Structure

Physi-Chem Properties

Molecular Weight:  134.07
Volume:  123.468
LogP:  -3.574
LogD:  -1.65
LogS:  -0.107
# Rotatable Bonds:  4
TPSA:  98.57
# H-Bond Aceptor:  5
# H-Bond Donor:  5
# Rings:  0
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.414
Synthetic Accessibility Score:  3.152
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.147
MDCK Permeability:  0.003984453156590462
Pgp-inhibitor:  0.001
Pgp-substrate:  0.037
Human Intestinal Absorption (HIA):  0.041
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.397
Plasma Protein Binding (PPB):  11.233051300048828%
Volume Distribution (VD):  0.569
Pgp-substrate:  87.22572326660156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.053
CYP2C19-inhibitor:  0.04
CYP2C19-substrate:  0.05
CYP2C9-inhibitor:  0.019
CYP2C9-substrate:  0.348
CYP2D6-inhibitor:  0.039
CYP2D6-substrate:  0.193
CYP3A4-inhibitor:  0.009
CYP3A4-substrate:  0.018

ADMET: Excretion

Clearance (CL):  5.287
Half-life (T1/2):  0.571

ADMET: Toxicity

hERG Blockers:  0.024
Human Hepatotoxicity (H-HT):  0.071
Drug-inuced Liver Injury (DILI):  0.013
AMES Toxicity:  0.926
Rat Oral Acute Toxicity:  0.09
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.326
Carcinogencity:  0.171
Eye Corrosion:  0.02
Eye Irritation:  0.099
Respiratory Toxicity:  0.111

