Structure

Physi-Chem Properties

Molecular Weight:  838.4
Volume:  805.424
LogP:  1.4
LogD:  0.319
LogS:  -3.626
# Rotatable Bonds:  8
TPSA:  267.66
# H-Bond Aceptor:  17
# H-Bond Donor:  9
# Rings:  8
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.152
Synthetic Accessibility Score:  6.062
Fsp3:  0.833
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:  -6.264
MDCK Permeability:  0.00011585321772145107
Pgp-inhibitor:  0.278
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.998
20% Bioavailability (F20%):  0.226
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.082
Plasma Protein Binding (PPB):  74.5840072631836%
Volume Distribution (VD):  0.371
Pgp-substrate:  12.07985782623291%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.636
CYP2C19-inhibitor:  0.007
CYP2C19-substrate:  0.229
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.026
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.099
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.027

ADMET: Excretion

Clearance (CL):  0.667
Half-life (T1/2):  0.67

ADMET: Toxicity

hERG Blockers:  0.215
Human Hepatotoxicity (H-HT):  0.199
Drug-inuced Liver Injury (DILI):  0.097
AMES Toxicity:  0.083
Rat Oral Acute Toxicity:  0.669
Maximum Recommended Daily Dose:  0.361
Skin Sensitization:  0.104
Carcinogencity:  0.377
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.962

Download Data

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

  Natural Product: NPC179261

Natural Product ID:  NPC179261
Common Name*:   (14Beta-Hydroxybufa-4,20,22-Trienolide-3Beta-O-{Alpha-L-Rhamnopyranosyl-[(1->4)-Beta-D-Glucopyranosyl]-(1->3)-Alpha-L-Rhamnopyranoside})
IUPAC Name:   5-[(3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-3-[(2R,3R,4S,5S,6S)-3-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
Synonyms:  
Standard InCHIKey:  VZARJLMRDRMOAU-FYEZBVCASA-N
Standard InCHI:  InChI=1S/C42H62O17/c1-18-28(45)30(47)32(49)37(54-18)59-36-34(51)39(55-19(2)35(36)58-38-33(50)31(48)29(46)26(16-43)57-38)56-22-9-12-40(3)21(15-22)6-7-25-24(40)10-13-41(4)23(11-14-42(25,41)52)20-5-8-27(44)53-17-20/h5,8,15,17-19,22-26,28-39,43,45-52H,6-7,9-14,16H2,1-4H3/t18-,19-,22-,23+,24-,25+,26+,28-,29+,30+,31-,32+,33+,34+,35-,36-,37-,38-,39-,40-,41+,42-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@H]([C@@H](O[C@@H](C)[C@@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1CC[C@@]2(C)C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](CC[C@]12O)c1ccc(=O)oc1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2375662
PubChem CID:   202218
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
NPO27354 Urginea depressa Species Hyacinthaceae Eukaryota n.a. n.a. n.a. PMID[23659371]
NPO17801 Drimia altissima Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2774 Drimia robusta Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18451 Senecio lydenburgensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27354 Urginea depressa Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2774 Drimia robusta Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17004 Plocamium suhrii Species Plocamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17801 Drimia altissima Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16153 Desmos dunalii Species Annonaceae 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
NPT179 Cell Line A2780 Homo sapiens IC50 = 111.0 nM PMID[505005]
NPT1383 Cell Line A2058 Homo sapiens IC50 = 180.0 nM PMID[505005]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 110.0 nM PMID[505005]

