4alpha-hydroxy-4,15-dihydrocostic acid methyl ester - Compound Card

4alpha-hydroxy-4,15-dihydrocostic acid methyl ester

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4alpha-hydroxy-4,15-dihydrocostic acid methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COC(=O)C(=C)[C@@H]1CC[C@@]2([C@@H](C1)[C@](C)(O)CCC2)C
InChI InChI=1S/C16H26O3/c1-11(14(17)19-4)12-6-9-15(2)7-5-8-16(3,18)13(15)10-12/h12-13,18H,1,5-10H2,2-4H3/t12-,13-,15-,16-/m1/s1
InChIKey PMRPCJXLEQCTBH-RRCSTGOVSA-N
Formula C16H26O3
HBA 3
HBD 1
MW 266.38
Rotatable Bonds 2
TPSA 46.53
LogP 3.07
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 266.19
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: 181463
Nmrshiftdb2: 70045540

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 266.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.350
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.450
Plasma Protein Binding
52.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
10.630
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.490
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.070
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
-0.220
Rat (Acute)
2.200
Rat (Chronic Oral)
1.880
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
314.940
Hydration Free Energy
-4.300
Log(D) at pH=7.4
3.110
Log(P)
3.29
Log S
-3.45
Log(Vapor Pressure)
-4.33
Melting Point
83.6
pKa Acid
10.37
pKa Basic
7.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9330
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9330
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8852
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8852
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8560
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8560
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8535
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8535
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7794
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7794
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7722
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7722
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7649
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7649
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7639
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7639
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7463
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7463
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7399
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7399
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7349
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7349
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7318
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7318
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7276
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7276
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7257
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7257
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7241
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7241
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7229
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7229
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7152
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7152
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7144
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7144
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7118
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7118
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7054
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7054
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7011
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7011
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7009
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7009

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