NP-MRD: Showing NP-Card for (+)-Subersic acid (NP0078826)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 23:55:04 UTC

Updated at

2022-04-28 23:55:05 UTC

NP-MRD ID

NP0078826

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Subersic acid

Description

(+)-Subersic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (+)-Subersic acid is found in Acanthodendrilla sp. (+)-Subersic acid was first documented in 2004 (PMID: 15620270). Based on a literature review very few articles have been published on (+)-subersic acid (PMID: 16854715).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201552D          

 30 32  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
   -0.7145   -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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    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
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    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    0.0000    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
    2.1434   -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
    1.0416    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 13 21  1  0  0  0  0
  9 22  1  0  0  0  0
  5 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 27  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  1  0  0  0  0
  1 30  1  1  0  0  0
M  END

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
   -1.4294   -1.4178   -2.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2519   -0.7755   -1.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -0.5494   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3422   -1.0011   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6846    0.0627   -0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154   -0.6697   -0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -1.6290    0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -0.4708   -1.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648   -1.1965   -1.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029   -0.2619   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0124   -0.0473    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0735    0.8206    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6997    1.0294    1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6745    1.8223    1.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2044    0.3335    2.8862 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5737    1.5193   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9716    1.3128   -1.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043    0.4384   -1.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123    0.2431   -3.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361    0.0428    0.5216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5991   -1.0090    1.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095    1.2528    1.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911    2.1487    1.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1826    1.4910    2.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8775    0.8726    1.0423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7675    1.9729    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7961   -0.2263    1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853    0.4239    0.0132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4701   -0.5956   -0.9464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354   -0.4178   -2.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692   -2.4812   -2.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702   -0.8279   -3.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442   -1.2529   -3.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2585   -1.5876    0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986   -1.7407   -1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7075    0.7951   -1.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6369    0.6187    0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4433   -2.6532    0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1583   -1.2563    1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4572   -1.6983    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154    0.2179   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285   -1.8889   -0.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -1.8619   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6003   -0.6110    1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5796   -0.5999    3.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4130    2.2073   -0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3769    1.8721   -2.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6714    0.7477   -3.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -1.2903    1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1157   -1.9433    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857   -0.7050    2.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3511    1.8271    0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696    0.9850    1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1288    2.9862    1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587    2.6241    2.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0633    0.7618    3.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414    2.2921    2.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2310    2.3907   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9701    2.7570    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7338    1.5739    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7354   -1.1555    0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8858    0.0771    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6873   -0.3848    2.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6935    1.3503   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5382   -0.3792   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876   -1.6403   -0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    0.6893   -2.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0253   -0.9949   -3.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 30  1  0
 30 29  1  0
 29 28  1  0
 28 25  1  0
 25 26  1  6
 25 27  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  1
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
 16 12  1  0
 12 11  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 20  3  1  0
 11 10  1  0
 20 28  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
  5 36  1  0
  5 37  1  0
  4 34  1  0
  4 35  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 67  1  0
 30 68  1  0
 29 65  1  0
 29 66  1  0
 28 64  1  6
 26 58  1  0
 26 59  1  0
 26 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
 24 56  1  0
 24 57  1  0
 23 54  1  0
 23 55  1  0
 22 52  1  0
 22 53  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 19 48  1  0
 17 47  1  0
 16 46  1  0
 11 44  1  0
 15 45  1  0
M  END


  Mrv1652304292201552D          

 30 32  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
   -0.7145   -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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    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
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    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    0.0000    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
    2.1434   -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
    1.0416    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 13 21  1  0  0  0  0
  9 22  1  0  0  0  0
  5 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 27  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  1  0  0  0  0
  1 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078826

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CCC1=C(C)CC[C@H]2C(C)(C)CCC[C@]12C)=C/CC1=C(O)C=CC(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O3/c1-18(7-10-20-17-21(25(29)30)11-13-23(20)28)8-12-22-19(2)9-14-24-26(3,4)15-6-16-27(22,24)5/h7,11,13,17,24,28H,6,8-10,12,14-16H2,1-5H3,(H,29,30)/b18-7+/t24-,27+/m0/s1

