Structure

Physi-Chem Properties

Molecular Weight:  1028.56
Volume:  1001.471
LogP:  2.816
LogD:  2.822
LogS:  -3.697
# Rotatable Bonds:  10
TPSA:  313.44
# H-Bond Aceptor:  20
# H-Bond Donor:  11
# Rings:  9
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.107
Synthetic Accessibility Score:  6.638
Fsp3:  0.942
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:  -5.927
MDCK Permeability:  3.683917748276144e-05
Pgp-inhibitor:  0.935
Pgp-substrate:  0.202
Human Intestinal Absorption (HIA):  0.978
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.062
Plasma Protein Binding (PPB):  78.08550262451172%
Volume Distribution (VD):  0.119
Pgp-substrate:  13.669551849365234%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.691
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.104
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.007
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.055
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.008

ADMET: Excretion

Clearance (CL):  0.386
Half-life (T1/2):  0.673

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.155
Drug-inuced Liver Injury (DILI):  0.009
AMES Toxicity:  0.095
Rat Oral Acute Toxicity:  0.127
Maximum Recommended Daily Dose:  0.842
Skin Sensitization:  0.049
Carcinogencity:  0.03
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.955

Download Data

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

  Natural Product: NPC166422

Natural Product ID:  NPC166422
Common Name*:   3-O-Beta-D-Xylopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-[Beta-D-Glucopyranosyl-(1->4)]-Alpha-L-Arabinopyranosyl Oleanolic Acid
IUPAC Name:   (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:  
Standard InCHIKey:  YMUVECXYJPPWBW-ZQPXAOBSSA-N
Standard InCHI:  InChI=1S/C52H84O20/c1-23-32(55)40(71-42-37(60)33(56)26(54)21-65-42)39(62)44(67-23)72-41-35(58)28(69-43-38(61)36(59)34(57)27(20-53)68-43)22-66-45(41)70-31-12-13-49(6)29(48(31,4)5)11-14-51(8)30(49)10-9-24-25-19-47(2,3)15-17-52(25,46(63)64)18-16-50(24,51)7/h9,23,25-45,53-62H,10-22H2,1-8H3,(H,63,64)/t23-,25-,26+,27+,28-,29-,30+,31-,32-,33-,34+,35-,36-,37+,38+,39+,40+,41+,42-,43-,44-,45-,49-,50+,51+,52-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)C1(C)C)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](CO1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2430029
PubChem CID:   73346237
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
NPO32682 anemone taipaiensis Species Ranunculaceae Eukaryota rhizomes n.a. n.a. PMID[23992864]

☑ 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 7560.0 nM PMID[503774]
NPT81 Cell Line A549 Homo sapiens IC50 = 8320.0 nM PMID[503774]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 2370.0 nM PMID[503774]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 5230.0 nM PMID[503774]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2250.0 nM PMID[503774]

☑ 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 NPC166422 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 NPC251263
1.0 High Similarity NPC151543
1.0 High Similarity NPC192600
1.0 High Similarity NPC114304
1.0 High Similarity NPC475467
1.0 High Similarity NPC46665
1.0 High Similarity NPC475287
1.0 High Similarity NPC241909
1.0 High Similarity NPC219180
1.0 High Similarity NPC114287
1.0 High Similarity NPC133818
1.0 High Similarity NPC473826
1.0 High Similarity NPC174720
1.0 High Similarity NPC323341
1.0 High Similarity NPC309714
1.0 High Similarity NPC295823
1.0 High Similarity NPC155410
0.9905 High Similarity NPC236638
0.9905 High Similarity NPC67857
0.9905 High Similarity NPC76972
0.9905 High Similarity NPC123199
0.9905 High Similarity NPC57484
0.9905 High Similarity NPC224381
0.9905 High Similarity NPC305981
0.9905 High Similarity NPC294453
0.9905 High Similarity NPC227551
0.9905 High Similarity NPC65105
0.9905 High Similarity NPC204414
0.9905 High Similarity NPC476068
0.9905 High Similarity NPC4328
0.9905 High Similarity NPC41061
0.9905 High Similarity NPC471550
0.9905 High Similarity NPC250247
0.9905 High Similarity NPC261506
0.9905 High Similarity NPC473714
0.9905 High Similarity NPC100639
0.9905 High Similarity NPC161717
0.9905 High Similarity NPC471385
0.9905 High Similarity NPC293330
0.9905 High Similarity NPC54636
0.9905 High Similarity NPC202828
0.9905 High Similarity NPC71065
0.9905 High Similarity NPC119592
0.9905 High Similarity NPC309907
0.9905 High Similarity NPC43550
0.9905 High Similarity NPC70809
0.9905 High Similarity NPC475140
0.9905 High Similarity NPC475160
0.9905 High Similarity NPC79643
0.9905 High Similarity NPC469782
0.9905 High Similarity NPC298034
0.9905 High Similarity NPC60557
0.9904 High Similarity NPC324875
0.9904 High Similarity NPC469946
0.9904 High Similarity NPC276093
0.9904 High Similarity NPC109079
0.9904 High Similarity NPC10320
0.9904 High Similarity NPC475504
0.9904 High Similarity NPC471383
0.9904 High Similarity NPC104400
0.9904 High Similarity NPC104071
0.9904 High Similarity NPC102439
0.9904 High Similarity NPC475516
0.9904 High Similarity NPC473373
0.9904 High Similarity NPC139044
0.9904 High Similarity NPC292677
0.9904 High Similarity NPC101744
0.9904 High Similarity NPC257468
0.9904 High Similarity NPC79718
0.9811 High Similarity NPC161674
0.9811 High Similarity NPC75287
0.9811 High Similarity NPC305267
0.9811 High Similarity NPC476992
0.9811 High Similarity NPC51465
0.9811 High Similarity NPC26626
0.9811 High Similarity NPC471384
0.9811 High Similarity NPC288205
0.981 High Similarity NPC96641
0.981 High Similarity NPC73318
0.981 High Similarity NPC258885
0.981 High Similarity NPC124296
0.981 High Similarity NPC163183
0.981 High Similarity NPC473343
0.981 High Similarity NPC150400
0.981 High Similarity NPC134835
0.9808 High Similarity NPC164419
0.972 High Similarity NPC33012
0.972 High Similarity NPC220160
0.972 High Similarity NPC475514
0.972 High Similarity NPC475119
0.972 High Similarity NPC102505
0.972 High Similarity NPC148417
0.972 High Similarity NPC136768
0.972 High Similarity NPC191827
0.972 High Similarity NPC473824
0.972 High Similarity NPC104137
0.972 High Similarity NPC85154
0.972 High Similarity NPC470876
0.972 High Similarity NPC68175
