NP-MRD: Showing NP-Card for (1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione (NP0313913)

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Record Information

Version

2.0

Created at

2022-09-11 11:44:17 UTC

Updated at

2022-09-11 11:44:17 UTC

NP-MRD ID

NP0313913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione

Description

Inumakilactone B 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. (1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione is found in Podocarpus neriifolius. (1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione was first documented in 2009 (PMID: 19571410). Based on a literature review a small amount of articles have been published on Inumakilactone B (PMID: 19504383).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112213442D          

 25 30  0  0  1  0            999 V2000
    0.0654    1.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6374    1.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383    1.3372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6671    2.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4679    2.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6968    3.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0400    1.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8112    0.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832    0.3464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6120    1.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1841    0.5446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9849    0.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7561   -0.0499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5273   -0.8425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0993   -1.4370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264   -1.0407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1497   -1.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -1.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2426   -2.5819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -1.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535   -0.6443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1544   -0.4462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7815   -0.0499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2095    0.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0103    0.7428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 22 21  1  6  0  0  0
  9 22  1  0  0  0  0
 16 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
  8 25  1  0  0  0  0
  3 25  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

     RDKit          3D

 43 48  0  0  0  0  0  0  0  0999 V2000
    4.2570   -2.4183    0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2022   -1.7777    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213   -0.2680    0.7200 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9280    0.1713   -0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3527   -0.1753   -1.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0653   -0.3320   -2.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8769   -0.3418   -1.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -0.1756   -0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099   -0.2816   -0.6310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7973    0.2496   -1.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789   -1.5992   -0.5305 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6285   -2.0578    0.5668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969   -1.4089   -0.5340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0498   -0.1740   -0.0119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2129    0.1756   -0.7490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115    0.9604    0.3775 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6844    1.5835    1.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477    2.0786   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    2.6735   -1.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670    2.4192   -0.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1001    1.8065    0.7489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8214    0.4607    0.5793 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3220    1.5491    0.9992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2910    0.3401    1.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8153    0.1806    0.6562 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3009   -3.4974    0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1468   -1.8900   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3664   -2.3760    0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347    0.0493    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5059   -0.6119   -2.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8719    0.2305   -2.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2679    1.1381   -2.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4887   -0.5711   -2.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809   -2.3673   -1.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594   -2.1225   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5448   -0.5230    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -0.5824   -1.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5490    2.6652    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810    1.3766    1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682    1.0803    2.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522    2.2570    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910   -0.1865    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    2.2925    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  1
 16 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 21 23  1  0
 23 24  1  0
 25 24  1  1
 25  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3  2  1  0
  2  1  2  3
 18 16  1  0
 25 23  1  0
  8 25  1  0
 13 11  1  0
 14 16  1  0
  9 22  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 22 42  1  1
 21 41  1  1
 23 43  1  1
  3 29  1  1
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  6
 13 35  1  6
 14 36  1  1
 15 37  1  0
  2 28  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652309112213442D          

 25 30  0  0  1  0            999 V2000
    0.0654    1.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6374    1.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383    1.3372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6671    2.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4679    2.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6968    3.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0400    1.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8112    0.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832    0.3464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6120    1.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1841    0.5446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9849    0.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7561   -0.0499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5273   -0.8425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0993   -1.4370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264   -1.0407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1497   -1.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -1.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2426   -2.5819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -1.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535   -0.6443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1544   -0.4462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7815   -0.0499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2095    0.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0103    0.7428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 22 21  1  6  0  0  0
  9 22  1  0  0  0  0
 16 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
  8 25  1  0  0  0  0
  3 25  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313913

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12[C@@H]3[C@H](OC1=O)[C@H]1O[C@]11[C@H](OC(=O)C=C1[C@@]3(C)[C@H]1O[C@H]1[C@@H]2O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O7/c1-4-7-18-6(5-8(19)22-7)16(2)11-9(14(18)25-18)24-15(21)17(11,3)12(20)10-13(16)23-10/h4-5,7,9-14,20H,1H2,2-3H3/t7-,9+,10+,11-,12+,13+,14-,16-,17-,18-/m1/s1

