NP-MRD: Showing NP-Card for (2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione (NP0302164)

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Record Information

Version

1.0

Created at

2022-09-10 15:32:24 UTC

Updated at

2022-09-10 15:32:24 UTC

NP-MRD ID

NP0302164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione

Description

Altercrasin A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. It was first documented in 2022 (PMID: 36109246). Based on a literature review a significant number of articles have been published on Altercrasin A (PMID: 36087713) (PMID: 36083970) (PMID: 36091400) (PMID: 36088383).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102217322D          

 30 33  0  0  1  0            999 V2000
    3.4779    2.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949    2.2732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6040    3.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8028    1.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4937    0.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0016    0.2080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8261    0.2368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3564    0.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1689    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4511   -0.0497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2635   -0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5457   -0.9683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3581   -1.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0154   -1.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2029   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9207   -0.6817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1083   -0.5384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3078   -1.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4582   -1.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4869   -1.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7742   -0.5850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5468   -1.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0547   -2.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223   -1.4068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2609   -2.0907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4380   -2.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6226   -2.8323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -0.6315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0615    0.7009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  6  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  6  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
   -3.6505   -4.0485    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839   -3.4130   -1.2733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3813   -2.8105   -1.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1412   -2.4611   -1.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795   -1.7177   -0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8822   -0.7823    0.1583 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1746   -0.7410   -0.8890 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0437   -1.9300   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602   -1.8626   -0.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0143   -0.5280   -0.6726 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4022   -0.6521   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9320    0.4661    0.6428 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1021   -0.0618    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9087    1.0697    1.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    1.5823    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1030    0.3606    0.1464 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8696    0.5829   -0.6517 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1726    1.2746   -1.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1382    1.4366    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133    2.6098    0.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3335    0.6470    0.3432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4921    0.9803   -0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6005    1.0202   -1.7282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5989    1.2850    0.4236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1942    2.6535    0.1539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1926    3.7505    0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7862    2.7060   -1.1009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9852    1.2361    1.7257 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693    0.8975    1.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8866    0.7540    2.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7310   -4.1869    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1893   -4.9898   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2855   -3.3110    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9335   -4.2430   -1.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0490   -3.5232   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -2.3835   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7228   -1.8103    0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -1.0432    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2586   -0.7653   -1.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -2.9303   -0.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9041   -2.7930   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593   -0.1891   -1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5806   -1.6150    0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0761   -0.7550   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3491    1.2982    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6834   -0.7242    2.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7077   -0.7172    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7112    0.7542    1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    0.2621    2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722    1.8799    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794    2.1182   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860    2.2079    1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046   -0.2482    1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0004    1.9596   -1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    1.8603   -2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3686    0.5356   -2.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746    0.4941    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0185    2.7902    0.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    4.7126    0.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481    3.8811   -0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    3.4982    1.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    3.5521   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    0.1200    3.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
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 29 30  1  0
 29 28  2  0
 28 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 24 22  1  0
 22 23  2  0
 21  6  1  0
 22 21  1  0
 17  7  1  0
 16 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  6
  3 35  1  0
  4 36  1  0
  5 37  1  0
  6 38  1  1
  7 39  1  6
  8 40  1  0
  9 41  1  0
 10 42  1  6
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 13 47  1  0
 13 48  1  0
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 18 54  1  0
 18 55  1  0
 18 56  1  0
 30 63  1  0
 24 57  1  1
 25 58  1  1
 26 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
M  END


  Mrv1652309102217322D          

 30 33  0  0  1  0            999 V2000
    3.4779    2.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949    2.2732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6040    3.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8028    1.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4937    0.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0016    0.2080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8261    0.2368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3564    0.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1689    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4511   -0.0497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2635   -0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5457   -0.9683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3581   -1.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0154   -1.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2029   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9207   -0.6817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1083   -0.5384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3078   -1.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4582   -1.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4869   -1.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7742   -0.5850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5468   -1.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0547   -2.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223   -1.4068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2609   -2.0907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4380   -2.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6226   -2.8323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -0.6315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0615    0.7009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  6  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  6  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)\C=C\[C@H]1[C@@H]2C=C[C@@H]3C[C@H](C)CC[C@H]3[C@]2(C)C(=O)[C@]11C(O)=N[C@@H]([C@@H](C)O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H33NO5/c1-12-5-8-16-15(11-12)7-10-17-18(9-6-13(2)26)24(21(29)23(16,17)4)20(28)19(14(3)27)25-22(24)30/h6-7,9-10,12-19,26-27H,5,8,11H2,1-4H3,(H,25,30)/b9-6+/t12-,13-,14-,15-,16-,17+,18+,19+,23+,24+/m1/s1

> <INCHI_KEY>
VDRRUDLAEDBVQI-MUOOTWISSA-N

> <FORMULA>
C24H33NO5

> <MOLECULAR_WEIGHT>
415.53

> <EXACT_MASS>
415.235873167

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.76340366477996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,3aS,5'S,5aS,7R,9aR,9bS)-2'-hydroxy-3-[(1E,3R)-3-hydroxybut-1-en-1-yl]-5'-[(1R)-1-hydroxyethyl]-7,9b-dimethyl-1,3,3a,4',5',5a,6,7,8,9,9a,9b-dodecahydrospiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione

> <JCHEM_LOGP>
3.417749604

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.740527227966908

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.38392039534327

> <JCHEM_PKA_STRONGEST_BASIC>
0.8840698735989827

> <JCHEM_POLAR_SURFACE_AREA>
107.19000000000001

> <JCHEM_REFRACTIVITY>
115.09209999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,3aS,5'S,5aS,7R,9aR,9bS)-2'-hydroxy-3-[(1E,3R)-3-hydroxybut-1-en-1-yl]-5'-[(1R)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'H-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       6.492   4.029   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.017   4.243   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.594   5.671   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.965   3.030   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.388   1.602   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   0.388   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.875   0.442   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.865   1.622   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.382   1.354   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.909  -0.093   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.425  -0.360   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.952  -1.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.469  -2.075   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.962  -2.987   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.445  -2.720   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.919  -1.273   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.402  -1.005   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.775  -2.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.189  -1.953   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.242  -3.492   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.912  -1.092   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.487  -2.572   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.435  -3.786   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.948  -2.626   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.087  -3.903   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.551  -3.795   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.762  -5.287   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0       6.422  -1.179   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       7.635  -0.231   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.581   1.308   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16    7   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    6   22   29                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24   29                                                       
CONECT   29   28   21   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₃NO₅

Average Mass

415.5300 Da

Monoisotopic Mass

415.23587 Da

IUPAC Name

(2R,3S,3aS,5'S,5aS,7R,9aR,9bS)-2'-hydroxy-3-[(1E,3R)-3-hydroxybut-1-en-1-yl]-5'-[(1R)-1-hydroxyethyl]-7,9b-dimethyl-1,3,3a,4',5',5a,6,7,8,9,9a,9b-dodecahydrospiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione

Traditional Name

(2R,3S,3aS,5'S,5aS,7R,9aR,9bS)-2'-hydroxy-3-[(1E,3R)-3-hydroxybut-1-en-1-yl]-5'-[(1R)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'H-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione

CAS Registry Number

Not Available

SMILES

C[C@@H](O)\C=C\[C@H]1[C@@H]2C=C[C@@H]3C[C@H](C)CC[C@H]3[C@]2(C)C(=O)[C@]11C(O)=N[C@@H]([C@@H](C)O)C1=O

InChI Identifier

InChI=1S/C24H33NO5/c1-12-5-8-16-15(11-12)7-10-17-18(9-6-13(2)26)24(21(29)23(16,17)4)20(28)19(14(3)27)25-22(24)30/h6-7,9-10,12-19,26-27H,5,8,11H2,1-4H3,(H,25,30)/b9-6+/t12-,13-,14-,15-,16-,17+,18+,19+,23+,24+/m1/s1

InChI Key

VDRRUDLAEDBVQI-MUOOTWISSA-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

Not Available

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

Seco-podocarpan diterpenoid
Diterpenoid
Cyclic carboximidic acid
Pyrroline
Secondary alcohol
Ketone
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	3.42	ChemAxon
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	107.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.09 m³·mol⁻¹	ChemAxon
Polarizability	45.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

34452007

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122395975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

O'Byrne LJ, Bodunde EO, Maher GM, Khashan AS, Greene RM, Browne JP, Mccarthy FP: Patient reported outcome measures evaluating postpartum maternal health and wellbeing: a systematic review and evaluation of measurement properties. Am J Obstet Gynecol MFM. 2022 Sep 7:100743. doi: 10.1016/j.ajogmf.2022.100743. [PubMed:36087713 ]
Panchal N, Desai C, Ghosal R: Fecal glucocorticoid metabolite levels in captive Indian leopards (Panthera pardus fusca) housed under three different enrichment regimes. PLoS One. 2022 Sep 9;17(9):e0261796. doi: 10.1371/journal.pone.0261796. eCollection 2022. [PubMed:36083970 ]
Yuksel S, Bonus M, Schwabe T, Pfleger C, Zimmer T, Enke U, Sass I, Gohlke H, Benndorf K, Kusch J: Uncoupling of Voltage- and Ligand-Induced Activation in HCN2 Channels by Glycine Inserts. Front Physiol. 2022 Aug 25;13:895324. doi: 10.3389/fphys.2022.895324. eCollection 2022. [PubMed:36091400 ]
Peter A, Balogh A, Csanadi Z, Danko K, Griger Z: Subclinical systolic and diastolic myocardial dysfunction in polyphasic polymyositis/dermatomyositis: a 2-year longitudinal study. Arthritis Res Ther. 2022 Sep 10;24(1):219. doi: 10.1186/s13075-022-02906-7. [PubMed:36088383 ]
Dagdigian PJ: Theoretical investigation of rotationally inelastic collisions of OH(X(2)Pi) with hydrogen atoms. J Chem Phys. 2022 Sep 14;157(10):104305. doi: 10.1063/5.0110724. [PubMed:36109246 ]
LOTUS database [Link]

Showing NP-Card for (2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione (NP0302164)

MOL for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

3D MOL for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

3D SDF for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

3D-SDF for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

PDB for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

3D PDB for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

SMILES for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

INCHI for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

Structure for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)

3D Structure for NP0302164 ((2r,3s,3as,5's,5as,7r,9ar,9bs)-2'-hydroxy-3-[(1e,3r)-3-hydroxybut-1-en-1-yl]-5'-[(1r)-1-hydroxyethyl]-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydro-5'h-spiro[cyclopenta[a]naphthalene-2,3'-pyrrole]-1,4'-dione)