☑ 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 NPC179261 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
0.9274 High Similarity NPC127656
0.916 High Similarity NPC219804
0.9068 High Similarity NPC135369
0.8992 High Similarity NPC474908
0.8992 High Similarity NPC475590
0.8992 High Similarity NPC120390
0.8992 High Similarity NPC475419
0.8952 High Similarity NPC155529
0.8917 High Similarity NPC74259
0.8917 High Similarity NPC474423
0.8908 High Similarity NPC72260
0.8889 High Similarity NPC158350
0.8843 High Similarity NPC117445
0.8843 High Similarity NPC308262
0.8843 High Similarity NPC208193
0.8833 High Similarity NPC173555
0.8833 High Similarity NPC314535
0.8824 High Similarity NPC32177
0.8824 High Similarity NPC469756
0.8824 High Similarity NPC219656
0.8824 High Similarity NPC55532
0.8824 High Similarity NPC292467
0.8824 High Similarity NPC30483
0.8824 High Similarity NPC236973
0.8824 High Similarity NPC470897
0.876 High Similarity NPC193893
0.876 High Similarity NPC264336
0.875 High Similarity NPC475629
0.875 High Similarity NPC475556
0.875 High Similarity NPC107607
0.8739 High Similarity NPC218093
0.8678 High Similarity NPC231518
0.8678 High Similarity NPC475219
0.8678 High Similarity NPC233500
0.8678 High Similarity NPC40749
0.8667 High Similarity NPC81222
0.8667 High Similarity NPC329905
0.8667 High Similarity NPC291820
0.8655 High Similarity NPC93883
0.8655 High Similarity NPC203862
0.8618 High Similarity NPC471090
0.8607 High Similarity NPC196130
0.8595 High Similarity NPC475136
0.8595 High Similarity NPC257610
0.8595 High Similarity NPC474466
0.8571 High Similarity NPC5311
0.8571 High Similarity NPC199428
0.8571 High Similarity NPC207637
0.8571 High Similarity NPC146652
0.8571 High Similarity NPC310341
0.8571 High Similarity NPC193382
0.8571 High Similarity NPC99620
0.8527 High Similarity NPC62172
0.8527 High Similarity NPC289700
0.8512 High Similarity NPC473633
0.8512 High Similarity NPC29639
0.8512 High Similarity NPC195560
0.8512 High Similarity NPC229962
0.8512 High Similarity NPC44899
0.8512 High Similarity NPC476085
0.8512 High Similarity NPC5883
0.8512 High Similarity NPC304260
0.85 High Similarity NPC99728
0.85 High Similarity NPC142066
0.85 High Similarity NPC34390
0.85 High Similarity NPC471355
0.85 High Similarity NPC244402
0.85 High Similarity NPC473852
0.85 High Similarity NPC196429
0.85 High Similarity NPC471351
0.85 High Similarity NPC152615
0.85 High Similarity NPC157376
0.85 High Similarity NPC158344
0.85 High Similarity NPC27507
0.85 High Similarity NPC243196
0.85 High Similarity NPC77319
0.85 High Similarity NPC471354
0.85 High Similarity NPC87250
0.85 High Similarity NPC474418
0.85 High Similarity NPC309034
0.85 High Similarity NPC50305
0.85 High Similarity NPC84987
0.85 High Similarity NPC471353
0.8487 Intermediate Similarity NPC471633
0.8487 Intermediate Similarity NPC69576
0.8487 Intermediate Similarity NPC31354
0.8487 Intermediate Similarity NPC84949
0.8455 Intermediate Similarity NPC471082
0.8455 Intermediate Similarity NPC43842
0.8443 Intermediate Similarity NPC207243
0.8443 Intermediate Similarity NPC198325
0.8443 Intermediate Similarity NPC50689
0.8443 Intermediate Similarity NPC233391
0.843 Intermediate Similarity NPC83287
0.843 Intermediate Similarity NPC160888
0.843 Intermediate Similarity NPC475357
0.843 Intermediate Similarity NPC475403
0.843 Intermediate Similarity NPC470515
0.843 Intermediate Similarity NPC472080
0.8417 Intermediate Similarity NPC148965
0.8403 Intermediate Similarity NPC469348
0.8403 Intermediate Similarity NPC469347
0.8403 Intermediate Similarity NPC473159
0.8397 Intermediate Similarity NPC75616
0.839 Intermediate Similarity NPC65167
0.839 Intermediate Similarity NPC114188
0.839 Intermediate Similarity NPC470748
