[(4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f]benzofuran-5-yl] (E)-3-phenylprop-2-enoate

Details

• Internal ID: 019191a4-b2a3-4bca-9949-c3a4de2c5f02
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-5-yl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC1C2C(CC3=C1C=CO3)C4(CCCC(C4(C(C2O)OC(=O)C=CC5=CC=CC=C5)O)(C)C)C
• SMILES (Isomeric): C[C@@H]1[C@H]2[C@H](CC3=C1C=CO3)[C@]4(CCCC([C@@]4([C@@H]([C@@H]2O)OC(=O)/C=C/C5=CC=CC=C5)O)(C)C)C
• InChI: InChI=1S/C29H36O5/c1-18-20-13-16-33-22(20)17-21-24(18)25(31)26(29(32)27(2,3)14-8-15-28(21,29)4)34-23(30)12-11-19-9-6-5-7-10-19/h5-7,9-13,16,18,21,24-26,31-32H,8,14-15,17H2,1-4H3/b12-11+/t18-,21-,24-,25+,26+,28+,29+/m0/s1
• InChI Key: IGNZARMTFKDIDD-PSGKSZDDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₅
• Molecular Weight: 464.60 g/mol
• Exact Mass: 464.25627424 g/mol
• Topological Polar Surface Area (TPSA): 79.90 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.12
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• (8beta,10beta,14alpha)-6beta-[(3-Phenyl-1-oxo-2-propenyl)oxy]-12,16-epoxycassa-12,15-diene-5alpha,7beta-diol
• [(4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f]benzofuran-5-yl] (E)-3-phenylprop-2-enoate
• 2-Propenoic acid, 3-phenyl-, (4aR,5R,6R,6aS,7R,11aS,11bR)-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydro-4a,6-dihydroxy-4,4,7,11b-tetramethylphenanthro[3,2-b]furan-5-yl ester, (2E)-
• Cinnamic acid 4,4,7beta,11balpha-tetramethyl-4abeta,6alpha-dihydroxy-1,2,3,4,4a,5,6,6aalpha,7,11,11abeta,11b-dodecahydrophenanthro[3,2-b]furan-5alpha-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	-	0.6063	60.63%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7203	72.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8445	84.45%
OATP1B3 inhibitior	+	0.7883	78.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6821	68.21%
BSEP inhibitior	+	0.8307	83.07%
P-glycoprotein inhibitior	+	0.6620	66.20%
P-glycoprotein substrate	-	0.6282	62.82%
CYP3A4 substrate	+	0.6943	69.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8772	87.72%
CYP3A4 inhibition	-	0.5487	54.87%
CYP2C9 inhibition	-	0.6884	68.84%
CYP2C19 inhibition	-	0.6318	63.18%
CYP2D6 inhibition	-	0.9144	91.44%
CYP1A2 inhibition	+	0.6158	61.58%
CYP2C8 inhibition	+	0.7640	76.40%
CYP inhibitory promiscuity	-	0.6950	69.50%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5749	57.49%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9433	94.33%
Skin irritation	-	0.6484	64.84%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8888	88.88%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5073	50.73%
skin sensitisation	-	0.8579	85.79%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8639	86.39%
Acute Oral Toxicity (c)	III	0.3772	37.72%
Estrogen receptor binding	+	0.7507	75.07%
Androgen receptor binding	+	0.7547	75.47%
Thyroid receptor binding	+	0.6073	60.73%
Glucocorticoid receptor binding	+	0.7529	75.29%
Aromatase binding	+	0.6688	66.88%
PPAR gamma	+	0.6058	60.58%
Honey bee toxicity	-	0.7978	79.78%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.88%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.73%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.07%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.70%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	93.41%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.27%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.12%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.06%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.63%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.53%	96.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.43%	91.71%
CHEMBL4208	P20618	Proteasome component C5	86.16%	90.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.49%	93.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.04%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.79%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.35%	95.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.16%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.24%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.79%	100.00%
CHEMBL5028	O14672	ADAM10	81.50%	97.50%

Plants that contains it

• Aeschynanthus pulcher
• Betula papyrifera
• Boronia alata
• Caesalpinia pulcherrima
• Cinnamomum philippinense
• Coronilla cretica
• Cryptochilus siamensis
• Cyperus capitatus
• Delphinium tricorne
• Ephedra altissima
• Erica cinerea
• Gymnosporia emarginata
• Haemanthus albiflos
• Helleborus viridis
• Hordeum bulbosum
• Iris sibirica
• Isolona pilosa
• Jatropha gossypiifolia
• Lepidaploa aurea
• Litsea nitida
• Lobelia langeana
• Magnolia henryi
• Micromelum minutum
• Peltophorum dubium
• Prunus pseudocerasus
• Salvia miniata
• Sibiraea angustata
• Tamarix dioica
• Tripterygium wilfordii
• Valeriana officinalis
• Xanthium spinosum subsp. spinosum

Cross-Links

• PubChem: 6479669
• NPASS: NPC210450
• LOTUS: LTS0272734
• wikiData: Q105112734