Istanbulin Β - Compound Card

Istanbulin Β

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Istanbulin Β

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC1=C2C[C@@]3(C)[C@H](C)CCC(=O)[C@@H]3C[C@@H]2OC1=O
InChI InChI=1S/C15H20O3/c1-8-4-5-12(16)11-6-13-10(7-15(8,11)3)9(2)14(17)18-13/h8,11,13H,4-7H2,1-3H3/t8-,11+,13+,15+/m1/s1
InChIKey IXMDYOSMFGVWJY-KIRGAOJCSA-N
Formula C15H20O3
HBA 3
HBD 0
MW 248.32
Rotatable Bonds 0
TPSA 43.37
LogP 2.64
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio aegyptius Asteraceae Plantae 121537

Showing of synonyms

  • Mohamed AEHH, Ahmed AA (2005). Eremophilane-type sesquiterpene derivatives from Senecio aegyptius var. discoideus. Journal of Natural Products,2005,68,439-442. [View] [PubMed]
Pubchem: 101967144
Nmrshiftdb2: 70034907

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)CC3C(C2)CCCC3=O

Level: 0

Mol. Weight: 248.32 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
47.01
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
11.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.24
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.18
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
-0.56
Rat (Acute)
2.09
Rat (Chronic Oral)
1.49
Fathead Minnow
3.88
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
328.07
Hydration Free Energy
-5.02
Log(D) at pH=7.4
1.91
Log(P)
1.96
Log S
-2.76
Log(Vapor Pressure)
-4.63
Melting Point
131.21
pKa Acid
9.23
pKa Basic
5.91
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 0.9011
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9011
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8727
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8727
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8530
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8530
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8353
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8353
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8284
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8284
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8171
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8171
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8117
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8117
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7974
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7974
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7761
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7761
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7730
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7730
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7632
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7632
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7494
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7494
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7486
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7486
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7465
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7465
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7410
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7410
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7406
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7406
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7375
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7375
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7358
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7358
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7293
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7293
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7242
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7242
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7107
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7107
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7065
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7065
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7044
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7044
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7028
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7028
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7023
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7023
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7014
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7014
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7005
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7005

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