Cedrecoumarin A - Compound Card

Cedrecoumarin A

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Cedrecoumarin A

Structure
Zoomed Structure
  • Family: Ptaeroxylaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Prenylated Coumarin
Canonical Smiles O=c1ccc2c(o1)cc(c1c2C=CC(O1)(C)C)O
InChI InChI=1S/C14H12O4/c1-14(2)6-5-9-8-3-4-12(16)17-11(8)7-10(15)13(9)18-14/h3-7,15H,1-2H3
InChIKey OGTYTYOKQRCQEM-UHFFFAOYSA-N
Formula C14H12O4
HBA 4
HBD 1
MW 244.25
Rotatable Bonds 0
TPSA 59.67
LogP 2.68
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 244.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cedrelopsis grevei Ptaeroxylaceae Plantae 864332
2 Cedrelopsis microfoliolata Ptaeroxylaceae Plantae 1304322

Showing of synonyms

  • Koorbanally NA, Randrianarivelojosia M, et al. (2002). Bioactive Constituents of Cedrelopsis microfoliata. Journal of natural products, 2002, 65(9), 1349–1352. [View]
  • Mulholland DA, Kotsos M, et al. (2002). Coumarins from Cedrelopsis grevei (Ptaeroxylaceae). Phytochemistry, 2002, 61(8), 919–922. [View]
Pubchem: 10263845
Nmrshiftdb2: 20122871

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(c1c23)ccc2oc(=O)cc3

Level: 0

Mol. Weight: 200.19 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.300
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.950
Plasma Protein Binding
42.15
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
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
8.430
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.260
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.420
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.440
Micronucleos
Toxic
NR-AhR
Toxic
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
4.190
Rat (Acute)
3.210
Rat (Chronic Oral)
1.640
Fathead Minnow
4.260
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
388.200
Hydration Free Energy
-9.770
Log(D) at pH=7.4
2.520
Log(P)
2.45
Log S
-3.72
Log(Vapor Pressure)
-6.68
Melting Point
227.67
pKa Acid
7.33
pKa Basic
4.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.9390
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8976
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8699
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8580
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8567
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8211
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7939
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7907
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7834
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7829
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7707
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7696
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7696
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7686
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7672
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7645
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7637
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7631
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7603
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7592
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7584
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7520
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7479
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7460
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7307
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7250
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7178
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7150
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7137
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7107
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7087
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7072
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7061
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7060
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7050
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7023

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