Mycophenolic Acid

Details

• Internal ID: 25505414-1667-44a8-a2d7-5fc92affb5f7
• Taxonomy: Organoheterocyclic compounds > Isocoumarans > Isobenzofuranones > Phthalides
• IUPAC Name: (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
• InChI: InChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
• InChI Key: HPNSFSBZBAHARI-RUDMXATFSA-N
• Popularity: 13,205 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.30 g/mol
• Exact Mass: 320.12598835 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.73
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 24280-93-1
• Mycophenolate
• Melbex
• Myfortic
• Mycophenolsaeure
• 483-60-3
• Lilly-68618
• Acido micofenolico
• Micofenolico acido
• (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
• NSC-129185
• Acide mycophenolique
• Acidum mycophenolicum
• 6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid
• CCRIS 5565
• NSC 129185
• Ly 68618
• (E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid
• UNII-HU9DX48N0T
• EINECS 246-119-3
• HU9DX48N0T
• (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic acid
• (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
• DTXSID4041070
• Acido micofenolico [INN-Spanish]
• CHEBI:168396
• Acide mycophenolique [INN-French]
• Acidum mycophenolicum [INN-Latin]
• MFCD00036814
• NSC129185
• Lilly 68618
• 4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (E)-
• CHEMBL866
• 4-Hexenoic acid, 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-, (E)-
• 4-Methyl-5-methoxy-7-hydroxy-6-(5-carboxy-3-methylpent-2-en-1-yl)-phthalide (E)-
• 6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methylhex-4-enoic acid
• 6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid (E)-
• Myfortic (mycophenolate sodium)
• 4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4E)-
• DTXCID2021070
• EC 246-119-3
• TNP00198
• RS-61443 [AS MOFETIL]
• 6-(1,3-Dihydro-7-hydroxy-5-methoxy-4-methyl-1-oxoisobenzofuran-6-yl)-4-methyl-4-hexanoic acid
• NCGC00016786-01
• CAS-24280-93-1
• Mycophenolic acid 100 microg/mL in Acetonitrile
• 6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid
• Acido micofenolico (INN-Spanish)
• MYCOPHENOLIC ACID (MART.)
• MYCOPHENOLIC ACID [MART.]
• Acide mycophenolique (INN-French)
• Acidum mycophenolicum (INN-Latin)
• Mycophenoic acid
• 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methyl-4-hexenoic acid
• Micofenolico acido [Spanish]
• (4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic Acid (Mycophenolic Acid)
• (E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid
• 4-Hexenoic acid,6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4E)-
• 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic acid
• MOA
• SMR000471887
• 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
• SR-01000597602
• MYCOPHENOLATE MOFETIL IMPURITY F (EP IMPURITY)
• MYCOPHENOLATE MOFETIL IMPURITY F [EP IMPURITY]
• Mycophenolsaure
• mycophenilic acid
• mycophenolic-acid
• (4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic Acid; Mycophenolate Mofetil Imp. F (EP); Mycophenolic Acid; Mycophenolate Mofetil Impurity F
• Prestwick_817
• EINECS 207-595-8
• Mycophenolic acid [USAN:INN:BAN]
• MPA - Mycophenolate
• Tocris-1505
• 1jr1
• starbld0040186
• Mycophenolic acid (TN)
• Prestwick2_000556
• Prestwick3_000556
• Spectrum5_001654
• Mycophenolic Acid (MPA)
• UPCMLD-DP028
• 4-Hexenoic acid, (E)-
• Mycophenolate;RS-61443
• SCHEMBL4549
• Mycophenolic (Mycophenolate)
• Mycophenolic acid, >=98%
• BSPBio_000631
• BSPBio_002534
• MYCOPHENOLATE [VANDF]
• MLS001074701
• MLS002222265
• MLS002695945
• BIDD:GT0456
• SPECTRUM1500674
• MYCOPHENOLIC ACID [MI]
• BPBio1_000695
• GTPL6832
• MEGxm0_000120
• Mycophenolic acid (USAN/INN)
• SCHEMBL2514376
• Mycophenolate; Myfortic; Melbex
• MYCOPHENOLIC ACID [INN]
• MYCOPHENOLIC ACID [USAN]
• UPCMLD-DP028:001
• ACon0_000960
• ACon1_000496
• BDBM19264
• CHEBI:92545
• HMS500H08
• EX-A975
• L04AA06
• MYCOPHENOLIC ACID [VANDF]
• HMS1569P13
• HMS1921A18
• HMS2089A17
• HMS2092G22
• HMS2096P13
• HMS2268H22
• HMS3403P09
• HMS3412F09
• HMS3676F09
• Pharmakon1600-01500674
• MYCOPHENOLIC ACID [WHO-DD]
• AMY40494
• BCP05321
• HY-B0421
• Tox21_110610
• CCG-39914
• HB3987
• NSC757424
• s2487
• Mycophenolic acid, analytical standard
• AKOS015888214
• Tox21_110610_1
• AC-4491
• BCP9000970
• DB01024
• DS-1638
• MYCOPHENOLIC ACID [ORANGE BOOK]
• NSC-757424
• SDCCGMLS-0066618.P001
