Verrucarin A

ID: ALA136985

Chembl Id: CHEMBL136985

Cas Number: 3148-09-2

PubChem CID: 6326658

Max Phase: Preclinical

Molecular Formula: C27H34O9

Molecular Weight: 502.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Verrucarin A | Verrucarin A|Muconomycin A|Antibiotic 379Y|3148-09-2|VER A|OL62X66O4I|CHEBI:230243|(4S,5R,10E,12Z,16R,16aS,17S,18R,19aR,23aR)-4-hydroxy-5,16a,21-trimethyl-4,5,6,7,16,16a,22,23-octahydro-3H,18H,19aH-spiro[16,18-methano[1,6,12]trioxacyclooctadecino[3,4-d]chromene-17,2'-oxirane]-3,9,14-trione|Spiro(16,18-methano-1H,3H,23H-(1,6,12)trioxacyclooctadecino(3,4-d)(1)benzopyran-17(18H),2'-oxirane)-3,9,14-trione, 4,5,6,7,16,16a,19a,22-octahydro-4-hydroxy-5,16a,21-trimethyl-, stereoisomer|379Show More⌵

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

Standard InChI:  InChI=1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3/b6-4+,7-5-/t17-,18-,19-,20-,23+,25-,26-,27+/m1/s1

Standard InChI Key:  NLUGUZJQJYVUHS-IDXDZYHTSA-N

Alternative Forms

1. Parent:

   

   ALA136985

   VERRUCARIN A

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: 502.56

Molecular Weight (Monoisotopic): 502.2203

AlogP: 2.17

#Rotatable Bonds: ┄

Polar Surface Area: 120.89

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.48

CX Basic pKa: ┄

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.23

Np Likeness Score: 3.03

References

1. Jarvis BB, Stahly GP, Pavanasasivam G, Mazzola EP..  (1980)  Antileukemic compounds derived from the chemical modification of macrocyclic trichothecenes. 1. Derivatives of verrucarin A.,  23  (9): [PMID:7411550] [10.1021/jm00183a018]

2. Jarvis BB, Midiwo JO, Mazzola EP..  (1984)  Antileukemic compounds derived by chemical modification of macrocyclic trichothecenes. 2. Derivatives of roridins A and H and verrucarins A and J.,  27  (2): [PMID:6694172] [10.1021/jm00368a025]

3. Amagata T, Rath C, Rigot JF, Tarlov N, Tenney K, Valeriote FA, Crews P..  (2003)  Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.,  46  (20): [PMID:13678412] [10.1021/jm030090t]

4. 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]

5. 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]

6. Steinmetz WE, Robustelli P, Edens E, Heineman D..  (2008)  Structure and conformational dynamics of trichothecene mycotoxins.,  71  (4): [PMID:18327910] [10.1021/np070562x]

7. 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]

8. Steinmetz WE, Rodarte CB, Lin A..  (2009)  3D QSAR study of the toxicity of trichothecene mycotoxins.,  44  (11): [PMID:19586689] [10.1016/j.ejmech.2009.06.012]

9. Kularatne SA, Venkatesh C, Santhapuram HK, Wang K, Vaitilingam B, Henne WA, Low PS..  (2010)  Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs.,  53  (21): [PMID:20936874] [10.1021/jm100729b]

10. 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