Structure

Physi-Chem Properties

Molecular Weight:  750.4
Volume:  738.277
LogP:  4.056
LogD:  2.845
LogS:  -4.435
# Rotatable Bonds:  22
TPSA:  215.2
# H-Bond Aceptor:  16
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.085
Synthetic Accessibility Score:  5.162
Fsp3:  0.917
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.259
MDCK Permeability:  0.00011972033098572865
Pgp-inhibitor:  0.989
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.915
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.009
Plasma Protein Binding (PPB):  85.73910522460938%
Volume Distribution (VD):  0.973
Pgp-substrate:  6.585054874420166%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.095
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.068
CYP2C9-inhibitor:  0.056
CYP2C9-substrate:  0.012
CYP2D6-inhibitor:  0.673
CYP2D6-substrate:  0.021
CYP3A4-inhibitor:  0.097
CYP3A4-substrate:  0.044

ADMET: Excretion

Clearance (CL):  1.167
Half-life (T1/2):  0.771

ADMET: Toxicity

hERG Blockers:  0.608
Human Hepatotoxicity (H-HT):  0.692
Drug-inuced Liver Injury (DILI):  0.953
AMES Toxicity:  0.178
Rat Oral Acute Toxicity:  0.08
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.912
Carcinogencity:  0.106
Eye Corrosion:  0.005
Eye Irritation:  0.012
Respiratory Toxicity:  0.905

Download Data

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

  Natural Product: NPC67099

Natural Product ID:  NPC67099
Common Name*:   Cleistrioside-5
IUPAC Name:   [(2S,3R,4R,5R,6S)-5-acetyloxy-6-[(2S,3R,4S,5S,6S)-5-acetyloxy-2-[(2S,3R,4S,5R,6R)-6-dodecoxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-3-hydroxy-6-methyloxan-4-yl]oxy-4-hydroxy-2-methyloxan-3-yl] acetate
Synonyms:   Cleistrioside-5
Standard InCHIKey:  DFGWXZRIFMDDNA-DAZFWBFJSA-N
Standard InCHI:  InChI=1S/C36H62O16/c1-8-9-10-11-12-13-14-15-16-17-18-44-34-26(41)25(40)29(19(2)45-34)51-35-28(43)32(31(21(4)46-35)49-23(6)38)52-36-33(50-24(7)39)27(42)30(20(3)47-36)48-22(5)37/h19-21,25-36,40-43H,8-18H2,1-7H3/t19-,20-,21-,25-,26+,27+,28+,29-,30-,31-,32-,33+,34+,35-,36-/m0/s1
SMILES:  CCCCCCCCCCCCO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OC(=O)C)O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL449465
PubChem CID:   11520558
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0000198] Oligosaccharides

