NP-MRD: Showing NP-Card for daphlongeranine A (NP0038874)

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Record Information

Version

2.0

Created at

2021-06-20 21:27:02 UTC

Updated at

2021-06-30 00:11:53 UTC

NP-MRD ID

NP0038874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

daphlongeranine A

Provided By

JEOL Database JEOL Logo

Description

(1S,2S,7R,12R,15S,19S,23S,25R)-25-(hydroxymethyl)-19-methyl-3,22-dioxa-17-azaheptacyclo[13.8.2.0¹,¹⁷.0²,⁷.0⁷,²⁵.0⁸,¹².0¹⁹,²³]Pentacos-8-ene-4,21-dione belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. daphlongeranine A is found in Daphniphyllum longeracemosum. daphlongeranine A was first documented in 2007 (Li, C.-S., et al.). Based on a literature review very few articles have been published on (1S,2S,7R,12R,15S,19S,23S,25R)-25-(hydroxymethyl)-19-methyl-3,22-dioxa-17-azaheptacyclo[13.8.2.0¹,¹⁷.0²,⁷.0⁷,²⁵.0⁸,¹².0¹⁹,²³]Pentacos-8-ene-4,21-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123273D          

 61 67  0  0  0  0            999 V2000
   -3.1761   -3.4117    2.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3464   -2.2189    2.8774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2791   -2.1684    4.3975 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8685   -1.7834    4.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -1.4009    5.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837   -2.0042    3.6069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.2972    2.4430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7001   -1.1819    1.3996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0462   -1.6250   -0.0272 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7091   -0.3458   -0.8352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7495   -0.6863   -2.3442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0732   -1.0251   -2.7469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478    0.6706   -0.4494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9240    1.9433   -1.3130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8144    2.9743   -1.1487 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6081    2.4456   -1.3603 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6221    3.5957   -1.2228 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9934    3.6283    0.2542 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7848    2.2025    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0557    1.5165   -0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    0.0215   -0.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8712   -0.6492   -1.0773 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1575   -0.7563   -0.2722 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9314   -1.6747    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8268   -2.3617    1.3645 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -1.7411    1.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -0.6292    1.1915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8681    0.9891    1.0580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6559   -0.1724    1.9135 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8712   -0.9043    2.2622 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7789   -4.3533    2.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159   -3.3198    2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -3.4921    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -3.1489    4.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -1.4386    4.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5801   -3.2834    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -2.4735   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -1.9451   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1265   -1.5515   -2.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092    0.1507   -2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461   -1.2090   -3.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.1579   -0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729    2.4481   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    1.6742   -2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    3.7763   -1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9087    3.4496   -0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2406    4.5606   -1.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0652   -0.1048   -2.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8098    1.4895    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0945    1.7179    1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4908   -1.0991    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4857   -0.3316    2.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 13  1  0  0  0  0
 21 10  1  0  0  0  0
  8 29  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 27 26  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  1  0  0  0  0
 10 13  1  0  0  0  0
  8  7  1  0  0  0  0
  2 30  1  0  0  0  0
 30 29  1  0  0  0  0
  2  7  1  0  0  0  0
 18 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  6  0  0  0
 21 20  1  0  0  0  0
 16 15  1  0  0  0  0
 19 20  2  0  0  0  0
 11 12  1  0  0  0  0
  8 27  1  0  0  0  0
  2  1  1  1  0  0  0
 20 16  1  0  0  0  0
  7 36  1  6  0  0  0
 29 28  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
  7  6  1  0  0  0  0
 13 42  1  6  0  0  0
  6  4  1  0  0  0  0
 27 57  1  1  0  0  0
  4  3  1  0  0  0  0
  4  5  2  0  0  0  0
  3  2  1  0  0  0  0
 24 25  2  0  0  0  0
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 16 47  1  6  0  0  0
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  3 34  1  0  0  0  0
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 22 53  1  0  0  0  0
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 14 43  1  0  0  0  0
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 15 46  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 12 41  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
M  END

