NP-MRD: Showing NP-Card for Bidebiline B (NP0069040)

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Record Information

Version

2.0

Created at

2022-04-28 14:18:16 UTC

Updated at

2022-04-28 14:18:16 UTC

NP-MRD ID

NP0069040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bidebiline B

Description

13-{3,5-Dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]Icosa-1(20),2(6),7,12,14,16,18-heptaen-13-yl}-15-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]Icosa-1(20),2(6),7,12,14(19),15,17-heptaene belongs to the class of organic compounds known as naphthylquinolines. These are polycyclic aromatic compounds containing a naphthene moiety linked to a quinoline through a CC or CN single bond. Bidebiline B is found in Polyalthia debilis. 13-{3,5-Dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]Icosa-1(20),2(6),7,12,14,16,18-heptaen-13-yl}-15-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]Icosa-1(20),2(6),7,12,14(19),15,17-heptaene is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241516592D          

 42 51  0  0  0  0            999 V2000
    0.6919   -1.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6649   -2.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004241516592D          

 42 51  0  0  0  0            999 V2000
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    2.8579    0.8250    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    3.5724   -1.2375    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  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  1  0  0  0  0
 12 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  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 14 22  2  0  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 23 41  1  0  0  0  0
 36 41  1  0  0  0  0
 35 42  1  0  0  0  0
 24 42  1  0  0  0  0
 28 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0069040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=CC=C1)C1=C3OCOC3=CC3=C1C(NCC3)=C2C1=C2NCCC3=C2C(=C2OCOC2=C3)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C35H26N2O5/c1-38-22-8-4-7-21-27(22)31(33-26-18(10-12-37-33)14-24-35(30(21)26)42-16-40-24)28-19-5-2-3-6-20(19)29-25-17(9-11-36-32(25)28)13-23-34(29)41-15-39-23/h2-8,13-14,36-37H,9-12,15-16H2,1H3

> <INCHI_KEY>
YYCWQXHRSIIBSO-UHFFFAOYSA-N

> <FORMULA>
C35H26N2O5

> <MOLECULAR_WEIGHT>
554.602

> <EXACT_MASS>
554.184171945

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
60.246469032266766

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaen-13-yl}-15-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene

> <ALOGPS_LOGP>
5.56

> <JCHEM_LOGP>
5.692507141666665

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.88023421294534

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.799201762711583

> <JCHEM_PKA_STRONGEST_BASIC>
3.8425006350795665

> <JCHEM_POLAR_SURFACE_AREA>
70.21000000000001

> <JCHEM_REFRACTIVITY>
161.99879999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaen-13-yl}-15-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.292  -2.835   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.322  -3.980   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.798  -5.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.767  -6.589   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.243  -8.053   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.750  -8.374   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.780  -7.229   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.304  -5.764   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.841  -4.940   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       7.872  -3.796   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.378  -4.116   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.854  -5.581   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.823  -6.725   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.299  -8.190   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.269  -9.334   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.430 -10.866   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.023 -11.492   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.992 -10.348   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.762  -9.014   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.286  -7.549   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.317  -6.405   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20    7   22                                                  
CONECT   22   21   10   14                                                  
CONECT   23    9   24   41                                                  
CONECT   24   23   25   42                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   42                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30   35                                                  
CONECT   35   34   36   42                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   23   36                                                  
CONECT   42   35   24   28                                                  
MASTER        0    0    0    0    0    0    0    0   42    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₂₆N₂O₅

Average Mass

554.6020 Da

Monoisotopic Mass

554.18417 Da

IUPAC Name

13-{3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaen-13-yl}-15-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=C2C(=CC=C1)C1=C3OCOC3=CC3=C1C(NCC3)=C2C1=C2NCCC3=C2C(=C2OCOC2=C3)C2=CC=CC=C12

InChI Identifier

InChI=1S/C35H26N2O5/c1-38-22-8-4-7-21-27(22)31(33-26-18(10-12-37-33)14-24-35(30(21)26)42-16-40-24)28-19-5-2-3-6-20(19)29-25-17(9-11-36-32(25)28)13-23-34(29)41-15-39-23/h2-8,13-14,36-37H,9-12,15-16H2,1H3

InChI Key

YYCWQXHRSIIBSO-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Polyalthia debilis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthylquinolines. These are polycyclic aromatic compounds containing a naphthene moiety linked to a quinoline through a CC or CN single bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Phenylquinolines

Direct Parent

Naphthylquinolines

Alternative Parents

Substituents

Naphthylquinoline
Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Benzodioxole
Alkaloid or derivatives
Anisole
Aralkylamine
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Benzenoid
Secondary amine
Oxacycle
Azacycle
Acetal
Ether
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organonitrogen compound
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	5.56	ALOGPS
logP	5.69	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	19.8	ChemAxon
pKa (Strongest Basic)	3.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.21 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	162 m³·mol⁻¹	ChemAxon
Polarizability	60.25 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

10918691

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Bidebiline B (NP0069040)

MOL for NP0069040 (Bidebiline B)

3D MOL for NP0069040 (Bidebiline B)

3D SDF for NP0069040 (Bidebiline B)

3D-SDF for NP0069040 (Bidebiline B)

PDB for NP0069040 (Bidebiline B)

3D PDB for NP0069040 (Bidebiline B)

SMILES for NP0069040 (Bidebiline B)

INCHI for NP0069040 (Bidebiline B)

Structure for NP0069040 (Bidebiline B)

3D Structure for NP0069040 (Bidebiline B)