*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
NPO27352 Cleistopholis patens Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[16643031]
NPO27352 Cleistopholis patens Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[3325614]
NPO27352 Cleistopholis patens 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
NPT457 Cell Line BT-549 Homo sapiens GI50 = 7900.0 nM PMID[533035]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 4840.0 nM PMID[533035]
NPT90 Cell Line DU-145 Homo sapiens GI50 = 7940.0 nM PMID[533035]
NPT306 Cell Line PC-3 Homo sapiens GI50 = 2370.0 nM PMID[533035]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 = 8780.0 nM PMID[533035]
NPT376 Cell Line A498 Homo sapiens GI50 = 6730.0 nM PMID[533035]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 = 5910.0 nM PMID[533035]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 = 6210.0 nM PMID[533035]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 = 7680.0 nM PMID[533035]
NPT392 Cell Line SNB-75 Homo sapiens GI50 = 3420.0 nM PMID[533035]
NPT374 Cell Line SF-539 Homo sapiens GI50 = 7110.0 nM PMID[533035]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 4350.0 nM PMID[533035]
NPT148 Cell Line HCT-15 Homo sapiens GI50 = 8390.0 nM PMID[533035]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 6320.0 nM PMID[533035]
NPT81 Cell Line A549 Homo sapiens GI50 = 6690.0 nM PMID[533035]
NPT385 Cell Line SR Homo sapiens GI50 = 3200.0 nM PMID[533035]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 = 4120.0 nM PMID[533035]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 90900.0 nM PMID[533035]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 91000.0 nM PMID[533036]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 8.0 ug.mL-1 PMID[533034]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 2.0 ug.mL-1 PMID[533034]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 4.0 ug.mL-1 PMID[533034]
NPT1477 Organism Staphylococcus haemolyticus Staphylococcus haemolyticus MIC = 4.0 ug.mL-1 PMID[533034]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 4.0 ug.mL-1 PMID[533034]
NPT1531 Organism Enterococcus faecium Enterococcus faecium MIC = 2.0 ug.mL-1 PMID[533034]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC = 8.0 ug.mL-1 PMID[533034]
NPT5305 Organism Corynebacterium jeikeium Corynebacterium jeikeium MIC > 32.0 ug.mL-1 PMID[533034]
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 2.0 ug.mL-1 PMID[533034]
NPT1228 Organism Streptococcus pyogenes Streptococcus pyogenes MIC = 8.0 ug.mL-1 PMID[533034]
NPT4066 Organism Streptococcus mitis Streptococcus mitis MIC = 8.0 ug.mL-1 PMID[533034]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 32.0 ug.mL-1 PMID[533034]
NPT19 Organism Escherichia coli Escherichia coli MIC > 32.0 ug.mL-1 PMID[533034]
NPT1238 Organism Staphylococcus Staphylococcus MIC = 2.0 ug.mL-1 PMID[533034]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 2.0 ug.mL-1 PMID[533034]
NPT1271 Organism Bacillus sp. Bacillus sp. MIC = 2.0 ug.mL-1 PMID[533034]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC = 4.0 ug.mL-1 PMID[533034]
NPT5904 Organism Corynebacterium sp. Corynebacterium sp. MIC = 8.0 ug.mL-1 PMID[533034]
NPT174 Organism Streptococcus Streptococcus MIC = 4.0 ug.mL-1 PMID[533034]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 9290.0 nM PMID[533035]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 32000.0 nM PMID[533035]
NPT1466 Organism Escherichia coli K12 Escherichia coli K-12 MIC > 64000.0 nM PMID[533035]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC > 64000.0 nM PMID[533035]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 32000.0 nM PMID[533036]

