Botryorhodine C - Compound Card

Botryorhodine C

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Botryorhodine C

Structure
Zoomed Structure
  • Family: Fungi - Botryosphaeriaceae
  • Kingdom: Fungi
  • Class: Depsidone
Canonical Smiles OCc1c(O)cc(c2c1Oc1c(C)cc(c(c1OC2=O)C)O)C
InChI InChI=1S/C17H16O6/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/h4-5,18-20H,6H2,1-3H3
InChIKey CYTMELDNMYVTKB-UHFFFAOYSA-N
Formula C17H16O6
HBA 6
HBD 3
MW 316.31
Rotatable Bonds 1
TPSA 96.22
LogP 2.84
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 316.09
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: 46916752
Nmrshiftdb2: 60071130

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 316.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.25
Plasma Protein Binding
71.41
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-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
9.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.63
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.04
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
4.31
Rat (Acute)
2.16
Rat (Chronic Oral)
2.75
Fathead Minnow
4.36
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
435.95
Hydration Free Energy
-8.72
Log(D) at pH=7.4
2.36
Log(P)
2.93
Log S
-4.24
Log(Vapor Pressure)
-7.55
Melting Point
227.12
pKa Acid
7.21
pKa Basic
3.9
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 0.9011
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9011
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8839
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8839
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8564
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8564
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8549
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8549
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8488
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8488
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8481
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8481
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8467
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8467
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8238
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8238
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.8042
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.8042
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8012
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8012
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7969
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7969
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7953
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7953
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7951
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7951
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7908
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7908
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7898
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7898
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7797
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7797
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7671
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7671
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7514
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7514
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7484
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7484
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7475
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7475
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7467
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7467
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7443
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7443
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7386
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7386
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7378
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7378
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7344
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7344
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7338
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7338
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7224
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7224
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7212
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7212
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7203
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7203
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7159
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7159
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7139
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7139
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 4 0.7120
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 4 0.7120
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7110
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7110
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7093
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7093
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7086
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7086
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7065
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7065
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7057
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7057

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