NP-MRD: Showing NP-Card for majusculoic acid (NP0028112)

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Record Information

Version

2.0

Created at

2021-06-19 20:05:16 UTC

Updated at

2021-06-29 23:54:41 UTC

NP-MRD ID

NP0028112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

majusculoic acid

Provided By

JEOL Database JEOL Logo

Description

Majusculoic acid is also known as majusculoate. majusculoic acid is found in marine cyanobacterial mat. majusculoic acid was first documented in 2005 (PMID: 15844960). Based on a literature review very few articles have been published on Majusculoic acid (PMID: 34063984) (PMID: 29446640) (PMID: 25535717).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122053D          

 41 41  0  0  0  0            999 V2000
    3.3528   -1.9607   -4.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.7466   -2.9401 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2177   -2.2321   -1.6773 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4029   -1.9946   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -3.2866   -0.1258 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -0.9525    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.6149    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    0.4994    2.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651    0.8910    3.5567 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6050    2.1444    3.3556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6189    1.8748    2.5249 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3140    3.0121    1.8173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5669    1.9752    1.0184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3067    0.9661    0.1888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4795    1.4477   -1.2476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2040    0.4304   -2.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.5635   -1.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    0.7379   -3.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2965   -1.4108   -4.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5824   -3.0219   -4.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227   -1.6078   -5.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -2.2778   -3.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -0.6798   -2.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.7134   -1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4663   -3.2973   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -0.2690    0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645   -1.2813    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852    1.1897    1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418    0.0629    3.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055    1.0897    4.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2069    2.9511    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    2.4988    4.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506    1.1130    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982    3.0050    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844    4.0056    1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773    2.2623    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    0.0229    0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    0.7478    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.6279   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    2.3831   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734    0.0145   -3.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
  3  4  1  0  0  0  0
 13 12  1  0  0  0  0
  4  6  2  0  0  0  0
 15 16  1  0  0  0  0
  6  7  1  0  0  0  0
 11 13  1  0  0  0  0
  7  8  2  0  0  0  0
 16 18  1  0  0  0  0
  8  9  1  0  0  0  0
 12 11  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 16 17  2  0  0  0  0
  2  1  1  0  0  0  0
 13 14  1  0  0  0  0
  4  5  1  0  0  0  0
 11 33  1  6  0  0  0
  2  3  1  0  0  0  0
 13 36  1  6  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 18 41  1  0  0  0  0
  2 22  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    3.3528   -1.9607   -4.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.7466   -2.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177   -2.2321   -1.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029   -1.9946   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -3.2866   -0.1258 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -0.9525    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.6149    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    0.4994    2.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651    0.8910    3.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6050    2.1444    3.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189    1.8748    2.5249 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3140    3.0121    1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    1.9752    1.0184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3067    0.9661    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    1.4477   -1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040    0.4304   -2.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.5635   -1.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    0.7379   -3.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2965   -1.4108   -4.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5824   -3.0219   -4.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227   -1.6078   -5.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -2.2778   -3.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -0.6798   -2.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.7134   -1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4663   -3.2973   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -0.2690    0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645   -1.2813    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852    1.1897    1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418    0.0629    3.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055    1.0897    4.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2069    2.9511    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    2.4988    4.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506    1.1130    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982    3.0050    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844    4.0056    1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773    2.2623    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    0.0229    0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    0.7478    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.6279   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    2.3831   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734    0.0145   -3.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
  3  4  1  0
 13 12  1  0
  4  6  2  0
 15 16  1  0
  6  7  1  0
 11 13  1  0
  7  8  2  0
 16 18  1  0
  8  9  1  0
 12 11  1  0
  9 10  1  0
 10 11  1  0
 16 17  2  0
  2  1  1  0
 13 14  1  0
  4  5  1  0
 11 33  1  6
  2  3  1  0
 13 36  1  6
 12 34  1  0
 12 35  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 18 41  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652306192122053D          

 41 41  0  0  0  0            999 V2000
    3.3528   -1.9607   -4.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.7466   -2.9401 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2177   -2.2321   -1.6773 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4029   -1.9946   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -3.2866   -0.1258 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -0.9525    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.6149    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    0.4994    2.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651    0.8910    3.5567 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6050    2.1444    3.3556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6189    1.8748    2.5249 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3140    3.0121    1.8173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5669    1.9752    1.0184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3067    0.9661    0.1888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4795    1.4477   -1.2476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2040    0.4304   -2.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.5635   -1.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    0.7379   -3.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2965   -1.4108   -4.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5824   -3.0219   -4.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227   -1.6078   -5.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -2.2778   -3.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -0.6798   -2.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.7134   -1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4663   -3.2973   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -0.2690    0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645   -1.2813    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852    1.1897    1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418    0.0629    3.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055    1.0897    4.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2069    2.9511    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    2.4988    4.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506    1.1130    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982    3.0050    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844    4.0056    1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773    2.2623    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    0.0229    0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    0.7478    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.6279   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    2.3831   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734    0.0145   -3.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
  3  4  1  0  0  0  0
 13 12  1  0  0  0  0
  4  6  2  0  0  0  0
 15 16  1  0  0  0  0
  6  7  1  0  0  0  0
 11 13  1  0  0  0  0
  7  8  2  0  0  0  0
 16 18  1  0  0  0  0
  8  9  1  0  0  0  0
 12 11  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 16 17  2  0  0  0  0
  2  1  1  0  0  0  0
 13 14  1  0  0  0  0
  4  5  1  0  0  0  0
 11 33  1  6  0  0  0
  2  3  1  0  0  0  0
 13 36  1  6  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 18 41  1  0  0  0  0
  2 22  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028112

