NP-MRD: Showing NP-Card for 5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one (NP0210010)

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Record Information

Version

2.0

Created at

2022-09-05 07:39:11 UTC

Updated at

2022-09-05 07:39:11 UTC

NP-MRD ID

NP0210010

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one

Description

Mangicol E belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Based on a literature review very few articles have been published on Mangicol E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052209392D          

 29 32  0  0  1  0            999 V2000
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1563    0.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3396   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5691   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5191   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0040   -2.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8245   -2.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -3.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1534   -4.2076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8480   -3.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618   -2.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342   -4.4469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0275   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6920   -4.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1841   -2.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3636   -2.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -1.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7790   -1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 12  1  1  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -5.3725    0.6425   -1.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5781    0.5782    0.0568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8014   -0.6828    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4079   -1.0281    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5194   -0.6092    0.1444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1209    0.6885   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834    1.6753   -0.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9157    1.5979   -0.7814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6481    1.8152   -2.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3467    2.8130   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4032    2.1447    1.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9771    0.8809    0.4995 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3541    0.0287    1.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    0.9833   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257    1.4190   -0.1206 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3394    2.7444    0.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    0.6351    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0304    1.1569    1.4717 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491   -0.7077    0.2397 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3500   -0.7908   -1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1762   -0.9097    0.9249 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0488   -1.8664    0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940   -1.9472    1.9065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2620    0.3756   -0.2488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0891   -0.5649    0.5281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6080   -1.9858    0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956   -2.7019   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6837   -1.6544   -0.9030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4115   -1.1799   -2.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657    1.5077   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4291    0.9035   -1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2681   -0.2515   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    1.4262    0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2579   -1.4901    0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4957   -0.5200    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863   -2.0932    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -0.3515    2.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265    2.6557   -0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1499    0.8906   -2.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889    1.9046   -2.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0676    2.7235   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1304    3.4866    0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2940    3.4274   -0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    2.7807    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3783    1.8231    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -1.0363    1.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4079    0.3382    1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7849    0.2863    2.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    0.0142   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7324    1.6797   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085    1.6800   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2393    3.1324    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2551   -1.8410   -1.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3585   -0.3891   -1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488   -0.1769   -1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9855   -1.1957    1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0920   -1.8847    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5791   -2.8090    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8313   -2.8652    2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278   -0.1828   -1.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653   -0.3732    1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -2.5397    1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -1.9866   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1493   -3.5293    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3334   -3.1870   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0188   -1.8270   -3.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
  5 28  1  0
 28 29  1  0
 28 27  1  0
 27 26  1  0
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 25 24  1  0
 24 12  1  0
 12 13  1  1
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 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  1
 19 22  1  0
 22 23  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  6
  8  7  1  0
  7  6  2  0
  6  2  1  0
 25  5  1  0
  8 24  1  0
  6  5  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
 28 66  1  6
 29 67  1  0
 29 68  1  0
 29 69  1  0
 27 64  1  0
 27 65  1  0
 26 62  1  0
 26 63  1  0
 25 61  1  1
 24 60  1  6
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
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 16 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 11 44  1  0
 11 45  1  0
 10 42  1  0
 10 43  1  0
  9 39  1  0
  9 40  1  0
  9 41  1  0
  7 38  1  0
M  END


  Mrv1652309052209392D          

 29 32  0  0  1  0            999 V2000
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1563    0.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3396   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5691   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5191   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0040   -2.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8245   -2.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -3.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1534   -4.2076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8480   -3.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618   -2.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342   -4.4469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0275   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6920   -4.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1841   -2.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3636   -2.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -1.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7790   -1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
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 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
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 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 12  1  1  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0210010

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@]23[C@@H](C)CC[C@H]2[C@@H]2[C@@](C)(CC(O)C(=O)C(C)(O)CO)CC[C@]2(C)C=C13

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O4/c1-15-8-9-25-16(2)6-7-17(25)20-22(3,12-18(15)25)10-11-23(20,4)13-19(27)21(28)24(5,29)14-26/h12,15-17,19-20,26-27,29H,6-11,13-14H2,1-5H3/t15-,16-,17-,19?,20-,22+,23+,24?,25-/m0/s1

> <INCHI_KEY>
WCMVXSJCZKPSHR-NLLTUSTDSA-N

> <FORMULA>
C25H40O4

> <MOLECULAR_WEIGHT>
404.591

> <EXACT_MASS>
404.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
46.295843510943186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,4-trihydroxy-2-methyl-5-[(1S,2S,5S,6R,7R,10R,13S)-2,7,10,13-tetramethyltetracyclo[10.3.0.0^{1,5}.0^{6,10}]pentadec-11-en-7-yl]pentan-3-one

> <JCHEM_LOGP>
3.565482208999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.439167948902941

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.380904227149415

> <JCHEM_PKA_STRONGEST_BASIC>
-3.139314051258153

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
115.03029999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,2,4-trihydroxy-2-methyl-5-[(1S,2S,5S,6R,7R,10R,13S)-2,7,10,13-tetramethyltetracyclo[10.3.0.0^{1,5}.0^{6,10}]pentadec-11-en-7-yl]pentan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.025   0.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.329  -0.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.234  -1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.329  -2.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.662  -3.319   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.702  -3.956   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.608  -5.201   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.139  -5.040   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.981  -6.608   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.886  -7.854   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.450  -6.769   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.289  -5.238   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.611  -8.301   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.918  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.292  -8.337   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.210  -4.349   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.679  -4.510   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.052  -3.103   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.454  -2.783   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25   28                                             
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   24                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   24                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22                                                            
CONECT   24   12    8   25                                                  
CONECT   25   24    5   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    5   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀O₄

Average Mass

404.5910 Da

Monoisotopic Mass

404.29266 Da

IUPAC Name

1,2,4-trihydroxy-2-methyl-5-[(1S,2S,5S,6R,7R,10R,13S)-2,7,10,13-tetramethyltetracyclo[10.3.0.0^{1,5}.0^{6,10}]pentadec-11-en-7-yl]pentan-3-one

Traditional Name

1,2,4-trihydroxy-2-methyl-5-[(1S,2S,5S,6R,7R,10R,13S)-2,7,10,13-tetramethyltetracyclo[10.3.0.0^{1,5}.0^{6,10}]pentadec-11-en-7-yl]pentan-3-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@]23[C@@H](C)CC[C@H]2[C@@H]2[C@@](C)(CC(O)C(=O)C(C)(O)CO)CC[C@]2(C)C=C13

InChI Identifier

InChI=1S/C25H40O4/c1-15-8-9-25-16(2)6-7-17(25)20-22(3,12-18(15)25)10-11-23(20,4)13-19(27)21(28)24(5,29)14-26/h12,15-17,19-20,26-27,29H,6-11,13-14H2,1-5H3/t15-,16-,17-,19?,20-,22+,23+,24?,25-/m0/s1

InChI Key

WCMVXSJCZKPSHR-NLLTUSTDSA-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 iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

11-noriridane monoterpenoid
Fatty alcohol
Acyloin
Beta-hydroxy ketone
Monosaccharide
Fatty acyl
Alpha-hydroxy ketone
Tertiary alcohol
Ketone
1,2-diol
Secondary alcohol
Polyol
Primary alcohol
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.57	ChemAxon
pKa (Strongest Acidic)	12.38	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.03 m³·mol⁻¹	ChemAxon
Polarizability	46.3 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

8962736

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10787423

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one (NP0210010)

MOL for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

3D MOL for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

3D SDF for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

3D-SDF for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

PDB for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

3D PDB for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

SMILES for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

INCHI for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

Structure for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)

3D Structure for NP0210010 (5-[(3s,3as,6s,7ar,10r,10ar,10bs)-3,6,7a,10-tetramethyl-1h,2h,3h,4h,5h,6h,8h,9h,10ah,10bh-cyclopenta[d]s-indacen-10-yl]-1,2,4-trihydroxy-2-methylpentan-3-one)