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Z-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-/m0/s1
InChIKey	GRILELGQNUBIAJ-XXYUJHKVSA-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
2	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]
Nyandoro SS, Munissi JJ, et al. (2017). Polyoxygenated cyclohexenes and other constituents of Cleistochlamys kirkii leaves. Journal of Natural Products,2017,80(1),114-125. [View] [PubMed]

Pubchem: 11781612

Nmrshiftdb2: 70128900

Chembl: CHEMBL4633269

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: -3.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.58
Plasma Protein Binding: 44.44
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: 0.59
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: 5.32
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: -0.08
Rat (Acute): 2.27
Rat (Chronic Oral): 2.43
Fathead Minnow: 4.55
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: 369.44
Hydration Free Energy: -6.6
Log(D) at pH=7.4: 2.07
Log(P): 1.93
Log S: -3.34
Log(Vapor Pressure): -6.23
Melting Point: 84.09
pKa Acid: 8.44
pKa Basic: 3.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9471
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9471
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9444
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9444
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9200
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9200
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.9110
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.9110
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8716
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8716
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8448
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8448
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8440
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8440
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.8227
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.8227
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8172
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8172
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7879
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7879
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7860
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7860
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7805
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7805
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7793
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7793
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7660
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7660
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7620
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7620
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7613
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7613
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7557
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7557
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7520
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7520
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7504
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7504
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7487
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7487
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	3	0.7486
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	3	0.7486
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7470
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7470
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7452
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7452
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7424
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7424
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7416
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7416
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7414
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7414
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7407
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7407
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7404
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7404
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7404
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7404
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7397
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7397
Heat shock cognate 71 kDa protein	P11142	HSP7C_HUMAN	Homo sapiens	3	0.7392
Heat shock cognate 71 kDa protein	P11142	HSP7C_HUMAN	Homo sapiens	3	0.7392
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7386
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7386
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7362
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7362
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7359
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7359
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7357
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7357
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7351
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7351
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7350
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7350
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7336
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7336
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7334
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7334
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7329
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7329
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7326
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7326
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7318
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7318
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7312
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7312
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7310
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7310
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7282
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7282
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7258
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7258
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7243
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7243
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7240
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7240
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7238
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7238
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7232
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7232
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	2	0.7220
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	2	0.7220
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7212
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7212
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7204
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7204
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7201
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7201
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7173
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7173
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7165
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7165
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7152
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7152
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7135
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7135
Pyridoxal kinase	O00764	PDXK_HUMAN	Homo sapiens	2	0.7135
Pyridoxal kinase	O00764	PDXK_HUMAN	Homo sapiens	2	0.7135
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	3	0.7134
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	3	0.7134
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	2	0.7126
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	2	0.7126
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7123
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7123
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7109
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7109
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7100
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7100
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7098
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7098
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7096
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7096
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7090
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7090
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7086
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7086
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7075
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7075
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7072
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7072
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	2	0.7071
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	2	0.7071
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7067
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7067
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7067
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7067
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7058
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7058
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7037
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7037
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7015
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7015
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7013
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7013
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	2	0.7007
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	2	0.7007
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7003
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7003

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