ID: ALA240545

Max Phase: Preclinical

Molecular Formula: C23H22O7

Molecular Weight: 410.42

Molecule Type: Small molecule

Representations

Synonyms (2): 12A-Hydroxyrotenone | Rotenolone
Synonyms from Alternative Forms(2):

Canonical SMILES:  C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@]2(O)C3=O)O1

Standard InChI:  InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1

Standard InChI Key:  JFVKWCYZKMUTLH-AYPBNUJASA-N

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

Properties

Molecular Weight: 410.42

Molecular Weight (Monoisotopic): 410.1366

AlogP: 2.81

#Rotatable Bonds: 3

Polar Surface Area: 83.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.08

CX Basic pKa:

CX LogP: 2.73

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.78

Np Likeness Score: 2.18

References

1. Matsuda H, Yoshida K, Miyagawa K, Asao Y, Takayama S, Nakashima S, Xu F, Yoshikawa M..  (2007)  Rotenoids and flavonoids with anti-invasion of HT1080, anti-proliferation of U937, and differentiation-inducing activity in HL-60 from Erycibe expansa.,  15  (3): [PMID:17158054] [10.1016/j.bmc.2006.09.024]

2. Cao S, Schilling JK, Miller JS, Andriantsiferana R, Rasamison VE, Kingston DG..  (2004)  Cytotoxic compounds from Mundulea chapelieri from the Madagascar Rainforest.,  67  (3): [PMID:15043430] [10.1021/np0303815]

3. Takashima J, Chiba N, Yoneda K, Ohsaki A..  (2002)  Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.,  65  (4): [PMID:11975515] [10.1021/np010126p]

4. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

5. Harinantenaina L, Brodie PJ, Slebodnick C, Callmander MW, Rakotobe E, Randrianasolo S, Randrianaivo R, Rasamison VE, Tendyke K, Shen Y, Suh EM, Kingston DG..  (2010)  Antiproliferative compounds from Pongamiopsis pervilleana from the Madagascar Dry Forest.,  73  (9): [PMID:20804165] [10.1021/np100430r]

6. Gao S, Xu YM, Valeriote FA, Gunatilaka AA..  (2011)  Pierreiones A-D, solid tumor selective pyranoisoflavones and other cytotoxic constituents from Antheroporum pierrei.,  74  (4): [PMID:21452840] [10.1021/np100763p]

7. Bueno Pérez L, Li J, Lantvit DD, Pan L, Ninh TN, Chai HB, Soejarto DD, Swanson SM, Lucas DM, Kinghorn AD..  (2013)  Bioactive constituents of Indigofera spicata.,  76  (8): [PMID:23895019] [10.1021/np400567c]

8. Tu Y, Wu C, Kang Y, Li Q, Zhu C, Li Y..  (2019)  Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.,  29  (10): [PMID:30910460] [10.1016/j.bmcl.2019.03.024]

9. Russell DA, Bridges HR, Serreli R, Kidd SL, Mateu N, Osberger TJ, Sore HF, Hirst J, Spring DR..  (2020)  Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells.,  83  (6): [PMID:32459967] [10.1021/acs.jnatprod.9b01224]

Source

Source(1):

• Scientific Literature