NP-MRD: Showing NP-Card for Gibberellin A91 (NP0049691)

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Record Information

Version

2.0

Created at

2022-03-17 21:16:32 UTC

Updated at

2022-03-17 21:16:33 UTC

NP-MRD ID

NP0049691

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A91

Description

Gibberellin A91, also known as GA91 or holmium selenide, 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. Gibberellin A91 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gibberellin A91 has been detected, but not quantified in, several different foods, such as cereals and cereal products, common pea, common wheats, and wheats. This could make gibberellin A91 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216562D          

 26 30  0  0  0  0            999 V2000
   -2.5043   -1.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5652   -0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910   -1.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -0.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6261   -1.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.9563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7217    1.4348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9392    1.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6261    2.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5214    0.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736   -0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520    0.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0433    0.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130    0.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607   -0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956   -0.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740    0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043    0.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130    1.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1476    1.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606    2.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736   -1.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -2.3740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  5 25  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv0541 02241216562D          

 26 30  0  0  0  0            999 V2000
   -2.5043   -1.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5652   -0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910   -1.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -0.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6261   -1.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.9563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7217    1.4348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9392    1.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6261    2.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5214    0.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736   -0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520    0.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0433    0.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130    0.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607   -0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956   -0.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740    0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043    0.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130    1.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1476    1.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606    2.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736   -1.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -2.3740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  5 25  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049691

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(O)C(O)C3(OC1=O)C1CCC4(O)CC1(CC4=C)C(C23)C(O)=O

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

> <INCHI_KEY>
VDQMXBWLDLPSSR-UHFFFAOYSA-N

> <FORMULA>
C19H24O7

> <MOLECULAR_WEIGHT>
364.3897

> <EXACT_MASS>
364.152203122

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.49706678003926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-0.517976126666666

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.986743288764526

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.110560782065914

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9049290624413885

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
86.81439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.675  -2.775   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.922  -1.801   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.850  -1.899   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.779  -1.022   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.169  -2.678   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -3.652   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.214   2.678   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.753   2.678   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.169   4.139   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.973   1.412   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.850   0.146   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.311  -0.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.577   0.536   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.947   1.022   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.584   1.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.487  -0.340   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.045  -0.828   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.312   0.146   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.116   1.704   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.675   1.704   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.584   2.678   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.142   2.970   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.726   4.431   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.311  -2.385   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.630  -3.165   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.630  -4.431   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11   16                                             
CONECT    5    4    6   25                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11    4   10   12                                                  
CONECT   12    2   11   13   24                                             
CONECT   13   12                                                            
CONECT   14   15   19                                                       
CONECT   15   10   14   16   21                                             
CONECT   16    4   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   14   18   20   22                                             
CONECT   20   19                                                            
CONECT   21   15   22                                                       
CONECT   22   19   21   23                                                  
CONECT   23   22                                                            
CONECT   24   12   25                                                       
CONECT   25    5   24   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
Disodium (orthosilicato(4-)-O)oxozirconate(2-)	HMDB
GA91	HMDB
Holmium selenide	HMDB
Sodium zirconium oxide silicate (na2Zro(sio4))	HMDB
Sodium zirconium silicate	HMDB
5,13,14-Trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylate	Generator

Chemical Formula

C₁₉H₂₄O₇

Average Mass

364.3897 Da

Monoisotopic Mass

364.15220 Da

IUPAC Name

5,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

Traditional Name

5,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

CAS Registry Number

160965-01-5

SMILES

CC12CC(O)C(O)C3(OC1=O)C1CCC4(O)CC1(CC4=C)C(C23)C(O)=O

InChI Identifier

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

InChI Key

VDQMXBWLDLPSSR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pisum sativum	FooDB	KNAPSACK
Triticum aestivum	FooDB	KNAPSACK

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

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.41	ALOGPS
logP	-0.52	ChemAxon
logS	-1.4	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	86.81 m³·mol⁻¹	ChemAxon
Polarizability	36.5 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

External Links

HMDB ID

HMDB0040651

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020446

KNApSAcK ID

C00000216

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A91 (NP0049691)

MOL for NP0049691 (Gibberellin A91)

3D MOL for NP0049691 (Gibberellin A91)

3D SDF for NP0049691 (Gibberellin A91)

3D-SDF for NP0049691 (Gibberellin A91)

PDB for NP0049691 (Gibberellin A91)

3D PDB for NP0049691 (Gibberellin A91)

SMILES for NP0049691 (Gibberellin A91)

INCHI for NP0049691 (Gibberellin A91)

Structure for NP0049691 (Gibberellin A91)

3D Structure for NP0049691 (Gibberellin A91)