Structure

Physi-Chem Properties

Molecular Weight:  650.33
Volume:  640.218
LogP:  1.336
LogD:  0.221
LogS:  -3.548
# Rotatable Bonds:  5
TPSA:  203.44
# H-Bond Aceptor:  12
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.161
Synthetic Accessibility Score:  5.762
Fsp3:  0.824
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.103
MDCK Permeability:  3.3945016184588894e-05
Pgp-inhibitor:  0.747
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.833
20% Bioavailability (F20%):  0.573
30% Bioavailability (F30%):  0.517

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.172
Plasma Protein Binding (PPB):  55.550811767578125%
Volume Distribution (VD):  0.466
Pgp-substrate:  17.697166442871094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.644
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.564
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.033
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.014
CYP3A4-inhibitor:  0.45
CYP3A4-substrate:  0.7

ADMET: Excretion

Clearance (CL):  1.511
Half-life (T1/2):  0.793

ADMET: Toxicity

hERG Blockers:  0.054
Human Hepatotoxicity (H-HT):  0.213
Drug-inuced Liver Injury (DILI):  0.039
AMES Toxicity:  0.15
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.838
Skin Sensitization:  0.042
Carcinogencity:  0.983
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.598

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

  Natural Product: NPC173347

Natural Product ID:  NPC173347
Common Name*:   (14R,17S,20S,22R)-14,17,20-Trihydroxy-3Beta-(O-Beta-D-Glucopyranosyl)-1-Oxowitha-5,24-Dienolide
IUPAC Name:   (2R)-2-[(1S)-1-[(3R,8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
Synonyms:  
Standard InCHIKey:  SYYXVJIFABSJBU-MJJWKRKWSA-N
Standard InCHI:  InChI=1S/C34H50O12/c1-16-12-24(46-28(40)17(16)2)32(5,41)34(43)11-10-33(42)21-7-6-18-13-19(44-29-27(39)26(38)25(37)22(15-35)45-29)14-23(36)31(18,4)20(21)8-9-30(33,34)3/h6,19-22,24-27,29,35,37-39,41-43H,7-15H2,1-5H3/t19-,20+,21-,22-,24-,25-,26+,27-,29-,30+,31+,32+,33-,34+/m1/s1
SMILES:  CC1=C(C)C(=O)O[C@H](C1)[C@@](C)([C@@]1(CC[C@]2([C@@H]3CC=C4C[C@H](CC(=O)[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501881
PubChem CID:   10508451
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001560] Withanolides and derivatives
            • [CHEMONTID:0001561] Withanolide glycosides and derivatives

*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
NPO13927 Withania coagulans Species Solanaceae Eukaryota fruits n.a. n.a. PMID[18952419]
NPO13927 Withania coagulans Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[23316950]
NPO13927 Withania coagulans Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13927 Withania coagulans Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13927 Withania coagulans Species Solanaceae 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
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 29.8 % PMID[533852]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 23.3 % PMID[533852]
NPT32 Organism Mus musculus Mus musculus Activity = 22.7 % PMID[533852]
NPT32 Organism Mus musculus Mus musculus Activity = 44.1 % PMID[533852]
NPT32 Organism Mus musculus Mus musculus Activity = 14.7 % PMID[533852]
NPT32 Organism Mus musculus Mus musculus Activity = 25.7 % PMID[533852]
NPT32 Organism Mus musculus Mus musculus Activity = 24.7 % PMID[533852]
NPT32 Organism Mus musculus Mus musculus Activity = 21.2 % PMID[533852]
NPT32 Organism Mus musculus Mus musculus Activity = 15.6 % PMID[533852]
NPT32 Organism Mus musculus Mus musculus ED50 = 25.0 mg.kg-1 PMID[533852]
NPT32 Organism Mus musculus Mus musculus Activity = 40.5 % PMID[533852]

