Structure

Physi-Chem Properties

Molecular Weight:  578.27
Volume:  562.244
LogP:  0.611
LogD:  -0.026
LogS:  -3.168
# Rotatable Bonds:  4
TPSA:  187.12
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.214
Synthetic Accessibility Score:  5.412
Fsp3:  0.8
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:  -6.638
MDCK Permeability:  6.609411502722651e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.888
20% Bioavailability (F20%):  0.991
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.156
Plasma Protein Binding (PPB):  46.31641387939453%
Volume Distribution (VD):  0.395
Pgp-substrate:  29.971105575561523%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.958
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.174
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.02
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.043
CYP3A4-inhibitor:  0.658
CYP3A4-substrate:  0.124

ADMET: Excretion

Clearance (CL):  2.387
Half-life (T1/2):  0.399

ADMET: Toxicity

hERG Blockers:  0.246
Human Hepatotoxicity (H-HT):  0.394
Drug-inuced Liver Injury (DILI):  0.041
AMES Toxicity:  0.042
Rat Oral Acute Toxicity:  0.749
Maximum Recommended Daily Dose:  0.937
Skin Sensitization:  0.565
Carcinogencity:  0.865
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.985

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

  Natural Product: NPC75616

Natural Product ID:  NPC75616
Common Name*:   5Beta,14Beta,16Beta-Trihydroxy-19-Oxo-3Beta-[(Alpha-L-Rhamnopyranosyl)Oxy)]Bufa-20,22-Dienolide
IUPAC Name:   (3S,5S,8R,9S,10S,13R,14S,16S,17R)-5,14,16-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms:  
Standard InCHIKey:  QRFYVPVSGUSPHI-SEIYVQFCSA-N
Standard InCHI:  InChI=1S/C30H42O11/c1-15-23(34)24(35)25(36)26(40-15)41-17-5-9-28(14-31)18-6-8-27(2)22(16-3-4-21(33)39-13-16)20(32)12-30(27,38)19(18)7-10-29(28,37)11-17/h3-4,13-15,17-20,22-26,32,34-38H,5-12H2,1-2H3/t15-,17-,18-,19+,20-,22-,23-,24+,25+,26-,27+,28-,29-,30-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@]2(C=O)[C@H]3CC[C@]4(C)[C@@H](c5ccc(=O)oc5)[C@H](C[C@@]4([C@@H]3CC[C@@]2(C1)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL136358
PubChem CID:   9985633
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
NPO6205 Helleborus orientalis Species Ranunculaceae Eukaryota rhizomes n.a. n.a. PMID[12608856]

☑ 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
NPT924 Cell Line HSC-2 Homo sapiens IC50 = 0.0085 ug.mL-1 PMID[545071]
NPT1083 Cell Line A-375 Homo sapiens IC50 = 0.055 ug.mL-1 PMID[545071]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 0.74 ug.mL-1 PMID[545071]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 9.5 ug.mL-1 PMID[545071]

