2-Methyl-acrylic acid (Z)-(4R,8R,9S,11R)-2-hydroxymethyl-11-methyl-7-methylene-6,12-dioxo-5,14-dioxa-tricyclo[9.2.1.0*4,8*]tetradeca-1(13),2-dien-9-yl ester

ID: ALA371358

Chembl Id: CHEMBL371358

Cas Number: 60066-35-5

PubChem CID: 5358393

Max Phase: Preclinical

Molecular Formula: C19H20O7

Molecular Weight: 360.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Goiazensolide | Goyazensolide | GOYAZENSOLIDE|Furanoheliangolide|60066-35-5|goiazensolide|(3aR,4S,6R,11aR,Z)-10-(Hydroxymethyl)-6-methyl-3-methylene-2,7-dioxo-2,3,3a,4,5,6,7,11a-octahydro-6,9-epoxycyclodeca[b]furan-4-yl methacrylate|[(2Z,4R,8R,9S,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradeca-1(13),2-dien-9-yl] 2-methylprop-2-enoate|NSC-249918|NSC 249918|CHEMBL371358|SCHEMBL7996210|DTXSID701317740|BDBM50433423|NSC249918|2-Propenoic acid, 2-methyShow More⌵

Canonical SMILES:  C=C(C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)/C(CO)=C\[C@H]2OC(=O)C(=C)[C@H]12

Standard InChI:  InChI=1S/C19H20O7/c1-9(2)17(22)25-14-7-19(4)15(21)6-12(26-19)11(8-20)5-13-16(14)10(3)18(23)24-13/h5-6,13-14,16,20H,1,3,7-8H2,2,4H3/b11-5-/t13-,14+,16+,19-/m1/s1

Standard InChI Key:  HTMCLLSRQWRPTN-OKMRAYSCSA-N

Alternative Forms

1. Parent:

   

   ALA371358

   GOIAZENSOLIDE

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: 360.36

Molecular Weight (Monoisotopic): 360.1209

AlogP: 1.14

#Rotatable Bonds: 3

Polar Surface Area: 99.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.40

CX LogD: 1.40

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: 3.32

References

1. Siedle B, García-Piñeres AJ, Murillo R, Schulte-Mönting J, Castro V, Rüngeler P, Klaas CA, Da Costa FB, Kisiel W, Merfort I..  (2004)  Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-kappaB.,  47  (24): [PMID:15537359] [10.1021/jm049937r]

2. Wagner S, Hofmann A, Siedle B, Terfloth L, Merfort I, Gasteiger J..  (2006)  Development of a structural model for NF-kappaB inhibition of sesquiterpene lactones using self-organizing neural networks.,  49  (7): [PMID:16570920] [10.1021/jm051125n]

3. García A, Bocanegra-García V, Palma-Nicolás JP, Rivera G..  (2012)  Recent advances in antitubercular natural products.,  49  [PMID:22280816] [10.1016/j.ejmech.2011.12.029]

4. Schomburg C, Schuehly W, Da Costa FB, Klempnauer KH, Schmidt TJ..  (2013)  Natural sesquiterpene lactones as inhibitors of Myb-dependent gene expression: structure-activity relationships.,  63  [PMID:23501116] [10.1016/j.ejmech.2013.02.018]

5. Ren Y, Gallucci JC, Li X, Chen L, Yu J, Kinghorn AD..  (2018)  Crystal Structures and Human Leukemia Cell Apoptosis Inducible Activities of Parthenolide Analogues Isolated from Piptocoma rufescens.,  81  (3): [PMID:29350920] [10.1021/acs.jnatprod.7b01079]

6. Chibli LA, Schmidt TJ, Nonato MC, Calil FA, Da Costa FB..  (2018)  Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.,  157  [PMID:30145372] [10.1016/j.ejmech.2018.08.033]

7. Ren Y, de Blanco EJC, Fuchs JR, Soejarto DD, Burdette JE, Swanson SM, Kinghorn AD..  (2019)  Potential Anticancer Agents Characterized from Selected Tropical Plants.,  82  (3): [PMID:30830783] [10.1021/acs.jnatprod.9b00018]

8. Patouret R, Barluenga S, Winssinger N..  (2022)  Withaferin A, a polyfunctional pharmacophore that includes covalent engagement of IPO5, is an inhibitor of influenza A replication.,  69  [PMID:35772286] [10.1016/j.bmc.2022.116883]

Source

Source(1):

• Scientific Literature