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Tardioxopiperazine B

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Alkaloid
- Subclass: Indole Alkaloid

Canonical Smiles	C=CC(c1[nH]c2c(c1C[C@@H]1NC(=O)[C@@H](NC1=O)C)cccc2CC=C(C)C)(C)C
InChI	InChI=1S/C24H31N3O2/c1-7-24(5,6)21-18(13-19-23(29)25-15(4)22(28)26-19)17-10-8-9-16(20(17)27-21)12-11-14(2)3/h7-11,15,19,27H,1,12-13H2,2-6H3,(H,25,29)(H,26,28)/t15-,19-/m0/s1
InChIKey	QNQMVKRHUCFRIY-KXBFYZLASA-N
Formula	C₂₄H₃₁N₃O₂
HBA	2
HBD	3
MW	393.53
Rotatable Bonds	6
TPSA	73.99
LogP	3.69
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	393.24
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus amstelodami	Trichocomaceae	Fungi	5054

Showing of synonyms

Elsbaey M, Sallam A, et al. (2019). Melanogenesis Inhibitors from the Endophytic Fungus Aspergillus amstelodami. Chem Biodivers,2019,16(8),e1900237. [View] [PubMed]

Pubchem: 10810597

Cas: 252028-91-4

Zinc: ZINC000014720495

Chebi: 193006

Nmrshiftdb2: 70003831

Chembl: CHEMBL249257

No compound-protein relationship available.

SMILES: N1CC(=O)NC(C1=O)Cc2c[nH]c(c23)cccc3

Level: 1

Mol. Weight: 393.53 g/mol

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 393.53 g/mol

SMILES: O=C1CNC(=O)CN1

Level: 0

Mol. Weight: 393.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.97
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.84
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.53

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.21
Plasma Protein Binding: 70.62
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.14
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.65
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.77
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.35
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: -13.44
Rat (Acute): 2.75
Rat (Chronic Oral): 2.48
Fathead Minnow: 4.58
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 475.12
Hydration Free Energy: -7.13
Log(D) at pH=7.4: 3.68
Log(P): 5.01
Log S: -4.6
Log(Vapor Pressure): -9.51
Melting Point: 175.73
pKa Acid: 10.2
pKa Basic: 5.84

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9466
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9383
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9363
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.9042
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.9023
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.9011
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8948
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8737
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8699
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8601
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8561
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8458
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	3	0.8398
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8370
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8318
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8293
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8287
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.8232
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8185
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8060
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	4	0.8031
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8009
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8004
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8003
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8001
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7945
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7928
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7927
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7877
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7874
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7873
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7866
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7855
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7733
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7688
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	4	0.7649
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7630
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7605
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7566
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7515
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	2	0.7494
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7487
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	3	0.7466
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7418
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7409
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7383
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7365
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7350
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7311
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7307
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7295
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7267
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7264
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7259
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	4	0.7255
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7232
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7131
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7128
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7126
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7117
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7076
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7064
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7063
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7062
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7054
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7043
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7037
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7019

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