ANPDB

Select a section from the left sidebar

7-hydroxy-6-hydromelodienone

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Isoprenoid
- Subclass: Meroisoprenoid

Canonical Smiles	COC(=O)/C=C/C(=O)C[C@@H](COC(=O)c1ccccc1)O
InChI	InChI=1S/C15H16O6/c1-20-14(18)8-7-12(16)9-13(17)10-21-15(19)11-5-3-2-4-6-11/h2-8,13,17H,9-10H2,1H3/b8-7+/t13-/m0/s1
InChIKey	DLQZZFILZYWBJV-GWJCSSMESA-N
Formula	C₁₅H₁₆O₆
HBA	6
HBD	1
MW	292.29
Rotatable Bonds	7
TPSA	89.9
LogP	0.89
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	292.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Sphaerocoryne gracilis	Annonaceae	Plantae	489348

Showing of synonyms

Maeda G, Munissi JJE, et al. (2020). A Meroisoprenoid, Heptenolides, and C‐Benzylated Flavonoids from Sphaerocoryne gracilis ssp. Gracilis. Journal of natural products,2020, 83(2), 316-322. [View] [PubMed]

Pubchem: 6438688

Cas: 135626-21-0

Nmrshiftdb2: 70082763

Chembl: CHEMBL4636742

CPRiL: 100857

SMILES: c1ccccc1

Level: 0

Mol. Weight: 292.29 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp): -4.69
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.400
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.37

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.070
Plasma Protein Binding: 38.28
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-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: 2.930
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.280
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.410
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.030
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: 1.690
Rat (Acute): 1.820
Rat (Chronic Oral): 2.640
Fathead Minnow: 4.230
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 342.600
Hydration Free Energy: -9.590
Log(D) at pH=7.4: 1.770
Log(P): 1.67
Log S: -2.38
Log(Vapor Pressure): -6.09
Melting Point: 89.21
pKa Acid: 10.02
pKa Basic: 3.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9515
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.9360
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.9281
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9142
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9113
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.9031
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9008
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8941
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.8772
Adenylate cyclase 2	A0A2U2H3Y1	A0A384LKY8_YERPE	Yersinia pestis	3	0.8727
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8629
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8555
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8433
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8431
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8391
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8284
Iota toxin component Ia	Q46220	Q46220_CLOPF	Clostridium perfringens	3	0.8277
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.8259
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8253
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8245
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8138
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8133
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.8063
7,8-dihydroneopterin aldolase	J7VEZ6	J7VEZ6_BACCE	Bacillus cereus BAG3X2-1	3	0.8057
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.8022
Cytochrome P450 2A6	P11509	CP2A6_HUMAN	Homo sapiens	3	0.7998
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7940
Beta-glucosidase	Q8T0W7	Q8T0W7_9NEOP	Neotermes koshunensis	3	0.7915
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7907
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7899
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7876
Heat shock cognate 71 kDa protein	P11142	HSP7C_HUMAN	Homo sapiens	3	0.7853
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7789
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7703
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7696
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7671
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7659
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7601
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	3	0.7593
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7590
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7568
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7542
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7518
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7509
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7484
M17 leucyl aminopeptidase	Q8IL11	Q8IL11_PLAF7	Plasmodium falciparum	3	0.7474
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7460
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7450
Nucleoside diphosphate kinase	P15266	NDK_MYXXA	Myxococcus xanthus	3	0.7439
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7438
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7436
Protein mono-ADP-ribosyltransferase PARP10	Q53GL7	PAR10_HUMAN	Homo sapiens	3	0.7422
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7418
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7418
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7386
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7365
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7345
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7344
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7344
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7344
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7341
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7331
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7327
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7326
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7323
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7322
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7322
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7296
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7291
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7290
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7289
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7283
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7282
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7282
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7265
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7263
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7263
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7262
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7262
Transcriptional regulator URE2	P23202	URE2_YEAST	Saccharomyces cerevisiae	3	0.7250
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7243
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7230
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7228
Alpha-hemolysin translocation ATP-binding protein HlyB	P08716	HLYBP_ECOLX	Escherichia coli	3	0.7214
Ceramide transfer protein	Q9Y5P4	CERT_HUMAN	Homo sapiens	3	0.7214
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7212
Type IV pilus retractation ATPase PilT	P24559	PILT_PSEAE	Pseudomonas aeruginosa	3	0.7206
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7202
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.7201
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7201
Protein claret segregational	P20480	NCD_DROME	Drosophila melanogaster	2	0.7200
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7199
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7193
Amino-acid acetyltransferase	Q5FAK7	Q5FAK7_NEIG1	Neisseria gonorrhoeae	2	0.7192
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7188
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7184
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7182
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7180
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7173
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7168
Pyridoxal kinase	O00764	PDXK_HUMAN	Homo sapiens	2	0.7162
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	2	0.7159
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7158
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7156
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7153
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7148
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7148
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7137
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	3	0.7135
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7133
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7128
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7125
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7120
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	4	0.7119
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7109
Putative snRNP Sm-like protein	Q8ZYG5	Q8ZYG5_PYRAE	Pyrobaculum aerophilum	2	0.7106
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7105
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7103
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7102
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	2	0.7100
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7099
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7096
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7094
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7090
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7088
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7086
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	2	0.7078
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7074
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7067
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7064
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	2	0.7064
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7064
GMP reductase	Q81JJ9	GUAC_BACAN	Bacillus anthracis	2	0.7062
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7056
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7052
ADP-dependent (S)-NAD(P)H-hydrate dehydratase	P94368	NNRD_BACSU	Bacillus subtilis	3	0.7043
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7042
Phenylpyruvate C(3)-methyltransferase	Q643C8	MPPJ_STRHY	Streptomyces hygroscopicus	2	0.7035
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	2	0.7034
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7032
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7027
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7024
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	2	0.7023
Karilysin	D0EM77	KLY_TANFA	Tannerella forsythia	2	0.7023
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7023
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7017
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7012
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7010
Nucleoside diphosphate kinase	Q9U1E1	Q9U1E1_LEIMA	Leishmania major	3	0.7004
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7004

Download SDF