0.972 High Similarity NPC309223
0.972 High Similarity NPC185466
0.972 High Similarity NPC473452
0.972 High Similarity NPC8524
0.972 High Similarity NPC475209
0.972 High Similarity NPC286457
0.972 High Similarity NPC123522
0.972 High Similarity NPC69811
0.972 High Similarity NPC110633
0.9717 High Similarity NPC475486
0.9717 High Similarity NPC164389
0.9714 High Similarity NPC139894
0.9714 High Similarity NPC473383
0.9712 High Similarity NPC474589
0.9712 High Similarity NPC164194
0.9712 High Similarity NPC90856
0.9712 High Similarity NPC127056
0.9712 High Similarity NPC270667
0.9712 High Similarity NPC279554
0.9712 High Similarity NPC29069
0.9712 High Similarity NPC174679
0.9712 High Similarity NPC475296
0.9712 High Similarity NPC59804
0.9712 High Similarity NPC136877
0.9712 High Similarity NPC56713
0.963 High Similarity NPC473459
0.963 High Similarity NPC475899
0.963 High Similarity NPC36831
0.963 High Similarity NPC237191
0.9626 High Similarity NPC160415
0.9626 High Similarity NPC291903
0.9626 High Similarity NPC37134
0.9626 High Similarity NPC58448
0.9619 High Similarity NPC108748
0.9619 High Similarity NPC235841
0.9619 High Similarity NPC211798
0.9619 High Similarity NPC473481
0.9619 High Similarity NPC297208
0.9619 High Similarity NPC30397
0.9619 High Similarity NPC179434
0.9615 High Similarity NPC57362
0.9615 High Similarity NPC237503
0.9615 High Similarity NPC167383
0.9615 High Similarity NPC306746
0.9615 High Similarity NPC204407
0.9541 High Similarity NPC51564
0.9541 High Similarity NPC25663
0.9541 High Similarity NPC477464
0.9541 High Similarity NPC135849
0.9541 High Similarity NPC207738
0.9541 High Similarity NPC473386
0.9541 High Similarity NPC471577
0.9537 High Similarity NPC471547
0.9537 High Similarity NPC323359
0.9537 High Similarity NPC300419
0.9537 High Similarity NPC471580
0.9528 High Similarity NPC1046
0.9528 High Similarity NPC256798
0.9528 High Similarity NPC128925
0.9528 High Similarity NPC80843
0.9524 High Similarity NPC7870
0.9524 High Similarity NPC476880
0.9524 High Similarity NPC476881
0.9524 High Similarity NPC269095
0.9524 High Similarity NPC476886
0.9524 High Similarity NPC476883
0.9524 High Similarity NPC78046
0.9524 High Similarity NPC75747
0.9524 High Similarity NPC110139
0.9524 High Similarity NPC102914
0.9524 High Similarity NPC274507
0.9524 High Similarity NPC476885
0.9524 High Similarity NPC476887
0.9524 High Similarity NPC476884
0.9524 High Similarity NPC68419
0.9524 High Similarity NPC476882
0.9524 High Similarity NPC108709
0.9524 High Similarity NPC199457
0.9519 High Similarity NPC177246
0.9519 High Similarity NPC476123
0.9519 High Similarity NPC284807
0.9519 High Similarity NPC28198
0.9455 High Similarity NPC153673
0.9455 High Similarity NPC37860
0.9455 High Similarity NPC268184
0.9455 High Similarity NPC476991
0.9455 High Similarity NPC142151
0.9455 High Similarity NPC267694
0.9455 High Similarity NPC110385
0.9455 High Similarity NPC144644
0.945 High Similarity NPC471548
0.945 High Similarity NPC109588
0.945 High Similarity NPC105800
0.945 High Similarity NPC232237
0.9439 High Similarity NPC47063
0.9439 High Similarity NPC204458
0.9439 High Similarity NPC475208
0.9439 High Similarity NPC238935
0.9439 High Similarity NPC189884
0.9439 High Similarity NPC138334
0.9434 High Similarity NPC31839

