NP-MRD: Showing NP-Card for (1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate (NP0225796)

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Record Information

Version

2.0

Created at

2022-09-06 04:37:38 UTC

Updated at

2022-09-06 04:37:38 UTC

NP-MRD ID

NP0225796

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate

Description

(1S)-4,7-Bis(acetoxymethyl)-1,6,7,7aalpha-tetrahydrocyclopenta[c]pyran-1alpha,6alpha,7beta-triol 1-(3-acetoxy-3-methylbutanoate)6-(3-methylbutanoate) belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. (1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate is found in Valeriana jatamansi. Based on a literature review very few articles have been published on (1S)-4,7-Bis(acetoxymethyl)-1,6,7,7aalpha-tetrahydrocyclopenta[c]pyran-1alpha,6alpha,7beta-triol 1-(3-acetoxy-3-methylbutanoate)6-(3-methylbutanoate).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062206372D          

 38 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062206372D          

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    6.3151    3.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5976    1.9378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  6  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0225796

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@H]1C=C2[C@H]([C@H](OC(=O)CC(C)(C)OC(C)=O)OC=C2COC(C)=O)[C@@]1(O)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O12/c1-14(2)8-21(30)36-20-9-19-18(11-33-15(3)27)12-34-24(23(19)26(20,32)13-35-16(4)28)37-22(31)10-25(6,7)38-17(5)29/h9,12,14,20,23-24,32H,8,10-11,13H2,1-7H3/t20-,23+,24-,26+/m0/s1

> <INCHI_KEY>
JARNEKBLBWLHCJ-FKIWKMFDSA-N

> <FORMULA>
C26H36O12

> <MOLECULAR_WEIGHT>
540.562

> <EXACT_MASS>
540.220676599

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.09013815637974

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,6S,7R,7aS)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate

> <JCHEM_LOGP>
0.6418634776666637

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.850648809861738

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.517702208502627

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8845567550265097

> <JCHEM_POLAR_SURFACE_AREA>
160.95999999999998

> <JCHEM_REFRACTIVITY>
128.74909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6S,7R,7aS)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1H,6H,7aH-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.147   5.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.623   6.783   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.147   8.117   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.163   6.783   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.933   8.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.473   8.117   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.243   9.451   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.783   9.451   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.553   8.117   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.093   8.117   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.863   9.451   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.093  10.785   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.403   9.451   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.173  10.785   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.840  11.555   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.507  10.015   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.943  12.118   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.483  12.118   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.253  13.452   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.253  10.785   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.783   6.783   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.243   6.783   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.768   5.319   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.013   4.414   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.013   2.874   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.347   0.564   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.681   2.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.015   2.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.348   2.874   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.015   0.564   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.259   5.319   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.302   4.185   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.769   5.623   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.787   4.468   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.297   4.772   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.788   6.232   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.315   3.617   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    9   22   32                                                  
CONECT   22   21    6   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   24   21   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
(1S)-4,7-Bis(acetoxymethyl)-1,6,7,7aalpha-tetrahydrocyclopenta[c]pyran-1a,6a,7b-triol 1-(3-acetoxy-3-methylbutanoate)6-(3-methylbutanoate)	Generator
(1S)-4,7-Bis(acetoxymethyl)-1,6,7,7aalpha-tetrahydrocyclopenta[c]pyran-1a,6a,7b-triol 1-(3-acetoxy-3-methylbutanoic acid)6-(3-methylbutanoic acid)	Generator
(1S)-4,7-Bis(acetoxymethyl)-1,6,7,7aalpha-tetrahydrocyclopenta[c]pyran-1alpha,6alpha,7beta-triol 1-(3-acetoxy-3-methylbutanoic acid)6-(3-methylbutanoic acid)	Generator
(1S)-4,7-Bis(acetoxymethyl)-1,6,7,7aalpha-tetrahydrocyclopenta[c]pyran-1α,6α,7β-triol 1-(3-acetoxy-3-methylbutanoate)6-(3-methylbutanoate)	Generator
(1S)-4,7-Bis(acetoxymethyl)-1,6,7,7aalpha-tetrahydrocyclopenta[c]pyran-1α,6α,7β-triol 1-(3-acetoxy-3-methylbutanoic acid)6-(3-methylbutanoic acid)	Generator

Chemical Formula

C₂₆H₃₆O₁₂

Average Mass

540.5620 Da

Monoisotopic Mass

540.22068 Da

IUPAC Name

(1S,6S,7R,7aS)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate

Traditional Name

(1S,6S,7R,7aS)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1H,6H,7aH-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@H]1C=C2[C@H]([C@H](OC(=O)CC(C)(C)OC(C)=O)OC=C2COC(C)=O)[C@@]1(O)COC(C)=O

InChI Identifier

InChI=1S/C26H36O12/c1-14(2)8-21(30)36-20-9-19-18(11-33-15(3)27)12-34-24(23(19)26(20,32)13-35-16(4)28)37-22(31)10-25(6,7)38-17(5)29/h9,12,14,20,23-24,32H,8,10-11,13H2,1-7H3/t20-,23+,24-,26+/m0/s1

InChI Key

JARNEKBLBWLHCJ-FKIWKMFDSA-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
Valeriana jatamansi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Iridoid-skeleton
Bicyclic monoterpenoid
Monoterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.64	ChemAxon
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	160.96 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	128.75 m³·mol⁻¹	ChemAxon
Polarizability	55.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

9937956

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11763260

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate (NP0225796)

MOL for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

3D MOL for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

3D SDF for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

3D-SDF for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

PDB for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

3D PDB for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

SMILES for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

INCHI for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

Structure for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)

3D Structure for NP0225796 ((1s,6s,7r,7as)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl 3-(acetyloxy)-3-methylbutanoate)