NP-MRD: Showing NP-Card for methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate (NP0214160)

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Record Information

Version

2.0

Created at

2022-09-05 13:23:00 UTC

Updated at

2022-09-05 13:23:00 UTC

NP-MRD ID

NP0214160

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate

Description

Calyciphylline O belongs to the class of organic compounds known as daphniphylline-type alkaloids. These are alkaloids (or derivatives thereof) from the genus Daphniphyllum, possessing 22 carbon polycyclic fused ring systems with or without the C8 side chain. The C8 unit consists of 6-oxabicyclo[3.2.1]Octane or 2,8-dioxabicyclo[3.2.1]Octane. methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate is found in Daphniphyllum calycinum. Based on a literature review very few articles have been published on calyciphylline O.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215232D          

 27 31  0  0  1  0            999 V2000
    5.7577    3.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614    2.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7469    2.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4018    1.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    1.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3117    1.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4628    1.1026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5491    0.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -0.0264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1718    0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818    0.6013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1976   -0.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168    1.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451    1.5115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5822    2.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752    2.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8466    2.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184    1.7569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3592    1.6669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4270    2.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7727    1.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880    0.2890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8314   -0.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995   -1.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7198   -0.5991    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 15 19  1  0  0  0  0
  7 19  1  0  0  0  0
 11 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    4.7584   -3.7052    1.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281   -2.5003    1.2373 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5144   -2.1821    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -3.0393   -0.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8454   -0.8415   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -1.0330   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4617    0.1073   -0.2178 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8954   -0.3728    0.3532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8513    0.6897    0.3590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774    1.9287   -0.1271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6722    1.9040   -1.4343 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1382    3.1754   -1.3776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4825    4.1933   -2.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160    3.5932    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2018    2.3263    0.7796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6581    2.5671    2.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    1.4489    3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9775    0.7729    2.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8017    1.2399    0.7769 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1826    0.6471   -1.5551 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3955    0.9322   -2.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423   -0.2678   -2.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9140   -0.7237   -1.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -1.4511   -0.5337 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5874   -2.2005    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0586   -3.2497   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7418   -1.3652    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6950   -3.7695    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9858   -3.6922    2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477   -4.5299    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2332   -0.4864   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840   -0.1784    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926   -1.6158    0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1111   -1.7830   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7610   -0.8387    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.8664    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1759    2.6772   -0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3884    2.0148   -2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1530    3.1113   -1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274    4.4033   -2.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2435    3.8537    0.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    4.3796    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197    3.5125    2.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    2.6375    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036    0.7621    3.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686    1.8111    3.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898    1.1118    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -0.3006    2.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7616    1.7013    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282   -0.0265   -2.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2211    1.4205   -1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    1.5053   -3.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9178    0.3290   -3.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0864   -1.1490   -2.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387    0.1362   -1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557   -1.3587   -2.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7453   -2.2099   -0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1108   -2.7375    0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7791   -2.7855   -1.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -3.6329   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5666   -4.0964   -0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6492   -2.0395    0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6891   -1.0168    1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9282   -0.5805   -0.1955 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
  3  5  1  0
  5  6  1  0
  7  6  1  6
  7 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 15 16  1  1
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  6
 24 25  1  0
 25 26  1  0
 25 27  1  0
  8  7  1  0
 20  7  1  0
 15 19  1  0
 10 15  1  0
 20 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
 19 49  1  6
 18 47  1  0
 18 48  1  0
 17 45  1  0
 17 46  1  0
 16 43  1  0
 16 44  1  0
 14 41  1  0
 14 42  1  0
 12 39  1  6
 13 40  1  0
 11 38  1  6
 10 37  1  6
  9 36  1  0
  8 35  1  1
 24 57  1  6
 23 55  1  0
 23 56  1  0
 22 53  1  0
 22 54  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 27 64  1  0
M  END


  Mrv1652309052215232D          

 27 31  0  0  1  0            999 V2000
    5.7577    3.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614    2.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7469    2.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4018    1.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    1.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3117    1.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4628    1.1026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5491    0.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -0.0264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1718    0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818    0.6013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1976   -0.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168    1.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451    1.5115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5822    2.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752    2.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8466    2.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184    1.7569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3592    1.6669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4270    2.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7727    1.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880    0.2890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8314   -0.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995   -1.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7198   -0.5991    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 15 19  1  0  0  0  0
  7 19  1  0  0  0  0
 11 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214160

