0
  1 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21 19  1  0  0  0  0
 14 19  1  1  0  0  0
 22  8  2  0  0  0  0
 13 23  1  1  0  0  0
 10 24  1  6  0  0  0
  1 25  1  6  0  0  0
 26 25  2  0  0  0  0
 25 24  1  0  0  0  0
  4 10  1  0  0  0  0
  3 27  1  1  0  0  0
  7 28  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053294

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(C)[C@@H](O)[C@@H](O)C[C@@]21OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O7/c1-8-5-17-7-18(8,25)4-3-10(17)19-6-9(20)13(21)16(2,15(24)26-19)12(19)11(17)14(22)23/h9-13,20-21,25H,1,3-7H2,2H3,(H,22,23)/t9-,10+,11+,12+,13-,16-,17-,18-,19+/m0/s1

> <INCHI_KEY>
WZRRJZYYGOOHRC-UQJCXHNCSA-N

> <FORMULA>
C19H24O7

> <MOLECULAR_WEIGHT>
364.394

> <EXACT_MASS>
364.152203113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.42068003764592

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8S,9S,10R,11S,12R,13S)-5,12,13-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-0.746677592666666

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.401409820121973

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.11056141731746

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9049286693550885

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
86.92479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8S,9S,10R,11S,12R,13S)-5,12,13-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-20         0                                  
HETATM    1  C   UNK     0      12.847 -10.441   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.513  -9.671   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.513  -8.149   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.847  -7.379   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.149  -7.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.483  -8.149   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.483  -9.671   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.175 -11.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.123 -11.210   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.164  -8.149   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.149 -10.441   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.164  -9.671   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.815  -8.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.498 -10.441   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.815  -9.671   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      14.164 -11.378   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0      10.146 -10.380   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.852 -11.741   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.503 -12.011   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.864 -12.792   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.145 -12.799   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      20.103 -12.339   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      16.829  -6.688   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0      14.168  -6.643   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.433  -9.124   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.510  -9.035   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.146  -7.450   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      21.120  -9.842   0.000  0.00  0.00           O+0
CONECT    1   12    2   18   25                                             
CONECT    2    1    3   17                                                  
CONECT    3    4    2   27                                                  
CONECT    4    3   10                                                       
CONECT    5   13    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   11    8   28                                             
CONECT    8    7    9   22                                                  
CONECT    9   15    8                                                       
CONECT   10   13   12   24    4                                             
CONECT   11   15    7                                                       
CONECT   12   10    1   14   16                                             
CONECT   13   10    5   15   23                                             
CONECT   14   12   15   19                                                  
CONECT   15   13   14   11    9                                             
CONECT   16   12                                                            
CONECT   17    2                                                            
CONECT   18    1                                                            
CONECT   19   20   21   14                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    8                                                            
CONECT   23   13                                                            
CONECT   24   10   25                                                       
CONECT   25    1   26   24                                                  
CONECT   26   25                                                            
CONECT   27    3                                                            
CONECT   28    7                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

Synonyms

Value	Source
2beta-Hydroxygibberellin 1	ChEBI
3beta-Hydroxygibberellin a1	ChEBI
GA8	ChEBI
Gibberellin 8	ChEBI
2b-Hydroxygibberellin 1	Generator
2Β-hydroxygibberellin 1	Generator
3b-Hydroxygibberellin a1	Generator
3Β-hydroxygibberellin a1	Generator

Molecular Formula

C₁₉H₂₄O₇

Average Mass

364.394

Monoisotopic Mass

364.152203113

IUPAC Name

(1R,2R,5S,8S,9S,10R,11S,12R,13S)-5,12,13-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

Traditional Name

(1R,2R,5S,8S,9S,10R,11S,12R,13S)-5,12,13-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(C)[C@@H](O)[C@@H](O)C[C@@]21OC3=O

InChI Identifier

InChI=1S/C19H24O7/c1-8-5-17-7-18(8,25)4-3-10(17)19-6-9(20)13(21)16(2,15(24)26-19)12(19)11(17)14(22)23/h9-13,20-21,25H,1,3-7H2,2H3,(H,22,23)/t9-,10+,11+,12+,13-,16-,17-,18-,19+/m0/s1

InChI Key

WZRRJZYYGOOHRC-UQJCXHNCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C19-gibberellin 6-carboxylic acids

Alternative Parents

Substituents

20-norgibberellane-6-carboxylic acid
2-hydroxy,20-norgibberellane
Diterpene lactone
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

lactone (CHEBI:28861 )
C19-gibberellin (CHEBI:28861 )
gibberellin monocarboxylic acid (CHEBI:28861 )
Gibberellins (C03579 )
Gibberellins (LMPR0104170005 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	-0.41	ALOGPS
logP	-0.75	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-0.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.92 m³·mol⁻¹	ChemAxon
Polarizability	36.42 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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 (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

Biological Properties

Cellular Locations

Not Available

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	Ascomycota	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280607

PDB ID

Not Available

ChEBI ID

28861

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for Gibberellin A8 (MMDBc0053294)

MOL for #<Metabolite:0x00007fece5741218>

3D MOL for #<Metabolite:0x00007fece5741218>

3D SDF for #<Metabolite:0x00007fece5741218>

3D-SDF for #<Metabolite:0x00007fece5741218>

PDB for #<Metabolite:0x00007fece5741218>

3D PDB for #<Metabolite:0x00007fece5741218>

SMILES for #<Metabolite:0x00007fece5741218>

INCHI for #<Metabolite:0x00007fece5741218>

Structure for #<Metabolite:0x00007fece5741218>

3D Structure for #<Metabolite:0x00007fece5741218>