(2'R,5aR,7aR,8R,9S,11aR,11bR)-9-[(S)-furan-3-yl-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxospiro[6,10,11,11a-tetrahydro-5aH-benzo[g][2]benzoxepine-8,3'-oxirane]-2'-carboxylic acid

Details

• Internal ID: 6ab8a729-f999-4af8-99a1-c8f11d86d240
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: (2'R,5aR,7aR,8R,9S,11aR,11bR)-9-[(S)-furan-3-yl-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxospiro[6,10,11,11a-tetrahydro-5aH-benzo[g][2]benzoxepine-8,3'-oxirane]-2'-carboxylic acid
• SMILES (Canonical): CC1(C2CC(=O)C3(C(C2(C=CC(=O)O1)C)CCC(C34C(O4)C(=O)O)(C)C(C5=COC=C5)OC6C(C(C(C(O6)CO)O)O)O)C)C
• SMILES (Isomeric): C[C@]1(CC[C@@H]2[C@]3(C=CC(=O)OC([C@@H]3CC(=O)[C@]2([C@@]14[C@@H](O4)C(=O)O)C)(C)C)C)[C@H](C5=COC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C32H42O13/c1-28(2)18-12-19(34)31(5)17(29(18,3)9-7-20(35)44-28)6-10-30(4,32(31)25(45-32)26(39)40)24(15-8-11-41-14-15)43-27-23(38)22(37)21(36)16(13-33)42-27/h7-9,11,14,16-18,21-25,27,33,36-38H,6,10,12-13H2,1-5H3,(H,39,40)/t16-,17-,18+,21-,22+,23-,24+,25+,27+,29-,30+,31+,32-/m1/s1
• InChI Key: MXZVBPOYCKIXHN-FNBRAXOMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₁₃
• Molecular Weight: 634.70 g/mol
• Exact Mass: 634.26254139 g/mol
• Topological Polar Surface Area (TPSA): 206.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.27
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7630	76.30%
Caco-2	-	0.8506	85.06%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7663	76.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7545	75.45%
OATP1B3 inhibitior	+	0.8404	84.04%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.6005	60.05%
P-glycoprotein inhibitior	+	0.7001	70.01%
P-glycoprotein substrate	+	0.5647	56.47%
CYP3A4 substrate	+	0.7053	70.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8752	87.52%
CYP3A4 inhibition	-	0.6221	62.21%
CYP2C9 inhibition	-	0.7266	72.66%
CYP2C19 inhibition	-	0.8367	83.67%
CYP2D6 inhibition	-	0.9313	93.13%
CYP1A2 inhibition	-	0.8305	83.05%
CYP2C8 inhibition	+	0.6198	61.98%
CYP inhibitory promiscuity	-	0.8832	88.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6386	63.86%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9127	91.27%
Skin irritation	-	0.6947	69.47%
Skin corrosion	-	0.9268	92.68%
Ames mutagenesis	-	0.7140	71.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.6652	66.52%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5926	59.26%
skin sensitisation	-	0.8814	88.14%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8466	84.66%
Acute Oral Toxicity (c)	I	0.4456	44.56%
Estrogen receptor binding	+	0.7312	73.12%
Androgen receptor binding	+	0.7753	77.53%
Thyroid receptor binding	+	0.5408	54.08%
Glucocorticoid receptor binding	+	0.7807	78.07%
Aromatase binding	+	0.6963	69.63%
PPAR gamma	+	0.7069	70.69%
Honey bee toxicity	-	0.7552	75.52%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	+	0.9773	97.73%

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	96.55%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.44%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.53%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	90.44%	90.17%
CHEMBL2581	P07339	Cathepsin D	90.43%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.33%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.23%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.97%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.49%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.39%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.82%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.99%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.68%	99.23%
CHEMBL3524	P56524	Histone deacetylase 4	81.95%	92.97%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.87%	89.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.18%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.39%	100.00%
CHEMBL5028	O14672	ADAM10	80.11%	97.50%

Plants that contains it

• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Craibia grandiflora
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Ficus formosana
• Gardenia fosbergii
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Litogyne gariepina
• Odixia angusta
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Quercus cerris
• Salvia officinalis
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Taxodium huegelii
• Vitex madiensis

Cross-Links

• PubChem: 53363753
• NPASS: NPC225343