NP-MRD: Showing NP-Card for Turbinatine (NP0026540)

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Record Information

Version

2.0

Created at

2021-06-19 18:23:17 UTC

Updated at

2021-06-29 23:52:08 UTC

NP-MRD ID

NP0026540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Turbinatine

Provided By

JEOL Database JEOL Logo

Description

Turbinatine is found in Chimarrhis turbinata. Turbinatine was first documented in 2003 (PMID: 12880329). Based on a literature review very few articles have been published on Turbinatine (PMID: 15568781).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120233D          

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M  END

     RDKit          3D

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 12 50  1  0
  4 43  1  6
  3 42  1  6
 26 61  1  6
  6 44  1  0
  7 45  1  0
  2 41  1  0
  1 39  1  0
  1 40  1  0
 11 46  1  0
 11 47  1  0
 11 48  1  0
M  END


  Mrv1652306192120233D          

 72 76  0  0  0  0            999 V2000
   -1.8999    2.6181    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167    1.3164   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210    0.2687   -0.8034 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1820    0.6945   -1.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2374    1.7132   -2.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257    2.3266   -3.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130    3.2405   -4.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    1.9984   -3.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909    3.0193   -3.7610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139    0.9630   -2.9526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6799    1.1428   -3.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    1.0348   -0.1620 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2046   -0.1544    0.8078 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0880    0.1337    1.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737    0.8170    1.9746 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8207    0.8347    3.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    1.4171    3.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3163    1.2756    5.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4702    0.5794    5.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2868    0.0021    5.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9543    0.1302    4.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.3119    3.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.0967    3.6173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0441   -1.6048    2.3298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1454   -0.5500    1.2903 N   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9994   -0.9569    0.1614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2482   -1.4638    0.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842   -2.2414   -0.2993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2393   -3.3798   -0.7288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688   -4.1825   -1.6681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0660   -5.3203   -2.1640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6469   -6.0215   -3.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2486   -4.7362   -1.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0107   -5.5099   -1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0986   -3.5772   -0.4963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2325   -4.1101    0.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703   -2.6857    0.4246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0656   -1.5585    0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    3.2166    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938    3.1368   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0764    0.9273    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997   -0.0893   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855   -0.2254   -1.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537    2.1690   -2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169    3.4885   -4.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883    0.2567   -3.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946    2.0169   -3.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    1.2390   -4.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781    1.9329    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208    1.2735   -0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -1.0026    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6993    1.2527    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689    1.9620    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2306    1.7178    5.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    0.4831    6.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.5373    6.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9130   -1.9494    4.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -0.4534    4.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -2.4739    1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -1.9579    2.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -1.7598   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429   -1.6100   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -3.5691   -2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009   -4.9203   -2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -6.0329   -1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5897   -6.1756   -3.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9935   -5.4012   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8812   -5.6415   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5116   -2.9971   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6347   -3.3433    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236   -3.2303    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4642   -0.9948    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 22 21  1  0  0  0  0
 22 14  2  0  0  0  0
 33 34  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 22 23  1  0  0  0  0
 14 13  1  0  0  0  0
 25 24  1  0  0  0  0
 24 23  1  0  0  0  0
 25 13  1  0  0  0  0
 31 32  1  0  0  0  0
 28 37  1  0  0  0  0
 37 35  1  0  0  0  0
 19 18  2  0  0  0  0
 35 33  1  0  0  0  0
 25 26  1  0  0  0  0
 13 12  1  0  0  0  0
 12  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3 26  1  0  0  0  0
 18 17  1  0  0  0  0
  4  5  1  0  0  0  0
 17 16  2  0  0  0  0
  5  8  1  0  0  0  0
 33 30  1  0  0  0  0
  5  6  2  0  0  0  0
 21 20  2  0  0  0  0
  6  7  1  0  0  0  0
 20 19  1  0  0  0  0
  8 10  1  0  0  0  0
 21 16  1  0  0  0  0
  8  9  2  0  0  0  0
 26 27  1  0  0  0  0
 30 29  1  0  0  0  0
  3  2  1  0  0  0  0
 29 28  1  0  0  0  0
  2  1  2  3  0  0  0
 10 11  1  0  0  0  0
 30 31  1  0  0  0  0
 28 27  1  0  0  0  0
 28 62  1  6  0  0  0
 33 67  1  1  0  0  0
 34 68  1  0  0  0  0
 35 69  1  6  0  0  0
 36 70  1  0  0  0  0
 37 71  1  1  0  0  0
 38 72  1  0  0  0  0
 31 64  1  0  0  0  0
 31 65  1  0  0  0  0
 30 63  1  6  0  0  0
 32 66  1  0  0  0  0
 19 55  1  0  0  0  0
 18 54  1  0  0  0  0
 17 53  1  0  0  0  0
 20 56  1  0  0  0  0
 15 52  1  0  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 23 57  1  0  0  0  0
 23 58  1  0  0  0  0
 13 51  1  6  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
  4 43  1  6  0  0  0
  3 42  1  6  0  0  0
 26 61  1  6  0  0  0
  6 44  1  0  0  0  0
  7 45  1  0  0  0  0
  2 41  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
 11 46  1  0  0  0  0
 11 47  1  0  0  0  0
 11 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C([H])=C(/C(=O)OC([H])([H])[H])[C@@]1([H])C([H])([H])[C@]2([H])N(C([H])([H])C([H])([H])C3=C2N([H])C2=C([H])C([H])=C([H])C([H])=C32)[C@@]([H])(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])[C@@]1([H])C([H])=C([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H34N2O9/c1-3-13-16(17(11-30)26(35)36-2)10-19-21-15(14-6-4-5-7-18(14)28-21)8-9-29(19)25(13)38-27-24(34)23(33)22(32)20(12-31)37-27/h3-7,11,13,16,19-20,22-25,27-28,30-34H,1,8-10,12H2,2H3/b17-11-/t13-,16-,19-,20-,22-,23+,24-,25-,27+/m0/s1