0.8387 Intermediate Similarity NPC202261
0.8387 Intermediate Similarity NPC106589
0.8387 Intermediate Similarity NPC257207
0.8387 Intermediate Similarity NPC295133
0.8374 Intermediate Similarity NPC133506
0.8361 Intermediate Similarity NPC278681
0.8361 Intermediate Similarity NPC470911
0.8361 Intermediate Similarity NPC470517
0.8361 Intermediate Similarity NPC470915
0.8361 Intermediate Similarity NPC470914
0.8347 Intermediate Similarity NPC20979
0.8347 Intermediate Similarity NPC476690
0.8347 Intermediate Similarity NPC100048
0.8347 Intermediate Similarity NPC290693
0.8346 Intermediate Similarity NPC476966
0.8346 Intermediate Similarity NPC471407
0.8333 Intermediate Similarity NPC329784
0.8333 Intermediate Similarity NPC106446
0.8333 Intermediate Similarity NPC240070
0.8319 Intermediate Similarity NPC216595
0.8319 Intermediate Similarity NPC231797
0.8319 Intermediate Similarity NPC473567
0.8295 Intermediate Similarity NPC316915
0.8293 Intermediate Similarity NPC473566
0.8293 Intermediate Similarity NPC475358
0.8293 Intermediate Similarity NPC112936
0.8291 Intermediate Similarity NPC472988
0.8291 Intermediate Similarity NPC38217
0.8291 Intermediate Similarity NPC295980
0.8281 Intermediate Similarity NPC173347
0.8279 Intermediate Similarity NPC16701
0.8279 Intermediate Similarity NPC10366
0.8268 Intermediate Similarity NPC45606
0.8268 Intermediate Similarity NPC220838
0.8264 Intermediate Similarity NPC477031
0.8264 Intermediate Similarity NPC63609
0.8254 Intermediate Similarity NPC297950
0.825 Intermediate Similarity NPC171126
0.825 Intermediate Similarity NPC307642
0.825 Intermediate Similarity NPC49413
0.825 Intermediate Similarity NPC290608
0.825 Intermediate Similarity NPC473128
0.825 Intermediate Similarity NPC40133
0.825 Intermediate Similarity NPC44298
0.824 Intermediate Similarity NPC41129
0.8235 Intermediate Similarity NPC208189
0.8235 Intermediate Similarity NPC65034
0.822 Intermediate Similarity NPC51925
0.822 Intermediate Similarity NPC125361
0.822 Intermediate Similarity NPC14630
0.822 Intermediate Similarity NPC154085
0.822 Intermediate Similarity NPC250089
0.822 Intermediate Similarity NPC43976
0.822 Intermediate Similarity NPC157530
0.822 Intermediate Similarity NPC296761
0.8217 Intermediate Similarity NPC471855
0.8217 Intermediate Similarity NPC231240
0.8211 Intermediate Similarity NPC213761
0.8211 Intermediate Similarity NPC153085
0.8211 Intermediate Similarity NPC268326
0.8211 Intermediate Similarity NPC35171
0.8205 Intermediate Similarity NPC190395
0.8205 Intermediate Similarity NPC33053
0.8205 Intermediate Similarity NPC234160
0.8203 Intermediate Similarity NPC140092
0.8203 Intermediate Similarity NPC188234
0.8203 Intermediate Similarity NPC232785
0.8203 Intermediate Similarity NPC276838
0.8203 Intermediate Similarity NPC329986
0.8203 Intermediate Similarity NPC125077
0.8197 Intermediate Similarity NPC185287
0.8197 Intermediate Similarity NPC477807
0.8197 Intermediate Similarity NPC157380
0.8182 Intermediate Similarity NPC11548
0.8182 Intermediate Similarity NPC477808
0.8168 Intermediate Similarity NPC194716
0.8167 Intermediate Similarity NPC328074
0.8167 Intermediate Similarity NPC317460
0.8167 Intermediate Similarity NPC473125
0.8167 Intermediate Similarity NPC470025
0.8167 Intermediate Similarity NPC44537
0.8167 Intermediate Similarity NPC321272
0.8167 Intermediate Similarity NPC42171
0.8167 Intermediate Similarity NPC112274
0.816 Intermediate Similarity NPC115349
0.8154 Intermediate Similarity NPC476221
0.8154 Intermediate Similarity NPC477709
0.8151 Intermediate Similarity NPC103491
0.8151 Intermediate Similarity NPC191439
0.8151 Intermediate Similarity NPC170974
0.8151 Intermediate Similarity NPC12795
0.8151 Intermediate Similarity NPC103627
0.8151 Intermediate Similarity NPC316708

