ID: ALA1545045

Max Phase: Preclinical

Molecular Formula: C15H22O2

Molecular Weight: 234.34

Molecule Type: Small molecule

Representations

Synonyms (1): Valerenic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC1=C2[C@H](/C=C(\C)C(=O)O)CC[C@@H](C)[C@H]2CC1

Standard InChI:  InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+/t9-,12+,13-/m1/s1

Standard InChI Key:  FEBNTWHYQKGEIQ-SUKRRCERSA-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 234.34

Molecular Weight (Monoisotopic): 234.1620

AlogP: 3.79

#Rotatable Bonds: 2

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: 4.85

CX Basic pKa:

CX LogP: 3.60

CX LogD: 1.09

Aromatic Rings: 0

Heavy Atoms: 17

QED Weighted: 0.58

Np Likeness Score: 2.55

References

1. PubChem BioAssay data set, 

2. Zaugg J, Eickmeier E, Ebrahimi SN, Baburin I, Hering S, Hamburger M..  (2011)  Positive GABA(A) receptor modulators from Acorus calamus and structural analysis of (+)-dioxosarcoguaiacol by 1D and 2D NMR and molecular modeling.,  74  (6): [PMID:21563811] [10.1021/np200181d]

3. PubChem BioAssay data set, 

4. Egbewande FA, Nilsson N, White JM, Coster MJ, Davis RA..  (2017)  The design, synthesis, and anti-inflammatory evaluation of a drug-like library based on the natural product valerenic acid.,  27  (14): [PMID:28558967] [10.1016/j.bmcl.2017.05.021]

5. Moradi-Afrapoli F, Ebrahimi SN, Smiesko M, Hamburger M..  (2017)  HPLC-Based Activity Profiling for GABAA Receptor Modulators in Extracts: Validation of an Approach Utilizing a Larval Zebrafish Locomotor Assay.,  80  (5): [PMID:28485933] [10.1021/acs.jnatprod.7b00081]

6. Merk D, Grisoni F, Friedrich L, Gelzinyte E, Schneider G..  (2018)  Computer-Assisted Discovery of Retinoid X Receptor Modulating Natural Products and Isofunctional Mimetics.,  61  (12): [PMID:29901398] [10.1021/acs.jmedchem.8b00494]

7. Stadler M, Monticelli S, Seidel T, Luger D, Salzer I, Boehm S, Holzer W, Schwarzer C, Urban E, Khom S, Langer T, Pace V, Hering S..  (2018)  Design, Synthesis, and Pharmacological Evaluation of Novel β2/3 Subunit-Selective γ-Aminobutyric Acid Type A (GABA_A) Receptor Modulators.,  62  (1): [PMID:30289721] [10.1021/acs.jmedchem.8b00859]

8. Syafni N, Faleschini MT, Garifulina A, Danton O, Gupta MP, Hering S, Hamburger M..  (2022)  Clerodane Diterpenes from Casearia corymbosa as Allosteric GABA_A Receptor Modulators.,  85  (5.0): [PMID:35475609] [10.1021/acs.jnatprod.1c00840]

9. Willems S, Zaienne D, Merk D..  (2021)  Targeting Nuclear Receptors in Neurodegeneration and Neuroinflammation.,  64  (14.0): [PMID:34251209] [10.1021/acs.jmedchem.1c00186]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays