4-epi-illicic acid - Compound Card

4-epi-illicic acid

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4-epi-illicic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C([C@@H]1CC[C@@]2([C@@H](C1)[C@@](C)(O)CCC2)C)C(=O)O
InChI InChI=1S/C15H24O3/c1-10(13(16)17)11-5-8-14(2)6-4-7-15(3,18)12(14)9-11/h11-12,18H,1,4-9H2,2-3H3,(H,16,17)/t11-,12-,14-,15+/m1/s1
InChIKey FXKCXGBBUBCRPU-GBOPCIDUSA-N
Formula C15H24O3
HBA 2
HBD 2
MW 252.35
Rotatable Bonds 2
TPSA 57.53
LogP 2.98
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 252.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus mauritanicus Asteraceae Plantae 64998
2 Tarchonanthus camphoratus Asteraceae Plantae 41650

Showing of synonyms

  • Hegazy MEF, Tawfik WA, et al. (2015). Sesquiterpene acid derivatives from Tarchonanthus camphoratus. Research Journal of Pharmaceutical, Biological and Chemical Sciences,2015,6(1),659-663. [View]
  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 6452036
Nmrshiftdb2: 70025724

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 252.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
58.84
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
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
4.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.42
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.74
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
-0.66
Rat (Acute)
2.26
Rat (Chronic Oral)
2.36
Fathead Minnow
3.93
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
330.06
Hydration Free Energy
-7.0
Log(D) at pH=7.4
0.04
Log(P)
2.86
Log S
-2.88
Log(Vapor Pressure)
-5.74
Melting Point
135.11
pKa Acid
4.02
pKa Basic
9.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9126
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9126
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8639
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8639
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8610
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8610
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8485
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8485
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8405
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8405
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8113
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8113
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7525
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7525
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7399
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7399
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7387
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7387
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7384
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7384
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7364
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7364
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7221
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7221
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7184
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7184
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7078
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7078
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7033
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7033

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