3alpha-hydroxyisoiphion-11(13)-en-4-one - Compound Card

3alpha-hydroxyisoiphion-11(13)-en-4-one

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3alpha-hydroxyisoiphion-11(13)-en-4-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COC(=O)C(=C)[C@H]1CC[C@@]2([C@@](C1)(C(=O)C)[C@H](O)CC2)C
InChI InChI=1S/C16H24O4/c1-10(14(19)20-4)12-5-7-15(3)8-6-13(18)16(15,9-12)11(2)17/h12-13,18H,1,5-9H2,2-4H3/t12-,13+,15-,16-/m0/s1
InChIKey XUOPWHOHGIDEAX-XRGAULLZSA-N
Formula C16H24O4
HBA 4
HBD 1
MW 280.36
Rotatable Bonds 3
TPSA 63.6
LogP 2.25
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 280.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 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]
Pubchem: 162816846

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCCC2

Level: 0

Mol. Weight: 280.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.480
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.460
Plasma Protein Binding
52.5
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
8.350
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.190
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.070
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.140
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
-0.290
Rat (Acute)
2.900
Rat (Chronic Oral)
1.850
Fathead Minnow
3.920
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
328.520
Hydration Free Energy
-7.590
Log(D) at pH=7.4
1.950
Log(P)
2.21
Log S
-2.72
Log(Vapor Pressure)
-5.38
Melting Point
109.4
pKa Acid
9.37
pKa Basic
4.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8576
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8576
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8221
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8221
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8202
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8202
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8114
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8114
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7816
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7816
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7772
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7772
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7680
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7680
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7606
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7606
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7524
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7524
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7427
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7427
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7410
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7410
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7326
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7326
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7260
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7260
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7244
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7244
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7198
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7198
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7098
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7098
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7089
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7089
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7080
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7080
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7025
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7025

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