NP-MRD: Showing NP-Card for 2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate (NP0284344)

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Record Information

Version

2.0

Created at

2022-09-09 12:00:05 UTC

Updated at

2022-09-09 12:00:05 UTC

NP-MRD ID

NP0284344

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

Description

2-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. 2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate is found in Manilkara zapota. 2-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161523532D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161523532D          

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M  END
> <DATABASE_ID>
NP0284344

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)CC(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(C1)OC(=O)C=CC1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O13/c1-35-23(33)24(34)9-17(29)21(37-22(32)12-7-15(27)20(31)16(28)8-12)18(10-24)36-19(30)5-3-11-2-4-13(25)14(26)6-11/h2-8,17-18,21,25-29,31,34H,9-10H2,1H3

> <INCHI_KEY>
VMLJFBIJZLTOFL-UHFFFAOYSA-N

> <FORMULA>
C24H24O13

> <MOLECULAR_WEIGHT>
520.443

> <EXACT_MASS>
520.121690833

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.173145098503696

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
1.4619681816666663

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.237333516261748

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.070466664612905

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246896819952239

> <JCHEM_POLAR_SURFACE_AREA>
220.50999999999996

> <JCHEM_REFRACTIVITY>
123.7685

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       5.454  -3.123   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.464  -4.303   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.991  -5.750   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.508  -6.018   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.011  -5.750   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002 -16.940   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   24                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14                                                       
CONECT   23   10   24   25                                                  
CONECT   24   23    5                                                       
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₄H₂₄O₁₃

Average Mass

520.4430 Da

Monoisotopic Mass

520.12169 Da

IUPAC Name

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

Traditional Name

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)CC(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(C1)OC(=O)C=CC1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C24H24O13/c1-35-23(33)24(34)9-17(29)21(37-22(32)12-7-15(27)20(31)16(28)8-12)18(10-24)36-19(30)5-3-11-2-4-13(25)14(26)6-11/h2-8,17-18,21,25-29,31,34H,9-10H2,1H3

InChI Key

VMLJFBIJZLTOFL-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
Manilkara zapota	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
Hydroxysteroid
Steroid
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Primary alcohol
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	1.54	ALOGPS
logP	1.46	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	123.77 m³·mol⁻¹	ChemAxon
Polarizability	49.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

85343295

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate (NP0284344)

MOL for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

PDB for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

SMILES for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

INCHI for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

Structure for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0284344 (2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate)