NP-MRD: Showing NP-Card for (1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol (NP0196395)

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Record Information

Version

2.0

Created at

2022-09-04 14:28:48 UTC

Updated at

2022-09-04 14:28:48 UTC

NP-MRD ID

NP0196395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol

Description

(1S,13R,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]Icosa-2,4(8),9,19-tetraen-13-ol, also known as sekisanin, belongs to the class of organic compounds known as tazettine-type amaryllidaceae alkaloids. (1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol is found in Brunsvigia gregaria, Crinum amabile, Crinum jagus, Cyrtanthus falcatus, Cyrtanthus obliquus, Eucharis amazonica, Hippeastrum puniceum, Hymenocallis littoralis, Hymenocallis rotata, Lapiedra martinezii, Narcissus asturiensis, Narcissus cantabricus, Narcissus confusus, Narcissus tazetta, Pancratium canariense, Pancratium maritimum, Pancratium trianthum, Sprekelia formosissima, Sternbergia clusiana, Sternbergia sicula and Zephyranthes candida. These are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework (1S,13R,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]Icosa-2,4(8),9,19-tetraen-13-ol is a very strong basic compound (based on its pKa) (1S,13R,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]Icosa-2,4(8),9,19-tetraen-13-ol is a potentially toxic compound.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291401042D          

 26 30  0  0  1  0            999 V2000
   -0.5727    1.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748    3.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4995    1.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432    0.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414   -0.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    0.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7654    0.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3335   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829    1.7768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0740    0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305    0.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495    1.0552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2661    0.3431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7176   -0.2731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0436    0.8791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4913    2.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.1529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770   -1.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664    2.4889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745    1.0599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
 11  5  2  0  0  0  0
 11  8  1  0  0  0  0
 12  3  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  2  0  0  0  0
 16  6  1  0  0  0  0
 17  4  1  0  0  0  0
 17 13  1  6  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  0  0  0  0
 19 16  1  0  0  0  0
 18 20  1  6  0  0  0
 21  2  1  0  0  0  0
 12 21  1  6  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
 24  8  1  0  0  0  0
 24 18  1  0  0  0  0
 12 25  1  1  0  0  0
 16 26  1  6  0  0  0
M  END

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
   -1.8992    3.9048    0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    2.7116    0.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160    1.6296    0.5907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2683    0.9778    1.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978   -0.0667    1.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -0.6198    0.2439 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1251   -0.2918   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221    0.7397   -0.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7545    1.0004   -1.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7731    0.2031   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4286   -0.8331    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122   -1.0953    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573   -2.2264    1.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4827   -2.4562    1.4802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1518   -2.1733    0.3224 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4585   -2.6326   -0.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123   -2.4827    0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9148   -1.7041   -0.9423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2772   -1.6837   -1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934   -0.4017   -0.7699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3135    0.6404   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    0.7204   -1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6810    2.0440   -1.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3043    1.9634   -2.1366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3305    4.7586   -0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959    3.7973   -0.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220    4.1127    1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960    2.0473    0.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4618    1.4052    2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430   -0.5132    2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    1.3355   -1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346   -1.4355    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -3.1459    0.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -2.1197    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187   -3.4299   -1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1773   -2.0575    1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8420   -3.5321    0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -0.8270   -1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -2.6152   -1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8883   -1.8094   -0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -0.1907   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307    1.2098   -1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264    0.1016   -0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    2.2519   -2.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442    2.7880   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
 21  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  6  5  1  1
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
  6 20  1  0
 15  6  1  0
 18 20  1  0
 12  7  1  0
 24  9  1  0
 20 41  1  6
 21 42  1  0
 21 43  1  0
  3 28  1  1
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
 23 44  1  0
 23 45  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END


  Mrv0541 08291401042D          

 26 30  0  0  1  0            999 V2000
   -0.5727    1.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748    3.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4995    1.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432    0.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414   -0.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    0.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7654    0.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3335   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829    1.7768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0740    0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305    0.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495    1.0552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2661    0.3431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7176   -0.2731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0436    0.8791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4913    2.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.1529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770   -1.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664    2.4889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745    1.0599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
 11  5  2  0  0  0  0
 11  8  1  0  0  0  0
 12  3  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  2  0  0  0  0
 16  6  1  0  0  0  0
 17  4  1  0  0  0  0
 17 13  1  6  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  0  0  0  0
 19 16  1  0  0  0  0
 18 20  1  6  0  0  0
 21  2  1  0  0  0  0
 12 21  1  6  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
 24  8  1  0  0  0  0
 24 18  1  0  0  0  0
 12 25  1  1  0  0  0
 16 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0196395

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@]([H])(OC)C=C[C@]11C3=CC4=C(OCO4)C=C3CO[C@@]1(O)CN2C

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO5/c1-19-9-18(20)17(4-3-12(21-2)6-16(17)19)13-7-15-14(22-10-23-15)5-11(13)8-24-18/h3-5,7,12,16,20H,6,8-10H2,1-2H3/t12-,16+,17+,18+/m1/s1

