NP-MRD: Showing NP-Card for voacalgine B (NP0042778)

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Record Information

Version

2.0

Created at

2021-06-21 00:21:12 UTC

Updated at

2021-06-30 00:18:04 UTC

NP-MRD ID

NP0042778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

voacalgine B

Provided By

JEOL Database JEOL Logo

Description

Voacalgine B belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. voacalgine B is found in Voacanga grandifolia. voacalgine B was first documented in 2013 (Hirasawa, Y., et al.). Based on a literature review very few articles have been published on Voacalgine B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102213D          

 50 54  0  0  0  0            999 V2000
   -1.0909   -0.1369    5.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    0.1400    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920    0.2690    3.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6077    0.2622    2.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9199    0.0917    2.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9096    0.1667    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5013    0.7130    0.5216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1469    0.1567    0.0563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7971    0.6593   -1.3703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6783   -0.2027   -2.0476 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6860    0.3013   -1.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    1.4819   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099    1.6829   -0.8647 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450    2.7730   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    0.6581   -1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903    0.4340   -1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120   -0.7072   -2.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7866   -1.5895   -2.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -2.6850   -3.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135   -1.3716   -2.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -0.2254   -2.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2575    2.3349   -0.4987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5788    1.9698    0.9613 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0736    0.5135    1.1144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4952    2.1125   -1.2895 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4300    2.7480   -2.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -0.1605    5.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855   -1.1106    5.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7623    0.6582    5.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3695   -0.1532    3.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    1.8062    0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    0.4513   -0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2417   -0.9389    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8028   -0.1489   -3.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760   -1.2558   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    3.3939    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5202    2.3532    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    1.1193   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743   -0.9069   -2.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -3.2147   -3.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911   -2.0608   -3.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    3.3970   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388    2.6662    1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106    2.1263    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256   -0.1659    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    2.6114   -3.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    3.8293   -2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6263    2.3664   -3.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0  0  0  0
  9  8  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
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 12 22  1  0  0  0  0
  8 33  1  6  0  0  0
 18 17  1  0  0  0  0
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 15 13  1  0  0  0  0
  4  2  1  0  0  0  0
 17 16  2  0  0  0  0
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  2  3  2  0  0  0  0
 22 25  1  0  0  0  0
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 23 45  1  0  0  0  0
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  5 30  1  0  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
  1 27  1  0  0  0  0
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  1 29  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 26 48  1  0  0  0  0
 26 49  1  0  0  0  0
 26 50  1  0  0  0  0
 19 42  1  0  0  0  0
M  END

     RDKit          3D

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   -0.6103    0.1400    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8450    2.7730   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    0.6581   -1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903    0.4340   -1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120   -0.7072   -2.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7866   -1.5895   -2.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -2.6850   -3.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135   -1.3716   -2.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -0.2254   -2.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2575    2.3349   -0.4987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5788    1.9698    0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736    0.5135    1.1144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4952    2.1125   -1.2895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300    2.7480   -2.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -0.1605    5.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4982    1.8062    0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3777    2.6114   -3.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
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 22 23  1  0
  9  8  1  0
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 11 21  1  0
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M  END


  Mrv1652306212102213D          

 50 54  0  0  0  0            999 V2000
   -1.0909   -0.1369    5.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    0.1400    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920    0.2690    3.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6077    0.2622    2.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5013    0.7130    0.5216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1469    0.1567    0.0563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7971    0.6593   -1.3703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6783   -0.2027   -2.0476 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6860    0.3013   -1.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    1.4819   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099    1.6829   -0.8647 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450    2.7730   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    0.6581   -1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903    0.4340   -1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5202    2.3532    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    1.1193   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743   -0.9069   -2.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -3.2147   -3.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3106    2.1263    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256   -0.1659    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    2.6114   -3.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    3.8293   -2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6263    2.3664   -3.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0  0  0  0
  9  8  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
 11 21  1  0  0  0  0
 15 21  2  0  0  0  0
 21 20  1  0  0  0  0
 11 12  2  0  0  0  0
 20 18  2  0  0  0  0
  8  7  1  0  0  0  0
 24  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
 12 22  1  0  0  0  0
  8 33  1  6  0  0  0
 18 17  1  0  0  0  0
 24 47  1  6  0  0  0
 15 13  1  0  0  0  0
  4  2  1  0  0  0  0
 17 16  2  0  0  0  0
  2  1  1  0  0  0  0
 16 15  1  0  0  0  0
  2  3  2  0  0  0  0
 22 25  1  0  0  0  0
 22 44  1  1  0  0  0
  9 25  1  0  0  0  0
  9 34  1  6  0  0  0
  9 10  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 25 26  1  0  0  0  0
 13 12  1  0  0  0  0
 18 19  1  0  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
 20 43  1  0  0  0  0
 17 41  1  0  0  0  0
 16 40  1  0  0  0  0
 23 45  1  0  0  0  0
 23 46  1  0  0  0  0
  5 30  1  0  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 26 48  1  0  0  0  0
 26 49  1  0  0  0  0
 26 50  1  0  0  0  0
 19 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1[H])N(C1=C2C([H])([H])[C@]2([H])N(C([H])([H])[H])[C@@]1([H])C([H])([H])[C@@]1([H])C(=C([H])OC([H])([H])[C@@]21[H])C(=O)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-11(24)16-9-26-10-17-13(16)7-20-21-15(8-19(17)22(20)2)14-6-12(25)4-5-18(14)23(21)3/h4-6,9,13,17,19-20,25H,7-8,10H2,1-3H3/t13-,17+,19-,20-/m0/s1

> <INCHI_KEY>
APHAMAWISTWJNT-KGFWFAMKSA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.434

> <EXACT_MASS>
352.178692641

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.71076137979589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1S,12S,13R,18R)-7-hydroxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethan-1-one

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.0664273136666664

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.217769649393023

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.55087238031538

> <JCHEM_PKA_STRONGEST_BASIC>
6.620005787444563

> <JCHEM_POLAR_SURFACE_AREA>
54.7

> <JCHEM_REFRACTIVITY>
100.74739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,12S,13R,18R)-7-hydroxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
   -1.0909   -0.1369    5.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    0.1400    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920    0.2690    3.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6077    0.2622    2.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9199    0.0917    2.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9096    0.1667    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5013    0.7130    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469    0.1567    0.0563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7971    0.6593   -1.3703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6783   -0.2027   -2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    0.3013   -1.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    1.4819   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099    1.6829   -0.8647 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450    2.7730   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    0.6581   -1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903    0.4340   -1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120   -0.7072   -2.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7866   -1.5895   -2.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -2.6850   -3.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135   -1.3716   -2.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -0.2254   -2.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2575    2.3349   -0.4987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5788    1.9698    0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736    0.5135    1.1144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4952    2.1125   -1.2895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300    2.7480   -2.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -0.1605    5.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855   -1.1106    5.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7623    0.6582    5.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3695   -0.1532    3.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    1.8062    0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    0.4513   -0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2417   -0.9389    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7030    0.5215   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028   -0.1489   -3.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760   -1.2558   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    3.3939    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000    3.3736   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5202    2.3532    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    1.1193   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743   -0.9069   -2.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -3.2147   -3.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911   -2.0608   -3.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    3.3970   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388    2.6662    1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106    2.1263    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256   -0.1659    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    2.6114   -3.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    3.8293   -2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6263    2.3664   -3.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
  9  8  1  0
 23 24  1  0
  8 24  1  0
 11 21  1  0
 15 21  2  0
 21 20  1  0
 11 12  2  0
 20 18  2  0
  8  7  1  0
 24  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
 12 22  1  0
  8 33  1  6
 18 17  1  0
 24 47  1  6
 15 13  1  0
  4  2  1  0
 17 16  2  0
  2  1  1  0
 16 15  1  0
  2  3  2  0
 22 25  1  0
 22 44  1  1
  9 25  1  0
  9 34  1  6
  9 10  1  0
 13 14  1  0
 10 11  1  0
 25 26  1  0
 13 12  1  0
 18 19  1  0
 10 35  1  0
 10 36  1  0
 20 43  1  0
 17 41  1  0
 16 40  1  0
 23 45  1  0
 23 46  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 19 42  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.091  -0.137   5.025  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.610   0.140   3.622  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.592   0.269   3.390  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.608   0.262   2.509  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.920   0.092   2.729  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.910   0.167   1.784  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.501   0.713   0.522  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.147   0.157   0.056  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.797   0.659  -1.370  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.678  -0.203  -2.048  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.686   0.301  -1.716  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.864   1.482  -1.021  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.210   1.683  -0.865  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.845   2.773  -0.157  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.909   0.658  -1.484  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.290   0.434  -1.610  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.712  -0.707  -2.298  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.787  -1.589  -2.836  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.268  -2.685  -3.495  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.414  -1.372  -2.712  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.966  -0.225  -2.023  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.258   2.335  -0.499  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.579   1.970   0.961  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.074   0.514   1.114  0.00  0.00           C+0
HETATM   25  N   UNK     0      -1.495   2.112  -1.290  0.00  0.00           N+0
HETATM   26  C   UNK     0      -1.430   2.748  -2.605  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.231  -0.161   5.702  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.585  -1.111   5.069  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.762   0.658   5.359  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.369  -0.153   3.684  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.498   1.806   0.607  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.283   0.451  -0.200  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.242  -0.939   0.031  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.703   0.522  -1.977  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.803  -0.149  -3.137  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.776  -1.256  -1.761  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.099   3.394   0.341  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.400   3.374  -0.882  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.520   2.353   0.593  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.018   1.119  -1.188  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.774  -0.907  -2.410  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.514  -3.215  -3.798  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.691  -2.061  -3.133  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.012   3.397  -0.539  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.339   2.666   1.343  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.311   2.126   1.584  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.226  -0.166   0.956  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.378   2.611  -3.138  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.290   3.829  -2.496  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.626   2.366  -3.242  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4   24    5    2                                                  
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    8    6   31   32                                             
CONECT    8    9   24    7   33                                             
CONECT    9    8   25   34   10                                             
CONECT   10    9   11   35   36                                             
CONECT   11   21   12   10                                                  
CONECT   12   11   22   13                                                  
CONECT   13   15   14   12                                                  
CONECT   14   13   37   38   39                                             
CONECT   15   21   13   16                                                  
CONECT   16   17   15   40                                                  
CONECT   17   18   16   41                                                  
CONECT   18   20   17   19                                                  
CONECT   19   18   42                                                       
CONECT   20   21   18   43                                                  
CONECT   21   11   15   20                                                  
CONECT   22   23   12   25   44                                             
CONECT   23   22   24   45   46                                             
CONECT   24   23    8    4   47                                             
CONECT   25   22    9   26                                                  
CONECT   26   25   48   49   50                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    5                                                            
CONECT   31    7                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   22                                                            
CONECT   45   23                                                            
CONECT   46   23                                                            
CONECT   47   24                                                            
CONECT   48   26                                                            
CONECT   49   26                                                            
CONECT   50   26                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  108    0
END

