NP-MRD: Showing NP-Card for methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate (NP0160645)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 18:38:39 UTC

Updated at

2022-09-02 18:38:39 UTC

NP-MRD ID

NP0160645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate

Description

21-O-Acetylpaxdaphnine B belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom. methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate is found in Daphniphyllum macropodum. Based on a literature review very few articles have been published on 21-O-Acetylpaxdaphnine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220382D          

 28 32  0  0  1  0            999 V2000
   -1.7804   -1.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905   -1.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0404   -1.1907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2429   -2.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009   -1.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041   -0.8117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3277   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    0.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825    1.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2030    1.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546    0.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3981    0.1202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9366    0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    0.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514   -0.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -1.2792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2513   -0.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0129   -0.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418   -2.0410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7290   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -2.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3769   -3.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675   -4.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -1.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -1.1978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4040    0.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927   -0.6289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
 26 25  1  6  0  0  0
 16 26  1  0  0  0  0
  3 26  1  0  0  0  0
  6 26  1  0  0  0  0
 12 27  1  1  0  0  0
 27 28  1  0  0  0  0
  3 28  1  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
   -0.4780   -2.9588    3.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9506   -1.7219    2.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619   -1.4963    1.3787 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4213   -1.2561    2.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -0.1347    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2247   -0.0636   -0.0134 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4980    1.2358   -0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999    1.3350   -0.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3778    2.4884   -1.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.6196   -1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5322    3.3815   -1.8652 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -1.2138   -0.8609 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4030   -1.1677   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299   -1.5465   -2.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475   -1.0148   -1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -0.5845   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4244   -0.2280   -0.1609 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9591    0.2685   -1.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4397   -0.8951   -2.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663    0.7747    0.9074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8644    2.0886    0.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5125    2.4701   -0.3103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6905    3.0393    1.7047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295    4.3439    1.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570    0.8676    1.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612   -0.2858    0.4980 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3825   -2.5689   -0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949   -2.6133    0.4920 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1387   -3.6174    2.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1896   -2.6475    4.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -3.4849    3.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954   -0.9198    3.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9108   -2.0039    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2513   -0.9194    3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0217   -2.1637    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742    0.8136    1.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1173   -0.3170    1.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9615    1.2900   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048    2.1383   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4099    3.0703   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883    1.5718   -2.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8944    3.1384   -2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -1.1393   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589   -0.2048   -2.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1249   -1.8951   -2.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792   -1.2639   -3.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0528   -2.6518   -2.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9630   -1.1449    0.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0420    0.2944   -1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4210    1.1477   -1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480   -1.7837   -2.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5022   -0.6307   -3.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815    0.3570    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586    4.6479    2.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302    4.3590    0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    5.0781    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763    1.8694    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5842    0.8733    2.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -3.0286    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108   -3.2921   -1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388   -2.7037   -0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6 12  1  0
 12 27  1  0
 27 28  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 25  1  0
 26 25  1  1
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 28  3  1  0
 19 15  1  0
 26  3  1  0
 26  6  1  0
 26 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  6
 27 59  1  0
 27 60  1  0
 28 61  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 17 48  1  1
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  1
 25 57  1  0
 25 58  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END


  Mrv1652309022220382D          

 28 32  0  0  1  0            999 V2000
   -1.7804   -1.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905   -1.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0404   -1.1907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2429   -2.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009   -1.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041   -0.8117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3277   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    0.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825    1.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2030    1.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546    0.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3981    0.1202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9366    0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    0.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514   -0.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -1.2792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2513   -0.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0129   -0.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418   -2.0410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7290   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -2.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3769   -3.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675   -4.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -1.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -1.1978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4040    0.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927   -0.6289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
 26 25  1  6  0  0  0
 16 26  1  0  0  0  0
  3 26  1  0  0  0  0
  6 26  1  0  0  0  0
 12 27  1  1  0  0  0
 27 28  1  0  0  0  0
  3 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CC[C@@]3(COC(C)=O)[C@@H](CN1)CCC1=C4[C@H](CC1)[C@@H](C[C@]234)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO4/c1-4-22-10-9-21(13-28-14(2)25)16(12-24-22)7-5-15-6-8-17-18(20(26)27-3)11-23(21,22)19(15)17/h16-18,24H,4-13H2,1-3H3/t16-,17-,18-,21-,22+,23-/m1/s1

