Structure

Physi-Chem Properties

Molecular Weight:  1094.59
Volume:  1056.331
LogP:  1.357
LogD:  1.574
LogS:  -2.522
# Rotatable Bonds:  15
TPSA:  377.29
# H-Bond Aceptor:  23
# H-Bond Donor:  15
# Rings:  8
# Heavy Atoms:  23

MedChem Properties

QED Drug-Likeness Score:  0.059
Synthetic Accessibility Score:  6.942
Fsp3:  0.962
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:  -6.14
MDCK Permeability:  0.0001506810513092205
Pgp-inhibitor:  0.991
Pgp-substrate:  0.105
Human Intestinal Absorption (HIA):  0.997
20% Bioavailability (F20%):  0.954
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  73.2354736328125%
Volume Distribution (VD):  -0.186
Pgp-substrate:  12.427762985229492%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.043
CYP2C19-inhibitor:  0.0
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.004
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.048
CYP3A4-inhibitor:  0.003
CYP3A4-substrate:  0.002

ADMET: Excretion

Clearance (CL):  -0.028
Half-life (T1/2):  0.723

ADMET: Toxicity

hERG Blockers:  0.358
Human Hepatotoxicity (H-HT):  0.123
Drug-inuced Liver Injury (DILI):  0.007
AMES Toxicity:  0.064
Rat Oral Acute Toxicity:  0.047
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.891
Carcinogencity:  0.003
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.038

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

  Natural Product: NPC246124

Natural Product ID:  NPC246124
Common Name*:   Gypenoside Lvi
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  SDPJKRBUXSIVOP-FMNOVIRCSA-N
Standard InCHI:  InChI=1S/C53H90O23/c1-22(2)10-9-13-53(8,76-47-42(68)38(64)36(62)29(73-47)21-70-45-40(66)33(59)26(58)20-69-45)23-11-14-52(7)32(23)24(56)16-31-50(5)17-25(57)44(49(3,4)30(50)12-15-51(31,52)6)75-48-43(39(65)35(61)28(19-55)72-48)74-46-41(67)37(63)34(60)27(18-54)71-46/h10,23-48,54-68H,9,11-21H2,1-8H3/t23-,24+,25+,26+,27+,28+,29+,30-,31+,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+,43+,44-,45-,46-,47-,48-,50-,51+,52+,53-/m0/s1
SMILES:  CC(=CCC[C@@](C)([C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)C[C@H]([C@@H](C(C)(C)[C@@H]3CC[C@@]21C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O1)O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3099572
PubChem CID:   76324667
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene saponins

*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
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota Stems n.a. n.a. PMID[20104880]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[22342101]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota aerial parts n.a. n.a. PMID[25895106]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16506 Synotis alata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4305 Pertusaria wulfenii Species Pertusariaceae 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 = 105.89 ug.mL-1 PMID[455648]

☑ 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 NPC246124 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 NPC180183
0.9899 High Similarity NPC208650
0.9899 High Similarity NPC63368
0.9899 High Similarity NPC14946
0.9899 High Similarity NPC181467
0.98 High Similarity NPC159005
0.98 High Similarity NPC6931
0.9798 High Similarity NPC127801
0.9798 High Similarity NPC194842
0.9798 High Similarity NPC152584
0.9798 High Similarity NPC269627
0.9798 High Similarity NPC208594
0.9798 High Similarity NPC160816
0.9798 High Similarity NPC208477
0.9798 High Similarity NPC69737
0.9697 High Similarity NPC165033
0.9697 High Similarity NPC273879
0.9604 High Similarity NPC220427
0.9596 High Similarity NPC155010
0.9596 High Similarity NPC189852
0.9596 High Similarity NPC114874
0.9596 High Similarity NPC16573
0.9596 High Similarity NPC473020
0.9596 High Similarity NPC157659
0.9596 High Similarity NPC16520
0.9596 High Similarity NPC286969
0.9596 High Similarity NPC8039
0.9596 High Similarity NPC211879
0.9596 High Similarity NPC131479
0.9596 High Similarity NPC120123
0.9596 High Similarity NPC245280
0.9596 High Similarity NPC31907
0.9596 High Similarity NPC472252
0.9515 High Similarity NPC65167
0.951 High Similarity NPC302057
0.9505 High Similarity NPC190395
0.9495 High Similarity NPC312553
0.9495 High Similarity NPC159036
0.9495 High Similarity NPC288694
0.9423 High Similarity NPC472716
0.9406 High Similarity NPC309448
0.9394 High Similarity NPC129372
0.9394 High Similarity NPC160734
0.9394 High Similarity NPC88000
0.9394 High Similarity NPC472023
0.9394 High Similarity NPC309425
0.9394 High Similarity NPC4831
0.9394 High Similarity NPC47566
0.9327 High Similarity NPC472715
0.932 High Similarity NPC296761
0.932 High Similarity NPC125361
0.932 High Similarity NPC154085
0.932 High Similarity NPC51925
0.932 High Similarity NPC43976
0.9314 High Similarity NPC231340
0.9307 High Similarity NPC476361
0.9307 High Similarity NPC476360
0.9307 High Similarity NPC470885
0.9307 High Similarity NPC148603
0.9307 High Similarity NPC221562
0.9307 High Similarity NPC187400
0.93 High Similarity NPC136816
0.9293 High Similarity NPC473200
0.9293 High Similarity NPC7341
0.9231 High Similarity NPC472717
0.9223 High Similarity NPC38217
0.9223 High Similarity NPC472988
0.9216 High Similarity NPC173859
0.9216 High Similarity NPC470512
0.9208 High Similarity NPC123796
0.9208 High Similarity NPC213190
0.9192 High Similarity NPC280825
0.9192 High Similarity NPC234287
0.9151 High Similarity NPC476693
0.9151 High Similarity NPC476671
0.9143 High Similarity NPC476547
0.9126 High Similarity NPC473469
0.9126 High Similarity NPC234160
0.9126 High Similarity NPC94272
0.9109 High Similarity NPC213674
0.9109 High Similarity NPC256133
0.9109 High Similarity NPC30289
0.9109 High Similarity NPC76497
0.9074 High Similarity NPC20979
0.9065 High Similarity NPC477810
0.9065 High Similarity NPC32707
0.9065 High Similarity NPC167183
0.9057 High Similarity NPC31896
0.9057 High Similarity NPC475312
0.9057 High Similarity NPC244431
0.9057 High Similarity NPC32361
0.9057 High Similarity NPC210569
0.9057 High Similarity NPC263359
0.9038 High Similarity NPC472896
0.9038 High Similarity NPC7213
0.9038 High Similarity NPC472897
0.9029 High Similarity NPC473199
0.9029 High Similarity NPC138057
0.9029 High Similarity NPC242748
0.9029 High Similarity NPC472899
0.9029 High Similarity NPC472900
0.9029 High Similarity NPC472898
0.902 High Similarity NPC473198
0.901 High Similarity NPC263756
0.901 High Similarity NPC117714
0.8991 High Similarity NPC10366
0.899 High Similarity NPC472989
0.8981 High Similarity NPC146652
0.8972 High Similarity NPC79900
0.8972 High Similarity NPC307642
0.8972 High Similarity NPC476546
0.8962 High Similarity NPC197231
0.8962 High Similarity NPC294129
0.8962 High Similarity NPC477032
0.8962 High Similarity NPC472987
0.8962 High Similarity NPC473021
0.8962 High Similarity NPC475247
0.8962 High Similarity NPC124677
0.8962 High Similarity NPC477028
0.8952 High Similarity NPC95051
0.8952 High Similarity NPC249265
0.8952 High Similarity NPC477809
0.8952 High Similarity NPC46190
0.8952 High Similarity NPC22779
0.8952 High Similarity NPC6806
0.8952 High Similarity NPC248746
0.8952 High Similarity NPC224098
0.8952 High Similarity NPC150372
0.8952 High Similarity NPC218571
0.8952 High Similarity NPC208383
0.8952 High Similarity NPC194207
0.8952 High Similarity NPC232054
0.8952 High Similarity NPC84956
0.8952 High Similarity NPC73243
0.8952 High Similarity NPC475550
0.8952 High Similarity NPC309278
0.8952 High Similarity NPC475333
0.8952 High Similarity NPC470433
0.8952 High Similarity NPC171073
0.8952 High Similarity NPC102016
0.8952 High Similarity NPC300557
0.8952 High Similarity NPC244086
0.8942 High Similarity NPC78034
0.8932 High Similarity NPC230948
0.8932 High Similarity NPC312774
0.8932 High Similarity NPC473734
0.8932 High Similarity NPC471434
0.8932 High Similarity NPC475521
0.8932 High Similarity NPC471435
0.8922 High Similarity NPC272015
0.8911 High Similarity NPC282669
0.8899 High Similarity NPC100048
0.8899 High Similarity NPC476690
0.8889 High Similarity NPC208832
0.8879 High Similarity NPC19888
0.8868 High Similarity NPC224314
0.8868 High Similarity NPC23808
0.8868 High Similarity NPC269297
0.8868 High Similarity NPC87998
0.8868 High Similarity NPC222202
0.8868 High Similarity NPC477811
0.8857 High Similarity NPC98696
0.8857 High Similarity NPC235824
0.8857 High Similarity NPC126147
0.8846 High Similarity NPC473923
0.8846 High Similarity NPC474569
0.8846 High Similarity NPC473476
0.8829 High Similarity NPC473566
0.8829 High Similarity NPC135369
0.8829 High Similarity NPC475358
0.8818 High Similarity NPC476692
0.8818 High Similarity NPC476691
0.8807 High Similarity NPC279638
0.8785 High Similarity NPC92710
0.8785 High Similarity NPC13193
0.8785 High Similarity NPC114188
0.8774 High Similarity NPC70204
0.8774 High Similarity NPC475670
0.8774 High Similarity NPC472901
0.8774 High Similarity NPC42482
0.8774 High Similarity NPC157530
0.8774 High Similarity NPC40440
0.8774 High Similarity NPC474573
0.8774 High Similarity NPC306131
0.8774 High Similarity NPC477026
0.8774 High Similarity NPC14630
0.8774 High Similarity NPC477027
0.8774 High Similarity NPC151134
0.8774 High Similarity NPC250089
0.8774 High Similarity NPC476835
0.8762 High Similarity NPC257964
0.8762 High Similarity NPC230507
0.8762 High Similarity NPC14704
0.8762 High Similarity NPC113044
0.8762 High Similarity NPC283829
0.8762 High Similarity NPC281939
0.8762 High Similarity NPC470432
0.8762 High Similarity NPC305423
0.8762 High Similarity NPC161676
0.875 High Similarity NPC75608

  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 NPC246124 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
0.8496 Intermediate Similarity NPD8377 Approved
0.8496 Intermediate Similarity NPD8294 Approved
0.8421 Intermediate Similarity NPD8378 Approved
0.8421 Intermediate Similarity NPD8296 Approved
0.8421 Intermediate Similarity NPD8335 Approved
0.8421 Intermediate Similarity NPD8380 Approved
0.8421 Intermediate Similarity NPD8379 Approved
0.8261 Intermediate Similarity NPD8033 Approved
0.8125 Intermediate Similarity NPD8133 Approved
0.8087 Intermediate Similarity NPD7516 Approved
0.8 Intermediate Similarity NPD7327 Approved
0.8 Intermediate Similarity NPD7328 Approved
0.7961 Intermediate Similarity NPD8171 Discontinued
0.7647 Intermediate Similarity NPD7503 Approved
0.7611 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD6412 Phase 2
0.7541 Intermediate Similarity NPD7507 Approved
0.7521 Intermediate Similarity NPD8328 Phase 3
0.7475 Intermediate Similarity NPD7525 Registered
0.7402 Intermediate Similarity NPD8450 Suspended
0.736 Intermediate Similarity NPD7319 Approved
0.7323 Intermediate Similarity NPD8449 Approved
0.7311 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7736 Approved
0.7143 Intermediate Similarity NPD7524 Approved
0.7069 Intermediate Similarity NPD6686 Approved
0.703 Intermediate Similarity NPD7645 Phase 2
0.7016 Intermediate Similarity NPD6370 Approved
0.6935 Remote Similarity NPD8517 Approved
0.6935 Remote Similarity NPD8516 Approved
0.6935 Remote Similarity NPD8515 Approved
0.6929 Remote Similarity NPD8293 Discontinued
0.6857 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6855 Remote Similarity NPD6054 Approved
0.6855 Remote Similarity NPD6059 Approved
0.6814 Remote Similarity NPD7638 Approved
0.68 Remote Similarity NPD8513 Phase 3
0.6796 Remote Similarity NPD6928 Phase 2
0.6763 Remote Similarity NPD7625 Phase 1
0.6762 Remote Similarity NPD6695 Phase 3
0.6754 Remote Similarity NPD7639 Approved
0.6754 Remote Similarity NPD7640 Approved
0.6694 Remote Similarity NPD6882 Approved
0.6694 Remote Similarity NPD8297 Approved
0.6667 Remote Similarity NPD7750 Discontinued
0.6667 Remote Similarity NPD6016 Approved
0.6667 Remote Similarity NPD6015 Approved
0.6641 Remote Similarity NPD7492 Approved
0.6634 Remote Similarity NPD7339 Approved
0.6634 Remote Similarity NPD6942 Approved
0.6614 Remote Similarity NPD5988 Approved
0.6613 Remote Similarity NPD6009 Approved
0.6612 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6589 Remote Similarity NPD6616 Approved
0.6587 Remote Similarity NPD6319 Approved
0.6577 Remote Similarity NPD8034 Phase 2
0.6577 Remote Similarity NPD8035 Phase 2
0.6569 Remote Similarity NPD6933 Approved
0.6562 Remote Similarity NPD6067 Discontinued
0.6538 Remote Similarity NPD7078 Approved
0.6504 Remote Similarity NPD4632 Approved
0.6476 Remote Similarity NPD6930 Phase 2
0.6476 Remote Similarity NPD6931 Approved
0.6471 Remote Similarity NPD5739 Approved
0.6471 Remote Similarity NPD7128 Approved
0.6471 Remote Similarity NPD6675 Approved
0.6471 Remote Similarity NPD6402 Approved
0.6465 Remote Similarity NPD4267 Clinical (unspecified phase)
0.646 Remote Similarity NPD7748 Approved
0.6446 Remote Similarity NPD6372 Approved
0.6446 Remote Similarity NPD6373 Approved
0.6435 Remote Similarity NPD7902 Approved
0.6408 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6381 Remote Similarity NPD6929 Approved
0.6373 Remote Similarity NPD6926 Approved
0.6373 Remote Similarity NPD1810 Approved
0.6373 Remote Similarity NPD1811 Approved
0.6373 Remote Similarity NPD6924 Approved
0.6372 Remote Similarity NPD6399 Phase 3
0.6364 Remote Similarity NPD6881 Approved
0.6364 Remote Similarity NPD7320 Approved
0.6364 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6033 Approved
0.6364 Remote Similarity NPD6899 Approved
0.6349 Remote Similarity NPD7115 Discovery
0.6346 Remote Similarity NPD6932 Approved
0.6341 Remote Similarity NPD6649 Approved
0.6341 Remote Similarity NPD8130 Phase 1
0.6341 Remote Similarity NPD6650 Approved
0.6339 Remote Similarity NPD3168 Discontinued
0.633 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6311 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6293 Remote Similarity NPD4755 Approved
0.6283 Remote Similarity NPD7515 Phase 2
0.6283 Remote Similarity NPD7087 Discontinued
0.6281 Remote Similarity NPD5697 Approved
0.6281 Remote Similarity NPD5701 Approved
0.626 Remote Similarity NPD7102 Approved
0.626 Remote Similarity NPD7290 Approved
0.626 Remote Similarity NPD6883 Approved
0.626 Remote Similarity NPD4634 Approved
0.625 Remote Similarity NPD5328 Approved
0.6239 Remote Similarity NPD4786 Approved
0.623 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6228 Remote Similarity NPD4202 Approved
0.6226 Remote Similarity NPD6683 Phase 2
0.6218 Remote Similarity NPD7632 Discontinued
0.621 Remote Similarity NPD6847 Approved
0.621 Remote Similarity NPD6617 Approved
0.621 Remote Similarity NPD6869 Approved
0.619 Remote Similarity NPD6925 Approved
0.619 Remote Similarity NPD5776 Phase 2
0.6186 Remote Similarity NPD5286 Approved
0.6186 Remote Similarity NPD5285 Approved
0.6186 Remote Similarity NPD4700 Approved
0.6186 Remote Similarity NPD4696 Approved
0.6183 Remote Similarity NPD7604 Phase 2
0.6182 Remote Similarity NPD6893 Approved
0.6179 Remote Similarity NPD6013 Approved
0.6179 Remote Similarity NPD6012 Approved
0.6179 Remote Similarity NPD6014 Approved
0.6176 Remote Similarity NPD4243 Approved
0.6174 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6174 Remote Similarity NPD7900 Approved
0.6168 Remote Similarity NPD7514 Phase 3
0.6168 Remote Similarity NPD7509 Discontinued
0.6154 Remote Similarity NPD6083 Phase 2
0.6154 Remote Similarity NPD5983 Phase 2
0.6154 Remote Similarity NPD6084 Phase 2
0.614 Remote Similarity NPD6079 Approved
0.6134 Remote Similarity NPD4159 Approved
0.6134 Remote Similarity NPD5344 Discontinued
0.6132 Remote Similarity NPD7145 Approved
0.6129 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6126 Remote Similarity NPD3618 Phase 1
0.6121 Remote Similarity NPD7991 Discontinued
0.6102 Remote Similarity NPD4225 Approved
0.6098 Remote Similarity NPD6011 Approved
0.609 Remote Similarity NPD6336 Discontinued
0.6083 Remote Similarity NPD5225 Approved
0.6083 Remote Similarity NPD5224 Approved
0.6083 Remote Similarity NPD4633 Approved
0.6083 Remote Similarity NPD5211 Phase 2
0.6083 Remote Similarity NPD5226 Approved
0.608 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6078 Remote Similarity NPD2686 Approved
0.6078 Remote Similarity NPD2687 Approved
0.6078 Remote Similarity NPD2254 Approved
0.6066 Remote Similarity NPD6008 Approved
0.6066 Remote Similarity NPD4768 Approved
0.6066 Remote Similarity NPD4767 Approved
0.6058 Remote Similarity NPD4785 Approved
0.6058 Remote Similarity NPD4784 Approved
0.6055 Remote Similarity NPD3667 Approved
0.6033 Remote Similarity NPD5175 Approved
0.6033 Remote Similarity NPD5174 Approved
0.6019 Remote Similarity NPD7332 Phase 2
0.6019 Remote Similarity NPD7151 Approved
0.6019 Remote Similarity NPD7152 Approved
0.6019 Remote Similarity NPD4748 Discontinued
0.6019 Remote Similarity NPD7150 Approved
0.6016 Remote Similarity NPD6940 Discontinued
0.6 Remote Similarity NPD7637 Suspended
0.6 Remote Similarity NPD5223 Approved
0.6 Remote Similarity NPD3669 Approved
0.6 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5984 Remote Similarity NPD5141 Approved
0.598 Remote Similarity NPD6922 Approved
0.598 Remote Similarity NPD6923 Approved
0.5968 Remote Similarity NPD4730 Approved
0.5968 Remote Similarity NPD4729 Approved
0.5968 Remote Similarity NPD8174 Phase 2
0.5966 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5965 Remote Similarity NPD6051 Approved
0.5965 Remote Similarity NPD4753 Phase 2
0.5963 Remote Similarity NPD6898 Phase 1
0.5963 Remote Similarity NPD6902 Approved
0.5935 Remote Similarity NPD5357 Phase 1
0.5932 Remote Similarity NPD4697 Phase 3
0.5932 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5932 Remote Similarity NPD5222 Approved
0.5932 Remote Similarity NPD5221 Approved
0.5926 Remote Similarity NPD8074 Phase 3
0.5922 Remote Similarity NPD7144 Approved
0.5922 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5922 Remote Similarity NPD7143 Approved
0.5912 Remote Similarity NPD5956 Approved
0.5902 Remote Similarity NPD4754 Approved
0.5891 Remote Similarity NPD6274 Approved
0.5887 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5882 Remote Similarity NPD5173 Approved
0.5878 Remote Similarity NPD7100 Approved
0.5878 Remote Similarity NPD7101 Approved
0.5877 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5873 Remote Similarity NPD5250 Approved
0.5873 Remote Similarity NPD5247 Approved
0.5873 Remote Similarity NPD5251 Approved
0.5873 Remote Similarity NPD5249 Phase 3
0.5873 Remote Similarity NPD5248 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