NP-MRD: Showing NP-Card for Acutumidine (NP0051337)

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Record Information

Version

2.0

Created at

2022-04-27 22:43:56 UTC

Updated at

2022-04-27 22:43:56 UTC

NP-MRD ID

NP0051337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acutumidine

Description

Acutumidine, also known as dauricumidine, 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. Acutumidine is found in Apis cerana, Hypserpa nitida, Menispermum canadense, Menispermum dauricum and Sinomenium acutum . Acutumidine was first documented in 2002 (PMID: 12377240). Based on a literature review a small amount of articles have been published on Acutumidine (PMID: 30989885) (PMID: 26452875) (PMID: 17723297) (PMID: 16038566).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200432D          

 26 29  0  0  1  0            999 V2000
    1.2675    0.3588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9892    0.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559   -0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674   -0.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214   -1.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9022   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329   -0.2696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1654   -0.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9672   -0.7780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0303    0.0446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0934    0.8672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8952    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    0.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7931   -0.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5560   -0.5838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094    1.8242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0272    1.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650    1.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -1.3125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    0.0446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    0.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4753   -1.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983   -1.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5637   -2.6010    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  1  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 18  1  6  0  0  0
  9 19  1  1  0  0  0
  7 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  6  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
   -5.5889    0.9640   -0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7438    0.3207   -1.4226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773    0.1519   -1.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.5333   -2.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354   -0.5327   -1.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702   -0.8174   -2.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307   -0.1577   -0.1273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3955   -1.4114    0.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4674   -2.5576   -0.1510 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0474   -1.8701    0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592   -0.5680    0.6296 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4250   -0.4285    1.9522 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726    0.7366    2.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    1.1190    1.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927    0.5278    0.3800 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3143    1.5840   -0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    1.6228   -0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502    2.7000   -0.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505    0.3200   -0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5321    0.2589   -1.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7129    0.9282   -1.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.6939   -0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5696   -1.9362   -0.4238 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -2.2297   -0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621    0.6670   -0.0689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2528    0.5877    1.1358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6210    0.9696   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2826    1.9778   -0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6388    0.2792    0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9524   -1.0284   -2.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459   -1.2414    1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2483   -2.4628   -0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2846   -2.4869    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3708   -1.2974    2.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018    1.5659    2.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6015    0.4762    3.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082    2.2188    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2145    0.6927    2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0253    2.6082   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    1.4023   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769    0.4874   -0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5525    0.7183   -2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5969    2.0219   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5742   -1.7869    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412   -3.3487   -0.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -1.9155   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3041    1.7085   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251   -0.3108    1.3731 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 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  1
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 23 24  1  0
  7 25  1  0
 25 26  1  0
 25  3  1  0
 15  7  1  0
 15 11  1  0
 11 22  1  6
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  8 31  1  1
 10 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  6
 26 48  1  0
M  END


  Mrv1652304282200432D          

 26 29  0  0  1  0            999 V2000
    1.2675    0.3588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9892    0.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559   -0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674   -0.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214   -1.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9022   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329   -0.2696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1654   -0.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9672   -0.7780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0303    0.0446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0934    0.8672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8952    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    0.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7931   -0.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5560   -0.5838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094    1.8242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0272    1.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650    1.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -1.3125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    0.0446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    0.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4753   -1.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983   -1.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5637   -2.6010    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  1  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 18  1  6  0  0  0
  9 19  1  1  0  0  0
  7 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  6  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051337

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H22ClNO6/c1-24-10-6-12(22)18(14(10)23)11(19)8-17-15(26-3)13(25-2)9(21)7-16(17,18)4-5-20-17/h6,11,14,20,23H,4-5,7-8H2,1-3H3/t11-,14+,16+,17+,18+/m0/s1

> <INCHI_KEY>
SBALNGLYQFMKPR-NQTWQHAWSA-N

> <FORMULA>
C18H22ClNO6

> <MOLECULAR_WEIGHT>
383.83

> <EXACT_MASS>
383.1135651

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.046069118179815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <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'-azaspiro[cyclopentane-1,7'-tricyclo[4.3.3.0^{1,6}]dodecane]-2',3-diene-2,4'-dione