☑ 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 NPC67099 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
0.9692 High Similarity NPC53760
0.9692 High Similarity NPC52268
0.9524 High Similarity NPC190418
0.9524 High Similarity NPC471761
0.9524 High Similarity NPC471760
0.9403 High Similarity NPC225748
0.9403 High Similarity NPC169085
0.9403 High Similarity NPC9763
0.9403 High Similarity NPC39266
0.9118 High Similarity NPC206823
0.9118 High Similarity NPC163812
0.9 High Similarity NPC477350
0.8955 High Similarity NPC211428
0.8889 High Similarity NPC477750
0.8889 High Similarity NPC477757
0.8889 High Similarity NPC477755
0.8889 High Similarity NPC477763
0.8889 High Similarity NPC477753
0.8889 High Similarity NPC477762
0.8873 High Similarity NPC476781
0.8873 High Similarity NPC476783
0.8873 High Similarity NPC476782
0.8873 High Similarity NPC216883
0.8806 High Similarity NPC50228
0.8806 High Similarity NPC250619
0.8806 High Similarity NPC97736
0.875 High Similarity NPC477328
0.875 High Similarity NPC477323
0.875 High Similarity NPC477326
0.875 High Similarity NPC113745
0.875 High Similarity NPC475425
0.875 High Similarity NPC477329
0.875 High Similarity NPC146380
0.875 High Similarity NPC109887
0.875 High Similarity NPC477330
0.875 High Similarity NPC281563
0.875 High Similarity NPC477320
0.875 High Similarity NPC477325
0.8676 High Similarity NPC285003
0.8676 High Similarity NPC241265
0.863 High Similarity NPC85759
0.863 High Similarity NPC22742
0.863 High Similarity NPC158302
0.863 High Similarity NPC477344
0.863 High Similarity NPC146992
0.863 High Similarity NPC477346
0.863 High Similarity NPC294748
0.8571 High Similarity NPC317023
0.8514 High Similarity NPC267592
0.8413 Intermediate Similarity NPC472025
0.84 Intermediate Similarity NPC477318
0.84 Intermediate Similarity NPC184915
0.84 Intermediate Similarity NPC472204
0.84 Intermediate Similarity NPC238056
0.84 Intermediate Similarity NPC44782
0.84 Intermediate Similarity NPC290012
0.84 Intermediate Similarity NPC183888
0.84 Intermediate Similarity NPC472205
0.84 Intermediate Similarity NPC477317
0.84 Intermediate Similarity NPC27289
0.84 Intermediate Similarity NPC475667
0.84 Intermediate Similarity NPC259294
0.84 Intermediate Similarity NPC307400
0.84 Intermediate Similarity NPC169345
0.84 Intermediate Similarity NPC186992
0.84 Intermediate Similarity NPC126685
0.84 Intermediate Similarity NPC477319
0.84 Intermediate Similarity NPC475270
0.84 Intermediate Similarity NPC477347
0.84 Intermediate Similarity NPC173328
0.84 Intermediate Similarity NPC476087
0.84 Intermediate Similarity NPC123204
0.84 Intermediate Similarity NPC143421
0.84 Intermediate Similarity NPC475327
0.84 Intermediate Similarity NPC472203
0.84 Intermediate Similarity NPC472202
0.84 Intermediate Similarity NPC472200
0.84 Intermediate Similarity NPC297768
0.84 Intermediate Similarity NPC269318
0.84 Intermediate Similarity NPC119583
0.84 Intermediate Similarity NPC89843
0.84 Intermediate Similarity NPC115013
0.84 Intermediate Similarity NPC224953
0.84 Intermediate Similarity NPC472201
0.84 Intermediate Similarity NPC477331
0.8382 Intermediate Similarity NPC206601
0.8358 Intermediate Similarity NPC12040
0.8358 Intermediate Similarity NPC76881
0.8254 Intermediate Similarity NPC148424
0.8235 Intermediate Similarity NPC477752
0.8235 Intermediate Similarity NPC477751
0.8235 Intermediate Similarity NPC477764
0.8235 Intermediate Similarity NPC477756
0.8209 Intermediate Similarity NPC6848
0.8182 Intermediate Similarity NPC477332
0.8182 Intermediate Similarity NPC472352
0.8182 Intermediate Similarity NPC60849
0.8116 Intermediate Similarity NPC477760
0.8116 Intermediate Similarity NPC477759
0.8116 Intermediate Similarity NPC477754
0.8116 Intermediate Similarity NPC477758
0.8116 Intermediate Similarity NPC477761
