Shikometabolin A

Details

• Internal ID: 1cd9cf11-a316-471f-a9f6-026682056596
• Taxonomy: Benzenoids > Naphthalenes > Naphthols and derivatives
• IUPAC Name: 3,10,14,19,21-pentahydroxy-18-[(1R)-1-hydroxy-4-methylpent-3-enyl]-12-(3-methylbut-2-enyl)pentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),6,10,12,14,17,19-nonaene-5,8,16-trione
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C(C(=CC(=O)C3=C2O)C(CC=C(C)C)O)O)O)C4=C(C5=C(C(=O)C=CC5=O)C(=C14)O)O)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C(C(=CC(=O)C3=C2O)[C@@H](CC=C(C)C)O)O)O)C4=C(C5=C(C(=O)C=CC5=O)C(=C14)O)O)C
• InChI: InChI=1S/C32H28O9/c1-12(2)5-7-14-20-25(31(40)23-18(35)10-9-17(34)22(23)29(20)38)26-21(14)30(39)24-19(36)11-15(16(33)8-6-13(3)4)28(37)27(24)32(26)41/h5-6,9-11,16,33,37-41H,7-8H2,1-4H3/t16-/m1/s1
• InChI Key: KYQNTUSTJQLIIZ-MRXNPFEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₂₈O₉
• Molecular Weight: 556.60 g/mol
• Exact Mass: 556.17333247 g/mol
• Topological Polar Surface Area (TPSA): 173.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.68
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	-	0.8406	84.06%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7659	76.59%
OATP2B1 inhibitior	-	0.5648	56.48%
OATP1B1 inhibitior	+	0.8813	88.13%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8716	87.16%
P-glycoprotein inhibitior	+	0.6471	64.71%
P-glycoprotein substrate	-	0.7376	73.76%
CYP3A4 substrate	+	0.5099	50.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8435	84.35%
CYP3A4 inhibition	-	0.6245	62.45%
CYP2C9 inhibition	+	0.7333	73.33%
CYP2C19 inhibition	+	0.6169	61.69%
CYP2D6 inhibition	-	0.5854	58.54%
CYP1A2 inhibition	+	0.8005	80.05%
CYP2C8 inhibition	-	0.8521	85.21%
CYP inhibitory promiscuity	+	0.8100	81.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9111	91.11%
Carcinogenicity (trinary)	Non-required	0.6119	61.19%
Eye corrosion	-	0.9947	99.47%
Eye irritation	-	0.8371	83.71%
Skin irritation	-	0.6945	69.45%
Skin corrosion	-	0.9184	91.84%
Ames mutagenesis	-	0.5264	52.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7624	76.24%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.6384	63.84%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6937	69.37%
Acute Oral Toxicity (c)	III	0.5582	55.82%
Estrogen receptor binding	+	0.8441	84.41%
Androgen receptor binding	+	0.6006	60.06%
Thyroid receptor binding	-	0.5338	53.38%
Glucocorticoid receptor binding	+	0.6486	64.86%
Aromatase binding	+	0.5615	56.15%
PPAR gamma	+	0.7644	76.44%
Honey bee toxicity	-	0.8608	86.08%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.28%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.08%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.00%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.53%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.80%	89.34%
CHEMBL3401	O75469	Pregnane X receptor	91.25%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.24%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.73%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	82.46%	94.75%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.06%	85.30%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.01%	99.17%

Plants that contains it

• Arnebia euchroma
• Arnebia guttata
• Lithospermum erythrorhizon

Cross-Links

• PubChem: 10460360
• NPASS: NPC212707