ID: ALA1934131

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Small molecule

Representations

Synonyms (1): Sphaeropsidin B
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C[C@]1(C)C=C2[C@@H](O)[C@@]3(O)OC(=O)[C@@]4(CCCC(C)(C)[C@H]34)[C@@]2(O)CC1

Standard InChI:  InChI=1S/C20H28O5/c1-5-17(4)9-10-19(23)12(11-17)13(21)20(24)14-16(2,3)7-6-8-18(14,19)15(22)25-20/h5,11,13-14,21,23-24H,1,6-10H2,2-4H3/t13-,14+,17+,18+,19-,20-/m1/s1

Standard InChI Key:  XJXDJAQAAAVDCT-RHOFUAETSA-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: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 2.06

#Rotatable Bonds: 1

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.66

CX Basic pKa:

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 0

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: 3.54

References

1. Evidente A, Venturi V, Masi M, Degrassi G, Cimmino A, Maddau L, Andolfi A..  (2011)  In vitro antibacterial activity of sphaeropsidins and chemical derivatives toward Xanthomonas oryzae pv. oryzae, the causal agent of rice bacterial blight.,  74  (12): [PMID:22124378] [10.1021/np200625m]

2. Zhang PL, Han Y, Zhang LT, Wang XL, Shen T, Ren D, Lou H, Wang XN..  (2017)  Botrysphones A-C and Botrysphins A-F, Triketides and Diterpenoids from the Fungus Botrysphaeria laricina.,  80  (6): [PMID:28609099] [10.1021/acs.jnatprod.6b01196]

3. Kato H, Sebe M, Nagaki M, Eguchi K, Kagiyama I, Hitora Y, Frisvad JC, Williams RM, Tsukamoto S..  (2019)  Taichunins A-D, Norditerpenes from Aspergillus taichungensis (IBT 19404).,  82  (5): [PMID:30995043] [10.1021/acs.jnatprod.8b01032]

4. El-Desoky AHH, Inada N, Maeyama Y, Kato H, Hitora Y, Sebe M, Nagaki M, Kai A, Eguchi K, Inazumi T, Sugimoto Y, Frisvad JC, Williams RM, Tsukamoto S..  (2021)  Taichunins E-T, Isopimarane Diterpenes and a 20-nor-Isopimarane, from Aspergillus taichungensis (IBT 19404): Structures and Inhibitory Effects on RANKL-Induced Formation of Multinuclear Osteoclasts.,  84  (9.0): [PMID:34464116] [10.1021/acs.jnatprod.1c00486]

Source

Source(1):

• Scientific Literature