NP-MRD: Showing NP-Card for xestospongiene R (NP0040190)

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Record Information

Version

2.0

Created at

2021-06-20 22:25:21 UTC

Updated at

2021-06-30 00:13:58 UTC

NP-MRD ID

NP0040190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

xestospongiene R

Provided By

JEOL Database JEOL Logo

Description

(4Z,6R,7R)-14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. xestospongiene R is found in Xestospongia testudinaria. xestospongiene R was first documented in 2011 (Jiang, W., et al.). Based on a literature review very few articles have been published on (4Z,6R,7R)-14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100253D          

 42 41  0  0  0  0            999 V2000
    5.3531   -0.7297   -0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -1.3862   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1159   -2.0927   -1.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204   -1.5511   -2.1109 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6963   -0.7087   -1.5096 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8595    0.7574   -1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    1.7359   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    1.6107    0.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7641    1.7209    0.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584    2.7241    1.3693 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0182    2.5736    2.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295    2.7585    1.2538 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4372    1.4685    1.7085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0859    1.6021    1.6281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7803    0.3172    2.0900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3085    0.4273    2.0803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8739    0.5270    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    1.5600    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    1.4542   -1.6271 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902    3.1743    1.0135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.9096   -1.9174   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -2.6091   -2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -1.2922   -3.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -0.9050   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -1.0287   -1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    1.0371   -2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    2.7439   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    0.6367    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504    0.9073    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    3.7009    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856    2.4231    2.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    3.5819    1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    2.9861    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290    1.2310    2.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7534    0.6300    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4147    2.4406    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717    1.8351    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.0838    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621   -0.5230    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254   -0.4768    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    1.2595    2.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7205   -0.3641    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 15 14  1  0  0  0  0
  2  3  1  0  0  0  0
 14 13  1  0  0  0  0
 19 18  1  0  0  0  0
 13 12  1  0  0  0  0
 12 10  1  0  0  0  0
 18 17  2  3  0  0  0
 10  8  1  0  0  0  0
  2  1  2  0  0  0  0
  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
 17 16  1  0  0  0  0
 18 20  1  0  0  0  0
  4  2  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 16 15  1  0  0  0  0
  8  9  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  3 21  1  0  0  0  0
  6 26  1  0  0  0  0
 17 42  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 10 30  1  6  0  0  0
  8 28  1  1  0  0  0
  7 27  1  0  0  0  0
 11 31  1  0  0  0  0
  9 29  1  0  0  0  0
M  END

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    5.3531   -0.7297   -0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -1.3862   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1159   -2.0927   -1.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204   -1.5511   -2.1109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963   -0.7087   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    0.7574   -1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    1.7359   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    1.6107    0.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7641    1.7209    0.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584    2.7241    1.3693 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0182    2.5736    2.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295    2.7585    1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4372    1.4685    1.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    1.6021    1.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803    0.3172    2.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.4273    2.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739    0.5270    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    1.5600    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    1.4542   -1.6271 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902    3.1743    1.0135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.9096   -1.9174   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -2.6091   -2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -1.2922   -3.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -0.9050   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -1.0287   -1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    1.0371   -2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    2.7439   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    0.6367    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504    0.9073    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    3.7009    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856    2.4231    2.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    3.5819    1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    2.9861    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290    1.2310    2.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7534    0.6300    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4147    2.4406    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717    1.8351    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.0838    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621   -0.5230    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254   -0.4768    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    1.2595    2.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7205   -0.3641    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 15 14  1  0
  2  3  1  0
 14 13  1  0
 19 18  1  0
 13 12  1  0
 12 10  1  0
 18 17  2  3
 10  8  1  0
  2  1  2  0
  8  7  1  0
  7  6  2  0
 17 16  1  0
 18 20  1  0
  4  2  1  0
 10 11  1  0
  6  5  1  0
 16 15  1  0
  8  9  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 21  1  0
  6 26  1  0
 17 42  1  0
 16 40  1  0
 16 41  1  0
 15 38  1  0
 15 39  1  0
 14 36  1  0
 14 37  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  0
 12 33  1  0
 10 30  1  6
  8 28  1  1
  7 27  1  0
 11 31  1  0
  9 29  1  0
M  END


