NP-MRD: Showing NP-Card for thunbergol B (NP0030165)

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Record Information

Version

2.0

Created at

2021-06-19 21:35:40 UTC

Updated at

2021-06-29 23:57:59 UTC

NP-MRD ID

NP0030165

Secondary Accession Numbers

None

Natural Product Identification

Common Name

thunbergol B

Provided By

JEOL Database JEOL Logo

Description

thunbergol B is found in Sargassum thunbergii. thunbergol B was first documented in 2006 (Seo, Y., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123353D          

 70 71  0  0  0  0            999 V2000
    1.2002    4.1160   -2.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0799    4.2338   -1.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    5.6013   -1.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8835    3.1644   -1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    3.0831   -0.8487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1121    2.2976    0.4685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3207    3.0075    1.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982    2.5638    1.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2096    2.5155    3.0213 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 70 71  0  0  0  0  0  0  0  0999 V2000
    1.2002    4.1160   -2.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192123353D          

 70 71  0  0  0  0            999 V2000
    1.2002    4.1160   -2.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0799    4.2338   -1.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8835    3.1644   -1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    3.0831   -0.8487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1121    2.2976    0.4685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3207    3.0075    1.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982    2.5638    1.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187    3.1737    2.9394 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2096    2.5155    3.0213 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0517    2.5745    1.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    3.9364    1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750    1.4667    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5565    1.3483    0.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4390   -0.0014   -0.6428 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3088   -0.1185   -1.6899 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4811   -1.4395   -2.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.9288   -2.6608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8793    0.0331   -1.1104 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5032   -0.9640   -0.0023 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0955   -1.2310   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813   -1.9010    0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -2.0715   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818   -2.7348    0.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3827   -1.5913   -1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3865   -0.9079   -2.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6274   -0.4248   -3.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -0.7471   -1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9211   -0.1163   -2.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    4.1898    2.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    4.9775    2.9669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343    4.3353    1.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0608    4.3575   -1.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531    3.1071   -2.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    4.8077   -3.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    5.9074   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419    6.3313   -1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302    5.6562   -0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750    2.2237   -2.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6384    4.0721   -0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036    2.5619   -1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6780    1.3104    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251    2.0891    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2907    1.6845    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    4.2422    2.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3497    3.0796    3.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0817    1.4742    3.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741    3.0149    3.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4090    4.6849    1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533    4.2201    0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906    3.9956    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5804    0.5531    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939    2.1646   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5908    1.4401    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3927   -0.1362   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3764   -0.8233    0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7472   -1.5320   -3.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634   -1.4758   -2.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3941   -2.3143   -1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.9168   -3.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367    1.0630   -0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -0.5218    0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810   -1.8910   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -2.2923    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8864   -2.7916   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553   -1.7487   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1471    0.5442   -3.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324   -1.1482   -4.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6974   -0.2914   -3.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    5.1321    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 19 16  1  0  0  0  0
  9  8  1  0  0  0  0
 16 15  1  0  0  0  0
  4  2  2  3  0  0  0
 11 10  1  0  0  0  0
  2  1  1  0  0  0  0
  8  7  2  0  0  0  0
  2  3  1  0  0  0  0
 13 11  2  0  0  0  0
 25 23  2  0  0  0  0
 25 26  1  0  0  0  0
 26 28  2  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 26 27  1  0  0  0  0
 23 24  1  0  0  0  0
 28 21  1  0  0  0  0
  7 30  1  0  0  0  0
  7  6  1  0  0  0  0
 11 12  1  0  0  0  0
 10  9  1  0  0  0  0
 21 20  1  0  0  0  0
 20 19  1  0  0  0  0
 19 29  1  0  0  0  0
 29 28  1  0  0  0  0
 30 32  1  0  0  0  0
 16 17  1  0  0  0  0
  6  5  1  0  0  0  0
 16 18  1  6  0  0  0
 30 31  2  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
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  9 46  1  0  0  0  0
  8 44  1  0  0  0  0
  6 42  1  0  0  0  0
  6 43  1  0  0  0  0
  5 40  1  0  0  0  0
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  4 39  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
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 32 70  1  0  0  0  0
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 18 60  1  0  0  0  0
 14 53  1  0  0  0  0
 14 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030165

