2alpha-hydroxy-4-epi-ilicic acid - Compound Card

2alpha-hydroxy-4-epi-ilicic acid

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2alpha-hydroxy-4-epi-ilicic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles O[C@H]1C[C@H](O)[C@H]2[C@@](C1)(C)CC[C@H](C2)C(=C)C(=O)O
InChI InChI=1S/C14H22O4/c1-8(13(17)18)9-3-4-14(2)7-10(15)6-12(16)11(14)5-9/h9-12,15-16H,1,3-7H2,2H3,(H,17,18)/t9-,10+,11+,12+,14+/m1/s1
InChIKey JDGJBTMARDZISJ-FGPLHTHASA-N
Formula C14H22O4
HBA 3
HBD 3
MW 254.33
Rotatable Bonds 2
TPSA 77.76
LogP 1.57
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 254.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dittrichia graveolens Asteraceae Plantae 1532790

Showing of synonyms

  • Abou-Douh AM (2008). New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens. Chemical and Pharmaceutical Bulletin,2008,56(11),1535-1545. [View] [PubMed]
Pubchem: 162816936
Nmrshiftdb2: 70056013

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 254.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
53.92
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
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
2.14
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.19
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.81
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.18
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
-1.47
Rat (Acute)
2.18
Rat (Chronic Oral)
2.54
Fathead Minnow
3.98
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
348.82
Hydration Free Energy
-9.98
Log(D) at pH=7.4
-1.26
Log(P)
1.69
Log S
-1.81
Log(Vapor Pressure)
-6.92
Melting Point
153.81
pKa Acid
4.25
pKa Basic
8.26
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 0.8703
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8703
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8598
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8598
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8515
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8515
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8416
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8416
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8318
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8318
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8310
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8310
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8307
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8307
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8242
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8242
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7828
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7828
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7780
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7780
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7666
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7666
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7657
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7657
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7622
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7622
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7621
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7621
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7521
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7521
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7478
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7478
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7202
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7202
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7133
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7132
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7132
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7124
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7124
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7092
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7092
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7077
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7077
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7072
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7072
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7050
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7050
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7028
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7028

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