(2E,4E)-2,4,6-Octatrienoic acid [(5R)-1,3,5,5aalpha,6,7,8,9,9a,9balpha-decahydro-9balpha-hydroxy-6,6,9abeta-trimethyl-1-oxonaphtho[1,2-c]furan]-5beta-yl ester

Details

• Internal ID: 26408f3f-bb23-4c36-9ef6-72b80cfff539
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(5R,5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1-oxo-3,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] (2E,4E,6E)-octa-2,4,6-trienoate
• SMILES (Canonical): CC=CC=CC=CC(=O)OC1C=C2COC(=O)C2(C3(C1C(CCC3)(C)C)C)O
• SMILES (Isomeric): C/C=C/C=C/C=C/C(=O)O[C@@H]1C=C2COC(=O)[C@@]2([C@@]3([C@@H]1C(CCC3)(C)C)C)O
• InChI: InChI=1S/C23H30O5/c1-5-6-7-8-9-11-18(24)28-17-14-16-15-27-20(25)23(16,26)22(4)13-10-12-21(2,3)19(17)22/h5-9,11,14,17,19,26H,10,12-13,15H2,1-4H3/b6-5+,8-7+,11-9+/t17-,19+,22+,23+/m1/s1
• InChI Key: DPTZOOXIEWHODB-XLDMSTKGSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀O₅
• Molecular Weight: 386.50 g/mol
• Exact Mass: 386.20932405 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.65
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• (2E,4E)-2,4,6-Octatrienoic acid [(5R)-1,3,5,5aalpha,6,7,8,9,9a,9balpha-decahydro-9balpha-hydroxy-6,6,9abeta-trimethyl-1-oxonaphtho[1,2-c]furan]-5beta-yl ester
• [(5R,5As,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1-oxo-3,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] (2E,4E,6E)-octa-2,4,6-trienoate
• MEGxm0_000041
• CHEMBL1078730
• ACon0_000051
• ACon1_001277
• NCGC00169507-01
• NCGC00169507-03
• 173560-30-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	-	0.5699	56.99%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8604	86.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8477	84.77%
OATP1B3 inhibitior	+	0.7965	79.65%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5604	56.04%
BSEP inhibitior	+	0.5982	59.82%
P-glycoprotein inhibitior	-	0.4552	45.52%
P-glycoprotein substrate	-	0.7381	73.81%
CYP3A4 substrate	+	0.6517	65.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9118	91.18%
CYP3A4 inhibition	-	0.8389	83.89%
CYP2C9 inhibition	+	0.5401	54.01%
CYP2C19 inhibition	-	0.8029	80.29%
CYP2D6 inhibition	-	0.9063	90.63%
CYP1A2 inhibition	+	0.5192	51.92%
CYP2C8 inhibition	-	0.5595	55.95%
CYP inhibitory promiscuity	-	0.7849	78.49%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5186	51.86%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9776	97.76%
Skin irritation	-	0.5175	51.75%
Skin corrosion	-	0.9250	92.50%
Ames mutagenesis	-	0.5554	55.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4326	43.26%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.6126	61.26%
skin sensitisation	-	0.8214	82.14%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6379	63.79%
Acute Oral Toxicity (c)	III	0.5896	58.96%
Estrogen receptor binding	+	0.7571	75.71%
Androgen receptor binding	+	0.6848	68.48%
Thyroid receptor binding	+	0.6649	66.49%
Glucocorticoid receptor binding	+	0.6681	66.81%
Aromatase binding	+	0.6586	65.86%
PPAR gamma	-	0.5446	54.46%
Honey bee toxicity	-	0.8545	85.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9950	99.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.65%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.75%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.20%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.44%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.02%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.97%	89.00%
CHEMBL2039	P27338	Monoamine oxidase B	85.61%	92.51%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.79%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.36%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.98%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.67%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.60%	99.23%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.51%	83.57%
CHEMBL1937	Q92769	Histone deacetylase 2	80.28%	94.75%

Plants that contains it

• Aegiceras corniculatum
• Ajuga integrifolia
• Allium multibulbosum
• Arbutus menziesii
• Bruguiera gymnorhiza
• Cinnamosma madagascariensis
• Echiochilon pauciflorum
• Helichrysum nudifolium
• Hypoxis nyasica
• Isoberlinia angolensis
• Macaranga sinensis
• Mirabilis jalapa
• Nicoteba betonica
• Otostegia fruticosa
• Paranephelius uniflorus
• Rhododendron aureum
• Seriphidium lessingianum
• Sonneratia alba
• Tephroseris integrifolia
• Terminalia tetraphylla
• Teucrium orientale
• Veltheimia capensis
• Xylopia aethiopica

Cross-Links

• PubChem: 10407821
• NPASS: NPC179798
• LOTUS: LTS0157713
• wikiData: Q77386004