  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 NPC166422 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
0.887 High Similarity NPD8328 Phase 3
0.8716 High Similarity NPD8132 Clinical (unspecified phase)
0.8673 High Similarity NPD8295 Clinical (unspecified phase)
0.8571 High Similarity NPD8133 Approved
0.8036 Intermediate Similarity NPD6412 Phase 2
0.7983 Intermediate Similarity NPD8377 Approved
0.7983 Intermediate Similarity NPD8294 Approved
0.7965 Intermediate Similarity NPD6686 Approved
0.7917 Intermediate Similarity NPD8379 Approved
0.7917 Intermediate Similarity NPD8296 Approved
0.7917 Intermediate Similarity NPD8335 Approved
0.7917 Intermediate Similarity NPD8380 Approved
0.7917 Intermediate Similarity NPD8378 Approved
0.785 Intermediate Similarity NPD7748 Approved
0.7805 Intermediate Similarity NPD7507 Approved
0.7798 Intermediate Similarity NPD7902 Approved
0.7769 Intermediate Similarity NPD8516 Approved
0.7769 Intermediate Similarity NPD8033 Approved
0.7769 Intermediate Similarity NPD8515 Approved
0.7769 Intermediate Similarity NPD8517 Approved
0.7664 Intermediate Similarity NPD7515 Phase 2
0.7623 Intermediate Similarity NPD8513 Phase 3
0.7619 Intermediate Similarity NPD7319 Approved
0.754 Intermediate Similarity NPD7736 Approved
0.7523 Intermediate Similarity NPD7900 Approved
0.7523 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7521 Intermediate Similarity NPD7328 Approved
0.7521 Intermediate Similarity NPD7327 Approved
0.7459 Intermediate Similarity NPD7516 Approved
0.7391 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD7503 Approved
0.7323 Intermediate Similarity NPD8293 Discontinued
0.7311 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD8035 Phase 2
0.7182 Intermediate Similarity NPD8034 Phase 2
0.7143 Intermediate Similarity NPD6370 Approved
0.7107 Intermediate Similarity NPD8297 Approved
0.7107 Intermediate Similarity NPD6882 Approved
0.7105 Intermediate Similarity NPD7638 Approved
0.7043 Intermediate Similarity NPD7640 Approved
0.7043 Intermediate Similarity NPD7639 Approved
0.7031 Intermediate Similarity NPD7492 Approved
0.7019 Intermediate Similarity NPD7645 Phase 2
0.7016 Intermediate Similarity NPD6009 Approved
0.7 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6054 Approved
0.6984 Remote Similarity NPD6319 Approved
0.6984 Remote Similarity NPD6059 Approved
0.6977 Remote Similarity NPD6616 Approved
0.6964 Remote Similarity NPD8171 Discontinued
0.6964 Remote Similarity NPD6399 Phase 3
0.6953 Remote Similarity NPD6067 Discontinued
0.6944 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7078 Approved
0.6917 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6911 Remote Similarity NPD4632 Approved
0.6891 Remote Similarity NPD6402 Approved
0.6891 Remote Similarity NPD5739 Approved
0.6891 Remote Similarity NPD6675 Approved
0.6891 Remote Similarity NPD7128 Approved
0.686 Remote Similarity NPD6372 Approved
0.686 Remote Similarity NPD6373 Approved
0.6803 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6797 Remote Similarity NPD6016 Approved
0.6797 Remote Similarity NPD6015 Approved
0.6777 Remote Similarity NPD7320 Approved
0.6777 Remote Similarity NPD6899 Approved
0.6777 Remote Similarity NPD6881 Approved
0.6748 Remote Similarity NPD6649 Approved
0.6748 Remote Similarity NPD6650 Approved
0.6748 Remote Similarity NPD8130 Phase 1
0.6746 Remote Similarity NPD7115 Discovery
0.6744 Remote Similarity NPD5988 Approved
0.6741 Remote Similarity NPD8450 Suspended
0.6726 Remote Similarity NPD6411 Approved
0.6694 Remote Similarity NPD5697 Approved
0.6694 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD8074 Phase 3
0.6667 Remote Similarity NPD6883 Approved
0.6667 Remote Similarity NPD7290 Approved
0.6667 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD8449 Approved
0.6637 Remote Similarity NPD6698 Approved
0.6637 Remote Similarity NPD46 Approved
0.6613 Remote Similarity NPD6847 Approved
0.6613 Remote Similarity NPD6617 Approved
0.6613 Remote Similarity NPD6869 Approved
0.6607 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6585 Remote Similarity NPD6013 Approved
0.6585 Remote Similarity NPD6014 Approved
0.6585 Remote Similarity NPD6012 Approved
0.6581 Remote Similarity NPD6083 Phase 2
0.6581 Remote Similarity NPD6084 Phase 2
0.6577 Remote Similarity NPD3618 Phase 1
0.6565 Remote Similarity NPD7604 Phase 2
0.6557 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6549 Remote Similarity NPD5328 Approved
