Structure

Physi-Chem Properties

Molecular Weight:  474.23
Volume:  472.609
LogP:  0.858
LogD:  0.131
LogS:  -3.288
# Rotatable Bonds:  4
TPSA:  134.27
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.448
Synthetic Accessibility Score:  5.055
Fsp3:  0.731
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.428
MDCK Permeability:  6.475049303844571e-05
Pgp-inhibitor:  0.05
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.889
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.598
Plasma Protein Binding (PPB):  54.658145904541016%
Volume Distribution (VD):  0.474
Pgp-substrate:  31.197856903076172%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.138
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.109
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.057
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.09
CYP3A4-inhibitor:  0.597
CYP3A4-substrate:  0.276

ADMET: Excretion

Clearance (CL):  3.083
Half-life (T1/2):  0.254

ADMET: Toxicity

hERG Blockers:  0.471
Human Hepatotoxicity (H-HT):  0.64
Drug-inuced Liver Injury (DILI):  0.097
AMES Toxicity:  0.066
Rat Oral Acute Toxicity:  0.978
Maximum Recommended Daily Dose:  0.995
Skin Sensitization:  0.698
Carcinogencity:  0.905
Eye Corrosion:  0.01
Eye Irritation:  0.023
Respiratory Toxicity:  0.979

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

  Natural Product: NPC55602

Natural Product ID:  NPC55602
Common Name*:   Bersaldegenin-3-Acetate
IUPAC Name:   [(1R,3S,5S,8R,9S,10R,13R,14S,17R)-10-formyl-1,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:   Bersaldegenin-3-Acetate
Standard InCHIKey:  BSHOWDODIUWLNU-LYKPKXNDSA-N
Standard InCHI:  InChI=1S/C26H34O8/c1-15(28)34-17-11-21(29)25(14-27)19-5-8-23(2)18(16-3-4-22(30)33-13-16)7-10-26(23,32)20(19)6-9-24(25,31)12-17/h3-4,13-14,17-21,29,31-32H,5-12H2,1-2H3/t17-,18+,19-,20+,21+,23+,24-,25-,26-/m0/s1
SMILES:  CC(=O)O[C@H]1C[C@H]([C@]2(C=O)[C@H]3CC[C@]4(C)[C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)c1ccc(=O)oc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL519993
PubChem CID:   21768173
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001557] Bufanolides 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
NPO21454 Iodes cirrhosa Species Icacinaceae Eukaryota root n.a. n.a. PMID[18327912]
NPO737 Aspergillus japonicus Species Aspergillaceae Eukaryota n.a. latex n.a. PMID[21854017]
NPO11343 Bryophyllum pinnatum Species Crassulaceae Eukaryota n.a. n.a. n.a. PMID[2607348]
NPO12761 Rheum hotaoense Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7322 Plagiochila acanthophylla Species Plagiochilaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21331 Syzygium samarangense Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11673 Koelreuteria paniculata Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9015 Solanum arundo Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO395 Teucrium pilosum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15212.1 Fraxinus chinensis subsp. rhynchophylla Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18228 Cycas beddomei Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12761 Rheum hotaoense Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11673 Koelreuteria paniculata Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3313 Crotalaria trichotoma Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21331 Syzygium samarangense Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11673 Koelreuteria paniculata Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11228 Fritillaria pallidiflora Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15212.1 Fraxinus chinensis subsp. rhynchophylla Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO737 Aspergillus japonicus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4919 Kalanchoe daigremontiana Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11343 Bryophyllum pinnatum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8403 Annona coriacea Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11540 Acacia leptostachya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21454 Iodes cirrhosa Species Icacinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3313 Crotalaria trichotoma Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28293 Aegilops geniculata Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13095 Pachycereus tehuantepecanus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10101 Rothmannia macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21331 Syzygium samarangense Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9015 Solanum arundo Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12761 Rheum hotaoense Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20444 Corticium caeruleum Species Plakinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO395 Teucrium pilosum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12045 Schottera nicaeensis Species Phyllophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18228 Cycas beddomei Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5310 Eucalyptus bakeri Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17461 Hedera canariensis Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9887 Protohermes grandis Species Corydalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11673 Koelreuteria paniculata Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18024 Acacia pruinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14318 Lespedeza davidii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9461 Gmelina leichhardtii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7322 Plagiochila acanthophylla Species Plagiochilaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15212.1 Fraxinus chinensis subsp. rhynchophylla Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4454 Maytenus salicifolia Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3670 Crotalaria podocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11228 Fritillaria pallidiflora Species Liliaceae 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
NPT91 Cell Line KB Homo sapiens ED50 < 40.0 ng/ml PMID[458451]
NPT81 Cell Line A549 Homo sapiens ED50 = 40.0 ng/ml PMID[458451]
NPT180 Cell Line HCT-8 Homo sapiens ED50 = 10.0 ng/ml PMID[458451]
NPT168 Cell Line P388 Mus musculus ED50 > 4.0 ng/ml PMID[458451]
NPT137 Cell Line L1210 Mus musculus ED50 > 4.0 ng/ml PMID[458451]

☑ 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 NPC55602 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
0.9735 High Similarity NPC184555
0.9402 High Similarity NPC233041
0.9262 High Similarity NPC248703
0.9224 High Similarity NPC41123
0.9224 High Similarity NPC145074
0.9224 High Similarity NPC114939
0.9204 High Similarity NPC73050
0.9113 High Similarity NPC289700
0.9113 High Similarity NPC62172
0.9091 High Similarity NPC221414
0.9043 High Similarity NPC469794
0.9043 High Similarity NPC72772
0.8968 High Similarity NPC75616
0.8889 High Similarity NPC146786
0.8772 High Similarity NPC16270
0.8761 High Similarity NPC137462
0.8761 High Similarity NPC304276
0.8707 High Similarity NPC171126
0.8689 High Similarity NPC159499
0.864 High Similarity NPC155529
0.8621 High Similarity NPC44537
0.8609 High Similarity NPC103491
0.8609 High Similarity NPC12795
0.8583 High Similarity NPC476962
0.8547 High Similarity NPC154815
0.8525 High Similarity NPC6193
0.8487 Intermediate Similarity NPC476959
0.848 Intermediate Similarity NPC89514
0.848 Intermediate Similarity NPC9499
0.848 Intermediate Similarity NPC284406
0.848 Intermediate Similarity NPC469754
0.848 Intermediate Similarity NPC471360
0.848 Intermediate Similarity NPC6108
0.848 Intermediate Similarity NPC471359
0.848 Intermediate Similarity NPC469751
0.848 Intermediate Similarity NPC219085
0.848 Intermediate Similarity NPC471358
0.848 Intermediate Similarity NPC469752
0.848 Intermediate Similarity NPC231529
0.848 Intermediate Similarity NPC197707
0.848 Intermediate Similarity NPC469755
0.848 Intermediate Similarity NPC469753
0.848 Intermediate Similarity NPC17896
0.848 Intermediate Similarity NPC471352
0.848 Intermediate Similarity NPC10823
0.848 Intermediate Similarity NPC471361
0.848 Intermediate Similarity NPC251866
0.848 Intermediate Similarity NPC86159
0.848 Intermediate Similarity NPC180079
0.848 Intermediate Similarity NPC70542
0.8462 Intermediate Similarity NPC247760
0.8438 Intermediate Similarity NPC158350
0.843 Intermediate Similarity NPC257610
0.8421 Intermediate Similarity NPC189863
0.8421 Intermediate Similarity NPC266570
0.8407 Intermediate Similarity NPC171014
0.8403 Intermediate Similarity NPC196931
0.8403 Intermediate Similarity NPC476963
0.8376 Intermediate Similarity NPC183603
0.8374 Intermediate Similarity NPC11895
0.8374 Intermediate Similarity NPC204812
0.8372 Intermediate Similarity NPC127656
0.8362 Intermediate Similarity NPC75389
0.8362 Intermediate Similarity NPC285298
0.8362 Intermediate Similarity NPC257082
0.8361 Intermediate Similarity NPC46570
0.8348 Intermediate Similarity NPC43063
0.8348 Intermediate Similarity NPC79298
0.8348 Intermediate Similarity NPC263729
0.8348 Intermediate Similarity NPC179380
0.8347 Intermediate Similarity NPC35171
0.8347 Intermediate Similarity NPC213761
0.8333 Intermediate Similarity NPC239273
0.8333 Intermediate Similarity NPC474518
0.832 Intermediate Similarity NPC179412
0.832 Intermediate Similarity NPC146456
0.832 Intermediate Similarity NPC471356
0.832 Intermediate Similarity NPC469757
0.832 Intermediate Similarity NPC117702
0.832 Intermediate Similarity NPC471357
0.8319 Intermediate Similarity NPC470953
0.8306 Intermediate Similarity NPC81736
0.8306 Intermediate Similarity NPC172154
0.8306 Intermediate Similarity NPC241456
0.8306 Intermediate Similarity NPC32868
0.8305 Intermediate Similarity NPC4573
0.8305 Intermediate Similarity NPC277769
0.8305 Intermediate Similarity NPC90952
0.8293 Intermediate Similarity NPC107493
0.8293 Intermediate Similarity NPC170538
0.8293 Intermediate Similarity NPC269642
0.8291 Intermediate Similarity NPC478209
0.8281 Intermediate Similarity NPC32793
0.8281 Intermediate Similarity NPC146857
0.8281 Intermediate Similarity NPC116075
0.8281 Intermediate Similarity NPC247190
0.8281 Intermediate Similarity NPC469749
0.8279 Intermediate Similarity NPC112936
0.8276 Intermediate Similarity NPC163216
0.8276 Intermediate Similarity NPC275060
0.8264 Intermediate Similarity NPC16701
