Sinaicin - Compound Card

Sinaicin

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Sinaicin

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1C[C@@H]2[C@H](C1=C)[C@H]1OC(=O)[C@@H](C1[C@H](CC2=C)O)C
InChI InChI=1S/C17H22O5/c1-7-5-12(19)15-9(3)17(20)22-16(15)14-8(2)13(6-11(7)14)21-10(4)18/h9,11-16,19H,1-2,5-6H2,3-4H3/t9-,11+,12+,13+,14+,15?,16-/m1/s1
InChIKey BKQBPJIALFPDKG-PEGXEUMZSA-N
Formula C17H22O5
HBA 5
HBD 1
MW 306.36
Rotatable Bonds 1
TPSA 72.83
LogP 1.61
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 306.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea sivasica Asteraceae-Compositae Plantae 1486579

Showing of synonyms

  • Al-Easa HS, Mann J, et al. (1990). Guaianolides from Centaurea sinaica. Phytochemistry,1990,29(4),1324-1325. [View]
Pubchem: 162954446

No compound-protein relationship available.

Structure

SMILES: C=C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 218.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
45.33
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
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
11.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.02
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.44
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.62
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3.0
Rat (Acute)
3.69
Rat (Chronic Oral)
1.75
Fathead Minnow
3.92
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
361.21
Hydration Free Energy
-6.8
Log(D) at pH=7.4
0.67
Log(P)
1.49
Log S
-2.36
Log(Vapor Pressure)
-6.63
Melting Point
142.48
pKa Acid
8.49
pKa Basic
5.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8627
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8627
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8444
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8444
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8185
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8185
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8111
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8111
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8084
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8084
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8016
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8016
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7965
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7965
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7877
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7877
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7875
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7875
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7812
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7812
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7784
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7784
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7728
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7728
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7715
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7715
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7709
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7709
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7679
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7679
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7644
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7644
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7631
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7631
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7629
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7629
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7610
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7610
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7575
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7575
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7566
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7566
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7543
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7543
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7537
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7537
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7532
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7532
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7459
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7459
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7431
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7431
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7373
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7373
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7331
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7331
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7322
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7322
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7270
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7270
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7245
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7245
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7230
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7230
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7226
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7226
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7219
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7219
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7214
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7214
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7208
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7208
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7203
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7203
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7191
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7191
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7185
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7185
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7178
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7178
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7168
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7168
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7166
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7166
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7162
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7162
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7157
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7157
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7146
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7146
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7136
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7136
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7129
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7129
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7119
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7119
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7111
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7111
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7106
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7106
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7106
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7106
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7080
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7080
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7076
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7076
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7056
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7056
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7053
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7053
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7042
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7042
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7031
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7031
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7001
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7001

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