Structure

Physi-Chem Properties

Molecular Weight:  232.15
Volume:  257.918
LogP:  2.868
LogD:  2.395
LogS:  -3.732
# Rotatable Bonds:  2
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.795
Synthetic Accessibility Score:  3.267
Fsp3:  0.533
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.584
MDCK Permeability:  1.7793379811337218e-05
Pgp-inhibitor:  0.331
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.765
30% Bioavailability (F30%):  0.531

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.857
Plasma Protein Binding (PPB):  85.72052764892578%
Volume Distribution (VD):  1.067
Pgp-substrate:  25.541603088378906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.857
CYP1A2-substrate:  0.913
CYP2C19-inhibitor:  0.276
CYP2C19-substrate:  0.814
CYP2C9-inhibitor:  0.167
CYP2C9-substrate:  0.647
CYP2D6-inhibitor:  0.222
CYP2D6-substrate:  0.423
CYP3A4-inhibitor:  0.071
CYP3A4-substrate:  0.413

ADMET: Excretion

Clearance (CL):  2.722
Half-life (T1/2):  0.608

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.1
Drug-inuced Liver Injury (DILI):  0.195
AMES Toxicity:  0.057
Rat Oral Acute Toxicity:  0.105
Maximum Recommended Daily Dose:  0.181
Skin Sensitization:  0.068
Carcinogencity:  0.028
Eye Corrosion:  0.004
Eye Irritation:  0.212
Respiratory Toxicity:  0.03

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

  Natural Product: NPC274833

Natural Product ID:  NPC274833
Common Name*:   6-O-Beta-D-Glucopyranosyl-20-O-Beta-D-Glucopyranosyldammar-25-En-24-One-3Beta,6Alpha,12Beta,20(S)-Tetrol
IUPAC Name:   (6S)-6-[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-1-en-3-one
Synonyms:   vina-ginsenoside R25
Standard InCHIKey:  KJZQRDAZSWKILI-OGGKGQCOSA-N
Standard InCHI:  InChI=1S/C42H70O15/c1-19(2)21(45)10-14-42(8,57-37-34(53)32(51)30(49)25(18-44)56-37)20-9-13-40(6)28(20)22(46)15-26-39(5)12-11-27(47)38(3,4)35(39)23(16-41(26,40)7)54-36-33(52)31(50)29(48)24(17-43)55-36/h20,22-37,43-44,46-53H,1,9-18H2,2-8H3/t20-,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]2C[C@]3(C)[C@@H]([C@@]4([C@@H]2C(C)(C)[C@@H](O)CC4)C)C[C@H]([C@H]2[C@@]3(C)CC[C@@H]2[C@@](O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)(CCC(=O)C(=C)C)C)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503328
PubChem CID:   10629247
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
NPO25128 Panax vietnamensis Species Araliaceae Eukaryota n.a. Vietnamese n.a. PMID[11325227]
NPO25128 Panax vietnamensis Species Araliaceae 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
NPT993 Cell Line Hepatocyte Mus musculus Survival = 35.6 % PMID[507244]
NPT993 Cell Line Hepatocyte Mus musculus Survival = 44.3 % PMID[507244]
NPT993 Cell Line Hepatocyte Mus musculus Survival = 38.4 % PMID[507244]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 19.2 % PMID[507244]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 48.2 % PMID[507244]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 28.3 % PMID[507244]
NPT993 Cell Line Hepatocyte Mus musculus Activity = 8.2 % PMID[507244]
NPT993 Cell Line Hepatocyte Mus musculus Activity = 20.5 % PMID[507244]
NPT993 Cell Line Hepatocyte Mus musculus Activity = 12.0 % PMID[507244]

