NP-MRD: Showing NP-Card for Sargaquinoic acid (NP0071805)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 17:09:07 UTC

Updated at

2022-04-28 17:09:07 UTC

NP-MRD ID

NP0071805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sargaquinoic acid

Description

Sargaquinoic acid, also known as sargaquinoate or MC14 compound, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Sargaquinoic acid is found in Iryanthera juruensis , Roldana barba-johannis, Sargassum fallax, Sargassum thunbergii and Sargassum yezoense. Sargaquinoic acid was first documented in 2018 (PMID: 29803170). Based on a literature review a small amount of articles have been published on Sargaquinoic acid (PMID: 34619494) (PMID: 31663108) (PMID: 30939856) (PMID: 30583359).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219092D          

 31 31  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 11 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END

     RDKit          3D

 67 67  0  0  0  0  0  0  0  0999 V2000
   -7.4203   -0.5968    1.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9485   -0.8414    1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296   -0.7944    2.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2818   -1.0936   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0011   -1.1391   -1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3904   -0.0341   -2.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9401   -0.2424   -2.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    0.6452   -1.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3941    1.8706   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7228    1.9145    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668    1.8320   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256    2.8809   -0.9528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5839    0.8177    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    0.6649    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836   -0.6259   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6533   -0.7202   -0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -1.9189   -1.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5312    0.1959   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9932    0.0704   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837    0.0532    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2843    0.1333    1.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1896    0.1044    2.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7121    0.1803    4.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6527   -0.0119    2.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1603   -0.0929    1.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6437   -0.2118    1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2420   -0.0626    0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7684   -0.1425   -0.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4619   -1.4544   -3.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419   -1.5975   -3.2251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3562   -2.3698   -3.5363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9294   -1.5531    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7208    0.1598    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7255   -0.1945    2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6785    0.1590    2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5304   -1.6581    2.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9866   -0.8279    3.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2188   -1.2604    0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0797   -0.9880   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8423   -2.1093   -1.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9007   -0.1308   -3.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6724    0.9635   -1.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0172    0.4313   -2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4209    2.1302   -1.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9247    2.7176   -1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819    2.8716    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0825    1.0970    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3170    3.7333   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.5111   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2713    3.3216   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    0.0844    0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711    1.5470   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3738    0.6348    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088   -0.7465   -1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -1.4798    0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809   -2.7199   -1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0397   -2.3209   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022   -1.6442   -2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538    1.0711    0.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749   -0.7641   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2812    1.0041   -1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070    0.2185    1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3174   -0.0320    3.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1339   -0.6956    2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8239   -0.7811    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0203    0.8267    1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346   -2.9895   -4.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
  7 29  1  0
 29 31  1  0
 29 30  2  0
 27 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 21 62  1  0
 24 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 31 67  1  0
M  END


  Mrv1652304282219092D          

 31 31  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 11 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(=C/CC\C(C)=C\CC\C(C)=C\CC1=CC(=O)C=C(C)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O4/c1-19(2)9-6-13-23(27(30)31)14-8-12-20(3)10-7-11-21(4)15-16-24-18-25(28)17-22(5)26(24)29/h9-10,14-15,17-18H,6-8,11-13,16H2,1-5H3,(H,30,31)/b20-10+,21-15+,23-14+

> <INCHI_KEY>
IKUIJYZNRMQNBM-PIIINLNPSA-N

> <FORMULA>
C27H36O4

> <MOLECULAR_WEIGHT>
424.581

> <EXACT_MASS>
424.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.49657328472762

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6E,10E)-6,10-dimethyl-12-(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
7.201195824000001

> <ALOGPS_LOGS>
-5.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.178833464864109

> <JCHEM_PKA_STRONGEST_BASIC>
-7.8433423536837115

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
132.06959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E,10E)-6,10-dimethyl-12-(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   20   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   11                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
Sargaquinoate	Generator
MC14 Compound	MeSH

Chemical Formula

C₂₇H₃₆O₄

Average Mass

424.5810 Da

Monoisotopic Mass

424.26136 Da

IUPAC Name

(2E,6E,10E)-6,10-dimethyl-12-(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

