Structure

Physi-Chem Properties

Molecular Weight:  750.46
Volume:  758.006
LogP:  4.014
LogD:  3.938
LogS:  -3.957
# Rotatable Bonds:  6
TPSA:  195.6
# H-Bond Aceptor:  12
# H-Bond Donor:  7
# Rings:  7
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.155
Synthetic Accessibility Score:  5.672
Fsp3:  0.927
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:  -5.605
MDCK Permeability:  7.1720651249052025e-06
Pgp-inhibitor:  0.977
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.691
20% Bioavailability (F20%):  0.017
30% Bioavailability (F30%):  0.644

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.047
Plasma Protein Binding (PPB):  86.90972900390625%
Volume Distribution (VD):  0.499
Pgp-substrate:  8.769725799560547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.627
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.436
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.034
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.077
CYP3A4-inhibitor:  0.087
CYP3A4-substrate:  0.058

ADMET: Excretion

Clearance (CL):  0.903
Half-life (T1/2):  0.423

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.229
Drug-inuced Liver Injury (DILI):  0.009
AMES Toxicity:  0.073
Rat Oral Acute Toxicity:  0.102
Maximum Recommended Daily Dose:  0.891
Skin Sensitization:  0.035
Carcinogencity:  0.052
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC127056

Natural Product ID:  NPC127056
Common Name*:   3Beta-[(O-Beta-D-Glucopyranosyl-(1->2)-Alpha-L-Arabinopyranosyl)Oxy]Olean-12-En-28-Oic Acid
IUPAC Name:   (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(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:  GXWUEMSASMVWKO-LFGJQLCQSA-N
Standard InCHI:  InChI=1S/C41H66O12/c1-36(2)14-16-41(35(48)49)17-15-39(6)21(22(41)18-36)8-9-26-38(5)12-11-27(37(3,4)25(38)10-13-40(26,39)7)52-34-32(28(44)23(43)20-50-34)53-33-31(47)30(46)29(45)24(19-42)51-33/h8,22-34,42-47H,9-20H2,1-7H3,(H,48,49)/t22-,23-,24+,25-,26+,27-,28-,29+,30-,31+,32+,33-,34-,38-,39+,40+,41-/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL540220
PubChem CID:   13878145
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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[11141124]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. leaf n.a. PMID[11735581]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[15844965]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17602526]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO25841 Caulophyllum thalictroides Species Berberidaceae Eukaryota underground parts n.a. n.a. PMID[19449879]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25841 Caulophyllum thalictroides Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5155 Peritassa compta Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5196 Eupatorium argentinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6729 Juniperus brevifolia Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO471 Ardisia neriifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3597 Rheedia acuminata Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6237 Cryptocarya aschersoniana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8418 Anemone flaccida Species Ranunculaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 10.8 ug.mL-1 PMID[558284]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1820.0 nM PMID[558285]