☑ 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 NPC274833 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
0.9903 High Similarity NPC472719
0.9903 High Similarity NPC207845
0.9804 High Similarity NPC8431
0.9623 High Similarity NPC472718
0.9238 High Similarity NPC51947
0.9238 High Similarity NPC473844
0.9143 High Similarity NPC88744
0.9074 High Similarity NPC73986
0.9065 High Similarity NPC11035
0.9065 High Similarity NPC204392
0.9065 High Similarity NPC91838
0.9065 High Similarity NPC1876
0.9065 High Similarity NPC240734
0.9065 High Similarity NPC275668
0.9057 High Similarity NPC240125
0.9057 High Similarity NPC91583
0.8981 High Similarity NPC470543
0.8981 High Similarity NPC210420
0.8981 High Similarity NPC474265
0.8981 High Similarity NPC145625
0.8899 High Similarity NPC146563
0.8889 High Similarity NPC272242
0.8868 High Similarity NPC287269
0.8846 High Similarity NPC94919
0.8818 High Similarity NPC473882
0.8818 High Similarity NPC474557
0.8818 High Similarity NPC54395
0.8818 High Similarity NPC469821
0.8807 High Similarity NPC471244
0.8807 High Similarity NPC471245
0.8807 High Similarity NPC157929
0.8796 High Similarity NPC154856
0.8796 High Similarity NPC475317
0.8796 High Similarity NPC52241
0.8739 High Similarity NPC469823
0.8739 High Similarity NPC137414
0.8739 High Similarity NPC469820
0.8739 High Similarity NPC88945
0.8739 High Similarity NPC279638
0.8727 High Similarity NPC471248
0.8727 High Similarity NPC260665
0.8727 High Similarity NPC94141
0.8727 High Similarity NPC102619
0.8725 High Similarity NPC472989
0.8716 High Similarity NPC63244
0.8716 High Similarity NPC122339
0.8704 High Similarity NPC131903
0.8661 High Similarity NPC477252
0.8661 High Similarity NPC473304
0.8661 High Similarity NPC156651
0.8654 High Similarity NPC20028
0.8649 High Similarity NPC17165
0.8649 High Similarity NPC74727
0.8649 High Similarity NPC477580
0.8649 High Similarity NPC165439
0.8636 High Similarity NPC243572
0.8636 High Similarity NPC477253
0.8636 High Similarity NPC473303
0.8636 High Similarity NPC233003
0.8636 High Similarity NPC130427
0.8624 High Similarity NPC473324
0.8624 High Similarity NPC137104
0.8624 High Similarity NPC474786
0.8624 High Similarity NPC471476
0.8624 High Similarity NPC320383
0.8611 High Similarity NPC472988
0.8611 High Similarity NPC224414
0.8611 High Similarity NPC38217
0.8609 High Similarity NPC475431
0.8598 High Similarity NPC130511
0.8598 High Similarity NPC307660
0.8596 High Similarity NPC108072
0.8585 High Similarity NPC120123
0.8585 High Similarity NPC157659
0.8585 High Similarity NPC155010
0.8585 High Similarity NPC189852
0.8585 High Similarity NPC286969
0.8585 High Similarity NPC211879
0.8585 High Similarity NPC114874
0.8585 High Similarity NPC16520
0.8585 High Similarity NPC473020
0.8585 High Similarity NPC131479
0.8585 High Similarity NPC8039
0.8585 High Similarity NPC31907
0.8585 High Similarity NPC472252
0.8585 High Similarity NPC245280
0.8584 High Similarity NPC475632
0.8584 High Similarity NPC239293
0.8584 High Similarity NPC469822
0.8584 High Similarity NPC86020
0.8571 High Similarity NPC229752
0.8571 High Similarity NPC477172
0.8559 High Similarity NPC189884
0.8559 High Similarity NPC132668
0.8559 High Similarity NPC251309
0.8559 High Similarity NPC204458
0.8559 High Similarity NPC138334
0.8559 High Similarity NPC47063
0.8545 High Similarity NPC285410
0.8545 High Similarity NPC477073
0.8545 High Similarity NPC250481
0.8545 High Similarity NPC263827
0.8532 High Similarity NPC469744
0.8532 High Similarity NPC51925
0.8532 High Similarity NPC274827
0.8532 High Similarity NPC125361
0.8532 High Similarity NPC43976
0.8532 High Similarity NPC296761
