NP-MRD: Showing NP-Card for makilactone L (NP0038312)

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Record Information

Version

1.0

Created at

2021-06-20 21:02:16 UTC

Updated at

2021-06-30 00:11:02 UTC

NP-MRD ID

NP0038312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

makilactone L

Provided By

JEOL Database JEOL Logo

Description

Makilactone L belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. makilactone L is found in Podocarpus macrophyllus and Podocarpus macrophyllus D. DON. It was first documented in 2021 (PMID: 34130314). Based on a literature review a significant number of articles have been published on Makilactone L (PMID: 34130164) (PMID: 34130147) (PMID: 34130137) (PMID: 34130228) (PMID: 34130233) (PMID: 34130182).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123023D          

 50 55  0  0  0  0            999 V2000
    4.2032   -1.3346    1.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9654   -0.5167    1.3211 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4635    0.7991    1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937   -0.4175    2.5161 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6610    0.2378    3.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551   -1.1719    0.0524 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9160   -2.5180    0.3940 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2457   -3.2803   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0157   -4.4667   -0.3113 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981   -2.6322   -1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -1.2908   -1.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4166   -0.5217   -3.1424 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7975   -0.1464   -3.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4272   -1.3020   -4.1515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0257   -1.3353   -5.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1385    1.6626   -1.7714 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.4980    0.6929   -2.7467 C   0  0  2  0  0  0  0  0  0  0  0  0
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  4 33  1  0  0  0  0
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  5 35  1  0  0  0  0
 18 44  1  0  0  0  0
  3 32  1  0  0  0  0
M  END

     RDKit          3D

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    2.9654   -0.5167    1.3211 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202123023D          

 50 55  0  0  0  0            999 V2000
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    2.9654   -0.5167    1.3211 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.4392    3.1266   -4.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6191    2.2466   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229    1.7086   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    0.2710   -2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 16 14  1  0  0  0  0
 17 19  1  0  0  0  0
 19 21  1  0  0  0  0
 19 28  1  0  0  0  0
 24 23  1  0  0  0  0
 21 23  1  0  0  0  0
 12 14  1  0  0  0  0
 21 22  2  0  0  0  0
 12 28  1  0  0  0  0
 14 15  1  0  0  0  0
 12 11  1  0  0  0  0
 19 20  1  1  0  0  0
 28 24  1  0  0  0  0
  8  9  2  0  0  0  0
 24 25  1  0  0  0  0
  6  2  1  0  0  0  0
 25 27  1  0  0  0  0
  6 36  1  6  0  0  0
 11 27  1  0  0  0  0
  2  1  1  0  0  0  0
 11 10  2  0  0  0  0
  2  4  1  0  0  0  0
 27  6  1  0  0  0  0
 27 26  1  1  0  0  0
 25 26  1  0  0  0  0
  7  8  1  0  0  0  0
 28 50  1  1  0  0  0
  8 10  1  0  0  0  0
  4  5  1  0  0  0  0
 12 13  1  6  0  0  0
 17 18  1  0  0  0  0
 16 17  1  0  0  0  0
  2  3  1  6  0  0  0
 16 15  1  0  0  0  0
 16 42  1  6  0  0  0
 17 43  1  6  0  0  0
 14 41  1  1  0  0  0
 24 48  1  1  0  0  0
 25 49  1  1  0  0  0
 10 37  1  0  0  0  0
 13 38  1  0  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  5 35  1  0  0  0  0
 18 44  1  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@](O[H])(C([H])([H])[H])[C@@]1([H])OC(=O)C([H])=C2[C@@]11O[C@]1([H])[C@@]1([H])OC(=O)[C@]3(C([H])([H])[H])[C@@]1([H])[C@]2(C([H])([H])[H])[C@]1([H])O[C@]1([H])[C@@]3([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O9/c1-16(24,5-20)14-19-6(4-7(21)25-14)17(2)10-8(13(19)28-19)27-15(23)18(10,3)11(22)9-12(17)26-9/h4,8-14,20,22,24H,5H2,1-3H3/t8-,9+,10+,11+,12+,13+,14+,16-,17+,18+,19-/m0/s1

