ID: ALA3098771

Max Phase: Phase

Molecular Formula: C20H22O2

Molecular Weight: 294.39

Molecule Type: Small molecule

Representations

Synonyms (7): (9z)-uab-30 | Retinoid 9cuab30 | Uab-30 | Uab30 | 9-CIS-UAB30 | 9CUAB30 | UAB-30
Synonyms from Alternative Forms(7):

Canonical SMILES:  CC(=C/C=C/C(C)=C/C(=O)O)/C=C1\CCCc2ccccc21

Standard InChI:  InChI=1S/C20H22O2/c1-15(7-5-8-16(2)14-20(21)22)13-18-11-6-10-17-9-3-4-12-19(17)18/h3-5,7-9,12-14H,6,10-11H2,1-2H3,(H,21,22)/b8-5+,15-7-,16-14+,18-13+

Standard InChI Key:  PPGNMFUMZSAZCW-VOYUZAMQSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 294.39

Molecular Weight (Monoisotopic): 294.1620

AlogP: 4.94

#Rotatable Bonds: 4

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.54

CX Basic pKa:

CX LogP: 5.00

CX LogD: 2.22

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.63

Np Likeness Score: 1.02

References

1. Desphande A, Xia G, Boerma LJ, Vines KK, Atigadda VR, Lobo-Ruppert S, Grubbs CJ, Moeinpour FL, Smith CD, Christov K, Brouillette WJ, Muccio DD..  (2014)  Methyl-substituted conformationally constrained rexinoid agonists for the retinoid X receptors demonstrate improved efficacy for cancer therapy and prevention.,  22  (1): [PMID:24359708] [10.1016/j.bmc.2013.11.039]

2. Atigadda VR, Xia G, Desphande A, Boerma LJ, Lobo-Ruppert S, Grubbs CJ, Smith CD, Brouillette WJ, Muccio DD..  (2014)  Methyl substitution of a rexinoid agonist improves potency and reveals site of lipid toxicity.,  57  (12): [PMID:24801499] [10.1021/jm5004792]

3. Atigadda VR, Xia G, Deshpande A, Wu L, Kedishvili N, Smith CD, Krontiras H, Bland KI, Grubbs CJ, Brouillette WJ, Muccio DD..  (2015)  Conformationally Defined Rexinoids and Their Efficacy in the Prevention of Mammary Cancers.,  58  (19): [PMID:26331194] [10.1021/acs.jmedchem.5b00829]

4. Unpublished dataset, 

5. Atigadda VR, Kashyap MP, Yang Z, Chattopadhyay D, Melo N, Sinha R, Belyaeva OV, Chou CF, Chang PL, Kedishvili NY, Grubbs CJ, Renfrow MB, Muccio DD, Elmets CA, Athar M..  (2022)  Conformationally Defined Rexinoids for the Prevention of Inflammation and Nonmelanoma Skin Cancers.,  65  (21.0): [PMID:36318154] [10.1021/acs.jmedchem.2c00735]

6. Liang C, Qiao G, Liu Y, Tian L, Hui N, Li J, Ma Y, Li H, Zhao Q, Cao W, Liu H, Ren X..  (2021)  Overview of all-trans-retinoic acid (ATRA) and its analogues: Structures, activities, and mechanisms in acute promyelocytic leukaemia.,  220  [PMID:33895500] [10.1016/j.ejmech.2021.113451]

Source

Source(2):

• Scientific Literature
• Clinical Candidates