NP-MRD: Showing NP-Card for 6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate (NP0210757)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 08:42:52 UTC

Updated at

2022-09-05 08:42:52 UTC

NP-MRD ID

NP0210757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate

Description

Isoparguerol belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate is found in Jania rubens and Laurencia saitoi. 6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate was first documented in 2004 (PMID: 15162360). Based on a literature review very few articles have been published on Isoparguerol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210422D          

 28 31  0  0  0  0            999 V2000
    0.6419   -0.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338   -0.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4116   -1.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480   -1.0964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400   -1.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -2.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462   -2.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685   -2.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604   -2.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827   -2.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969   -2.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5889   -3.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2980   -2.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1271   -3.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9377   -3.6431    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -4.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3931   -5.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0666   -3.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2524   -3.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -4.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -5.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159   -4.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6240   -3.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097   -3.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8921   -4.0992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0381   -3.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7462   -2.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178   -2.5067    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
  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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 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
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 24 28  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
   -4.9989   -3.6922    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2309   -2.4896    0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1280   -2.1363    1.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152   -1.7365   -0.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615   -0.5829   -0.0150 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4537   -0.9014   -0.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    0.2810   -0.8530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6502    0.4746   -2.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672    0.0345   -0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2369   -1.1830   -0.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6288   -1.5719   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293   -0.3976   -0.1376 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8474    0.2078   -1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8068   -0.8045    0.5445 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6882   -2.2190   -0.4748 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.6325   -1.2193    1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9259   -1.5626    2.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8783    0.6921    0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5583    1.1298    0.0797 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8323    1.9054    1.1509 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3375    1.5771    2.4151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568    1.6222    1.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1347    1.5836   -0.2596 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5682    1.8343   -0.4527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8088    2.7667   -1.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3924    2.2520    0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4719    1.2811    0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4301    0.6404   -0.6619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4443   -3.5559   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3583   -4.6028    0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8295   -3.7985    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -0.3853    1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942   -1.5483    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596   -1.5539   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3347   -0.4719   -2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7994   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1217    1.2404   -2.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5986   -1.9618   -1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0152   -2.1382   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797   -2.2433    0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1756   -0.5764   -2.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967    1.0121   -1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432    0.6678   -1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5508    0.0411    0.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867   -2.0840    2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3592   -0.3248    2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5097   -1.8097    1.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    0.2698    1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5340    1.5574    0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    1.8620   -0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007    3.0011    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917    2.1311    2.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976    2.4964    1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7927    0.6746    1.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    2.3821   -0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375    3.0305   -1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0622    1.9472    1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7418    3.3059    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8675    0.6137    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2903    1.7851   -0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7425    0.4513   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  0
 20 19  1  0
 19 18  1  0
 18 12  1  0
 12 13  1  6
 12 11  1  0
 11 10  1  0
 10  9  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28  5  1  0
  9  7  1  0
 28 24  1  0
  9 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  1
  6 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
 23 55  1  6
 22 53  1  0
 22 54  1  0
 20 51  1  6
 21 52  1  0
 19 50  1  6
 18 48  1  0
 18 49  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 11 39  1  0
 11 40  1  0
 10 38  1  0
 14 44  1  1
 16 45  1  0
 16 46  1  0
 17 47  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  6
M  END


  Mrv1652309052210422D          

 28 31  0  0  0  0            999 V2000
    0.6419   -0.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338   -0.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4116   -1.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480   -1.0964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400   -1.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -2.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462   -2.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685   -2.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604   -2.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827   -2.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969   -2.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5889   -3.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2980   -2.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1271   -3.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9377   -3.6431    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -4.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3931   -5.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0666   -3.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2524   -3.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -4.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -5.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159   -4.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6240   -3.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097   -3.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8921   -4.0992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0381   -3.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7462   -2.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178   -2.5067    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
  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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 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
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 24 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2(C)C(CC(O)C3CC(C)(CC=C23)C(Br)CO)C2(O)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C22H33BrO5/c1-12(25)28-17-10-21(3)14-4-6-20(2,19(23)11-24)9-13(14)16(26)8-18(21)22(27)7-5-15(17)22/h4,13,15-19,24,26-27H,5-11H2,1-3H3

