NP-MRD: Showing NP-Card for Gibberellin A29 (NP0048133)

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Record Information

Version

2.0

Created at

2022-03-17 20:51:37 UTC

Updated at

2022-03-17 20:51:37 UTC

NP-MRD ID

NP0048133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A29

Description

(2E,6Z)-2,6-Nonadien-1-Yl acetate, also known as 1-acetate(2E,6Z)-2,6-nonadien-1-ol or 2(e)-6(e)-nonadienyl acetate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol (2E,6Z)-2,6-Nonadien-1-Yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa) (2E,6Z)-2,6-Nonadien-1-Yl acetate is a fatty, green, and leafy tasting compound. Gibberellin A29 is found in Alstroemeria hybrida, Arabidopsis thaliana, Betula pendula , Calonyction aculeatum, Citrus unshiu , Eucalyptus globulus , Fragaria x ananassa Duch.cv.Elsanta, Helianthus annuus , Ipomoea alba, Ipomoea purpurea, Lathyrus odoratus , Leucaena leucocephala , Lolium perenne , Lolium temulentum , Pharbitis purpurea, Picea abies , Prunus subhirtella, Eriobotrya japonica , Saccharum spp., Salix pentandra, Saponaria glutinosa, Silene armeria, Solanum lycopersicum , Thlaspi arvense and Zea mays. Outside of the human body,.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211472D          

 25 29  0  0  0  0            999 V2000
   -1.1571   -1.2280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516   -0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0711   -1.3697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -0.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430   -1.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3933   -1.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6295   -2.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6295   -0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3853    0.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6295    1.4642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737    1.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    2.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0626    0.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3068   -0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0154   -0.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7240    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5823    0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853    1.2280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    1.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099    1.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4406    2.3617    0.0000 C   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  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv0541 02241211472D          

 25 29  0  0  0  0            999 V2000
   -1.1571   -1.2280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516   -0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0711   -1.3697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -0.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430   -1.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3933   -1.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6295   -2.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6295   -0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3853    0.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6295    1.4642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737    1.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    2.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0626    0.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3068   -0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0154   -0.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7240    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5823    0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853    1.2280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    1.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099    1.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4406    2.3617    0.0000 C   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  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(O)CC3(OC1=O)C1CCC4(O)CC1(CC4=C)C(C23)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O6/c1-9-5-17-8-18(9,24)4-3-11(17)19-7-10(20)6-16(2,15(23)25-19)13(19)12(17)14(21)22/h10-13,20,24H,1,3-8H2,2H3,(H,21,22)

> <INCHI_KEY>
BKBYHSYZKIAJDA-UHFFFAOYSA-N

> <FORMULA>
C19H24O6

> <MOLECULAR_WEIGHT>
348.3903

> <EXACT_MASS>
348.1572885

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.60800576955347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
0.1723185543333336

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.12640542362605

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.195147073301521

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9049278765738004

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
85.7173

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,13-dihydroxy-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      -2.160  -2.292   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.336  -1.146   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.133  -2.557   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.837  -0.970   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.014  -2.557   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.601  -2.998   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.042  -4.409   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.747  -1.763   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.042  -0.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.453   0.617   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.042   2.733   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.631   2.733   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.014   4.144   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.925   1.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.719   0.177   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.984   0.970   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.661   1.146   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.573  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.895  -0.881   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.218   0.177   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.954   1.763   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.453   2.292   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.661   2.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.072   2.998   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.689   4.409   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15   18                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    2    8   10   15                                             
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15    4    9   14                                                  
CONECT   16   17   21                                                       
CONECT   17   14   16   18   23                                             
CONECT   18    4   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   16   20   22   24                                             
CONECT   22   21                                                            
CONECT   23   17   24                                                       
CONECT   24   21   23   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
(2E,6Z)-2,6-Nonadien-1-yl acetic acid	Generator
(2E,6Z)-Nona-2,6-dienyl acetate	HMDB
1-Acetate(2E,6Z)-2,6-nonadien-1-ol	HMDB
2(e)-6(e)-Nonadienyl acetate	HMDB
2-trans-6-cis-Nonadienyl acetate	HMDB
Acetate(2E,6Z)-2,6-nonadien-1-ol	HMDB
Acetate(e,Z)-2,6-nonadien-1-ol	HMDB
FEMA 3952	HMDB
Nonadienyl acetate	HMDB
trans,cis-2,6-Nonadienyl acetate	HMDB
trans-2,cis-6-Nonadienyl acetate	HMDB
trans-2-cis-6-Nonadienyl acetate	HMDB
2-Epi-gibberellin a29	HMDB
GA81	HMDB
5,13-Dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylate	Generator