> <INCHI_KEY>
XAYUCVICBPYPRE-LPRPFWDGSA-N

> <FORMULA>
C27H34N2O9

> <MOLECULAR_WEIGHT>
530.574

> <EXACT_MASS>
530.226430683

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.371822325178655

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2Z)-2-[(2S,3S,4S,12bS)-3-ethenyl-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
0.7910391563333348

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.208396598661105

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.227240000790827

> <JCHEM_PKA_STRONGEST_BASIC>
4.9482948670068625

> <JCHEM_POLAR_SURFACE_AREA>
164.94

> <JCHEM_REFRACTIVITY>
135.2413

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z)-2-[(2S,3S,4S,12bS)-3-ethenyl-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -1.8999    2.6181    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167    1.3164   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210    0.2687   -0.8034 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1820    0.6945   -1.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2374    1.7132   -2.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257    2.3266   -3.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130    3.2405   -4.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    1.9984   -3.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909    3.0193   -3.7610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139    0.9630   -2.9526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6799    1.1428   -3.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    1.0348   -0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2046   -0.1544    0.8078 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0880    0.1337    1.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737    0.8170    1.9746 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8207    0.8347    3.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    1.4171    3.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3163    1.2756    5.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4702    0.5794    5.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2868    0.0021    5.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9543    0.1302    4.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.3119    3.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.0967    3.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441   -1.6048    2.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -0.5500    1.2903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9994   -0.9569    0.1614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2482   -1.4638    0.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842   -2.2414   -0.2993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2393   -3.3798   -0.7288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688   -4.1825   -1.6681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0660   -5.3203   -2.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469   -6.0215   -3.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2486   -4.7362   -1.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0107   -5.5099   -1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0986   -3.5772   -0.4963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2325   -4.1101    0.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703   -2.6857    0.4246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0656   -1.5585    0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    3.2166    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938    3.1368   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0764    0.9273    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997   -0.0893   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855   -0.2254   -1.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537    2.1690   -2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169    3.4885   -4.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883    0.2567   -3.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946    2.0169   -3.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    1.2390   -4.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781    1.9329    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208    1.2735   -0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -1.0026    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6993    1.2527    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689    1.9620    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2306    1.7178    5.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    0.4831    6.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.5373    6.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9130   -1.9494    4.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -0.4534    4.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -2.4739    1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -1.9579    2.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -1.7598   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429   -1.6100   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -3.5691   -2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009   -4.9203   -2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -6.0329   -1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5897   -6.1756   -3.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9935   -5.4012   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8812   -5.6415   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5116   -2.9971   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6347   -3.3433    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236   -3.2303    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4642   -0.9948    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 22 21  1  0
 22 14  2  0
 33 34  1  0
 35 36  1  0
 37 38  1  0
 22 23  1  0
 14 13  1  0
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 31 32  1  0
 28 37  1  0
 37 35  1  0
 19 18  2  0
 35 33  1  0
 25 26  1  0
 13 12  1  0
 12  4  1  0
  4  3  1  0
  3 26  1  0
 18 17  1  0
  4  5  1  0
 17 16  2  0
  5  8  1  0
 33 30  1  0
  5  6  2  0
 21 20  2  0
  6  7  1  0
 20 19  1  0
  8 10  1  0
 21 16  1  0
  8  9  2  0
 26 27  1  0
 30 29  1  0
  3  2  1  0
 29 28  1  0
  2  1  2  3
 10 11  1  0
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 28 62  1  6
 33 67  1  1
 34 68  1  0
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 13 51  1  6
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 12 50  1  0
  4 43  1  6
  3 42  1  6
 26 61  1  6
  6 44  1  0
  7 45  1  0
  2 41  1  0
  1 39  1  0
  1 40  1  0
 11 46  1  0
 11 47  1  0
 11 48  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.900   2.618   0.098  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.117   1.316  -0.132  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.221   0.269  -0.803  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.182   0.695  -1.348  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.237   1.713  -2.488  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.826   2.327  -3.042  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.813   3.240  -4.067  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.557   1.998  -3.127  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.791   3.019  -3.761  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.414   0.963  -2.953  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.680   1.143  -3.590  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.114   1.035  -0.162  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.205  -0.154   0.808  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.088   0.134   1.986  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.274   0.817   1.975  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.821   0.835   3.241  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.008   1.417   3.701  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.316   1.276   5.057  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.470   0.579   5.918  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.287   0.002   5.443  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.954   0.130   4.080  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.873  -0.312   3.275  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.656  -1.097   3.617  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.044  -1.605   2.330  0.00  0.00           C+0
