Wilfolic acid C

Details

• Internal ID: 571e2dca-58b9-41f9-a01a-d537bde7a355
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,4aS,6aS,6aR,6bS,8aS,9R,11R,12aS,14aS,14bR)-11-hydroxy-2,4a,6a,6a,8a,9,14a-heptamethyl-10-oxo-3,4,5,6,6b,7,8,9,11,12,12a,13,14,14b-tetradecahydro-1H-picene-2-carboxylic acid
• SMILES (Canonical): CC1C(=O)C(CC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C)C)O
• SMILES (Isomeric): C[C@H]1C(=O)[C@@H](C[C@@H]2[C@@]1(CC[C@H]3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@](CC5)(C)C(=O)O)C)C)C)C)C)O
• InChI: InChI=1S/C30H48O4/c1-18-23(32)19(31)16-21-27(18,4)9-8-20-28(21,5)13-15-30(7)22-17-26(3,24(33)34)11-10-25(22,2)12-14-29(20,30)6/h18-22,31H,8-17H2,1-7H3,(H,33,34)/t18-,19+,20-,21+,22+,25+,26+,27+,28+,29+,30-/m0/s1
• InChI Key: KVLFXTHBJNNYDP-KWDXJSKJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.70 g/mol
• Exact Mass: 472.35526001 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 7.60
• Atomic LogP (AlogP): 6.49
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• CHEMBL459197
• Wilforic acid C
• 158629-70-0
• 2alpha-Hydroxypolpunonic acid
• CHEBI:132375
• DTXSID901113596
• BDBM50242236
• (2alpha,4beta,5beta,8alpha,9beta,10alpha,13alpha,14beta,20alpha)-2-Hydroxy-5,9,13-trimethyl-3-oxo-24,25,26-trinoroleanan-29-oic acid
• (2R,4aS,6aR,6bS,8aS,9R,11R,12aS,12bS,14aS,14bR)-11-hydroxy-2,4a,6a,8a,9,12b,14a-heptamethyl-10-oxodocosahydropicene-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9704	97.04%
Caco-2	-	0.6128	61.28%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8524	85.24%
OATP2B1 inhibitior	-	0.5732	57.32%
OATP1B1 inhibitior	+	0.9097	90.97%
OATP1B3 inhibitior	+	0.9160	91.60%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	+	0.6846	68.46%
P-glycoprotein inhibitior	-	0.6986	69.86%
P-glycoprotein substrate	-	0.7400	74.00%
CYP3A4 substrate	+	0.6429	64.29%
CYP2C9 substrate	-	0.8363	83.63%
CYP2D6 substrate	-	0.8429	84.29%
CYP3A4 inhibition	-	0.8033	80.33%
CYP2C9 inhibition	-	0.9560	95.60%
CYP2C19 inhibition	-	0.9484	94.84%
CYP2D6 inhibition	-	0.9727	97.27%
CYP1A2 inhibition	-	0.7888	78.88%
CYP2C8 inhibition	-	0.7540	75.40%
CYP inhibitory promiscuity	-	0.9920	99.20%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7222	72.22%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9224	92.24%
Skin irritation	+	0.6765	67.65%
Skin corrosion	-	0.9162	91.62%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4165	41.65%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.7973	79.73%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5957	59.57%
Acute Oral Toxicity (c)	III	0.6775	67.75%
Estrogen receptor binding	+	0.6867	68.67%
Androgen receptor binding	+	0.6637	66.37%
Thyroid receptor binding	+	0.6174	61.74%
Glucocorticoid receptor binding	+	0.7231	72.31%
Aromatase binding	+	0.7299	72.99%
PPAR gamma	+	0.6082	60.82%
Honey bee toxicity	-	0.8158	81.58%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9830	98.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.75%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.23%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	90.89%	90.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.31%	96.38%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.82%	93.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.56%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.60%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.54%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	84.30%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.08%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.32%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.67%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.23%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.83%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.23%	92.94%
CHEMBL237	P41145	Kappa opioid receptor	81.03%	98.10%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	80.47%	95.52%

Plants that contains it

• Adenopeltis serrata
• Bituminaria bituminosa
• Centaurea seridis
• Chrozophora tinctoria
• Cneorum pulverulentum
• Dalbergia stipulacea
• Delphinium ajacis
• Elaeagnus commutata
• Eucalyptus flocktoniae
• Flindersia brayleyana
• Heracleum sphondylium
• Jungermannia obovata
• Kummerowia striata
• Mascarenhasia arborescens
• Meconopsis napaulensis
• Merremia umbellata
• Millettia conraui
• Palafoxia rosea
• Pedicularis condensata
• Perityle vaseyi
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus garckeanus
• Porella swartziana
• Quercus mongolica
• Rheum webbianum
• Salacia chinensis
• Salvia coulteri
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Solanum sisymbriifolium
• Thymbra spicata
• Tripterygium doianum
• Tripterygium wilfordii
• Turraeanthus mannii

Cross-Links

• PubChem: 44559659
• NPASS: NPC26029
• LOTUS: LTS0058139
• wikiData: Q105146588