  Mrv1652306212100253D          

 42 41  0  0  0  0            999 V2000
    5.3531   -0.7297   -0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -1.3862   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1159   -2.0927   -1.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204   -1.5511   -2.1109 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6963   -0.7087   -1.5096 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8595    0.7574   -1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    1.7359   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    1.6107    0.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7641    1.7209    0.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584    2.7241    1.3693 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0182    2.5736    2.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295    2.7585    1.2538 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4372    1.4685    1.7085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0859    1.6021    1.6281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7803    0.3172    2.0900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3085    0.4273    2.0803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8739    0.5270    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    1.5600    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    1.4542   -1.6271 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902    3.1743    1.0135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.9096   -1.9174   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -2.6091   -2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -1.2922   -3.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -0.9050   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -1.0287   -1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    1.0371   -2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    2.7439   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    0.6367    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504    0.9073    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    3.7009    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856    2.4231    2.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    3.5819    1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    2.9861    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290    1.2310    2.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7534    0.6300    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4147    2.4406    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717    1.8351    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.0838    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621   -0.5230    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254   -0.4768    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    1.2595    2.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7205   -0.3641    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 15 14  1  0  0  0  0
  2  3  1  0  0  0  0
 14 13  1  0  0  0  0
 19 18  1  0  0  0  0
 13 12  1  0  0  0  0
 12 10  1  0  0  0  0
 18 17  2  3  0  0  0
 10  8  1  0  0  0  0
  2  1  2  0  0  0  0
  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
 17 16  1  0  0  0  0
 18 20  1  0  0  0  0
  4  2  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 16 15  1  0  0  0  0
  8  9  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  3 21  1  0  0  0  0
  6 26  1  0  0  0  0
 17 42  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 10 30  1  6  0  0  0
  8 28  1  1  0  0  0
  7 27  1  0  0  0  0
 11 31  1  0  0  0  0
  9 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])C(\[H])=C(\[H])[C@@]([H])(O[H])[C@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])=C(Br)Br

> <INCHI_IDENTIFIER>
InChI=1S/C14H22Br2O4/c15-13(16)9-4-2-1-3-7-11(17)12(18)8-5-6-10-14(19)20/h5,8-9,11-12,17-18H,1-4,6-7,10H2,(H,19,20)/b8-5-/t11-,12-/m1/s1

> <INCHI_KEY>
ZFXQBFPZXYPLPE-OBBGCOQJSA-N

> <FORMULA>
C14H22Br2O4

> <MOLECULAR_WEIGHT>
414.134

> <EXACT_MASS>
411.988485

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.078522930669784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z,6R,7R)-14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoic acid

> <ALOGPS_LOGP>
3.94

> <JCHEM_LOGP>
3.4502550896666655

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.670584208998807

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.444047776246488

> <JCHEM_PKA_STRONGEST_BASIC>
-3.169703041352933

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
97.51670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,6R,7R)-14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    5.3531   -0.7297   -0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -1.3862   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1159   -2.0927   -1.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204   -1.5511   -2.1109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963   -0.7087   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    0.7574   -1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    1.7359   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    1.6107    0.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7641    1.7209    0.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584    2.7241    1.3693 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0182    2.5736    2.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295    2.7585    1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4372    1.4685    1.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    1.6021    1.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803    0.3172    2.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.4273    2.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739    0.5270    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    1.5600    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    1.4542   -1.6271 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902    3.1743    1.0135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.9096   -1.9174   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -2.6091   -2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -1.2922   -3.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -0.9050   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -1.0287   -1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    1.0371   -2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    2.7439   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    0.6367    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504    0.9073    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    3.7009    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856    2.4231    2.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    3.5819    1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    2.9861    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290    1.2310    2.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7534    0.6300    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4147    2.4406    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717    1.8351    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.0838    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621   -0.5230    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254   -0.4768    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    1.2595    2.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7205   -0.3641    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 15 14  1  0
  2  3  1  0
 14 13  1  0
 19 18  1  0
 13 12  1  0
 12 10  1  0
 18 17  2  3
 10  8  1  0
  2  1  2  0
  8  7  1  0
  7  6  2  0
 17 16  1  0
 18 20  1  0
  4  2  1  0
 10 11  1  0
  6  5  1  0
 16 15  1  0
  8  9  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 21  1  0
  6 26  1  0
 17 42  1  0
 16 40  1  0
 16 41  1  0
 15 38  1  0
 15 39  1  0
 14 36  1  0
 14 37  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  0
 12 33  1  0
 10 30  1  6
  8 28  1  1
  7 27  1  0
 11 31  1  0
  9 29  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       5.353  -0.730  -0.379  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.130  -1.386  -1.383  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.116  -2.093  -1.971  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.820  -1.551  -2.111  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.696  -0.709  -1.510  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.860   0.757  -1.807  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.147   1.736  -0.932  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.354   1.611   0.551  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.764   1.721   0.787  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.658   2.724   1.369  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.018   2.574   2.752  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.129   2.759   1.254  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.437   1.468   1.708  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.086   1.602   1.628  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.780   0.317   2.090  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.309   0.427   2.080  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.874   0.527   0.690  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.534   1.560   0.141  0.00  0.00           C+0
HETATM   19 Br   UNK     0      -5.156   1.454  -1.627  0.00  0.00          Br+0
HETATM   20 Br   UNK     0      -4.890   3.174   1.014  0.00  0.00          Br+0
HETATM   21  H   UNK     0       6.910  -1.917  -1.424  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.541  -2.609  -2.047  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.970  -1.292  -3.165  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.616  -0.905  -0.437  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.743  -1.029  -1.948  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.748   1.037  -2.855  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.271   2.744  -1.327  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.057   0.637   0.948  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.150   0.907   0.393  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.055   3.701   1.065  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.986   2.423   2.736  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.758   3.582   1.878  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.840   2.986   0.221  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.729   1.231   2.738  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.753   0.630   1.078  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.415   2.441   2.254  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.372   1.835   0.596  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.458   0.084   3.112  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.462  -0.523   1.460  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.725  -0.477   2.542  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.618   1.260   2.720  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.720  -0.364   0.083  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3    1    4                                                  
CONECT    3    2   21                                                       
CONECT    4    5    2   22   23                                             
CONECT    5    4    6   24   25                                             
CONECT    6    7    5   26                                                  
CONECT    7    8    6   27                                                  
CONECT    8   10    7    9   28                                             
CONECT    9    8   29                                                       
CONECT   10   12    8   11   30                                             
CONECT   11   10   31                                                       
CONECT   12   13   10   32   33                                             
CONECT   13   14   12   34   35                                             
CONECT   14   15   13   36   37                                             
CONECT   15   14   16   38   39                                             
CONECT   16   17   15   40   41                                             
CONECT   17   18   16   42                                                  
CONECT   18   19   17   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   82    0
END