> <INCHI_KEY>
YLWAQARRNQVEHD-IEGACIPQSA-N

> <FORMULA>
C18H21NO5

> <MOLECULAR_WEIGHT>
331.363

> <EXACT_MASS>
331.141972787

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.74381687929405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13R,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
1.2791916213333336

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.086838077509851

> <JCHEM_PKA_STRONGEST_BASIC>
7.557602653536734

> <JCHEM_POLAR_SURFACE_AREA>
60.390000000000015

> <JCHEM_REFRACTIVITY>
87.32260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tazettin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      -1.069   2.665   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.873   5.984   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.666   1.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.627   0.986   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.864  -1.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.348   3.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.895   1.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.332  -2.283   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.071   0.109   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.895   1.182   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.356  -1.133   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.888   3.317   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.872   0.329   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.888  -0.294   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.404   1.168   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.586   1.970   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.363   0.641   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.339  -0.510   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.081   1.641   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       0.201  -1.547   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.650   4.655   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.428  -0.285   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.644   2.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.824  -1.972   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       3.111   4.646   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.126   1.979   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   21                                                            
CONECT    3    4   12                                                       
CONECT    4    3   17                                                       
CONECT    5   11   14                                                       
CONECT    6   12   16                                                       
CONECT    7   13   15                                                       
CONECT    8   11   24                                                       
CONECT    9   18   19                                                       
CONECT   10   22   23                                                       
CONECT   11    5    8   13                                                  
CONECT   12    3    6   21   25                                             
CONECT   13    7   11   17                                                  
CONECT   14    5   15   22                                                  
CONECT   15    7   14   23                                                  
CONECT   16    6   17   19   26                                             
CONECT   17    4   13   16   18                                             
CONECT   18    9   17   20   24                                             
CONECT   19    1    9   16                                                  
CONECT   20   18                                                            
CONECT   21    2   12                                                       
CONECT   22   10   14                                                       
CONECT   23   10   15                                                       
CONECT   24    8   18                                                       
CONECT   25   12                                                            
CONECT   26   16                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
Sekisanin	Kegg

Chemical Formula

C₁₈H₂₁NO₅

Average Mass

331.3630 Da

Monoisotopic Mass

331.14197 Da

IUPAC Name

(1S,13R,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol

Traditional Name

tazettin

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@]([H])(OC)C=C[C@]11C3=CC4=C(OCO4)C=C3CO[C@@]1(O)CN2C

InChI Identifier

InChI=1S/C18H21NO5/c1-19-9-18(20)17(4-3-12(21-2)6-16(17)19)13-7-15-14(22-10-23-15)5-11(13)8-24-18/h3-5,7,12,16,20H,6,8-10H2,1-2H3/t12-,16+,17+,18+/m1/s1

InChI Key

YLWAQARRNQVEHD-IEGACIPQSA-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
Brunsvigia gregaria	LOTUS Database	35616633
Crinum amabile	LOTUS Database	35616633
Crinum jagus	LOTUS Database	35616633
Cyrtanthus falcatus	LOTUS Database	35616633
Cyrtanthus obliquus	LOTUS Database	35616633
Eucharis amazonica	LOTUS Database	35616633
Hippeastrum puniceum	LOTUS Database	35616633
Hymenocallis littoralis	LOTUS Database	35616633
Hymenocallis rotata	LOTUS Database	35616633
Lapiedra martinezii	LOTUS Database	35616633
Narcissus asturiensis	LOTUS Database	35616633
Narcissus cantabricus	LOTUS Database	35616633
Narcissus confusus	LOTUS Database	35616633
Narcissus tazetta	LOTUS Database	35616633
Pancratium canariense	LOTUS Database	35616633
Pancratium maritimum	LOTUS Database	35616633
Pancratium trianthum	LOTUS Database	35616633
Sprekelia formosissima	LOTUS Database	35616633
Sternbergia clusiana	LOTUS Database	35616633
Sternbergia sicula	LOTUS Database	35616633
Zephyranthes candida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tazettine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Tazettine-type amaryllidaceae alkaloids

Direct Parent

Tazettine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Tazettine alkaloid skeleton
Benzopyran
Isochromane
2-benzopyran
Benzodioxole
Indole or derivatives
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Hemiacetal
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Acetal
Ether
Dialkyl ether
Azacycle
Organoheterocyclic compound
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Indole alkaloids (C12179 )
Isoquinoline alkaloids (C12179 )

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	0.48	ALOGPS
logP	1.28	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	7.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.32 m³·mol⁻¹	ChemAxon
Polarizability	34.74 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

C00024438

Chemspider ID

Not Available

KEGG Compound ID

C12179

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol (NP0196395)

MOL for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

3D MOL for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

3D SDF for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

3D-SDF for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

PDB for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

3D PDB for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

SMILES for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

INCHI for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

Structure for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)

3D Structure for NP0196395 ((1s,13r,16s,18s)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-13-ol)