Structure

Physi-Chem Properties

Molecular Weight:  108.07
Volume:  117.86
LogP:  -0.123
LogD:  -0.271
LogS:  0.11
# Rotatable Bonds:  0
TPSA:  52.04
# H-Bond Aceptor:  2
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.484
Synthetic Accessibility Score:  1.668
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.916
MDCK Permeability:  0.00024384136486332864
Pgp-inhibitor:  0.0
Pgp-substrate:  0.974
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.313
Plasma Protein Binding (PPB):  22.804922103881836%
Volume Distribution (VD):  1.463
Pgp-substrate:  74.39147186279297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.371
CYP1A2-substrate:  0.143
CYP2C19-inhibitor:  0.302
CYP2C19-substrate:  0.448
CYP2C9-inhibitor:  0.198
CYP2C9-substrate:  0.285
CYP2D6-inhibitor:  0.026
CYP2D6-substrate:  0.782
CYP3A4-inhibitor:  0.253
CYP3A4-substrate:  0.182

ADMET: Excretion

Clearance (CL):  8.444
Half-life (T1/2):  0.267

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.17
Drug-inuced Liver Injury (DILI):  0.326
AMES Toxicity:  0.972
Rat Oral Acute Toxicity:  0.919
Maximum Recommended Daily Dose:  0.031
Skin Sensitization:  0.917
Carcinogencity:  0.61
Eye Corrosion:  0.861
Eye Irritation:  0.994
Respiratory Toxicity:  0.991

Download Data

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

  Natural Product: NPC301874

Natural Product ID:  NPC301874
Common Name*:   Benzene-1,4-Diamine
IUPAC Name:   benzene-1,4-diamine
Synonyms:   4-Phenylenediamine; P-Phenylenediamine
Standard InCHIKey:  CBCKQZAAMUWICA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
SMILES:  Nc1ccc(cc1)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL403741
PubChem CID:   7814
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000284] Aniline and substituted anilines

*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
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 12589.3 nM PMID[532195]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 14125.4 nM PMID[532195]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 15848.9 nM PMID[532195]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 3539.7 nM PMID[532196]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 6294.6 nM PMID[532195]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 12589.3 nM PMID[532195]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 25118.9 nM PMID[532196]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 125.9 nM PMID[532195]
NPT445 Individual Protein Peripheral myelin protein 22 Rattus norvegicus Potency n.a. 2869.5 nM PMID[532195]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 32196.8 nM PMID[532195]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 44668.4 nM PMID[532196]
NPT804 Cell Line HT-22 Mus musculus EC50 = 879.0 nM PMID[532198]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 1548.6 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 48557.7 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 8670.1 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 10590.1 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 6859 nM PubChem BioAssay data set
NPT615 Tissue Skin Homo sapiens log Kp = -7.22 n.a. PMID[532193]
NPT32 Organism Mus musculus Mus musculus Activity = 397.0 U/L PMID[532194]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 3548.1 nM PMID[532195]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 3162.3 nM PMID[532196]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 10000.0 nM PMID[532195]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 19011.5 nM PMID[532195]
NPT2 Others Unspecified Potency n.a. 36125.4 nM PMID[532195]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[532197]
NPT2 Others Unspecified AC50 n.a. 7079.5 nM PMID[532199]
NPT2 Others Unspecified Ac50 n.a. 44.67 uM PMID[532199]
NPT2 Others Unspecified Ac50 n.a. 7.079 uM PMID[532199]
NPT2 Others Unspecified Ac50 n.a. 17.78 uM PMID[532199]
NPT2 Others Unspecified AC50 n.a. 44668.4 nM PMID[532199]
NPT2 Others Unspecified AC50 n.a. 17782.8 nM PMID[532199]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[532200]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[532200]
NPT2 Others Unspecified Potency n.a. 38727.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34822.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68868.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21971.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54954.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48755.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27643.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30762.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3857.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 841.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61924 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 5470.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19331.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 29849.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61379.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48557.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 77272 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 33491.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3089.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19409.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10963.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12301.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2131.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54704.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 26603.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21778.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43277.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 16930.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61652.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34376.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 39071.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15417.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 23710.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6682.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9688.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6886.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 17228.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 8412.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27417.1 nM PubChem BioAssay data set

☑ 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 NPC301874 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
0.942 High Similarity NPC271732
0.8267 Intermediate Similarity NPC66775
0.825 Intermediate Similarity NPC134825
0.8072 Intermediate Similarity NPC262295
0.8049 Intermediate Similarity NPC229477
0.7882 Intermediate Similarity NPC173991
0.7882 Intermediate Similarity NPC315403
0.7791 Intermediate Similarity NPC191444
0.7791 Intermediate Similarity NPC92689
0.7778 Intermediate Similarity NPC307456
0.7765 Intermediate Similarity NPC111233
0.7765 Intermediate Similarity NPC30445
0.7674 Intermediate Similarity NPC176858
0.7647 Intermediate Similarity NPC43655
0.759 Intermediate Similarity NPC15839
0.7471 Intermediate Similarity NPC107135
0.7471 Intermediate Similarity NPC240134
0.7416 Intermediate Similarity NPC108800
0.7356 Intermediate Similarity NPC297532
0.7021 Intermediate Similarity NPC317642
0.7 Intermediate Similarity NPC78154
0.6962 Remote Similarity NPC219246
0.6957 Remote Similarity NPC476483
0.6947 Remote Similarity NPC316435
0.6907 Remote Similarity NPC474430
0.6867 Remote Similarity NPC325662
0.6867 Remote Similarity NPC98269
0.6768 Remote Similarity NPC313362
0.6701 Remote Similarity NPC70201
0.6667 Remote Similarity NPC328877
0.6634 Remote Similarity NPC37584
0.6591 Remote Similarity NPC119677
0.6569 Remote Similarity NPC302790
0.6566 Remote Similarity NPC311660
0.6543 Remote Similarity NPC229235
0.6535 Remote Similarity NPC24060
0.6531 Remote Similarity NPC326792
0.6506 Remote Similarity NPC113000
0.6506 Remote Similarity NPC112609
0.6506 Remote Similarity NPC122327
0.65 Remote Similarity NPC38262
0.65 Remote Similarity NPC256838
0.6471 Remote Similarity NPC79618
0.6471 Remote Similarity NPC434
0.6471 Remote Similarity NPC172170
0.6465 Remote Similarity NPC291610
0.6429 Remote Similarity NPC75496
0.6395 Remote Similarity NPC12857
0.6286 Remote Similarity NPC226914
0.6279 Remote Similarity NPC290638
0.6263 Remote Similarity NPC323726
0.6262 Remote Similarity NPC314141
0.6235 Remote Similarity NPC276699
0.6235 Remote Similarity NPC98976
0.6232 Remote Similarity NPC11150
0.6163 Remote Similarity NPC139658
0.6163 Remote Similarity NPC271642
0.6154 Remote Similarity NPC20322
0.6154 Remote Similarity NPC169016
0.6118 Remote Similarity NPC299134
0.6117 Remote Similarity NPC313810
0.61 Remote Similarity NPC213774
0.6095 Remote Similarity NPC164802
0.6091 Remote Similarity NPC125416
0.6078 Remote Similarity NPC178681
0.6055 Remote Similarity NPC470550
0.6055 Remote Similarity NPC205652
0.6022 Remote Similarity NPC258046
0.6 Remote Similarity NPC76327
0.6 Remote Similarity NPC222982
0.5893 Remote Similarity NPC313449
0.5888 Remote Similarity NPC255721
0.5849 Remote Similarity NPC44836
0.5833 Remote Similarity NPC9336
0.5826 Remote Similarity NPC475915
0.5818 Remote Similarity NPC296163
0.5818 Remote Similarity NPC187036
0.5814 Remote Similarity NPC244738
0.5804 Remote Similarity NPC313673
0.5795 Remote Similarity NPC35599
0.5758 Remote Similarity NPC469330
0.5739 Remote Similarity NPC279385
0.5739 Remote Similarity NPC179605
0.5714 Remote Similarity NPC277704
0.5714 Remote Similarity NPC288232
0.5714 Remote Similarity NPC218710
0.5714 Remote Similarity NPC149436
0.5714 Remote Similarity NPC143156
0.5714 Remote Similarity NPC317031
0.5702 Remote Similarity NPC229353
0.57 Remote Similarity NPC329430
0.5699 Remote Similarity NPC104070
0.569 Remote Similarity NPC103292
0.5688 Remote Similarity NPC329358
0.5676 Remote Similarity NPC264782
0.5676 Remote Similarity NPC57051
0.5676 Remote Similarity NPC322735
0.5664 Remote Similarity NPC147957
0.5641 Remote Similarity NPC198841
0.5641 Remote Similarity NPC268534
0.5641 Remote Similarity NPC269586
0.563 Remote Similarity NPC474926
0.5625 Remote Similarity NPC329190
0.5614 Remote Similarity NPC31651
0.5614 Remote Similarity NPC192209
0.5612 Remote Similarity NPC476160
0.561 Remote Similarity NPC50266
0.5603 Remote Similarity NPC150323
0.5603 Remote Similarity NPC130931
0.56 Remote Similarity NPC322040

  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 NPC301874 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
0.7882 Intermediate Similarity NPD9108 Approved
0.7528 Intermediate Similarity NPD462 Approved
0.7528 Intermediate Similarity NPD464 Approved
0.7528 Intermediate Similarity NPD463 Approved
0.7444 Intermediate Similarity NPD9188 Approved
0.7283 Intermediate Similarity NPD9352 Approved
0.7283 Intermediate Similarity NPD716 Approved
0.7204 Intermediate Similarity NPD9304 Approved
0.7128 Intermediate Similarity NPD9353 Approved
0.6957 Remote Similarity NPD1394 Approved
0.6882 Remote Similarity NPD665 Phase 2
0.6842 Remote Similarity NPD9270 Clinical (unspecified phase)
0.6837 Remote Similarity NPD2795 Clinical (unspecified phase)
0.6768 Remote Similarity NPD233 Clinical (unspecified phase)
0.67 Remote Similarity NPD993 Approved
0.67 Remote Similarity NPD990 Approved
0.6667 Remote Similarity NPD292 Approved
0.6667 Remote Similarity NPD294 Approved
0.6634 Remote Similarity NPD1824 Discontinued
0.6531 Remote Similarity NPD479 Approved
0.6517 Remote Similarity NPD9395 Approved
0.6506 Remote Similarity NPD9591 Approved
0.6506 Remote Similarity NPD9590 Approved
0.6506 Remote Similarity NPD9588 Approved
0.6506 Remote Similarity NPD9592 Approved
0.6506 Remote Similarity NPD9589 Approved
0.6506 Remote Similarity NPD9593 Approved
0.6506 Remote Similarity NPD80 Approved
0.6506 Remote Similarity NPD9594 Approved
0.6505 Remote Similarity NPD1107 Approved
0.6505 Remote Similarity NPD1108 Approved
0.6471 Remote Similarity NPD458 Approved
0.6471 Remote Similarity NPD445 Discontinued
0.6436 Remote Similarity NPD563 Approved
0.6436 Remote Similarity NPD564 Approved
0.6392 Remote Similarity NPD9070 Clinical (unspecified phase)
0.6381 Remote Similarity NPD2038 Approved
0.6381 Remote Similarity NPD2999 Approved
0.6381 Remote Similarity NPD2039 Approved
0.6381 Remote Similarity NPD526 Approved
0.6381 Remote Similarity NPD3001 Approved
0.6373 Remote Similarity NPD261 Approved
0.6364 Remote Similarity NPD190 Phase 1
0.6346 Remote Similarity NPD916 Discontinued
0.6346 Remote Similarity NPD1539 Approved
0.6337 Remote Similarity NPD1728 Clinical (unspecified phase)
0.6321 Remote Similarity NPD561 Approved
0.6321 Remote Similarity NPD560 Approved
0.6311 Remote Similarity NPD278 Approved
0.63 Remote Similarity NPD4734 Approved
0.63 Remote Similarity NPD4735 Approved
0.63 Remote Similarity NPD708 Approved
0.6286 Remote Similarity NPD909 Clinical (unspecified phase)
0.6275 Remote Similarity NPD156 Phase 3
0.6262 Remote Similarity NPD1311 Approved
0.6216 Remote Similarity NPD1306 Clinical (unspecified phase)
0.6214 Remote Similarity NPD3545 Approved
0.6214 Remote Similarity NPD3546 Approved
0.6207 Remote Similarity NPD9563 Approved
0.6207 Remote Similarity NPD295 Approved
0.6207 Remote Similarity NPD9397 Approved
0.6207 Remote Similarity NPD293 Approved
0.6207 Remote Similarity NPD296 Approved
0.6207 Remote Similarity NPD9393 Approved
0.6207 Remote Similarity NPD9564 Approved
0.6207 Remote Similarity NPD79 Approved
0.6154 Remote Similarity NPD5253 Approved
0.6154 Remote Similarity NPD6299 Approved
0.6154 Remote Similarity NPD4115 Approved
0.6154 Remote Similarity NPD1054 Approved
0.6154 Remote Similarity NPD1112 Phase 3
0.6154 Remote Similarity NPD1111 Phase 3
0.6154 Remote Similarity NPD2243 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4114 Approved
0.6154 Remote Similarity NPD6300 Approved
0.6147 Remote Similarity NPD202 Clinical (unspecified phase)
0.6139 Remote Similarity NPD1417 Approved
0.6139 Remote Similarity NPD1419 Approved
0.6139 Remote Similarity NPD9475 Clinical (unspecified phase)
0.6136 Remote Similarity NPD589 Approved
0.6136 Remote Similarity NPD590 Approved
0.6118 Remote Similarity NPD505 Clinical (unspecified phase)
0.6111 Remote Similarity NPD456 Approved
0.6095 Remote Similarity NPD1342 Approved
0.6095 Remote Similarity NPD477 Phase 1
0.6092 Remote Similarity NPD603 Approved
0.6091 Remote Similarity NPD1596 Approved
0.6091 Remote Similarity NPD1312 Approved
0.6091 Remote Similarity NPD2464 Approved
0.6091 Remote Similarity NPD1171 Approved
0.6091 Remote Similarity NPD2463 Approved
0.6091 Remote Similarity NPD5244 Approved
0.6091 Remote Similarity NPD5245 Approved
0.6091 Remote Similarity NPD2467 Approved
0.6091 Remote Similarity NPD5243 Approved
0.6078 Remote Similarity NPD2244 Clinical (unspecified phase)
0.6058 Remote Similarity NPD1064 Approved
0.6058 Remote Similarity NPD1065 Approved
0.6038 Remote Similarity NPD7633 Discontinued
0.6038 Remote Similarity NPD2520 Approved
0.6038 Remote Similarity NPD2522 Approved
0.6038 Remote Similarity NPD4116 Approved
0.6036 Remote Similarity NPD153 Clinical (unspecified phase)
0.6036 Remote Similarity NPD299 Phase 3
0.6 Remote Similarity NPD224 Phase 2
0.6 Remote Similarity NPD9507 Approved
0.6 Remote Similarity NPD2964 Clinical (unspecified phase)
0.5982 Remote Similarity NPD541 Approved
0.5982 Remote Similarity NPD922 Approved
0.5982 Remote Similarity NPD1216 Clinical (unspecified phase)
0.5978 Remote Similarity NPD785 Approved
0.5955 Remote Similarity NPD508 Approved
0.5955 Remote Similarity NPD507 Approved
0.5929 Remote Similarity NPD764 Phase 3
0.5929 Remote Similarity NPD492 Approved
0.5929 Remote Similarity NPD759 Approved
0.5926 Remote Similarity NPD2519 Approved
0.5926 Remote Similarity NPD3010 Approved
0.5926 Remote Similarity NPD3009 Approved
0.5926 Remote Similarity NPD3036 Approved
0.5926 Remote Similarity NPD2518 Approved
0.5926 Remote Similarity NPD3566 Approved
0.5926 Remote Similarity NPD3865 Approved
0.5926 Remote Similarity NPD3565 Approved
0.5926 Remote Similarity NPD2521 Approved
0.5914 Remote Similarity NPD9505 Clinical (unspecified phase)
0.5913 Remote Similarity NPD9528 Approved
0.5913 Remote Similarity NPD9527 Approved
0.5909 Remote Similarity NPD1813 Discontinued
0.5897 Remote Similarity NPD8128 Discontinued
0.5895 Remote Similarity NPD9184 Approved
0.5895 Remote Similarity NPD9186 Approved
