NP-MRD: Showing NP-Card for (2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate (NP0233704)

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Record Information

Version

2.0

Created at

2022-09-06 15:24:19 UTC

Updated at

2022-09-06 15:24:19 UTC

NP-MRD ID

NP0233704

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate

Description

Deoxylophotoxin belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate is found in Leptogorgia violacea. (2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate was first documented in 2005 (PMID: 16032357). Based on a literature review very few articles have been published on deoxylophotoxin (PMID: 17190454).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062217242D          

 29 32  0  0  1  0            999 V2000
    4.7363    2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3029    2.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055    2.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0668    1.4868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8694    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    1.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155    0.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5690   -0.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3063    0.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2388    0.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8644    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6430    1.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -1.1095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2649   -1.5390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452   -0.7143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7274   -1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586   -0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -0.2851    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0281    0.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    1.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789    0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019    0.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697   -0.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6976    1.8956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1310    2.4953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    2.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    1.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    2.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  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  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 18 23  1  1  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
  4 29  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -1.8671   -1.9799   -3.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2444   -1.7302   -1.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574   -2.2253   -1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3935   -0.9411   -0.9229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1375   -1.8881    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2910   -1.8232    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -1.4770   -0.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3996   -1.4810    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807   -1.8650    1.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153   -2.0892    1.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537   -2.5103    3.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898   -2.6699    3.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6588   -1.1290   -0.2283 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4249   -0.2275    0.6764 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    0.1195   -0.6166 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2968    0.2070   -1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658    1.2841   -0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9657    1.4850   -0.0635 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6599    1.4439   -0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    1.6890    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4668    2.6767    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0072    3.2086    2.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456    2.8521    0.3946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5606    1.1968    0.3492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4225    2.3485    0.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0993    2.6489    1.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866    3.8440    1.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539    1.8958    2.6019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2208    0.2621   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8922   -1.5949   -3.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5018   -2.5450   -3.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6815   -3.3148   -1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6749   -2.1078   -0.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4024   -1.6467   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810   -0.6901   -1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -2.9422   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -1.5830    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052   -1.9882    2.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6700   -2.6934    4.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557   -2.0394   -0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7921    1.1933   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -0.6238   -1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9944    0.1349   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670    2.2433   -0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542    1.2291   -1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986    0.8806    0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7851    1.2537   -1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6282    0.7317    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9966    4.1779    2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0019    3.5247    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5856    4.6083    0.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847   -0.0642   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072    0.7304   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 28  2  0
 26 25  1  0
 25 24  1  0
 24 29  1  0
 29  4  1  0
  4  5  1  0
  5  6  1  0
  6 10  2  0
 10 11  1  0
 11 12  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 23  1  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 19  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 20 24  1  0
  7  6  1  0
 15 13  1  0
 19 18  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
 24 48  1  1
 29 52  1  0
 29 53  1  0
  4 35  1  6
  5 36  1  0
  5 37  1  0
 11 39  1  0
  9 38  1  0
 13 40  1  6
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  1
 19 47  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652309062217242D          

 29 32  0  0  1  0            999 V2000
    4.7363    2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3029    2.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055    2.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0668    1.4868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8694    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    1.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155    0.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5690   -0.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3063    0.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2388    0.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8644    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6430    1.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -1.1095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2649   -1.5390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452   -0.7143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7274   -1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586   -0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -0.2851    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0281    0.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    1.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789    0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019    0.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697   -0.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6976    1.8956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1310    2.4953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    2.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    1.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    2.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  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  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 18 23  1  1  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
  4 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233704

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H](CC2=C(C=O)C=C(O2)[C@@H]2O[C@]2(C)C[C@H]2OC(=O)C1=C2)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O7/c1-11(2)13-5-17-14(10-23)7-19(28-17)20-22(4,29-20)9-15-8-16(21(25)27-15)18(6-13)26-12(3)24/h7-8,10,13,15,18,20H,1,5-6,9H2,2-4H3/t13-,15+,18+,20+,22-/m1/s1