☑ 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 NPC127056 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 NPC59804
1.0 High Similarity NPC475296
1.0 High Similarity NPC474589
1.0 High Similarity NPC29069
1.0 High Similarity NPC270667
1.0 High Similarity NPC136877
1.0 High Similarity NPC174679
1.0 High Similarity NPC90856
1.0 High Similarity NPC164194
1.0 High Similarity NPC56713
1.0 High Similarity NPC279554
0.9902 High Similarity NPC235841
0.9902 High Similarity NPC164419
0.9902 High Similarity NPC108748
0.9902 High Similarity NPC473481
0.9902 High Similarity NPC211798
0.9902 High Similarity NPC297208
0.9902 High Similarity NPC179434
0.9902 High Similarity NPC30397
0.9901 High Similarity NPC306746
0.9901 High Similarity NPC57362
0.9901 High Similarity NPC167383
0.9901 High Similarity NPC204407
0.9901 High Similarity NPC237503
0.9806 High Similarity NPC473373
0.9806 High Similarity NPC292677
0.9806 High Similarity NPC1046
0.9806 High Similarity NPC79718
0.9806 High Similarity NPC276093
0.9806 High Similarity NPC102439
0.9806 High Similarity NPC139044
0.9806 High Similarity NPC256798
0.9806 High Similarity NPC475516
0.9806 High Similarity NPC10320
0.9806 High Similarity NPC324875
0.9806 High Similarity NPC104400
0.9806 High Similarity NPC471383
0.9806 High Similarity NPC104071
0.9806 High Similarity NPC257468
0.9806 High Similarity NPC139894
0.9806 High Similarity NPC469946
0.9806 High Similarity NPC101744
0.9806 High Similarity NPC128925
0.9806 High Similarity NPC473383
0.9806 High Similarity NPC475504
0.9806 High Similarity NPC109079
0.9806 High Similarity NPC80843
0.9804 High Similarity NPC269095
0.9804 High Similarity NPC78046
0.9804 High Similarity NPC274507
0.9804 High Similarity NPC476887
0.9804 High Similarity NPC75747
0.9804 High Similarity NPC68419
0.9804 High Similarity NPC199457
0.9804 High Similarity NPC108709
0.9804 High Similarity NPC7870
0.9804 High Similarity NPC476880
0.9804 High Similarity NPC476882
0.9804 High Similarity NPC476886
0.9804 High Similarity NPC102914
0.9804 High Similarity NPC476881
0.9804 High Similarity NPC476885
0.9804 High Similarity NPC476883
0.9804 High Similarity NPC476884
0.9804 High Similarity NPC110139
0.9802 High Similarity NPC284807
0.9802 High Similarity NPC177246
0.9802 High Similarity NPC476123
0.9802 High Similarity NPC28198
0.9712 High Similarity NPC204458
0.9712 High Similarity NPC473343
0.9712 High Similarity NPC475208
0.9712 High Similarity NPC323341
0.9712 High Similarity NPC155410
0.9712 High Similarity NPC475287
0.9712 High Similarity NPC241909
0.9712 High Similarity NPC295823
0.9712 High Similarity NPC134835
0.9712 High Similarity NPC475467
0.9712 High Similarity NPC251263
0.9712 High Similarity NPC166422
0.9712 High Similarity NPC163183
0.9712 High Similarity NPC151543
0.9712 High Similarity NPC133818
0.9712 High Similarity NPC138334
0.9712 High Similarity NPC238935
0.9712 High Similarity NPC192600
0.9712 High Similarity NPC174720
0.9712 High Similarity NPC96641
0.9712 High Similarity NPC150400
0.9712 High Similarity NPC124296
0.9712 High Similarity NPC46665
0.9712 High Similarity NPC189884
0.9712 High Similarity NPC258885
0.9712 High Similarity NPC114304
0.9712 High Similarity NPC309714
0.9712 High Similarity NPC219180
0.9712 High Similarity NPC47063
0.9712 High Similarity NPC473826
