NP-MRD: Showing NP-Card for Gibberellin A83 (NP0050192)

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Record Information

Version

2.0

Created at

2022-04-27 20:30:22 UTC

Updated at

2022-04-27 20:30:22 UTC

NP-MRD ID

NP0050192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A83

Description

(1R,2S,3S,4S,5S,8S,9S,12R,13R)-5-hydroxy-13-(hydroxymethyl)-4,8-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]Pentadecane-2,4-dicarboxylic acid belongs to the class of organic compounds known as c20-gibberellin 6-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position. Gibberellin A83 is found in Lupinus albus . Based on a literature review very few articles have been published on (1R,2S,3S,4S,5S,8S,9S,12R,13R)-5-hydroxy-13-(hydroxymethyl)-4,8-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]Pentadecane-2,4-dicarboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222302D          

 26 29  0  0  1  0            999 V2000
    3.3060    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601    0.5041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6741    0.0457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9342    0.4105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8801    1.2337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5660    1.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    2.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    1.4630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5753    0.7329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0175    1.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    1.5339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1721    2.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    0.6945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1471    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861    0.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1577    0.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9732   -0.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773   -1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846   -0.9322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354   -0.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1084   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7179   -1.3826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -0.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000    0.1393    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  1  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
  9 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  3 22  1  6  0  0  0
  3 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  2 26  1  6  0  0  0
M  END


  Mrv1652304272222302D          

 26 29  0  0  1  0            999 V2000
    3.3060    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601    0.5041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6741    0.0457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9342    0.4105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8801    1.2337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5660    1.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    2.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    1.4630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5753    0.7329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0175    1.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    1.5339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1721    2.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    0.6945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1471    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861    0.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1577    0.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9732   -0.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773   -1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846   -0.9322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354   -0.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1084   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7179   -1.3826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -0.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000    0.1393    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  1  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
  9 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  3 22  1  6  0  0  0
  3 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  2 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@H](O)[C@](C)([C@H]1[C@H](C(O)=O)[C@@]13C[C@@H](CO)[C@@H](C1)CC[C@@H]23)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O6/c1-18-6-5-13(22)19(2,17(25)26)15(18)14(16(23)24)20-7-10(3-4-12(18)20)11(8-20)9-21/h10-15,21-22H,3-9H2,1-2H3,(H,23,24)(H,25,26)/t10-,11+,12+,13+,14-,15+,18+,19-,20-/m1/s1

> <INCHI_KEY>
YZDQGRUATRTIAO-PCAOEKNSSA-N

> <FORMULA>
C20H30O6

> <MOLECULAR_WEIGHT>
366.454

> <EXACT_MASS>
366.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.74607344332334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3S,4S,5S,8S,9S,12R,13R)-5-hydroxy-13-(hydroxymethyl)-4,8-dimethyltetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
1.3441164700000008

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.698050391009154

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.026000765394091

> <JCHEM_PKA_STRONGEST_BASIC>
-1.527865629683459

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
92.59219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4S,5S,8S,9S,12R,13R)-5-hydroxy-13-(hydroxymethyl)-4,8-dimethyltetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic 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       6.171   2.478   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.272   0.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.992   0.085   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.610   0.766   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.510   2.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.790   3.159   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.268   3.824   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.990   2.731   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.074   1.368   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.033   2.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.204   2.863   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.321   4.227   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.288   4.196   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.636   1.296   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.275   0.397   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.078   0.755   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.267   1.734   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.161   0.213   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.817  -1.288   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.944  -2.337   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.345  -1.740   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.359  -1.319   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.802  -1.224   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.073  -2.581   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.342  -1.177   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.653   0.260   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4   22   23                                             
CONECT    4    3    5   18                                                  
CONECT    5    4    6    7    8                                             
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    5    9   13                                                  
CONECT    9    8   10   15   18                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14    9                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18    9    4   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    3                                                            
CONECT   23    3   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    2                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,4S,5S,8S,9S,12R,13R)-5-Hydroxy-13-(hydroxymethyl)-4,8-dimethyltetracyclo[10.2.1.0,.0,]pentadecane-2,4-dicarboxylate	Generator

Chemical Formula

C₂₀H₃₀O₆

Average Mass

366.4540 Da

Monoisotopic Mass

366.20424 Da

IUPAC Name

(1R,2S,3S,4S,5S,8S,9S,12R,13R)-5-hydroxy-13-(hydroxymethyl)-4,8-dimethyltetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid

Traditional Name

(1R,2S,3S,4S,5S,8S,9S,12R,13R)-5-hydroxy-13-(hydroxymethyl)-4,8-dimethyltetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@H](O)[C@](C)([C@H]1[C@H](C(O)=O)[C@@]13C[C@@H](CO)[C@@H](C1)CC[C@@H]23)C(O)=O

InChI Identifier

InChI=1S/C20H30O6/c1-18-6-5-13(22)19(2,17(25)26)15(18)14(16(23)24)20-7-10(3-4-12(18)20)11(8-20)9-21/h10-15,21-22H,3-9H2,1-2H3,(H,23,24)(H,25,26)/t10-,11+,12+,13+,14-,15+,18+,19-,20-/m1/s1

InChI Key

YZDQGRUATRTIAO-PCAOEKNSSA-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c20-gibberellin 6-carboxylic acids. These are c20-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

C20-gibberellin 6-carboxylic acids

Alternative Parents

Substituents

Gibberellane-6-carboxylic acid
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.11	ALOGPS
logP	1.34	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.59 m³·mol⁻¹	ChemAxon
Polarizability	38.75 Å³	ChemAxon
Number of Rings	4	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

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

101630863

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gibberellin A83 (NP0050192)

MOL for NP0050192 (Gibberellin A83)

3D MOL for NP0050192 (Gibberellin A83)

3D SDF for NP0050192 (Gibberellin A83)

3D-SDF for NP0050192 (Gibberellin A83)

PDB for NP0050192 (Gibberellin A83)

3D PDB for NP0050192 (Gibberellin A83)

SMILES for NP0050192 (Gibberellin A83)

INCHI for NP0050192 (Gibberellin A83)

Structure for NP0050192 (Gibberellin A83)

3D Structure for NP0050192 (Gibberellin A83)