NP-MRD: Showing NP-Card for Suspensolide D (NP0057597)

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Record Information

Version

2.0

Created at

2022-04-28 03:00:41 UTC

Updated at

2022-04-28 03:00:41 UTC

NP-MRD ID

NP0057597

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Suspensolide D

Description

(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-7-hydroxy-7-(hydroxymethyl)-4-({[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Suspensolide D is found in Viburnum suspensum. Based on a literature review very few articles have been published on (1S,4aS,6S,7R,7aS)-6-(acetyloxy)-7-hydroxy-7-(hydroxymethyl)-4-({[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205002D          

 36 38  0  0  1  0            999 V2000
   -3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0294    3.2820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8499    3.3682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1854    2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    4.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0874    4.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4999    3.3682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 34 36  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282205002D          

 36 38  0  0  1  0            999 V2000
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 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  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
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 23 26  1  1  0  0  0
 22 27  1  1  0  0  0
 21 28  1  1  0  0  0
 28 29  1  0  0  0  0
 13 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057597

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H36O13/c1-10(2)4-16(27)36-21-17-13(5-15(34-11(3)26)23(17,31)9-25)12(7-32-21)8-33-22-20(30)19(29)18(28)14(6-24)35-22/h7,10,13-15,17-22,24-25,28-31H,4-6,8-9H2,1-3H3/t13-,14+,15+,17-,18-,19-,20+,21+,22+,23-/m1/s1

> <INCHI_KEY>
MGKRLWXJXLLAHI-XCDDUOSKSA-N

> <FORMULA>
C23H36O13

> <MOLECULAR_WEIGHT>
520.528

> <EXACT_MASS>
520.215591219

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.19060876709395

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-7-hydroxy-7-(hydroxymethyl)-4-({[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <ALOGPS_LOGP>
-1.09

> <JCHEM_LOGP>
-2.319592761000001

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.69150078279327

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.083471585848574

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835523452752

> <JCHEM_POLAR_SURFACE_AREA>
201.67

> <JCHEM_REFRACTIVITY>
117.55329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-7-hydroxy-7-(hydroxymethyl)-4-({[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.655   6.126   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.186   6.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.813   4.880   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.956   7.621   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -9.496   7.621   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0     -10.266   6.287   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -10.266   8.955   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.195   6.618   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.319   7.629   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.453   8.672   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0     -13.337   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2    5   16                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4   10   11                                             
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3                                                            
CONECT   11    3   12                                                       
CONECT   12   11                                                            
CONECT   13    2   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    1   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   22                                                            
CONECT   28   21   29                                                       
CONECT   29   28                                                            
CONECT   30   13   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1S,4AS,6S,7R,7as)-6-(acetyloxy)-7-hydroxy-7-(hydroxymethyl)-4-({[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₃H₃₆O₁₃

Average Mass

520.5280 Da

Monoisotopic Mass

520.21559 Da

IUPAC Name

Traditional Name

(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-7-hydroxy-7-(hydroxymethyl)-4-({[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H36O13/c1-10(2)4-16(27)36-21-17-13(5-15(34-11(3)26)23(17,31)9-25)12(7-32-21)8-33-22-20(30)19(29)18(28)14(6-24)35-22/h7,10,13-15,17-22,24-25,28-31H,4-6,8-9H2,1-3H3/t13-,14+,15+,17-,18-,19-,20+,21+,22+,23-/m1/s1

InChI Key

MGKRLWXJXLLAHI-XCDDUOSKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 suspensum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Hexose monosaccharide
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Fatty acid ester
Fatty acyl
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	-1.1	ALOGPS
logP	-2.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	117.55 m³·mol⁻¹	ChemAxon
Polarizability	52.19 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

163045591

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Suspensolide D (NP0057597)

MOL for NP0057597 (Suspensolide D)

3D MOL for NP0057597 (Suspensolide D)

3D SDF for NP0057597 (Suspensolide D)

3D-SDF for NP0057597 (Suspensolide D)

PDB for NP0057597 (Suspensolide D)

3D PDB for NP0057597 (Suspensolide D)

SMILES for NP0057597 (Suspensolide D)

INCHI for NP0057597 (Suspensolide D)

Structure for NP0057597 (Suspensolide D)

3D Structure for NP0057597 (Suspensolide D)