NP-MRD: Showing NP-Card for 2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol (NP0300033)

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Record Information

Version

2.0

Created at

2022-09-10 12:12:41 UTC

Updated at

2022-09-10 12:12:41 UTC

NP-MRD ID

NP0300033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol

Description

Ancistrocladidine belongs to the class of organic compounds known as naphthylisoquinolines. These are polycyclic aromatic compounds containing a naphthalene moiety linked to an isoquinoline through a CC or CN single bond. 2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol is found in Ancistrocladus heyneanus, Ancistrocladus tanzaniensis, Ancistrocladus tectorius and Dioncophyllum thollonii. 2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol was first documented in 2004 (PMID: 15165131). Based on a literature review a small amount of articles have been published on Ancistrocladidine (PMID: 15501259) (PMID: 27273153) (PMID: 16958530).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102214122D          

 30 33  0  0  1  0            999 V2000
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  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
   -1.4289   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  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
    0.0000    0.0000    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 C   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  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  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  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
    1.4289   -2.4750    0.0000 O   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
   -1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    0.9414   -3.8138   -1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921   -2.7270   -0.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494   -1.6014   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3060   -1.6303   -0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776   -0.5250    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4080    0.5845    0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0344    0.6128    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368    1.7233    1.1459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1898    2.7592    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218   -0.4910    0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1272   -0.4808    0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951   -0.9123    1.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277   -1.3778    2.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682   -0.9197    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8547   -0.5006    0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2214   -0.5348    0.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0302   -0.1247   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4765    0.3073   -1.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883    0.3320   -1.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6128    0.7756   -2.8532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3707    1.2040   -3.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429   -0.0713   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643   -0.0446   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    0.3699   -1.9208 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2317    1.6909    1.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905    2.9002    1.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4958    1.5799    0.9438 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2694    0.5294    0.4641 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2259    0.0282    1.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -0.6271   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -4.6151   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668   -3.4254   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6974   -4.1734   -0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380   -2.4927   -0.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121    2.7244   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529    3.7347    0.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2848    2.5994    0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0957   -2.4587    2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1195   -1.0821    2.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3734   -0.8580    3.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272   -1.2660    2.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6288   -0.8831    1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0914   -0.1578   -0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1212    0.6283   -2.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6764    1.6577   -4.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0879    1.9813   -3.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9196    0.3388   -4.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108    0.7027   -2.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4443    3.4110    2.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    2.7289    2.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913    3.6234    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484    0.9048   -0.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6491    0.0627    2.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950    0.7075    1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4831   -1.0123    1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7877   -0.8167   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8616   -1.5792    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 12  1  0
 12 13  1  0
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 11 23  1  0
 23 24  1  0
 23 22  2  0
 11 10  1  0
 10  7  2  0
  7  8  1  0
  8  9  1  0
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  6  5  2  0
  5 30  1  0
 30 28  1  0
 28 29  1  0
 28 27  1  0
 27 25  2  0
 25 26  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
 22 19  1  0
  3 10  1  0
 22 15  1  0
 25  6  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 18 44  1  0
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 16 42  1  0
 14 41  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 24 48  1  0
  9 35  1  0
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 30 56  1  0
 30 57  1  0
 28 52  1  6
 29 53  1  0
 29 54  1  0
 29 55  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
  4 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
M  END


  Mrv1652309102214122D          

 30 33  0  0  1  0            999 V2000
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  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
   -1.4289   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  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
    0.0000    0.0000    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 C   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  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  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  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
    1.4289   -2.4750    0.0000 O   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
   -1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300033

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=CC(C)=C(C(O)=C12)C1=C(OC)C2=C(C[C@H](C)N=C2C)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C25H27NO4/c1-13-10-16-8-7-9-18(28-4)22(16)24(27)20(13)23-19(29-5)12-17-11-14(2)26-15(3)21(17)25(23)30-6/h7-10,12,14,27H,11H2,1-6H3/t14-/m0/s1

