Isoforskolin

Details

• Internal ID: 6adededf-388f-46db-b20c-a56597c95b53
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-6-yl] acetate
• 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(28-12(2)23)17(26)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16-,17-,19-,20-,21+,22-/m0/s1
• InChI Key: CLOQVZCSBYBUPB-KGGHGJDLSA-N
• Popularity: 4 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

• Excolabdone C
• Coleonol B
• 64657-21-2
• UNII-256AFQ3YUN
• 256AFQ3YUN
• Isoforskolin (constituent of forskohlii) [DSC]
• 6beta-acetoxy-8,13-epoxy-1alpha,7beta,9alpha-trihydroxylabd-14-en-11-one
• [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-6-yl] acetate
• 1H-Naphtho(2,1-b)pyran-1-one, 6-(acetyloxy)-3-ethenyldodecahydro-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-, (3R-(3alpha,4abeta,5beta,6beta,6aalpha,10alpha,10abeta,10balpha))-
• 6.BETA.-ACETOXY-8,13-EPOXY-1.ALPHA.,7.BETA.,9.ALPHA.-TRIHYDROXYLABD-14-EN-11-ONE
• 1H-NAPHTHO(2,1-B)PYRAN-1-ONE, 6-(ACETYLOXY)-3-ETHENYLDODECAHYDRO-5,10,10B-TRIHYDROXY-3,4A,7,7,10A-PENTAMETHYL-, (3R-(3.ALPHA.,4A.BETA.,5.BETA.,6.BETA.,6A.ALPHA.,10.ALPHA.,10A.BETA.,10B.ALPHA.))-
• ((3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo(f)chromen-6-yl) acetate
• RefChem:149342
• ISOFORSKOLIN (CONSTITUENT OF FORSKOHLII)
• Iso-Forskolin
• MLS000517267
• SMR000127420
• (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-Trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyldodecahydro-1H-benzo[f]chromen-6-yl acetate
• (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6-(Acetyloxy)-3-ethenyldodecahydro-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-1-one
• 6BETA-ACETOXY-8,13-EPOXY-1ALPHA,7BETA,9ALPHA-TRIHYDROXY-LABD-14-EN-11-ONE
• MFCD00078929
• Isoforskolin (Standard)
• orb1297414
• orb3139255
• SCHEMBL4928148
• CHEMBL1519619
• BDBM83744
• cid_9549169
• HY-N6927R
• REGID_for_CID_9549169
• HMS2267A05
• HY-N6927
• TN1520
• AKOS037514904
• EBC-615437
• (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-6-yl acetate
• AC-35072
• MS-27083
• CS-0027682
• Q27253921
• [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-5,10,10b-tris(oxidanyl)-1-oxidanylidene-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-6-yl] ethanoate
• [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-6-yl] acetate
• acetic acid [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f][1]benzopyran-6-yl] ester
• acetic acid [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-trihydroxy-1-keto-3,4a,7,7,10a-pentamethyl-3-vinyl-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-6-yl] ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8608	86.08%
Caco-2	-	0.7071	70.71%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6274	62.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8978	89.78%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.8514	85.14%
P-glycoprotein inhibitior	-	0.5748	57.48%
P-glycoprotein substrate	-	0.8807	88.07%
CYP3A4 substrate	+	0.6736	67.36%
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	-	0.7363	73.63%
CYP inhibitory promiscuity	-	0.9606	96.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6519	65.19%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9318	93.18%
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	-	0.5462	54.62%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5235	52.35%
skin sensitisation	-	0.7935	79.35%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8904	89.04%
Acute Oral Toxicity (c)	III	0.7869	78.69%
Estrogen receptor binding	+	0.8012	80.12%
Androgen receptor binding	+	0.6387	63.87%
Thyroid receptor binding	+	0.6241	62.41%
Glucocorticoid receptor binding	+	0.7221	72.21%
Aromatase binding	+	0.6809	68.09%
PPAR gamma	-	0.5819	58.19%
Honey bee toxicity	-	0.7229	72.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9477	94.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.89%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	93.08%	83.82%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.93%	82.50%
CHEMBL340	P08684	Cytochrome P450 3A4	89.34%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.58%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.17%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.81%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.22%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.20%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.67%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.31%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.30%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.69%	92.94%
CHEMBL2581	P07339	Cathepsin D	81.22%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.77%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.72%	93.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.49%	85.14%

Plants that contains it

• Coleus barbatus var. barbatus
• Excoecaria cochinchinensis

Cross-Links

• PubChem: 9549169
• LOTUS: LTS0048268
• wikiData: Q27253921