NP-MRD: Showing NP-Card for 5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid (NP0318104)

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Record Information

Version

2.0

Created at

2022-09-11 18:24:01 UTC

Updated at

2022-09-11 18:24:01 UTC

NP-MRD ID

NP0318104

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid

Description

3-[2-(Benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-2-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylic acid belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. 5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid is found in Alstonia scholaris. 3-[2-(Benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-2-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533005011512312D          

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M  END

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M  END


  Mrv1533005011512312D          

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 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318104

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C(=CCOC(=O)C2=CC=CC=C2)C(OCC(O)C(O)C(O)C(O)C=O)OC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O13/c1-34-19(28)9-15-14(7-8-35-23(33)13-5-3-2-4-6-13)24(36-11-16(15)22(31)32)37-12-18(27)21(30)20(29)17(26)10-25/h2-7,10-11,15,17-18,20-21,24,26-27,29-30H,8-9,12H2,1H3,(H,31,32)

> <INCHI_KEY>
QUCKWTGRXASUQM-UHFFFAOYSA-N

> <FORMULA>
C24H28O13

> <MOLECULAR_WEIGHT>
524.475

> <EXACT_MASS>
524.152990962

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.38018181848688

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-2-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylic acid

> <ALOGPS_LOGP>
-0.32

> <JCHEM_LOGP>
-1.0952479656666663

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.25697903042305

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.035731012375244

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5250914409121608

> <JCHEM_POLAR_SURFACE_AREA>
206.34999999999997

> <JCHEM_REFRACTIVITY>
123.13860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    7   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   19   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    6   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-[2-(Benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-2-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate	Generator

Chemical Formula

C₂₄H₂₈O₁₃

Average Mass

524.4750 Da

Monoisotopic Mass

524.15299 Da

IUPAC Name

3-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-2-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylic acid

Traditional Name

5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C(=CCOC(=O)C2=CC=CC=C2)C(OCC(O)C(O)C(O)C(O)C=O)OC=C1C(O)=O

InChI Identifier

InChI=1S/C24H28O13/c1-34-19(28)9-15-14(7-8-35-23(33)13-5-3-2-4-6-13)24(36-11-16(15)22(31)32)37-12-18(27)21(30)20(29)17(26)10-25/h2-7,10-11,15,17-18,20-21,24,26-27,29-30H,8-9,12H2,1H3,(H,31,32)

InChI Key

QUCKWTGRXASUQM-UHFFFAOYSA-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
Alstonia Alstonia scholaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Secoiridoid-skeleton
Aromatic monoterpenoid
Benzoate ester
Monocyclic monoterpenoid
Tricarboxylic acid or derivatives
Benzoic acid or derivatives
Benzoyl
Sugar acid
Monocyclic benzene moiety
Benzenoid
Beta-hydroxy aldehyde
Monosaccharide
Vinylogous ester
Alpha-hydroxyaldehyde
Methyl ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Aldehyde
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-0.32	ALOGPS
logP	-1.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	206.35 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	123.14 m³·mol⁻¹	ChemAxon
Polarizability	50.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid (NP0318104)

MOL for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

3D MOL for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

3D SDF for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

3D-SDF for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

PDB for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

3D PDB for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

SMILES for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

INCHI for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

Structure for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)

3D Structure for NP0318104 (5-[2-(benzoyloxy)ethylidene]-4-(2-methoxy-2-oxoethyl)-6-[(2,3,4,5-tetrahydroxy-6-oxohexyl)oxy]-4,6-dihydropyran-3-carboxylic acid)