Transgleinadiene - Compound Card

Transgleinadiene

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Transgleinadiene

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles COc1cc(OC)c2c(c1/C=C/C(=C)C)oc(=O)cc2
InChI InChI=1S/C16H16O4/c1-10(2)5-6-11-13(18-3)9-14(19-4)12-7-8-15(17)20-16(11)12/h5-9H,1H2,2-4H3/b6-5+
InChIKey XUEBXQXWALAJLA-AATRIKPKSA-N
Formula C16H16O4
HBA 4
HBD 0
MW 272.3
Rotatable Bonds 4
TPSA 48.67
LogP 3.4
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 272.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus aurantium Rutaceae Plantae 43166

Showing of synonyms

  • Bissim S, Kenmogne S, et al. (2019). Bioactive acridone alkaloids and their derivatives from Citrus aurantium (Rutaceae). Phytochemistry Letters, 2019, 29, 148-153. [View]
Pubchem: 14503616
Nmrshiftdb2: 60075166

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 272.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.47
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.050
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.040
Plasma Protein Binding
48.47
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.780
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.520
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.950
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.220
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
4.760
Rat (Acute)
2.120
Rat (Chronic Oral)
1.940
Fathead Minnow
4.820
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
378.350
Hydration Free Energy
-8.220
Log(D) at pH=7.4
2.700
Log(P)
3.07
Log S
-4.51
Log(Vapor Pressure)
-5.48
Melting Point
150.63
pKa Acid
8.06
pKa Basic
4.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9727
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.9028
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8986
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8903
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8755
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8736
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8690
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8637
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8613
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8555
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8362
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8162
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8045
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7919
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7879
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7851
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7818
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7783
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7712
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7655
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7625
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7547
uroporphyrinogen-III C-methyltransferase P95417 P95417_PSEAI Pseudomonas aeruginosa 3 0.7516
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7501
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7494
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7459
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7437
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 3 0.7430
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7401
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7366
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7357
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7310
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7304
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7270
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7264
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7228
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7205
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7193
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7174
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7136
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7127
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7126
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7124
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7118
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7098
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7097
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7094
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7067
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7045
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7033
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7033
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7021
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7019

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