NP-MRD: Showing NP-Card for Gibberellin A98 (NP0049865)

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Record Information

Version

2.0

Created at

2022-03-17 21:19:22 UTC

Updated at

2022-03-17 21:19:22 UTC

NP-MRD ID

NP0049865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A98

Description

Gibberellin A98, also known as GA98, 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 A98 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gibberellin A98 has been detected, but not quantified in, several different foods, such as black-eyed pea, herbs and spices, jujubes, common verbena, and sesbania flowers. Gibberellin A98 is found in Pinus sativum. This could make gibberellin A98 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241220012D          

 26 30  0  0  0  0            999 V2000
   -0.6933    0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9064    0.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2151   -0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4239    0.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270    0.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788    1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774    1.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2918    0.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063   -0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7530    0.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547    1.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9661   -0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2939   -0.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2918   -0.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028    0.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6933    1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776    0.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274   -1.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2151   -1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -1.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013   -1.4541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3 22  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 26  1  0  0  0  0
  8  9  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 20  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 21  2  0  0  0  0
 17 18  1  0  0  0  0
 17 25  2  0  0  0  0
 18 19  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
M  END


  Mrv0541 02241220012D          

 26 30  0  0  0  0            999 V2000
   -0.6933    0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9064    0.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2151   -0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4239    0.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270    0.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788    1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774    1.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2918    0.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063   -0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7530    0.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547    1.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9661   -0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2939   -0.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2918   -0.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028    0.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6933    1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776    0.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274   -1.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2151   -1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -1.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013   -1.4541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3 22  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 26  1  0  0  0  0
  8  9  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 20  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 21  2  0  0  0  0
 17 18  1  0  0  0  0
 17 25  2  0  0  0  0
 18 19  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(O)CC3(COC1=O)C1CCC4(O)CC1(CC4=C)C(C23)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-10-5-18-8-20(10,25)4-3-12(18)19-7-11(21)6-17(2,16(24)26-9-19)14(19)13(18)15(22)23/h11-14,21,25H,1,3-9H2,2H3,(H,22,23)

> <INCHI_KEY>
MEKWLWHELUEYHS-UHFFFAOYSA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.4168

> <EXACT_MASS>
362.172938564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.12274782407031

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,16-dihydroxy-11-methyl-6-methylidene-12-oxo-13-oxapentacyclo[9.3.3.1⁵,⁸.0¹,¹⁰.0²,⁸]octadecane-9-carboxylic acid

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.42368828866666636

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.199216971836005

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.246733004478766

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9048824007538662

> <JCHEM_POLAR_SURFACE_AREA>
104.05999999999999

> <JCHEM_REFRACTIVITY>
90.48259999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,16-dihydroxy-11-methyl-6-methylidene-12-oxo-13-oxapentacyclo[9.3.3.1⁵,⁸.0¹,¹⁰.0²,⁸]octadecane-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  C   UNK     0      -1.294   1.611   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.692   0.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.402  -0.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.791   0.251   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.237   1.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.387   2.699   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.878   2.296   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.278   0.803   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.185  -0.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310   0.015   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.272   1.211   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.715   2.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   2.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197  -1.236   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.670  -0.277   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.415  -1.627   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.278  -1.380   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.552   1.303   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.294   3.150   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.812   1.211   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.042  -0.975   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.171  -2.050   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.402  -3.384   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.710  -2.050   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.042  -2.714   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -4.968   3.384   0.000  0.00  0.00           O+0
CONECT    1    2    5    6   19                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   10   14                                             
CONECT    5    1    4   13                                                  
CONECT    6    1    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    2    8   16   17                                             
CONECT   10    4   11                                                       
CONECT   11   10   12   15   20                                             
CONECT   12   11   13                                                       
CONECT   13    5   12                                                       
CONECT   14    4   15                                                       
CONECT   15   11   14   21                                                  
CONECT   16    9                                                            
CONECT   17    9   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19    1   18                                                       
CONECT   20   11                                                            
CONECT   21   15                                                            
CONECT   22    3   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   17                                                            
CONECT   26    7                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
GA98	HMDB
5,16-Dihydroxy-11-methyl-6-methylidene-12-oxo-13-oxapentacyclo[9.3.3.1⁵,⁸.0¹,¹⁰.0²,⁸]octadecane-9-carboxylate	Generator

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4168 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

5,16-dihydroxy-11-methyl-6-methylidene-12-oxo-13-oxapentacyclo[9.3.3.1⁵,⁸.0¹,¹⁰.0²,⁸]octadecane-9-carboxylic acid

Traditional Name

5,16-dihydroxy-11-methyl-6-methylidene-12-oxo-13-oxapentacyclo[9.3.3.1⁵,⁸.0¹,¹⁰.0²,⁸]octadecane-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CC(O)CC3(COC1=O)C1CCC4(O)CC1(CC4=C)C(C23)C(O)=O

InChI Identifier

InChI=1S/C20H26O6/c1-10-5-18-8-20(10,25)4-3-12(18)19-7-11(21)6-17(2,16(24)26-9-19)14(19)13(18)15(22)23/h11-14,21,25H,1,3-9H2,2H3,(H,22,23)

InChI Key

MEKWLWHELUEYHS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pinus sativum	Plant	KNApSAcK
Spinacia oleracea	FooDB	KNAPSACK
Triticum aestivum	FooDB	KNAPSACK
Vicia faba	FooDB	KNAPSACK
Zea mays L.	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
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	0.44	ALOGPS
logP	0.42	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-0.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.48 m³·mol⁻¹	ChemAxon
Polarizability	37.12 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041510

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021483

KNApSAcK ID

C00000299

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

131753151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A98 (NP0049865)

MOL for NP0049865 (Gibberellin A98)

3D MOL for NP0049865 (Gibberellin A98)

3D SDF for NP0049865 (Gibberellin A98)

3D-SDF for NP0049865 (Gibberellin A98)

PDB for NP0049865 (Gibberellin A98)

3D PDB for NP0049865 (Gibberellin A98)

SMILES for NP0049865 (Gibberellin A98)

INCHI for NP0049865 (Gibberellin A98)

Structure for NP0049865 (Gibberellin A98)

3D Structure for NP0049865 (Gibberellin A98)