NP-MRD: Showing NP-Card for (1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid (NP0316212)

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Record Information

Version

2.0

Created at

2022-09-11 15:14:54 UTC

Updated at

2022-09-11 15:14:54 UTC

NP-MRD ID

NP0316212

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid

Description

Scabronine A, also known as episcabronine a, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid is found in Sarcodon scabrosus. (1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid was first documented in 2013 (PMID: 23765646). Based on a literature review very few articles have been published on Scabronine A (PMID: 25065736).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217142D          

 28 31  0  0  1  0            999 V2000
    3.8643    1.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4350    2.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042    2.8512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1322    1.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5372    2.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3860    2.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3154    3.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967    3.7435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8020    3.5217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2023    4.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821    4.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    4.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521    3.5045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5620    4.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162    4.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4432    5.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3470    3.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    2.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0264    2.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7583    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1310    0.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    0.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    2.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970    2.8029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6188    2.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3376    1.6033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7298    0.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4247    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  2  0  0  0  0
 13 23  1  0  0  0  0
 24 23  1  6  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    3.9059   -0.8690    3.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -1.0539    1.6698 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -0.5111    1.1636 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0343    0.4649    0.0881 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4794   -0.5618   -0.9702 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5667    0.0695   -2.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516   -1.4968   -0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341   -1.5375    0.3492 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4426   -1.4491    0.2624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1511   -1.9833    1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0873   -2.4698   -0.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610   -2.5806   -1.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914   -1.2971   -1.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3162   -0.7935   -2.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8499    0.3347   -2.9365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346   -1.4921   -3.5177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5003   -1.5021   -0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8419   -0.0640   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746    0.5317    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620    1.6670    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    1.8980    2.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2397    2.9341    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5691   -0.1885   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146   -0.1567   -0.2118 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5943    1.0668    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9348    1.2517   -0.5185 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2540    2.6135   -0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602    3.2891   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8332   -1.2861    3.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0363   -1.3959    3.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    0.2169    3.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0965   -0.0996    2.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    1.0220    0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301   -1.0453   -0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796    0.4370   -2.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783   -2.5387    0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0200   -3.0739    1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2200   -1.4283    2.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -1.8136    1.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -2.1353   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -3.4681   -0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8811   -3.2735   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792   -3.0961   -2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6985   -1.0754   -4.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424   -2.0419   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3674   -2.0034    0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0822    0.4218   -1.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6744    0.0045    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6027    1.3944    1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    2.7012    1.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    2.2499    3.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2353    0.9314    2.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160    2.5989   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869    3.4662   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292    3.6090    1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823   -0.1833   -1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238    1.2127    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016    1.9370   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8580    1.1037   -1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482    2.8543   -2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859    4.3209   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758    3.3626   -1.9955 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  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 19 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 13 14  1  6
 14 16  1  0
 14 15  2  0
  8  3  1  0
 24  9  1  0
 26  4  1  0
 23 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  1
  4 33  1  1
  5 34  1  1
  6 35  1  0
  8 36  1  1
 10 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 17 45  1  0
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 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 24 56  1  6
 25 57  1  0
 25 58  1  0
 26 59  1  6
 28 60  1  0
 28 61  1  0
 28 62  1  0
 16 44  1  0
M  END


  Mrv1652309112217142D          

 28 31  0  0  1  0            999 V2000
    3.8643    1.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4350    2.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042    2.8512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1322    1.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5372    2.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3860    2.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3154    3.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967    3.7435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8020    3.5217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2023    4.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821    4.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    4.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521    3.5045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5620    4.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162    4.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4432    5.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3470    3.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    2.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0264    2.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7583    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1310    0.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    0.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    2.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970    2.8029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6188    2.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3376    1.6033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7298    0.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4247    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  2  0  0  0  0
 13 23  1  0  0  0  0
 24 23  1  6  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H]2C(O)O[C@@H]1[C@]1(C)CC[C@]3(CCC(C(C)C)=C3[C@H]1C[C@H]2OC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O6/c1-11(2)12-6-7-22(20(24)25)9-8-21(3)13(16(12)22)10-14(26-4)15-17(27-5)18(21)28-19(15)23/h11,13-15,17-19,23H,6-10H2,1-5H3,(H,24,25)/t13-,14-,15+,17+,18+,19?,21-,22+/m1/s1

> <INCHI_KEY>
SJRSXOFCFKORFT-AQBQCHLVSA-N

> <FORMULA>
C22H34O6

> <MOLECULAR_WEIGHT>
394.508

> <EXACT_MASS>
394.235538815

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.04892916813829

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,10R,12R,13S,16S)-14-hydroxy-12,16-dimethoxy-2-methyl-8-(propan-2-yl)-15-oxatetracyclo[11.2.1.0^{2,10}.0^{5,9}]hexadec-8-ene-5-carboxylic acid

> <JCHEM_LOGP>
2.4059899343333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.010342065166688

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.389246082930534

> <JCHEM_PKA_STRONGEST_BASIC>
-3.721979675245915

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
103.05839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,10R,12R,13S,16S)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0^{2,10}.0^{5,9}]hexadec-8-ene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       7.213   2.489   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.279   4.071   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.528   5.322   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.580   3.407   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.336   4.748   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.921   4.406   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.922   6.232   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.580   6.988   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.097   6.574   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.844   8.118   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.313   7.899   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.773   7.883   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.017   6.542   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.916   7.919   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.337   8.319   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.694   9.530   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.514   6.206   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.369   4.673   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.783   4.061   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.282   2.452   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.978   0.991   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.001   1.496   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.801   5.216   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.341   5.232   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.755   3.749   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.097   2.993   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.829   1.437   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.126   0.488   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11   24                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17   23                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   13   24                                                  
CONECT   24   23    9   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    4   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
Episcabronine a	MeSH

Chemical Formula

C₂₂H₃₄O₆

Average Mass

394.5080 Da

Monoisotopic Mass

394.23554 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H]2C(O)O[C@@H]1[C@]1(C)CC[C@]3(CCC(C(C)C)=C3[C@H]1C[C@H]2OC)C(O)=O

InChI Identifier

InChI=1S/C22H34O6/c1-11(2)12-6-7-22(20(24)25)9-8-21(3)13(16(12)22)10-14(26-4)15-17(27-5)18(21)28-19(15)23/h11,13-15,17-19,23H,6-10H2,1-5H3,(H,24,25)/t13-,14-,15+,17+,18+,19?,21-,22+/m1/s1

InChI Key

SJRSXOFCFKORFT-AQBQCHLVSA-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
Sarcodon scabrosus	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
Monosaccharide
Oxolane
Hemiacetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

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

8128143

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9952533

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nakada M: Enantioselective total syntheses of cyathane diterpenoids. Chem Rec. 2014 Aug;14(4):641-62. doi: 10.1002/tcr.201402019. Epub 2014 Jul 28. [PubMed:25065736 ]
Kobayakawa Y, Nakada M: Total syntheses of (-)-scabronines G and A, and (-)-episcabronine A. Angew Chem Int Ed Engl. 2013 Jul 15;52(29):7569-73. doi: 10.1002/anie.201303224. Epub 2013 Jun 13. [PubMed:23765646 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid (NP0316212)

MOL for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

3D MOL for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

3D SDF for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

3D-SDF for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

PDB for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

3D PDB for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

SMILES for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

INCHI for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

Structure for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)

3D Structure for NP0316212 ((1r,2r,5s,10r,12r,13s,16s)-14-hydroxy-8-isopropyl-12,16-dimethoxy-2-methyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]hexadec-8-ene-5-carboxylic acid)