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=C(\[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@@]1([H])OC2=C(C([H])=C(O[H])C([H])=C2C1([H])[H])C([H])([H])[H])\C([H])([H])[H])\C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O5/c1-18(2)9-6-12-21(26(29)30)13-7-10-19(3)11-8-14-27(5,31)24-17-22-16-23(28)15-20(4)25(22)32-24/h9,11,13,15-16,24,28,31H,6-8,10,12,14,17H2,1-5H3,(H,29,30)/b19-11+,21-13-/t24-,27-/m0/s1

> <INCHI_KEY>
YZHTYWFHNCTOEN-ARMZJCMISA-N

> <FORMULA>
C27H38O5

> <MOLECULAR_WEIGHT>
442.596

> <EXACT_MASS>
442.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.28243592709564

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,6E,10S)-10-hydroxy-10-[(2S)-5-hydroxy-7-methyl-2,3-dihydro-1-benzofuran-2-yl]-6-methyl-2-(4-methylpent-3-en-1-yl)undeca-2,6-dienoic acid

> <ALOGPS_LOGP>
4.92

> <JCHEM_LOGP>
6.380925029333332

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.092606634701207

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.135537896117506

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2286836558907286

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
130.92039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,6E,10S)-10-hydroxy-10-[(2S)-5-hydroxy-7-methyl-2,3-dihydro-1-benzofuran-2-yl]-6-methyl-2-(4-methylpent-3-en-1-yl)undeca-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 71  0  0  0  0  0  0  0  0999 V2000
    1.2002    4.1160   -2.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0799    4.2338   -1.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    5.6013   -1.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8835    3.1644   -1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    3.0831   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121    2.2976    0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3207    3.0075    1.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982    2.5638    1.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187    3.1737    2.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2096    2.5155    3.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0517    2.5745    1.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    3.9364    1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750    1.4667    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5565    1.3483    0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4390   -0.0014   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088   -0.1185   -1.6899 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4811   -1.4395   -2.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.9288   -2.6608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8793    0.0331   -1.1104 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5032   -0.9640   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0955   -1.2310   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813   -1.9010    0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -2.0715   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818   -2.7348    0.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3827   -1.5913   -1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3865   -0.9079   -2.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6274   -0.4248   -3.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -0.7471   -1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9211   -0.1163   -2.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    4.1898    2.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    4.9775    2.9669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343    4.3353    1.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0608    4.3575   -1.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531    3.1071   -2.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    4.8077   -3.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    5.9074   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419    6.3313   -1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302    5.6562   -0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750    2.2237   -2.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6384    4.0721   -0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036    2.5619   -1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6780    1.3104    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251    2.0891    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2907    1.6845    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    4.2422    2.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3497    3.0796    3.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0817    1.4742    3.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741    3.0149    3.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4090    4.6849    1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533    4.2201    0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906    3.9956    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5804    0.5531    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939    2.1646   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5908    1.4401    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3927   -0.1362   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3764   -0.8233    0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7472   -1.5320   -3.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634   -1.4758   -2.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3941   -2.3143   -1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.9168   -3.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367    1.0630   -0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -0.5218    0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810   -1.8910   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -2.2923    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8864   -2.7916   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553   -1.7487   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1471    0.5442   -3.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324   -1.1482   -4.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6974   -0.2914   -3.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    5.1321    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 19 16  1  0
  9  8  1  0
 16 15  1  0
  4  2  2  3
 11 10  1  0
  2  1  1  0
  8  7  2  0
  2  3  1  0
 13 11  2  0
 25 23  2  0
 25 26  1  0
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 21 22  2  0
 22 23  1  0
 26 27  1  0
 23 24  1  0
 28 21  1  0
  7 30  1  0
  7  6  1  0
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 10  9  1  0
 21 20  1  0
 20 19  1  0
 19 29  1  0
 29 28  1  0
 30 32  1  0
 16 17  1  0
  6  5  1  0
 16 18  1  6
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 10 47  1  0
 10 48  1  0
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  4 39  1  0
  1 33  1  0
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 17 57  1  0
 17 58  1  0
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 18 60  1  0
 14 53  1  0