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC[C@]12[C@@H]3CCC[C@@]33C[C@H](O)C4C3NC1[C@H](CC[C@]24C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H37NO3/c1-13(2)14-7-10-21(3)18-15(25)12-22-9-5-6-16(22)23(21,11-8-17(26)27-4)19(14)24-20(18)22/h13-16,18-20,24-25H,5-12H2,1-4H3/t14-,15+,16-,18?,19?,20?,21+,22-,23+/m1/s1

> <INCHI_KEY>
SCMNGYBPXCTRJK-WTYMGFRSSA-N

> <FORMULA>
C23H37NO3

> <MOLECULAR_WEIGHT>
375.553

> <EXACT_MASS>
375.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
43.38384281604812

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-[(1S,2R,3R,7R,9S,14R)-9-hydroxy-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,11}]hexadecan-2-yl]propanoate

> <JCHEM_LOGP>
2.8719727889999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.861895914981929

> <JCHEM_PKA_STRONGEST_BASIC>
10.411579334704019

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
104.12389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[(1S,2R,3R,7R,9S,14R)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,11}]hexadecan-2-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      10.748   5.963   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.261   5.560   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.861   4.048   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.083   3.112   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.321   3.409   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.182   2.062   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.597   2.058   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.758   0.534   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.346  -0.049   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.187   0.920   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.742   2.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.086   1.122   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.369  -0.332   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.405   2.459   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.951   2.821   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.087   4.200   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.007   5.443   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.447   4.889   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.394   3.280   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.404   3.112   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.530   4.797   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.078   3.259   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.042   1.949   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.324   0.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.152  -0.929   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.532  -2.392   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.810  -1.118   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19   20                                             
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   10   16   19                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15    7                                                  
CONECT   20   11    7   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    8   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₇NO₃

Average Mass

375.5530 Da

Monoisotopic Mass

375.27734 Da

IUPAC Name

methyl 3-[(1S,2R,3R,7R,9S,14R)-9-hydroxy-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,11}]hexadecan-2-yl]propanoate

Traditional Name

methyl 3-[(1S,2R,3R,7R,9S,14R)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,11}]hexadecan-2-yl]propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC[C@]12[C@@H]3CCC[C@@]33C[C@H](O)C4C3NC1[C@H](CC[C@]24C)C(C)C

InChI Identifier

InChI=1S/C23H37NO3/c1-13(2)14-7-10-21(3)18-15(25)12-22-9-5-6-16(22)23(21,11-8-17(26)27-4)19(14)24-20(18)22/h13-16,18-20,24-25H,5-12H2,1-4H3/t14-,15+,16-,18?,19?,20?,21+,22-,23+/m1/s1

InChI Key

SCMNGYBPXCTRJK-WTYMGFRSSA-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
Daphniphyllum calycinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as daphniphylline-type alkaloids. These are alkaloids (or derivatives thereof) from the genus Daphniphyllum, possessing 22 carbon polycyclic fused ring systems with or without the C8 side chain. The C8 unit consists of 6-oxabicyclo[3.2.1]Octane or 2,8-dioxabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Daphniphylline-type alkaloids

Sub Class

Not Available

Direct Parent

Daphniphylline-type alkaloids

Alternative Parents

Substituents

Daphniphylline-type alkaloid
Sesquiterpenoid
Delta amino acid or derivatives
Quinolidine
Fatty acid ester
Fatty acyl
Piperidine
Methyl ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.87	ChemAxon
pKa (Strongest Acidic)	14.86	ChemAxon
pKa (Strongest Basic)	10.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.12 m³·mol⁻¹	ChemAxon
Polarizability	43.38 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

C00047206

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

102282915

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate (NP0214160)

MOL for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

3D MOL for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

3D SDF for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

3D-SDF for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

PDB for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

3D PDB for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

SMILES for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

INCHI for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

Structure for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)

3D Structure for NP0214160 (methyl 3-[(1s,2r,3r,7r,9s,14r)-9-hydroxy-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹¹]hexadecan-2-yl]propanoate)