NP-MRD: Showing NP-Card for (1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate (NP0308463)

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Record Information

Version

2.0

Created at

2022-09-11 02:14:27 UTC

Updated at

2022-09-11 02:14:27 UTC

NP-MRD ID

NP0308463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate

Description

(1R,5R,8R,9S,10S,11S,14S,16R,17R,18S)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-10-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. (1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate is found in Delphinium nuttallianum. Based on a literature review very few articles have been published on (1R,5R,8R,9S,10S,11S,14S,16R,17R,18S)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112204142D          

 28 34  0  0  1  0            999 V2000
   -1.1906    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    0.6350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9611    1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940    0.6205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2838    1.2844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176   -0.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0434   -0.6807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4083   -1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3560    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4804    0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733    0.1461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0890   -0.6085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2832   -0.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6437   -0.9351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6973   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -2.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -3.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -1.8511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301   -0.4517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7342   -0.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.1655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7582   -0.6559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -0.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006   -1.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23  2  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 25  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  1  0  0  0
 16 27  1  6  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
M  END

     RDKit          3D

 55 61  0  0  0  0  0  0  0  0999 V2000
    3.6812   -2.8366    1.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6089   -2.1732    0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5686   -2.7398   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5635   -1.6406   -0.2556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4435   -2.0165   -1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4028   -0.9023   -1.5484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3332   -1.2728   -2.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443   -0.3911   -0.2483 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8054    0.7819   -0.8219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0270    0.3079   -1.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347    1.7762    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286    1.8623    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558    2.6108    2.2727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698    1.1143    1.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8219    0.0958    0.4664 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0436    0.5934   -0.6791 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2360   -0.3523   -0.7482 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3664    0.0908    0.1106 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2651    1.4500    0.4255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565    2.3333    0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732    3.7836    0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2432    1.8794   -0.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4063   -0.7849    1.3531 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0033   -0.7136    1.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -1.1249    1.0178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9938   -1.9964    1.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7210    0.3531   -1.9034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298    1.3189   -1.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279   -3.8457    0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4236   -2.3969    1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497   -3.5326    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9444   -3.0636   -0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -2.2383   -2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0114   -2.8796   -0.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5374   -2.2320   -2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -1.1291    0.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2504   -0.7317   -1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9352    0.9028   -1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9328    0.4209   -2.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2295    1.4275    0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259    2.7590   -0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2384    1.8641    1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1034    0.6278    2.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3406    1.6366   -0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5512   -0.5421   -1.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243   -0.1026   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1217    4.1107    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    3.9249    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7853    4.3189   -0.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1288   -0.4555    2.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367   -1.4255    2.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    0.3317    2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749   -2.9596    1.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2542    1.5298   -2.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172    2.2731   -1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  2  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 27  1  0
 27 28  1  0
 28  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 15 14  1  1
 15  8  1  0
  8  6  1  0
  6  7  1  6
  6  5  1  0
  4  5  1  6
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 23 18  1  0
  4 17  1  0
 25  4  1  0
 15 16  1  0
 25 15  1  0
  6 27  1  0
  8  9  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 18 46  1  6
 17 45  1  6
 16 44  1  1
 28 54  1  0
 28 55  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
  8 36  1  1
  7 35  1  0
  5 33  1  0
  5 34  1  0
  3 31  1  0
  3 32  1  0
  1 29  1  0
  1 30  1  0
 23 50  1  1
 24 51  1  0
 24 52  1  0
 26 53  1  0
M  END


  Mrv1652309112204142D          

 28 34  0  0  1  0            999 V2000
   -1.1906    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    0.6350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9611    1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940    0.6205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2838    1.2844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176   -0.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0434   -0.6807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4083   -1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3560    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4804    0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733    0.1461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0890   -0.6085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2832   -0.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6437   -0.9351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6973   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -2.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -3.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -1.8511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301   -0.4517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7342   -0.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.1655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7582   -0.6559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -0.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006   -1.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23  2  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 25  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  1  0  0  0
 16 27  1  6  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@@H]2[C@H]3N4C[C@]5(C)CC(=O)C[C@@]33[C@@H]5[C@]4(O)C[C@@]22CC(=C)[C@@H]1C[C@@]32O

