NP-MRD: Showing NP-Card for Cryptoheptine (NP0085782)

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Record Information

Version

2.0

Created at

2022-04-29 06:15:05 UTC

Updated at

2022-04-29 06:15:05 UTC

NP-MRD ID

NP0085782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cryptoheptine

Description

12-Methyl-2,12-diazatetracyclo[9.7.0.0³,⁸.0¹³,¹⁸]Octadeca-2,4,6,8,10,13,15,17-octaen-9-ol belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom). Cryptoheptine is found in Cryptolepis sanguinolenta and Libocedrus yateensis. Based on a literature review very few articles have been published on 12-methyl-2,12-diazatetracyclo[9.7.0.0³,⁸.0¹³,¹⁸]Octadeca-2,4,6,8,10,13,15,17-octaen-9-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -2.3237    2.6934   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    1.3713   -0.1225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918    0.9735   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920    1.8161   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0177    1.5097   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8973    2.5637   -0.3391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5724    0.3012   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9662    0.4035   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7045   -0.7773   -0.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -2.0073   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7103   -2.1188   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0144   -0.9349   -0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -1.2073    0.1444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766   -0.4113    0.3747 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6839   -0.9501   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -2.2320   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5219   -2.3807   -0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3801   -1.3045   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.0218   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230    0.1370   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3866    2.6366    0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7849    3.3600    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420    3.1227   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    2.8262   -0.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6829    3.4771   -0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292    1.3678   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890   -0.7431   -0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6866   -2.9172    0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289   -3.0809    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -0.3393    1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4978   -3.0784   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292   -3.3932   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4363   -1.4888   -0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458    0.8271   -0.4590 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
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 20  2  1  0
 14  3  1  0
 16 15  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  1
 19 34  1  0
 18 33  1  0
 17 32  1  0
 16 31  1  0
M  END


  Mrv1652304292208152D          

 20 23  0  0  0  0            999 V2000
    6.3554    4.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292    3.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1732    2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9969    2.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4489    2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0772    1.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2535    1.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8015    2.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9940    1.9446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586    2.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694    2.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2199    1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3979    1.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750    2.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0969    2.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942    3.5652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539    4.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3739    3.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284    3.7981    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
  6  7  2  0  0  0  0
  3  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 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
 11 16  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 19  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=CC(O)=C3C=CC=CC3=NC2C2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H14N2O/c1-19-14-9-5-3-7-12(14)17-15(19)10-16(20)11-6-2-4-8-13(11)18-17/h2-10,17,20H,1H3

> <INCHI_KEY>
MLODBEIKDGFCLJ-UHFFFAOYSA-N

> <FORMULA>
C17H14N2O

> <MOLECULAR_WEIGHT>
262.312

> <EXACT_MASS>
262.110613079

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.026437428538443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-methyl-2,12-diazatetracyclo[9.7.0.0^{3,8}.0^{13,18}]octadeca-2,4,6,8,10,13(18),14,16-octaen-9-ol

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.2290568191680324

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.245465932123087

> <JCHEM_PKA_STRONGEST_BASIC>
7.684180501145284

> <JCHEM_POLAR_SURFACE_AREA>
35.830000000000005

> <JCHEM_REFRACTIVITY>
85.5292

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-methyl-2,12-diazatetracyclo[9.7.0.0^{3,8}.0^{13,18}]octadeca-2,4,6,8,10,13(18),14,16-octaen-9-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      11.863   7.905   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.881   6.719   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.523   5.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.061   5.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.905   4.118   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.211   2.743   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.673   2.656   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.830   3.945   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.322   3.630   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.136   4.612   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.663   4.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.010   2.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.476   2.636   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.594   3.899   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.247   5.294   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.781   5.426   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.709   6.655   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       6.261   8.128   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.165   6.152   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.386   7.090   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   11   15   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   10   17   20                                                  
CONECT   20   19    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄N₂O

Average Mass

262.3120 Da

Monoisotopic Mass

262.11061 Da

IUPAC Name

12-methyl-2,12-diazatetracyclo[9.7.0.0^{3,8}.0^{13,18}]octadeca-2,4,6,8,10,13(18),14,16-octaen-9-ol

Traditional Name

12-methyl-2,12-diazatetracyclo[9.7.0.0^{3,8}.0^{13,18}]octadeca-2,4,6,8,10,13(18),14,16-octaen-9-ol

CAS Registry Number

Not Available

SMILES

CN1C2=CC(O)=C3C=CC=CC3=NC2C2=C1C=CC=C2

InChI Identifier

InChI=1S/C17H14N2O/c1-19-14-9-5-3-7-12(14)17-15(19)10-16(20)11-6-2-4-8-13(11)18-17/h2-10,17,20H,1H3

InChI Key

MLODBEIKDGFCLJ-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
Cryptolepis sanguinolenta	Plant	KNApSAcK
Libocedrus yateensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Not Available

Direct Parent

Benzazepines

Alternative Parents

Substituents

Benzazepine
Indole or derivatives
Tertiary aliphatic/aromatic amine
Azepine
Benzenoid
Tertiary amine
Azacycle
Enamine
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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	2.5	ALOGPS
logP	2.23	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.25	ChemAxon
pKa (Strongest Basic)	7.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.53 m³·mol⁻¹	ChemAxon
Polarizability	29.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00055784

Chemspider ID

10235669

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cryptoheptine (NP0085782)

MOL for NP0085782 (Cryptoheptine)

3D MOL for NP0085782 (Cryptoheptine)

3D SDF for NP0085782 (Cryptoheptine)

3D-SDF for NP0085782 (Cryptoheptine)

PDB for NP0085782 (Cryptoheptine)

3D PDB for NP0085782 (Cryptoheptine)

SMILES for NP0085782 (Cryptoheptine)

INCHI for NP0085782 (Cryptoheptine)

Structure for NP0085782 (Cryptoheptine)

3D Structure for NP0085782 (Cryptoheptine)