☑ 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 NPC75616 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
0.9841 High Similarity NPC62172
0.9841 High Similarity NPC289700
0.9453 High Similarity NPC158350
0.937 High Similarity NPC155529
0.9225 High Similarity NPC248703
0.9084 High Similarity NPC127656
0.9062 High Similarity NPC180079
0.9062 High Similarity NPC471352
0.9062 High Similarity NPC471360
0.9062 High Similarity NPC469755
0.9062 High Similarity NPC284406
0.9062 High Similarity NPC86159
0.9062 High Similarity NPC471359
0.9062 High Similarity NPC9499
0.9062 High Similarity NPC471358
0.9062 High Similarity NPC89514
0.9062 High Similarity NPC471361
0.9062 High Similarity NPC219085
0.9062 High Similarity NPC6108
0.9062 High Similarity NPC17896
0.9062 High Similarity NPC10823
0.9062 High Similarity NPC469753
0.9062 High Similarity NPC197707
0.9062 High Similarity NPC251866
0.9062 High Similarity NPC469752
0.9062 High Similarity NPC70542
0.9062 High Similarity NPC469751
0.9062 High Similarity NPC469754
0.9 High Similarity NPC32793
0.9 High Similarity NPC116075
0.9 High Similarity NPC247190
0.9 High Similarity NPC469749
0.9 High Similarity NPC146857
0.8992 High Similarity NPC173347
0.8968 High Similarity NPC55602
0.8931 High Similarity NPC329636
0.8906 High Similarity NPC179412
0.8906 High Similarity NPC146456
0.8906 High Similarity NPC471357
0.8906 High Similarity NPC117702
0.8906 High Similarity NPC471356
0.8906 High Similarity NPC469757
0.8864 High Similarity NPC194716
0.8855 High Similarity NPC104585
0.8855 High Similarity NPC225385
0.8855 High Similarity NPC157817
0.8855 High Similarity NPC298783
0.8828 High Similarity NPC469750
0.8828 High Similarity NPC250556
0.8797 High Similarity NPC329675
0.8797 High Similarity NPC59288
0.8779 High Similarity NPC93416
0.8769 High Similarity NPC232785
0.8769 High Similarity NPC125077
0.8769 High Similarity NPC276838
0.8769 High Similarity NPC188234
0.8769 High Similarity NPC140092
0.8769 High Similarity NPC329986
0.873 High Similarity NPC184555
0.8712 High Similarity NPC142756
0.8702 High Similarity NPC159338
0.8702 High Similarity NPC16569
0.8702 High Similarity NPC253456
0.8692 High Similarity NPC245094
0.8692 High Similarity NPC311534
0.8682 High Similarity NPC159499
0.8672 High Similarity NPC27363
0.8636 High Similarity NPC42670
0.8636 High Similarity NPC19124
0.8626 High Similarity NPC476966
0.8626 High Similarity NPC91
0.8626 High Similarity NPC221414
0.8615 High Similarity NPC329784
0.8615 High Similarity NPC240070
0.8571 High Similarity NPC477709
0.8571 High Similarity NPC476221
0.8516 High Similarity NPC233500
0.8496 Intermediate Similarity NPC471855
0.8496 Intermediate Similarity NPC231240
0.8462 Intermediate Similarity NPC318135
0.8462 Intermediate Similarity NPC233041
0.845 Intermediate Similarity NPC196130
0.8444 Intermediate Similarity NPC171619
0.8438 Intermediate Similarity NPC145074
0.8438 Intermediate Similarity NPC114939
0.8438 Intermediate Similarity NPC41123
0.8433 Intermediate Similarity NPC88668
0.8433 Intermediate Similarity NPC316915
0.8397 Intermediate Similarity NPC179261
0.8385 Intermediate Similarity NPC6193
0.8359 Intermediate Similarity NPC219656
0.8346 Intermediate Similarity NPC231529
0.8346 Intermediate Similarity NPC471407
0.8345 Intermediate Similarity NPC5153
0.8345 Intermediate Similarity NPC48414
0.8321 Intermediate Similarity NPC241456
0.8321 Intermediate Similarity NPC32868
0.8308 Intermediate Similarity NPC107493
0.8295 Intermediate Similarity NPC257610
0.8295 Intermediate Similarity NPC281840
0.8295 Intermediate Similarity NPC470312
0.8295 Intermediate Similarity NPC112936
0.8284 Intermediate Similarity NPC213634
0.8281 Intermediate Similarity NPC473617
0.8281 Intermediate Similarity NPC473828
0.8271 Intermediate Similarity NPC473620
