(+)-Tazettine

ID: ALA457605

Cas Number: 507-79-9

PubChem CID: 5321780

Max Phase: Preclinical

Molecular Formula: C18H21NO5

Molecular Weight: 331.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-Tazettine | Tazettine|Sekisanolin|Sekisanoline|Ungernine|(+)-Tazettine|Sekisanin|UNII-76WEU12CSO|76WEU12CSO|Tazetine|Tazettin|Ungernin|507-79-9|CHEBI:32185|NSC 652297|Sekisanine|NSC 115495|(1S,13S,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|NSC-115495|NSC-652297|TACETTINE|TAZETTINE [MI]|CHEMBL457605|SCHEMBL5792215|DTXSID10878333|8H-(1,3)DIOXOLO(6,7)(2)BENZOPYRANO(3,4-C)INDOL-6A(3H)-OL, 4,4A,5,6-TETRAHYDRO-3-METHOXY-5-MEShow More⌵

Canonical SMILES:  CO[C@@H]1C=C[C@@]23c4cc5c(cc4CO[C@]2(O)CN(C)[C@H]3C1)OCO5

Standard InChI:  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

Standard InChI Key:  YLWAQARRNQVEHD-PBZHRCKQSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   -0.7654   -2.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0550   -1.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0609   -0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7757   -0.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4861   -0.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4818   -1.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1957   -3.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1977   -2.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9087   -3.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9073   -2.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954   -2.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1840   -2.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976   -3.5804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795   -2.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805   -3.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -3.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0399   -3.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390   -2.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7700   -1.6546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7838   -2.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3486   -1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5271   -1.0679    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409   -3.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7806    0.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685    0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 14 15  1  0
  9  7  1  0
  7 15  2  0
  1  2  1  0
 14  8  2  0
  1 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  1  1  0
  8 10  1  0
  2 19  1  0
  9 10  2  0
 18 20  1  0
 20 19  1  0
  1  6  1  6
 19 21  1  0
  2  3  1  0
  2 22  1  1
  3  4  1  0
 18 23  1  6
  4  5  1  0
  4 24  1  1
  5  6  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA457605

   TAZETTINE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 331.37

Molecular Weight (Monoisotopic): 331.1420

AlogP: 1.16

#Rotatable Bonds: 1

Polar Surface Area: 60.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.09

CX Basic pKa: 7.56

CX LogP: 1.28

CX LogD: 0.89

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 2.38

References

1. Antoun MD, Mendoza NT, Ríos YR, Proctor GR, Wickramaratne DB, Pezzuto JM, Kinghorn AD..  (1993)  Cytotoxicity of Hymenocallis expansa alkaloids.,  56  (8): [PMID:8229020] [10.1021/np50098a030]

2. Kaur K, Jain M, Kaur T, Jain R..  (2009)  Antimalarials from nature.,  17  (9): [PMID:19299148] [10.1016/j.bmc.2009.02.050]

3. Van Goietsenoven G, Andolfi A, Lallemand B, Cimmino A, Lamoral-Theys D, Gras T, Abou-Donia A, Dubois J, Lefranc F, Mathieu V, Kornienko A, Kiss R, Evidente A..  (2010)  Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.,  73  (7): [PMID:20550100] [10.1021/np9008255]

4. McNulty J, Nair JJ, Little JR, Brennan JD, Bastida J..  (2010)  Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids.,  20  (17): [PMID:20655219] [10.1016/j.bmcl.2010.06.130]

5. Luo Z, Wang F, Zhang J, Li X, Zhang M, Hao X, Xue Y, Li Y, Horgen FD, Yao G, Zhang Y..  (2012)  Cytotoxic alkaloids from the whole plants of Zephyranthes candida.,  75  (12): [PMID:23190013] [10.1021/np3005425]

6. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

7. Liu Y,He S,Chen Y,Liu Y,Feng F,Liu W,Guo Q,Zhao L,Sun H.  (2020)  Overview of AKR1C3: Inhibitor Achievements and Disease Insights.,  63  (20.0): [PMID:32463235] [10.1021/acs.jmedchem.9b02138]

Source

Source(1):

• Scientific Literature