NP-MRD: Showing NP-Card for (1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate (NP0160194)

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Record Information

Version

2.0

Created at

2022-09-02 18:05:21 UTC

Updated at

2022-09-02 18:05:21 UTC

NP-MRD ID

NP0160194

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate

Description

(1S,4S)-4-bromo-1-{[(1S,4S,5S,6R,9S,10R)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]Undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on (1S,4S)-4-bromo-1-{[(1S,4S,5S,6R,9S,10R)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]Undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220052D          

 28 31  0  0  1  0            999 V2000
    2.0188   -3.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240   -1.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321   -2.9213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -2.3486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7054   -1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7850   -0.8792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0962   -0.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748    0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952    0.2631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3753   -0.3774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4274   -0.1869    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5519   -1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920   -1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0384   -1.1962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6789   -1.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2290   -0.3935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202    0.2559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0846    0.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -0.4904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4226   -3.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2456   -2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -2.2346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4308   -2.1776    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1469   -1.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -1.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9479   -0.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -1.6073    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  6  0  0  0
  5  6  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 15  1  1  0  0  0
  7 20  1  0  0  0  0
 10 20  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
  5 28  1  0  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    2.4596    3.8570    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768    2.5806    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885    2.6467    1.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0621    1.3774   -0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5900    0.1107    0.0809 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2012   -0.2380   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    0.3491    0.3697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0655    0.0840    1.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5540   -0.0020    2.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -0.1153    0.9177 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2939   -1.2159    0.8314 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7214   -0.8128    2.0858 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8436   -1.3587   -0.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805   -0.9249   -1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    0.0436   -1.3157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0627    0.2251   -2.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153    1.2775   -0.9569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090    1.1792    0.3580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2020    1.1368    0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916   -0.4504   -0.1071 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0745   -0.3922    1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4813    0.1695    1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3990   -0.1053    0.5211 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1727    1.5102   -0.2312 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.8079   -0.9927   -0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477   -2.4671   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875   -0.8055   -1.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244   -0.7380   -0.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120    4.6731   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0876    3.7127   -0.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    4.1448    0.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0392   -1.3785   -0.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -0.1585   -1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1759    1.4287    0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6073   -0.9194    2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    0.8830    2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7233   -0.8806    2.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9175    0.8780    2.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8035   -2.1548    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0719   -2.4569   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8665   -0.8801   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -1.7798   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6116   -0.4186   -2.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    1.1297   -2.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5773   -0.7013   -2.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303    0.4325   -3.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    2.0547    0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5726    1.6640    1.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604   -1.5106   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4986   -0.0245    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856   -1.4830    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    1.2690    1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8217   -0.2599    2.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788   -0.6721    0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2581   -2.6026    0.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976   -2.9969   -0.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855   -3.0124   -0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4778   -1.5595   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7459   -0.7072   -1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3689    0.1898   -2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8797   -1.6810   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3466   -0.1507   -1.8906 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  1
 10 18  1  0
 18 19  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  6
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 15 20  1  0
  5 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28  5  1  0
 20  7  1  0
 11 10  1  0
 20 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 18 47  1  1
 19 48  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 14 42  1  0
 14 43  1  0
 13 40  1  0
 13 41  1  0
 11 39  1  1
 20 49  1  6
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  1
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
M  END


  Mrv1652309022220052D          

 28 31  0  0  1  0            999 V2000
    2.0188   -3.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240   -1.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321   -2.9213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -2.3486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7054   -1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7850   -0.8792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0962   -0.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748    0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952    0.2631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3753   -0.3774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4274   -0.1869    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5519   -1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920   -1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0384   -1.1962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6789   -1.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2290   -0.3935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202    0.2559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0846    0.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -0.4904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4226   -3.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2456   -2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -2.2346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4308   -2.1776    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1469   -1.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -1.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9479   -0.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -1.6073    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  6  0  0  0
  5  6  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 15  1  1  0  0  0
  7 20  1  0  0  0  0
 10 20  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
  5 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@]1(C[C@@H]2CC[C@]34[C@H](O)O[C@](C)(CC[C@@H]3Br)[C@@H]24)CC[C@H](Br)C(C)(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H34Br2O4/c1-13(25)27-21(9-7-15(23)19(2,3)12-21)11-14-5-10-22-16(24)6-8-20(4,17(14)22)28-18(22)26/h14-18,26H,5-12H2,1-4H3/t14-,15-,16-,17+,18+,20+,21-,22-/m0/s1

