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6,8-dihydroxyisocoumarin-3-carboxylic acid

Family: Fungi - Bionectriaceae
Kingdom: Fungi
Class: Coumarin

Canonical Smiles	Oc1cc(O)c2c(c1)cc(oc2=O)C(=O)O
InChI	InChI=1S/C10H6O6/c11-5-1-4-2-7(9(13)14)16-10(15)8(4)6(12)3-5/h1-3,11-12H,(H,13,14)
InChIKey	GWMILDFJBMOCEW-UHFFFAOYSA-N
Formula	C₁₀H₆O₆
HBA	5
HBD	3
MW	222.15
Rotatable Bonds	1
TPSA	107.97
LogP	0.9
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	16
Formal Charge	0
Fraction CSP3	0.0
Exact Mass	222.02
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Bionectria sp.	Bionectriaceae	Fungi	—

Showing of synonyms

Kamdem RST, Wang H, et al. (2018). Induction of new metabolites from the endophytic fungus Bionectria sp. through bacterial co-culture.. Fitoterapia,2018, 124, 132-136. [View] [PubMed]

Pubchem: 71552030

Zinc: ZINC000205376048

Nmrshiftdb2: 70112356

No compound-protein relationship available.

SMILES: c1cccc(c12)ccoc2=O

Level: 0

Mol. Weight: 222.15 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.22
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.69
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.96
Plasma Protein Binding: 39.79
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.18
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.05
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.25
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.18
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: 2.48
Rat (Acute): 2.25
Rat (Chronic Oral): 2.98
Fathead Minnow: 4.0
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 411.63
Hydration Free Energy: -12.67
Log(D) at pH=7.4: -0.97
Log(P): 1.65
Log S: -2.74
Log(Vapor Pressure): -7.29
Melting Point: 301.39
pKa Acid: 5.12
pKa Basic: 3.92

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9257
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9164
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9059
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.9031
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.9021
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8967
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8953
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8941
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8885
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8883
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8856
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8832
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8778
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8736
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8702
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8663
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8541
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8523
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8459
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8430
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8416
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.8400
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8364
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8361
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8353
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8343
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8278
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8188
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.8169
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8138
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	3	0.8104
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8067
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8019
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7961
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7933
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7881
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7847
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7826
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7796
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7751
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7748
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7697
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7636
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7606
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.7589
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7554
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7514
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	4	0.7487
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7472
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7456
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7419
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7395
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7384
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7383
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7373
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7364
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7354
Cytidylate kinase	B1MB31	B1MB31_MYCA9	Mycobacteroides abscessus	4	0.7343
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7338
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7332
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7326
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7309
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7299
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7292
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	3	0.7291
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7274
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7258
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7255
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7230
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7211
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7205
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7192
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	4	0.7187
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7177
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7176
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7168
CDP-alcohol phosphatidyltransferase AF-2299-like N-terminal domain-containing protein	O27985	O27985_ARCFU	Archaeoglobus fulgidus	4	0.7162
CalS13	Q8KND8	Q8KND8_MICEC	Micromonospora echinospora	3	0.7148
Thymidylate synthase	P07607	TYSY_MOUSE	Mus musculus	4	0.7144
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7143
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7126
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7122
Nucleoside permease	Q9KPL5	Q9KPL5_VIBCH	Vibrio cholerae serotype O1	3	0.7118
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7116
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7108
Deoxycytidylate deaminase	H6WFU3	H6WFU3_9CAUD	Cyanophage S-TIM5	4	0.7098
Mannosylglycerate synthase	D0MI02	D0MI02_RHOM4	Rhodothermus marinus	3	0.7096
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7091
Activated CDC42 kinase 1	Q07912	ACK1_HUMAN	Homo sapiens	3	0.7087
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7073
Egl nine homolog 1	Q9GZT9	EGLN1_HUMAN	Homo sapiens	2	0.7073
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7065
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7062
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7046
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7026
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7008
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7007

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