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Cleistodiendiol

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

Canonical Smiles	CC(=O)O[C@H]1C=C[C@H]([C@@H](/C/1=C/OC(=O)c1ccccc1)O)O
InChI	InChI=1S/C16H16O6/c1-10(17)22-14-8-7-13(18)15(19)12(14)9-21-16(20)11-5-3-2-4-6-11/h2-9,13-15,18-19H,1H3/b12-9+/t13-,14+,15-/m1/s1
InChIKey	BEAWCJLFOGVYMB-FVRSTRTBSA-N
Formula	C₁₆H₁₆O₆
HBA	6
HBD	2
MW	304.3
Rotatable Bonds	3
TPSA	93.06
LogP	0.95
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	304.09
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)OC=C2CC=CCC2

Level: 1

Mol. Weight: 304.3 g/mol

SMILES: C=C1CC=CCC1

Level: 0

Mol. Weight: 304.3 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 304.3 g/mol

Anti-plasmodial

Cytotoxic

Absorption

Caco-2 (logPapp): -4.94
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.33
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.58

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.44
Plasma Protein Binding: 50.73
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: 4.2
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.28
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.93
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.7
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: -1.13
Rat (Acute): 2.34
Rat (Chronic Oral): 2.76
Fathead Minnow: 4.04
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: 358.2
Hydration Free Energy: -10.45
Log(D) at pH=7.4: 1.11
Log(P): 1.0
Log S: -2.21
Log(Vapor Pressure): -7.29
Melting Point: 116.72
pKa Acid: 5.58
pKa Basic: 1.0

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8654
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8654
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8506
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8506
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8344
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8344
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8321
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8321
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8259
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8259
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8119
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8119
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7979
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7979
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7931
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7931
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7773
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7773
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7654
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7654
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7638
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7638
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7546
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7546
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7497
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7497
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7391
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7391
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7367
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7367
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27793	DRTS_TRYCR	Trypanosoma cruzi	3	0.7356
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27793	DRTS_TRYCR	Trypanosoma cruzi	3	0.7356
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7334
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7334
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7265
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7265
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7201
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7201
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7183
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7183
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7174
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7174
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7163
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7163
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7151
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7151
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7097
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7097
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7094
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7094
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7090
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7090
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7057
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7057
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7044
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7044
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	2	0.7042
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	2	0.7042
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7038
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7038
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7007
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7007

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