> <INCHI_KEY>
LCHSSOYHOCFOEO-SVSTZMKHSA-N

> <FORMULA>
C19H22O9

> <MOLECULAR_WEIGHT>
394.376

> <EXACT_MASS>
394.126382288

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.51145189078532

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,5R,10S,11S,13R,14S,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0^{2,4}.0^{4,9}.0^{11,13}.0^{15,18}]octadec-8-ene-7,16-dione

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-1.276939952

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.591620053499124

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.955407220995813

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1062222063848015

> <JCHEM_POLAR_SURFACE_AREA>
138.35

> <JCHEM_REFRACTIVITY>
87.94720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,10S,11S,13R,14S,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0^{2,4}.0^{4,9}.0^{11,13}.0^{15,18}]octadec-8-ene-7,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 55  0  0  0  0  0  0  0  0999 V2000
    4.2032   -1.3346    1.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9654   -0.5167    1.3211 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4635    0.7991    1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937   -0.4175    2.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    0.2378    3.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551   -1.1719    0.0524 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9160   -2.5180    0.3940 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2457   -3.2803   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0157   -4.4667   -0.3113 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981   -2.6322   -1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -1.2908   -1.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4166   -0.5217   -3.1424 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7975   -0.1464   -3.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4272   -1.3020   -4.1515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0257   -1.3353   -5.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -0.4983   -5.2378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8453    0.9775   -5.3167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8091    1.5521   -6.1990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924    1.6303   -3.9124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2417    2.3182   -3.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987    2.6766   -3.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736    3.5007   -4.6605 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8529    2.5766   -2.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1385    1.6626   -1.7714 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0151    1.0212   -0.7521 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2689    0.1762    0.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2234   -0.4832   -0.6948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4980    0.6929   -2.7467 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9206   -1.4163    0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7440   -0.8436    2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -2.3446    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    1.1923    1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -1.4041    2.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    0.2032    2.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    0.2256    4.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786   -1.2795   -0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159   -3.3115   -2.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4353    0.4021   -3.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -1.0522   -4.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296    0.4648   -4.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -2.1275   -3.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0793   -0.8099   -5.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223    1.1367   -5.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4497    2.4127   -6.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0649    1.5978   -3.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2748    2.7781   -2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    3.1266   -4.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6191    2.2466   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229    1.7086   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    0.2710   -2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 16 14  1  0
 17 19  1  0
 19 21  1  0
 19 28  1  0
 24 23  1  0
 21 23  1  0
 12 14  1  0
 21 22  2  0
 12 28  1  0
 14 15  1  0
 12 11  1  0
 19 20  1  1
 28 24  1  0
  8  9  2  0
 24 25  1  0
  6  2  1  0
 25 27  1  0
  6 36  1  6
 11 27  1  0
  2  1  1  0
 11 10  2  0
  2  4  1  0
 27  6  1  0
 27 26  1  1
 25 26  1  0
  7  8  1  0
 28 50  1  1
  8 10  1  0
  4  5  1  0
 12 13  1  6
 17 18  1  0
 16 17  1  0
  2  3  1  6
 16 15  1  0
 16 42  1  6
 17 43  1  6
 14 41  1  1
 24 48  1  1
 25 49  1  1
 10 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
 18 44  1  0
  3 32  1  0
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       4.203  -1.335   1.754  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.965  -0.517   1.321  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.463   0.799   1.020  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.994  -0.418   2.516  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.661   0.238   3.606  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.355  -1.172   0.052  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.916  -2.518   0.394  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.246  -3.280  -0.506  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.016  -4.467  -0.311  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.798  -2.632  -1.754  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.773  -1.291  -1.856  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.417  -0.522  -3.142  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.798  -0.146  -3.749  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.427  -1.302  -4.152  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.026  -1.335  -5.505  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.108  -0.498  -5.238  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.845   0.978  -5.317  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.809   1.552  -6.199  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.892   1.630  -3.912  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.242   2.318  -3.629  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.199   2.677  -3.803  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.474   3.501  -4.660  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.853   2.577  -2.603  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.139   1.663  -1.771  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.015   1.021  -0.752  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.269   0.176   0.144  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.223  -0.483  -0.695  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.498   0.693  -2.747  0.00  0.00           C+0
HETATM   29  H   UNK     0       4.921  -1.416   0.929  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.744  -0.844   2.571  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.933  -2.345   2.079  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.668   1.192   1.895  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.660  -1.404   2.852  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.126   0.203   2.294  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.042   0.226   4.357  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.179  -1.280  -0.670  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.516  -3.312  -2.548  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.435   0.402  -3.048  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.348  -1.052  -4.036  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.730   0.465  -4.650  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.003  -2.127  -3.754  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.079  -0.810  -5.597  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.122   1.137  -5.805  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.450   2.413  -6.488  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.065   1.598  -3.688  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.275   2.778  -2.636  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.439   3.127  -4.343  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.619   2.247  -1.234  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.723   1.709  -0.314  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.405   0.271  -2.287  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    6    1    4    3                                             
CONECT    3    2   32                                                       
CONECT    4    2    5   33   34                                             
CONECT    5    4   35                                                       
CONECT    6    7    2   36   27                                             
CONECT    7    6    8                                                       
CONECT    8    9    7   10                                                  
CONECT    9    8                                                            
CONECT   10   11    8   37                                                  
CONECT   11   12   27   10                                                  
CONECT   12   14   28   11   13                                             
CONECT   13   12   38   39   40                                             
CONECT   14   16   12   15   41                                             
CONECT   15   14   16                                                       
CONECT   16   14   17   15   42                                             
CONECT   17   19   18   16   43                                             
CONECT   18   17   44                                                       
CONECT   19   17   21   28   20                                             
CONECT   20   19   45   46   47                                             
CONECT   21   19   23   22                                                  
CONECT   22   21                                                            
CONECT   23   24   21                                                       
CONECT   24   23   28   25   48                                             
CONECT   25   24   27   26   49                                             
CONECT   26   27   25                                                       
CONECT   27   25   11    6   26                                             
CONECT   28   19   12   24   50                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37   10                                                            
CONECT   38   13                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   18                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   28                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  110    0
END

RDKit          3D

50 55  0  0  0  0  0  0  0  0999 V2000
    4.2032   -1.3346    1.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9654   -0.5167    1.3211 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4635    0.7991    1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937   -0.4175    2.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    0.2378    3.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551   -1.1719    0.0524 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9160   -2.5180    0.3940 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2457   -3.2803   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0157   -4.4667   -0.3113 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981   -2.6322   -1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -1.2908   -1.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4166   -0.5217   -3.1424 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7975   -0.1464   -3.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4272   -1.3020   -4.1515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0257   -1.3353   -5.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -0.4983   -5.2378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8453    0.9775   -5.3167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8091    1.5521   -6.1990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924    1.6303   -3.9124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2417    2.3182   -3.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987    2.6766   -3.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736    3.5007   -4.6605 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8529    2.5766   -2.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1385    1.6626   -1.7714 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0151    1.0212   -0.7521 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2689    0.1762    0.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2234   -0.4832   -0.6948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4980    0.6929   -2.7467 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9206   -1.4163    0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7440   -0.8436    2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -2.3446    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    1.1923    1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -1.4041    2.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    0.2032    2.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    0.2256    4.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786   -1.2795   -0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159   -3.3115   -2.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4353    0.4021   -3.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -1.0522   -4.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296    0.4648   -4.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -2.1275   -3.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0793   -0.8099   -5.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223    1.1367   -5.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4497    2.4127   -6.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0649    1.5978   -3.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2748    2.7781   -2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    3.1266   -4.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6191    2.2466   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229    1.7086   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    0.2710   -2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 16 14  1  0
 17 19  1  0
 19 21  1  0
 19 28  1  0
 24 23  1  0
 21 23  1  0
 12 14  1  0
 21 22  2  0
 12 28  1  0
 14 15  1  0
 12 11  1  0
 19 20  1  1
 28 24  1  0
  8  9  2  0
 24 25  1  0
  6  2  1  0
 25 27  1  0
  6 36  1  6
 11 27  1  0
  2  1  1  0
 11 10  2  0
  2  4  1  0
 27  6  1  0
 27 26  1  1
 25 26  1  0
  7  8  1  0
 28 50  1  1
  8 10  1  0
  4  5  1  0
 12 13  1  6
 17 18  1  0
 16 17  1  0
  2  3  1  6
 16 15  1  0
 16 42  1  6
 17 43  1  6
 14 41  1  1
 24 48  1  1
 25 49  1  1
 10 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
 18 44  1  0
  3 32  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₉

