NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0241408)

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Record Information

Version

2.0

Created at

2022-09-07 01:28:51 UTC

Updated at

2022-09-07 01:28:51 UTC

NP-MRD ID

NP0241408

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

Alboside I 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. (2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Chiococca alba. Based on a literature review very few articles have been published on Alboside I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203282D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072203282D          

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 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  6  0  0  0
  5 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241408

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O[C@H]2[C@H](O[C@@H]3OC=C[C@H]4C[C@H](O)[C@H](C)[C@@H]34)O[C@H](CO)[C@@H](O)[C@@H]2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O11/c1-12-16(28)10-14-7-8-33-24(20(12)14)36-25-23(22(31)21(30)18(11-26)34-25)35-19(29)6-4-13-3-5-15(27)17(9-13)32-2/h3-9,12,14,16,18,20-28,30-31H,10-11H2,1-2H3/b6-4+/t12-,14-,16-,18+,20+,21+,22-,23+,24-,25-/m0/s1

> <INCHI_KEY>
KWGAFQKENQSNHF-LFVRPZHJSA-N

> <FORMULA>
C25H32O11

> <MOLECULAR_WEIGHT>
508.52

> <EXACT_MASS>
508.19446185

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.09204056316017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.9212274063333329

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.693268102382252

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.86706589063745

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8334252515697074

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
124.71790000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.121  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.455   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.788   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.454   6.160   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.788   6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.788   8.470   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.122   9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.455   6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.455   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   14   18                                                  
CONECT   25   12   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   11   32                                                  
CONECT   32   31                                                            
CONECT   33    5   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₁₁

Average Mass

508.5200 Da

Monoisotopic Mass

508.19446 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O[C@H]2[C@H](O[C@@H]3OC=C[C@H]4C[C@H](O)[C@H](C)[C@@H]34)O[C@H](CO)[C@@H](O)[C@@H]2O)=CC=C1O

InChI Identifier

InChI=1S/C25H32O11/c1-12-16(28)10-14-7-8-33-24(20(12)14)36-25-23(22(31)21(30)18(11-26)34-25)35-19(29)6-4-13-3-5-15(27)17(9-13)32-2/h3-9,12,14,16,18,20-28,30-31H,10-11H2,1-2H3/b6-4+/t12-,14-,16-,18+,20+,21+,22-,23+,24-,25-/m0/s1

InChI Key

KWGAFQKENQSNHF-LFVRPZHJSA-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
Chiococca alba	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
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Bicyclic monoterpenoid
Methoxyphenol
Monoterpenoid
Phenoxy compound
Styrene
Phenol ether
Anisole
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Oxane
Monosaccharide
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Primary alcohol
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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

C00038401

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

100982915

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0241408)

MOL for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0241408 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,6s,7r,7as)-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)