Melilotigenin C

Details

• Internal ID: 2b4ff1c5-0394-46b1-a5be-f5cb7140391e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-one
• SMILES (Canonical): CC1(CC2C3=CCC4C5(CCC(=O)C(C5CCC4(C3(CCC2(C(C1)O)C)C)C)(C)CO)C)C
• SMILES (Isomeric): C[C@]12CCC(=O)[C@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(C[C@H]5O)(C)C)C)C)C)(C)CO
• InChI: InChI=1S/C30H48O3/c1-25(2)16-20-19-8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-30(22,7)29(19,6)15-14-26(20,3)24(33)17-25/h8,20-22,24,31,33H,9-18H2,1-7H3/t20-,21+,22+,24+,26+,27-,28+,29+,30+/m0/s1
• InChI Key: ZSSKGAAIGRYCEP-SDDNWOMQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₃
• Molecular Weight: 456.70 g/mol
• Exact Mass: 456.36034539 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 6.32
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 188970-21-0
• (4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-one
• CHEMBL4170605
• AKOS032961995
• (4,22)-22,23-Dihydroxyolean-12-en-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.5518	55.18%
Blood Brain Barrier	+	0.6635	66.35%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8371	83.71%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9080	90.80%
OATP1B3 inhibitior	+	0.9383	93.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6193	61.93%
BSEP inhibitior	+	0.9129	91.29%
P-glycoprotein inhibitior	-	0.8121	81.21%
P-glycoprotein substrate	-	0.7932	79.32%
CYP3A4 substrate	+	0.6373	63.73%
CYP2C9 substrate	-	0.8407	84.07%
CYP2D6 substrate	-	0.7921	79.21%
CYP3A4 inhibition	-	0.7962	79.62%
CYP2C9 inhibition	-	0.8199	81.99%
CYP2C19 inhibition	-	0.8580	85.80%
CYP2D6 inhibition	-	0.9362	93.62%
CYP1A2 inhibition	-	0.8624	86.24%
CYP2C8 inhibition	-	0.6274	62.74%
CYP inhibitory promiscuity	-	0.8325	83.25%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5958	59.58%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9358	93.58%
Skin irritation	-	0.5879	58.79%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.7228	72.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4053	40.53%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.7589	75.89%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6820	68.20%
Acute Oral Toxicity (c)	III	0.7593	75.93%
Estrogen receptor binding	+	0.8099	80.99%
Androgen receptor binding	+	0.7097	70.97%
Thyroid receptor binding	+	0.6887	68.87%
Glucocorticoid receptor binding	+	0.8457	84.57%
Aromatase binding	+	0.7123	71.23%
PPAR gamma	+	0.6674	66.74%
Honey bee toxicity	-	0.9044	90.44%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9814	98.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.71%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.81%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.47%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.28%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.78%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.32%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.49%	96.77%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.29%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.02%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.30%	93.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.77%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.20%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.90%	94.45%

Plants that contains it

• Abies alba
• Abies pinsapo subsp. marocana
• Ampelocera edentula
• Angelica acutiloba
• Arnica mollis
• Brassica carinata
• Bryonia alba
• Carpha glomerata
• Croton gratissimus
• Cyanostegia angustifolia
• Dactylorhiza viridis
• Diplopterygium glaucum
• Eucalyptus resinifera
• Euphrasia nana
• Eurycoma harmandiana
• Ixeris japonica
• Lysimachia fordiana
• Orthosiphon aristatus
• Oxytropis falcata
• Pterolobium hexapetalum
• Ranunculus asiaticus
• Remirea maritima
• Sinapis alba
• Solanum lanceolatum
• Viburnum erubescens
• Wikstroemia indica
• Xanthorhiza simplicissima

Cross-Links

• PubChem: 10551785
• NPASS: NPC100284
• LOTUS: LTS0175730
• wikiData: Q104400892