0.8056 Intermediate Similarity NPC308096
0.8056 Intermediate Similarity NPC291228
0.8 Intermediate Similarity NPC34877
0.8 Intermediate Similarity NPC290179
0.7937 Intermediate Similarity NPC303727
0.7917 Intermediate Similarity NPC184550
0.7917 Intermediate Similarity NPC185419
0.7794 Intermediate Similarity NPC325773
0.7778 Intermediate Similarity NPC145112
0.7778 Intermediate Similarity NPC58629
0.7778 Intermediate Similarity NPC107914
0.7778 Intermediate Similarity NPC246558
0.7778 Intermediate Similarity NPC242073
0.7778 Intermediate Similarity NPC89145
0.7778 Intermediate Similarity NPC269166
0.7778 Intermediate Similarity NPC157514
0.7778 Intermediate Similarity NPC165198
0.7778 Intermediate Similarity NPC67660
0.7727 Intermediate Similarity NPC320032
0.75 Intermediate Similarity NPC470313
0.75 Intermediate Similarity NPC38295
0.75 Intermediate Similarity NPC472026
0.75 Intermediate Similarity NPC156089
0.75 Intermediate Similarity NPC473500
0.746 Intermediate Similarity NPC23134
0.746 Intermediate Similarity NPC124963
0.746 Intermediate Similarity NPC233726
0.746 Intermediate Similarity NPC326533
0.7412 Intermediate Similarity NPC477349
0.7333 Intermediate Similarity NPC55652
0.7286 Intermediate Similarity NPC268243
0.725 Intermediate Similarity NPC236649
0.725 Intermediate Similarity NPC21693
0.7241 Intermediate Similarity NPC163409
0.7241 Intermediate Similarity NPC44682
0.7241 Intermediate Similarity NPC477348
0.7241 Intermediate Similarity NPC477345
0.7241 Intermediate Similarity NPC238264
0.7231 Intermediate Similarity NPC130683
0.7231 Intermediate Similarity NPC323361
0.7206 Intermediate Similarity NPC322855
0.7179 Intermediate Similarity NPC244002
0.716 Intermediate Similarity NPC248415
0.7143 Intermediate Similarity NPC51662
0.7143 Intermediate Similarity NPC157193
0.7143 Intermediate Similarity NPC282143
0.7143 Intermediate Similarity NPC42503
0.7143 Intermediate Similarity NPC299781
0.7125 Intermediate Similarity NPC163362
0.7125 Intermediate Similarity NPC127295
0.7083 Intermediate Similarity NPC147292
0.7079 Intermediate Similarity NPC473765
0.7079 Intermediate Similarity NPC476066
0.7079 Intermediate Similarity NPC475593
0.7079 Intermediate Similarity NPC475525
0.7079 Intermediate Similarity NPC475540
0.7079 Intermediate Similarity NPC475375
0.7079 Intermediate Similarity NPC475164
0.7079 Intermediate Similarity NPC475241
0.7079 Intermediate Similarity NPC473605
0.7067 Intermediate Similarity NPC474078
0.7059 Intermediate Similarity NPC219040
0.7013 Intermediate Similarity NPC138273
0.7 Intermediate Similarity NPC470591
0.7 Intermediate Similarity NPC210157
0.6984 Remote Similarity NPC14144
0.6977 Remote Similarity NPC285588
0.6962 Remote Similarity NPC110813
0.6923 Remote Similarity NPC209798
0.6923 Remote Similarity NPC471375
0.6923 Remote Similarity NPC471374
0.6905 Remote Similarity NPC83839
0.6892 Remote Similarity NPC32148
0.6875 Remote Similarity NPC133377
0.6866 Remote Similarity NPC289979
0.6854 Remote Similarity NPC470283
0.6848 Remote Similarity NPC471426
0.6848 Remote Similarity NPC471427
0.6848 Remote Similarity NPC51579
0.6848 Remote Similarity NPC471428
0.6842 Remote Similarity NPC471879
0.6835 Remote Similarity NPC279575
0.6829 Remote Similarity NPC216941
0.6829 Remote Similarity NPC469469
0.6825 Remote Similarity NPC321087
0.6825 Remote Similarity NPC277475
0.6824 Remote Similarity NPC470657
0.6824 Remote Similarity NPC471410
0.6824 Remote Similarity NPC471411
0.6818 Remote Similarity NPC110072
0.6795 Remote Similarity NPC308489
0.6795 Remote Similarity NPC166250
0.6786 Remote Similarity NPC288471
0.6778 Remote Similarity NPC94582
0.6778 Remote Similarity NPC57964
0.6774 Remote Similarity NPC2313
0.6774 Remote Similarity NPC475157
0.6774 Remote Similarity NPC154132

