NP-MRD: Showing NP-Card for Lyciumoside VII (NP0047660)

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Record Information

Version

2.0

Created at

2022-03-17 20:43:50 UTC

Updated at

2022-03-17 20:43:50 UTC

NP-MRD ID

NP0047660

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lyciumoside VII

Description

Lyciumoside VII belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Lyciumoside VII is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lyciumoside VII has been detected, but not quantified in, a few different foods, such as coffee and coffee products, herbs and spices, and tea. This could make lyciumoside VII a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307092D          

 65 68  0  0  0  0            999 V2000
    5.1927   10.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061307092D          

 65 68  0  0  0  0            999 V2000
    5.1927   10.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0047660

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OCC2OC(OC\C(C)=C\CC\C(C)=C/CC\C(C)=C\CCC(C)(OC3OC(CO)C(O)C(O)C3O)C=C)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H74O21/c1-7-44(6,65-42-38(57)34(53)30(49)26(18-46)62-42)16-10-15-22(3)12-8-11-21(2)13-9-14-23(4)19-58-43-39(64-41-37(56)33(52)29(48)25(17-45)61-41)35(54)31(50)27(63-43)20-59-40-36(55)32(51)28(47)24(5)60-40/h7,11,14-15,24-43,45-57H,1,8-10,12-13,16-20H2,2-6H3/b21-11-,22-15+,23-14+

> <INCHI_KEY>
SXABFGWDVXEPQT-WMKUFMTOSA-N

> <FORMULA>
C44H74O21

> <MOLECULAR_WEIGHT>
939.0458

> <EXACT_MASS>
938.47225943

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
98.65866741887135

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3,4-dihydroxy-6-{[(2E,6Z,10E)-2,6,10,14-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,6,10,15-tetraen-1-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)methoxy]-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
-1.3502827700000006

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.185273998394399

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.751751236086752

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6489650351574907

> <JCHEM_POLAR_SURFACE_AREA>
336.8300000000001

> <JCHEM_REFRACTIVITY>
227.6960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3,4-dihydroxy-6-{[(2E,6Z,10E)-2,6,10,14-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,6,10,15-tetraen-1-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)methoxy]-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.693  19.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.543  17.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.463  17.710   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  16.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338  19.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.004  20.020   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.004  21.560   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.671  22.330   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.337  21.560   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.337  20.020   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.003  17.710   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      18.672  20.020   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      17.338  22.330   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      14.671  23.870   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      12.003  22.330   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      14.671  19.250   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      12.003  19.250   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   24                                                            
CONECT    6   44                                                            
CONECT    7    1   44                                                       
CONECT    8   11   12                                                       
CONECT    9   13   14                                                       
CONECT   10   15   16                                                       
CONECT   11    8   21                                                       
CONECT   12    8   22                                                       
CONECT   13    9   21                                                       
CONECT   14    9   23                                                       
CONECT   15   10   22                                                       
CONECT   16   10   44                                                       
CONECT   17   25   45                                                       
CONECT   18   26   46                                                       
CONECT   19   23   58                                                       
CONECT   20   27   59                                                       
CONECT   21    2   11   13                                                  
CONECT   22    3   12   15                                                  
CONECT   23    4   14   19                                                  
CONECT   24    5   28   60                                                  
CONECT   25   17   29   61                                                  
CONECT   26   18   30   62                                                  
CONECT   27   20   31   63                                                  
CONECT   28   24   32   47                                                  
CONECT   29   25   33   48                                                  
CONECT   30   26   34   49                                                  
CONECT   31   27   35   50                                                  
CONECT   32   28   36   51                                                  
CONECT   33   29   37   52                                                  
CONECT   34   30   38   53                                                  
CONECT   35   31   39   54                                                  
CONECT   36   32   40   55                                                  
CONECT   37   33   41   56                                                  
CONECT   38   34   42   57                                                  
CONECT   39   35   43   64                                                  
CONECT   40   36   59   60                                                  
CONECT   41   37   61   64                                                  
CONECT   42   38   62   65                                                  
CONECT   43   39   58   63                                                  
CONECT   44    6    7   16   65                                             
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   28                                                            
CONECT   48   29                                                            
CONECT   49   30                                                            
CONECT   50   31                                                            
CONECT   51   32                                                            
CONECT   52   33                                                            
CONECT   53   34                                                            
CONECT   54   35                                                            
CONECT   55   36                                                            
CONECT   56   37                                                            
CONECT   57   38                                                            
CONECT   58   19   43                                                       
CONECT   59   20   40                                                       
CONECT   60   24   40                                                       
CONECT   61   25   41                                                       
CONECT   62   26   42                                                       
CONECT   63   27   43                                                       
CONECT   64   39   41                                                       
CONECT   65   42   44                                                       
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₇₄O₂₁

Average Mass

939.0458 Da

Monoisotopic Mass

938.47226 Da

IUPAC Name

2-[(3,4-dihydroxy-6-{[(2E,6Z,10E)-2,6,10,14-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,6,10,15-tetraen-1-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)methoxy]-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

212773-44-9

SMILES

CC1OC(OCC2OC(OC\C(C)=C\CC\C(C)=C/CC\C(C)=C\CCC(C)(OC3OC(CO)C(O)C(O)C3O)C=C)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C44H74O21/c1-7-44(6,65-42-38(57)34(53)30(49)26(18-46)62-42)16-10-15-22(3)12-8-11-21(2)13-9-14-23(4)19-58-43-39(64-41-37(56)33(52)29(48)25(17-45)61-41)35(54)31(50)27(63-43)20-59-40-36(55)32(51)28(47)24(5)60-40/h7,11,14-15,24-43,45-57H,1,8-10,12-13,16-20H2,2-6H3/b21-11-,22-15+,23-14+

InChI Key

SXABFGWDVXEPQT-WMKUFMTOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Oligosaccharide
Diterpenoid
Fatty acyl glycoside
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty acyl
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-0.19	ALOGPS
logP	-1.4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	336.83 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	227.7 m³·mol⁻¹	ChemAxon
Polarizability	98.66 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

HMDB0033501

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011553

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

131751440

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Lyciumoside VII (NP0047660)

MOL for NP0047660 (Lyciumoside VII)

3D MOL for NP0047660 (Lyciumoside VII)

3D SDF for NP0047660 (Lyciumoside VII)

3D-SDF for NP0047660 (Lyciumoside VII)

PDB for NP0047660 (Lyciumoside VII)

3D PDB for NP0047660 (Lyciumoside VII)

SMILES for NP0047660 (Lyciumoside VII)

INCHI for NP0047660 (Lyciumoside VII)

Structure for NP0047660 (Lyciumoside VII)

3D Structure for NP0047660 (Lyciumoside VII)