NP-MRD: Showing NP-Card for (21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene (NP0306788)

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Record Information

Version

2.0

Created at

2022-09-10 23:29:38 UTC

Updated at

2022-09-10 23:29:39 UTC

NP-MRD ID

NP0306788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Boehmeriasin A 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)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene is found in Boehmeria siamensis. (21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene was first documented in 2006 (PMID: 16445628). Based on a literature review a small amount of articles have been published on Boehmeriasin A (PMID: 30716712) (PMID: 25626146) (PMID: 21779519) (PMID: 20183275).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201292D          

 28 32  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
    5.5753   -3.0175    0.0000 C   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
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
  8 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 27  1  0  0  0  0
 27 22  1  1  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -3.9896    5.3282   -0.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132    3.9418   -0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357    3.2222   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    3.8152   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3505    3.0244   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    1.6603   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7323    0.8763   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141   -0.4890   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274   -1.1171    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -2.4756    0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616   -3.1279    0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0509   -4.5044    0.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9569   -5.3658    0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1043   -2.3701    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3719   -2.9254    0.2319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5566   -2.1953    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0010   -0.9718    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792   -0.3389   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6717    1.0547   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052    1.8314   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920   -1.4226    0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9575   -0.6349   -0.2811 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1501   -1.3749   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1428   -0.4150   -1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4976    0.6033   -0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3684    1.1537    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0410    0.5500    0.4745 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0561    1.5473   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596    5.6863   -1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0326    5.6205   -0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6866    5.8157    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    4.8937   -0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192    3.5184   -0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1324   -3.1053    0.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609   -5.2918    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -5.2407   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329   -6.4131    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3975   -2.8722    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5088   -1.3545    0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6612   -1.7771   -0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9105   -0.4164    0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8037    1.4005   -0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6599   -2.2127   -0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9181   -1.8735    1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9438   -2.2425   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5993   -1.6412    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6317    0.1013   -1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0343   -0.9350   -1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2714    0.1202    0.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0863    1.4077   -0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6660    1.1552    1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897    2.2557    0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825    0.3453    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871    1.6854   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    2.4900    0.4197 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 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
 27 28  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
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 19  6  1  0
 28  7  1  0
 18  9  1  0
 27 22  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
 21 43  1  0
 21 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  1
 28 54  1  0
 28 55  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
M  END


  Mrv1652309112201292D          

 28 32  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
    5.5753   -3.0175    0.0000 C   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
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
  8 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 27  1  0  0  0  0
 27 22  1  1  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306788

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO3/c1-26-16-7-8-17-18-10-15-6-4-5-9-25(15)14-22(18)21-13-24(28-3)23(27-2)12-20(21)19(17)11-16/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m0/s1

> <INCHI_KEY>
ANTGAFQZQJMDNP-HNNXBMFYSA-N

> <FORMULA>
C24H27NO3

> <MOLECULAR_WEIGHT>
377.484

> <EXACT_MASS>
377.199093733

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.29888000092732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.370604007333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.747930655042265

> <JCHEM_POLAR_SURFACE_AREA>
30.93

> <JCHEM_REFRACTIVITY>
112.01249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-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      10.407  -5.633   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.391  -3.304   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.383  -2.140   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.342  -0.394   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   28  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   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17    9   19                                                  
CONECT   19   18    6   20                                                  
CONECT   20   19    3                                                       
CONECT   21    8   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27    7                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₇NO₃

Average Mass

377.4840 Da

Monoisotopic Mass

377.19909 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H27NO3/c1-26-16-7-8-17-18-10-15-6-4-5-9-25(15)14-22(18)21-13-24(28-3)23(27-2)12-20(21)19(17)11-16/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m0/s1

InChI Key

ANTGAFQZQJMDNP-HNNXBMFYSA-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
Naphthalene
Quinolizidine
Tetrahydroisoquinoline
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Piperidine
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
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	4.37	ChemAxon
pKa (Strongest Basic)	7.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	112.01 m³·mol⁻¹	ChemAxon
Polarizability	44.3 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

28496848

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52939850

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guzelcan EA, Baxendale IR, Cetin-Atalay R, Baumann M: Synthesis of new derivatives of boehmeriasin A and their biological evaluation in liver cancer. Eur J Med Chem. 2019 Mar 15;166:243-255. doi: 10.1016/j.ejmech.2019.01.056. Epub 2019 Jan 24. [PubMed:30716712 ]
Christodoulou MS, Calogero F, Baumann M, Garcia-Argaez AN, Pieraccini S, Sironi M, Dapiaggi F, Bucci R, Broggini G, Gazzola S, Liekens S, Silvani A, Lahtela-Kakkonen M, Martinet N, Nonell-Canals A, Santamaria-Navarro E, Baxendale IR, Dalla Via L, Passarella D: Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2. Eur J Med Chem. 2015 Mar 6;92:766-75. doi: 10.1016/j.ejmech.2015.01.038. Epub 2015 Jan 20. [PubMed:25626146 ]
Leighty MW, Georg GI: Total Syntheses and Cytotoxicity of (R)- and (S)-Boehmeriasin A. ACS Med Chem Lett. 2011 Apr 14;2(4):313-315. doi: 10.1021/ml1003074. [PubMed:21779519 ]
Semwal DK, Rawat U, Semwal R, Singh R, Krishan P, Singh M, Singh GJ: Chemical constituents from the leaves of Boehmeria rugulosa with antidiabetic and antimicrobial activities. J Asian Nat Prod Res. 2009 Dec;11(12):1045-55. doi: 10.1080/10286020903352526. [PubMed:20183275 ]
Yan J, Luo D, Luo Y, Gao X, Zhang G: Induction of G1 arrest and differentiation in MDA-MB-231 breast cancer cell by boehmeriasin A, a novel compound from plant. Int J Gynecol Cancer. 2006 Jan-Feb;16(1):165-70. doi: 10.1111/j.1525-1438.2006.00291.x. [PubMed:16445628 ]
LOTUS database [Link]

Showing NP-Card for (21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene (NP0306788)

MOL for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

3D MOL for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

3D SDF for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

3D-SDF for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

PDB for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

3D PDB for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

SMILES for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

INCHI for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

Structure for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)

3D Structure for NP0306788 ((21s)-5,10,11-trimethoxy-16-azapentacyclo[12.8.0.0²,⁷.0⁸,¹³.0¹⁶,²¹]docosa-1(14),2(7),3,5,8(13),9,11-heptaene)