NP-MRD: Showing NP-Card for (1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate (NP0157048)

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Record Information

Version

2.0

Created at

2022-09-02 14:20:58 UTC

Updated at

2022-09-02 14:20:58 UTC

NP-MRD ID

NP0157048

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1R,6R,7S,7aR)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1H,6H,7H,7aH-cyclopenta[c]pyran-1-yl (3S)-3-methylpentanoate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate is found in Valeriana jatamansi. Based on a literature review very few articles have been published on (1R,6R,7S,7aR)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1H,6H,7H,7aH-cyclopenta[c]pyran-1-yl (3S)-3-methylpentanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022216202D          

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M  END

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M  END


  Mrv1652309022216202D          

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 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 28 35  1  0  0  0  0
 35 18  1  6  0  0  0
  9 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157048

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)CC(=O)O[C@H]1OC=C(COC(C)=O)C2=C[C@@H](OC(=O)CC(C)C)[C@@](O)(COC(C)=O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O10/c1-7-15(4)9-22(29)35-24-23-19(18(12-32-24)11-31-16(5)26)10-20(34-21(28)8-14(2)3)25(23,30)13-33-17(6)27/h10,12,14-15,20,23-24,30H,7-9,11,13H2,1-6H3/t15-,20+,23-,24+,25-/m0/s1

> <INCHI_KEY>
VJPHRAFHYZGASA-FLPVFDBPSA-N

> <FORMULA>
C25H36O10

> <MOLECULAR_WEIGHT>
496.553

> <EXACT_MASS>
496.230847359

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.137382680533435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
1.960513957333333

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.850696517384463

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.517702223744905

> <JCHEM_PKA_STRONGEST_BASIC>
-3.884556748389554

> <JCHEM_POLAR_SURFACE_AREA>
134.66

> <JCHEM_REFRACTIVITY>
122.51649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-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      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.147  -7.190   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.520  -8.597   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.290  -9.931   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.830  -9.931   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.600 -11.265   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.600  -8.597   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.140  -8.597   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.910  -7.264   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.910  -9.931   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.989  -8.436   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.989  -9.976   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.457  -8.597   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.831 -10.004   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.736 -11.250   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.267 -11.089   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.109 -12.657   0.000  0.00  0.00           O+0
HETATM   35  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   35                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   29   30   35                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   28   18    9                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1R,6R,7S,7AR)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1H,6H,7H,7ah-cyclopenta[c]pyran-1-yl (3S)-3-methylpentanoic acid	Generator

Chemical Formula

C₂₅H₃₆O₁₀

Average Mass

496.5530 Da

Monoisotopic Mass

496.23085 Da

IUPAC Name

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

Traditional Name

(1R,6R,7S,7aR)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1H,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(COC(C)=O)C2=C[C@@H](OC(=O)CC(C)C)[C@@](O)(COC(C)=O)[C@H]12

InChI Identifier

InChI=1S/C25H36O10/c1-7-15(4)9-22(29)35-24-23-19(18(12-32-24)11-31-16(5)26)10-20(34-21(28)8-14(2)3)25(23,30)13-33-17(6)27/h10,12,14-15,20,23-24,30H,7-9,11,13H2,1-6H3/t15-,20+,23-,24+,25-/m0/s1

InChI Key

VJPHRAFHYZGASA-FLPVFDBPSA-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 tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic 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	2.75	ALOGPS
logP	1.96	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	134.66 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	122.52 m³·mol⁻¹	ChemAxon
Polarizability	52.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

163010533

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate (NP0157048)

MOL for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D MOL for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D SDF for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D-SDF for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

PDB for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D PDB for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

SMILES for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

INCHI for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

Structure for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)

3D Structure for NP0157048 ((1r,6r,7s,7ar)-4,7-bis[(acetyloxy)methyl]-7-hydroxy-6-[(3-methylbutanoyl)oxy]-1h,6h,7ah-cyclopenta[c]pyran-1-yl (3s)-3-methylpentanoate)