Structure

Physi-Chem Properties

Molecular Weight:  354.91
Volume:  233.579
LogP:  2.066
LogD:  2.216
LogS:  -3.5
# Rotatable Bonds:  1
TPSA:  84.11
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.531
Synthetic Accessibility Score:  3.756
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.146
MDCK Permeability:  1.0181271136389114e-05
Pgp-inhibitor:  0.753
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.971
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.154
Plasma Protein Binding (PPB):  93.66405487060547%
Volume Distribution (VD):  0.745
Pgp-substrate:  10.04573917388916%

ADMET: Metabolism

CYP1A2-inhibitor:  0.373
CYP1A2-substrate:  0.958
CYP2C19-inhibitor:  0.303
CYP2C19-substrate:  0.031
CYP2C9-inhibitor:  0.249
CYP2C9-substrate:  0.007
CYP2D6-inhibitor:  0.032
CYP2D6-substrate:  0.048
CYP3A4-inhibitor:  0.733
CYP3A4-substrate:  0.334

ADMET: Excretion

Clearance (CL):  2.947
Half-life (T1/2):  0.847

ADMET: Toxicity

hERG Blockers:  0.491
Human Hepatotoxicity (H-HT):  0.99
Drug-inuced Liver Injury (DILI):  0.984
AMES Toxicity:  0.088
Rat Oral Acute Toxicity:  0.996
Maximum Recommended Daily Dose:  0.889
Skin Sensitization:  0.428
Carcinogencity:  0.946
Eye Corrosion:  0.003
Eye Irritation:  0.601
Respiratory Toxicity:  0.989

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

  Natural Product: NPC253687

Natural Product ID:  NPC253687
Common Name*:   Ageladine A
IUPAC Name:   4-(4,5-dibromo-1H-pyrrol-2-yl)-1H-imidazo[4,5-c]pyridin-2-amine
Synonyms:  
Standard InCHIKey:  QAKGJAQGTQLMFN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H7Br2N5/c11-4-3-6(15-9(4)12)7-8-5(1-2-14-7)16-10(13)17-8/h1-3,15H,(H3,13,16,17)
SMILES:  N=c1[nH]c2c([nH]1)ccnc2c1[nH]c(c(c1)Br)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL230806
PubChem CID:   10089677
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000328] Imidazopyridines
        • [CHEMONTID:0003590] Imidazo-[4,5-c]pyridines

*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
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota n.a. at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia 1997-AUG PMID[10514317]
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota n.a. n.a. n.a. PMID[14677933]
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota n.a. Okinawan n.a. PMID[26083682]
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota n.a. papua new guinean n.a. PMID[9784179]
NPO11199 Agelas nakamurai Species Agelasidae 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
NPT1089 Individual Protein Matrix metalloproteinase 12 Homo sapiens IC50 = 3660.0 nM PMID[573729]
NPT1089 Individual Protein Matrix metalloproteinase 12 Homo sapiens IC50 = 3660.0 nM PMID[573730]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens IC50 = 1700.0 nM PMID[573731]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens IC50 = 1.2 ug.mL-1 PMID[573732]
NPT569 Individual Protein Matrix metalloproteinase 8 Homo sapiens IC50 = 0.39 ug.mL-1 PMID[573732]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens IC50 = 0.79 ug.mL-1 PMID[573732]
NPT1089 Individual Protein Matrix metalloproteinase 12 Homo sapiens IC50 = 0.33 ug.mL-1 PMID[573732]
NPT1090 Individual Protein Matrix metalloproteinase 13 Homo sapiens IC50 = 0.47 ug.mL-1 PMID[573732]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens IC50 = 1.7 ug.mL-1 PMID[573732]
NPT4015 Individual Protein Matrix metalloproteinase 14 Homo sapiens IC50 = 0.2 ug.mL-1 PMID[573732]
NPT3114 Individual Protein Dual-specificity tyrosine-phosphorylation regulated kinase 1A Homo sapiens Activity <= 5.0 % PMID[573732]
NPT3276 Individual Protein Tyrosine-protein kinase TYK2 Homo sapiens Activity <= 5.0 % PMID[573732]
NPT3434 Individual Protein SPS1/STE20-related protein kinase YSK4 Homo sapiens Activity <= 5.0 % PMID[573732]
NPT5455 Individual Protein Casein kinase I isoform alpha Sus scrofa IC50 = 50000.0 nM PMID[573732]
NPT1265 Individual Protein Serine/threonine-protein kinase PIM1 Homo sapiens IC50 = 10000.0 nM PMID[573732]
NPT1089 Individual Protein Matrix metalloproteinase 12 Homo sapiens IC50 = 3660.0 nM PMID[573733]
NPT69 Individual Protein Matrix metalloproteinase-1 Homo sapiens IC50 = 2.0 ug.mL-1 PMID[573732]
NPT177 Tissue Aorta Rattus norvegicus Inhibition = 100.0 % PMID[573732]
NPT177 Tissue Aorta Rattus norvegicus Inhibition = 19.0 % PMID[573732]
NPT177 Tissue Aorta Rattus norvegicus Inhibition = 10.0 % PMID[573732]
NPT177 Tissue Aorta Rattus norvegicus Inhibition = 9.0 % PMID[573732]
NPT177 Tissue Aorta Rattus norvegicus IC50 = 24.0 ug.mL-1 PMID[573732]
NPT2 Others Unspecified Activity <= 5.0 % PMID[573732]
NPT84 Individual Protein Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus IC50 = 30000.0 nM PMID[573732]