0.8261 Intermediate Similarity NPC290746
0.8261 Intermediate Similarity NPC79250
0.8254 Intermediate Similarity NPC73050
0.8244 Intermediate Similarity NPC41129
0.8244 Intermediate Similarity NPC219804
0.8244 Intermediate Similarity NPC204812
0.8231 Intermediate Similarity NPC475219
0.8231 Intermediate Similarity NPC231518
0.8231 Intermediate Similarity NPC170084
0.8231 Intermediate Similarity NPC46570
0.8231 Intermediate Similarity NPC476204
0.8227 Intermediate Similarity NPC471172
0.8217 Intermediate Similarity NPC270850
0.8217 Intermediate Similarity NPC305260
0.8217 Intermediate Similarity NPC44899
0.8217 Intermediate Similarity NPC213761
0.8217 Intermediate Similarity NPC35171
0.8217 Intermediate Similarity NPC5292
0.8217 Intermediate Similarity NPC29639
0.8217 Intermediate Similarity NPC304260
0.8217 Intermediate Similarity NPC5883
0.8217 Intermediate Similarity NPC278681
0.8209 Intermediate Similarity NPC473593
0.8203 Intermediate Similarity NPC84987
0.8203 Intermediate Similarity NPC471355
0.8203 Intermediate Similarity NPC99728
0.8203 Intermediate Similarity NPC157376
0.8203 Intermediate Similarity NPC50305
0.8203 Intermediate Similarity NPC473852
0.8203 Intermediate Similarity NPC471354
0.8203 Intermediate Similarity NPC243196
0.8203 Intermediate Similarity NPC471353
0.8203 Intermediate Similarity NPC27507
0.8203 Intermediate Similarity NPC471351
0.8203 Intermediate Similarity NPC244402
0.8203 Intermediate Similarity NPC309034
0.8203 Intermediate Similarity NPC34390
0.8203 Intermediate Similarity NPC142066
0.8203 Intermediate Similarity NPC87250
0.8203 Intermediate Similarity NPC158344
0.8203 Intermediate Similarity NPC474483
0.8203 Intermediate Similarity NPC196429
0.8203 Intermediate Similarity NPC77319
0.8203 Intermediate Similarity NPC474418
0.8195 Intermediate Similarity NPC42399
0.8195 Intermediate Similarity NPC287423
0.8195 Intermediate Similarity NPC298841
0.8188 Intermediate Similarity NPC596
0.8175 Intermediate Similarity NPC44537
0.8169 Intermediate Similarity NPC194854
0.8169 Intermediate Similarity NPC48813
0.8168 Intermediate Similarity NPC471082
0.8168 Intermediate Similarity NPC269642
0.8168 Intermediate Similarity NPC193893
0.8156 Intermediate Similarity NPC471171
0.8154 Intermediate Similarity NPC475556
0.8154 Intermediate Similarity NPC474466
0.8154 Intermediate Similarity NPC475136
0.8154 Intermediate Similarity NPC79579
0.8154 Intermediate Similarity NPC475629
0.8154 Intermediate Similarity NPC476127
0.8154 Intermediate Similarity NPC476150
0.814 Intermediate Similarity NPC153440
0.814 Intermediate Similarity NPC13710
0.814 Intermediate Similarity NPC45475
0.814 Intermediate Similarity NPC471249
0.814 Intermediate Similarity NPC83287
0.814 Intermediate Similarity NPC16701
0.8134 Intermediate Similarity NPC473888
0.8134 Intermediate Similarity NPC114306
0.8134 Intermediate Similarity NPC477490
0.8125 Intermediate Similarity NPC99620
0.8125 Intermediate Similarity NPC5311
0.8125 Intermediate Similarity NPC207637
0.8125 Intermediate Similarity NPC310341
0.8125 Intermediate Similarity NPC199428
0.8125 Intermediate Similarity NPC193382
0.8125 Intermediate Similarity NPC469794
0.8125 Intermediate Similarity NPC72772
0.812 Intermediate Similarity NPC293112
0.812 Intermediate Similarity NPC47113
0.812 Intermediate Similarity NPC473635
0.812 Intermediate Similarity NPC174367
0.8116 Intermediate Similarity NPC471089
0.8116 Intermediate Similarity NPC141215
0.8116 Intermediate Similarity NPC190065
0.8112 Intermediate Similarity NPC475462
0.8112 Intermediate Similarity NPC16729
0.8106 Intermediate Similarity NPC11895
0.8106 Intermediate Similarity NPC469789
0.8092 Intermediate Similarity NPC312481
0.8092 Intermediate Similarity NPC40749
0.8092 Intermediate Similarity NPC129434
0.8092 Intermediate Similarity NPC173555

