NP-MRD: Showing NP-Card for 7beta-hydroxy-7H-mitraciliatine (NP0042878)

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Record Information

Version

1.0

Created at

2021-06-21 00:26:00 UTC

Updated at

2021-06-30 00:18:14 UTC

NP-MRD ID

NP0042878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7beta-hydroxy-7H-mitraciliatine

Provided By

JEOL Database JEOL Logo

Description

7Beta-Hydroxy-7H-mitraciliatine 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. 7beta-hydroxy-7H-mitraciliatine is found in Mitragyna speciosa. It was first documented in 2014 (Ali, Z., et al.). Based on a literature review very few articles have been published on 7beta-Hydroxy-7H-mitraciliatine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102263D          

 60 63  0  0  0  0            999 V2000
    3.7554   -0.1820   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3141   -0.6658   -1.1368 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.0695    2.7707    2.2725 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102263D          

 60 63  0  0  0  0            999 V2000
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    2.3141   -0.6658   -1.1368 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.3327   -2.6680   -2.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282   -3.4585    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5436   -3.1607    1.7321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2712   -4.7200    0.6486 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368   -5.7049    1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169    0.9097   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019   -0.5148   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3583   -0.5836   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192   -1.7403   -1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255   -0.1868   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650   -0.9120    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0952    1.6293   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    1.4688    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8245    2.8524    3.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047    3.1237    2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    3.7467    0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332    4.7153    1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941    3.5797    2.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9408    1.8027   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150    4.0838   -2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9934    8.0068    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6910    0.8992    3.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5193   -0.9784    1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -1.2373    2.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -0.4333   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -3.9696   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574   -2.9245   -1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -1.9277   -3.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0819   -3.5531   -3.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -6.6750    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5854   -5.4888    2.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -5.7582    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 16 15  1  0  0  0  0
 20 21  1  0  0  0  0
 15 14  2  0  0  0  0
 21 22  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  2  0  0  0  0
 22  3  1  0  0  0  0
 22 23  1  0  0  0  0
  3  4  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  0  0  0  0
 20 50  1  1  0  0  0
  3  2  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
 10 20  1  0  0  0  0
 23 27  1  0  0  0  0
  8 19  1  0  0  0  0
 23 24  2  0  0  0  0
 12 11  1  0  0  0  0
 24 25  1  0  0  0  0
 11 10  2  0  0  0  0
 25 26  1  0  0  0  0
  5  6  1  0  0  0  0
 27 28  2  0  0  0  0
  6  7  1  0  0  0  0
 27 29  1  0  0  0  0
 12 19  1  0  0  0  0
 29 30  1  0  0  0  0
  5 20  1  0  0  0  0
 16 17  1  0  0  0  0
 19 16  2  0  0  0  0
 17 18  1  0  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 22 53  1  6  0  0  0
  3 36  1  1  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
 15 46  1  0  0  0  0
 14 45  1  0  0  0  0
 13 44  1  0  0  0  0
  9 43  1  0  0  0  0
  2 34  1  0  0  0  0
  2 35  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 24 54  1  0  0  0  0
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 26 57  1  0  0  0  0
 30 58  1  0  0  0  0
 30 59  1  0  0  0  0
 30 60  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
 18 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C(=NC3=C([H])C([H])=C([H])C(OC([H])([H])[H])=C13)[C@]1([H])N(C([H])([H])C2([H])[H])C([H])([H])[C@]([H])(C([H])([H])C([H])([H])[H])[C@@]([H])(C(=C(\[H])OC([H])([H])[H])\C(=O)OC([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(27)20-17(7-6-8-19(20)29-3)24-21(23)18(25)11-15(14)16(13-28-2)22(26)30-4/h6-8,13-15,18,27H,5,9-12H2,1-4H3/b16-13+/t14-,15-,18+,23+/m0/s1

> <INCHI_KEY>
RYENLSMHLCNXJT-KPWJTKAOSA-N

> <FORMULA>
C23H30N2O5

> <MOLECULAR_WEIGHT>
414.502

> <EXACT_MASS>
414.215472074

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.69575974344582

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(2S,3R,7aR,12bR)-3-ethyl-7a-hydroxy-8-methoxy-1H,2H,3H,4H,6H,7H,7aH,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.748353732999999

