(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol

Details

• Internal ID: ac8ea1b5-9c91-4216-816c-8a0aeed0d064
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Tetraterpenoids > Carotenoids > Xanthophylls
• IUPAC Name: (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
• SMILES (Canonical): CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2C(=CC(CC2(C)C)O)C)C)C
• SMILES (Isomeric): CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C2C(=C[C@@H](CC2(C)C)O)C)/C)/C
• InChI: InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37?/m0/s1
• InChI Key: KBPHJBAIARWVSC-CFWGZHMLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₆O₂
• Molecular Weight: 568.90 g/mol
• Exact Mass: 568.42803102 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 11.00
• Atomic LogP (AlogP): 10.40
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	-	0.7944	79.44%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6198	61.98%
OATP2B1 inhibitior	-	0.7150	71.50%
OATP1B1 inhibitior	+	0.7737	77.37%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9947	99.47%
P-glycoprotein inhibitior	+	0.7859	78.59%
P-glycoprotein substrate	-	0.5509	55.09%
CYP3A4 substrate	+	0.6532	65.32%
CYP2C9 substrate	-	0.8191	81.91%
CYP2D6 substrate	-	0.7760	77.60%
CYP3A4 inhibition	-	0.8808	88.08%
CYP2C9 inhibition	-	0.7723	77.23%
CYP2C19 inhibition	+	0.5225	52.25%
CYP2D6 inhibition	-	0.9368	93.68%
CYP1A2 inhibition	-	0.9079	90.79%
CYP2C8 inhibition	+	0.5242	52.42%
CYP inhibitory promiscuity	-	0.6267	62.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7348	73.48%
Carcinogenicity (trinary)	Non-required	0.5753	57.53%
Eye corrosion	-	0.9776	97.76%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.6972	69.72%
Skin corrosion	-	0.9646	96.46%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8887	88.87%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8229	82.29%
skin sensitisation	+	0.8612	86.12%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.6966	69.66%
Acute Oral Toxicity (c)	III	0.7696	76.96%
Estrogen receptor binding	+	0.8326	83.26%
Androgen receptor binding	+	0.6904	69.04%
Thyroid receptor binding	+	0.7189	71.89%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	-	0.4936	49.36%
PPAR gamma	+	0.7543	75.43%
Honey bee toxicity	-	0.7885	78.85%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9234	92.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.94%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	92.94%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.80%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.58%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	85.95%	94.75%
CHEMBL1870	P28702	Retinoid X receptor beta	85.51%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.27%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.86%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.20%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.04%	92.94%
CHEMBL2004	P48443	Retinoid X receptor gamma	82.52%	100.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.37%	85.30%
CHEMBL2061	P19793	Retinoid X receptor alpha	81.35%	91.67%
CHEMBL2581	P07339	Cathepsin D	81.33%	98.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.10%	90.24%
CHEMBL3524	P56524	Histone deacetylase 4	80.63%	92.97%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.54%	91.71%
CHEMBL4208	P20618	Proteasome component C5	80.12%	90.00%

Plants that contains it

• Amentotaxus yunnanensis
• Arabidopsis thaliana
• Averrhoa carambola
• Boronia megastigma
• Calendula officinalis
• Capsicum annuum
• Citrus × aurantium
• Citrus limon
• Citrus trifoliata
• Coffea arabica
• Cuscuta australis
• Duranta erecta
• Hippophae rhamnoides
• Lycium barbarum
• Lycium chinense
• Oryza sativa
• Perilla frutescens
• Psidium guajava
• Pteris multifida
• Spinacia oleracea
• Taraxacum officinale
• Thalictrum foliolosum

Cross-Links

• PubChem: 25245095
• NPASS: NPC281457
• LOTUS: LTS0035691
• wikiData: Q103815943