  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 NPC75616 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
0.9062 High Similarity NPD7319 Approved
0.8828 High Similarity NPD7507 Approved
0.8661 High Similarity NPD7503 Approved
0.8231 Intermediate Similarity NPD8033 Approved
0.814 Intermediate Similarity NPD7327 Approved
0.814 Intermediate Similarity NPD7328 Approved
0.8092 Intermediate Similarity NPD8296 Approved
0.8092 Intermediate Similarity NPD8335 Approved
0.8092 Intermediate Similarity NPD8380 Approved
0.8092 Intermediate Similarity NPD8378 Approved
0.8092 Intermediate Similarity NPD8379 Approved
0.8077 Intermediate Similarity NPD7516 Approved
0.8015 Intermediate Similarity NPD8377 Approved
0.8015 Intermediate Similarity NPD8294 Approved
0.8 Intermediate Similarity NPD7736 Approved
0.782 Intermediate Similarity NPD8513 Phase 3
0.7761 Intermediate Similarity NPD6370 Approved
0.7717 Intermediate Similarity NPD6686 Approved
0.7692 Intermediate Similarity NPD8133 Approved
0.7687 Intermediate Similarity NPD8516 Approved
0.7687 Intermediate Similarity NPD8517 Approved
0.7687 Intermediate Similarity NPD8515 Approved
0.7652 Intermediate Similarity NPD7115 Discovery
0.7647 Intermediate Similarity NPD7492 Approved
0.7612 Intermediate Similarity NPD6054 Approved
0.7612 Intermediate Similarity NPD6319 Approved
0.7591 Intermediate Similarity NPD6616 Approved
0.7574 Intermediate Similarity NPD8328 Phase 3
0.7536 Intermediate Similarity NPD8293 Discontinued
0.7536 Intermediate Similarity NPD7078 Approved
0.75 Intermediate Similarity NPD6412 Phase 2
0.7481 Intermediate Similarity NPD6882 Approved
0.7426 Intermediate Similarity NPD6015 Approved
0.7426 Intermediate Similarity NPD6016 Approved
0.7388 Intermediate Similarity NPD6009 Approved
0.7388 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD5988 Approved
0.7353 Intermediate Similarity NPD6059 Approved
0.7348 Intermediate Similarity NPD6053 Discontinued
0.7348 Intermediate Similarity NPD8297 Approved
0.7293 Intermediate Similarity NPD4632 Approved
0.7222 Intermediate Similarity NPD7638 Approved
0.7176 Intermediate Similarity NPD6881 Approved
0.7176 Intermediate Similarity NPD6899 Approved
0.7165 Intermediate Similarity NPD7640 Approved
0.7165 Intermediate Similarity NPD7639 Approved
0.7143 Intermediate Similarity NPD6649 Approved
0.7143 Intermediate Similarity NPD6650 Approved
0.7099 Intermediate Similarity NPD5697 Approved
0.7068 Intermediate Similarity NPD4634 Approved
0.7068 Intermediate Similarity NPD7102 Approved
0.7068 Intermediate Similarity NPD7290 Approved
0.7068 Intermediate Similarity NPD6883 Approved
0.7045 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD7128 Approved
0.7023 Intermediate Similarity NPD5739 Approved
0.7023 Intermediate Similarity NPD6675 Approved
0.7023 Intermediate Similarity NPD6402 Approved
0.7015 Intermediate Similarity NPD8130 Phase 1
0.7015 Intermediate Similarity NPD6847 Approved
0.7015 Intermediate Similarity NPD6617 Approved
0.7015 Intermediate Similarity NPD6869 Approved
0.6992 Remote Similarity NPD6014 Approved
0.6992 Remote Similarity NPD6013 Approved
0.6992 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6992 Remote Similarity NPD6372 Approved
0.6992 Remote Similarity NPD6373 Approved
0.6992 Remote Similarity NPD6012 Approved
0.695 Remote Similarity NPD7604 Phase 2
0.6946 Remote Similarity NPD7799 Discontinued
0.6929 Remote Similarity NPD5983 Phase 2
0.6923 Remote Similarity NPD8074 Phase 3
0.6917 Remote Similarity NPD7320 Approved
0.6917 Remote Similarity NPD6011 Approved
0.6875 Remote Similarity NPD6033 Approved
0.6866 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6853 Remote Similarity NPD6336 Discontinued
0.6842 Remote Similarity NPD5701 Approved
0.6822 Remote Similarity NPD4225 Approved
0.6818 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6794 Remote Similarity NPD5211 Phase 2
0.6769 Remote Similarity NPD5285 Approved
0.6769 Remote Similarity NPD5286 Approved
0.6769 Remote Similarity NPD4696 Approved
0.6767 Remote Similarity NPD6008 Approved
0.6765 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6735 Remote Similarity NPD7260 Phase 2
0.6692 Remote Similarity NPD5141 Approved
0.6691 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6691 Remote Similarity NPD6371 Approved
0.6667 Remote Similarity NPD7100 Approved
0.6667 Remote Similarity NPD5225 Approved
0.6667 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD5226 Approved
0.6667 Remote Similarity NPD7625 Phase 1
0.6667 Remote Similarity NPD7632 Discontinued
