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Hyperenone A

Family: Hypericaceae
Kingdom: Plantae
Class: Lactone

Canonical Smiles	C=CC(c1c(OC)oc(cc1=O)c1ccccc1)(C)C
InChI	InChI=1S/C17H18O3/c1-5-17(2,3)15-13(18)11-14(20-16(15)19-4)12-9-7-6-8-10-12/h5-11H,1H2,2-4H3
InChIKey	CCCULUWXVWYUFL-UHFFFAOYSA-N
Formula	C₁₇H₁₈O₃
HBA	3
HBD	0
MW	270.33
Rotatable Bonds	4
TPSA	39.44
LogP	3.78
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	270.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hypericum riparium	Hypericaceae	Plantae	269018

Showing of synonyms

Tala MF, Talontsi FM, et al. (2015). Antimicrobial and cytotoxic constituents from native Cameroonian medicinal plant Hypericum riparium.. Fitoterapia,2015, 102, 149-155. [View] [PubMed]

Pubchem: 354049

Cas: 96608-94-5

Zinc: ZINC000001608436

Nmrshiftdb2: 70016614

No compound-protein relationship available.

SMILES: c1ccccc1-c2cc(=O)cco2

Level: 1

Mol. Weight: 172.18 g/mol

SMILES: O=c1ccocc1

Level: 0

Mol. Weight: 96.08 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -4.47
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.02
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.97

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.22
Plasma Protein Binding: 69.01
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.17
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 2.11
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.15
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.41
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: 3.97
Rat (Acute): 1.92
Rat (Chronic Oral): 1.58
Fathead Minnow: 4.68
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: 359.32
Hydration Free Energy: -9.7
Log(D) at pH=7.4: 3.87
Log(P): 4.14
Log S: -4.65
Log(Vapor Pressure): -4.97
Melting Point: 68.61
pKa Acid: 9.53
pKa Basic: 2.8

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.9342
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.9338
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8999
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8980
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8813
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8706
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8703
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8573
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8544
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.8531
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.8522
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.8475
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8304
Protein S100-A4	P26447	S10A4_HUMAN	Homo sapiens	3	0.8259
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8225
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.8211
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8206
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.8113
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8082
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8012
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8008
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8006
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7963
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7926
2-Hydroxyacid oxidase 1	Q9UJM8	HAOX1_HUMAN	Homo sapiens	3	0.7906
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7900
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7824
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	3	0.7784
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2	Q9R1E6	ENPP2_MOUSE	Mus musculus	3	0.7782
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7749
Cytochrome P450 2B4	P00178	CP2B4_RABIT	Oryctolagus cuniculus	3	0.7749
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7673
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7671
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7662
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7650
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7649
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7632
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7631
Cytochrome P450 2B6	P20813	CP2B6_HUMAN	Homo sapiens	3	0.7630
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7623
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7614
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7607
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7603
Troponin C, slow skeletal and cardiac muscles	P63316	TNNC1_HUMAN	Homo sapiens	3	0.7601
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7551
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7531
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7524
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7524
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7492
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7475
Oxysterols receptor LXR-beta	P55055	NR1H2_HUMAN	Homo sapiens	3	0.7467
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7449
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7446
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7444
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7443
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7440
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7438
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7422
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7421
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7421
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7415
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7412
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	Q08AH3	ACS2A_HUMAN	Homo sapiens	2	0.7400
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7389
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7376
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7375
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7374
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7372
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7361
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	3	0.7356
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7344
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7342
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic	P80030	FABI_BRANA	Brassica napus	3	0.7317
Glutamine synthetase	P9WN39	GLN1B_MYCTU	Mycobacterium tuberculosis	3	0.7312
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7312
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7296
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7271
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7256
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7245
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7244
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7234
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7222
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7221
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7220
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7213
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7211
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7211
Troponin C, slow skeletal and cardiac muscles	P63316	TNNC1_HUMAN	Homo sapiens	3	0.7205
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7203
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7198
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7193
Angiopoietin-1 receptor	Q02763	TIE2_HUMAN	Homo sapiens	3	0.7188
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7174
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	2	0.7168
Farnesyl pyrophosphate synthase	P14324	FPPS_HUMAN	Homo sapiens	2	0.7163
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7157
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7143
NmrA-like family domain-containing protein 1	Q9HBL8	NMRL1_HUMAN	Homo sapiens	2	0.7142
Enoyl-ACP reductase	Q9BH77	Q9BH77_PLAFA	Plasmodium falciparum	3	0.7141
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7141
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7112
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7108
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7101
Casein kinase I isoform delta	P48730	KC1D_HUMAN	Homo sapiens	3	0.7098
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7095
Myosin light chain kinase family member 4	Q86YV6	MYLK4_HUMAN	Homo sapiens	3	0.7091
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7083
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7074
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7053
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7048
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7047
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7036
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	2	0.7025
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7025
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	3	0.7012
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7006

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