Structure

Physi-Chem Properties

Molecular Weight:  540.24
Volume:  542.674
LogP:  2.071
LogD:  1.532
LogS:  -4.751
# Rotatable Bonds:  8
TPSA:  118.34
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.311
Synthetic Accessibility Score:  5.314
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.213
MDCK Permeability:  6.081809624447487e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.895
Human Intestinal Absorption (HIA):  0.083
20% Bioavailability (F20%):  0.977
30% Bioavailability (F30%):  0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.584
Plasma Protein Binding (PPB):  85.99817657470703%
Volume Distribution (VD):  2.097
Pgp-substrate:  11.232453346252441%

ADMET: Metabolism

CYP1A2-inhibitor:  0.031
CYP1A2-substrate:  0.133
CYP2C19-inhibitor:  0.31
CYP2C19-substrate:  0.375
CYP2C9-inhibitor:  0.872
CYP2C9-substrate:  0.011
CYP2D6-inhibitor:  0.027
CYP2D6-substrate:  0.044
CYP3A4-inhibitor:  0.935
CYP3A4-substrate:  0.764

ADMET: Excretion

Clearance (CL):  6.753
Half-life (T1/2):  0.808

ADMET: Toxicity

hERG Blockers:  0.701
Human Hepatotoxicity (H-HT):  0.835
Drug-inuced Liver Injury (DILI):  0.706
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.955
Maximum Recommended Daily Dose:  0.967
Skin Sensitization:  0.195
Carcinogencity:  0.126
Eye Corrosion:  0.005
Eye Irritation:  0.024
Respiratory Toxicity:  0.957

Download Data

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

  Natural Product: NPC116717

Natural Product ID:  NPC116717
Common Name*:   Nimbin
IUPAC Name:   n.a.
Synonyms:   Nimbin
Standard InCHIKey:  NHOIBRJOQAYBJT-IMGVWCFESA-N
Standard InCHI:  InChI=1S/C30H36O9/c1-15-18(17-9-11-37-14-17)12-19-23(15)30(5)20(13-22(33)35-6)29(4)21(32)8-10-28(3,27(34)36-7)25(29)24(26(30)39-19)38-16(2)31/h8-11,14,18-20,24-26H,12-13H2,1-7H3/t18-,19-,20-,24-,25+,26-,28-,29+,30-/m1/s1
SMILES:  CC1=C2[C@@H](C[C@H]1c1ccoc1)O[C@@H]1[C@@H]([C@H]3[C@@](C)(C=CC(=O)[C@]3(C)[C@@H](CC(=O)OC)[C@]21C)C(=O)OC)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1774397
PubChem CID:   108058
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids
          • [CHEMONTID:0002380] Limonoids

*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
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[12193038]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota bark n.a. n.a. PMID[1479382]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. bark n.a. PMID[1479382]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[1593280]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[1791471]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[18816111]
NPO5587 Chisocheton ceramicus Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[19081726]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota fruits n.a. n.a. PMID[20669933]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota Seeds n.a. n.a. PMID[21381696]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. seed n.a. PMID[21381696]
NPO5587 Chisocheton ceramicus Species Meliaceae Eukaryota n.a. bark n.a. PMID[21428417]
NPO5587 Chisocheton ceramicus Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[21428417]
NPO5587 Chisocheton ceramicus Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[23395661]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[2607354]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[2614419]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[2614426]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[26339153]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota Leaves n.a. n.a. PMID[28493718]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. bark n.a. PMID[9134742]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. fruit n.a. PMID[9134742]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. leaf n.a. PMID[9134742]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9322367]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9917277]
NPO3846 Melia indica Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8783 Stachys palustris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3846 Melia indica Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26224 Walsura piscidia Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8783 Stachys palustris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8783 Stachys palustris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2423 Melochia corchorifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3846 Melia indica Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO774 Cleome pungens Species Cleomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26224 Walsura piscidia Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1058 Pestalotiopsis heterocornis Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1594 [enterobacter] aerogenes Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8249 Marcetella moquiniana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9217 Daphniphyllum angustifolium Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2006 Centaurea sinaica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15379 Phalaenopsis schilleriana Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5587 Chisocheton ceramicus Species Meliaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 20000.0 nM PMID[518240]
NPT134 Cell Line SK-BR-3 Homo sapiens IC50 > 20000.0 nM PMID[518240]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 15900.0 nM PMID[518240]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 20000.0 nM PMID[518240]
NPT847 Organism Reticulitermes speratus Reticulitermes speratus Survival = 80.5 % PMID[518241]
NPT847 Organism Reticulitermes speratus Reticulitermes speratus Survival = 83.0 % PMID[518241]
NPT847 Organism Reticulitermes speratus Reticulitermes speratus Survival = 84.5 % PMID[518241]
NPT847 Organism Reticulitermes speratus Reticulitermes speratus Survival = 84.0 % PMID[518241]
NPT1175 Organism Spodoptera litura Spodoptera litura AFI = 33.7 % PMID[518242]

