Structure

Physi-Chem Properties

Molecular Weight:  109.05
Volume:  115.654
LogP:  0.853
LogD:  0.696
LogS:  -0.307
# Rotatable Bonds:  1
TPSA:  35.25
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.544
Synthetic Accessibility Score:  1.855
Fsp3:  0.0
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:  -4.573
MDCK Permeability:  0.00016170441813301295
Pgp-inhibitor:  0.0
Pgp-substrate:  0.548
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.938
Plasma Protein Binding (PPB):  63.462215423583984%
Volume Distribution (VD):  2.245
Pgp-substrate:  52.282135009765625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.754
CYP1A2-substrate:  0.189
CYP2C19-inhibitor:  0.05
CYP2C19-substrate:  0.1
CYP2C9-inhibitor:  0.037
CYP2C9-substrate:  0.592
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.509
CYP3A4-inhibitor:  0.01
CYP3A4-substrate:  0.163

ADMET: Excretion

Clearance (CL):  9.158
Half-life (T1/2):  0.607

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.649
Drug-inuced Liver Injury (DILI):  0.164
AMES Toxicity:  0.918
Rat Oral Acute Toxicity:  0.853
Maximum Recommended Daily Dose:  0.526
Skin Sensitization:  0.433
Carcinogencity:  0.776
Eye Corrosion:  0.873
Eye Irritation:  0.99
Respiratory Toxicity:  0.923

Download Data

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

  Natural Product: NPC215445

Natural Product ID:  NPC215445
Common Name*:   O-Phenylhydroxylamine
IUPAC Name:   O-phenylhydroxylamine
Synonyms:   Phenyl-O-Hydroxylamine
Standard InCHIKey:  UOKZUTXLHRTLFH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H7NO/c7-8-6-4-2-1-3-5-6/h1-5H,7H2
SMILES:  NOc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1213940
PubChem CID:   2794249
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0004742] Phenoxy compounds

*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
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. tuber n.a. PMID[12913245]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[1293938]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[16181762]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22223386]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota Lateral roots n.a. n.a. PMID[22607495]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22628040]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22907155]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[23225552]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[23707213]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[23707213]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[24793215]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[27761113]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[30892884]
NPO29861 Aconitum carmichaeli Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29861 Aconitum carmichaeli Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]

☑ 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[466532]

☑ 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 NPC215445 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
0.8873 High Similarity NPC100980
0.84 Intermediate Similarity NPC65517
0.84 Intermediate Similarity NPC322285
0.8182 Intermediate Similarity NPC124576
0.8077 Intermediate Similarity NPC204932
0.7975 Intermediate Similarity NPC270094
0.7848 Intermediate Similarity NPC4154
0.7683 Intermediate Similarity NPC265146
0.7683 Intermediate Similarity NPC125306
0.7683 Intermediate Similarity NPC38459
0.7683 Intermediate Similarity NPC124436
0.7683 Intermediate Similarity NPC319826
0.7683 Intermediate Similarity NPC23837
0.7683 Intermediate Similarity NPC33756
0.759 Intermediate Similarity NPC150837
0.759 Intermediate Similarity NPC286904
0.759 Intermediate Similarity NPC175313
0.759 Intermediate Similarity NPC248817
0.75 Intermediate Similarity NPC197783
0.75 Intermediate Similarity NPC155393
0.7412 Intermediate Similarity NPC407
0.7412 Intermediate Similarity NPC280254
0.7412 Intermediate Similarity NPC307235
0.7412 Intermediate Similarity NPC206876
0.7412 Intermediate Similarity NPC184169
0.7412 Intermediate Similarity NPC23167
0.7356 Intermediate Similarity NPC151764
0.7326 Intermediate Similarity NPC27974
0.7326 Intermediate Similarity NPC157213
0.7326 Intermediate Similarity NPC104216
0.7326 Intermediate Similarity NPC25493
0.7326 Intermediate Similarity NPC113460
0.7294 Intermediate Similarity NPC252149
0.7241 Intermediate Similarity NPC258219
0.7241 Intermediate Similarity NPC242240
0.7241 Intermediate Similarity NPC177844
0.7241 Intermediate Similarity NPC98772
0.7241 Intermediate Similarity NPC99886
0.7241 Intermediate Similarity NPC123273
0.7241 Intermediate Similarity NPC302546
0.7241 Intermediate Similarity NPC8002
0.7241 Intermediate Similarity NPC177420
0.7241 Intermediate Similarity NPC280347
0.7241 Intermediate Similarity NPC259134
0.7241 Intermediate Similarity NPC318325
0.7159 Intermediate Similarity NPC312304
0.7159 Intermediate Similarity NPC300478
0.7159 Intermediate Similarity NPC55561
0.7159 Intermediate Similarity NPC47950
0.7159 Intermediate Similarity NPC71853
0.7159 Intermediate Similarity NPC288923
0.7159 Intermediate Similarity NPC277758
0.7159 Intermediate Similarity NPC318429
0.7159 Intermediate Similarity NPC192
0.7159 Intermediate Similarity NPC300017
0.7126 Intermediate Similarity NPC19680
0.7126 Intermediate Similarity NPC47422
0.7079 Intermediate Similarity NPC155908
0.7079 Intermediate Similarity NPC174048
0.7079 Intermediate Similarity NPC321956
0.7079 Intermediate Similarity NPC270547
0.7079 Intermediate Similarity NPC322888
0.7079 Intermediate Similarity NPC231150
0.7079 Intermediate Similarity NPC306074
0.7079 Intermediate Similarity NPC304541
0.7079 Intermediate Similarity NPC204210
0.7079 Intermediate Similarity NPC45040
0.7065 Intermediate Similarity NPC107619
0.7065 Intermediate Similarity NPC315921
0.7 Intermediate Similarity NPC181709
0.7 Intermediate Similarity NPC325292
0.7 Intermediate Similarity NPC55903
0.7 Intermediate Similarity NPC210497
0.7 Intermediate Similarity NPC306884
0.7 Intermediate Similarity NPC138117
0.7 Intermediate Similarity NPC3358
0.7 Intermediate Similarity NPC147284
0.7 Intermediate Similarity NPC162314
0.7 Intermediate Similarity NPC271440
0.7 Intermediate Similarity NPC94139
0.7 Intermediate Similarity NPC29373
0.6989 Remote Similarity NPC125732
0.6923 Remote Similarity NPC152415
0.6923 Remote Similarity NPC81010
0.6923 Remote Similarity NPC128062
0.6923 Remote Similarity NPC151715
0.6923 Remote Similarity NPC316301
0.6923 Remote Similarity NPC16649
0.6923 Remote Similarity NPC27323
0.6923 Remote Similarity NPC32977
0.6923 Remote Similarity NPC471581
0.6923 Remote Similarity NPC245187
0.6923 Remote Similarity NPC114325
0.6923 Remote Similarity NPC76938
0.6915 Remote Similarity NPC70201
0.6915 Remote Similarity NPC29601
0.6882 Remote Similarity NPC313918
0.6854 Remote Similarity NPC70436
0.6848 Remote Similarity NPC26244
0.6848 Remote Similarity NPC32714
0.6848 Remote Similarity NPC8392
0.6848 Remote Similarity NPC313650
0.6848 Remote Similarity NPC286006
0.6848 Remote Similarity NPC257182
0.6848 Remote Similarity NPC246679
0.6848 Remote Similarity NPC107522
0.6848 Remote Similarity NPC274678
0.6813 Remote Similarity NPC295295
0.6774 Remote Similarity NPC132271
0.6774 Remote Similarity NPC202986
0.6774 Remote Similarity NPC82664
0.6774 Remote Similarity NPC216520
0.6774 Remote Similarity NPC283711
0.6774 Remote Similarity NPC292730
0.6774 Remote Similarity NPC259512
0.6774 Remote Similarity NPC473388
0.6774 Remote Similarity NPC312132
0.6771 Remote Similarity NPC68055
0.6771 Remote Similarity NPC311660
0.6739 Remote Similarity NPC289769
0.6737 Remote Similarity NPC289381
0.6737 Remote Similarity NPC155847
0.6707 Remote Similarity NPC66655
0.6702 Remote Similarity NPC175298
0.6702 Remote Similarity NPC225464
0.6702 Remote Similarity NPC475078
0.6702 Remote Similarity NPC6597
0.6702 Remote Similarity NPC79241
0.6702 Remote Similarity NPC201967
0.6702 Remote Similarity NPC291789
0.6702 Remote Similarity NPC95755
0.6702 Remote Similarity NPC156313
0.6702 Remote Similarity NPC140619
0.6702 Remote Similarity NPC32674
0.6702 Remote Similarity NPC470161
0.6702 Remote Similarity NPC260000
0.6702 Remote Similarity NPC109955
0.6702 Remote Similarity NPC77492
0.6702 Remote Similarity NPC474073
0.6702 Remote Similarity NPC88420
0.6702 Remote Similarity NPC152097
0.6701 Remote Similarity NPC256838
0.6667 Remote Similarity NPC328178
0.6667 Remote Similarity NPC222146
0.6633 Remote Similarity NPC42383
0.6632 Remote Similarity NPC307039
0.6632 Remote Similarity NPC216468
0.6632 Remote Similarity NPC252821
0.6632 Remote Similarity NPC78119
0.6632 Remote Similarity NPC280869
0.6632 Remote Similarity NPC299762
0.6632 Remote Similarity NPC275104
0.6632 Remote Similarity NPC260775
0.6632 Remote Similarity NPC92730
0.6632 Remote Similarity NPC314803
0.6632 Remote Similarity NPC128723
0.6632 Remote Similarity NPC245561
0.6632 Remote Similarity NPC33675
0.6632 Remote Similarity NPC132725
0.6632 Remote Similarity NPC132078
0.6632 Remote Similarity NPC122005
0.6632 Remote Similarity NPC171843
0.6632 Remote Similarity NPC51333
0.6632 Remote Similarity NPC100870
0.6632 Remote Similarity NPC471576
0.6632 Remote Similarity NPC130193
0.6632 Remote Similarity NPC131587
0.6632 Remote Similarity NPC80027
0.6628 Remote Similarity NPC146703
0.6598 Remote Similarity NPC178902
0.6588 Remote Similarity NPC133050
0.6588 Remote Similarity NPC117180
0.6562 Remote Similarity NPC174911
0.6562 Remote Similarity NPC72729
0.6562 Remote Similarity NPC161571
0.6562 Remote Similarity NPC130103
0.6562 Remote Similarity NPC52472
0.6562 Remote Similarity NPC129373
0.6562 Remote Similarity NPC166761
0.6562 Remote Similarity NPC10588
0.6562 Remote Similarity NPC213730
0.6562 Remote Similarity NPC48730
0.6562 Remote Similarity NPC130756
0.6562 Remote Similarity NPC294741
0.6562 Remote Similarity NPC275053
0.6562 Remote Similarity NPC12931
0.6562 Remote Similarity NPC70677
0.6562 Remote Similarity NPC223393
0.6562 Remote Similarity NPC13755
0.6562 Remote Similarity NPC248573
0.6562 Remote Similarity NPC107101
0.6562 Remote Similarity NPC225506
0.6562 Remote Similarity NPC253746
0.6562 Remote Similarity NPC248396
0.6515 Remote Similarity NPC11150
0.6512 Remote Similarity NPC103326
0.6512 Remote Similarity NPC329319
0.6512 Remote Similarity NPC87299
0.6512 Remote Similarity NPC99394
0.65 Remote Similarity NPC44836

