NP-MRD: Showing NP-Card for n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine (NP0226913)

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Record Information

Version

2.0

Created at

2022-09-06 06:06:11 UTC

Updated at

2022-09-06 06:06:12 UTC

NP-MRD ID

NP0226913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine

Description

N-[(E)-2-[(2R)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine 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. n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine is found in Astroides calycularis. Based on a literature review very few articles have been published on N-[(E)-2-[(2R)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062208062D          

 28 30  0  0  1  0            999 V2000
   -4.2868    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 N   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  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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 N   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
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   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
  2  4  1  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 10 28  1  0  0  0  0
M  END


  Mrv1652309062208062D          

 28 30  0  0  1  0            999 V2000
   -4.2868    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 N   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  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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 N   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
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   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
  2  4  1  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 10 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226913

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N6O4/c19-17(20)23-6-5-9-1-4-13-14(7-9)27-15(16(28-13)24-18(21)22)10-2-3-11(25)12(26)8-10/h1-8,15-16,25-26H,(H4,19,20,23)(H4,21,22,24)/b6-5+/t15?,16-/m1/s1

> <INCHI_KEY>
MCLIKJGPKULDHY-MJILUMFLSA-N

> <FORMULA>
C18H20N6O4

> <MOLECULAR_WEIGHT>
384.396

> <EXACT_MASS>
384.154603148

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
38.673493246595015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(E)-2-[(2R)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine

> <JCHEM_LOGP>
0.4921227127329554

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.67848944795049

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.09672069383302

> <JCHEM_PKA_STRONGEST_BASIC>
11.287250474490795

> <JCHEM_POLAR_SURFACE_AREA>
182.72000000000003

> <JCHEM_REFRACTIVITY>
122.69810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(E)-2-[(2R)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine

> <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  N   UNK     0      -8.002   0.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -6.668  -2.310   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -5.335   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
CONECT   23   14   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   10                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀N₆O₄

Average Mass

384.3960 Da

Monoisotopic Mass

384.15460 Da

IUPAC Name

N-[(E)-2-[(2R)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine

Traditional Name

N-[(E)-2-[(2R)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine

CAS Registry Number

Not Available

SMILES

NC(=N)N\C=C\C1=CC=C2O[C@@H](NC(N)=N)C(OC2=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C18H20N6O4/c19-17(20)23-6-5-9-1-4-13-14(7-9)27-15(16(28-13)24-18(21)22)10-2-3-11(25)12(26)8-10/h1-8,15-16,25-26H,(H4,19,20,23)(H4,21,22,24)/b6-5+/t15?,16-/m1/s1

InChI Key

MCLIKJGPKULDHY-MJILUMFLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Astroides calycularis	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
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Para-dioxin
Monocyclic benzene moiety
Guanidine
Oxacycle
Carboximidamide
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
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	0.49	ChemAxon
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	11.29	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	182.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.7 m³·mol⁻¹	ChemAxon
Polarizability	38.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

162889100

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine (NP0226913)

MOL for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

3D MOL for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

3D SDF for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

3D-SDF for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

PDB for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

3D PDB for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

SMILES for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

INCHI for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

Structure for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)

3D Structure for NP0226913 (n-[(1e)-2-[(2r)-2-carbamimidamido-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl]guanidine)