NP-MRD: Showing NP-Card for (-)-8-Oxotetrahydrothalifendine (NP0067784)

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Record Information

Version

2.0

Created at

2022-04-28 12:38:01 UTC

Updated at

2022-04-28 12:38:01 UTC

NP-MRD ID

NP0067784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-8-Oxotetrahydrothalifendine

Description

8-Oxotetrahydrothalifendine, also known as 8-otht CPD, belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. (-)-8-Oxotetrahydrothalifendine is found in Arcangelisia gusanlung H.S.Lo, Coscinium fenestratum (Gaertn.) Colebr. and Hydrastis canadensis . (-)-8-Oxotetrahydrothalifendine was first documented in 1998 (PMID: 9784149). Based on a literature review very few articles have been published on 8-Oxotetrahydrothalifendine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214382D          

 25 29  0  0  1  0            999 V2000
    6.6024    0.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0040    1.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807    2.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7558    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775    0.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293    1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060    2.2060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5075    2.9266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3324    2.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7340    3.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0842    3.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577    2.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2811    2.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795    1.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    1.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312    2.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328    2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270    1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532    1.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.8388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9823    2.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5589    3.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8289    1.5480    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  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 25  1  0  0  0  0
M  END

     RDKit          3D

 42 46  0  0  0  0  0  0  0  0999 V2000
   -5.0648   -1.3069    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4321   -0.6182   -0.7714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6568    0.5076   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2478    1.7458   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5915    1.9586   -0.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4166    2.8249   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706    2.6549   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847    1.3896   -0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2954    0.3170   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -1.0226   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4046   -2.0397   -0.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2903   -1.1072   -0.1586 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -2.2836    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2744   -1.8427    1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271   -1.0901    0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6485   -1.2657    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6383   -0.5903    0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2443    0.2791   -0.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8862    0.4572   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193   -0.2145   -0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996    0.0170   -0.5740 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0423    1.2400    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135    0.8062   -1.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125    0.6484   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0300   -0.5910    0.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557   -1.1437    1.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0679   -0.8930    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1124   -2.3880    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2233    1.1634   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866    3.8420   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4069    3.4980   -0.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8717   -2.7897   -0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4649   -2.9731    0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484   -1.1413    2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087   -2.6875    2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -1.9586    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    1.1564   -1.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879    0.2220   -1.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    2.1740   -0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233    1.1009    1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3821    1.4209    0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4191    0.5232   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9  8  1  0
  8 22  1  0
 22 21  1  0
 21 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 20  2  0
 20 19  1  0
 19 18  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 25 17  1  0
 17 16  2  0
 12 10  1  0
 10 11  2  0
  8  7  2  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
  4  3  1  0
 10  9  1  0
 20 21  1  0
 17 18  1  0
 16 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 22 39  1  0
 22 40  1  0
 21 38  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 19 37  1  0
 24 41  1  0
 24 42  1  0
 16 36  1  0
  7 31  1  0
  6 30  1  0
  5 29  1  0
M  END


  Mrv1652304282214382D          

 25 29  0  0  1  0            999 V2000
    6.6024    0.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0040    1.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807    2.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7558    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775    0.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293    1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060    2.2060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5075    2.9266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3324    2.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7340    3.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0842    3.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577    2.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2811    2.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795    1.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    1.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312    2.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328    2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270    1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532    1.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.8388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9823    2.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5589    3.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8289    1.5480    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  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(C[C@@H]3N(CCC4=C3C=C3OCOC3=C4)C2=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO5/c1-23-18-14(21)3-2-11-6-13-12-8-16-15(24-9-25-16)7-10(12)4-5-20(13)19(22)17(11)18/h2-3,7-8,13,21H,4-6,9H2,1H3/t13-/m0/s1

> <INCHI_KEY>
XSILRSUKELEZIF-ZDUSSCGKSA-N

> <FORMULA>
C19H17NO5

> <MOLECULAR_WEIGHT>
339.347

> <EXACT_MASS>
339.110672651

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.43981589845832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-17-hydroxy-16-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-2(10),3,8,15,17,19-hexaen-14-one

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
2.2972523220000003

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.346918636717165

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6365615661120683

> <JCHEM_POLAR_SURFACE_AREA>
68.23

> <JCHEM_REFRACTIVITY>
90.04280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-17-hydroxy-16-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-2(10),3,8,15,17,19-hexaen-14-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      12.324   1.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.074   2.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.284   4.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.744   4.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.994   2.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.785   1.498   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.455   2.796   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.664   4.118   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.414   5.463   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.954   5.486   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.704   6.832   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.624   6.785   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.084   6.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.334   5.416   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.125   4.094   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.375   2.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.835   2.726   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.045   4.048   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.795   5.393   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.544   3.704   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.406   2.171   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.822   1.566   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.034   5.533   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.243   6.855   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.614   2.890   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23    3   24                                                       
CONECT   24   23                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
8-OTHT CPD	MeSH

Chemical Formula

C₁₉H₁₇NO₅

Average Mass

339.3470 Da

Monoisotopic Mass

339.11067 Da

IUPAC Name

(1S)-17-hydroxy-16-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-2(10),3,8,15,17,19-hexaen-14-one

Traditional Name

(1S)-17-hydroxy-16-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-2(10),3,8,15,17,19-hexaen-14-one

CAS Registry Number

Not Available

SMILES

COC1=C2C(C[C@@H]3N(CCC4=C3C=C3OCOC3=C4)C2=O)=CC=C1O

InChI Identifier

InChI=1S/C19H17NO5/c1-23-18-14(21)3-2-11-6-13-12-8-16-15(24-9-25-16)7-10(12)4-5-20(13)19(22)17(11)18/h2-3,7-8,13,21H,4-6,9H2,1H3/t13-/m0/s1

InChI Key

XSILRSUKELEZIF-ZDUSSCGKSA-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
Arcangelisia gusanlung	Plant	KNApSAcK
Coscinium fenestratum	Plant	KNApSAcK
Hydrastis canadensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroprotoberberine skeleton
Isoquinolone
Tetrahydroisoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Acetal
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
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	2.12	ALOGPS
logP	2.3	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.35	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.04 m³·mol⁻¹	ChemAxon
Polarizability	35.44 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

C00025599

Chemspider ID

21174903

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100916731

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gentry EJ, Jampani HB, Keshavarz-Shokri A, Morton MD, Velde DV, Telikepalli H, Mitscher LA, Shawar R, Humble D, Baker W: Antitubercular natural products: berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2. J Nat Prod. 1998 Oct;61(10):1187-93. doi: 10.1021/np9701889. [PubMed:9784149 ]

Showing NP-Card for (-)-8-Oxotetrahydrothalifendine (NP0067784)

MOL for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

3D MOL for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

3D SDF for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

3D-SDF for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

PDB for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

3D PDB for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

SMILES for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

INCHI for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

Structure for NP0067784 ((-)-8-Oxotetrahydrothalifendine)

3D Structure for NP0067784 ((-)-8-Oxotetrahydrothalifendine)