NP-MRD: Showing NP-Card for (+)-Trifoliolasine B (NP0072511)

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Record Information

Version

2.0

Created at

2022-04-28 17:51:34 UTC

Updated at

2022-04-28 17:51:34 UTC

NP-MRD ID

NP0072511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Trifoliolasine B

Description

(2R)-N'-[2-({[(1R,2R,3R,4S,5S,6S,8R,9R,10R,13S,16S,17R,18S)-11-ethyl-4,8,9-trihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-13-yl]methoxy}carbonyl)phenyl]-2-methylbutanediimidic acid belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. (+)-Trifoliolasine B is found in Delphinium trifoliatum and Delphinium trifoliolatum FINET et GAGNEP. Based on a literature review very few articles have been published on (2R)-N'-[2-({[(1R,2R,3R,4S,5S,6S,8R,9R,10R,13S,16S,17R,18S)-11-ethyl-4,8,9-trihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-13-yl]methoxy}carbonyl)phenyl]-2-methylbutanediimidic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282219512D          

 49 55  0  0  1  0            999 V2000
    0.6564   -1.0270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0108   -1.0264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6083   -1.1495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    0.3484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3864    0.3404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0942   -0.0351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8888    0.5185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5896    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.6359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9425   -0.1538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4107   -0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -0.7502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4822    0.0658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0347    0.8560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3533    1.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8343   -1.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057   -0.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3628    0.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -0.4896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6710    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -0.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905   -1.5568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347   -2.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -0.6284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1584   -1.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1263   -1.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188    1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588    2.0201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    1.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6068    2.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264    2.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548    3.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635    4.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439    4.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    3.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177    2.3024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7373    2.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2286    1.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0657    3.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8853    3.2474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3766    2.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2136    4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0332    4.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7223    4.6670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9534   -2.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -3.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8882   -1.9066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  6  0  0  0
 10 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
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 13 17  1  1  0  0  0
 11 18  1  1  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 20 23  1  1  0  0  0
 23 24  1  0  0  0  0
  6 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
  5 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
  3 47  1  0  0  0  0
 47 48  1  0  0  0  0
  1 49  1  6  0  0  0
M  END


  Mrv1652304282219512D          

 49 55  0  0  1  0            999 V2000
    0.6564   -1.0270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0108   -1.0264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6083   -1.1495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    0.3484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3864    0.3404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0942   -0.0351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8888    0.5185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5896    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.6359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9425   -0.1538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4107   -0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -0.7502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4822    0.0658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0347    0.8560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3533    1.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8343   -1.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057   -0.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3628    0.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -0.4896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6710    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -0.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905   -1.5568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347   -2.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -0.6284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1584   -1.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1263   -1.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188    1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588    2.0201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    1.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6068    2.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264    2.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548    3.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635    4.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439    4.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    3.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177    2.3024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7373    2.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2286    1.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0657    3.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8853    3.2474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3766    2.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2136    4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0332    4.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7223    4.6670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9534   -2.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -3.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8882   -1.9066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  6  0  0  0
 10 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
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 13 17  1  1  0  0  0
 11 18  1  1  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 20 23  1  1  0  0  0
 23 24  1  0  0  0  0
  6 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
  5 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
  3 47  1  0  0  0  0
 47 48  1  0  0  0  0
  1 49  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0072511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC(=O)C3=C(NC(=O)C[C@@H](C)C(N)=O)C=CC=C3)CC[C@H](OC)[C@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@](O)([C@@H](OC)[C@H]23)[C@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C36H51N3O10/c1-6-39-16-33(17-49-31(43)19-9-7-8-10-22(19)38-25(40)13-18(2)30(37)42)12-11-24(47-4)35-21-14-20-23(46-3)15-34(44,26(21)27(20)41)36(45,32(35)39)29(48-5)28(33)35/h7-10,18,20-21,23-24,26-29,32,41,44-45H,6,11-17H2,1-5H3,(H2,37,42)(H,38,40)/t18-,20-,21-,23+,24+,26-,27+,28-,29+,32-,33+,34-,35-,36+/m1/s1

> <INCHI_KEY>
XRSXVXWWMSONJI-AFECXZAASA-N

> <FORMULA>
C36H51N3O10

> <MOLECULAR_WEIGHT>
685.815

> <EXACT_MASS>
685.357444854

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
70.25105095456232

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R,3R,4S,5S,6S,8R,9R,10R,13S,16S,17R,18S)-11-ethyl-4,8,9-trihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3R)-3-carbamoyl-3-methylpropanamido]benzoate

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
-0.13421999900000223

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.609028471144764

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.001657128651097

> <JCHEM_PKA_STRONGEST_BASIC>
9.666344830783947

> <JCHEM_POLAR_SURFACE_AREA>
190.11

> <JCHEM_REFRACTIVITY>
177.53880000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R,3R,4S,5S,6S,8R,9R,10R,13S,16S,17R,18S)-11-ethyl-4,8,9-trihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3R)-3-carbamoyl-3-methylpropanamido]benzoate

