NP-MRD: Showing NP-Card for (2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate (NP0258989)

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Record Information

Version

2.0

Created at

2022-09-08 00:42:15 UTC

Updated at

2022-09-08 00:42:15 UTC

NP-MRD ID

NP0258989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate

Description

(2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]Icosa-1(20),13,15(19)-trien-9-yl (3S)-3-hydroxybutanoate belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. (2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate is found in Clivia miniata and Clivia nobilis. Based on a literature review very few articles have been published on (2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]Icosa-1(20),13,15(19)-trien-9-yl (3S)-3-hydroxybutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082202422D          

 29 33  0  0  1  0            999 V2000
   -3.0875   -6.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8072   -5.9429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3390   -5.3122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9951   -5.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7148   -5.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466   -4.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9027   -4.8766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224   -4.1006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1542   -3.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739   -2.6940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2629   -1.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6913   -1.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0511   -1.7315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -2.5488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4701   -3.1795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2822   -3.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -2.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3746   -2.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9064   -2.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6261   -3.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -3.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -4.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655   -5.0716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7216   -4.5861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898   -3.9554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6706   -2.4330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6111   -1.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8101   -1.4124    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  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 13  1  1  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 26 25  1  1  0  0  0
  8 26  1  0  0  0  0
 16 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 19 29  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    6.3824    1.0379    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6310    1.6900    1.2140 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4760    1.8229    2.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    0.9492    1.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572    0.8638    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7642    1.3701   -0.6753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2310    0.2227    0.5729 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    0.1582   -0.5540 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1738   -1.2940   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048   -1.3287   -1.8884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2309   -2.6610   -2.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425   -3.3358   -1.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000   -2.4113   -0.7908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030   -2.9753    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619   -1.1400   -1.0566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0212   -0.2430    0.0959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2501    0.5376    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5164   -0.0017    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6670    0.7083    0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6057    1.9816    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3717    2.5384    1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2210    1.8331    0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9009    2.4522    1.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8272    3.6271    1.5629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1951    1.6698    0.8073 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0428    0.7855   -0.3128 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9085    2.4547    1.1559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8064    1.5416    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0118    0.3838    0.3681 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    1.3979   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2553   -0.0655    0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4645    1.2371    0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3871    2.7331    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8193    0.9458    2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9142    1.5375    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6931   -0.0448    1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440    0.6691   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813   -1.6628   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803   -1.8748   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -0.4937   -2.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946   -2.4968   -3.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019   -3.2789   -2.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -3.6399   -2.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283   -4.2748   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -2.3103    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5987   -3.4518    0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3233   -3.8432    0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808   -0.6019   -1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088   -0.7401    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064   -0.9911   -0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3146    3.5465    1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308    1.2912   -1.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2133    1.9242   -0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6383    1.2504    1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  2  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 29  1  0
 29 28  1  0
 28 27  1  0
 19 18  1  0
 18 17  2  0
 26  8  1  0
 17 22  1  0
 15 10  1  0
 17 16  1  0
 27 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  4 35  1  0
  4 36  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  6
 16 49  1  1
 26 52  1  6
 21 51  1  0
 28 53  1  0
 28 54  1  0
 18 50  1  0
M  END


  Mrv1652309082202422D          

 29 33  0  0  1  0            999 V2000
   -3.0875   -6.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8072   -5.9429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3390   -5.3122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9951   -5.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7148   -5.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466   -4.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9027   -4.8766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224   -4.1006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1542   -3.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739   -2.6940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2629   -1.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6913   -1.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0511   -1.7315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -2.5488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4701   -3.1795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2822   -3.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -2.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3746   -2.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9064   -2.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6261   -3.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -3.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -4.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655   -5.0716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7216   -4.5861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898   -3.9554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6706   -2.4330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6111   -1.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8101   -1.4124    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  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 13  1  1  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 26 25  1  1  0  0  0
  8 26  1  0  0  0  0
 16 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 19 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)CC(=O)O[C@H]1C[C@H]2CCN(C)[C@H]2[C@H]2[C@H]1OC(=O)C1=CC3=C(OCO3)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO7/c1-10(23)5-17(24)28-16-6-11-3-4-22(2)19(11)18-12-7-14-15(27-9-26-14)8-13(12)21(25)29-20(16)18/h7-8,10-11,16,18-20,23H,3-6,9H2,1-2H3/t10-,11+,16-,18-,19+,20-/m0/s1

> <INCHI_KEY>
QYVZOJWDWWFSQK-CEQGWQHPSA-N

> <FORMULA>
C21H25NO7

> <MOLECULAR_WEIGHT>
403.431

> <EXACT_MASS>
403.163102149

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.332674994238346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{15,19}]icosa-1(20),13,15(19)-trien-9-yl (3S)-3-hydroxybutanoate

> <JCHEM_LOGP>
1.182343958333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.407214828097857

> <JCHEM_PKA_STRONGEST_BASIC>
8.997507186044148

> <JCHEM_POLAR_SURFACE_AREA>
94.53000000000002

> <JCHEM_REFRACTIVITY>
100.7439

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{15,19}]icosa-1(20),13,15(19)-trien-9-yl (3S)-3-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.763 -12.542   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.240 -11.093   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.233  -9.916   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.724 -10.822   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.201  -9.374   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.194  -8.197   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.685  -9.103   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.162  -7.655   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.154  -6.477   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.631  -5.029   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.358  -3.671   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.290  -2.560   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.095  -3.232   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.453  -2.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.115  -4.758   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.877  -5.935   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.393  -5.664   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.917  -4.216   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.433  -3.945   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.425  -5.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.902  -6.570   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.386  -6.841   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.863  -8.290   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.856  -9.467   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.347  -8.561   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.354  -7.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.852  -4.542   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.741  -3.006   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.246  -2.637   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    8   16                                                  
CONECT   27   20   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   19                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,7R,9S,10R)-4-Methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0,.0,.0,]icosa-1(20),13,15(19)-trien-9-yl (3S)-3-hydroxybutanoic acid	Generator

Chemical Formula

C₂₁H₂₅NO₇

Average Mass

403.4310 Da

Monoisotopic Mass

403.16310 Da

IUPAC Name

(2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{15,19}]icosa-1(20),13,15(19)-trien-9-yl (3S)-3-hydroxybutanoate

Traditional Name

(2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{15,19}]icosa-1(20),13,15(19)-trien-9-yl (3S)-3-hydroxybutanoate

CAS Registry Number

Not Available

SMILES

C[C@H](O)CC(=O)O[C@H]1C[C@H]2CCN(C)[C@H]2[C@H]2[C@H]1OC(=O)C1=CC3=C(OCO3)C=C21

InChI Identifier

InChI=1S/C21H25NO7/c1-10(23)5-17(24)28-16-6-11-3-4-22(2)19(11)18-12-7-14-15(27-9-26-14)8-13(12)21(25)29-20(16)18/h7-8,10-11,16,18-20,23H,3-6,9H2,1-2H3/t10-,11+,16-,18-,19+,20-/m0/s1

InChI Key

QYVZOJWDWWFSQK-CEQGWQHPSA-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
Clivia miniata	LOTUS Database	35616633
Clivia nobilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Homolycorine-type amaryllidaceae alkaloids

Direct Parent

Homolycorine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Homolycorine skeleton
Benzopyran
Isochromane
2-benzopyran
Indole or derivatives
Benzodioxole
Beta-hydroxy acid
Fatty acid ester
Aralkylamine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Benzenoid
Hydroxy acid
Fatty acyl
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Lactone
Carboxylic acid ester
Amino acid or derivatives
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.18	ChemAxon
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.74 m³·mol⁻¹	ChemAxon
Polarizability	41.33 Å³	ChemAxon
Number of Rings	5	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

163022269

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate (NP0258989)

MOL for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

3D MOL for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

3D SDF for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

3D-SDF for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

PDB for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

3D PDB for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

SMILES for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

INCHI for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

Structure for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)

3D Structure for NP0258989 ((2s,3r,7r,9s,10r)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl (3s)-3-hydroxybutanoate)