NP-MRD: Showing NP-Card for (11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene (NP0182319)

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Record Information

Version

2.0

Created at

2022-09-03 20:58:34 UTC

Updated at

2022-09-03 20:58:34 UTC

NP-MRD ID

NP0182319

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene

Description

WIN 55212-2, also known as win 55,212 or (R)-win-55212, belongs to the class of organic compounds known as naphthoylindoles. These are polycyclic compounds containing an indole moiety that is N-linked to the carboxamide group attached to naphthalene. (11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene was first documented in 2003 (PMID: 14512703). Based on a literature review a significant number of articles have been published on WIN 55212-2 (PMID: 35674874) (PMID: 33371336) (PMID: 32710782) (PMID: 31181184) (PMID: 29883990) (PMID: 29627825).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032222582D          

 32 37  0  0  1  0            999 V2000
    1.8226   -0.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127    0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278   -0.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7927   -0.5543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633   -1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -1.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194   -2.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0345   -2.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2140   -2.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710   -3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914   -3.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -2.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9421   -1.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1216   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959    1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    2.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390    2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926    0.8115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463    1.1470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0138    0.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674    0.9977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537    1.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6073    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2748    1.6688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1885    0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4349    0.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
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  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  6 15  2  0  0  0  0
 10 15  1  0  0  0  0
  3 16  1  0  0  0  0
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 16 21  1  0  0  0  0
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 31 32  1  0  0  0  0
 20 32  1  0  0  0  0
M  END

     RDKit          3D

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    2.2428   -1.1970    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7239    2.7493    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2728    1.4655    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0694    0.3341    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8922   -1.5537   -1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312   -2.4219   -1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.8132   -3.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1196   -2.3509   -3.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365   -1.4955   -2.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3063   -1.1194   -1.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -0.2959   -0.6297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244    0.2825   -1.0484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8894    1.1540   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3722    0.6290    1.0830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225    1.6750    1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4245    1.9351    1.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2289    0.8399    1.5267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5002   -0.2582    1.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4167    3.9535   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    3.6283    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    1.3332    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5719   -2.7595   -1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6602   -3.4865   -3.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326   -2.6505   -4.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    1.0179   -1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3348    2.1217   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8075    1.5075   -0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    1.4464    2.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8361    2.8142    1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351    2.2157    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1109   -1.1938    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032222582D          

 32 37  0  0  1  0            999 V2000
    1.8226   -0.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127    0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278   -0.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7927   -0.5543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633   -1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -1.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194   -2.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4326    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0182319

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C(=O)C2=C3C=CC=CC3=CC=C2)C2=CC=CC3=C2N1[C@H](CN1CCOCC1)CO3

> <INCHI_IDENTIFIER>
InChI=1S/C27H26N2O3/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28/h2-11,20H,12-17H2,1H3/t20-/m1/s1

> <INCHI_KEY>
HQVHOQAKMCMIIM-HXUWFJFHSA-N

> <FORMULA>
C27H26N2O3

> <MOLECULAR_WEIGHT>
426.516

> <EXACT_MASS>
426.194342705

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.80330958924822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11R)-2-methyl-11-[(morpholin-4-yl)methyl]-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0^{4,12}]dodeca-2,4,6,8(12)-tetraene

> <JCHEM_LOGP>
4.474789923333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.375089612598222

