7-hydroxy-3,3-dimethyl-10-methoxy-3H-benzo[f]chromene-8-carboxylic acid - Compound Card

7-hydroxy-3,3-dimethyl-10-methoxy-3H-benzo[f]chromene-8-carboxylic acid

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7-hydroxy-3,3-dimethyl-10-methoxy-3H-benzo[f]chromene-8-carboxylic acid

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Naphthohydroquinone
Canonical Smiles COc1cc(C(=O)O)c(c2c1c1C=CC(Oc1cc2)(C)C)O
InChI InChI=1S/C17H16O5/c1-17(2)7-6-9-12(22-17)5-4-10-14(9)13(21-3)8-11(15(10)18)16(19)20/h4-8,18H,1-3H3,(H,19,20)
InChIKey QKIYZHRZSUVGEG-UHFFFAOYSA-N
Formula C17H16O5
HBA 4
HBD 2
MW 300.31
Rotatable Bonds 2
TPSA 75.99
LogP 3.44
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 300.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas bussei Rubiaceae Plantae 387051
2 Pentas bussei Rubiaceae Plantae 387051
3 Pentas bussei Rubiaceae Plantae 387051
4 Pentas parvifolia Rubiaceae Plantae 296969
5 Pentas parvifolia Rubiaceae Plantae 296969

Showing of synonyms

  • Endale M, Ekberg A, et al. (2012). Busseihydroquinones A-D from the roots of Pentas bussei. Journal of Natural Products,2012,75(7),1299-1304. [View] [PubMed]
  • Bukuru J, De Kimpe N, et al. (2003). Isolation and structural elucidation of natural products from Pentas bussei K. Krause, Pentas lanceolata (Forsk.) Deflers and Pentas parvifolia Hiern (Rubiaceae). Ph.D. Thesis, University of Ghent, Faculty of Bioscience Engineering, Belgium,2003. [View] [PubMed]
  • Abdissa N, Pan F, et al. (2016). Naphthalene derivatives from the roots of Pentas parvifolia and Pentas bussei. Journal of Natural Products,2016,79(9),2181-2187. [View] [PubMed]
Pubchem: 70688905
Nmrshiftdb2: 70099808

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(c1c23)ccc2cccc3

Level: 0

Mol. Weight: 300.31 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.870
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.290
Plasma Protein Binding
50.2
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
6.250
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.630
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.220
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.540
Micronucleos
Toxic
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
3.560
Rat (Acute)
2.290
Rat (Chronic Oral)
3.370
Fathead Minnow
4.120
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
383.760
Hydration Free Energy
-8.790
Log(D) at pH=7.4
1.440
Log(P)
4.76
Log S
-4.09
Log(Vapor Pressure)
-6.87
Melting Point
206.73
pKa Acid
7.26
pKa Basic
5.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9055
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9055
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9029
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9029
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8915
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8915
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8896
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8896
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8889
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8889
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8763
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8763
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8453
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8453
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.8243
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.8243
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8236
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8236
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8109
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8109
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7919
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7919
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7747
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7747
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7631
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7631
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7604
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7604
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7556
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7556
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7516
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7516
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7348
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7348
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7342
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7342
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7340
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7340
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7174
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7174
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7145
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7145
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7077
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7077

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