Amarouciaxanthin B/Sidnyaxanthin

Details

• Internal ID: 7bb805c0-5f83-4de9-8203-c1e48d4684d6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4S)-4-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-ynyl]-3,5,5-trimethylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=C(C(CC(C1)O)(C)C)C#CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C(=O)CC2(C(=CC(=O)CC2(C)C)C)O)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(=O)C[C@]2(C(=CC(=O)CC2(C)C)C)O)/C)/C
• InChI: InChI=1S/C40H52O4/c1-28(17-13-18-30(3)21-22-36-32(5)23-34(41)25-38(36,7)8)15-11-12-16-29(2)19-14-20-31(4)37(43)27-40(44)33(6)24-35(42)26-39(40,9)10/h11-20,24,34,41,44H,23,25-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t34-,40-/m1/s1
• InChI Key: XUKJTNSSWNXSQU-OMEVNMJGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₂O₄
• Molecular Weight: 596.80 g/mol
• Exact Mass: 596.38656014 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 8.70
• Atomic LogP (AlogP): 8.58
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• Amarouciaxanthin B/ Sidnyaxanthin
• Sidnyaxanthin
• CHEMBL445440
• Amarouciaxanthin B/Sidnyaxanthin
• LMPR01070079
• Q63395986
• (4S)-4-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-ynyl]-3,5,5-trimethylcyclohex-2-en-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	-	0.8213	82.13%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8419	84.19%
OATP2B1 inhibitior	+	0.5723	57.23%
OATP1B1 inhibitior	+	0.8361	83.61%
OATP1B3 inhibitior	+	0.9191	91.91%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9712	97.12%
P-glycoprotein inhibitior	+	0.7931	79.31%
P-glycoprotein substrate	+	0.5098	50.98%
CYP3A4 substrate	+	0.6969	69.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8793	87.93%
CYP3A4 inhibition	-	0.6765	67.65%
CYP2C9 inhibition	-	0.8313	83.13%
CYP2C19 inhibition	-	0.6229	62.29%
CYP2D6 inhibition	-	0.9362	93.62%
CYP1A2 inhibition	-	0.9495	94.95%
CYP2C8 inhibition	+	0.4662	46.62%
CYP inhibitory promiscuity	-	0.8702	87.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8041	80.41%
Carcinogenicity (trinary)	Non-required	0.6568	65.68%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9154	91.54%
Skin irritation	-	0.6913	69.13%
Skin corrosion	-	0.9657	96.57%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8352	83.52%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6264	62.64%
skin sensitisation	+	0.5206	52.06%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4886	48.86%
Acute Oral Toxicity (c)	I	0.3708	37.08%
Estrogen receptor binding	+	0.8279	82.79%
Androgen receptor binding	+	0.7297	72.97%
Thyroid receptor binding	+	0.6869	68.69%
Glucocorticoid receptor binding	+	0.7811	78.11%
Aromatase binding	+	0.5978	59.78%
PPAR gamma	+	0.7543	75.43%
Honey bee toxicity	-	0.7022	70.22%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9968	99.68%

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	97.12%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.90%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.37%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.66%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.25%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	90.32%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.94%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.66%	93.99%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.54%	100.00%
CHEMBL1871	P10275	Androgen Receptor	86.37%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.72%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.67%	92.94%
CHEMBL4208	P20618	Proteasome component C5	84.44%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.07%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.99%	86.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.92%	99.23%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.86%	96.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.38%	94.80%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	82.17%	80.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.16%	91.07%

Plants that contains it

• Achillea macrophylla
• Agave aurea
• Ageratina havanensis
• Ajuga spectabilis
• Alstroemeria revoluta
• Astragalus tragacantha
• Baphia nitida
• Chamaecyparis lawsoniana
• Corynanthe mayumbensis
• Crataegus viridis var. ovata
• Crinum erubescens
• Cylindrolobus foetidus
• Emilia sonchifolia
• Encephalartos altensteinii
• Euphorbia kamerunica
• Euphorbia marginata
• Excoecaria oppositifolia
• Gardenia collinsae
• Grindelia hirsutula
• Gymnosporia senegalensis
• Jungermannia hyalina
• Kobresia nepalensis
• Ligularia muliensis
• Marrubium alysson
• Melaleuca viminalis
• Melampodium americanum
• Neolitsea aciculata
• Neolitsea pulchella
• Nuphar lutea
• Pentzia incana
• Prangos pabularia
• Selliguea feei
• Shuteria vestita
• Simaba orinocensis
• Stevia chamaedrys
• Teucrium oxylepis
• Thelypteris triphylla
• Trifolium subterraneum
• Trillium camschatcense
• Ursinia abrotanifolia

Cross-Links

• PubChem: 16061221
• NPASS: NPC78159
• LOTUS: LTS0266828
• wikiData: Q63395986