NP-MRD: Showing NP-Card for (1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate (NP0309805)

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Record Information

Version

2.0

Created at

2022-09-11 04:39:21 UTC

Updated at

2022-09-11 04:39:21 UTC

NP-MRD ID

NP0309805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate

Description

(1R,4aR,6R,7S,7aR)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl (3S)-3-methylpentanoate belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. (1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate is found in Viburnum luzonicum. Based on a literature review very few articles have been published on (1R,4aR,6R,7S,7aR)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl (3S)-3-methylpentanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112206392D          

 34 36  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309112206392D          

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M  END
> <DATABASE_ID>
NP0309805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)CC(=O)O[C@H]1OC=C(CO)[C@@H]2C[C@@H](O)[C@@](O)(COC(=O)\C=C\C3=CC=C(O)C=C3)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O9/c1-3-15(2)10-22(30)34-24-23-19(17(12-26)13-32-24)11-20(28)25(23,31)14-33-21(29)9-6-16-4-7-18(27)8-5-16/h4-9,13,15,19-20,23-24,26-28,31H,3,10-12,14H2,1-2H3/b9-6+/t15-,19-,20+,23-,24+,25-/m0/s1

> <INCHI_KEY>
RYYMDCNLERUECM-YEYGRHMPSA-N

> <FORMULA>
C25H32O9

> <MOLECULAR_WEIGHT>
476.522

> <EXACT_MASS>
476.20463261

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.12995252793081

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.185011535666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.660878041404462

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398404860083033

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7762755843018443

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
122.1381

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.147  -7.190   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.520  -8.597   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.290  -9.931   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.989  -8.436   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.989  -9.976   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.457  -8.597   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.831 -10.004   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.736 -11.250   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.109 -12.657   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.267 -11.089   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.173 -12.335   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.704 -12.174   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.331 -10.767   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.862 -10.606   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.767 -11.852   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.299 -11.691   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.141 -13.259   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.609 -13.420   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   34                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   34                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
CONECT   34   19    9   15                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1R,4AR,6R,7S,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-1-yl (3S)-3-methylpentanoic acid	Generator

Chemical Formula

C₂₅H₃₂O₉

Average Mass

476.5220 Da

Monoisotopic Mass

476.20463 Da

IUPAC Name

(1R,4aR,6R,7S,7aR)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl (3S)-3-methylpentanoate

Traditional Name

(1R,4aR,6R,7S,7aR)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-1-yl (3S)-3-methylpentanoate

CAS Registry Number

Not Available

SMILES

CC[C@H](C)CC(=O)O[C@H]1OC=C(CO)[C@@H]2C[C@@H](O)[C@@](O)(COC(=O)\C=C\C3=CC=C(O)C=C3)[C@H]12

InChI Identifier

InChI=1S/C25H32O9/c1-3-15(2)10-22(30)34-24-23-19(17(12-26)13-32-24)11-20(28)25(23,31)14-33-21(29)9-6-16-4-7-18(27)8-5-16/h4-9,13,15,19-20,23-24,26-28,31H,3,10-12,14H2,1-2H3/b9-6+/t15-,19-,20+,23-,24+,25-/m0/s1

InChI Key

RYYMDCNLERUECM-YEYGRHMPSA-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
Viburnum luzonicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Iridoid-skeleton
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
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
logP	2.19	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	122.14 m³·mol⁻¹	ChemAxon
Polarizability	49.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163190006

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,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate (NP0309805)

MOL for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D MOL for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D SDF for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D-SDF for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

PDB for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D PDB for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

SMILES for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

INCHI for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

Structure for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D Structure for NP0309805 ((1r,4ar,6r,7s,7ar)-6,7-dihydroxy-4-(hydroxymethyl)-7-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)