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Showing NP-Card for aeroplysinin 1 (NP0277913)

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Record Information
Version2.0
Created at2022-09-09 02:45:17 UTC
Updated at2022-09-09 02:45:17 UTC
NP-MRD IDNP0277913
Secondary Accession NumbersNone
Natural Product Identification
Common Nameaeroplysinin 1
DescriptionAeroplysinin 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 ). aeroplysinin 1 is found in Aiolochroia crassa, Aplysina aerophoba, Aplysina archeri, Aplysina cauliformis, Aplysina fistularis, Pseudoceratina arabica, Pseudoceratina durissima, Tylodina perversa and Verongula gigantea. aeroplysinin 1 was first documented in 1970 (PMID: 5495054). Based on a literature review very few articles have been published on Aeroplysinin I.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0277913 (aeroplysinin 1)


  Mrv1652309092204452D          

 15 15  0  0  1  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  2  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  2  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  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  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
Download

3D MOL for NP0277913 (aeroplysinin 1)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -3.7169    1.0839   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167    0.1756    0.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4874    0.0095    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791   -1.0203    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9006   -2.2314    1.6902 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -1.3343    0.4002 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1517   -1.5013    1.6771 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074   -0.4086   -0.4325 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9437   -1.1526   -1.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741    0.2094    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122    1.1110   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882    1.8454   -1.1589 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740    0.7190   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082    0.9184   -0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6274    2.4068   -1.5263 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8456    1.0215   -1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7387    0.7733    0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6148    2.1259    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808   -2.3564   -0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658   -2.4199    1.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525   -1.6558   -1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426    0.8051    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1130   -0.5769    0.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1047    1.4527   -1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  3  0
  8 13  1  0
 13 14  2  0
 14 15  1  0
 14  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  6
  7 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 13 24  1  0
M  END
Download

3D SDF for NP0277913 (aeroplysinin 1)


  Mrv1652309092204452D          

 15 15  0  0  1  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  2  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  2  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  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  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>
NP0277913

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Br)[C@H](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/t8-,9-/m0/s1

> <INCHI_KEY>
BGYNLOSBKBOJJD-IUCAKERBSA-N

> <FORMULA>
C9H9Br2NO3

> <MOLECULAR_WEIGHT>
338.983

> <EXACT_MASS>
336.894919

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
24.33837014845746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
-0.2646023259999999

> <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

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

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0277913 (aeroplysinin 1)

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PDB for NP0277913 (aeroplysinin 1)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         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

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3D PDB for NP0277913 (aeroplysinin 1)
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SMILES for NP0277913 (aeroplysinin 1)
COC1=C(Br)[C@H](O)[C@](O)(CC#N)C=C1Br
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INCHI for NP0277913 (aeroplysinin 1)
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/t8-,9-/m0/s1
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View in JSmol
Synonyms
ValueSource
Aeroplysinin-IMeSH
3,5-Dibromo-1,2-dihydroxy-4-methoxy-3,5-cyclohexadiene-1-acetonitrileMeSH
Aeroplysinin I, trans-(+-)-isomerMeSH
Aeroplysinin I, (1R-trans)-isomerMeSH
Aeroplysinin-1MeSH
Chemical FormulaC9H9Br2NO3
Average Mass338.9830 Da
Monoisotopic Mass336.89492 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
COC1=C(Br)[C@H](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/t8-,9-/m0/s1
InChI KeyBGYNLOSBKBOJJD-IUCAKERBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aiolochroia crassaLOTUS Database
Aplysina aerophobaLOTUS Database
Aplysina archeriLOTUS Database
Aplysina cauliformisLOTUS Database
Aplysina fistularisLOTUS Database
Pseudoceratina arabicaLOTUS Database
Pseudoceratina durissimaLOTUS Database
Tylodina perversaLOTUS Database
Verongula giganteaLOTUS Database
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 ).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentTertiary 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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00038366  
Chemspider ID90646  
KEGG Compound IDC17099  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound100308  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Fulmor W, Van Lear GE, Morton GO, Mills RD: Isolation and absolute configuration of the aeroplysinin I enantiomorphic pair from ianthella ardis. Tetrahedron Lett. 1970 Nov;(52):4551-2. doi: 10.1016/s0040-4039(00)89414-9. [PubMed:5495054  ] 
  2. LOTUS database [Link]