(1R,2R,4S)-1-[(1E,3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15-octaen-17-ynyl]-2,6,6-trimethylcyclohexane-1,2,4-triol

Details

• Internal ID: bf871d34-659f-4b3d-a6a9-1aa0313e7786
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,2R,4S)-1-[(1E,3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15-octaen-17-ynyl]-2,6,6-trimethylcyclohexane-1,2,4-triol
• SMILES (Canonical): CC1=C(C(CC(C1)O)(C)C)C#CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2(C(CC(CC2(C)O)O)(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=C/[C@@]2([C@](C[C@H](CC2(C)C)O)(C)O)O)/C)/C
• InChI: InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40(44)38(8,9)27-35(42)28-39(40,10)43/h11-20,23-24,34-35,41-44H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39-,40-/m1/s1
• InChI Key: ZEXQVPRPMQVOFT-DGDOQUKGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₆O₄
• Molecular Weight: 600.90 g/mol
• Exact Mass: 600.41786026 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 9.10
• Atomic LogP (AlogP): 8.16
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• (3S,3'R,5R,6R)-7',8'-Didehydro-5,6-dihydro-3,3',5,6-tetrahydroxy-beta,beta-carotene
• DTXSID701138928
• Q63396480

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9106	91.06%
Caco-2	-	0.8307	83.07%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6495	64.95%
OATP2B1 inhibitior	-	0.5682	56.82%
OATP1B1 inhibitior	+	0.8752	87.52%
OATP1B3 inhibitior	+	0.9328	93.28%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9892	98.92%
P-glycoprotein inhibitior	+	0.7532	75.32%
P-glycoprotein substrate	-	0.5360	53.60%
CYP3A4 substrate	+	0.6672	66.72%
CYP2C9 substrate	-	0.5858	58.58%
CYP2D6 substrate	-	0.8142	81.42%
CYP3A4 inhibition	-	0.8291	82.91%
CYP2C9 inhibition	-	0.7873	78.73%
CYP2C19 inhibition	-	0.5632	56.32%
CYP2D6 inhibition	-	0.9325	93.25%
CYP1A2 inhibition	-	0.8851	88.51%
CYP2C8 inhibition	+	0.4503	45.03%
CYP inhibitory promiscuity	-	0.8119	81.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6072	60.72%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.7173	71.73%
Skin corrosion	-	0.9147	91.47%
Ames mutagenesis	+	0.6209	62.09%
Human Ether-a-go-go-Related Gene inhibition	+	0.8386	83.86%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6406	64.06%
skin sensitisation	-	0.5605	56.05%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6548	65.48%
Acute Oral Toxicity (c)	III	0.5079	50.79%
Estrogen receptor binding	+	0.7964	79.64%
Androgen receptor binding	+	0.6956	69.56%
Thyroid receptor binding	+	0.6902	69.02%
Glucocorticoid receptor binding	+	0.8056	80.56%
Aromatase binding	+	0.6063	60.63%
PPAR gamma	+	0.7385	73.85%
Honey bee toxicity	-	0.7102	71.02%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9596	95.96%

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	94.14%	96.09%
CHEMBL3524	P56524	Histone deacetylase 4	93.13%	92.97%
CHEMBL221	P23219	Cyclooxygenase-1	93.01%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.67%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	90.84%	94.75%
CHEMBL2996	Q05655	Protein kinase C delta	88.36%	97.79%
CHEMBL3492	P49721	Proteasome Macropain subunit	88.13%	90.24%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.09%	92.94%
CHEMBL1870	P28702	Retinoid X receptor beta	84.75%	95.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.21%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.02%	100.00%
CHEMBL2004	P48443	Retinoid X receptor gamma	83.64%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	83.42%	95.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.22%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.95%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.83%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.62%	89.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	80.81%	97.47%

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: 102146782
• NPASS: NPC124598
• LOTUS: LTS0081229
• wikiData: Q63396480