NP-MRD: Showing NP-Card for Lepedine (NP0067213)

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Record Information

Version

2.0

Created at

2022-04-28 11:37:13 UTC

Updated at

2022-04-28 11:37:14 UTC

NP-MRD ID

NP0067213

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lepedine

Description

(1R,2S,5R,8R,9R,10S,11R,13R,14S,15R,16R)-7-ethyl-2-methoxy-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]Nonadecane-11,14-diol 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. Lepedine is found in Aconitum pseudohuilense and Aconitum pseudohuiliense. Based on a literature review very few articles have been published on (1R,2S,5R,8R,9R,10S,11R,13R,14S,15R,16R)-7-ethyl-2-methoxy-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]Nonadecane-11,14-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213372D          

 27 32  0  0  1  0            999 V2000
    7.3921    1.1327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8095    0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4341   -0.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888   -0.4301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0076    0.2243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1411   -0.0518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5274    0.6150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1023    1.2561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7266    0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6233    0.7632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9612    1.2358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2934    2.0343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1301    1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8722    2.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2759    3.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550    0.5589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1321   -0.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3367   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698   -0.6167    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7028   -0.7979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0336   -1.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188    0.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9262    1.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    1.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2742   -1.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7773   -1.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1485    1.4620    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
  1 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  1  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  6  0  0  0
 16 24  1  1  0  0  0
  4 25  1  6  0  0  0
 25 26  1  0  0  0  0
  1 27  1  1  0  0  0
M  END

     RDKit          3D

 62 67  0  0  0  0  0  0  0  0999 V2000
    4.2915   -0.8804   -2.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5300   -0.5229   -1.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3420   -1.4462    0.1098 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6162   -0.5668    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    0.5364    1.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045    0.6085    0.0190 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8586    0.8146   -1.0663 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3184    0.8928   -2.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6907    1.5462    0.1024 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1155    1.6772   -1.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962    0.3420   -1.3755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2929    0.4944   -1.2918 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7185    1.3459   -2.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8777   -0.8636   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.7097   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1366   -1.6050    0.2179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2647   -1.6407    1.6153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587   -2.8323    2.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3144   -0.4766   -0.1659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3462    0.6828    0.8513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6143    1.2728    0.9623 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202    2.4117    1.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191    2.2948    2.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6165    1.1020    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -0.6798   -0.3973 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8430   -1.7891    0.2948 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6367   -3.0454   -0.2516 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052   -1.8384   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4670   -0.2387   -2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -2.3129    0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900   -1.2481    2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492   -0.2103    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    0.5224    2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1843    1.4954    1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465    1.6417   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9491    1.3691   -2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.4906    0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848    2.0927   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299    2.4224   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4472   -0.1486   -2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.8098   -3.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419    2.3383   -2.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8133    1.3775   -2.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9987   -0.7305   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264   -1.2934   -2.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2710   -1.4950    0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -2.7624   -0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488   -2.5849   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671   -2.7330    3.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8191   -3.5324    1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0268   -3.2975    1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020    0.3121    1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7384    2.5442    2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7697    3.3406    1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3016    1.3124    2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5790    3.0798    2.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5181    2.4467    3.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814    2.1106   -0.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4711    0.5283    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -0.9022   -1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6068   -1.8064    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -3.0638   -1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 24  1  0
 24 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 16  1  1
 19 11  1  0
 11 10  1  0
 10  9  1  0
  9 20  1  0
  9  6  1  0
  6  5  1  1
  5  4  1  0
  4  3  1  0
  3 26  1  0
 26 27  1  0
 26 25  1  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
 20 21  1  0
 25  6  1  0
 11 12  1  0
  7  6  1  0
 20 19  1  0
 25 19  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 22 53  1  0
 22 54  1  0
 24 58  1  0
 24 59  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  6
 18 49  1  0
 18 50  1  0
 18 51  1  0
 11 40  1  6
 10 38  1  0
 10 39  1  0
  9 37  1  1
 20 52  1  1
  5 33  1  0
  5 34  1  0
  4 31  1  0
  4 32  1  0
  3 30  1  6
 26 61  1  1
 27 62  1  0
 25 60  1  6
  1 28  1  0
  1 29  1  0
  7 35  1  1
  8 36  1  0
M  END


  Mrv1652304282213372D          

 27 32  0  0  1  0            999 V2000
    7.3921    1.1327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8095    0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4341   -0.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888   -0.4301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0076    0.2243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1411   -0.0518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5274    0.6150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1023    1.2561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7266    0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6233    0.7632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9612    1.2358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2934    2.0343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1301    1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8722    2.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2759    3.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550    0.5589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1321   -0.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3367   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698   -0.6167    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7028   -0.7979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0336   -1.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188    0.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9262    1.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    1.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2742   -1.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7773   -1.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1485    1.4620    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
  1 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  1  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  6  0  0  0
 16 24  1  1  0  0  0
  4 25  1  6  0  0  0
 25 26  1  0  0  0  0
  1 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067213

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C)CC[C@H](OC)[C@@]34[C@@H]2C[C@@H]([C@@H]13)[C@@]12CC[C@@H]([C@H](O)[C@@H]41)C(=C)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C23H35NO3/c1-5-24-11-21(3)8-7-16(27-4)23-15(21)10-14(19(23)24)22-9-6-13(12(2)20(22)26)17(25)18(22)23/h13-20,25-26H,2,5-11H2,1,3-4H3/t13-,14+,15-,16+,17+,18-,19-,20-,21+,22+,23-/m1/s1

> <INCHI_KEY>
XXZZJNAAUWXZNM-HKJMZRRTSA-N

> <FORMULA>
C23H35NO3

> <MOLECULAR_WEIGHT>
373.537

> <EXACT_MASS>
373.261693991

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.84737489546996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5R,8R,9R,10S,11R,13R,14S,15R,16R)-7-ethyl-2-methoxy-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecane-11,14-diol

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.251966520666668

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.719808155322738

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.993079366326686

> <JCHEM_PKA_STRONGEST_BASIC>
10.08147570820557

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
104.36280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,8R,9R,10S,11R,13R,14S,15R,16R)-7-ethyl-2-methoxy-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecane-11,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.799   2.114   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.578   0.720   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.877  -0.705   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.299  -0.803   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.214   0.419   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597  -0.097   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.451   1.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.524   2.345   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.690   1.366   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.363   1.425   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.128   2.307   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      11.748   3.797   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      13.309   3.633   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.961   5.122   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.715   6.465   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.636   1.043   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.847  -0.360   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.362  -0.769   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.224  -1.151   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.778  -1.489   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.396  -2.900   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.502   0.389   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.329   2.101   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.821   2.350   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      11.712  -2.226   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.651  -3.447   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.211   2.729   0.000  0.00  0.00           C+0
CONECT    1    2   10   13   27                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6   10   11                                             
CONECT    6    5    7   20                                                  
CONECT    7    6    8   16   23                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1    5                                                  
CONECT   11    8    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    1                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    7   17   24                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   22                                                  
CONECT   20   19    6   21                                                  
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22    7                                                       
CONECT   24   16                                                            
CONECT   25    4   26                                                       
CONECT   26   25                                                            
CONECT   27    1                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₅NO₃

Average Mass

373.5370 Da

Monoisotopic Mass

373.26169 Da

IUPAC Name

(1R,2S,5R,8R,9R,10S,11R,13R,14S,15R,16R)-7-ethyl-2-methoxy-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecane-11,14-diol

Traditional Name

(1R,2S,5R,8R,9R,10S,11R,13R,14S,15R,16R)-7-ethyl-2-methoxy-5-methyl-12-methylidene-7-azahexacyclo[7.6.2.2^{10,13}.0^{1,8}.0^{5,16}.0^{10,15}]nonadecane-11,14-diol

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(C)CC[C@H](OC)[C@@]34[C@@H]2C[C@@H]([C@@H]13)[C@@]12CC[C@@H]([C@H](O)[C@@H]41)C(=C)[C@H]2O

InChI Identifier

InChI=1S/C23H35NO3/c1-5-24-11-21(3)8-7-16(27-4)23-15(21)10-14(19(23)24)22-9-6-13(12(2)20(22)26)17(25)18(22)23/h13-20,25-26H,2,5-11H2,1,3-4H3/t13-,14+,15-,16+,17+,18-,19-,20-,21+,22+,23-/m1/s1

InChI Key

XXZZJNAAUWXZNM-HKJMZRRTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aconitum pseudohuilense	Plant	KNApSAcK
Aconitum pseudohuiliense	Plant	KNApSAcK

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
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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	1.8	ALOGPS
logP	1.25	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.99	ChemAxon
pKa (Strongest Basic)	10.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.36 m³·mol⁻¹	ChemAxon
Polarizability	42.85 Å³	ChemAxon
Number of Rings	6	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

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

162834738

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lepedine (NP0067213)

MOL for NP0067213 (Lepedine)

3D MOL for NP0067213 (Lepedine)

3D SDF for NP0067213 (Lepedine)

3D-SDF for NP0067213 (Lepedine)

PDB for NP0067213 (Lepedine)

3D PDB for NP0067213 (Lepedine)

SMILES for NP0067213 (Lepedine)

INCHI for NP0067213 (Lepedine)

Structure for NP0067213 (Lepedine)

3D Structure for NP0067213 (Lepedine)