NP-MRD: Showing NP-Card for methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0147086)

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Record Information

Version

2.0

Created at

2022-09-02 02:37:04 UTC

Updated at

2022-09-02 02:37:04 UTC

NP-MRD ID

NP0147086

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

Description

Methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate 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. methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Rhinanthus angustifolius. Methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231522242D          

 36 39  0  0  0  0            999 V2000
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004231522242D          

 36 39  0  0  0  0            999 V2000
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 30 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
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147086

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=COC(OC2OC(COC(=O)C3=CC=CC=C3)C(O)C(O)C2O)C2C1C(O)CC2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O12/c1-24(31)8-13(25)15-12(21(30)32-2)9-34-22(16(15)24)36-23-19(28)18(27)17(26)14(35-23)10-33-20(29)11-6-4-3-5-7-11/h3-7,9,13-19,22-23,25-28,31H,8,10H2,1-2H3

> <INCHI_KEY>
ONZHSAPTMOLEHV-UHFFFAOYSA-N

> <FORMULA>
C24H30O12

> <MOLECULAR_WEIGHT>
510.492

> <EXACT_MASS>
510.173726406

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.422375866342165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <ALOGPS_LOGP>
0.01

> <JCHEM_LOGP>
-0.5467214256666671

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.1837978779614

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.205250184621782

> <JCHEM_PKA_STRONGEST_BASIC>
-2.910322159173373

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
118.65110000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.789  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.123  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.123  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.456  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.790  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.124  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.124  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.790  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.456  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.189  -1.518   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.627  -1.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   12   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   10   28                                                  
CONECT   28   27                                                            
CONECT   29    8   30   34                                                  
CONECT   30   29    5   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   29   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator

Chemical Formula

C₂₄H₃₀O₁₂

Average Mass

510.4920 Da

Monoisotopic Mass

510.17373 Da

IUPAC Name

methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=COC(OC2OC(COC(=O)C3=CC=CC=C3)C(O)C(O)C2O)C2C1C(O)CC2(C)O

InChI Identifier

InChI=1S/C24H30O12/c1-24(31)8-13(25)15-12(21(30)32-2)9-34-22(16(15)24)36-23-19(28)18(27)17(26)14(35-23)10-33-20(29)11-6-4-3-5-7-11/h3-7,9,13-19,22-23,25-28,31H,8,10H2,1-2H3

InChI Key

ONZHSAPTMOLEHV-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
Rhinanthus angustifolius	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
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Benzoate ester
Bicyclic monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Benzoyl
Oxane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Cyclic alcohol
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Acetal
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	0.01	ALOGPS
logP	-0.55	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	118.65 m³·mol⁻¹	ChemAxon
Polarizability	50.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0147086)

MOL for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0147086 (methyl 1-({6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)