☑ 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 NPC116717 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
0.9724 High Similarity NPC291150
0.9662 High Similarity NPC197137
0.9655 High Similarity NPC5180
0.9452 High Similarity NPC471001
0.94 High Similarity NPC470118
0.931 High Similarity NPC34056
0.9272 High Similarity NPC469847
0.9262 High Similarity NPC29695
0.9262 High Similarity NPC308205
0.9262 High Similarity NPC322546
0.9262 High Similarity NPC182427
0.9247 High Similarity NPC470999
0.9139 High Similarity NPC141538
0.9139 High Similarity NPC92979
0.9139 High Similarity NPC296807
0.9139 High Similarity NPC155939
0.9133 High Similarity NPC471002
0.9085 High Similarity NPC475226
0.9067 High Similarity NPC471000
0.9032 High Similarity NPC471168
0.902 High Similarity NPC470119
0.902 High Similarity NPC214495
0.902 High Similarity NPC475066
0.8986 High Similarity NPC471292
0.898 High Similarity NPC238843
0.898 High Similarity NPC199044
0.8961 High Similarity NPC472671
0.894 High Similarity NPC18135
0.8931 High Similarity NPC285227
0.8903 High Similarity NPC191828
0.8889 High Similarity NPC471175
0.8882 High Similarity NPC470996
0.8874 High Similarity NPC156189
0.8874 High Similarity NPC196846
0.8874 High Similarity NPC159927
0.8874 High Similarity NPC469335
0.8846 High Similarity NPC470792
0.8846 High Similarity NPC471166
0.8846 High Similarity NPC471003
0.8846 High Similarity NPC471167
0.8836 High Similarity NPC56197
0.8831 High Similarity NPC471169
0.8831 High Similarity NPC175964
0.8816 High Similarity NPC272590
0.8808 High Similarity NPC234494
0.88 High Similarity NPC471174
0.8784 High Similarity NPC80635
0.8784 High Similarity NPC223415
0.8774 High Similarity NPC167142
0.8774 High Similarity NPC472283
0.8766 High Similarity NPC264943
0.8758 High Similarity NPC469848
0.8758 High Similarity NPC33938
0.875 High Similarity NPC470997
0.8734 High Similarity NPC126984
0.8734 High Similarity NPC27541
0.8734 High Similarity NPC61967
0.8734 High Similarity NPC62692
0.8726 High Similarity NPC472668
0.8725 High Similarity NPC251865
0.871 High Similarity NPC204663
0.8701 High Similarity NPC34421
0.8701 High Similarity NPC237259
0.8701 High Similarity NPC98206
0.8684 High Similarity NPC472654
0.8684 High Similarity NPC470790
0.8684 High Similarity NPC470791
0.8679 High Similarity NPC472670
0.8679 High Similarity NPC307781
0.8675 High Similarity NPC216755
0.8675 High Similarity NPC255414
0.8675 High Similarity NPC302987
0.8675 High Similarity NPC221809
0.8675 High Similarity NPC71821
0.8671 High Similarity NPC292389
0.8671 High Similarity NPC472669
0.8671 High Similarity NPC469338
0.8658 High Similarity NPC470741
0.8654 High Similarity NPC195131
0.8654 High Similarity NPC472777
0.8654 High Similarity NPC472776
0.8654 High Similarity NPC472778
0.8645 High Similarity NPC469336
0.8645 High Similarity NPC469850
0.8636 High Similarity NPC472672
0.8636 High Similarity NPC246164
0.8636 High Similarity NPC476201
0.8636 High Similarity NPC268905
0.8627 High Similarity NPC196864
0.8627 High Similarity NPC477404
0.8625 High Similarity NPC472764
0.8625 High Similarity NPC476224
0.8618 High Similarity NPC471007
0.8616 High Similarity NPC469849
0.8616 High Similarity NPC276551
0.8616 High Similarity NPC470940
0.8608 High Similarity NPC5741
0.8608 High Similarity NPC197596
0.8608 High Similarity NPC472771
0.8608 High Similarity NPC69028
0.8599 High Similarity NPC474932
0.8599 High Similarity NPC477403
0.8598 High Similarity NPC478177
0.8591 High Similarity NPC121158
0.8581 High Similarity NPC253201
0.8581 High Similarity NPC302054
