Structure

Physi-Chem Properties

Molecular Weight:  800.49
Volume:  804.076
LogP:  2.875
LogD:  2.972
LogS:  -2.828
# Rotatable Bonds:  10
TPSA:  239.22
# H-Bond Aceptor:  14
# H-Bond Donor:  10
# Rings:  6
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.11
Synthetic Accessibility Score:  5.991
Fsp3:  0.952
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:  -5.584
MDCK Permeability:  6.470116932177916e-05
Pgp-inhibitor:  0.994
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.872
20% Bioavailability (F20%):  0.958
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  80.3064956665039%
Volume Distribution (VD):  0.259
Pgp-substrate:  7.739652633666992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.081
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.343
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.029
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.028
CYP3A4-substrate:  0.046

ADMET: Excretion

Clearance (CL):  0.811
Half-life (T1/2):  0.673

ADMET: Toxicity

hERG Blockers:  0.122
Human Hepatotoxicity (H-HT):  0.191
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.057
Rat Oral Acute Toxicity:  0.087
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.236
Carcinogencity:  0.005
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.282

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

  Natural Product: NPC165033

Natural Product ID:  NPC165033
Common Name*:   Gypenoside L
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-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-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:  LTJZMSTVPKBWKB-HGZKDYFJSA-N
Standard InCHI:  InChI=1S/C42H72O14/c1-20(2)10-9-13-42(8,52)21-11-14-41(7)28(21)22(45)16-27-39(5)17-23(46)35(38(3,4)26(39)12-15-40(27,41)6)56-37-34(32(50)30(48)25(19-44)54-37)55-36-33(51)31(49)29(47)24(18-43)53-36/h10,21-37,43-52H,9,11-19H2,1-8H3/t21-,22+,23+,24+,25+,26-,27+,28-,29+,30+,31-,32-,33+,34+,35-,36-,37-,39-,40+,41+,42-/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2[C@H](O)C[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3C[C@@H](O)[C@H]3[C@@]2(C)CC[C@@H]3[C@](CCC=C(C)C)(O)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3099605
PubChem CID:   76335475
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 = 34.94 ug.mL-1 PMID[527451]
NPT81 Cell Line A549 Homo sapiens Activity = 37.2 % PMID[527452]
NPT81 Cell Line A549 Homo sapiens IC50 = 78.6 ug.mL-1 PMID[527452]

☑ 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 NPC165033 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 NPC273879
0.9896 High Similarity NPC211879
0.9896 High Similarity NPC31907
0.9896 High Similarity NPC16520
0.9896 High Similarity NPC114874
0.9896 High Similarity NPC286969
0.9896 High Similarity NPC155010
0.9896 High Similarity NPC8039
0.9896 High Similarity NPC120123
0.9896 High Similarity NPC131479
0.9896 High Similarity NPC472252
0.9896 High Similarity NPC157659
0.9896 High Similarity NPC245280
0.9896 High Similarity NPC16573
0.9896 High Similarity NPC473020
0.9896 High Similarity NPC189852
0.9796 High Similarity NPC181467
0.9792 High Similarity NPC288694
0.9792 High Similarity NPC312553
0.9792 High Similarity NPC159036
0.9697 High Similarity NPC180183
0.9697 High Similarity NPC246124
0.9694 High Similarity NPC269627
0.9694 High Similarity NPC152584
0.9694 High Similarity NPC127801
0.9694 High Similarity NPC160816
0.9694 High Similarity NPC194842
0.9694 High Similarity NPC208477
0.9694 High Similarity NPC69737
0.9694 High Similarity NPC208594
0.9688 High Similarity NPC88000
0.9688 High Similarity NPC472023
0.9688 High Similarity NPC47566
0.9688 High Similarity NPC160734
0.9688 High Similarity NPC309425
0.9688 High Similarity NPC129372
0.9688 High Similarity NPC4831
0.96 High Similarity NPC125361
0.96 High Similarity NPC296761
0.96 High Similarity NPC154085
0.96 High Similarity NPC43976
0.96 High Similarity NPC51925
0.9596 High Similarity NPC14946
0.9596 High Similarity NPC63368
0.9596 High Similarity NPC208650
0.9596 High Similarity NPC231340
0.9592 High Similarity NPC470885
0.9592 High Similarity NPC221562
0.9592 High Similarity NPC187400
0.9588 High Similarity NPC136816
0.9583 High Similarity NPC473200
0.9583 High Similarity NPC7341
0.95 High Similarity NPC472988
0.95 High Similarity NPC38217
0.95 High Similarity NPC159005
0.95 High Similarity NPC6931
0.95 High Similarity NPC220427
0.949 High Similarity NPC213190
0.9479 High Similarity NPC280825
0.9479 High Similarity NPC234287
0.9412 High Similarity NPC65167
0.94 High Similarity NPC190395
0.94 High Similarity NPC234160
0.94 High Similarity NPC473469
0.9314 High Similarity NPC472717
0.9307 High Similarity NPC7213
0.9307 High Similarity NPC472897
0.9307 High Similarity NPC472896
0.93 High Similarity NPC472900
0.93 High Similarity NPC472898
0.93 High Similarity NPC242748
0.93 High Similarity NPC472899
0.93 High Similarity NPC473199
0.93 High Similarity NPC309448
0.9293 High Similarity NPC473198
0.9271 High Similarity NPC472989
0.9223 High Similarity NPC472987
0.9223 High Similarity NPC472715
0.9223 High Similarity NPC473021
0.9216 High Similarity NPC302057
0.92 High Similarity NPC475521
0.92 High Similarity NPC312774
0.9192 High Similarity NPC272015
0.9184 High Similarity NPC282669
0.9135 High Similarity NPC475312
0.9135 High Similarity NPC472716
0.9118 High Similarity NPC235824
0.9109 High Similarity NPC474569
0.9109 High Similarity NPC473923
0.9109 High Similarity NPC473476
0.9091 High Similarity NPC117714
0.9091 High Similarity NPC263756
0.9048 High Similarity NPC476693
0.9038 High Similarity NPC114188
0.9038 High Similarity NPC197231
0.9029 High Similarity NPC157530
0.9029 High Similarity NPC472901
0.9029 High Similarity NPC250089
0.9029 High Similarity NPC14630
0.9029 High Similarity NPC476835
0.901 High Similarity NPC475365
0.901 High Similarity NPC476360
0.901 High Similarity NPC75608
0.901 High Similarity NPC476361
0.901 High Similarity NPC148603
0.9 High Similarity NPC256133
0.9 High Similarity NPC76497
0.9 High Similarity NPC30289
0.9 High Similarity NPC213674
0.898 High Similarity NPC243728
0.898 High Similarity NPC473890
0.8952 High Similarity NPC19888
0.8932 High Similarity NPC476541
0.8932 High Similarity NPC476540
0.8932 High Similarity NPC476539
0.8932 High Similarity NPC476538
0.8922 High Similarity NPC470512
0.8922 High Similarity NPC181845
0.8922 High Similarity NPC26798
0.8922 High Similarity NPC173859
0.8911 High Similarity NPC162354
0.8911 High Similarity NPC123796
0.89 High Similarity NPC31346
0.8889 High Similarity NPC216260
0.8889 High Similarity NPC5358
0.8889 High Similarity NPC158088
0.8868 High Similarity NPC144068
0.8868 High Similarity NPC476671
0.8857 High Similarity NPC476547
0.8846 High Similarity NPC477026
0.8846 High Similarity NPC40440
0.8846 High Similarity NPC42482
0.8846 High Similarity NPC306131
0.8846 High Similarity NPC474573
0.8846 High Similarity NPC475670
0.8846 High Similarity NPC477027
0.8846 High Similarity NPC70204
0.8835 High Similarity NPC470432
0.8835 High Similarity NPC305423
0.8835 High Similarity NPC94272
0.8835 High Similarity NPC283829
0.8835 High Similarity NPC226642
0.8835 High Similarity NPC230507
0.8835 High Similarity NPC33053
0.8835 High Similarity NPC113044
0.8835 High Similarity NPC161676
0.8835 High Similarity NPC14704
0.8824 High Similarity NPC110656
0.8824 High Similarity NPC473734
0.8824 High Similarity NPC57065
0.8824 High Similarity NPC203354
0.8824 High Similarity NPC93352
0.8824 High Similarity NPC471434
0.8824 High Similarity NPC473127
0.8824 High Similarity NPC109792
0.8824 High Similarity NPC54521
0.8824 High Similarity NPC230948
0.8824 High Similarity NPC471435
0.8824 High Similarity NPC173583
0.88 High Similarity NPC473790
0.8796 High Similarity NPC20979
0.8796 High Similarity NPC476690
0.8796 High Similarity NPC100048
0.8788 High Similarity NPC76486
0.8785 High Similarity NPC167183
0.8785 High Similarity NPC32707
0.8785 High Similarity NPC477810
0.8774 High Similarity NPC32361
0.8774 High Similarity NPC210569
0.8774 High Similarity NPC263359
0.8774 High Similarity NPC31896
0.8774 High Similarity NPC244431
0.8774 High Similarity NPC474265
0.8774 High Similarity NPC210420
0.8762 High Similarity NPC191439
0.8762 High Similarity NPC103627
0.8762 High Similarity NPC170974
0.875 High Similarity NPC295980
0.875 High Similarity NPC98696
0.875 High Similarity NPC475634
0.8738 High Similarity NPC138057
0.8725 High Similarity NPC473129
0.8725 High Similarity NPC473124
0.8725 High Similarity NPC99627
0.8725 High Similarity NPC473123
0.8716 High Similarity NPC476692
0.8716 High Similarity NPC476691
0.8716 High Similarity NPC10366
0.8713 High Similarity NPC470434
0.8713 High Similarity NPC267510
0.8704 High Similarity NPC146652
0.87 High Similarity NPC476895
0.8692 High Similarity NPC307642
0.8692 High Similarity NPC476546
0.8692 High Similarity NPC79900
0.8687 High Similarity NPC207617
0.8687 High Similarity NPC90583
0.8679 High Similarity NPC475247
0.8679 High Similarity NPC13190
0.8679 High Similarity NPC263827

  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 NPC165033 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
0.8559 High Similarity NPD8377 Approved
0.8559 High Similarity NPD8294 Approved
0.8482 Intermediate Similarity NPD8033 Approved
0.8482 Intermediate Similarity NPD8335 Approved
0.8482 Intermediate Similarity NPD8379 Approved
0.8482 Intermediate Similarity NPD8380 Approved
0.8482 Intermediate Similarity NPD8378 Approved
0.8482 Intermediate Similarity NPD8296 Approved
0.8304 Intermediate Similarity NPD7516 Approved
0.8214 Intermediate Similarity NPD7327 Approved
0.8214 Intermediate Similarity NPD7328 Approved
0.802 Intermediate Similarity NPD8171 Discontinued
0.8018 Intermediate Similarity NPD8133 Approved
0.7845 Intermediate Similarity NPD7503 Approved
0.7818 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD6412 Phase 2
0.7731 Intermediate Similarity NPD7507 Approved
0.7708 Intermediate Similarity NPD7525 Registered
0.7563 Intermediate Similarity NPD8328 Phase 3
0.7541 Intermediate Similarity NPD7319 Approved
0.75 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7524 Approved
0.7317 Intermediate Similarity NPD7736 Approved
0.7297 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD6686 Approved
0.7245 Intermediate Similarity NPD7645 Phase 2
0.7222 Intermediate Similarity NPD8449 Approved
0.719 Intermediate Similarity NPD6370 Approved
0.7165 Intermediate Similarity NPD8450 Suspended
0.7097 Intermediate Similarity NPD8293 Discontinued
0.7059 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6054 Approved
0.7025 Intermediate Similarity NPD6059 Approved
0.7 Intermediate Similarity NPD6928 Phase 2
0.7 Intermediate Similarity NPD7638 Approved
0.6961 Remote Similarity NPD6695 Phase 3
0.6937 Remote Similarity NPD7640 Approved
0.6937 Remote Similarity NPD7639 Approved
0.6912 Remote Similarity NPD7625 Phase 1
0.6864 Remote Similarity NPD6882 Approved
0.6864 Remote Similarity NPD8297 Approved
0.6857 Remote Similarity NPD7750 Discontinued
0.6837 Remote Similarity NPD6942 Approved
0.6837 Remote Similarity NPD7339 Approved
0.6829 Remote Similarity NPD8517 Approved
0.6829 Remote Similarity NPD6015 Approved
0.6829 Remote Similarity NPD8516 Approved
0.6829 Remote Similarity NPD8513 Phase 3
0.6829 Remote Similarity NPD8515 Approved
0.6829 Remote Similarity NPD6016 Approved
0.68 Remote Similarity NPD7492 Approved
0.6777 Remote Similarity NPD6009 Approved
0.6774 Remote Similarity NPD5988 Approved
0.6768 Remote Similarity NPD6933 Approved
0.6759 Remote Similarity NPD8035 Phase 2
0.6759 Remote Similarity NPD8034 Phase 2
0.6748 Remote Similarity NPD6319 Approved
0.6746 Remote Similarity NPD6616 Approved
0.672 Remote Similarity NPD6067 Discontinued
0.6693 Remote Similarity NPD7078 Approved
0.6667 Remote Similarity NPD6931 Approved
0.6667 Remote Similarity NPD6930 Phase 2
0.6667 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4632 Approved
0.6638 Remote Similarity NPD6402 Approved
0.6638 Remote Similarity NPD7128 Approved
0.6638 Remote Similarity NPD5739 Approved
0.6638 Remote Similarity NPD6675 Approved
0.6636 Remote Similarity NPD7748 Approved
0.661 Remote Similarity NPD6372 Approved
0.661 Remote Similarity NPD6373 Approved
0.6607 Remote Similarity NPD7902 Approved
0.66 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6569 Remote Similarity NPD6929 Approved
0.6566 Remote Similarity NPD1810 Approved
0.6566 Remote Similarity NPD6924 Approved
0.6566 Remote Similarity NPD6926 Approved
0.6566 Remote Similarity NPD1811 Approved
0.6545 Remote Similarity NPD6399 Phase 3
0.6542 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6535 Remote Similarity NPD6932 Approved
0.6525 Remote Similarity NPD6899 Approved
0.6525 Remote Similarity NPD7320 Approved
0.6525 Remote Similarity NPD6881 Approved
0.6514 Remote Similarity NPD3168 Discontinued
0.6512 Remote Similarity NPD6033 Approved
0.6509 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6504 Remote Similarity NPD7115 Discovery
0.65 Remote Similarity NPD8413 Clinical (unspecified phase)
0.65 Remote Similarity NPD6649 Approved
0.65 Remote Similarity NPD8130 Phase 1
0.65 Remote Similarity NPD6650 Approved
0.6471 Remote Similarity NPD4061 Clinical (unspecified phase)
0.646 Remote Similarity NPD4755 Approved
0.6455 Remote Similarity NPD7515 Phase 2
0.6455 Remote Similarity NPD7087 Discontinued
0.6441 Remote Similarity NPD5697 Approved
0.6441 Remote Similarity NPD5701 Approved
0.6422 Remote Similarity NPD5328 Approved
0.6417 Remote Similarity NPD4634 Approved
0.6417 Remote Similarity NPD7290 Approved
0.6417 Remote Similarity NPD6883 Approved
0.6417 Remote Similarity NPD7102 Approved
0.6415 Remote Similarity NPD4786 Approved
0.6408 Remote Similarity NPD6683 Phase 2
0.6396 Remote Similarity NPD4202 Approved
0.6387 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6379 Remote Similarity NPD7632 Discontinued
0.6373 Remote Similarity NPD5776 Phase 2
0.6373 Remote Similarity NPD6925 Approved
0.6364 Remote Similarity NPD4243 Approved
0.6364 Remote Similarity NPD6869 Approved
0.6364 Remote Similarity NPD6847 Approved
0.6364 Remote Similarity NPD6617 Approved
0.6355 Remote Similarity NPD6893 Approved
0.6348 Remote Similarity NPD4696 Approved
0.6348 Remote Similarity NPD5285 Approved
0.6348 Remote Similarity NPD4700 Approved
0.6348 Remote Similarity NPD5286 Approved
0.6346 Remote Similarity NPD7509 Discontinued
0.6346 Remote Similarity NPD7514 Phase 3
0.6339 Remote Similarity NPD7900 Approved
0.6339 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6333 Remote Similarity NPD6012 Approved
0.6333 Remote Similarity NPD6014 Approved
0.6333 Remote Similarity NPD6013 Approved
0.6328 Remote Similarity NPD7604 Phase 2
0.6316 Remote Similarity NPD6083 Phase 2
0.6316 Remote Similarity NPD6084 Phase 2
0.6311 Remote Similarity NPD7145 Approved
0.6306 Remote Similarity NPD6079 Approved
0.6299 Remote Similarity NPD5983 Phase 2
0.6296 Remote Similarity NPD3618 Phase 1
0.6293 Remote Similarity NPD5344 Discontinued
0.6293 Remote Similarity NPD4159 Approved
0.6283 Remote Similarity NPD7991 Discontinued
0.6281 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6263 Remote Similarity NPD2687 Approved
0.6263 Remote Similarity NPD2686 Approved
0.6263 Remote Similarity NPD2254 Approved
0.6261 Remote Similarity NPD4225 Approved
0.625 Remote Similarity NPD6011 Approved
0.6239 Remote Similarity NPD5224 Approved
0.6239 Remote Similarity NPD5226 Approved
0.6239 Remote Similarity NPD5211 Phase 2
0.6239 Remote Similarity NPD5225 Approved
0.6239 Remote Similarity NPD4633 Approved
0.6238 Remote Similarity NPD4785 Approved
0.6238 Remote Similarity NPD4784 Approved
0.6231 Remote Similarity NPD6336 Discontinued
0.623 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6226 Remote Similarity NPD3667 Approved
0.6218 Remote Similarity NPD6008 Approved
0.6218 Remote Similarity NPD4768 Approved
0.6218 Remote Similarity NPD4767 Approved
0.62 Remote Similarity NPD7152 Approved
0.62 Remote Similarity NPD7151 Approved
0.62 Remote Similarity NPD7150 Approved
0.619 Remote Similarity NPD4748 Discontinued
0.619 Remote Similarity NPD7332 Phase 2
0.6186 Remote Similarity NPD5174 Approved
0.6186 Remote Similarity NPD5175 Approved
0.6168 Remote Similarity NPD3669 Approved
0.6168 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6162 Remote Similarity NPD6922 Approved
0.6162 Remote Similarity NPD6923 Approved
0.6161 Remote Similarity NPD7637 Suspended
0.616 Remote Similarity NPD6940 Discontinued
0.6154 Remote Similarity NPD5223 Approved
0.6134 Remote Similarity NPD5141 Approved
0.6132 Remote Similarity NPD6898 Phase 1
0.6132 Remote Similarity NPD6902 Approved
0.6126 Remote Similarity NPD6051 Approved
0.6126 Remote Similarity NPD4753 Phase 2
0.6121 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6116 Remote Similarity NPD4729 Approved
0.6116 Remote Similarity NPD4730 Approved
0.6116 Remote Similarity NPD8174 Phase 2
0.61 Remote Similarity NPD7144 Approved
0.61 Remote Similarity NPD7143 Approved
0.61 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6087 Remote Similarity NPD5222 Approved
0.6087 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6087 Remote Similarity NPD4697 Phase 3
0.6087 Remote Similarity NPD5221 Approved
0.6083 Remote Similarity NPD5357 Phase 1
0.6061 Remote Similarity NPD8074 Phase 3
0.605 Remote Similarity NPD4754 Approved
0.6045 Remote Similarity NPD5956 Approved
0.6036 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6034 Remote Similarity NPD5173 Approved
0.6033 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6032 Remote Similarity NPD6274 Approved
0.6019 Remote Similarity NPD5275 Approved
0.6019 Remote Similarity NPD4190 Phase 3
0.6016 Remote Similarity NPD5250 Approved
0.6016 Remote Similarity NPD7100 Approved
0.6016 Remote Similarity NPD7101 Approved
0.6016 Remote Similarity NPD5249 Phase 3
0.6016 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