HETATM   25  N   UNK     0      -0.145  -0.550   1.290  0.00  0.00           N+0
HETATM   26  C   UNK     0      -0.999  -0.957   0.161  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.248  -1.464   0.646  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.984  -2.241  -0.299  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.239  -3.380  -0.729  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.969  -4.183  -1.668  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.066  -5.320  -2.164  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.647  -6.021  -3.258  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.249  -4.736  -1.019  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.011  -5.510  -1.952  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.099  -3.577  -0.496  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.232  -4.110   0.204  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.270  -2.686   0.425  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.066  -1.559   0.822  0.00  0.00           O+0
HETATM   39  H   UNK     0      -2.655   3.217   0.601  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.994   3.137  -0.189  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.076   0.927   0.210  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.800  -0.089  -1.665  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.586  -0.225  -1.802  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.854   2.169  -2.740  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.117   3.489  -4.266  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.288   0.257  -3.389  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.195   2.017  -3.179  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.554   1.239  -4.673  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.778   1.933   0.367  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.121   1.274  -0.523  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.660  -1.003   0.274  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.699   1.253   1.169  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.669   1.962   3.035  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.231   1.718   5.446  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.729   0.483   6.969  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.632  -0.537   6.120  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.913  -1.949   4.255  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.034  -0.453   4.178  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.496  -2.474   1.930  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.036  -1.958   2.634  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.488  -1.760  -0.387  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.243  -1.610  -1.157  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.236  -3.569  -2.540  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.101  -4.920  -2.493  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.854  -6.033  -1.359  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.590  -6.176  -3.031  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.994  -5.401  -0.184  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.881  -5.641  -1.518  0.00  0.00           H+0
HETATM   69  H   UNK     0      -5.512  -2.997  -1.331  0.00  0.00           H+0
HETATM   70  H   UNK     0      -6.635  -3.343   0.662  0.00  0.00           H+0
HETATM   71  H   UNK     0      -4.024  -3.230   1.345  0.00  0.00           H+0
HETATM   72  H   UNK     0      -4.464  -0.995   1.351  0.00  0.00           H+0
CONECT    1    2   39   40                                                  
CONECT    2    3    1   41                                                  
CONECT    3    4   26    2   42                                             
CONECT    4   12    3    5   43                                             
CONECT    5    4    8    6                                                  
CONECT    6    5    7   44                                                  
CONECT    7    6   45                                                       
CONECT    8    5   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   46   47   48                                             
CONECT   12   13    4   49   50                                             
CONECT   13   14   25   12   51                                             
CONECT   14   15   22   13                                                  
CONECT   15   16   14   52                                                  
CONECT   16   15   17   21                                                  
CONECT   17   18   16   53                                                  
CONECT   18   19   17   54                                                  
CONECT   19   18   20   55                                                  
CONECT   20   21   19   56                                                  
CONECT   21   22   20   16                                                  
CONECT   22   21   14   23                                                  
CONECT   23   22   24   57   58                                             
CONECT   24   25   23   59   60                                             
CONECT   25   24   13   26                                                  
CONECT   26   25    3   27   61                                             
CONECT   27   26   28                                                       
CONECT   28   37   29   27   62                                             
CONECT   29   30   28                                                       
CONECT   30   33   29   31   63                                             
CONECT   31   32   30   64   65                                             
CONECT   32   31   66                                                       
CONECT   33   34   35   30   67                                             
CONECT   34   33   68                                                       
CONECT   35   36   37   33   69                                             
CONECT   36   35   70                                                       
CONECT   37   38   28   35   71                                             
CONECT   38   37   72                                                       
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    2                                                            
CONECT   42    3                                                            
CONECT   43    4                                                            
CONECT   44    6                                                            
CONECT   45    7                                                            
CONECT   46   11                                                            
CONECT   47   11                                                            
CONECT   48   11                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   15                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   23                                                            
CONECT   58   23                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   26                                                            
CONECT   62   28                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   31                                                            
CONECT   66   32                                                            
CONECT   67   33                                                            
CONECT   68   34                                                            
CONECT   69   35                                                            
CONECT   70   36                                                            
CONECT   71   37                                                            
CONECT   72   38                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  152    0
END

