NP-MRD: Showing NP-Card for Ajadine (NP0081004)

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Record Information

Version

2.0

Created at

2022-04-29 01:59:31 UTC

Updated at

2022-04-29 01:59:31 UTC

NP-MRD ID

NP0081004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ajadine

Description

N-[2-({[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-4-(acetyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-13-yl]methoxy}carbonyl)phenyl]ethanimidic 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. Ajadine is found in Consolida ajacis, Consolida ambigua, Consolida orientalis, Delphinium ajacis L. and Delphinium stapeliosum . Based on a literature review very few articles have been published on N-[2-({[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-4-(acetyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-13-yl]methoxy}carbonyl)phenyl]ethanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203592D          

 47 53  0  0  1  0            999 V2000
   -0.5794    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -0.0809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.5674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1068   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6909   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2713   -2.0278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0833   -1.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7818   -0.1701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3551   -0.0202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2971   -0.2217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -1.0257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9370   -1.5782    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7321   -2.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -1.4331    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7789   -0.5704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1226   -0.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6259   -0.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781    0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -1.7277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7273   -2.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828   -2.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -1.7091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9894   -3.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4277    0.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3237   -0.3602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4233   -1.2323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5295    0.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4203    0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202    0.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6988   -2.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217   -3.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1170   -2.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -2.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887   -3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642   -3.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -4.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2377   -4.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132   -4.9687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254   -5.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -5.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621   -6.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744   -5.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -5.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867   -4.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500   -4.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    1.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9  2  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 11 25  1  6  0  0  0
 10 26  1  0  0  0  0
 27 26  1  1  0  0  0
  4 27  1  0  0  0  0
  8 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 10 30  1  6  0  0  0
  7 31  1  1  0  0  0
 31 32  1  0  0  0  0
  4 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 37 46  1  0  0  0  0
  1 47  1  0  0  0  0
M  END

     RDKit          3D

 95101  0  0  0  0  0  0  0  0999 V2000
    0.7591   -2.6430    3.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133   -2.5567    2.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0840   -1.1852    1.7425 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442   -0.6573    1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1462    0.6244    0.6044 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2677    0.5937   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1601    0.4302   -4.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3307   -0.3375   -2.4791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608    1.8360    1.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304    2.4431    2.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8629    1.3998    2.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5270    0.4924    3.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
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 43 92  1  1
 46 93  1  0
 46 94  1  0
 46 95  1  0
 42 91  1  6
 34 80  1  0
 35 81  1  0
 35 82  1  0
 36 83  1  1
 38 84  1  0
 38 85  1  0
 38 86  1  0
 28 74  1  0
 29 75  1  6
 31 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  6
 26 73  1  1
M  END


  Mrv1652304292203592D          

 47 53  0  0  1  0            999 V2000
   -0.5794    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -0.0809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.5674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1068   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6909   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2713   -2.0278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0833   -1.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7818   -0.1701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3551   -0.0202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2971   -0.2217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -1.0257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9370   -1.5782    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7321   -2.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -1.4331    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7789   -0.5704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1226   -0.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6259   -0.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781    0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -1.7277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7273   -2.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828   -2.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -1.7091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9894   -3.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4277    0.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3237   -0.3602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4233   -1.2323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5295    0.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4203    0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202    0.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6988   -2.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217   -3.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1170   -2.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -2.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887   -3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642   -3.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -4.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2377   -4.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132   -4.9687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254   -5.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -5.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621   -6.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744   -5.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -5.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867   -4.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500   -4.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    1.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9  2  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 11 25  1  6  0  0  0
 10 26  1  0  0  0  0
 27 26  1  1  0  0  0
  4 27  1  0  0  0  0
  8 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 10 30  1  6  0  0  0
  7 31  1  1  0  0  0
 31 32  1  0  0  0  0
  4 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 37 46  1  0  0  0  0
  1 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC(=O)C3=C(NC(C)=O)C=CC=C3)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC(C)=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/C35H48N2O10/c1-7-37-16-32(17-46-30(40)20-10-8-9-11-23(20)36-18(2)38)13-12-25(44-5)34-22-14-21-24(43-4)15-33(41,26(22)27(21)47-19(3)39)35(42,31(34)37)29(45-6)28(32)34/h8-11,21-22,24-29,31,41-42H,7,12-17H2,1-6H3,(H,36,38)/t21-,22-,24+,25+,26-,27+,28-,29+,31+,32+,33-,34+,35-/m1/s1