 14 54  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.200   4.116  -2.518  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.080   4.234  -1.730  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.333   5.601  -1.160  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.884   3.164  -1.573  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.201   3.083  -0.849  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.112   2.298   0.469  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.321   3.007   1.547  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.098   2.564   1.911  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.819   3.174   2.939  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.210   2.515   3.021  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.052   2.575   1.754  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.184   3.936   1.125  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.675   1.467   1.302  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.556   1.348   0.087  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.439  -0.001  -0.643  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.309  -0.119  -1.690  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.481  -1.440  -2.462  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.506   0.929  -2.661  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.879   0.033  -1.110  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.503  -0.964  -0.002  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.096  -1.231  -0.372  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.881  -1.901   0.342  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.124  -2.071  -0.262  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.082  -2.735   0.448  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.383  -1.591  -1.554  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.387  -0.908  -2.268  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.627  -0.425  -3.663  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.157  -0.747  -1.645  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.921  -0.116  -2.210  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.938   4.190   2.203  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.411   4.978   2.967  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.234   4.335   1.877  0.00  0.00           O+0
HETATM   33  H   UNK     0       2.061   4.357  -1.886  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.353   3.107  -2.914  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.187   4.808  -3.366  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.510   5.907  -0.531  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.442   6.331  -1.968  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.230   5.656  -0.541  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.575   2.224  -2.027  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.638   4.072  -0.686  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.904   2.562  -1.512  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.678   1.310   0.268  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.125   2.089   0.835  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.291   1.685   1.402  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.951   4.242   2.735  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.350   3.080   3.927  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.082   1.474   3.346  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.774   3.015   3.820  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.409   4.685   1.893  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.253   4.220   0.627  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.991   3.996   0.390  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.580   0.553   1.888  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.394   2.165  -0.622  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.591   1.440   0.443  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.393  -0.136  -1.173  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.376  -0.823   0.081  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.747  -1.532  -3.271  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.463  -1.476  -2.949  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.394  -2.314  -1.812  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.717   0.917  -3.237  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.737   1.063  -0.756  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.593  -0.522   0.992  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.081  -1.891  -0.041  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.692  -2.292   1.335  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.886  -2.792  -0.093  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.355  -1.749  -2.012  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.147   0.544  -3.833  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.232  -1.148  -4.383  0.00  0.00           H+0
HETATM   69  H   UNK     0      -2.697  -0.291  -3.854  0.00  0.00           H+0
HETATM   70  H   UNK     0      -3.501   5.132   2.381  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   36   37   38                                             
CONECT    4    5    2   39                                                  
CONECT    5    4    6   40   41                                             
CONECT    6    7    5   42   43                                             
CONECT    7    8   30    6                                                  
CONECT    8    9    7   44                                                  
CONECT    9    8   10   45   46                                             
CONECT   10   11    9   47   48                                             
CONECT   11   10   13   12                                                  
CONECT   12   11   49   50   51                                             
CONECT   13   11   14   52                                                  
CONECT   14   15   13   53   54                                             
CONECT   15   16   14   55   56                                             
CONECT   16   19   15   17   18                                             
CONECT   17   16   57   58   59                                             
CONECT   18   16   60                                                       
CONECT   19   16   20   29   61                                             
CONECT   20   21   19   62   63                                             
CONECT   21   22   28   20                                                  
CONECT   22   21   23   64                                                  
CONECT   23   25   22   24                                                  
CONECT   24   23   65                                                       
CONECT   25   23   26   66                                                  
CONECT   26   25   28   27                                                  
CONECT   27   26   67   68   69                                             
CONECT   28   26   21   29                                                  
CONECT   29   19   28                                                       
CONECT   30    7   32   31                                                  
CONECT   31   30                                                            
CONECT   32   30   70                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    6                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   15                                                            
CONECT   57   17                                                            
CONECT   58   17                                                            
CONECT   59   17                                                            
CONECT   60   18                                                            
CONECT   61   19                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   22                                                            
CONECT   65   24                                                            
CONECT   66   25                                                            
CONECT   67   27                                                            
CONECT   68   27                                                            
CONECT   69   27                                                            
CONECT   70   32                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  142    0
END

