NP-MRD: Showing NP-Card for Noscomin (NP0001595)

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Record Information

Version

1.0

Created at

2020-09-23 01:57:54 UTC

Updated at

2021-08-10 02:55:32 UTC

NP-MRD ID

NP0001595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Noscomin

Provided By

NPAtlas

Description

3-{[(1R,2R,4bR,7R,8aS,10aS)-7-hydroxy-1,2,4b,8,8-pentamethyl-1,2,3,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxybenzoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Noscomin is found in Nostoc commune. It was first documented in 1999 (PMID: 10096870). Based on a literature review very few articles have been published on 3-{[(1R,2R,4bR,7R,8aS,10aS)-7-hydroxy-1,2,4b,8,8-pentamethyl-1,2,3,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxybenzoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 69 72  0  0  0  0            999 V2000
    1.4805    0.5878    1.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8513    1.0188    0.5503 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117433D          

 69 72  0  0  0  0            999 V2000
    1.4805    0.5878    1.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8513    1.0188    0.5503 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1977    2.3557    0.2578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2900    2.1161    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.9212   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0223   -0.3434   -0.1931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6308   -1.2346   -1.2520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0554   -1.5213   -0.9552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6284   -0.5992    0.1089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0611   -0.8929    0.3575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1614   -2.3314    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9723   -0.6734   -0.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5044   -0.0226    1.5411 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8840   -0.2156    1.7732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3073    1.4257    1.2455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8842    1.7375    0.8503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2956    0.8332   -0.1677 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6492    1.2830   -1.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4202   -0.0159   -0.5033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5750    0.6556   -1.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -1.1970   -0.3073 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7608   -0.9390   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5687   -0.6645    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9084   -0.3886    0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7285   -0.1016    1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9474    0.1463    1.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1698   -0.1042    2.9604 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4866   -0.3835   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -0.6512   -1.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3507   -0.9314   -1.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682   -1.1927   -2.8720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5186    1.0764    2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2370    0.9582    2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908   -0.4792    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450    1.1826    0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6183    2.8959   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3168    2.9768    1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    2.9742    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0580   -0.8875    0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0642   -2.2105   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5184   -0.8598   -2.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1820   -2.5624   -0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628   -1.5199   -1.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0714   -0.8747    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925   -2.4096    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0971   -3.0549    0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4539   -2.5061    1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6306    0.2245   -0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035   -0.6437   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7055   -1.5322   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224   -0.2804    2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0461   -0.9180    2.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0450    1.8302    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5113    1.9884    2.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2747    1.6825    1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    2.8079    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    1.6589   -1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.1576   -1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708    0.5295   -2.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682    1.0929   -1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091    0.0456   -2.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8755    1.5506   -1.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139   -1.6478    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9696   -2.0260   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1238   -0.6645    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927    0.7417    3.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5611   -0.1613   -0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2075   -0.6381   -2.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1471   -1.1742   -3.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  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  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
  6 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 24 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 19  2  1  0  0  0  0
 30 22  1  0  0  0  0
 17  5  1  0  0  0  0
 17  9  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  1  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  4 38  1  0  0  0  0
  6 39  1  1  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  9 44  1  1  0  0  0
 11 45  1  0  0  0  0
 11 46  1  0  0  0  0
 11 47  1  0  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 13 51  1  1  0  0  0
 14 52  1  0  0  0  0
 15 53  1  0  0  0  0
 15 54  1  0  0  0  0
 16 55  1  0  0  0  0
 16 56  1  0  0  0  0
 18 57  1  0  0  0  0
 18 58  1  0  0  0  0
 18 59  1  0  0  0  0
 20 60  1  0  0  0  0
 20 61  1  0  0  0  0
 20 62  1  0  0  0  0
 21 63  1  0  0  0  0
 21 64  1  0  0  0  0
 23 65  1  0  0  0  0
 27 66  1  0  0  0  0
 28 67  1  0  0  0  0
 29 68  1  0  0  0  0
 31 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C(O[H])C(=C1[H])C([H])([H])[C@@]1(C([H])([H])[H])[C@@]2([H])C(=C([H])C([H])([H])[C@@]1([H])C([H])([H])[H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O4/c1-16-6-8-19-20(9-11-22-25(2,3)23(29)12-13-26(19,22)4)27(16,5)15-18-14-17(24(30)31)7-10-21(18)28/h7-8,10,14,16,20,22-23,28-29H,6,9,11-13,15H2,1-5H3,(H,30,31)/t16-,20-,22-,23-,26+,27-/m1/s1

> <INCHI_KEY>
HWGPBUBDNCZOBN-FVBFRTCBSA-N

> <FORMULA>
C27H38O4

> <MOLECULAR_WEIGHT>
426.597

> <EXACT_MASS>
426.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.031985273149445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(1R,2R,4bR,7R,8aS,10aS)-7-hydroxy-1,2,4b,8,8-pentamethyl-1,2,3,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxybenzoic acid

