NP-MRD: Showing NP-Card for (+)-Calycanthine (NP0051344)

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Record Information

Version

2.0

Created at

2022-04-27 22:44:13 UTC

Updated at

2022-04-27 22:44:13 UTC

NP-MRD ID

NP0051344

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Calycanthine

Description

Calycanthine belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system. (+)-Calycanthine is found in Bhesa archboldiana, Calycanthus floridus, Calycanthus floridus var. glaucus, Calycanthus occidentails, Calycanthus occidentalis, Calycanthus praecox, Chimonanthus praecox, Idiospermum australiense, Idiospermun australiense, Meratia praecox, Palicourea alpina, Palicourea coriacea, Palicourea fendleri and Psychotria forsteriana. (+)-Calycanthine was first documented in 2017 (PMID: 28718647). Based on a literature review a small amount of articles have been published on calycanthine (PMID: 28877378) (PMID: 35244129) (PMID: 34871491) (PMID: 30299963).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200442D          

 26 31  0  0  1  0            999 V2000
   -0.5463   -2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -1.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010   -1.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0928   -2.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651   -3.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545   -3.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342   -3.8817    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3682   -3.7961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5082   -2.7958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9151   -2.0919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926   -3.2512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1529   -3.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895   -3.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447   -4.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -3.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1498   -2.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933   -2.9674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0210   -4.0552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1742   -4.9382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -5.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990   -4.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -5.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2515   -1.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113   -1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6695   -2.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678   -2.8857    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
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 11 14  1  0  0  0  0
  8 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 19 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 15 26  1  0  0  0  0
M  END

     RDKit          3D

 52 57  0  0  0  0  0  0  0  0999 V2000
    2.2140    2.5571    2.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3335    1.4686    1.8080 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355    0.1819    1.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309   -0.8879    1.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2641   -0.7076    0.3085 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2861   -0.9191   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980   -2.1473   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -2.3073   -2.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746   -1.2570   -2.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0580   -0.0106   -2.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723    0.1337   -1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8813    1.4350   -0.5484 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268    1.6649    0.4391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3123    0.6941    0.2875 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1460    0.8452    1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -0.2364    1.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500   -1.5171    1.5966 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4329   -2.6160    1.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862   -1.6835    0.3012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8197   -1.4235   -0.7948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9301   -0.1120   -1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7756    0.0936   -2.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    1.3657   -3.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736    2.4032   -2.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150    2.1780   -1.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978    0.9309   -0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8515    2.2808    3.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7806    2.8333    1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5758    3.4188    2.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2550    0.0762    3.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    0.0450    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1752   -0.9864    2.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842   -1.8720    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9382   -3.0493   -1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634   -3.2757   -2.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0612   -1.3618   -3.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6861    0.8032   -2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4966    2.2264   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445    2.7222    0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6894    1.8249    1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5274    0.9231    2.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696   -0.1163    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -0.1465    2.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -3.4016    2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2367   -2.2267    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8670   -3.0823    0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -2.7419    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -2.2308   -1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3623   -0.7086   -2.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5812    1.4788   -3.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2779    3.3772   -2.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    3.0635   -1.0624 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 19  1  0
 19 20  1  0
 20 21  1  0
 21 26  2  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 22  2  0
 26 14  1  0
 14 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
 13  2  1  0
  6 11  1  0
 14  5  1  0
  6  5  1  0
 17 19  1  0
 22 21  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
 19 47  1  6
 20 48  1  0
 25 52  1  0
 24 51  1  0
 23 50  1  0
 22 49  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 13 39  1  1
 12 38  1  0
 10 37  1  0
  9 36  1  0
  8 35  1  0
  7 34  1  0
M  END


  Mrv1652304282200442D          

 26 31  0  0  1  0            999 V2000
   -0.5463   -2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -1.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010   -1.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0928   -2.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651   -3.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545   -3.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342   -3.8817    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3682   -3.7961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5082   -2.7958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9151   -2.0919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926   -3.2512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1529   -3.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895   -3.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447   -4.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -3.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1498   -2.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933   -2.9674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0210   -4.0552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1742   -4.9382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -5.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990   -4.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -5.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2515   -1.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113   -1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6695   -2.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678   -2.8857    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
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 11 14  1  0  0  0  0
  8 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 19 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 15 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051344

