azadiradione

ID: ALA1215754

Chembl Id: CHEMBL1215754

Cas Number: 26241-51-0

PubChem CID: 12308714

Max Phase: Preclinical

Molecular Formula: C28H34O5

Molecular Weight: 450.58

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Azadiradione | Azadiradione|26241-51-0|CHEBI:67280|Azadiradione (~90%)|CHEMBL1215754|BDBM92410|HY-N9615|AKOS040763659|AT40289|Q27135739|(5alpha,7alpha,13alpha,17alpha)-17-(furan-3-yl)-4,4,8-trimethyl-3,16-dioxoandrosta-1,14-dien-7-yl acetate|[(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate|24-Nor-5alpha,13alpha,17alpha-chola-1,14,20,22-tetraene-3,16-dione, 21,23-epoxy-7alpha-hydroxy-4,4,8-trimethyl-,aShow More⌵

Canonical SMILES:  CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@]3(C)C(=CC(=O)[C@H]3c3ccoc3)[C@@]21C

Standard InChI:  InChI=1S/C28H34O5/c1-16(29)33-23-14-20-25(2,3)22(31)8-11-26(20,4)19-7-10-27(5)21(28(19,23)6)13-18(30)24(27)17-9-12-32-15-17/h8-9,11-13,15,19-20,23-24H,7,10,14H2,1-6H3/t19-,20+,23-,24-,26-,27-,28-/m1/s1

Standard InChI Key:  KWAMDQVQFVBEAU-HMWIRDDCSA-N

Alternative Forms

1. Parent:

   

   ALA1215754

   AZADIRADIONE

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: 450.58

Molecular Weight (Monoisotopic): 450.2406

AlogP: 5.42

#Rotatable Bonds: 2

Polar Surface Area: 73.58

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.84

CX LogD: 4.84

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.56

Np Likeness Score: 3.34

References

1. Chianese G, Yerbanga SR, Lucantoni L, Habluetzel A, Basilico N, Taramelli D, Fattorusso E, Taglialatela-Scafati O..  (2010)  Antiplasmodial triterpenoids from the fruits of neem, Azadirachta indica.,  73  (8): [PMID:20669933] [10.1021/np100325q]

2. Kikuchi T, Ishii K, Noto T, Takahashi A, Tabata K, Suzuki T, Akihisa T..  (2011)  Cytotoxic and apoptosis-inducing activities of limonoids from the seeds of Azadirachta indica (neem).,  74  (4): [PMID:21381696] [10.1021/np100783k]

3. García A, Bocanegra-García V, Palma-Nicolás JP, Rivera G..  (2012)  Recent advances in antitubercular natural products.,  49  [PMID:22280816] [10.1016/j.ejmech.2011.12.029]

4. Fernandez-Mateos A, Pascual Coca G, Perez Alonso J, Rubio Gonzalez R, Simmonds M, Blaney W.  (1998)  Diastereoselective synthesis of the model insect antifeedants related to azadiradione and epoxyazadiradione based on intramolecular insertion of -aryl--diazoketones,  54  (49): [10.1016/S0040-4020(98)00939-9]

5. Govindachari T, Suresh G, Gopalakrishnan G, Masilamani S, Banumathi B.  (2000)  Antifungal activity of some tetranortriterpenoids,  71  (4): [10.1016/S0367-326X(99)00155-0]

6. Ishida M, Serit M, Nakata K, Raj Juneja L, Kim M, Takahashi S.  (1992)  Several Antifeedants from Neem Oil,Azadirachta indicaA. Juss., againstReticulitermes speratusKolbe (Isoptera: Rhinotermitidae),  56  (11): [10.1271/bbb.56.1835]

7. Suresh G, Gopalakrishnan G, Wesley SD, Pradeep Singh ND, Malathi R, Rajan SS..  (2002)  Insect antifeedant activity of tetranortriterpenoids from the Rutales. A perusal of structural relations.,  50  (16): [PMID:12137465] [10.1021/jf025534t]

Source

Source(1):

• Scientific Literature