NP-MRD: Showing NP-Card for Acutumine (NP0067922)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 12:45:52 UTC

Updated at

2022-04-28 12:45:52 UTC

NP-MRD ID

NP0067922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acutumine

Description

Acutumine, also known as dauricumine, 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. Acutumine is found in Apis cerana, Hypserpa nitida, Menispermum dauricum, Menispermum dauricum DC. and Sinomenium acutum Rehder & Wilson . Acutumine was first documented in 2019 (PMID: 31022719). Based on a literature review a small amount of articles have been published on Acutumine (PMID: 33523640) (PMID: 32843671) (PMID: 35112449) (PMID: 32313070).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214452D          

 27 30  0  0  1  0            999 V2000
    1.2685    0.3733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1318   -0.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9916   -0.7487    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3007   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7470   -0.2660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0400   -1.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8544   -1.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3758   -0.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1902   -0.6616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828    0.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -1.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5186   -1.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958   -1.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221    0.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239    0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8215    1.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -0.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309   -1.2701    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    0.8987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8813    1.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282    0.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068   -0.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   -0.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1796    1.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9949    2.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443    1.4201    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  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  6  0  0  0
 15 18  1  0  0  0  0
  3 19  1  1  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  1  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 27  1  6  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -5.1137    1.4169    1.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1601    0.3738    1.6993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1044    0.3641    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4593    1.4232    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967    1.0433   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    1.8601   -1.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2718   -0.4105   -0.4752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0926   -0.9477   -1.8688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0262    0.1050   -2.9745 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3963   -0.7573   -2.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501   -0.7524   -0.7325 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8440    0.4859   -0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    0.9181   -1.7036 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542    2.1762   -2.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    1.2012    0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6686    2.3600    0.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351    2.5310    1.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1522    0.7158    1.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4242    1.1952    2.7819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960   -0.2910    1.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551   -0.9271    0.2263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1882   -2.4399    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770   -3.0017   -0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8689   -1.9441   -0.6457 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414   -2.0155    0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5314   -0.8829    0.1980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4673   -1.4077   -0.6533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9119    1.3124    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6185    1.3518    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6526    2.4224    1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6656    2.4502    0.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4353   -1.9683   -2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5085    0.2013   -2.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8144   -1.5397   -2.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7051    3.0255   -1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1861    2.2718   -3.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4691    2.3945   -2.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5195    1.7643    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1883    3.5239    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3925    2.5085    2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8648    0.2011    1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2663   -1.0435    2.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793   -2.8073    1.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1591   -2.7885   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -3.2925   -1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612   -3.8760   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -2.8294    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0478   -2.3704    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299   -1.1087    0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856   -1.5343    1.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0095   -0.6611   -1.0293 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  6
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 24  1  6
 24 25  1  0
 24 23  1  0
 23 22  1  0
 21 22  1  1
 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  0
  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  1
 27 51  1  0
M  END


  Mrv1652304282214452D          

 27 30  0  0  1  0            999 V2000
    1.2685    0.3733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1318   -0.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9916   -0.7487    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3007   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7470   -0.2660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0400   -1.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8544   -1.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3758   -0.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1902   -0.6616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828    0.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -1.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5186   -1.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958   -1.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221    0.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239    0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8215    1.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -0.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309   -1.2701    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    0.8987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8813    1.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282    0.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068   -0.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   -0.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1796    1.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9949    2.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443    1.4201    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  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  6  0  0  0
 15 18  1  0  0  0  0
  3 19  1  1  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  1  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0067922

> <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-FMAJMWNWSA-N

> <FORMULA>
C19H24ClNO6

> <MOLECULAR_WEIGHT>
397.85

> <EXACT_MASS>
397.1292152

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.6722443153895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,1'S,5S,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