  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 NPC215445 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
0.8873 High Similarity NPD9087 Approved
0.84 Intermediate Similarity NPD9088 Approved
0.7975 Intermediate Similarity NPD9089 Approved
0.7848 Intermediate Similarity NPD9093 Approved
0.7683 Intermediate Similarity NPD111 Approved
0.7683 Intermediate Similarity NPD9073 Approved
0.7412 Intermediate Similarity NPD9094 Approved
0.7326 Intermediate Similarity NPD9295 Approved
0.7159 Intermediate Similarity NPD9365 Approved
0.7065 Intermediate Similarity NPD9273 Approved
0.6923 Remote Similarity NPD9296 Approved
0.6923 Remote Similarity NPD2933 Approved
0.6923 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2934 Approved
0.6848 Remote Similarity NPD2860 Approved
0.6848 Remote Similarity NPD844 Approved
0.6848 Remote Similarity NPD2859 Approved
0.6813 Remote Similarity NPD845 Approved
0.6774 Remote Similarity NPD288 Approved
0.6707 Remote Similarity NPD9294 Approved
0.6702 Remote Similarity NPD68 Approved
0.6702 Remote Similarity NPD9096 Approved
0.6702 Remote Similarity NPD9095 Approved
0.6702 Remote Similarity NPD9097 Approved
0.6701 Remote Similarity NPD9610 Approved
0.6701 Remote Similarity NPD9608 Approved
0.6632 Remote Similarity NPD3020 Approved
0.6562 Remote Similarity NPD3028 Approved
0.6562 Remote Similarity NPD289 Clinical (unspecified phase)
0.6562 Remote Similarity NPD1242 Phase 1
0.65 Remote Similarity NPD9624 Approved
0.6495 Remote Similarity NPD291 Approved
0.6495 Remote Similarity NPD846 Approved
0.6495 Remote Similarity NPD940 Approved
0.6489 Remote Similarity NPD1809 Phase 2
0.6429 Remote Similarity NPD9261 Approved
0.64 Remote Similarity NPD1444 Approved
0.64 Remote Similarity NPD1445 Approved
0.6395 Remote Similarity NPD9250 Approved
0.6373 Remote Similarity NPD556 Approved
0.6373 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6364 Remote Similarity NPD9501 Approved
0.6337 Remote Similarity NPD5374 Approved
0.6337 Remote Similarity NPD9507 Approved
0.6337 Remote Similarity NPD5373 Approved
0.6311 Remote Similarity NPD9280 Clinical (unspecified phase)
0.63 Remote Similarity NPD9697 Approved
0.6263 Remote Similarity NPD9500 Approved
0.6238 Remote Similarity NPD3134 Approved
0.6238 Remote Similarity NPD968 Approved
0.6214 Remote Similarity NPD1792 Phase 2
0.619 Remote Similarity NPD821 Approved
0.619 Remote Similarity NPD9377 Approved
0.619 Remote Similarity NPD9379 Approved
0.6176 Remote Similarity NPD290 Approved
0.6176 Remote Similarity NPD9552 Approved
0.6176 Remote Similarity NPD1358 Approved
0.6176 Remote Similarity NPD9263 Approved
0.6176 Remote Similarity NPD9264 Approved
0.6176 Remote Similarity NPD9267 Approved
0.6176 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6154 Remote Similarity NPD2671 Approved
0.6154 Remote Similarity NPD2673 Approved
0.6154 Remote Similarity NPD9376 Approved
0.6117 Remote Similarity NPD74 Approved
0.6117 Remote Similarity NPD9266 Approved
0.6117 Remote Similarity NPD2684 Approved
0.6095 Remote Similarity NPD308 Approved
0.6075 Remote Similarity NPD595 Approved
0.6075 Remote Similarity NPD9618 Approved
0.6075 Remote Similarity NPD593 Approved
0.6075 Remote Similarity NPD286 Approved
0.6075 Remote Similarity NPD9614 Approved
0.6058 Remote Similarity NPD3021 Approved
0.6058 Remote Similarity NPD5451 Approved
0.6058 Remote Similarity NPD3022 Approved
0.6044 Remote Similarity NPD9257 Approved
0.6044 Remote Similarity NPD9259 Approved
0.6038 Remote Similarity NPD1105 Clinical (unspecified phase)
0.6019 Remote Similarity NPD2342 Discontinued
0.6019 Remote Similarity NPD191 Approved
0.6019 Remote Similarity NPD256 Approved
0.6019 Remote Similarity NPD255 Approved
0.6 Remote Similarity NPD159 Clinical (unspecified phase)
0.5981 Remote Similarity NPD2228 Approved
0.5981 Remote Similarity NPD594 Approved
0.5981 Remote Similarity NPD592 Approved
0.5981 Remote Similarity NPD2234 Approved
0.5981 Remote Similarity NPD2229 Approved
0.5963 Remote Similarity NPD9568 Approved
0.5943 Remote Similarity NPD228 Approved
0.5926 Remote Similarity NPD1793 Approved
0.5926 Remote Similarity NPD1791 Approved
0.5926 Remote Similarity NPD475 Phase 2
0.5915 Remote Similarity NPD9072 Clinical (unspecified phase)
