NP-MRD: Showing NP-Card for Decursidate (NP0138662)

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Record Information

Version

2.0

Created at

2022-06-29 17:39:52 UTC

Updated at

2022-06-29 17:39:52 UTC

NP-MRD ID

NP0138662

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Decursidate

Description

Decursidate, also known as decursidic acid, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Decursidate is found in Angelica decursiva. Decursidate was first documented in 2001 (PMID: 11355765). Based on a literature review very few articles have been published on Decursidate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    6.7529   -0.7601    1.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0183   -0.3241    0.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9486   -0.0844   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6396   -0.2503    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5664   -0.0096   -0.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1964   -0.2125   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1058   -0.0254   -0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333   -0.2468   -0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3922   -0.6347    0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3263   -0.0212   -1.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6644   -0.1980   -0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0360    0.6834    0.3671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8931    2.0213    0.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891    0.4423    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4185    1.0085   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7827    0.8255   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2410    0.0680    1.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6029   -0.1431    1.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2882   -0.4852    1.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9350   -0.3073    1.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8207    0.4137   -2.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1201    0.5914   -2.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1670    0.3452   -1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4983    0.5128   -1.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6831   -0.8199    2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3223   -1.7993    1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9926   -0.1060    2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199   -0.5842    1.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -0.5545    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054    0.3104   -1.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3005    0.0235   -1.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8125   -1.2721   -0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4511    0.3531    1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    2.4113    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478    1.6039   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4924    1.2633   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0693    0.5429    1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6081   -1.0822    2.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2003   -0.7575    2.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0162    0.6097   -2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3598    0.9309   -3.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6651    0.8265   -2.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 23  2  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
 21  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  5  4  2  0
  4  3  1  0
 20 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 24 42  1  0
 22 41  1  0
 21 40  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  1
 13 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
  4 28  1  0
M  END


  Mrv1652306292219392D          

 24 25  0  0  1  0            999 V2000
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 15 23  1  1  0  0  0
  4 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138662

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)OC[C@@H](O)C2=CC=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-23-17-10-12(2-8-15(17)20)3-9-18(22)24-11-16(21)13-4-6-14(19)7-5-13/h2-10,16,19-21H,11H2,1H3/b9-3+/t16-/m1/s1

> <INCHI_KEY>
CLQSQZGNPFWGAE-UOWSJYKBSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.336

> <EXACT_MASS>
330.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.79541111550216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.844649915666667

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.014116994789555

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.324340822697389

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3746598843841396

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
88.82910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23   15                                                            
CONECT   24    4                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
Decursidic acid	Generator
2-(4'-Hydroxyphenyl)glycol mono trans-ferulate	MeSH

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3360 Da

Monoisotopic Mass

330.11034 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

272122-56-2

SMILES

COC1=C(O)C=CC(\C=C\C(=O)OC[C@@H](O)C2=CC=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C18H18O6/c1-23-17-10-12(2-8-15(17)20)3-9-18(22)24-11-16(21)13-4-6-14(19)7-5-13/h2-10,16,19-21H,11H2,1H3/b9-3+/t16-/m1/s1

InChI Key

CLQSQZGNPFWGAE-UOWSJYKBSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Angelica decursiva	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Aromatic alcohol
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

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

33823838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102004630

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yao NH, Kong LY, Niwa M: Two new compounds from Peucedanum decursivum. J Asian Nat Prod Res. 2001;3(1):1-7. doi: 10.1080/10286020108042832. [PubMed:11355765 ]

Showing NP-Card for Decursidate (NP0138662)

MOL for NP0138662 (Decursidate)

3D MOL for NP0138662 (Decursidate)

3D SDF for NP0138662 (Decursidate)

3D-SDF for NP0138662 (Decursidate)

PDB for NP0138662 (Decursidate)

3D PDB for NP0138662 (Decursidate)

SMILES for NP0138662 (Decursidate)

INCHI for NP0138662 (Decursidate)

Structure for NP0138662 (Decursidate)

3D Structure for NP0138662 (Decursidate)