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Orsellide C

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

Canonical Smiles	CO[C@H]1O[C@H](C)CC(=O)[C@H]1OC(=O)c1c(C)cc(cc1O)O
InChI	InChI=1S/C15H18O7/c1-7-4-9(16)6-10(17)12(7)14(19)22-13-11(18)5-8(2)21-15(13)20-3/h4,6,8,13,15-17H,5H2,1-3H3/t8-,13-,15+/m1/s1
InChIKey	SCIDNYISLWFEKY-YVILZHTOSA-N
Formula	C₁₅H₁₈O₇
HBA	7
HBD	2
MW	310.3
Rotatable Bonds	3
TPSA	102.29
LogP	1.28
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.47
Exact Mass	310.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chaetomium sp. NF00757	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: 11709350

Zinc: ZINC000034633996

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 310.3 g/mol

SMILES: O=C1CCOCC1

Level: 0

Mol. Weight: 310.3 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 310.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.87
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.740
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.570
Plasma Protein Binding: 51.0
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: 10.230
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.090
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.060
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.760
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: 1.620
Rat (Acute): 2.150
Rat (Chronic Oral): 2.590
Fathead Minnow: 4.040
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: 357.980
Hydration Free Energy: -10.180
Log(D) at pH=7.4: 1.760
Log(P): 2.26
Log S: -3.0
Log(Vapor Pressure): -6.15
Melting Point: 133.97
pKa Acid: 6.81
pKa Basic: 3.92

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.9099
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8970
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8790
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8739
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8696
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8541
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8378
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8330
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8248
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8230
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8178
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8158
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8130
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.8109
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8092
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8085
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7995
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
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7889
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7861
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7837
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7831
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7831
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7821
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7816
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7785
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7657
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7613
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7571
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7544
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR0	INHA_MYCTO	Mycobacterium tuberculosis	3	0.7523
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7468
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7401
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7391
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7390
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7379
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7313
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7285
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7283
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7282
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7278
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7273
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7259
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7233
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7228
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7161
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7147
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7102
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7068
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7056
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7055
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7047
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7017
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7012

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