  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 NPC179261 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
0.9652 High Similarity NPD7503 Approved
0.8908 High Similarity NPD8294 Approved
0.8908 High Similarity NPD8377 Approved
0.8833 High Similarity NPD8380 Approved
0.8833 High Similarity NPD8379 Approved
0.8833 High Similarity NPD8296 Approved
0.8833 High Similarity NPD8378 Approved
0.8833 High Similarity NPD8335 Approved
0.8678 High Similarity NPD8033 Approved
0.843 Intermediate Similarity NPD7328 Approved
0.843 Intermediate Similarity NPD7327 Approved
0.8361 Intermediate Similarity NPD7516 Approved
0.7969 Intermediate Similarity NPD7507 Approved
0.7951 Intermediate Similarity NPD8133 Approved
0.7786 Intermediate Similarity NPD7319 Approved
0.7686 Intermediate Similarity NPD6686 Approved
0.7603 Intermediate Similarity NPD6412 Phase 2
0.7519 Intermediate Similarity NPD8513 Phase 3
0.7444 Intermediate Similarity NPD7736 Approved
0.7385 Intermediate Similarity NPD8517 Approved
0.7385 Intermediate Similarity NPD8515 Approved
0.7385 Intermediate Similarity NPD8516 Approved
0.7273 Intermediate Similarity NPD8328 Phase 3
0.7209 Intermediate Similarity NPD7115 Discovery
0.7197 Intermediate Similarity NPD6370 Approved
0.7167 Intermediate Similarity NPD7638 Approved
0.7165 Intermediate Similarity NPD6882 Approved
0.7165 Intermediate Similarity NPD8297 Approved
0.7111 Intermediate Similarity NPD8293 Discontinued
0.7107 Intermediate Similarity NPD7639 Approved
0.7107 Intermediate Similarity NPD7640 Approved
0.709 Intermediate Similarity NPD7492 Approved
0.7077 Intermediate Similarity NPD6009 Approved
0.7063 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7625 Phase 1
0.7045 Intermediate Similarity NPD6054 Approved
0.7045 Intermediate Similarity NPD6319 Approved
0.7037 Intermediate Similarity NPD6616 Approved
0.7025 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.6985 Remote Similarity NPD7078 Approved
0.6977 Remote Similarity NPD4632 Approved
0.6953 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6053 Discontinued
0.6891 Remote Similarity NPD8171 Discontinued
0.6866 Remote Similarity NPD6016 Approved
0.6866 Remote Similarity NPD6015 Approved
0.685 Remote Similarity NPD6899 Approved
0.685 Remote Similarity NPD6881 Approved
0.6822 Remote Similarity NPD6650 Approved
0.6822 Remote Similarity NPD6649 Approved
0.6822 Remote Similarity NPD8130 Phase 1
0.6818 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5988 Approved
0.6791 Remote Similarity NPD6059 Approved
0.6772 Remote Similarity NPD5697 Approved
0.6744 Remote Similarity NPD6883 Approved
0.6744 Remote Similarity NPD7102 Approved
0.6744 Remote Similarity NPD7290 Approved
0.6723 Remote Similarity NPD7838 Discovery
0.6693 Remote Similarity NPD6675 Approved
0.6693 Remote Similarity NPD6402 Approved
0.6693 Remote Similarity NPD7128 Approved
0.6693 Remote Similarity NPD5739 Approved
0.6692 Remote Similarity NPD6847 Approved
0.6692 Remote Similarity NPD6869 Approved
0.6692 Remote Similarity NPD6617 Approved
0.669 Remote Similarity NPD8450 Suspended
0.6667 Remote Similarity NPD6372 Approved
0.6667 Remote Similarity NPD6014 Approved
0.6667 Remote Similarity NPD6013 Approved
0.6667 Remote Similarity NPD6373 Approved
0.6667 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6642 Remote Similarity NPD7604 Phase 2
0.664 Remote Similarity NPD5344 Discontinued
0.6639 Remote Similarity NPD6051 Approved
0.662 Remote Similarity NPD8449 Approved
0.6618 Remote Similarity NPD5983 Phase 2
0.6614 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6613 Remote Similarity NPD4225 Approved
0.6589 Remote Similarity NPD7320 Approved
0.6589 Remote Similarity NPD6011 Approved
0.6587 Remote Similarity NPD7632 Discontinued
0.656 Remote Similarity NPD6648 Approved
0.6547 Remote Similarity NPD6336 Discontinued
0.6532 Remote Similarity NPD6083 Phase 2
0.6532 Remote Similarity NPD6084 Phase 2
0.6522 Remote Similarity NPD6067 Discontinued
0.6512 Remote Similarity NPD5701 Approved
0.65 Remote Similarity NPD8074 Phase 3
0.6489 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6489 Remote Similarity NPD4634 Approved
0.6471 Remote Similarity NPD7524 Approved
0.6457 Remote Similarity NPD5211 Phase 2
0.6434 Remote Similarity NPD7260 Phase 2
0.6429 Remote Similarity NPD5286 Approved
0.6429 Remote Similarity NPD5285 Approved
0.6429 Remote Similarity NPD4696 Approved
0.6393 Remote Similarity NPD7637 Suspended
0.6386 Remote Similarity NPD7799 Discontinued
