NP-MRD: Showing NP-Card for (2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol (NP0138423)

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Record Information

Version

1.0

Created at

2022-06-29 17:28:52 UTC

Updated at

2022-06-29 17:28:52 UTC

NP-MRD ID

NP0138423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol

Description

Isopaynantheine belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group. It was first documented in 2007 (PMID: 17685239). Based on a literature review a significant number of articles have been published on Isopaynantheine (PMID: 35468648) (PMID: 33063871) (PMID: 22341683) (PMID: 20352614).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214172D          

 29 32  0  0  1  0            999 V2000
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    1.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    2.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    3.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0985    3.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038   -0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 12 10  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 17 28  1  6  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -3.2995   -3.5108    1.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -2.2064    1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0676   -1.4497    1.5453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8663   -2.3662    1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2853   -1.6129    1.0475 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403   -2.0848    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963   -1.7286    0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -0.2230    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5441    0.4112    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7953    1.7413    0.6281 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9668    1.9270    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6301    3.0858   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490    2.9708   -1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3762    1.7164   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7186    0.5558   -0.8577 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708   -0.7146   -1.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5034   -0.8720   -1.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5069    0.6916   -0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3828   -0.2693    1.4335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8486    0.5651    1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9422   -0.3179    0.5636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1380    0.3381    0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    1.6302    0.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953    2.4383    1.1179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4153    3.8079    0.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1307   -0.3775   -0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9436   -1.5632   -0.9888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2847    0.2353   -1.1486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2486   -0.4431   -1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500   -4.1352    1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2601   -4.0366    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460   -1.7137    1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8886   -1.0184    2.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1219   -2.9030    0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8192   -3.1037    2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8741   -1.6142   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0349   -3.2032   -0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8517   -1.9981    1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2722   -2.1854   -0.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489    2.5054    0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008    4.0539   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972    3.8711   -1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3330    1.6643   -1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6303   -1.9378   -2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5223   -0.2156   -2.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3101   -0.5288   -1.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824   -0.2315    2.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1466    0.9997    2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5874    1.3386    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4677   -0.7943   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3000    2.0277    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0749    3.9098   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039    4.2607    1.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    4.3346    0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8791   -0.7473   -2.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0750    0.2984   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7220   -1.2721   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 22 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
  3 21  1  0
  9 19  1  0
 18 11  1  0
 18  8  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 23 51  1  0
 21 50  1  6
 20 48  1  0
 20 49  1  0
 19 47  1  1
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
 10 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
  4 34  1  0
  4 35  1  0
  3 33  1  1
  2 32  1  0
  1 30  1  0
  1 31  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
M  END


  Mrv1652304282214172D          

 29 32  0  0  1  0            999 V2000
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    1.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    2.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    3.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0985    3.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038   -0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 12 10  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 17 28  1  6  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0138423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\C=C(/[C@H]1C[C@H]2N(CCC3=C2NC2=CC=CC(OC)=C32)C[C@@H]1C=C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H28N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13+/t14-,16-,19+/m0/s1

> <INCHI_KEY>
JGZKIGWXPPFMRG-CGJCNEAHSA-N

> <FORMULA>
C23H28N2O4

> <MOLECULAR_WEIGHT>
396.487

> <EXACT_MASS>
396.20490739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.80687548081066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(2R,4S,5R)-5-ethenyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
2.995605600333334

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.670265610387272

> <JCHEM_PKA_STRONGEST_BASIC>
6.898711484113814

> <JCHEM_POLAR_SURFACE_AREA>
63.78999999999999

> <JCHEM_REFRACTIVITY>
112.95729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(2R,4S,5R)-5-ethenyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.404  -0.063   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.477   1.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.181   2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.812   1.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.739   0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.035  -0.768   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.962  -2.307   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.593  -3.012   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.254  -0.341   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.409   0.946   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.372   2.147   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.871   0.858   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.179  -0.517   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.024  -1.805   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.561  -1.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.641  -0.606   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.204   0.682   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.489   2.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.026   2.146   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.356   3.345   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.894   3.257   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.586   1.881   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.124   1.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.336   4.720   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.874   4.809   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.509   6.008   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.184   7.383   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.741   0.594   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.434  -0.782   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   12                                                       
CONECT   20   18   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   17   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₃₅NO₂

Average Mass

285.4720 Da

Monoisotopic Mass

285.26678 Da

IUPAC Name

methyl (2E)-2-[(2R,4S,5R)-5-ethenyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(2R,4S,5R)-5-ethenyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

CAS Registry Number

6918-48-5

SMILES

CCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO

InChI Identifier

InChI=1S/C17H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)16(18)15-19/h13-14,16-17,19-20H,2-12,15,18H2,1H3/b14-13+/t16-,17+/m0/s1

InChI Key

RBEJCQPPFCKTRZ-LHMZYYNSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Beta-carboline
Pyridoindole
Quinolizine
3-alkylindole
Indole
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Pyrrole
Enoate ester
Methyl ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	3.18	ALOGPS
logP	3	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.67	ChemAxon
pKa (Strongest Basic)	6.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.96 m³·mol⁻¹	ChemAxon
Polarizability	43.81 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

C00025182

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

101804033

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Manwill PK, Flores-Bocanegra L, Khin M, Raja HA, Cech NB, Oberlies NH, Todd DA: Kratom (Mitragyna speciosa) Validation: Quantitative Analysis of Indole and Oxindole Alkaloids Reveals Chemotypes of Plants and Products. Planta Med. 2022 Apr 25. doi: 10.1055/a-1795-5876. [PubMed:35468648 ]
Muller T, Graler MH: Development and validation of a QTrap method for sensitive quantification of sphingosine 1-phosphate. Biomed Chromatogr. 2021 Mar;35(3):e5004. doi: 10.1002/bmc.5004. Epub 2020 Nov 5. [PubMed:33063871 ]
Ferreiros N, Labocha S, Schroder M, Radeke HH, Geisslinger G: LC-MS/MS determination of FTY720 and FTY720-phosphate in murine intracellular compartments and human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Mar 1;887-888:122-7. doi: 10.1016/j.jchromb.2012.01.023. Epub 2012 Jan 30. [PubMed:22341683 ]
Lan T, Bi H, Xu S, Le K, Xie Z, Liu Y, Huang H: Determination of sphingosine kinase activity in biological samples by liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2010 Oct;24(10):1075-83. doi: 10.1002/bmc.1407. [PubMed:20352614 ]
Rammouz G, Usta J, Ribeiro SJ, Messaddeq Y, Couderc F, Poinsot V: Analysis of sphingosine 1-phosphate by capillary electrophoresis coupled to laser-induced fluorescence detection: use of a transparent fused-silica capillary. J Capill Electrophor Microchip Technol. 2007;10(1-2):25-31. [PubMed:17685239 ]

Showing NP-Card for (2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol (NP0138423)

MOL for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

3D MOL for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

3D SDF for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

3D-SDF for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

PDB for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

3D PDB for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

SMILES for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

INCHI for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

Structure for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)

3D Structure for NP0138423 ((2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol)