NP-MRD: Showing NP-Card for (21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol (NP0222570)

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Record Information

Version

2.0

Created at

2022-09-06 00:26:24 UTC

Updated at

2022-09-06 00:26:24 UTC

NP-MRD ID

NP0222570

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol

Description

Boehmeriasin B belongs to the class of organic compounds known as phenanthroquinolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the quinolizidine is fused to the second benzene ring of a phenanthrene. (21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol is found in Boehmeria siamensis. (21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol was first documented in 2003 (PMID: 14598211). Based on a literature review very few articles have been published on Boehmeriasin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062202262D          

 27 31  0  0  1  0            999 V2000
    6.6555    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -2.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -3.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -4.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -2.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -3.1734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951   -1.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  0  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 21  1  1  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    5.1794   -4.3234   -1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883   -2.9599   -1.0173 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210   -2.4645   -0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5804   -3.3158   -0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3386   -2.7556   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -1.4005   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443   -0.8757    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2799    0.4889    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806    1.3399   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5707    2.7004   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934    3.6199   -0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    4.9841   -0.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0326    5.4108   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8277    3.1002   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9091    3.9288   -0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0469    1.7139   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    0.8134   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954   -0.5647   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444   -1.0753   -0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101    1.0867    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891    0.0678    0.2450 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    0.4182   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0172    0.0621    0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7727   -1.1046    1.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6364   -1.9505    1.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143   -1.0957    1.0082 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2352   -1.8477    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3059   -4.6749   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851   -4.9268   -1.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1638   -4.4793   -1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7079   -4.3837   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5377   -3.4463   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001    3.1053    0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    5.0645   -0.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    4.9700    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0057    6.5091    0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7921    4.9298   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0398    1.3497   -0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047   -0.4561   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013    1.5684    1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573    1.8906   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9212    1.5293   -0.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0328   -0.0314   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3729    0.9438    1.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9000   -0.2141    0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4710   -0.7025    2.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6726   -1.7332    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8869   -2.2273   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099   -2.8667    1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -0.8181    2.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6508   -2.3121   -0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579   -2.5892    1.1045 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  7  1  0
  7  8  2  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 18  6  1  0
 27  7  1  0
 17  9  1  0
 26 21  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
 20 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  1
 27 51  1  0
 27 52  1  0
 10 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
M  END


  Mrv1652309062202262D          

 27 31  0  0  1  0            999 V2000
    6.6555    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -2.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -3.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -4.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -2.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -3.1734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951   -1.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  0  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 21  1  1  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C3=C(CN4CCCC[C@H]4C3)C3=CC(OC)=C(O)C=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H25NO3/c1-26-15-6-7-16-17-9-14-5-3-4-8-24(14)13-21(17)20-12-23(27-2)22(25)11-19(20)18(16)10-15/h6-7,10-12,14,25H,3-5,8-9,13H2,1-2H3/t14-/m0/s1

> <INCHI_KEY>
HIIPBPYYJOYQBL-AWEZNQCLSA-N

> <FORMULA>
C23H25NO3

> <MOLECULAR_WEIGHT>
363.457

> <EXACT_MASS>
363.183443669

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.202413756514616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(21S)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(14),2,4,6,8,10,12-heptaen-10-ol

> <JCHEM_LOGP>
4.122184093531933

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.70360347086759

> <JCHEM_PKA_STRONGEST_BASIC>
7.7497817913762095

> <JCHEM_POLAR_SURFACE_AREA>
41.93

> <JCHEM_REFRACTIVITY>
107.53019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(21S)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(14),2,4,6,8,10,12-heptaen-10-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      12.424   0.188   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.870  -2.431   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.366  -3.887   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.375  -5.051   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.870  -6.506   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.879  -7.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.887  -4.760   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.895  -5.924   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.391  -3.304   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.383  -2.140   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.342  -0.394   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    9   18                                                  
CONECT   18   17    6   19                                                  
CONECT   19   18    3                                                       
CONECT   20    8   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26    7                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₅NO₃

Average Mass

363.4570 Da

Monoisotopic Mass

363.18344 Da

IUPAC Name

(21S)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(14),2,4,6,8,10,12-heptaen-10-ol

Traditional Name

(21S)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(14),2,4,6,8,10,12-heptaen-10-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C3=C(CN4CCCC[C@H]4C3)C3=CC(OC)=C(O)C=C3C2=C1

InChI Identifier

InChI=1S/C23H25NO3/c1-26-15-6-7-16-17-9-14-5-3-4-8-24(14)13-21(17)20-12-23(27-2)22(25)11-19(20)18(16)10-15/h6-7,10-12,14,25H,3-5,8-9,13H2,1-2H3/t14-/m0/s1

InChI Key

HIIPBPYYJOYQBL-AWEZNQCLSA-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
Boehmeria siamensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthroquinolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the quinolizidine is fused to the second benzene ring of a phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthroquinolizidines

Direct Parent

Phenanthroquinolizidines

Alternative Parents

Substituents

Phenanthroquinolizidine
Phenanthrol
2-naphthol
Naphthalene
Quinolizidine
Tetrahydroisoquinoline
Anisole
Aralkylamine
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Piperidine
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Ether
Azacycle
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
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	4.12	ChemAxon
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	7.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.53 m³·mol⁻¹	ChemAxon
Polarizability	42.2 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102420434

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Luo Y, Liu Y, Luo D, Gao X, Li B, Zhang G: Cytotoxic alkaloids from Boehmeria siamensis. Planta Med. 2003 Sep;69(9):842-5. doi: 10.1055/s-2003-43215. [PubMed:14598211 ]
LOTUS database [Link]

Showing NP-Card for (21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol (NP0222570)

MOL for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

3D MOL for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

3D SDF for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

3D-SDF for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

PDB for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

3D PDB for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

SMILES for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

INCHI for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

Structure for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)

3D Structure for NP0222570 ((21s)-5,11-dimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaen-10-ol)