> <INCHI_KEY>
CESMSNGGFQBVOV-AWEZNQCLSA-N

> <FORMULA>
C25H27NO4

> <MOLECULAR_WEIGHT>
405.494

> <EXACT_MASS>
405.194008353

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.282102048383194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3S)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol

> <JCHEM_LOGP>
4.5972388340000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.682318212007385

> <JCHEM_PKA_STRONGEST_BASIC>
5.711459351317329

> <JCHEM_POLAR_SURFACE_AREA>
60.28

> <JCHEM_REFRACTIVITY>
119.1411

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3S)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -2.667  -7.700   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   15   23                                                  
CONECT   23   22   11   24                                                  
CONECT   24   23                                                            
CONECT   25    6   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    5                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₇NO₄

Average Mass

405.4940 Da

Monoisotopic Mass

405.19401 Da

IUPAC Name

2-[(3S)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol

Traditional Name

2-[(3S)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=CC(C)=C(C(O)=C12)C1=C(OC)C2=C(C[C@H](C)N=C2C)C=C1OC

InChI Identifier

InChI=1S/C25H27NO4/c1-13-10-16-8-7-9-18(28-4)22(16)24(27)20(13)23-19(29-5)12-17-11-14(2)26-15(3)21(17)25(23)30-6/h7-10,12,14,27H,11H2,1-6H3/t14-/m0/s1

InChI Key

CESMSNGGFQBVOV-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
Ancistrocladus heyneanus	LOTUS Database	35616633
Ancistrocladus tanzaniensis	LOTUS Database	35616633
Ancistrocladus tectorius	LOTUS Database	35616633
Dioncophyllum tholloni	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthylisoquinolines. These are polycyclic aromatic compounds containing a naphthalene moiety linked to an isoquinoline through a CC or CN single bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Naphthylisoquinolines

Direct Parent

Naphthylisoquinolines

Alternative Parents

Substituents

Naphthylisoquinoline
1-naphthol
Dihydroisoquinoline
Naphthalene
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Ketimine
Ether
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Imine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.6	ChemAxon
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	5.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.28 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	119.14 m³·mol⁻¹	ChemAxon
Polarizability	45.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025360

Chemspider ID

168251

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bringmann G, Dreyer M, Faber JH, Dalsgaard PW, Staerk D, Jaroszewski JW, Ndangalasi H, Mbago F, Brun R, Christensen SB: Ancistrotanzanine C and related 5,1'- and 7,3'-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis. J Nat Prod. 2004 May;67(5):743-8. doi: 10.1021/np0340549. [PubMed:15165131 ]
Bringmann G, Dreyer M, Michel M, Tayman FS, Brun R: Ancistroheynine B and two further 7,3'-coupled naphthylisoquinoline alkaloids from Ancistrocladus heyneanus Wall. Phytochemistry. 2004 Nov;65(21):2903-7. doi: 10.1016/j.phytochem.2004.05.026. [PubMed:15501259 ]
Bringmann G, Manchala N, Buttner T, Hertlein-Amslinger B, Seupel R: First Atroposelective Total Synthesis of Enantiomerically Pure Ancistrocladidine and Ancistrotectorine. Chemistry. 2016 Jul 4;22(28):9792-6. doi: 10.1002/chem.201600701. Epub 2016 Jun 6. [PubMed:27273153 ]
Bungard CJ, Morris JC: Total synthesis of the 7,3'-linked naphthylisoquinoline alkaloid ancistrocladidine. J Org Chem. 2006 Sep 15;71(19):7354-63. doi: 10.1021/jo0611364. [PubMed:16958530 ]
LOTUS database [Link]

Showing NP-Card for 2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol (NP0300033)

MOL for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

3D MOL for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

3D SDF for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

3D-SDF for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

PDB for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

3D PDB for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

SMILES for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

INCHI for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

Structure for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)

3D Structure for NP0300033 (2-[(3s)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol)