roridin E

ID: ALA509175

Chembl Id: CHEMBL509175

Cas Number: 16891-85-3

PubChem CID: 44593339

Max Phase: Preclinical

Molecular Formula: C29H38O8

Molecular Weight: 514.62

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Roridin E | Roridin E|Roridine E|16891-85-3|98826FBF79|(1R,3R,8R,12E,17R,18E,20Z,24R,25S,26S)-17-[(1R)-1-hydroxyethyl]-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,12,18,20-tetraene-26,2'-oxirane]-11,22-dione|Verrucarin A, 2',3'-didehydro-7'-deoxo-2'-deoxy-7'-((1R)-1-hydroxyethyl)-, (2'E,7'R)-|Verrucarin A, 2',3'-didehydro-7'-deoxo-2'-deoxy-7'-(1-hydroxyethyl)-, (2'E,7'R(R))-|Verrucarin A, 2',3'-didehydro-7'-deoxo-2'-deoxy-7'-[(1R)-1-hydroxyethyl]-, (2'E,7'RShow More⌵

Canonical SMILES:  CC1=C[C@H]2O[C@@H]3C[C@H]4OC(=O)/C=C\C=C\[C@H]([C@@H](C)O)OCC/C(C)=C/C(=O)OC[C@@]2(CC1)[C@]4(C)[C@]31CO1

Standard InChI:  InChI=1S/C29H38O8/c1-18-9-11-28-16-34-26(32)14-19(2)10-12-33-21(20(3)30)7-5-6-8-25(31)37-22-15-24(36-23(28)13-18)29(17-35-29)27(22,28)4/h5-8,13-14,20-24,30H,9-12,15-17H2,1-4H3/b7-5+,8-6-,19-14+/t20-,21-,22-,23-,24-,27-,28-,29+/m1/s1

Standard InChI Key:  KEEQQEKLEZRLDS-FLGSVKSYSA-N

Alternative Forms

1. Parent:

   

   ALA509175

   RORIDIN E

Molecule Features

Natural Product: No

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: 514.62

Molecular Weight (Monoisotopic): 514.2567

AlogP: 3.34

#Rotatable Bonds: 1

Polar Surface Area: 103.82

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.32

Np Likeness Score: 3.17

References

1. Isaka M, Punya J, Lertwerawat Y, Tanticharoen M, Thebtaranonth Y..  (1999)  Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria.,  62  (2): [PMID:10075777] [10.1021/np980323x]

2. Whyte AC, Gloer JB, Scott JA, Malloch D..  (1996)  Cercophorins A-C: novel antifungal and cytotoxic metabolites from the coprophilous fungus Cercophora areolata.,  59  (8): [PMID:8792624] [10.1021/np9603232]

3. Alvi KA, Rabenstein J, Woodard J, Baker DD, Bergthold JD, Lynch J, Lieu KL, Braude IA..  (2002)  14'-Hydroxymytoxin B and 16-hydroxyroridin E, two new cytotoxic trichothecenes from Myrothecium roridum.,  65  (5): [PMID:12027756] [10.1021/np010449l]

4. Namikoshi M, Akano K, Meguro S, Kasuga I, Mine Y, Takahashi T, Kobayashi H..  (2001)  A new macrocyclic trichothecene, 12,13-deoxyroridin E, produced by the marine-derived fungus Myrothecium roridum collected in Palau.,  64  (3): [PMID:11277768] [10.1021/np000443g]

5. Lebar MD, Hahn KN, Mutka T, Maignan P, McClintock JB, Amsler CD, van Olphen A, Kyle DE, Baker BJ..  (2011)  CNS and antimalarial activity of synthetic meridianin and psammopemmin analogs.,  19  (19): [PMID:21907583] [10.1016/j.bmc.2011.08.033]

6. Lee SR, Seok S, Ryoo R, Choi SU, Kim KH..  (2019)  Macrocyclic Trichothecene Mycotoxins from a Deadly Poisonous Mushroom, Podostroma cornu-damae.,  82  (1): [PMID:30457333] [10.1021/acs.jnatprod.8b00823]

7. Shen L, Ai CZ, Song YC, Wang FW, Jiao RH, Zhang AH, Man HZ, Tan RX..  (2019)  Cytotoxic Trichothecene Macrolides Produced by the Endophytic Myrothecium roridum.,  82  (6): [PMID:31117520] [10.1021/acs.jnatprod.8b01034]

Source

Source(1):

• Scientific Literature