ID: ALA375927

Max Phase: Preclinical

Molecular Formula: C20H26O4

Molecular Weight: 330.42

Molecule Type: Small molecule

Representations

Synonyms (1): (-)-Dihydroguaiareticacid
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(C[C@@H](C)[C@H](C)Cc2ccc(O)c(OC)c2)ccc1O

Standard InChI:  InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14-/m1/s1

Standard InChI Key:  ADFOLUXMYYCTRR-ZIAGYGMSSA-N

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

Properties

Molecular Weight: 330.42

Molecular Weight (Monoisotopic): 330.1831

AlogP: 4.17

#Rotatable Bonds: 7

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.97

CX Basic pKa:

CX LogP: 5.05

CX LogD: 5.05

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: 0.57

References

1. Davis RA, Carroll AR, Duffy S, Avery VM, Guymer GP, Forster PI, Quinn RJ..  (2007)  Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum.,  70  (7): [PMID:17583952] [10.1021/np070073x]

2. Davis RA, Barnes EC, Longden J, Avery VM, Healy PC..  (2009)  Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum.,  17  (3): [PMID:19138858] [10.1016/j.bmc.2008.12.030]

3. Davis RA, Innocenti A, Poulsen SA, Supuran CT..  (2010)  Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.,  18  (1): [PMID:19962903] [10.1016/j.bmc.2009.11.021]

4. Davis RA, Hofmann A, Osman A, Hall RA, Mühlschlegel FA, Vullo D, Innocenti A, Supuran CT, Poulsen SA..  (2011)  Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.,  54  (6): [PMID:21332115] [10.1021/jm1013242]

5. Tsai WJ, Shen CC, Tsai TH, Lin LC..  (2014)  Lignans from the aerial parts of Saururus chinensis: isolation, structural characterization, and their effects on platelet aggregation.,  77  (1): [PMID:24387347] [10.1021/np400772h]

6. Yamauchi S, Tanimura R, Nishiwaki H, Nishi K, Sugahara T, Maruyama M, Ano Y, Akiyama K, Kishida T..  (2016)  Enantioselective syntheses of both enantiomers of 9'-dehydroxyimperanene and 7,8-dihydro-9'-dehydroxyimperanene and the comparison of biological activity between 9-norlignans and dihydroguaiaretic acids.,  26  (13): [PMID:27210431] [10.1016/j.bmcl.2016.05.020]

7. Reyes-Melo K, García A, Romo-Mancillas A, Garza-González E, Rivas-Galindo VM, Miranda LD, Vargas-Villarreal J, Favela-Hernández JMJ, Camacho-Corona MDR..  (2017)  meso-Dihydroguaiaretic acid derivatives with antibacterial and antimycobacterial activity.,  25  (20): [PMID:28844400] [10.1016/j.bmc.2017.07.047]

8. Yamauchi S, Wukirsari T, Ochi Y, Nishiwaki H, Nishi K, Sugahara T, Akiyama K, Kishida T..  (2017)  Syntheses of cytotoxic novel arctigenin derivatives bearing halogen and alkyl groups on aromatic rings.,  27  (17): [PMID:28754364] [10.1016/j.bmcl.2017.06.070]

9. Vuorinen A, Engeli RT, Leugger S, Bachmann F, Akram M, Atanasov AG, Waltenberger B, Temml V, Stuppner H, Krenn L, Ateba SB, Njamen D, Davis RA, Odermatt A, Schuster D..  (2017)  Potential Antiosteoporotic Natural Product Lead Compounds That Inhibit 17β-Hydroxysteroid Dehydrogenase Type 2.,  80  (4): [PMID:28319389] [10.1021/acs.jnatprod.6b00950]

10. Liu Y, Yu HY, Wang YM, Tian T, Wu WM, Zhou M, Meng XG, Ruan HL..  (2017)  Neuroprotective Lignans from the Fruits of Schisandra bicolor var. tuberculata.,  80  (4): [PMID:28333453] [10.1021/acs.jnatprod.7b00035]

Source

Source(1):

• Scientific Literature