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Empetrikarinol B

Family: Plantae - Hypericaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene

Canonical Smiles	CCC(C(=O)c1c(O)cc(c2c1O[C@](C)(CCC=C(C)C)[C@H](C2)O)O)C
InChI	InChI=1S/C21H30O5/c1-6-13(4)19(25)18-16(23)11-15(22)14-10-17(24)21(5,26-20(14)18)9-7-8-12(2)3/h8,11,13,17,22-24H,6-7,9-10H2,1-5H3/t13?,17-,21+/m0/s1
InChIKey	OOUQAKUAWXZBEN-PTPQSVRFSA-N
Formula	C₂₁H₃₀O₅
HBA	5
HBD	3
MW	362.47
Rotatable Bonds	6
TPSA	86.99
LogP	4.13
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.57
Exact Mass	362.21
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hypericum roeperianum	Hypericaceae	Plantae	—

Showing of synonyms

Fobofou SA, Franke K, et al. (2015). Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum.. Bioorganic & medicinal chemistry,2015, 23(19), 6327-6334. [View] [PubMed]

Pubchem: 71458439

Nmrshiftdb2: 70029724

Chembl: CHEMBL2152494

No compound-protein relationship available.

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 362.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.76
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.8
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): 0.85
Plasma Protein Binding: 75.49
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: 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: 10.44
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.27
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.48
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.24
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: Safe
T. Pyriformis: 0.38
Rat (Acute): 2.28
Rat (Chronic Oral): 2.69
Fathead Minnow: 4.16
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 390.74
Hydration Free Energy: -10.14
Log(D) at pH=7.4: 3.52
Log(P): 5.11
Log S: -5.41
Log(Vapor Pressure): -7.32
Melting Point: 130.21
pKa Acid: 7.49
pKa Basic: 5.62

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9452
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.9046
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9027
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.8682
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8599
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8441
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8386
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.8300
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8296
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8272
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8241
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8163
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8144
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8143
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8136
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8118
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8062
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.8028
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8010
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7960
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7949
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7945
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7943
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7886
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7873
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7830
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7812
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7795
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7790
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7780
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7774
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.7771
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7728
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7696
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7695
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7687
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7686
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7663
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7657
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7566
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7564
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7558
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7553
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7538
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7535
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7531
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7495
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7465
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7461
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7454
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7440
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7436
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7426
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7421
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7418
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7391
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7388
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7383
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7351
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7351
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7342
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7340
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7338
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7334
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7322
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7314
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7309
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7302
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7281
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7267
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7243
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7201
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7194
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7183
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7176
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7172
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7167
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7166
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7162
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7133
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7130
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7113
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7113
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7097
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7087
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7083
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7077
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7074
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7058
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7047
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7042
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7034
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7028
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7017
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7016
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7007

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