ANPDB

Select a section from the left sidebar

Biscognienyne B

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

Canonical Smiles	CC(=CC[C@]12O[C@H]1[C@H](O)C=C([C@H]2O)C#CC(=C)C)C
InChI	InChI=1S/C16H20O3/c1-10(2)5-6-12-9-13(17)15-16(19-15,14(12)18)8-7-11(3)4/h7,9,13-15,17-18H,1,8H2,2-4H3/t13-,14-,15+,16-/m1/s1
InChIKey	UAAPCPSYCUMTPM-LVQVYYBASA-N
Formula	C₁₆H₂₀O₃
HBA	3
HBD	2
MW	260.33
Rotatable Bonds	2
TPSA	52.99
LogP	1.72
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	260.14
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: 132942887

Chebi: 167050

Nmrshiftdb2: 80017523

Metabolights: MTBLC167050

No compound-protein relationship available.

SMILES: C12C(O2)CC=CC1

Level: 0

Mol. Weight: 260.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.86
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.05
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.84

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.28
Plasma Protein Binding: 19.98
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: 14.6
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.07
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.06
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.16
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: 0.77
Rat (Acute): 2.19
Rat (Chronic Oral): 1.88
Fathead Minnow: 4.09
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 337.49
Hydration Free Energy: -9.81
Log(D) at pH=7.4: 1.4
Log(P): 2.91
Log S: -2.83
Log(Vapor Pressure): -5.96
Melting Point: 104.07
pKa Acid: 6.02
pKa Basic: 2.07

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.9170
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.9170
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9139
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9139
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8845
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8845
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8837
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8837
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8780
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8780
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8667
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8667
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8651
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8651
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8569
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8569
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8361
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8361
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.8008
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.8008
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7966
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7966
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7712
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7712
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7567
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7567
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7463
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7463
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7451
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7451
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7404
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7404
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7403
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7403
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7353
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7353
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7298
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7298
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7287
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7287
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7278
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7278
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7271
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7271
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7266
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7266
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7260
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7260
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7250
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7250
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7241
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7241
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7240
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7240
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7193
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7193
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7189
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7189
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7121
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7121
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7079
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7079
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7064
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7064
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7042
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7042
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7035
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7035
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7032
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7032
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7027
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7027
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7002
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7002
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7000
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7000

Download SDF