NP-MRD: Showing NP-Card for Oxosarcocapnidine (NP0067083)

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Record Information

Version

2.0

Created at

2022-04-28 11:15:42 UTC

Updated at

2022-04-28 11:15:42 UTC

NP-MRD ID

NP0067083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxosarcocapnidine

Description

4-Hydroxy-5,17-dimethoxy-2-oxa-11-azatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]Octadeca-1(17),3(8),4,6,10,12,14(18),15-octaen-9-one belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring. Oxosarcocapnidine is found in Ceratocapnos palaestinus, Corydalis rutifolia, Sarcocapnos crassifolia, Sarcocapnos enneaphylla and Sarcocapnos saetabensis. 4-Hydroxy-5,17-dimethoxy-2-oxa-11-azatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]Octadeca-1(17),3(8),4,6,10,12,14(18),15-octaen-9-one is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    5.7996    1.2284   -0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459    1.6146   -0.1972 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4332    0.6579   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729   -0.6708   -0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -1.5918    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437   -1.1652    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261    0.1876    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1487    1.1031    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8281    2.4358    0.1906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1177    0.7200    0.4489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.1916    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    1.2213    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9156    2.5355    0.4129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665    3.5556    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6601    0.9088    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0957   -0.3826    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1328   -1.3977    0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6147   -2.6916   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7464   -3.7467   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4374   -3.5261    0.0848 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588   -2.2762    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7814   -1.1478    0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132   -2.2761    0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030   -3.4112    0.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3233    2.1379   -0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8786    0.4712   -1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2749    0.8724    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956   -1.0198   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -2.6556   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5687    3.1138    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5826    3.4971    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4933    3.4527   -0.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4152    4.5643    0.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4172    1.7090    0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1627   -0.6061   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039   -2.8557   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618   -4.7578   -0.1299 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  2  0
  6  7  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
 23  6  1  0
 22 11  2  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
  9 30  1  0
M  END


  Mrv1533004261513502D          

 24 27  0  0  0  0            999 V2000
    4.8037    2.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873    1.5348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586   -0.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166   -1.5370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8336   -0.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.5141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1097    0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0816    2.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8700    2.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028    0.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461    1.0136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9894    0.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    2.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192   -0.1486    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  9 24  2  0  0  0  0
 13 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(OC3=C(OC)C=CC4=CC=NC(=C34)C2=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO5/c1-22-11-6-4-10-15(20)14-13-9(7-8-19-14)3-5-12(23-2)18(13)24-17(10)16(11)21/h3-8,21H,1-2H3

> <INCHI_KEY>
JBWYXHCUKXERPB-UHFFFAOYSA-N

> <FORMULA>
C18H13NO5

> <MOLECULAR_WEIGHT>
323.304

> <EXACT_MASS>
323.079372523

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
32.474782230348175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-5,17-dimethoxy-2-oxa-11-azatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),3,5,7,10(18),11,13,15-octaen-9-one

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.498387022666666

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.442823461061014

> <JCHEM_PKA_STRONGEST_BASIC>
3.2541051480586503

> <JCHEM_POLAR_SURFACE_AREA>
77.88000000000001

> <JCHEM_REFRACTIVITY>
85.64489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-5,17-dimethoxy-2-oxa-11-azatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),3,5,7,10(18),11,13,15-octaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       8.967   4.366   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.310   2.865   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.181   1.817   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.523   0.316   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.395  -0.731   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.923  -0.277   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.963  -1.481   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.631  -2.869   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.423  -1.481   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.249  -2.826   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.777  -3.280   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.648  -2.233   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.991  -0.731   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.138   0.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.205   1.817   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.676   2.271   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.019   3.773   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.491   4.227   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.805   1.224   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.193   1.892   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.580   1.224   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.709   2.271   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.366   3.773   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.463  -0.277   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   24                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20    6   22                                                  
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
CONECT   24   19    9   13                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₃NO₅

Average Mass

323.3040 Da

Monoisotopic Mass

323.07937 Da

IUPAC Name

4-hydroxy-5,17-dimethoxy-2-oxa-11-azatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),3,5,7,10(18),11,13,15-octaen-9-one

Traditional Name

4-hydroxy-5,17-dimethoxy-2-oxa-11-azatetracyclo[8.7.1.0³,⁸.0¹⁴,¹⁸]octadeca-1(17),3,5,7,10(18),11,13,15-octaen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(OC3=C(OC)C=CC4=CC=NC(=C34)C2=O)=C1O

InChI Identifier

InChI=1S/C18H13NO5/c1-22-11-6-4-10-15(20)14-13-9(7-8-19-14)3-5-12(23-2)18(13)24-17(10)16(11)21/h3-8,21H,1-2H3

InChI Key

JBWYXHCUKXERPB-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
Ceratocapnos palaestinus	Plant	KNApSAcK
Corydalis rutifolia	Plant	KNApSAcK
Sarcocapnos crassifolia	Plant	KNApSAcK
Sarcocapnos enneaphylla	Plant	KNApSAcK
Sarcocapnos saetabensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Dibenzoxepines

Direct Parent

Dibenzoxepines

Alternative Parents

Substituents

Dibenzoxepine
Isoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
Ether
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
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	3.09	ALOGPS
logP	2.5	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.44	ChemAxon
pKa (Strongest Basic)	3.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.88 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.64 m³·mol⁻¹	ChemAxon
Polarizability	32.47 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14194054

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oxosarcocapnidine (NP0067083)

MOL for NP0067083 (Oxosarcocapnidine)

3D MOL for NP0067083 (Oxosarcocapnidine)

3D SDF for NP0067083 (Oxosarcocapnidine)

3D-SDF for NP0067083 (Oxosarcocapnidine)

PDB for NP0067083 (Oxosarcocapnidine)

3D PDB for NP0067083 (Oxosarcocapnidine)

SMILES for NP0067083 (Oxosarcocapnidine)

INCHI for NP0067083 (Oxosarcocapnidine)

Structure for NP0067083 (Oxosarcocapnidine)

3D Structure for NP0067083 (Oxosarcocapnidine)