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
-0.6300011876666667

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.7418582896567

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.176873702161238

> <JCHEM_PKA_STRONGEST_BASIC>
6.677606810134289

> <JCHEM_POLAR_SURFACE_AREA>
85.30000000000001

> <JCHEM_REFRACTIVITY>
101.1811

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,1'S,5S,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                                 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       2.368   0.697   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.979  -0.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.718  -1.398   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.428  -1.703   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.394  -0.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.941  -1.936   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.462  -2.182   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.435  -0.989   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.955  -1.235   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.888   0.451   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.008  -3.622   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.035  -4.815   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.968  -3.130   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.552  -2.883   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.041   0.060   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.045   1.598   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.534   1.991   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.336  -0.774   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       4.911  -2.371   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       3.889   1.678   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.378   2.071   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.213   0.777   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.239  -0.417   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.675  -0.974   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.935   3.507   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.457   3.742   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.696   2.651   0.000  0.00  0.00           O+0
CONECT    1    2    5   10   17                                             
CONECT    2    1    3   20   23                                             
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    6   15                                             
CONECT    6    5    7   13                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    1                                                       
CONECT   11    7   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14                                                       
CONECT   14   13                                                            
CONECT   15    5   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    1                                                       
CONECT   18   15                                                            
CONECT   19    3                                                            
CONECT   20    2   21   27                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22    2   24                                                  
CONECT   24   23                                                            
CONECT   25   21   26                                                       
CONECT   26   25                                                            
CONECT   27   20                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Dauricumine	MeSH

Chemical Formula

C₁₉H₂₄ClNO₆

Average Mass

397.8500 Da

Monoisotopic Mass

397.12922 Da

IUPAC Name

(1R,1'S,5S,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

(1R,1'S,5S,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-FMAJMWNWSA-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
Apis cerana	LOTUS Database	35616633
Hypserpa nitida	LOTUS Database	35616633
Menispermum dauricum	LOTUS Database	35616633
Menispermum dauricum DC.	Plant	KNApSAcK
Sinomenium acutum Rehder & Wilson	Plant	KNApSAcK

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
Alkyl chloride
Alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic oxide
Alkyl halide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:80789 )

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	1.12	ALOGPS
logP	-0.63	ChemAxon
logS	-2.3	ALOGPS
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	38.67 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

C00025765

Chemspider ID

8376347

KEGG Compound ID

C16910

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10200848

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hsu IT, Tomanik M, Herzon SB: Metric-Based Analysis of Convergence in Complex Molecule Synthesis. Acc Chem Res. 2021 Feb 16;54(4):903-916. doi: 10.1021/acs.accounts.0c00817. Epub 2021 Feb 1. [PubMed:33523640 ]
Hu P, Chi HM, DeBacker KC, Gong X, Keim JH, Hsu IT, Snyder SA: Quaternary-centre-guided synthesis of complex polycyclic terpenes. Nature. 2019 May;569(7758):703-707. doi: 10.1038/s41586-019-1179-2. Epub 2019 Apr 25. [PubMed:31022719 ]
Huang YF, He F, Wang CJ, Xie Y, Zhang YY, Sang Z, Qiu P, Luo P, Xiao SY, Li J, Wu FC, Liu L, Zhou H: Discovery of chemical markers for improving the quality and safety control of Sinomenium acutum stem by the simultaneous determination of multiple alkaloids using UHPLC-QQQ-MS/MS. Sci Rep. 2020 Aug 25;10(1):14182. doi: 10.1038/s41598-020-71133-4. [PubMed:32843671 ]
Grunenfelder DC, Navarro R, Wang H, Fastuca NJ, Butler JR, Reisman SE: Enantioselective Synthesis of (-)-10-Hydroxyacutuminine. Angew Chem Int Ed Engl. 2022 Apr 11;61(16):e202117480. doi: 10.1002/anie.202117480. Epub 2022 Feb 23. [PubMed:35112449 ]
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 ]

Showing NP-Card for Acutumine (NP0067922)

MOL for NP0067922 (Acutumine)

3D MOL for NP0067922 (Acutumine)

3D SDF for NP0067922 (Acutumine)

3D-SDF for NP0067922 (Acutumine)

PDB for NP0067922 (Acutumine)

3D PDB for NP0067922 (Acutumine)

SMILES for NP0067922 (Acutumine)

INCHI for NP0067922 (Acutumine)

Structure for NP0067922 (Acutumine)

3D Structure for NP0067922 (Acutumine)