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC[C@@]23[C@@H]4NC5=C(C=CC=C5)[C@]2(CCN4C)[C@@H]1NC1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N4/c1-25-13-11-22-16-8-4-5-9-17(16)23-19(25)21(22)12-14-26(2)20(22)24-18-10-6-3-7-15(18)21/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21-,22-/m1/s1

> <INCHI_KEY>
XSYCDVWYEVUDKQ-GXRSIYKFSA-N

> <FORMULA>
C22H26N4

> <MOLECULAR_WEIGHT>
346.478

> <EXACT_MASS>
346.215746853

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.50290757447907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3^{2,10}.0^{1,10}.0^{4,9}.0^{13,18}]tetracosa-4,6,8,13(18),14,16-hexaene

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.8468884386666664

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.861890429830531

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.861890429830527

> <JCHEM_PKA_STRONGEST_BASIC>
7.599012478897538

> <JCHEM_POLAR_SURFACE_AREA>
30.54

> <JCHEM_REFRACTIVITY>
107.9082

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3^{2,10}.0^{1,10}.0^{4,9}.0^{13,18}]tetracosa-4,6,8,13(18),14,16-hexaene

> <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      -1.020  -4.635   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.408  -3.222   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.122  -3.045   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.040  -4.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.428  -5.694   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.102  -5.871   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.677  -7.246   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.421  -7.086   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.682  -5.219   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.575  -3.905   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       3.906  -6.069   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.152  -6.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.100  -7.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.190  -7.582   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.241  -5.986   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.013  -5.058   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.414  -5.539   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.906  -7.570   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.192  -9.218   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.728  -9.721   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.852  -8.628   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.027 -10.225   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.203  -3.530   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.621  -2.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.850  -3.858   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.660  -5.387   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   13   18                                             
CONECT    8    7    9   15   21                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7                                                       
CONECT   14   11                                                            
CONECT   15    8   16   26                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17    7   19                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20    8                                                       
CONECT   22   19                                                            
CONECT   23   16   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   15                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,10S,11R)-21,24-Dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3(2,10).0(1,10).0(4,9).0(13,18)]tetracosa-4,6,8,13,15,17-hexaene	ChEBI

Chemical Formula

C₂₂H₂₆N₄

Average Mass

346.4780 Da

Monoisotopic Mass

346.21575 Da

IUPAC Name

(1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3^{2,10}.0^{1,10}.0^{4,9}.0^{13,18}]tetracosa-4,6,8,13(18),14,16-hexaene

Traditional Name

(1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3^{2,10}.0^{1,10}.0^{4,9}.0^{13,18}]tetracosa-4,6,8,13(18),14,16-hexaene

CAS Registry Number

Not Available

SMILES

CN1CC[C@@]23[C@@H]4NC5=C(C=CC=C5)[C@]2(CCN4C)[C@@H]1NC1=CC=CC=C31

InChI Identifier

InChI=1S/C22H26N4/c1-25-13-11-22-16-8-4-5-9-17(16)23-19(25)21(22)12-14-26(2)20(22)24-18-10-6-3-7-15(18)21/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21-,22-/m1/s1

InChI Key

XSYCDVWYEVUDKQ-GXRSIYKFSA-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
Bhesa archboldiana	LOTUS Database	35616633
Calycanthus floridus	Plant	KNApSAcK
Calycanthus floridus var. glaucus	Plant	KNApSAcK
Calycanthus occidentails	Plant	KNApSAcK
Calycanthus occidentalis	Plant	KNApSAcK
Calycanthus praecox	Plant	KNApSAcK
Chimonanthus praecox	LOTUS Database	35616633
Idiospermum australiense	LOTUS Database	35616633
Idiospermun australiense	-	KNApSAcK
Meratia praecox	-	KNApSAcK
Palicourea alpina	Plant	KNApSAcK
Palicourea coriacea	Plant	KNApSAcK
Palicourea fendleri	LOTUS Database	35616633
Psychotria forsteriana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

