NP-MRD: Showing NP-Card for 6-O-p-Hydroxybenzoylaucubin (NP0137883)

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Record Information

Version

2.0

Created at

2022-05-31 16:37:41 UTC

Updated at

2022-05-31 16:37:41 UTC

NP-MRD ID

NP0137883

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-O-p-Hydroxybenzoylaucubin

Description

6-O-p-Hydroxybenzoylaucubin belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. 6-O-p-Hydroxybenzoylaucubin was first documented in 2010 (PMID: 20839124). Based on a literature review very few articles have been published on 6-O-p-Hydroxybenzoylaucubin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218372D          

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M  END

     RDKit          3D

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M  END


  Mrv1652305312218372D          

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 30 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  1  0  0  0
 34 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  6  0  0  0
 37 40  1  0  0  0  0
 27 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0137883

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(OC(=O)C2=CC=C(O)C=C2)C=C(CO)[C@]2([H])[C@@]1([H])C=CO[C@@]2([H])O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O11/c23-8-11-7-14(31-20(29)10-1-3-12(25)4-2-10)13-5-6-30-21(16(11)13)33-22-19(28)18(27)17(26)15(9-24)32-22/h1-7,13-19,21-28H,8-9H2/t13-,14+,15+,16+,17+,18-,19+,21-,22-/m0/s1

> <INCHI_KEY>
JZWZFNOVWZEQMF-QNAXTHAFSA-N

> <FORMULA>
C22H26O11

> <MOLECULAR_WEIGHT>
466.439

> <EXACT_MASS>
466.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.66106798319602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.9901353753333331

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.206573899816059

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.492495784755208

> <JCHEM_PKA_STRONGEST_BASIC>
-2.741605910230378

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
110.9797

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0       0.821   1.032   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.744   1.408   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.287   2.552   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.793   2.232   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.189   4.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.696   4.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.171   5.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.141   6.946   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.617   8.411   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.365   6.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.841   5.161   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.250  -4.334   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       2.530  -1.303   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -0.049  -1.438   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.864  -2.073   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       1.197  -3.613   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       2.530  -5.923   0.000  0.00  0.00           H+0
HETATM   29  O   UNK     0       5.198  -4.383   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       7.865  -5.923   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.865  -2.843   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.531  -6.693   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0       6.531  -8.233   0.000  0.00  0.00           H+0
HETATM   36  O   UNK     0       7.865  -7.463   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.198  -7.463   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0       3.864  -8.233   0.000  0.00  0.00           H+0
HETATM   39  O   UNK     0       5.198  -9.003   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.864  -6.693   0.000  0.00  0.00           C+0
HETATM   41  H   UNK     0       5.198  -5.923   0.000  0.00  0.00           H+0
HETATM   42  O   UNK     0       2.530  -7.463   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19   24                                             
CONECT   18   17                                                            
CONECT   19   17    2   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   17   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29   40                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32   34                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   30   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   27   41   42                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₁₁

Average Mass

466.4390 Da

Monoisotopic Mass

466.14751 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

1016987-87-3

SMILES

[H][C@@]1(OC(=O)C2=CC=C(O)C=C2)C=C(CO)[C@]2([H])[C@@]1([H])C=CO[C@@]2([H])O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C22H26O11/c23-8-11-7-14(31-20(29)10-1-3-12(25)4-2-10)13-5-6-30-21(16(11)13)33-22-19(28)18(27)17(26)15(9-24)32-22/h1-7,13-19,21-28H,8-9H2/t13-,14+,15+,16+,17+,18-,19+,21-,22-/m0/s1

InChI Key

JZWZFNOVWZEQMF-QNAXTHAFSA-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 iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Benzoate ester
Bicyclic monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen compound
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

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

28424249

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91885091

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang G, Yin W, Zhou ZY, Hsieh KL, Liu JK: New iridoids from the fruits of Crescentia cujete. J Asian Nat Prod Res. 2010 Sep;12(9):770-5. doi: 10.1080/10286020.2010.503189. [PubMed:20839124 ]

Showing NP-Card for 6-O-p-Hydroxybenzoylaucubin (NP0137883)

MOL for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

3D MOL for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

3D SDF for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

3D-SDF for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

PDB for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

3D PDB for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

SMILES for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

INCHI for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

Structure for NP0137883 (6-O-p-Hydroxybenzoylaucubin)

3D Structure for NP0137883 (6-O-p-Hydroxybenzoylaucubin)