☑ 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 NPC173347 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
0.9504 High Similarity NPC311534
0.9417 High Similarity NPC318135
0.9344 High Similarity NPC245094
0.9268 High Similarity NPC476966
0.912 High Similarity NPC471855
0.912 High Similarity NPC231240
0.9106 High Similarity NPC471357
0.9106 High Similarity NPC146456
0.9106 High Similarity NPC469757
0.9106 High Similarity NPC329784
0.9106 High Similarity NPC240070
0.9106 High Similarity NPC117702
0.9055 High Similarity NPC158350
0.9048 High Similarity NPC247190
0.9048 High Similarity NPC116075
0.9048 High Similarity NPC32793
0.9048 High Similarity NPC469749
0.9048 High Similarity NPC316915
0.9048 High Similarity NPC146857
0.9024 High Similarity NPC47113
0.9024 High Similarity NPC174367
0.9016 High Similarity NPC27363
0.9008 High Similarity NPC129434
0.9 High Similarity NPC232258
0.8992 High Similarity NPC290746
0.8992 High Similarity NPC79250
0.8992 High Similarity NPC75616
0.8976 High Similarity NPC329636
0.896 High Similarity NPC329986
0.896 High Similarity NPC86159
0.896 High Similarity NPC471361
0.896 High Similarity NPC70542
0.896 High Similarity NPC89514
0.896 High Similarity NPC140092
0.896 High Similarity NPC232785
0.896 High Similarity NPC180079
0.896 High Similarity NPC251866
0.896 High Similarity NPC197707
0.896 High Similarity NPC469754
0.896 High Similarity NPC471360
0.896 High Similarity NPC471407
0.896 High Similarity NPC284406
0.896 High Similarity NPC17896
0.896 High Similarity NPC469752
0.896 High Similarity NPC188234
0.896 High Similarity NPC471359
0.896 High Similarity NPC469753
0.896 High Similarity NPC469755
0.896 High Similarity NPC471358
0.896 High Similarity NPC9499
0.896 High Similarity NPC6108
0.896 High Similarity NPC125077
0.896 High Similarity NPC469751
0.896 High Similarity NPC471352
0.896 High Similarity NPC10823
0.896 High Similarity NPC219085
0.896 High Similarity NPC276838
0.8952 High Similarity NPC42399
0.8934 High Similarity NPC269642
0.8934 High Similarity NPC28532
0.8906 High Similarity NPC194716
0.8898 High Similarity NPC104585
0.8898 High Similarity NPC142756
0.8898 High Similarity NPC225385
0.8898 High Similarity NPC298783
0.8898 High Similarity NPC157817
0.8871 High Similarity NPC250556
0.8871 High Similarity NPC469750
0.8852 High Similarity NPC170084
0.8852 High Similarity NPC476204
0.8852 High Similarity NPC202051
0.8837 High Similarity NPC329675
0.8837 High Similarity NPC62172
0.8837 High Similarity NPC289700
0.8837 High Similarity NPC59288
0.8819 High Similarity NPC155529
0.88 High Similarity NPC179412
0.88 High Similarity NPC471356
0.879 High Similarity NPC241456
0.879 High Similarity NPC32868
0.878 High Similarity NPC107493
0.877 High Similarity NPC107607
0.876 High Similarity NPC291564
0.875 High Similarity NPC207637
0.875 High Similarity NPC477709
0.875 High Similarity NPC476221
0.874 High Similarity NPC253456
0.874 High Similarity NPC16569
0.874 High Similarity NPC159338
0.8739 High Similarity NPC260665
0.873 High Similarity NPC473620
0.871 High Similarity NPC204812
0.8699 High Similarity NPC475182
0.8699 High Similarity NPC231518
0.8699 High Similarity NPC475219
0.8699 High Similarity NPC46570
0.8692 High Similarity NPC127656
0.8689 High Similarity NPC29639
0.8689 High Similarity NPC81222
0.8689 High Similarity NPC477071
0.8689 High Similarity NPC44899
0.8689 High Similarity NPC291820
0.8689 High Similarity NPC5292
0.8689 High Similarity NPC475041
