Structure

Physi-Chem Properties

Molecular Weight:  868.52
Volume:  864.937
LogP:  3.478
LogD:  3.602
LogS:  -4.26
# Rotatable Bonds:  7
TPSA:  237.45
# H-Bond Aceptor:  15
# H-Bond Donor:  9
# Rings:  8
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.131
Synthetic Accessibility Score:  6.194
Fsp3:  0.957
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.381
MDCK Permeability:  1.5020004866528325e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.201
Human Intestinal Absorption (HIA):  0.817
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.043
Plasma Protein Binding (PPB):  83.51517486572266%
Volume Distribution (VD):  0.316
Pgp-substrate:  13.144098281860352%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.518
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.309
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.008
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.065
CYP3A4-inhibitor:  0.097
CYP3A4-substrate:  0.047

ADMET: Excretion

Clearance (CL):  0.597
Half-life (T1/2):  0.598

ADMET: Toxicity

hERG Blockers:  0.102
Human Hepatotoxicity (H-HT):  0.178
Drug-inuced Liver Injury (DILI):  0.007
AMES Toxicity:  0.067
Rat Oral Acute Toxicity:  0.227
Maximum Recommended Daily Dose:  0.941
Skin Sensitization:  0.318
Carcinogencity:  0.022
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.986

Download Data

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

  Natural Product: NPC117714

Natural Product ID:  NPC117714
Common Name*:   Nephelioside V
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R)-2-[[(3S,4aR,6aR,6bS,8S,8aS,12aS,14aR,14bR)-8-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-hydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   nephelioside V
Standard InCHIKey:  OHNDWYDTYQVTSN-TZNBZXACSA-N
Standard InCHI:  InChI=1S/C46H76O15/c1-41(2)15-16-43(5)23(17-41)22-9-10-28-44(6)13-12-30(42(3,4)27(44)11-14-45(28,7)46(22,8)18-29(43)50)59-40-37(61-39-35(55)33(53)32(52)26(19-47)58-39)36(25(49)21-57-40)60-38-34(54)31(51)24(48)20-56-38/h9,23-40,47-55H,10-21H2,1-8H3/t23-,24-,25+,26+,27-,28+,29-,30-,31-,32+,33-,34+,35+,36-,37+,38-,39-,40-,43-,44-,45+,46+/m0/s1
SMILES:  CC1(C)CC[C@@]2(C)[C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@@H]2O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL477836
PubChem CID:   21575019
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO19602 Nephelium maingayi Species Sapindaceae Eukaryota bark n.a. n.a. PMID[14987059]
NPO19602 Nephelium maingayi Species Sapindaceae 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
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 13.6 ug ml-1 PMID[512263]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 11.7 ug ml-1 PMID[512263]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 13.9 ug ml-1 PMID[512263]
NPT737 Cell Line HUVEC Homo sapiens ED50 = 17.7 ug ml-1 PMID[512263]

