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Biscognienyne F

Family: Fungi - Amphisphaeriaceae
Kingdom: Fungi
Class: Terpenoid
- Subclass: Meroterpenoid

Canonical Smiles	CC(CC[C@@]12[C@@H](O1)[C@@H](C=C([C@H]2O)C#CC(=C)C)O)CO
InChI	InChI=1S/C16H22O4/c1-10(2)4-5-12-8-13(18)15-16(20-15,14(12)19)7-6-11(3)9-17/h8,11,13-15,17-19H,1,6-7,9H2,2-3H3/t11?,13-,14-,15+,16-/m1/s1
InChIKey	JPHGXUKATFVYBM-XKSJNWPBSA-N
Formula	C₁₆H₂₂O₄
HBA	4
HBD	3
MW	278.35
Rotatable Bonds	4
TPSA	73.22
LogP	0.77
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	278.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pseudopestalotiopsis theae	Amphisphaeriaceae	Fungi	218556

Showing of synonyms

Akone SH, Wang H, et al. (2022). Prenylated cyclohexene-type meroterpenoids and sulfur-containing xanthones produced by Pseudopestalotiopsis theae. Phytochemistry, 2022, 197:113124. [View] [PubMed]

Pubchem: 170989649

No compound-protein relationship available.

SMILES: C12C(O2)CC=CC1

Level: 0

Mol. Weight: 278.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.02
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.21
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.32
Plasma Protein Binding: 17.6
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: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 14.23
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.67
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.08
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.62
Micronucleos: Safe
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: Safe
T. Pyriformis: 1.14
Rat (Acute): 2.49
Rat (Chronic Oral): 1.95
Fathead Minnow: 3.93
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 373.79
Hydration Free Energy: -11.93
Log(D) at pH=7.4: 0.5
Log(P): 1.45
Log S: -1.99
Log(Vapor Pressure): -6.92
Melting Point: 87.59
pKa Acid: 6.01
pKa Basic: 2.79

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8854
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8854
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8835
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8835
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8800
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8800
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8785
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8785
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8532
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8532
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8490
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8490
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8374
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8374
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8332
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8332
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.8329
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.8329
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8276
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8276
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8049
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8049
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7997
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7997
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7982
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7982
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	4	0.7935
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	4	0.7935
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7843
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7843
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7811
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7811
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7720
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7720
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7692
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7692
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7666
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7666
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7664
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7664
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7597
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7597
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7581
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7581
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7575
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7575
Putative cytochrome P450 120	Q59990	CP120_SYNY3	Synechocystis sp	3	0.7469
Putative cytochrome P450 120	Q59990	CP120_SYNY3	Synechocystis sp	3	0.7469
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7425
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7425
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7421
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7421
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7417
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7417
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7412
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7412
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7377
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7377
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7370
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7370
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7338
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7338
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7319
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7319
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7287
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7287
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7277
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7277
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7274
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7274
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7265
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7265
Vitamin D3 receptor	P11473	VDR_HUMAN	Homo sapiens	4	0.7230
Vitamin D3 receptor	P11473	VDR_HUMAN	Homo sapiens	4	0.7230
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7226
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7226
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7178
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7178
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7158
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7158
Vitamin D3 receptor A	Q9PTN2	VDRA_DANRE	Danio rerio	3	0.7137
Vitamin D3 receptor A	Q9PTN2	VDRA_DANRE	Danio rerio	3	0.7137
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7127
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7127
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7127
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7127
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7117
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7117
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7105
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7105
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7086
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7086
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7047
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7047
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7041
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7041
Vitamin D3 receptor	P11473	VDR_HUMAN	Homo sapiens	4	0.7027
Vitamin D3 receptor	P11473	VDR_HUMAN	Homo sapiens	4	0.7027

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