NP-MRD: Showing NP-Card for (2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate (NP0280898)

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Record Information

Version

2.0

Created at

2022-09-09 06:56:30 UTC

Updated at

2022-09-09 06:56:31 UTC

NP-MRD ID

NP0280898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

Description

Tremulacinol belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate was first documented in 2004 (PMID: 15104498). Based on a literature review very few articles have been published on tremulacinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092208562D          

 38 41  0  0  1  0            999 V2000
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    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092208562D          

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 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  6  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  1  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H](OC2=CC=CC=C2COC(=O)[C@]2(O)C=CCC[C@@H]2O)[C@@H](OC(=O)C2=CC=CC=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O11/c28-14-19-21(30)22(31)23(38-24(32)16-8-2-1-3-9-16)25(37-19)36-18-11-5-4-10-17(18)15-35-26(33)27(34)13-7-6-12-20(27)29/h1-5,7-11,13,19-23,25,28-31,34H,6,12,14-15H2/t19-,20+,21+,22-,23+,25+,27+/m1/s1

> <INCHI_KEY>
VMTVSRVEQGYRCZ-RFONQLSFSA-N

> <FORMULA>
C27H30O11

> <MOLECULAR_WEIGHT>
530.526

> <EXACT_MASS>
530.178811786

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.99234961586963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6R)-2-(2-{[(1S,6S)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

> <JCHEM_LOGP>
1.4999397236666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.698050857345581

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.089135450529112

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092992635964

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
131.05300000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6R)-2-(2-{[(1S,6S)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.152 -11.283   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.185 -11.283   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.175 -12.462   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.648 -13.909   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.132 -14.177   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.142 -12.997   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.625 -13.265   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    4   32                                                  
CONECT   32   31                                                            
CONECT   33    2   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₁

Average Mass

530.5260 Da

Monoisotopic Mass

530.17881 Da

IUPAC Name

(2R,3S,4R,5R,6R)-2-(2-{[(1S,6S)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

Traditional Name

(2R,3S,4R,5R,6R)-2-(2-{[(1S,6S)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H](OC2=CC=CC=C2COC(=O)[C@]2(O)C=CCC[C@@H]2O)[C@@H](OC(=O)C2=CC=CC=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H30O11/c28-14-19-21(30)22(31)23(38-24(32)16-8-2-1-3-9-16)25(37-19)36-18-11-5-4-10-17(18)15-35-26(33)27(34)13-7-6-12-20(27)29/h1-5,7-11,13,19-23,25,28-31,34H,6,12,14-15H2/t19-,20+,21+,22-,23+,25+,27+/m1/s1

InChI Key

VMTVSRVEQGYRCZ-RFONQLSFSA-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 phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Benzyloxycarbonyl
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Phenol ether
Benzoyl
Beta-hydroxy acid
Benzenoid
Oxane
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
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	1.5	ChemAxon
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	131.05 m³·mol⁻¹	ChemAxon
Polarizability	52.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

101731472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ishikawa T, Nishigaya K, Takami K, Uchikoshi H, Chen IS, Tsai IL: Isolation of salicin derivatives from Homalium cochinchinensis and their antiviral activities. J Nat Prod. 2004 Apr;67(4):659-63. doi: 10.1021/np034052o. [PubMed:15104498 ]
LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate (NP0280898)

MOL for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D MOL for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D SDF for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D-SDF for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

PDB for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D PDB for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

SMILES for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

INCHI for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

Structure for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D Structure for NP0280898 ((2r,3s,4r,5r,6r)-2-(2-{[(1s,6s)-1,6-dihydroxycyclohex-2-ene-1-carbonyloxy]methyl}phenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)