NP-MRD: Showing NP-Card for Ipecosidic acid (NP0069979)

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Record Information

Version

2.0

Created at

2022-04-28 15:15:59 UTC

Updated at

2022-04-28 15:15:59 UTC

NP-MRD ID

NP0069979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ipecosidic acid

Description

(2S,3R,4S)-4-{[(1S)-2-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid 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. Ipecosidic acid is found in Cephaelis ipecacuanha . Based on a literature review very few articles have been published on (2S,3R,4S)-4-{[(1S)-2-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217162D          

 39 42  0  0  1  0            999 V2000
    2.2818   -7.0806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4796   -7.2730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.3185   -6.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863   -6.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3 37  1  1  0  0  0
  2 38  1  6  0  0  0
  1 39  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282217162D          

 39 42  0  0  1  0            999 V2000
    2.2818   -7.0806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.1095   -6.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451   -8.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8496   -7.6791    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  4  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  6  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 21 32  1  0  0  0  0
 31 33  1  0  0  0  0
 30 34  1  0  0  0  0
 11 35  1  6  0  0  0
 35 36  2  0  0  0  0
  3 37  1  1  0  0  0
  2 38  1  6  0  0  0
  1 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0069979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N1CCC2=C(C=C(O)C(O)=C2)[C@@H]1C[C@H]1[C@@H](C=C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H33NO12/c1-3-13-15(7-17-14-8-19(31)18(30)6-12(14)4-5-27(17)11(2)29)16(24(35)36)10-37-25(13)39-26-23(34)22(33)21(32)20(9-28)38-26/h3,6,8,10,13,15,17,20-23,25-26,28,30-34H,1,4-5,7,9H2,2H3,(H,35,36)/t13-,15+,17+,20-,21-,22+,23-,25+,26+/m1/s1

> <INCHI_KEY>
QCXXDKLITYYVTE-QIAPLWSDSA-N

> <FORMULA>
C26H33NO12

> <MOLECULAR_WEIGHT>
551.545

> <EXACT_MASS>
551.200275507

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.536877443724364

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S)-4-{[(1S)-2-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
-0.8743602659999983

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.190037983938955

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.209163231988594

> <JCHEM_PKA_STRONGEST_BASIC>
-1.322822632005972

> <JCHEM_POLAR_SURFACE_AREA>
206.67999999999998

> <JCHEM_REFRACTIVITY>
132.4924

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,6S)-4-{[(1S)-2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl]methyl}-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.259 -13.217   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.762 -13.576   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.702 -12.459   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.140 -10.983   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.637 -10.623   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.697 -11.741   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.195 -11.381   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.254 -12.499   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.095  -9.881   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.585  -8.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.555  -7.229   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.030  -5.764   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.537  -5.444   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.567  -6.589   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.091  -8.053   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.303  -4.090   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.667  -3.292   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.999  -4.059   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.259  -4.687   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -2.935  -2.884   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.024  -4.012   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.499  -2.396   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.559  -2.810   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.385   0.120   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.921  -8.062   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.785  -9.475   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.204 -12.818   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.324 -15.053   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       5.319 -14.334   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   38                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   35                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   32                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   22   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   21                                                       
CONECT   33   31                                                            
CONECT   34   30                                                            
CONECT   35   11   36                                                       
CONECT   36   35                                                            
CONECT   37    3                                                            
CONECT   38    2                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S)-4-{[(1S)-2-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate	Generator

Chemical Formula

C₂₆H₃₃NO₁₂

Average Mass

551.5450 Da

Monoisotopic Mass

551.20028 Da

IUPAC Name

Traditional Name

(4S,5R,6S)-4-{[(1S)-2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl]methyl}-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)N1CCC2=C(C=C(O)C(O)=C2)[C@@H]1C[C@H]1[C@@H](C=C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(O)=O

InChI Identifier

InChI=1S/C26H33NO12/c1-3-13-15(7-17-14-8-19(31)18(30)6-12(14)4-5-27(17)11(2)29)16(24(35)36)10-37-25(13)39-26-23(34)22(33)21(32)20(9-28)38-26/h3,6,8,10,13,15,17,20-23,25-26,28,30-34H,1,4-5,7,9H2,2H3,(H,35,36)/t13-,15+,17+,20-,21-,22+,23-,25+,26+/m1/s1

InChI Key

QCXXDKLITYYVTE-QIAPLWSDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cephaelis ipecacuanha	Plant	KNApSAcK

Chemical Taxonomy

Description

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
O-glycosyl compound
Secoiridoid-skeleton
Glycosyl compound
Tetrahydroisoquinoline
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Benzenoid
Oxane
Monosaccharide
Acetamide
Vinylogous ester
Tertiary carboxylic acid amide
Secondary alcohol
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.24	ALOGPS
logP	-0.87	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	206.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.49 m³·mol⁻¹	ChemAxon
Polarizability	54.54 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

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

162957838

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ipecosidic acid (NP0069979)

MOL for NP0069979 (Ipecosidic acid)

3D MOL for NP0069979 (Ipecosidic acid)

3D SDF for NP0069979 (Ipecosidic acid)

3D-SDF for NP0069979 (Ipecosidic acid)

PDB for NP0069979 (Ipecosidic acid)

3D PDB for NP0069979 (Ipecosidic acid)

SMILES for NP0069979 (Ipecosidic acid)

INCHI for NP0069979 (Ipecosidic acid)

Structure for NP0069979 (Ipecosidic acid)

3D Structure for NP0069979 (Ipecosidic acid)