Tenuazonic acid - Compound Card

Tenuazonic acid

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Tenuazonic acid

Structure
Zoomed Structure
  • Family: Fungi - Pleosporineae
  • Kingdom: Fungi
  • Class: Alkaloid
Canonical Smiles CC[C@@H]([C@H]1NC(=O)C(=C1O)C(=O)C)C
InChI InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)/t5-,8+/m0/s1
InChIKey CEIZFXOZIQNICU-YLWLKBPMSA-N
Formula C10H15NO3
HBA 3
HBD 2
MW 197.23
Rotatable Bonds 3
TPSA 66.4
LogP 0.93
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 197.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Alternaria species Pleosporineae Fungi 5598

Showing of synonyms

  • Aly AH, Edrada-Ebel R, et al. (2008). Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. Journal of Natural Products,2008,71(6),972-980. [View] [PubMed]
Pubchem: 54723289
Nmrshiftdb2: 80005817
CPRiL: 52656
Structure

SMILES: O=C1C=CCN1

Level: 0

Mol. Weight: 197.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.99
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.23
Plasma Protein Binding
31.12
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.63
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.45
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.06
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.58
Rat (Acute)
2.02
Rat (Chronic Oral)
2.18
Fathead Minnow
3.53
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
317.36
Hydration Free Energy
-13.08
Log(D) at pH=7.4
0.33
Log(P)
1.26
Log S
-1.54
Log(Vapor Pressure)
-5.77
Melting Point
112.25
pKa Acid
7.35
pKa Basic
6.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8593
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8593
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8556
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8556
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8551
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8551
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8445
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8445
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8375
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8375
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8297
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8297
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7595
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7595
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7493
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7493
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7492
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7492
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7431
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7431
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 3 0.7398
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 3 0.7398
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7262
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7262
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7099
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7099
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7004
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7004

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