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Madagascin

Family: Plantae - Hypericaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthraquinone

Canonical Smiles	CC(=CCOc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)C)C
InChI	InChI=1S/C20H18O5/c1-10(2)4-5-25-12-8-14-18(16(22)9-12)20(24)17-13(19(14)23)6-11(3)7-15(17)21/h4,6-9,21-22H,5H2,1-3H3
InChIKey	AIEGEPAELPMAPY-UHFFFAOYSA-N
Formula	C₂₀H₁₈O₅
HBA	5
HBD	2
MW	338.36
Rotatable Bonds	3
TPSA	83.83
LogP	3.53
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.2
Exact Mass	338.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Harungana madagascariensis	Hypericaceae	Plantae	198768
2	Harungana madagascariensis	Hypericaceae	Plantae	198768

Showing of synonyms

Kouam SF, Khan SN, et al. (2006). Alpha-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis.. Journal of natural products,2006, 69(2), 229-233. [View] [PubMed]
Tankeo SB, Damen F, et al. (2016). Antibacterial activities of the methanol extracts, fractions and compounds from Harungana madagascariensis Lam. ex Poir. (Hypericaceae).. Journal of ethnopharmacology,2016, 190, 100-105. [View] [PubMed]

Pubchem: 378693

Zinc: ZINC000005940186

Nmrshiftdb2: 60061596

Chembl: CHEMBL1800811

CPRiL: 167437

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 338.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.53
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.65
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.05
Plasma Protein Binding: 65.14
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.79
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.29
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.04
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.04
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 3.17
Rat (Acute): 2.39
Rat (Chronic Oral): 2.71
Fathead Minnow: 4.85
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 446.76
Hydration Free Energy: -9.53
Log(D) at pH=7.4: 3.31
Log(P): 5.63
Log S: -7.05
Log(Vapor Pressure): -8.11
Melting Point: 187.42
pKa Acid: 7.15
pKa Basic: 4.52

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.9445
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9323
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9220
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8932
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8757
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8690
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8632
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8585
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8387
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8249
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8186
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8144
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.8131
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.8130
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	4	0.8105
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8078
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.8028
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8023
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7939
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7917
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7901
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.7864
Casein kinase I isoform delta	P48730	KC1D_HUMAN	Homo sapiens	3	0.7851
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7846
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7803
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7782
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7779
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	4	0.7727
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7673
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7633
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7617
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7603
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7598
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7567
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7562
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7539
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7504
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7499
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7493
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7491
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7489
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7483
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7482
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7466
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7454
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7452
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7435
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7428
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7422
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7420
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7405
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7404
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7393
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7380
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7368
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7357
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7346
Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	CP11A_BOVIN	Bos taurus	4	0.7344
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7334
Fructose-1,6-bisphosphatase 1	P00636	F16P1_PIG	Sus scrofa	3	0.7331
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7326
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7310
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7306
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7294
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7279
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7268
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7255
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7252
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7244
Prostaglandin E synthase 2	Q9N0A4	PGES2_MACFA	Macaca fascicularis	3	0.7237
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7233
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7218
Tyrosine-protein kinase Lyn	P25911	LYN_MOUSE	Mus musculus	3	0.7205
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7193
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7146
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7144
Casein kinase I isoform delta	P48730	KC1D_HUMAN	Homo sapiens	3	0.7140
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7139
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7138
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7134
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7130
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7128
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7127
Dodecin	Q5SIE3	DODEC_THET8	Thermus thermophilus	4	0.7126
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7121
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7114
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7111
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7110
Orotidine 5'-phosphate decarboxylase	Q9KQT7	PYRF_VIBCH	Vibrio cholerae serotype O1	4	0.7108
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7095
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	4	0.7078
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7078
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7063
Bifunctional F420 biosynthesis protein FbiB	P9WP79	FBIB_MYCTU	Mycobacterium tuberculosis	5	0.7060
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7054
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7049
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7048
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7029
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7028
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7026
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7023
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7023
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7017
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7013

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