0.8689 High Similarity NPC304260
0.8689 High Similarity NPC5883
0.8678 High Similarity NPC203862
0.8672 High Similarity NPC19124
0.8672 High Similarity NPC93416
0.8672 High Similarity NPC42670
0.8667 High Similarity NPC473882
0.8661 High Similarity NPC91
0.8661 High Similarity NPC473593
0.8651 High Similarity NPC298841
0.8651 High Similarity NPC287423
0.864 High Similarity NPC248202
0.8629 High Similarity NPC156789
0.8629 High Similarity NPC193893
0.8618 High Similarity NPC470312
0.8618 High Similarity NPC471406
0.8618 High Similarity NPC79579
0.8618 High Similarity NPC476150
0.8618 High Similarity NPC476127
0.8615 High Similarity NPC171619
0.8607 High Similarity NPC475632
0.8607 High Similarity NPC239293
0.8607 High Similarity NPC473617
0.8607 High Similarity NPC86020
0.8607 High Similarity NPC153440
0.8607 High Similarity NPC473828
0.8607 High Similarity NPC218093
0.8594 High Similarity NPC213634
0.8583 High Similarity NPC311592
0.8583 High Similarity NPC75167
0.8571 High Similarity NPC473635
0.856 High Similarity NPC160084
0.856 High Similarity NPC469789
0.8548 High Similarity NPC40749
0.8537 High Similarity NPC236973
0.8537 High Similarity NPC122971
0.8537 High Similarity NPC319570
0.8537 High Similarity NPC32177
0.8537 High Similarity NPC292467
0.8537 High Similarity NPC55532
0.8537 High Similarity NPC30483
0.8537 High Similarity NPC469756
0.8537 High Similarity NPC305260
0.8537 High Similarity NPC470897
0.8537 High Similarity NPC270850
0.8527 High Similarity NPC473805
0.8527 High Similarity NPC473519
0.8525 High Similarity NPC474483
0.8525 High Similarity NPC93883
0.8516 High Similarity NPC231529
0.8512 High Similarity NPC116024
0.8512 High Similarity NPC181145
0.8504 High Similarity NPC470780
0.85 High Similarity NPC474265
0.85 High Similarity NPC210420
0.8492 Intermediate Similarity NPC473474
0.8492 Intermediate Similarity NPC30188
0.8492 Intermediate Similarity NPC3381
0.8492 Intermediate Similarity NPC470922
0.8492 Intermediate Similarity NPC177820
0.8487 Intermediate Similarity NPC52241
0.8487 Intermediate Similarity NPC154856
0.8487 Intermediate Similarity NPC475317
0.8487 Intermediate Similarity NPC83005
0.8485 Intermediate Similarity NPC596
0.848 Intermediate Similarity NPC23786
0.848 Intermediate Similarity NPC470265
0.8473 Intermediate Similarity NPC262813
0.8468 Intermediate Similarity NPC475187
0.8468 Intermediate Similarity NPC281840
0.8468 Intermediate Similarity NPC48692
0.8468 Intermediate Similarity NPC475629
0.8468 Intermediate Similarity NPC475556
0.8468 Intermediate Similarity NPC72260
0.8468 Intermediate Similarity NPC474585
0.8468 Intermediate Similarity NPC476961
0.8462 Intermediate Similarity NPC102015
0.8462 Intermediate Similarity NPC475487
0.8462 Intermediate Similarity NPC88668
0.8462 Intermediate Similarity NPC478151
0.8455 Intermediate Similarity NPC113448
0.8455 Intermediate Similarity NPC45475
0.845 Intermediate Similarity NPC173435
0.845 Intermediate Similarity NPC262796
0.845 Intermediate Similarity NPC478064
0.845 Intermediate Similarity NPC329993
0.845 Intermediate Similarity NPC264566
0.845 Intermediate Similarity NPC476074
0.845 Intermediate Similarity NPC301639
0.845 Intermediate Similarity NPC478065
0.845 Intermediate Similarity NPC475167
0.845 Intermediate Similarity NPC475377
0.845 Intermediate Similarity NPC45346
0.845 Intermediate Similarity NPC134914
0.845 Intermediate Similarity NPC477197
0.845 Intermediate Similarity NPC172374