Aminoquinolines and derivatives

Alternative Parents

Substituents

Aminoquinoline
Diazanaphthalene
Naphthyridine
Tetrahydroquinoline
Secondary aliphatic/aromatic amine
Benzenoid
Piperidine
Azacycle
Secondary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aminal (CHEBI:3333 )
calycanthaceous alkaloid (CHEBI:3333 )
organonitrogen heterocyclic compound (CHEBI:3333 )
Alkaloids (C10573 )

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	3.37	ALOGPS
logP	2.85	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.86	ChemAxon
pKa (Strongest Basic)	7.6	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	0	ChemAxon
Refractivity	107.91 m³·mol⁻¹	ChemAxon
Polarizability	38.5 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

C00002318

Chemspider ID

10344696

KEGG Compound ID

C10573

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5392245

PDB ID

Not Available

ChEBI ID

3333

Good Scents ID

rw1810471

References

General References

Kato L, Moraes AP, de Oliveira CMA, Vaz BG, de Almeida Goncalves L, E Silva EC, Janfelt C: The Spatial Distribution of Alkaloids in Psychotria prunifolia (Kunth) Steyerm and Palicourea coriacea (Cham.) K. Schum Leaves Analysed by Desorption Electrospray Ionisation Mass Spectrometry Imaging. Phytochem Anal. 2018 Jan;29(1):69-76. doi: 10.1002/pca.2715. Epub 2017 Sep 6. [PubMed:28877378 ]
Khatua A, Shyamal P, Pal S, Mondal A, Bisai A: Concise total syntheses of bis(cyclotryptamine) alkaloids via thio-urea catalyzed one-pot sequential Michael addition. Chem Commun (Camb). 2022 Mar 22;58(24):3929-3932. doi: 10.1039/d2cc01008a. [PubMed:35244129 ]
Bai L, Ma Y, Jiang X: Total Synthesis of (-)-Calycanthine via Iron-Catalyzed Stereoselective Oxidative Dimerization. J Am Chem Soc. 2021 Dec 15;143(49):20609-20615. doi: 10.1021/jacs.1c10498. Epub 2021 Dec 6. [PubMed:34871491 ]
Babu KN, Roy A, Singh M, Bisai A: Thiourea-Catalyzed Enantioselective Malonate Addition onto 3-Sulfonyl-3'-indolyl-2-oxindoles: Formal Total Syntheses of (-)-Chimonanthine, (-)-Folicanthine, and (+)-Calycanthine. Org Lett. 2018 Oct 19;20(20):6327-6331. doi: 10.1021/acs.orglett.8b02327. Epub 2018 Oct 9. [PubMed:30299963 ]
Kinthada LK, Medisetty SR, Parida A, Babu KN, Bisai A: FeCl3-Catalyzed Allylation Reactions onto 3-Hydroxy-2-oxindoles: Formal Total Syntheses of Bis-cyclotryptamine Alkaloids, (+/-)-Chimonanthine, and (+/-)-Folicanthine. J Org Chem. 2017 Aug 18;82(16):8548-8567. doi: 10.1021/acs.joc.7b01232. Epub 2017 Aug 7. [PubMed:28718647 ]

Showing NP-Card for (+)-Calycanthine (NP0051344)

MOL for NP0051344 ((+)-Calycanthine)

3D MOL for NP0051344 ((+)-Calycanthine)

3D SDF for NP0051344 ((+)-Calycanthine)

3D-SDF for NP0051344 ((+)-Calycanthine)

PDB for NP0051344 ((+)-Calycanthine)

3D PDB for NP0051344 ((+)-Calycanthine)

SMILES for NP0051344 ((+)-Calycanthine)

INCHI for NP0051344 ((+)-Calycanthine)

Structure for NP0051344 ((+)-Calycanthine)

3D Structure for NP0051344 ((+)-Calycanthine)