NP-MRD: Showing NP-Card for (-)-Vincawajine (NP0066714)

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Record Information

Version

2.0

Created at

2022-04-28 10:57:58 UTC

Updated at

2022-04-28 10:57:58 UTC

NP-MRD ID

NP0066714

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Vincawajine

Description

[(1R,10S,12S,13S,14S,16S,17S,18R)-18-(acetyloxy)-4-methoxy-14-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2(7),3,5,8-tetraen-13-yl]methyl acetate belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. (-)-Vincawajine is found in Vinca major . Based on a literature review very few articles have been published on [(1R,10S,12S,13S,14S,16S,17S,18R)-18-(acetyloxy)-4-methoxy-14-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2(7),3,5,8-tetraen-13-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212572D          

 31 36  0  0  1  0            999 V2000
    4.0852    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1588    0.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840    0.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    1.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    2.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    1.9148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5090    1.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    0.4549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786    1.1322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0446    2.0239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5605    2.5212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3961    2.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4877    1.7616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3130    0.8841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2679    0.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    1.2284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7693    1.9801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2523    2.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8289    0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788    1.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2438    1.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8938    1.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3589    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    1.5188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3042    0.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353   -0.6116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7600    2.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    1.8949    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
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
 10  8  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
  7 13  1  0  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  1 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 59 64  0  0  0  0  0  0  0  0999 V2000
    7.0809    1.1354    1.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9203    0.3640    1.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8043    1.0383    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010    2.3957    0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7066    3.0677   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    2.3637   -0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4929    1.0081   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6181    0.3815    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504    0.5879   -0.4609 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1101   -0.3881   -1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4064   -0.6394   -1.6254 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7975   -0.7175   -0.1659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0728    0.0761    0.1003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7870    1.5519   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9547    1.6651   -1.3618 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4518    1.8090   -0.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2645    2.7937   -0.8189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100    0.4908   -2.1881 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060    0.0893   -2.2914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6364   -1.0356   -3.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1231   -0.2311   -0.9584 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6728   -1.5991   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.8082    0.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3815   -1.0751    0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0509   -1.2745    2.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8961   -0.1850    0.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766   -0.1559    0.5907 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1679   -1.2210    1.0541 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649   -1.3899    2.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098   -2.5498    2.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0206   -0.5761    3.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3522    1.6943    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9493    0.5244    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8769    1.9376    2.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7280    2.9276    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365    4.1544   -0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -0.6929    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3942    0.1505   -2.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450   -1.3168   -1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -1.5568   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -1.7826    0.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4149   -0.1784    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889    2.0031    0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458    2.0751   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2860    2.5316   -1.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0158    0.9733   -2.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -2.0299   -2.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0717   -0.7957   -4.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7225   -1.0774   -3.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9181    0.5201   -0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4885   -1.7253   -1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8935   -2.3822   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5248   -1.9850    2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0945   -1.6420    1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1547   -0.2547    2.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800    0.4542    1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0961   -2.6389    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011   -3.4730    2.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7931   -2.3864    3.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
  9 10  1  6
  9 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
  9  7  1  0
  7  8  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
  8  3  1  0
  7  6  1  0
  9 16  1  0
 18 15  1  0
 21 13  1  0
 27 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
 15 45  1  6
 14 43  1  0
 14 44  1  0
 13 42  1  1
 12 41  1  1
 11 40  1  6
 10 38  1  0
 10 39  1  0
 27 56  1  1
 30 57  1  0
 30 58  1  0
 30 59  1  0
  8 37  1  0
 19 46  1  6
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  1
 22 51  1  0
 22 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
M  END


  Mrv1652304282212572D          

 31 36  0  0  1  0            999 V2000
    4.0852    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1588    0.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840    0.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    1.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    2.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    1.9148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5090    1.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    0.4549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786    1.1322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0446    2.0239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5605    2.5212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3961    2.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4877    1.7616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3130    0.8841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2679    0.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    1.2284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7693    1.9801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2523    2.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8289    0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788    1.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2438    1.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8938    1.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3589    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    1.5188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3042    0.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353   -0.6116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7600    2.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    1.8949    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
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
 10  8  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
  7 13  1  0  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  1 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066714

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2N=C3[C@@H]4C[C@@H]5[C@H]6[C@H](C[C@@]3([C@@H]6OC(C)=O)C2=C1)N4[C@@H](C)[C@H]5COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O5/c1-11-16(10-30-12(2)27)15-8-19-22-24(17-7-14(29-4)5-6-18(17)25-22)9-20(26(11)19)21(15)23(24)31-13(3)28/h5-7,11,15-16,19-21,23H,8-10H2,1-4H3/t11-,15-,16+,19-,20-,21-,23+,24+/m0/s1

