Theasapogenol B

Details

• Internal ID: f855ed15-52ea-437a-b6b6-edc0a3d5d908
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,4R,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-3,4,5,10-tetrol
• SMILES (Canonical): CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CC(C2(C(C1O)O)CO)O)C)C)(C)C)O)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC([C@H]([C@@H]5O)O)(C)C)CO)O)C)C)(C)C)O
• InChI: InChI=1S/C30H50O5/c1-25(2)14-18-17-8-9-20-27(5)12-11-21(32)26(3,4)19(27)10-13-28(20,6)29(17,7)15-22(33)30(18,16-31)24(35)23(25)34/h8,18-24,31-35H,9-16H2,1-7H3/t18-,19-,20+,21-,22+,23-,24-,27-,28+,29+,30-/m0/s1
• InChI Key: AYDKOFQQBHRXEW-AAUPIIFFSA-N
• Popularity: 51 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₅
• Molecular Weight: 490.70 g/mol
• Exact Mass: 490.36582469 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.05
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• Jegosapogenol A
• Giganteumgenin M
• Careyagenol A
• 13844-01-4
• Escinidin
• Barringtogenol C
• Proschiwalligenin PB1
• Saniculagenin D
• Jegosapogenol
• EXS7QH1WV9
• CHEBI:2994
• Aescinidin
• Acutangenol B
• Olean-12-ene-3beta,16alpha,21beta,22alpha,28-pentol
• (3beta,16alpha,21beta,22alpha)Olean-12-ene-3,16,21,22,28-pentol
• 22-O-Acetyl-21-O-(4'-O-angeloyl)-beta-d-fucopyranosyl theasapogenol B
• Olean-12-ene-3,16,21,22,28-pentol, (3.beta.,16.alpha.,21.beta.,22.alpha.)-
• Barringtogenol
• (3R,4R,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-3,4,5,10-tetrol
• UNII-EXS7QH1WV9
• Olean-12-ene-3.beta.,16.alpha.,21.beta.,22.alpha.,28-pentol
• CHEMBL487606
• SCHEMBL1049164
• DTXSID00930116
• AKOS040752176
• Olean-12-ene-3,16,21,22,28-pentol
• C08931
• Q27105918
• (3beta,16alpha,21beta,22alpha)-olean-12-ene-3,16,21,22,28-pentol
• Olean-12-ene-3,16,21,22,28-pentol, (3beta,16alpha,21beta,22alpha)-
• (3R,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-3,4,5,10-tetraol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	-	0.6629	66.29%
Blood Brain Barrier	+	0.7385	73.85%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7305	73.05%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.9182	91.82%
OATP1B3 inhibitior	-	0.2681	26.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5967	59.67%
BSEP inhibitior	+	0.6260	62.60%
P-glycoprotein inhibitior	-	0.7752	77.52%
P-glycoprotein substrate	-	0.8351	83.51%
CYP3A4 substrate	+	0.6621	66.21%
CYP2C9 substrate	-	0.6197	61.97%
CYP2D6 substrate	-	0.7438	74.38%
CYP3A4 inhibition	-	0.8723	87.23%
CYP2C9 inhibition	-	0.8595	85.95%
CYP2C19 inhibition	-	0.8633	86.33%
CYP2D6 inhibition	-	0.9368	93.68%
CYP1A2 inhibition	-	0.8936	89.36%
CYP2C8 inhibition	-	0.6065	60.65%
CYP inhibitory promiscuity	-	0.9163	91.63%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7411	74.11%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9268	92.68%
Skin irritation	-	0.5811	58.11%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	-	0.8154	81.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4360	43.60%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8312	83.12%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7694	76.94%
Acute Oral Toxicity (c)	III	0.7710	77.10%
Estrogen receptor binding	+	0.7467	74.67%
Androgen receptor binding	+	0.7175	71.75%
Thyroid receptor binding	+	0.6006	60.06%
Glucocorticoid receptor binding	+	0.7433	74.33%
Aromatase binding	+	0.6344	63.44%
PPAR gamma	+	0.5865	58.65%
Honey bee toxicity	-	0.8664	86.64%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9683	96.83%

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%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.05%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.68%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	91.97%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	90.73%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.74%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.25%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.26%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.75%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.32%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.68%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.44%	95.56%

Plants that contains it

• Aesculus hippocastanum
• Aesculus indica
• Aesculus turbinata
• Barringtonia racemosa
• Camellia sinensis
• Dodonaea viscosa
• Hydrocotyle ranunculoides
• Planchonia careya
• Solanum lycopersicum

Cross-Links

• PubChem: 185465
• NPASS: NPC159168
• LOTUS: LTS0106188
• wikiData: Q27105918