2-Hydroxy-5-methoxy-3-((1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-[1,4]benzoquinone

ID: ALA155085

Chembl Id: CHEMBL155085

Max Phase: Preclinical

Molecular Formula: C22H30O4

Molecular Weight: 358.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ilimaquinone

Canonical SMILES:  C=C1CCC[C@H]2[C@](C)(CC3=C(O)C(=O)C=C(OC)C3=O)[C@@H](C)CC[C@]12C

Standard InChI:  InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18+,21+,22+/m0/s1

Standard InChI Key:  JJWITJNSXCXULM-YVUMSICPSA-N

Alternative Forms

1. Parent:

   

   ALA155085

   ILIMAQUINONE

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: 358.48

Molecular Weight (Monoisotopic): 358.2144

AlogP: 4.67

#Rotatable Bonds: 3

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.87

CX Basic pKa: ┄

CX LogP: 4.37

CX LogD: 2.83

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: 3.23

References

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12. Arai M, Kawachi T, Sato H, Setiawan A, Kobayashi M..  (2014)  Marine spongian sesquiterpene phenols, dictyoceratin-C and smenospondiol, display hypoxia-selective growth inhibition against cancer cells.,  24  (14): [PMID:24865416] [10.1016/j.bmcl.2014.04.116]

13. Kiem PV, Huyen LT, Hang DT, Nhiem NX, Tai BH, Anh HL, Cuong PV, Quang TH, Minh CV, Dau NV, Kim YA, Subedi L, Kim SY, Kim SH..  (2017)  Sesquiterpene derivatives from marine sponge Smenospongia cerebriformis and their anti-inflammatory activity.,  27  (7): [PMID:28262525] [10.1016/j.bmcl.2017.02.040]

14. Nguyen HM, Ito T, Kurimoto SI, Ogawa M, Win NN, Hung VQ, Nguyen HT, Kubota T, Kobayashi J, Morita H..  (2017)  New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.,  27  (14): [PMID:28558970] [10.1016/j.bmcl.2017.05.060]

15. Jiso A, Kittiwisut S, Chantakul R, Yuenyongsawad S, Putchakarn S, Schäberle TF, Temkitthaworn P, Ingkaninan K, Chaithirayanon K, Plubrukarn A..  (2020)  Quintaquinone, a Merosesquiterpene from the Yellow Sponge Verongula cf. rigida Esper.,  83  (2): [PMID:32040314] [10.1021/acs.jnatprod.9b00886]

Source

Source(1):

• Scientific Literature