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10,11-epoxycurvularin

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Lactone
- Subclass: Macrolide

Canonical Smiles	C[C@H]1CCC[C@H]2O[C@@H]2C(=O)c2c(CC(=O)O1)cc(O)cc2O
InChI	InChI=1S/C16H18O6/c1-8-3-2-4-12-16(22-12)15(20)14-9(6-13(19)21-8)5-10(17)7-11(14)18/h5,7-8,12,16-18H,2-4,6H2,1H3/t8-,12+,16-/m0/s1
InChIKey	BVDHPBILFRQGEC-XLIXJNEVSA-N
Formula	C₁₆H₁₈O₆
HBA	6
HBD	2
MW	306.31
Rotatable Bonds	0
TPSA	96.36
LogP	1.71
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	306.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Penicillium species	Trichocomaceae	Fungi	5073

Showing of synonyms

Aly AH, Debbab A, et al. (2011). NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum. Bioorganic and Medicinal Chemistry,2011,19(1),414-421. [View] [PubMed]

Pubchem: 14314906

Zinc: ZINC000031161553

Nmrshiftdb2: 80008155

Chembl: CHEMBL1643632

No compound-protein relationship available.

SMILES: C12C(O2)CCCCOC(=O)Cc3c(C1=O)cccc3

Level: 0

Mol. Weight: 306.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.19
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.88
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.81

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.26
Plasma Protein Binding: 24.33
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: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 16.59
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.06
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.89
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.42
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: -0.23
Rat (Acute): 2.51
Rat (Chronic Oral): 2.5
Fathead Minnow: 4.04
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 414.66
Hydration Free Energy: -10.24
Log(D) at pH=7.4: 0.57
Log(P): 1.61
Log S: -2.7
Log(Vapor Pressure): -7.2
Melting Point: 187.79
pKa Acid: 7.06
pKa Basic: 5.85

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9255
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9255
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.9220
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.9220
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9079
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9079
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9024
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9024
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9014
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9014
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8899
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8899
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8760
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8760
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8753
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8753
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8494
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8494
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8438
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8438
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8411
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8411
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8310
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8310
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8252
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8252
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8192
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8192
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8064
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8064
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8039
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8039
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8018
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8018
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7964
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7964
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7964
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7964
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7932
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7932
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7925
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7925
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7758
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7758
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7753
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7753
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7702
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7702
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7666
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7666
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7638
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7638
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7621
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7621
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7593
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7593
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7579
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7579
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7545
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7545
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7485
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7485
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7457
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7457
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7450
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7450
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7434
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7434
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7429
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7429
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7418
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7418
histidine kinase	Q9WZV7	Q9WZV7_THEMA	Thermotoga maritima	3	0.7411
histidine kinase	Q9WZV7	Q9WZV7_THEMA	Thermotoga maritima	3	0.7411
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7393
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7393
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7392
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7392
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7378
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7378
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7359
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7359
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7350
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7350
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7338
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7338
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7320
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7320
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7286
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7286
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7275
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7275
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7241
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7241
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7239
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7239
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7231
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7231
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7210
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7210
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7206
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7206
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7195
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7195
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7195
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7195
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7183
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7183
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7177
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7177
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7170
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7170
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7170
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7170
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	4	0.7157
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	4	0.7157
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7114
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7114
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7113
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7113
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7093
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7093
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7092
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7092
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7082
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7082
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7066
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7066
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7055
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7055
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7053
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7053
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7044
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7044
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7026
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7026
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7023
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7023
Vitamin D3 receptor A	Q9PTN2	VDRA_DANRE	Danio rerio	4	0.7014
Vitamin D3 receptor A	Q9PTN2	VDRA_DANRE	Danio rerio	4	0.7014
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7013
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7013
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7002
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7002
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7002
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7002
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7001
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7001

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