NP-MRD: Showing NP-Card for (1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione (NP0216337)

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Record Information

Version

2.0

Created at

2022-09-05 16:15:29 UTC

Updated at

2022-09-05 16:15:30 UTC

NP-MRD ID

NP0216337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione

Description

Dauricumine, also known as acutumine, belongs to the class of organic compounds known as acutumine and related alkaloids. These are alkaloids with a structure based on the tricyclic acutumine skeleton, which contains an indoline moiety and two cyclopentene rings. (1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione is found in Menispermum dauricum. (1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione was first documented in 2006 (PMID: 16964757). Based on a literature review a small amount of articles have been published on dauricumine (PMID: 17723297) (PMID: 26992921).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218152D          

 27 30  0  0  1  0            999 V2000
    4.7086   -0.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642    0.5797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401    0.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858   -0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905    0.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5456   -0.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    0.8972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1160    1.7214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7608    2.2359    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    1.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    1.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0272    1.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640    1.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628    2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506    0.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663    0.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3675   -0.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640   -0.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.0522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809    0.6071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9266   -0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313    0.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940    0.9619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    1.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255    1.1873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1448    1.9827    0.0000 O   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
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 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
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 24  1  1  0  0  0
 24 25  1  0  0  0  0
  7 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    5.8618    0.8008   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0554   -0.2824   -0.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7871   -0.4130   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4563   -0.8285    1.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066   -0.8210    1.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840   -1.3570    2.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -0.1172    0.2189 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9850    1.2491    0.6909 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6656    2.3511   -0.6470 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2977    0.8888    1.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8919   -0.2825    0.6454 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1636    0.1680    0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621    0.2772    0.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9153    1.4791    1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3908    0.4900   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6499    0.9068   -1.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966    1.5648   -2.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2601    0.3803   -2.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005    0.9842   -3.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -0.4093   -1.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -0.7170   -0.3193 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2727   -2.2434   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9990   -2.5375    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0283   -1.4368    1.4976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756   -1.3958    2.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -0.0700   -0.7768 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7142    1.2017   -1.3472 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0321    0.7252    0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3405    1.7309   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8327    0.6973   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2113   -1.1398    1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7143    1.7275    1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9410    1.7670    1.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394    0.5201    2.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450    1.2366    1.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719    2.2082    1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898    1.9604    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5917    0.9353   -3.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3803    2.5618   -2.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9717    1.7823   -2.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    0.1474   -2.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233   -1.3385   -2.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2280   -2.7382   -1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -2.5165    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8426   -2.5497   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142   -3.5239    1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8081   -2.0742    3.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563   -1.7611    2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1253   -0.3798    2.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547   -0.8669   -1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2246    1.0580   -2.1946 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
  7  5  1  1
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 24  1  0
 24 25  1  0
 24 23  1  0
 23 22  1  0
 21 22  1  6
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 15 12  2  0
 12 13  1  0
 13 14  1  0
  7 26  1  0
 26 27  1  0
 26  3  1  0
 21  7  1  0
 21 11  1  0
 11 12  1  6
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  8 32  1  1
 10 33  1  0
 10 34  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 23 45  1  0
 23 46  1  0
 22 43  1  0
 22 44  1  0
 20 41  1  0
 20 42  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 26 50  1  6
 27 51  1  0
M  END


  Mrv1652309052218152D          

 27 30  0  0  1  0            999 V2000
    4.7086   -0.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642    0.5797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401    0.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858   -0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905    0.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5456   -0.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    0.8972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1160    1.7214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7608    2.2359    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    1.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    1.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0272    1.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640    1.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628    2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506    0.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663    0.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3675   -0.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640   -0.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.0522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809    0.6071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9266   -0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313    0.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940    0.9619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    1.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255    1.1873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1448    1.9827    0.0000 O   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
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 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
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 24  1  1  0  0  0
 24 25  1  0  0  0  0
  7 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0216337

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)[C@@]2([C@@H](Cl)C[C@]34N(C)CC[C@]23CC(=O)C(OC)=C4OC)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24ClNO6/c1-21-6-5-17-8-10(22)14(26-3)16(27-4)18(17,21)9-12(20)19(17)13(23)7-11(25-2)15(19)24/h7,12,15,24H,5-6,8-9H2,1-4H3/t12-,15-,17+,18+,19-/m0/s1

> <INCHI_KEY>
FSXRARBVZZKCGJ-ONBYKIOGSA-N

> <FORMULA>
C19H24ClNO6

> <MOLECULAR_WEIGHT>
397.85

> <EXACT_MASS>
397.1292152

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.480449163076045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,1'S,5R,6'S,8'S)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0^{1,6}]dodecane]-2',3-diene-2,4'-dione

