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(+)-sydowic acid

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Phenolic
- Subclass: Phenolic Acid Derivative

Canonical Smiles	Oc1cc(ccc1[C@@]1(C)CCCC(O1)(C)C)C(=O)O
InChI	InChI=1S/C15H20O4/c1-14(2)7-4-8-15(3,19-14)11-6-5-10(13(17)18)9-12(11)16/h5-6,9,16H,4,7-8H2,1-3H3,(H,17,18)/t15-/m1/s1
InChIKey	PPKSRWBBMMEDGG-OAHLLOKOSA-N
Formula	C₁₅H₂₀O₄
HBA	3
HBD	2
MW	264.32
Rotatable Bonds	2
TPSA	66.76
LogP	3.28
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.53
Exact Mass	264.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus austroafricanus	Eurotiomycetidae	Fungi	1220192
2	Aspergillus versicolor	Trichocomaceae	Fungi	46472

Showing of synonyms

Ebrahim W, El-Neketi M, et al. (2016). Metabolites from the fungal endophyte Aspergillus austroafricanus in axenic culture and in fungal−bacterial mixed cultures. Journal of Natural Products,2016,79,914-922. [View] [PubMed]
Elsbaey M, Tanaka C, et al. (2019). New secondary metabolites from the mangrove endophytic fungus Aspergillus versicolor. Phytochemistry Letters,2019,32,70-76. [View]

Pubchem: 11737144

Cas: 120442-16-2

Nmrshiftdb2: 70000353

Chembl: CHEMBL4519267

No compound-protein relationship available.

SMILES: c1ccccc1C2CCCCO2

Level: 1

Mol. Weight: 264.32 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 264.32 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.88
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.710
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.92

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.460
Plasma Protein Binding: 62.47
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: 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: 10.800
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.220
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.100
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 2.570
Micronucleos: Safe
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: -0.300
Rat (Acute): 2.300
Rat (Chronic Oral): 2.640
Fathead Minnow: 3.920
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 319.430
Hydration Free Energy: -9.170
Log(D) at pH=7.4: 0.850
Log(P): 3.46
Log S: -3.13
Log(Vapor Pressure): -5.88
Melting Point: 180.73
pKa Acid: 5.66
pKa Basic: 6.31

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8949
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8949
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8436
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8436
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8150
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8150
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8139
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8139
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8135
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8135
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7899
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7899
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7817
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7817
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7777
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7777
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7777
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7777
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7759
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7759
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7754
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7754
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7752
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7752
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7706
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7706
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	3	0.7504
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	3	0.7504
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7478
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7478
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7464
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7464
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7438
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7438
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7436
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7436
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7431
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7431
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7399
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7399
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7347
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7347
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7298
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7298
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7289
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7289
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7235
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7235
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7166
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7166
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7144
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7144
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7143
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7143
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7138
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7138
Angiotensin-converting enzyme	Q10714	ACE_DROME	Drosophila melanogaster	2	0.7096
Angiotensin-converting enzyme	Q10714	ACE_DROME	Drosophila melanogaster	2	0.7096
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7004
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7004

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