0.5893 Remote Similarity NPD7481 Approved
0.5893 Remote Similarity NPD7480 Approved
0.5893 Remote Similarity NPD457 Approved
0.5889 Remote Similarity NPD5372 Approved
0.5889 Remote Similarity NPD5371 Approved
0.5877 Remote Similarity NPD2338 Clinical (unspecified phase)
0.5876 Remote Similarity NPD7160 Approved
0.587 Remote Similarity NPD263 Approved
0.587 Remote Similarity NPD830 Approved
0.587 Remote Similarity NPD262 Approved
0.587 Remote Similarity NPD831 Approved
0.5856 Remote Similarity NPD1720 Phase 2
0.5856 Remote Similarity NPD1723 Phase 2
0.5841 Remote Similarity NPD9700 Clinical (unspecified phase)
0.5841 Remote Similarity NPD9476 Approved
0.5833 Remote Similarity NPD9 Approved
0.5833 Remote Similarity NPD9376 Approved
0.5833 Remote Similarity NPD297 Approved
0.5833 Remote Similarity NPD9351 Phase 3
0.5833 Remote Similarity NPD9348 Approved
0.5833 Remote Similarity NPD9349 Approved
0.5833 Remote Similarity NPD9350 Approved
0.5826 Remote Similarity NPD1123 Approved
0.5826 Remote Similarity NPD1236 Phase 3
0.5826 Remote Similarity NPD1124 Approved
0.5826 Remote Similarity NPD9543 Approved
0.5826 Remote Similarity NPD1517 Clinical (unspecified phase)
0.5826 Remote Similarity NPD1079 Discontinued
0.5818 Remote Similarity NPD452 Phase 1
0.5818 Remote Similarity NPD2587 Approved
0.5818 Remote Similarity NPD2914 Approved
0.5818 Remote Similarity NPD2913 Approved
0.5818 Remote Similarity NPD5180 Approved
0.5818 Remote Similarity NPD453 Phase 1
0.5818 Remote Similarity NPD5181 Approved
0.5818 Remote Similarity NPD3387 Approved
0.5818 Remote Similarity NPD5179 Approved
0.5814 Remote Similarity NPD9728 Phase 1
0.5806 Remote Similarity NPD2539 Approved
0.5806 Remote Similarity NPD2538 Approved
0.5804 Remote Similarity NPD9720 Approved
0.5804 Remote Similarity NPD9719 Approved
0.5794 Remote Similarity NPD2678 Approved
0.5794 Remote Similarity NPD2679 Approved
0.5794 Remote Similarity NPD1721 Clinical (unspecified phase)
0.578 Remote Similarity NPD308 Approved
0.5766 Remote Similarity NPD5629 Discontinued
0.5766 Remote Similarity NPD5631 Phase 3
0.5766 Remote Similarity NPD4085 Approved
0.5758 Remote Similarity NPD735 Approved
0.5758 Remote Similarity NPD736 Approved
0.5752 Remote Similarity NPD9247 Phase 3
0.575 Remote Similarity NPD2036 Approved
0.5741 Remote Similarity NPD3548 Approved
0.5739 Remote Similarity NPD1525 Approved
0.5732 Remote Similarity NPD173 Clinical (unspecified phase)
0.5727 Remote Similarity NPD181 Approved
0.5726 Remote Similarity NPD964 Approved
0.5714 Remote Similarity NPD260 Discontinued
0.5714 Remote Similarity NPD2925 Approved
0.5714 Remote Similarity NPD2924 Approved
0.5714 Remote Similarity NPD1617 Discontinued
0.5714 Remote Similarity NPD525 Clinical (unspecified phase)
0.5702 Remote Similarity NPD8263 Discontinued
0.5702 Remote Similarity NPD726 Discontinued
0.5702 Remote Similarity NPD9392 Approved
0.5702 Remote Similarity NPD9396 Approved
0.57 Remote Similarity NPD5554 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