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Eleutherinol

Family: Fungi - Trichocomaceae
Kingdom: Fungi, Plantae
Class: Polyketide
- Subclass: Naphthopyranone

Canonical Smiles	O=c1cc(O)c2c(c1)cc(c1c2oc(C)cc1O)C
InChI	InChI=1S/C15H12O4/c1-7-3-9-5-10(16)6-12(18)14(9)15-13(7)11(17)4-8(2)19-15/h3-6,17-18H,1-2H3
InChIKey	PTGIWTMFHZSGPA-UHFFFAOYSA-N
Formula	C₁₅H₁₂O₄
HBA	4
HBD	2
MW	256.26
Rotatable Bonds	0
TPSA	70.67
LogP	2.97
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	256.07
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Eleutherine bulbosa	Iridaceae	Plantae	1210469
2	Aspergillus wentii	Trichocomaceae	Fungi	5066

Showing of synonyms

Gallo FR, Palazzino G, et al. (2010). Polyketides from Eleutherine bulbosa.. Natural product research,2010, 24(16), 1578-1586. [View] [PubMed]
Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]

Pubchem: 136623083

CPRiL: 280401

SMILES: o1cccc(c1c23)ccc2cc(=O)cc3

Level: 0

Mol. Weight: 256.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.68
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.54
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.89

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.35
Plasma Protein Binding: 77.04
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 2.54
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.13
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.47
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.0
Micronucleos: Toxic
NR-AhR: Toxic
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: 4.6
Rat (Acute): 2.32
Rat (Chronic Oral): 2.46
Fathead Minnow: 4.38
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 425.18
Hydration Free Energy: -10.52
Log(D) at pH=7.4: 2.16
Log(P): 2.88
Log S: -4.56
Log(Vapor Pressure): -7.14
Melting Point: 279.22
pKa Acid: 9.29
pKa Basic: 5.03

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9368
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9330
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9281
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9254
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8980
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8934
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.8872
Protoporphyrinogen oxidase, mitochondrial	O24164	PPOM_TOBAC	Nicotiana tabacum	3	0.8776
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.8771
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8607
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8596
Dicamba O-demethylase, oxygenase component	Q5S3I3	DDMC_STEMA	Stenotrophomonas maltophilia	3	0.8472
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8459
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8458
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8440
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.8431
Choline kinase alpha	P35790	CHKA_HUMAN	Homo sapiens	4	0.8423
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8423
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.8392
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8365
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8297
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8281
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.8183
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.8105
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8083
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8079
Terminal oxygenase component of carbazole	Q84II6	Q84II6_JANS3	Janthinobacterium sp	3	0.7921
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7921
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7920
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7883
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7860
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7857
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7852
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	3	0.7760
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7682
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7620
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7616
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7615
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7608
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7596
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7590
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7589
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7559
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7539
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7506
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7499
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7488
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7471
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7468
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7453
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7402
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7377
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7350
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	4	0.7333
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7320
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7294
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7282
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7247
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7245
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7238
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7237
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7235
Orotidine 5'-phosphate decarboxylase	O58462	PYRF_PYRHO	Pyrococcus horikoshii	3	0.7231
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7224
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7223
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7217
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7214
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7202
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7194
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	3	0.7183
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7177
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7177
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	4	0.7148
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7135
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7122
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7052
Abscisic acid receptor PYL1	Q8VZS8	PYL1_ARATH	Arabidopsis thaliana	3	0.7049
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7042
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7039
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7013
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7011
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7002

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