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Trichocarpeol C

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

Canonical Smiles	CO[C@@H]1C=C[C@H]([C@H]([C@]1(O)COC(=O)c1ccccc1)OC)OC(=O)c1ccccc1
InChI	InChI=1S/C23H24O7/c1-27-19-14-13-18(30-22(25)17-11-7-4-8-12-17)20(28-2)23(19,26)15-29-21(24)16-9-5-3-6-10-16/h3-14,18-20,26H,15H2,1-2H3/t18-,19-,20-,23+/m1/s1
InChIKey	ZYDQTXYDXQNYIN-URFJDIBFSA-N
Formula	C₂₃H₂₄O₇
HBA	7
HBD	1
MW	412.44
Rotatable Bonds	7
TPSA	91.29
LogP	2.4
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	412.15
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]

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 412.44 g/mol

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 412.44 g/mol

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 412.44 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 412.44 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 412.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.61
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.420
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.750
Plasma Protein Binding: 73.3
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: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.690
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.850
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.850
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.200
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: -32.360
Rat (Acute): 2.770
Rat (Chronic Oral): 2.710
Fathead Minnow: 4.440
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: 383.500
Hydration Free Energy: -4.090
Log(D) at pH=7.4: 3.400
Log(P): 3.52
Log S: -4.07
Log(Vapor Pressure): -8.29
Melting Point: 127.12
pKa Acid: 8.47
pKa Basic: -2.33

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	0.9760
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9666
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9315
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.9238
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9211
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9208
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9203
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9186
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9137
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8973
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8882
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.8580
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8495
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8489
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8480
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8442
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.8387
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8344
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8267
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8236
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8169
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.8105
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8090
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8072
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7956
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7940
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7939
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7890
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7884
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7876
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7869
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7856
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7850
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7843
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7801
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7790
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7782
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7781
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7777
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7734
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	4	0.7692
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7688
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7658
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7647
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7626
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7622
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7621
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7584
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7556
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7551
Serine protease 1	P00760	TRY1_BOVIN	Bos taurus	3	0.7548
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7533
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7522
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7519
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7491
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7484
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7466
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7441
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7424
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7421
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7417
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7413
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7396
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7393
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	2	0.7391
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7389
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7388
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7379
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7360
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7343
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7333
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7327
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7323
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7312
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7309
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7306
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7303
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	2	0.7275
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7271
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7260
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7256
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7254
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7240
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7235
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7229
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7221
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7214
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7208
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7197
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7196
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7194
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7186
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7184
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7180
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7169
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7161
M17 leucyl aminopeptidase	Q8IL11	Q8IL11_PLAF7	Plasmodium falciparum	3	0.7156
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7155
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7154
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7141
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7122
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7116
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7115
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7108
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7102
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7083
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7080
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7058
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7054
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7052
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7051
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7049
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7047
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7033
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7026
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7014
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7013

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