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.473692881706501

> <JCHEM_PKA_STRONGEST_BASIC>
7.316485354756701

> <JCHEM_POLAR_SURFACE_AREA>
80.59000000000002

> <JCHEM_REFRACTIVITY>
115.34659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(2S,3R,7aR,12bR)-3-ethyl-7a-hydroxy-8-methoxy-1H,2H,3H,4H,6H,7H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    3.7554   -0.1820   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9950    1.3481    1.8859 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0695    2.7707    2.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478    3.7006    1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935    3.2196    1.5499 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8354    3.4501    2.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3192    1.7180    1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1413    1.3643    0.2737 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6943    2.5642   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881    2.6835   -1.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122    3.9630   -1.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    5.0995   -0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1076    5.9944    0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043    7.3148    0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233    3.6961    0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3817    0.8202    2.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4688   -0.6607    1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2083   -0.9864    0.2803 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0854   -2.4721   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5713   -2.9215   -1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597   -2.0904   -2.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327   -2.6680   -2.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282   -3.4585    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5436   -3.1607    1.7321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2712   -4.7200    0.6486 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368   -5.7049    1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169    0.9097   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019   -0.5148   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3583   -0.5836   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192   -1.7403   -1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255   -0.1868   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650   -0.9120    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0952    1.6293   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    1.4688    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8245    2.8524    3.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047    3.1237    2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    3.7467    0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332    4.7153    1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941    3.5797    2.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9408    1.8027   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150    4.0838   -2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9011    6.0694   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994    7.5615   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    8.0068    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    7.4512    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910    0.8992    3.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5193   -0.9784    1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -1.2373    2.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -0.4333   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -3.9696   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574   -2.9245   -1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -1.9277   -3.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0819   -3.5531   -3.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -6.6750    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5854   -5.4888    2.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -5.7582    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 16 15  1  0
 20 21  1  0
 15 14  2  0
 21 22  1  0
 14 13  1  0
 13 12  2  0
 22  3  1  0
 22 23  1  0
  3  4  1  0
  8  9  1  1
 10  8  1  0
 20 50  1  1
  3  2  1  0
  8  7  1  0
  2  1  1  0
 10 20  1  0
 23 27  1  0
  8 19  1  0
 23 24  2  0
 12 11  1  0
 24 25  1  0
 11 10  2  0
 25 26  1  0
  5  6  1  0
 27 28  2  0
  6  7  1  0
 27 29  1  0
 12 19  1  0
 29 30  1  0
  5 20  1  0
 16 17  1  0
 19 16  2  0
 17 18  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  6
  3 36  1  1
  4 37  1  0
  4 38  1  0
 15 46  1  0
 14 45  1  0
 13 44  1  0
  9 43  1  0
  2 34  1  0
  2 35  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 24 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 30 58  1  0
 30 59  1  0
 30 60  1  0
 18 47  1  0
 18 48  1  0
 18 49  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       3.755  -0.182  -1.228  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.314  -0.666  -1.137  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.652  -0.416   0.239  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.612   1.089   0.578  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.995   1.348   1.886  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.069   2.771   2.272  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.148   3.701   1.468  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.294   3.220   1.550  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.835   3.450   2.844  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.319   1.718   1.226  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.141   1.364   0.274  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.694   2.564  -0.203  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.588   2.684  -1.247  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.012   3.963  -1.609  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.537   5.099  -0.926  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.631   4.975   0.132  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.108   5.994   0.869  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.504   7.315   0.520  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.223   3.696   0.476  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.382   0.820   2.001  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.469  -0.661   1.625  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.208  -0.986   0.280  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.085  -2.472  -0.047  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.571  -2.922  -1.132  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.160  -2.090  -2.052  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.333  -2.668  -2.618  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.728  -3.458   0.873  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.544  -3.161   1.732  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.271  -4.720   0.649  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.837  -5.705   1.514  0.00  0.00           C+0
HETATM   31  H   UNK     0       3.817   0.910  -1.207  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.202  -0.515  -2.171  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.358  -0.584  -0.408  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.319  -1.740  -1.352  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.726  -0.187  -1.929  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.265  -0.912   1.002  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.095   1.629  -0.224  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.639   1.469   0.611  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.825   2.852   3.340  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.105   3.124   2.187  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.489   3.747   0.426  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.233   4.715   1.875  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.794   3.580   2.739  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.941   1.803  -1.773  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.715   4.084  -2.430  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.901   6.069  -1.252  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.199   7.561  -0.502  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.993   8.007   1.197  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.582   7.451   0.656  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.691   0.899   3.052  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.519  -0.978   1.596  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.005  -1.237   2.430  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.350  -0.433  -0.487  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.656  -3.970  -1.394  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.057  -2.925  -1.837  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.789  -1.928  -3.281  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.082  -3.553  -3.212  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.407  -6.675   1.249  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.585  -5.489   2.557  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.922  -5.758   1.378  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1   34   35                                             
CONECT    3   22    4    2   36                                             
CONECT    4    5    3   37   38                                             
CONECT    5    4    6   20                                                  
CONECT    6    5    7   39   40                                             
CONECT    7    8    6   41   42                                             
CONECT    8    9   10    7   19                                             
CONECT    9    8   43                                                       
CONECT   10    8   20   11                                                  
CONECT   11   12   10                                                       
CONECT   12   13   11   19                                                  
CONECT   13   14   12   44                                                  
CONECT   14   15   13   45                                                  
CONECT   15   16   14   46                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   47   48   49                                             
CONECT   19    8   12   16                                                  
CONECT   20   21   50   10    5                                             
CONECT   21   20   22   51   52                                             
CONECT   22   21    3   23   53                                             
CONECT   23   22   27   24                                                  
CONECT   24   23   25   54                                                  
CONECT   25   24   26                                                       
CONECT   26   25   55   56   57                                             
CONECT   27   23   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   58   59   60                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    6                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43    9                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   24                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   30                                                            
CONECT   59   30                                                            
CONECT   60   30                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
    3.7554   -0.1820   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3141   -0.6658   -1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -0.4164    0.2387 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6118    1.0887    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9950    1.3481    1.8859 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0695    2.7707    2.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478    3.7006    1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935    3.2196    1.5499 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8354    3.4501    2.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3192    1.7180    1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1413    1.3643    0.2737 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6943    2.5642   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881    2.6835   -1.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122    3.9630   -1.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    5.0995   -0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307    4.9750    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076    5.9944    0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043    7.3148    0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233    3.6961    0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3817    0.8202    2.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4688   -0.6607    1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2083   -0.9864    0.2803 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0854   -2.4721   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5713   -2.9215   -1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597   -2.0904   -2.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327   -2.6680   -2.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282   -3.4585    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5436   -3.1607    1.7321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2712   -4.7200    0.6486 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368   -5.7049    1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169    0.9097   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019   -0.5148   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3583   -0.5836   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192   -1.7403   -1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255   -0.1868   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650   -0.9120    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0952    1.6293   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    1.4688    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8245    2.8524    3.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047    3.1237    2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    3.7467    0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332    4.7153    1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941    3.5797    2.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9408    1.8027   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150    4.0838   -2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9011    6.0694   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994    7.5615   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    8.0068    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    7.4512    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910    0.8992    3.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5193   -0.9784    1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -1.2373    2.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -0.4333   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -3.9696   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574   -2.9245   -1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -1.9277   -3.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0819   -3.5531   -3.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -6.6750    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5854   -5.4888    2.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -5.7582    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 16 15  1  0
 20 21  1  0
 15 14  2  0
 21 22  1  0
 14 13  1  0
 13 12  2  0
 22  3  1  0
 22 23  1  0
  3  4  1  0
  8  9  1  1
 10  8  1  0
 20 50  1  1
  3  2  1  0
  8  7  1  0
  2  1  1  0
 10 20  1  0
 23 27  1  0
  8 19  1  0
 23 24  2  0
 12 11  1  0
 24 25  1  0
 11 10  2  0
 25 26  1  0
  5  6  1  0
 27 28  2  0
  6  7  1  0
 27 29  1  0
 12 19  1  0
 29 30  1  0
  5 20  1  0
 16 17  1  0
 19 16  2  0
 17 18  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  6
  3 36  1  1
  4 37  1  0
  4 38  1  0
 15 46  1  0
 14 45  1  0
 13 44  1  0
  9 43  1  0
  2 34  1  0
  2 35  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 24 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 30 58  1  0
 30 59  1  0
 30 60  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
7b-Hydroxy-7H-mitraciliatine	Generator
7Β-hydroxy-7H-mitraciliatine	Generator

