NP-MRD: Showing NP-Card for boschnaloside (NP0224499)

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Record Information

Version

2.0

Created at

2022-09-06 02:52:31 UTC

Updated at

2022-09-06 02:52:32 UTC

NP-MRD ID

NP0224499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

boschnaloside

Description

8-Epiiridotrial glucoside, also known as boschnaloside, 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. Thus, 8-epiiridotrial glucoside is considered to be an isoprenoid. boschnaloside is found in Boschniakia rossica, Cordylanthus ramosus, Euphrasia nemorosa, Euphrasia pectinata, Euphrasia salisburgensis, Incarvillea emodi, Leucocarpus perfoliatus, Pedicularis kansuensis, Pedicularis palustris, Pedicularis plicata, Pedicularis verticillata, Penstemon barbatus, Penstemon roseus and Veronica anagallis-aquatica. Based on a literature review very few articles have been published on 8-epiiridotrial glucoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204522D          

 24 26  0  0  1  0            999 V2000
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24  5  1  6  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H]2[C@@H]1[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC=C2C=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O8/c1-7-2-3-9-8(4-17)6-22-15(11(7)9)24-16-14(21)13(20)12(19)10(5-18)23-16/h4,6-7,9-16,18-21H,2-3,5H2,1H3/t7-,9-,10-,11-,12-,13+,14-,15+,16+/m1/s1

> <INCHI_KEY>
MRIFZKMKTDPBHR-XLOWEYQUSA-N

> <FORMULA>
C16H24O8

> <MOLECULAR_WEIGHT>
344.36

> <EXACT_MASS>
344.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.35317603432088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,7R,7aR)-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-4-carbaldehyde

> <JCHEM_LOGP>
-1.0662243089999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198724996713914

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207031723485965

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760151199

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
80.18740000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
boschnaloside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.258   2.547   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.258  -5.153   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  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24   11    5    2                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Boschnaloside	Kegg

Chemical Formula

C₁₆H₂₄O₈

Average Mass

344.3600 Da

Monoisotopic Mass

344.14712 Da

IUPAC Name

(1S,4aS,7R,7aR)-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-4-carbaldehyde

Traditional Name

boschnaloside

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H]2[C@@H]1[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC=C2C=O

InChI Identifier

InChI=1S/C16H24O8/c1-7-2-3-9-8(4-17)6-22-15(11(7)9)24-16-14(21)13(20)12(19)10(5-18)23-16/h4,6-7,9-16,18-21H,2-3,5H2,1H3/t7-,9-,10-,11-,12-,13+,14-,15+,16+/m1/s1

InChI Key

MRIFZKMKTDPBHR-XLOWEYQUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Boschniakia rossica	LOTUS Database	35616633
Cordylanthus ramosus	LOTUS Database	35616633
Euphrasia nemorosa	LOTUS Database	35616633
Euphrasia pectinata	LOTUS Database	35616633
Euphrasia salisburgensis	LOTUS Database	35616633
Incarvillea emodi	LOTUS Database	35616633
Leucocarpus perfoliatus	LOTUS Database	35616633
Pedicularis kansuensis	LOTUS Database	35616633
Pedicularis palustris	LOTUS Database	35616633
Pedicularis plicata	LOTUS Database	35616633
Pedicularis verticillata	LOTUS Database	35616633
Penstemon barbatus	LOTUS Database	35616633
Penstemon roseus	LOTUS Database	35616633
Veronica anagallis-aquatica	LOTUS Database	35616633

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
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Vinylogous ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Primary alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

terpene glycoside (CHEBI:2320 )
Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (C11652 )
Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (LMPR0102070023 )

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	-1.1	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.19 m³·mol⁻¹	ChemAxon
Polarizability	34.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00058387

Chemspider ID

137353

KEGG Compound ID

C11652

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155942

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for boschnaloside (NP0224499)

MOL for NP0224499 (boschnaloside)

3D MOL for NP0224499 (boschnaloside)

3D SDF for NP0224499 (boschnaloside)

3D-SDF for NP0224499 (boschnaloside)

PDB for NP0224499 (boschnaloside)

3D PDB for NP0224499 (boschnaloside)

SMILES for NP0224499 (boschnaloside)

INCHI for NP0224499 (boschnaloside)

Structure for NP0224499 (boschnaloside)

3D Structure for NP0224499 (boschnaloside)