NP-MRD: Showing NP-Card for (1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium (NP0146739)

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Record Information

Version

2.0

Created at

2022-09-02 02:11:43 UTC

Updated at

2022-09-02 02:11:43 UTC

NP-MRD ID

NP0146739

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium

Description

Latifolian B belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. (1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium is found in Gnetum latifolium. (1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium was first documented in 2005 (PMID: 16038553). Based on a literature review very few articles have been published on Latifolian B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204122D          

 32 37  0  0  1  0            999 V2000
    3.6610   -3.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -2.5647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -2.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3780   -1.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0107   -2.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2504   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0539   -2.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -3.7694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636   -1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -0.8348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3347    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.1007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2560    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758   -0.6789    0.0000 N   0  3  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32  5  1  6  0  0  0
 21 32  1  0  0  0  0
 11 32  1  0  0  0  0
M  CHG  1  32   1
M  END

     RDKit          3D

 56 61  0  0  0  0  0  0  0  0999 V2000
    2.3850   -3.7665    2.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697   -2.8834    3.5689 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2610   -1.6833    3.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612   -1.3498    1.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.1591    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862    0.6401    2.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910    0.2982    3.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852   -0.8807    4.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -1.2447    5.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222    1.8685    1.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203    1.8550    0.6135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3649    2.7054   -0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0440    4.0151   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892    4.8601   -1.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1193    6.1840   -1.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4502    4.3378   -2.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0064    5.1609   -3.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8725    3.0085   -2.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3103    2.2200   -1.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    0.8315   -1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189   -0.0642   -0.2665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6915   -1.3167   -1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7715   -2.1286   -1.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809   -3.3161   -1.9905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7936   -4.1305   -2.2061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468   -3.6739   -2.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644   -4.8422   -3.2185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341   -2.8532   -2.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274   -1.6753   -1.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234   -0.8606   -1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275    0.4020   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3093    0.4527    0.2405 N   0  0  2  0  0  4  0  0  0  0  0  0
    1.5293   -4.3155    2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0172   -4.5221    3.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046   -3.2576    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -1.9974    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872    0.9372    4.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -2.1273    5.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6103    1.7809    1.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2624    2.7800    2.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    2.2261    0.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7977    4.4365    0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5955    6.5381   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7075    6.1185   -3.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6306    2.6375   -2.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937    0.8779   -0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447    0.3791   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386   -0.4087    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784   -1.8916   -0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6828   -3.8305   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000   -5.1419   -3.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979   -3.1793   -2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894   -0.6066   -2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -1.4308   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061    0.7896   -0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    1.1969   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 32 31  1  6
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
 32  5  1  0
 32 11  1  0
 19 12  1  0
 32 21  1  0
 29 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  1
 13 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  1
 23 49  1  0
 25 50  1  0
 27 51  1  0
 28 52  1  0
 30 53  1  0
 30 54  1  0
 31 55  1  0
 31 56  1  0
  7 37  1  0
  9 38  1  0
M  CHG  1  32   1
M  END


  Mrv1652309022204122D          

 32 37  0  0  1  0            999 V2000
    3.6610   -3.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -2.5647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -2.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3780   -1.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0107   -2.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2504   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0539   -2.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -3.7694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636   -1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -0.8348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3347    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.1007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2560    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758   -0.6789    0.0000 N   0  3  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32  5  1  6  0  0  0
 21 32  1  0  0  0  0
 11 32  1  0  0  0  0
M  CHG  1  32   1
M  END
> <DATABASE_ID>
NP0146739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C[C@@H]3C4=CC(O)=C(O)C=C4C[C@H]4C5=CC(O)=C(O)C=C5CC[N@@+]234)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H23NO6/c1-32-25-11-17-14(8-24(25)31)5-19-16-10-23(30)21(28)7-13(16)4-18-15-9-22(29)20(27)6-12(15)2-3-26(17,18)19/h6-11,18-19H,2-5H2,1H3,(H4-,27,28,29,30,31)/p+1/t18-,19+,26-/m0/s1

