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5-alpha-acetoxy-2-beta-(benzoyloxy)-1alpha,6beta-dihydroxycyclohex-3-en-1-yl)methyl benzoate

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Cycloalkene
- Subclass: Oxygenated Cyclohexene

Canonical Smiles	CC(=O)O[C@@H]1C=C[C@H]([C@@]([C@H]1O)(O)COC(=O)c1ccccc1)OC(=O)c1ccccc1
InChI	InChI=1S/C23H22O8/c1-15(24)30-18-12-13-19(31-22(27)17-10-6-3-7-11-17)23(28,20(18)25)14-29-21(26)16-8-4-2-5-9-16/h2-13,18-20,25,28H,14H2,1H3/t18-,19-,20+,23+/m1/s1
InChIKey	ATPRNHQOENJXMX-UGTOYMOASA-N
Formula	C₂₃H₂₂O₈
HBA	8
HBD	2
MW	426.42
Rotatable Bonds	6
TPSA	119.36
LogP	1.66
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.26
Exact Mass	426.13
Number of Lipinski Rule Violations	0

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

Showing of synonyms

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]

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2C(C=CCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 426.42 g/mol

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 426.42 g/mol

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 426.42 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 426.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 426.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.49
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.56
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.89
Plasma Protein Binding: 84.58
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: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.11
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.09
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.43
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.23
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: -42.99
Rat (Acute): 2.17
Rat (Chronic Oral): 3.58
Fathead Minnow: 4.17
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: 416.28
Hydration Free Energy: -3.59
Log(D) at pH=7.4: 2.54
Log(P): 3.03
Log S: -3.92
Log(Vapor Pressure): -9.34
Melting Point: 162.05
pKa Acid: 7.01
pKa Basic: -0.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9428
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.9409
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9344
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.9125
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9049
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8791
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8751
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8712
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8653
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8634
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8591
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8510
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8413
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8412
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8390
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8389
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8319
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8278
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8251
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8246
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8245
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8155
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8153
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8125
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8068
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8048
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8014
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7867
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7822
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7822
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7820
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7817
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7809
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7779
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7737
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7707
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7697
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7684
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7630
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7624
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7624
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7601
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7591
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7579
Inorganic pyrophosphatase	Q3JUV5	Q3JUV5_BURP1	Burkholderia pseudomallei	2	0.7569
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7567
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7564
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7528
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	2	0.7522
Ribosomal protein S6 kinase beta-1	P23443	KS6B1_HUMAN	Homo sapiens	2	0.7515
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7490
Pyruvate kinase PKM	P14618	KPYM_HUMAN	Homo sapiens	3	0.7486
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	2	0.7482
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7475
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	2	0.7473
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7457
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7433
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7430
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7426
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7425
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7377
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7376
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7375
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7365
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7363
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7361
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7355
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7334
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7326
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7324
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7317
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	2	0.7307
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	2	0.7297
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7296
Dipeptidyl peptidase 4	P14740	DPP4_RAT	Rattus norvegicus	2	0.7285
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7285
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7268
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7203
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7190
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7187
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	4	0.7186
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7185
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7170
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7165
UDP-N-acetylenolpyruvoylglucosamine reductase	P08373	MURB_ECOLI	Escherichia coli	3	0.7163
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7157
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7140
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7126
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	2	0.7117
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7116
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7110
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7106
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7102
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7096
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7091
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7070
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7068
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7037
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	4	0.7026
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7025
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7012
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7007
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7006

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