Forskolin Racemate

Details

• Internal ID: 2e00a266-1b8e-4afe-83f4-8b3208b012a1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-5-yl) acetate
• SMILES (Canonical): CC(=O)OC1C(C2C(CCC(C2(C3(C1(OC(CC3=O)(C)C=C)C)O)C)O)(C)C)O
• SMILES (Isomeric): CC(=O)OC1C(C2C(CCC(C2(C3(C1(OC(CC3=O)(C)C=C)C)O)C)O)(C)C)O
• InChI: InChI=1S/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(26)17(28-12(2)23)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3
• InChI Key: OHCQJHSOBUTRHG-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₇
• Molecular Weight: 410.50 g/mol
• Exact Mass: 410.23045342 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 66428-89-5
• 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-
• SR-01000075497
• UPCMLD-DP135
• Lopac0_000487
• CHEMBL1358402
• SCHEMBL14614874
• UPCMLD-DP135:001
• UPCMLD-DP135:002
• CHEBI:93891
• DTXSID00860823
• HMS3261B15
• Tox21_500487
• AKOS030228565
• CCG-204578
• LP00487
• NCGC00015445-02
• NCGC00015445-03
• NCGC00015445-04
• NCGC00015445-05
• NCGC00093892-01
• NCGC00161668-01
• NCGC00162171-01
• NCGC00261172-01
• EU-0100487
• FT-0626543
• F 6886
• SR-01000075497-1
• SR-01000075497-5
• BRD-A70449690-001-01-4
• Q27165646
• 1H-Naphtho[2, 5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy- 3,4a,7,7,10a-pentamethyl-, [3R-(3.alpha.,4a.beta., 5.beta.,6.beta.,6a.alpha.,10.alpha.,10a.beta.,10b.alpha.)]-
• 3-Ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxododecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate
• acetic acid (3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f][1]benzopyran-5-yl) ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8608	86.08%
Caco-2	-	0.6268	62.68%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6274	62.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.5516	55.16%
P-glycoprotein inhibitior	+	0.7664	76.64%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.6467	64.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8633	86.33%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9350	93.50%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.6719	67.19%
CYP inhibitory promiscuity	-	0.9606	96.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6519	65.19%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9383	93.83%
Skin irritation	-	0.5564	55.64%
Skin corrosion	-	0.8506	85.06%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7935	79.35%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8530	85.30%
Acute Oral Toxicity (c)	III	0.7869	78.69%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.6457	64.57%
Thyroid receptor binding	+	0.5938	59.38%
Glucocorticoid receptor binding	+	0.6646	66.46%
Aromatase binding	+	0.6860	68.60%
PPAR gamma	-	0.5477	54.77%
Honey bee toxicity	-	0.7376	73.76%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9477	94.77%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2960	P40145	Adenylate cyclase type VIII	93.7 nM	EC50	via Super-PRED
CHEMBL1293237	P54132	Bloom syndrome protein	11.2 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	794.3 nM	Potency	via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	501.2 nM	Potency	via Super-PRED
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	794.3 nM	Potency	via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	177.8 nM	Potency	via Super-PRED
CHEMBL1293298	Q01453	Peripheral myelin protein 22	21.3 nM	Potency	via Super-PRED
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	47 nM	EC50	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	79.4 nM; 501.2 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.88%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.39%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	89.59%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.07%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.60%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.20%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.05%	82.69%
CHEMBL2581	P07339	Cathepsin D	84.68%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.50%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.49%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.32%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.21%	91.24%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.58%	93.04%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.57%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.79%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.53%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.19%	97.09%

Plants that contains it

• Plectranthus barbatus

Cross-Links

• PubChem: 3413
• LOTUS: LTS0003808
• wikiData: Q27165646