Compound information

Natural Products
NACP153656
Molecular Formula
C23H29N5O5
Molecular Weight
455.216869028 g/mol
Structure
IUPAC Name
2-[[2-(benzyloxycarbonylamino)-3-phenyl-propanoyl]amino]-5-guanidino-pentanoic acid
InChI
InChI=1S/C23H29N5O5/c24-22(25)26-13-7-12-18(21(30)31)27-20(29)19(14-16-8-3-1-4-9-16)28-23(32)33-15-17-10-5-2-6-11-17/h1-6,8-11,18-19H,7,12-15H2,(H,27,29)(H,28,32)(H,30,31)(H4,24,25,26)
InChI Key
XHGIWCXAACQYGK-UHFFFAOYSA-N
SMILES
O=C(OCC=1C=CC=CC1)NC(C(=O)NC(C(=O)O)CCCNC(=N)N)CC=2C=CC=CC2
CAS
32949-41-0
SuperClass
Organic acids and derivatives
Class
Carboxylic acids and derivatives
SubClass
Amino acids, peptides, and analogues
Source
CNP0257443

Warheads

Carbamate


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 33 Ring Count 2
Heteroatom Count 10 Rotatable Bond Count 12
Hydrogen Bond Acceptor Count 5 Hydrogen Bond Donor Count 6
Topological Polar Surface Area 166.63 Å2 LogP 0.768
LogS -3.065 LogD 0.272


Absorption

Property Value Property Value
Pgp inhibitor 0.002 Pgp substrate 0.88
HIA 0.0 F20 % 0.126
F30 % 0.0 Caco-2 -6.621
MDCK -5.828


Distribution

Property Value Property Value
BBB Penetration 0.862 PPB 75.568
VD 0.582 Fu 0.483


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.001 CYP1A2 substrate 0.555
CYP2A6 substrate 0.333 CYP2B6 substrate 0.383
CYP2C19 inhibitor 0.051 CYP2C19 substrate 0.294
CYP2C8 substrate 0.487 CYP2C9 inhibitor 0.138
CYP2C9 substrate 0.06 CYP2D6 inhibitor 0.123
CYP2D6 substrate 0.282 CYP2E1 substrate 0.356
CYP3A4 inhibitor 0.052 CYP3A4 substrate 0.125


Excretion

Property Value Property Value
T1/2 0.695 CL 1.454


Toxicity

Property Value Property Value
hERG Blockers 0.194 Hepatotoxicity 0.526
Mutagenicity 0.031 Rat Oral Acute Toxicity 0.158
FDAMDD 0.111 Skin Sensitization 0.003
Carcinogenicity 0.0 Eye Corrosion 0.002
Eye Irritation 0.0 Respiratory Toxicity 0.102


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors -1.331 IGC50 2.258
LC50FM 3.212 LC50DM 3.336


Tox21 Pathway

Property Value Property Value
NR-AR 0.34 NR-AR-LBD 0.26
NR-AhR 0.003 NR-Aromatase 0.025
NR-ER 0.277 NR-ER-LBD 0.328
NR-PPAR-gamma 0.474 SR-ARE 0.1
SR-ATAD5 0.365 SR-HSE 0.143
SR-MMP 0.01 SR-p53 0.025


Similar covalent inhibitors

CI005325

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CI002644

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CI003307

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CI006078

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CI005320

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CI006079

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CI000667

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CI004288

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CI004314

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CI004063

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CI002272

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CI002273

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CI000107

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CI000712

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CI001365

Similarity Score: 0.51

CI001889

Similarity Score: 0.51

CI001964

Similarity Score: 0.51

CI004866

Similarity Score: 0.51



Similar covalent drugs

No similar covalent drugs found for this compound.