RDKit          3D

70 71  0  0  0  0  0  0  0  0999 V2000
    1.2002    4.1160   -2.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0799    4.2338   -1.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    5.6013   -1.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8835    3.1644   -1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    3.0831   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121    2.2976    0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3207    3.0075    1.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982    2.5638    1.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187    3.1737    2.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2096    2.5155    3.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0517    2.5745    1.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    3.9364    1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750    1.4667    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5565    1.3483    0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4390   -0.0014   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088   -0.1185   -1.6899 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4811   -1.4395   -2.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.9288   -2.6608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8793    0.0331   -1.1104 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5032   -0.9640   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0955   -1.2310   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813   -1.9010    0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -2.0715   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0818   -2.7348    0.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3827   -1.5913   -1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3865   -0.9079   -2.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1571   -0.7471   -1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9381    4.1898    2.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    4.9775    2.9669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343    4.3353    1.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0608    4.3575   -1.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531    3.1071   -2.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    4.8077   -3.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    5.9074   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5750    2.2237   -2.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3497    3.0796    3.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0817    1.4742    3.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741    3.0149    3.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9906    3.9956    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7472   -1.5320   -3.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5934   -0.5218    0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810   -1.8910   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -2.2923    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8864   -2.7916   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553   -1.7487   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6974   -0.2914   -3.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    5.1321    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
 19 16  1  0
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 16 15  1  0
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 14 53  1  0
 14 54  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₅

Average Mass

442.5960 Da

Monoisotopic Mass

442.27192 Da

IUPAC Name

(2Z,6E,10S)-10-hydroxy-10-[(2S)-5-hydroxy-7-methyl-2,3-dihydro-1-benzofuran-2-yl]-6-methyl-2-(4-methylpent-3-en-1-yl)undeca-2,6-dienoic acid

Traditional Name

(2Z,6E,10S)-10-hydroxy-10-[(2S)-5-hydroxy-7-methyl-2,3-dihydro-1-benzofuran-2-yl]-6-methyl-2-(4-methylpent-3-en-1-yl)undeca-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(=C(\[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@@]1([H])OC2=C(C([H])=C(O[H])C([H])=C2C1([H])[H])C([H])([H])[H])\C([H])([H])[H])\C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H38O5/c1-18(2)9-6-12-21(26(29)30)13-7-10-19(3)11-8-14-27(5,31)24-17-22-16-23(28)15-20(4)25(22)32-24/h9,11,13,15-16,24,28,31H,6-8,10,12,14,17H2,1-5H3,(H,29,30)/b19-11+,21-13-/t24-,27-/m0/s1

InChI Key

YZHTYWFHNCTOEN-ARMZJCMISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Sargassum thunbergii	JEOL database	Seo, Y., et al, Chem. Pharm. Bull. 54, 1730 (2006)

Chemical Taxonomy

Classification

Not classified

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	4.92	ALOGPS
logP	6.38	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	5.14	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	130.92 m³·mol⁻¹	ChemAxon
Polarizability	49.28 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Seo, Y., et al. (2006). Seo, Y., et al, Chem. Pharm. Bull. 54, 1730 (2006). Chem. Pharm. Bull..

Showing NP-Card for thunbergol B (NP0030165)

MOL for NP0030165 (thunbergol B)

3D MOL for NP0030165 (thunbergol B)

3D SDF for NP0030165 (thunbergol B)

3D-SDF for NP0030165 (thunbergol B)

PDB for NP0030165 (thunbergol B)

3D PDB for NP0030165 (thunbergol B)

SMILES for NP0030165 (thunbergol B)

INCHI for NP0030165 (thunbergol B)

Structure for NP0030165 (thunbergol B)

3D Structure for NP0030165 (thunbergol B)