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO5/c1-10-4-19-8-21(26)17-18(3)5-12(25)6-20(17)16(23(21)9-18)14(19)15(28-11(2)24)13(10)7-22(19,20)27/h13-17,26-27H,1,4-9H2,2-3H3/t13-,14+,15-,16+,17+,18-,19-,20-,21+,22-/m0/s1

> <INCHI_KEY>
VOFHPANLWJZICP-ZASRTIFCSA-N

> <FORMULA>
C22H27NO5

> <MOLECULAR_WEIGHT>
385.46

> <EXACT_MASS>
385.188922973

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.6955060568514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,8R,9S,10S,11S,14S,16R,17R,18S)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-10-yl acetate

> <JCHEM_LOGP>
-0.5430588556666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.950198880101265

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.89393407446461

> <JCHEM_PKA_STRONGEST_BASIC>
7.177022013357135

> <JCHEM_POLAR_SURFACE_AREA>
87.07

> <JCHEM_REFRACTIVITY>
98.09529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,8R,9S,10S,11S,14S,16R,17R,18S)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.223   0.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.718   0.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.494   1.597   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.091   1.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.661   1.913   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.216   1.158   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.130   2.398   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.379  -0.088   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.548  -1.271   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.229  -2.652   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.002  -0.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.131   0.747   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.007   2.014   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.497   1.091   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.803   0.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.900  -1.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.395  -0.629   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.202  -1.746   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.302  -3.282   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.021  -4.137   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.120  -5.674   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.360  -3.455   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.056  -0.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.370  -0.066   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.138   0.309   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.282  -1.224   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0       5.329  -0.655   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       6.161  -2.019   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17   25                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8   27                                             
CONECT    7    6                                                            
CONECT    8    6    9   15                                                  
CONECT    9    8   10   11   28                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8   16   25                                             
CONECT   16   15   17   27                                                  
CONECT   17   16    4   18                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18    2   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    4   15   26                                             
CONECT   26   25                                                            
CONECT   27   16    6   28                                                  
CONECT   28   27    9                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   68    0
END

View in JSmol

Synonyms

Value	Source
(1R,5R,8R,9S,10S,11S,14S,16R,17R,18S)-16,18-Dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-10-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₇NO₅

Average Mass

385.4600 Da

Monoisotopic Mass

385.18892 Da

IUPAC Name

(1R,5R,8R,9S,10S,11S,14S,16R,17R,18S)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-10-yl acetate

Traditional Name

(1R,5R,8R,9S,10S,11S,14S,16R,17R,18S)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@@H]2[C@H]3N4C[C@]5(C)CC(=O)C[C@@]33[C@@H]5[C@]4(O)C[C@@]22CC(=C)[C@@H]1C[C@@]32O

InChI Identifier

InChI=1S/C22H27NO5/c1-10-4-19-8-21(26)17-18(3)5-12(25)6-20(17)16(23(21)9-18)14(19)15(28-11(2)24)13(10)7-22(19,20)27/h13-17,26-27H,1,4-9H2,2-3H3/t13-,14+,15-,16+,17+,18-,19-,20-,21+,22-/m0/s1

InChI Key

VOFHPANLWJZICP-ZASRTIFCSA-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
Delphinium nuttallianum	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
Isoindolone
Indole or derivatives
Indolizidine
Alkaloid or derivatives
Isoindoline
Isoindole or derivatives
Azepane
N-alkylpyrrolidine
Piperidine
Cyclic alcohol
Tertiary alcohol
Pyrrolidine
Carboxylic acid ester
Hemiaminal
Cyclic ketone
Ketone
Alkanolamine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Organonitrogen 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	-0.54	ChemAxon
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	7.18	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.1 m³·mol⁻¹	ChemAxon
Polarizability	43.7 Å³	ChemAxon
Number of Rings	7	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

139053726

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate (NP0308463)

MOL for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

3D MOL for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

3D SDF for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

3D-SDF for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

PDB for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

3D PDB for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

SMILES for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

INCHI for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

Structure for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)

3D Structure for NP0308463 ((1r,5r,8r,9s,10s,11s,14s,16r,17r,18s)-16,18-dihydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl acetate)