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Forskolin

Forskolin structure

CAS No:
66575-29-9
Formula:
C22H34O7
Chemical Name:
Forskolin
Synonyms:
1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-;1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,[3R-(3α,4aβ,5β,6β,6aα,10α,10aβ,10bα)]-;(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(Acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-1-one;Forskolin;Coleonol;Colforsin;HL 362;L 75-1362B;ForsLean;NSC 357088;NSC 375489;(-)-Forskolin;64657-11-0
Categories:
Biochemical Engineering > Plant Extracts

Description

Forskolin is a potent adenylate cyclase activator, with IC50 and EC50 of 41 nM and 0.5 μM for type I adenylyl cyclase, respectively.

Forskolin is a labdane diterpenoid isolated from the Indian Coleus plant. It has a role as a plant metabolite, an anti-HIV agent, a protein kinase A agonist, an adenylate cyclase agonist, an antihypertensive agent and a platelet aggregation inhibitor. It is a labdane diterpenoid, an acetate ester, an organic heterotricyclic compound, a triol, a cyclic ketone and a tertiary alpha-hydroxy ketone.|Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant Coleus forskohlii. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.

Forskolin Basic Attributes

Molecular Weight：

410.5

Exact Mass：

410.50

EC Number：

266-410-9

UNII：

1F7A44V6OU

DSSTox ID：

DTXSID8040484

HScode：

29329990

Characteristics

PSA：

113

XLogP3：

Appearance：

off-white powder

Density：

1.2±0.1 g/cm3

Melting Point：

232 °C

Boiling Point：

520℃

Flash Point：

172℃

Refractive Index：

1.552

Water Solubility：

soluble in ethanol, dimethylsulfoxide and chloroform. Insolule in water.DMSO: 5 mg/mL stable at least 6 months at room temperature

Storage Conditions：

−20°C

Toxicity：

Oral-Rat LD50 2550 mg/kg; Oral-Mouse LD50: 2300 mg/kg

Flammability characteristics：

Flammable, spicy and irritating smoke emitted from the fire

Specific rotation：

D25 -26.19° (c = 1.68 in CHCl3)

Collision Cross Section：

191.9 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

22-36/37

RTECS Number：

QL6150000

Marks：

Storage features：

Treasury is ventilated, low temperature and dry; stored and transported separately from strong acid, strong alkali and food

Precautionary statement(s)：

P280

Hazard Statements：

H312

GHS Classification：

|Warning|H312 (97.73%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P280, P302+P352, P312, P322, P363, and P501|Aggregated GHS information provided by 45 companies from 3 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity class：

moderately toxic

Drug Information

MeSH：

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)|Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)|Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

MeSH Entry Terms：

Coleonol

Forskolin Use and Manufacturing

Uses

Cyclic AMP (cAMP) is an important signal carrier necessary for the proper biological response of cells to hormones, neurotransmitters, and other extracellular signalsForskolin is a naturally occurring diterpene that is produced by the Indian Coleus plant (C. forskohlii). It directly activates adenylyl cyclase through its catalytic subunit and is commonly used to raise levels of cAMP in a wide variety of intact cells and tissue preparations. Forskolin binds to adenylyl cyclase in membranes from stably transfected Sf9 cells expressing type 1 adenylyl cyclase with an IC50 value of 41 nM and demonstrates an EC50 value of 0.5 μM in an activation assay assessing formation of cAMP from ATP. Forskolin also interacts with glucose transporters and certain ion channels and has been used for examining adenylyl cyclase expression, regulation, and G protein signaling.[Cayman Chemical]

Use Classification：

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C20 isoprenoids (diterpenes) [PR0104]

Computed Properties

Molecular Weight:410.5
XLogP3:1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:410.23045342
Monoisotopic Mass:410.23045342
Topological Polar Surface Area:113
Heavy Atom Count:29
Complexity:747
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Forskolin

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
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