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Azaphilone

Family: Fungi - Chaetomiaceae
Kingdom: Fungi
Class: Alkaloid

Canonical Smiles	C/C=C/C1=CC2=CC(=O)[C@]([C@@H]([C@H]2CO1)OC(=O)c1c(C)cc(cc1O)O)(C)O
InChI	InChI=1S/C21H22O7/c1-4-5-14-7-12-8-17(24)21(3,26)19(15(12)10-27-14)28-20(25)18-11(2)6-13(22)9-16(18)23/h4-9,15,19,22-23,26H,10H2,1-3H3/b5-4+/t15-,19+,21-/m0/s1
InChIKey	HNVJWWBKFFDQAA-NRKPLWJESA-N
Formula	C₂₁H₂₂O₇
HBA	7
HBD	3
MW	386.4
Rotatable Bonds	3
TPSA	113.29
LogP	2.3
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	386.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chaetomium sp. NF00766	Chaetomiaceae	Fungi	5149

Showing of synonyms

Xu Q.L, Xiao Y.S, et al. (2018). Novel chaetospirolactone and orsellide F from an endophytic fungus Chaetomium sp.. Journal of Asian natural products research, 2018, 20(3), 234-241. [View] [PubMed]

Pubchem: 57384025

Zinc: ZINC000084634324

Chembl: CHEMBL2024575

CPRiL: 140467

SMILES: c1ccccc1C(=O)OC(CC(=O)C2)C(C=23)COC=C3

Level: 1

Mol. Weight: 386.4 g/mol

SMILES: C1=COCC(C1=2)CCC(=O)C2

Level: 0

Mol. Weight: 386.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 386.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.98
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.77
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.37

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.92
Plasma Protein Binding: 72.93
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 7.08
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.0
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.52
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.65
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: Toxic
T. Pyriformis: -4.14
Rat (Acute): 2.38
Rat (Chronic Oral): 2.85
Fathead Minnow: 4.22
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 439.31
Hydration Free Energy: -10.05
Log(D) at pH=7.4: 2.25
Log(P): 3.25
Log S: -4.36
Log(Vapor Pressure): -8.19
Melting Point: 194.52
pKa Acid: 8.12
pKa Basic: 3.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.9301
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.9294
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.9282
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8957
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8803
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8768
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8744
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8738
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8496
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8491
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8372
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8313
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8297
Cholesterol side-chain cleavage enzyme, mitochondrial	P05108	CP11A_HUMAN	Homo sapiens	3	0.8263
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8122
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8007
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q8ZMF7	ISPF_SALTY	Salmonella typhimurium	4	0.7994
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7973
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7909
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7899
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7893
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7870
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7866
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7823
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7801
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7697
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7685
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7678
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7673
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7654
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7609
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7596
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7589
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7490
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7468
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7462
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7448
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7419
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7402
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7377
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7366
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7351
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7306
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7277
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7230
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7194
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7193
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7186
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7173
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7167
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	2	0.7161
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7155
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7129
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7117
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7098
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7023
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7022
Catechol 2,3-dioxygenase	Q6REQ5	Q6REQ5_9NOCA	Rhodococcus sp. DK17	3	0.7008

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