cinnamodial

ID: ALA373458

Chembl Id: CHEMBL373458

Cas Number: 23599-45-3

PubChem CID: 442354

Max Phase: Preclinical

Molecular Formula: C17H24O5

Molecular Weight: 308.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-277293 | Cinnamodial|23599-45-3|CHEBI:3711|CHEMBL373458|[(1R,4S,4aS,8aS)-3,4-diformyl-4-hydroxy-4a,8,8-trimethyl-5,6,7,8a-tetrahydro-1H-naphthalen-1-yl] acetate|NSC-277293|C09638|1,2-Naphthalenedicarboxaldehyde, 4-(acetyloxy)-1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-5,5,5a-trimethyl-, (1S-(1alpha,4beta,4aalpha,8abeta))-|AC1L9CNT|(-)-cinnamodial|SCHEMBL15557354|DTXSID10178249|Q27106174|1,2-Naphthalenedicarboxaldehyde, 4-(acetyloxy)-1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-5,5,8a-trimethyl-, (1S,4R,Show More⌵

Canonical SMILES:  CC(=O)O[C@@H]1C=C(C=O)[C@](O)(C=O)[C@@]2(C)CCCC(C)(C)[C@H]12

Standard InChI:  InChI=1S/C17H24O5/c1-11(20)22-13-8-12(9-18)17(21,10-19)16(4)7-5-6-15(2,3)14(13)16/h8-10,13-14,21H,5-7H2,1-4H3/t13-,14+,16+,17-/m1/s1

Standard InChI Key:  UKLMEFSRPRDOLD-YQFWSFKMSA-N

Alternative Forms

1. Parent:

   

   ALA373458

   CINNAMODIAL

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: 308.37

Molecular Weight (Monoisotopic): 308.1624

AlogP: 1.82

#Rotatable Bonds: 3

Polar Surface Area: 80.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.05

CX Basic pKa: ┄

CX LogP: 1.23

CX LogD: 1.23

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: 3.24

References

1. Harinantenaina L, Asakawa Y, De Clercq E..  (2007)  Cinnamacrins A-C, cinnafragrin D, and cytostatic metabolites with alpha-glucosidase inhibitory activity from Cinnamosma macrocarpa.,  70  (2): [PMID:17286431] [10.1021/np060435l]

2. Taniguchi M, Kubo I..  (1993)  Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.,  56  (9): [PMID:8254349] [10.1021/np50099a012]

3. Treyvaud Amiguet V, Petit P, Ta CA, Nuñez R, Sánchez-Vindas P, Alvarez LP, Smith ML, Arnason JT, Durst T..  (2006)  Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense.,  69  (7): [PMID:16872133] [10.1021/np0504863]

4. Mahmoud II, Kinghorn AD, Cordell GA, Farnsworth NR..  (1980)  Potential anticancer agents. XVI. Isolation of bicyclofarnesane sesquiterpenoids from Capsicodendron dinisii.,  43  (3): [PMID:7400822] [10.1021/np50009a008]

5. Karmahapatra S, Kientz C, Shetty S, Yalowich JC, Rakotondraibe LH..  (2018)  Capsicodendrin from Cinnamosma fragrans Exhibits Antiproliferative and Cytotoxic Activity in Human Leukemia Cells: Modulation by Glutathione.,  81  (3): [PMID:29406734] [10.1021/acs.jnatprod.7b00887]

Source

Source(1):

• Scientific Literature