> <JCHEM_POLAR_SURFACE_AREA>
43.699999999999996

> <JCHEM_REFRACTIVITY>
125.4746

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(11R)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0^{4,12}]dodeca-2,4,6,8(12)-tetraene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.402  -1.196   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.497   0.050   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.957   0.050   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.052  -1.196   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.480  -1.035   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.678  -2.603   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.210  -2.764   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.836  -4.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.931  -5.416   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.399  -5.255   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.506  -6.501   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.037  -6.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.664  -4.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.759  -3.688   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.227  -3.848   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.481   1.515   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.926   2.141   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.087   3.673   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.159   4.578   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.566   3.952   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.727   2.420   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.973   1.515   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       4.380   2.141   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.626   1.236   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       7.033   1.862   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       7.194   3.394   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.600   4.020   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.846   3.115   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.685   1.584   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.278   0.957   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.541   3.673   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.295   4.578   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   10                                                  
CONECT   16    3   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21    2   23                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   23   32                                                       
CONECT   32   31   20                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl)methanone	ChEBI
Win 55,212	ChEBI
(2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl)methanone monomethanesulfonate	MeSH
(3R)-((2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone monomethanesulfonate	MeSH
(3R)-((2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone	MeSH
((3R)-2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo(1,2,3-de)-1,4-benzoxazin-6-yl)-1-naphthalenyl-methanone, methanesulfonate (1:1)	MeSH
(+)-((2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone monomethanesulfonate	MeSH
(R)-(+)-WIN-55212-2	MeSH
(R)-WIN-55212	MeSH
WIN 55212-2 mesylate	MeSH
(3S)-((2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone	MeSH
(R)-(+)-WIN 55212-2 mesylate	MeSH
2,3-Dihydro-5-methyl-3((4-morpholinyl)methyl) pyrrolo(1,2,3,-de)-1,4-benzoxazin-6-yl)-1-naphthalenyl methanone	MeSH

Chemical Formula

C₂₇H₂₆N₂O₃

Average Mass

426.5160 Da

Monoisotopic Mass

426.19434 Da

IUPAC Name

(11R)-2-methyl-11-[(morpholin-4-yl)methyl]-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0^{4,12}]dodeca-2,4,6,8(12)-tetraene

Traditional Name

(11R)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0^{4,12}]dodeca-2,4,6,8(12)-tetraene

CAS Registry Number

Not Available

SMILES

CC1=C(C(=O)C2=C3C=CC=CC3=CC=C2)C2=CC=CC3=C2N1[C@H](CN1CCOCC1)CO3

InChI Identifier

InChI=1S/C27H26N2O3/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28/h2-11,20H,12-17H2,1H3/t20-/m1/s1

InChI Key

HQVHOQAKMCMIIM-HXUWFJFHSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoylindoles. These are polycyclic compounds containing an indole moiety that is N-linked to the carboxamide group attached to naphthalene.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Naphthoylindoles

Direct Parent

Naphthoylindoles

Alternative Parents

Substituents

Naphthoylindole
Benzoylindole
1-naphthalenecarboxylic acid or derivatives
Indolecarboxylic acid derivative
Benzoxazine
Naphthalene
Indole
Aryl ketone
Alkyl aryl ether
Morpholine
Oxazinane
Substituted pyrrole
Benzenoid
Vinylogous amide
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Ketone
Dialkyl ether
Ether
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:73295 )
morpholines (CHEBI:73295 )
naphthyl ketone (CHEBI:73295 )
synthetic cannabinoid (CHEBI:73295 )

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	4.47	ChemAxon
pKa (Strongest Basic)	6.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	125.47 m³·mol⁻¹	ChemAxon
Polarizability	46.8 Å³	ChemAxon
Number of Rings	6	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