0.9712 High Similarity NPC73318
0.9712 High Similarity NPC114287
0.9709 High Similarity NPC191763
0.9709 High Similarity NPC31839
0.9706 High Similarity NPC137917
0.9706 High Similarity NPC127853
0.9703 High Similarity NPC283849
0.9703 High Similarity NPC473538
0.9619 High Similarity NPC250247
0.9619 High Similarity NPC475140
0.9619 High Similarity NPC164389
0.9619 High Similarity NPC294453
0.9619 High Similarity NPC65105
0.9619 High Similarity NPC57484
0.9619 High Similarity NPC67857
0.9619 High Similarity NPC471385
0.9619 High Similarity NPC70809
0.9619 High Similarity NPC471550
0.9619 High Similarity NPC476068
0.9619 High Similarity NPC202828
0.9619 High Similarity NPC293330
0.9619 High Similarity NPC224381
0.9619 High Similarity NPC100639
0.9619 High Similarity NPC305981
0.9619 High Similarity NPC54636
0.9619 High Similarity NPC60557
0.9619 High Similarity NPC76972
0.9619 High Similarity NPC261506
0.9619 High Similarity NPC123199
0.9619 High Similarity NPC227551
0.9619 High Similarity NPC4328
0.9619 High Similarity NPC71065
0.9619 High Similarity NPC161717
0.9619 High Similarity NPC41061
0.9619 High Similarity NPC309907
0.9619 High Similarity NPC469782
0.9619 High Similarity NPC204414
0.9619 High Similarity NPC475160
0.9619 High Similarity NPC298034
0.9619 High Similarity NPC236638
0.9619 High Similarity NPC473714
0.9619 High Similarity NPC475486
0.9619 High Similarity NPC79643
0.9619 High Similarity NPC119592
0.9619 High Similarity NPC43550
0.9615 High Similarity NPC37739
0.9615 High Similarity NPC48249
0.9615 High Similarity NPC116794
0.9615 High Similarity NPC471967
0.9615 High Similarity NPC46388
0.9612 High Similarity NPC242611
0.9612 High Similarity NPC220984
0.9604 High Similarity NPC475611
0.9528 High Similarity NPC305267
0.9528 High Similarity NPC37134
0.9528 High Similarity NPC51465
0.9528 High Similarity NPC58448
0.9528 High Similarity NPC160415
0.9528 High Similarity NPC476992
0.9528 High Similarity NPC288205
0.9528 High Similarity NPC26626
0.9528 High Similarity NPC75287
0.9528 High Similarity NPC471384
0.9528 High Similarity NPC291903
0.9528 High Similarity NPC161674
0.9524 High Similarity NPC271138
0.9524 High Similarity NPC269315
0.9505 High Similarity NPC173583
0.9439 High Similarity NPC475209
0.9439 High Similarity NPC471547
0.9439 High Similarity NPC33012
0.9439 High Similarity NPC191827
0.9439 High Similarity NPC286457
0.9439 High Similarity NPC85154
0.9439 High Similarity NPC69811
0.9439 High Similarity NPC123522
0.9439 High Similarity NPC148417
0.9439 High Similarity NPC473452
0.9439 High Similarity NPC323359
0.9439 High Similarity NPC475119
0.9439 High Similarity NPC8524
0.9439 High Similarity NPC68175
0.9439 High Similarity NPC475514
0.9439 High Similarity NPC473824
0.9439 High Similarity NPC110633
0.9439 High Similarity NPC300419
0.9439 High Similarity NPC136768
0.9439 High Similarity NPC185466
0.9439 High Similarity NPC104137
0.9439 High Similarity NPC102505
0.9439 High Similarity NPC220160
0.9439 High Similarity NPC309223
0.9439 High Similarity NPC473405
0.9439 High Similarity NPC470876
0.9434 High Similarity NPC475633
0.9429 High Similarity NPC161434
0.9429 High Similarity NPC195132
0.9429 High Similarity NPC100383
0.9417 High Similarity NPC285576
0.9352 High Similarity NPC471548
0.9352 High Similarity NPC232237

