NP-MRD: Showing NP-Card for Gibberellin A14-aldehyde (NP0054919)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 01:07:25 UTC

Updated at

2022-04-28 01:07:25 UTC

NP-MRD ID

NP0054919

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A14-aldehyde

Description

(1S,2S,3S,4S,5S,8S,9S,12R)-2-formyl-5-hydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]Pentadecane-4-carboxylic acid belongs to the class of organic compounds known as c20-gibberellins. These are gibberellins with carboxy groups in positions 7 and 18 and some also in 20, while others have an aldehyde group in the latter position. Gibberellin A14-aldehyde is found in Gibberella fujikuroi. Based on a literature review very few articles have been published on (1S,2S,3S,4S,5S,8S,9S,12R)-2-formyl-5-hydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]Pentadecane-4-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282203072D          

 24 27  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  1  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
    1.0659    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  2  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  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
   -0.1471    0.2126    0.0000 C   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
    1.7509    2.0485    0.0000 C   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  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  1  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
  5 19  1  1  0  0  0
  3 20  1  6  0  0  0
  3 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0054919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@H](O)[C@](C)([C@H]1[C@H](C=O)[C@]13C[C@@H](CC[C@@H]21)C(=C)C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-11-8-20-9-12(11)4-5-14(20)18(2)7-6-15(22)19(3,17(23)24)16(18)13(20)10-21/h10,12-16,22H,1,4-9H2,2-3H3,(H,23,24)/t12-,13+,14+,15+,16+,18+,19-,20+/m1/s1

> <INCHI_KEY>
YMDYUWHAQBYOMU-MFOCMZDKSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
51.73772856940555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.1965792933333335

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.715422941835826

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.463860493159369

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0380755502734225

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
89.59259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,4S,5S,8S,9S,12R)-2-formyl-5-hydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-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       1.990   2.731   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.074   1.368   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.033   2.185   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.204   2.863   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.321   4.227   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.288   4.196   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.636   1.296   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.078   0.755   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       2.161   0.213   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.817  -1.288   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.944  -2.337   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.268   3.824   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.359  -1.319   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.802  -1.224   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.073  -2.581   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.342  -1.177   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.653   0.260   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4   20   21                                             
CONECT    4    3    5   16                                                  
CONECT    5    4    6    7   19                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   15   16                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8                                                       
CONECT   16    8    4   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    5                                                            
CONECT   20    3                                                            
CONECT   21    3   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,3S,4S,5S,8S,9S,12R)-2-Formyl-5-hydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0,.0,]pentadecane-4-carboxylate	Generator

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

(1S,2S,3S,4S,5S,8S,9S,12R)-2-formyl-5-hydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylic acid

Traditional Name

(1S,2S,3S,4S,5S,8S,9S,12R)-2-formyl-5-hydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@H](O)[C@](C)([C@H]1[C@H](C=O)[C@]13C[C@@H](CC[C@@H]21)C(=C)C3)C(O)=O

InChI Identifier

InChI=1S/C20H28O4/c1-11-8-20-9-12(11)4-5-14(20)18(2)7-6-15(22)19(3,17(23)24)16(18)13(20)10-21/h10,12-16,22H,1,4-9H2,2-3H3,(H,23,24)/t12-,13+,14+,15+,16+,18+,19-,20+/m1/s1

InChI Key

YMDYUWHAQBYOMU-MFOCMZDKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium fujikuroi	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c20-gibberellins. These are gibberellins with carboxy groups in positions 7 and 18 and some also in 20, while others have an aldehyde group in the latter position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C20-gibberellins

Alternative Parents

Substituents

Gibberellane diterpenoid
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	2.43	ALOGPS
logP	2.2	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.59 m³·mol⁻¹	ChemAxon
Polarizability	51.74 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

162822675

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gibberellin A14-aldehyde (NP0054919)

MOL for NP0054919 (Gibberellin A14-aldehyde)

3D MOL for NP0054919 (Gibberellin A14-aldehyde)

3D SDF for NP0054919 (Gibberellin A14-aldehyde)

3D-SDF for NP0054919 (Gibberellin A14-aldehyde)

PDB for NP0054919 (Gibberellin A14-aldehyde)

3D PDB for NP0054919 (Gibberellin A14-aldehyde)

SMILES for NP0054919 (Gibberellin A14-aldehyde)

INCHI for NP0054919 (Gibberellin A14-aldehyde)

Structure for NP0054919 (Gibberellin A14-aldehyde)

3D Structure for NP0054919 (Gibberellin A14-aldehyde)