NP-MRD: Showing NP-Card for Theasaponin A5 (NP0338509)

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Record Information

Version

2.0

Created at

2024-09-11 15:49:03 UTC

Updated at

2024-09-11 15:49:03 UTC

NP-MRD ID

NP0338509

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Theasaponin A5

Description

Theasaponin A5, also known as GA5, 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. Thus, theasaponin A5 is considered to be an isoprenoid lipid molecule. Theasaponin A5 was first documented in 1971 (PMID: 24488428). Theasaponin A5 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221162D          

 26 30  0  0  1  0            999 V2000
   -0.4782   -3.9694    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4710   -4.7949    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1934   -3.5531    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2442   -3.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -4.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042   -4.7985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2993   -5.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042   -3.9694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2442   -2.7313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9514   -3.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958   -6.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478   -2.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970   -4.3785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028   -5.3253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4774   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -3.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9038   -3.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -5.2101    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2958   -3.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958   -4.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6056   -6.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8246   -4.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3341   -4.2916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686   -4.7953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -2.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482   -2.0188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  1  0  0  0
  9 15  1  0  0  0  0
  3 13  1  1  0  0  0
  1  2  1  0  0  0  0
  6 14  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  1  1  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  6  0  0  0
  6 18  1  0  0  0  0
 16 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  2  0  0  0  0
 18 21  1  1  0  0  0
 18 22  1  6  0  0  0
 22 17  1  0  0  0  0
 22 23  2  0  0  0  0
  7 11  2  0  0  0  0
  7 24  1  0  0  0  0
 10 12  2  0  0  0  0
  3 25  1  0  0  0  0
 25 15  1  0  0  0  0
  9 26  1  0  0  0  0
M  END


  Mrv0541 02241221162D          

 26 30  0  0  1  0            999 V2000
   -0.4782   -3.9694    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4710   -4.7949    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1934   -3.5531    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2442   -3.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -4.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042   -4.7985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2993   -5.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9042   -3.9694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2442   -2.7313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9514   -3.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958   -6.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478   -2.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970   -4.3785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028   -5.3253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4774   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -3.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9038   -3.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -5.2101    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2958   -3.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958   -4.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6056   -6.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8246   -4.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3341   -4.2916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686   -4.7953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -2.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482   -2.0188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  1  0  0  0
  9 15  1  0  0  0  0
  3 13  1  1  0  0  0
  1  2  1  0  0  0  0
  6 14  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  1  1  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  6  0  0  0
  6 18  1  0  0  0  0
 16 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  2  0  0  0  0
 18 21  1  1  0  0  0
 18 22  1  6  0  0  0
 22 17  1  0  0  0  0
 22 23  2  0  0  0  0
  7 11  2  0  0  0  0
  7 24  1  0  0  0  0
 10 12  2  0  0  0  0
  3 25  1  0  0  0  0
 25 15  1  0  0  0  0
  9 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338509

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@]3(C)C=CC[C@@]21OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O5/c1-10-8-17-9-18(10,23)7-4-11(17)19-6-3-5-16(2,15(22)24-19)13(19)12(17)14(20)21/h3,5,11-13,23H,1,4,6-9H2,2H3,(H,20,21)/t11-,12-,13-,16-,17+,18+,19-/m1/s1

> <INCHI_KEY>
ZOWHLBOPCIHIHW-KQBHUUJHSA-N

> <FORMULA>
C19H22O5

> <MOLECULAR_WEIGHT>
330.375

> <EXACT_MASS>
330.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.48204936310678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,8S,9S,10R,11S)-5-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-12-ene-9-carboxylic acid

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.2699094306666674

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.32984793805357

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.255557382102413

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9049275069247206

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
85.20799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gibberellin A5

> <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      -0.893  -7.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.879  -8.950   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.228  -6.632   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.456  -6.639   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.442  -8.173   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.555  -8.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.559  -9.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.555  -7.410   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.456  -5.098   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.776  -5.855   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.552 -11.476   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.263  -5.456   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -2.234  -8.173   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.992  -9.941   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -0.891  -4.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.856  -6.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.554  -5.954   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.856  -9.726   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.152  -7.445   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.152  -8.958   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.864 -11.224   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.273  -8.011   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.357  -8.011   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.995  -8.951   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.240  -5.011   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.210  -3.768   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3   13    1    8   25                                             
CONECT    4    1    9                                                       
CONECT    5    1   10                                                       
CONECT    6    8   14    2   18                                             
CONECT    7    2   11   24                                                  
CONECT    8    6    3   16   17                                             
CONECT    9   10   15    4   26                                             
CONECT   10    9    5   12                                                  
CONECT   11    7                                                            
CONECT   12   10                                                            
CONECT   13    3                                                            
CONECT   14    6                                                            
CONECT   15    9   25                                                       
CONECT   16    8   19                                                       
CONECT   17    8   22                                                       
CONECT   18    6   20   21   22                                             
CONECT   19   16   20                                                       
CONECT   20   18   19                                                       
CONECT   21   18                                                            
CONECT   22   18   17   23                                                  
CONECT   23   22                                                            
CONECT   24    7                                                            
CONECT   25    3   15                                                       
CONECT   26    9                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
GA5	ChEBI

Chemical Formula

C₁₉H₂₂O₅

Average Mass

330.3750 Da

Monoisotopic Mass

330.14672 Da

IUPAC Name

(1R,2R,5S,8S,9S,10R,11S)-5-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-12-ene-9-carboxylic acid

Traditional Name

gibberellin A5

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@]3(C)C=CC[C@@]21OC3=O

InChI Identifier

InChI=1S/C19H22O5/c1-10-8-17-9-18(10,23)7-4-11(17)19-6-3-5-16(2,15(22)24-19)13(19)12(17)14(20)21/h3,5,11-13,23H,1,4,6-9H2,2H3,(H,20,21)/t11-,12-,13-,16-,17+,18+,19-/m1/s1

InChI Key

ZOWHLBOPCIHIHW-KQBHUUJHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

lactone (CHEBI:29598 )
C19-gibberellin (CHEBI:29598 )
gibberellin monocarboxylic acid (CHEBI:29598 )
Gibberellins (C11871 )
Gibberellins (LMPR0104170028 )

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	1.55	ALOGPS
logP	1.27	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-0.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.21 m³·mol⁻¹	ChemAxon
Polarizability	45.48 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

FDB001831

KNApSAcK ID

C00000005

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-15217

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281988

PDB ID

Not Available

ChEBI ID

29598

Good Scents ID

Not Available

References

General References

Jones RL, Stoddart JL, Macmillan J, Cloke C: Structural modification of gibberellins by in-vitro hydroxylating systems. Planta. 1971 Sep;101(3):231-41. doi: 10.1007/BF00386830. [PubMed:24488428 ]

Showing NP-Card for Theasaponin A5 (NP0338509)

MOL for NP0338509 (Theasaponin A5)

3D MOL for NP0338509 (Theasaponin A5)

3D SDF for NP0338509 (Theasaponin A5)

3D-SDF for NP0338509 (Theasaponin A5)

PDB for NP0338509 (Theasaponin A5)

3D PDB for NP0338509 (Theasaponin A5)

SMILES for NP0338509 (Theasaponin A5)

INCHI for NP0338509 (Theasaponin A5)

Structure for NP0338509 (Theasaponin A5)

3D Structure for NP0338509 (Theasaponin A5)