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Neochinulin D

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

Canonical Smiles	C=CC(c1[nH]c2c(c1/C=C/1\NC(=O)[C@@H](NC1=O)C)ccc(c2)CC=C(C)C)(C)C
InChI	InChI=1S/C24H29N3O2/c1-7-24(5,6)21-18(13-20-23(29)25-15(4)22(28)27-20)17-11-10-16(9-8-14(2)3)12-19(17)26-21/h7-8,10-13,15,26H,1,9H2,2-6H3,(H,25,29)(H,27,28)/b20-13-/t15-/m0/s1
InChIKey	YCCLECFRSYOPML-HYTQYMIGSA-N
Formula	C₂₄H₂₉N₃O₂
HBA	2
HBD	3
MW	391.52
Rotatable Bonds	5
TPSA	73.99
LogP	4.12
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	391.23
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: 92468099

Cas: 57765-86-3

Zinc: ZINC000014612874

Nmrshiftdb2: 80008788

No compound-protein relationship available.

SMILES: N1C(=O)CNC(=O)C1=Cc2c[nH]c(c23)cccc3

Level: 1

Mol. Weight: 391.52 g/mol

SMILES: C=C1C(=O)NCC(=O)N1

Level: 0

Mol. Weight: 391.52 g/mol

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 391.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.05
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.86
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.3
Plasma Protein Binding: 59.6
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.52
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.54
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.4
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.59
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: -13.69
Rat (Acute): 2.61
Rat (Chronic Oral): 2.77
Fathead Minnow: 4.73
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 495.81
Hydration Free Energy: -7.06
Log(D) at pH=7.4: 4.02
Log(P): 4.81
Log S: -5.12
Log(Vapor Pressure): -10.18
Melting Point: 192.32
pKa Acid: 9.41
pKa Basic: 5.47

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.8680
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8373
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8348
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8288
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.8271
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8196
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8106
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8032
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8026
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7978
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7976
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7914
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7830
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7782
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7764
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7748
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7726
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7698
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7608
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7575
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7569
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7483
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7463
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7407
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7404
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7354
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7341
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7232
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7186
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7151
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7127
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7047
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7013
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7007

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