> <INCHI_KEY>
NPZNRRDKNMSIDD-KDCJINKYSA-N

> <FORMULA>
C22H24O7

> <MOLECULAR_WEIGHT>
400.427

> <EXACT_MASS>
400.152203113

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.56997797782703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4R,6R,10S,12S)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1^{6,9}.0^{2,4}]octadeca-1(16),9(18),14-trien-10-yl acetate

> <JCHEM_LOGP>
2.31492722

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.225222233619766

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904761864661826

> <JCHEM_POLAR_SURFACE_AREA>
95.34

> <JCHEM_REFRACTIVITY>
103.39589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4R,6R,10S,12S)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1^{6,9}.0^{2,4}]octadeca-1(16),9(18),14-trien-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.841   5.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.899   4.251   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.397   4.607   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.458   2.775   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.956   3.131   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.014   2.012   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.602   0.378   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.262  -1.014   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.638   0.123   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.512   1.658   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.680   2.662   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.134   2.152   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.143  -2.071   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.828  -2.873   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.791  -1.333   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.825  -2.532   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.136  -1.652   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.078  -0.532   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.519   0.943   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.462   2.063   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.187   1.090   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.737   1.608   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.544  -0.408   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.902   3.539   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.845   4.658   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.346   4.302   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.906   2.826   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.289   5.421   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.400   3.895   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   18                                                       
CONECT   24   20   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24    4                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₇

Average Mass

400.4270 Da

Monoisotopic Mass

400.15220 Da

IUPAC Name

(2R,4R,6R,10S,12S)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1^{6,9}.0^{2,4}]octadeca-1(16),9(18),14-trien-10-yl acetate

Traditional Name

(2R,4R,6R,10S,12S)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1^{6,9}.0^{2,4}]octadeca-1(16),9(18),14-trien-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H](CC2=C(C=O)C=C(O2)[C@@H]2O[C@]2(C)C[C@H]2OC(=O)C1=C2)C(C)=C

InChI Identifier

InChI=1S/C22H24O7/c1-11(2)13-5-17-14(10-23)7-19(28-17)20-22(4,29-20)9-15-8-16(21(25)27-15)18(6-13)26-12(3)24/h7-8,10,13,15,18,20H,1,5-6,9H2,2-4H3/t13-,15+,18+,20+,22-/m1/s1

InChI Key

NPZNRRDKNMSIDD-KDCJINKYSA-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
Leptogorgia violacea	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Aryl-aldehyde
Dicarboxylic acid or derivatives
2-furanone
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	2.31	ChemAxon
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.34 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.4 m³·mol⁻¹	ChemAxon
Polarizability	40.57 Å³	ChemAxon
Number of Rings	4	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

C00041494

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

101607295

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sanchez MC, Ortega MJ, Zubia E, Carballo JL: Cembrane diterpenes from the gorgonian Lophogorgia peruana. J Nat Prod. 2006 Dec;69(12):1749-55. doi: 10.1021/np060388x. [PubMed:17190454 ]
Cases M, Gonzalez-Lopez de Turiso F, Hadjisoteriou MS, Pattenden G: Synthetic studies towards furanocembrane diterpenes. A total synthesis of bis-deoxylophotoxin. Org Biomol Chem. 2005 Aug 7;3(15):2786-804. doi: 10.1039/b504545b. Epub 2005 Jun 28. [PubMed:16032357 ]
LOTUS database [Link]

Showing NP-Card for (2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate (NP0233704)

MOL for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

3D MOL for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

3D SDF for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

3D-SDF for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

PDB for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

3D PDB for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

SMILES for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

INCHI for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

Structure for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)

3D Structure for NP0233704 ((2r,4r,6r,10s,12s)-15-formyl-4-methyl-8-oxo-12-(prop-1-en-2-yl)-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-1(16),9(18),14-trien-10-yl acetate)