> <ALOGPS_LOGP>
6.10

> <JCHEM_LOGP>
5.723509554666669

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.920957653313222

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.375933519249717

> <JCHEM_PKA_STRONGEST_BASIC>
-0.806973689716146

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
123.96969999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1R,2R,4bR,7R,8aS,10aS)-7-hydroxy-1,2,4b,8,8-pentamethyl-3,5,6,7,8a,9,10,10a-octahydro-2H-phenanthren-1-yl]methyl}-4-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
    1.4805    0.5878    1.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8513    1.0188    0.5503 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1977    2.3557    0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2900    2.1161    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.9212   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0223   -0.3434   -0.1931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6308   -1.2346   -1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0554   -1.5213   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284   -0.5992    0.1089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0611   -0.8929    0.3575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1614   -2.3314    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9723   -0.6734   -0.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5044   -0.0226    1.5411 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8840   -0.2156    1.7732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3073    1.4257    1.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    1.7375    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2956    0.8332   -0.1677 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6492    1.2830   -1.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4202   -0.0159   -0.5033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5750    0.6556   -1.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -1.1970   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7608   -0.9390   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5687   -0.6645    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9084   -0.3886    0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7285   -0.1016    1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9474    0.1463    1.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1698   -0.1042    2.9604 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4866   -0.3835   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -0.6512   -1.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3507   -0.9314   -1.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682   -1.1927   -2.8720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5186    1.0764    2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2370    0.9582    2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908   -0.4792    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450    1.1826    0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6183    2.8959   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3168    2.9768    1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    2.9742    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0580   -0.8875    0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0642   -2.2105   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5184   -0.8598   -2.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1820   -2.5624   -0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628   -1.5199   -1.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0714   -0.8747    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925   -2.4096    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0971   -3.0549    0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4539   -2.5061    1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6306    0.2245   -0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035   -0.6437   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7055   -1.5322   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224   -0.2804    2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0461   -0.9180    2.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0450    1.8302    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5113    1.9884    2.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2747    1.6825    1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    2.8079    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    1.6589   -1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.1576   -1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708    0.5295   -2.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682    1.0929   -1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091    0.0456   -2.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8755    1.5506   -1.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139   -1.6478    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9696   -2.0260   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1238   -0.6645    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927    0.7417    3.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5611   -0.1613   -0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2075   -0.6381   -2.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1471   -1.1742   -3.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
  6 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
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 29 30  2  0
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 19  2  1  0
 30 22  1  0
 17  5  1  0
 17  9  1  0
  1 32  1  0
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 28 67  1  0
 29 68  1  0
 31 69  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.480   0.588   1.948  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.851   1.019   0.550  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.198   2.356   0.258  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.290   2.116   0.132  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.782   0.921  -0.065  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.022  -0.343  -0.193  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.631  -1.235  -1.252  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.055  -1.521  -0.955  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.628  -0.599   0.109  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.061  -0.893   0.358  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.161  -2.331   0.858  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.972  -0.673  -0.790  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.504  -0.023   1.541  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.884  -0.216   1.773  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.307   1.426   1.246  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.884   1.738   0.850  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.296   0.833  -0.168  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.649   1.283  -1.556  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.420  -0.016  -0.503  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.575   0.656  -1.830  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.320  -1.197  -0.307  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.761  -0.939  -0.468  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.569  -0.665   0.616  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.908  -0.389   0.512  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.729  -0.102   1.706  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.947   0.146   1.567  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.170  -0.104   2.960  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.487  -0.384  -0.741  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.722  -0.651  -1.846  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.351  -0.931  -1.709  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.668  -1.193  -2.872  0.00  0.00           O+0
HETATM   32  H   UNK     0       0.519   1.076   2.215  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.237   0.958   2.697  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.391  -0.479   2.109  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.945   1.183   0.527  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.618   2.896  -0.585  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.317   2.977   1.170  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.928   2.974   0.209  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.058  -0.888   0.749  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.064  -2.211  -1.220  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.518  -0.860  -2.270  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.182  -2.562  -0.536  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.663  -1.520  -1.884  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.071  -0.875   1.054  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.192  -2.410   1.310  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.097  -3.055   0.042  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.454  -2.506   1.686  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.631   0.225  -0.607  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.503  -0.644  -1.778  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.705  -1.532  -0.825  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.922  -0.280   2.442  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.046  -0.918   2.446  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.045   1.830   0.506  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.511   1.988   2.187  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.275   1.683   1.779  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.908   2.808   0.492  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.690   1.659  -1.634  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.986   2.158  -1.790  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.471   0.530  -2.321  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.568   1.093  -1.989  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.309   0.046  -2.704  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.876   1.551  -1.917  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.214  -1.648   0.716  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.970  -2.026  -0.978  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.124  -0.665   1.621  0.00  0.00           H+0
HETATM   66  H   UNK     0       5.893   0.742   3.459  0.00  0.00           H+0
HETATM   67  H   UNK     0       7.561  -0.161  -0.824  0.00  0.00           H+0
HETATM   68  H   UNK     0       6.207  -0.638  -2.806  0.00  0.00           H+0
HETATM   69  H   UNK     0       4.147  -1.174  -3.753  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   19   35                                             
CONECT    3    2    4   36   37                                             
CONECT    4    3    5   38                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7   19   39                                             
CONECT    7    6    8   40   41                                             
CONECT    8    7    9   42   43                                             
CONECT    9    8   10   17   44                                             
CONECT   10    9   11   12   13                                             
CONECT   11   10   45   46   47                                             
CONECT   12   10   48   49   50                                             
CONECT   13   10   14   15   51                                             
CONECT   14   13   52                                                       
CONECT   15   13   16   53   54                                             
CONECT   16   15   17   55   56                                             
CONECT   17   16   18    5    9                                             
CONECT   18   17   57   58   59                                             
CONECT   19    6   20   21    2                                             
CONECT   20   19   60   61   62                                             
CONECT   21   19   22   63   64                                             
CONECT   22   21   23   30                                                  
CONECT   23   22   24   65                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   66                                                       
CONECT   28   24   29   67                                                  
CONECT   29   28   30   68                                                  
CONECT   30   29   31   22                                                  
CONECT   31   30   69                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    6                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   11                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   15                                                            
CONECT   55   16                                                            
CONECT   56   16                                                            
CONECT   57   18                                                            
CONECT   58   18                                                            
CONECT   59   18                                                            
CONECT   60   20                                                            
CONECT   61   20                                                            
CONECT   62   20                                                            
CONECT   63   21                                                            
CONECT   64   21                                                            
CONECT   65   23                                                            
CONECT   66   27                                                            
CONECT   67   28                                                            
CONECT   68   29                                                            
CONECT   69   31                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  144    0
END

RDKit          3D

69 72  0  0  0  0  0  0  0  0999 V2000
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 20 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 23 65  1  0
 27 66  1  0
 28 67  1  0
 29 68  1  0
 31 69  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-{[(1R,2R,4BR,7R,8as,10as)-7-hydroxy-1,2,4b,8,8-pentamethyl-1,2,3,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxybenzoate	Generator
8-((5-Carboxy-2-hydroxy)benzyl)-2-hydroxy-1,1,4a,7,8-pentamethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene	MeSH

Chemical Formula

C₂₇H₃₈O₄

Average Mass

426.5970 Da

Monoisotopic Mass

426.27701 Da

IUPAC Name

3-{[(1R,2R,4bR,7R,8aS,10aS)-7-hydroxy-1,2,4b,8,8-pentamethyl-1,2,3,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxybenzoic acid

Traditional Name

3-{[(1R,2R,4bR,7R,8aS,10aS)-7-hydroxy-1,2,4b,8,8-pentamethyl-3,5,6,7,8a,9,10,10a-octahydro-2H-phenanthren-1-yl]methyl}-4-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C([H])=C(O[H])C(=C1[H])C([H])([H])[C@@]1(C([H])([H])[H])[C@@]2([H])C(=C([H])C([H])([H])[C@@]1([H])C([H])([H])[H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C2([H])[H]

InChI Identifier

InChI=1S/C27H38O4/c1-16-6-8-19-20(9-11-22-25(2,3)23(29)12-13-26(19,22)4)27(16,5)15-18-14-17(24(30)31)7-10-21(18)28/h7-8,10,14,16,20,22-23,28-29H,6,9,11-13,15H2,1-5H3,(H,30,31)/t16-,20-,22-,23-,26+,27-/m1/s1

InChI Key

HWGPBUBDNCZOBN-FVBFRTCBSA-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
Nostoc commune	NPAtlas	10096870

Species Where Detected

Species Name	Source	Reference
Nostoc commune Vaucher EAWAG122b	KNApSAcK Database	22123792

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
Cleistanthane diterpenoid
Hydrophenanthrene
Phenanthrene
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	6.1	ALOGPS
logP	5.72	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	123.97 m³·mol⁻¹	ChemAxon
Polarizability	49.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA006116

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8585662

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10410225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jaki B, Orjala J, Sticher O: A novel extracellular diterpenoid with antibacterial activity from the cyanobacterium Nostoc commune. J Nat Prod. 1999 Mar;62(3):502-3. doi: 10.1021/np980444x. [PubMed:10096870 ]

Showing NP-Card for Noscomin (NP0001595)

MOL for NP0001595 (Noscomin)

3D MOL for NP0001595 (Noscomin)

3D SDF for NP0001595 (Noscomin)

3D-SDF for NP0001595 (Noscomin)

PDB for NP0001595 (Noscomin)

3D PDB for NP0001595 (Noscomin)

SMILES for NP0001595 (Noscomin)

INCHI for NP0001595 (Noscomin)

Structure for NP0001595 (Noscomin)

3D Structure for NP0001595 (Noscomin)