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
-1.0130491250000007

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.718668009821233

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.17696644092926

> <JCHEM_PKA_STRONGEST_BASIC>
8.606592638933355

> <JCHEM_POLAR_SURFACE_AREA>
94.09000000000002

> <JCHEM_REFRACTIVITY>
95.88639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,1'S,5S,6'S,8'S)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-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       2.366   0.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.713   0.794   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.398  -1.058   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.912  -1.336   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.400  -2.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.684  -2.038   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.368  -0.503   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.175  -1.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.672  -1.452   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.790   0.083   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.908   1.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.404   1.981   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.212   0.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.214  -0.503   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.638  -1.090   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.991   3.405   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.517   3.609   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.735   2.617   0.000  0.00  0.00           O+0
HETATM   19 Cl   UNK     0       4.845  -2.450   0.000  0.00  0.00          Cl+0
HETATM   20  N   UNK     0      -0.056   0.083   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       0.062   1.619   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.559   1.981   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.887  -3.127   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.627  -2.849   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.917  -3.682   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.919  -4.855   0.000  0.00  0.00           C+0
CONECT    1    2    7   10   22                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    1    8   20                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9    1   11   14                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16                                                            
CONECT   18   11                                                            
CONECT   19    9                                                            
CONECT   20    7   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    1                                                       
CONECT   23    6   24                                                       
CONECT   24   23                                                            
CONECT   25    5   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
Dauricumidine	MeSH

Chemical Formula

C₁₈H₂₂ClNO₆

Average Mass

383.8300 Da

Monoisotopic Mass

383.11357 Da

IUPAC Name

(1R,1'S,5S,6'S,8'S)-8'-chloro-5-hydroxy-2',3',4-trimethoxy-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'-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@]34NCC[C@]23CC(=O)C(OC)=C4OC)[C@@H]1O

InChI Identifier

InChI=1S/C18H22ClNO6/c1-24-10-6-12(22)18(14(10)23)11(19)8-17-15(26-3)13(25-2)9(21)7-16(17,18)4-5-20-17/h6,11,14,20,23H,4-5,7-8H2,1-3H3/t11-,14+,16+,17+,18+/m0/s1

InChI Key

SBALNGLYQFMKPR-NQTWQHAWSA-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 canadense	LOTUS Database	35616633
Menispermum dauricum	Plant	KNApSAcK
Sinomenium acutum	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
Dihydroindole
Cyclohexenone
Pyrrolidine
Vinylogous ester
Ketone
Secondary alcohol
Cyclic ketone
Secondary aliphatic amine
Azacycle
Secondary amine
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Alkyl halide
Hydrocarbon derivative
Alcohol
Alkyl chloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:2452 )

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	0.74	ALOGPS
logP	-1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	8.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.89 m³·mol⁻¹	ChemAxon
Polarizability	37.05 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

C00002310

Chemspider ID

391157

KEGG Compound ID

C10565

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442840

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yu BW, Chen JY, Wang YP, Cheng KF, Li XY, Qin GW: Alkaloids from Menispermum dauricum. Phytochemistry. 2002 Oct;61(4):439-42. doi: 10.1016/s0031-9422(02)00162-0. [PubMed:12377240 ]
Shao J, Shi CF, Wei JX, Li YX, Guo XJ: [Chemical constituents from rhizome of Menispermum dauricum and their anti-hypoxic activities]. Zhongguo Zhong Yao Za Zhi. 2019 Feb;44(4):723-729. doi: 10.19540/j.cnki.cjcmm.20181121.003. [PubMed:30989885 ]
Wei J, Fang L, Liang X, Su D, Guo X: A sensitive and selective UPLC-MS/MS method for simultaneous determination of 10 alkaloids from Rhizoma Menispermi in rat plasma and its application to a pharmacokinetic study. Talanta. 2015 Nov 1;144:662-70. doi: 10.1016/j.talanta.2015.07.023. Epub 2015 Jul 8. [PubMed:26452875 ]
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 ]
Bao GH, Qin GW, Wang R, Tang XC: Morphinane alkaloids with cell protective effects from Sinomenium acutum. J Nat Prod. 2005 Jul;68(7):1128-30. doi: 10.1021/np050112+. [PubMed:16038566 ]

Showing NP-Card for Acutumidine (NP0051337)

MOL for NP0051337 (Acutumidine)

3D MOL for NP0051337 (Acutumidine)

3D SDF for NP0051337 (Acutumidine)

3D-SDF for NP0051337 (Acutumidine)

PDB for NP0051337 (Acutumidine)

3D PDB for NP0051337 (Acutumidine)

SMILES for NP0051337 (Acutumidine)

INCHI for NP0051337 (Acutumidine)

Structure for NP0051337 (Acutumidine)

3D Structure for NP0051337 (Acutumidine)