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Showing NP-Card for Cuauchichicine (NP0050779)

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Record Information
Version2.0
Created at2022-04-27 22:06:35 UTC
Updated at2022-04-27 22:06:35 UTC
NP-MRD IDNP0050779
Secondary Accession NumbersNone
Natural Product Identification
Common NameCuauchichicine
DescriptionCuauchichicine belongs to the class of organic compounds known as veatchine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the veatchine skeleton, a pentacyclic compound, in which the carbon skeleton is the same as kaurane. Cuauchichicine is found in Garrya laurifolia and Garrya ovata var. lindheimeri. Based on a literature review very few articles have been published on Cuauchichicine.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050779 (Cuauchichicine)


  Mrv1652304282200062D          

 25 30  0  0  1  0            999 V2000
    1.2263   -0.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -1.2332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0129   -0.3015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9172    0.8055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2991    0.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1847    0.8967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4572    0.3893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5835   -0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167    0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7267   -0.5721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8922    0.9204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3513    1.5932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3391    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297    1.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162    0.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407    0.7547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2871    0.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438    0.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651    1.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597    1.4654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2363   -0.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864   -2.0134    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  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  1  0  0  0
 14 17  1  1  0  0  0
  8 17  1  1  0  0  0
 13 18  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  1  0  0  0
M  END
Download

3D MOL for NP0050779 (Cuauchichicine)

Download
3D SDF for NP0050779 (Cuauchichicine)

  Mrv1652304282200062D          

 25 30  0  0  1  0            999 V2000
    1.2263   -0.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -1.2332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0129   -0.3015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9172    0.8055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2991    0.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1847    0.8967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4572    0.3893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5835   -0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167    0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7267   -0.5721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8922    0.9204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3513    1.5932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3391    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297    1.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162    0.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407    0.7547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2871    0.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438    0.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651    1.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597    1.4654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2363   -0.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864   -2.0134    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  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  1  0  0  0
 14 17  1  1  0  0  0
  8 17  1  1  0  0  0
 13 18  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H]2C[C@@]3(CC[C@@H]4[C@@]5(C)CCC[C@@]4([C@@H]4OCCN4C5)[C@@H]3CC2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO2/c1-14-15-4-5-17-21(12-15,18(14)24)9-6-16-20(2)7-3-8-22(16,17)19-23(13-20)10-11-25-19/h14-17,19H,3-13H2,1-2H3/t14-,15-,16-,17-,19+,20+,21-,22+/m1/s1

> <INCHI_KEY>
BGZNEAVTIQGRHL-DHZZTMSNSA-N

> <FORMULA>
C22H33NO2

> <MOLECULAR_WEIGHT>
343.511

> <EXACT_MASS>
343.251129307

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.663073041919674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,6R,8R,11R,12R,18S)-6,12-dimethyl-17-oxa-14-azahexacyclo[10.6.3.1^{5,8}.0^{1,11}.0^{2,8}.0^{14,18}]docosan-7-one

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
4.325626705333333

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.010109579328831

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
97.41499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,6R,8R,11R,12R,18S)-6,12-dimethyl-17-oxa-14-azahexacyclo[10.6.3.1^{5,8}.0^{1,11}.0^{2,8}.0^{14,18}]docosan-7-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0050779 (Cuauchichicine)
Download
PDB for NP0050779 (Cuauchichicine)
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       2.289  -0.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.350  -2.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.887  -2.302   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.757  -0.563   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.579   1.504   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.425   0.484   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.211   1.674   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.853   0.727   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.089  -0.831   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.495  -1.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.778   0.359   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.357  -1.068   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.665   1.718   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.656   2.974   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.633   3.946   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.109   3.313   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.204   1.891   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.204   1.794   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.116   1.409   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       6.136   0.255   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       7.548   0.868   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.401   2.401   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.898   2.735   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.041  -1.282   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.388  -3.758   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24   25                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   19                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   16                                                  
CONECT    8    7    9   11   17                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    7                                                       
CONECT   17   14    8                                                       
CONECT   18   13                                                            
CONECT   19    5   20   23                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
CONECT   24   20    3                                                       
CONECT   25    3                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

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3D PDB for NP0050779 (Cuauchichicine)
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SMILES for NP0050779 (Cuauchichicine)
C[C@@H]1[C@H]2C[C@@]3(CC[C@@H]4[C@@]5(C)CCC[C@@]4([C@@H]4OCCN4C5)[C@@H]3CC2)C1=O
Download
INCHI for NP0050779 (Cuauchichicine)
InChI=1S/C22H33NO2/c1-14-15-4-5-17-21(12-15,18(14)24)9-6-16-20(2)7-3-8-22(16,17)19-23(13-20)10-11-25-19/h14-17,19H,3-13H2,1-2H3/t14-,15-,16-,17-,19+,20+,21-,22+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC22H33NO2
Average Mass343.5110 Da
Monoisotopic Mass343.25113 Da
IUPAC Name(1S,2S,5R,6R,8R,11R,12R,18S)-6,12-dimethyl-17-oxa-14-azahexacyclo[10.6.3.1^{5,8}.0^{1,11}.0^{2,8}.0^{14,18}]docosan-7-one
Traditional Name(1S,2S,5R,6R,8R,11R,12R,18S)-6,12-dimethyl-17-oxa-14-azahexacyclo[10.6.3.1^{5,8}.0^{1,11}.0^{2,8}.0^{14,18}]docosan-7-one
CAS Registry NumberNot Available
SMILES
C[C@@H]1[C@H]2C[C@@]3(CC[C@@H]4[C@@]5(C)CCC[C@@]4([C@@H]4OCCN4C5)[C@@H]3CC2)C1=O
InChI Identifier
InChI=1S/C22H33NO2/c1-14-15-4-5-17-21(12-15,18(14)24)9-6-16-20(2)7-3-8-22(16,17)19-23(13-20)10-11-25-19/h14-17,19H,3-13H2,1-2H3/t14-,15-,16-,17-,19+,20+,21-,22+/m1/s1
InChI KeyBGZNEAVTIQGRHL-DHZZTMSNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Garrya laurifoliaPlant
Garrya ovata var. lindheimeriPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as veatchine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the veatchine skeleton, a pentacyclic compound, in which the carbon skeleton is the same as kaurane.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentVeatchine-type diterpenoid alkaloids  
Alternative Parents
Substituents
  • Veatchine-type diterpenoid alkaloid
    • 

  • Alkaloid or derivatives
    • 

  • Piperidine
    • 

  • Oxazolidine
    • 

  • Hemiaminal
    • 

  • Ketone
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP3.02ALOGPS
logP4.33ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)7.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity97.42 m³·mol⁻¹ChemAxon
Polarizability39.66 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001628  
Chemspider ID62988639  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21733103  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available