  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 NPC173347 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
0.896 High Similarity NPD7319 Approved
0.8871 High Similarity NPD7507 Approved
0.8699 High Similarity NPD8033 Approved
0.8468 Intermediate Similarity NPD8294 Approved
0.8468 Intermediate Similarity NPD8377 Approved
0.8438 Intermediate Similarity NPD7736 Approved
0.84 Intermediate Similarity NPD8378 Approved
0.84 Intermediate Similarity NPD8335 Approved
0.84 Intermediate Similarity NPD8380 Approved
0.84 Intermediate Similarity NPD8379 Approved
0.84 Intermediate Similarity NPD8296 Approved
0.84 Intermediate Similarity NPD7503 Approved
0.8359 Intermediate Similarity NPD8293 Discontinued
0.8306 Intermediate Similarity NPD7328 Approved
0.8306 Intermediate Similarity NPD7327 Approved
0.8268 Intermediate Similarity NPD8328 Phase 3
0.824 Intermediate Similarity NPD7516 Approved
0.8235 Intermediate Similarity NPD6412 Phase 2
0.8189 Intermediate Similarity NPD6370 Approved
0.813 Intermediate Similarity NPD8133 Approved
0.811 Intermediate Similarity NPD8513 Phase 3
0.808 Intermediate Similarity NPD7115 Discovery
0.8062 Intermediate Similarity NPD7492 Approved
0.8031 Intermediate Similarity NPD6059 Approved
0.8031 Intermediate Similarity NPD6319 Approved
0.8031 Intermediate Similarity NPD6054 Approved
0.8017 Intermediate Similarity NPD6686 Approved
0.8 Intermediate Similarity NPD6616 Approved
0.7969 Intermediate Similarity NPD8515 Approved
0.7969 Intermediate Similarity NPD8517 Approved
0.7969 Intermediate Similarity NPD8516 Approved
0.7939 Intermediate Similarity NPD7078 Approved
0.7937 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7903 Intermediate Similarity NPD8297 Approved
0.7903 Intermediate Similarity NPD6882 Approved
0.7829 Intermediate Similarity NPD6016 Approved
0.7829 Intermediate Similarity NPD6015 Approved
0.7805 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7795 Intermediate Similarity NPD6009 Approved
0.7769 Intermediate Similarity NPD5988 Approved
0.7705 Intermediate Similarity NPD6402 Approved
0.7705 Intermediate Similarity NPD5739 Approved
0.7705 Intermediate Similarity NPD7128 Approved
0.7705 Intermediate Similarity NPD6675 Approved
0.7698 Intermediate Similarity NPD4632 Approved
0.7661 Intermediate Similarity NPD6372 Approved
0.7661 Intermediate Similarity NPD6373 Approved
0.7619 Intermediate Similarity NPD6053 Discontinued
0.7581 Intermediate Similarity NPD6899 Approved
0.7581 Intermediate Similarity NPD6881 Approved
0.7581 Intermediate Similarity NPD7320 Approved
0.754 Intermediate Similarity NPD8130 Phase 1
0.754 Intermediate Similarity NPD6650 Approved
0.754 Intermediate Similarity NPD6649 Approved
0.75 Intermediate Similarity NPD5701 Approved
0.75 Intermediate Similarity NPD5697 Approved
0.75 Intermediate Similarity NPD7638 Approved
0.7481 Intermediate Similarity NPD6033 Approved
0.746 Intermediate Similarity NPD7102 Approved
0.746 Intermediate Similarity NPD7290 Approved
0.746 Intermediate Similarity NPD4634 Approved
0.746 Intermediate Similarity NPD6883 Approved
0.7438 Intermediate Similarity NPD7639 Approved
0.7438 Intermediate Similarity NPD7640 Approved
0.7419 Intermediate Similarity NPD6008 Approved
0.7402 Intermediate Similarity NPD6869 Approved
0.7402 Intermediate Similarity NPD6617 Approved
0.7402 Intermediate Similarity NPD6847 Approved
0.7381 Intermediate Similarity NPD6014 Approved
0.7381 Intermediate Similarity NPD6012 Approved
0.7381 Intermediate Similarity NPD6013 Approved
0.7339 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD7604 Phase 2
0.7302 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD6011 Approved
0.7293 Intermediate Similarity NPD5983 Phase 2
0.7273 Intermediate Similarity NPD4755 Approved
0.7266 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD6336 Discontinued
0.7185 Intermediate Similarity NPD6067 Discontinued
0.7177 Intermediate Similarity NPD5211 Phase 2
0.7154 Intermediate Similarity NPD5285 Approved
0.7154 Intermediate Similarity NPD4700 Approved
0.7154 Intermediate Similarity NPD5286 Approved
0.7154 Intermediate Similarity NPD4696 Approved
0.7153 Intermediate Similarity NPD8074 Phase 3
0.7132 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD6083 Phase 2
0.7131 Intermediate Similarity NPD6084 Phase 2
0.7073 Intermediate Similarity NPD4225 Approved
0.7063 Intermediate Similarity NPD5141 Approved
0.7054 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6371 Approved
0.7045 Intermediate Similarity NPD6274 Approved
0.704 Intermediate Similarity NPD5224 Approved