> <INCHI_KEY>
CKHNDLWTFRQLAJ-UAJZKUBTSA-N

> <FORMULA>
C22H34Br2O4

> <MOLECULAR_WEIGHT>
522.318

> <EXACT_MASS>
520.082386

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
48.55858965687302

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S)-4-bromo-1-{[(1S,4S,5S,6R,9S,10R)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0^{1,5}]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate

> <ALOGPS_LOGP>
4.90

> <JCHEM_LOGP>
4.6755525303333325

> <ALOGPS_LOGS>
-6.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.898818394756807

> <JCHEM_PKA_STRONGEST_BASIC>
-4.155256834133373

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
114.75959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.88e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S)-4-bromo-1-{[(1S,4S,5S,6R,9S,10R)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0^{1,5}]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.768  -6.097   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.660  -5.028   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.032  -3.533   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.180  -5.453   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.071  -4.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.317  -3.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.465  -1.641   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.180  -1.177   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.140   0.329   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.671   0.491   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.700  -0.705   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0      -0.798  -0.349   0.000  0.00  0.00          Br+0
HETATM   13  C   UNK     0       1.030  -2.209   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.412  -2.889   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.805  -2.233   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.001  -3.203   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.161  -0.735   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.211   0.478   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.891   1.859   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.298  -0.915   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.789  -5.661   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.325  -5.555   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.001  -4.171   0.000  0.00  0.00           C+0
HETATM   24 Br   UNK     0      -4.538  -4.065   0.000  0.00  0.00          Br+0
HETATM   25  C   UNK     0      -2.141  -2.894   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.548  -2.269   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.769  -1.399   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.605  -3.000   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   21   28                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18   20                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18                                                            
CONECT   20   15    7   10                                                  
CONECT   21    5   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25    5                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
(1S,4S)-4-Bromo-1-{[(1S,4S,5S,6R,9S,10R)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0,]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetic acid	Generator

Chemical Formula

C₂₂H₃₄Br₂O₄

Average Mass

522.3180 Da

Monoisotopic Mass

520.08239 Da

IUPAC Name

(1S,4S)-4-bromo-1-{[(1S,4S,5S,6R,9S,10R)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0^{1,5}]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate

Traditional Name

(1S,4S)-4-bromo-1-{[(1S,4S,5S,6R,9S,10R)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0^{1,5}]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@]1(C[C@@H]2CC[C@]34[C@H](O)O[C@](C)(CC[C@@H]3Br)[C@@H]24)CC[C@H](Br)C(C)(C)C1

InChI Identifier

InChI=1S/C22H34Br2O4/c1-13(25)27-21(9-7-15(23)19(2,3)12-21)11-14-5-10-22-16(24)6-8-20(4,17(14)22)28-18(22)26/h14-18,26H,5-12H2,1-4H3/t14-,15-,16-,17+,18+,20+,21-,22-/m0/s1

InChI Key

CKHNDLWTFRQLAJ-UAJZKUBTSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cyclohexyl halide
Oxepane
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organobromide
Organohalogen compound
Alkyl bromide
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alkyl halide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.9	ALOGPS
logP	4.68	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.76 m³·mol⁻¹	ChemAxon
Polarizability	48.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162926292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate (NP0160194)

MOL for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

3D MOL for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

3D SDF for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

3D-SDF for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

PDB for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

3D PDB for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

SMILES for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

INCHI for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

Structure for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)

3D Structure for NP0160194 ((1s,4s)-4-bromo-1-{[(1s,4s,5s,6r,9s,10r)-9-bromo-10-hydroxy-6-methyl-11-oxatricyclo[4.3.2.0¹,⁵]undecan-4-yl]methyl}-3,3-dimethylcyclohexyl acetate)