(-)-Praeruptorin B

Details

• Internal ID: 089e006d-90aa-41ae-b885-13adcadcf80b
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: [(9R,10R)-8,8-dimethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@H](C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C24H26O7/c1-7-13(3)22(26)29-20-18-16(11-9-15-10-12-17(25)28-19(15)18)31-24(5,6)21(20)30-23(27)14(4)8-2/h7-12,20-21H,1-6H3/b13-7-,14-8-/t20-,21-/m1/s1
• InChI Key: PNTWXEIQXBRCPS-IOWUNYDSSA-N
• Popularity: 80 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆O₇
• Molecular Weight: 426.50 g/mol
• Exact Mass: 426.16785316 g/mol
• Topological Polar Surface Area (TPSA): 88.10 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• (-)-Praeruptorin B
• Anomalin
• 4970-26-7
• MLS000574876
• CHEMBL1610853
• HMS2198A05
• HY-N0947
• REGID_for_CID_10251869
• AKOS040760645
• SMR000156222
• CS-0016081

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	+	0.6934	69.34%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7240	72.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9420	94.20%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9345	93.45%
P-glycoprotein inhibitior	+	0.9075	90.75%
P-glycoprotein substrate	-	0.8514	85.14%
CYP3A4 substrate	+	0.5679	56.79%
CYP2C9 substrate	-	0.6435	64.35%
CYP2D6 substrate	-	0.8752	87.52%
CYP3A4 inhibition	+	0.6239	62.39%
CYP2C9 inhibition	-	0.6806	68.06%
CYP2C19 inhibition	+	0.7432	74.32%
CYP2D6 inhibition	-	0.8778	87.78%
CYP1A2 inhibition	-	0.5415	54.15%
CYP2C8 inhibition	-	0.5736	57.36%
CYP inhibitory promiscuity	+	0.6952	69.52%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4415	44.15%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8606	86.06%
Skin irritation	-	0.7534	75.34%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	+	0.5826	58.26%
Human Ether-a-go-go-Related Gene inhibition	+	0.8073	80.73%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.5268	52.68%
skin sensitisation	-	0.6848	68.48%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.7549	75.49%
Acute Oral Toxicity (c)	III	0.7765	77.65%
Estrogen receptor binding	+	0.8330	83.30%
Androgen receptor binding	+	0.7247	72.47%
Thyroid receptor binding	+	0.5243	52.43%
Glucocorticoid receptor binding	+	0.6638	66.38%
Aromatase binding	-	0.5865	58.65%
PPAR gamma	+	0.6830	68.30%
Honey bee toxicity	-	0.7451	74.51%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	35481.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	501.2 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.39%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.45%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.94%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.40%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.64%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.21%	94.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	86.12%	85.30%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.94%	81.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.04%	96.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.98%	89.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.72%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.47%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.91%	94.75%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.50%	85.49%
CHEMBL3401	O75469	Pregnane X receptor	80.35%	94.73%

Plants that contains it

• Angelica cincta
• Angelica taiwaniana
• Angelica tatianae
• Kitagawia praeruptora
• Levisticum officinale
• Musineon divaricatum
• Peucedanum austriacum
• Saposhnikovia divaricata
• Seseli asperulum
• Seseli coronatum
• Seseli cuneifolium
• Seseli eriocephalum
• Seseli grandivittatum
• Seseli lehmannianum

Cross-Links

• PubChem: 10251869
• NPASS: NPC287182
• ChEMBL: CHEMBL1610853
• LOTUS: LTS0138479
• wikiData: Q104393569