0.704 Intermediate Similarity NPD5226 Approved
0.704 Intermediate Similarity NPD5225 Approved
0.704 Intermediate Similarity NPD4633 Approved
0.7037 Intermediate Similarity NPD7799 Discontinued
0.7025 Intermediate Similarity NPD7748 Approved
0.7015 Intermediate Similarity NPD7101 Approved
0.7015 Intermediate Similarity NPD7100 Approved
0.7008 Intermediate Similarity NPD4768 Approved
0.7008 Intermediate Similarity NPD4767 Approved
0.6992 Remote Similarity NPD7902 Approved
0.6984 Remote Similarity NPD5175 Approved
0.6984 Remote Similarity NPD5174 Approved
0.6975 Remote Similarity NPD5328 Approved
0.696 Remote Similarity NPD5223 Approved
0.6953 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6942 Remote Similarity NPD4202 Approved
0.6942 Remote Similarity NPD6399 Phase 3
0.694 Remote Similarity NPD6335 Approved
0.6912 Remote Similarity NPD6909 Approved
0.6912 Remote Similarity NPD6908 Approved
0.6905 Remote Similarity NPD7632 Discontinued
0.6899 Remote Similarity NPD4730 Approved
0.6899 Remote Similarity NPD4729 Approved
0.6867 Remote Similarity NPD7625 Phase 1
0.6866 Remote Similarity NPD6317 Approved
0.686 Remote Similarity NPD7515 Phase 2
0.686 Remote Similarity NPD6079 Approved
0.685 Remote Similarity NPD4754 Approved
0.6829 Remote Similarity NPD5695 Phase 3
0.6822 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6815 Remote Similarity NPD6313 Approved
0.6815 Remote Similarity NPD6314 Approved
0.68 Remote Similarity NPD5696 Approved
0.6794 Remote Similarity NPD5250 Approved
0.6794 Remote Similarity NPD5249 Phase 3
0.6794 Remote Similarity NPD5251 Approved
0.6794 Remote Similarity NPD5248 Approved
0.6794 Remote Similarity NPD5247 Approved
0.6788 Remote Similarity NPD6921 Approved
0.6777 Remote Similarity NPD6698 Approved
0.6777 Remote Similarity NPD46 Approved
0.6769 Remote Similarity NPD5128 Approved
0.6761 Remote Similarity NPD5956 Approved
0.675 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7900 Approved
0.6738 Remote Similarity NPD8337 Approved
0.6738 Remote Similarity NPD8336 Approved
0.6723 Remote Similarity NPD6684 Approved
0.6723 Remote Similarity NPD7334 Approved
0.6723 Remote Similarity NPD6409 Approved
0.6723 Remote Similarity NPD7521 Approved
0.6723 Remote Similarity NPD5330 Approved
0.6723 Remote Similarity NPD7146 Approved
0.6721 Remote Similarity NPD5693 Phase 1
0.6713 Remote Similarity NPD7260 Phase 2
0.6694 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6694 Remote Similarity NPD4753 Phase 2
0.6667 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8338 Approved
0.664 Remote Similarity NPD5220 Clinical (unspecified phase)
0.664 Remote Similarity NPD5222 Approved
0.664 Remote Similarity NPD4697 Phase 3
0.664 Remote Similarity NPD5221 Approved
0.6617 Remote Similarity NPD5216 Approved
0.6617 Remote Similarity NPD5215 Approved
0.6617 Remote Similarity NPD5217 Approved
0.6612 Remote Similarity NPD6903 Approved
0.6587 Remote Similarity NPD5173 Approved
0.6585 Remote Similarity NPD7983 Approved
0.6585 Remote Similarity NPD6411 Approved
0.6585 Remote Similarity NPD8035 Phase 2
0.6585 Remote Similarity NPD8034 Phase 2
0.6583 Remote Similarity NPD3618 Phase 1
0.6571 Remote Similarity NPD7829 Approved
0.6571 Remote Similarity NPD7830 Approved
0.6557 Remote Similarity NPD6904 Approved
0.6557 Remote Similarity NPD6673 Approved
0.6557 Remote Similarity NPD6080 Approved
0.6555 Remote Similarity NPD3666 Approved
0.6555 Remote Similarity NPD4786 Approved
0.6555 Remote Similarity NPD3133 Approved
0.6555 Remote Similarity NPD3665 Phase 1
0.6544 Remote Similarity NPD6868 Approved
0.6541 Remote Similarity NPD5169 Approved
0.6541 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6541 Remote Similarity NPD5135 Approved
0.6535 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6532 Remote Similarity NPD8171 Discontinued
0.6532 Remote Similarity NPD5778 Approved
0.6532 Remote Similarity NPD5779 Approved
0.6529 Remote Similarity NPD3573 Approved
0.6504 Remote Similarity NPD5785 Approved
0.6493 Remote Similarity NPD5127 Approved
0.6479 Remote Similarity NPD8451 Approved
0.6475 Remote Similarity NPD6672 Approved
0.6475 Remote Similarity NPD5737 Approved
0.6454 Remote Similarity NPD7642 Approved
0.6452 Remote Similarity NPD7236 Approved
0.6452 Remote Similarity NPD7637 Suspended
0.6452 Remote Similarity NPD5281 Approved
0.6452 Remote Similarity NPD5284 Approved
0.6446 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6443 Remote Similarity NPD6334 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