Kuhlmannin

Details

• Internal ID: cf716eb1-0053-4914-ab7c-7bd5618b508b
• Taxonomy: Phenylpropanoids and polyketides > Neoflavonoids > Neoflavones
• IUPAC Name: 6-hydroxy-7,8-dimethoxy-4-phenylchromen-2-one
• SMILES (Canonical): COC1=C(C=C2C(=CC(=O)OC2=C1OC)C3=CC=CC=C3)O
• SMILES (Isomeric): COC1=C(C=C2C(=CC(=O)OC2=C1OC)C3=CC=CC=C3)O
• InChI: InChI=1S/C17H14O5/c1-20-16-13(18)8-12-11(10-6-4-3-5-7-10)9-14(19)22-15(12)17(16)21-2/h3-9,18H,1-2H3
• InChI Key: ABUBCBFUQXIEAU-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29 g/mol
• Exact Mass: 298.08412354 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 6-Hydroxy-7,8-dimethoxy-4-phenylcoumarin
• SPBio_002203
• Spectrum_000560
• SpecPlus_000638
• Spectrum2_001992
• Spectrum3_001261
• Spectrum4_001594
• Spectrum5_000308
• 6-hydroxy-7,8-dimethoxy-4-phenylchromen-2-one
• BSPBio_002822
• KBioGR_002208
• KBioSS_001040
• SPECTRUM240862
• DivK1c_006734
• CHEMBL1568181
• SCHEMBL12062100
• KBio1_001678
• KBio2_001040
• KBio2_003608
• KBio2_006176
• KBio3_002322
• CHEBI:108605
• CCG-39477
• LMPK12100011
• SDCCGMLS-0066486.P001
• NCGC00095925-01
• NCGC00095925-02
• NCGC00178451-01
• 20972-79-6
• SR-05000002551
• SR-05000002551-1
• 6-hydroxy-7,8-dimethoxy-4-phenyl-1-benzopyran-2-one
• BRD-K18149487-001-02-8
• Q27187527

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9733	97.33%
Caco-2	+	0.6974	69.74%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7509	75.09%
OATP2B1 inhibitior	-	0.8657	86.57%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6242	62.42%
P-glycoprotein inhibitior	+	0.7218	72.18%
P-glycoprotein substrate	-	0.9409	94.09%
CYP3A4 substrate	-	0.5717	57.17%
CYP2C9 substrate	-	0.8431	84.31%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.6847	68.47%
CYP2C9 inhibition	-	0.6315	63.15%
CYP2C19 inhibition	-	0.5811	58.11%
CYP2D6 inhibition	-	0.9055	90.55%
CYP1A2 inhibition	+	0.5316	53.16%
CYP2C8 inhibition	+	0.5175	51.75%
CYP inhibitory promiscuity	-	0.5084	50.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5671	56.71%
Eye corrosion	-	0.9750	97.50%
Eye irritation	+	0.6356	63.56%
Skin irritation	-	0.6468	64.68%
Skin corrosion	-	0.9811	98.11%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4498	44.98%
Micronuclear	+	0.9059	90.59%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.9516	95.16%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6675	66.75%
Acute Oral Toxicity (c)	II	0.5637	56.37%
Estrogen receptor binding	+	0.8310	83.10%
Androgen receptor binding	+	0.8398	83.98%
Thyroid receptor binding	+	0.6394	63.94%
Glucocorticoid receptor binding	+	0.8528	85.28%
Aromatase binding	+	0.6400	64.00%
PPAR gamma	+	0.8236	82.36%
Honey bee toxicity	-	0.9091	90.91%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9330	93.30%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.46%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.09%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.74%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.57%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.87%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.49%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.69%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.99%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.67%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.03%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.75%	93.99%
CHEMBL1907	P15144	Aminopeptidase N	80.74%	93.31%

Plants that contains it

• Arnica longifolia
• Dalbergia nigra
• Kaempferia galanga
• Rubus rigidus

Cross-Links

• PubChem: 4412068
• NPASS: NPC110067
• ChEMBL: CHEMBL1568181
• LOTUS: LTS0239553
• wikiData: Q27187527