☑ 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 NPC253687 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
0.807 Intermediate Similarity NPC307191
0.7771 Intermediate Similarity NPC470204
0.7738 Intermediate Similarity NPC274229
0.7725 Intermediate Similarity NPC470203
0.7706 Intermediate Similarity NPC97343
0.767 Intermediate Similarity NPC108011
0.7661 Intermediate Similarity NPC82331
0.756 Intermediate Similarity NPC122141
0.7556 Intermediate Similarity NPC231536
0.7529 Intermediate Similarity NPC474958
0.7529 Intermediate Similarity NPC17751
0.7529 Intermediate Similarity NPC280864
0.7471 Intermediate Similarity NPC317105
0.7471 Intermediate Similarity NPC247987
0.7432 Intermediate Similarity NPC188821
0.7432 Intermediate Similarity NPC474180
0.7414 Intermediate Similarity NPC477611
0.7378 Intermediate Similarity NPC316069
0.7378 Intermediate Similarity NPC63545
0.7371 Intermediate Similarity NPC280297
0.7333 Intermediate Similarity NPC179787
0.7333 Intermediate Similarity NPC469811
0.7333 Intermediate Similarity NPC201380
0.7289 Intermediate Similarity NPC321911
0.7273 Intermediate Similarity NPC474389
0.7262 Intermediate Similarity NPC141926
0.7262 Intermediate Similarity NPC232798
0.7219 Intermediate Similarity NPC34844
0.7169 Intermediate Similarity NPC143872
0.716 Intermediate Similarity NPC325903
0.711 Intermediate Similarity NPC225018
0.7108 Intermediate Similarity NPC204141
0.7095 Intermediate Similarity NPC473380
0.7095 Intermediate Similarity NPC240088
0.7062 Intermediate Similarity NPC54214
0.7053 Intermediate Similarity NPC136957
0.7053 Intermediate Similarity NPC19696
0.7037 Intermediate Similarity NPC216159
0.7035 Intermediate Similarity NPC236711
0.7 Intermediate Similarity NPC82295
0.6994 Remote Similarity NPC105127
0.6983 Remote Similarity NPC317054
0.6971 Remote Similarity NPC206148
0.6971 Remote Similarity NPC149265
0.6966 Remote Similarity NPC476421
0.6966 Remote Similarity NPC227489
0.6966 Remote Similarity NPC226835
0.6966 Remote Similarity NPC28096
0.6964 Remote Similarity NPC288838
0.6961 Remote Similarity NPC265710
0.6947 Remote Similarity NPC174281
0.6947 Remote Similarity NPC475286
0.6944 Remote Similarity NPC280852
0.6938 Remote Similarity NPC474357
0.6933 Remote Similarity NPC96102
0.6928 Remote Similarity NPC197068
0.6923 Remote Similarity NPC16659
0.6923 Remote Similarity NPC470323
0.6915 Remote Similarity NPC473342
0.6915 Remote Similarity NPC477167
0.6915 Remote Similarity NPC477166
0.6915 Remote Similarity NPC304187
0.6909 Remote Similarity NPC110126
0.6897 Remote Similarity NPC300238
0.689 Remote Similarity NPC125746
0.689 Remote Similarity NPC935
0.689 Remote Similarity NPC84911
0.689 Remote Similarity NPC267078
0.6867 Remote Similarity NPC284635
0.6867 Remote Similarity NPC115611
0.6856 Remote Similarity NPC473761
0.6853 Remote Similarity NPC116555
0.6842 Remote Similarity NPC53947
0.6829 Remote Similarity NPC261195
0.6829 Remote Similarity NPC29886
0.6828 Remote Similarity NPC63571
0.6827 Remote Similarity NPC156003
0.6824 Remote Similarity NPC114209
0.6821 Remote Similarity NPC120070
0.6821 Remote Similarity NPC476297
0.6821 Remote Similarity NPC476219
0.6807 Remote Similarity NPC73767
0.6806 Remote Similarity NPC48117
0.6806 Remote Similarity NPC329765
0.6806 Remote Similarity NPC476526
0.6798 Remote Similarity NPC49217
0.6791 Remote Similarity NPC310633
0.6772 Remote Similarity NPC27740
0.6766 Remote Similarity NPC230002
0.6766 Remote Similarity NPC469767
0.6766 Remote Similarity NPC469768
0.6766 Remote Similarity NPC469783
0.6766 Remote Similarity NPC469779
0.6766 Remote Similarity NPC469761
0.6766 Remote Similarity NPC469780
0.6766 Remote Similarity NPC469784
0.6766 Remote Similarity NPC279081
0.6758 Remote Similarity NPC136441
0.6753 Remote Similarity NPC166209
0.6753 Remote Similarity NPC77241
0.6753 Remote Similarity NPC13456
0.6753 Remote Similarity NPC269203
0.6738 Remote Similarity NPC111566
0.6726 Remote Similarity NPC469766
0.6718 Remote Similarity NPC475935
0.6718 Remote Similarity NPC52909
0.6718 Remote Similarity NPC94211
0.6707 Remote Similarity NPC316811
0.6705 Remote Similarity NPC470233
0.6703 Remote Similarity NPC471579
0.6702 Remote Similarity NPC19342
0.6701 Remote Similarity NPC475914
0.6701 Remote Similarity NPC220797
0.6701 Remote Similarity NPC474318
0.6701 Remote Similarity NPC153123
0.6701 Remote Similarity NPC201266
0.6701 Remote Similarity NPC237414
0.6701 Remote Similarity NPC268744
0.6686 Remote Similarity NPC190296
0.6686 Remote Similarity NPC42483
0.6686 Remote Similarity NPC2272
0.6686 Remote Similarity NPC282531
0.6683 Remote Similarity NPC470703
0.6667 Remote Similarity NPC198988
0.6667 Remote Similarity NPC303820
0.6667 Remote Similarity NPC205254
0.6667 Remote Similarity NPC106771
0.6667 Remote Similarity NPC23420
0.6648 Remote Similarity NPC2165
0.6648 Remote Similarity NPC216643
0.6648 Remote Similarity NPC195507
0.6634 Remote Similarity NPC470702
0.6634 Remote Similarity NPC473218
0.6634 Remote Similarity NPC475736
0.6628 Remote Similarity NPC470111
0.6627 Remote Similarity NPC325252
0.6623 Remote Similarity NPC84268
0.661 Remote Similarity NPC135141
0.661 Remote Similarity NPC92796
0.6608 Remote Similarity NPC159856
0.6608 Remote Similarity NPC314372
0.6585 Remote Similarity NPC477114
0.6585 Remote Similarity NPC267811
0.657 Remote Similarity NPC474195
0.6559 Remote Similarity NPC40530
0.6559 Remote Similarity NPC314281
0.6548 Remote Similarity NPC469308
0.6543 Remote Similarity NPC469814
0.6533 Remote Similarity NPC470505
0.6533 Remote Similarity NPC231655
0.6532 Remote Similarity NPC471957
0.652 Remote Similarity NPC282247
0.6509 Remote Similarity NPC88097
0.6505 Remote Similarity NPC276540
0.6505 Remote Similarity NPC233050
0.65 Remote Similarity NPC46358
0.65 Remote Similarity NPC478184
0.6485 Remote Similarity NPC101165
0.648 Remote Similarity NPC215584
0.648 Remote Similarity NPC44773
0.6478 Remote Similarity NPC48564
0.6478 Remote Similarity NPC265605
0.6478 Remote Similarity NPC182570
0.6473 Remote Similarity NPC469717
0.6457 Remote Similarity NPC105818
0.6457 Remote Similarity NPC24678
0.6445 Remote Similarity NPC474196
0.6436 Remote Similarity NPC191415
0.6436 Remote Similarity NPC476524
0.6436 Remote Similarity NPC243381
0.6436 Remote Similarity NPC275292
0.6436 Remote Similarity NPC476525
0.6429 Remote Similarity NPC109447
0.6429 Remote Similarity NPC218268
0.6429 Remote Similarity NPC478183
0.6425 Remote Similarity NPC56765
0.642 Remote Similarity NPC216713
0.642 Remote Similarity NPC245244
0.642 Remote Similarity NPC146373
0.642 Remote Similarity NPC470823
0.642 Remote Similarity NPC166424
0.6409 Remote Similarity NPC73687
0.6402 Remote Similarity NPC48938
0.6402 Remote Similarity NPC102755
0.6389 Remote Similarity NPC229173
0.6387 Remote Similarity NPC476527
0.6386 Remote Similarity NPC471322
0.6384 Remote Similarity NPC469786
0.6384 Remote Similarity NPC259644
0.6384 Remote Similarity NPC200214
0.6384 Remote Similarity NPC469765
0.6384 Remote Similarity NPC25008
0.6384 Remote Similarity NPC73952
0.6384 Remote Similarity NPC469760
0.6384 Remote Similarity NPC469763
0.6383 Remote Similarity NPC164228
0.6382 Remote Similarity NPC9635
0.6374 Remote Similarity NPC59084
0.6368 Remote Similarity NPC284678
0.6368 Remote Similarity NPC110158

  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 NPC253687 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
0.8121 Intermediate Similarity NPD438 Approved
0.8121 Intermediate Similarity NPD439 Approved
0.7939 Intermediate Similarity NPD1016 Phase 2
0.7939 Intermediate Similarity NPD1015 Phase 2
0.7844 Intermediate Similarity NPD1333 Phase 3
0.7778 Intermediate Similarity NPD971 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD1567 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD2478 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD2930 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4649 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD1895 Discontinued
0.7329 Intermediate Similarity NPD174 Discontinued
0.7325 Intermediate Similarity NPD809 Discontinued
0.7303 Intermediate Similarity NPD5962 Phase 2
0.7232 Intermediate Similarity NPD2367 Phase 2
0.7225 Intermediate Similarity NPD1313 Approved
0.7215 Intermediate Similarity NPD803 Phase 1
0.7198 Intermediate Similarity NPD2793 Discontinued
0.7151 Intermediate Similarity NPD3341 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2333 Discontinued
0.7135 Intermediate Similarity NPD3419 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD9598 Discontinued
0.7104 Intermediate Similarity NPD706 Phase 1
0.7083 Intermediate Similarity NPD2364 Suspended
0.7011 Intermediate Similarity NPD3378 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD2875 Clinical (unspecified phase)
0.6981 Remote Similarity NPD9305 Clinical (unspecified phase)
0.6974 Remote Similarity NPD9392 Approved
0.6974 Remote Similarity NPD9396 Approved
0.6968 Remote Similarity NPD2446 Approved
0.6968 Remote Similarity NPD2445 Approved
0.6937 Remote Similarity NPD715 Phase 3
0.6933 Remote Similarity NPD198 Clinical (unspecified phase)
0.6928 Remote Similarity NPD1722 Approved
0.6895 Remote Similarity NPD2316 Clinical (unspecified phase)
0.6845 Remote Similarity NPD207 Discontinued
0.6839 Remote Similarity NPD5300 Clinical (unspecified phase)
0.6831 Remote Similarity NPD1873 Clinical (unspecified phase)
0.6828 Remote Similarity NPD645 Clinical (unspecified phase)
0.6828 Remote Similarity NPD2963 Phase 1
0.6828 Remote Similarity NPD3913 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5145 Clinical (unspecified phase)
0.6807 Remote Similarity NPD786 Approved
0.6802 Remote Similarity NPD2128 Phase 1
0.6798 Remote Similarity NPD1215 Discontinued
0.6798 Remote Similarity NPD2392 Clinical (unspecified phase)
0.6793 Remote Similarity NPD1707 Approved
0.6793 Remote Similarity NPD412 Approved
0.6793 Remote Similarity NPD1708 Approved
0.6786 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6782 Remote Similarity NPD2927 Phase 3
0.6778 Remote Similarity NPD6828 Phase 2
0.6778 Remote Similarity NPD6827 Clinical (unspecified phase)
0.6763 Remote Similarity NPD2837 Discontinued
0.676 Remote Similarity NPD2390 Clinical (unspecified phase)
0.6757 Remote Similarity NPD1332 Clinical (unspecified phase)
0.6744 Remote Similarity NPD2172 Phase 1
0.6743 Remote Similarity NPD1869 Phase 2
0.674 Remote Similarity NPD1037 Clinical (unspecified phase)
0.6738 Remote Similarity NPD5757 Discontinued
0.6723 Remote Similarity NPD1853 Clinical (unspecified phase)
0.672 Remote Similarity NPD2456 Phase 2
