NP-MRD: Showing NP-Card for (4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one (NP0248041)

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Record Information

Version

2.0

Created at

2022-09-07 10:07:54 UTC

Updated at

2022-09-07 10:07:54 UTC

NP-MRD ID

NP0248041

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one

Description

(4AS)-4abeta,5alpha-Dihydroxy-3-(methoxymethyl)-6alpha-vinyl-4a,5,6,7-tetrahydro-4H-1-benzopyran-4-one belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Based on a literature review very few articles have been published on (4aS)-4abeta,5alpha-Dihydroxy-3-(methoxymethyl)-6alpha-vinyl-4a,5,6,7-tetrahydro-4H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.5627    1.0269    1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976    1.0592    1.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417    0.2662    1.0525 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7835   -0.5801   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541   -1.3530   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -1.0239   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6249   -1.7851   -1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709   -1.2670   -1.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1115    0.0161   -1.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    0.5693   -1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121    1.0993   -0.4877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3582    0.2048    0.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702    0.8617   -0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421    2.0976   -0.8573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127    0.2205    0.1437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5620   -0.2050    1.3743 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349    1.1201    0.4696 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6568    1.7633   -0.6473 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8232    0.3849    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3476    1.6081    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0438    1.7049    2.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7720   -0.4591    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906   -1.2308    0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899    0.0570   -0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146   -2.2748   -1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6562   -1.9095   -1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2931    1.3919   -2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505   -0.1952   -2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9788   -0.6599    0.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336    0.7348    1.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4610   -0.2086    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6444    0.6415    1.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    1.8743    1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1165    1.6337   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  1
 15 13  1  0
 13 14  2  0
 13  9  1  0
 15  6  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 10 27  1  0
 10 28  1  0
  8 26  1  0
  5 25  1  0
  4 23  1  0
  4 24  1  0
  3 22  1  1
  2 21  1  0
  1 19  1  0
  1 20  1  0
 17 33  1  1
 18 34  1  0
 16 32  1  0
M  END


  Mrv1652309072212072D          

 18 19  0  0  1  0            999 V2000
   -0.7145   -1.2375    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
    0.7145   -1.2375    0.0000 C   0  0  2  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
    1.4289    0.0000    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
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  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
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  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  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0248041

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COCC1=COC2=CC[C@@H](C=C)[C@@H](O)[C@@]2(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O5/c1-3-8-4-5-10-13(16,11(8)14)12(15)9(6-17-2)7-18-10/h3,5,7-8,11,14,16H,1,4,6H2,2H3/t8-,11-,13-/m1/s1

> <INCHI_KEY>
PTPJFJWUFUTPEZ-XTWCZFFVSA-N

> <FORMULA>
C13H16O5

> <MOLECULAR_WEIGHT>
252.266

> <EXACT_MASS>
252.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.765268071199532

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,5R,6S)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-4a,5,6,7-tetrahydro-4H-chromen-4-one

> <JCHEM_LOGP>
-0.1048700386666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.169681230295527

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.91803224525032

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5030538662182122

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
66.2824

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,5R,6S)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5H-chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16   17                                             
CONECT   16   15                                                            
CONECT   17   15    3   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
(4AS)-4abeta,5a-dihydroxy-3-(methoxymethyl)-6a-vinyl-4a,5,6,7-tetrahydro-4H-1-benzopyran-4-one	Generator
(4AS)-4abeta,5α-dihydroxy-3-(methoxymethyl)-6α-vinyl-4a,5,6,7-tetrahydro-4H-1-benzopyran-4-one	Generator

Chemical Formula

C₁₃H₁₆O₅

Average Mass

252.2660 Da

Monoisotopic Mass

252.09977 Da

IUPAC Name

(4aS,5R,6S)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-4a,5,6,7-tetrahydro-4H-chromen-4-one

Traditional Name

(4aS,5R,6S)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5H-chromen-4-one

CAS Registry Number

Not Available

SMILES

COCC1=COC2=CC[C@@H](C=C)[C@@H](O)[C@@]2(O)C1=O

InChI Identifier

InChI=1S/C13H16O5/c1-3-8-4-5-10-13(16,11(8)14)12(15)9(6-17-2)7-18-10/h3,5,7-8,11,14,16H,1,4,6H2,2H3/t8-,11-,13-/m1/s1

InChI Key

PTPJFJWUFUTPEZ-XTWCZFFVSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Vinylogous ester
Tertiary alcohol
1,2-diol
Ketone
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-0.1	ChemAxon
pKa (Strongest Acidic)	10.92	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.28 m³·mol⁻¹	ChemAxon
Polarizability	25.77 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439988

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102142198

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one (NP0248041)

MOL for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

3D MOL for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

3D SDF for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

3D-SDF for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

PDB for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

3D PDB for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

SMILES for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

INCHI for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

Structure for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)

3D Structure for NP0248041 ((4as,5r,6s)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5h-chromen-4-one)