NP-MRD: Showing NP-Card for 1-O-acetyl-3-O-methylnarcissidine (NP0036983)

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Record Information

Version

2.0

Created at

2021-06-20 20:01:00 UTC

Updated at

2021-06-30 00:08:56 UTC

NP-MRD ID

NP0036983

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-O-acetyl-3-O-methylnarcissidine

Provided By

JEOL Database JEOL Logo

Description

1-O-Acetyl-3-O-methylnarcissidine belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. 1-O-acetyl-3-O-methylnarcissidine is found in Narcissus serotinus. 1-O-acetyl-3-O-methylnarcissidine was first documented in 2012 (Pigni, N. B., et al.). Based on a literature review very few articles have been published on 1-O-Acetyl-3-O-methylnarcissidine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122013D          

 55 58  0  0  0  0            999 V2000
   -1.9277    3.6346    2.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6585    2.6542    1.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9548    1.8295    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0552   -0.1008   -0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906    0.7854    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215    0.7188    0.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937   -0.3337   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122013D          

 55 58  0  0  0  0            999 V2000
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   -4.4101   -1.3125    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134   -0.2417    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -0.2504   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755   -0.2557   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905   -1.9352   -2.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880   -5.2682    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -4.2105    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5632   -5.6515   -0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.9115   -3.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117   -1.8281   -6.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -2.1450   -5.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780   -3.4831   -5.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942   -3.4222   -3.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4729   -5.1894   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -5.5920   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7454   -4.0513   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781   -1.4774   -3.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.9152   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3430    0.0526   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.7155   -1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9869    1.9686   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -1.8073   -0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 11  1  0  0  0  0
  5 27  1  0  0  0  0
 25 24  1  0  0  0  0
 24 23  2  0  0  0  0
 23 28  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
  8  9  1  0  0  0  0
 11 28  1  0  0  0  0
  9 10  1  0  0  0  0
  8  3  2  0  0  0  0
  3  2  1  0  0  0  0
  6  7  2  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
  6  5  1  0  0  0  0
 20 21  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  1  0  0  0  0
 23 20  1  0  0  0  0
 11 37  1  6  0  0  0
 20 17  1  0  0  0  0
 18 19  1  0  0  0  0
 17 12  1  0  0  0  0
 21 22  1  0  0  0  0
 28 26  1  0  0  0  0
 28 55  1  1  0  0  0
 13 14  1  0  0  0  0
  3  4  1  0  0  0  0
 14 15  1  0  0  0  0
  4  5  2  0  0  0  0
 14 16  2  0  0  0  0
  4 32  1  0  0  0  0
  7 33  1  0  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
 20 46  1  6  0  0  0
 17 42  1  6  0  0  0
 12 38  1  6  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 24 50  1  0  0  0  0
 10 34  1  0  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036983

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2[C@@]3([H])N(C1([H])[H])C([H])([H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1[C@]3([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC([H])([H])[H])[C@]2([H])OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H27NO6/c1-11(23)28-20-17-14-9-16(25-3)15(24-2)8-12(14)10-22-7-6-13(18(17)22)19(26-4)21(20)27-5/h6,8-9,17-21H,7,10H2,1-5H3/t17-,18+,19+,20-,21-/m0/s1

> <INCHI_KEY>
YUUHTZSDSDKWDN-ZPAWYTMASA-N

> <FORMULA>
C21H27NO6

> <MOLECULAR_WEIGHT>
389.448

> <EXACT_MASS>
389.183837593

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.89322425276082

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13R,14R,15S,16S)-4,5,13,14-tetramethoxy-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,4,6,11-tetraen-15-yl acetate