Average Mass

394.3760 Da

Monoisotopic Mass

394.12638 Da

IUPAC Name

(1S,2R,4S,5R,10S,11S,13R,14S,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0^{2,4}.0^{4,9}.0^{11,13}.0^{15,18}]octadec-8-ene-7,16-dione

Traditional Name

(1S,2R,4S,5R,10S,11S,13R,14S,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0^{2,4}.0^{4,9}.0^{11,13}.0^{15,18}]octadec-8-ene-7,16-dione

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@](O[H])(C([H])([H])[H])[C@@]1([H])OC(=O)C([H])=C2[C@@]11O[C@]1([H])[C@@]1([H])OC(=O)[C@]3(C([H])([H])[H])[C@@]1([H])[C@]2(C([H])([H])[H])[C@]1([H])O[C@]1([H])[C@@]3([H])O[H]

InChI Identifier

InChI=1S/C19H22O9/c1-16(24,5-20)14-19-6(4-7(21)25-14)17(2)10-8(13(19)28-19)27-15(23)18(10,3)11(22)9-12(17)26-9/h4,8-14,20,22,24H,5H2,1-3H3/t8-,9+,10+,11+,12+,13+,14+,16-,17+,18+,19-/m0/s1

InChI Key

LCHSSOYHOCFOEO-SVSTZMKHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Podocarpus macrophyllus	LOTUS Database	35616633
Podocarpus macrophyllus D. DON	JEOL database	Sato, K., et al, Chem. Pharm. Bull. 57, 668 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Dihydropyranone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organic oxide
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	-0.01	ALOGPS
logP	-1.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.96	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.95 m³·mol⁻¹	ChemAxon
Polarizability	37.51 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

