NP-MRD: Showing NP-Card for (6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate (NP0240535)

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Record Information

Version

2.0

Created at

2022-09-07 00:23:08 UTC

Updated at

2022-09-07 00:23:08 UTC

NP-MRD ID

NP0240535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate

Description

(6-Chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-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. (6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate is found in Premna odorata. Based on a literature review very few articles have been published on (6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202232D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072202232D          

 37 40  0  0  0  0            999 V2000
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 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  0  0  0  0
 24 37  1  0  0  0  0
 20 37  1  0  0  0  0
 14 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC=CC3C(O)C(Cl)C(O)(COC(=O)C=CC4=CC=C(O)C=C4)C23)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO12/c25-21-17(29)13-7-8-34-22(37-23-20(32)19(31)18(30)14(9-26)36-23)16(13)24(21,33)10-35-15(28)6-3-11-1-4-12(27)5-2-11/h1-8,13-14,16-23,26-27,29-33H,9-10H2

> <INCHI_KEY>
UNCYGAPGGIHSCE-UHFFFAOYSA-N

> <FORMULA>
C24H29ClO12

> <MOLECULAR_WEIGHT>
544.93

> <EXACT_MASS>
544.1347541

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.1151407042657

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
-0.5085899296666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.054445409255608

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397682685505712

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760192899

> <JCHEM_POLAR_SURFACE_AREA>
195.6

> <JCHEM_REFRACTIVITY>
125.30120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)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  O   UNK     0      -1.875  -4.859   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.875  -3.319   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.209  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.543  -3.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.876  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.210  -3.319   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.544  -2.549   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.544  -1.009   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.877  -0.239   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.210  -0.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.876  -1.009   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.542  -2.549   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.792  -3.319   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.752  -3.956   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -0.320  -1.303   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   37                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   37                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
CONECT   37   24   20   14                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(6-Chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₄H₂₉ClO₁₂

Average Mass

544.9300 Da

Monoisotopic Mass

544.13475 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2OC=CC3C(O)C(Cl)C(O)(COC(=O)C=CC4=CC=C(O)C=C4)C23)C(O)C(O)C1O

InChI Identifier

InChI=1S/C24H29ClO12/c25-21-17(29)13-7-8-34-22(37-23-20(32)19(31)18(30)14(9-26)36-23)16(13)24(21,33)10-35-15(28)6-3-11-1-4-12(27)5-2-11/h1-8,13-14,16-23,26-27,29-33H,9-10H2

InChI Key

UNCYGAPGGIHSCE-UHFFFAOYSA-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
Premna odorata	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
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Iridoid-skeleton
O-glycosyl compound
Glycosyl compound
Monoterpenoid
Aromatic monoterpenoid
Bicyclic monoterpenoid
Styrene
Fatty acid ester
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Chlorohydrin
Halohydrin
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Organic oxygen compound
Hydrocarbon derivative
Alkyl chloride
Carbonyl group
Primary alcohol
Organic oxide
Alkyl halide
Alcohol
Organooxygen compound
Organochloride
Organohalogen 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

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

162855674

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate (NP0240535)

MOL for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0240535 ((6-chloro-5,7-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)