Aflatoxin B2

Details

• Internal ID: 0e7f04d4-7532-469b-a299-f04e49428798
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Aflatoxins > Difurocoumarocyclopentenones
• IUPAC Name: (3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,9,11,13(17)-tetraene-16,18-dione
• InChI: InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h6,8,17H,2-5H2,1H3/t8-,17+/m0/s1
• InChI Key: WWSYXEZEXMQWHT-WNWIJWBNSA-N
• Popularity: 767 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.29 g/mol
• Exact Mass: 314.07903816 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 7220-81-7
• Dihydroaflatoxin B1
• Dihydroaflatoxine B1
• CCRIS 13
• 7SKR7S646P
• BRN 1355115
• CHEBI:48209
• DTXSID70222535
• 5-19-10-00552 (Beilstein Handbook Reference)
• (3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,9,11,13(17)-tetraene-16,18-dione
• (6aR,9aS)-4-methoxy-2,3,6a,8,9,9a-hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene-1,11-dione
• 2,3,6aalpha,8,9,9aalpha-Hexahydro-4-methoxycyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione
• 2,3,6aalpha,8,9,9aalpha-hexahydro-4-methoxycyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione
• Cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 2,3,6a-alpha,8,9,9a-alpha-hexahydro-4-methoxy-
• (3S,7R)-11-methoxy-6,8,19-trioxapentacyclo(10.7.0.02,9.03,7.013,17)nonadeca-1,9,11,13(17)-tetraene-16,18-dione
• (6aR,9aS)-4-methoxy-2,3,6a,8,9,9a-hexahydrocyclopenta(c)furo(3',2':4,5)furo(2,3-h)chromene-1,11-dione
• CYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN-1,11-DIONE, 2,3,6A,8,9,9A-HEXAHYDRO-4-METHOXY-, (6AR-CIS)-
• RefChem:110030
• DTXCID00145026
• 11-methoxy-6,8,19-trioxapentacyclo(10.7.0.02,9.03,7.013,17)nonadeca-1(12),2(9),10,13(17)-tetraene-16,18-dione
• 230-618-8
• aflatoxin-B(2)
• AFB2
• (6aR,9aS)-2,3,6a,8,9,9ahexahydro-4-methoxy-cyclopenta[c]furo[3',2':4,5]furo[2,3h][1]benzopyran-1,11-dione
• AFLATOXINB2
• 2,3,6aalpha,8,9,9aalpha-hexahydro-4-methoxycyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene-1,11-dione
• Aflatoxin B2 0.5 microg/mL in Acetonitrile
• UNII-7SKR7S646P
• HSDB 3454
• CYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN-1,11-DIONE, 2,3,6A,8,9,9A-HEXAHYDRO-4-METHOXY-, (6AR,9AS)-
• Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione, 2,3,6a,8,9,9a-hexahydro-4-methoxy-, (6aR,9aS)-
• EINECS 230-618-8
• MFCD00078140
• AFLATOXIN B [MI]
• AFLATOXIN B2 [HSDB]
• SCHEMBL14424508
• Aflatoxin B2, reference material
• MSK7206
• WWSYXEZEXMQWHT-WNWIJWBNSA-N
• GLXC-21058
• MSK7206-100A
• Aflatoxin B2, from Aspergillus flavus
• FA17233
• Cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 2,3,6aalpha,8,9,9aalpha-hexahydro-4-methoxy-
• DA-70627
• ST50405316
• 4,5]furo[2,3-h][1]benzopyran-1,11-dione
• G12271
• 220A817
• Aflatoxin B2 solution in Acetonitrile, 100ug/mL
• Q26840819
• (6aR-cis)-2,3,6a,8,9,9a-hexahydro-4-methoxycyclopenta[c]furo[3',2'
• (6aR,9aS)-2,3,6a,8,9,9a-Hexahydro-4-methoxycyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione;Dihydroaflatoxin B1;Dihyd roaflatoxine B1
• (6aR-cis)-2,3,6a,8,9,9a-hexahydro-4-methoxycyclopenta[c]furo[3',2';4,5]furo[2,3-h][1]benzopyran-1,11-dione
• (9aS,6aR)-4-methoxy-2,3,6a,9a-tetrahydro-8H,9H-cyclopenta[1,2-c]oxolano[3',2'- 5,4]furano[2,3-h]chromene-1,11-dione
• 2,3,6AALPHA,8,9,9AALPHA-HEXAHYDRO-4- METHOXYCYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN- 1,11-DIONE
• 2,3,6aalpha,8,9,9aalpha-Hexahydro-4-methoxycyclopenta(c)furo(2',3':4,5)furo(2,3-h)chromene-1,11-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9891	98.91%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8395	83.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9192	91.92%
OATP1B3 inhibitior	+	0.9823	98.23%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5516	55.16%
P-glycoprotein inhibitior	-	0.6001	60.01%
P-glycoprotein substrate	-	0.8423	84.23%
CYP3A4 substrate	+	0.6129	61.29%
CYP2C9 substrate	+	0.6233	62.33%
CYP2D6 substrate	-	0.8438	84.38%
CYP3A4 inhibition	-	0.7265	72.65%
CYP2C9 inhibition	+	0.8683	86.83%
CYP2C19 inhibition	+	0.8267	82.67%
CYP2D6 inhibition	-	0.5407	54.07%
CYP1A2 inhibition	+	0.9087	90.87%
CYP2C8 inhibition	+	0.5465	54.65%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4465	44.65%
Eye corrosion	-	0.9521	95.21%
Eye irritation	-	0.8007	80.07%
Skin irritation	-	0.8278	82.78%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7012	70.12%
Micronuclear	-	0.5567	55.67%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8148	81.48%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7012	70.12%
Acute Oral Toxicity (c)	I	0.4611	46.11%
Estrogen receptor binding	+	0.6465	64.65%
Androgen receptor binding	+	0.7436	74.36%
Thyroid receptor binding	-	0.7202	72.02%
Glucocorticoid receptor binding	+	0.7245	72.45%
Aromatase binding	-	0.5660	56.60%
PPAR gamma	+	0.8931	89.31%
Honey bee toxicity	-	0.7591	75.91%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8002	80.02%

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	98.08%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.51%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.20%	94.00%
CHEMBL2581	P07339	Cathepsin D	88.96%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.37%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.86%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.28%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.14%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.99%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.92%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.34%	92.94%
CHEMBL2535	P11166	Glucose transporter	84.68%	98.75%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.41%	82.67%
CHEMBL4040	P28482	MAP kinase ERK2	83.78%	83.82%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.43%	94.80%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.27%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.67%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.52%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.37%	85.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.71%	93.99%
CHEMBL1871	P10275	Androgen Receptor	80.63%	96.43%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.04%	89.50%

Plants that contains it

• Ficus carica

Cross-Links

• PubChem: 2724360
• NPASS: NPC273986
• LOTUS: LTS0275600
• wikiData: Q26840819