ID: ALA330348

Max Phase: Preclinical

Molecular Formula: C30H26O10

Molecular Weight: 546.53

Molecule Type: Small molecule

Representations

Synonyms (2): Hypocrellin A | Rel-Hypocrellin A
Synonyms from Alternative Forms(2):

Canonical SMILES:  COc1c2c3c4c(c(OC)c(=O)c5c(O)cc(OC)c(c6c(OC)cc(O)c(c1=O)c63)c54)[C@@H](C(C)=O)[C@@](C)(O)C2

Standard InChI:  InChI=1S/C30H26O10/c1-10(31)25-24-22-16-11(9-30(25,2)36)28(39-5)26(34)17-12(32)7-14(37-3)19(21(16)17)20-15(38-4)8-13(33)18(23(20)22)27(35)29(24)40-6/h7-8,25,32-33,36H,9H2,1-6H3/t25-,30+/m1/s1

Standard InChI Key:  BQJKVFXDDMQLBE-RNAHPLFWSA-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: 546.53

Molecular Weight (Monoisotopic): 546.1526

AlogP: 3.32

#Rotatable Bonds: 5

Polar Surface Area: 148.82

Molecular Species: ACID

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.47

CX Basic pKa: 3.19

CX LogP: 3.13

CX LogD: 1.72

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.22

Np Likeness Score: 1.43

References

1. Wang HK, Xie JX, Chang JJ, Hwang KM, Liu SY, Ballas LM, Jiang JB, Lee KH..  (1992)  Antitumor agents. 134. New shiraiachrome-A- and calphostin-C-related perylene derivatives as cytotoxic and antiviral agents and inhibitors of protein kinase C.,  35  (15): [PMID:1379638] [10.1021/jm00093a001]

2. Wang HK, Xie JX, Chang JJ, Hwang KM, Liu SY, Ballas LM, Jiang JB, Lee KH..  (1992)  Antitumor agents. 134. New shiraiachrome-A- and calphostin-C-related perylene derivatives as cytotoxic and antiviral agents and inhibitors of protein kinase C.,  35  (15): [PMID:1379638] [10.1021/jm00093a001]

3. Li G, Wang H, Zhu R, Sun L, Wang L, Li M, Li Y, Liu Y, Zhao Z, Lou H..  (2012)  Phaeosphaerins A-F, cytotoxic perylenequinones from an endolichenic fungus, Phaeosphaeria sp.,  75  (2): [PMID:22276650] [10.1021/np200614h]

4. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

5. Li YT, Yang C, Wu Y, Lv JJ, Feng X, Tian X, Zhou Z, Pan X, Liu S, Tian LW..  (2021)  Axial Chiral Binaphthoquinone and Perylenequinones from the Stromata of Hypocrella bambusae Are SARS-CoV-2 Entry Inhibitors.,  84  (2.0): [PMID:33560122] [10.1021/acs.jnatprod.0c01136]

Source

Source(1):

• Scientific Literature