Macrosporin-7-O-sulphate - Compound Card

Macrosporin-7-O-sulphate

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Macrosporin-7-O-sulphate

Structure
Zoomed Structure
  • Family: Fungi - Phaeosphaeriaceae
  • Kingdom: Fungi
  • Class: Quinone
    • Subclass: Sulphunated Anthraquinone
Canonical Smiles COc1cc(O)c2c(c1)C(=O)c1c(C2=O)cc(c(c1)C)OS(=O)(=O)O[Na]
InChI InChI=1S/C16H12O8S.Na/c1-7-3-9-10(6-13(7)24-25(20,21)22)16(19)14-11(15(9)18)4-8(23-2)5-12(14)17;/h3-6,17H,1-2H3,(H,20,21,22);/q;+1/p-1
InChIKey QPOBCRFPDXHZDS-UHFFFAOYSA-M
Formula C16H11NaO8S
HBA 8
HBD 1
MW 386.31
Rotatable Bonds 4
TPSA 116.2
LogP 1.21
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 386.01
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ampelomyces species Phaeosphaeriaceae Fungi 50729

Showing of synonyms

  • Aly AH, Edrada-Ebel R, et al. (2008). Bioactive metabolites from the endophytic fungus Ampelomyces sp. isolated from the medicinal plant Urospermum picroides. Phytochemistry,2008,69(8),1716-1725. [View] [PubMed]
Pubchem: 24882466

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 386.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.0
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.670
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.170
Plasma Protein Binding
11.35
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.840
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.180
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
0.000
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.050
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
4.340
Rat (Acute)
2.140
Rat (Chronic Oral)
2.220
Fathead Minnow
4.940
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
467.180
Hydration Free Energy
-7.110
Log(D) at pH=7.4
1.640
Log(P)
3.43
Log S
-3.8
Log(Vapor Pressure)
-7.3
Melting Point
187.46
pKa Acid
4.96
pKa Basic
4.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9291
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9291
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9232
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9232
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9184
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9184
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9109
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9109
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9103
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9103
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9086
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9086
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9043
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9043
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8783
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8783
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8596
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8596
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8550
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8550
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8434
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8434
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8392
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8392
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8367
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8367
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8298
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8298
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8194
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8194
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8180
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8180
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7978
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7978
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7974
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7974
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7930
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7930
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7791
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7791
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7623
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7623
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7610
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7610
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7549
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7549
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7540
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7540
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7520
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7520
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7512
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7512
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7487
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7487
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7447
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7447
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7394
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7394
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7394
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7394
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7363
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7363
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7314
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7314
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7297
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7297
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7295
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7295
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7252
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7252
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7106
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7106
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7104
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7104
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7096
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7096
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7088
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7088
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7085
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7085
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7081
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7081
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7054
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7054
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7046
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7046
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7014
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7014

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