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Trichocarpeol A

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

Canonical Smiles	CO[C@H]1[C@@H](C=C[C@@H]([C@]1(O)COC(=O)c1ccccc1)Cl)OC(=O)c1ccccc1
InChI	InChI=1S/C22H21ClO6/c1-27-19-17(29-21(25)16-10-6-3-7-11-16)12-13-18(23)22(19,26)14-28-20(24)15-8-4-2-5-9-15/h2-13,17-19,26H,14H2,1H3/t17-,18+,19+,22-/m1/s1
InChIKey	WSMPBOHVRLOUFL-MDPIYQRISA-N
Formula	C₂₂H₂₁ClO₆
HBA	6
HBD	1
MW	416.86
Rotatable Bonds	6
TPSA	82.06
LogP	2.99
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	416.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Monanthotaxis trichocarpa	Annonaceae	Plantae	1202425

Showing of synonyms

Maeda G, van der Wal J, et al. (2020). Oxygenated Cyclohexene Derivatives and Other Constituents from the Roots of Monanthotaxis trichocarpa. Journal of natural products,2020, 83(2), 210-215. [View] [PubMed]

Pubchem: 156021825

Chembl: CHEMBL4646788

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CC=CC(C2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 416.86 g/mol

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 416.86 g/mol

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 416.86 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 416.86 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 416.86 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.61
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.610
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.65

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.970
Plasma Protein Binding: 67.76
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 1.660
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.120
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.710
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.070
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: -18.140
Rat (Acute): 2.820
Rat (Chronic Oral): 2.500
Fathead Minnow: 4.420
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: 394.260
Hydration Free Energy: -5.260
Log(D) at pH=7.4: 3.940
Log(P): 4.12
Log S: -4.74
Log(Vapor Pressure): -8.21
Melting Point: 110.21
pKa Acid: 9.07
pKa Basic: -1.84

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9605
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9375
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9342
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9191
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.9047
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8965
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8835
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8736
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8706
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8652
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8578
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8496
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8460
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8323
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8267
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8191
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8188
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8152
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.8073
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8046
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8039
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8021
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.8016
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7992
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7863
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7836
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7835
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7809
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7805
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7797
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7797
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7790
Heat shock cognate 71 kDa protein	P11142	HSP7C_HUMAN	Homo sapiens	3	0.7754
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7749
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7704
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	4	0.7703
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7697
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7657
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7626
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7624
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7607
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7594
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7574
7,8-dihydroneopterin aldolase	J7VEZ6	J7VEZ6_BACCE	Bacillus cereus BAG3X2-1	3	0.7532
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	4	0.7500
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7495
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7493
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7460
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7459
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7455
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7447
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7443
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7436
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7435
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7424
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7420
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7389
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7388
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7383
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7382
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7373
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7370
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7368
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7366
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7363
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7323
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7318
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7308
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7286
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7251
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7246
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7246
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7244
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7237
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7236
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7227
UDP-N-acetylenolpyruvoylglucosamine reductase	P08373	MURB_ECOLI	Escherichia coli	3	0.7225
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7218
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7215
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7212
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7204
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7200
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	4	0.7191
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7177
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7170
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7161
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7160
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7136
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7124
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7104
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7101
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7097
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7093
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7087
Poly [ADP-ribose] polymerase tankyrase-1	O95271	TNKS1_HUMAN	Homo sapiens	3	0.7085
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7078
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7075
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7059
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7058
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7055
Probable nicotinate-nucleotide adenylyltransferase	C3L5T6	NADD_BACAC	Bacillus anthracis	2	0.7047
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7044
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7040
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7039
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7008

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