> <INCHI_KEY>
GQGQFMYAQIAQJH-UHFFFAOYSA-N

> <FORMULA>
C22H33BrO5

> <MOLECULAR_WEIGHT>
457.405

> <EXACT_MASS>
456.151137

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.96953480771339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(1-bromo-2-hydroxyethyl)-8,11-dihydroxy-1,5-dimethyltetracyclo[8.6.0.0^{2,7}.0^{11,14}]hexadec-2-en-15-yl acetate

> <JCHEM_LOGP>
1.5150374433333347

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.566672709075544

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.044756523761812

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8557865411876877

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
109.8583

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-(1-bromo-2-hydroxyethyl)-8,11-dihydroxy-1,5-dimethyltetracyclo[8.6.0.0^{2,7}.0^{11,14}]hexadec-2-en-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.198  -0.358   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.743  -1.799   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.768  -2.991   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.263  -2.047   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.808  -3.487   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.328  -3.735   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.873  -5.176   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.848  -3.983   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.393  -5.424   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.368  -4.232   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.888  -4.480   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.433  -5.920   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.756  -5.133   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.437  -7.087   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0      12.950  -6.800   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0      10.929  -8.541   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.934  -9.708   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.458  -7.112   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.938  -6.864   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.963  -8.056   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.508  -9.496   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.443  -7.808   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.898  -6.368   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.378  -6.119   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.532  -7.652   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.938  -6.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.393  -5.224   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.833  -4.679   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   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   12   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    7   24                                                  
CONECT   24   23   25   26   28                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    5   24                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃BrO₅

Average Mass

457.4050 Da

Monoisotopic Mass

456.15114 Da

IUPAC Name

5-(1-bromo-2-hydroxyethyl)-8,11-dihydroxy-1,5-dimethyltetracyclo[8.6.0.0^{2,7}.0^{11,14}]hexadec-2-en-15-yl acetate

Traditional Name

5-(1-bromo-2-hydroxyethyl)-8,11-dihydroxy-1,5-dimethyltetracyclo[8.6.0.0^{2,7}.0^{11,14}]hexadec-2-en-15-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2(C)C(CC(O)C3CC(C)(CC=C23)C(Br)CO)C2(O)CCC12

InChI Identifier

InChI=1S/C22H33BrO5/c1-12(25)28-17-10-21(3)14-4-6-20(2,19(23)11-24)9-13(14)16(26)8-18(21)22(27)7-5-15(17)22/h4,13,15-19,24,26-27H,5-11H2,1-3H3

InChI Key

GQGQFMYAQIAQJH-UHFFFAOYSA-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
Jania rubens	LOTUS Database	35616633
Laurencia saitoi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Bromohydrin
Secondary alcohol
Carboxylic acid ester
Cyclobutanol
Halohydrin
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alkyl bromide
Organohalogen compound
Organobromide
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alkyl halide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.52	ChemAxon
pKa (Strongest Acidic)	14.04	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.86 m³·mol⁻¹	ChemAxon
Polarizability	45.97 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

Not Available

Chemspider ID

383842

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

434037

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Awad NE: Bioactive brominated diterpenes from the marine red alga Jania Rubens (L.) Lamx. Phytother Res. 2004 Apr;18(4):275-9. doi: 10.1002/ptr.1273. [PubMed:15162360 ]
LOTUS database [Link]

Showing NP-Card for 6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate (NP0210757)

MOL for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

3D MOL for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

3D SDF for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

3D-SDF for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

PDB for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

3D PDB for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

SMILES for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

INCHI for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

Structure for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)

3D Structure for NP0210757 (6-(1-bromo-2-hydroxyethyl)-2a,4-dihydroxy-6,8b-dimethyl-1h,2h,2bh,3h,4h,4ah,5h,7h,9h,10h,10ah-cyclobuta[a]phenanthren-10-yl acetate)