0.6357 Remote Similarity NPD5141 Approved
0.6356 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6356 Remote Similarity NPD7338 Clinical (unspecified phase)
0.635 Remote Similarity NPD7100 Approved
0.635 Remote Similarity NPD7101 Approved
0.6338 Remote Similarity NPD6033 Approved
0.6328 Remote Similarity NPD5224 Approved
0.6328 Remote Similarity NPD5226 Approved
0.6328 Remote Similarity NPD4633 Approved
0.6328 Remote Similarity NPD5225 Approved
0.6316 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6308 Remote Similarity NPD6008 Approved
0.629 Remote Similarity NPD7748 Approved
0.6279 Remote Similarity NPD5174 Approved
0.6279 Remote Similarity NPD5175 Approved
0.6277 Remote Similarity NPD6335 Approved
0.6271 Remote Similarity NPD6695 Phase 3
0.627 Remote Similarity NPD7902 Approved
0.627 Remote Similarity NPD4755 Approved
0.626 Remote Similarity NPD7899 Clinical (unspecified phase)
0.626 Remote Similarity NPD5281 Approved
0.626 Remote Similarity NPD5954 Clinical (unspecified phase)
0.626 Remote Similarity NPD5284 Approved
0.625 Remote Similarity NPD6274 Approved
0.625 Remote Similarity NPD5956 Approved
0.625 Remote Similarity NPD5223 Approved
0.6241 Remote Similarity NPD6371 Approved
0.624 Remote Similarity NPD5695 Phase 3
0.622 Remote Similarity NPD5696 Approved
0.6212 Remote Similarity NPD4730 Approved
0.6212 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6212 Remote Similarity NPD4729 Approved
0.621 Remote Similarity NPD4202 Approved
0.6207 Remote Similarity NPD4195 Approved
0.6204 Remote Similarity NPD6317 Approved
0.6198 Remote Similarity NPD7750 Discontinued
0.6179 Remote Similarity NPD6698 Approved
0.6179 Remote Similarity NPD46 Approved
0.6172 Remote Similarity NPD4700 Approved
0.617 Remote Similarity NPD7829 Approved
0.617 Remote Similarity NPD7830 Approved
0.6159 Remote Similarity NPD6313 Approved
0.6159 Remote Similarity NPD6314 Approved
0.6154 Remote Similarity NPD7525 Registered
0.6148 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6129 Remote Similarity NPD6079 Approved
0.6129 Remote Similarity NPD7515 Phase 2
0.6129 Remote Similarity NPD5693 Phase 1
0.6124 Remote Similarity NPD4159 Approved
0.6119 Remote Similarity NPD5249 Phase 3
0.6119 Remote Similarity NPD5247 Approved
0.6119 Remote Similarity NPD5248 Approved
0.6119 Remote Similarity NPD5250 Approved
0.6119 Remote Similarity NPD5251 Approved
0.6116 Remote Similarity NPD6409 Approved
0.6116 Remote Similarity NPD7146 Approved
0.6116 Remote Similarity NPD7334 Approved
0.6116 Remote Similarity NPD5330 Approved
0.6116 Remote Similarity NPD6684 Approved
0.6116 Remote Similarity NPD7521 Approved
0.6111 Remote Similarity NPD5210 Approved
0.6111 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6111 Remote Similarity NPD8336 Approved
0.6111 Remote Similarity NPD8337 Approved
0.6111 Remote Similarity NPD4629 Approved
0.6098 Remote Similarity NPD4753 Phase 2
0.608 Remote Similarity NPD6399 Phase 3
0.6066 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6061 Remote Similarity NPD4768 Approved
0.6061 Remote Similarity NPD4767 Approved
0.6054 Remote Similarity NPD6845 Suspended
0.6042 Remote Similarity NPD8448 Approved
0.6032 Remote Similarity NPD7900 Approved
0.6032 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6028 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6028 Remote Similarity NPD6908 Approved
0.6028 Remote Similarity NPD6909 Approved
0.6027 Remote Similarity NPD8392 Approved
0.6027 Remote Similarity NPD8391 Approved
0.6027 Remote Similarity NPD8390 Approved
0.6017 Remote Similarity NPD6931 Approved
0.6017 Remote Similarity NPD6930 Phase 2
0.6017 Remote Similarity NPD7514 Phase 3
0.6016 Remote Similarity NPD6903 Approved
0.6 Remote Similarity NPD8034 Phase 2
0.6 Remote Similarity NPD5694 Approved
0.6 Remote Similarity NPD6050 Approved
0.6 Remote Similarity NPD8035 Phase 2
0.6 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5987 Remote Similarity NPD7236 Approved
0.5974 Remote Similarity NPD7266 Discontinued
0.5972 Remote Similarity NPD8451 Approved
0.597 Remote Similarity NPD5128 Approved
0.5968 Remote Similarity NPD6673 Approved
0.5968 Remote Similarity NPD6904 Approved
0.5968 Remote Similarity NPD5328 Approved
0.5968 Remote Similarity NPD6080 Approved
0.5965 Remote Similarity NPD8470 Clinical (unspecified phase)
0.5956 Remote Similarity NPD5217 Approved
0.5956 Remote Similarity NPD5215 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