3,8-Dihydrodiligustilide

3,8-Dihydrodiligustilide
Identifiers

IUPAC name (1S,2S,6Z,10S,11S)-16-Butyl-6-butylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione
Synonyms	(3Z')-(3a'R,6'R,3R,6R,7R)-3,8-Dihydro-6.6',7.3a'-diligustilide^[1]
PubChem (CID)	102175205
Chemical and physical data
Formula	C₂₄H₃₀O₄
Molar mass	382.5 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCC1[C@]23CC[C@H](C=C2C(=O)O1)[C@H]4[C@@H]3C5=C(CC4)/C(=C/CCC)/OC5=O
InChI InChI=1S/C24H30O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7,13-15,19,21H,3-6,8-12H2,1-2H3/b18-7-/t14-,15+,19?,21-,24+/m1/s1 Key:YTEUTQUNVHWZOR-LGNHLWLRSA-N

3,8-Dihydrodiligustilide is a non-steroidal phytoprogestogen that is found in Ligusticum chuanxiong.^[1]^[2] It is a potent agonist of the progesterone receptor (EC₅₀ = 90 nM).^[1] Another compound in the plant, riligustilide, is also a phytoprogestogen, but is almost 1,000-fold less potent and is very weak in comparison (EC₅₀ ≈ 81 μM).^[1]

References

1 2 3 4 Lim LS, Shen P, Gong YH, Yong EL (2006). "Dimeric progestins from rhizomes of Ligusticum chuanxiong". Phytochemistry. 67 (7): 728–34. doi:10.1016/j.phytochem.2006.01.024. PMID 16516938.
↑ Ahmed, H.M.M.; Yeh, J.Y.; Lin, W.J.; Forsberg, N.E.; Cheng, W.T.K.; Ou, B.R (2014). "Validation of a luciferase bioassay to detect the progestative activity in gilts whose estrus was induced by an uterotonic herb (Ligusticum chuanxiong)". Livestock Science. 163: 159–164. doi:10.1016/j.livsci.2014.02.012. ISSN 1871-1413.

Progesterone receptor modulators

Agonists	Progesterone derivatives: 5α-Dihydroprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 20α-Dihydroprogesterone Dimepregnen Diosgenin Progesterone Quingestrone Retroprogesterone derivatives: Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives: 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Amadinone Amadinone acetate Anagestone Anagestone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Flumedroxone Flumedroxone acetate Gestaclone Haloprogesterone Hydromadinone (hydromadinone acetate) Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone 19-Norprogesterone derivatives: 19-Norprogesterone Demegestone Gestadienol Gestonorone caproate (gestronol hexanoate) Gestronol (gestonorone) Nomegestrol Nomegestrol acetate Norgestomet Org-2058 Oxogestone Oxogestone phenpropionate Promegestone Segesterone Segesterone acetate (nestorone) Trimegestone Testosterone derivatives: 6,6-Difluoronorethisterone 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione Δ^4-Tibolone Allylestrenol Altrenogest Bolandiol Bolandiol dipropionate Bolandione Chloroethynyl norgestrel Cingestol Danazol Desogestrel Dienedione Dienogest Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethisterone Dimethyltrienolone Ethisterone Ethyldienolone Ethylestrenol (ethylnandrol) Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Methyldienolone Metribolone (R-1881) Metynodiol Metynodiol diacetate Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norelgestromin Norethisterone (norethindrone) Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Normethandrone (methylestrenolone, normethandrolone, normethisterone) Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tetrahydrogestrinone Tibolone Tigestol Tosagestin Trenbolone (trienolone) Trestolone Trestolone acetate Spirolactone derivatives: Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate SC-5233 SC-8109 Spironolactone Spirorenone Non-steroidal: 3,8-Dihydrodiligustilide Riligustilide Tanaproget ZM-182345

Mixed (SPRMs)	Apigenin Asoprisnil Asoprisnil ecamate Guggulsterone Kaempferol J1042 LG-120838 Naringenin PRA-910 Syringic acid Telapristone Antagonistic: Mifepristone Org-31710 Org-33628 Ulipristal acetate ZK-137316

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Lilopristone Lonaprisan Onapristone Toripristone Valproic acid Vilaprisan Zanoterone ZM-150271 ZM-172406

mPRs
(PAQRs)

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 11-Deoxycorticosterone 17α-Hydroxyprogesterone 17α,21-Dihydroxyprogesterone 21-Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone

Antagonists	Mifepristone

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Steroid hormone metabolism modulators

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