0.672 Remote Similarity NPD2457 Phase 2
0.6719 Remote Similarity NPD6278 Clinical (unspecified phase)
0.6707 Remote Similarity NPD2071 Approved
0.6707 Remote Similarity NPD2068 Approved
0.6707 Remote Similarity NPD2069 Approved
0.6707 Remote Similarity NPD2070 Approved
0.6686 Remote Similarity NPD2150 Discontinued
0.6686 Remote Similarity NPD9724 Phase 1
0.6684 Remote Similarity NPD5462 Discontinued
0.6684 Remote Similarity NPD2880 Discontinued
0.6667 Remote Similarity NPD2406 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6816 Phase 3
0.6649 Remote Similarity NPD2839 Phase 2
0.6647 Remote Similarity NPD1030 Approved
0.6647 Remote Similarity NPD1029 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1027 Approved
0.6646 Remote Similarity NPD992 Clinical (unspecified phase)
0.6646 Remote Similarity NPD1598 Discontinued
0.6646 Remote Similarity NPD991 Phase 2
0.6633 Remote Similarity NPD7445 Phase 1
0.6633 Remote Similarity NPD1506 Discontinued
0.6632 Remote Similarity NPD2960 Clinical (unspecified phase)
0.663 Remote Similarity NPD4181 Approved
0.6629 Remote Similarity NPD418 Approved
0.6615 Remote Similarity NPD3485 Clinical (unspecified phase)
0.6615 Remote Similarity NPD460 Discontinued
0.6615 Remote Similarity NPD6265 Discontinued
0.6611 Remote Similarity NPD1248 Discontinued
0.66 Remote Similarity NPD2442 Approved
0.66 Remote Similarity NPD2443 Approved
0.6593 Remote Similarity NPD3347 Clinical (unspecified phase)
0.659 Remote Similarity NPD4374 Clinical (unspecified phase)
0.6588 Remote Similarity NPD2006 Phase 2
0.6583 Remote Similarity NPD2008 Discontinued
0.6571 Remote Similarity NPD491 Approved
0.6571 Remote Similarity NPD695 Discontinued
0.6571 Remote Similarity NPD1303 Phase 1
0.6559 Remote Similarity NPD1928 Discontinued
0.6559 Remote Similarity NPD6277 Clinical (unspecified phase)
0.6557 Remote Similarity NPD966 Clinical (unspecified phase)
0.6556 Remote Similarity NPD509 Phase 3
0.6554 Remote Similarity NPD1192 Clinical (unspecified phase)
0.6552 Remote Similarity NPD8458 Clinical (unspecified phase)
0.6548 Remote Similarity NPD4318 Clinical (unspecified phase)
0.6545 Remote Similarity NPD1994 Approved
0.6545 Remote Similarity NPD2818 Discontinued
0.6545 Remote Similarity NPD1993 Approved
0.6545 Remote Similarity NPD1995 Approved
0.6534 Remote Similarity NPD977 Approved
0.6534 Remote Similarity NPD975 Approved
0.6534 Remote Similarity NPD976 Approved
0.6533 Remote Similarity NPD9099 Clinical (unspecified phase)
0.6533 Remote Similarity NPD9098 Phase 3
0.6527 Remote Similarity NPD490 Clinical (unspecified phase)
0.6524 Remote Similarity NPD5806 Clinical (unspecified phase)
0.6522 Remote Similarity NPD4128 Approved
0.652 Remote Similarity NPD8488 Clinical (unspecified phase)
0.6517 Remote Similarity NPD2026 Approved
0.6515 Remote Similarity NPD4872 Clinical (unspecified phase)
0.6514 Remote Similarity NPD1257 Approved
0.6513 Remote Similarity NPD3830 Phase 1
0.6513 Remote Similarity NPD1174 Phase 2
0.6508 Remote Similarity NPD2868 Clinical (unspecified phase)
0.65 Remote Similarity NPD4023 Clinical (unspecified phase)
0.6497 Remote Similarity NPD939 Clinical (unspecified phase)
0.6497 Remote Similarity NPD1290 Phase 2
0.6494 Remote Similarity NPD3100 Discontinued
0.6494 Remote Similarity NPD1183 Approved