     RDKit          3D

 61 67  0  0  0  0  0  0  0  0999 V2000
   -3.1761   -3.4117    2.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3464   -2.2189    2.8774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2791   -2.1684    4.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685   -1.7834    4.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -1.4009    5.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837   -2.0042    3.6069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.2972    2.4430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7001   -1.1819    1.3996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0462   -1.6250   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7091   -0.3458   -0.8352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7495   -0.6863   -2.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732   -1.0251   -2.7469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478    0.6706   -0.4494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9240    1.9433   -1.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144    2.9743   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9934    3.6283    0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9684   -1.4386    4.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5801   -3.2834    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -2.4735   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -1.9451   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 37  1  0
  9 38  1  0
M  END


  Mrv1652306202123273D          

 61 67  0  0  0  0            999 V2000
   -3.1761   -3.4117    2.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3464   -2.2189    2.8774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2791   -2.1684    4.3975 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8685   -1.7834    4.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -1.4009    5.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837   -2.0042    3.6069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.2972    2.4430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7001   -1.1819    1.3996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0462   -1.6250   -0.0272 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7091   -0.3458   -0.8352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7495   -0.6863   -2.3442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0732   -1.0251   -2.7469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478    0.6706   -0.4494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9240    1.9433   -1.3130 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0038874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]12C([H])([H])[C@@]34N(C([H])([H])[C@]5(C([H])([H])[H])C([H])([H])C(=O)O[C@]35[H])C([H])([H])[C@@]1([H])C([H])([H])C([H])([H])[C@]1([H])C(=C([H])C([H])([H])C1([H])[H])[C@]21C([H])([H])C([H])([H])C(=O)O[C@]41[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H31NO5/c1-21-9-18(28)30-19(21)24-11-22(13-26)15(10-25(24)12-21)6-5-14-3-2-4-16(14)23(22)8-7-17(27)29-20(23)24/h4,14-15,19-20,26H,2-3,5-13H2,1H3/t14-,15-,19+,20+,21+,22-,23+,24-/m1/s1

> <INCHI_KEY>
WFFPYMROVFKGGJ-DFAHMUSMSA-N

> <FORMULA>
C24H31NO5

> <MOLECULAR_WEIGHT>
413.514

> <EXACT_MASS>
413.220223102

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.77991722994672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,7R,12R,15S,19S,23S,25R)-25-(hydroxymethyl)-19-methyl-3,22-dioxa-17-azaheptacyclo[13.8.2.0^{1,17}.0^{2,7}.0^{7,25}.0^{8,12}.0^{19,23}]pentacos-8-ene-4,21-dione