☑ 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 NPC117714 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
1.0 High Similarity NPC263756
0.9894 High Similarity NPC30289
0.9894 High Similarity NPC76497
0.9894 High Similarity NPC256133
0.9894 High Similarity NPC213674
0.9789 High Similarity NPC123796
0.9688 High Similarity NPC471435
0.9688 High Similarity NPC230948
0.9688 High Similarity NPC473734
0.9688 High Similarity NPC471434
0.9688 High Similarity NPC148603
0.9588 High Similarity NPC470512
0.9588 High Similarity NPC138057
0.9588 High Similarity NPC173859
0.9583 High Similarity NPC162354
0.949 High Similarity NPC78034
0.949 High Similarity NPC281939
0.9485 High Similarity NPC173583
0.9485 High Similarity NPC110656
0.9485 High Similarity NPC473127
0.9485 High Similarity NPC203354
0.9381 High Similarity NPC473124
0.9381 High Similarity NPC473123
0.9293 High Similarity NPC257964
0.9286 High Similarity NPC54521
0.9286 High Similarity NPC57065
0.9286 High Similarity NPC109792
0.9278 High Similarity NPC159036
0.9278 High Similarity NPC288694
0.9278 High Similarity NPC312553
0.92 High Similarity NPC126147
0.9192 High Similarity NPC127801
0.9192 High Similarity NPC160816
0.9192 High Similarity NPC208477
0.9192 High Similarity NPC194842
0.9192 High Similarity NPC269627
0.9192 High Similarity NPC69737
0.9192 High Similarity NPC152584
0.9192 High Similarity NPC208594
0.9184 High Similarity NPC189852
0.9184 High Similarity NPC157659
0.9184 High Similarity NPC155010
0.9184 High Similarity NPC114874
0.9184 High Similarity NPC16520
0.9184 High Similarity NPC120123
0.9184 High Similarity NPC16573
0.9184 High Similarity NPC473020
0.9184 High Similarity NPC131479
0.9184 High Similarity NPC473129
0.9184 High Similarity NPC31907
0.9184 High Similarity NPC472252
0.9184 High Similarity NPC99627
0.9184 High Similarity NPC286969
0.9184 High Similarity NPC8039
0.9184 High Similarity NPC245280
0.9184 High Similarity NPC211879
0.9149 High Similarity NPC477927
0.9149 High Similarity NPC305160
0.9149 High Similarity NPC72817
0.9118 High Similarity NPC164419
0.91 High Similarity NPC190395
0.91 High Similarity NPC14946
0.91 High Similarity NPC208650
0.91 High Similarity NPC181467
0.91 High Similarity NPC63368
0.9091 High Similarity NPC187400
0.9091 High Similarity NPC273879
0.9091 High Similarity NPC221562
0.9091 High Similarity NPC470885
0.9091 High Similarity NPC165033
0.9072 High Similarity NPC64348
0.9072 High Similarity NPC473790
0.9072 High Similarity NPC473200
0.9072 High Similarity NPC7341
0.9029 High Similarity NPC276093
0.9029 High Similarity NPC469946
0.9029 High Similarity NPC109079
0.9029 High Similarity NPC10320
0.9029 High Similarity NPC473373
0.9029 High Similarity NPC292677
0.9029 High Similarity NPC139044
0.9029 High Similarity NPC475504
0.9029 High Similarity NPC101744
0.9029 High Similarity NPC104400
0.9029 High Similarity NPC475516
0.9029 High Similarity NPC324875
0.9029 High Similarity NPC471383
0.9029 High Similarity NPC257468
0.9029 High Similarity NPC79718
0.9029 High Similarity NPC102439
0.9029 High Similarity NPC104071
0.902 High Similarity NPC127056
0.902 High Similarity NPC59804
0.902 High Similarity NPC475296
0.902 High Similarity NPC279554
0.902 High Similarity NPC174679
0.902 High Similarity NPC474589
0.902 High Similarity NPC270667
0.902 High Similarity NPC29069
0.902 High Similarity NPC90856
0.902 High Similarity NPC136877
0.902 High Similarity NPC164194
0.902 High Similarity NPC56713
0.901 High Similarity NPC220427
0.901 High Similarity NPC180183
0.901 High Similarity NPC159005
0.901 High Similarity NPC6931
0.901 High Similarity NPC246124
0.9 High Similarity NPC242748
0.9 High Similarity NPC309448
0.898 High Similarity NPC47566
0.898 High Similarity NPC309425
0.898 High Similarity NPC88000
0.898 High Similarity NPC472023
0.898 High Similarity NPC160734
0.898 High Similarity NPC4831
0.898 High Similarity NPC129372
0.8969 High Similarity NPC280825
0.8969 High Similarity NPC234287
0.8942 High Similarity NPC114304
0.8942 High Similarity NPC133818
0.8942 High Similarity NPC323341
0.8942 High Similarity NPC174720
0.8942 High Similarity NPC219180
0.8942 High Similarity NPC258885
0.8942 High Similarity NPC96641
0.8942 High Similarity NPC151543
0.8942 High Similarity NPC309714
0.8942 High Similarity NPC251263
0.8942 High Similarity NPC473826
0.8942 High Similarity NPC241909
0.8942 High Similarity NPC166422
0.8942 High Similarity NPC295823
0.8942 High Similarity NPC114287
0.8942 High Similarity NPC150400
0.8942 High Similarity NPC473343
0.8942 High Similarity NPC73318
0.8942 High Similarity NPC46665
0.8942 High Similarity NPC134835
0.8942 High Similarity NPC475467
0.8942 High Similarity NPC192600
0.8942 High Similarity NPC475287
0.8942 High Similarity NPC155410
0.8942 High Similarity NPC124296
0.8942 High Similarity NPC163183
0.8932 High Similarity NPC473481
0.8932 High Similarity NPC157474
0.8932 High Similarity NPC179434
0.8932 High Similarity NPC108748
0.8932 High Similarity NPC110494
0.8932 High Similarity NPC297208
0.8932 High Similarity NPC211798
0.8932 High Similarity NPC235841
0.8932 High Similarity NPC30397
0.8922 High Similarity NPC204407
0.8922 High Similarity NPC57362
0.8922 High Similarity NPC285253
0.8922 High Similarity NPC221110
0.8922 High Similarity NPC302057
0.8922 High Similarity NPC180459
0.8922 High Similarity NPC237503
0.8922 High Similarity NPC195116
0.8922 High Similarity NPC167383
0.8922 High Similarity NPC306746
0.8911 High Similarity NPC473469
0.8911 High Similarity NPC231340
0.8911 High Similarity NPC234160
0.8889 High Similarity NPC272015
0.8889 High Similarity NPC136816
0.8878 High Similarity NPC282669
0.8866 High Similarity NPC240372
0.8857 High Similarity NPC164389
0.8857 High Similarity NPC305981
0.8857 High Similarity NPC471385
0.8857 High Similarity NPC4328
0.8857 High Similarity NPC294453
0.8857 High Similarity NPC65105
0.8857 High Similarity NPC41061
0.8857 High Similarity NPC469782
0.8857 High Similarity NPC261506
0.8857 High Similarity NPC161717
0.8857 High Similarity NPC202828
0.8857 High Similarity NPC476068
0.8857 High Similarity NPC70809
0.8857 High Similarity NPC60557
0.8857 High Similarity NPC67857
0.8857 High Similarity NPC119592
0.8857 High Similarity NPC236638
0.8857 High Similarity NPC309907
0.8857 High Similarity NPC471550
0.8857 High Similarity NPC76972
0.8857 High Similarity NPC79643
0.8857 High Similarity NPC123199
0.8857 High Similarity NPC71065
0.8857 High Similarity NPC473714
0.8857 High Similarity NPC224381
0.8857 High Similarity NPC475160
0.8857 High Similarity NPC227551
0.8857 High Similarity NPC475486
0.8857 High Similarity NPC204414

  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 NPC117714 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
0.8125 Intermediate Similarity NPD8377 Approved
0.8125 Intermediate Similarity NPD8294 Approved
0.807 Intermediate Similarity NPD8328 Phase 3
0.8053 Intermediate Similarity NPD8380 Approved
0.8053 Intermediate Similarity NPD8378 Approved
0.8053 Intermediate Similarity NPD8379 Approved
0.8053 Intermediate Similarity NPD8296 Approved
0.8053 Intermediate Similarity NPD8335 Approved
0.8037 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8018 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD8033 Approved
0.7849 Intermediate Similarity NPD7645 Phase 2
0.7748 Intermediate Similarity NPD8133 Approved
0.7723 Intermediate Similarity NPD8171 Discontinued
0.7685 Intermediate Similarity NPD6412 Phase 2
0.7632 Intermediate Similarity NPD7328 Approved
0.7632 Intermediate Similarity NPD7327 Approved
0.7565 Intermediate Similarity NPD7516 Approved
0.7436 Intermediate Similarity NPD7503 Approved
0.7297 Intermediate Similarity NPD6686 Approved
0.719 Intermediate Similarity NPD7507 Approved
0.7143 Intermediate Similarity NPD7748 Approved
0.712 Intermediate Similarity NPD8449 Approved
0.7103 Intermediate Similarity NPD7902 Approved
0.7063 Intermediate Similarity NPD8450 Suspended
0.7041 Intermediate Similarity NPD7525 Registered
0.7027 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD7319 Approved
0.7 Intermediate Similarity NPD8516 Approved
0.7 Intermediate Similarity NPD8515 Approved
0.7 Intermediate Similarity NPD8517 Approved
0.7 Intermediate Similarity NPD8513 Phase 3
0.6952 Remote Similarity NPD7515 Phase 2
0.6935 Remote Similarity NPD7736 Approved
0.6822 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7900 Approved
0.6803 Remote Similarity NPD6370 Approved
0.6727 Remote Similarity NPD7638 Approved
0.672 Remote Similarity NPD8293 Discontinued
0.6667 Remote Similarity NPD7639 Approved
0.6667 Remote Similarity NPD7640 Approved
0.6639 Remote Similarity NPD6059 Approved
0.6639 Remote Similarity NPD6054 Approved
0.6613 Remote Similarity NPD6067 Discontinued
0.6598 Remote Similarity NPD1810 Approved
0.6598 Remote Similarity NPD1811 Approved
0.6571 Remote Similarity NPD7524 Approved
0.6535 Remote Similarity NPD6928 Phase 2
0.6531 Remote Similarity NPD7339 Approved
0.6531 Remote Similarity NPD6942 Approved
0.6525 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6481 Remote Similarity NPD8034 Phase 2
0.6481 Remote Similarity NPD8035 Phase 2
0.6471 Remote Similarity NPD8297 Approved
0.6471 Remote Similarity NPD6882 Approved
0.6465 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6015 Approved
0.6452 Remote Similarity NPD6016 Approved
0.6442 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7492 Approved
0.64 Remote Similarity NPD5988 Approved
0.6393 Remote Similarity NPD6009 Approved
0.6389 Remote Similarity NPD3168 Discontinued
0.6378 Remote Similarity NPD6616 Approved
0.6371 Remote Similarity NPD6319 Approved
0.6356 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6695 Phase 3
0.6331 Remote Similarity NPD7625 Phase 1
0.6328 Remote Similarity NPD7078 Approved
0.6289 Remote Similarity NPD2254 Approved
0.6289 Remote Similarity NPD2687 Approved
0.6289 Remote Similarity NPD2686 Approved
0.6283 Remote Similarity NPD4225 Approved
0.6281 Remote Similarity NPD4632 Approved
0.6273 Remote Similarity NPD6399 Phase 3
0.6271 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6262 Remote Similarity NPD7750 Discontinued
0.6239 Remote Similarity NPD6675 Approved
0.6239 Remote Similarity NPD7128 Approved
0.6239 Remote Similarity NPD5739 Approved
0.6239 Remote Similarity NPD6402 Approved
0.6226 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6218 Remote Similarity NPD6372 Approved
0.6218 Remote Similarity NPD6373 Approved
0.619 Remote Similarity NPD3670 Clinical (unspecified phase)
0.619 Remote Similarity NPD3669 Approved
0.6174 Remote Similarity NPD5344 Discontinued
0.6168 Remote Similarity NPD3618 Phase 1
0.6167 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6033 Approved
0.6147 Remote Similarity NPD5328 Approved
0.614 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6139 Remote Similarity NPD6933 Approved
0.6134 Remote Similarity NPD6881 Approved
0.6134 Remote Similarity NPD7320 Approved
0.6134 Remote Similarity NPD6899 Approved
0.6132 Remote Similarity NPD4786 Approved
0.6129 Remote Similarity NPD7115 Discovery