0.6667 Remote Similarity NPD7101 Approved
0.6642 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6621 Remote Similarity NPD8451 Approved
0.6617 Remote Similarity NPD5174 Approved
0.6617 Remote Similarity NPD5175 Approved
0.6615 Remote Similarity NPD4755 Approved
0.6614 Remote Similarity NPD7637 Suspended
0.6597 Remote Similarity NPD7829 Approved
0.6597 Remote Similarity NPD7830 Approved
0.6597 Remote Similarity NPD6067 Discontinued
0.6596 Remote Similarity NPD6335 Approved
0.6593 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6591 Remote Similarity NPD5223 Approved
0.6585 Remote Similarity NPD5760 Phase 2
0.6585 Remote Similarity NPD5761 Phase 2
0.6575 Remote Similarity NPD8448 Approved
0.6573 Remote Similarity NPD6921 Approved
0.6571 Remote Similarity NPD6274 Approved
0.6565 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6554 Remote Similarity NPD8392 Approved
0.6554 Remote Similarity NPD8391 Approved
0.6554 Remote Similarity NPD8390 Approved
0.6544 Remote Similarity NPD4729 Approved
0.6544 Remote Similarity NPD4730 Approved
0.6525 Remote Similarity NPD6317 Approved
0.6515 Remote Similarity NPD4700 Approved
0.6489 Remote Similarity NPD6084 Phase 2
0.6489 Remote Similarity NPD6083 Phase 2
0.6484 Remote Similarity NPD7983 Approved
0.6484 Remote Similarity NPD6079 Approved
0.6484 Remote Similarity NPD6411 Approved
0.6483 Remote Similarity NPD7642 Approved
0.6479 Remote Similarity NPD6314 Approved
0.6479 Remote Similarity NPD6313 Approved
0.6478 Remote Similarity NPD7236 Approved
0.6471 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6466 Remote Similarity NPD5344 Discontinued
0.6449 Remote Similarity NPD5248 Approved
0.6449 Remote Similarity NPD5251 Approved
0.6449 Remote Similarity NPD5247 Approved
0.6449 Remote Similarity NPD5249 Phase 3
0.6449 Remote Similarity NPD5250 Approved
0.6443 Remote Similarity NPD5956 Approved
0.6438 Remote Similarity NPD8340 Approved
0.6438 Remote Similarity NPD8341 Approved
0.6438 Remote Similarity NPD8342 Approved
0.6438 Remote Similarity NPD8299 Approved
0.6434 Remote Similarity NPD5779 Approved
0.6434 Remote Similarity NPD5778 Approved
0.6406 Remote Similarity NPD46 Approved
0.6406 Remote Similarity NPD6698 Approved
0.6405 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6397 Remote Similarity NPD4767 Approved
0.6397 Remote Similarity NPD4768 Approved
0.6391 Remote Similarity NPD6648 Approved
0.6385 Remote Similarity NPD7748 Approved
0.638 Remote Similarity NPD7239 Suspended
0.6364 Remote Similarity NPD7641 Discontinued
0.6364 Remote Similarity NPD7902 Approved
0.6358 Remote Similarity NPD8338 Approved
0.6358 Remote Similarity NPD6845 Suspended
0.6357 Remote Similarity NPD7515 Phase 2
0.6345 Remote Similarity NPD6909 Approved
0.6345 Remote Similarity NPD6908 Approved
0.6345 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6328 Remote Similarity NPD6101 Approved
0.6328 Remote Similarity NPD5328 Approved
0.6328 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6308 Remote Similarity NPD6399 Phase 3
0.6308 Remote Similarity NPD4202 Approved
0.6307 Remote Similarity NPD7685 Pre-registration
0.6304 Remote Similarity NPD5128 Approved
0.6288 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6288 Remote Similarity NPD4697 Phase 3
0.6288 Remote Similarity NPD5222 Approved
0.6288 Remote Similarity NPD5221 Approved
0.6286 Remote Similarity NPD5217 Approved
0.6286 Remote Similarity NPD5215 Approved
0.6286 Remote Similarity NPD5216 Approved
0.6279 Remote Similarity NPD5785 Approved
0.6279 Remote Similarity NPD7838 Discovery
0.625 Remote Similarity NPD7513 Clinical (unspecified phase)
0.625 Remote Similarity NPD4754 Approved
0.6241 Remote Similarity NPD5173 Approved
0.6233 Remote Similarity NPD8444 Approved
0.6231 Remote Similarity NPD8035 Phase 2
0.6231 Remote Similarity NPD8034 Phase 2
0.6231 Remote Similarity NPD5284 Approved
0.6231 Remote Similarity NPD5281 Approved
0.6224 Remote Similarity NPD6868 Approved
0.6214 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5135 Approved
0.6214 Remote Similarity NPD5169 Approved
0.6212 Remote Similarity NPD5695 Phase 3
0.62 Remote Similarity NPD8336 Approved
0.62 Remote Similarity NPD8337 Approved
0.6194 Remote Similarity NPD5696 Approved
0.6183 Remote Similarity NPD8171 Discontinued
0.6175 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6172 Remote Similarity NPD7524 Approved
0.6172 Remote Similarity NPD3573 Approved
0.617 Remote Similarity NPD5127 Approved
0.6167 Remote Similarity NPD8055 Clinical (unspecified phase)

  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