NP-MRD: Showing NP-Card for (+)-Tabernaebovine (NP0077744)

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Record Information

Version

2.0

Created at

2022-04-28 22:54:21 UTC

Updated at

2022-04-28 22:54:22 UTC

NP-MRD ID

NP0077744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Tabernaebovine

Description

(1S,9S,12S,13S,15R,20R)-12-ethyl-4-[(1R,9R,12S,13S,15R,20R)-12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6-trien-9-yl]-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2(7),3,5-triene 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. (+)-Tabernaebovine is found in Tabernaemontana bovina. Based on a literature review very few articles have been published on (1S,9S,12S,13S,15R,20R)-12-ethyl-4-[(1R,9R,12S,13S,15R,20R)-12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6-trien-9-yl]-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2(7),3,5-triene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200542D          

 46 57  0  0  1  0            999 V2000
    9.0336    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4718    1.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7141    0.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5182    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0800    0.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8377    1.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7605   -0.5472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3824   -0.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0902   -0.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9057   -1.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5099   -1.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2985   -1.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4829   -0.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8788   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0840   -1.3062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5884   -1.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7694   -1.8664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4460   -1.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9416   -0.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2738   -2.5259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5972   -3.2849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4162   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9118   -2.7247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8512   -2.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8644   -1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7783   -3.1855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9802    3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1634    2.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4045    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3051    1.7342    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9646    1.2386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8653    0.4197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8418    0.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1063    0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467    0.5918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5461    1.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7872    1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455    2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    1.9064    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  4  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 15 10  1  6  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  1  0  0  0
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 21 26  1  1  0  0  0
 20 26  1  1  0  0  0
 17 27  1  6  0  0  0
 27 28  1  0  0  0  0
  8 29  1  0  0  0  0
 30  2  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
  1 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 30 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 36 43  1  0  0  0  0
 43 44  1  1  0  0  0
 42 44  1  1  0  0  0
 36 45  1  6  0  0  0
 45 46  1  0  0  0  0
M  END

     RDKit          3D

 96107  0  0  0  0  0  0  0  0999 V2000
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  5 55  1  0
  6 56  1  1
  8 57  1  0
  8 58  1  0
  8 59  1  0
 36 87  1  0
 11 61  1  0
 10 60  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 17 66  1  0
 17 67  1  0
 18 68  1  0
 18 69  1  0
 18 70  1  0
 19 71  1  6
 21 72  1  1
 22 73  1  0
 22 74  1  0
 24 75  1  0
 24 76  1  0
 25 77  1  0
 25 78  1  0
 35 86  1  1
 31 82  1  0
 30 81  1  0
 29 80  1  0
 28 79  1  0
 34 83  1  0
 34 84  1  0
 34 85  1  0
 39 88  1  0
 39 89  1  0
 40 90  1  0
 40 91  1  0
 42 92  1  0
 42 93  1  0
 43 94  1  1
 45 95  1  1
 46 96  1  6
M  END


  Mrv1652304292200542D          

 46 57  0  0  1  0            999 V2000
    9.0336    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4718    1.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7141    0.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5182    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0800    0.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8377    1.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7605   -0.5472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3824   -0.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0902   -0.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9057   -1.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5099   -1.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2985   -1.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4829   -0.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8788   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0840   -1.3062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5884   -1.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7694   -1.8664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4460   -1.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9416   -0.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2738   -2.5259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5972   -3.2849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4162   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9118   -2.7247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8512   -2.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8644   -1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7783   -3.1855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9504   -1.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4548   -2.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5669    0.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7236    1.5621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8230    2.3811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6326    2.5396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9802    3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1634    2.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4045    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3051    1.7342    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9646    1.2386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8653    0.4197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8418    0.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2657    0.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1063    0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467    0.5918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5461    1.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7872    1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455    2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    1.9064    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  4  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 15 10  1  6  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 15 25  1  0  0  0  0
 21 26  1  1  0  0  0
 20 26  1  1  0  0  0
 17 27  1  6  0  0  0
 27 28  1  0  0  0  0
  8 29  1  0  0  0  0
 30  2  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
  1 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 30 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 36 43  1  0  0  0  0
 43 44  1  1  0  0  0
 42 44  1  1  0  0  0
 36 45  1  6  0  0  0
 45 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CC[C@@H]3N(C)C4=C(C=C(C=C4)[C@]45CC[C@]6(CC)[C@@H]7O[C@@H]7CN7CC[C@]4([C@H]67)C4=C(C=CC=C4)N5C)[C@@]33CCN(C[C@H]4O[C@@H]14)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C40H50N4O2/c1-5-36-14-13-31-38(17-19-43(34(36)38)22-29-32(36)45-29)26-21-24(11-12-27(26)41(31)3)40-16-15-37(6-2)33-30(46-33)23-44-20-18-39(40,35(37)44)25-9-7-8-10-28(25)42(40)4/h7-12,21,29-35H,5-6,13-20,22-23H2,1-4H3/t29-,30-,31+,32-,33-,34+,35+,36-,37-,38+,39-,40-/m1/s1