0.6122 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6121 Remote Similarity NPD7632 Discontinued
0.6117 Remote Similarity NPD6929 Approved
0.6116 Remote Similarity NPD6649 Approved
0.6116 Remote Similarity NPD6650 Approved
0.6116 Remote Similarity NPD8130 Phase 1
0.6111 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6095 Remote Similarity NPD3667 Approved
0.6077 Remote Similarity NPD8074 Phase 3
0.6066 Remote Similarity NPD6429 Approved
0.6066 Remote Similarity NPD6430 Approved
0.6058 Remote Similarity NPD6931 Approved
0.6058 Remote Similarity NPD6930 Phase 2
0.6053 Remote Similarity NPD4755 Approved
0.605 Remote Similarity NPD5697 Approved
0.605 Remote Similarity NPD5701 Approved
0.604 Remote Similarity NPD8264 Approved
0.6036 Remote Similarity NPD6079 Approved
0.6036 Remote Similarity NPD6411 Approved
0.6033 Remote Similarity NPD7102 Approved
0.6033 Remote Similarity NPD6883 Approved
0.6033 Remote Similarity NPD7290 Approved
0.6033 Remote Similarity NPD4634 Approved
0.602 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5984 Remote Similarity NPD6617 Approved
0.5984 Remote Similarity NPD6847 Approved
0.5984 Remote Similarity NPD6869 Approved
0.5982 Remote Similarity NPD4202 Approved
0.5969 Remote Similarity NPD7604 Phase 2
0.5966 Remote Similarity NPD5357 Phase 1
0.595 Remote Similarity NPD6014 Approved
0.595 Remote Similarity NPD6012 Approved
0.595 Remote Similarity NPD6013 Approved
0.5948 Remote Similarity NPD4700 Approved
0.5948 Remote Similarity NPD5286 Approved
0.5948 Remote Similarity NPD5285 Approved
0.5948 Remote Similarity NPD4696 Approved
0.5946 Remote Similarity NPD46 Approved
0.5946 Remote Similarity NPD7838 Discovery
0.5946 Remote Similarity NPD6698 Approved
0.5941 Remote Similarity NPD6926 Approved
0.5941 Remote Similarity NPD6924 Approved
0.5938 Remote Similarity NPD5983 Phase 2
0.5922 Remote Similarity NPD6925 Approved
0.5922 Remote Similarity NPD6932 Approved
0.5922 Remote Similarity NPD5776 Phase 2
0.5917 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5913 Remote Similarity NPD6084 Phase 2
0.5913 Remote Similarity NPD6083 Phase 2
0.5909 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5905 Remote Similarity NPD7509 Discontinued
0.59 Remote Similarity NPD4243 Approved
0.5897 Remote Similarity NPD4159 Approved
0.5893 Remote Similarity NPD7087 Discontinued
0.5878 Remote Similarity NPD6336 Discontinued
0.5877 Remote Similarity NPD7991 Discontinued
0.5868 Remote Similarity NPD6011 Approved
0.5865 Remote Similarity NPD7145 Approved
0.5856 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5856 Remote Similarity NPD6101 Approved
0.5854 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5847 Remote Similarity NPD5226 Approved
0.5847 Remote Similarity NPD4633 Approved
0.5847 Remote Similarity NPD5211 Phase 2
0.5847 Remote Similarity NPD5225 Approved
0.5847 Remote Similarity NPD5224 Approved
0.5833 Remote Similarity NPD3666 Approved
0.5833 Remote Similarity NPD371 Approved
0.5833 Remote Similarity NPD3665 Phase 1
0.5833 Remote Similarity NPD3133 Approved
0.5833 Remote Similarity NPD4767 Approved
0.5833 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5833 Remote Similarity NPD4768 Approved
0.5833 Remote Similarity NPD6008 Approved
0.5826 Remote Similarity NPD4697 Phase 3
0.5826 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5826 Remote Similarity NPD5221 Approved
0.5826 Remote Similarity NPD5222 Approved
0.5818 Remote Similarity NPD3573 Approved
0.5814 Remote Similarity NPD6921 Approved
0.5812 Remote Similarity NPD6648 Approved
0.581 Remote Similarity NPD6683 Phase 2
0.5804 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5804 Remote Similarity NPD6674 Discontinued
0.5798 Remote Similarity NPD5175 Approved
0.5798 Remote Similarity NPD5174 Approved
0.5794 Remote Similarity NPD6940 Discontinued
0.5784 Remote Similarity NPD4785 Approved
0.5784 Remote Similarity NPD4784 Approved
0.578 Remote Similarity NPD6893 Approved
0.5776 Remote Similarity NPD5173 Approved
0.5769 Remote Similarity NPD5125 Phase 3
0.5769 Remote Similarity NPD5126 Approved
0.5763 Remote Similarity NPD5223 Approved
0.5755 Remote Similarity NPD7332 Phase 2
0.5755 Remote Similarity NPD7514 Phase 3
0.5755 Remote Similarity NPD4748 Discontinued
0.5752 Remote Similarity NPD7983 Approved
0.5752 Remote Similarity NPD7637 Suspended
0.575 Remote Similarity NPD5141 Approved
0.5743 Remote Similarity NPD7150 Approved
0.5743 Remote Similarity NPD7151 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