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.0321400819999997

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.541125009698161

> <JCHEM_POLAR_SURFACE_AREA>
66.46000000000001

> <JCHEM_REFRACTIVITY>
103.20249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13R,14R,15S,16S)-4,5,13,14-tetramethoxy-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,4,6,11-tetraen-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -1.9277    3.6346    2.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6585    2.6542    1.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9548    1.8295    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960    1.9807    0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0389    1.0885   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917    0.0356   -1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0552   -0.1008   -0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906    0.7854    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215    0.7188    0.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937   -0.3337   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009   -0.8629   -1.9872 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5432   -2.1873   -2.4671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8145   -3.0255   -1.3226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191   -4.0206   -1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557   -4.8362   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3416   -4.2196   -2.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3985   -2.9146   -3.4803 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5013   -2.1620   -4.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696   -2.4264   -5.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -3.1291   -2.9157 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7838   -4.1848   -1.9452 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -4.7751   -1.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3426   -1.8798   -2.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -1.1998   -2.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824    0.0429   -1.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2351    0.0003   -0.8366 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931    1.2621   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4528   -1.1717   -1.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6260    4.1472    2.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043    4.3851    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508    3.1755    2.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116    2.7875    0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6139   -0.9010   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4101   -1.3125    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134   -0.2417    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -0.2504   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755   -0.2557   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905   -1.9352   -2.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880   -5.2682    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -4.2105    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5632   -5.6515   -0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.9115   -3.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117   -1.8281   -6.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -2.1450   -5.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780   -3.4831   -5.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942   -3.4222   -3.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4729   -5.1894   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -5.5920   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7454   -4.0513   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781   -1.4774   -3.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.9152   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3430    0.0526   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.7155   -1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9869    1.9686   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -1.8073   -0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 11  1  0
  5 27  1  0
 25 24  1  0
 24 23  2  0
 23 28  1  0
 26 25  1  0
 27 26  1  0
  8  9  1  0
 11 28  1  0
  9 10  1  0
  8  3  2  0
  3  2  1  0
  6  7  2  0
  2  1  1  0
  7  8  1  0
 12 13  1  0
  6  5  1  0
 20 21  1  0
 11 12  1  0
 17 18  1  0
 23 20  1  0
 11 37  1  6
 20 17  1  0
 18 19  1  0
 17 12  1  0
 21 22  1  0
 28 26  1  0
 28 55  1  1
 13 14  1  0
  3  4  1  0
 14 15  1  0
  4  5  2  0
 14 16  2  0
  4 32  1  0
  7 33  1  0
 27 53  1  0
 27 54  1  0
 20 46  1  6
 17 42  1  6
 12 38  1  6
 25 51  1  0
 25 52  1  0
 24 50  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.928   3.635   2.274  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.659   2.654   1.553  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.955   1.829   0.708  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.596   1.981   0.411  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.039   1.089  -0.460  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.692   0.036  -1.051  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.055  -0.101  -0.771  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.691   0.785   0.109  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.021   0.719   0.446  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.794  -0.334  -0.113  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.101  -0.863  -1.987  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.543  -2.187  -2.467  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.815  -3.026  -1.323  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.719  -4.021  -1.513  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.856  -4.836  -0.265  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.342  -4.220  -2.547  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.399  -2.915  -3.480  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.501  -2.162  -4.707  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.570  -2.426  -5.606  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.837  -3.129  -2.916  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.784  -4.185  -1.945  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.054  -4.775  -1.696  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.343  -1.880  -2.265  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.478  -1.200  -2.445  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.482   0.043  -1.619  0.00  0.00           C+0
HETATM   26  N   UNK     0       2.235   0.000  -0.837  0.00  0.00           N+0
HETATM   27  C   UNK     0       1.493   1.262  -0.861  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.453  -1.172  -1.303  0.00  0.00           C+0
HETATM   29  H   UNK     0      -2.626   4.147   2.943  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.504   4.385   1.599  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.151   3.176   2.895  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.012   2.788   0.839  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.614  -0.901  -1.241  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.410  -1.313   0.194  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.813  -0.242   0.274  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.844  -0.250  -1.203  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.276  -0.256  -2.890  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.490  -1.935  -2.959  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.888  -5.268   0.003  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.236  -4.210   0.546  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.563  -5.652  -0.441  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.003  -3.912  -3.704  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.412  -1.828  -6.507  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.532  -2.145  -5.170  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.578  -3.483  -5.890  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.494  -3.422  -3.745  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.473  -5.189  -2.618  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.914  -5.592  -0.983  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.745  -4.051  -1.256  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.278  -1.477  -3.115  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.548   0.915  -2.279  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.343   0.053  -0.943  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.495   1.716  -1.862  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.987   1.969  -0.184  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.292  -1.807  -0.422  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    8    2    4                                                  
CONECT    4    3    5   32                                                  
CONECT    5   27    6    4                                                  
CONECT    6   11    7    5                                                  
CONECT    7    6    8   33                                                  
CONECT    8    9    3    7                                                  
CONECT    9    8   10                                                       
CONECT   10    9   34   35   36                                             
CONECT   11    6   28   12   37                                             
CONECT   12   13   11   17   38                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   39   40   41                                             
CONECT   16   14                                                            
CONECT   17   18   20   12   42                                             
CONECT   18   17   19                                                       
CONECT   19   18   43   44   45                                             
CONECT   20   21   23   17   46                                             
CONECT   21   20   22                                                       
CONECT   22   21   47   48   49                                             
CONECT   23   24   28   20                                                  
CONECT   24   25   23   50                                                  
CONECT   25   24   26   51   52                                             
CONECT   26   25   27   28                                                  
CONECT   27    5   26   53   54                                             
CONECT   28   23   11   26   55                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    4                                                            
CONECT   33    7                                                            
CONECT   34   10                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   17                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   27                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

