NP-MRD: Showing NP-Card for 2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile (NP0309211)

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Record Information

Version

1.0

Created at

2022-09-11 03:39:07 UTC

Updated at

2022-09-11 03:39:07 UTC

NP-MRD ID

NP0309211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile

Description

Aeroplysinin I belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile is found in Aiolochroia crassa, Aplysina aerophoba, Aplysina caissara, Aplysina cauliformis and Pseudoceratina durissima. Aeroplysinin I is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161522162D          

 15 15  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
   -0.7145   -0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804    3.4200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.1434   -0.4125    0.0000 Br  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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Br)C(O)C(O)(CC#N)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C9H9Br2NO3/c1-15-7-5(10)4-9(14,2-3-12)8(13)6(7)11/h4,8,13-14H,2H2,1H3

> <INCHI_KEY>
BGYNLOSBKBOJJD-UHFFFAOYSA-N

> <FORMULA>
C9H9Br2NO3

> <MOLECULAR_WEIGHT>
338.983

> <EXACT_MASS>
336.894919

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
24.33837014845739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
-0.2646023259999999

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.682748621846638

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.252439307890672

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8195019548521563

> <JCHEM_POLAR_SURFACE_AREA>
73.47999999999999

> <JCHEM_REFRACTIVITY>
63.927

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.797   4.937   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.270   6.384   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0       4.001  -0.770   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   13                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
3,5-Dibromo-1,2-dihydroxy-4-methoxy-3,5-cyclohexadiene-1-acetonitrile	MeSH
Aeroplysinin	MeSH
Aeroplysinin I, (1R-trans)-isomer	MeSH
Aeroplysinin I, trans-(+-)-isomer	MeSH
Aeroplysinin-1	MeSH
Aeroplysinin-I	MeSH

Chemical Formula

C₉H₉Br₂NO₃

Average Mass

338.9830 Da

Monoisotopic Mass

336.89492 Da

IUPAC Name

2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile

Traditional Name

2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile

CAS Registry Number

Not Available

SMILES

COC1=C(Br)C(O)C(O)(CC#N)C=C1Br

InChI Identifier

InChI=1S/C9H9Br2NO3/c1-15-7-5(10)4-9(14,2-3-12)8(13)6(7)11/h4,8,13-14H,2H2,1H3

InChI Key

BGYNLOSBKBOJJD-UHFFFAOYSA-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
Aiolochroia crassa	LOTUS Database	35616633
Aplysina aerophoba	LOTUS Database	35616633
Aplysina caissara	LOTUS Database	35616633
Aplysina cauliformis	LOTUS Database	35616633
Pseudoceratina durissima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
1,2-diol
Bromohydrin
Halohydrin
Secondary alcohol
Carbonitrile
Nitrile
Bromoalkene
Haloalkene
Vinyl bromide
Vinyl halide
Organohalogen compound
Organobromide
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.44	ALOGPS
logP	-0.26	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.25	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	73.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.93 m³·mol⁻¹	ChemAxon
Polarizability	24.34 Å³	ChemAxon
Number of Rings	1	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

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

2036

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile (NP0309211)

MOL for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

3D MOL for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

3D SDF for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

3D-SDF for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

PDB for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

3D PDB for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

SMILES for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

INCHI for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

Structure for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)

3D Structure for NP0309211 (2-(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile)