NP-MRD: Showing NP-Card for [5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate (NP0239396)

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Record Information

Version

2.0

Created at

2022-09-06 22:59:25 UTC

Updated at

2022-09-06 22:59:25 UTC

NP-MRD ID

NP0239396

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate

Description

AC1MWGJ9 belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups. [5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate is found in Rehmannia glutinosa. AC1MWGJ9 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121514262D          

 42 44  0  0  0  0            999 V2000
    8.2802    2.4750    0.0000 C   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


  Mrv0541 04121514262D          

 42 44  0  0  0  0            999 V2000
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    1.8500    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    4.9500    0.0000 C   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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 21 27  1  0  0  0  0
 10 27  1  0  0  0  0
 14 27  1  0  0  0  0
  8 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 33 38  1  0  0  0  0
  6 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239396

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1OC(OC2OC=CC3C(OC(C)=O)C=C(COC(C)=O)C23)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O15/c1-12(28)35-10-18-9-20(37-14(3)30)19-7-8-34-26(22(18)19)42-27-25(40-17(6)33)24(39-16(5)32)23(38-15(4)31)21(41-27)11-36-13(2)29/h7-9,19-27H,10-11H2,1-6H3

> <INCHI_KEY>
QDMIKXRCDANJJI-UHFFFAOYSA-N

> <FORMULA>
C27H34O15

> <MOLECULAR_WEIGHT>
598.554

> <EXACT_MASS>
598.189770395

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
58.30645511129973

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl acetate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
-0.5351174403333332

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.080230869900257

> <JCHEM_POLAR_SURFACE_AREA>
185.49

> <JCHEM_REFRACTIVITY>
134.08579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      15.456   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.123   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.123   2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.789   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.340  -2.261   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.864  -3.725   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.310  -1.116   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.340   3.801   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.864   5.265   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.642   5.586   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.895   6.410   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.121   6.930   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.453   6.930   0.000  0.00  0.00           C+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       7.454   9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.121   8.470   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.454  10.780   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.455   6.930   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.455   8.470   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.122   9.240   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      12.789   9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   38                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   21   10   14                                                  
CONECT   28    8   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33    6   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₅

Average Mass

598.5540 Da

Monoisotopic Mass

598.18977 Da

IUPAC Name

[5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl acetate

Traditional Name

[5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1OC(OC2OC=CC3C(OC(C)=O)C=C(COC(C)=O)C23)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

InChI Identifier

InChI=1S/C27H34O15/c1-12(28)35-10-18-9-20(37-14(3)30)19-7-8-34-26(22(18)19)42-27-25(40-17(6)33)24(39-16(5)32)23(38-15(4)31)21(41-27)11-36-13(2)29/h7-9,19-27H,10-11H2,1-6H3

InChI Key

QDMIKXRCDANJJI-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
Rehmannia glutinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Hexacarboxylic acids and derivatives

Direct Parent

Hexacarboxylic acids and derivatives

Alternative Parents

Substituents

Hexacarboxylic acid or derivatives
Iridoid o-glycoside
Terpene glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	1.53	ALOGPS
logP	-0.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	185.49 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	134.09 m³·mol⁻¹	ChemAxon
Polarizability	58.31 Å³	ChemAxon
Number of Rings	3	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

3699157

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate (NP0239396)

MOL for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

3D MOL for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

3D SDF for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

3D-SDF for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

PDB for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

3D PDB for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

SMILES for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

INCHI for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

Structure for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)

3D Structure for NP0239396 ([5-(acetyloxy)-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl acetate)