0.8581 High Similarity NPC178932
0.858 High Similarity NPC475641
0.858 High Similarity NPC475237
0.8571 High Similarity NPC472765
0.8571 High Similarity NPC327922
0.8571 High Similarity NPC472766
0.8562 High Similarity NPC125182
0.8562 High Similarity NPC69647
0.8562 High Similarity NPC470875
0.8562 High Similarity NPC195325
0.8553 High Similarity NPC224394
0.8553 High Similarity NPC165218
0.8553 High Similarity NPC476197
0.8553 High Similarity NPC285567
0.8553 High Similarity NPC472773
0.8553 High Similarity NPC663
0.8544 High Similarity NPC305016
0.8544 High Similarity NPC477402
0.8543 High Similarity NPC185456
0.8535 High Similarity NPC286722
0.8526 High Similarity NPC44675
0.8526 High Similarity NPC214541
0.8526 High Similarity NPC476262
0.8523 High Similarity NPC20500
0.8519 High Similarity NPC118086
0.8516 High Similarity NPC75906
0.8516 High Similarity NPC84063
0.8514 High Similarity NPC90953
0.8509 High Similarity NPC476861
0.8509 High Similarity NPC476850
0.8509 High Similarity NPC478179
0.8509 High Similarity NPC173516
0.85 High Similarity NPC123088
0.8491 Intermediate Similarity NPC472767
0.8491 Intermediate Similarity NPC68848
0.8491 Intermediate Similarity NPC470939
0.8491 Intermediate Similarity NPC6326
0.8491 Intermediate Similarity NPC329938
0.8481 Intermediate Similarity NPC84349
0.8481 Intermediate Similarity NPC473473
0.8481 Intermediate Similarity NPC237155
0.8481 Intermediate Similarity NPC307383
0.8481 Intermediate Similarity NPC475295
0.8476 Intermediate Similarity NPC236004
0.8476 Intermediate Similarity NPC94763
0.8472 Intermediate Similarity NPC298190
0.8471 Intermediate Similarity NPC209364
0.8471 Intermediate Similarity NPC469485
0.8471 Intermediate Similarity NPC60973
0.8457 Intermediate Similarity NPC471397
0.8457 Intermediate Similarity NPC472673
0.8452 Intermediate Similarity NPC247563
0.8452 Intermediate Similarity NPC242068
0.8447 Intermediate Similarity NPC478178
0.8447 Intermediate Similarity NPC472141
0.8442 Intermediate Similarity NPC470998
0.8442 Intermediate Similarity NPC329180
0.8438 Intermediate Similarity NPC283209
0.8438 Intermediate Similarity NPC419
0.8438 Intermediate Similarity NPC469846
0.8438 Intermediate Similarity NPC14499
0.8438 Intermediate Similarity NPC476035
0.8438 Intermediate Similarity NPC477405
0.8438 Intermediate Similarity NPC475039
0.8431 Intermediate Similarity NPC470941
0.8428 Intermediate Similarity NPC287559
0.8428 Intermediate Similarity NPC25255
0.8428 Intermediate Similarity NPC470789
0.8418 Intermediate Similarity NPC173544
0.8418 Intermediate Similarity NPC299038
0.8418 Intermediate Similarity NPC36655
0.8418 Intermediate Similarity NPC472772
0.8418 Intermediate Similarity NPC261597
0.8418 Intermediate Similarity NPC88007
0.8418 Intermediate Similarity NPC195954
0.8408 Intermediate Similarity NPC25351
0.8397 Intermediate Similarity NPC469503
0.8397 Intermediate Similarity NPC294511
0.8397 Intermediate Similarity NPC121615
0.8395 Intermediate Similarity NPC472775
0.8395 Intermediate Similarity NPC472774
0.8395 Intermediate Similarity NPC473766
0.8395 Intermediate Similarity NPC473753
0.8387 Intermediate Similarity NPC46551
0.8387 Intermediate Similarity NPC476122
0.8385 Intermediate Similarity NPC476856
0.8385 Intermediate Similarity NPC476857
0.8385 Intermediate Similarity NPC476858
0.8378 Intermediate Similarity NPC310043
0.8378 Intermediate Similarity NPC470742
0.8375 Intermediate Similarity NPC82851
0.8375 Intermediate Similarity NPC193798
0.8366 Intermediate Similarity NPC262198
0.8365 Intermediate Similarity NPC475967

