NP-MRD: Showing NP-Card for meso-Chimonanthine (NP0068778)

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Record Information

Version

2.0

Created at

2022-04-28 14:02:10 UTC

Updated at

2022-04-28 14:02:10 UTC

NP-MRD ID

NP0068778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

meso-Chimonanthine

Description

Meso-chimonanthine belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. meso-Chimonanthine is found in Chimonanthus fragrans, Chimonanthus praecox, Psychotria forsteriana, Psychotria lyciiflora and Psychotria muscosa. meso-Chimonanthine was first documented in 2002 (PMID: 12148978). Based on a literature review a small amount of articles have been published on meso-chimonanthine (PMID: 23203932) (PMID: 28144659) (PMID: 24409339) (PMID: 17082868).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216022D          

 26 31  0  0  1  0            999 V2000
   -0.2529   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -1.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -1.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540   -0.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111    0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914    0.4333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -0.0647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1788   -0.8441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8366   -1.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -0.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -0.0809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720    0.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085   -1.6236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7333   -1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1008   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -2.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -2.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959   -2.9010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -2.4030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8133   -2.3868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -1.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507   -1.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982   -3.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  4  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
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  1  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END

     RDKit          3D

 52 57  0  0  0  0  0  0  0  0999 V2000
    3.5017   -1.2933    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2392   -1.9326    0.7278 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -1.7653    1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -0.7032    1.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -0.3033    0.3143 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7401   -0.0552   -0.3415 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7178    0.3598   -1.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5515    1.6145   -1.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4186    1.5477   -0.7394 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8669    2.8941   -0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.1277    0.2983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1784    0.4779    1.3500 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -0.8015    0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6309   -1.6570    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8310   -2.8500    0.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9882   -3.1775   -0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641   -2.3215   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432   -1.1345   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5679    0.7885    0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427    2.0173    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614    2.8250    0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    2.3891   -0.8552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250    1.1727   -1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3949    0.3839   -0.9667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0084   -0.9161   -1.4081 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -1.4926   -0.2614 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0852   -1.3255   -0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -0.3008    1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1275   -1.9019    1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0926   -2.7642    2.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -1.4827    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803   -1.1734    2.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757    0.1770    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752    0.4942   -2.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354   -0.4043   -2.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888    1.6611   -2.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9353    2.5343   -1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9639    2.9852   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372    3.1764    0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978    3.6518   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655    1.9796    0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3945    0.7954    2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3018   -1.4062    2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6661   -3.5089    0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1187   -4.1009   -1.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107   -2.6194   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    2.3620    1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0554    3.8070    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525    3.0119   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0653    0.8773   -2.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1606   -1.3812   -2.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804   -2.3385   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
  5 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
  5  6  1  0
  6  7  1  6
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 26  2  1  0
 19 24  1  0
 11  6  1  0
 18 13  1  0
 19  5  1  0
 18  6  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
 26 52  1  6
 25 51  1  0
 23 50  1  0
 22 49  1  0
 21 48  1  0
 20 47  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  1
 12 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
M  END


  Mrv1652304282216022D          

 26 31  0  0  1  0            999 V2000
   -0.2529   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -1.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -1.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540   -0.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111    0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914    0.4333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -0.0647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1788   -0.8441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8366   -1.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -0.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -0.0809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720    0.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085   -1.6236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7333   -1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1008   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -2.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -2.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959   -2.9010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -2.4030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8133   -2.3868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -1.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507   -1.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982   -3.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  4  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
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  1  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC[C@@]2([C@H]1NC1=CC=CC=C21)[C@]12CCN(C)[C@H]1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N4/c1-25-13-11-21(15-7-3-5-9-17(15)23-19(21)25)22-12-14-26(2)20(22)24-18-10-6-4-8-16(18)22/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20+,21+,22-

> <INCHI_KEY>
HOYXPMHLHJOGHD-ZDNVTZCJSA-N

> <FORMULA>
C22H26N4

> <MOLECULAR_WEIGHT>
346.478

> <EXACT_MASS>
346.215746853

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.52387936450525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,8aR)-3a-[(3aS,8aS)-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
2.8468884386666664

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.861890429830527

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.861890429830527

> <JCHEM_PKA_STRONGEST_BASIC>
7.580988007057347

> <JCHEM_POLAR_SURFACE_AREA>
30.54

> <JCHEM_REFRACTIVITY>
107.9082

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,8aR)-3a-[(3aS,8aS)-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indole

