NP-MRD: Showing NP-Card for (2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0320500)

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Record Information

Version

2.0

Created at

2022-09-11 22:11:17 UTC

Updated at

2022-09-11 22:11:17 UTC

NP-MRD ID

NP0320500

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Aceroside VII 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. (2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Acer nikoense and Betula pendula. (2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol was first documented in 2010 (PMID: 20118587). Based on a literature review a small amount of articles have been published on aceroside VII (PMID: 23512500) (PMID: 22972321).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122200112D          

 33 35  0  0  1  0            999 V2000
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    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309122200112D          

 33 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0320500

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1O[C@H](OC(CCCCC2=CC=C(O)C=C2)CCC2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O8/c26-15-21-22(29)23(30)24(31)25(33-21)32-20(14-9-17-7-12-19(28)13-8-17)4-2-1-3-16-5-10-18(27)11-6-16/h5-8,10-13,20-31H,1-4,9,14-15H2/t20?,21-,22-,23+,24-,25-/m0/s1

> <INCHI_KEY>
MAUAGULXOHJIER-MVMXRKHSSA-N

> <FORMULA>
C25H34O8

> <MOLECULAR_WEIGHT>
462.539

> <EXACT_MASS>
462.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.83629144500481

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.967767017

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.594578927161244

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.99769886096072

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835415258596

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
121.4458

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
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   18                                                       
CONECT   18   17   12                                                       
CONECT   19    7   20                                                       
CONECT   20   19   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   27                                                       
CONECT   27   26   21                                                       
CONECT   28    5   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₈

Average Mass

462.5390 Da

Monoisotopic Mass

462.22537 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@@H]1O[C@H](OC(CCCCC2=CC=C(O)C=C2)CCC2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C25H34O8/c26-15-21-22(29)23(30)24(31)25(33-21)32-20(14-9-17-7-12-19(28)13-8-17)4-2-1-3-16-5-10-18(27)11-6-16/h5-8,10-13,20-31H,1-4,9,14-15H2/t20?,21-,22-,23+,24-,25-/m0/s1

InChI Key

MAUAGULXOHJIER-MVMXRKHSSA-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
Acer nikoense	LOTUS Database	35616633
Betula pendula	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 of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	2.97	ChemAxon
pKa (Strongest Acidic)	10	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	121.45 m³·mol⁻¹	ChemAxon
Polarizability	49.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

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

133554322

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Novakovic M, Stankovic M, Vuckovic I, Todorovic N, Trifunovic S, Tesevic V, Vajs V, Milosavljevic S: Diarylheptanoids from Alnus glutinosa bark and their chemoprotective effect on human lymphocytes DNA. Planta Med. 2013 Apr;79(6):499-505. doi: 10.1055/s-0032-1328301. Epub 2013 Mar 19. [PubMed:23512500 ]
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 ]
Park D, Kim HJ, Jung SY, Yook CS, Jin C, Lee YS: A new diarylheptanoid glycoside from the stem bark of Alnus hirsuta and protective effects of diarylheptanoid derivatives in human HepG2 cells. Chem Pharm Bull (Tokyo). 2010 Feb;58(2):238-41. doi: 10.1248/cpb.58.238. [PubMed:20118587 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0320500)

MOL for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0320500 ((2s,3s,4r,5r,6s)-2-{[1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)