  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 NPC116717 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
0.8086 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD5760 Phase 2
0.8063 Intermediate Similarity NPD5761 Phase 2
0.7861 Intermediate Similarity NPD8434 Phase 2
0.7778 Intermediate Similarity NPD6765 Approved
0.7778 Intermediate Similarity NPD6764 Approved
0.76 Intermediate Similarity NPD6784 Approved
0.76 Intermediate Similarity NPD6785 Approved
0.7312 Intermediate Similarity NPD4628 Phase 3
0.7152 Intermediate Similarity NPD920 Approved
0.7125 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1471 Phase 3
0.7052 Intermediate Similarity NPD1247 Approved
0.7052 Intermediate Similarity NPD8127 Discontinued
0.7045 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD919 Approved
0.703 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.6994 Remote Similarity NPD5494 Approved
0.6988 Remote Similarity NPD6273 Approved
0.6964 Remote Similarity NPD3226 Approved
0.6923 Remote Similarity NPD6599 Discontinued
0.6923 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6909 Remote Similarity NPD643 Clinical (unspecified phase)
0.6901 Remote Similarity NPD7819 Suspended
0.6802 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6796 Remote Similarity NPD6559 Discontinued
0.6792 Remote Similarity NPD8032 Phase 2
0.6782 Remote Similarity NPD7075 Discontinued
0.6765 Remote Similarity NPD7458 Discontinued
0.6754 Remote Similarity NPD4107 Approved
0.675 Remote Similarity NPD8404 Phase 2
0.6746 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6727 Remote Similarity NPD1243 Approved
0.6724 Remote Similarity NPD4966 Approved
0.6724 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6724 Remote Similarity NPD4965 Approved
0.6724 Remote Similarity NPD4967 Phase 2
0.6722 Remote Similarity NPD5844 Phase 1
0.6707 Remote Similarity NPD6002 Phase 3
0.6707 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6004 Phase 3
0.6707 Remote Similarity NPD7236 Approved
0.6707 Remote Similarity NPD6005 Phase 3
0.6707 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6704 Remote Similarity NPD7473 Discontinued
0.6687 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6687 Remote Similarity NPD3748 Approved
0.6687 Remote Similarity NPD2799 Discontinued
0.6686 Remote Similarity NPD7411 Suspended
0.6685 Remote Similarity NPD3926 Phase 2
0.6667 Remote Similarity NPD3817 Phase 2
0.6667 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6667 Remote Similarity NPD17 Approved
0.6667 Remote Similarity NPD6799 Approved
0.6667 Remote Similarity NPD7799 Discontinued
0.6648 Remote Similarity NPD6234 Discontinued
0.6647 Remote Similarity NPD6801 Discontinued
0.6646 Remote Similarity NPD2796 Approved
0.6645 Remote Similarity NPD3972 Approved
0.6632 Remote Similarity NPD4482 Phase 3
0.6629 Remote Similarity NPD6808 Phase 2
0.6627 Remote Similarity NPD2532 Approved
0.6627 Remote Similarity NPD2534 Approved
0.6627 Remote Similarity NPD2533 Approved
0.6627 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6608 Remote Similarity NPD7239 Suspended
0.6606 Remote Similarity NPD5763 Approved
0.6606 Remote Similarity NPD5762 Approved
0.6606 Remote Similarity NPD2346 Discontinued
0.6605 Remote Similarity NPD6355 Discontinued
0.6604 Remote Similarity NPD6832 Phase 2
0.659 Remote Similarity NPD6386 Approved
0.659 Remote Similarity NPD6385 Approved
0.6587 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6587 Remote Similarity NPD4110 Phase 3
0.6575 Remote Similarity NPD3818 Discontinued
0.6573 Remote Similarity NPD7199 Phase 2
0.6568 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6552 Remote Similarity NPD37 Approved
0.6548 Remote Similarity NPD3887 Approved
0.6545 Remote Similarity NPD2438 Suspended
0.6543 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6541 Remote Similarity NPD8313 Approved
0.6541 Remote Similarity NPD8312 Approved
0.6538 Remote Similarity NPD1608 Approved
0.6536 Remote Similarity NPD6232 Discontinued
0.6534 Remote Similarity NPD3882 Suspended
0.6532 Remote Similarity NPD7028 Phase 2
0.6527 Remote Similarity NPD2800 Approved
0.6522 Remote Similarity NPD7685 Pre-registration
0.6519 Remote Similarity NPD3267 Approved
0.6519 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6519 Remote Similarity NPD3266 Approved
0.6514 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6506 Remote Similarity NPD2344 Approved
0.65 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6497 Remote Similarity NPD3749 Approved
0.6491 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6488 Remote Similarity NPD3750 Approved
0.6484 Remote Similarity NPD7228 Approved
