Costic acid methyl ester - Compound Card

Costic acid methyl ester

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Costic 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)CCC2)C
InChI InChI=1S/C16H24O2/c1-11-6-5-8-16(3)9-7-13(10-14(11)16)12(2)15(17)18-4/h13-14H,1-2,5-10H2,3-4H3/t13-,14+,16-/m1/s1
InChIKey WQPKMCCPWWJBMZ-IJEWVQPXSA-N
Formula C16H24O2
HBA 2
HBD 0
MW 248.37
Rotatable Bonds 2
TPSA 26.3
LogP 3.88
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 248.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia arborescens Asteraceae Plantae 72386

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]
Pubchem: 14707110
Nmrshiftdb2: 60074687

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 248.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.270
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.690
Plasma Protein Binding
59.28
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
9.850
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.160
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.660
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.970
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
1.390
Rat (Acute)
2.260
Rat (Chronic Oral)
1.910
Fathead Minnow
3.940
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
303.790
Hydration Free Energy
-1.420
Log(D) at pH=7.4
4.120
Log(P)
4.72
Log S
-5.12
Log(Vapor Pressure)
-3.28
Melting Point
51.1
pKa Acid
11.62
pKa Basic
6.35
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 0.9493
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9493
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9309
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9309
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9302
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9302
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9266
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9252
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9252
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9245
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9245
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9208
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9208
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9207
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9207
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9201
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9201
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9153
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9153
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8767
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8767
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8747
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8747
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8584
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8584
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8453
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8453
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8384
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8384
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8373
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8373
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8286
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8286
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8286
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8286
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7998
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7998
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7978
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7978
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7948
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7948
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7935
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7935
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7924
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7924
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7879
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7879
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7815
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7815
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7807
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7807
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7800
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7800
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7798
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7798
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7779
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7779
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7774
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7774
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7771
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7771
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7766
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7766
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7763
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7763
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7742
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7742
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7737
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7737
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7735
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7735
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7734
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7734
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7722
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7722
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7717
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7717
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7716
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7716
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7708
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7708
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7705
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7705
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7702
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7702
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7700
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7700
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7696
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7696
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7695
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7695
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7690
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7690
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7685
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7685
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7681
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7681
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7681
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7681
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7679
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7679
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7676
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7676
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7676
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7676
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7675
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7675
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7671
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7671
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7666
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7666
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7660
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7660
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7657
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7657
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7654
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7654
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7651
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7651
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7643
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7643
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7636
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7636
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7630
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7630
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7626
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7626
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7622
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7622
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7620
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7620
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7614
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7614
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7612
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7612
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7612
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7612
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7585
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7585
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7557
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7557
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7548
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7548
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7544
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7544
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7535
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7535
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7507
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7507
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7501
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7501
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7474
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7474
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7470
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7470
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7418
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7418
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7418
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7418
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7411
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7411
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7393
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7393
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7374
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7374
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7359
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7359
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7321
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7321
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7308
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7308
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7296
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7296
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7287
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7287
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7280
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7280
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7233
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7233
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7216
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7216
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7190
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7190
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7184
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7184
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7184
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7184
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7166
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7166
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7072
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7072
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7036
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7036
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7036
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7036
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7011
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7011

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