NP-MRD: Showing NP-Card for (1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate (NP0154759)

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Record Information

Version

2.0

Created at

2022-09-02 11:43:13 UTC

Updated at

2022-09-02 11:43:13 UTC

NP-MRD ID

NP0154759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate

Description

Paniculamine belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. (1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate was first documented in 2016 (PMID: 27525345). Based on a literature review very few articles have been published on Paniculamine (PMID: 28858498).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213432D          

 28 33  0  0  1  0            999 V2000
    6.6137    1.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8249    1.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6401    0.6766    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.8673    0.9653    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.4776    0.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873   -0.2312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4568    0.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0868   -0.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6971   -1.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8481   -1.7312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5086   -2.4831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749   -1.0767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2381   -0.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3748   -0.0413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9858   -0.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8883   -0.5457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7822   -0.6841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1586   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2814   -1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0965   -1.9685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9411   -2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109   -1.3270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3891   -1.5119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9539   -2.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806   -1.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -1.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147   -0.7691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3702   -0.0741    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  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
  6 16  1  0  0  0  0
 12 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 17 22  1  0  0  0  0
 12 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  CHG  2   3   1   4  -1
M  END

     RDKit          3D

 63 68  0  0  0  0  0  0  0  0999 V2000
   -3.6520    2.4994    1.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694    2.2256    0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.7797    0.6168 N   0  0  1  0  0  4  0  0  0  0  0  0
   -2.9247    0.1989    1.6779 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9795    0.5420   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4365   -0.6456   -1.3245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8519   -0.5421   -2.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842   -1.8789   -0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9888   -2.7765   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9321   -2.0757    0.7503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3606   -1.8926    2.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -0.8455    0.1570 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9672   -0.5625   -1.2605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4142    0.8523   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554    1.3201   -0.0619 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9096    0.4436    0.7686 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3328    0.7007    0.3772 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5109    0.6086    1.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9703    0.1972    2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -0.8001    1.0154 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9850   -1.5890    0.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559   -0.7520   -0.0525 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6811    0.1371   -0.0876 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7651    0.8601    0.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2200   -0.4954   -1.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6985    0.4778   -2.1903 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5840    1.1611   -0.2782 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5082    1.4397   -1.6104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537    2.3341    1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    1.7776    2.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767    3.5116    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5376    2.5733    1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3998    2.8138   -0.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1235    1.4389   -1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0450    0.2590   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5087   -1.4026   -3.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -0.5204   -3.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4243    0.3835   -2.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7729   -1.6517    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5330   -2.4600   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349   -3.4524    0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5374   -3.4768   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0878   -2.8208    0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1190   -2.6682    2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5167   -1.2789   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    0.7834   -2.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1802    1.5533   -1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743    2.3696    0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802    0.6177    1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400    1.5184    2.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9950   -0.3001    2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6337    1.0592    2.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0807   -0.2838    3.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754   -1.4863    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537   -2.4230    0.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548   -2.0799    1.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3816   -0.7548   -1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8921    1.6833   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1572   -1.0546   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5965   -1.1651   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1381    0.5117   -3.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305    2.1499    0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2406    2.3530   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  1
  3  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 10  1  1
 12 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 17 18  1  1
 17 15  1  0
 15 14  1  0
 14 13  1  0
 15 16  1  0
 17 27  1  0
 27 28  1  0
 27 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 16  3  1  0
 13  6  1  0
 13 12  1  0
 16 12  1  0
 17 22  1  0
 23 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  1
 11 44  1  0
 22 57  1  6
 21 55  1  0
 21 56  1  0
 20 54  1  1
 19 52  1  0
 19 53  1  0
 18 50  1  0
 18 51  1  0
 15 48  1  6
 14 46  1  0
 14 47  1  0
 13 45  1  6
 16 49  1  1
 27 62  1  1
 28 63  1  0
 24 58  1  0
 25 59  1  0
 25 60  1  0
 26 61  1  0
M  CHG  2   3   1   4  -1
M  END


  Mrv1652309022213432D          

 28 33  0  0  1  0            999 V2000
    6.6137    1.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8249    1.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6401    0.6766    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.8673    0.9653    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.4776    0.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873   -0.2312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4568    0.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0868   -0.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6971   -1.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8481   -1.7312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5086   -2.4831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749   -1.0767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2381   -0.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3748   -0.0413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9858   -0.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8883   -0.5457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7822   -0.6841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1586   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2814   -1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0965   -1.9685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9411   -2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109   -1.3270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3891   -1.5119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9539   -2.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806   -1.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -1.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147   -0.7691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3702   -0.0741    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  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
  6 16  1  0  0  0  0
 12 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 17 22  1  0  0  0  0
 12 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  CHG  2   3   1   4  -1
M  END
> <DATABASE_ID>
NP0154759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[N+]1([O-])C[C@]2(C)CC[C@H](O)[C@@]34[C@@H]5C[C@@H]6CC[C@@]5([C@@H](C[C@H]23)C14)[C@H](O)[C@]6(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C22H35NO5/c1-3-23(28)10-19(2)6-5-16(25)22-14(19)9-13(17(22)23)20-7-4-12(8-15(20)22)21(27,11-24)18(20)26/h12-18,24-27H,3-11H2,1-2H3/t12-,13-,14+,15+,16-,17?,18-,19-,20-,21-,22-,23?/m0/s1

> <INCHI_KEY>
FAABWRZXAULJAP-PETNMGKNSA-N

> <FORMULA>
C22H35NO5

> <MOLECULAR_WEIGHT>
393.524

> <EXACT_MASS>
393.251523231

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
42.84542839321882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,9R,10R,11S,12R,13S,15R,16R)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecan-7-ium-7-olate

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-1.1432880200000008

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.069382321088366

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.772115288367559

> <JCHEM_PKA_STRONGEST_BASIC>
3.723137130499033

> <JCHEM_POLAR_SURFACE_AREA>
103.98

> <JCHEM_REFRACTIVITY>
103.4353

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,9R,10R,11S,12R,13S,15R,16R)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecan-7-ium-7-olate

> <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      12.346   3.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.873   2.764   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      10.528   1.263   0.000  0.00  0.00           N+1
HETATM    4  O   UNK     0       9.086   1.802   0.000  0.00  0.00           O-1
HETATM    5  C   UNK     0      12.092   1.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.483  -0.432   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.919   0.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.229  -1.830   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.501  -3.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.917  -3.232   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.283  -4.635   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.847  -2.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.778  -0.148   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.166  -0.077   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.307  -1.074   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.991  -1.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.060  -1.277   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.896  -0.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.125  -2.133   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.780  -3.675   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.357  -3.830   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.234  -2.477   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.460  -2.822   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.647  -4.131   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.137  -2.033   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.792  -2.784   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.254  -1.436   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.424  -0.138   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   13                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8   16                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16   22                                             
CONECT   13   12    3   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    6   12                                                  
CONECT   17   14   18   22   27                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17   12                                                  
CONECT   23   20   24   25   27                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   23   17   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₅NO₅

Average Mass

393.5240 Da

Monoisotopic Mass

393.25152 Da

IUPAC Name

(1R,2S,5R,9R,10R,11S,12R,13S,15R,16R)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecan-7-ium-7-olate

Traditional Name

(1R,2S,5R,9R,10R,11S,12R,13S,15R,16R)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecan-7-ium-7-olate

CAS Registry Number

Not Available

SMILES

CC[N+]1([O-])C[C@]2(C)CC[C@H](O)[C@@]34[C@@H]5C[C@@H]6CC[C@@]5([C@@H](C[C@H]23)C14)[C@H](O)[C@]6(O)CO

InChI Identifier

InChI=1S/C22H35NO5/c1-3-23(28)10-19(2)6-5-16(25)22-14(19)9-13(17(22)23)20-7-4-12(8-15(20)22)21(27,11-24)18(20)26/h12-18,24-27H,3-11H2,1-2H3/t12-,13-,14+,15+,16-,17?,18-,19-,20-,21-,22-,23?/m0/s1

InChI Key

FAABWRZXAULJAP-PETNMGKNSA-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 atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Azepane
Piperidine
Trialkyl amine oxide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Polyol
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Primary alcohol
Organooxygen compound
Organonitrogen compound
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	-0.2	ALOGPS
logP	-1.1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.77	ChemAxon
pKa (Strongest Basic)	3.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.44 m³·mol⁻¹	ChemAxon
Polarizability	42.85 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00024945

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

132525567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kou KGM, Kulyk S, Marth CJ, Lee JC, Doering NA, Li BX, Gallego GM, Lebold TP, Sarpong R: A Unifying Synthesis Approach to the C(18)-, C(19)-, and C(20)-Diterpenoid Alkaloids. J Am Chem Soc. 2017 Oct 4;139(39):13882-13896. doi: 10.1021/jacs.7b07706. Epub 2017 Sep 20. [PubMed:28858498 ]
Kou KG, Li BX, Lee JC, Gallego GM, Lebold TP, DiPasquale AG, Sarpong R: Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine, N-Ethyl-1alpha-hydroxy-17-veratroyldictyzine, and Paniculamine. J Am Chem Soc. 2016 Aug 31;138(34):10830-3. doi: 10.1021/jacs.6b07268. Epub 2016 Aug 22. [PubMed:27525345 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate (NP0154759)

MOL for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

3D MOL for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

3D SDF for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

3D-SDF for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

PDB for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

3D PDB for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

SMILES for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

INCHI for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

Structure for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)

3D Structure for NP0154759 ((1r,2s,5r,9r,10r,11s,12r,13s,15r,16r)-7-ethyl-2,11,12-trihydroxy-12-(hydroxymethyl)-5-methyl-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecan-7-ium-7-olate)