Botryorhodine A - Compound Card

Botryorhodine A

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Botryorhodine A

Structure
Zoomed Structure
  • Family: Fungi - Botryosphaeriaceae
  • Kingdom: Fungi
  • Class: Depsidone
Canonical Smiles O=Cc1c(O)cc(c2c1Oc1c(C)cc(cc1OC2=O)O)C
InChI InChI=1S/C16H12O6/c1-7-4-11(19)10(6-17)15-13(7)16(20)21-12-5-9(18)3-8(2)14(12)22-15/h3-6,18-19H,1-2H3
InChIKey QQDBQWUHQOGQCJ-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 2
MW 300.27
Rotatable Bonds 1
TPSA 93.06
LogP 2.85
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 300.06
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: 46178006
Nmrshiftdb2: 60071132

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 300.27 g/mol

Antifungal
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
57.35
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
8.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.89
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.8
Micronucleos
Toxic
NR-AhR
Safe
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
5.23
Rat (Acute)
2.23
Rat (Chronic Oral)
2.24
Fathead Minnow
4.4
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
429.91
Hydration Free Energy
-7.99
Log(D) at pH=7.4
2.68
Log(P)
3.49
Log S
-5.12
Log(Vapor Pressure)
-7.89
Melting Point
246.15
pKa Acid
6.97
pKa Basic
2.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9115
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9115
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.9091
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.9091
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8772
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8772
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8683
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8683
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8654
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8654
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8632
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8632
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8610
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8610
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8608
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8608
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8520
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8520
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8265
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8265
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8195
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8195
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8159
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8159
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8106
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8106
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8068
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8068
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.8066
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.8066
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7814
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7814
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7742
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7742
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7736
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7736
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7733
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7733
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7685
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7685
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7651
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7651
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7556
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7556
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7527
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7527
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7523
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7523
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.7512
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.7512
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7498
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7498
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7454
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7454
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7445
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7445
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7427
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7427
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7413
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7413
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7392
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7392
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7381
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7381
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7367
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7367
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7354
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7354
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7325
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7325
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7319
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7319
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7299
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7299
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7294
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7294
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7268
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7268
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7254
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7254
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7232
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7232
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7176
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7176
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7168
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7168
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7164
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7164
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7147
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7147
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7145
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7145
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7140
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7140
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7121
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7121
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7085
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7085
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7082
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7082
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7071
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7071
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7071
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7071
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7051
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7051
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7035
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7035
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7016
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7016
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7001
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7001

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