RDKit          3D

55 58  0  0  0  0  0  0  0  0999 V2000
   -1.9277    3.6346    2.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6585    2.6542    1.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9548    1.8295    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960    1.9807    0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0389    1.0885   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917    0.0356   -1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0552   -0.1008   -0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906    0.7854    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215    0.7188    0.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937   -0.3337   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009   -0.8629   -1.9872 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5432   -2.1873   -2.4671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8145   -3.0255   -1.3226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191   -4.0206   -1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557   -4.8362   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3416   -4.2196   -2.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3985   -2.9146   -3.4803 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5013   -2.1620   -4.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696   -2.4264   -5.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -3.1291   -2.9157 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7838   -4.1848   -1.9452 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -4.7751   -1.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3426   -1.8798   -2.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -1.1998   -2.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824    0.0429   -1.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2351    0.0003   -0.8366 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931    1.2621   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4528   -1.1717   -1.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6260    4.1472    2.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043    4.3851    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508    3.1755    2.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116    2.7875    0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6139   -0.9010   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4101   -1.3125    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134   -0.2417    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -0.2504   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755   -0.2557   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905   -1.9352   -2.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880   -5.2682    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -4.2105    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5632   -5.6515   -0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.9115   -3.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117   -1.8281   -6.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -2.1450   -5.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780   -3.4831   -5.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942   -3.4222   -3.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4729   -5.1894   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -5.5920   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7454   -4.0513   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781   -1.4774   -3.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.9152   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3430    0.0526   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.7155   -1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9869    1.9686   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -1.8073   -0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 11  1  0
  5 27  1  0
 25 24  1  0
 24 23  2  0
 23 28  1  0
 26 25  1  0
 27 26  1  0
  8  9  1  0
 11 28  1  0
  9 10  1  0
  8  3  2  0
  3  2  1  0
  6  7  2  0
  2  1  1  0
  7  8  1  0
 12 13  1  0
  6  5  1  0
 20 21  1  0
 11 12  1  0
 17 18  1  0
 23 20  1  0
 11 37  1  6
 20 17  1  0
 18 19  1  0
 17 12  1  0
 21 22  1  0
 28 26  1  0
 28 55  1  1
 13 14  1  0
  3  4  1  0
 14 15  1  0
  4  5  2  0
 14 16  2  0
  4 32  1  0
  7 33  1  0
 27 53  1  0
 27 54  1  0
 20 46  1  6
 17 42  1  6
 12 38  1  6
 25 51  1  0
 25 52  1  0
 24 50  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₇NO₆

Average Mass

389.4480 Da

Monoisotopic Mass

389.18384 Da

IUPAC Name

(1S,13R,14R,15S,16S)-4,5,13,14-tetramethoxy-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,4,6,11-tetraen-15-yl acetate

Traditional Name

(1S,13R,14R,15S,16S)-4,5,13,14-tetramethoxy-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,4,6,11-tetraen-15-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C1=C2[C@@]3([H])N(C1([H])[H])C([H])([H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1[C@]3([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC([H])([H])[H])[C@]2([H])OC([H])([H])[H]

InChI Identifier

InChI=1S/C21H27NO6/c1-11(23)28-20-17-14-9-16(25-3)15(24-2)8-12(14)10-22-7-6-13(18(17)22)19(26-4)21(20)27-5/h6,8-9,17-21H,7,10H2,1-5H3/t17-,18+,19+,20-,21-/m0/s1

InChI Key

YUUHTZSDSDKWDN-ZPAWYTMASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Narcissus serotinus	JEOL database	Pigni, N. B., et al, J. Nat. Prod. 75, 1643 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Tetrahydroisoquinoline
Indole or derivatives
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Pyrroline
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Azacycle
Organic oxygen compound
Amine
Organic oxide
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen 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	1.67	ALOGPS
logP	1.03	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	8.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.2 m³·mol⁻¹	ChemAxon
Polarizability	41.89 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71466972

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pigni, N. B., et al. (2012). Pigni, N. B., et al, J. Nat. Prod. 75, 1643 (2012). J. Nat. Prod..

Showing NP-Card for 1-O-acetyl-3-O-methylnarcissidine (NP0036983)

MOL for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

3D MOL for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

3D SDF for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

3D-SDF for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

PDB for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

3D PDB for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

SMILES for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

INCHI for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

Structure for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)

3D Structure for NP0036983 (1-O-acetyl-3-O-methylnarcissidine)