0.8261 Intermediate Similarity NPC295843
0.824 Intermediate Similarity NPC469750
0.824 Intermediate Similarity NPC473635
0.824 Intermediate Similarity NPC293112
0.824 Intermediate Similarity NPC250556
0.8226 Intermediate Similarity NPC469789
0.822 Intermediate Similarity NPC474315
0.8217 Intermediate Similarity NPC329636
0.8211 Intermediate Similarity NPC312481
0.8197 Intermediate Similarity NPC278681
0.8197 Intermediate Similarity NPC305260
0.8197 Intermediate Similarity NPC270850
0.8197 Intermediate Similarity NPC5292
0.8197 Intermediate Similarity NPC476960
0.8182 Intermediate Similarity NPC134430
0.8182 Intermediate Similarity NPC475809
0.8182 Intermediate Similarity NPC157380
0.8182 Intermediate Similarity NPC55296
0.8167 Intermediate Similarity NPC238667
0.816 Intermediate Similarity NPC469790
0.816 Intermediate Similarity NPC8369
0.8154 Intermediate Similarity NPC194716
0.8151 Intermediate Similarity NPC476163
0.8145 Intermediate Similarity NPC23786
0.8145 Intermediate Similarity NPC470265
0.8136 Intermediate Similarity NPC179642
0.813 Intermediate Similarity NPC476961
0.813 Intermediate Similarity NPC251226
0.813 Intermediate Similarity NPC79579
0.812 Intermediate Similarity NPC476802
0.812 Intermediate Similarity NPC177064
0.812 Intermediate Similarity NPC89171
0.8115 Intermediate Similarity NPC113448
0.8115 Intermediate Similarity NPC153440
0.8103 Intermediate Similarity NPC34768
0.8103 Intermediate Similarity NPC295366
0.8099 Intermediate Similarity NPC148458
0.8099 Intermediate Similarity NPC190286
0.8092 Intermediate Similarity NPC59288
0.8092 Intermediate Similarity NPC329675
0.8087 Intermediate Similarity NPC97487
0.8087 Intermediate Similarity NPC189588
0.8087 Intermediate Similarity NPC196471
0.8087 Intermediate Similarity NPC187302
0.8087 Intermediate Similarity NPC10232
0.8087 Intermediate Similarity NPC112009
0.8083 Intermediate Similarity NPC25909
0.8083 Intermediate Similarity NPC478212
0.8083 Intermediate Similarity NPC122056
0.8083 Intermediate Similarity NPC241977
0.808 Intermediate Similarity NPC27363
0.808 Intermediate Similarity NPC473979
0.807 Intermediate Similarity NPC471412
0.8065 Intermediate Similarity NPC67569
0.8065 Intermediate Similarity NPC4021
0.8065 Intermediate Similarity NPC159456
0.8062 Intermediate Similarity NPC93416
0.8051 Intermediate Similarity NPC474243
0.8049 Intermediate Similarity NPC77689
0.8049 Intermediate Similarity NPC475520
0.8049 Intermediate Similarity NPC264954
0.8049 Intermediate Similarity NPC475041
0.8049 Intermediate Similarity NPC230513
0.8049 Intermediate Similarity NPC473839
0.8049 Intermediate Similarity NPC211093
0.8049 Intermediate Similarity NPC473636
0.8047 Intermediate Similarity NPC276838
0.8047 Intermediate Similarity NPC125077
0.8047 Intermediate Similarity NPC188234
0.8047 Intermediate Similarity NPC140092
0.8047 Intermediate Similarity NPC232785
0.8047 Intermediate Similarity NPC329986
0.8034 Intermediate Similarity NPC302788
0.8033 Intermediate Similarity NPC185287
0.8031 Intermediate Similarity NPC287423
0.8017 Intermediate Similarity NPC165969
0.8017 Intermediate Similarity NPC67259
0.8017 Intermediate Similarity NPC201763
0.8017 Intermediate Similarity NPC147912
0.8016 Intermediate Similarity NPC8374
0.8 Intermediate Similarity NPC193934
0.8 Intermediate Similarity NPC69291
0.8 Intermediate Similarity NPC100267
0.8 Intermediate Similarity NPC271980
0.8 Intermediate Similarity NPC475970
0.8 Intermediate Similarity NPC475524
0.8 Intermediate Similarity NPC88668
0.7984 Intermediate Similarity NPC159338
0.7984 Intermediate Similarity NPC16569
0.7984 Intermediate Similarity NPC474370
0.7984 Intermediate Similarity NPC474585
0.7984 Intermediate Similarity NPC154491
0.7984 Intermediate Similarity NPC173347
0.7984 Intermediate Similarity NPC268530
0.7984 Intermediate Similarity NPC472004
0.7984 Intermediate Similarity NPC253456
0.7983 Intermediate Similarity NPC197428
0.7982 Intermediate Similarity NPC251680
0.7982 Intermediate Similarity NPC35751

