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Trichodermamide C

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Alkaloid

Canonical Smiles	COc1c(OC)ccc2c1oc(=O)c(c2)N(C(=O)C1=NO[C@@H]2[C@@](C1)(O)[C@H](O)C=C[C@H]2O)C
InChI	InChI=1S/C21H22N2O9/c1-23(12-8-10-4-6-14(29-2)17(30-3)16(10)31-20(12)27)19(26)11-9-21(28)15(25)7-5-13(24)18(21)32-22-11/h4-8,13,15,18,24-25,28H,9H2,1-3H3/t13-,15-,18+,21+/m1/s1
InChIKey	PCMUPOUDXMFDRE-NYGSYELISA-N
Formula	C₂₁H₂₂N₂O₉
HBA	10
HBD	3
MW	446.41
Rotatable Bonds	4
TPSA	151.26
LogP	-0.06
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	446.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Penicillium citrinum	Trichocomaceae	Fungi	5077

Showing of synonyms

El-Neketi M, Ebrahim W, et al. (2013). Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the Moroccan plant Ceratonia siliqua. Journal of Natural Products,2013,76(6),1099-1104. [View] [PubMed]

Pubchem: 25067253

Zinc: ZINC000029048285

Nmrshiftdb2: 70023955

Chembl: CHEMBL262328

Comptox: DTXSID50894032

No compound-protein relationship available.

SMILES: C1C=CCC(C12)ON=C(C2)C(=O)Nc(c3)c(=O)oc(c34)cccc4

Level: 1

Mol. Weight: 446.41 g/mol

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 446.41 g/mol

SMILES: C1C=CCC(C12)ON=CC2

Level: 0

Mol. Weight: 446.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.36
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.740
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.72

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.020
Plasma Protein Binding: 73.12
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: 1.750
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.300
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.900
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.800
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -77.560
Rat (Acute): 2.410
Rat (Chronic Oral): 2.510
Fathead Minnow: 4.040
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 526.960
Hydration Free Energy: -3.520
Log(D) at pH=7.4: 0.390
Log(P): -0.04
Log S: -2.79
Log(Vapor Pressure): -10.77
Melting Point: 207.64
pKa Acid: 5.85
pKa Basic: 3.41

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8957
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8957
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8860
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8860
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8764
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8764
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8763
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8763
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8743
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8743
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8500
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8500
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8487
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8487
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8422
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8422
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8247
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8247
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8240
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8240
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8048
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8048
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8027
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8027
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.8020
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.8020
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8001
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8001
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7940
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7940
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7933
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7933
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7895
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7895
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7873
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7873
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7862
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7862
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7823
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7823
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7769
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7769
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7761
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7761
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7705
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7705
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7669
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7669
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7640
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7640
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7544
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7544
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7537
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7537
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7512
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7512
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7465
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7465
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7464
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7464
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7430
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7430
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7422
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7422
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7364
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7364
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7362
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7362
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7332
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7332
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7327
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7327
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7326
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7326
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7315
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7315
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7300
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7300
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7296
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7296
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7281
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7281
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7258
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7258
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7256
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7256
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7237
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7237
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7223
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7223
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7190
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7190
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7187
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7187
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7182
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7182
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7172
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7172
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7159
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7159
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7153
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7153
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	2	0.7147
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	2	0.7147
Adenosine 5'-monophosphoramidase HINT1	P49773	HINT1_HUMAN	Homo sapiens	3	0.7136
Adenosine 5'-monophosphoramidase HINT1	P49773	HINT1_HUMAN	Homo sapiens	3	0.7136
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7128
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7128
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7100
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7100
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7096
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7096
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7092
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7092
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7086
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7086
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7081
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7081
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7068
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7068
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7063
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7063
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7062
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7062
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7060
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7060
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7052
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7052
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	2	0.7044
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	2	0.7044
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7038
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7038
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7038
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7038
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7030
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7030
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7020
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7020
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7004
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7004

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