> <INCHI_KEY>
QAXHHTKPOZDKNR-ANSQWYIGSA-O

> <FORMULA>
C25H24NO6

> <MOLECULAR_WEIGHT>
434.467

> <EXACT_MASS>
434.159813917

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
46.14790173675007

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,9R,17S)-5,12,13,20,21-pentahydroxy-4-methoxy-1lambda5-azahexacyclo[15.8.0.0^{1,9}.0^{2,7}.0^{10,15}.0^{18,23}]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
0.0455980588615878

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.278920164631412

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.785373115691543

> <JCHEM_PKA_STRONGEST_BASIC>
-4.913396272207042

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
130.54139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9R,17S)-5,12,13,20,21-pentahydroxy-4-methoxy-1lambda5-azahexacyclo[15.8.0.0^{1,9}.0^{2,7}.0^{10,15}.0^{18,23}]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.834  -6.261   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.386  -4.788   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.886  -4.438   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.439  -2.965   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.743  -2.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.887  -3.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.334  -5.213   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.834  -5.563   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.282  -7.036   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.492  -3.086   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.683  -1.558   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.846   0.479   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.358   0.188   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.342   1.934   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.350   3.098   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.830   2.225   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.179   1.061   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.691   1.352   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.699   0.188   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.211   0.479   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.715   1.934   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.228   2.225   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.732   3.680   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.236   1.061   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.748   1.352   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.732  -0.394   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.219  -0.685   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.715  -2.140   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.203  -2.431   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       2.195  -1.267   0.000  0.00  0.00           N+1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   22   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    5   21   11                                             
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄NO₆

Average Mass

434.4670 Da

Monoisotopic Mass

434.15981 Da

IUPAC Name

(1S,9R,17S)-5,12,13,20,21-pentahydroxy-4-methoxy-1lambda5-azahexacyclo[15.8.0.0^{1,9}.0^{2,7}.0^{10,15}.0^{18,23}]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium

Traditional Name

(1S,9R,17S)-5,12,13,20,21-pentahydroxy-4-methoxy-1lambda5-azahexacyclo[15.8.0.0^{1,9}.0^{2,7}.0^{10,15}.0^{18,23}]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C[C@@H]3C4=CC(O)=C(O)C=C4C[C@H]4C5=CC(O)=C(O)C=C5CC[N@@+]234)C=C1O

InChI Identifier

InChI=1S/C25H23NO6/c1-32-25-11-17-14(8-24(25)31)5-19-16-10-23(30)21(28)7-13(16)4-18-15-9-22(29)20(27)6-12(15)2-3-26(17,18)19/h6-11,18-19H,2-5H2,1H3,(H4-,27,28,29,30,31)/p+1/t18-,19+,26-/m0/s1

InChI Key

QAXHHTKPOZDKNR-ANSQWYIGSA-O

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
Gnetum latifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroprotoberberine skeleton
Tetrahydroisoquinoline
Indole or derivatives
Anisole
Phenol ether
Aralkylamine
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Azacycle
Ether
Organoheterocyclic compound
Polyol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organic nitrogen compound
Organic cation
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	2.02	ALOGPS
logP	0.046	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	8.79	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	130.54 m³·mol⁻¹	ChemAxon
Polarizability	46.15 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042678

Chemspider ID

9528252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11353317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rochfort SJ, Towerzey L, Carroll A, King G, Michael A, Pierens G, Rali T, Redburn J, Whitmore J, Quinn RJ: Latifolians A and B, novel JNK3 kinase inhibitors from the Papua New Guinean plant Gnetum latifolium. J Nat Prod. 2005 Jul;68(7):1080-2. doi: 10.1021/np049616i. [PubMed:16038553 ]
LOTUS database [Link]

Showing NP-Card for (1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium (NP0146739)

MOL for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

3D MOL for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

3D SDF for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

3D-SDF for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

PDB for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

3D PDB for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

SMILES for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

INCHI for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

Structure for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)

3D Structure for NP0146739 ((1s,9r,17s)-5,12,13,20,21-pentahydroxy-4-methoxy-1λ⁵-azahexacyclo[15.8.0.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁸,²³]pentacosa-2(7),3,5,10,12,14,18,20,22-nonaen-1-ylium)