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
1.1610977296666662

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.0640053109118

> <JCHEM_PKA_STRONGEST_BASIC>
9.654620199481263

> <JCHEM_POLAR_SURFACE_AREA>
76.07

> <JCHEM_REFRACTIVITY>
107.97389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,7R,12R,15S,19S,23S,25R)-25-(hydroxymethyl)-19-methyl-3,22-dioxa-17-azaheptacyclo[13.8.2.0^{1,17}.0^{2,7}.0^{7,25}.0^{8,12}.0^{19,23}]pentacos-8-ene-4,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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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      -3.176  -3.412   2.402  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.346  -2.219   2.877  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.279  -2.168   4.397  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.869  -1.783   4.689  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.457  -1.401   5.773  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.084  -2.004   3.607  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.874  -2.297   2.443  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.700  -1.182   1.400  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.046  -1.625  -0.027  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.709  -0.346  -0.835  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.750  -0.686  -2.344  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.073  -1.025  -2.747  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.848   0.671  -0.449  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.924   1.943  -1.313  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.814   2.974  -1.149  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.608   2.446  -1.360  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.622   3.596  -1.223  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.993   3.628   0.254  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.785   2.203   0.645  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.056   1.517  -0.255  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.734   0.022  -0.256  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.871  -0.649  -1.077  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.158  -0.756  -0.272  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.931  -1.675   0.888  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.827  -2.362   1.365  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.661  -1.741   1.339  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.737  -0.629   1.192  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.868   0.989   1.058  0.00  0.00           C+0
HETATM   29  N   UNK     0      -1.656  -0.172   1.914  0.00  0.00           N+0
HETATM   30  C   UNK     0      -2.871  -0.904   2.262  0.00  0.00           C+0
HETATM   31  H   UNK     0      -2.779  -4.353   2.797  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.216  -3.320   2.735  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.178  -3.492   1.310  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.454  -3.149   4.853  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.968  -1.439   4.830  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.580  -3.283   2.067  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.421  -2.474  -0.335  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.085  -1.945  -0.159  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.127  -1.552  -2.586  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.409   0.151  -2.958  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.046  -1.209  -3.702  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.802   0.158  -0.649  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.873   2.448  -1.085  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.000   1.674  -2.372  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.001   3.776  -1.876  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.909   3.450  -0.164  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.715   1.996  -2.352  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.516   3.367  -1.820  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.241   4.561  -1.573  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.337   4.286   0.833  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.031   3.943   0.393  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.233   1.803   1.545  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.065  -0.105  -2.010  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.588  -1.669  -1.365  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.929  -1.204  -0.909  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.534   0.203   0.087  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.971   0.074   1.996  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.810   1.490   1.320  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.095   1.718   1.313  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.491  -1.099   1.378  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.486  -0.332   2.965  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2   30    7    1    3                                             
CONECT    3    4    2   34   35                                             
CONECT    4    6    3    5                                                  
CONECT    5    4                                                            
CONECT    6    7    4                                                       
CONECT    7    8    2   36    6                                             
CONECT    8   29    7   27    9                                             
CONECT    9    8   10   37   38                                             
CONECT   10   21   13   11    9                                             
CONECT   11   10   12   39   40                                             
CONECT   12   11   41                                                       
CONECT   13   28   10   14   42                                             
CONECT   14   13   15   43   44                                             
CONECT   15   14   16   45   46                                             
CONECT   16   17   15   20   47                                             
CONECT   17   16   18   48   49                                             
CONECT   18   17   19   50   51                                             
CONECT   19   18   20   52                                                  
CONECT   20   21   19   16                                                  
CONECT   21   10   22   20   27                                             
CONECT   22   21   23   53   54                                             
CONECT   23   22   24   55   56                                             
CONECT   24   23   26   25                                                  
CONECT   25   24                                                            
CONECT   26   27   24                                                       
CONECT   27   26    8   57   21                                             
CONECT   28   13   29   58   59                                             
CONECT   29    8   30   28                                                  
CONECT   30    2   29   60   61                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    7                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   22                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  134    0
END

RDKit          3D

61 67  0  0  0  0  0  0  0  0999 V2000
   -3.1761   -3.4117    2.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3464   -2.2189    2.8774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2791   -2.1684    4.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685   -1.7834    4.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -1.4009    5.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837   -2.0042    3.6069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -2.2972    2.4430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7001   -1.1819    1.3996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0462   -1.6250   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7091   -0.3458   -0.8352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7495   -0.6863   -2.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732   -1.0251   -2.7469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478    0.6706   -0.4494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9240    1.9433   -1.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144    2.9743   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6081    2.4456   -1.3603 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6221    3.5957   -1.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9934    3.6283    0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7848    2.2025    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0557    1.5165   -0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    0.0215   -0.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8712   -0.6492   -1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1575   -0.7563   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9314   -1.6747    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8268   -2.3617    1.3645 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -1.7411    1.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -0.6292    1.1915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8681    0.9891    1.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559   -0.1724    1.9135 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8712   -0.9043    2.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -4.3533    2.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159   -3.3198    2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -3.4921    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -3.1489    4.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -1.4386    4.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5801   -3.2834    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -2.4735   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -1.9451   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1265   -1.5515   -2.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092    0.1507   -2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461   -1.2090   -3.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.1579   -0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729    2.4481   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    1.6742   -2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    3.7763   -1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9087    3.4496   -0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154    1.9963   -2.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    3.3673   -1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2406    4.5606   -1.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    4.2857    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0315    3.9433    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334    1.8030    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652   -0.1048   -2.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876   -1.6690   -1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9287   -1.2044   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5336    0.2031    0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9713    0.0740    1.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8098    1.4895    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0945    1.7179    1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4908   -1.0991    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4857   -0.3316    2.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 13  1  0
 21 10  1  0
  8 29  1  1
 16 17  1  0
 17 18  1  0
 27 26  1  0
 21 22  1  6
 22 23  1  0
 23 24  1  0
 24 26  1  0
 10 13  1  0
  8  7  1  0
  2 30  1  0
 30 29  1  0
  2  7  1  0
 18 19  1  0
 13 14  1  0
 14 15  1  0
 10 11  1  6
 21 20  1  0
 16 15  1  0
 19 20  2  0
 11 12  1  0
  8 27  1  0
  2  1  1  1
 20 16  1  0
  7 36  1  6
 29 28  1  0
  8  9  1  0
 10  9  1  0
  7  6  1  0
 13 42  1  6
  6  4  1  0
 27 57  1  1
  4  3  1  0
  4  5  2  0
  3  2  1  0
 24 25  2  0
 27 21  1  0
 16 47  1  6
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
  3 34  1  0
  3 35  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  9 37  1  0
  9 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₁NO₅