RDKit          3D

72 76  0  0  0  0  0  0  0  0999 V2000
   -1.8999    2.6181    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167    1.3164   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210    0.2687   -0.8034 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1820    0.6945   -1.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2374    1.7132   -2.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257    2.3266   -3.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130    3.2405   -4.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    1.9984   -3.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909    3.0193   -3.7610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139    0.9630   -2.9526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6799    1.1428   -3.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    1.0348   -0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2046   -0.1544    0.8078 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0880    0.1337    1.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737    0.8170    1.9746 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8207    0.8347    3.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    1.4171    3.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3163    1.2756    5.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4702    0.5794    5.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2868    0.0021    5.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9543    0.1302    4.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.3119    3.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.0967    3.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441   -1.6048    2.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -0.5500    1.2903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9994   -0.9569    0.1614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2482   -1.4638    0.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842   -2.2414   -0.2993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2393   -3.3798   -0.7288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688   -4.1825   -1.6681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0660   -5.3203   -2.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469   -6.0215   -3.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2486   -4.7362   -1.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0107   -5.5099   -1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0986   -3.5772   -0.4963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2325   -4.1101    0.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703   -2.6857    0.4246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0656   -1.5585    0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    3.2166    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938    3.1368   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0764    0.9273    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997   -0.0893   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855   -0.2254   -1.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537    2.1690   -2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1169    3.4885   -4.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883    0.2567   -3.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946    2.0169   -3.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    1.2390   -4.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781    1.9329    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208    1.2735   -0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -1.0026    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6993    1.2527    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689    1.9620    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2306    1.7178    5.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    0.4831    6.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.5373    6.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9130   -1.9494    4.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -0.4534    4.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -2.4739    1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -1.9579    2.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -1.7598   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429   -1.6100   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -3.5691   -2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009   -4.9203   -2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -6.0329   -1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5897   -6.1756   -3.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9935   -5.4012   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8812   -5.6415   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5116   -2.9971   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6347   -3.3433    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236   -3.2303    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4642   -0.9948    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 22 21  1  0
 22 14  2  0
 33 34  1  0
 35 36  1  0
 37 38  1  0
 22 23  1  0
 14 13  1  0
 25 24  1  0
 24 23  1  0
 25 13  1  0
 31 32  1  0
 28 37  1  0
 37 35  1  0
 19 18  2  0
 35 33  1  0
 25 26  1  0
 13 12  1  0
 12  4  1  0
  4  3  1  0
  3 26  1  0
 18 17  1  0
  4  5  1  0
 17 16  2  0
  5  8  1  0
 33 30  1  0
  5  6  2  0
 21 20  2  0
  6  7  1  0
 20 19  1  0
  8 10  1  0
 21 16  1  0
  8  9  2  0
 26 27  1  0
 30 29  1  0
  3  2  1  0
 29 28  1  0
  2  1  2  3
 10 11  1  0
 30 31  1  0
 28 27  1  0
 28 62  1  6
 33 67  1  1
 34 68  1  0
 35 69  1  6
 36 70  1  0
 37 71  1  1
 38 72  1  0
 31 64  1  0
 31 65  1  0
 30 63  1  6
 32 66  1  0
 19 55  1  0
 18 54  1  0
 17 53  1  0
 20 56  1  0
 15 52  1  0
 24 59  1  0
 24 60  1  0
 23 57  1  0
 23 58  1  0
 13 51  1  6
 12 49  1  0
 12 50  1  0
  4 43  1  6
  3 42  1  6
 26 61  1  6
  6 44  1  0
  7 45  1  0
  2 41  1  0
  1 39  1  0
  1 40  1  0
 11 46  1  0
 11 47  1  0
 11 48  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄N₂O₉

Average Mass

530.5740 Da

Monoisotopic Mass

530.22643 Da

IUPAC Name

methyl (2Z)-2-[(2S,3S,4S,12bS)-3-ethenyl-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate

Traditional Name

methyl (2Z)-2-[(2S,3S,4S,12bS)-3-ethenyl-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O\C([H])=C(/C(=O)OC([H])([H])[H])[C@@]1([H])C([H])([H])[C@]2([H])N(C([H])([H])C([H])([H])C3=C2N([H])C2=C([H])C([H])=C([H])C([H])=C32)[C@@]([H])(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])[C@@]1([H])C([H])=C([H])[H]

InChI Identifier

InChI=1S/C27H34N2O9/c1-3-13-16(17(11-30)26(35)36-2)10-19-21-15(14-6-4-5-7-18(14)28-21)8-9-29(19)25(13)38-27-24(34)23(33)22(32)20(12-31)37-27/h3-7,11,13,16,19-20,22-25,27-28,30-34H,1,8-10,12H2,2H3/b17-11-/t13-,16-,19-,20-,22-,23+,24-,25-,27+/m0/s1

InChI Key

XAYUCVICBPYPRE-LPRPFWDGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Chimarrhis turbinata	JEOL database	Cardoso, C. L., et al, J. Nat. Prod. 66, 1017 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Beta-carboline
Pyridoindole
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Quinolizine
3-alkylindole
Indole
Indole or derivatives
Piperidine
Monosaccharide
Benzenoid
Oxane
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Pyrrole
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Hemiaminal
Secondary alcohol
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Enol
Organooxygen compound
Alcohol
Organopnictogen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Primary 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	0.32	ALOGPS
logP	0.79	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.94 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.24 m³·mol⁻¹	ChemAxon
Polarizability	56.37 Å³	ChemAxon
Number of Rings	5	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

23327200

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cardoso CL, Castro-Gamboa I, Silva DH, Furlan M, Epifanio Rde A, Pinto Ada C, Moraes de Rezende C, Lima JA, Bolzani Vda S: Indole glucoalkaloids from Chimarrhis turbinata and their evaluation as antioxidant agents and acetylcholinesterase inhibitors. J Nat Prod. 2004 Nov;67(11):1882-5. doi: 10.1021/np049863m. [PubMed:15568781 ]
Cardoso CL, Siqueira Silva DH, Tomazela DM, Verli H, Young MC, Furlan M, Eberlin MN, da Silva Bolzani V: Turbinatine, a potential key intermediate in the biosynthesis of corynanthean-type indole alkaloids. J Nat Prod. 2003 Jul;66(7):1017-21. doi: 10.1021/np020547m. [PubMed:12880329 ]
Cardoso, C. L., et al. (2003). Cardoso, C. L., et al, J. Nat. Prod. 66, 1017 (2003). J. Nat. Prod..

Showing NP-Card for Turbinatine (NP0026540)

MOL for NP0026540 (Turbinatine)

3D MOL for NP0026540 (Turbinatine)

3D SDF for NP0026540 (Turbinatine)

3D-SDF for NP0026540 (Turbinatine)

PDB for NP0026540 (Turbinatine)

3D PDB for NP0026540 (Turbinatine)

SMILES for NP0026540 (Turbinatine)

INCHI for NP0026540 (Turbinatine)

Structure for NP0026540 (Turbinatine)

3D Structure for NP0026540 (Turbinatine)