RDKit          3D

42 41  0  0  0  0  0  0  0  0999 V2000
    5.3531   -0.7297   -0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -1.3862   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1159   -2.0927   -1.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204   -1.5511   -2.1109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963   -0.7087   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    0.7574   -1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    1.7359   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    1.6107    0.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7641    1.7209    0.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584    2.7241    1.3693 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0182    2.5736    2.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295    2.7585    1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4372    1.4685    1.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    1.6021    1.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803    0.3172    2.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.4273    2.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739    0.5270    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    1.5600    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    1.4542   -1.6271 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902    3.1743    1.0135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.9096   -1.9174   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -2.6091   -2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704   -1.2922   -3.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -0.9050   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -1.0287   -1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    1.0371   -2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    2.7439   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    0.6367    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504    0.9073    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    3.7009    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856    2.4231    2.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    3.5819    1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    2.9861    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290    1.2310    2.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7534    0.6300    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4147    2.4406    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717    1.8351    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.0838    3.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621   -0.5230    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254   -0.4768    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    1.2595    2.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7205   -0.3641    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 15 14  1  0
  2  3  1  0
 14 13  1  0
 19 18  1  0
 13 12  1  0
 12 10  1  0
 18 17  2  3
 10  8  1  0
  2  1  2  0
  8  7  1  0
  7  6  2  0
 17 16  1  0
 18 20  1  0
  4  2  1  0
 10 11  1  0
  6  5  1  0
 16 15  1  0
  8  9  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 21  1  0
  6 26  1  0
 17 42  1  0
 16 40  1  0
 16 41  1  0
 15 38  1  0
 15 39  1  0
 14 36  1  0
 14 37  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  0
 12 33  1  0
 10 30  1  6
  8 28  1  1
  7 27  1  0
 11 31  1  0
  9 29  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4Z,6R,7R)-14,14-Dibromo-6,7-dihydroxytetradeca-4,13-dienoate	Generator

Chemical Formula

C₁₄H₂₂Br₂O₄

Average Mass

414.1340 Da

Monoisotopic Mass

411.98848 Da

IUPAC Name

(4Z,6R,7R)-14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoic acid

Traditional Name

(4Z,6R,7R)-14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C([H])([H])C(\[H])=C(\[H])[C@@]([H])(O[H])[C@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])=C(Br)Br

InChI Identifier

InChI=1S/C14H22Br2O4/c15-13(16)9-4-2-1-3-7-11(17)12(18)8-5-6-10-14(19)20/h5,8-9,11-12,17-18H,1-4,6-7,10H2,(H,19,20)/b8-5-/t11-,12-/m1/s1

InChI Key

ZFXQBFPZXYPLPE-OBBGCOQJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xestospongia testudinaria	JEOL database	Jiang, W., et al, Tetrahedron 67, 58 (2011).

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Halogenated fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
1,2-diol
Ketene acetal or derivatives
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Bromoalkene
Haloalkene
Monocarboxylic acid or derivatives
Vinyl halide
Vinyl bromide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organohalogen compound
Organobromide
Organooxygen compound
Alcohol
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	3.94	ALOGPS
logP	3.45	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	97.52 m³·mol⁻¹	ChemAxon
Polarizability	35.08 Å³	ChemAxon
Number of Rings	0	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

27025265

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51002949

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang, W., et al. (2011). Jiang, W., et al, Tetrahedron 67, 58 (2011).. Tetrahedron.

Showing NP-Card for xestospongiene R (NP0040190)

MOL for NP0040190 (xestospongiene R)

3D MOL for NP0040190 (xestospongiene R)

3D SDF for NP0040190 (xestospongiene R)

3D-SDF for NP0040190 (xestospongiene R)

PDB for NP0040190 (xestospongiene R)

3D PDB for NP0040190 (xestospongiene R)

SMILES for NP0040190 (xestospongiene R)

INCHI for NP0040190 (xestospongiene R)

Structure for NP0040190 (xestospongiene R)

3D Structure for NP0040190 (xestospongiene R)