4470978

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

WIN_55,212-2

METLIN ID

Not Available

PubChem Compound

5311501

PDB ID

Not Available

ChEBI ID

73295

Good Scents ID

Not Available

References

General References

He Q, Zhang W, Zhang J, Deng Y: Cannabinoid Analogue WIN 55212-2 Protects Paraquat-Induced Lung Injury and Enhances Macrophage M2 Polarization. Inflammation. 2022 Dec;45(6):2256-2267. doi: 10.1007/s10753-022-01688-z. Epub 2022 Jun 8. [PubMed:35674874 ]
Liu QR, Canseco-Alba A, Liang Y, Ishiguro H, Onaivi ES: Low Basal CB2R in Dopamine Neurons and Microglia Influences Cannabinoid Tetrad Effects. Int J Mol Sci. 2020 Dec 21;21(24):9763. doi: 10.3390/ijms21249763. [PubMed:33371336 ]
Perez-Valenzuela EJ, Andres Coke ME, Grace AA, Fuentealba Evans JA: Adolescent Exposure to WIN 55212-2 Render the Nigrostriatal Dopaminergic Pathway Activated During Adulthood. Int J Neuropsychopharmacol. 2020 Dec 3;23(9):626-637. doi: 10.1093/ijnp/pyaa053. [PubMed:32710782 ]
Perez-Valenzuela E, Castillo-Faundez R, Fuentealba JA: Comparing dopaminergic dynamics in the dorsolateral striatum between adolescent and adult rats: Effect of an acute dose of WIN55212-2. Brain Res. 2019 Sep 15;1719:235-242. doi: 10.1016/j.brainres.2019.06.005. Epub 2019 Jun 7. [PubMed:31181184 ]
Gholizadeh F, Ghahremani MH, Aliebrahimi S, Shadboorestan A, Ostad SN: Assessment of Cannabinoids Agonist and Antagonist in Invasion Potential of K562 Cancer Cells. Iran Biomed J. 2019 Mar;23(2):153-8. doi: 10.29252/.23.2.153. Epub 2018 Jun 9. [PubMed:29883990 ]
Donnerer J, Liebmann I: Effect of CB1 Ligands on Neurogenic and Myogenic Contractile Responses in the Guinea-Pig Ileum. Pharmacology. 2018;101(5-6):330-336. doi: 10.1159/000488682. Epub 2018 Apr 6. [PubMed:29627825 ]
Neves LMS, Goncalves ECD, Cavalli J, Vieira G, Laurindo LR, Simoes RR, Coelho IS, Santos ARS, Marcolino AM, Cola M, Dutra RC: Photobiomodulation Therapy Improves Acute Inflammatory Response in Mice: the Role of Cannabinoid Receptors/ATP-Sensitive K(+) Channel/p38-MAPK Signalling Pathway. Mol Neurobiol. 2018 Jul;55(7):5580-5593. doi: 10.1007/s12035-017-0792-z. Epub 2017 Oct 4. [PubMed:28980210 ]
Aguilar MA, Ledesma JC, Rodriguez-Arias M, Penalva C, Manzanedo C, Minarro J, Arenas MC: Adolescent Exposure to the Synthetic Cannabinoid WIN 55212-2 Modifies Cocaine Withdrawal Symptoms in Adult Mice. Int J Mol Sci. 2017 Jun 21;18(6):1326. doi: 10.3390/ijms18061326. [PubMed:28635664 ]
Araujo DSM, Miya-Coreixas VS, Pandolfo P, Calaza KC: Cannabinoid receptors and TRPA1 on neuroprotection in a model of retinal ischemia. Exp Eye Res. 2017 Jan;154:116-125. doi: 10.1016/j.exer.2016.11.015. Epub 2016 Nov 19. [PubMed:27876485 ]
Rodriguez-Arias M, Roger-Sanchez C, Villanova I, Revert N, Manzanedo C, Minarro J, Aguilar MA: Corrigendum to "Effects of Cannabinoid Exposure during Adolescence on the Conditioned Rewarding Effects of WIN 55212-2 and Cocaine in Mice: Influence of the Novelty-Seeking Trait". Neural Plast. 2016;2016:6702083. doi: 10.1155/2016/6702083. Epub 2016 Jul 28. [PubMed:27547455 ]
Costain WJ, Tauskela JS, Rasquinha I, Comas T, Hewitt M, Marleau V, Soo EC: Pharmacological characterization of emerging synthetic cannabinoids in HEK293T cells and hippocampal neurons. Eur J Pharmacol. 2016 Sep 5;786:234-245. doi: 10.1016/j.ejphar.2016.05.040. Epub 2016 May 31. [PubMed:27260125 ]
