NP-MRD: Showing NP-Card for 4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone (NP0155094)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 12:06:01 UTC

Updated at

2022-09-02 12:06:01 UTC

NP-MRD ID

NP0155094

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone

Description

4,7'-Dihydroxy-3,5',6,15'-tetramethylidene-3,3a,4,5,6,6a,7,8,9a,9b-decahydro-2H-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadecan]-13'(16')-ene-2,4',8,14'-tetrone belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. 4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone is found in Nahuatlea hypoleuca. Based on a literature review very few articles have been published on 4,7'-dihydroxy-3,5',6,15'-tetramethylidene-3,3a,4,5,6,6a,7,8,9a,9b-decahydro-2H-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadecan]-13'(16')-ene-2,4',8,14'-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214062D          

 38 44  0  0  0  0            999 V2000
   -0.7775    1.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0473    1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3909    0.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3596   -0.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0569    0.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    1.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    1.6729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622    1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195    1.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5647    3.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966    3.8961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    2.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205    3.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987    3.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4754    4.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663    3.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209    4.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5759    3.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3846    2.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9918    3.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796    2.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1985    1.6521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    1.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1710    2.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3566    2.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178    1.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4273    0.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1977    1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7459    2.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 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
 21 22  1  0  0  0  0
 22 23  1  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
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 18 37  1  0  0  0  0
 37 38  2  0  0  0  0
 21 38  1  0  0  0  0
 32 38  1  0  0  0  0
M  END

     RDKit          3D

 68 74  0  0  0  0  0  0  0  0999 V2000
    6.7783    0.1793    1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    0.4475    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9491    1.4384   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0118    2.0851   -1.2069 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7109    1.5269   -1.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    1.1055   -0.6476 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4590   -0.0913   -0.0104 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7725   -0.5368    1.2248 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5497   -1.3861    1.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530    0.5849    2.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8116    1.0047    1.5026 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6967    0.6118    2.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6355    0.5580    1.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6328   -0.4274    0.6056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5233   -1.7886    1.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087   -2.2530    1.8167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7762   -2.5747    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872   -1.5623    0.3445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5504   -1.9962   -0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1240   -2.8866   -1.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9157   -1.4729   -1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0345   -0.0507   -0.4556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2376    0.4066   -1.0503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230    0.7857   -0.9442 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2972    2.2239   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3913    2.9112   -0.8744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    2.8869   -0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853    4.0901   -1.3571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0211    1.9779   -0.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947    0.8394   -0.0495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8782   -0.4007   -0.2048 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6019   -0.2578   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5782    0.5233    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4009    0.8436   -1.0890 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2370   -0.3798   -1.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276   -0.9401   -2.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129   -0.8918   -1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1963   -1.7120   -2.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7500    0.6958    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6987   -0.5411    1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399    1.8900    0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5425   -0.9417   -0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8837   -1.1533    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066   -1.0430    2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838    0.1750    3.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877    1.3820    2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296    2.1222    1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401   -0.3149    3.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274    1.4163    3.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333    1.5701    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3613    0.1463    2.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5577   -3.4608    0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -2.9275    1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3152   -1.1423    1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1600   -3.3620   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7492   -3.2103   -2.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6640   -2.0925   -0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0355   -1.3815   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1122   -0.0740    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0226    0.0232   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5536    0.4818   -1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3676    4.0234   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3961    2.5371   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798    0.9509    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441   -0.5879   -1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    1.7458   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527   -1.8460   -3.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9871   -0.5031   -3.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 31  1  0
 31 30  1  0
 30 29  1  0
 29 27  1  0
 27 28  2  0
 27 25  1  0
 25 26  2  3
 25 24  1  0
 24 22  1  0
 22 23  1  0
 22 21  1  0
 21 19  1  0
 19 20  2  3
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 14 32  1  0
 32 33  2  0
 33 34  1  0
 34  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
 34 35  1  0
 35 36  2  3
 35 37  1  0
 37 38  2  0
  7  8  1  0
 33 11  1  0
  7  6  1  0
 14 15  1  1
 37 32  1  0
 18 31  1  0
 24 30  1  0
  9 44  1  0
  8 43  1  6
 10 45  1  0
 10 46  1  0
 11 47  1  6
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 31 65  1  6
 30 64  1  1
 26 62  1  0
 26 63  1  0
 24 61  1  6
 22 59  1  1
 23 60  1  0
 21 57  1  0
 21 58  1  0
 20 55  1  0
 20 56  1  0
 18 54  1  1
 17 52  1  0
 17 53  1  0
 34 66  1  6
  6 41  1  1
  1 39  1  0
  1 40  1  0
  7 42  1  6
 36 67  1  0
 36 68  1  0
M  END


  Mrv1652309022214062D          

 38 44  0  0  0  0            999 V2000
   -0.7775    1.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0473    1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3909    0.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3596   -0.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0569    0.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    1.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    1.6729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622    1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195    1.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5647    3.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966    3.8961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    2.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205    3.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987    3.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4754    4.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663    3.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209    4.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5759    3.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3846    2.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9918    3.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796    2.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1985    1.6521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    1.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1710    2.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3566    2.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178    1.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4273    0.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1977    1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7459    2.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 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
 21 22  1  0  0  0  0
 22 23  1  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
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 18 37  1  0  0  0  0
 37 38  2  0  0  0  0
 21 38  1  0  0  0  0
 32 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155094

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2CCC3(C4C5OC(=O)C(=C)C5C(O)CC(=C)C4CC3=O)C3=C2C(C2OC(=O)C(=C)C12)C(=C)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O8/c1-10-7-16(31)20-13(4)29(36)38-27(20)23-15(10)9-18(33)30(23)6-5-14-8-17(32)19-12(3)28(35)37-26(19)21-11(2)25(34)24(30)22(14)21/h14-17,19-21,23,26-27,31-32H,1-9H2

> <INCHI_KEY>
XZUWIBKUNURJFV-UHFFFAOYSA-N

> <FORMULA>
C30H30O8

> <MOLECULAR_WEIGHT>
518.562

> <EXACT_MASS>
518.194067926

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.78754764212695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,7'-dihydroxy-3,5',6,15'-tetramethylidene-3,3a,4,5,6,6a,7,8,9a,9b-decahydro-2H-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
1.654085873000001

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.039077055851273

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.435721464991367

> <JCHEM_PKA_STRONGEST_BASIC>
-2.903200402050345

> <JCHEM_POLAR_SURFACE_AREA>
127.20000000000002

> <JCHEM_REFRACTIVITY>
133.76809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.451   1.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.088   1.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.730   0.514   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.224   0.142   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.538  -1.366   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.446   1.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.973   0.631   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.469  -0.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.092   1.894   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.363   2.398   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.021   3.123   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.476   2.619   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.291   3.602   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.783   3.288   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.019   4.625   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.054   5.765   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.740   7.273   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.458   5.133   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.465   6.673   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.802   7.437   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.224   6.658   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.487   7.539   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.964   7.101   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.999   8.241   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.542   5.674   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.051   5.369   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.185   6.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.229   3.840   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.570   3.084   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.829   3.198   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.786   4.332   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.266   4.086   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.633   2.682   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.398   1.345   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.102   2.849   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.067   1.709   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.789   4.357   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.126   5.121   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   13   19   37                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   38                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   33   38                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   18   38                                                  
CONECT   38   37   21   32                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₈

Average Mass

518.5620 Da

Monoisotopic Mass

518.19407 Da

IUPAC Name

4,7'-dihydroxy-3,5',6,15'-tetramethylidene-3,3a,4,5,6,6a,7,8,9a,9b-decahydro-2H-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone

Traditional Name

4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone

CAS Registry Number

Not Available

SMILES

OC1CC2CCC3(C4C5OC(=O)C(=C)C5C(O)CC(=C)C4CC3=O)C3=C2C(C2OC(=O)C(=C)C12)C(=C)C3=O

InChI Identifier

InChI=1S/C30H30O8/c1-10-7-16(31)20-13(4)29(36)38-27(20)23-15(10)9-18(33)30(23)6-5-14-8-17(32)19-12(3)28(35)37-26(19)21-11(2)25(34)24(30)22(14)21/h14-17,19-21,23,26-27,31-32H,1-9H2

InChI Key

XZUWIBKUNURJFV-UHFFFAOYSA-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
Gochnatia hypoleuca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Guaianolide-skeleton
Terpene lactone
Guaiane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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
logP	0.9	ALOGPS
logP	1.65	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	133.77 m³·mol⁻¹	ChemAxon
Polarizability	52.79 Å³	ChemAxon
Number of Rings	7	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163085513

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone (NP0155094)

MOL for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

3D MOL for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

3D SDF for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

3D-SDF for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

PDB for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

3D PDB for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

SMILES for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

INCHI for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

Structure for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)

3D Structure for NP0155094 (4,7'-dihydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3ah-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadecan]-13'(16')-ene-2,4',8,14'-tetrone)