NP-MRD: Showing NP-Card for (1s,1's,5s,6's)-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 (NP0156283)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 13:28:19 UTC

Updated at

2022-09-02 13:28:19 UTC

NP-MRD ID

NP0156283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,1's,5s,6's)-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

Dechloroacutumine 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,5s,6's)-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 Hypserpa nitida and Menispermum dauricum. (1s,1's,5s,6's)-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 2009 (PMID: 19202273). Based on a literature review a small amount of articles have been published on dechloroacutumine (PMID: 26521650) (PMID: 32313070) (PMID: 24032758) (PMID: 23427090).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215282D          

 26 29  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  1  0  0  0  0  0  0  0  0  0
    2.1160    1.7214    0.0000 C   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  2  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  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  1  0  0  0
 23 24  1  0  0  0  0
  7 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  6  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    5.1153    2.1810   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7838    2.5588   -0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624    1.6261    0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    1.9024    1.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593    0.7349    1.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096    0.6666    2.4392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -0.2577    0.3975 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4760   -1.6155    1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124   -1.9016    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6985   -1.1783    0.0644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8517   -0.3708    0.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265   -1.0320    1.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882   -0.4805    1.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    0.9056    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1159    1.5690    0.7467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8082    2.5776    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0065    1.6313   -0.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9296    2.9013   -0.4690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496    0.8491   -1.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655   -0.4109   -0.6180 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8557   -1.3691   -1.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1342   -2.4938   -1.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1912   -2.1921   -0.8418 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -1.8193   -1.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7540    0.1905   -0.1284 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8613   -0.4486    0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    1.8342    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6575    3.1148   -0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2265    1.4733   -1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8183    2.9089    1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121   -1.4772    2.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9922   -2.3846    0.4789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1268   -2.9970    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870   -1.5810    2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -1.3196    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7127   -0.1102    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355    0.2361    2.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    2.2217   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1757    3.4575   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6662    2.8804    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    1.4385   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382    0.5813   -2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8958   -0.8855   -2.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8400   -1.7865   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5035   -2.6905   -2.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3170   -3.4711   -1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -0.7304   -1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3761   -2.2513   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471   -2.2907   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8168    0.0715   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6880   -0.9666    1.2103 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
  9 10  1  0
 10 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  1  0
 20 21  1  6
 20 19  1  0
 19 17  1  0
 17 18  2  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14 11  2  0
 11 12  1  0
 12 13  1  0
  7 25  1  0
 25 26  1  0
 25  3  1  0
 20  7  1  0
 20 10  1  0
 10 11  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 22 45  1  0
 22 46  1  0
 21 43  1  0
 21 44  1  0
 19 41  1  0
 19 42  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 25 50  1  6
 26 51  1  0
M  END


  Mrv1652309022215282D          

 26 29  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  1  0  0  0  0  0  0  0  0  0
    2.1160    1.7214    0.0000 C   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  2  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  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  1  0  0  0
 23 24  1  0  0  0  0
  7 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0156283

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H25NO6/c1-20-8-7-17-10-11(21)14(25-3)16(26-4)19(17,20)6-5-18(17)13(22)9-12(24-2)15(18)23/h9,15,23H,5-8,10H2,1-4H3/t15-,17+,18-,19-/m1/s1

> <INCHI_KEY>
BUBCJFLNVLBOBA-QXCFHYIPSA-N

> <FORMULA>
C19H25NO6

> <MOLECULAR_WEIGHT>
363.41

> <EXACT_MASS>
363.168187529

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.72258566783787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,1'S,5S,6'S)-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

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
-0.6809879706666663

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.99201193639176

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.236552509888401

> <JCHEM_PKA_STRONGEST_BASIC>
7.111055269463771

> <JCHEM_POLAR_SURFACE_AREA>
85.30000000000001

> <JCHEM_REFRACTIVITY>
96.65819999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,1'S,5S,6'S)-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                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-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  C   UNK     0       2.465   3.623   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.617   2.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.051   2.320   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.866   3.311   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.304   4.745   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.468   0.673   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.991   0.443   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.553  -0.990   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.493  -0.530   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.069  -1.964   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.442  -0.213   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.578   1.133   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.730  -0.152   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.245   0.257   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       0.176   1.795   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -1.309   2.205   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.461   2.216   0.000  0.00  0.00           C+0
HETATM   26  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   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20   25                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20   23                                             
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    7   10   21                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   10   24                                                  
CONECT   24   23                                                            
CONECT   25    7    3   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₅NO₆

Average Mass

363.4100 Da

Monoisotopic Mass

363.16819 Da

IUPAC Name

(1S,1'S,5S,6'S)-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,5S,6'S)-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(CC[C@]34N(C)CC[C@]23CC(=O)C(OC)=C4OC)[C@@H]1O

InChI Identifier

InChI=1S/C19H25NO6/c1-20-8-7-17-10-11(21)14(25-3)16(26-4)19(17,20)6-5-18(17)13(22)9-12(24-2)15(18)23/h9,15,23H,5-8,10H2,1-4H3/t15-,17+,18-,19-/m1/s1

InChI Key

BUBCJFLNVLBOBA-QXCFHYIPSA-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
Hypserpa nitida	LOTUS Database	35616633
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
Ketone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Azacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Carbonyl group
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	0.42	ALOGPS
logP	-0.68	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	7.11	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.66 m³·mol⁻¹	ChemAxon
Polarizability	36.72 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

C00027340

Chemspider ID

4475991

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317068

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hori R, Sugimoto G, Matsui M, Yamauchi Y, Takikawa H, Sugimoto Y: Conversion of dechlorodauricumine into miharumine by a cell-free preparation from cultured roots of Menispermum dauricum. Biosci Biotechnol Biochem. 2009 Feb;73(2):440-2. doi: 10.1271/bbb.80596. Epub 2009 Feb 7. [PubMed:19202273 ]
King SM, Herzon SB: The Hasubanan and Acutumine Alkaloids. Alkaloids Chem Biol. 2014;73:161-222. doi: 10.1016/B978-0-12-411565-1.00003-2. Epub 2013 Dec 25. [PubMed:26521650 ]
Kim CY, Mitchell AJ, Glinkerman CM, Li FS, Pluskal T, Weng JK: The chloroalkaloid (-)-acutumine is biosynthesized via a Fe(II)- and 2-oxoglutarate-dependent halogenase in Menispermaceae plants. Nat Commun. 2020 Apr 20;11(1):1867. doi: 10.1038/s41467-020-15777-w. [PubMed:32313070 ]
Calandra NA, King SM, Herzon SB: Development of enantioselective synthetic routes to the hasubanan and acutumine alkaloids. J Org Chem. 2013 Oct 18;78(20):10031-57. doi: 10.1021/jo401889b. Epub 2013 Sep 27. [PubMed:24032758 ]
King SM, Calandra NA, Herzon SB: Total syntheses of (-)-acutumine and (-)-dechloroacutumine. Angew Chem Int Ed Engl. 2013 Mar 25;52(13):3642-5. doi: 10.1002/anie.201210076. Epub 2013 Feb 20. [PubMed:23427090 ]
LOTUS database [Link]

Showing NP-Card for (1s,1's,5s,6's)-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 (NP0156283)

MOL for NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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 NP0156283 ((1s,1's,5s,6's)-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)