Dihydrokawain

Details

• Internal ID: 1dff533a-240d-41e5-810c-246f1203c80c
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: (2S)-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
• SMILES (Canonical): COC1=CC(=O)OC(C1)CCC2=CC=CC=C2
• SMILES (Isomeric): COC1=CC(=O)O[C@H](C1)CCC2=CC=CC=C2
• InChI: InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3/t12-/m0/s1
• InChI Key: VOOYTQRREPYRIW-LBPRGKRZSA-N
• Popularity: 33 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.27 g/mol
• Exact Mass: 232.109944368 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• Dihydrokawain
• 587-63-3
• Kavain, dihydro-
• Kawain, dihydro-
• Marindinin
• 7,8-Dihydrokawain
• NW8ZGW9XRZ
• UNII-NW8ZGW9XRZ
• (+)-Dihydrokavain
• CCRIS 9371
• 7,8-Dihydro-kawain
• (S)-(+)-7,8-Dihydrokavain
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (6S)-
• NSC 112163
• NSC-112163
• (S)-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one
• DTXSID8033433
• (S)-(+)-DIHYDROKAWAIN
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-phenethyl-
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (S)-
• (6S)-5,6-Dihydro-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one
• (2S)-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
• 7,8-Dihydrokawain;7,8-Dihydrokavain;Marindinin
• DIHYDROKAWAIN [MI]
• CHEMBL569329
• MEGxp0_001719
• SCHEMBL5672433
• ACon0_000958
• ACon1_000519
• CHEBI:157713
• DTXCID501476403
• HMS3887C05
• HY-N0920
• Tox21_201033
• MFCD01694032
• NSC112163
• s9446
• AKOS028109012
• CCG-266804
• CS-4244
• NCGC00169002-01
• NCGC00169002-05
• NCGC00258586-01
• AC-34187
• CAS-587-63-3
• MS-23329
• (S)-(+)-7,8-Dihydrokavain, analytical standard
• 2H-Pyran-2-one,6-dihydro-4-methoxy-6-phenethyl-
• Q-100678
• BRD-K31961554-001-01-9
• Q27285076
• 2H-Pyran-2-one,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.9560	95.60%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6103	61.03%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.9209	92.09%
OATP1B3 inhibitior	+	0.9635	96.35%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6407	64.07%
P-glycoprotein inhibitior	-	0.8260	82.60%
P-glycoprotein substrate	-	0.7584	75.84%
CYP3A4 substrate	-	0.5239	52.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8743	87.43%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.8553	85.53%
CYP2C19 inhibition	+	0.8215	82.15%
CYP2D6 inhibition	-	0.8786	87.86%
CYP1A2 inhibition	+	0.7115	71.15%
CYP2C8 inhibition	-	0.5861	58.61%
CYP inhibitory promiscuity	+	0.7257	72.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8528	85.28%
Carcinogenicity (trinary)	Non-required	0.6124	61.24%
Eye corrosion	-	0.8755	87.55%
Eye irritation	-	0.5582	55.82%
Skin irritation	-	0.6351	63.51%
Skin corrosion	-	0.9815	98.15%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6677	66.77%
Micronuclear	-	0.8456	84.56%
Hepatotoxicity	+	0.9625	96.25%
skin sensitisation	-	0.8118	81.18%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.7531	75.31%
Acute Oral Toxicity (c)	III	0.5847	58.47%
Estrogen receptor binding	+	0.6560	65.60%
Androgen receptor binding	+	0.7226	72.26%
Thyroid receptor binding	-	0.7143	71.43%
Glucocorticoid receptor binding	-	0.7385	73.85%
Aromatase binding	-	0.6117	61.17%
PPAR gamma	-	0.8458	84.58%
Honey bee toxicity	-	0.8750	87.50%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.8668	86.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.32%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.16%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.07%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.23%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.50%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.26%	95.89%
CHEMBL1907	P15144	Aminopeptidase N	84.19%	93.31%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.11%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.45%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.25%	85.14%

Plants that contains it

• Aniba hostmanniana
• Piper methysticum

Cross-Links

• PubChem: 10220256
• NPASS: NPC23453
• LOTUS: LTS0040568
• wikiData: Q27285076