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(E)-acetylmelodorinol

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

Canonical Smiles	O=C(c1ccccc1)OC[C@@H](/C=C/1\C=CC(=O)O1)OC(=O)C
InChI	InChI=1S/C16H14O6/c1-11(17)21-14(9-13-7-8-15(18)22-13)10-20-16(19)12-5-3-2-4-6-12/h2-9,14H,10H2,1H3/b13-9+/t14-/m1/s1
InChIKey	GRILELGQNUBIAJ-KADHNRKRSA-N
Formula	C₁₆H₁₄O₆
HBA	6
HBD	0
MW	302.28
Rotatable Bonds	5
TPSA	78.9
LogP	1.77
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	302.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cleistochlamys kirkii	Annonaceae	Plantae	1237197

Showing of synonyms

Nyandoro SS, Maeda G, et al. (2019). A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii. Molecules 2019, 24(15), 2746. [View] [PubMed]

Pubchem: 102328632

Zinc: ZINC000001625131

Nmrshiftdb2: 60065688

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCCC=C2C=CC(=O)O2

Level: 1

Mol. Weight: 302.28 g/mol

SMILES: C=C1C=CC(=O)O1

Level: 0

Mol. Weight: 302.28 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 302.28 g/mol

Anti-plasmodial

Cytotoxic

Absorption

Caco-2 (logPapp): -4.77
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.68
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.28

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.58
Plasma Protein Binding: 45.57
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: 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: 4.4
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.66
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.35
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.37
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: 0.18
Rat (Acute): 2.28
Rat (Chronic Oral): 2.44
Fathead Minnow: 4.74
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 371.81
Hydration Free Energy: -6.58
Log(D) at pH=7.4: 2.05
Log(P): 1.94
Log S: -3.43
Log(Vapor Pressure): -6.25
Melting Point: 92.64
pKa Acid: 8.41
pKa Basic: 3.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8517
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8477
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.8454
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	3	0.8369
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.8090
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.8065
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8046
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7987
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7955
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7763
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7726
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7638
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7604
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7554
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7527
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7525
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7490
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7478
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7462
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7432
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7423
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7422
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7409
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7334
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7318
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7303
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7298
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.7294
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7275
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7262
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	2	0.7256
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7255
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	2	0.7252
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7234
Type IV pilus retractation ATPase PilT	P24559	PILT_PSEAE	Pseudomonas aeruginosa	3	0.7231
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7228
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7222
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7222
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7218
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7216
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7215
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7195
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7189
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7188
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	2	0.7184
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7177
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7156
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	O88703	HCN2_MOUSE	Mus musculus	3	0.7148
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7139
Metallophosphoesterase	A3DJ38	A3DJ38_HUNT2	Clostridium thermocellum	2	0.7135
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7130
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7128
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7127
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7124
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7120
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7117
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7117
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7111
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7103
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7099
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7098
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7084
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7084
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7080
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7078
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7076
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7073
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7070
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7057
Metallophosphoesterase	A3DJ38	A3DJ38_HUNT2	Clostridium thermocellum	2	0.7055
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7049
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7039
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7038
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7022
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7017
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	2	0.7008
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	2	0.7007
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7007
Amino-acid acetyltransferase	Q5FAK7	Q5FAK7_NEIG1	Neisseria gonorrhoeae	2	0.7000

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