NP-MRD: Showing NP-Card for 6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate (NP0318400)

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Record Information

Version

2.0

Created at

2022-09-11 18:52:23 UTC

Updated at

2022-09-11 18:52:23 UTC

NP-MRD ID

NP0318400

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate

Description

6-Chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate 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-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate is found in Veronica longifolia. 6-Chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251504352D          

 36 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004251504352D          

 36 39  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0318400

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H27ClO13/c23-18-17(35-19(31)8-1-2-10(26)11(27)5-8)9-3-4-33-20(13(9)22(18,32)7-25)36-21-16(30)15(29)14(28)12(6-24)34-21/h1-5,9,12-18,20-21,24-30,32H,6-7H2

> <INCHI_KEY>
MTRQBGBLTPNJPL-UHFFFAOYSA-N

> <FORMULA>
C22H27ClO13

> <MOLECULAR_WEIGHT>
534.9

> <EXACT_MASS>
534.1140186

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.38756116858596

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.25

> <JCHEM_LOGP>
-1.350746120666666

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.813628091841993

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.556693812645124

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760192899

> <JCHEM_POLAR_SURFACE_AREA>
215.82999999999996

> <JCHEM_REFRACTIVITY>
117.5364

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0      12.789   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.340  -2.261   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.310  -1.116   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.864  -3.725   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.642  -4.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.118  -5.510   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.088  -6.655   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.563  -8.119   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.419  -6.334   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.449  -7.479   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.895  -4.870   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0       0.877   0.770   0.000  0.00  0.00          Cl+0
HETATM   26  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.989   2.786   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.949   3.423   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.044   4.669   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.121   6.930   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.788   6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.788   8.470   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.455   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   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16                                                       
CONECT   24   12   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   30                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   26    7   11                                                  
CONECT   31    5   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₂H₂₇ClO₁₃

Average Mass

534.9000 Da

Monoisotopic Mass

534.11402 Da

IUPAC Name

6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate

Traditional Name

6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2OC=CC3C(OC(=O)C4=CC=C(O)C(O)=C4)C(Cl)C(O)(CO)C23)C(O)C(O)C1O

InChI Identifier

InChI=1S/C22H27ClO13/c23-18-17(35-19(31)8-1-2-10(26)11(27)5-8)9-3-4-33-20(13(9)22(18,32)7-25)36-21-16(30)15(29)14(28)12(6-24)34-21/h1-5,9,12-18,20-21,24-30,32H,6-7H2

InChI Key

MTRQBGBLTPNJPL-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
Veronica longifolia	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
Hexose monosaccharide
O-glycosyl compound
Iridoid-skeleton
Dihydroxybenzoic acid
P-hydroxybenzoic acid alkyl ester
Glycosyl compound
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Monoterpenoid
Bicyclic monoterpenoid
Benzoate ester
Aromatic monoterpenoid
Benzoic acid or derivatives
Catechol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Secondary alcohol
Halohydrin
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Organooxygen compound
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organochloride
Alkyl halide
Alkyl chloride
Alcohol
Organic oxygen compound
Primary 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	-0.25	ALOGPS
logP	-1.4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.54 m³·mol⁻¹	ChemAxon
Polarizability	49.39 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

75244302

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-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate (NP0318400)

MOL for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

3D MOL for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

3D SDF for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

3D-SDF for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

PDB for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

3D PDB for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

SMILES for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

INCHI for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

Structure for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)

3D Structure for NP0318400 (6-chloro-7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dihydroxybenzoate)