> <JCHEM_VEBER_RULE>
1

$$$$

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      -0.472  -0.846   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.025  -2.319   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.660  -2.554   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.527  -1.545   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.081  -0.072   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.581   0.278   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.344   0.809   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.572  -0.121   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.067  -1.576   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.295  -2.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.743  -1.510   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.112  -0.151   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       7.041   1.077   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.562  -3.031   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.102  -3.061   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.155  -1.937   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.655  -2.287   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.102  -3.761   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.049  -4.885   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.549  -4.535   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       4.286  -5.415   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.058  -4.486   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.518  -4.455   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       1.071  -2.982   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.335  -2.101   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.557  -5.829   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   14                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12                                                            
CONECT   14    9   15   22   25                                             
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   14   23                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   14                                                       
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆N₄

Average Mass

346.4780 Da

Monoisotopic Mass

346.21575 Da

IUPAC Name

(3aR,8aR)-3a-[(3aS,8aS)-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole

Traditional Name

(3aR,8aR)-3a-[(3aS,8aS)-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl]-1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indole

CAS Registry Number

Not Available

SMILES

CN1CC[C@@]2([C@H]1NC1=CC=CC=C21)[C@]12CCN(C)[C@H]1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C22H26N4/c1-25-13-11-21(15-7-3-5-9-17(15)23-19(21)25)22-12-14-26(2)20(22)24-18-10-6-4-8-16(18)22/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20+,21+,22-

InChI Key

HOYXPMHLHJOGHD-ZDNVTZCJSA-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
Chimonanthus fragrans	Plant	KNApSAcK
Chimonanthus praecox	LOTUS Database	35616633
Psychotria forsteriana	Plant	KNApSAcK
Psychotria lyciiflora	Plant	KNApSAcK
Psychotria muscosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Indole
Dihydroindole
Secondary aliphatic/aromatic amine
Benzenoid
N-alkylpyrrolidine
Pyrrole
Pyrrolidine
Azacycle
Secondary amine
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chimonanthine (CHEBI:38971 )

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	3.51	ALOGPS
logP	2.85	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.86	ChemAxon
pKa (Strongest Basic)	7.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	30.54 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	107.91 m³·mol⁻¹	ChemAxon
Polarizability	38.52 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00026840

Chemspider ID

9902430

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11727714

PDB ID

Not Available

ChEBI ID

38971

Good Scents ID

Not Available

References

General References

Snell RH, Durbin MJ, Woodward RL, Willis MC: Catalytic enantioselective desymmetrisation as a tool for the synthesis of hodgkinsine and hodgkinsine B. Chemistry. 2012 Dec 21;18(52):16754-64. doi: 10.1002/chem.201203150. Epub 2012 Nov 30. [PubMed:23203932 ]
Kumar N, Das MK, Ghosh S, Bisai A: Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids. Chem Commun (Camb). 2017 Feb 9;53(13):2170-2173. doi: 10.1039/c6cc10228j. [PubMed:28144659 ]
Lathrop SP, Movassaghi M: Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids. Chem Sci. 2014 Jan 1;5(1). doi: 10.1039/C3SC52451E. [PubMed:24409339 ]
Menozzi C, Dalko PI, Cossy J: Concise synthesis of the (+/-)-Nb-desmethyl-meso-chimonanthine. Chem Commun (Camb). 2006 Nov 28;(44):4638-40. doi: 10.1039/b610497e. Epub 2006 Oct 3. [PubMed:17082868 ]
Lebsack AD, Link JT, Overman LE, Stearns BA: Enantioselective total synthesis of quadrigemine C and psycholeine. J Am Chem Soc. 2002 Aug 7;124(31):9008-9. doi: 10.1021/ja0267425. [PubMed:12148978 ]

Showing NP-Card for meso-Chimonanthine (NP0068778)

MOL for NP0068778 (meso-Chimonanthine)

3D MOL for NP0068778 (meso-Chimonanthine)

3D SDF for NP0068778 (meso-Chimonanthine)

3D-SDF for NP0068778 (meso-Chimonanthine)

PDB for NP0068778 (meso-Chimonanthine)

3D PDB for NP0068778 (meso-Chimonanthine)

SMILES for NP0068778 (meso-Chimonanthine)

INCHI for NP0068778 (meso-Chimonanthine)

Structure for NP0068778 (meso-Chimonanthine)

3D Structure for NP0068778 (meso-Chimonanthine)