NP-MRD: Showing NP-Card for Gibberellin A86 (NP0049123)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:29 UTC

Updated at

2022-03-17 21:07:29 UTC

NP-MRD ID

NP0049123

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gibberellin A86

Description

1-Thiocyanato-4-(methylthio)butane, also known as 4-(methylthio)butyl thiocyanate, 9CI, belongs to the class of organic compounds known as thiocyanates. These are salts or esters of thiocyanic acid, with the general formula RSC#N (R=alkyl, aryl). 1-Thiocyanato-4-(methylthio)butane is possibly neutral. Outside of the human body, 1-Thiocyanato-4-(methylthio)butane has been detected, but not quantified in, brassicas. This could make 1-thiocyanato-4-(methylthio)butane a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241210262D          

 27 31  0  0  0  0            999 V2000
   -2.1003   -1.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3498   -1.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -1.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500   -0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3250   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9253   -0.0372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748    1.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4497    1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1499    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6503    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2753    1.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249    1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    1.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    0.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -0.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    0.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2747   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0252   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -0.4873    0.0000 O   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 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  4 24  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 23  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv0541 02241210262D          

 27 31  0  0  0  0            999 V2000
   -2.1003   -1.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3498   -1.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -1.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500   -0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3250   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9253   -0.0372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748    1.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4497    1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1499    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6503    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2753    1.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249    1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    1.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    0.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -0.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    0.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2747   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0252   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -0.4873    0.0000 O   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 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  4 24  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 23  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049123

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12C3C(C(O)=O)C45CC(O)(C(O)CC4C3(CCC1O)OC2=O)C(=C)C5O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O8/c1-7-13(22)17-6-18(7,26)10(21)5-8(17)19-4-3-9(20)16(2,15(25)27-19)12(19)11(17)14(23)24/h8-13,20-22,26H,1,3-6H2,2H3,(H,23,24)

> <INCHI_KEY>
JMGSTZUVIHCAAA-UHFFFAOYSA-N

> <FORMULA>
C19H24O8

> <MOLECULAR_WEIGHT>
380.3891

> <EXACT_MASS>
380.147117744

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
36.905568106554554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,7,12-tetrahydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

> <ALOGPS_LOGP>
-0.63

> <JCHEM_LOGP>
-1.7487871936666664

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.069812424913817

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.032164249007831

> <JCHEM_PKA_STRONGEST_BASIC>
-3.041959893052673

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
88.3299

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,7,12-tetrahydroxy-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      -3.921  -3.430   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.520  -2.870   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.120  -3.151   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.420  -1.750   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.960  -1.750   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.640  -2.030   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.340  -0.910   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.461  -0.069   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.140   3.430   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.839   2.030   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.280   0.629   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.260  -0.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.800  -0.910   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.081   0.629   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.381   2.450   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.360   3.430   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.660   2.030   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.260   1.750   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.260   3.290   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.041   1.190   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.640   0.769   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.520  -0.069   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.260   0.069   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.980  -1.330   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.379  -1.890   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.780  -0.910   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.461  -0.910   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12   24                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11   15                                                  
CONECT   11   10   12   23                                                  
CONECT   12    4   11   13                                                  
CONECT   13    2    7   12   14                                             
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16   17                                                            
CONECT   17   16   18   21                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   17   20   22   26                                             
CONECT   22   21   23                                                       
CONECT   23   11   18   22   24                                             
CONECT   24    4   23   25                                                  
CONECT   25   24   26                                                       
CONECT   26   21   25   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
4-(Methylthio)butyl thiocyanate, 9ci	HMDB
GA86	HMDB
4,5,7,12-Tetrahydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylate	Generator

Chemical Formula

C₁₉H₂₄O₈

Average Mass

380.3891 Da

Monoisotopic Mass

380.14712 Da

IUPAC Name

4,5,7,12-tetrahydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

Traditional Name

4,5,7,12-tetrahydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane-9-carboxylic acid

CAS Registry Number

138703-93-2

SMILES

CC12C3C(C(O)=O)C45CC(O)(C(O)CC4C3(CCC1O)OC2=O)C(=C)C5O

InChI Identifier

InChI=1S/C19H24O8/c1-7-13(22)17-6-18(7,26)10(21)5-8(17)19-4-3-9(20)16(2,15(25)27-19)12(19)11(17)14(23)24/h8-13,20-22,26H,1,3-6H2,2H3,(H,23,24)

InChI Key

JMGSTZUVIHCAAA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Prunus avium	FooDB	KNAPSACK
Prunus cerasus	FooDB	KNAPSACK
Prunus persica	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiocyanates. These are salts or esters of thiocyanic acid, with the general formula RSC#N (R=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thiocyanates

Sub Class

Not Available

Direct Parent

Thiocyanates

Alternative Parents

Substituents

Dialkylthioether
Sulfenyl compound
Thioether
Thiocyanate
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
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	-0.63	ALOGPS
logP	-1.7	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.33 m³·mol⁻¹	ChemAxon
Polarizability	36.91 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038446

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017804

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

89295500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gibberellin A86 (NP0049123)

MOL for NP0049123 (Gibberellin A86)

3D MOL for NP0049123 (Gibberellin A86)

3D SDF for NP0049123 (Gibberellin A86)

3D-SDF for NP0049123 (Gibberellin A86)

PDB for NP0049123 (Gibberellin A86)

3D PDB for NP0049123 (Gibberellin A86)

SMILES for NP0049123 (Gibberellin A86)

INCHI for NP0049123 (Gibberellin A86)

Structure for NP0049123 (Gibberellin A86)

3D Structure for NP0049123 (Gibberellin A86)