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Showing NP-Card for bleekerine (NP0258138)

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Record Information
Version2.0
Created at2022-09-07 23:27:41 UTC
Updated at2022-09-07 23:27:41 UTC
NP-MRD IDNP0258138
Secondary Accession NumbersNone
Natural Product Identification
Common Namebleekerine
DescriptionBleekerine belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. bleekerine is found in Ochrosia vitiensis. Based on a literature review very few articles have been published on Bleekerine.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0258138 (bleekerine)


  Mrv1652309082201272D          

 30 34  0  0  1  0            999 V2000
    3.8117   -6.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5395   -5.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779   -5.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8885   -5.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058   -4.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9952   -4.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7231   -3.4992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615   -2.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9893   -2.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720   -3.0279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6104   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4210   -2.5565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9594   -1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7700   -2.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421   -2.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8030   -3.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5491   -2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2270   -3.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9731   -2.9488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0413   -2.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1589   -4.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8368   -4.5932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7687   -5.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4128   -4.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7348   -4.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9318   -4.1943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5037   -3.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6931   -3.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547   -3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3442   -3.8067    0.0000 C   0  0  2  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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
  5 30  1  0  0  0  0
 10 30  1  0  0  0  0
M  END
Download

3D MOL for NP0258138 (bleekerine)

Download
3D SDF for NP0258138 (bleekerine)

  Mrv1652309082201272D          

 30 34  0  0  1  0            999 V2000
    3.8117   -6.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5395   -5.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779   -5.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8885   -5.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058   -4.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9952   -4.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7231   -3.4992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615   -2.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9893   -2.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720   -3.0279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6104   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4210   -2.5565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9594   -1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7700   -2.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421   -2.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8030   -3.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5491   -2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2270   -3.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9731   -2.9488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0413   -2.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1589   -4.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8368   -4.5932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7687   -5.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4128   -4.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7348   -4.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9318   -4.1943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5037   -3.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6931   -3.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547   -3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3442   -3.8067    0.0000 C   0  0  2  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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
  5 30  1  0  0  0  0
 10 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258138

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](C)[C@@H]2CN3C=CC4=C5C=C(OC)C(OC)=CC5=NC4=C3C[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C23H24N2O5/c1-12-16-10-25-6-5-13-15-8-20(27-2)21(28-3)9-18(15)24-22(13)19(25)7-14(16)17(11-30-12)23(26)29-4/h5-6,8-9,11-12,14,16H,7,10H2,1-4H3/t12-,14-,16-/m0/s1

> <INCHI_KEY>
TWZUULCDVYYPNU-NOLJZWGESA-N

> <FORMULA>
C23H24N2O5

> <MOLECULAR_WEIGHT>
408.454

> <EXACT_MASS>
408.168521881

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.83631464805245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylate

> <JCHEM_LOGP>
2.8568636840000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.7528079287881733

> <JCHEM_POLAR_SURFACE_AREA>
71.81

> <JCHEM_REFRACTIVITY>
110.3324

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0258138 (bleekerine)
Download
PDB for NP0258138 (bleekerine)
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  C   UNK     0       7.115 -12.347   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.607 -10.893   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.612  -9.726   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.125 -10.013   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.104  -8.273   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.591  -7.986   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.083  -6.532   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.088  -5.365   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.580  -3.911   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.601  -5.652   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.606  -4.485   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      10.119  -4.772   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      11.124  -3.605   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.637  -3.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.145  -5.346   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.566  -5.941   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.958  -5.284   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.224  -6.162   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.617  -5.505   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.744  -3.970   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.097  -7.696   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.362  -8.574   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      18.235 -10.109   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.704  -8.354   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.438  -7.476   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      12.939  -7.829   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      12.140  -6.513   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.627  -6.226   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.622  -7.393   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.109  -7.106   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   16   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   15   28                                                  
CONECT   28   27   12   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

Download
3D PDB for NP0258138 (bleekerine)
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SMILES for NP0258138 (bleekerine)
COC(=O)C1=CO[C@@H](C)[C@@H]2CN3C=CC4=C5C=C(OC)C(OC)=CC5=NC4=C3C[C@H]12
Download
INCHI for NP0258138 (bleekerine)
InChI=1S/C23H24N2O5/c1-12-16-10-25-6-5-13-15-8-20(27-2)21(28-3)9-18(15)24-22(13)19(25)7-14(16)17(11-30-12)23(26)29-4/h5-6,8-9,11-12,14,16H,7,10H2,1-4H3/t12-,14-,16-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC23H24N2O5
Average Mass408.4540 Da
Monoisotopic Mass408.16852 Da
IUPAC Namemethyl (15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylate
Traditional Namemethyl (15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C1=CO[C@@H](C)[C@@H]2CN3C=CC4=C5C=C(OC)C(OC)=CC5=NC4=C3C[C@H]12
InChI Identifier
InChI=1S/C23H24N2O5/c1-12-16-10-25-6-5-13-15-8-20(27-2)21(28-3)9-18(15)24-22(13)19(25)7-14(16)17(11-30-12)23(26)29-4/h5-6,8-9,11-12,14,16H,7,10H2,1-4H3/t12-,14-,16-/m0/s1
InChI KeyTWZUULCDVYYPNU-NOLJZWGESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ochrosia vitiensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassPyridoindoles  
Direct ParentBeta carbolines  
Alternative Parents
Substituents
  • Beta-carboline
    • 

  • Indole
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Pyridine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Methyl ester
    • 

  • Vinylogous ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.86ChemAxon
pKa (Strongest Basic)3.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area71.81 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.33 m³·mol⁻¹ChemAxon
Polarizability44.84 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390553  
KEGG Compound IDC09046  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441992  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]