NP-MRD: Showing NP-Card for [(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate (NP0225372)

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Record Information

Version

2.0

Created at

2022-09-06 04:04:42 UTC

Updated at

2022-09-06 04:04:42 UTC

NP-MRD ID

NP0225372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate

Description

Cedrusinin triacetate belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. [(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate is found in Cryptomeria japonica. Based on a literature review very few articles have been published on Cedrusinin triacetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206042D          

 33 35  0  0  1  0            999 V2000
   -4.7610    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1735    4.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2136    3.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    2.2201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4685    1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2755    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9784   -0.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3374    0.3078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1735    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9985    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4110    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9985    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2360    3.6020    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  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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
 16 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END


  Mrv1652309062206042D          

 33 35  0  0  1  0            999 V2000
   -4.7610    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1735    4.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2136    3.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    2.2201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4685    1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2755    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9784   -0.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3374    0.3078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1735    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9985    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4110    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9985    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2360    3.6020    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  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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
 16 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0225372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1OC(C)=O)[C@H]1OC2=CC=C(CCCOC(C)=O)C=C2[C@@H]1COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O8/c1-15(26)30-11-5-6-18-7-9-22-20(12-18)21(14-31-16(2)27)25(33-22)19-8-10-23(32-17(3)28)24(13-19)29-4/h7-10,12-13,21,25H,5-6,11,14H2,1-4H3/t21-,25+/m0/s1

> <INCHI_KEY>
RPGAWEBIJRTSRG-SQJMNOBHSA-N

> <FORMULA>
C25H28O8

> <MOLECULAR_WEIGHT>
456.491

> <EXACT_MASS>
456.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.15272054668379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2S,3R)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate

> <JCHEM_LOGP>
2.9072748126666674

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.593755037417842

> <JCHEM_POLAR_SURFACE_AREA>
97.36000000000001

> <JCHEM_REFRACTIVITY>
118.4856

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.887   9.391   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.657   8.057   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.887   6.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.347   6.724   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.577   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.037   5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.132   6.636   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.132   4.144   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.608   2.679   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.114   2.359   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.590   0.895   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.560  -0.250   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -8.096   0.574   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -7.347   4.056   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.887   4.056   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.657   5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -11.197   5.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -11.967   6.724   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -11.197   8.057   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -13.507   6.724   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11   20                                                       
CONECT   20   19    8   21                                                  
CONECT   21   20    6   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    5   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    3   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
Cedrusinin triacetic acid	Generator

Chemical Formula

C₂₅H₂₈O₈

Average Mass

456.4910 Da

Monoisotopic Mass

456.17842 Da

IUPAC Name

[(2S,3R)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate

Traditional Name

[(2S,3R)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1OC(C)=O)[C@H]1OC2=CC=C(CCCOC(C)=O)C=C2[C@@H]1COC(C)=O

InChI Identifier

InChI=1S/C25H28O8/c1-15(26)30-11-5-6-18-7-9-22-20(12-18)21(14-31-16(2)27)25(33-22)19-8-10-23(32-17(3)28)24(13-19)29-4/h7-10,12-13,21,25H,5-6,11,14H2,1-4H3/t21-,25+/m0/s1

InChI Key

RPGAWEBIJRTSRG-SQJMNOBHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cryptomeria japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Norlignan skeleton
Neolignan skeleton
Phenol ester
Benzofuran
Coumaran
Tricarboxylic acid or derivatives
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.91	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.36 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	118.49 m³·mol⁻¹	ChemAxon
Polarizability	49.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

101932601

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate (NP0225372)

MOL for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

3D MOL for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

3D SDF for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

3D-SDF for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

PDB for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

3D PDB for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

SMILES for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

INCHI for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

Structure for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)

3D Structure for NP0225372 ([(2s,3r)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3-(acetyloxy)propyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate)