NP-MRD: Showing NP-Card for (12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one (NP0288484)

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Record Information

Version

2.0

Created at

2022-09-09 18:12:16 UTC

Updated at

2022-09-09 18:12:16 UTC

NP-MRD ID

NP0288484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one

Description

Bruceol belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. (12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one is found in Philotheca brucei. (12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one was first documented in 2019 (PMID: 30548759). Based on a literature review a small amount of articles have been published on Bruceol (PMID: 31849214) (PMID: 32662646).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220122D          

 24 28  0  0  1  0            999 V2000
    0.5590   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5803   -0.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316   -0.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094   -0.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681    0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860    0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093    0.6715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    1.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3901    1.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    2.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777    2.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202    1.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    1.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6716    0.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8831    0.9474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2514    0.4770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4111    1.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655    1.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5622    2.3234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3689    3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873    2.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    1.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5139    1.9218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  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  2  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 15  2  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 20 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -2.7018    1.5540   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854    1.2553    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733    1.5977    1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2761    2.2250    0.5282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0155    1.8076    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701    2.5641   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2440    2.0334   -0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1575    2.7707   -1.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    2.2908   -1.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2097    3.0466   -2.0578 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6300    0.9742   -1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6932    0.1549   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4678    0.6984   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5254   -0.0935    0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3242    0.4700    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592   -0.2236    1.3236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9301   -0.1648    0.3431 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5503   -0.9835   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2666   -1.6967   -0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697   -2.1320    0.4094 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6148   -3.5935    0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.4544    0.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702   -1.6622    1.5852 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1508   -1.8939    2.8034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3406    2.4766   -1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8348    1.7135   -1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3337    0.7565   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1796    0.7612    1.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375    2.5573    0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381    1.7506    2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672    3.6147   -0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184    0.5875   -1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889   -0.8884   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9601    0.3239    2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636   -0.6739    0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5915   -0.2952   -1.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780   -1.7223   -1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3798   -2.6207   -1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692   -1.0776   -1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532   -4.0868   -0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015   -3.7220    1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3512   -4.0689    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4091   -2.2687    1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2595   -2.6620    3.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5 15  2  0
 15 16  1  0
 16 23  1  0
 23 24  1  0
 23 20  1  0
 20 21  1  6
 20 19  1  0
 19 18  1  0
 18 17  1  0
 20 22  1  0
 22 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
 17  2  1  0
  7 13  1  0
  6  5  1  0
 14 15  1  0
 17 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 16 34  1  1
 23 43  1  1
 24 44  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
 19 38  1  0
 19 39  1  0
 18 36  1  0
 18 37  1  0
 17 35  1  1
 12 33  1  0
 11 32  1  0
  6 31  1  0
M  END


  Mrv1652309092220122D          

 24 28  0  0  1  0            999 V2000
    0.5590   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5803   -0.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316   -0.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094   -0.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681    0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860    0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093    0.6715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    1.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3901    1.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    2.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777    2.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202    1.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    1.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6716    0.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8831    0.9474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2514    0.4770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4111    1.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655    1.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5622    2.3234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3689    3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873    2.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    1.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5139    1.9218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  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  2  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 15  2  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 20 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0288484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C3[C@@H]4[C@H](O)[C@@](C)(CC[C@H]14)OC3=C1C=CC(=O)OC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O5/c1-18(2)10-6-7-19(3)17(21)14(10)15-12(23-18)8-11-9(16(15)24-19)4-5-13(20)22-11/h4-5,8,10,14,17,21H,6-7H2,1-3H3/t10-,14+,17-,19+/m0/s1

> <INCHI_KEY>
AINCADFEINJXSR-IJNOJWPESA-N

> <FORMULA>
C19H20O5

> <MOLECULAR_WEIGHT>
328.364

> <EXACT_MASS>
328.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.16491205002724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S,15R,16S,17R)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0^{2,7}.0^{9,18}.0^{12,17}]nonadeca-1,3,7,9(18)-tetraen-5-one

> <JCHEM_LOGP>
2.1425146313333343

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.557077578323145

> <JCHEM_PKA_STRONGEST_BASIC>
-3.429934267241455

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
87.19349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(12S,15R,16S,17R)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0^{2,7}.0^{9,18}.0^{12,17}]nonadeca-1,3,7,9(18)-tetraen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.043  -2.173   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.083  -0.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.432  -0.907   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.631  -0.996   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.674   0.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.239   0.086   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.134   1.352   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.671   1.253   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.525   2.535   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.061   2.436   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.842   3.915   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.305   4.014   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.451   2.733   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.860   3.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.120   1.677   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.649   1.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.469   0.890   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.767   1.961   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.496   3.611   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.049   4.337   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.689   5.834   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.776   4.395   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.327   3.234   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.826   3.587   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   17                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14    5   16                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20   14                                                       
CONECT   23   20   16   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

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Synonyms

Value	Source
16-Hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo(13.3.1.02,7.09,18.012,17)nonadeca-1,3,7,9(18)-tetraen-5-one	MeSH

Chemical Formula

C₁₉H₂₀O₅

Average Mass

328.3640 Da

Monoisotopic Mass

328.13107 Da

IUPAC Name

(12S,15R,16S,17R)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0^{2,7}.0^{9,18}.0^{12,17}]nonadeca-1,3,7,9(18)-tetraen-5-one

Traditional Name

(12S,15R,16S,17R)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0^{2,7}.0^{9,18}.0^{12,17}]nonadeca-1,3,7,9(18)-tetraen-5-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C3[C@@H]4[C@H](O)[C@@](C)(CC[C@H]14)OC3=C1C=CC(=O)OC1=C2

InChI Identifier

InChI=1S/C19H20O5/c1-18(2)10-6-7-19(3)17(21)14(10)15-12(23-18)8-11-9(16(15)24-19)4-5-13(20)22-11/h4-5,8,10,14,17,21H,6-7H2,1-3H3/t10-,14+,17-,19+/m0/s1

InChI Key

AINCADFEINJXSR-IJNOJWPESA-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
Eriostemon brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
1-benzopyran
Benzopyran
Chromane
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Cyclic alcohol
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	2.14	ChemAxon
pKa (Strongest Acidic)	13.56	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.19 m³·mol⁻¹	ChemAxon
Polarizability	34.16 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

C00019828

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

56841144

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Day AJ, Sumby CJ, George JH: Biomimetic Synthetic Studies on the Bruceol Family of Meroterpenoid Natural Products. J Org Chem. 2020 Feb 21;85(4):2103-2117. doi: 10.1021/acs.joc.9b02862. Epub 2020 Jan 6. [PubMed:31849214 ]
Day AJ, George JH: Isolation and Biomimetic Oxidation of Prenylbruceol A, an Anticipated Meroterpenoid Natural Product from Philotheca myoporoides. J Nat Prod. 2020 Jul 24;83(7):2305-2309. doi: 10.1021/acs.jnatprod.0c00348. Epub 2020 Jul 14. [PubMed:32662646 ]
Day AJ, Lee JHZ, Phan QD, Lam HC, Ametovski A, Sumby CJ, Bell SG, George JH: Biomimetic and Biocatalytic Synthesis of Bruceol. Angew Chem Int Ed Engl. 2019 Jan 28;58(5):1427-1431. doi: 10.1002/anie.201812432. Epub 2018 Dec 28. [PubMed:30548759 ]
LOTUS database [Link]

Showing NP-Card for (12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one (NP0288484)

MOL for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

3D MOL for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

3D SDF for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

3D-SDF for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

PDB for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

3D PDB for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

SMILES for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

INCHI for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

Structure for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)

3D Structure for NP0288484 ((12s,15r,16s,17r)-16-hydroxy-11,11,15-trimethyl-6,10,19-trioxapentacyclo[13.3.1.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]nonadeca-1,3,7,9(18)-tetraen-5-one)