Phaseolin

Details

• Internal ID: 81815ceb-b199-4f4b-ac5f-c312e742c652
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (2R,11R)-17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC3=C2OC4C3COC5=C4C=CC(=C5)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4[C@H]3COC5=C4C=CC(=C5)O)C
• InChI: InChI=1S/C20H18O4/c1-20(2)8-7-14-16(24-20)6-5-12-15-10-22-17-9-11(21)3-4-13(17)19(15)23-18(12)14/h3-9,15,19,21H,10H2,1-2H3/t15-,19-/m0/s1
• InChI Key: LWTDZKXXJRRKDG-KXBFYZLASA-N
• Popularity: 344 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.12050905 g/mol
• Topological Polar Surface Area (TPSA): 47.90 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.19
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Phaseolin
• 13401-40-6
• (-)-Phaseollin
• (+/-)-Phaseollin
• I7OEP19ZWL
• Phaseolin fungicide
• Phaseollin, (+/-)
• UNII-I7OEP19ZWL
• UNII-8OHL7771FZ
• 8OHL7771FZ
• CHEMBL448350
• 3H,7H-Furo(3,2-c:5,4-f')bis(1)benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, cis-
• 3H,7H-Furo(3,2-c:5,4-f')bis(1)benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, cis-(+/-)-
• 3H,7H-Pyrano(2',3':6,7)benzofuro(3,2-C)(1)benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, (6bR,12bR)-rel-
• 91110-20-2
• Phaseolin; Phaseolin (phytoalexin)
• 3H,7H-Furo(3,2-c:5,4-f')bis(1)benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, (6bR-cis)-
• 3H,7H-Furo[3,2-c:5,4-f']bis[1]benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, (6bR-cis)-
• PHASEOLIN [MI]
• D07TDM
• SCHEMBL33736
• PHASEOLLIN, (+/-)-
• DTXSID701029664
• HY-N3087
• BDBM50317438
• LMPK12070020
• MFCD00210543
• AKOS032948435
• CS-0023187
• Q7180982
• 3H,7H-Furo[3,2-c:5,4-f']bis[1]benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-
• (2R,11R)-17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol
• (6BR,12BR)-6B,12B-DIHYDRO-3,3-DIMETHYL-3H,7H-FURO(3,2-C:5,4-F')BIS(1)BENZOPYRAN-10-OL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.8119	81.19%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7829	78.29%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.8827	88.27%
OATP1B3 inhibitior	+	0.9734	97.34%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7176	71.76%
P-glycoprotein inhibitior	-	0.5388	53.88%
P-glycoprotein substrate	+	0.5250	52.50%
CYP3A4 substrate	+	0.6098	60.98%
CYP2C9 substrate	+	0.8070	80.70%
CYP2D6 substrate	-	0.7007	70.07%
CYP3A4 inhibition	-	0.5161	51.61%
CYP2C9 inhibition	+	0.6678	66.78%
CYP2C19 inhibition	+	0.7011	70.11%
CYP2D6 inhibition	-	0.5932	59.32%
CYP1A2 inhibition	+	0.8308	83.08%
CYP2C8 inhibition	+	0.6200	62.00%
CYP inhibitory promiscuity	+	0.7297	72.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5162	51.62%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.6767	67.67%
Skin irritation	-	0.7580	75.80%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	+	0.5963	59.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5082	50.82%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.6526	65.26%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4501	45.01%
Acute Oral Toxicity (c)	III	0.5599	55.99%
Estrogen receptor binding	+	0.8464	84.64%
Androgen receptor binding	+	0.7147	71.47%
Thyroid receptor binding	+	0.7909	79.09%
Glucocorticoid receptor binding	+	0.7336	73.36%
Aromatase binding	-	0.5246	52.46%
PPAR gamma	+	0.7746	77.46%
Honey bee toxicity	-	0.8273	82.73%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9504	95.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.68%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.63%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.93%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.10%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.09%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.43%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.36%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.15%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.89%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.93%	90.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.49%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.88%	93.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.36%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	82.20%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.16%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.70%	97.14%
CHEMBL2535	P11166	Glucose transporter	81.67%	98.75%
CHEMBL226	P30542	Adenosine A1 receptor	81.39%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.68%	95.89%
CHEMBL242	Q92731	Estrogen receptor beta	80.17%	98.35%

Plants that contains it

• Elephantopus mollis
• Erythrina abyssinica
• Erythrina addisoniae
• Erythrina burttii
• Erythrina lysistemon
• Erythrina sigmoidea
• Erythrina suberosa
• Erythrina variegata
• Glycyrrhiza inflata
• Lespedeza cyrtobotrya
• Phaseolus coccineus
• Phaseolus vulgaris
• Sophora moorcroftiana
• Teucrium betonicum

Cross-Links

• PubChem: 91572
• NPASS: NPC225696
• ChEMBL: CHEMBL448350
• LOTUS: LTS0203010
• wikiData: Q7180982