NP-MRD: Showing NP-Card for Chrestifoline C (NP0067010)

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Record Information

Version

2.0

Created at

2022-04-28 11:12:54 UTC

Updated at

2022-04-28 11:12:54 UTC

NP-MRD ID

NP0067010

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chrestifoline C

Description

(3R)-11-[(1-Methoxy-9H-carbazol-3-yl)methyl]-3,5-dimethyl-3beta-(4-methyl-3-pentenyl)-3,11-dihydropyrano[3,2-a]carbazole belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Chrestifoline C is found in Murraya euchrestifolia. Based on a literature review very few articles have been published on (3R)-11-[(1-Methoxy-9H-carbazol-3-yl)methyl]-3,5-dimethyl-3beta-(4-methyl-3-pentenyl)-3,11-dihydropyrano[3,2-a]carbazole.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213122D          

 41 47  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282213122D          

 41 47  0  0  1  0            999 V2000
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    6.7418   -1.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -1.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5670   -2.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1442   -2.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723    0.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 26 34  1  1  0  0  0
 21 35  1  0  0  0  0
 19 36  1  0  0  0  0
 36 37  2  0  0  0  0
 17 37  1  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
 36 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067010

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CN2C3=C(C=CC=C3)C3=C2C2=C(O[C@](C)(CCC=C(C)C)C=C2)C(C)=C3)=CC2=C1NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H36N2O2/c1-23(2)11-10-17-37(4)18-16-28-35-30(19-24(3)36(28)41-37)27-13-7-9-15-32(27)39(35)22-25-20-29-26-12-6-8-14-31(26)38-34(29)33(21-25)40-5/h6-9,11-16,18-21,38H,10,17,22H2,1-5H3/t37-/m1/s1

> <INCHI_KEY>
WZDZCOAWFXDCTD-DIPNUNPCSA-N

> <FORMULA>
C37H36N2O2

> <MOLECULAR_WEIGHT>
540.707

> <EXACT_MASS>
540.277678407

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
63.68962590486368

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(3R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3H,11H-pyrano[3,2-a]carbazol-11-yl]methyl}-1-methoxy-9H-carbazole

> <ALOGPS_LOGP>
8.51

> <JCHEM_LOGP>
9.150716276333334

> <ALOGPS_LOGS>
-6.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.003441145855803

> <JCHEM_PKA_STRONGEST_BASIC>
-4.601605175990603

> <JCHEM_POLAR_SURFACE_AREA>
39.18

> <JCHEM_REFRACTIVITY>
170.01909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.83e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(3R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)pyrano[3,2-a]carbazol-11-yl]methyl}-1-methoxy-9H-carbazole

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.902  -2.796   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.392  -3.187   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.797  -4.673   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.714  -5.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.224  -5.376   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.819  -3.890   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.671  -3.499   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.077  -2.013   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.392  -6.671   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.367  -7.863   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.802  -7.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.003  -8.268   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.770  -9.790   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.335 -10.349   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.133  -9.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.475  -2.093   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.070  -0.607   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.033   0.594   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.188   1.881   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.881   3.257   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.418   3.345   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.263   2.057   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.570   0.682   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.415  -0.606   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.953  -0.517   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.645   0.858   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.800   2.146   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.044   0.214   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.186  -1.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.585  -1.964   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.726  -3.497   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.125  -4.141   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.469  -4.387   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.962   1.658   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.111   4.720   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.702   1.476   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.629  -0.063   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.260  -0.768   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.035   0.064   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.038   1.603   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.407   2.308   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    2   17                                                       
CONECT   17   16   18   37                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   36                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   35                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   34                                             
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   26                                                            
CONECT   35   21                                                            
CONECT   36   19   37   41                                                  
CONECT   37   36   17   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Value	Source
(3R)-11-[(1-Methoxy-9H-carbazol-3-yl)methyl]-3,5-dimethyl-3b-(4-methyl-3-pentenyl)-3,11-dihydropyrano[3,2-a]carbazole	Generator
(3R)-11-[(1-Methoxy-9H-carbazol-3-yl)methyl]-3,5-dimethyl-3β-(4-methyl-3-pentenyl)-3,11-dihydropyrano[3,2-a]carbazole	Generator

Chemical Formula

C₃₇H₃₆N₂O₂

Average Mass

540.7070 Da

Monoisotopic Mass

540.27768 Da

IUPAC Name

3-{[(3R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3H,11H-pyrano[3,2-a]carbazol-11-yl]methyl}-1-methoxy-9H-carbazole

Traditional Name

3-{[(3R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)pyrano[3,2-a]carbazol-11-yl]methyl}-1-methoxy-9H-carbazole

CAS Registry Number

Not Available

SMILES

COC1=CC(CN2C3=C(C=CC=C3)C3=C2C2=C(O[C@](C)(CCC=C(C)C)C=C2)C(C)=C3)=CC2=C1NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C37H36N2O2/c1-23(2)11-10-17-37(4)18-16-28-35-30(19-24(3)36(28)41-37)27-13-7-9-15-32(27)39(35)22-25-20-29-26-12-6-8-14-31(26)38-34(29)33(21-25)40-5/h6-9,11-16,18-21,38H,10,17,22H2,1-5H3/t37-/m1/s1

InChI Key

WZDZCOAWFXDCTD-DIPNUNPCSA-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
Murraya euchrestifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
N-alkylindole
Benzopyran
1-benzopyran
Indole
Anisole
Phenol ether
Alkyl aryl ether
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Oxacycle
Ether
Azacycle
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen 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	8.51	ALOGPS
logP	9.15	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.18 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	170.02 m³·mol⁻¹	ChemAxon
Polarizability	63.69 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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

102058942

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Chrestifoline C (NP0067010)

MOL for NP0067010 (Chrestifoline C)

3D MOL for NP0067010 (Chrestifoline C)

3D SDF for NP0067010 (Chrestifoline C)

3D-SDF for NP0067010 (Chrestifoline C)

PDB for NP0067010 (Chrestifoline C)

3D PDB for NP0067010 (Chrestifoline C)

SMILES for NP0067010 (Chrestifoline C)

INCHI for NP0067010 (Chrestifoline C)

Structure for NP0067010 (Chrestifoline C)

3D Structure for NP0067010 (Chrestifoline C)