> <INCHI_KEY>
NVBKJHMKBGTOJC-LYQRILJPSA-N

> <FORMULA>
C24H28N2O5

> <MOLECULAR_WEIGHT>
424.497

> <EXACT_MASS>
424.19982201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.866710948394974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,10S,12S,13S,14S,16S,17S,18R)-18-(acetyloxy)-4-methoxy-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-13-yl]methyl acetate

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
1.9601037033333348

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.568613057787812

> <JCHEM_POLAR_SURFACE_AREA>
77.42999999999999

> <JCHEM_REFRACTIVITY>
113.72330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,10S,12S,13S,14S,16S,17S,18R)-18-(acetyloxy)-4-methoxy-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-13-yl]methyl acetate

> <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       7.626   3.299   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.763   1.765   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.503   0.879   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.106   1.527   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.969   3.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.229   3.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.458   3.574   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.817   2.058   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.727   0.849   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.267   2.113   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.083   3.778   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.046   4.706   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.606   4.974   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.910   3.288   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.584   1.650   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.500   0.948   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.986   2.293   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.436   3.696   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.338   4.945   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.414   1.717   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.627   2.665   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.055   2.089   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.268   3.037   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.270   0.564   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.259   2.835   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.435   1.305   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.197   0.388   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.373  -1.142   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.336   0.535   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.885   4.185   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.282   3.537   0.000  0.00  0.00           C+0
CONECT    1    2    6   30                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   13   25                                             
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   16                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    7                                                       
CONECT   14   12   15   25                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   10                                                       
CONECT   17   15   18   20                                                  
CONECT   18   17   11   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   14    7   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    1   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
[(1R,10S,12S,13S,14S,16S,17S,18R)-18-(Acetyloxy)-4-methoxy-14-methyl-8,15-diazahexacyclo[14.2.1.0,.0,.0,.0,]nonadeca-2(7),3,5,8-tetraen-13-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₂₈N₂O₅

Average Mass

424.4970 Da

Monoisotopic Mass

424.19982 Da

IUPAC Name

[(1R,10S,12S,13S,14S,16S,17S,18R)-18-(acetyloxy)-4-methoxy-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-13-yl]methyl acetate

Traditional Name

[(1R,10S,12S,13S,14S,16S,17S,18R)-18-(acetyloxy)-4-methoxy-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-13-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C2N=C3[C@@H]4C[C@@H]5[C@H]6[C@H](C[C@@]3([C@@H]6OC(C)=O)C2=C1)N4[C@@H](C)[C@H]5COC(C)=O

InChI Identifier

InChI=1S/C24H28N2O5/c1-11-16(10-30-12(2)27)15-8-19-22-24(17-7-14(29-4)5-6-18(17)25-22)9-20(26(11)19)21(15)23(24)31-13(3)28/h5-7,11,15-16,19-21,23H,8-10H2,1-4H3/t11-,15-,16+,19-,20-,21-,23+,24+/m0/s1

InChI Key

NVBKJHMKBGTOJC-LYQRILJPSA-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
Vinca major	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ajmaline-sarpagine alkaloids

Sub Class

Not Available

Direct Parent

Ajmaline-sarpagine alkaloids

Alternative Parents

Substituents

Sarpagine-skeleton
3-alkylindole
Quinolizidine
Indole or derivatives
Quinuclidine
Anisole
Aralkylamine
Azepane
Alkyl aryl ether
Benzenoid
Piperidine
Dicarboxylic acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Ketimine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Amine
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	2.44	ALOGPS
logP	1.96	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	6.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	113.72 m³·mol⁻¹	ChemAxon
Polarizability	45.87 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	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

163067639

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Vincawajine (NP0066714)

MOL for NP0066714 ((-)-Vincawajine)

3D MOL for NP0066714 ((-)-Vincawajine)

3D SDF for NP0066714 ((-)-Vincawajine)

3D-SDF for NP0066714 ((-)-Vincawajine)

PDB for NP0066714 ((-)-Vincawajine)

3D PDB for NP0066714 ((-)-Vincawajine)

SMILES for NP0066714 ((-)-Vincawajine)

INCHI for NP0066714 ((-)-Vincawajine)

Structure for NP0066714 ((-)-Vincawajine)

3D Structure for NP0066714 ((-)-Vincawajine)