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC136159

Natural Product ID:  NPC136159
Common Name*:   Canaline
IUPAC Name:   (2S)-2-amino-4-aminooxybutanoic acid
Synonyms:   Canaline
Standard InCHIKey:  FQPGMQABJNQLLF-VKHMYHEASA-N
Standard InCHI:  InChI=1S/C4H10N2O3/c5-3(4(7)8)1-2-9-6/h3H,1-2,5-6H2,(H,7,8)/t3-/m0/s1
SMILES:  C(CON)[C@@H](C(=O)O)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1231652
PubChem CID:   441443
25246035
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids and derivatives
              • [CHEMONTID:0002404] Alpha amino acids
                • [CHEMONTID:0004146] L-alpha-amino acids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO24668 Ophiocoma dentata Species Ophiocomidae Eukaryota n.a. n.a. n.a. PMID[8145229]
NPO27984 Achillea moschata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27984 Achillea moschata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27984 Achillea moschata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24668 Ophiocoma dentata Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28743 Ticorea longiflora n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26620 Pulicaria arabica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27984 Achillea moschata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6635 Deamia testudo Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.0 nM PMID[468365]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC136159 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8776 High Similarity NPC60672
0.8776 High Similarity NPC322091
0.8511 High Similarity NPC153370
0.8261 Intermediate Similarity NPC285322
0.8261 Intermediate Similarity NPC208793
0.8182 Intermediate Similarity NPC326992
0.8182 Intermediate Similarity NPC121517
0.8182 Intermediate Similarity NPC168375
0.8085 Intermediate Similarity NPC309658
0.7872 Intermediate Similarity NPC329263
0.7826 Intermediate Similarity NPC291186
0.7826 Intermediate Similarity NPC167986
0.7778 Intermediate Similarity NPC326212
0.7778 Intermediate Similarity NPC66043
0.7778 Intermediate Similarity NPC237525
0.766 Intermediate Similarity NPC132307
0.766 Intermediate Similarity NPC325097
0.766 Intermediate Similarity NPC126925
0.76 Intermediate Similarity NPC270805
0.76 Intermediate Similarity NPC93888
0.7551 Intermediate Similarity NPC181588
0.7547 Intermediate Similarity NPC327831
0.75 Intermediate Similarity NPC327698
0.75 Intermediate Similarity NPC118459
0.7455 Intermediate Similarity NPC190385
0.74 Intermediate Similarity NPC140872
0.74 Intermediate Similarity NPC93081
0.7391 Intermediate Similarity NPC53449
0.7347 Intermediate Similarity NPC136476
0.7347 Intermediate Similarity NPC49952
0.7273 Intermediate Similarity NPC272614
0.7273 Intermediate Similarity NPC116709
0.7273 Intermediate Similarity NPC21290
0.7255 Intermediate Similarity NPC324825
0.7255 Intermediate Similarity NPC316231
0.7255 Intermediate Similarity NPC112890
0.7234 Intermediate Similarity NPC219143
0.7234 Intermediate Similarity NPC226265
0.7143 Intermediate Similarity NPC93861
0.7143 Intermediate Similarity NPC327895
0.7143 Intermediate Similarity NPC112224
0.7143 Intermediate Similarity NPC43169
0.7115 Intermediate Similarity NPC125736
0.7111 Intermediate Similarity NPC63621
0.7 Intermediate Similarity NPC297220
0.7 Intermediate Similarity NPC185755
0.7 Intermediate Similarity NPC213876
0.6957 Remote Similarity NPC18188
0.6939 Remote Similarity NPC198301
0.6923 Remote Similarity NPC226027
0.6923 Remote Similarity NPC43204
0.6923 Remote Similarity NPC193989
0.6923 Remote Similarity NPC328378
0.6923 Remote Similarity NPC245027
0.6923 Remote Similarity NPC162620
0.6923 Remote Similarity NPC170739
0.6923 Remote Similarity NPC62045
0.6923 Remote Similarity NPC84636
0.6923 Remote Similarity NPC174246
0.6923 Remote Similarity NPC152451
0.6863 Remote Similarity NPC316168
0.6852 Remote Similarity NPC329495
0.6852 Remote Similarity NPC197087
0.6852 Remote Similarity NPC190184
0.6833 Remote Similarity NPC106216
0.6833 Remote Similarity NPC88898
0.6792 Remote Similarity NPC273330
0.6792 Remote Similarity NPC137958
0.6792 Remote Similarity NPC315977
0.678 Remote Similarity NPC322206
0.6731 Remote Similarity NPC327542
0.6731 Remote Similarity NPC227850
0.6727 Remote Similarity NPC316889
0.6727 Remote Similarity NPC321118
0.661 Remote Similarity NPC68974
0.6607 Remote Similarity NPC2801
0.6604 Remote Similarity NPC286989
0.6591 Remote Similarity NPC114517
0.6545 Remote Similarity NPC317815
0.6538 Remote Similarity NPC204364
0.6531 Remote Similarity NPC317691
0.6531 Remote Similarity NPC110533
0.6531 Remote Similarity NPC254482
0.6531 Remote Similarity NPC326808
0.6522 Remote Similarity NPC9294
0.6508 Remote Similarity NPC221764
0.6508 Remote Similarity NPC196359
0.6508 Remote Similarity NPC135539
0.6508 Remote Similarity NPC78312
0.6491 Remote Similarity NPC38463
0.6491 Remote Similarity NPC325985
0.6481 Remote Similarity NPC114990
0.6429 Remote Similarity NPC279661
0.6429 Remote Similarity NPC183845
0.6406 Remote Similarity NPC107224
0.64 Remote Similarity NPC276294
0.64 Remote Similarity NPC107645
0.6379 Remote Similarity NPC278209
0.6364 Remote Similarity NPC200550
0.6364 Remote Similarity NPC155156
0.6346 Remote Similarity NPC198196
0.6316 Remote Similarity NPC102815
0.6316 Remote Similarity NPC10915
0.6275 Remote Similarity NPC323974
0.6271 Remote Similarity NPC176164
0.6271 Remote Similarity NPC189301
0.625 Remote Similarity NPC118524
0.6226 Remote Similarity NPC101249
0.6182 Remote Similarity NPC319175
0.6167 Remote Similarity NPC316826
0.6167 Remote Similarity NPC254541
0.6167 Remote Similarity NPC327748
0.6167 Remote Similarity NPC320598
0.6167 Remote Similarity NPC321468
0.6167 Remote Similarity NPC317143
0.6167 Remote Similarity NPC321536
0.6154 Remote Similarity NPC191136
0.6136 Remote Similarity NPC198126
0.6102 Remote Similarity NPC318260
0.6102 Remote Similarity NPC317147
0.6066 Remote Similarity NPC143722
0.6066 Remote Similarity NPC321419
0.6066 Remote Similarity NPC327170
0.6066 Remote Similarity NPC329564
0.6066 Remote Similarity NPC177191
0.6047 Remote Similarity NPC126681
0.6042 Remote Similarity NPC69179
0.6038 Remote Similarity NPC228932
0.6034 Remote Similarity NPC322573
0.6029 Remote Similarity NPC185084
0.6 Remote Similarity NPC11433
0.6 Remote Similarity NPC17244
0.6 Remote Similarity NPC245346
0.6 Remote Similarity NPC145217
0.6 Remote Similarity NPC302003
0.6 Remote Similarity NPC84444
0.5968 Remote Similarity NPC118429
0.5932 Remote Similarity NPC313263
0.5926 Remote Similarity NPC118187
0.5902 Remote Similarity NPC473599
0.5902 Remote Similarity NPC268927
0.5902 Remote Similarity NPC276928
0.5902 Remote Similarity NPC64250
0.5862 Remote Similarity NPC145235
0.5846 Remote Similarity NPC470108
0.5846 Remote Similarity NPC327985
0.5818 Remote Similarity NPC318523
0.5789 Remote Similarity NPC202525
0.5781 Remote Similarity NPC103130
0.5781 Remote Similarity NPC226453
0.5781 Remote Similarity NPC289691
0.5758 Remote Similarity NPC470109
0.5714 Remote Similarity NPC273037
0.5714 Remote Similarity NPC477644
0.5692 Remote Similarity NPC160661
0.5692 Remote Similarity NPC325597
0.5692 Remote Similarity NPC472609
0.5692 Remote Similarity NPC174304
0.5692 Remote Similarity NPC278881
0.569 Remote Similarity NPC245768
0.5672 Remote Similarity NPC319046
0.5672 Remote Similarity NPC470110
0.566 Remote Similarity NPC43264
0.5625 Remote Similarity NPC316685
0.5625 Remote Similarity NPC327252
0.5614 Remote Similarity NPC50457
0.5606 Remote Similarity NPC325534
0.56 Remote Similarity NPC314466

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC136159 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8511 High Similarity NPD8614 Approved
0.8261 Intermediate Similarity NPD8610 Approved
0.7826 Intermediate Similarity NPD8805 Approved
0.7826 Intermediate Similarity NPD8804 Approved
0.766 Intermediate Similarity NPD8798 Approved
0.7609 Intermediate Similarity NPD8609 Approved
0.76 Intermediate Similarity NPD8624 Approved
0.7551 Intermediate Similarity NPD8810 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD9023 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD8809 Approved
0.74 Intermediate Similarity NPD8808 Approved
0.7273 Intermediate Similarity NPD8211 Approved
0.7273 Intermediate Similarity NPD8210 Phase 3
0.7255 Intermediate Similarity NPD9044 Approved
0.7234 Intermediate Similarity NPD8216 Approved
0.7234 Intermediate Similarity NPD8217 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8982 Approved
0.7 Intermediate Similarity NPD8801 Approved
0.6957 Remote Similarity NPD8623 Phase 1
0.6923 Remote Similarity NPD8802 Approved
0.6923 Remote Similarity NPD9021 Approved
0.6923 Remote Similarity NPD9017 Approved
0.6923 Remote Similarity NPD9018 Approved
0.6923 Remote Similarity NPD8803 Clinical (unspecified phase)
0.6923 Remote Similarity NPD9016 Clinical (unspecified phase)
0.6863 Remote Similarity NPD8209 Phase 2
0.6863 Remote Similarity NPD8208 Clinical (unspecified phase)
0.6852 Remote Similarity NPD8785 Approved
0.6792 Remote Similarity NPD9025 Approved
0.6792 Remote Similarity NPD8871 Approved
0.6792 Remote Similarity NPD8872 Phase 3
0.6545 Remote Similarity NPD8849 Clinical (unspecified phase)
0.6545 Remote Similarity NPD8851 Phase 1
0.6531 Remote Similarity NPD8214 Approved
0.6531 Remote Similarity NPD8215 Approved
0.6508 Remote Similarity NPD8868 Approved
0.6429 Remote Similarity NPD9419 Clinical (unspecified phase)
0.6415 Remote Similarity NPD8873 Approved
0.6346 Remote Similarity NPD9020 Approved
0.6275 Remote Similarity NPD9019 Approved
0.6271 Remote Similarity NPD9433 Approved
0.625 Remote Similarity NPD1429 Clinical (unspecified phase)
0.6226 Remote Similarity NPD8867 Approved
0.6226 Remote Similarity NPD8866 Approved
0.6207 Remote Similarity NPD8981 Clinical (unspecified phase)
0.6207 Remote Similarity NPD8980 Approved
0.6207 Remote Similarity NPD8979 Approved
0.6182 Remote Similarity NPD9212 Clinical (unspecified phase)
0.6136 Remote Similarity NPD8618 Approved
0.6047 Remote Similarity NPD7371 Approved
0.6032 Remote Similarity NPD1151 Approved
0.6 Remote Similarity NPD8865 Approved
0.6 Remote Similarity NPD8842 Clinical (unspecified phase)
0.6 Remote Similarity NPD9230 Discontinued
0.5968 Remote Similarity NPD9014 Approved
0.5926 Remote Similarity NPD8850 Approved
0.5909 Remote Similarity NPD8617 Approved
0.5909 Remote Similarity NPD8619 Approved
0.5781 Remote Similarity NPD9047 Approved
0.5781 Remote Similarity NPD9048 Approved
0.5781 Remote Similarity NPD9045 Approved
0.5781 Remote Similarity NPD9046 Phase 3
0.5763 Remote Similarity NPD8971 Approved
0.5714 Remote Similarity NPD8946 Approved
0.5714 Remote Similarity NPD574 Approved
0.5714 Remote Similarity NPD8947 Approved
0.5692 Remote Similarity NPD348 Approved
0.5672 Remote Similarity NPD337 Discontinued
0.5636 Remote Similarity NPD398 Approved
0.5636 Remote Similarity NPD1458 Approved
0.5636 Remote Similarity NPD399 Approved
0.5636 Remote Similarity NPD400 Approved
0.5636 Remote Similarity NPD8972 Approved
0.5636 Remote Similarity NPD1459 Approved
0.5636 Remote Similarity NPD8973 Approved
0.5625 Remote Similarity NPD9112 Discontinued
0.5625 Remote Similarity NPD575 Clinical (unspecified phase)
0.5606 Remote Similarity NPD8952 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data