0.8532 High Similarity NPC154085
0.8522 High Similarity NPC476675
0.8522 High Similarity NPC470478
0.8519 High Similarity NPC234160
0.8519 High Similarity NPC67745
0.8519 High Similarity NPC471461
0.8505 High Similarity NPC476360
0.8505 High Similarity NPC476361
0.8505 High Similarity NPC475521
0.8505 High Similarity NPC273879
0.8505 High Similarity NPC165033
0.8496 Intermediate Similarity NPC78836
0.8491 Intermediate Similarity NPC159036
0.8491 Intermediate Similarity NPC312553
0.8491 Intermediate Similarity NPC310031
0.8491 Intermediate Similarity NPC288694
0.8491 Intermediate Similarity NPC80191
0.8468 Intermediate Similarity NPC46388
0.8468 Intermediate Similarity NPC471967
0.8468 Intermediate Similarity NPC37739
0.8468 Intermediate Similarity NPC256798
0.8468 Intermediate Similarity NPC474927
0.8468 Intermediate Similarity NPC128925
0.8462 Intermediate Similarity NPC469841
0.8462 Intermediate Similarity NPC469842
0.8455 Intermediate Similarity NPC59804
0.8455 Intermediate Similarity NPC475296
0.8455 Intermediate Similarity NPC129340
0.8455 Intermediate Similarity NPC106760
0.8455 Intermediate Similarity NPC90856
0.8455 Intermediate Similarity NPC78046
0.8455 Intermediate Similarity NPC136877
0.8455 Intermediate Similarity NPC85391
0.8455 Intermediate Similarity NPC270667
0.8455 Intermediate Similarity NPC474589
0.8455 Intermediate Similarity NPC269095
0.8455 Intermediate Similarity NPC174679
0.8455 Intermediate Similarity NPC164194
0.8455 Intermediate Similarity NPC127056
0.8455 Intermediate Similarity NPC29069
0.8455 Intermediate Similarity NPC56713
0.8455 Intermediate Similarity NPC279554
0.8448 Intermediate Similarity NPC28532
0.844 Intermediate Similarity NPC89860
0.844 Intermediate Similarity NPC189663
0.844 Intermediate Similarity NPC471094
0.844 Intermediate Similarity NPC63841
0.844 Intermediate Similarity NPC55973
0.844 Intermediate Similarity NPC469733
0.844 Intermediate Similarity NPC473410
0.844 Intermediate Similarity NPC469984
0.844 Intermediate Similarity NPC195708
0.844 Intermediate Similarity NPC232133
0.844 Intermediate Similarity NPC469729
0.8435 Intermediate Similarity NPC471406
0.8435 Intermediate Similarity NPC308459
0.8435 Intermediate Similarity NPC475187
0.8435 Intermediate Similarity NPC470312
0.8426 Intermediate Similarity NPC208594
0.8426 Intermediate Similarity NPC473199
0.8426 Intermediate Similarity NPC69737
0.8426 Intermediate Similarity NPC127801
0.8426 Intermediate Similarity NPC56656
0.8426 Intermediate Similarity NPC160816
0.8426 Intermediate Similarity NPC152584
0.8426 Intermediate Similarity NPC194842
0.8426 Intermediate Similarity NPC208477
0.8426 Intermediate Similarity NPC12823
0.8426 Intermediate Similarity NPC269627
0.8411 Intermediate Similarity NPC16573
0.8411 Intermediate Similarity NPC34562
0.8407 Intermediate Similarity NPC160415
0.8407 Intermediate Similarity NPC58448
0.8396 Intermediate Similarity NPC4831
0.8396 Intermediate Similarity NPC14634
0.8396 Intermediate Similarity NPC129372
0.8396 Intermediate Similarity NPC160734
0.8396 Intermediate Similarity NPC472023
0.8396 Intermediate Similarity NPC309425
0.8396 Intermediate Similarity NPC47566
0.8396 Intermediate Similarity NPC88000
0.8393 Intermediate Similarity NPC271138
0.8393 Intermediate Similarity NPC62696
0.8393 Intermediate Similarity NPC477944
0.8393 Intermediate Similarity NPC269315
0.8393 Intermediate Similarity NPC293038
0.8393 Intermediate Similarity NPC477074
0.8393 Intermediate Similarity NPC471252
0.8378 Intermediate Similarity NPC213320
0.8378 Intermediate Similarity NPC30397
0.8378 Intermediate Similarity NPC179434
0.8378 Intermediate Similarity NPC164419

  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 NPC274833 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
0.8727 High Similarity NPD8133 Approved
0.8198 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD6412 Phase 2
0.8165 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.8067 Intermediate Similarity NPD8328 Phase 3
0.7966 Intermediate Similarity NPD8377 Approved
0.7966 Intermediate Similarity NPD8294 Approved
0.7934 Intermediate Similarity NPD7507 Approved
0.7899 Intermediate Similarity NPD8380 Approved
0.7899 Intermediate Similarity NPD8379 Approved
0.7899 Intermediate Similarity NPD8378 Approved
0.7899 Intermediate Similarity NPD8296 Approved
0.7899 Intermediate Similarity NPD8335 Approved
0.7899 Intermediate Similarity NPD8033 Approved
0.7863 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD7736 Approved
0.7742 Intermediate Similarity NPD7319 Approved
0.7686 Intermediate Similarity NPD6370 Approved
0.7647 Intermediate Similarity NPD7328 Approved
0.7647 Intermediate Similarity NPD7327 Approved
0.7642 Intermediate Similarity NPD8034 Phase 2
0.7642 Intermediate Similarity NPD8035 Phase 2
0.7632 Intermediate Similarity NPD6686 Approved
0.7583 Intermediate Similarity NPD7516 Approved
0.757 Intermediate Similarity NPD8171 Discontinued
0.7521 Intermediate Similarity NPD6054 Approved
0.7459 Intermediate Similarity NPD7503 Approved
0.744 Intermediate Similarity NPD8293 Discontinued
0.7377 Intermediate Similarity NPD6059 Approved
0.7373 Intermediate Similarity NPD6882 Approved
0.7373 Intermediate Similarity NPD8297 Approved
0.7317 Intermediate Similarity NPD6015 Approved
0.7317 Intermediate Similarity NPD6016 Approved
0.728 Intermediate Similarity NPD7492 Approved
0.7273 Intermediate Similarity NPD6009 Approved
0.7258 Intermediate Similarity NPD5988 Approved
0.7238 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD6319 Approved
0.7222 Intermediate Similarity NPD6616 Approved
0.7167 Intermediate Similarity NPD4632 Approved
0.7165 Intermediate Similarity NPD7078 Approved
0.7143 Intermediate Similarity NPD7902 Approved
0.7143 Intermediate Similarity NPD6650 Approved
0.7143 Intermediate Similarity NPD6649 Approved
0.7131 Intermediate Similarity NPD7115 Discovery
0.7119 Intermediate Similarity NPD6372 Approved
0.7119 Intermediate Similarity NPD6373 Approved
0.7063 Intermediate Similarity NPD6067 Discontinued
0.7048 Intermediate Similarity NPD4788 Approved
0.704 Intermediate Similarity NPD8515 Approved
0.704 Intermediate Similarity NPD8517 Approved
0.704 Intermediate Similarity NPD8513 Phase 3
0.704 Intermediate Similarity NPD8516 Approved
0.7034 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD6881 Approved
0.7034 Intermediate Similarity NPD6899 Approved
0.7027 Intermediate Similarity NPD7748 Approved
0.7009 Intermediate Similarity NPD5739 Approved
0.7009 Intermediate Similarity NPD6402 Approved
0.7009 Intermediate Similarity NPD6675 Approved
0.7009 Intermediate Similarity NPD7128 Approved
0.7 Intermediate Similarity NPD8130 Phase 1
0.6949 Remote Similarity NPD5697 Approved
0.6937 Remote Similarity NPD6399 Phase 3
0.693 Remote Similarity NPD7638 Approved
0.6917 Remote Similarity NPD6883 Approved
0.6917 Remote Similarity NPD7102 Approved
0.6917 Remote Similarity NPD7290 Approved
0.6917 Remote Similarity NPD4634 Approved
0.6891 Remote Similarity NPD7320 Approved
0.6875 Remote Similarity NPD7900 Approved
0.6875 Remote Similarity NPD7901 Clinical (unspecified phase)
0.687 Remote Similarity NPD5286 Approved
0.687 Remote Similarity NPD5285 Approved
0.687 Remote Similarity NPD7639 Approved
0.687 Remote Similarity NPD7640 Approved
0.687 Remote Similarity NPD4696 Approved
0.686 Remote Similarity NPD6847 Approved
0.686 Remote Similarity NPD6869 Approved
0.686 Remote Similarity NPD6617 Approved
0.6852 Remote Similarity NPD3618 Phase 1
0.6847 Remote Similarity NPD6079 Approved
0.6847 Remote Similarity NPD7515 Phase 2
0.6846 Remote Similarity NPD6033 Approved
0.6842 Remote Similarity NPD4755 Approved
0.6833 Remote Similarity NPD6012 Approved
0.6833 Remote Similarity NPD6013 Approved
0.6833 Remote Similarity NPD6014 Approved
0.6818 Remote Similarity NPD5328 Approved
0.6807 Remote Similarity NPD5701 Approved
0.6797 Remote Similarity NPD7604 Phase 2
0.6786 Remote Similarity NPD4202 Approved
0.6774 Remote Similarity NPD6940 Discontinued
0.6772 Remote Similarity NPD5983 Phase 2
0.6752 Remote Similarity NPD5211 Phase 2
0.6752 Remote Similarity NPD5224 Approved
0.6752 Remote Similarity NPD5225 Approved
0.6752 Remote Similarity NPD5226 Approved
0.6752 Remote Similarity NPD4633 Approved
0.675 Remote Similarity NPD6011 Approved
0.6731 Remote Similarity NPD6115 Approved
0.6731 Remote Similarity NPD6697 Approved
0.6731 Remote Similarity NPD6118 Approved
0.6731 Remote Similarity NPD6114 Approved
0.6724 Remote Similarity NPD4700 Approved
0.6723 Remote Similarity NPD6008 Approved
0.6721 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6084 Phase 2
0.6696 Remote Similarity NPD6083 Phase 2
0.6695 Remote Similarity NPD5174 Approved
0.6695 Remote Similarity NPD5175 Approved
0.6694 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6692 Remote Similarity NPD6336 Discontinued
0.6667 Remote Similarity NPD5223 Approved
0.6667 Remote Similarity NPD4786 Approved
0.6639 Remote Similarity NPD5141 Approved
0.6639 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6635 Remote Similarity NPD6116 Phase 1
0.6612 Remote Similarity NPD4730 Approved
0.6612 Remote Similarity NPD4729 Approved
0.6609 Remote Similarity NPD5221 Approved
0.6609 Remote Similarity NPD4697 Phase 3
0.6609 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6609 Remote Similarity NPD5222 Approved
0.6604 Remote Similarity NPD7525 Registered
0.6604 Remote Similarity NPD6928 Phase 2
0.6585 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6583 Remote Similarity NPD4768 Approved
0.6583 Remote Similarity NPD4767 Approved
0.6574 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6574 Remote Similarity NPD3669 Approved
0.6552 Remote Similarity NPD5173 Approved
0.6538 Remote Similarity NPD6117 Approved
0.6522 Remote Similarity NPD5210 Approved
0.6522 Remote Similarity NPD4629 Approved
0.6518 Remote Similarity NPD4753 Phase 2
0.6512 Remote Similarity NPD6921 Approved
0.6508 Remote Similarity NPD6274 Approved
0.6504 Remote Similarity NPD5248 Approved
0.6504 Remote Similarity NPD5247 Approved
0.6504 Remote Similarity NPD5249 Phase 3
0.6504 Remote Similarity NPD5251 Approved
0.6504 Remote Similarity NPD5250 Approved
0.6496 Remote Similarity NPD5696 Approved
0.6493 Remote Similarity NPD5956 Approved
0.6484 Remote Similarity NPD7101 Approved
0.6484 Remote Similarity NPD7100 Approved
0.6481 Remote Similarity NPD3667 Approved
0.6475 Remote Similarity NPD5128 Approved
0.6471 Remote Similarity NPD7632 Discontinued
0.6471 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6442 Remote Similarity NPD3703 Phase 2
0.6429 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6417 Remote Similarity NPD4754 Approved
0.6406 Remote Similarity NPD6335 Approved
0.6397 Remote Similarity NPD8449 Approved
0.6396 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6393 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6389 Remote Similarity NPD1779 Approved
0.6389 Remote Similarity NPD1780 Approved
0.6389 Remote Similarity NPD7625 Phase 1
0.6379 Remote Similarity NPD5695 Phase 3
0.6379 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3133 Approved
0.6364 Remote Similarity NPD3665 Phase 1
0.6364 Remote Similarity NPD3666 Approved
0.6356 Remote Similarity NPD4225 Approved
0.635 Remote Similarity NPD8450 Suspended
0.6346 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6343 Remote Similarity NPD8337 Approved
0.6343 Remote Similarity NPD8336 Approved
0.6328 Remote Similarity NPD6317 Approved
0.632 Remote Similarity NPD5217 Approved
0.632 Remote Similarity NPD5215 Approved
0.632 Remote Similarity NPD5216 Approved
0.6283 Remote Similarity NPD6672 Approved
0.6283 Remote Similarity NPD5737 Approved
0.6279 Remote Similarity NPD6313 Approved
0.6279 Remote Similarity NPD6314 Approved
0.6275 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6275 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6275 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6269 Remote Similarity NPD8074 Phase 3
0.626 Remote Similarity NPD6908 Approved
0.626 Remote Similarity NPD6291 Clinical (unspecified phase)
0.626 Remote Similarity NPD6909 Approved
0.625 Remote Similarity NPD6409 Approved
0.625 Remote Similarity NPD5330 Approved
0.625 Remote Similarity NPD7521 Approved
0.625 Remote Similarity NPD6684 Approved
0.625 Remote Similarity NPD7334 Approved
0.625 Remote Similarity NPD6868 Approved
0.625 Remote Similarity NPD7146 Approved
0.624 Remote Similarity NPD5169 Approved
0.624 Remote Similarity NPD5135 Approved
0.624 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6218 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6204 Remote Similarity NPD7645 Phase 2
0.6195 Remote Similarity NPD7524 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