> <INCHI_KEY>
KSROFXNZRLENBT-XWBRHDOPSA-N

> <FORMULA>
C23H33NO4

> <MOLECULAR_WEIGHT>
387.52

> <EXACT_MASS>
387.240958547

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.98591903979957

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,5S,8S,14R,15R)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0^{1,5}.0^{2,8}.0^{14,17}]heptadec-11(17)-ene-15-carboxylate

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.0697433873333324

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.892397498569215

> <JCHEM_POLAR_SURFACE_AREA>
64.63000000000001

> <JCHEM_REFRACTIVITY>
105.46299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,5S,8S,14R,15R)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0^{1,5}.0^{2,8}.0^{14,17}]heptadec-11(17)-ene-15-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.324  -2.738   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.662  -2.902   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.075  -2.223   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.453  -3.890   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.562  -2.937   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.941  -1.515   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.478  -0.848   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.339   0.771   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.901   2.013   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.379   3.567   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.662   1.720   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.743   0.224   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.748   1.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.246   1.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.063  -0.092   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.456  -1.544   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.748  -2.388   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.069  -1.507   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.624  -0.031   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.185  -3.810   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.094  -5.172   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.695  -5.149   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.437  -6.641   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.166  -8.027   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.614  -3.705   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.875  -2.236   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.754   0.248   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -1.293  -1.174   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26   28                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12   26                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   27                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   17   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   20   26                                                       
CONECT   26   25   16    3    6                                             
CONECT   27   12   28                                                       
CONECT   28   27    3                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₃NO₄

Average Mass

387.5200 Da

Monoisotopic Mass

387.24096 Da

IUPAC Name

methyl (1R,2R,5S,8S,14R,15R)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0^{1,5}.0^{2,8}.0^{14,17}]heptadec-11(17)-ene-15-carboxylate

Traditional Name

methyl (1R,2R,5S,8S,14R,15R)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0^{1,5}.0^{2,8}.0^{14,17}]heptadec-11(17)-ene-15-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@@]12CC[C@@]3(COC(C)=O)[C@@H](CN1)CCC1=C4[C@H](CC1)[C@@H](C[C@]234)C(=O)OC

InChI Identifier

InChI=1S/C23H33NO4/c1-4-22-10-9-21(13-28-14(2)25)16(12-24-22)7-5-15-6-8-17-18(20(26)27-3)11-23(21,22)19(15)17/h16-18,24H,4-13H2,1-3H3/t16-,17-,18-,21-,22+,23-/m1/s1

InChI Key

KSROFXNZRLENBT-XWBRHDOPSA-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 macropodum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Delta amino acids and derivatives

Alternative Parents

Substituents

Delta amino acid or derivatives
Azaspirodecane
Monoterpenoid
Azepane
Dicarboxylic acid or derivatives
Piperidine
Methyl ester
Carboxylic acid ester
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
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	2.82	ALOGPS
logP	2.07	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	10.89	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	105.46 m³·mol⁻¹	ChemAxon
Polarizability	42.99 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	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

101456792

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate (NP0160645)

MOL for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

3D MOL for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

3D SDF for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

3D-SDF for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

PDB for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

3D PDB for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

SMILES for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

INCHI for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

Structure for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)

3D Structure for NP0160645 (methyl (1r,2r,5s,8s,14r,15r)-2-[(acetyloxy)methyl]-5-ethyl-6-azapentacyclo[9.5.1.0¹,⁵.0²,⁸.0¹⁴,¹⁷]heptadec-11(17)-ene-15-carboxylate)