RDKit          3D

50 54  0  0  0  0  0  0  0  0999 V2000
   -1.0909   -0.1369    5.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    0.1400    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920    0.2690    3.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6077    0.2622    2.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9199    0.0917    2.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9096    0.1667    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5013    0.7130    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469    0.1567    0.0563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7971    0.6593   -1.3703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6783   -0.2027   -2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    0.3013   -1.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    1.4819   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099    1.6829   -0.8647 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450    2.7730   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    0.6581   -1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903    0.4340   -1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120   -0.7072   -2.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7866   -1.5895   -2.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -2.6850   -3.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135   -1.3716   -2.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -0.2254   -2.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2575    2.3349   -0.4987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5788    1.9698    0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736    0.5135    1.1144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4952    2.1125   -1.2895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300    2.7480   -2.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -0.1605    5.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855   -1.1106    5.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7623    0.6582    5.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3695   -0.1532    3.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    1.8062    0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    0.4513   -0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2417   -0.9389    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7030    0.5215   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028   -0.1489   -3.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760   -1.2558   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    3.3939    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000    3.3736   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5202    2.3532    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    1.1193   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743   -0.9069   -2.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -3.2147   -3.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911   -2.0608   -3.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    3.3970   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388    2.6662    1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106    2.1263    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256   -0.1659    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    2.6114   -3.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    3.8293   -2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6263    2.3664   -3.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
  9  8  1  0
 23 24  1  0
  8 24  1  0
 11 21  1  0
 15 21  2  0
 21 20  1  0
 11 12  2  0
 20 18  2  0
  8  7  1  0
 24  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
 12 22  1  0
  8 33  1  6
 18 17  1  0
 24 47  1  6
 15 13  1  0
  4  2  1  0
 17 16  2  0
  2  1  1  0
 16 15  1  0
  2  3  2  0
 22 25  1  0
 22 44  1  1
  9 25  1  0
  9 34  1  6
  9 10  1  0
 13 14  1  0
 10 11  1  0
 25 26  1  0
 13 12  1  0
 18 19  1  0
 10 35  1  0
 10 36  1  0
 20 43  1  0
 17 41  1  0
 16 40  1  0
 23 45  1  0
 23 46  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 19 42  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₂O₃

Average Mass

352.4340 Da

Monoisotopic Mass

352.17869 Da

IUPAC Name

1-[(1S,12S,13R,18R)-7-hydroxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethan-1-one

Traditional Name

1-[(1S,12S,13R,18R)-7-hydroxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethanone

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1[H])N(C1=C2C([H])([H])[C@]2([H])N(C([H])([H])[H])[C@@]1([H])C([H])([H])[C@@]1([H])C(=C([H])OC([H])([H])[C@@]21[H])C(=O)C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H24N2O3/c1-11(24)16-9-26-10-17-13(16)7-20-21-15(8-19(17)22(20)2)14-6-12(25)4-5-18(14)23(21)3/h4-6,9,13,17,19-20,25H,7-8,10H2,1-3H3/t13-,17+,19-,20-/m0/s1

InChI Key

APHAMAWISTWJNT-KGFWFAMKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Voacanga grandifolia	JEOL database	Hirasawa, Y., et. al, Tetrahedron 69, 10869 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Beta-carboline
Pyridoindole
3-alkylindole
Hydroxyindole
N-alkylindole
Indole
Indole or derivatives
Phenol
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
N-methylpyrrole
Piperidine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Vinylogous ester
Pyrrole
Ketone
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	2.42	ALOGPS
logP	2.07	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	6.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.75 m³·mol⁻¹	ChemAxon
Polarizability	38.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

102225983

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hirasawa, Y., et al. (2013). Hirasawa, Y., et. al, Tetrahedron 69, 10869 (2013). Tetrahedron.

Showing NP-Card for voacalgine B (NP0042778)

MOL for NP0042778 (voacalgine B)

3D MOL for NP0042778 (voacalgine B)

3D SDF for NP0042778 (voacalgine B)

3D-SDF for NP0042778 (voacalgine B)

PDB for NP0042778 (voacalgine B)

3D PDB for NP0042778 (voacalgine B)

SMILES for NP0042778 (voacalgine B)

INCHI for NP0042778 (voacalgine B)

Structure for NP0042778 (voacalgine B)

3D Structure for NP0042778 (voacalgine B)