  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 NPC127056 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
0.8962 High Similarity NPD8132 Clinical (unspecified phase)
0.8938 High Similarity NPD8328 Phase 3
0.8909 High Similarity NPD8295 Clinical (unspecified phase)
0.8468 Intermediate Similarity NPD8133 Approved
0.8257 Intermediate Similarity NPD6412 Phase 2
0.8182 Intermediate Similarity NPD6686 Approved
0.8077 Intermediate Similarity NPD7748 Approved
0.8034 Intermediate Similarity NPD8377 Approved
0.8034 Intermediate Similarity NPD8294 Approved
0.8019 Intermediate Similarity NPD7902 Approved
0.8 Intermediate Similarity NPD7507 Approved
0.7966 Intermediate Similarity NPD8380 Approved
0.7966 Intermediate Similarity NPD8379 Approved
0.7966 Intermediate Similarity NPD8296 Approved
0.7966 Intermediate Similarity NPD8378 Approved
0.7966 Intermediate Similarity NPD8033 Approved
0.7966 Intermediate Similarity NPD8335 Approved
0.7885 Intermediate Similarity NPD7515 Phase 2
0.7805 Intermediate Similarity NPD7319 Approved
0.7736 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD7900 Approved
0.7724 Intermediate Similarity NPD7736 Approved
0.7712 Intermediate Similarity NPD7327 Approved
0.7712 Intermediate Similarity NPD7328 Approved
0.7667 Intermediate Similarity NPD8516 Approved
0.7667 Intermediate Similarity NPD8515 Approved
0.7667 Intermediate Similarity NPD8517 Approved
0.7667 Intermediate Similarity NPD8513 Phase 3
0.7647 Intermediate Similarity NPD7516 Approved
0.7521 Intermediate Similarity NPD7503 Approved
0.75 Intermediate Similarity NPD8293 Discontinued
0.7434 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD8035 Phase 2
0.7383 Intermediate Similarity NPD8034 Phase 2
0.7317 Intermediate Similarity NPD6370 Approved
0.7297 Intermediate Similarity NPD7638 Approved
0.7288 Intermediate Similarity NPD6882 Approved
0.7288 Intermediate Similarity NPD8297 Approved
0.7232 Intermediate Similarity NPD7640 Approved
0.7232 Intermediate Similarity NPD7639 Approved
0.7228 Intermediate Similarity NPD7645 Phase 2
0.7203 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7492 Approved
0.719 Intermediate Similarity NPD6009 Approved
0.7179 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD6399 Phase 3
0.7154 Intermediate Similarity NPD6319 Approved
0.7154 Intermediate Similarity NPD6059 Approved
0.7154 Intermediate Similarity NPD6054 Approved
0.7143 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6616 Approved
0.712 Intermediate Similarity NPD6067 Discontinued
0.7094 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7078 Approved
0.7083 Intermediate Similarity NPD4632 Approved
0.7069 Intermediate Similarity NPD7128 Approved
0.7069 Intermediate Similarity NPD5739 Approved
0.7069 Intermediate Similarity NPD6675 Approved
0.7069 Intermediate Similarity NPD6402 Approved
0.7034 Intermediate Similarity NPD6372 Approved
0.7034 Intermediate Similarity NPD6373 Approved
0.7 Intermediate Similarity NPD8171 Discontinued
0.6975 Remote Similarity NPD5955 Clinical (unspecified phase)
0.696 Remote Similarity NPD6015 Approved
0.696 Remote Similarity NPD6016 Approved
0.6949 Remote Similarity NPD7320 Approved
0.6949 Remote Similarity NPD6881 Approved
0.6949 Remote Similarity NPD6899 Approved
0.6917 Remote Similarity NPD6650 Approved
0.6917 Remote Similarity NPD8130 Phase 1
0.6917 Remote Similarity NPD6649 Approved
0.6911 Remote Similarity NPD7115 Discovery
0.6909 Remote Similarity NPD6411 Approved
0.6905 Remote Similarity NPD5988 Approved
0.6864 Remote Similarity NPD5701 Approved
0.6864 Remote Similarity NPD5697 Approved
0.6833 Remote Similarity NPD7102 Approved
0.6833 Remote Similarity NPD7290 Approved
0.6833 Remote Similarity NPD6883 Approved
0.6822 Remote Similarity NPD8074 Phase 3
0.6818 Remote Similarity NPD6698 Approved
0.6818 Remote Similarity NPD46 Approved
0.6789 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6777 Remote Similarity NPD6617 Approved
0.6777 Remote Similarity NPD6869 Approved
0.6777 Remote Similarity NPD6847 Approved
0.6759 Remote Similarity NPD3618 Phase 1
0.6754 Remote Similarity NPD6084 Phase 2
0.6754 Remote Similarity NPD6083 Phase 2
0.675 Remote Similarity NPD6014 Approved
0.675 Remote Similarity NPD6013 Approved
0.675 Remote Similarity NPD6012 Approved
0.6729 Remote Similarity NPD4786 Approved
0.6727 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6101 Approved
0.6727 Remote Similarity NPD5328 Approved
0.6723 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7604 Phase 2
