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Orsellide F

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

Canonical Smiles	CCCCO[C@H]1O[C@H](C)[C@H](C(=O)[C@H]1OC(=O)c1c(C)cc(cc1O)O)O
InChI	InChI=1S/C18H24O8/c1-4-5-6-24-18-16(15(22)14(21)10(3)25-18)26-17(23)13-9(2)7-11(19)8-12(13)20/h7-8,10,14,16,18-21H,4-6H2,1-3H3/t10-,14-,16-,18+/m1/s1
InChIKey	CFNGGJBGFYWXHF-XLDSIYFKSA-N
Formula	C₁₈H₂₄O₈
HBA	8
HBD	3
MW	368.38
Rotatable Bonds	6
TPSA	122.52
LogP	1.42
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.56
Exact Mass	368.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chaetomium sp. NF00755	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: 139591368

Nmrshiftdb2: 80016048

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 368.38 g/mol

SMILES: O=C1CCOCC1

Level: 0

Mol. Weight: 368.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 368.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.3
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.75
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.74

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.56
Plasma Protein Binding: 59.06
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: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.62
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.33
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.0
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.6
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: 0.22
Rat (Acute): 2.24
Rat (Chronic Oral): 2.91
Fathead Minnow: 4.07
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: 386.4
Hydration Free Energy: -10.34
Log(D) at pH=7.4: 2.56
Log(P): 2.91
Log S: -3.07
Log(Vapor Pressure): -7.89
Melting Point: 129.19
pKa Acid: 6.23
pKa Basic: 3.1

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	0.9227
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9009
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.9001
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8954
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8742
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8742
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8695
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8638
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8617
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8590
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8549
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.8472
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8461
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8445
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8383
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8273
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8266
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8204
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8146
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.8145
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8133
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8069
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8043
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7989
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7978
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7962
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7953
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7939
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7903
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7899
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7884
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7838
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7822
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7818
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7782
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7770
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7618
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7610
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7589
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7573
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7565
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7512
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7391
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7389
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7371
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7369
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7346
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7333
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7324
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7321
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7289
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7247
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7226
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7222
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7216
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7204
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7187
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7174
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7153
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7136
CDP-alcohol phosphatidyltransferase AF-2299-like N-terminal domain-containing protein	O27985	O27985_ARCFU	Archaeoglobus fulgidus	4	0.7131
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7125
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7121
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7118
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7117
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7116
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7113
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7108
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7102
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7098
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7096
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7054
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7031
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7028
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7023
Phosphoglycerate kinase	Q83AU6	PGK_COXBU	Coxiella burnetii	3	0.7020
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7008
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7001

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