NP-MRD: Showing NP-Card for (+)-4-Gingesulfonic acid (NP0075000)

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Record Information

Version

2.0

Created at

2022-04-28 20:19:16 UTC

Updated at

2022-04-28 20:19:16 UTC

NP-MRD ID

NP0075000

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-4-Gingesulfonic acid

Description

(4R)-8-(4-hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulfonic acid belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. (+)-4-Gingesulfonic acid is found in Zingiber officinale ROSCOE . Based on a literature review very few articles have been published on (4R)-8-(4-hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 44  0  0  0  0  0  0  0  0999 V2000
   -6.2263   -0.1331   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5985    0.8798    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2508    0.4854    1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645    0.2753   -0.0094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9481   -0.1355    0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706   -0.4538   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -0.5643   -1.5273 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -0.6673    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -0.9557   -1.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287   -1.1796   -0.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570   -2.4618   -0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5672   -2.6960   -0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4290   -1.5984   -0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7479   -1.7901    0.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048   -0.3156   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9247    0.7149   -0.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5204    2.0511   -0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961   -0.0920   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330    1.8120   -0.8677 S   0  0  1  0  0  6  0  0  0  0  0  0
   -2.0977    1.5932   -2.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864    2.3714   -1.4502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4218    2.9510    0.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732    0.0030   -1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9674   -1.1568    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3315    0.0075   -0.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6531    1.8592    0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2483    0.9011    1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7590    1.2728    1.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502   -0.4240    1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730   -0.4974   -0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330   -1.0613    1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6138    0.6159    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5988   -1.5453    0.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8810    0.2147    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170   -1.7885   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3975   -0.0531   -1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5300   -3.2740   -0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141   -3.7006    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1092   -2.7130    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3479    2.7026   -0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5714    2.3179    0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697    2.2171   -1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354    0.9166   -0.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644    3.0945    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 18  2  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
  4 19  1  0
 19 22  1  1
 19 20  2  0
 19 21  2  0
 11 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  6
  5 31  1  0
  5 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 18 43  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 14 39  1  0
 12 38  1  0
 11 37  1  0
 22 44  1  0
M  END


  Mrv1652304282222192D          

 22 22  0  0  1  0            999 V2000
    0.3829    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3329   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829   -0.6039    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  2  0  0  0  0
 16 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075000

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@H](CC(=O)CCC1=CC(OC)=C(O)C=C1)S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O6S/c1-3-4-13(22(18,19)20)10-12(16)7-5-11-6-8-14(17)15(9-11)21-2/h6,8-9,13,17H,3-5,7,10H2,1-2H3,(H,18,19,20)/t13-/m1/s1

> <INCHI_KEY>
YJMGVBJYAHWWPU-CYBMUJFWSA-N

> <FORMULA>
C15H22O6S

> <MOLECULAR_WEIGHT>
330.4

> <EXACT_MASS>
330.113709602

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.80777874735362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-8-(4-hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulfonic acid

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
2.5899644156666675

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.945876304139146

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.9962662902097215

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890822645589822

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
82.42499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-8-(4-hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulfonic 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       0.715   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.055   2.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.715   4.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.255   4.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.025   2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.255   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.565   2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.875   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.645   2.874   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.185   0.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.955  -1.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.495  -1.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.265  -2.461   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       9.955   1.540   0.000  0.00  0.00           S+0
HETATM   17  O   UNK     0      11.288   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.621   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.725   2.874   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.595   2.874   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.055   0.206   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.715  -1.127   0.000  0.00  0.00           C+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20    2                                                            
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(4R)-8-(4-Hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulfonate	Generator
(4R)-8-(4-Hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulphonate	Generator
(4R)-8-(4-Hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulphonic acid	Generator

Chemical Formula

C₁₅H₂₂O₆S

Average Mass

330.4000 Da

Monoisotopic Mass

330.11371 Da

IUPAC Name

(4R)-8-(4-hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulfonic acid

Traditional Name

(4R)-8-(4-hydroxy-3-methoxyphenyl)-6-oxooctane-4-sulfonic acid

CAS Registry Number

Not Available

SMILES

CCC[C@H](CC(=O)CCC1=CC(OC)=C(O)C=C1)S(O)(=O)=O

InChI Identifier

InChI=1S/C15H22O6S/c1-3-4-13(22(18,19)20)10-12(16)7-5-11-6-8-14(17)15(9-11)21-2/h6,8-9,13,17H,3-5,7,10H2,1-2H3,(H,18,19,20)/t13-/m1/s1

InChI Key

YJMGVBJYAHWWPU-CYBMUJFWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zingiber officinale	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Alkanesulfonic acid
Sulfonyl
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Ketone
Ether
Organooxygen compound
Organic oxygen compound
Organosulfur compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	0.57	ALOGPS
logP	2.59	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	-1	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	82.42 m³·mol⁻¹	ChemAxon
Polarizability	33.81 Å³	ChemAxon
Number of Rings	1	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

555056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

639642

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-4-Gingesulfonic acid (NP0075000)

MOL for NP0075000 ((+)-4-Gingesulfonic acid)

3D MOL for NP0075000 ((+)-4-Gingesulfonic acid)

3D SDF for NP0075000 ((+)-4-Gingesulfonic acid)

3D-SDF for NP0075000 ((+)-4-Gingesulfonic acid)

PDB for NP0075000 ((+)-4-Gingesulfonic acid)

3D PDB for NP0075000 ((+)-4-Gingesulfonic acid)

SMILES for NP0075000 ((+)-4-Gingesulfonic acid)

INCHI for NP0075000 ((+)-4-Gingesulfonic acid)

Structure for NP0075000 ((+)-4-Gingesulfonic acid)

3D Structure for NP0075000 ((+)-4-Gingesulfonic acid)