NP-MRD: Showing NP-Card for (2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate (NP0247484)

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Record Information

Version

2.0

Created at

2022-09-07 09:21:29 UTC

Updated at

2022-09-07 09:21:29 UTC

NP-MRD ID

NP0247484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate

Description

(2R,7R,9R,9aS)-7-[(2R)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1H-quinolizin-2-yl 2-phenylacetate belongs to the class of organic compounds known as lupinine-type alkaloids. These are lupin alkaloids with a structure based on the lupinine skeleton, which is a bicyclic compound consisting of a quinolizidine. (2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate is found in Cadia purpurea. Based on a literature review very few articles have been published on (2R,7R,9R,9aS)-7-[(2R)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1H-quinolizin-2-yl 2-phenylacetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211212D          

 29 32  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 23  1  1  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 14  1  6  0  0  0
 28 29  1  0  0  0  0
 11 29  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
    4.1965   -0.9452    0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2606    0.2240   -0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5846    0.8598   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258   -0.0978   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1922   -0.9789   -1.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1623   -1.8697   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5849   -1.8936    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0270   -1.0157    1.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0484   -0.1234    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0666    0.8530   -0.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7989    0.2740   -0.6080 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1480    0.1990   -1.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2487    0.7963   -1.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9687    0.1572   -0.8808 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3659    0.2171   -1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425   -0.1834    0.2277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5255   -0.3371    0.0972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2092    0.9073   -0.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6963    0.6891   -0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1884   -0.5718   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1076   -1.5280   -1.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4299   -2.6159   -1.9652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9058   -1.4310   -0.7333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329    0.9359    1.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721    0.8970    1.4654 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0684    0.1792    2.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7169    0.8548    3.8244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276    0.3130    0.3995 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8834    1.0992    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045    1.1162   -1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845    1.7770    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9074   -1.0164   -2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6239   -2.5756   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3553   -2.6027    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3659   -1.0432    2.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6522    0.5385    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8142   -0.7451   -0.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854    0.6929   -2.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -0.8544   -2.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371    0.4871   -2.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432    1.8882   -1.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6765   -0.3987   -1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6599    1.2786   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407   -1.1123    0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9289   -0.5305    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0351    0.9898   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9209    1.8220    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8471    0.5807    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2826    1.5840   -0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7684   -0.3717   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9137   -1.0976   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9381   -3.5164   -1.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3287    0.7672    2.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    1.9345    0.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9190    1.9514    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052    0.0270    3.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -0.8053    2.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2455    0.7520    4.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965   -0.7065    0.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522    1.2167    1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095    2.1086   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
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 16 15  1  0
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 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 29  1  0
 29 28  1  0
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 10  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
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  7  8  1  0
  8  9  2  0
 16 17  1  0
 17 18  1  0
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 28 25  1  0
  9  4  1  0
 23 17  1  0
 28 14  1  0
 27 58  1  0
 26 56  1  0
 26 57  1  0
 25 55  1  1
 24 53  1  0
 24 54  1  0
 16 44  1  1
 15 42  1  0
 15 43  1  0
 13 40  1  0
 13 41  1  0
 12 38  1  0
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 11 37  1  1
 29 60  1  0
 29 61  1  0
 28 59  1  1
  3 30  1  0
  3 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
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 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
M  END


  Mrv1652309072211212D          

 29 32  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 23  1  1  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 14  1  6  0  0  0
 28 29  1  0  0  0  0
 11 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1C[C@H](CN2CC[C@H](C[C@@H]12)OC(=O)CC1=CC=CC=C1)[C@H]1CCCC(O)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32N2O4/c26-15-18-12-17(20-7-4-8-22(27)24-20)14-25-10-9-19(13-21(18)25)29-23(28)11-16-5-2-1-3-6-16/h1-3,5-6,17-21,26H,4,7-15H2,(H,24,27)/t17-,18+,19-,20-,21+/m1/s1

> <INCHI_KEY>
SNZVYWPNUDUKMW-XNTOXWQXSA-N

> <FORMULA>
C23H32N2O4

> <MOLECULAR_WEIGHT>
400.519

> <EXACT_MASS>
400.236207518

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.23171284182355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,7R,9R,9aS)-7-[(2R)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1H-quinolizin-2-yl 2-phenylacetate

> <JCHEM_LOGP>
-0.7878730014571982

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.421857289425272

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.078715700413319

> <JCHEM_PKA_STRONGEST_BASIC>
9.575716257691065

> <JCHEM_POLAR_SURFACE_AREA>
82.36

> <JCHEM_REFRACTIVITY>
110.79049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,7R,9R,9aS)-7-[(2R)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1H-quinolizin-2-yl phenylacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       9.336  -0.770   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17                                                       
CONECT   24   16   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   14   29                                                  
CONECT   29   28   11                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(2R,7R,9R,9AS)-7-[(2R)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1H-quinolizin-2-yl 2-phenylacetic acid	Generator

Chemical Formula

C₂₃H₃₂N₂O₄

Average Mass

400.5190 Da

Monoisotopic Mass

400.23621 Da

IUPAC Name

(2R,7R,9R,9aS)-7-[(2R)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1H-quinolizin-2-yl 2-phenylacetate

Traditional Name

(2R,7R,9R,9aS)-7-[(2R)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1H-quinolizin-2-yl phenylacetate

CAS Registry Number

Not Available

SMILES

OC[C@@H]1C[C@H](CN2CC[C@H](C[C@@H]12)OC(=O)CC1=CC=CC=C1)[C@H]1CCCC(O)=N1

InChI Identifier

InChI=1S/C23H32N2O4/c26-15-18-12-17(20-7-4-8-22(27)24-20)14-25-10-9-19(13-21(18)25)29-23(28)11-16-5-2-1-3-6-16/h1-3,5-6,17-21,26H,4,7-15H2,(H,24,27)/t17-,18+,19-,20-,21+/m1/s1

InChI Key

SNZVYWPNUDUKMW-XNTOXWQXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Cadia purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lupinine-type alkaloids. These are lupin alkaloids with a structure based on the lupinine skeleton, which is a bicyclic compound consisting of a quinolizidine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Lupinine-type alkaloids

Direct Parent

Lupinine-type alkaloids

Alternative Parents

Substituents

Lupinine
Quinolizidine
Quinolizine
Tetrahydropyridine
Monocyclic benzene moiety
Hydropyridine
Piperidine
Benzenoid
1,3-aminoalcohol
Cyclic carboximidic acid
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Lactim
Organoheterocyclic compound
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Organonitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Amine
Hydrocarbon derivative
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	-0.79	ChemAxon
pKa (Strongest Acidic)	6.08	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	110.79 m³·mol⁻¹	ChemAxon
Polarizability	43.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162927582

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate (NP0247484)

MOL for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

3D MOL for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

3D SDF for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

3D-SDF for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

PDB for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

3D PDB for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

SMILES for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

INCHI for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

Structure for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)

3D Structure for NP0247484 ((2r,7r,9r,9as)-7-[(2r)-6-hydroxy-2,3,4,5-tetrahydropyridin-2-yl]-9-(hydroxymethyl)-octahydro-1h-quinolizin-2-yl 2-phenylacetate)