Chemical Formula

C₂₃H₃₀N₂O₅

Average Mass

414.5020 Da

Monoisotopic Mass

414.21547 Da

IUPAC Name

methyl (2E)-2-[(2S,3R,7aR,12bR)-3-ethyl-7a-hydroxy-8-methoxy-1H,2H,3H,4H,6H,7H,7aH,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(2S,3R,7aR,12bR)-3-ethyl-7a-hydroxy-8-methoxy-1H,2H,3H,4H,6H,7H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12C(=NC3=C([H])C([H])=C([H])C(OC([H])([H])[H])=C13)[C@]1([H])N(C([H])([H])C2([H])[H])C([H])([H])[C@]([H])(C([H])([H])C([H])([H])[H])[C@@]([H])(C(=C(\[H])OC([H])([H])[H])\C(=O)OC([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(27)20-17(7-6-8-19(20)29-3)24-21(23)18(25)11-15(14)16(13-28-2)22(26)30-4/h6-8,13-15,18,27H,5,9-12H2,1-4H3/b16-13+/t14-,15-,18+,23+/m0/s1

InChI Key

RYENLSMHLCNXJT-KPWJTKAOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Mitragyna speciosa	JEOL database	Ali, Z., et al. J. Tetrahedron Lett. 55, 369 (2014)

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
Quinolizidine
Quinolizine
3-alkylindole
Indole or derivatives
Anisole
Phenol ether
Aralkylamine
Alkyl aryl ether
Piperidine
Benzenoid
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Ketimine
Tertiary aliphatic amine
Tertiary amine
Organic 1,3-dipolar compound
Azacycle
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Organooxygen compound
Imine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Alcohol
Amine
Organic oxygen 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	2.49	ALOGPS
logP	2.75	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	7.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.35 m³·mol⁻¹	ChemAxon
Polarizability	45.7 Å³	ChemAxon
Number of Rings	4	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

32033854

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102232174

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ali, Z., et al. (2014). Ali, Z., et al. J. Tetrahedron Lett. 55, 369 (2014). J. Tetrahedron Lett..

Showing NP-Card for 7beta-hydroxy-7H-mitraciliatine (NP0042878)

MOL for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

3D MOL for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

3D SDF for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

3D-SDF for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

PDB for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

3D PDB for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

SMILES for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

INCHI for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

Structure for NP0042878 (7beta-hydroxy-7H-mitraciliatine)

3D Structure for NP0042878 (7beta-hydroxy-7H-mitraciliatine)