NP-MRD: Showing NP-Card for 6-O-(3,4,5-trimethoxybenzoyl)-ajugol (NP0074360)

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Record Information

Version

2.0

Created at

2022-04-28 19:31:50 UTC

Updated at

2022-04-28 19:31:50 UTC

NP-MRD ID

NP0074360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-O-(3,4,5-trimethoxybenzoyl)-ajugol

Description

(1S,4aS,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 6-O-(3,4,5-trimethoxybenzoyl)-ajugol is found in Tabebuia impetiginosa . Based on a literature review very few articles have been published on (1S,4aS,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221312D          

 38 41  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282221312D          

 38 41  0  0  1  0            999 V2000
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  1  0  0  0  0
 19 37  1  6  0  0  0
 19 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C(=O)O[C@@H]1C[C@](C)(O)[C@@H]2[C@@H]1C=CO[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O13/c1-25(31)9-15(36-22(30)11-7-13(32-2)21(34-4)14(8-11)33-3)12-5-6-35-23(17(12)25)38-24-20(29)19(28)18(27)16(10-26)37-24/h5-8,12,15-20,23-24,26-29,31H,9-10H2,1-4H3/t12-,15-,16-,17-,18-,19+,20-,23+,24+,25+/m1/s1

> <INCHI_KEY>
ISDOCUIPMQVNLK-AGCMVEMMSA-N

> <FORMULA>
C25H34O13

> <MOLECULAR_WEIGHT>
542.534

> <EXACT_MASS>
542.199941155

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.44237186403775

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
-0.8340164826666663

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.180580794389964

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20492172137141

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601928057

> <JCHEM_POLAR_SURFACE_AREA>
182.82999999999998

> <JCHEM_REFRACTIVITY>
127.27239999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       6.258   3.613   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.259   9.003   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.925  11.313   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.187  -0.692   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.235  -3.621   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.759  -5.086   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.253  -5.406   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.222  -4.262   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.698  -2.797   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.284  -4.582   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.315  -3.437   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.777  -6.871   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.807  -8.015   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.789  -6.230   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.313  -7.695   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.430   5.598   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.992   5.131   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18                                                       
CONECT   18   17                                                            
CONECT   19    5   20   37   38                                             
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28   34                                                       
CONECT   34   33                                                            
CONECT   35   27   36                                                       
CONECT   36   35                                                            
CONECT   37   19                                                            
CONECT   38   19                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1S,4AS,5R,7S,7as)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoic acid	Generator

Chemical Formula

C₂₅H₃₄O₁₃

Average Mass

542.5340 Da

Monoisotopic Mass

542.19994 Da

IUPAC Name

(1S,4aS,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate

Traditional Name

(1S,4aS,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C(=O)O[C@@H]1C[C@](C)(O)[C@@H]2[C@@H]1C=CO[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C25H34O13/c1-25(31)9-15(36-22(30)11-7-13(32-2)21(34-4)14(8-11)33-3)12-5-6-35-23(17(12)25)38-24-20(29)19(28)18(27)16(10-26)37-24/h5-8,12,15-20,23-24,26-29,31H,9-10H2,1-4H3/t12-,15-,16-,17-,18-,19+,20-,23+,24+,25+/m1/s1

InChI Key

ISDOCUIPMQVNLK-AGCMVEMMSA-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
Handroanthus impetiginosus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Iridoid o-glycoside
Terpene glycoside
Hexose monosaccharide
Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
O-glycosyl compound
M-methoxybenzoic acid or derivatives
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Benzoate ester
Aromatic monoterpenoid
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
Benzoyl
Anisole
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.08	ALOGPS
logP	-0.83	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.27 m³·mol⁻¹	ChemAxon
Polarizability	54.44 Å³	ChemAxon
Number of Rings	4	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

163018924

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-O-(3,4,5-trimethoxybenzoyl)-ajugol (NP0074360)

MOL for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

3D MOL for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

3D SDF for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

3D-SDF for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

PDB for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

3D PDB for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

SMILES for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

INCHI for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

Structure for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)

3D Structure for NP0074360 (6-O-(3,4,5-trimethoxybenzoyl)-ajugol)