NP-MRD: Showing NP-Card for Aceroside VIII (NP0070831)

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Record Information

Version

2.0

Created at

2022-04-28 16:15:12 UTC

Updated at

2022-04-28 16:15:12 UTC

NP-MRD ID

NP0070831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aceroside VIII

Description

Aceroside VIII belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. Aceroside VIII is found in Acer nikoense , Alnus firma, Betula pendula and Betula platyphylla. Aceroside VIII was first documented in 2012 (PMID: 22972321). Based on a literature review a small amount of articles have been published on Aceroside VIII (PMID: 27240338) (PMID: 25590368) (PMID: 23079232).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218152D          

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M  END

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M  END


  Mrv1652304282218152D          

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    5.2096   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197   -5.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598   -4.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3699   -4.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6400   -5.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0999   -6.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2897   -5.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4501   -5.5736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -7.7564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -7.4446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715   -5.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -4.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0015   -4.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715   -3.7027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7996   -3.0260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973   -2.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0768   -2.6381    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0609   -3.4630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7189   -3.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347   -1.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -1.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980   -2.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  1  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  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  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
  5 29  1  6  0  0  0
  4 30  1  1  0  0  0
  3 31  1  6  0  0  0
  2 32  1  1  0  0  0
 32 33  1  0  0  0  0
 34 33  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
 37 38  1  0  0  0  0
 34 38  1  0  0  0  0
 38 39  1  6  0  0  0
 37 40  1  1  0  0  0
 40 41  1  0  0  0  0
 37 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0070831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@]1(O)CO[C@@H](OC[C@H]2O[C@@H](O[C@H](CCCCC3=CC=C(O)C=C3)CCC3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O12/c31-16-30(38)17-40-29(27(30)37)39-15-23-24(34)25(35)26(36)28(42-23)41-22(14-9-19-7-12-21(33)13-8-19)4-2-1-3-18-5-10-20(32)11-6-18/h5-8,10-13,22-29,31-38H,1-4,9,14-17H2/t22-,23-,24-,25+,26-,27+,28-,29-,30-/m1/s1

> <INCHI_KEY>
JLMGCBFIPZDHLZ-GYOMMSMMSA-N

> <FORMULA>
C30H42O12

> <MOLECULAR_WEIGHT>
594.654

> <EXACT_MASS>
594.267626792

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.55246431166432

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
1.691267956999999

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.577821755196872

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.99187784686351

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
198.75999999999996

> <JCHEM_REFRACTIVITY>
148.116

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <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  O   UNK     0       1.659 -10.404   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.147 -10.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.861 -11.277   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.357 -12.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.155 -13.023   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.163 -11.859   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.676 -12.150   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.684 -10.986   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.180  -9.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.163  -7.785   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.651  -7.494   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.147  -6.039   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.155  -4.875   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -5.166   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.171  -6.621   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.651  -3.419   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.196 -11.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.204 -10.113   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.716 -10.404   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.725  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.237  -9.531   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.245  -8.367   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.757  -8.658   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.261 -10.113   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.253 -11.277   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.741 -10.986   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.774 -10.404   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.659 -14.479   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.365 -13.897   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.373 -10.986   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.357  -8.658   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.869  -8.367   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.373  -6.912   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.493  -5.649   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.422  -4.420   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.877  -4.925   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.847  -6.464   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.075  -7.393   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.545  -3.537   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -6.080  -3.422   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -5.410  -4.777   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   32                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18    8   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25                                                            
CONECT   29    5                                                            
CONECT   30    4                                                            
CONECT   31    3                                                            
CONECT   32    2   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   40   42                                             
CONECT   38   37   34   39                                                  
CONECT   39   38                                                            
CONECT   40   37   41                                                       
CONECT   41   40                                                            
CONECT   42   37                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₁₂

Average Mass

594.6540 Da

Monoisotopic Mass

594.26763 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@@]1(O)CO[C@@H](OC[C@H]2O[C@@H](O[C@H](CCCCC3=CC=C(O)C=C3)CCC3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O

InChI Identifier

InChI=1S/C30H42O12/c31-16-30(38)17-40-29(27(30)37)39-15-23-24(34)25(35)26(36)28(42-23)41-22(14-9-19-7-12-21(33)13-8-19)4-2-1-3-18-5-10-20(32)11-6-18/h5-8,10-13,22-29,31-38H,1-4,9,14-17H2/t22-,23-,24-,25+,26-,27+,28-,29-,30-/m1/s1

InChI Key

JLMGCBFIPZDHLZ-GYOMMSMMSA-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
Acer nikoense	Plant	KNApSAcK
Alnus firma	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Betula platyphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Tertiary alcohol
Oxolane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.28	ALOGPS
logP	1.69	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	148.12 m³·mol⁻¹	ChemAxon
Polarizability	62.55 Å³	ChemAxon
Number of Rings	4	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

C00029631

Chemspider ID

10272905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21637600

PDB ID

Not Available

ChEBI ID

184017

Good Scents ID

Not Available

References

General References

Lee M, Park JH, Min DS, Yoo H, Park JH, Kim YC, Sung SH: Antifibrotic activity of diarylheptanoids from Betula platyphylla toward HSC-T6 cells. Biosci Biotechnol Biochem. 2012;76(9):1616-20. doi: 10.1271/bbb.110887. Epub 2012 Sep 7. [PubMed:22972321 ]
Cho N, Kim HW, Kim TB, Ransom TT, Beutler JA, Sung SH: Preparative Purification of Anti-Proliferative Diarylheptanoids from Betula platyphylla by High-Speed Counter-Current Chromatography. Molecules. 2016 May 28;21(6). pii: molecules21060700. doi: 10.3390/molecules21060700. [PubMed:27240338 ]
Ryu HW, Lee DH, Shin DH, Kim SH, Kwon SH: Aceroside VIII is a new natural selective HDAC6 inhibitor that synergistically enhances the anticancer activity of HDAC inhibitor in HT29 cells. Planta Med. 2015 Feb;81(3):222-7. doi: 10.1055/s-0034-1396149. Epub 2015 Jan 15. [PubMed:25590368 ]
Lee KY, Jeong EJ, Huh J, Cho N, Kim TB, Jeon BJ, Kim SH, Kim HP, Sung SH: Cognition-enhancing and neuroprotective activities of the standardized extract of Betula platyphylla bark and its major diarylheptanoids. Phytomedicine. 2012 Nov 15;19(14):1315-20. doi: 10.1016/j.phymed.2012.09.012. Epub 2012 Oct 15. [PubMed:23079232 ]

Showing NP-Card for Aceroside VIII (NP0070831)

MOL for NP0070831 (Aceroside VIII)

3D MOL for NP0070831 (Aceroside VIII)

3D SDF for NP0070831 (Aceroside VIII)

3D-SDF for NP0070831 (Aceroside VIII)

PDB for NP0070831 (Aceroside VIII)

3D PDB for NP0070831 (Aceroside VIII)

SMILES for NP0070831 (Aceroside VIII)

INCHI for NP0070831 (Aceroside VIII)

Structure for NP0070831 (Aceroside VIII)

3D Structure for NP0070831 (Aceroside VIII)