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H23BrO2/c1-2-6-14(16)8-5-3-4-7-12-11-13(12)9-10-15(17)18/h3,5,8,12-13H,2,4,6-7,9-11H2,1H3,(H,17,18)/b5-3+,14-8-/t12-,13-/m0/s1

> <INCHI_KEY>
XSRLEFWNCQOETJ-SULJWLEGSA-N

> <FORMULA>
C15H23BrO2

> <MOLECULAR_WEIGHT>
315.251

> <EXACT_MASS>
314.088143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.219973427265444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1S,2S)-2-[(3E,5Z)-6-bromonona-3,5-dien-1-yl]cyclopropyl]propanoic acid

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
4.554909347333332

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.817384648219677

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
80.49699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
majusculoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    3.3528   -1.9607   -4.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.7466   -2.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177   -2.2321   -1.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029   -1.9946   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -3.2866   -0.1258 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -0.9525    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.6149    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    0.4994    2.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651    0.8910    3.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6050    2.1444    3.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189    1.8748    2.5249 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3140    3.0121    1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    1.9752    1.0184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3067    0.9661    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    1.4477   -1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040    0.4304   -2.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.5635   -1.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    0.7379   -3.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2965   -1.4108   -4.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5824   -3.0219   -4.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227   -1.6078   -5.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -2.2778   -3.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -0.6798   -2.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.7134   -1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4663   -3.2973   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -0.2690    0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645   -1.2813    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852    1.1897    1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418    0.0629    3.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055    1.0897    4.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2069    2.9511    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    2.4988    4.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506    1.1130    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982    3.0050    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844    4.0056    1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773    2.2623    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    0.0229    0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    0.7478    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.6279   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    2.3831   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734    0.0145   -3.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
  3  4  1  0
 13 12  1  0
  4  6  2  0
 15 16  1  0
  6  7  1  0
 11 13  1  0
  7  8  2  0
 16 18  1  0
  8  9  1  0
 12 11  1  0
  9 10  1  0
 10 11  1  0
 16 17  2  0
  2  1  1  0
 13 14  1  0
  4  5  1  0
 11 33  1  6
  2  3  1  0
 13 36  1  6
 12 34  1  0
 12 35  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 18 41  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
  1 19  1  0
  1 20  1  0
  1 21  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       3.353  -1.961  -4.181  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.499  -1.747  -2.940  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.218  -2.232  -1.677  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.403  -1.995  -0.426  0.00  0.00           C+0
HETATM    5 Br   UNK     0       1.075  -3.287  -0.126  0.00  0.00          Br+0
HETATM    6  C   UNK     0       2.652  -0.953   0.388  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.952  -0.615   1.609  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.212   0.499   2.310  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.465   0.891   3.557  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.605   2.144   3.356  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.619   1.875   2.525  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.314   3.012   1.817  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.567   1.975   1.018  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.307   0.966   0.189  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.480   1.448  -1.248  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.204   0.430  -2.083  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.796  -0.564  -1.700  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.166   0.738  -3.395  0.00  0.00           O+0
HETATM   19  H   UNK     0       4.297  -1.411  -4.107  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.582  -3.022  -4.320  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.823  -1.608  -5.071  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.549  -2.278  -3.070  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.261  -0.680  -2.850  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.182  -1.713  -1.596  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.466  -3.297  -1.769  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.453  -0.269   0.109  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.165  -1.281   1.952  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.985   1.190   1.980  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.842   0.063   3.916  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.205   1.090   4.341  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.207   2.951   2.918  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.272   2.499   4.338  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.251   1.113   2.971  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.398   3.005   1.796  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.884   4.006   1.882  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.377   2.262   0.568  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.748   0.023   0.195  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.287   0.748   0.631  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.495   1.628  -1.696  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.049   2.383  -1.269  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.673   0.015  -3.820  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3   22   23                                             
CONECT    3    4    2   24   25                                             
CONECT    4    3    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7   26                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   28                                                  
CONECT    9    8   10   29   30                                             
CONECT   10    9   11   31   32                                             
CONECT   11   13   12   10   33                                             
CONECT   12   13   11   34   35                                             
CONECT   13   12   11   14   36                                             
CONECT   14   15   13   37   38                                             
CONECT   15   14   16   39   40                                             
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   41                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   18                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   82    0
END

