NP-MRD: Showing NP-Card for Calycanthidine (NP0050846)

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Record Information

Version

2.0

Created at

2022-04-27 22:15:19 UTC

Updated at

2022-04-27 22:15:19 UTC

NP-MRD ID

NP0050846

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calycanthidine

Description

(+)-Calycanthidine 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. Calycanthidine is found in Calycanthus floridus and Chimonanthus praecox. Calycanthidine was first documented in 2008 (PMID: 18973012). Based on a literature review a small amount of articles have been published on (+)-calycanthidine (PMID: 24409339) (PMID: 29262505) (PMID: 24668298).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200152D          

 27 32  0  0  1  0            999 V2000
    1.8020   -1.3501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0724   -0.5706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8972   -0.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366   -1.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598   -1.8480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435   -2.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401   -1.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5041   -0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647   -0.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3446    0.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4146   -0.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212   -0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772   -1.3338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -1.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.2088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6131    0.9883    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9554    1.4863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    0.9720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9576    1.6904    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
  4  5  1  0  0  0  0
  1  5  1  6  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
   -1.6326   -3.0701    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796   -1.8175    0.4270 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837   -1.4123    1.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116    0.0002    1.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4564    0.3571    0.1254 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9180    0.2166   -0.3139 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3367    0.6201   -1.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8512   -0.4177   -2.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -1.6010   -1.7563 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214   -2.6499   -2.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -1.2705   -0.4955 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7797   -1.0787   -0.5662 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817   -0.0739    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2549    0.1645    1.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    1.2114    1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1972    2.0031    2.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486    1.7519    1.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9766    0.7350    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1883    1.5774   -0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580    2.9245   -0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478    3.8583   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1898    3.5492   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452    2.2354   -0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317    1.2726    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242   -0.1386    0.2098 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8421   -0.8136    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -0.6834   -0.3529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7686   -3.7169   -0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0280   -3.6052    0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3910   -3.1761   -0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159   -1.4948    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522   -2.0956    2.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4515    0.0574    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405    0.6430    2.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856    1.6662   -1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4738    0.5330   -1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937   -0.5979   -3.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0901   -0.1955   -3.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3671   -2.2422   -2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -3.1538   -3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360   -3.4331   -1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -1.8960    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130   -1.5849   -1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343   -0.4490    0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    1.3835    2.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    2.8344    2.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2025    2.4262    1.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1947    3.1221   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5218    4.8942   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    4.3534   -0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5840    2.0083   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8126   -0.5480    0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174   -1.9101    0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0068   -0.4581    1.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -0.8149   -1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  6  7  1  6
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
  6  5  1  0
  5  4  1  1
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 27  1  0
 27 25  1  0
 25 26  1  0
 25 24  1  0
 24 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 11  9  1  0
 14 13  1  0
 27  5  1  0
 23 24  1  0
 18  6  1  0
 19  5  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
  8 37  1  0
  8 38  1  0
  7 35  1  0
  7 36  1  0
 11 42  1  1
 12 43  1  0
 17 47  1  0
 16 46  1  0
 15 45  1  0
 14 44  1  0
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 55  1  6
 26 52  1  0
 26 53  1  0
 26 54  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
M  END


  Mrv1652304282200152D          

 27 32  0  0  1  0            999 V2000
    1.8020   -1.3501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0724   -0.5706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8972   -0.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366   -1.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598   -1.8480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435   -2.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401   -1.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5041   -0.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647   -0.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3446    0.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4146   -0.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212   -0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772   -1.3338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -1.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.2088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6131    0.9883    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9554    1.4863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    0.9720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9576    1.6904    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
  4  5  1  0  0  0  0
  1  5  1  6  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050846

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC[C@]2([C@@H]1NC1=C2C=CC=C1)[C@]12CCN(C)[C@H]1N(C)C1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H28N4/c1-25-14-12-22(16-8-4-6-10-18(16)24-20(22)25)23-13-15-26(2)21(23)27(3)19-11-7-5-9-17(19)23/h4-11,20-21,24H,12-15H2,1-3H3/t20-,21+,22+,23+/m1/s1

> <INCHI_KEY>
GSQUXSFTXJRLQJ-LDVJMBRRSA-N

> <FORMULA>
C23H28N4

> <MOLECULAR_WEIGHT>
360.505

> <EXACT_MASS>
360.231396918

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.32647461183609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
3.4821541700000003

