NP-MRD: Showing NP-Card for (-)-Jerantinine D (NP0076726)

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Record Information

Version

2.0

Created at

2022-04-28 21:55:08 UTC

Updated at

2022-04-28 21:55:08 UTC

NP-MRD ID

NP0076726

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Jerantinine D

Description

Jerantinine D belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. Jerantinine D is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (-)-Jerantinine D is found in Tabernaemontana corymbosa. Based on a literature review very few articles have been published on jerantinine D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223552D          

 30 35  0  0  1  0            999 V2000
    5.4447    0.2692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3453   -0.5498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0049   -1.0454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7638   -0.7220    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8632    0.0970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2037    0.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3031    1.4116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5228   -0.3986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055   -1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1465   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870   -1.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -0.8732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0442   -0.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4681    0.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8382   -0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2764   -1.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6773   -1.8508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4722   -0.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2299   -0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    0.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5494    1.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4258    0.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640   -0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0471   -3.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882   -3.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7067   -3.5024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6073   -4.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -1.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5651   -2.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  6  0  0  0
  4  8  1  6  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  3 29  1  6  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 54 59  0  0  0  0  0  0  0  0999 V2000
   -3.2849   -0.9750   -1.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -1.0811   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -1.5445   -0.0237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4640   -0.4879    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8099    0.8202    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6332    1.9769    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9033    1.8684    0.2062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    3.2088   -0.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424    4.3321   -0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4845    0.9167    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672    2.0123    0.0864 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859    1.4302   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8885    1.9855   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9969    1.1956   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080    1.7647   -1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2692    3.1487   -1.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9350   -0.1769   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1033   -0.9049   -0.6004 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7495   -0.7309    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6422    0.0740    0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.2803    0.7102 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4863   -0.4606    2.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -1.9171    2.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -2.5448    1.3397 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4678   -3.8591    1.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2412   -4.8539    1.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -4.0125    0.4540 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9846   -3.7803   -0.8705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501   -2.8263    0.1063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2561   -1.5746    0.2839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3353   -1.2266   -3.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6145    0.1051   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122   -1.5309   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3575   -1.8766   -2.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3703   -0.1049   -1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5053   -0.4550    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4732   -0.7012    1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9425    4.0786   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0530    5.0319    0.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4121    4.8809   -1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1658    3.0079   -0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    3.0632   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4390    3.5262   -1.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972    3.7305   -0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1998    3.3282   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1773   -1.8927   -0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7352   -1.7992    0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -0.1067    2.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675    0.1354    2.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8208   -2.2099    2.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -2.2280    3.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -4.8469    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520   -2.7518    0.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2617   -1.8809   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  1  0
 12 20  2  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14 13  2  0
 20 21  1  0
 21 22  1  1
 22 23  1  0
 23 24  1  0
 24 30  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 30  3  1  0
 29 27  1  0
 29  3  1  0
 21 10  1  0
 30 21  1  0
 13 12  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 19 47  1  0
 18 46  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 13 42  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 30 54  1  6
 27 52  1  1
 29 53  1  1
M  END


  Mrv1652304282223552D          

 30 35  0  0  1  0            999 V2000
    5.4447    0.2692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3453   -0.5498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0049   -1.0454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7638   -0.7220    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8632    0.0970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2037    0.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3031    1.4116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5228   -0.3986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055   -1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1465   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870   -1.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -0.8732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0442   -0.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4681    0.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8382   -0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2764   -1.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6773   -1.8508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4722   -0.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2299   -0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    0.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5494    1.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4258    0.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640   -0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0471   -3.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882   -3.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7067   -3.5024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6073   -4.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -1.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5651   -2.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  6  0  0  0
  4  8  1  6  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  3 29  1  6  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076726

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]12CC(C(=O)OC)=C3NC4=C(C=C(O)C(OC)=C4)[C@@]33CCN([C@@H]13)C(=O)[C@@H]1O[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O6/c1-4-21-9-10(19(27)29-3)16-22(11-7-13(25)14(28-2)8-12(11)23-16)5-6-24(20(21)22)18(26)15-17(21)30-15/h7-8,15,17,20,23,25H,4-6,9H2,1-3H3/t15-,17+,20+,21-,22+/m1/s1