RDKit          3D

41 41  0  0  0  0  0  0  0  0999 V2000
    3.3528   -1.9607   -4.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.7466   -2.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177   -2.2321   -1.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029   -1.9946   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -3.2866   -0.1258 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -0.9525    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.6149    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    0.4994    2.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651    0.8910    3.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6050    2.1444    3.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189    1.8748    2.5249 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3140    3.0121    1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    1.9752    1.0184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3067    0.9661    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    1.4477   -1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040    0.4304   -2.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.5635   -1.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    0.7379   -3.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2965   -1.4108   -4.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5824   -3.0219   -4.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227   -1.6078   -5.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -2.2778   -3.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -0.6798   -2.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.7134   -1.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4663   -3.2973   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -0.2690    0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645   -1.2813    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852    1.1897    1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418    0.0629    3.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055    1.0897    4.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2069    2.9511    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    2.4988    4.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506    1.1130    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3982    3.0050    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844    4.0056    1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773    2.2623    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    0.0229    0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    0.7478    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.6279   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    2.3831   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734    0.0145   -3.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
  3  4  1  0
 13 12  1  0
  4  6  2  0
 15 16  1  0
  6  7  1  0
 11 13  1  0
  7  8  2  0
 16 18  1  0
  8  9  1  0
 12 11  1  0
  9 10  1  0
 10 11  1  0
 16 17  2  0
  2  1  1  0
 13 14  1  0
  4  5  1  0
 11 33  1  6
  2  3  1  0
 13 36  1  6
 12 34  1  0
 12 35  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 18 41  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END

View in JSmol

Synonyms

Value	Source
Majusculoate	Generator

Chemical Formula

C₁₅H₂₃BrO₂

Average Mass

315.2510 Da

Monoisotopic Mass

314.08814 Da

IUPAC Name

3-[(1S,2S)-2-[(3E,5Z)-6-bromonona-3,5-dien-1-yl]cyclopropyl]propanoic acid

Traditional Name

majusculoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H23BrO2/c1-2-6-14(16)8-5-3-4-7-12-11-13(12)9-10-15(17)18/h3,5,8,12-13H,2,4,6-7,9-11H2,1H3,(H,17,18)/b5-3+,14-8-/t12-,13-/m0/s1

InChI Key

XSRLEFWNCQOETJ-SULJWLEGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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
marine cyanobacterial mat	JEOL database	MacMillan, J. B., et al, J. Nat. Prod. 68, 604 (2005)

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	5.45	ALOGPS
logP	4.55	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	80.5 m³·mol⁻¹	ChemAxon
Polarizability	31.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

9776867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiao HX, Yan QX, He ZH, Zou ZB, Le QQ, Chen TT, Cai B, Yang XW, Luo SL: Total Synthesis and Anti-Inflammatory Bioactivity of (-)-Majusculoic Acid and Its Derivatives. Mar Drugs. 2021 May 21;19(6). pii: md19060288. doi: 10.3390/md19060288. [PubMed:34063984 ]
Chen R, Li L, Lin N, Zhou R, Hua Y, Deng H, Zhang Y: Asymmetric Total Synthesis of (+)-Majusculoic Acid via a Dimerization-Dedimerization Strategy and Absolute Configuration Assignment. Org Lett. 2018 Mar 2;20(5):1477-1480. doi: 10.1021/acs.orglett.8b00349. Epub 2018 Feb 15. [PubMed:29446640 ]
Kumar M, Singh P, Tripathi J, Srivastava A, Tripathi MK, Ravi AK, Asthana RK: Identification and structure elucidation of antimicrobial compounds from Lyngbya aestuarii and Aphanothece bullosa. Cell Mol Biol (Noisy-le-grand). 2014 Dec 24;60(5):82-9. [PubMed:25535717 ]
Macmillan JB, Molinski TF: Majusculoic acid, a brominated cyclopropyl fatty acid from a marine cyanobacterial mat assemblage. J Nat Prod. 2005 Apr;68(4):604-6. doi: 10.1021/np049596k. [PubMed:15844960 ]
MacMillan, J. B., et al. (2005). MacMillan, J. B., et al, J. Nat. Prod. 68, 604 (2005). J. Nat. Prod..

Showing NP-Card for majusculoic acid (NP0028112)

MOL for NP0028112 (majusculoic acid)

3D MOL for NP0028112 (majusculoic acid)

3D SDF for NP0028112 (majusculoic acid)

3D-SDF for NP0028112 (majusculoic acid)

PDB for NP0028112 (majusculoic acid)

3D PDB for NP0028112 (majusculoic acid)

SMILES for NP0028112 (majusculoic acid)

INCHI for NP0028112 (majusculoic acid)

Structure for NP0028112 (majusculoic acid)

3D Structure for NP0028112 (majusculoic acid)