NP-MRD: Showing NP-Card for (3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid (NP0230682)

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Record Information

Version

2.0

Created at

2022-09-06 11:12:42 UTC

Updated at

2022-09-06 11:12:42 UTC

NP-MRD ID

NP0230682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid

Description

Stellatic acid, also known as stellatate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Stellatic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid is found in Aspergillus stellatus. (3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid was first documented in 2004 (PMID: 15612624). Based on a literature review very few articles have been published on stellatic acid (PMID: 26351860).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213122D          

 27 29  0  0  1  0            999 V2000
    6.4925   -0.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7885   -0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8089   -1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0640   -0.4012    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9574    0.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464    0.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518   -0.1562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2505    0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3189   -0.7554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0835   -1.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2810   -1.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7139   -1.1384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4785   -1.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9115   -1.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444   -0.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -1.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736   -2.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959   -1.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0252   -0.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785    0.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2723    2.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493   -0.3477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 12 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
    5.1874    1.2785   -1.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5295    0.1438   -1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6039   -0.8959   -2.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280   -0.0894   -0.1411 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5407    1.2549    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    1.1120    1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564   -0.1757    0.8710 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9734   -1.2628    1.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2837   -0.3811   -0.4851 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9755   -1.7433   -0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6369   -2.2729   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3831   -1.1967   -0.2061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4937   -1.9135    0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556   -0.6930   -1.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -0.7690   -1.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414    0.2216   -1.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7975    0.0132   -1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6275    0.9345   -1.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3098   -1.2965   -1.4654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8690    1.5925   -1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4565    2.4312   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    1.7050    0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    1.3421    1.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2406    0.5946    2.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671    1.6243    1.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    0.3077    1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1741   -0.0516    0.5660 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1852    2.0630   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7812    1.4799   -2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227   -0.7883   -2.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8829   -0.7032   -3.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5683   -1.9208   -2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -0.8442    0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3962    1.4869    1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653    2.0721   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    1.0315    2.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322    1.9664    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6263   -2.0605    1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5098   -0.8342    2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227   -1.6828    2.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552    0.3634   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -1.7724   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471   -2.4438   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353   -3.0210    0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210   -2.8364   -1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3906   -1.3151    0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327   -2.3869    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982   -2.7851   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.2216   -1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7179   -1.4183   -2.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285   -1.7867   -1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8820   -2.0455   -2.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2745    2.0426   -2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8095    1.7748   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    3.3052   -0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3988    2.9288   -0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7726    1.4320    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8695    1.3334    3.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050   -0.3190    2.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848    0.3707    3.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0595    2.0537    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0924    2.3617    2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397    0.4953    2.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -0.4786    2.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1210    0.8456   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
  9  4  1  0
 27 12  1  0
 27  7  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  1 28  1  0
  1 29  1  0
  4 33  1  1
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  6
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  6
 19 52  1  0
M  END


  Mrv1652309062213122D          

 27 29  0  0  1  0            999 V2000
    6.4925   -0.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7885   -0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8089   -1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0640   -0.4012    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9574    0.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464    0.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518   -0.1562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2505    0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3189   -0.7554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0835   -1.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2810   -1.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7139   -1.1384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4785   -1.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9115   -1.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444   -0.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -1.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736   -2.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959   -1.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0252   -0.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785    0.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2723    2.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493   -0.3477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 12 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1CC[C@]2(C)[C@@H]1CC[C@]1(C)C\C=C(\CC\C=C(C)\CC[C@@H]21)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O2/c1-17(2)20-12-16-25(5)21(20)13-15-24(4)14-11-19(23(26)27)8-6-7-18(3)9-10-22(24)25/h7,11,20-22H,1,6,8-10,12-16H2,2-5H3,(H,26,27)/b18-7+,19-11-/t20-,21-,22-,24+,25-/m1/s1

> <INCHI_KEY>
FSKFLBQJBSQQKA-DMZCBJAKSA-N

> <FORMULA>
C25H38O2

> <MOLECULAR_WEIGHT>
370.577

> <EXACT_MASS>
370.287180464

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.50956803857528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,5aR,14aR,14bR)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,9H,10H,13H,14H,14aH,14bH-cycloundeca[e]indene-8-carboxylic acid

> <JCHEM_LOGP>
6.670213005666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.037356626636844

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
113.94429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,5aR,14aR,14bR)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,6H,9H,10H,13H,14H,14aH-cycloundeca[e]indene-8-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      12.119  -0.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.805  -1.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.843  -3.025   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.453  -0.749   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.254   0.778   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.740   1.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.003  -0.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.068   0.932   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.062  -1.410   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.622  -2.886   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.125  -3.243   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.066  -2.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.627  -3.601   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.568  -2.482   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.510  -1.364   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.012  -1.721   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.572  -3.197   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.631  -4.316   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.926  -3.555   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.047  -0.603   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.392   0.873   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.013   1.335   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.887   2.603   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.375   4.055   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.363   2.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.401   0.624   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.505  -0.649   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   27                                             
CONECT    8    7                                                            
CONECT    9    7    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   27                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   12    7                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Stellatate	Generator

Chemical Formula

C₂₅H₃₈O₂

Average Mass

370.5770 Da

Monoisotopic Mass

370.28718 Da

IUPAC Name

(3S,3aR,5aR,14aR,14bR)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,9H,10H,13H,14H,14aH,14bH-cycloundeca[e]indene-8-carboxylic acid

Traditional Name

(3S,3aR,5aR,14aR,14bR)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,6H,9H,10H,13H,14H,14aH-cycloundeca[e]indene-8-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1CC[C@]2(C)[C@@H]1CC[C@]1(C)C\C=C(\CC\C=C(C)\CC[C@@H]21)C(O)=O

InChI Identifier

InChI=1S/C25H38O2/c1-17(2)20-12-16-25(5)21(20)13-15-24(4)14-11-19(23(26)27)8-6-7-18(3)9-10-22(24)25/h7,11,20-22H,1,6,8-10,12-16H2,2-5H3,(H,26,27)/b18-7+,19-11-/t20-,21-,22-,24+,25-/m1/s1

InChI Key

FSKFLBQJBSQQKA-DMZCBJAKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aspergillus stellatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	6.67	ChemAxon
pKa (Strongest Acidic)	5.04	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	2	ChemAxon
Refractivity	113.94 m³·mol⁻¹	ChemAxon
Polarizability	44.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00041547

Chemspider ID

35517211

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102515494

PDB ID

Not Available

ChEBI ID

169999

Good Scents ID

Not Available

References

General References

Matsuda Y, Mitsuhashi T, Quan Z, Abe I: Molecular Basis for Stellatic Acid Biosynthesis: A Genome Mining Approach for Discovery of Sesterterpene Synthases. Org Lett. 2015 Sep 18;17(18):4644-7. doi: 10.1021/acs.orglett.5b02404. Epub 2015 Sep 9. [PubMed:26351860 ]
Frisvad JC, Samson RA: Emericella venezuelensis, a new species with stellate ascospores producing sterigmatocystin and aflatoxin B1. Syst Appl Microbiol. 2004 Nov;27(6):672-80. doi: 10.1078/0723202042369910. [PubMed:15612624 ]
LOTUS database [Link]

Showing NP-Card for (3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid (NP0230682)

MOL for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

3D MOL for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

3D SDF for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

3D-SDF for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

PDB for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

3D PDB for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

SMILES for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

INCHI for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

Structure for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)

3D Structure for NP0230682 ((3s,3ar,5ar,14ar,14br)-5a,12,14b-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,6h,9h,10h,13h,14h,14ah-cycloundeca[e]indene-8-carboxylic acid)