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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:04:47 UTC
Update Date2022-03-07 02:55:06 UTC
HMDB IDHMDB0036897
Secondary Accession Numbers
  • HMDB36897
Metabolite Identification
Common NameGibberellin A17
DescriptionGibberellin A17 (GA17) belongs to the class of organic compounds known as C20-gibberellin 20-carboxylic acids. These are C20-gibberellins with a carboxyl group at the 6-position. Thus, gibberellin A17 is considered to be an isoprenoid lipid molecule. Gibberellin A17 is found in apple. Gibberellin A17 is isolated from seeds of Phaseolus vulgaris (kidney bean).
Structure
Data?1595283052
Synonyms
ValueSource
GA17ChEBI
Gibberellin 17ChEBI
(1alpha,4aalpha,4bbeta,10beta)-7-Hydroxy-1-methyl-8-methylenegibbane-1,4a,10-tricarboxylic acidHMDB
(1α,4aα,4bβ,10β)-7-Hydroxy-1-methyl-8-methylenegibbane-1,4a,10-tricarboxylic acidHMDB
Gibberellin A17HMDB
Chemical FormulaC20H26O7
Average Molecular Weight378.4162
Monoisotopic Molecular Weight378.167853186
IUPAC Name(1S,2S,3R,4R,8R,9R,12S)-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid
Traditional Name(1S,2S,3R,4R,8R,9R,12S)-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid
CAS Registry Number18411-79-5
SMILES
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C20H26O7/c1-10-8-18-9-19(10,27)7-4-11(18)20(16(25)26)6-3-5-17(2,15(23)24)13(20)12(18)14(21)22/h11-13,27H,1,3-9H2,2H3,(H,21,22)(H,23,24)(H,25,26)/t11-,12-,13-,17-,18+,19+,20-/m1/s1
InChI KeyAUKMHZZVLPQAOX-CDNFTCFOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c20-gibberellin 20-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentC20-gibberellin 20-carboxylic acids
Alternative Parents
Substituents
  • Gibberellane-20-carboxylic acid
  • Gibberellane-6-carboxylic acid
  • Tricarboxylic acid or derivatives
  • Tertiary alcohol
  • Cyclic alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.8 g/LALOGPS
logP0.87ALOGPS
logP1.62ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-0.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.25 m³·mol⁻¹ChemAxon
Polarizability37.91 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-215.98630932474
DeepCCS[M+Na]+191.15330932474
AllCCS[M+H]+185.232859911
AllCCS[M+H-H2O]+182.832859911
AllCCS[M+NH4]+187.532859911
AllCCS[M+Na]+188.132859911
AllCCS[M-H]-189.232859911
AllCCS[M+Na-2H]-189.332859911
AllCCS[M+HCOO]-189.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gibberellin A17[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O4179.4Standard polar33892256
Gibberellin A17[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O2665.1Standard non polar33892256
Gibberellin A17[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O3035.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gibberellin A17,1TMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O2885.2Semi standard non polar33892256
Gibberellin A17,1TMS,isomer #2C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2848.3Semi standard non polar33892256
Gibberellin A17,1TMS,isomer #3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O2878.6Semi standard non polar33892256
Gibberellin A17,1TMS,isomer #4C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O2873.0Semi standard non polar33892256
Gibberellin A17,2TMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O2844.6Semi standard non polar33892256
Gibberellin A17,2TMS,isomer #2C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O2846.5Semi standard non polar33892256
Gibberellin A17,2TMS,isomer #3C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2832.1Semi standard non polar33892256
Gibberellin A17,2TMS,isomer #4C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2841.5Semi standard non polar33892256
Gibberellin A17,2TMS,isomer #5C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2848.5Semi standard non polar33892256
Gibberellin A17,2TMS,isomer #6C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O2859.9Semi standard non polar33892256
Gibberellin A17,3TMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O2850.8Semi standard non polar33892256
Gibberellin A17,3TMS,isomer #2C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2839.1Semi standard non polar33892256
Gibberellin A17,3TMS,isomer #3C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2852.6Semi standard non polar33892256
Gibberellin A17,3TMS,isomer #4C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2862.7Semi standard non polar33892256
Gibberellin A17,4TMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C2881.3Semi standard non polar33892256
Gibberellin A17,1TBDMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O3100.6Semi standard non polar33892256
Gibberellin A17,1TBDMS,isomer #2C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3081.2Semi standard non polar33892256
Gibberellin A17,1TBDMS,isomer #3C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O3112.3Semi standard non polar33892256
Gibberellin A17,1TBDMS,isomer #4C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O3108.4Semi standard non polar33892256
Gibberellin A17,2TBDMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O3324.0Semi standard non polar33892256
Gibberellin A17,2TBDMS,isomer #2C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O3317.8Semi standard non polar33892256
Gibberellin A17,2TBDMS,isomer #3C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3287.8Semi standard non polar33892256
Gibberellin A17,2TBDMS,isomer #4C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3304.7Semi standard non polar33892256
Gibberellin A17,2TBDMS,isomer #5C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3304.7Semi standard non polar33892256
Gibberellin A17,2TBDMS,isomer #6C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O3335.8Semi standard non polar33892256
Gibberellin A17,3TBDMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O3538.8Semi standard non polar33892256
Gibberellin A17,3TBDMS,isomer #2C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3518.5Semi standard non polar33892256
Gibberellin A17,3TBDMS,isomer #3C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3518.1Semi standard non polar33892256
Gibberellin A17,3TBDMS,isomer #4C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3523.7Semi standard non polar33892256
Gibberellin A17,4TBDMS,isomer #1C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C3728.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gibberellin A17 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A17 10V, Negative-QTOFsplash10-00pi-0019000000-38d46803d0ab55a105852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A17 20V, Negative-QTOFsplash10-000i-0095000000-32b77eb8d1862f3a1ed42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A17 40V, Negative-QTOFsplash10-00or-2149000000-850250252d6fcf16bfeb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A17 10V, Positive-QTOFsplash10-004i-0019000000-297451eaf3d428e1b08f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A17 20V, Positive-QTOFsplash10-00nr-0029000000-959436bec37b01f89fac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gibberellin A17 40V, Positive-QTOFsplash10-004r-1039000000-96f19ff4a547778c9a7a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015858
KNApSAcK IDC00000017
Chemspider ID4574148
KEGG Compound IDNot Available
BioCyc IDCPD1F-86
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5460657
PDB IDNot Available
ChEBI ID24236
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. 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. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.