0.6494 Remote Similarity NPD426 Approved
0.6494 Remote Similarity NPD428 Approved
0.6494 Remote Similarity NPD427 Approved
0.6494 Remote Similarity NPD162 Approved
0.6489 Remote Similarity NPD4441 Phase 2
0.6486 Remote Similarity NPD2751 Phase 1
0.6486 Remote Similarity NPD2864 Phase 1
0.6485 Remote Similarity NPD1600 Suspended
0.6478 Remote Similarity NPD268 Approved
0.6478 Remote Similarity NPD270 Clinical (unspecified phase)
0.6478 Remote Similarity NPD271 Approved
0.6477 Remote Similarity NPD4615 Phase 2
0.6477 Remote Similarity NPD1917 Discontinued
0.6474 Remote Similarity NPD2591 Phase 2
0.6474 Remote Similarity NPD4902 Discontinued
0.6473 Remote Similarity NPD3521 Phase 2
0.6471 Remote Similarity NPD4352 Phase 1
0.6468 Remote Similarity NPD8410 Clinical (unspecified phase)
0.6467 Remote Similarity NPD2142 Approved
0.6467 Remote Similarity NPD2141 Approved
0.6467 Remote Similarity NPD2140 Approved
0.6465 Remote Similarity NPD4142 Discontinued
0.6465 Remote Similarity NPD4458 Phase 2
0.6465 Remote Similarity NPD4459 Clinical (unspecified phase)
0.6462 Remote Similarity NPD7023 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7111 Discontinued
0.6452 Remote Similarity NPD1272 Clinical (unspecified phase)
0.6452 Remote Similarity NPD2731 Phase 2
0.6447 Remote Similarity NPD6264 Discontinued
0.6439 Remote Similarity NPD4341 Clinical (unspecified phase)
0.6436 Remote Similarity NPD1675 Phase 1
0.6436 Remote Similarity NPD1674 Clinical (unspecified phase)
0.6425 Remote Similarity NPD1042 Clinical (unspecified phase)
0.6424 Remote Similarity NPD3475 Approved
0.6424 Remote Similarity NPD3476 Approved
0.6421 Remote Similarity NPD4298 Clinical (unspecified phase)
0.6417 Remote Similarity NPD5730 Phase 2
0.6417 Remote Similarity NPD1327 Discontinued
0.6417 Remote Similarity NPD40 Phase 2
0.6404 Remote Similarity NPD2408 Discontinued
0.6402 Remote Similarity NPD1095 Clinical (unspecified phase)
0.64 Remote Similarity NPD2430 Phase 2
0.64 Remote Similarity NPD499 Phase 3
0.6396 Remote Similarity NPD7459 Phase 2
0.6396 Remote Similarity NPD1982 Phase 1
0.6394 Remote Similarity NPD6470 Phase 3
0.6393 Remote Similarity NPD9582 Phase 3
0.639 Remote Similarity NPD2411 Approved
0.6387 Remote Similarity NPD6721 Phase 1
0.6387 Remote Similarity NPD5642 Approved
0.6387 Remote Similarity NPD2872 Phase 2
0.638 Remote Similarity NPD9583 Approved
0.6378 Remote Similarity NPD409 Clinical (unspecified phase)
0.6368 Remote Similarity NPD5520 Phase 2
0.6364 Remote Similarity NPD9709 Approved
0.6364 Remote Similarity NPD2931 Phase 1
0.6364 Remote Similarity NPD9708 Approved
0.6358 Remote Similarity NPD1918 Clinical (unspecified phase)
0.6358 Remote Similarity NPD1988 Phase 1
0.6358 Remote Similarity NPD9357 Approved
0.6354 Remote Similarity NPD2009 Clinical (unspecified phase)
0.6354 Remote Similarity NPD7394 Phase 2
0.635 Remote Similarity NPD3015 Discontinued
0.6346 Remote Similarity NPD5465 Phase 2
0.6339 Remote Similarity NPD2639 Approved
0.6339 Remote Similarity NPD6794 Approved
0.6339 Remote Similarity NPD2642 Approved
0.6335 Remote Similarity NPD6610 Clinical (unspecified phase)
0.6335 Remote Similarity NPD5787 Discontinued
0.633 Remote Similarity NPD3409 Phase 1

  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