NP-MRD: Showing NP-Card for Carolinianine (NP0051040)

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Record Information

Version

2.0

Created at

2022-04-27 22:29:13 UTC

Updated at

2022-04-27 22:29:14 UTC

NP-MRD ID

NP0051040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carolinianine

Description

Carolinianine belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Carolinianine is found in Lycopodium carolinianum var. affine. Based on a literature review very few articles have been published on Carolinianine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.8745    2.4165    0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8925    1.5559    0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289    0.2389    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9877   -0.5466   -0.5790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2715   -2.0044   -0.3430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5283   -2.2266    0.9920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1516   -2.8026   -0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1386   -2.3912   -0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4079   -0.9307   -0.4562 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5915   -0.4412    0.2179 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -1.2964    0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822   -2.4590    1.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0127   -0.8048    0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1122    0.4015   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1615    1.4571    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629    1.0041    0.4752 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7942    1.6961   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5563    1.2573   -0.0449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7047    2.1072   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206   -0.1028   -0.2858 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7646    2.6384    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2605    1.9634    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351    3.3971    1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765   -0.2568    0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2019   -0.3728   -1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001   -2.2570   -0.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853   -3.0308    1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2673   -3.8889   -0.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032   -2.5312   -1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0752   -2.6395    0.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9054   -3.0518   -0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6727   -0.9012   -1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3093   -0.5024    1.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -1.5615    0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9087    0.1926   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489    0.7895   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1973    2.3294   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    1.8239    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    1.1887    1.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9863    1.2180   -1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497    2.7835   -0.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5822    1.4177    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244    3.1650   -0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8645    1.9583   -1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 20  1  0
 20 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 18 19  1  0
 19  2  1  0
 20  4  1  0
 10 16  1  0
 10  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  6
  5 26  1  6
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  6
 18 42  1  1
 17 40  1  0
 17 41  1  0
 16 39  1  1
 15 37  1  0
 15 38  1  0
 14 35  1  0
 14 36  1  0
 13 33  1  0
 13 34  1  0
 19 43  1  0
 19 44  1  0
M  END


  Mrv1652304282200292D          

 20 23  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  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
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   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
    2.8579   -2.4750    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
    3.5724   -0.4125    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  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  6  0  0  0
 10  9  1  1  0  0  0
  4 10  1  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
  3 13  1  0  0  0  0
 13 14  1  1  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@@H]2[C@H](O)CC[C@H]3N2[C@@H](C[C@@H]2CCCC(=O)N32)C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2O2/c1-10-7-12-9-11-3-2-4-16(20)18(11)15-6-5-14(19)13(8-10)17(12)15/h8,11-15,19H,2-7,9H2,1H3/t11-,12+,13+,14+,15-/m0/s1

> <INCHI_KEY>
YRHGJVCKHYJQQO-JARUQAPTSA-N

> <FORMULA>
C16H24N2O2

> <MOLECULAR_WEIGHT>
276.38

> <EXACT_MASS>
276.183778021

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.019356203403845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,7S,9R,13R,14R)-14-hydroxy-11-methyl-2,17-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-11-en-3-one

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
0.9353682959999993

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.529020253255407

> <JCHEM_PKA_STRONGEST_BASIC>
6.568387509490794

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
77.4198

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7S,9R,13R,14R)-14-hydroxy-11-methyl-2,17-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-11-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    8                                                       
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₄N₂O₂

Average Mass

276.3800 Da

Monoisotopic Mass

276.18378 Da

IUPAC Name

(1S,7S,9R,13R,14R)-14-hydroxy-11-methyl-2,17-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-11-en-3-one

Traditional Name

(1S,7S,9R,13R,14R)-14-hydroxy-11-methyl-2,17-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-11-en-3-one

CAS Registry Number

Not Available

SMILES

CC1=C[C@@H]2[C@H](O)CC[C@H]3N2[C@@H](C[C@@H]2CCCC(=O)N32)C1

InChI Identifier

InChI=1S/C16H24N2O2/c1-10-7-12-9-11-3-2-4-16(20)18(11)15-6-5-14(19)13(8-10)17(12)15/h8,11-15,19H,2-7,9H2,1H3/t11-,12+,13+,14+,15-/m0/s1

InChI Key

YRHGJVCKHYJQQO-JARUQAPTSA-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
Lycopodium carolinianum var. affine	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridopyrimidines

Sub Class

Not Available

Direct Parent

Pyridopyrimidines

Alternative Parents

Substituents

Pyridopyrimidine
Delta-lactam
Piperidinone
1,3-diazinane
Piperidine
Pyridine
Pyrimidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Alcohol
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

pyridopyrimidine (CHEBI:3430 )
Quinolizidine alkaloids (C09856 )

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	0.83	ALOGPS
logP	0.94	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	14.53	ChemAxon
pKa (Strongest Basic)	6.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.42 m³·mol⁻¹	ChemAxon
Polarizability	31.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00001934

Chemspider ID

390904

KEGG Compound ID

C09856

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442470

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Carolinianine (NP0051040)

MOL for NP0051040 (Carolinianine)

3D MOL for NP0051040 (Carolinianine)

3D SDF for NP0051040 (Carolinianine)

3D-SDF for NP0051040 (Carolinianine)

PDB for NP0051040 (Carolinianine)

3D PDB for NP0051040 (Carolinianine)

SMILES for NP0051040 (Carolinianine)

INCHI for NP0051040 (Carolinianine)

Structure for NP0051040 (Carolinianine)

3D Structure for NP0051040 (Carolinianine)