Aflatoxin B1

Details

• Internal ID: 886f4ee4-04a2-488f-8d7e-86382957d8bb
• 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-1,4,9,11,13(17)-pentaene-16,18-dione
• SMILES (Canonical): COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C5C=COC5OC4=C1
• SMILES (Isomeric): COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4[C@@H]5C=CO[C@@H]5OC4=C1
• InChI: InChI=1S/C17H12O6/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/h4-6,8,17H,2-3H2,1H3/t8-,17+/m0/s1
• InChI Key: OQIQSTLJSLGHID-WNWIJWBNSA-N
• Popularity: 17,226 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₆
• Molecular Weight: 312.27 g/mol
• Exact Mass: 312.06338810 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 1162-65-8
• AFB1
• AFBI
• NSC 529592
• NSC-529592
• HSDB 3453
• CCRIS 12
• BRN 1269174
• 9N2N2Y55MH
• DTXSID9020035
• NSC529592
• (3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
• 2,3,6aalpha,9aalpha-Tetrahydro-4-methoxycyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione
• CHEBI:2504
• (6aR,9aS)-4-methoxy-2,3,6a,9a-tetrahydrocyclopenta[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,9a-tetrahydro-4-methoxy-
• Cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 2,3,6a,9a-tetrahydro-4-methoxy-, (6aR,9aS)-
• Cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 2,3,6aalpha,9aalpha-tetrahydro-4-methoxy-
• Cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 2,3,6a,9a-tetrahydro-4-methoxy-, (6aR-cis)-
• (6AR-CIS)-2,3,6A,9A-TETRAHYDRO-4-METHOXYCYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN-1,11-DIONE
• Aflatoxin B(1)
• HSDB3453
• (3S,7R)-11-methoxy-6,8,19-trioxapentacyclo(10.7.0.02,9.03,7.013,17)nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
• (6aR,9aS)-4-methoxy-2,3,6a,9a-tetrahydrocyclopenta(c)furo(3',2':4,5)furo(2,3-h)chromene-1,11-dione
• RefChem:5519
• AFLATOXIN B-1
• DTXCID10820519
• 214-603-3
• 11-methoxy-6,8,19-trioxapentacyclo(10.7.0.02,9.03,7.013,17)nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
• MFCD00869647
• 1H,11H-Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione,2,3,6a,9a-tetrahydro-4-methoxy-, (6aR,9aS)-
• (-)-Aflatoxin B1
• 10279-73-9
• Aflatoxin B1 2 microg/mL in Acetonitrile
• EINECS 214-603-3
• UNII-9N2N2Y55MH
• Aflatoxin B1 from Aspergillus flavus, from Aspergillus flavus
• 5-carboxylate
• 03 - Mycotoxins
• 779 - Aflatoxin
• Aflatoxin B1 (Standard)
• (+/-)-Aflatoxin B1
• AFLATOXIN B1 [MI]
• AFLATOXIN B1 [HSDB]
• BIDD:ER0313
• SCHEMBL126480
• 5 - Mycotoxins in animal feed
• CHEMBL1697694
• SCHEMBL29370340
• HY-N6615R
• Aflatoxin B1, reference material
• DTXSID00873175
• MSK7205
• BDBM120261
• GLXC-20590
• 804 - Mycotoxins in dried fruits
• EX-A5480
• HY-N6615
• 794 - Aflatoxin analysis of spices
• MSK7205-100A
• AKOS030241596
• Compound feed - Aflatoxin B1 (blank)
• FA17232
• NCGC00247669-01
• NCGC00247669-04
• 2,3,6aalpha,9aalpha-Tetrahydro-4-methoxycyclopenta(c)furo(2',3':4,5)furo(2,3-h)chromene-1,11-dione
• DA-70626
• Aflatoxin B1 3.79microg/g in Acetonitrile
• CS-0034371
• Discontinued See D444270 (the trihydrate)
• NS00000079
• ST50405315
• Defatted peanut meal (blank) - Aflatoxin B1
• 162A658
• Aflatoxin B1 Solution in Acetonitrile, 100ug/mL
• Defatted peanut meal (high level) - Aflatoxin B1
• Q4689278
• WLN: T F5 C6 B655 DOV GV OO QO RUT&&TTJ LO1
• Methyl 4-(4-Fluorophenyl)-6-isopropyl-2-(methylsulfonyl)pyrimidine-
• Aflatoxin B1, B2, G1, G2 and Ochratoxin A Mixture 1 microg/mL in Acetonitrile
• (6aR,9aS)-2,3,6a,9a-Tetrahydro-4-methoxy-1H,11H-cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione;(-)-Aflatoxin B1;AFB 1
• (9aS,6aR)-4-methoxy-2,3,6a,9a-tetrahydrocyclopenta[2,1-c]furano[3',2'-5,4]fura no[2,3-h]chromene-1,11-dione
• 1H,11H-CYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN-1,11-DIONE, 2,3,6A,9A-TETRAHYDRO-4-METHOXY-, (6AR,9AS)-
• Cyclopenta[c]furo[3',5]furo[2,3-h][1]benzopyran-1,11-dione, 2,3,6a,9a-tetrahydro-4-methoxy-
• Cyclopenta[c]furo[3',5]furo[2,3-h][1]benzopyran-1,11-dione, 2,3,6a,9a-tetrahydro-4-methoxy-, (6aR-cis)-
• Cyclopenta[c]furo[3',5]furo[2,3-h][1]benzopyran-1,11-dione, 2,3,6a.alpha.,9a.alpha.-tetrahydro-4-methoxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.5686	56.86%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8353	83.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9119	91.19%
OATP1B3 inhibitior	+	0.9837	98.37%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5906	59.06%
P-glycoprotein inhibitior	-	0.5248	52.48%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.5849	58.49%
CYP2C9 substrate	+	0.6167	61.67%
CYP2D6 substrate	-	0.8509	85.09%
CYP3A4 inhibition	+	0.5184	51.84%
CYP2C9 inhibition	+	0.6650	66.50%
CYP2C19 inhibition	+	0.7727	77.27%
CYP2D6 inhibition	-	0.5513	55.13%
CYP1A2 inhibition	+	0.8746	87.46%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.6208	62.08%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.7481	74.81%
Eye corrosion	-	0.9538	95.38%
Eye irritation	-	0.8920	89.20%
Skin irritation	-	0.7659	76.59%
Skin corrosion	-	0.9506	95.06%
Ames mutagenesis	+	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6553	65.53%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	-	0.7446	74.46%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6978	69.78%
Acute Oral Toxicity (c)	I	0.8088	80.88%
Estrogen receptor binding	+	0.7602	76.02%
Androgen receptor binding	+	0.6843	68.43%
Thyroid receptor binding	-	0.6693	66.93%
Glucocorticoid receptor binding	+	0.7342	73.42%
Aromatase binding	+	0.5571	55.71%
PPAR gamma	+	0.8074	80.74%
Honey bee toxicity	-	0.7506	75.06%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9178	91.78%

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	97.98%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	94.32%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.14%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.09%	94.00%
CHEMBL2535	P11166	Glucose transporter	87.76%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.43%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.14%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.72%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.51%	99.23%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.78%	89.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.45%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.95%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.66%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.20%	92.62%
CHEMBL2581	P07339	Cathepsin D	80.16%	98.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 186907
• LOTUS: LTS0005941
• wikiData: Q4689278