0.6549 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6101 Approved
0.6545 Remote Similarity NPD4786 Approved
0.6538 Remote Similarity NPD5983 Phase 2
0.6525 Remote Similarity NPD4225 Approved
0.6518 Remote Similarity NPD3573 Approved
0.6514 Remote Similarity NPD3667 Approved
0.6504 Remote Similarity NPD6011 Approved
0.65 Remote Similarity NPD7632 Discontinued
0.6493 Remote Similarity NPD6033 Approved
0.648 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6475 Remote Similarity NPD6008 Approved
0.6466 Remote Similarity NPD6336 Discontinued
0.6455 Remote Similarity NPD3669 Approved
0.6455 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6441 Remote Similarity NPD4755 Approved
0.6435 Remote Similarity NPD6079 Approved
0.6435 Remote Similarity NPD7983 Approved
0.6429 Remote Similarity NPD7521 Approved
0.6429 Remote Similarity NPD7334 Approved
0.6429 Remote Similarity NPD6684 Approved
0.6429 Remote Similarity NPD7146 Approved
0.6429 Remote Similarity NPD6409 Approved
0.6429 Remote Similarity NPD5330 Approved
0.6412 Remote Similarity NPD6921 Approved
0.6406 Remote Similarity NPD6940 Discontinued
0.6404 Remote Similarity NPD7285 Clinical (unspecified phase)
0.64 Remote Similarity NPD4634 Approved
0.6387 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6379 Remote Similarity NPD5778 Approved
0.6379 Remote Similarity NPD5779 Approved
0.6379 Remote Similarity NPD4202 Approved
0.6333 Remote Similarity NPD4696 Approved
0.6333 Remote Similarity NPD5285 Approved
0.6333 Remote Similarity NPD5286 Approved
0.6333 Remote Similarity NPD4700 Approved
0.633 Remote Similarity NPD7525 Registered
0.6316 Remote Similarity NPD6903 Approved
0.6316 Remote Similarity NPD5737 Approved
0.6316 Remote Similarity NPD6672 Approved
0.6301 Remote Similarity NPD7625 Phase 1
0.6296 Remote Similarity NPD6697 Approved
0.6296 Remote Similarity NPD6115 Approved
0.6296 Remote Similarity NPD6118 Approved
0.6296 Remote Similarity NPD6114 Approved
0.6279 Remote Similarity NPD6274 Approved
0.6273 Remote Similarity NPD1779 Approved
0.6273 Remote Similarity NPD1780 Approved
0.6271 Remote Similarity NPD5695 Phase 3
0.626 Remote Similarity NPD7100 Approved
0.626 Remote Similarity NPD7101 Approved
0.625 Remote Similarity NPD8337 Approved
0.625 Remote Similarity NPD5696 Approved
0.625 Remote Similarity NPD3665 Phase 1
0.625 Remote Similarity NPD8336 Approved
0.625 Remote Similarity NPD3666 Approved
0.625 Remote Similarity NPD3133 Approved
0.6231 Remote Similarity NPD8137 Clinical (unspecified phase)
0.623 Remote Similarity NPD5225 Approved
0.623 Remote Similarity NPD5224 Approved
0.623 Remote Similarity NPD4633 Approved
0.623 Remote Similarity NPD5211 Phase 2
0.623 Remote Similarity NPD5226 Approved
0.6218 Remote Similarity NPD5221 Approved
0.6218 Remote Similarity NPD4697 Phase 3
0.6218 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6218 Remote Similarity NPD5222 Approved
0.621 Remote Similarity NPD4768 Approved
0.621 Remote Similarity NPD4767 Approved
0.6204 Remote Similarity NPD6116 Phase 1
0.6183 Remote Similarity NPD6335 Approved
0.6179 Remote Similarity NPD5175 Approved
0.6179 Remote Similarity NPD5174 Approved
0.6176 Remote Similarity NPD8448 Approved
0.6167 Remote Similarity NPD5173 Approved
0.6165 Remote Similarity NPD6908 Approved
0.6165 Remote Similarity NPD6909 Approved
0.6159 Remote Similarity NPD8391 Approved
0.6159 Remote Similarity NPD8390 Approved
0.6159 Remote Similarity NPD8392 Approved
0.6154 Remote Similarity NPD6868 Approved
0.6148 Remote Similarity NPD8299 Approved
0.6148 Remote Similarity NPD8340 Approved
0.6148 Remote Similarity NPD8342 Approved
0.6148 Remote Similarity NPD5344 Discontinued
0.6148 Remote Similarity NPD5223 Approved
0.6148 Remote Similarity NPD8341 Approved
0.6134 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6129 Remote Similarity NPD5141 Approved
0.6121 Remote Similarity NPD4753 Phase 2
0.6111 Remote Similarity NPD6117 Approved
0.6111 Remote Similarity NPD4729 Approved
0.6111 Remote Similarity NPD4730 Approved
0.6107 Remote Similarity NPD6317 Approved
0.6106 Remote Similarity NPD3668 Phase 3
0.6103 Remote Similarity NPD8451 Approved
0.6083 Remote Similarity NPD7614 Phase 1
0.6083 Remote Similarity NPD7839 Suspended
0.6083 Remote Similarity NPD7732 Phase 3
0.6074 Remote Similarity NPD7830 Approved
0.6074 Remote Similarity NPD7829 Approved
0.6071 Remote Similarity NPD8338 Approved
0.6068 Remote Similarity NPD7838 Discovery

  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