0.6698 Remote Similarity NPD3667 Approved
0.6697 Remote Similarity NPD3573 Approved
0.6696 Remote Similarity NPD4225 Approved
0.6693 Remote Similarity NPD5983 Phase 2
0.6667 Remote Similarity NPD7632 Discontinued
0.6667 Remote Similarity NPD6011 Approved
0.6641 Remote Similarity NPD6033 Approved
0.6639 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6639 Remote Similarity NPD6008 Approved
0.6636 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6636 Remote Similarity NPD3669 Approved
0.6615 Remote Similarity NPD6336 Discontinued
0.6609 Remote Similarity NPD4755 Approved
0.6607 Remote Similarity NPD6079 Approved
0.6607 Remote Similarity NPD7983 Approved
0.6606 Remote Similarity NPD7334 Approved
0.6606 Remote Similarity NPD6684 Approved
0.6606 Remote Similarity NPD6409 Approved
0.6606 Remote Similarity NPD7521 Approved
0.6606 Remote Similarity NPD5330 Approved
0.6606 Remote Similarity NPD7146 Approved
0.6577 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6567 Remote Similarity NPD8449 Approved
0.6562 Remote Similarity NPD6921 Approved
0.656 Remote Similarity NPD6940 Discontinued
0.6557 Remote Similarity NPD4634 Approved
0.6552 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6549 Remote Similarity NPD5779 Approved
0.6549 Remote Similarity NPD4202 Approved
0.6549 Remote Similarity NPD5778 Approved
0.6519 Remote Similarity NPD8450 Suspended
0.6509 Remote Similarity NPD7525 Registered
0.6496 Remote Similarity NPD4696 Approved
0.6496 Remote Similarity NPD5285 Approved
0.6496 Remote Similarity NPD4700 Approved
0.6496 Remote Similarity NPD5286 Approved
0.6486 Remote Similarity NPD6672 Approved
0.6486 Remote Similarity NPD6903 Approved
0.6486 Remote Similarity NPD5737 Approved
0.6476 Remote Similarity NPD6697 Approved
0.6476 Remote Similarity NPD6115 Approved
0.6476 Remote Similarity NPD6114 Approved
0.6476 Remote Similarity NPD6118 Approved
0.6449 Remote Similarity NPD1779 Approved
0.6449 Remote Similarity NPD1780 Approved
0.6435 Remote Similarity NPD5695 Phase 3
0.6434 Remote Similarity NPD7625 Phase 1
0.6429 Remote Similarity NPD6274 Approved
0.6422 Remote Similarity NPD3665 Phase 1
0.6422 Remote Similarity NPD3666 Approved
0.6422 Remote Similarity NPD3133 Approved
0.641 Remote Similarity NPD5696 Approved
0.6406 Remote Similarity NPD7101 Approved
0.6406 Remote Similarity NPD7100 Approved
0.6391 Remote Similarity NPD8337 Approved
0.6391 Remote Similarity NPD8336 Approved
0.6387 Remote Similarity NPD5226 Approved
0.6387 Remote Similarity NPD4633 Approved
0.6387 Remote Similarity NPD5225 Approved
0.6387 Remote Similarity NPD5211 Phase 2
0.6387 Remote Similarity NPD5224 Approved
0.6381 Remote Similarity NPD6116 Phase 1
0.6379 Remote Similarity NPD5222 Approved
0.6379 Remote Similarity NPD4697 Phase 3
0.6379 Remote Similarity NPD5221 Approved
0.6379 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6378 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4768 Approved
0.6364 Remote Similarity NPD4767 Approved
0.6333 Remote Similarity NPD5175 Approved
0.6333 Remote Similarity NPD5174 Approved
0.6328 Remote Similarity NPD6335 Approved
0.6325 Remote Similarity NPD5173 Approved
0.6308 Remote Similarity NPD6909 Approved
0.6308 Remote Similarity NPD6908 Approved
0.6303 Remote Similarity NPD5344 Discontinued
0.6303 Remote Similarity NPD5223 Approved
0.6299 Remote Similarity NPD6868 Approved
0.6293 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6288 Remote Similarity NPD8341 Approved
0.6288 Remote Similarity NPD8299 Approved
0.6288 Remote Similarity NPD8342 Approved
0.6288 Remote Similarity NPD8340 Approved
0.6286 Remote Similarity NPD6117 Approved
0.6283 Remote Similarity NPD4753 Phase 2
0.6281 Remote Similarity NPD5141 Approved
0.6273 Remote Similarity NPD3668 Phase 3
0.626 Remote Similarity NPD4730 Approved
0.626 Remote Similarity NPD4729 Approved
0.625 Remote Similarity NPD6317 Approved
0.6241 Remote Similarity NPD8451 Approved
0.6239 Remote Similarity NPD7839 Suspended
0.6239 Remote Similarity NPD7732 Phase 3
0.6239 Remote Similarity NPD7614 Phase 1
0.6228 Remote Similarity NPD7838 Discovery
0.6212 Remote Similarity NPD7830 Approved
0.6212 Remote Similarity NPD7829 Approved
0.6204 Remote Similarity NPD8338 Approved
0.6202 Remote Similarity NPD7641 Discontinued
0.6202 Remote Similarity NPD6314 Approved
0.6202 Remote Similarity NPD6313 Approved
0.6198 Remote Similarity NPD4754 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