> <INCHI_KEY>
RIYHRKNIDKXDII-UEKCLBEQSA-N

> <FORMULA>
C27H38O3

> <MOLECULAR_WEIGHT>
410.598

> <EXACT_MASS>
410.282095084

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.92666118830823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2E)-5-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-4-hydroxybenzoic acid

> <ALOGPS_LOGP>
6.69

> <JCHEM_LOGP>
7.270880331999999

> <ALOGPS_LOGS>
-5.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.47516188685041

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.347914248682027

> <JCHEM_PKA_STRONGEST_BASIC>
-6.114865026966986

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
125.01809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2E)-5-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-4-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668 -10.010   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      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.944   1.360   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.390   1.360   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2    6   27   30                                             
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   13                                                            
CONECT   22    9                                                            
CONECT   23    5                                                            
CONECT   24    2   25   28   29                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    1                                                       
CONECT   28   24                                                            
CONECT   29   24                                                            
CONECT   30    1                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
(+)-Subersate	Generator
Subersic acid	MeSH

Chemical Formula

C₂₇H₃₈O₃

Average Mass

410.5980 Da

Monoisotopic Mass

410.28210 Da

IUPAC Name

3-[(2E)-5-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-4-hydroxybenzoic acid

Traditional Name

3-[(2E)-5-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-4-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

C\C(CCC1=C(C)CC[C@H]2C(C)(C)CCC[C@]12C)=C/CC1=C(O)C=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C27H38O3/c1-18(7-10-20-17-21(25(29)30)11-13-23(20)28)8-12-22-19(2)9-14-24-26(3,4)15-6-16-27(22,24)5/h7,11,13,17,24,28H,6,8-10,12,14-16H2,1-5H3,(H,29,30)/b18-7+/t24-,27+/m0/s1

InChI Key

RIYHRKNIDKXDII-UEKCLBEQSA-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
Acanthodendrilla sp.	Animalia	KNApSAcK

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

Labdane diterpenoid
Diterpenoid
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:66532 )
carbobicyclic compound (CHEBI:66532 )
meroterpenoid (CHEBI:66532 )

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	6.69	ALOGPS
logP	7.27	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	125.02 m³·mol⁻¹	ChemAxon
Polarizability	47.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

9536819

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11361892

PDB ID

Not Available

ChEBI ID

66532

Good Scents ID

Not Available

References

General References

Fekih AW, Gafsi K, Ferreiro-Mederos L, Hanquet G: Hemisynthesis of new labdane derivatives from (-)-sclareol. Nat Prod Res. 2006 Aug;20(10):887-95. doi: 10.1080/14786410500160686. [PubMed:16854715 ]
Williams DE, Telliez JB, Liu J, Tahir A, van Soest R, Andersen RJ: Meroterpenoid MAPKAP (MK2) inhibitors isolated from the indonesian marine sponge Acanthodendrilla sp. J Nat Prod. 2004 Dec;67(12):2127-9. doi: 10.1021/np049808d. [PubMed:15620270 ]

Showing NP-Card for (+)-Subersic acid (NP0078826)

MOL for NP0078826 ((+)-Subersic acid)

3D MOL for NP0078826 ((+)-Subersic acid)

3D SDF for NP0078826 ((+)-Subersic acid)

3D-SDF for NP0078826 ((+)-Subersic acid)

PDB for NP0078826 ((+)-Subersic acid)

3D PDB for NP0078826 ((+)-Subersic acid)

SMILES for NP0078826 ((+)-Subersic acid)

INCHI for NP0078826 ((+)-Subersic acid)

Structure for NP0078826 ((+)-Subersic acid)

3D Structure for NP0078826 ((+)-Subersic acid)