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

44179143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Aparicio JD, Espindola D, Montesinos VN, Litter MI, Donati E, Benimeli CS, Polti MA: Evaluation of the sequential coupling of a bacterial treatment with a physicochemical process for the remediation of wastewater containing Cr and organic pollutants. J Hazard Mater. 2021 Jun 6;418:126307. doi: 10.1016/j.jhazmat.2021.126307. [PubMed:34130164 ]
Page AML, Chapman MA: Identifying genomic regions targeted during eggplant domestication using transcriptome data. J Hered. 2021 Jun 15. pii: 6299724. doi: 10.1093/jhered/esab035. [PubMed:34130314 ]
Konig IFM, Reis AC, Goncalves RRP, Oliveira MVS, Silva CM, Melo DS, Peconick AP, Thomasi SS, Remedio RN: Repellent activity of acetylcarvacrol and its effects on salivary gland morphology in unfed Rhipicephalus sanguineus sensu lato ticks (Acari: Ixodidae). Ticks Tick Borne Dis. 2021 Sep;12(5):101760. doi: 10.1016/j.ttbdis.2021.101760. Epub 2021 Jun 4. [PubMed:34130147 ]
Mondal H, Karmakar M, Ghosh NN, Maiti DK, Chattopadhyay PK, Singha NR: One-pot synthesis of sodium alginate-grafted-terpolymer hydrogel for As(III) and V(V) removal: In situ anchored comonomer and DFT studies on structures. J Environ Manage. 2021 Sep 15;294:112932. doi: 10.1016/j.jenvman.2021.112932. Epub 2021 Jun 12. [PubMed:34130137 ]
Breton C, Aparicio T, Le Malicot K, Ducreux M, Lecomte T, Bachet JB, Taieb J, Legoux JL, De Gramont A, Bennouna J, Bouche O, Boussari O, Manfredi S, Gornet JM: Predictive factors of severe early treatment-related toxicity in patients receiving first-line treatment for metastatic colorectal cancer: Pooled analysis of 2190 patients enrolled in Federation Francophone de Cancerologie Digestive (FFCD) trials. Eur J Cancer. 2021 Aug;153:40-50. doi: 10.1016/j.ejca.2021.04.040. Epub 2021 Jun 12. [PubMed:34130228 ]
Ji B, Zhang H, Zhou L, Yang J, Zhang K, Yuan X, Ma J, Qian Y: Effect of the rapid increase of salinity on anoxic-oxic biofilm reactor for treatment of high-salt and high-ammonia-nitrogen wastewater. Bioresour Technol. 2021 Oct;337:125363. doi: 10.1016/j.biortech.2021.125363. Epub 2021 Jun 4. [PubMed:34130233 ]
Wan X, Cheng C, Gu Y, Shu X, Xie L, Zhao Y: Acute and chronic toxicity of microcystin-LR and phenanthrene alone or in combination to the cladoceran (Daphnia magna). Ecotoxicol Environ Saf. 2021 Sep 1;220:112405. doi: 10.1016/j.ecoenv.2021.112405. Epub 2021 Jun 12. [PubMed:34130182 ]
Wang H, Liu J, Zhang Z, Li J, Zhang H, Zhan Y: Alkaline thermal pretreatment of waste activated sludge for enhanced hydrogen production in microbial electrolysis cells. J Environ Manage. 2021 Sep 15;294:113000. doi: 10.1016/j.jenvman.2021.113000. Epub 2021 Jun 12. [PubMed:34130135 ]
Ikiz O, Kahramansoy N, Erkol H, Kocoglu E, Firat T: Effects of lycopene in intestinal ischemia reperfusion injury via intestinal immunoglobulin A. J Surg Res. 2021 Jun 12;267:63-70. doi: 10.1016/j.jss.2021.04.039. [PubMed:34130240 ]
Olsen SU, Hesseberg K, Aas AM, Ranhoff AH, Bye A: Refeeding syndrome occurs among older adults regardless of refeeding rates: A systematic review. Nutr Res. 2021 Jul;91:1-12. doi: 10.1016/j.nutres.2021.05.004. Epub 2021 May 21. [PubMed:34130206 ]
Sato, K., et al. (2009). Sato, K., et al, Chem. Pharm. Bull. 57, 668 (2009). Chem. Pharm. Bull..

Showing NP-Card for makilactone L (NP0038312)

MOL for NP0038312 (makilactone L)

3D MOL for NP0038312 (makilactone L)

3D SDF for NP0038312 (makilactone L)

3D-SDF for NP0038312 (makilactone L)

PDB for NP0038312 (makilactone L)

3D PDB for NP0038312 (makilactone L)

SMILES for NP0038312 (makilactone L)

INCHI for NP0038312 (makilactone L)

Structure for NP0038312 (makilactone L)

3D Structure for NP0038312 (makilactone L)