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Madeleinol B

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

Canonical Smiles	CC(=CCCC1(C)Oc2c(CC1O)c(O)cc(c2C(=O)C(C)C)O)C
InChI	InChI=1S/C20H28O5/c1-11(2)7-6-8-20(5)16(23)9-13-14(21)10-15(22)17(19(13)25-20)18(24)12(3)4/h7,10,12,16,21-23H,6,8-9H2,1-5H3
InChIKey	OTCGNFYHXWMHCW-UHFFFAOYSA-N
Formula	C₂₀H₂₈O₅
HBA	5
HBD	3
MW	348.44
Rotatable Bonds	5
TPSA	86.99
LogP	3.74
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	348.19
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: 78073027

Nmrshiftdb2: 70029725

Chembl: CHEMBL3613752

No compound-protein relationship available.

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 348.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.67
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.77
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.46

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.86
Plasma Protein Binding: 43.18
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.98
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.53
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.15
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.85
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: 2.88
Rat (Acute): 2.08
Rat (Chronic Oral): 2.58
Fathead Minnow: 4.35
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: 389.03
Hydration Free Energy: -10.75
Log(D) at pH=7.4: 2.89
Log(P): 4.67
Log S: -4.92
Log(Vapor Pressure): -6.78
Melting Point: 134.32
pKa Acid: 7.43
pKa Basic: 5.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9467
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9162
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9104
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8994
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8981
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8957
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8923
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8468
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8463
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8452
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8402
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8380
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8330
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8228
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8228
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8208
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8033
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7984
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7951
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7947
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7931
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7923
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7923
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7882
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7837
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7746
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7731
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7728
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7710
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7699
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7606
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7546
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7545
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7532
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7515
orotidine-5'-phosphate decarboxylase	Q8T6J6	Q8T6J6_PLAFA	Plasmodium falciparum	4	0.7490
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7489
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7488
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7483
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7476
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7472
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7444
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7443
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7436
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7432
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	3	0.7429
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7422
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7420
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7412
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7394
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7350
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7333
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7328
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7318
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7317
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7316
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7309
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7307
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7293
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7292
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7278
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7261
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7250
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7204
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7203
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7181
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7152
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7146
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7129
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7096
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7074
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7072
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7062
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7061
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7037
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7035
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7022
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7014

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