(4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: 9242a114-59bc-43d7-873f-2c7cdd4b6a08
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O
• InChI: InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30+/m0/s1
• InChI Key: MIJYXULNPSFWEK-ZZAAMMQTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₃
• Molecular Weight: 456.70 g/mol
• Exact Mass: 456.36034539 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 7.50
• Atomic LogP (AlogP): 7.23
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.5596	55.96%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8699	86.99%
OATP2B1 inhibitior	-	0.7192	71.92%
OATP1B1 inhibitior	+	0.8808	88.08%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.9111	91.11%
P-glycoprotein inhibitior	-	0.9165	91.65%
P-glycoprotein substrate	-	0.9082	90.82%
CYP3A4 substrate	+	0.6412	64.12%
CYP2C9 substrate	-	0.8404	84.04%
CYP2D6 substrate	-	0.8509	85.09%
CYP3A4 inhibition	-	0.8695	86.95%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.9169	91.69%
CYP2C8 inhibition	-	0.7001	70.01%
CYP inhibitory promiscuity	-	0.9046	90.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5962	59.62%
Eye corrosion	-	0.9948	99.48%
Eye irritation	-	0.9085	90.85%
Skin irritation	+	0.6328	63.28%
Skin corrosion	-	0.9644	96.44%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5287	52.87%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	+	0.5630	56.30%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7559	75.59%
Acute Oral Toxicity (c)	III	0.8316	83.16%
Estrogen receptor binding	+	0.8127	81.27%
Androgen receptor binding	+	0.6710	67.10%
Thyroid receptor binding	+	0.6460	64.60%
Glucocorticoid receptor binding	+	0.8447	84.47%
Aromatase binding	+	0.6767	67.67%
PPAR gamma	+	0.6306	63.06%
Honey bee toxicity	-	0.8853	88.53%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	72 nM	Ki	via Super-PRED
CHEMBL4081	P13726	Coagulation factor III	4.975 nM	IC50	via Super-PRED
CHEMBL4804	P30305	Dual specificity phosphatase Cdc25B	980 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	93.38%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.20%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.13%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.78%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.68%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.96%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.80%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.76%	100.00%
CHEMBL2581	P07339	Cathepsin D	82.43%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.92%	93.00%

Plants that contains it

• Achyranthes bidentata
• Agrimonia pilosa
• Akebia quinata
• Akebia trifoliata
• Bassia scoparia
• Campsis grandiflora
• Campsis radicans
• Chaenomeles sinensis
• Chaenomeles speciosa
• Cissampelos pareira
• Cornus officinalis
• Crataegus pinnatifida
• Diospyros kaki
• Dipsacus inermis
• Eriobotrya japonica
• Forsythia suspensa
• Forsythia viridissima
• Gentiana crassicaulis
• Gentiana dahurica
• Gentiana macrophylla
• Gentiana straminea
• Gleditsia japonica
• Gleditsia sinensis
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Isodon rubescens
• Knoxia roxburghii
• Ligustrum lucidum
• Liquidambar formosana
• Lonicera confusa
• Lonicera hypoglauca
• Lonicera macrantha
• Lycopus lucidus
• Mentha arvensis
• Mentha canadensis
• Morus alba
• Morus indica
• Myristica fragrans
• Panax ginseng
• Panax japonicus
• Perilla frutescens
• Phlomoides umbrosa
• Pogostemon cablin
• Prunella vulgaris
• Punica granatum
• Pyrola japonica
• Rhododendron dauricum
• Scleromitrion diffusum
• Styrax benzoin
• Styrax tonkinensis
• Swertia chirata
• Syzygium aromaticum
• Tetradium ruticarpum
• Verbena officinalis
• Viscum album
• Viscum coloratum
• Ziziphus jujuba

Cross-Links

• PubChem: 45483610
• NPASS: NPC255662
• LOTUS: LTS0038539
• wikiData: Q105165035