0.5909 Remote Similarity NPD317 Approved
0.5909 Remote Similarity NPD16 Approved
0.5909 Remote Similarity NPD1102 Approved
0.5909 Remote Similarity NPD9615 Approved
0.5909 Remote Similarity NPD1103 Approved
0.5909 Remote Similarity NPD856 Approved
0.5909 Remote Similarity NPD9613 Approved
0.5909 Remote Similarity NPD9616 Approved
0.5909 Remote Similarity NPD318 Approved
0.5905 Remote Similarity NPD4750 Phase 3
0.5888 Remote Similarity NPD769 Approved
0.5888 Remote Similarity NPD5535 Approved
0.5888 Remote Similarity NPD7843 Approved
0.5882 Remote Similarity NPD9244 Approved
0.5872 Remote Similarity NPD9342 Approved
0.5872 Remote Similarity NPD2557 Approved
0.5872 Remote Similarity NPD709 Approved
0.5859 Remote Similarity NPD9609 Approved
0.5859 Remote Similarity NPD9611 Approved
0.5859 Remote Similarity NPD9612 Approved
0.5856 Remote Similarity NPD316 Approved
0.5851 Remote Similarity NPD9249 Phase 1
0.5833 Remote Similarity NPD498 Approved
0.5833 Remote Similarity NPD495 Approved
0.5833 Remote Similarity NPD5283 Phase 1
0.5833 Remote Similarity NPD496 Approved
0.5833 Remote Similarity NPD1241 Discontinued
0.5818 Remote Similarity NPD3596 Phase 2
0.5804 Remote Similarity NPD3049 Approved
0.5804 Remote Similarity NPD1798 Approved
0.5804 Remote Similarity NPD1797 Approved
0.5795 Remote Similarity NPD9490 Approved
0.5794 Remote Similarity NPD1139 Approved
0.5794 Remote Similarity NPD1137 Approved
0.5789 Remote Similarity NPD9258 Approved
0.5789 Remote Similarity NPD9256 Approved
0.578 Remote Similarity NPD9299 Approved
0.578 Remote Similarity NPD1476 Clinical (unspecified phase)
0.578 Remote Similarity NPD497 Approved
0.578 Remote Similarity NPD9281 Approved
0.5766 Remote Similarity NPD254 Approved
0.5766 Remote Similarity NPD313 Approved
0.5766 Remote Similarity NPD1408 Clinical (unspecified phase)
0.5766 Remote Similarity NPD1758 Phase 1
0.5755 Remote Similarity NPD910 Approved
0.5752 Remote Similarity NPD9384 Approved
0.5752 Remote Similarity NPD2423 Clinical (unspecified phase)
0.5752 Remote Similarity NPD2556 Approved
0.5752 Remote Similarity NPD9381 Approved
0.5752 Remote Similarity NPD2554 Approved
0.5741 Remote Similarity NPD1138 Approved
0.5741 Remote Similarity NPD7635 Approved
0.5727 Remote Similarity NPD7157 Approved
0.5727 Remote Similarity NPD6671 Approved
0.5727 Remote Similarity NPD6387 Discontinued
0.5714 Remote Similarity NPD1182 Approved
0.5714 Remote Similarity NPD1759 Phase 1
0.5714 Remote Similarity NPD7534 Approved
0.5714 Remote Similarity NPD6581 Approved
0.5714 Remote Similarity NPD7533 Approved
0.5714 Remote Similarity NPD5304 Approved
0.5714 Remote Similarity NPD2486 Discontinued
0.5714 Remote Similarity NPD6580 Approved
0.5714 Remote Similarity NPD2226 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5303 Approved
0.5702 Remote Similarity NPD1980 Approved
0.5702 Remote Similarity NPD3421 Phase 3
0.5702 Remote Similarity NPD155 Clinical (unspecified phase)
0.5702 Remote Similarity NPD1983 Approved
0.5702 Remote Similarity NPD1981 Approved
0.5676 Remote Similarity NPD7325 Clinical (unspecified phase)
0.5676 Remote Similarity NPD405 Clinical (unspecified phase)
0.5676 Remote Similarity NPD9493 Approved
0.567 Remote Similarity NPD9251 Approved
0.5664 Remote Similarity NPD3444 Approved
0.5664 Remote Similarity NPD4093 Discontinued
0.5664 Remote Similarity NPD2595 Approved
0.5664 Remote Similarity NPD3445 Approved
0.5664 Remote Similarity NPD2594 Approved
0.5664 Remote Similarity NPD6382 Discontinued
0.5664 Remote Similarity NPD3443 Approved
0.5664 Remote Similarity NPD6830 Clinical (unspecified phase)
0.5648 Remote Similarity NPD6124 Clinical (unspecified phase)
0.5638 Remote Similarity NPD9538 Approved
0.5625 Remote Similarity NPD5536 Phase 2
0.5614 Remote Similarity NPD2668 Approved
0.5614 Remote Similarity NPD2667 Approved
0.5614 Remote Similarity NPD2286 Discontinued
0.5614 Remote Similarity NPD1751 Approved
0.5614 Remote Similarity NPD5238 Clinical (unspecified phase)
0.5614 Remote Similarity NPD1010 Approved
0.5612 Remote Similarity NPD1202 Approved
0.5603 Remote Similarity NPD2562 Approved
0.5603 Remote Similarity NPD2231 Phase 2
0.5603 Remote Similarity NPD2235 Phase 2
0.5603 Remote Similarity NPD2561 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