Average Mass

413.5140 Da

Monoisotopic Mass

413.22022 Da

IUPAC Name

(1S,2S,7R,12R,15S,19S,23S,25R)-25-(hydroxymethyl)-19-methyl-3,22-dioxa-17-azaheptacyclo[13.8.2.0^{1,17}.0^{2,7}.0^{7,25}.0^{8,12}.0^{19,23}]pentacos-8-ene-4,21-dione

Traditional Name

(1S,2S,7R,12R,15S,19S,23S,25R)-25-(hydroxymethyl)-19-methyl-3,22-dioxa-17-azaheptacyclo[13.8.2.0^{1,17}.0^{2,7}.0^{7,25}.0^{8,12}.0^{19,23}]pentacos-8-ene-4,21-dione

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@]12C([H])([H])[C@@]34N(C([H])([H])[C@]5(C([H])([H])[H])C([H])([H])C(=O)O[C@]35[H])C([H])([H])[C@@]1([H])C([H])([H])C([H])([H])[C@]1([H])C(=C([H])C([H])([H])C1([H])[H])[C@]21C([H])([H])C([H])([H])C(=O)O[C@]41[H]

InChI Identifier

InChI=1S/C24H31NO5/c1-21-9-18(28)30-19(21)24-11-22(13-26)15(10-25(24)12-21)6-5-14-3-2-4-16(14)23(22)8-7-17(27)29-20(23)24/h4,14-15,19-20,26H,2-3,5-13H2,1H3/t14-,15-,19+,20+,21+,22-,23+,24-/m1/s1

InChI Key

WFFPYMROVFKGGJ-DFAHMUSMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃ / CD₃OH (9:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daphniphyllum longeracemosum	JEOL database	Li, C.-S., et al, Org. Lett. 9, 2509 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indolizidine
Furopyrrole
Azepane
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Gamma butyrolactone
N-alkylpyrrolidine
Oxane
Piperidine
Furan
Pyrrolidine
Pyrrole
Oxolane
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Lactone
Azacycle
Oxacycle
Carboxylic acid derivative
Amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary 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	2.35	ALOGPS
logP	1.16	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	15.06	ChemAxon
pKa (Strongest Basic)	9.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	107.97 m³·mol⁻¹	ChemAxon
Polarizability	43.78 Å³	ChemAxon
Number of Rings	7	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

Not Available

Chemspider ID

28284207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16726063

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, C.-S., et al. (2007). Li, C.-S., et al, Org. Lett. 9, 2509 (2007). Org. Lett..

Showing NP-Card for daphlongeranine A (NP0038874)

MOL for NP0038874 (daphlongeranine A)

3D MOL for NP0038874 (daphlongeranine A)

3D SDF for NP0038874 (daphlongeranine A)

3D-SDF for NP0038874 (daphlongeranine A)

PDB for NP0038874 (daphlongeranine A)

3D PDB for NP0038874 (daphlongeranine A)

SMILES for NP0038874 (daphlongeranine A)

INCHI for NP0038874 (daphlongeranine A)

Structure for NP0038874 (daphlongeranine A)

3D Structure for NP0038874 (daphlongeranine A)