NP-MRD: Showing NP-Card for loganin pentaacetate (NP0290081)

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Record Information

Version

2.0

Created at

2022-09-09 20:35:47 UTC

Updated at

2022-09-09 20:35:47 UTC

NP-MRD ID

NP0290081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

loganin pentaacetate

Description

Loganin pentaacetate belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups. loganin pentaacetate is found in Ophiorrhiza pumila. Based on a literature review very few articles have been published on Loganin pentaacetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309092222352D          

 42 44  0  0  1  0            999 V2000
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 41 42  1  1  0  0  0
M  END

     RDKit          3D

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M  END

  Mrv1652309092222352D          

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    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  6  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 36 41  1  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0290081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@@H]2[C@@H](C)[C@H](C[C@H]12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O15/c1-11-19(37-13(3)29)8-17-18(25(33)34-7)9-36-26(21(11)17)42-27-24(40-16(6)32)23(39-15(5)31)22(38-14(4)30)20(41-27)10-35-12(2)28/h9,11,17,19-24,26-27H,8,10H2,1-7H3/t11-,17+,19-,20+,21+,22+,23-,24+,26-,27-/m0/s1

> <INCHI_KEY>
AEJMLRVPTZEQEF-HISSRJBZSA-N

> <FORMULA>
C27H36O15

> <MOLECULAR_WEIGHT>
600.57

> <EXACT_MASS>
600.205420459

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
59.071716559292454

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,6S,7R,7aS)-6-(acetyloxy)-7-methyl-1-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_LOGP>
0.3684815873333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.08763326653711

> <JCHEM_POLAR_SURFACE_AREA>
185.49

> <JCHEM_REFRACTIVITY>
133.23190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
loganin pentaacetate

> <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  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.455  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.789  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.789   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.123  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.789  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.789  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.123  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.122  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.455  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.122  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.121  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.454  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.787  -7.700   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.877  -1.897   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.433  -0.564   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   10   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    8   34   41                                                  
CONECT   34   33    5   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   36   33   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

View in JSmol

Synonyms

Value	Source
Loganin pentaacetic acid	Generator

Chemical Formula

C₂₇H₃₆O₁₅

Average Mass

600.5700 Da

Monoisotopic Mass

600.20542 Da

IUPAC Name

methyl (1S,4aS,6S,7R,7aS)-6-(acetyloxy)-7-methyl-1-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

loganin pentaacetate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@@H]2[C@@H](C)[C@H](C[C@H]12)OC(C)=O

InChI Identifier

InChI=1S/C27H36O15/c1-11-19(37-13(3)29)8-17-18(25(33)34-7)9-36-26(21(11)17)42-27-24(40-16(6)32)23(39-15(5)31)22(38-14(4)30)20(41-27)10-35-12(2)28/h9,11,17,19-24,26-27H,8,10H2,1-7H3/t11-,17+,19-,20+,21+,22+,23-,24+,26-,27-/m0/s1

InChI Key

AEJMLRVPTZEQEF-HISSRJBZSA-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

Species Name	Source	Reference
Ophiorrhiza pumila	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Hexacarboxylic acids and derivatives

Direct Parent

Hexacarboxylic acids and derivatives

Alternative Parents

Substituents

Hexacarboxylic acid or derivatives
Iridoid o-glycoside
Terpene glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

terpene glycoside (CHEBI:6514 )
Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (C11663 )
Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (LMPR0102070030 )

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	0.37	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	185.49 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	133.23 m³·mol⁻¹	ChemAxon
Polarizability	59.07 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

391580

KEGG Compound ID

C11663

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443344

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for loganin pentaacetate (NP0290081)

MOL for NP0290081 (loganin pentaacetate)

3D MOL for NP0290081 (loganin pentaacetate)

3D SDF for NP0290081 (loganin pentaacetate)

3D-SDF for NP0290081 (loganin pentaacetate)

PDB for NP0290081 (loganin pentaacetate)

3D PDB for NP0290081 (loganin pentaacetate)

SMILES for NP0290081 (loganin pentaacetate)

INCHI for NP0290081 (loganin pentaacetate)

Structure for NP0290081 (loganin pentaacetate)

3D Structure for NP0290081 (loganin pentaacetate)