Gestodene - Moligand™, ≥98% , Progesterone receptor agonist, CAS No.60282-87-3, Progesterone receptor agonist

CAS: 60282-87-3 Cat. No.: G304109 Molecular Weight: 310.43 EC Number: 262-145-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

SHB 331 | WL 70 | (8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one | 17alpha -Ethynyl-17beta-hydroxy-18-methyl-4,15-estradien-3-one | 17-alpha-Ethinyl-13-ethyl-17-beta-hydroxy

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Gestodene(SHB 331;WL 70) is a progestogen hormonal contraceptive. Target: Estrogen Receptor/ERR Gestodene is androgenically neutral, meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects (e.g. acne, hirsutism, weight gain) often associated with second-generation contraceptive pills, such as those containing levonorgestrel. When 40 micrograms of gestodene was taken, six out of seven women did not ovulate, and one out of seven had a cycle with luteal insufficiency. These data indicate that 40 micrograms of gestodene is the borderline dose for inhibition of ovulation. A combination of 75 micrograms gestodene with 30 micrograms ethinyl estradiol was found to inhibit ovulation in ten subjects, and no follicular maturation was noted . gestodene bound with high affinity to the progesterone receptor, as did other synthetic and natural progestogens. However, gestodene did not bind to the estradiol receptor. The relative binding affinities of all tested synthetic and natural ligands showed no organ-specific differences and no differences between neoplastically transformed and normal tissues . Clinical indications: Female contraception

Specifications

Synonyms

SHB 331 | WL 70 | (8R, 9S, 10R, 13S, 14S, 17R)-13-Ethyl-17-ethynyl-17-hydroxy-6, 7, 8, 9, 10, 11, 12, 13, 14, 17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one | 17alpha -Ethynyl-17beta-hydroxy-18-methyl-4, 15-estradien-3-one | 17-alpha-Ethinyl-13-ethyl-17-beta-hydroxy

Specifications & Purity

Moligand™, ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Progesterone receptor agonist

Purity

≥98%

Product Properties

• ALogP: 2.9

Names and Identifiers

• Pubchem Sid: 504762353
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762353
• Canonical Smiles: CCC12CCC3C(C1C=CC2(C#C)O)CCC4=CC(=O)CCC34
• IUPAC Name: (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
• InChIKey: SIGSPDASOTUPFS-XUDSTZEESA-N
• INCHI: 1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
• Isomeric SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1C=C[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
• Molecular Weight: 310.43
• Reaxy-Rn: 37913880
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37913880&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Estrane steroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Estrane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Estrogens and derivatives
• Alternative Parents: 3-oxosteroids 17-hydroxysteroids Cyclohexenones Ynones Tertiary alcohols Acetylides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Estrogen-skeleton - 3-oxosteroid - Hydroxysteroid - Oxosteroid - 17-hydroxysteroid - Cyclohexenone - Ynone - Tertiary alcohol - Ketone - Cyclic ketone - Acetylide - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Carbonyl group - Alcohol - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

Discover Target: F2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

Discover Target: GABRA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOB Tclin Monoamine oxidase B (8835 Activities)

Discover Target: MAOB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

Discover Target: SLC6A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

Discover Target: OPRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

Discover Target: PDE3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

Discover Target: HTR2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

Discover Target: TBXA2R

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

Discover Target: PDE4A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH3 Tclin Histamine H3 receptor (10389 Activities)

Discover Target: HRH3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

Discover Target: ABCC2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCB11 Tchem Bile salt export pump (2311 Activities)

Discover Target: ABCB11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

Discover Target: ABCC3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

Discover Target: ABCC4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pneumocystis carinii (749 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania infantum (5912 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma brucei (78846 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma brucei brucei (13300 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Entamoeba histolytica (2676 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cryptosporidium parvum (1150 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasmodium falciparum (966862 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania amazonensis (3813 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania donovani (89745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania major (2877 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania mexicana (936 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma cruzi (99888 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trichomonas vaginalis (2376 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Toxoplasma gondii (4585 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma brucei rhodesiense (7991 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Refractive Index: 1.588
• Flash Point(°C): 196.9ºC
• Boil Point(°C): 462.7ºC
• Melt Point(°C): 190-192°C
• Molecular Weight: 310.400 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 310.193 Da
• Monoisotopic Mass: 310.193 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 648.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Qianyu Li, Guoliang Li, Lihua Fan, Yanxin Yu, Jin Liu.  (2021)  Click reaction triggered turn-on fluorescence strategy for highly sensitive and selective determination of steroid hormones in food samples.  FOOD CHEMISTRY,      [PMID:34875430] [10.1016/j.foodchem.2021.131565]

2. Xu Jiaqi, Li Qianyu, Li Wenrui, Wu Di, Wu Yongning, Li Guoliang.  (2025)  Efficient adsorption and detection of steroid hormones in foods through the combination of novel magnetic TAPB-COF materials with click isotope probes.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:39820674] [10.1007/s00216-024-05727-6]