NP-MRD: Showing NP-Card for (1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate (NP0249339)

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Record Information

Version

2.0

Created at

2022-09-07 11:52:22 UTC

Updated at

2022-09-07 11:52:22 UTC

NP-MRD ID

NP0249339

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate

Description

Aplysulphurin belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. (1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate is found in Darwinella oxeata. (1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate was first documented in 2008 (PMID: 18788476). Based on a literature review very few articles have been published on Aplysulphurin (PMID: 32281798).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213522D          

 27 30  0  0  1  0            999 V2000
    1.9720   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666   -1.4805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -0.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.0269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5127    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    0.8115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4959    1.1470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358    2.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    2.4525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0009    3.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390    2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    3.2693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6650    3.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0560    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193    3.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0072    4.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317    4.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608    5.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5969    5.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684    3.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463    1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926    0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 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
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 15 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  2  0  0  0  0
 13 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    7.0083    2.3408    0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0800    1.4501   -0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2591    1.3487   -1.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0554    0.7455    0.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334   -0.0700   -0.2699 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2504   -1.4010    0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041   -2.0085   -0.2810 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6456   -3.1069    0.4844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2713   -3.1960    0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9347   -3.8511    1.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -2.4770   -0.1224 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6636   -3.0131   -1.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7497   -1.0794   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    0.0409    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5022   -0.0980    0.1495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8878   -0.8777    1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743   -0.5947   -1.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026   -0.9469   -0.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2718    0.0117    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5898    1.3266    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0720    2.1749   -0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    2.0539    1.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917    1.2934    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180    1.2684    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049    1.3918   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981    0.2576   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1120   -0.9217   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6553    3.3932    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0547    2.0677    1.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9996    2.2747    0.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4990   -0.0669   -1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -2.2470   -1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6727   -2.7389    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3142   -3.4132   -1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -2.2202   -2.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3710   -3.8363   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4057   -0.2361    2.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -1.7228    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269   -1.1270    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090    0.2616   -1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7054   -1.4100   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6722   -2.0153   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1147   -0.9952   -1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5464   -0.4308    1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2916    0.2123   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9755    2.7493   -0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2640    2.8672   -1.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3816    1.4985   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2070    1.9198    1.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9808    3.1526    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.8567    2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7423    1.7003    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7445    1.8835   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    2.2041    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018    2.3561   -0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 26  1  0
 26 27  1  0
 27 13  2  0
 13 14  1  0
 14 24  2  0
 24 25  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 13 11  1  0
 23 15  1  0
 27  7  1  0
 25 26  2  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 11 33  1  1
  7 32  1  6
  5 31  1  6
  1 28  1  0
  1 29  1  0
  1 30  1  0
 24 54  1  0
 25 55  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
M  END


  Mrv1652309072213522D          

 27 30  0  0  1  0            999 V2000
    1.9720   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666   -1.4805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -0.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.0269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5127    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    0.8115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4959    1.1470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358    2.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    2.4525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0009    3.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390    2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    3.2693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6650    3.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0560    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193    3.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0072    4.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317    4.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608    5.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5969    5.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684    3.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463    1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926    0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 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
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 15 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  2  0  0  0  0
 13 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249339

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@@H]2O[C@H](OC(C)=O)C3=C2C1=C(C=C3)[C@]1(C)CCCC(C)(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O5/c1-12-16-15(22(5)10-6-9-21(3,4)11-22)8-7-14-17(16)20(26-18(12)24)27-19(14)25-13(2)23/h7-8,12,19-20H,6,9-11H2,1-5H3/t12-,19+,20-,22-/m1/s1

> <INCHI_KEY>
AQSIHMBSEUHXNO-CIEOHCGFSA-N

> <FORMULA>
C22H28O5

> <MOLECULAR_WEIGHT>
372.461

> <EXACT_MASS>
372.193674002

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.2650134930357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,9R)-9-methyl-10-oxo-7-[(1R)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0^{4,12}]dodeca-4(12),5,7-trien-3-yl acetate

> <JCHEM_LOGP>
5.160235652333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.576198682148457

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
99.47129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,9R)-9-methyl-10-oxo-7-[(1R)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0^{4,12}]dodeca-4(12),5,7-trien-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.681  -3.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.776  -2.603   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.244  -2.764   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.402  -1.196   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.497   0.050   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.957   0.050   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.481   1.515   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.926   2.141   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.087   3.673   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.494   4.299   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.159   4.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.002   6.109   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.566   3.952   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.295   4.578   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.510   6.103   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.975   5.626   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.971   6.050   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.156   7.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.880   8.716   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.419   8.769   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.100  10.275   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.847   9.344   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.234   7.462   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.541   3.673   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.380   2.141   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.973   1.515   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.727   2.420   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   15                                                       
CONECT   24   14   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   27                                                  
CONECT   27   26   13    7                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Aplysulfurin	Generator

Chemical Formula

C₂₂H₂₈O₅

Average Mass

372.4610 Da

Monoisotopic Mass

372.19367 Da

IUPAC Name

(1S,3R,9R)-9-methyl-10-oxo-7-[(1R)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0^{4,12}]dodeca-4(12),5,7-trien-3-yl acetate

Traditional Name

(1S,3R,9R)-9-methyl-10-oxo-7-[(1R)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0^{4,12}]dodeca-4(12),5,7-trien-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@@H]2O[C@H](OC(C)=O)C3=C2C1=C(C=C3)[C@]1(C)CCCC(C)(C)C1

InChI Identifier

InChI=1S/C22H28O5/c1-12-16-15(22(5)10-6-9-21(3,4)11-22)8-7-14-17(16)20(26-18(12)24)27-19(14)25-13(2)23/h7-8,12,19-20H,6,9-11H2,1-5H3/t12-,19+,20-,22-/m1/s1

InChI Key

AQSIHMBSEUHXNO-CIEOHCGFSA-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
Darwinella oxeata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Isocoumaran
Furopyran
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Furan
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.16	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.47 m³·mol⁻¹	ChemAxon
Polarizability	41.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

101606484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nirmal N, Praba GO, Velmurugan D: Modeling studies on phospholipase A2-inhibitor complexes. Indian J Biochem Biophys. 2008 Aug;45(4):256-62. [PubMed:18788476 ]
Shilling AJ, Witowski CG, Maschek JA, Azhari A, Vesely BA, Kyle DE, Amsler CD, McClintock JB, Baker BJ: Spongian Diterpenoids Derived from the Antarctic Sponge Dendrilla antarctica Are Potent Inhibitors of the Leishmania Parasite. J Nat Prod. 2020 May 22;83(5):1553-1562. doi: 10.1021/acs.jnatprod.0c00025. Epub 2020 Apr 13. [PubMed:32281798 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate (NP0249339)

MOL for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

3D MOL for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

3D SDF for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

3D-SDF for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

PDB for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

3D PDB for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

SMILES for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

INCHI for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

Structure for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)

3D Structure for NP0249339 ((1s,3r,9r)-9-methyl-10-oxo-7-[(1r)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-yl acetate)