secalonic acid A

ID: ALA500027

Chembl Id: CHEMBL500027

Cas Number: 35287-72-0

PubChem CID: 169680

Max Phase: Preclinical

Molecular Formula: C32H30O14

Molecular Weight: 638.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]12Oc3ccc(-c4ccc5c(c4O)C(=O)C4=C(O)C[C@@H](C)[C@H](O)[C@@]4(C(=O)OC)O5)c(O)c3C(=O)C1=C(O)C[C@@H](C)[C@@H]2O

Standard InChI:  InChI=1S/C32H30O14/c1-11-9-15(33)21-25(37)19-17(45-31(21,27(11)39)29(41)43-3)7-5-13(23(19)35)14-6-8-18-20(24(14)36)26(38)22-16(34)10-12(2)28(40)32(22,46-18)30(42)44-4/h5-8,11-12,27-28,33-36,39-40H,9-10H2,1-4H3/t11-,12-,27+,28+,31+,32+/m1/s1

Standard InChI Key:  DRYDKQOPVBDZMQ-ZKHWAINJSA-N

Alternative Forms

1. Parent:

   

   ALA500027

   SECALONIC ACID A

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

Calculated Properties

Molecular Weight: 638.58

Molecular Weight (Monoisotopic): 638.1636

AlogP: 2.16

#Rotatable Bonds: 3

Polar Surface Area: 226.58

Molecular Species: NEUTRAL

HBA: 14

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.24

CX Basic pKa:

CX LogP: 2.25

CX LogD: 1.85

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.27

Np Likeness Score: 1.24

References

1. Pettit GR, Meng Y, Herald DL, Graham KA, Pettit RK, Doubek DL..  (2003)  Isolation and structure of ruprechstyril from Ruprechtia tangarana.,  66  (8): [PMID:12932125] [10.1021/np0300986]

2. Cardellina JH, Roxas-Duncan VI, Montgomery V, Eccard V, Campbell Y, Hu X, Khavrutskii I, Tawa GJ, Wallqvist A, Gloer JB, Phatak NL, Höller U, Soman AG, Joshi BK, Hein SM, Wicklow DT, Smith LA..  (2012)  Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.,  3  (5): [PMID:24900483] [10.1021/ml200312s]

3. El-Elimat T, Raja HA, Day CS, McFeeters H, McFeeters RL, Oberlies NH..  (2017)  α-Pyrone derivatives, tetra/hexahydroxanthones, and cyclodepsipeptides from two freshwater fungi.,  25  (2): [PMID:27964996] [10.1016/j.bmc.2016.11.059]

4. Lünne F, Köhler J, Stroh C, Müller L, Daniliuc CG, Mück-Lichtenfeld C, Würthwein EU, Esselen M, Humpf HU, Kalinina SA..  (2021)  Insights into Ergochromes of the Plant Pathogen Claviceps purpurea.,  84  (10.0): [PMID:34553942] [10.1021/acs.jnatprod.1c00264]

Source

Source(1):

• Scientific Literature