NP-MRD: Showing NP-Card for castoramine (NP0242740)

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Record Information

Version

2.0

Created at

2022-09-07 03:07:30 UTC

Updated at

2022-09-07 03:07:30 UTC

NP-MRD ID

NP0242740

Secondary Accession Numbers

None

Natural Product Identification

Common Name

castoramine

Description

Castoramine belongs to the class of organic compounds known as quinolizines. Quinolizines are compounds containing a quinolizine moiety, which consists of two fused pyridine rings sharing a nitrogen atom. castoramine is found in Castor fiber. castoramine was first documented in 2005 (PMID: 15624924). Based on a literature review very few articles have been published on Castoramine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.3584    3.3290    1.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093    2.5138   -0.1186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7115    2.1912   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3004    1.0282    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -0.1394    0.2702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9762   -1.4192   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -2.3781    0.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765   -3.4154    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7814   -3.0942   -1.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1850   -1.9065   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1365    0.1172   -0.5022 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937   -1.0100   -0.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9483   -1.0465    0.1359 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9087   -2.0126   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0739   -2.0245    0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    0.2434    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010    1.3638   -0.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971    1.2651    0.1017 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3209    4.1886    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    3.6714    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589    2.6609    2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807    3.1325   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3281    3.0840   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    1.9853   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6806    1.3353    1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963    0.6922   -0.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0038   -0.1569    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4923   -2.3440    1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4324   -4.3048    0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416   -1.4731   -2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1100   -1.9291   -0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9434   -1.1122   -1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525   -1.5075    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061   -1.5824   -1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4767   -3.0070   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8539   -2.3327    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6508    0.5466    1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7122    0.2492   -0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9864    1.2069   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3615    2.3232   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5354    1.0684    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
  5  6  1  0
  6 10  2  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
 18  2  1  0
  7  6  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  1
 12 31  1  0
 12 32  1  0
 13 33  1  1
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  1
 10 30  1  0
  8 29  1  0
  7 28  1  0
M  END


  Mrv1652309072205072D          

 18 20  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   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  1  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
    4.2868    0.8250    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0242740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H](N2C[C@@H](CO)CC[C@@H]12)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H23NO2/c1-11-2-4-15(13-6-7-18-10-13)16-8-12(9-17)3-5-14(11)16/h6-7,10-12,14-15,17H,2-5,8-9H2,1H3/t11-,12+,14+,15+/m1/s1

> <INCHI_KEY>
FFVCMXOAPCVMHQ-DHMWGJHJSA-N

> <FORMULA>
C15H23NO2

> <MOLECULAR_WEIGHT>
249.354

> <EXACT_MASS>
249.172878985

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.552380522769404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3S,6S,9R,9aS)-6-(furan-3-yl)-9-methyl-octahydro-1H-quinolizin-3-yl]methanol

> <JCHEM_LOGP>
2.2099782696666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.431402983462512

> <JCHEM_PKA_STRONGEST_BASIC>
9.067350131066092

> <JCHEM_POLAR_SURFACE_AREA>
36.61

> <JCHEM_REFRACTIVITY>
71.51160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,6S,9R,9aS)-6-(furan-3-yl)-9-methyl-octahydro-1H-quinolizin-3-yl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.421   2.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.897   3.910   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.437   3.910   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.913   2.445   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    5   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2   11                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₃NO₂

Average Mass

249.3540 Da

Monoisotopic Mass

249.17288 Da

IUPAC Name

[(3S,6S,9R,9aS)-6-(furan-3-yl)-9-methyl-octahydro-1H-quinolizin-3-yl]methanol

Traditional Name

[(3S,6S,9R,9aS)-6-(furan-3-yl)-9-methyl-octahydro-1H-quinolizin-3-yl]methanol

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H](N2C[C@@H](CO)CC[C@@H]12)C1=COC=C1

InChI Identifier

InChI=1S/C15H23NO2/c1-11-2-4-15(13-6-7-18-10-13)16-8-12(9-17)3-5-14(11)16/h6-7,10-12,14-15,17H,2-5,8-9H2,1H3/t11-,12+,14+,15+/m1/s1

InChI Key

FFVCMXOAPCVMHQ-DHMWGJHJSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Castor fiber	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolizines. Quinolizines are compounds containing a quinolizine moiety, which consists of two fused pyridine rings sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolizines

Sub Class

Not Available

Direct Parent

Quinolizines

Alternative Parents

Substituents

Quinolizidine
Quinolizine
Aralkylamine
Piperidine
1,3-aminoalcohol
Furan
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
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	2.21	ChemAxon
pKa (Strongest Acidic)	15.43	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.51 m³·mol⁻¹	ChemAxon
Polarizability	28.55 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

9543597

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Castoramine

METLIN ID

Not Available

PubChem Compound

11368680

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Goodenough KM, Moran WJ, Raubo P, Harrity JP: Development of a flexible approach to Nuphar alkaloids via two enantiospecific piperidine-forming reactions. J Org Chem. 2005 Jan 7;70(1):207-13. doi: 10.1021/jo048455k. [PubMed:15624924 ]
LOTUS database [Link]

Showing NP-Card for castoramine (NP0242740)

MOL for NP0242740 (castoramine)

3D MOL for NP0242740 (castoramine)

3D SDF for NP0242740 (castoramine)

3D-SDF for NP0242740 (castoramine)

PDB for NP0242740 (castoramine)

3D PDB for NP0242740 (castoramine)

SMILES for NP0242740 (castoramine)

INCHI for NP0242740 (castoramine)

Structure for NP0242740 (castoramine)

3D Structure for NP0242740 (castoramine)