NP-MRD: Showing NP-Card for (1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate (NP0210921)

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Record Information

Version

2.0

Created at

2022-09-05 08:57:51 UTC

Updated at

2022-09-05 08:57:51 UTC

NP-MRD ID

NP0210921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate

Description

(1R,4aR,7R,7aR)-4a-hydroxy-7-methyl-1-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl (2E)-3-phenylprop-2-enoate 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. (1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate is found in Phlogacanthus curviflorus. Based on a literature review very few articles have been published on (1R,4aR,7R,7aR)-4a-hydroxy-7-methyl-1-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl (2E)-3-phenylprop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210572D          

 34 37  0  0  1  0            999 V2000
    1.4743   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309052210572D          

 34 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0210921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(CC[C@@]2(O)C=CO[C@H](O[C@H]3O[C@H](CO)[C@H](O)[C@@H](O)[C@H]3O)[C@@H]12)OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O10/c1-23(34-16(26)8-7-14-5-3-2-4-6-14)9-10-24(30)11-12-31-22(20(23)24)33-21-19(29)18(28)17(27)15(13-25)32-21/h2-8,11-12,15,17-22,25,27-30H,9-10,13H2,1H3/b8-7+/t15-,17+,18-,19-,20+,21-,22-,23-,24-/m1/s1

> <INCHI_KEY>
ZBNLXIAXKWPLCF-VQXGFVMGSA-N

> <FORMULA>
C24H30O10

> <MOLECULAR_WEIGHT>
478.494

> <EXACT_MASS>
478.183897166

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.57789147266443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aR,7R,7aR)-4a-hydroxy-7-methyl-1-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
0.2201019270000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.115856815741335

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.196539496926757

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760235099

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
117.45370000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,7R,7aR)-4a-hydroxy-7-methyl-1-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,5H,6H,7aH-cyclopenta[c]pyran-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.752  -3.956   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  O   UNK     0       0.792  -3.319   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.542  -2.549   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.542  -1.009   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.875  -3.319   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.875  -4.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.209  -5.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.209  -7.169   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.543  -7.939   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.876  -7.169   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.876  -5.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.543  -4.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.429   0.999   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.258  -9.773   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.259  -4.383   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14   34                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    2   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   34                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
CONECT   34   21   16    2                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1R,4AR,7R,7ar)-4a-hydroxy-7-methyl-1-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-7-yl (2E)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₄H₃₀O₁₀

Average Mass

478.4940 Da

Monoisotopic Mass

478.18390 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]1(CC[C@@]2(O)C=CO[C@H](O[C@H]3O[C@H](CO)[C@H](O)[C@@H](O)[C@H]3O)[C@@H]12)OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C24H30O10/c1-23(34-16(26)8-7-14-5-3-2-4-6-14)9-10-24(30)11-12-31-22(20(23)24)33-21-19(29)18(28)17(27)15(13-25)32-21/h2-8,11-12,15,17-22,25,27-30H,9-10,13H2,1H3/b8-7+/t15-,17+,18-,19-,20+,21-,22-,23-,24-/m1/s1

InChI Key

ZBNLXIAXKWPLCF-VQXGFVMGSA-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
Phlogacanthus curviflorus	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
Cinnamic acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Styrene
Fatty acid ester
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Oxane
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Primary alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
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

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

163187075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate (NP0210921)

MOL for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0210921 ((1r,4ar,7r,7ar)-4a-hydroxy-7-methyl-1-{[(2r,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl (2e)-3-phenylprop-2-enoate)