Botryorhodine B - Compound Card

Botryorhodine B

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Botryorhodine B

Structure
Zoomed Structure
  • Family: Fungi - Botryosphaeriaceae
  • Kingdom: Fungi
  • Class: Depsidone
Canonical Smiles O=Cc1c(O)cc(c2c1Oc1c(C)cc(c(c1OC2=O)C)O)C
InChI InChI=1S/C17H14O6/c1-7-4-12(20)10(6-18)16-13(7)17(21)23-15-9(3)11(19)5-8(2)14(15)22-16/h4-6,19-20H,1-3H3
InChIKey KZZIDFSUFCJBAK-UHFFFAOYSA-N
Formula C17H14O6
HBA 6
HBD 2
MW 314.29
Rotatable Bonds 1
TPSA 93.06
LogP 3.16
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 314.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Diplodia quercivora Botryosphaeriaceae Fungi 1281306

Showing of synonyms

  • Abdou R, Scherlach K, et al. (2010). Botryorhodines A–D, antifungal and cytotoxic depsidones from Botryosphaeria rhodina, an endophyte of the medicinal plant Bidens pilosa. Phytochemistry,2010,71(1),110-116. [View] [PubMed]
Pubchem: 46209444
Nmrshiftdb2: 60071131

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)Oc3c(OC2=O)cccc3

Level: 0

Mol. Weight: 314.29 g/mol

Antifungal
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
57.56
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.46
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.84
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.08
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
5.25
Rat (Acute)
2.27
Rat (Chronic Oral)
2.13
Fathead Minnow
4.46
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
432.36
Hydration Free Energy
-7.57
Log(D) at pH=7.4
2.86
Log(P)
3.87
Log S
-5.1
Log(Vapor Pressure)
-8.0
Melting Point
237.17
pKa Acid
6.72
pKa Basic
2.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8765
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8765
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8670
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8670
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8647
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8647
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8642
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8642
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8598
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8598
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8590
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8590
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8450
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8450
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8444
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8444
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8248
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8248
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8247
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8247
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8199
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8199
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.8157
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.8157
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8020
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8020
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.8018
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.8018
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7926
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7926
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7792
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7792
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7727
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7727
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7706
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7706
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7626
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7626
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7556
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7556
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7537
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7537
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7439
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7439
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7397
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7397
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7341
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7341
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7333
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7333
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7329
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7329
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7302
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7302
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7287
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7287
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7272
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7272
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7270
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7270
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7214
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7214
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7171
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7171
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7165
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7165
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7126
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7126
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7088
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7088
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7086
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7086
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.7077
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.7077

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