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Orsellide A

Family: Fungi - Chaetomiaceae
Kingdom: Fungi
Class: Phenolic
- Subclass: Deoxyhexose

Canonical Smiles	CO[C@H]1O[C@H](C)[C@H](C(=O)[C@H]1OC(=O)c1c(C)cc(cc1O)O)O
InChI	InChI=1S/C15H18O8/c1-6-4-8(16)5-9(17)10(6)14(20)23-13-12(19)11(18)7(2)22-15(13)21-3/h4-5,7,11,13,15-18H,1-3H3/t7-,11-,13-,15+/m1/s1
InChIKey	NIESVUZNUQXFRG-ORSFXWGCSA-N
Formula	C₁₅H₁₈O₈
HBA	8
HBD	3
MW	326.3
Rotatable Bonds	3
TPSA	122.52
LogP	0.25
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.47
Exact Mass	326.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chaetomium sp. NF00756	Chaetomiaceae	Fungi	5149
2	Chaetomium sp. NF00770	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: 11544388

No compound-protein relationship available.

SMILES: C1COCC(C1=O)OC(=O)c2ccccc2

Level: 1

Mol. Weight: 326.3 g/mol

SMILES: O=C1CCOCC1

Level: 0

Mol. Weight: 326.3 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 326.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.31
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.790
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.72

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.480
Plasma Protein Binding: 46.6
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: 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: 9.240
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.380
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.190
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.330
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: Toxic
T. Pyriformis: 1.380
Rat (Acute): 2.120
Rat (Chronic Oral): 2.930
Fathead Minnow: 4.080
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 373.270
Hydration Free Energy: -11.340
Log(D) at pH=7.4: 1.530
Log(P): 1.67
Log S: -2.54
Log(Vapor Pressure): -7.15
Melting Point: 152.18
pKa Acid: 6.13
pKa Basic: 2.36

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9224
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.9135
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8934
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8889
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8746
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8710
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8375
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8296
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8240
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8231
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8226
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8153
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8143
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8142
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8061
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8049
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8003
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7924
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7893
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7876
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7840
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7827
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7807
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7767
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7711
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7630
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7613
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7573
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7557
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7552
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7549
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7532
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7531
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7510
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7484
Benzoylformate decarboxylase	P20906	MDLC_PSEPU	Pseudomonas putida	3	0.7453
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7441
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7396
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7393
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7390
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	4	0.7374
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7361
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7335
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7297
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7284
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7266
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7257
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7239
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7216
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7185
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	2	0.7184
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7157
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7132
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7126
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7104
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7087
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7086
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7072
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7038
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7011
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7005

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