Bichromonol - Compound Card

Bichromonol

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Bichromonol

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Dimeric Coumarin
Canonical Smiles COc1c(O)cc2c(c1c1c(O)ccc3c1oc(=O)cc3)oc(=O)cc2
InChI InChI=1S/C19H12O7/c1-24-19-12(21)8-10-4-7-14(23)26-18(10)16(19)15-11(20)5-2-9-3-6-13(22)25-17(9)15/h2-8,20-21H,1H3
InChIKey LWUIOTCDQMPCRC-UHFFFAOYSA-N
Formula C19H12O7
HBA 7
HBD 2
MW 352.3
Rotatable Bonds 2
TPSA 110.11
LogP 2.99
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.05
Exact Mass 352.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum roeperianum Hypericaceae Plantae —

Showing of synonyms

  • Fobofou SAT, Franke K, et al. (2023). Bichromonol, a dimeric coumarin with anti-HIV activity from the stem bark of Hypericum roeperianum.. Natural product research,2023, 37(12), 1947-1953. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=c(o1)ccc(c12)cccc2-c3cccc(c34)ccc(=O)o4

Level: 1

Mol. Weight: 352.3 g/mol

Structure

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

Level: 0

Mol. Weight: 352.3 g/mol

Antiviral

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.700
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.630
Plasma Protein Binding
92.6
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.330
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.990
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.940
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.810
Micronucleos
Toxic
NR-AhR
Toxic
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
-0.170
Rat (Acute)
2.430
Rat (Chronic Oral)
2.250
Fathead Minnow
5.120
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
515.400
Hydration Free Energy
-9.330
Log(D) at pH=7.4
2.310
Log(P)
2.0
Log S
-5.35
Log(Vapor Pressure)
-9.22
Melting Point
305.98
pKa Acid
9.95
pKa Basic
3.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9252
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8968
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8702
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8521
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8487
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8412
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8283
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8130
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8012
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7900
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7824
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7704
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7700
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7663
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7498
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7497
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7477
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7476
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7450
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7396
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7366
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7343
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7321
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7308
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7304
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7304
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7291
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7288
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7262
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7249
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7245
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7203
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 3 0.7125
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 3 0.7124
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7112
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7103
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7100
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7095
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7079
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 2 0.7075
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7024
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7024

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