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Haenamindole

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

Canonical Smiles	O=C1N[C@@H](CC2CCCCC2)C(=O)N([C@@H]1C[C@]1(C)c2ccccc2N2[C@H]1N[C@@H](CC2=O)c1ccccc1)O
InChI	InChI=1S/C30H36N4O4/c1-30(18-25-27(36)31-23(28(37)34(25)38)16-19-10-4-2-5-11-19)21-14-8-9-15-24(21)33-26(35)17-22(32-29(30)33)20-12-6-3-7-13-20/h3,6-9,12-15,19,22-23,25,29,32,38H,2,4-5,10-11,16-18H2,1H3,(H,31,36)/t22-,23-,25+,29+,30+/m0/s1
InChIKey	SYRKXVJXAYRATF-OEBFQYBYSA-N
Formula	C₃₀H₃₆N₄O₄
HBA	5
HBD	3
MW	516.64
Rotatable Bonds	5
TPSA	101.98
LogP	3.8
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	38
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	516.27
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Emericella dentata	Trichocomaceae	Fungi	286160

Showing of synonyms

Hamed A, Abdel-Razek A.S, et al. (2021). Meleagrin from marine fungus Emericella dentata Nq45: crystal structure and diverse biological activity studies. Nat Prod Res,2021,35(21),3830-3838. [View] [PubMed]

Pubchem: 139588722

Nmrshiftdb2: 80021308

No compound-protein relationship available.

SMILES: c1ccccc1C(CC2=O)NC(N2c(c34)cccc4)C3CC(C5=O)NC(=O)C(N5)CC6CCCCC6

Level: 3

Mol. Weight: 516.64 g/mol

SMILES: c1cccc(c12)N3C(NCCC3=O)C2CC(C4=O)NC(=O)C(N4)CC5CCCCC5

Level: 2

Mol. Weight: 516.64 g/mol

SMILES: N1CC(=O)NC(C1=O)CC2C(N3c(c24)cccc4)NC(CC3=O)c5ccccc5

Level: 2

Mol. Weight: 516.64 g/mol

SMILES: N1CC(=O)NC(C1=O)CC2C(NCCC3=O)N3c(c24)cccc4

Level: 1

Mol. Weight: 516.64 g/mol

SMILES: c1cccc(c12)N3C(C2)NC(CC3=O)c4ccccc4

Level: 1

Mol. Weight: 516.64 g/mol

SMILES: N1CC(=O)NC(C1=O)CC2CCCCC2

Level: 1

Mol. Weight: 516.64 g/mol

SMILES: c1cccc(c12)N3C(C2)NCCC3=O

Level: 0

Mol. Weight: 516.64 g/mol

SMILES: O=C1CNC(=O)CN1

Level: 0

Mol. Weight: 516.64 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 516.64 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 516.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.26
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.82
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.12

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.16
Plasma Protein Binding: 110.0
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: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.05
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.24
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.36
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.41
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: -3415.56
Rat (Acute): 2.8
Rat (Chronic Oral): 2.63
Fathead Minnow: 10.49
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 457.6
Hydration Free Energy: -2.8
Log(D) at pH=7.4: 3.01
Log(P): 3.21
Log S: -3.98
Log(Vapor Pressure): -8.83
Melting Point: 191.82
pKa Acid: 6.69
pKa Basic: 4.68

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.9407
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9156
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9123
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8882
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8837
Acetolactate synthase catalytic subunit, mitochondrial	P07342	ILVB_YEAST	Saccharomyces cerevisiae	3	0.8776
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8758
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8689
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8666
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8614
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8601
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8446
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8339
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8300
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8297
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8205
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8189
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.8137
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8120
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.8118
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8039
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7947
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7946
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7936
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7906
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7867
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7822
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7757
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7749
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7720
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7653
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7618
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7605
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7581
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7577
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7533
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7509
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7507
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7485
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7480
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7473
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7432
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7432
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7398
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7378
Dipeptidyl peptidase 4	P14740	DPP4_RAT	Rattus norvegicus	2	0.7359
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7351
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7348
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7347
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7310
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7309
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7300
Kelch-like ECH-associated protein 1	Q14145	KEAP1_HUMAN	Homo sapiens	3	0.7296
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7288
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7284
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7273
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7272
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7234
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7227
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7223
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7218
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7217
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7212
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7195
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7179
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7169
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7090
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7086
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7080
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7076
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7071
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7068
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7064
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7053
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7033
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7019
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7018
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7017
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7016

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