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Dioxoauroglaucin

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Benzaldehyde
- Subclass: Prenylated Benzaldehyde

Canonical Smiles	O=Cc1c(/C=C\C2OOC(C=C2)C)c(O)cc(c1O)CC=C(C)C
InChI	InChI=1S/C19H22O5/c1-12(2)4-6-14-10-18(21)16(17(11-20)19(14)22)9-8-15-7-5-13(3)23-24-15/h4-5,7-11,13,15,21-22H,6H2,1-3H3/b9-8-
InChIKey	UOHLQZAQDSZVES-HJWRWDBZSA-N
Formula	C₁₉H₂₂O₅
HBA	5
HBD	2
MW	330.38
Rotatable Bonds	5
TPSA	75.99
LogP	3.71
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	330.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus sp	Trichocomaceae	Fungi	5065

Showing of synonyms

Elissawy A, Ebada S, et al. (2019). New secondary metabolites from the mangrove-derived fungus Aspergillus sp. AV-2. Phytochemistry Letters,2019,29,1-5. [View]

Pubchem: 146682458

Nmrshiftdb2: 80017517

No compound-protein relationship available.

SMILES: c1ccccc1C=CC2C=CCOO2

Level: 1

Mol. Weight: 330.38 g/mol

SMILES: C1=CCOOC1

Level: 0

Mol. Weight: 330.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 330.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.68
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.49
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.53
Plasma Protein Binding: 20.1
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: 8.16
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.35
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.18
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.68
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: 1.33
Rat (Acute): 2.31
Rat (Chronic Oral): 2.13
Fathead Minnow: 4.48
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 381.32
Hydration Free Energy: -10.66
Log(D) at pH=7.4: 2.61
Log(P): 4.81
Log S: -4.07
Log(Vapor Pressure): -7.34
Melting Point: 91.21
pKa Acid: 6.79
pKa Basic: 4.16

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.9221
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9128
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8949
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8948
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8831
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8165
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8122
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8101
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7986
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7965
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7918
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7892
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7880
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7845
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7690
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.7683
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7631
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7594
Acyl-homoserine-lactone synthase	Q4VSJ8	Q4VSJ8_BURGL	Burkholderia glumae	4	0.7584
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7541
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7538
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7525
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7513
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7504
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7484
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7478
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7398
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7371
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7331
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7331
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7310
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7298
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7277
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7269
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7245
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7237
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7220
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7159
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7157
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7138
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7108
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7079

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