Isosteviol

Details

• Internal ID: c23db4a0-e1db-453f-9803-d47e184ee8af
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• InChI: InChI=1S/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14-,17-,18+,19+,20-/m0/s1
• InChI Key: KFVUFODCZDRVSS-XGBBNYNSSA-N
• Popularity: 139 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.44
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 27975-19-5
• iso-steviol
• Ketoisostevic Acid
• (-)-Isosteviol
• CCRIS 6121
• NSC 231875
• UNII-091QB7QO95
• ent-16-ketobeyeran-19-oic acid
• 091QB7QO95
• 17-Nor-8-beta,13-beta-kauran-18-oic acid, 13-methyl-16-oxo-
• (4-alpha,8-beta,13-beta)-13-Methyl-16-oxo-17-norkauran-18-oic acid
• 17-Norkauran-18-oic acid, 13-methyl-16-oxo-, (4-alpha,8-beta,13-beta)-
• NSC-231875
• 17-Norkauran-18-oic acid, 13-methyl-16-oxo-, (4a,8b,13b)-
• (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-Trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid
• CHEMBL462653
• SCHEMBL3489810
• DTXSID70950664
• CHEBI:189936
• HY-N0872
• BDBM50504374
• MFCD28411514
• NSC731915
• s3905
• AKOS030496339
• CCG-267685
• CS-3919
• NSC-731915
• NCGC00485884-01
• I1069
• A876816
• Q27236439
• (4alpha,8beta,13beta)-13-methyl-16-oxo-17-norkauran-18-oic acid
• (4-alpha,8-beta,13-beta)-13-methyl-16-oxo-17-norkauran-18-oicacid
• 17-NORKAURAN-18-OIC ACID, 13-METHYL-16-OXO-, (4.ALPHA.,8.BETA.,13.BETA.)-
• 17-NORKAURAN-18-OIC ACID, 13-METHYL-16-OXO-, (4alpha,8beta,13beta)-
• (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	+	0.9032	90.32%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8371	83.71%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8668	86.68%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	-	0.4682	46.82%
P-glycoprotein inhibitior	-	0.6517	65.17%
P-glycoprotein substrate	-	0.8905	89.05%
CYP3A4 substrate	+	0.5712	57.12%
CYP2C9 substrate	+	0.5878	58.78%
CYP2D6 substrate	-	0.8517	85.17%
CYP3A4 inhibition	-	0.8853	88.53%
CYP2C9 inhibition	-	0.8129	81.29%
CYP2C19 inhibition	-	0.9064	90.64%
CYP2D6 inhibition	-	0.9729	97.29%
CYP1A2 inhibition	-	0.8141	81.41%
CYP2C8 inhibition	-	0.8799	87.99%
CYP inhibitory promiscuity	-	0.9850	98.50%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6292	62.92%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.7999	79.99%
Skin irritation	+	0.6570	65.70%
Skin corrosion	-	0.8892	88.92%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4909	49.09%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7342	73.42%
skin sensitisation	-	0.7768	77.68%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6156	61.56%
Acute Oral Toxicity (c)	II	0.5667	56.67%
Estrogen receptor binding	+	0.8072	80.72%
Androgen receptor binding	+	0.6159	61.59%
Thyroid receptor binding	+	0.7108	71.08%
Glucocorticoid receptor binding	+	0.7865	78.65%
Aromatase binding	+	0.6217	62.17%
PPAR gamma	-	0.6376	63.76%
Honey bee toxicity	-	0.9500	95.00%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9911	99.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL244	P00742	Coagulation factor X	641.68 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.68%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.16%	96.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.96%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.22%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.97%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.83%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.88%	93.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.91%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.46%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.40%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.49%	91.19%

Plants that contains it

• Ceriops decandra

Cross-Links

• PubChem: 99514
• LOTUS: LTS0237695
• wikiData: Q27236439