Rodriguez-Arias M, Roger-Sanchez C, Vilanova I, Revert N, Manzanedo C, Minarro J, Aguilar MA: Effects of Cannabinoid Exposure during Adolescence on the Conditioned Rewarding Effects of WIN 55212-2 and Cocaine in Mice: Influence of the Novelty-Seeking Trait. Neural Plast. 2016;2016:6481862. doi: 10.1155/2016/6481862. Epub 2015 Dec 31. [PubMed:26881125 ]
Chiodi V, Ferrante A, Ferraro L, Potenza RL, Armida M, Beggiato S, Pezzola A, Bader M, Fuxe K, Popoli P, Domenici MR: Striatal adenosine-cannabinoid receptor interactions in rats over-expressing adenosine A2A receptors. J Neurochem. 2016 Mar;136(5):907-17. doi: 10.1111/jnc.13421. Epub 2015 Nov 24. [PubMed:26526685 ]
Toguri JT, Moxsom R, Szczesniak AM, Zhou J, Kelly ME, Lehmann C: Cannabinoid 2 receptor activation reduces leukocyte adhesion and improves capillary perfusion in the iridial microvasculature during systemic inflammation. Clin Hemorheol Microcirc. 2015;61(2):237-49. doi: 10.3233/CH-151996. [PubMed:26410875 ]
Soni N, Kohlmeier KA: Endocannabinoid CB1 receptor-mediated rises in Ca(2+) and depolarization-induced suppression of inhibition within the laterodorsal tegmental nucleus. Brain Struct Funct. 2016 Apr;221(3):1255-77. doi: 10.1007/s00429-014-0969-4. Epub 2015 Jan 9. [PubMed:25573246 ]
Pozzi O, Misiano P, Clark GD, Visentin L: Antagonism between the anti-inflammatory activity of the cannabinoid WIN 55212-2 and SR 141716A. Pharmacology. 2003 Nov;69(3):158-63. doi: 10.1159/000072669. [PubMed:14512703 ]
Yoshihara S, Morimoto H, Ohori M, Yamada Y, Abe T, Arisaka O: The cannabinoid receptor agonist WIN 55212-2 inhibits neurogenic inflammations in airway tissues. J Pharmacol Sci. 2005 May;98(1):77-82. doi: 10.1254/jphs.fp0050171. Epub 2005 May 12. [PubMed:15888960 ]
Rawls SM, Gomez T, Raffa RB: An NMDA antagonist (LY 235959) attenuates abstinence-induced withdrawal of planarians following acute exposure to a cannabinoid agonist (WIN 55212-2). Pharmacol Biochem Behav. 2007 Mar;86(3):499-504. doi: 10.1016/j.pbb.2007.01.010. Epub 2007 Jan 20. [PubMed:17306870 ]
Rodriguez-Arias M, Manzanedo C, Roger-Sanchez C, Do Couto BR, Aguilar MA, Minarro J: Effect of adolescent exposure to WIN 55212-2 on the acquisition and reinstatement of MDMA-induced conditioned place preference. Prog Neuropsychopharmacol Biol Psychiatry. 2010 Feb 1;34(1):166-71. doi: 10.1016/j.pnpbp.2009.10.019. Epub 2009 Oct 30. [PubMed:19883712 ]
Yuce B, Kemmer M, Qian G, Muller M, Sibaev A, Li Y, Kreis ME, Storr M: Cannabinoid 1 receptors modulate intestinal sensory and motor function in rat. Neurogastroenterol Motil. 2010 Jun;22(6):672-e205. doi: 10.1111/j.1365-2982.2010.01473.x. Epub 2010 Feb 18. [PubMed:20158615 ]
LOTUS database [Link]

Showing NP-Card for (11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene (NP0182319)

MOL for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

3D MOL for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

3D SDF for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

3D-SDF for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

PDB for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

3D PDB for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

SMILES for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

INCHI for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

Structure for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)

3D Structure for NP0182319 ((11r)-2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0⁴,¹²]dodeca-2,4,6,8(12)-tetraene)