> <JCHEM_LOGP>
-0.6300011876666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.741858289656694

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.176873702161238

> <JCHEM_PKA_STRONGEST_BASIC>
6.677606810134286

> <JCHEM_POLAR_SURFACE_AREA>
85.30000000000001

> <JCHEM_REFRACTIVITY>
101.18109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,1'S,5R,6'S,8'S)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0^{1,6}]dodecane]-2',3-diene-2,4'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       8.789  -0.215   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.960   1.082   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.421   1.013   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.573  -0.273   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.089   0.136   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.885  -0.824   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.019   1.675   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.950   3.213   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       5.154   4.174   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       2.465   3.623   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.617   2.337   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.051   2.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.866   3.311   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.304   4.745   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.468   0.673   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.991   0.443   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.553  -0.990   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.493  -0.530   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.069  -1.964   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.442  -0.213   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.578   1.133   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.730  -0.152   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.245   0.257   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.176   1.795   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -1.309   2.205   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.461   2.216   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.870   3.701   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   21   26                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   21   24                                             
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    7   11   22                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   11   25                                                  
CONECT   25   24                                                            
CONECT   26    7    3   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Acutumine	MeSH

Chemical Formula

C₁₉H₂₄ClNO₆

Average Mass

397.8500 Da

Monoisotopic Mass

397.12922 Da

IUPAC Name

(1S,1'S,5R,6'S,8'S)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0^{1,6}]dodecane]-2',3-diene-2,4'-dione

Traditional Name

(1S,1'S,5R,6'S,8'S)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0^{1,6}]dodecane]-2',3-diene-2,4'-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)[C@@]2([C@@H](Cl)C[C@]34N(C)CC[C@]23CC(=O)C(OC)=C4OC)[C@H]1O

InChI Identifier

InChI=1S/C19H24ClNO6/c1-21-6-5-17-8-10(22)14(26-3)16(27-4)18(17,21)9-12(20)19(17)13(23)7-11(25-2)15(19)24/h7,12,15,24H,5-6,8-9H2,1-4H3/t12-,15-,17+,18+,19-/m0/s1

InChI Key

FSXRARBVZZKCGJ-ONBYKIOGSA-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

Species Name	Source	Reference
Menispermum dauricum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acutumine and related alkaloids. These are alkaloids with a structure based on the tricyclic acutumine skeleton, which contains an indoline moiety and two cyclopentene rings.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Acutumine and related alkaloids

Sub Class

Not Available

Direct Parent

Acutumine and related alkaloids

Alternative Parents

Substituents

Acutumine skeketon
Indole or derivatives
Cyclohexenone
N-alkylpyrrolidine
Pyrrolidine
Vinylogous ester
Cyclic ketone
Ketone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Amine
Alkyl halide
Alkyl chloride
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.63	ChemAxon
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	6.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.18 m³·mol⁻¹	ChemAxon
Polarizability	38.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00027335

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

101106309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cheng P, Ma YB, Yao SY, Zhang Q, Wang EJ, Yan MH, Zhang XM, Zhang FX, Chen JJ: Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida. Bioorg Med Chem Lett. 2007 Oct 1;17(19):5316-20. doi: 10.1016/j.bmcl.2007.08.027. Epub 2007 Aug 16. [PubMed:17723297 ]
Lee JY, Kim KJ, Kim J, Choi SU, Kim SH, Ryu SY: Anti-osteoclastogenic effects of isoquinoline alkaloids from the rhizome extract of Sinomenium acutum. Arch Pharm Res. 2016 May;39(5):713-20. doi: 10.1007/s12272-016-0734-8. Epub 2016 Mar 18. [PubMed:26992921 ]
Min YD, Choi SU, Lee KR: Aporphine alkaloids and their reversal activity of multidrug resistance (MDR) from the stems and rhizomes of Sinomenium acutum. Arch Pharm Res. 2006 Aug;29(8):627-32. doi: 10.1007/BF02968246. [PubMed:16964757 ]
LOTUS database [Link]

Showing NP-Card for (1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione (NP0216337)

MOL for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

3D MOL for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

3D SDF for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

3D-SDF for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

PDB for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

3D PDB for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

SMILES for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

INCHI for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

Structure for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)

3D Structure for NP0216337 ((1s,1's,5r,6's,8's)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-10'-methyl-10'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0¹,⁶]dodecane]-2',3-diene-2,4'-dione)