NP-MRD: Showing NP-Card for (4S)-(+)-Ascochin (NP0013965)

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Record Information

Version

2.0

Created at

2021-01-05 23:14:38 UTC

Updated at

2021-07-15 17:15:57 UTC

NP-MRD ID

NP0013965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4S)-(+)-Ascochin

Provided By

NPAtlas

Description

(4S)-(+)-Ascochin is found in Ascochyta. Based on a literature review very few articles have been published on (4S)-6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carbaldehyde.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119513D          

 27 28  0  0  0  0            999 V2000
   -3.5012    0.6184    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2076    0.8082    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7753    2.0837    0.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603    2.3866    0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317    3.5479   -0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4935    1.2569    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8468    1.5273   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2330    2.8533   -0.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7386    0.4783   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3264   -0.8345   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2111   -1.9060   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -1.0952    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5335   -2.4645    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3606   -3.4082    0.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0647   -0.0325    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3558   -0.3659    0.3710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7987   -1.0922   -0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9243   -0.3661    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349    1.4547    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197    3.0231   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7853    0.6650   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -1.6847   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4970   -2.6607    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015   -1.0762    1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9452   -1.4199   -1.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4787   -1.9101   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3829   -0.3867   -1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16  2  1  0  0  0  0
 15  6  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  8 20  1  0  0  0  0
  9 21  1  0  0  0  0
 11 22  1  0  0  0  0
 13 23  1  0  0  0  0
 16 24  1  1  0  0  0
 17 25  1  0  0  0  0
 17 26  1  0  0  0  0
 17 27  1  0  0  0  0
M  END


  Mrv1652306242119513D          

 27 28  0  0  0  0            999 V2000
   -3.5012    0.6184    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2076    0.8082    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7753    2.0837    0.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603    2.3866    0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317    3.5479   -0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4935    1.2569    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8468    1.5273   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2330    2.8533   -0.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7386    0.4783   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3264   -0.8345   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2111   -1.9060   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -1.0952    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5335   -2.4645    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3606   -3.4082    0.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0647   -0.0325    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3558   -0.3659    0.3710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7987   -1.0922   -0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9243   -0.3661    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349    1.4547    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197    3.0231   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7853    0.6650   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -1.6847   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4970   -2.6607    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015   -1.0762    1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9452   -1.4199   -1.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4787   -1.9101   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3829   -0.3867   -1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16  2  1  0  0  0  0
 15  6  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  8 20  1  0  0  0  0
  9 21  1  0  0  0  0
 11 22  1  0  0  0  0
 13 23  1  0  0  0  0
 16 24  1  1  0  0  0
 17 25  1  0  0  0  0
 17 26  1  0  0  0  0
 17 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)OC(=C([H])[H])[C@]([H])(C2=C1C([H])=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O5/c1-5-6(2)17-12(16)11-9(15)3-8(14)7(4-13)10(5)11/h3-5,14-15H,2H2,1H3/t5-/m1/s1

> <INCHI_KEY>
XLKIJHXPWYIGIM-RXMQYKEDSA-N

> <FORMULA>
C12H10O5

> <MOLECULAR_WEIGHT>
234.207

> <EXACT_MASS>
234.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.283932725246714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carbaldehyde

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
2.807161636

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.394306793904219

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.144127826042824

> <JCHEM_PKA_STRONGEST_BASIC>
-5.473715301377713

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
61.172999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-4H-2-benzopyran-5-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.501   0.618   0.795  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.208   0.808   0.499  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.775   2.084   0.336  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.460   2.387   0.103  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.032   3.548  -0.049  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.494   1.257   0.029  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.847   1.527  -0.174  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.233   2.853  -0.329  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.739   0.478  -0.212  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.326  -0.835  -0.055  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.211  -1.906  -0.090  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.992  -1.095   0.145  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.534  -2.465   0.318  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.361  -3.408   0.283  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.065  -0.033   0.186  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.356  -0.366   0.371  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.799  -1.092  -0.912  0.00  0.00           C+0
HETATM   18  H   UNK     0      -3.924  -0.366   0.940  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.135   1.455   0.892  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.220   3.023  -0.475  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.785   0.665  -0.368  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.189  -1.685  -0.238  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.497  -2.661   0.473  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.502  -1.076   1.228  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.945  -1.420  -1.512  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.479  -1.910  -0.633  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.383  -0.387  -1.550  0.00  0.00           H+0
CONECT    1    2   18   19                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   20                                                       
CONECT    9    7   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   22                                                       
CONECT   12   10   13   15                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13                                                            
CONECT   15   12   16    6                                                  
CONECT   16   15   17    2   24                                             
CONECT   17   16   25   26   27                                             
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    8                                                            
CONECT   21    9                                                            
CONECT   22   11                                                            
CONECT   23   13                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26   17                                                            
CONECT   27   17                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₂H₁₀O₅

Average Mass

234.2070 Da

Monoisotopic Mass

234.05282 Da

IUPAC Name

(4S)-6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carbaldehyde

Traditional Name

(4S)-6,8-dihydroxy-4-methyl-3-methylidene-1-oxo-4H-2-benzopyran-5-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=C)OC(=O)C2=C1C(C=O)=C(O)C=C2O

InChI Identifier

InChI=1S/C12H10O5/c1-5-6(2)17-12(16)11-9(15)3-8(14)7(4-13)10(5)11/h3-5,14-15H,2H2,1H3/t5-/m1/s1

InChI Key

XLKIJHXPWYIGIM-RXMQYKEDSA-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
Ascochyta	NPAtlas	25855820

Chemical Taxonomy

Classification

Not classified

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	1.73	ALOGPS
logP	2.81	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.17 m³·mol⁻¹	ChemAxon
Polarizability	22.28 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA015359

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17272145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16114834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (4S)-(+)-Ascochin (NP0013965)

MOL for NP0013965 ((4S)-(+)-Ascochin)

3D MOL for NP0013965 ((4S)-(+)-Ascochin)

3D SDF for NP0013965 ((4S)-(+)-Ascochin)

3D-SDF for NP0013965 ((4S)-(+)-Ascochin)

PDB for NP0013965 ((4S)-(+)-Ascochin)

3D PDB for NP0013965 ((4S)-(+)-Ascochin)

SMILES for NP0013965 ((4S)-(+)-Ascochin)

INCHI for NP0013965 ((4S)-(+)-Ascochin)

Structure for NP0013965 ((4S)-(+)-Ascochin)

3D Structure for NP0013965 ((4S)-(+)-Ascochin)