Yuanhuacin

Details

• Internal ID: b51a68fa-a065-4352-866a-edaceb5682c2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
• IUPAC Name: [(1R,2R,6S,7S,8R,10S,11S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1E,3E)-nona-1,3-dienyl]-5-oxo-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] benzoate
• SMILES (Canonical): CCCCCC=CC=CC12OC3C4C5C(O5)(C(C6(C(C4(O1)C(C(C3(O2)C(=C)C)OC(=O)C7=CC=CC=C7)C)C=C(C6=O)C)O)O)CO
• SMILES (Isomeric): CCCCC/C=C/C=C/C12O[C@@H]3[C@@H]4[C@H]5[C@](O5)([C@H]([C@]6([C@H]([C@@]4(O1)[C@@H]([C@H]([C@@]3(O2)C(=C)C)OC(=O)C7=CC=CC=C7)C)C=C(C6=O)C)O)O)CO
• InChI: InChI=1S/C37H44O10/c1-6-7-8-9-10-11-15-18-34-45-30-26-29-33(20-38,44-29)32(41)35(42)25(19-22(4)27(35)39)37(26,47-34)23(5)28(36(30,46-34)21(2)3)43-31(40)24-16-13-12-14-17-24/h10-19,23,25-26,28-30,32,38,41-42H,2,6-9,20H2,1,3-5H3/b11-10+,18-15+/t23-,25-,26+,28-,29+,30-,32-,33+,34?,35-,36+,37+/m1/s1
• InChI Key: CGSGRJNIABXQJQ-CAAOHEDASA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₄O₁₀
• Molecular Weight: 648.70 g/mol
• Exact Mass: 648.29344760 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

• Yuanhuatie
• Yuanhuacium ester A
• Gnidilatidin
• Stillingia factor S(sub 6)
• Yuanhuacine
• Odoracin
• 60195-70-2
• Simplexin, 12-(benzoyloxy)-22,23,24,25-tetradehydro-, (12-beta,22E,24E)-
• Yuanhuacin A
• YHL-14
• CHEMBL3943353
• SCHEMBL15730513
• NSC270919
• NSC 261422
• NSC 270919
• NSC-270919
• PD128875
• LS-145414
• [(1R,2R,6S,7S,8R,10S,11S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1E,3E)-nona-1,3-dienyl]-5-oxo-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8970	89.70%
Caco-2	-	0.8229	82.29%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7033	70.33%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.7787	77.87%
OATP1B3 inhibitior	+	0.9207	92.07%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9266	92.66%
P-glycoprotein inhibitior	+	0.7739	77.39%
P-glycoprotein substrate	+	0.6575	65.75%
CYP3A4 substrate	+	0.7129	71.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	+	0.6654	66.54%
CYP2C9 inhibition	-	0.6720	67.20%
CYP2C19 inhibition	-	0.7414	74.14%
CYP2D6 inhibition	-	0.9031	90.31%
CYP1A2 inhibition	-	0.7407	74.07%
CYP2C8 inhibition	+	0.8177	81.77%
CYP inhibitory promiscuity	-	0.6746	67.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5898	58.98%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.9129	91.29%
Skin irritation	-	0.6361	63.61%
Skin corrosion	-	0.9211	92.11%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7448	74.48%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8580	85.80%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6466	64.66%
Acute Oral Toxicity (c)	III	0.5390	53.90%
Estrogen receptor binding	+	0.7732	77.32%
Androgen receptor binding	+	0.7397	73.97%
Thyroid receptor binding	+	0.6213	62.13%
Glucocorticoid receptor binding	+	0.7015	70.15%
Aromatase binding	+	0.6214	62.14%
PPAR gamma	+	0.6603	66.03%
Honey bee toxicity	-	0.8061	80.61%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5148	51.48%
Fish aquatic toxicity	+	0.9950	99.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.02%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.49%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	96.11%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.98%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.29%	99.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.79%	94.62%
CHEMBL2996	Q05655	Protein kinase C delta	92.96%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.50%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.34%	96.09%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	89.18%	85.94%
CHEMBL1951	P21397	Monoamine oxidase A	87.28%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.86%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.46%	96.47%
CHEMBL3401	O75469	Pregnane X receptor	84.51%	94.73%
CHEMBL4040	P28482	MAP kinase ERK2	84.33%	83.82%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.09%	83.00%
CHEMBL5028	O14672	ADAM10	83.76%	97.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.81%	96.90%
CHEMBL299	P17252	Protein kinase C alpha	82.76%	98.03%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.86%	92.32%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	81.42%	92.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.35%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.31%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.21%	93.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.06%	93.00%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	80.95%	96.00%

Plants that contains it

• Daphne genkwa
• Daphne odora
• Daphne oleoides
• Lasiosiphon kraussianus

Cross-Links

• PubChem: 6440205
• NPASS: NPC92598
• LOTUS: LTS0202039
• wikiData: Q104396027