0.648 Remote Similarity NPD7497 Discontinued
0.6477 Remote Similarity NPD5353 Approved
0.6477 Remote Similarity NPD5402 Approved
0.6477 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6464 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6464 Remote Similarity NPD2403 Approved
0.6457 Remote Similarity NPD1934 Approved
0.6456 Remote Similarity NPD1876 Approved
0.6452 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6442 Remote Similarity NPD4140 Approved
0.6442 Remote Similarity NPD2979 Phase 3
0.6437 Remote Similarity NPD4380 Phase 2
0.6424 Remote Similarity NPD1241 Discontinued
0.642 Remote Similarity NPD6859 Clinical (unspecified phase)
0.642 Remote Similarity NPD3268 Approved
0.642 Remote Similarity NPD2313 Discontinued
0.6412 Remote Similarity NPD6652 Clinical (unspecified phase)
0.6404 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6393 Remote Similarity NPD2163 Approved
0.6392 Remote Similarity NPD5327 Phase 3
0.6391 Remote Similarity NPD8166 Discontinued
0.6391 Remote Similarity NPD7003 Approved
0.6387 Remote Similarity NPD5585 Approved
0.6387 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6379 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6378 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6375 Remote Similarity NPD5647 Approved
0.6375 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6369 Remote Similarity NPD970 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6653 Approved
0.6359 Remote Similarity NPD8285 Discontinued
0.6358 Remote Similarity NPD5403 Approved
0.6354 Remote Similarity NPD7229 Phase 3
0.6353 Remote Similarity NPD2309 Approved
0.6349 Remote Similarity NPD8150 Discontinued
0.6347 Remote Similarity NPD1551 Phase 2
0.6347 Remote Similarity NPD6100 Approved
0.6347 Remote Similarity NPD6099 Approved
0.6346 Remote Similarity NPD1778 Approved
0.6345 Remote Similarity NPD3057 Approved
0.6344 Remote Similarity NPD7240 Approved
0.6337 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5401 Approved
0.6333 Remote Similarity NPD2181 Clinical (unspecified phase)
0.633 Remote Similarity NPD8407 Phase 2
0.6328 Remote Similarity NPD2801 Approved
0.6328 Remote Similarity NPD1465 Phase 2
0.6325 Remote Similarity NPD7097 Phase 1
0.6324 Remote Similarity NPD7074 Phase 3
0.6319 Remote Similarity NPD3764 Approved
0.6319 Remote Similarity NPD5242 Approved
0.631 Remote Similarity NPD2353 Approved
0.631 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6307 Remote Similarity NPD6873 Phase 2
0.6303 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6303 Remote Similarity NPD447 Suspended
0.6303 Remote Similarity NPD5735 Approved
0.6298 Remote Similarity NPD6959 Discontinued
0.6284 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6284 Remote Similarity NPD6166 Phase 2
0.6284 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6282 Remote Similarity NPD5691 Approved
0.628 Remote Similarity NPD6663 Approved
0.6272 Remote Similarity NPD1549 Phase 2
0.6271 Remote Similarity NPD6280 Approved
0.6271 Remote Similarity NPD6279 Approved
0.627 Remote Similarity NPD7054 Approved
0.627 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6266 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6266 Remote Similarity NPD1281 Approved
0.6264 Remote Similarity NPD7315 Approved
0.6263 Remote Similarity NPD2972 Approved
0.6263 Remote Similarity NPD3533 Approved
0.6262 Remote Similarity NPD5980 Discovery
0.6258 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6257 Remote Similarity NPD8368 Discontinued
0.6257 Remote Similarity NPD7058 Phase 2
0.6257 Remote Similarity NPD7057 Phase 3
0.6257 Remote Similarity NPD7768 Phase 2
0.625 Remote Similarity NPD2935 Discontinued
0.6242 Remote Similarity NPD4307 Phase 2
0.6238 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6237 Remote Similarity NPD7472 Approved
0.6236 Remote Similarity NPD8455 Phase 2
0.6235 Remote Similarity NPD9494 Approved
0.6223 Remote Similarity NPD4338 Clinical (unspecified phase)
0.622 Remote Similarity NPD6798 Discontinued
0.622 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6218 Remote Similarity NPD9545 Approved
0.6216 Remote Similarity NPD7177 Discontinued
0.6213 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6213 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6205 Remote Similarity NPD1933 Approved
0.6205 Remote Similarity NPD230 Phase 1
0.6203 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6196 Remote Similarity NPD4575 Clinical (unspecified phase)
0.619 Remote Similarity NPD7033 Discontinued
0.6188 Remote Similarity NPD4359 Approved
0.6181 Remote Similarity NPD2491 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