NP-MRD: Showing NP-Card for citrifolinoside (NP0232722)

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Record Information

Version

2.0

Created at

2022-09-06 14:03:11 UTC

Updated at

2022-09-06 14:03:11 UTC

NP-MRD ID

NP0232722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

citrifolinoside

Description

Citrifolinoside, also known as yopaaoside a, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Citrifolinoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. citrifolinoside is found in Morinda citrifolia. citrifolinoside was first documented in 2001 (PMID: 11348221). Based on a literature review very few articles have been published on citrifolinoside (PMID: 17078712).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062216032D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062216032D          

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    0.0064   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3374   -0.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180   -1.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763    1.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5675    0.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7290    1.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    1.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2356    2.4216    0.0000 O   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
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23  5  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 32 40  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 27 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0232722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](O[C@@H]2OC=C([C@H]3[C@@H]4O[C@@H]4[C@]4(OC(=O)C(=C4)C(=O)C4=CC=C(OC)C(O)=C4)[C@@H]23)C(=O)OC)O[C@H](CO)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O15/c1-36-14-5-4-10(6-13(14)30)18(31)11-7-28(43-25(11)35)17-16(21-23(28)41-21)12(24(34)38-3)9-39-26(17)42-27-22(37-2)20(33)19(32)15(8-29)40-27/h4-7,9,15-17,19-23,26-27,29-30,32-33H,8H2,1-3H3/t15-,16-,17-,19-,20+,21+,22-,23+,26+,27+,28-/m1/s1

> <INCHI_KEY>
NUMSWUCLFNXPFE-WVQLPIEPSA-N

> <FORMULA>
C28H30O15

> <MOLECULAR_WEIGHT>
606.533

> <EXACT_MASS>
606.158470266

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.37094361453373

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1'S,2R,2'S,4'S,6'S,7'S)-7'-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-4-(3-hydroxy-4-methoxybenzoyl)-5-oxo-5H-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

> <JCHEM_LOGP>
-0.34885562666666603

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.709839638748935

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.301714965410005

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849638114885

> <JCHEM_POLAR_SURFACE_AREA>
209.26999999999998

> <JCHEM_REFRACTIVITY>
137.7403

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,2R,2'S,4'S,6'S,7'S)-7'-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-4-(3-hydroxy-4-methoxybenzoyl)-5-oxo-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

> <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      10.852   8.335   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.906   7.119   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.486   5.693   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.012   5.482   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.541   4.477   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.120   3.051   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.175   1.835   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.649   2.046   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.704   0.831   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.284  -0.596   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.809  -0.807   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.389  -2.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.915  -2.445   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.494  -3.871   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.443  -3.449   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.023  -4.876   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.918  -3.238   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.972  -4.454   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.338  -1.811   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.813  -1.600   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.867  -2.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.070   3.473   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.015   4.688   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.151   5.963   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.041   7.031   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.672   5.536   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.621   3.997   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.571   2.457   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.091   2.030   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.568   0.582   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.560  -0.596   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.052   0.311   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.528  -1.137   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.012  -1.408   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.980  -0.230   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.497  -0.501   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.020  -1.949   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.457   1.218   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.449   2.396   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.059   1.489   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.228   3.305   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.688   3.355   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       4.173   4.520   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    8   23   27                                                  
CONECT   23   22    5   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   26                                                       
CONECT   26   25   24   27                                                  
CONECT   27   26   22   28   43                                             
CONECT   28   27   29                                                       
CONECT   29   28   30   41                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   40                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   32                                                       
CONECT   41   29   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   27                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
Yopaaoside a	MeSH

Chemical Formula

C₂₈H₃₀O₁₅

Average Mass

606.5330 Da

Monoisotopic Mass

606.15847 Da

IUPAC Name

methyl (1'S,2R,2'S,4'S,6'S,7'S)-7'-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-4-(3-hydroxy-4-methoxybenzoyl)-5-oxo-5H-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

Traditional Name

methyl (1'S,2R,2'S,4'S,6'S,7'S)-7'-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-4-(3-hydroxy-4-methoxybenzoyl)-5-oxo-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](O[C@@H]2OC=C([C@H]3[C@@H]4O[C@@H]4[C@]4(OC(=O)C(=C4)C(=O)C4=CC=C(OC)C(O)=C4)[C@@H]23)C(=O)OC)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C28H30O15/c1-36-14-5-4-10(6-13(14)30)18(31)11-7-28(43-25(11)35)17-16(21-23(28)41-21)12(24(34)38-3)9-39-26(17)42-27-22(37-2)20(33)19(32)15(8-29)40-27/h4-7,9,15-17,19-23,26-27,29-30,32-33H,8H2,1-3H3/t15-,16-,17-,19-,20+,21+,22-,23+,26+,27+,28-/m1/s1

InChI Key

NUMSWUCLFNXPFE-WVQLPIEPSA-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
Morinda citrifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Methoxyphenol
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Aryl ketone
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
2-furanone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Benzenoid
Oxane
Vinylogous ester
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Carboxylic acid ester
Lactone
Ketone
Secondary alcohol
Dialkyl ether
Carboxylic acid derivative
Ether
Oxirane
Organoheterocyclic compound
Acetal
Oxacycle
Organic oxide
Alcohol
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:65637 )
epoxide (CHEBI:65637 )
phenols (CHEBI:65637 )
beta-D-glucoside (CHEBI:65637 )
enone (CHEBI:65637 )
methyl ester (CHEBI:65637 )
aromatic ketone (CHEBI:65637 )
gamma-lactone (CHEBI:65637 )
oxaspiro compound (CHEBI:65637 )
iridoid monoterpenoid (CHEBI:65637 )

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	-0.35	ChemAxon
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	209.27 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	137.74 m³·mol⁻¹	ChemAxon
Polarizability	57.37 Å³	ChemAxon
Number of Rings	6	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

28532951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70680257

PDB ID

Not Available

ChEBI ID

65637

Good Scents ID

Not Available

References

General References

Schripsema J, Caprini GP, Dagnino D: Revision of the structures of citrifolinin A, citrifolinoside, yopaaoside A, yopaaoside B, and morindacin, iridoids from Morinda citrifolia L. and Morinda coreia Ham. Org Lett. 2006 Nov 9;8(23):5337-40. doi: 10.1021/ol0622108. [PubMed:17078712 ]
Sang S, He K, Liu G, Zhu N, Cheng X, Wang M, Zheng Q, Dong Z, Ghai G, Rosen RT, Ho CT: A new unusual iridoid with inhibition of activator protein-1 (AP-1) from the leaves of Morinda citrifolia L. Org Lett. 2001 May 3;3(9):1307-9. doi: 10.1021/ol0156648. [PubMed:11348221 ]
LOTUS database [Link]

Showing NP-Card for citrifolinoside (NP0232722)

MOL for NP0232722 (citrifolinoside)

3D MOL for NP0232722 (citrifolinoside)

3D SDF for NP0232722 (citrifolinoside)

3D-SDF for NP0232722 (citrifolinoside)

PDB for NP0232722 (citrifolinoside)

3D PDB for NP0232722 (citrifolinoside)

SMILES for NP0232722 (citrifolinoside)

INCHI for NP0232722 (citrifolinoside)

Structure for NP0232722 (citrifolinoside)

3D Structure for NP0232722 (citrifolinoside)