Chemical Formula

C₁₉H₂₄O₆

Average Mass

348.3903 Da

Monoisotopic Mass

348.15729 Da

IUPAC Name

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

CAS Registry Number

29774-53-6

SMILES

CC12CC(O)CC3(OC1=O)C1CCC4(O)CC1(CC4=C)C(C23)C(O)=O

InChI Identifier

InChI=1S/C19H24O6/c1-9-5-17-8-18(9,24)4-3-11(17)19-7-10(20)6-16(2,15(23)25-19)13(19)12(17)14(21)22/h10-13,20,24H,1,3-8H2,2H3,(H,21,22)

InChI Key

BKBYHSYZKIAJDA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	KNAPSACK
Alstroemeria hybrida	Plant	KNApSAcK
Arabidopsis thaliana	Plant	KNApSAcK
Betula pendula	Plant	KNApSAcK
Brassica napus	FooDB	KNAPSACK
Calonyction aculeatum	Plant	KNApSAcK
Carthamus tinctorius	FooDB	KNAPSACK
Citrus reticulata	FooDB	KNAPSACK
Citrus unshiu	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	KNAPSACK
Eriobotrya japonica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Eucalyptus globulus	Plant	KNApSAcK
Fragaria x ananassa	FooDB	KNAPSACK
Fragaria x ananassa Duch.cv.Elsanta	Plant	KNApSAcK
Helianthus annuus L.	Plant	KNApSAcK
Hordeum vulgare	FooDB	KNAPSACK
Ipomoea alba	LOTUS Database	35616633
Ipomoea purpurea	LOTUS Database	35616633
Juglans regia	FooDB	KNAPSACK
Lactuca sativa	FooDB	KNAPSACK
Lathyrus odoratus	Plant	KNApSAcK
Leucaena glauca	Plant	KNApSAcK
Lolium perenne	Plant	KNApSAcK
Lolium temulentum	Plant	KNApSAcK
Mangifera indica	FooDB	KNAPSACK
Oryza sativa	FooDB	KNAPSACK
Pharbitis purpurea	Plant	KNApSAcK
Phaseolus coccineus	FooDB	KNAPSACK
Phaseolus lunatus	FooDB	KNAPSACK
Phaseolus vulgaris	FooDB	KNAPSACK
Picea abies	Plant	KNApSAcK
Pisum sativum	FooDB	KNAPSACK
Prunus armeniaca	FooDB	KNAPSACK
Prunus avium	FooDB	KNAPSACK
Prunus domestica	FooDB	KNAPSACK
Prunus subhirtella	Plant	KNApSAcK
Raphanus sativus	FooDB	KNAPSACK
Rhaphiolepis bibas	Plant	KNApSAcK
Saccharum spp.	Plant	KNApSAcK
Salix pentandra	Plant	KNApSAcK
Saponaria glutinosa	LOTUS Database	35616633
Sechium edule	FooDB	KNAPSACK
Silene armeria	Plant	KNApSAcK
Solanum lycopersicum	Plant	KNApSAcK
Solanum lycopersicum var. lycopersicum	FooDB	KNAPSACK
Spinacia oleracea	FooDB	KNAPSACK
Thlaspi arvense	Plant	KNApSAcK
Triticum aestivum	FooDB	KNAPSACK
Vicia faba	FooDB	KNAPSACK
Vigna unguiculata	FooDB	KNAPSACK
Zea mays	LOTUS Database	35616633
Zea mays L.	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	0.09	ALOGPS
logP	0.17	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.2	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	85.72 m³·mol⁻¹	ChemAxon
Polarizability	35.61 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

HMDB0038079

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017291

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

124355621

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A29 (NP0048133)

MOL for NP0048133 (Gibberellin A29)

3D MOL for NP0048133 (Gibberellin A29)

3D SDF for NP0048133 (Gibberellin A29)

3D-SDF for NP0048133 (Gibberellin A29)

PDB for NP0048133 (Gibberellin A29)

3D PDB for NP0048133 (Gibberellin A29)

SMILES for NP0048133 (Gibberellin A29)

INCHI for NP0048133 (Gibberellin A29)

Structure for NP0048133 (Gibberellin A29)

3D Structure for NP0048133 (Gibberellin A29)