> <INCHI_KEY>
VLRYBJQMQSJMHB-TXKOSJJRSA-N

> <FORMULA>
C18H18O7

> <MOLECULAR_WEIGHT>
346.335

> <EXACT_MASS>
346.10525292

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.92789076142682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,5R,10S,11R,13S,14R,15R,18R)-5-ethenyl-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_LOGP>
0.494170157

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.41288444767865

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4930043425853574

> <JCHEM_POLAR_SURFACE_AREA>
97.89

> <JCHEM_REFRACTIVITY>
80.21690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5R,10S,11R,13S,14R,15R,18R)-5-ethenyl-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

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.122   3.236   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.190   2.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.685   2.496   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.112   3.976   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.607   4.346   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.034   5.825   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.675   3.236   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.248   1.756   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.315   0.647   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.742   2.126   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.810   1.017   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.305   1.386   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.878  -0.093   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.451  -1.573   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.519  -2.682   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.956  -1.943   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.746  -3.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.710  -3.318   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.053  -4.820   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.283  -2.739   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.393  -1.203   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.888  -0.833   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.325  -0.093   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.258   1.017   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.753   1.386   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   11   22                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11   13                                                       
CONECT   13   12   11   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21    9   16                                                  
CONECT   23   21   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24    8    3   23                                             
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₇

Average Mass

346.3350 Da

Monoisotopic Mass

346.10525 Da

IUPAC Name

(1S,2R,4R,5R,10S,11R,13S,14R,15R,18R)-5-ethenyl-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,4R,5R,10S,11R,13S,14R,15R,18R)-5-ethenyl-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

C[C@]12[C@@H]3[C@H](OC1=O)[C@H]1O[C@]11[C@H](OC(=O)C=C1[C@@]3(C)[C@H]1O[C@H]1[C@@H]2O)C=C

InChI Identifier

InChI=1S/C18H18O7/c1-4-7-18-6(5-8(19)22-7)16(2)11-9(14(18)25-18)24-15(21)17(11,3)12(20)10-13(16)23-10/h4-5,7,9-14,20H,1H2,2-3H3/t7-,9+,10+,11-,12+,13+,14-,16-,17-,18-/m1/s1

InChI Key

VLRYBJQMQSJMHB-TXKOSJJRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Podocarpus neriifolius	LOTUS Database	35616633

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
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
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	0.49	ChemAxon
pKa (Strongest Acidic)	13.41	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.89 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.22 m³·mol⁻¹	ChemAxon
Polarizability	32.93 Å³	ChemAxon
Number of Rings	6	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

C00000281

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

101593067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sato K, Inaba Y, Park HS, Akiyama T, Koyama T, Fukaya H, Aoyagi Y, Takeya K: Cytotoxic bisnor- and norditerpene dilactones having 7alpha,8alpha-epoxy-9,11-enolide substructure from Podocarpus macrophyllus D. DON. Chem Pharm Bull (Tokyo). 2009 Jul;57(7):668-79. doi: 10.1248/cpb.57.668. [PubMed:19571410 ]
Huang SY, Fan LY, Shen YC, Liao CC, Hsu LC, Hsu YW, Wu TS, Hsiao PC, Shen CC, Don MJ, Kuo YH: A new dimeric phenylpropanoid and cytotoxic norditerpene constituents from Podocarpus nakaii. J Asian Nat Prod Res. 2009;11(5):410-6. doi: 10.1080/10286020902877739. [PubMed:19504383 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione (NP0313913)

MOL for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

3D MOL for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

3D SDF for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

3D-SDF for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

PDB for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

3D PDB for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

SMILES for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

INCHI for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

Structure for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)

3D Structure for NP0313913 ((1s,2r,4r,5r,10s,11r,13s,14r,15r,18r)-5-ethenyl-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹¹,¹³.0¹⁵,¹⁸]octadec-8-ene-7,16-dione)