NP-MRD: Showing NP-Card for Gibberellin A82 (NP0050191)

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Record Information

Version

2.0

Created at

2022-04-27 20:30:19 UTC

Updated at

2022-04-27 20:30:19 UTC

NP-MRD ID

NP0050191

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A82

Description

(1R,2R,5R,6R,8R,9S,10R,11S,12S)-12-hydroxy-6-(hydroxymethyl)-11-methyl-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]Heptadecane-9-carboxylic acid 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 A82 is found in Lupinus albus and Phaeosphaeria sp. L489. Based on a literature review very few articles have been published on (1R,2R,5R,6R,8R,9S,10R,11S,12S)-12-hydroxy-6-(hydroxymethyl)-11-methyl-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]Heptadecane-9-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222302D          

 25 29  0  0  1  0            999 V2000
    3.2496    1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    0.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5442   -0.1497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9673    0.6119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8168    1.5554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6287    1.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    0.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490    0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -0.7782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0055    1.5796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5844    0.8073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0463    1.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7047    1.4920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3014    2.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583    2.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575    0.6347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0867    0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4046    0.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216    0.2451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9689   -0.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6080   -1.4466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927   -1.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0164   -0.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071    0.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  1  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 11 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  3 24  1  6  0  0  0
  2 25  1  6  0  0  0
M  END


  Mrv1652304272222302D          

 25 29  0  0  1  0            999 V2000
    3.2496    1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    0.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5442   -0.1497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9673    0.6119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8168    1.5554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6287    1.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    0.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490    0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -0.7782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0055    1.5796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5844    0.8073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0463    1.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7047    1.4920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3014    2.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583    2.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575    0.6347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0867    0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4046    0.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216    0.2451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9689   -0.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6080   -1.4466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927   -1.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0164   -0.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071    0.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  1  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 11 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  3 24  1  6  0  0  0
  2 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050191

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12[C@H]3[C@H](C(O)=O)[C@@]45C[C@@H](CO)[C@@H](C4)CC[C@H]5[C@@]3(CC[C@@H]1O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-17-12(21)4-5-19(25-16(17)24)11-3-2-9-6-18(11,7-10(9)8-20)13(14(17)19)15(22)23/h9-14,20-21H,2-8H2,1H3,(H,22,23)/t9-,10+,11-,12+,13-,14-,17-,18-,19-/m1/s1

> <INCHI_KEY>
UNOALJORZQRLGV-BFZXAUSBSA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.411

> <EXACT_MASS>
350.172938557

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.25183467967535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.549240709666666

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.445587816297298

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.226820682811469

> <JCHEM_PKA_STRONGEST_BASIC>
-1.527864311717392

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
86.15299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,6R,8R,9S,10R,11S,12S)-12-hydroxy-6-(hydroxymethyl)-11-methyl-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                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       6.066   2.163   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.996   0.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.749  -0.279   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.672   1.142   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.391   2.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.907   3.177   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.661   1.548   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.265   0.131   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.024  -1.453   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.877   2.949   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.091   1.507   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.086   2.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.315   2.785   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.563   4.225   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.042   4.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.601   1.185   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.162   0.415   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.118   0.588   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.489   1.376   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.280   0.457   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.809  -1.328   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.002  -2.700   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.360  -2.174   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.631  -1.609   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.480   0.002   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4    8   24                                             
CONECT    4    3    5   20                                                  
CONECT    5    4    6    7   10                                             
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   15                                                  
CONECT   11   10   12   17   20                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   11    4   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    3                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5R,6R,8R,9S,10R,11S,12S)-12-Hydroxy-6-(hydroxymethyl)-11-methyl-16-oxo-15-oxapentacyclo[9.3.2.1,.0,.0,]heptadecane-9-carboxylate	Generator

Chemical Formula

C₁₉H₂₆O₆

Average Mass

350.4110 Da

Monoisotopic Mass

350.17294 Da

IUPAC Name

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

Traditional Name

(1R,2R,5R,6R,8R,9S,10R,11S,12S)-12-hydroxy-6-(hydroxymethyl)-11-methyl-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

C[C@]12[C@H]3[C@H](C(O)=O)[C@@]45C[C@@H](CO)[C@@H](C4)CC[C@H]5[C@@]3(CC[C@@H]1O)OC2=O

InChI Identifier

InChI=1S/C19H26O6/c1-17-12(21)4-5-19(25-16(17)24)11-3-2-9-6-18(11,7-10(9)8-20)13(14(17)19)15(22)23/h9-14,20-21H,2-8H2,1H3,(H,22,23)/t9-,10+,11-,12+,13-,14-,17-,18-,19-/m1/s1

InChI Key

UNOALJORZQRLGV-BFZXAUSBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lupinus albus	Plant	KNApSAcK
Phaeosphaeria sp. L489	Fungi	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
Diterpene lactone
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Primary alcohol
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	0.87	ALOGPS
logP	0.55	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-1.5	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	2	ChemAxon
Refractivity	86.15 m³·mol⁻¹	ChemAxon
Polarizability	36.25 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9079500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10904240

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gibberellin A82 (NP0050191)

MOL for NP0050191 (Gibberellin A82)

3D MOL for NP0050191 (Gibberellin A82)

3D SDF for NP0050191 (Gibberellin A82)

3D-SDF for NP0050191 (Gibberellin A82)

PDB for NP0050191 (Gibberellin A82)

3D PDB for NP0050191 (Gibberellin A82)

SMILES for NP0050191 (Gibberellin A82)

INCHI for NP0050191 (Gibberellin A82)

Structure for NP0050191 (Gibberellin A82)

3D Structure for NP0050191 (Gibberellin A82)