> <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  C   UNK     0       1.225  -1.917   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.020  -1.916   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.136  -2.146   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.510  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.359   0.650   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.721   0.635   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.176  -0.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.659   0.968   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.967   2.178   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.730   1.187   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.493  -0.287   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.500  -1.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.890  -1.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.767   0.123   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.798   1.598   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.393   3.142   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.424  -2.929   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.104  -0.386   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.144   0.814   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.464  -0.914   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.119   0.216   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.467  -0.851   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.222  -2.906   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.611  -3.887   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.538  -1.173   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.162  -2.090   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.969  -2.134   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.089   2.308   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.723   3.771   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.253   3.947   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.170   2.709   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.866   5.359   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.396   5.535   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.009   6.948   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.092   8.185   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.562   8.009   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.949   6.597   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      -7.313   4.298   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      -8.843   4.473   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -9.760   3.236   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -9.456   5.886   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -10.986   6.062   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -11.903   4.825   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -11.599   7.475   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -13.129   7.650   0.000  0.00  0.00           O+0
HETATM   46  N   UNK     0     -10.682   8.712   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0      -1.780  -4.205   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.115  -5.703   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       1.658  -3.559   0.000  0.00  0.00           O+0
CONECT    1    2   13   25   49                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4   47                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22   28                                             
CONECT    6    5    7   25                                                  
CONECT    7    6    2    8   20                                             
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12    1   14   17                                             
CONECT   14   13    8   15                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   13                                                            
CONECT   18   11   19                                                       
CONECT   19   18                                                            
CONECT   20    7   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21    5                                                       
CONECT   23   20   24                                                       
CONECT   24   23                                                            
CONECT   25    6    1   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28    5   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   33   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47    3   48                                                       
CONECT   48   47                                                            
CONECT   49    1                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  110    0
END

View in JSmol

Synonyms

Value	Source
(2R)-N'-[2-({[(1R,2R,3R,4S,5S,6S,8R,9R,10R,13S,16S,17R,18S)-11-ethyl-4,8,9-trihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-13-yl]methoxy}carbonyl)phenyl]-2-methylbutanediimidate	Generator

Chemical Formula

C₃₆H₅₁N₃O₁₀

Average Mass

685.8150 Da

Monoisotopic Mass

685.35744 Da

IUPAC Name

[(1R,2R,3R,4S,5S,6S,8R,9R,10R,13S,16S,17R,18S)-11-ethyl-4,8,9-trihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3R)-3-carbamoyl-3-methylpropanamido]benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC(=O)C3=C(NC(=O)C[C@@H](C)C(N)=O)C=CC=C3)CC[C@H](OC)[C@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@](O)([C@@H](OC)[C@H]23)[C@H]14

InChI Identifier

InChI=1S/C36H51N3O10/c1-6-39-16-33(17-49-31(43)19-9-7-8-10-22(19)38-25(40)13-18(2)30(37)42)12-11-24(47-4)35-21-14-20-23(46-3)15-34(44,26(21)27(20)41)36(45,32(35)39)29(48-5)28(33)35/h7-10,18,20-21,23-24,26-29,32,41,44-45H,6,11-17H2,1-5H3,(H2,37,42)(H,38,40)/t18-,20-,21-,23+,24+,26-,27+,28-,29+,32-,33+,34-,35-,36+/m1/s1

InChI Key

XRSXVXWWMSONJI-AFECXZAASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Delphinium trifoliatum	Plant	KNApSAcK
Delphinium trifoliolatum FINET et GAGNEP	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Quinolidine
Benzoate ester
Alkaloid or derivatives
Benzoic acid or derivatives
Benzoyl
Azepane
Benzenoid
Piperidine
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	1.2	ALOGPS
logP	-0.13	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.11 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	177.54 m³·mol⁻¹	ChemAxon
Polarizability	70.25 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162865123

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Trifoliolasine B (NP0072511)

MOL for NP0072511 ((+)-Trifoliolasine B)

3D MOL for NP0072511 ((+)-Trifoliolasine B)

3D SDF for NP0072511 ((+)-Trifoliolasine B)

3D-SDF for NP0072511 ((+)-Trifoliolasine B)

PDB for NP0072511 ((+)-Trifoliolasine B)

3D PDB for NP0072511 ((+)-Trifoliolasine B)

SMILES for NP0072511 ((+)-Trifoliolasine B)

INCHI for NP0072511 ((+)-Trifoliolasine B)

Structure for NP0072511 ((+)-Trifoliolasine B)

3D Structure for NP0072511 ((+)-Trifoliolasine B)