> <INCHI_KEY>
JGSVLTPLGGGCRI-FKAXQFMSSA-N

> <FORMULA>
C40H50N4O2

> <MOLECULAR_WEIGHT>
618.866

> <EXACT_MASS>
618.393376866

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
70.59353467437333

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9R,12S,13S,15R,20R)-12-ethyl-9-[(1S,9S,12S,13S,15R,20R)-12-ethyl-8-methyl-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-trien-4-yl]-8-methyl-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-triene

> <ALOGPS_LOGP>
4.99

> <JCHEM_LOGP>
5.904749145666667

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
7.987309050238803

> <JCHEM_POLAR_SURFACE_AREA>
38.02

> <JCHEM_REFRACTIVITY>
181.0785999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,12S,13S,15R,20R)-12-ethyl-9-[(1S,9S,12S,13S,15R,20R)-12-ethyl-8-methyl-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-trien-4-yl]-8-methyl-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-triene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      16.863   3.395   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.814   2.267   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.266   0.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.767   0.451   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.816   1.578   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.364   3.050   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.220  -1.021   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      19.381  -0.010   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      20.702  -0.801   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.357  -2.302   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.485  -3.351   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.957  -2.898   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.302  -1.397   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.174  -0.349   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.823  -2.438   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.898  -3.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.370  -3.484   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.766  -2.067   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.691  -0.836   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.444  -4.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.048  -6.132   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.577  -6.317   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      18.502  -5.086   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      20.255  -4.477   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.280  -2.938   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.519  -5.946   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.841  -3.298   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.916  -4.530   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.725   1.491   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.417   2.916   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.603   4.445   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      16.114   4.741   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      16.763   6.137   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.372   5.370   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.955   4.766   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.769   3.237   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.001   2.312   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      12.815   0.783   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      14.638   0.434   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      15.429   1.755   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.398   0.180   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.167   1.105   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      10.353   2.633   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       8.936   2.030   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      10.538   4.162   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.122   3.559   0.000  0.00  0.00           C+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   15   19                                             
CONECT    8    7    9   29                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   10    7   16   25                                             
CONECT   16   15   17   23                                                  
CONECT   17   16   18   20   27                                             
CONECT   18   17   19                                                       
CONECT   19   18    7                                                       
CONECT   20   17   21   26                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   15                                                       
CONECT   26   21   20                                                       
CONECT   27   17   28                                                       
CONECT   28   27                                                            
CONECT   29    8                                                            
CONECT   30    2   31   37   40                                             
CONECT   31   30   32   34                                                  
CONECT   32   31    1   33                                                  
CONECT   33   32                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   43   45                                             
CONECT   37   36   30   38                                                  
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39   30                                                       
CONECT   41   38   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42   36   44                                                  
CONECT   44   43   42                                                       
CONECT   45   36   46                                                       
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₀N₄O₂

Average Mass

618.8660 Da

Monoisotopic Mass

618.39338 Da

IUPAC Name

(1R,9R,12S,13S,15R,20R)-12-ethyl-9-[(1S,9S,12S,13S,15R,20R)-12-ethyl-8-methyl-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-trien-4-yl]-8-methyl-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-triene

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@]12CC[C@@H]3N(C)C4=C(C=C(C=C4)[C@]45CC[C@]6(CC)[C@@H]7O[C@@H]7CN7CC[C@]4([C@H]67)C4=C(C=CC=C4)N5C)[C@@]33CCN(C[C@H]4O[C@@H]14)[C@@H]23

InChI Identifier

InChI=1S/C40H50N4O2/c1-5-36-14-13-31-38(17-19-43(34(36)38)22-29-32(36)45-29)26-21-24(11-12-27(26)41(31)3)40-16-15-37(6-2)33-30(46-33)23-44-20-18-39(40,35(37)44)25-9-7-8-10-28(25)42(40)4/h7-12,21,29-35H,5-6,13-20,22-23H2,1-4H3/t29-,30-,31+,32-,33-,34+,35+,36-,37-,38+,39-,40-/m1/s1

InChI Key

JGSVLTPLGGGCRI-FKAXQFMSSA-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 bovina	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
Plumeran-type alkaloid
Neolignan skeleton
Carbazole
Quinolidine
Indole or derivatives
Indolizidine
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Para-oxazepine
Epoxypiperidine
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Oxacycle
Ether
Oxirane
Dialkyl ether
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.99	ALOGPS
logP	5.9	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	7.99	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.02 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	181.08 m³·mol⁻¹	ChemAxon
Polarizability	70.59 Å³	ChemAxon
Number of Rings	12	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

26666401

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162874695

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Tabernaebovine (NP0077744)

MOL for NP0077744 ((+)-Tabernaebovine)

3D MOL for NP0077744 ((+)-Tabernaebovine)

3D SDF for NP0077744 ((+)-Tabernaebovine)

3D-SDF for NP0077744 ((+)-Tabernaebovine)

PDB for NP0077744 ((+)-Tabernaebovine)

3D PDB for NP0077744 ((+)-Tabernaebovine)

SMILES for NP0077744 ((+)-Tabernaebovine)

INCHI for NP0077744 ((+)-Tabernaebovine)

Structure for NP0077744 ((+)-Tabernaebovine)

3D Structure for NP0077744 ((+)-Tabernaebovine)