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.861430810620998

> <JCHEM_PKA_STRONGEST_BASIC>
7.751108558880519

> <JCHEM_POLAR_SURFACE_AREA>
21.75

> <JCHEM_REFRACTIVITY>
112.143

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-calycanthidine

> <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       3.364  -2.520   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.868  -1.065   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.408  -1.095   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.855  -2.569   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.592  -3.450   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.561  -4.989   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.355  -2.919   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.408  -1.795   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.961  -0.321   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.243   0.021   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.641  -0.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.159  -1.023   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.824  -2.490   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.895  -3.718   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.373   0.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.878   1.845   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.650   2.774   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.387   1.894   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.833   0.420   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.781  -0.704   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.281  -0.354   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.166   1.120   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.887   2.244   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       6.417   1.814   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       6.864   0.341   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.601  -0.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.388   3.155   0.000  0.00  0.00           C+0
CONECT    1    2    5   13                                                  
CONECT    2    1    3   11   15                                             
CONECT    3    2    4   10                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3                                                       
CONECT   11    2   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    1   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16   19   26                                             
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   15   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   16   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   15                                                       
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Value	Source
Calycanthidine	ChEBI

Chemical Formula

C₂₃H₂₈N₄

Average Mass

360.5050 Da

Monoisotopic Mass

360.23140 Da

IUPAC Name

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

Traditional Name

(+)-calycanthidine

CAS Registry Number

Not Available

SMILES

CN1CC[C@]2([C@@H]1NC1=C2C=CC=C1)[C@]12CCN(C)[C@H]1N(C)C1=C2C=CC=C1

InChI Identifier

InChI=1S/C23H28N4/c1-25-14-12-22(16-8-4-6-10-18(16)24-20(22)25)23-13-15-26(2)21(23)27(3)19-11-7-5-9-17(19)23/h4-11,20-21,24H,12-15H2,1-3H3/t20-,21+,22+,23+/m1/s1

InChI Key

GSQUXSFTXJRLQJ-LDVJMBRRSA-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
Calycanthus floridus	Plant	KNApSAcK
Chimonanthus praecox	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
Dialkylarylamine
Secondary aliphatic/aromatic amine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Pyrrole
Secondary amine
Azacycle
Amine
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

calycanthidine (CHEBI:3332 )
Indole alkaloids (C09097 )

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	3.68	ALOGPS
logP	3.48	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.86	ChemAxon
pKa (Strongest Basic)	7.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	21.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	112.14 m³·mol⁻¹	ChemAxon
Polarizability	40.33 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

C00001700

Chemspider ID

390583

KEGG Compound ID

C09097

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442031

PDB ID

Not Available

ChEBI ID

3332

Good Scents ID

rw1818671

References

General References

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 ]
Wu WJ, Wang Q, Zhang W, Li L: [Discrimination and clinical value of plasma metabolomic profiles in multidrug resistant epithelial ovarian cancer]. Zhonghua Zhong Liu Za Zhi. 2017 Dec 23;39(12):896-902. doi: 10.3760/cma.j.issn.0253-3766.2017.12.004. [PubMed:29262505 ]
Morikawa T, Nakanishi Y, Ninomiya K, Matsuda H, Nakashima S, Miki H, Miyashita Y, Yoshikawa M, Hayakawa T, Muraoka O: Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox. J Nat Med. 2014 Jul;68(3):539-49. doi: 10.1007/s11418-014-0832-1. Epub 2014 Mar 26. [PubMed:24668298 ]
Liu ZX, Liu ZX: [Chemical constituents from the seed of Chimonanthus praecox extracted by supercritical carbon dioxide]. Zhong Yao Cai. 2008 Jul;31(7):992-5. [PubMed:18973012 ]

Showing NP-Card for Calycanthidine (NP0050846)

MOL for NP0050846 (Calycanthidine)

3D MOL for NP0050846 (Calycanthidine)

3D SDF for NP0050846 (Calycanthidine)

3D-SDF for NP0050846 (Calycanthidine)

PDB for NP0050846 (Calycanthidine)

3D PDB for NP0050846 (Calycanthidine)

SMILES for NP0050846 (Calycanthidine)

INCHI for NP0050846 (Calycanthidine)

Structure for NP0050846 (Calycanthidine)

3D Structure for NP0050846 (Calycanthidine)