Phthalic anhydride

Details

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Internal ID acec7215-4a47-452a-b547-f9b512df9cf8
Taxonomy Organoheterocyclic compounds > Benzofurans > Benzofuranones > Phthalic anhydrides
IUPAC Name 2-benzofuran-1,3-dione
SMILES (Canonical) C1=CC=C2C(=C1)C(=O)OC2=O
SMILES (Isomeric) C1=CC=C2C(=C1)C(=O)OC2=O
InChI InChI=1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H
InChI Key LGRFSURHDFAFJT-UHFFFAOYSA-N
Popularity 3,294 references in papers

Physical and Chemical Properties

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Molecular Formula C8H4O3
Molecular Weight 148.11 g/mol
Exact Mass 148.016043985 g/mol
Topological Polar Surface Area (TPSA) 43.40 Ų
XlogP 1.30
Atomic LogP (AlogP) 1.00
H-Bond Acceptor 3
H-Bond Donor 0
Rotatable Bonds 0

Synonyms

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85-44-9
Isobenzofuran-1,3-dione
1,3-Isobenzofurandione
2-Benzofuran-1,3-dione
1,3-Dioxophthalan
1,3-Phthalandione
Phthalsaeureanhydrid
o-Phthalic acid anhydride
Phthalic acid anhydride
Phthalandione
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Phthalic anhydride

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9970 99.70%
Caco-2 + 0.6942 69.42%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.8429 84.29%
Subcellular localzation Mitochondria 0.4979 49.79%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9567 95.67%
OATP1B3 inhibitior + 0.9756 97.56%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.9424 94.24%
P-glycoprotein inhibitior - 0.9886 98.86%
P-glycoprotein substrate - 0.9960 99.60%
CYP3A4 substrate - 0.7697 76.97%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8017 80.17%
CYP3A4 inhibition - 0.9801 98.01%
CYP2C9 inhibition - 0.8290 82.90%
CYP2C19 inhibition - 0.8108 81.08%
CYP2D6 inhibition - 0.9392 93.92%
CYP1A2 inhibition + 0.5996 59.96%
CYP2C8 inhibition - 0.9670 96.70%
CYP inhibitory promiscuity - 0.9574 95.74%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8662 86.62%
Carcinogenicity (trinary) Non-required 0.7085 70.85%
Eye corrosion + 0.9012 90.12%
Eye irritation + 1.0000 100.00%
Skin irritation + 0.5795 57.95%
Skin corrosion - 0.8842 88.42%
Ames mutagenesis - 0.8900 89.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8473 84.73%
Micronuclear - 0.5100 51.00%
Hepatotoxicity + 0.9125 91.25%
skin sensitisation + 0.4757 47.57%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity - 0.8556 85.56%
Mitochondrial toxicity + 1.0000 100.00%
Nephrotoxicity + 0.7296 72.96%
Acute Oral Toxicity (c) III 0.8057 80.57%
Estrogen receptor binding - 0.9255 92.55%
Androgen receptor binding - 0.6807 68.07%
Thyroid receptor binding - 0.7796 77.96%
Glucocorticoid receptor binding - 0.9473 94.73%
Aromatase binding - 0.7828 78.28%
PPAR gamma - 0.8377 83.77%
Honey bee toxicity - 0.9019 90.19%
Biodegradation + 0.9250 92.50%
Crustacea aquatic toxicity + 0.6300 63.00%
Fish aquatic toxicity + 0.9236 92.36%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL2903 P16050 Arachidonate 15-lipoxygenase 31622.8 nM
Potency
via CMAUP
CHEMBL1075138 Q9NUW8 Tyrosyl-DNA phosphodiesterase 1 35481.3 nM
Potency
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.67% 95.56%
CHEMBL2581 P07339 Cathepsin D 91.65% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 86.98% 91.11%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.59% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.17% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 81.04% 94.73%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.56% 82.69%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Angelica acutiloba
Angelica gigas
Angelica sinensis
Conioselinum anthriscoides
Ligusticum officinale
Lonicera japonica

Cross-Links

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PubChem 6811
NPASS NPC45613
ChEMBL CHEMBL1371297
LOTUS LTS0180864
wikiData Q410882