(3S,4S,4aS,5R,6R,6aS,7R,11aS,11bR)-5,6-dibenzoyloxy-3,4a-dihydroxy-4,7,11b-trimethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-4-carboxylic acid

Details

• Internal ID: f5755183-a5aa-4d81-9a9b-4de0159194a0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids
• IUPAC Name: (3S,4S,4aS,5R,6R,6aS,7R,11aS,11bR)-5,6-dibenzoyloxy-3,4a-dihydroxy-4,7,11b-trimethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-4-carboxylic acid
• SMILES (Canonical): CC1C2C(CC3=C1C=CO3)C4(CCC(C(C4(C(C2OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6)O)(C)C(=O)O)O)C
• SMILES (Isomeric): C[C@@H]1[C@H]2[C@H](CC3=C1C=CO3)[C@]4(CC[C@@H]([C@]([C@@]4([C@@H]([C@@H]2OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6)O)(C)C(=O)O)O)C
• InChI: InChI=1S/C34H36O9/c1-19-22-15-17-41-24(22)18-23-26(19)27(42-29(36)20-10-6-4-7-11-20)28(43-30(37)21-12-8-5-9-13-21)34(40)32(23,2)16-14-25(35)33(34,3)31(38)39/h4-13,15,17,19,23,25-28,35,40H,14,16,18H2,1-3H3,(H,38,39)/t19-,23-,25-,26-,27+,28+,32+,33+,34-/m0/s1
• InChI Key: VTLVDCBXQBNNSN-GLRYWNFZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₆O₉
• Molecular Weight: 588.60 g/mol
• Exact Mass: 588.23593272 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9475	94.75%
Caco-2	-	0.7568	75.68%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7071	70.71%
OATP2B1 inhibitior	-	0.7201	72.01%
OATP1B1 inhibitior	+	0.8103	81.03%
OATP1B3 inhibitior	+	0.8502	85.02%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	+	0.8639	86.39%
P-glycoprotein inhibitior	+	0.7510	75.10%
P-glycoprotein substrate	-	0.5780	57.80%
CYP3A4 substrate	+	0.6988	69.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8682	86.82%
CYP3A4 inhibition	-	0.6168	61.68%
CYP2C9 inhibition	-	0.8075	80.75%
CYP2C19 inhibition	-	0.8375	83.75%
CYP2D6 inhibition	-	0.9499	94.99%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.7800	78.00%
CYP inhibitory promiscuity	-	0.9327	93.27%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9117	91.17%
Skin irritation	-	0.6118	61.18%
Skin corrosion	-	0.9127	91.27%
Ames mutagenesis	-	0.7540	75.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.8805	88.05%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5488	54.88%
skin sensitisation	-	0.9138	91.38%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.4553	45.53%
Acute Oral Toxicity (c)	I	0.3185	31.85%
Estrogen receptor binding	+	0.7273	72.73%
Androgen receptor binding	+	0.7363	73.63%
Thyroid receptor binding	+	0.5527	55.27%
Glucocorticoid receptor binding	+	0.7227	72.27%
Aromatase binding	+	0.5590	55.90%
PPAR gamma	+	0.6038	60.38%
Honey bee toxicity	-	0.8326	83.26%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9951	99.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.75%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.60%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.09%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.43%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.49%	99.23%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.87%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	91.16%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.00%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	86.12%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.26%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.63%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.51%	98.95%
CHEMBL5028	O14672	ADAM10	83.15%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.61%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.50%	97.14%
CHEMBL1914	P06276	Butyrylcholinesterase	82.43%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.01%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.94%	91.07%
CHEMBL4302	P08183	P-glycoprotein 1	80.33%	92.98%

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: 10698605
• NPASS: NPC36856
• LOTUS: LTS0076280
• wikiData: Q105292835