Botryorhodine D - Compound Card

Botryorhodine D

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Botryorhodine D

Structure
Zoomed Structure
  • Family: Botryosphaeriaceae
  • Kingdom: Fungi
  • Class: Depsidone
Canonical Smiles OCc1c(O)cc(c2c1Oc1c(C)cc(cc1OC2=O)O)C
InChI InChI=1S/C16H14O6/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/h3-5,17-19H,6H2,1-2H3
InChIKey KDERZBIXGNVSOM-UHFFFAOYSA-N
Formula C16H14O6
HBA 6
HBD 3
MW 302.28
Rotatable Bonds 1
TPSA 96.22
LogP 2.53
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 302.08
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: 42637419
Nmrshiftdb2: 60071129

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 212.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.31
Plasma Protein Binding
70.54
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
9.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.6
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.65
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.99
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
4.29
Rat (Acute)
2.17
Rat (Chronic Oral)
2.86
Fathead Minnow
4.27
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
433.82
Hydration Free Energy
-9.2
Log(D) at pH=7.4
2.18
Log(P)
2.56
Log S
-4.22
Log(Vapor Pressure)
-7.48
Melting Point
236.36
pKa Acid
7.44
pKa Basic
3.51
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 0.9029
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9029
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8947
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8947
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8924
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8924
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8857
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8857
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8843
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8843
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8699
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8699
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8658
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8658
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8511
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8511
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.8510
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.8510
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8226
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8226
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8162
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8162
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8042
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8042
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7993
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7993
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7846
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7846
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7830
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7830
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7781
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7781
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7778
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7778
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7752
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7752
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7670
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7670
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7525
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7525
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7505
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7505
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7495
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7495
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7418
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7418
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7398
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7398
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 4 0.7362
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 4 0.7362
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7342
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7342
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7318
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7318
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7308
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7308
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7305
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7305
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7286
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7286
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7283
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7283
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7218
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7218
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7216
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7216
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7209
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7209
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7183
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7183
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7181
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7181
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7169
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7169
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7147
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7147
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7135
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7135
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 4 0.7124
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 4 0.7124
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7110
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7110
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7074
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7074
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7009
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7009

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