Tanzawaic acid F - Compound Card

Tanzawaic acid F

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Tanzawaic acid F

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Carboxylic Acid
Canonical Smiles OC(=O)/C=C/C=C/[C@H]1[C@@H](C)C=C[C@@H]2[C@@H]1[C@H](C)CC(C2)C(=O)O
InChI InChI=1S/C18H24O4/c1-11-7-8-13-10-14(18(21)22)9-12(2)17(13)15(11)5-3-4-6-16(19)20/h3-8,11-15,17H,9-10H2,1-2H3,(H,19,20)(H,21,22)/b5-3+,6-4+/t11-,12+,13-,14?,15-,17-/m0/s1
InChIKey CTZUNMXSKIMIEE-GNUZFWQPSA-N
Formula C18H24O4
HBA 2
HBD 2
MW 304.39
Rotatable Bonds 4
TPSA 74.6
LogP 3.37
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 304.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium citrinum Trichocomaceae Fungi 5077

Showing of synonyms

  • El-Neketi M, Ebrahim W, et al. (2013). Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the Moroccan plant Ceratonia siliqua. Journal of Natural Products,2013,76(6),1099-1104. [View] [PubMed]
Pubchem: 21775855
Nmrshiftdb2: 70023958

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 304.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.28
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.92
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
77.73
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
-2.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.65
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.98
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.4
Micronucleos
Safe
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
1.33
Rat (Acute)
2.56
Rat (Chronic Oral)
2.47
Fathead Minnow
4.03
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
395.53
Hydration Free Energy
-6.31
Log(D) at pH=7.4
-0.66
Log(P)
4.5
Log S
-4.61
Log(Vapor Pressure)
-8.51
Melting Point
217.44
pKa Acid
5.0
pKa Basic
7.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9311
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9311
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9260
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9260
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9068
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9068
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8744
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8744
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8587
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8587
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8392
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8392
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8354
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8354
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8339
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8339
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8339
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8339
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8287
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8287
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8139
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8139
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7901
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7901
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7812
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7812
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7811
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7811
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7778
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7778
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7716
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7716
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7610
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7610
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7578
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7578
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7511
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7511
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7507
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7507
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7493
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7493
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7469
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7469
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7426
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7426
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7403
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7343
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7343
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7319
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7319
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7283
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7283
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7229
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7229
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7217
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7217
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7196
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7196
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7168
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7168
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7158
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7158
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7156
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7156
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7142
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7142
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7137
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7137
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7122
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7122
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7076
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7076
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7040
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7040
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7019
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7019
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7010
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7010
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7008
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7008

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