• (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methyl-hex-4-enoic acid
• IDI1_000146
• NCGC00016786-02
• NCGC00016786-03
• NCGC00016786-04
• NCGC00016786-05
• NCGC00016786-06
• NCGC00016786-07
• NCGC00016786-08
• NCGC00016786-09
• NCGC00016786-10
• NCGC00016786-11
• NCGC00016786-12
• NCGC00016786-15
• NCGC00025190-01
• NCGC00025190-02
• NCGC00025190-03
• NCGC00025190-04
• NCGC00025190-05
• NCGC00025190-07
• NCGC00025190-08
• NCGC00025190-09
• NCGC00025190-10
• (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxohydroisobenzofuran-5-yl)-4-methylhex -4-enoic acid
• -Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (E)-
• BM164624
• Mycophenolic Acid - CAS 24280-93-1
• SBI-0051945.P003
• A-249
• M2216
• SW196951-2
• C20380
• D05096
• EN300-122327
• M 5255
• M02087
• AB00052466-13
• AB00052466-14
• AB00052466_15
• AB00052466_16
• EN300-1273238
• A817192
• Mycophenolate mofetil impurity, mycophenolic acid-
• Q420553
• SR-01000597602-1
• SR-01000597602-3
• SR-01000597602-4
• BRD-K63750851-001-06-6
• BRD-K63750851-001-13-2
• Z2315575694
• MYCOPHENOLATE MOFETIL IMPURITY, MYCOPHENOLIC ACID- [USP IMPURITY]
• MYCOPHENOLATE MOFETIL IMPURITY, MYCOPHENOLIC ACID-(USP IMPURITY)
• Mycophenolic acid, powder, BioReagent, suitable for cell culture, >=98%
• 6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid;NSC 129185
• 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthanlanyl)-4-methyl-4-hexanoic acid
• '6-(1,3-DIHYDRO-7-HYDROXY-5-METHOXY-4-METHYL-1-OXOISOBENZOFURAN-6-YL)-4-METHYL-4-HEXANOIC ACID'
• (E)-6-(1,3-dihydro-4-hydroxy-6- methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid
• (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid
• 1162256-90-7
• 4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4E)- (9CI)
• 4-Hexenoic acid, 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-, (E)- (8CI)
• 4-Hexenoic acid,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5- isobenzofuranyl)-4-methyl-, (E)-
• E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9912	99.12%
Caco-2	+	0.5454	54.54%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8423	84.23%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8542	85.42%
BSEP inhibitior	-	0.7428	74.28%
P-glycoprotein inhibitior	-	0.9165	91.65%
P-glycoprotein substrate	-	0.8803	88.03%
CYP3A4 substrate	+	0.5543	55.43%
CYP2C9 substrate	-	0.6009	60.09%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6769	67.69%
CYP inhibitory promiscuity	-	0.7237	72.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6634	66.34%
Eye corrosion	-	0.9920	99.20%
Eye irritation	+	0.7178	71.78%
Skin irritation	-	0.8722	87.22%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	+	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5950	59.50%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.8806	88.06%
skin sensitisation	-	0.8509	85.09%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.9184	91.84%
Acute Oral Toxicity (c)	II	0.7418	74.18%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	-	0.5527	55.27%
Thyroid receptor binding	-	0.6996	69.96%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.9149	91.49%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.9949	99.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	7 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	141.3 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	63.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.75%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.68%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.96%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.88%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.87%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.16%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.60%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.33%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	84.51%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	83.08%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.07%	95.50%
CHEMBL4208	P20618	Proteasome component C5	82.46%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.34%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.02%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.58%	99.15%

Plants that contains it

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Cross-Links

• PubChem: 446541
• LOTUS: LTS0068811
• wikiData: Q420553