  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 NPC55602 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
0.848 Intermediate Similarity NPD7319 Approved
0.824 Intermediate Similarity NPD7507 Approved
0.8053 Intermediate Similarity NPD7638 Approved
0.7982 Intermediate Similarity NPD7639 Approved
0.7982 Intermediate Similarity NPD7640 Approved
0.792 Intermediate Similarity NPD7503 Approved
0.7886 Intermediate Similarity NPD7115 Discovery
0.784 Intermediate Similarity NPD6319 Approved
0.7815 Intermediate Similarity NPD6881 Approved
0.7815 Intermediate Similarity NPD6899 Approved
0.7769 Intermediate Similarity NPD6649 Approved
0.7769 Intermediate Similarity NPD6650 Approved
0.7731 Intermediate Similarity NPD5697 Approved
0.7705 Intermediate Similarity NPD6053 Discontinued
0.7705 Intermediate Similarity NPD6882 Approved
0.7705 Intermediate Similarity NPD8297 Approved
0.7692 Intermediate Similarity NPD7736 Approved
0.7686 Intermediate Similarity NPD6883 Approved
0.7686 Intermediate Similarity NPD7102 Approved
0.7686 Intermediate Similarity NPD7290 Approved
0.7647 Intermediate Similarity NPD6675 Approved
0.7647 Intermediate Similarity NPD5739 Approved
0.7647 Intermediate Similarity NPD6402 Approved
0.7647 Intermediate Similarity NPD7128 Approved
0.7623 Intermediate Similarity NPD6617 Approved
0.7623 Intermediate Similarity NPD6847 Approved
0.7623 Intermediate Similarity NPD6869 Approved
0.7623 Intermediate Similarity NPD8130 Phase 1
0.7603 Intermediate Similarity NPD6013 Approved
0.7603 Intermediate Similarity NPD6012 Approved
0.7603 Intermediate Similarity NPD6014 Approved
0.7603 Intermediate Similarity NPD6372 Approved
0.7603 Intermediate Similarity NPD6373 Approved
0.7597 Intermediate Similarity NPD7492 Approved
0.7559 Intermediate Similarity NPD6054 Approved
0.754 Intermediate Similarity NPD7327 Approved
0.754 Intermediate Similarity NPD7328 Approved
0.7538 Intermediate Similarity NPD6616 Approved
0.7521 Intermediate Similarity NPD6011 Approved
0.7521 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD4632 Approved
0.7481 Intermediate Similarity NPD7078 Approved
0.748 Intermediate Similarity NPD7516 Approved
0.7442 Intermediate Similarity NPD6370 Approved
0.7438 Intermediate Similarity NPD5701 Approved
0.7398 Intermediate Similarity NPD4634 Approved
0.7395 Intermediate Similarity NPD5211 Phase 2
0.7395 Intermediate Similarity NPD7632 Discontinued
0.7373 Intermediate Similarity NPD5286 Approved
0.7373 Intermediate Similarity NPD4696 Approved
0.7373 Intermediate Similarity NPD5285 Approved
0.7364 Intermediate Similarity NPD8380 Approved
0.7364 Intermediate Similarity NPD8335 Approved
0.7364 Intermediate Similarity NPD6016 Approved
0.7364 Intermediate Similarity NPD8379 Approved
0.7364 Intermediate Similarity NPD6015 Approved
0.7364 Intermediate Similarity NPD8378 Approved
0.7364 Intermediate Similarity NPD8296 Approved
0.7323 Intermediate Similarity NPD6009 Approved
0.7308 Intermediate Similarity NPD5988 Approved
0.7287 Intermediate Similarity NPD8294 Approved
0.7287 Intermediate Similarity NPD6059 Approved
0.7287 Intermediate Similarity NPD8377 Approved
0.7273 Intermediate Similarity NPD5141 Approved
0.7252 Intermediate Similarity NPD7604 Phase 2
0.725 Intermediate Similarity NPD5225 Approved
0.725 Intermediate Similarity NPD4633 Approved
0.725 Intermediate Similarity NPD5224 Approved
0.725 Intermediate Similarity NPD5226 Approved
0.7231 Intermediate Similarity NPD5983 Phase 2
0.7231 Intermediate Similarity NPD8033 Approved
0.7218 Intermediate Similarity NPD8293 Discontinued
0.7217 Intermediate Similarity NPD7637 Suspended
0.7217 Intermediate Similarity NPD6079 Approved
0.7213 Intermediate Similarity NPD6008 Approved
0.7209 Intermediate Similarity NPD7101 Approved
0.7209 Intermediate Similarity NPD7100 Approved
0.7203 Intermediate Similarity NPD6084 Phase 2
0.7203 Intermediate Similarity NPD4755 Approved
0.7203 Intermediate Similarity NPD6083 Phase 2
0.72 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD5174 Approved
0.719 Intermediate Similarity NPD5175 Approved
0.7167 Intermediate Similarity NPD5223 Approved
0.7143 Intermediate Similarity NPD6336 Discontinued
0.7132 Intermediate Similarity NPD6335 Approved
0.7109 Intermediate Similarity NPD6274 Approved
0.7097 Intermediate Similarity NPD4729 Approved
0.7097 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6686 Approved
0.7097 Intermediate Similarity NPD4730 Approved
0.7083 Intermediate Similarity NPD4700 Approved
0.7054 Intermediate Similarity NPD6317 Approved
0.7043 Intermediate Similarity NPD5328 Approved
0.704 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD5778 Approved
0.7009 Intermediate Similarity NPD5779 Approved
0.7 Intermediate Similarity NPD6314 Approved
0.7 Intermediate Similarity NPD6313 Approved
0.7 Intermediate Similarity NPD4225 Approved
0.6984 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6984 Remote Similarity NPD5248 Approved
0.6984 Remote Similarity NPD5250 Approved
0.6984 Remote Similarity NPD5247 Approved
0.6984 Remote Similarity NPD5251 Approved
0.6984 Remote Similarity NPD5249 Phase 3
0.6975 Remote Similarity NPD5222 Approved
0.6975 Remote Similarity NPD5221 Approved
0.6975 Remote Similarity NPD4697 Phase 3
0.6975 Remote Similarity NPD5220 Clinical (unspecified phase)
0.697 Remote Similarity NPD8513 Phase 3
0.6957 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6953 Remote Similarity NPD8133 Approved
0.6949 Remote Similarity NPD7748 Approved
0.6935 Remote Similarity NPD4768 Approved
0.6935 Remote Similarity NPD4767 Approved
0.6923 Remote Similarity NPD6411 Approved
0.6923 Remote Similarity NPD7515 Phase 2
0.6917 Remote Similarity NPD5173 Approved
0.6891 Remote Similarity NPD5695 Phase 3
0.688 Remote Similarity NPD6412 Phase 2
0.6866 Remote Similarity NPD8328 Phase 3
0.6864 Remote Similarity NPD4202 Approved
0.686 Remote Similarity NPD5696 Approved
0.6846 Remote Similarity NPD6868 Approved
0.6842 Remote Similarity NPD6909 Approved
0.6842 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6842 Remote Similarity NPD8517 Approved
0.6842 Remote Similarity NPD8515 Approved
0.6842 Remote Similarity NPD8516 Approved
0.6842 Remote Similarity NPD6908 Approved
0.6838 Remote Similarity NPD5785 Approved
0.6825 Remote Similarity NPD5128 Approved
0.6824 Remote Similarity NPD7236 Approved
0.6818 Remote Similarity NPD5760 Phase 2
0.6818 Remote Similarity NPD5761 Phase 2
0.6797 Remote Similarity NPD5215 Approved
0.6797 Remote Similarity NPD5217 Approved
0.6797 Remote Similarity NPD5216 Approved
0.6788 Remote Similarity NPD6033 Approved
0.6783 Remote Similarity NPD6684 Approved
0.6783 Remote Similarity NPD6409 Approved
0.6783 Remote Similarity NPD7521 Approved
0.6783 Remote Similarity NPD7334 Approved
0.6783 Remote Similarity NPD5330 Approved
0.6783 Remote Similarity NPD7146 Approved
0.678 Remote Similarity NPD5693 Phase 1
0.678 Remote Similarity NPD8035 Phase 2
0.678 Remote Similarity NPD8034 Phase 2
0.678 Remote Similarity NPD5284 Approved
0.678 Remote Similarity NPD5281 Approved
0.6777 Remote Similarity NPD7902 Approved
0.6774 Remote Similarity NPD4754 Approved
0.6763 Remote Similarity NPD7260 Phase 2
0.6752 Remote Similarity NPD6101 Approved
0.6752 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6752 Remote Similarity NPD4753 Phase 2
0.675 Remote Similarity NPD6356 Clinical (unspecified phase)
0.675 Remote Similarity NPD5210 Approved
0.675 Remote Similarity NPD4629 Approved
0.6746 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6724 Remote Similarity NPD3573 Approved
0.6723 Remote Similarity NPD6399 Phase 3
0.6719 Remote Similarity NPD6371 Approved
0.6719 Remote Similarity NPD5169 Approved
0.6719 Remote Similarity NPD5135 Approved
0.6719 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6711 Remote Similarity NPD7239 Suspended
0.6667 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD5127 Approved
0.6639 Remote Similarity NPD5694 Approved
0.6639 Remote Similarity NPD6050 Approved
0.6638 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6638 Remote Similarity NPD3618 Phase 1
0.6614 Remote Similarity NPD7899 Clinical (unspecified phase)
0.661 Remote Similarity NPD6080 Approved
0.661 Remote Similarity NPD6904 Approved
0.661 Remote Similarity NPD6051 Approved
0.661 Remote Similarity NPD6673 Approved
0.6609 Remote Similarity NPD3665 Phase 1
0.6609 Remote Similarity NPD3133 Approved
0.6609 Remote Similarity NPD3666 Approved
0.6597 Remote Similarity NPD6334 Approved
0.6597 Remote Similarity NPD6333 Approved
0.6593 Remote Similarity NPD6921 Approved
0.6579 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6564 Remote Similarity NPD7799 Discontinued
0.6555 Remote Similarity NPD5207 Approved
0.6555 Remote Similarity NPD5692 Phase 3
0.6541 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6532 Remote Similarity NPD6648 Approved
0.6529 Remote Similarity NPD7900 Approved
0.6529 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5737 Approved
0.6525 Remote Similarity NPD6672 Approved
0.6522 Remote Similarity NPD6695 Phase 3
0.6515 Remote Similarity NPD5167 Approved
0.65 Remote Similarity NPD7983 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