9-methoxy-2,2-dimethyl-2H-benzo[h]chromene-7,10-diol - Compound Card

9-methoxy-2,2-dimethyl-2H-benzo[h]chromene-7,10-diol

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9-methoxy-2,2-dimethyl-2H-benzo[h]chromene-7,10-diol

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Naphthalene Derivative
Canonical Smiles COc1cc(O)c2c(c1O)c1OC(C)(C)C=Cc1cc2
InChI InChI=1S/C16H16O4/c1-16(2)7-6-9-4-5-10-11(17)8-12(19-3)14(18)13(10)15(9)20-16/h4-8,17-18H,1-3H3
InChIKey NYSUAOVYCCTQEP-UHFFFAOYSA-N
Formula C16H16O4
HBA 4
HBD 2
MW 272.3
Rotatable Bonds 1
TPSA 58.92
LogP 3.44
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 272.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas bussei Rubiaceae Plantae 387051
2 Pentas parvifolia Rubiaceae Plantae 296969

Showing of synonyms

  • 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]

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c1c23)ccc2cccc3

Level: 0

Mol. Weight: 272.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.950
Plasma Protein Binding
50.88
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.230
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.160
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
5.260
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
3.730
Rat (Acute)
2.420
Rat (Chronic Oral)
2.560
Fathead Minnow
4.390
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
378.540
Hydration Free Energy
-9.350
Log(D) at pH=7.4
3.530
Log(P)
3.23
Log S
-4.68
Log(Vapor Pressure)
-5.86
Melting Point
175.08
pKa Acid
8.09
pKa Basic
5.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9375
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9375
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8847
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8847
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8503
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8503
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8292
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8292
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8236
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8236
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8214
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8214
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8152
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8152
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8014
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8014
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7925
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7925
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7859
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7859
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7661
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7661
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7617
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7617
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7544
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7544
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7460
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7460
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7437
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7437
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7429
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7429
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7407
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7407
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7391
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7391
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7376
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7376
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7374
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7374
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7270
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7270
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7254
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7254
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7210
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7210
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7181
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7181
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7151
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7151
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7070
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7070
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7064
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7064
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7048
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7048
Thiosulfate reductase Q72LA4 Q72LA4_THET2 Thermus thermophilus 4 0.7015
Thiosulfate reductase Q72LA4 Q72LA4_THET2 Thermus thermophilus 4 0.7015

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