ID: ALA400514

Max Phase: Preclinical

Molecular Formula: C26H32O7

Molecular Weight: 456.54

Molecule Type: Small molecule

Representations

Synonyms (1): Berkeleydione
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C1[C@@]2(C)C[C@H]3C(C)=C4CC(=O)OC(C)(C)C4=CC[C@]3(C)[C@]1(C(=O)OC)C(=O)[C@@](C)(O)C2=O

Standard InChI:  InChI=1S/C26H32O7/c1-13-15-11-18(27)33-22(3,4)16(15)9-10-24(6)17(13)12-23(5)14(2)26(24,21(30)32-8)20(29)25(7,31)19(23)28/h9,17,31H,2,10-12H2,1,3-8H3/t17-,23+,24-,25-,26-/m0/s1

Standard InChI Key:  RBGYOLFHIDJTOX-VMXKAMJHSA-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: 456.54

Molecular Weight (Monoisotopic): 456.2148

AlogP: 3.01

#Rotatable Bonds: 1

Polar Surface Area: 106.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.48

CX Basic pKa:

CX LogP: 2.95

CX LogD: 2.95

Aromatic Rings: 0

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: 2.67

References

1. Stierle DB, Stierle AA, Patacini B..  (2007)  The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium.,  70  (11): [PMID:17970594] [10.1021/np070329z]

2. Stierle DB, Stierle AA, Patacini B, McIntyre K, Girtsman T, Bolstad E..  (2011)  Berkeleyones and related meroterpenes from a deep water acid mine waste fungus that inhibit the production of interleukin 1-β from induced inflammasomes.,  74  (10): [PMID:21916432] [10.1021/np2003066]

3. Qi B, Liu X, Mo T, Zhu Z, Li J, Wang J, Shi X, Zeng K, Wang X, Tu P, Abe I, Shi S..  (2017)  3,5-Dimethylorsellinic Acid Derived Meroterpenoids from Penicillium chrysogenum MT-12, an Endophytic Fungus Isolated from Huperzia serrata.,  80  (10): [PMID:28960979] [10.1021/acs.jnatprod.7b00438]

Source

Source(1):

• Scientific Literature