NP-MRD: Showing NP-Card for (1R,4R,5S)-5-Hydroxyfenchone glucoside (NP0335845)

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Record Information

Version

2.0

Created at

2024-09-11 03:30:51 UTC

Updated at

2024-09-11 03:30:52 UTC

NP-MRD ID

NP0335845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1R,4R,5S)-5-Hydroxyfenchone glucoside

Description

(1R,4R,5S)-5-Hydroxyfenchone glucoside belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Based on a literature review very few articles have been published on (1R,4R,5S)-5-Hydroxyfenchone glucoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262306032D          

 23 25  0  0  0  0            999 V2000
    1.0215    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7352   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7352    0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7352    1.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626    0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9483   -0.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2726   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475   -1.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -1.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1303    0.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8440    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8440   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1303   -1.0291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2997    0.6236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1318    1.4403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575    0.6209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CC(C)(CC2OC2OC(CO)C(O)C(O)C2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1/C16H26O7/c1-15(2)7-4-16(3,14(15)21)5-8(7)22-13-12(20)11(19)10(18)9(6-17)23-13/h7-13,17-20H,4-6H2,1-3H3

> <INCHI_KEY>
WZIIAEDQDFVGCF-UHFFFAOYNA-N

> <FORMULA>
C16H26O7

> <MOLECULAR_WEIGHT>
330.377

> <EXACT_MASS>
330.167853177

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.09229267506251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,3-trimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}bicyclo[2.2.1]heptan-2-one

> <JCHEM_LOGP>
-0.014680488666666346

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200090023933111

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210561278452845

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835428036153

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
78.5496

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,3,3-trimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}bicyclo[2.2.1]heptan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       1.907   0.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.907  -1.154   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.239  -1.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.569  -1.154   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.569   0.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.239   1.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.239   2.694   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.904   1.156   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.637  -0.335   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.109  -1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.569  -2.694   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.572  -1.924   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.762  -1.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770   0.386   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.110   1.149   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.442   0.386   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.442  -1.154   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.110  -1.921   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.559   1.164   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.113   2.689   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.774   1.159   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.774  -1.924   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.109  -1.154   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10   11                                             
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7    9                                             
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    3    6                                                       
CONECT   10    4                                                            
CONECT   11    4                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   22                                                  
CONECT   18   13   17                                                       
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₆O₇

Average Mass

330.3770 Da

Monoisotopic Mass

330.16785 Da

IUPAC Name

1,3,3-trimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}bicyclo[2.2.1]heptan-2-one

Traditional Name

1,3,3-trimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}bicyclo[2.2.1]heptan-2-one

CAS Registry Number

Not Available

SMILES

CC1(C)C2CC(C)(CC2OC2OC(CO)C(O)C(O)C2O)C1=O

InChI Identifier

InChI=1/C16H26O7/c1-15(2)7-4-16(3,14(15)21)5-8(7)22-13-12(20)11(19)10(18)9(6-17)23-13/h7-13,17-20H,4-6H2,1-3H3

InChI Key

WZIIAEDQDFVGCF-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Bicyclic monoterpenoid
Fenchane monoterpenoid
Norbornane monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
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	-0.015	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.55 m³·mol⁻¹	ChemAxon
Polarizability	34.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Showing NP-Card for (1R,4R,5S)-5-Hydroxyfenchone glucoside (NP0335845)

MOL for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

3D MOL for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

3D SDF for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

3D-SDF for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

PDB for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

3D PDB for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

SMILES for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

INCHI for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

Structure for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)

3D Structure for NP0335845 ((1R,4R,5S)-5-Hydroxyfenchone glucoside)