ANPDB

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Trichocarpeol B

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)O)OC(=O)c1ccccc1
InChI	InChI=1S/C22H22O7/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/h2-13,17-19,23,26H,14H2,1H3/t17-,18-,19+,22+/m1/s1
InChIKey	XGMBJQHARMGQFJ-IWQHBPENSA-N
Formula	C₂₂H₂₂O₇
HBA	7
HBD	2
MW	398.41
Rotatable Bonds	6
TPSA	102.29
LogP	1.75
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	398.14
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: 398.41 g/mol

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 398.41 g/mol

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 398.41 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 398.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 398.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.85
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.400
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.56

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.830
Plasma Protein Binding: 79.28
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: 2.850
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.200
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.010
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.010
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: -18.890
Rat (Acute): 2.390
Rat (Chronic Oral): 3.110
Fathead Minnow: 4.120
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: 392.170
Hydration Free Energy: -5.960
Log(D) at pH=7.4: 2.890
Log(P): 2.68
Log S: -3.54
Log(Vapor Pressure): -8.83
Melting Point: 151.23
pKa Acid: 7.34
pKa Basic: -1.53

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	0.9492
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9472
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9433
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9391
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9203
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9128
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	3	0.8997
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8924
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8580
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8552
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8497
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8234
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8227
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8202
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	4	0.8164
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8159
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.8115
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.8064
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8034
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8019
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.8007
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7896
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7861
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7861
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7855
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7827
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7790
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7773
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7707
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7681
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7668
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7571
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7566
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7562
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7542
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7527
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7521
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7493
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7469
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7468
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7464
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7461
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7358
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	4	0.7345
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7340
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7339
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7334
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7333
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7326
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7276
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7272
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7239
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7217
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7212
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7207
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7203
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7199
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7185
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7180
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7166
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7137
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7119
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7115
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7101
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7097
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7087
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7071
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7065
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7064
7,8-dihydroneopterin aldolase	J7VEZ6	J7VEZ6_BACCE	Bacillus cereus BAG3X2-1	3	0.7052
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7046
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7043
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7030
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7016
Karilysin	D0EM77	KLY_TANFA	Tannerella forsythia	2	0.7016
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	2	0.7007

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