NP-MRD: Showing NP-Card for (2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal (NP0263277)

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Record Information

Version

2.0

Created at

2022-09-08 06:24:45 UTC

Updated at

2022-09-08 06:24:45 UTC

NP-MRD ID

NP0263277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

Description

Americanin A belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety. (2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal is found in Morinda citrifolia. (2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal was first documented in 2012 (PMID: 22293351). Based on a literature review a small amount of articles have been published on Americanin A (PMID: 30682527) (PMID: 26997427) (PMID: 26595875) (PMID: 25613173).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    6.6577    2.4179   -1.3617 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    2.9843   -0.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441    2.5256    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    1.4780   -0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1082    0.9213    0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4348    1.4163    1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2605    0.8615    1.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7273   -0.2270    1.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3822   -0.7424    0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5511   -0.1874   -0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -1.8493   -0.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -2.1492   -0.4447 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7155   -3.6519   -0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0687   -4.3626    0.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701   -1.6033    0.7399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4280   -0.7438    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7173   -1.1726    0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7549   -0.3200    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4626    0.9862   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4644    1.8802   -0.6736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1683    1.4485   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8540    2.7685   -0.6761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1588    0.5627    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.8452    1.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6693    3.8399    0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5303    3.0225    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7895    0.9987   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269    2.2680    1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7323    1.2512    2.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0444   -0.6162   -1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454   -1.7056   -1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591   -4.0006   -1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013   -3.9448   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -4.1423    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913   -2.4300    1.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441   -2.1908    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7770   -0.6344    0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4230    1.5512   -0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6177    3.3777   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    0.9590    0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 10  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 24  1  0
 24 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 15 12  1  0
 23 16  1  0
  8  9  1  0
 14 34  1  0
 13 32  1  0
 13 33  1  0
 12 31  1  6
 10 30  1  0
  4 27  1  0
  3 26  1  0
  2 25  1  0
  6 28  1  0
  7 29  1  0
 15 35  1  1
 17 36  1  0
 18 37  1  0
 20 38  1  0
 22 39  1  0
 23 40  1  0
M  END


  Mrv1652309082208242D          

 24 26  0  0  1  0            999 V2000
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 15 24  1  0  0  0  0
  8 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1OC2=CC(\C=C\C=O)=CC=C2O[C@H]1C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)23-17(10-20)18(24-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1+/t17-,18-/m0/s1

> <INCHI_KEY>
NTXXGPYGMQQSML-QLJMBOKNSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.33547251404501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(2S,3S)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

> <JCHEM_LOGP>
2.037377135

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.653886056944035

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207264273796575

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904143046329557

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
87.299

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(2S,3S)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16                                                       
CONECT   24   15    8                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3200 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

(2E)-3-[(2S,3S)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

Traditional Name

(2E)-3-[(2S,3S)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

CAS Registry Number

Not Available

SMILES

OC[C@@H]1OC2=CC(\C=C\C=O)=CC=C2O[C@H]1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)23-17(10-20)18(24-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1+/t17-,18-/m0/s1

InChI Key

NTXXGPYGMQQSML-QLJMBOKNSA-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
Morinda citrifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxanes

Sub Class

Phenylbenzodioxanes

Direct Parent

Phenylbenzo-1,4-dioxanes

Alternative Parents

Substituents

2-phenylbenzo-1,4-dioxane
Benzo-1,4-dioxane
Cinnamaldehyde
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Para-dioxin
Benzenoid
Enal
Alpha,beta-unsaturated aldehyde
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aldehyde
Organic oxygen compound
Primary alcohol
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	2.04	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.3 m³·mol⁻¹	ChemAxon
Polarizability	33.34 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031592

Chemspider ID

24700119

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44575382

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

De La Cruz-Sanchez NG, Gomez-Rivera A, Alvarez-Fitz P, Ventura-Zapata E, Perez-Garcia MD, Aviles-Flores M, Gutierrez-Roman AS, Gonzalez-Cortazar M: Antibacterial activity of Morinda citrifolia Linneo seeds against Methicillin-Resistant Staphylococcus spp. Microb Pathog. 2019 Mar;128:347-353. doi: 10.1016/j.micpath.2019.01.030. Epub 2019 Jan 23. [PubMed:30682527 ]
Shin Y, Jang EJ, Park HJ, Hong JY, Kang SS, Lee SK: Suppression of melanin synthesis by Americanin A in melan-a cells via regulation of microphthalmia-associated transcription factor. Exp Dermatol. 2016 Aug;25(8):646-7. doi: 10.1111/exd.13013. Epub 2016 Jun 1. [PubMed:26997427 ]
Jung C, Hong JY, Bae SY, Kang SS, Park HJ, Lee SK: Antitumor Activity of Americanin A Isolated from the Seeds of Phytolacca americana by Regulating the ATM/ATR Signaling Pathway and the Skp2-p27 Axis in Human Colon Cancer Cells. J Nat Prod. 2015 Dec 24;78(12):2983-93. doi: 10.1021/acs.jnatprod.5b00743. Epub 2015 Nov 23. [PubMed:26595875 ]
Pazar E, Akgul Y: Chemical composition of the endocarps of fruits of Styrax officinalis L. Nat Prod Res. 2015;29(15):1466-8. doi: 10.1080/14786419.2014.1003063. Epub 2015 Jan 23. [PubMed:25613173 ]
Masuda M, Murata K, Naruto S, Uwaya A, Isami F, Matsuda H: Matrix metalloproteinase-1 inhibitory activities of Morinda citrifolia seed extract and its constituents in UVA-irradiated human dermal fibroblasts. Biol Pharm Bull. 2012;35(2):210-5. doi: 10.1248/bpb.35.210. [PubMed:22293351 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal (NP0263277)

MOL for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

3D MOL for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

3D SDF for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

3D-SDF for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

PDB for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

3D PDB for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

SMILES for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

INCHI for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

Structure for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)

3D Structure for NP0263277 ((2e)-3-[(2s,3s)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal)