NP-MRD: Showing NP-Card for 9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate (NP0197482)

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Record Information

Version

2.0

Created at

2022-09-04 15:45:33 UTC

Updated at

2022-09-04 15:45:33 UTC

NP-MRD ID

NP0197482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate

Description

9,10,19-Trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl acetate 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. 9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate is found in Aconitum coreanum. 9,10,19-Trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251514052D          

 28 34  0  0  0  0            999 V2000
    8.8504    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6024    1.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1599    1.3767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970    1.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5491    1.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0635    0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6131   -0.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2541   -0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0026   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3084   -0.4492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1576    0.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754    1.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613    0.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4407    1.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -0.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341    0.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3806    1.0517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1626    0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0169    0.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7291    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8747    0.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4788   -0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798   -0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7313   -1.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8061   -1.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 21 23  1  0  0  0  0
  7 23  1  0  0  0  0
 11 23  1  0  0  0  0
 21 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 57 63  0  0  0  0  0  0  0  0999 V2000
    5.0254    1.3471    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8307    0.8221   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5986   -0.6376   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1144   -0.8274    0.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6967   -2.2518    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2358   -2.3744    0.4280 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5862   -1.6682   -0.6621 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9648   -1.8292   -0.0828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4494   -3.2184   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9350   -0.8024   -0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822    0.5613   -0.2783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2745    1.5945   -0.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8533    2.4935    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7798    3.5737   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679    2.3751    1.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0576    0.7074   -0.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823   -0.2453   -0.4431 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2919   -0.1892   -1.0462 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8201    1.1728   -1.2995 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7790    1.0541   -2.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361    1.6968   -0.1021 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8690    1.4235    1.1829 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7371    2.2130    1.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -0.0446    1.2605 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9656   -0.6175    2.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849   -0.2222    1.0463 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2374   -1.5468    1.5472 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871   -1.7695    1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9381    0.7283    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2111    2.4125    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1047   -1.2122    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720   -1.0606   -1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2234   -2.7877    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313   -2.7806   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -3.4067    0.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4293   -2.0579   -1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629   -3.2037   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887   -3.6987   -1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -3.8914    0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620   -0.9095    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870   -0.9912   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2970    0.6703    0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2043    4.5408   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2410    3.3330   -1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5132    3.6988    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510    0.4406   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881    1.7617   -0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590   -0.8471   -1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117    1.9213   -1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301    0.3611   -2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489    2.7515   -0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518    1.7199    2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521    2.8654    0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2489    0.0695    3.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999    0.5887    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8944   -2.7714    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2787   -1.0350    1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  1
  8 28  1  0
 28 27  1  0
 27  6  1  0
  6  5  1  0
  4  5  1  1
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 21  1  0
 21 19  1  0
 19 20  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  6
 17  7  1  0
 17 26  1  0
 26 24  1  0
 24 25  1  1
 24 22  1  0
 22 23  1  0
 16 11  1  0
  7  8  1  0
 26 27  1  0
  7  6  1  0
 18  4  1  0
 24  4  1  0
 22 21  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 11 42  1  1
 10 40  1  0
 10 41  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 28 56  1  0
 28 57  1  0
  6 35  1  1
  5 33  1  0
  5 34  1  0
  3 31  1  0
  3 32  1  0
  1 29  1  0
  1 30  1  0
 21 51  1  6
 19 49  1  6
 20 50  1  0
 18 48  1  6
 16 46  1  0
 16 47  1  0
  7 36  1  6
 26 55  1  1
 25 54  1  0
 22 52  1  1
 23 53  1  0
M  END


  Mrv1533004251514052D          

 28 34  0  0  0  0            999 V2000
    8.8504    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6024    1.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1599    1.3767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970    1.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5491    1.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0635    0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6131   -0.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2541   -0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0026   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3084   -0.4492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1576    0.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754    1.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613    0.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4407    1.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -0.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341    0.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3806    1.0517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1626    0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0169    0.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7291    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8747    0.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4788   -0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798   -0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7313   -1.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8061   -1.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 21 23  1  0  0  0  0
  7 23  1  0  0  0  0
 11 23  1  0  0  0  0
 21 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2(C)CN3C4CC56CC(=C)C7C(O)C5C(C1)(C24)C3C6(O)C7O

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO5/c1-9-4-20-7-12-15-19(3)5-11(28-10(2)24)6-21(15)16(20)14(25)13(9)17(26)22(20,27)18(21)23(12)8-19/h11-18,25-27H,1,4-8H2,2-3H3

> <INCHI_KEY>
XGTNTUKODZZCGL-UHFFFAOYSA-N

> <FORMULA>
C22H29NO5

> <MOLECULAR_WEIGHT>
387.476

> <EXACT_MASS>
387.204573038

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.26849159064349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate

> <ALOGPS_LOGP>
-0.30

> <JCHEM_LOGP>
-1.136819563666667

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.18485503640676

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.813620703346462

> <JCHEM_PKA_STRONGEST_BASIC>
8.782874708833907

> <JCHEM_POLAR_SURFACE_AREA>
90.23

> <JCHEM_REFRACTIVITY>
98.698

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      16.521   5.174   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.058   3.705   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      17.098   2.570   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.554   3.371   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.092   1.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.052   0.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.211  -0.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.408  -1.664   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.072  -1.793   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      11.776  -0.839   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.494   1.006   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.221   2.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.701   1.433   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.335   2.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.987   1.496   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.556   2.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.404  -0.034   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.904   0.448   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.177   1.963   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.637   0.380   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.232   0.128   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.561   1.420   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.833   0.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.227  -1.126   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.736  -0.424   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.832  -1.961   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.372  -1.288   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.105  -2.805   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   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20   25                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21    5                                                       
CONECT   23   21    7   11                                                  
CONECT   24   21   10   25                                                  
CONECT   25   24   13   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   17   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   68    0
END

View in JSmol

Synonyms

Value	Source
9,10,19-Trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-3-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₉NO₅

Average Mass

387.4760 Da

Monoisotopic Mass

387.20457 Da

IUPAC Name

9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate

Traditional Name

9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2(C)CN3C4CC56CC(=C)C7C(O)C5C(C1)(C24)C3C6(O)C7O

InChI Identifier

InChI=1S/C22H29NO5/c1-9-4-20-7-12-15-19(3)5-11(28-10(2)24)6-21(15)16(20)14(25)13(9)17(26)22(20,27)18(21)23(12)8-19/h11-18,25-27H,1,4-8H2,2-3H3

InChI Key

XGTNTUKODZZCGL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum coreanum	LOTUS Database	35616633

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
Azaspirodecane
Quinolizidine
Isoindole or derivatives
Isoindoline
Indolizidine
Alkaloid or derivatives
Indole or derivatives
Azepane
Piperidine
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Tertiary alcohol
Amino acid or derivatives
Tertiary aliphatic amine
1,2-aminoalcohol
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
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	-0.3	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.7 m³·mol⁻¹	ChemAxon
Polarizability	41.27 Å³	ChemAxon
Number of Rings	7	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

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

3101182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate (NP0197482)

MOL for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

3D MOL for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

3D SDF for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

3D-SDF for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

PDB for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

3D PDB for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

SMILES for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

INCHI for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

Structure for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)

3D Structure for NP0197482 (9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl acetate)