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(Z)-2′-hydroxyacetylmelodorinol

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Cycloalkene
- Subclass: Heptenolide

Canonical Smiles	CC(=O)O[C@@H](/C=C\1/C=CC(=O)O1)COC(=O)c1ccccc1O
InChI	InChI=1S/C16H14O7/c1-10(17)22-12(8-11-6-7-15(19)23-11)9-21-16(20)13-4-2-3-5-14(13)18/h2-8,12,18H,9H2,1H3/b11-8-/t12-/m0/s1
InChIKey	GCPYGUDMVVGEMD-KGTBHZDVSA-N
Formula	C₁₆H₁₄O₇
HBA	7
HBD	1
MW	318.28
Rotatable Bonds	5
TPSA	99.13
LogP	1.48
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	318.07
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: 156020928

Chembl: CHEMBL4647409

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 318.28 g/mol

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

Level: 0

Mol. Weight: 318.28 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 318.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.81
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.72
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.05

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.75
Plasma Protein Binding: 37.61
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: 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: 7.24
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.51
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.36
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.55
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: -0.04
Rat (Acute): 2.26
Rat (Chronic Oral): 2.53
Fathead Minnow: 4.39
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 398.19
Hydration Free Energy: -8.49
Log(D) at pH=7.4: 1.77
Log(P): 2.46
Log S: -3.3
Log(Vapor Pressure): -7.15
Melting Point: 95.4
pKa Acid: 7.85
pKa Basic: 3.98

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	0.9479
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	3	0.9446
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9406
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9324
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9255
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9254
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8918
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8907
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8848
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	O88703	HCN2_MOUSE	Mus musculus	3	0.8822
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8804
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.8795
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8656
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8626
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8623
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8580
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8537
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	3	0.8395
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8379
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	3	0.8260
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.8111
Cyclic nucleotide-binding domain-containing protein	E0RR11	E0RR11_SPITD	Spirochaeta thermophila	3	0.8111
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8066
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8039
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.7967
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7937
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7917
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7878
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7830
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7764
Protein RecA	Q59560	RECA_MYCS2	Mycolicibacterium smegmatis155)	3	0.7734
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7696
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7695
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7671
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7621
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7600
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7568
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7541
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7495
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7494
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7490
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7488
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7480
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7477
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7469
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7468
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7467
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7444
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7442
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7438
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7435
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7425
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7425
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7415
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7411
cAMP-activated global transcriptional regulator Vfr	P55222	VFR_PSEAE	Pseudomonas aeruginosa	3	0.7402
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7400
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7397
LD-carboxypeptidase	A0A6L8PVW7	A0A1Q4LWC0_BACAN	Bacillus anthracis	3	0.7394
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7389
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7371
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7371
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase	Q9WY79	MURE_THEMA	Thermotoga maritima	3	0.7368
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7361
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7359
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7339
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7336
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7334
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7324
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7319
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7297
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7293
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7284
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7280
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7277
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7276
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7271
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7270
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7264
Large structural protein	Q91L20	Q91L20_9MONO	Human metapneumovirus	3	0.7263
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7258
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7242
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7238
Peptide deformylase 1B, chloroplastic/mitochondrial	Q9FUZ2	DEF1B_ARATH	Arabidopsis thaliana	3	0.7237
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7232
Benzoylformate decarboxylase	P20906	MDLC_PSEPU	Pseudomonas putida	3	0.7232
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7232
Ribosome-inactivating protein dianthin-30	P24476	RIP0_DIACA	Dianthus caryophyllus	3	0.7225
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7219
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7207
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7198
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7191
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	2	0.7191
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7187
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7187
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7175
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7164
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7161
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7158
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7150
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7145
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7144
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7138
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7130
Peptidoglycan recognition protein 1	Q9GK12	PGRP1_CAMDR	Camelus dromedarius	3	0.7129
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7127
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	3	0.7110
S-methyl-5'-thioadenosine phosphorylase	Q13126	MTAP_HUMAN	Homo sapiens	3	0.7107
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7107
Amino-acid acetyltransferase	Q5FAK7	Q5FAK7_NEIG1	Neisseria gonorrhoeae	2	0.7098
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7098
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	2	0.7098
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7090
Type IV pilus retractation ATPase PilT	P24559	PILT_PSEAE	Pseudomonas aeruginosa	3	0.7089
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7086
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7082
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7077
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	3	0.7076
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7072
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7071
Nucleoside diphosphate kinase	P15266	NDK_MYXXA	Myxococcus xanthus	2	0.7069
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7062
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7056
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7054
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7052
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7046
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7038
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7034
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7032
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7032
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	4	0.7031
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7031
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2	O95340	PAPS2_HUMAN	Homo sapiens	2	0.7029
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7023
Heat shock cognate 71 kDa protein	P19120	HSP7C_BOVIN	Bos taurus	3	0.7020
Genome polyprotein	A9LIE0	A9LIE0_9FLAV	dengue virus type 3	3	0.7020
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7018
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7015
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	2	0.7008
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7006
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7004
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7004
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7003

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