NP-MRD: Showing NP-Card for Cularicine (NP0050963)

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Record Information

Version

2.0

Created at

2022-04-27 22:25:50 UTC

Updated at

2022-04-27 22:25:50 UTC

NP-MRD ID

NP0050963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cularicine

Description

(13S)-14-methyl-2,6,8-trioxa-14-azapentacyclo[11.7.1.0³,¹¹.0⁵,⁹.0¹⁷,²¹]Henicosa-1(20),3,5(9),10,17(21),18-hexaen-20-ol belongs to the class of organic compounds known as cularin alkaloids and derivatives. These are derivatives of benzylisoquinolines in which a phenolic oxygen is incorporated into a seven-membered ring. Cularicine is found in Corydalis claviculata, Sarcocapnos baetica and Sarcocapnos enneaphylla. Based on a literature review very few articles have been published on (13S)-14-methyl-2,6,8-trioxa-14-azapentacyclo[11.7.1.0³,¹¹.0⁵,⁹.0¹⁷,²¹]Henicosa-1(20),3,5(9),10,17(21),18-hexaen-20-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -1.4981    3.0259    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    1.8456   -0.7544 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1071    1.5714   -0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6849    0.6000    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634   -0.6399    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4666   -1.8781    0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -3.0308    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772   -2.9484    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6673   -4.1461    0.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683   -1.7324   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127   -0.5405   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8794    0.7706   -0.4597 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1314    1.0020    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312    0.3441    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402    1.1383    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141    0.6661    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9673   -0.6287   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508   -1.4017   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5633   -0.9532   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019   -1.9552   -0.3823 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -0.8437   -0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0548    0.1565    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0892    1.2124    0.3153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3006    3.7652   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5405    3.5391   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6295    2.8834    1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    1.2463   -1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6673    2.5434   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8651    0.9918    1.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6964    0.2884   -0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340   -1.8631    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2069   -4.0013    0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3209   -4.2087   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295    0.6168   -1.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2428    2.0506    0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2393    0.4688    1.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    2.1679    0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -2.4313   -0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561   -0.1380    1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9928    0.4467   -0.1423 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  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 19  2  0
 19 20  1  0
 19 18  1  0
 18 17  2  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 23 16  1  0
 16 15  2  0
 12  2  1  0
 15 14  1  0
 11  5  1  0
 16 17  1  0
 20 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
 12 34  1  6
 13 35  1  0
 13 36  1  0
 18 38  1  0
 22 39  1  0
 22 40  1  0
 15 37  1  0
M  END


  Mrv1652304282200252D          

 23 27  0  0  1  0            999 V2000
    0.8083   -1.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6110   -1.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -0.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -0.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782   -0.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419   -1.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882    0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481    1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507    1.2029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    0.6031    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2825    0.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    0.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306   -0.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748   -0.9193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9012   -0.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4116    0.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6410    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462    1.1058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7303    0.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567   -0.2124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1870    1.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055   -2.1497    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  0  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  2  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
  9 22  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2=CC=C(O)C3=C2[C@@H]1CC1=C(O3)C=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO4/c1-19-5-4-10-2-3-13(20)18-17(10)12(19)6-11-7-15-16(22-9-21-15)8-14(11)23-18/h2-3,7-8,12,20H,4-6,9H2,1H3/t12-/m0/s1

> <INCHI_KEY>
RUNKBNVIYGVBMW-LBPRGKRZSA-N

> <FORMULA>
C18H17NO4

> <MOLECULAR_WEIGHT>
311.337

> <EXACT_MASS>
311.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.24416815344001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(13S)-14-methyl-2,6,8-trioxa-14-azapentacyclo[11.7.1.0^{3,11}.0^{5,9}.0^{17,21}]henicosa-1(21),3(11),4,9,17,19-hexaen-20-ol

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.874141994666666

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.621731181049144

> <JCHEM_PKA_STRONGEST_BASIC>
6.198758499459584

> <JCHEM_POLAR_SURFACE_AREA>
51.160000000000004

> <JCHEM_REFRACTIVITY>
84.87870000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(13S)-14-methyl-2,6,8-trioxa-14-azapentacyclo[11.7.1.0^{3,11}.0^{5,9}.0^{17,21}]henicosa-1(21),3(11),4,9,17,19-hexaen-20-ol

> <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       1.509  -3.301   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.007  -2.945   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.270  -1.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.391  -0.350   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.893  -0.705   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.452  -2.181   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.165   0.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.276   1.890   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.775   2.245   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.832   1.126   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.261   1.701   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.601   0.943   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.844  -0.578   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.806  -1.716   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.282  -1.128   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.478  -0.157   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.235   1.363   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.797   1.913   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.606   2.064   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.697   0.977   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.999  -0.396   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.216   3.721   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.117  -4.013   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    3                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   12                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22    9                                                            
CONECT   23    2                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₇NO₄

Average Mass

311.3370 Da

Monoisotopic Mass

311.11576 Da

IUPAC Name

(13S)-14-methyl-2,6,8-trioxa-14-azapentacyclo[11.7.1.0^{3,11}.0^{5,9}.0^{17,21}]henicosa-1(21),3(11),4,9,17,19-hexaen-20-ol

Traditional Name

(13S)-14-methyl-2,6,8-trioxa-14-azapentacyclo[11.7.1.0^{3,11}.0^{5,9}.0^{17,21}]henicosa-1(21),3(11),4,9,17,19-hexaen-20-ol

CAS Registry Number

Not Available

SMILES

CN1CCC2=CC=C(O)C3=C2[C@@H]1CC1=C(O3)C=C2OCOC2=C1

InChI Identifier

InChI=1S/C18H17NO4/c1-19-5-4-10-2-3-13(20)18-17(10)12(19)6-11-7-15-16(22-9-21-15)8-14(11)23-18/h2-3,7-8,12,20H,4-6,9H2,1H3/t12-/m0/s1

InChI Key

RUNKBNVIYGVBMW-LBPRGKRZSA-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
Corydalis claviculata	Plant	KNApSAcK
Sarcocapnos baetica	LOTUS Database	35616633
Sarcocapnos enneaphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cularin alkaloids and derivatives. These are derivatives of benzylisoquinolines in which a phenolic oxygen is incorporated into a seven-membered ring.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cularin alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Cularin alkaloids and derivatives

Alternative Parents

Substituents

Cularin or derivatives
Dibenzoxepine
Diaryl ether
Tetrahydroisoquinoline
Benzodioxole
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Acetal
Ether
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:3955 )

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	2.31	ALOGPS
logP	2.87	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	8.62	ChemAxon
pKa (Strongest Basic)	6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.88 m³·mol⁻¹	ChemAxon
Polarizability	32.24 Å³	ChemAxon
Number of Rings	5	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

C00001839

Chemspider ID

390707

KEGG Compound ID

C09398

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442201

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cularicine (NP0050963)

MOL for NP0050963 (Cularicine)

3D MOL for NP0050963 (Cularicine)

3D SDF for NP0050963 (Cularicine)

3D-SDF for NP0050963 (Cularicine)

PDB for NP0050963 (Cularicine)

3D PDB for NP0050963 (Cularicine)

SMILES for NP0050963 (Cularicine)

INCHI for NP0050963 (Cularicine)

Structure for NP0050963 (Cularicine)

3D Structure for NP0050963 (Cularicine)