Traditional Name

(2E,6E,10E)-6,10-dimethyl-12-(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(=C/CC\C(C)=C\CC\C(C)=C\CC1=CC(=O)C=C(C)C1=O)C(O)=O

InChI Identifier

InChI=1S/C27H36O4/c1-19(2)9-6-13-23(27(30)31)14-8-12-20(3)10-7-11-21(4)15-16-24-18-25(28)17-22(5)26(24)29/h9-10,14-15,17-18H,6-8,11-13,16H2,1-5H3,(H,30,31)/b20-10+,21-15+,23-14+

InChI Key

IKUIJYZNRMQNBM-PIIINLNPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Iryanthera juruensis	Plant	KNApSAcK
Roldana barba-johannis	Plant	KNApSAcK
Sargassum fallax	Chromalveolata	KNApSAcK
Sargassum thunbergii	Chromalveolata	KNApSAcK
Sargassum yezoense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Long-chain fatty acid
Prenylbenzoquinone
P-benzoquinone
Quinone
Methyl-branched fatty acid
Branched fatty acid
Unsaturated fatty acid
Fatty acid
Fatty acyl
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	5.74	ALOGPS
logP	7.2	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	5.18	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	132.07 m³·mol⁻¹	ChemAxon
Polarizability	49.5 Å³	ChemAxon
Number of Rings	1	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031302

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101145056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yoon JH, Youn K, Jun M: Protective effect of sargahydroquinoic acid against Abeta25-35-evoked damage via PI3K/Akt mediated Nrf2 antioxidant defense system. Biomed Pharmacother. 2021 Dec;144:112271. doi: 10.1016/j.biopha.2021.112271. Epub 2021 Oct 4. [PubMed:34619494 ]
Kwon M, Lee B, Lim S, Kim HR: Effects of Sargaquinoic Acid in Sargassum Serratifolium on Inducing Brown Adipocyte-like Phenotype in Mouse Adipocytes In Vitro. Planta Med. 2020 Jan;86(1):45-54. doi: 10.1055/a-1023-7385. Epub 2019 Oct 29. [PubMed:31663108 ]
Munedzimwe TC, van Zyl RL, Heslop DC, Edkins AL, Beukes DR: Semi-Synthesis and Evaluation of Sargahydroquinoic Acid Derivatives as Potential Antimalarial Agents. Medicines (Basel). 2019 Apr 1;6(2). pii: medicines6020047. doi: 10.3390/medicines6020047. [PubMed:30939856 ]
Lim S, Choi AH, Kwon M, Joung EJ, Shin T, Lee SG, Kim NG, Kim HR: Evaluation of antioxidant activities of various solvent extract from Sargassum serratifolium and its major antioxidant components. Food Chem. 2019 Apr 25;278:178-184. doi: 10.1016/j.foodchem.2018.11.058. Epub 2018 Nov 10. [PubMed:30583359 ]
Azam MS, Kwon M, Choi J, Kim HR: Sargaquinoic acid ameliorates hyperpigmentation through cAMP and ERK-mediated downregulation of MITF in alpha-MSH-stimulated B16F10 cells. Biomed Pharmacother. 2018 Aug;104:582-589. doi: 10.1016/j.biopha.2018.05.083. Epub 2018 May 25. [PubMed:29803170 ]

Showing NP-Card for Sargaquinoic acid (NP0071805)

MOL for NP0071805 (Sargaquinoic acid)

3D MOL for NP0071805 (Sargaquinoic acid)

3D SDF for NP0071805 (Sargaquinoic acid)

3D-SDF for NP0071805 (Sargaquinoic acid)

PDB for NP0071805 (Sargaquinoic acid)

3D PDB for NP0071805 (Sargaquinoic acid)

SMILES for NP0071805 (Sargaquinoic acid)

INCHI for NP0071805 (Sargaquinoic acid)

Structure for NP0071805 (Sargaquinoic acid)

3D Structure for NP0071805 (Sargaquinoic acid)