NP-MRD: Showing NP-Card for 5-Epi-dihydrolyfoline (NP0081391)

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Record Information

Version

2.0

Created at

2022-04-29 02:21:47 UTC

Updated at

2022-04-29 02:21:47 UTC

NP-MRD ID

NP0081391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Epi-dihydrolyfoline

Description

5-Epi-Dihydrolyfoline belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 5-Epi-dihydrolyfoline is found in Lagerstroemia indica . 5-Epi-dihydrolyfoline was first documented in 2009 (PMID: 19260657). Based on a literature review a small amount of articles have been published on 5-epi-Dihydrolyfoline (PMID: 25885429) (PMID: 21796576).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204212D          

 31 35  0  0  1  0            999 V2000
    4.9211   -0.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337   -0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9311   -1.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7236   -1.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5246   -1.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2472   -2.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2638   -3.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5577   -3.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351   -3.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -2.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -2.3827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1515   -4.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800   -4.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -4.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041   -5.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865   -4.6452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3916   -4.0736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5667   -4.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400   -3.3841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5381   -2.6615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -2.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7897   -3.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1113   -1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2865   -1.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8884   -2.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3152   -3.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387    0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5236    0.5178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3161    0.7473    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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 19 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
  3 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
   -3.7272   -4.5328   -0.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162   -4.6439   -0.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5722   -3.5868   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0210   -2.2975   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2336   -1.1671   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751   -1.3652    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944   -2.6745    0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897   -3.7746    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955   -5.0709    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539   -0.3188    0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5018    0.7983    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    2.1018    1.0126 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6315    2.0237    1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137    0.8766    0.1887 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9506   -0.0306    0.9032 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2163   -1.2813    0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -1.0729   -1.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530   -0.7413   -1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523    0.2325   -0.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5169    3.2533    1.4459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    3.8349    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060    3.9343    1.4930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6233    4.3994   -0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7971    3.8171   -1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1684    2.4435   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3721    2.4635   -0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515    1.3345    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183    0.1945    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583   -0.8948    1.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9071    0.1547   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407    1.2844   -0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4213   -4.3057   -0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0065   -5.5117   -1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -3.7564   -1.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0485   -2.1069   -0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5234   -2.8575    0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3555   -5.8776    0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8579   -0.7764    1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839    0.7419    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572    0.8919    1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795    2.0701   -0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219    2.9978    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9755    1.8622    2.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5656    1.3504   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2159    1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383    0.5210    0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3239   -1.4880    0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8011   -2.1944    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3379   -0.3168   -1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8684   -2.0211   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7156   -1.7054   -1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730   -0.3325   -2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977    5.5111   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929    4.1533   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854    4.5303   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5816    4.0065   -2.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9529    3.3992   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7860    1.3950    1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4911   -0.8967    1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5052    1.2385   -1.6589 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
  8  3  1  0
 19 10  1  0
 31 25  2  0
 30  5  1  0
 19 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  7 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  0
 11 40  1  0
 12 41  1  6
 13 42  1  0
 13 43  1  0
 14 44  1  6
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 26 57  1  0
 27 58  1  0
 29 59  1  0
 31 60  1  0
M  END


  Mrv1652304292204212D          

 31 35  0  0  1  0            999 V2000
    4.9211   -0.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337   -0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9311   -1.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7236   -1.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5246   -1.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2472   -2.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2638   -3.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5577   -3.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351   -3.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -2.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -2.3827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1515   -4.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800   -4.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -4.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041   -5.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865   -4.6452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3916   -4.0736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5667   -4.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400   -3.3841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5381   -2.6615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -2.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7897   -3.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1113   -1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2865   -1.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8884   -2.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3152   -3.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387    0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5236    0.5178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3161    0.7473    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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 19 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
  3 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)[C@@H]1C[C@H](C[C@H]3CCCCN13)OC(=O)CCC1=CC=C(O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H29NO5/c1-30-24-14-18-19(13-23(24)28)21-12-17(11-16-4-2-3-9-26(16)21)31-25(29)8-6-15-5-7-22(27)20(18)10-15/h5,7,10,13-14,16-17,21,27-28H,2-4,6,8-9,11-12H2,1H3/t16-,17+,21+/m1/s1

> <INCHI_KEY>
DUKDUISHTJYQFV-WWMYMODYSA-N

> <FORMULA>
C25H29NO5

> <MOLECULAR_WEIGHT>
423.509

> <EXACT_MASS>
423.204573038

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.62740007957676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.1^{8,12}.0^{2,7}.0^{19,24}]hexacosa-2(7),3,5,8(26),9,11-hexaen-15-one

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.719240620624234

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.844504185291385

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.036984451577895

> <JCHEM_PKA_STRONGEST_BASIC>
7.2527508943685834

> <JCHEM_POLAR_SURFACE_AREA>
79.23

> <JCHEM_REFRACTIVITY>
117.78499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.1^{8,12}.0^{2,7}.0^{19,24}]hexacosa-2(7),3,5,8(26),9,11-hexaen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.186  -1.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.075  -0.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.596  -0.957   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.228  -2.452   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.338  -3.519   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.817  -3.091   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.313  -3.459   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.661  -4.202   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.692  -5.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.374  -6.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.026  -5.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.995  -4.256   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.467  -4.448   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.483  -7.501   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.416  -8.611   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.937  -9.040   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.968 -10.579   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.442  -8.671   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.331  -7.604   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.791  -7.635   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.995  -6.317   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       4.738  -4.968   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.277  -4.937   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.074  -6.255   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.941  -3.650   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.401  -3.681   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.658  -5.030   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.455  -6.348   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.486   0.110   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.444   0.967   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.923   1.395   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   30                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22    5   24                                                  
CONECT   24   23   19                                                       
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   21                                                       
CONECT   29    3                                                            
CONECT   30    2   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
Dihydrolyfoline	MeSH

Chemical Formula

C₂₅H₂₉NO₅

Average Mass

423.5090 Da

Monoisotopic Mass

423.20457 Da

IUPAC Name

(1S,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.1^{8,12}.0^{2,7}.0^{19,24}]hexacosa-2(7),3,5,8(26),9,11-hexaen-15-one

Traditional Name

(1S,17S,19R)-4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.1^{8,12}.0^{2,7}.0^{19,24}]hexacosa-2(7),3,5,8(26),9,11-hexaen-15-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)[C@@H]1C[C@H](C[C@H]3CCCCN13)OC(=O)CCC1=CC=C(O)C2=C1

InChI Identifier

InChI=1S/C25H29NO5/c1-30-24-14-18-19(13-23(24)28)21-12-17(11-16-4-2-3-9-26(16)21)31-25(29)8-6-15-5-7-22(27)20(18)10-15/h5,7,10,13-14,16-17,21,27-28H,2-4,6,8-9,11-12H2,1H3/t16-,17+,21+/m1/s1

InChI Key

DUKDUISHTJYQFV-WWMYMODYSA-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

Species Name	Source	Reference
Lagerstroemia indica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Quinolizidine
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Piperidine
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Lactone
Amino acid or derivatives
Oxacycle
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.55	ALOGPS
logP	3.72	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.04	ChemAxon
pKa (Strongest Basic)	7.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	117.78 m³·mol⁻¹	ChemAxon
Polarizability	45.63 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

C00047364

Chemspider ID

28286271

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42640298

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mei R, Xu D, Hu H, Song D, Zhang H, Ma D, Xie X, She X: Biomimetic Total Syntheses of (+)-Dihydrolyfoline and (-)-5-epi-Dihydrolyfoline. Org Lett. 2015 May 1;17(9):2230-3. doi: 10.1021/acs.orglett.5b00846. Epub 2015 Apr 17. [PubMed:25885429 ]
Lee I, Youn U, Kim H, Min B, Kim JS, Bae K: Biphenyl and biphenyl ether quinolizidine N-oxide alkaloids from Lagerstroemia indica L. Planta Med. 2011 Dec;77(18):2037-41. doi: 10.1055/s-0031-1280064. Epub 2011 Jul 27. [PubMed:21796576 ]
Kim HJ, Lee IS, Youn U, Chen QC, Ngoc TM, Ha do T, Liu H, Min BS, Lee JY, Seong RS, Bae K: Biphenylquinolizidine alkaloids from Lagerstroemia indica. J Nat Prod. 2009 Apr;72(4):749-52. doi: 10.1021/np800619g. [PubMed:19260657 ]

Showing NP-Card for 5-Epi-dihydrolyfoline (NP0081391)

MOL for NP0081391 (5-Epi-dihydrolyfoline)

3D MOL for NP0081391 (5-Epi-dihydrolyfoline)

3D SDF for NP0081391 (5-Epi-dihydrolyfoline)

3D-SDF for NP0081391 (5-Epi-dihydrolyfoline)

PDB for NP0081391 (5-Epi-dihydrolyfoline)

3D PDB for NP0081391 (5-Epi-dihydrolyfoline)

SMILES for NP0081391 (5-Epi-dihydrolyfoline)

INCHI for NP0081391 (5-Epi-dihydrolyfoline)

Structure for NP0081391 (5-Epi-dihydrolyfoline)

3D Structure for NP0081391 (5-Epi-dihydrolyfoline)