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

Details

• Internal ID: 7b2a4846-cebb-4da9-aa89-d5c303b715bf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2R,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O
• SMILES (Isomeric): C[C@@H]1CC[C@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O
• InChI: InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30-/m1/s1
• InChI Key: WCGUUGGRBIKTOS-XUTPQDOASA-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: 7.30
• Atomic LogP (AlogP): 7.09
• 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	+	0.6086	60.86%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8699	86.99%
OATP2B1 inhibitior	-	0.7168	71.68%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.8278	82.78%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.8292	82.92%
CYP3A4 substrate	+	0.6600	66.00%
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	-	0.5587	55.87%
CYP inhibitory promiscuity	-	0.9046	90.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5962	59.62%
Eye corrosion	-	0.9948	99.48%
Eye irritation	-	0.9387	93.87%
Skin irritation	+	0.6328	63.28%
Skin corrosion	-	0.9644	96.44%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4928	49.28%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5916	59.16%
skin sensitisation	+	0.5630	56.30%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.8316	83.16%
Estrogen receptor binding	+	0.7492	74.92%
Androgen receptor binding	+	0.7283	72.83%
Thyroid receptor binding	+	0.6846	68.46%
Glucocorticoid receptor binding	+	0.8495	84.95%
Aromatase binding	+	0.6607	66.07%
PPAR gamma	+	0.5573	55.73%
Honey bee toxicity	-	0.8551	85.51%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	158.5 nM	Potency	via Super-PRED
CHEMBL5533	Q04206	Nuclear factor NF-kappa-B p65 subunit	31 nM	IC50	via Super-PRED
CHEMBL1741186	P51449	Nuclear receptor ROR-gamma	130 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.51%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.14%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.47%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.72%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.40%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.53%	85.30%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.38%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.97%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.12%	93.00%
CHEMBL5028	O14672	ADAM10	80.08%	97.50%

Plants that contains it

• Agrimonia pilosa
• Campsis grandiflora
• Campsis radicans
• Chaenomeles sinensis
• Chaenomeles speciosa
• Cornus officinalis
• Crataegus pinnatifida
• Cynomorium coccineum subsp. songaricum
• Diospyros kaki
• Dipsacus inermis
• Echinops setifer
• Elsholtzia ciliata
• Eriobotrya japonica
• Eucommia ulmoides
• Forsythia suspensa
• Forsythia viridissima
• Ilex cornuta
• Ipomoea nil
• Ipomoea purpurea
• Isodon rubescens
• Knoxia roxburghii
• Leuzea uniflora
• Ligustrum lucidum
• Liquidambar formosana
• Lonicera confusa
• Lonicera hypoglauca
• Lonicera japonica
• Lonicera macrantha
• Lycopus lucidus
• Mentha arvensis
• Mentha canadensis
• Mosla chinensis
• Myristica fragrans
• Nepeta tenuifolia
• Patrinia scabiosifolia
• Patrinia villosa
• Perilla frutescens
• Potentilla chinensis
• Prunella vulgaris
• Pseudostellaria heterophylla
• Punica granatum
• Pyrola japonica
• Rubus chingii
• Rubus coreanus
• Salvia miltiorrhiza
• Salvia tonalensis
• Scleromitrion diffusum
• Sigesbeckia glabrescens
• Sigesbeckia pubescens
• Styrax benzoin
• Styrax tonkinensis
• Syzygium aromaticum
• Tetradium ruticarpum
• Uncaria macrophylla
• Uncaria rhynchophylla
• Uncaria sinensis
• Vaccaria hispanica
• Verbena officinalis
• Viscum album
• Viscum coloratum
• Vitex trifolia
• Vitex trifolia subsp. litoralis
• Ziziphus jujuba

Cross-Links

• PubChem: 45483617
• NPASS: NPC288537
• LOTUS: LTS0245303
• wikiData: Q105301745