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Cleistenediol A

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Cyclohexene Derivative
- Subclass: Polyoxygenated Cyclohexene Derivative

Canonical Smiles	CO[C@@H]1C=C[C@H]([C@H]([C@]1(O)COC(=O)c1ccccc1)O)OC(=O)C
InChI	InChI=1S/C17H20O7/c1-11(18)24-13-8-9-14(22-2)17(21,15(13)19)10-23-16(20)12-6-4-3-5-7-12/h3-9,13-15,19,21H,10H2,1-2H3/t13-,14-,15-,17+/m1/s1
InChIKey	GELRWHNGKKHLNY-ANQUJSFKSA-N
Formula	C₁₇H₂₀O₇
HBA	7
HBD	2
MW	336.34
Rotatable Bonds	5
TPSA	102.29
LogP	0.45
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.41
Exact Mass	336.12
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)OCC2CC=CCC2

Level: 1

Mol. Weight: 336.34 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 336.34 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 336.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.99
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.510
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.66

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.390
Plasma Protein Binding: 51.09
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: 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: 3.910
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.300
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.300
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.190
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: -1.480
Rat (Acute): 2.200
Rat (Chronic Oral): 2.750
Fathead Minnow: 4.070
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 342.100
Hydration Free Energy: -10.670
Log(D) at pH=7.4: 1.030
Log(P): 1.39
Log S: -2.13
Log(Vapor Pressure): -7.57
Melting Point: 137.56
pKa Acid: 7.05
pKa Basic: 0.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9375
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9375
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9142
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9142
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9119
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9119
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9084
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9084
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9065
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9065
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8819
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8819
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8714
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8714
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8509
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8509
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8044
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8044
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8036
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8036
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8029
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8029
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.8002
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.8002
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7959
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7959
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7799
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7799
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7752
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7752
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7737
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7737
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7719
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7719
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7667
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7667
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7645
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7645
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7638
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7638
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7551
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7551
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7538
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7538
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7497
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7497
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7493
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7493
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7444
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7444
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7418
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7418
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7375
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7375
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7344
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7344
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7330
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7330
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7314
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7314
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7290
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7290
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7285
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7285
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7272
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7272
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7270
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7270
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7247
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7247
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7243
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7243
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7237
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7237
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7230
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7230
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7213
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7213
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7213
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7213
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7212
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7212
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7207
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7207
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7180
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7180
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7173
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7173
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7166
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7166
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7148
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7148
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7145
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7145
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7139
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7139
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7131
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7131
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	4	0.7129
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7129
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7129
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	4	0.7129
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7117
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7117
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7097
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7097
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7079
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7079
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7071
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7071
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7070
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7070
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7069
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7069
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7049
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7049
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7034
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7034
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7025
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	4	0.7025
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7025
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	4	0.7025
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7006
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7006
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7005
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7005
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7003
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7003

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