> <INCHI_KEY>
NCDJGOXCXAXUIG-PVUPTQESSA-N

> <FORMULA>
C22H24N2O6

> <MOLECULAR_WEIGHT>
412.442

> <EXACT_MASS>
412.163436501

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.60565817655528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12S,13R,15R,20R)-12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2(7),3,5,9-tetraene-10-carboxylate

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
0.7523364249999993

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.136486108317865

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.830737655467686

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1016046360460292

> <JCHEM_POLAR_SURFACE_AREA>
100.63000000000001

> <JCHEM_REFRACTIVITY>
107.54439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12S,13R,15R,20R)-12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2(7),3,5,9-tetraene-10-carboxylate

> <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  N   UNK     0      10.163   0.502   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       9.978  -1.026   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.209  -1.951   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.626  -1.348   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.811   0.181   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.580   1.106   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.766   2.635   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.043  -0.744   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.024  -3.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.607  -4.084   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.376  -3.159   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.561  -1.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.549  -0.469   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.341   0.852   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.165  -0.981   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.116  -2.109   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.864  -3.455   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.615  -1.765   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.163  -0.293   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.211   0.835   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.712   0.491   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.759   2.307   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.662   0.052   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.613  -1.076   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.421  -5.613   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.005  -6.216   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.653  -6.538   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.467  -8.067   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.440  -2.876   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.255  -4.405   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4    9   29                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    4                                                       
CONECT    9    3   10                                                       
CONECT   10    9   11   25                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11    2   13   15                                             
CONECT   13   12   14                                                       
CONECT   14   13    1                                                       
CONECT   15   12   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   15                                                       
CONECT   22   20                                                            
CONECT   23   19   24                                                       
CONECT   24   23                                                            
CONECT   25   10   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29    3   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄N₂O₆

Average Mass

412.4420 Da

Monoisotopic Mass

412.16344 Da

IUPAC Name

methyl (1R,12S,13R,15R,20R)-12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2(7),3,5,9-tetraene-10-carboxylate

Traditional Name

methyl (1R,12S,13R,15R,20R)-12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2(7),3,5,9-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@]12CC(C(=O)OC)=C3NC4=C(C=C(O)C(OC)=C4)[C@@]33CCN([C@@H]13)C(=O)[C@@H]1O[C@H]21

InChI Identifier

InChI=1S/C22H24N2O6/c1-4-21-9-10(19(27)29-3)16-22(11-7-13(25)14(28-2)8-12(11)23-16)5-6-24(20(21)22)18(26)15-17(21)30-15/h7-8,15,17,20,23,25H,4-6,9H2,1-3H3/t15-,17+,20+,21-,22+/m1/s1

InChI Key

NCDJGOXCXAXUIG-PVUPTQESSA-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
Tabernaemontana corymbosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Carbazole
Indolizidine
Dihydroindole
Indole or derivatives
Anisole
Para-oxazepine
Delta-lactam
Epoxypiperidine
Piperidinone
Secondary aliphatic/aromatic amine
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Piperidine
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Lactam
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Enamine
Oxirane
Azacycle
Ether
Organoheterocyclic compound
Secondary amine
Organonitrogen compound
Amine
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:66122 )
epoxide (CHEBI:66122 )
phenols (CHEBI:66122 )
organic heterohexacyclic compound (CHEBI:66122 )
indole alkaloid (CHEBI:66122 )
methyl ester (CHEBI:66122 )
lactam (CHEBI:66122 )
alkaloid ester (CHEBI:66122 )

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	2.39	ALOGPS
logP	0.75	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.83	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.54 m³·mol⁻¹	ChemAxon
Polarizability	42.61 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00039493

Chemspider ID

24721314

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25058085

PDB ID

Not Available

ChEBI ID

66122

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Jerantinine D (NP0076726)

MOL for NP0076726 ((-)-Jerantinine D)

3D MOL for NP0076726 ((-)-Jerantinine D)

3D SDF for NP0076726 ((-)-Jerantinine D)

3D-SDF for NP0076726 ((-)-Jerantinine D)

PDB for NP0076726 ((-)-Jerantinine D)

3D PDB for NP0076726 ((-)-Jerantinine D)

SMILES for NP0076726 ((-)-Jerantinine D)

INCHI for NP0076726 ((-)-Jerantinine D)

Structure for NP0076726 ((-)-Jerantinine D)

3D Structure for NP0076726 ((-)-Jerantinine D)