> <INCHI_KEY>
QFEWDYKEKVVRHZ-QVKHUSFCSA-N

> <FORMULA>
C35H48N2O10

> <MOLECULAR_WEIGHT>
656.773

> <EXACT_MASS>
656.330895754

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
70.60463497592863

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-4-(acetyloxy)-11-ethyl-8,9-dihydroxy-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-acetamidobenzoate

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
0.7459989996666635

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.698522149004841

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.052203307594548

> <JCHEM_PKA_STRONGEST_BASIC>
9.66661019490535

> <JCHEM_POLAR_SURFACE_AREA>
153.09

> <JCHEM_REFRACTIVITY>
169.40029999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-4-(acetyloxy)-11-ethyl-8,9-dihydroxy-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-acetamidobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.082   1.521   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.123  -0.151   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.233  -1.434   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.594  -2.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.199  -4.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.290  -4.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.373  -3.785   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.022  -2.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.459  -0.318   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530  -0.038   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.288  -0.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.462  -1.915   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.616  -2.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.100  -3.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.617  -2.675   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.054  -1.065   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.829  -0.025   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.635  -0.616   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.479   0.717   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.779  -3.225   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.958  -4.505   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.555  -4.518   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.335  -3.190   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.314  -5.858   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.532   1.270   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.604  -0.672   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.790  -2.300   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.988   0.300   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.651   0.407   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.464   1.663   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.171  -5.344   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.654  -6.924   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.085  -3.822   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.943  -5.197   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.219  -6.556   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.680  -6.609   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.034  -7.863   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.310  -9.222   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      -0.771  -9.275   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0      -0.047 -10.634   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.492 -10.687   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.863 -11.941   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.126 -10.529   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -4.665 -10.476   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -5.389  -9.117   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -4.573  -7.810   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.205   2.739   0.000  0.00  0.00           C+0
CONECT    1    2   47                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27   33                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   31                                                  
CONECT    8    7    9   13   27                                             
CONECT    9    8    2   10                                                  
CONECT   10    9   11   26   30                                             
CONECT   11   10   12   17   25                                             
CONECT   12   11   13   20                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   12   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   11                                                            
CONECT   26   10   27   28                                                  
CONECT   27   26    4    8                                                  
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   10                                                            
CONECT   31    7   32                                                       
CONECT   32   31                                                            
CONECT   33    4   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   46                                                  
CONECT   38   37   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   38   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   37                                                       
CONECT   47    1                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  106    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₃₅H₄₈N₂O₁₀

Average Mass

656.7730 Da

Monoisotopic Mass

656.33090 Da

IUPAC Name

[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13S,16S,17R,18S)-4-(acetyloxy)-11-ethyl-8,9-dihydroxy-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-acetamidobenzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC(=O)C3=C(NC(C)=O)C=CC=C3)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC(C)=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/C35H48N2O10/c1-7-37-16-32(17-46-30(40)20-10-8-9-11-23(20)36-18(2)38)13-12-25(44-5)34-22-14-21-24(43-4)15-33(41,26(22)27(21)47-19(3)39)35(42,31(34)37)29(45-6)28(32)34/h8-11,21-22,24-29,31,41-42H,7,12-17H2,1-6H3,(H,36,38)/t21-,22-,24+,25+,26-,27+,28-,29+,31+,32+,33-,34+,35-/m1/s1

InChI Key

QFEWDYKEKVVRHZ-QVKHUSFCSA-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
Consolida ajacis	LOTUS Database	35616633
Consolida ambigua	LOTUS Database	35616633
Consolida orientalis	LOTUS Database	35616633
Delphinium ajacis L.	Plant	KNApSAcK
Delphinium stapeliosum	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
Acylaminobenzoic acid or derivatives
Quinolidine
Benzoate ester
Acetanilide
N-acetylarylamine
Alkaloid or derivatives
Anilide
Benzoic acid or derivatives
N-arylamide
Benzoyl
Azepane
Benzenoid
Piperidine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Acetamide
Vinylogous amide
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid ester
Carboxamide group
Amino acid or derivatives
1,2-diol
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	1.98	ALOGPS
logP	0.75	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.05	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	153.09 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	169.4 m³·mol⁻¹	ChemAxon
Polarizability	70.6 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

101596819

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Ajadine (NP0081004)

MOL for NP0081004 (Ajadine)

3D MOL for NP0081004 (Ajadine)

3D SDF for NP0081004 (Ajadine)

3D-SDF for NP0081004 (Ajadine)

PDB for NP0081004 (Ajadine)

3D PDB for NP0081004 (Ajadine)

SMILES for NP0081004 (Ajadine)

INCHI for NP0081004 (Ajadine)

Structure for NP0081004 (Ajadine)

3D Structure for NP0081004 (Ajadine)