  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 NPC67099 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
0.8308 Intermediate Similarity NPD6123 Approved
0.7937 Intermediate Similarity NPD7346 Approved
0.7778 Intermediate Similarity NPD893 Approved
0.7778 Intermediate Similarity NPD890 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD891 Phase 3
0.7778 Intermediate Similarity NPD888 Phase 3
0.7778 Intermediate Similarity NPD892 Phase 3
0.7662 Intermediate Similarity NPD7329 Approved
0.7619 Intermediate Similarity NPD2269 Approved
0.746 Intermediate Similarity NPD904 Phase 3
0.746 Intermediate Similarity NPD905 Approved
0.7231 Intermediate Similarity NPD889 Approved
0.7231 Intermediate Similarity NPD887 Approved
0.7231 Intermediate Similarity NPD895 Approved
0.7231 Intermediate Similarity NPD894 Approved
0.7164 Intermediate Similarity NPD2267 Suspended
0.7105 Intermediate Similarity NPD3181 Approved
0.6892 Remote Similarity NPD897 Approved
0.6892 Remote Similarity NPD898 Approved
0.6892 Remote Similarity NPD896 Approved
0.6842 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6812 Remote Similarity NPD369 Approved
0.6667 Remote Similarity NPD8993 Phase 1
0.6667 Remote Similarity NPD8997 Approved
0.6667 Remote Similarity NPD8998 Phase 2
0.6667 Remote Similarity NPD8999 Phase 3
0.6667 Remote Similarity NPD9000 Phase 3
0.6618 Remote Similarity NPD3728 Approved
0.6618 Remote Similarity NPD3730 Approved
0.6471 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6471 Remote Similarity NPD3669 Approved
0.6462 Remote Similarity NPD8965 Approved
0.6462 Remote Similarity NPD8966 Approved
0.6374 Remote Similarity NPD8171 Discontinued
0.6351 Remote Similarity NPD847 Phase 1
0.6232 Remote Similarity NPD9036 Phase 3
0.6232 Remote Similarity NPD9035 Clinical (unspecified phase)
0.619 Remote Similarity NPD8788 Approved
0.6186 Remote Similarity NPD8083 Approved
0.6186 Remote Similarity NPD8139 Approved
0.6186 Remote Similarity NPD8085 Approved
0.6186 Remote Similarity NPD8138 Approved
0.6186 Remote Similarity NPD8086 Approved
0.6186 Remote Similarity NPD8084 Approved
0.6186 Remote Similarity NPD8082 Approved
0.6176 Remote Similarity NPD1400 Approved
0.6176 Remote Similarity NPD1399 Approved
0.6173 Remote Similarity NPD1810 Approved
0.6173 Remote Similarity NPD1811 Approved
0.6162 Remote Similarity NPD8393 Approved
0.6133 Remote Similarity NPD8961 Approved
0.6122 Remote Similarity NPD8276 Approved
0.6122 Remote Similarity NPD8275 Approved
0.6061 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6061 Remote Similarity NPD8081 Approved
0.6058 Remote Similarity NPD8133 Approved
0.602 Remote Similarity NPD7140 Approved
0.602 Remote Similarity NPD7139 Approved
0.602 Remote Similarity NPD7141 Clinical (unspecified phase)
0.5941 Remote Similarity NPD8140 Approved
0.5941 Remote Similarity NPD8307 Discontinued
0.5873 Remote Similarity NPD7536 Approved
0.5846 Remote Similarity NPD9006 Approved
0.5844 Remote Similarity NPD1457 Discontinued
0.5844 Remote Similarity NPD7909 Approved
0.5833 Remote Similarity NPD6428 Approved
0.5825 Remote Similarity NPD6941 Approved
0.5825 Remote Similarity NPD8305 Approved
0.5825 Remote Similarity NPD8306 Approved
0.5825 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5806 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5802 Remote Similarity NPD2686 Approved
0.5802 Remote Similarity NPD2687 Approved
0.5802 Remote Similarity NPD2254 Approved
0.58 Remote Similarity NPD8045 Clinical (unspecified phase)
0.5769 Remote Similarity NPD8087 Discontinued
0.5735 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5728 Remote Similarity NPD6686 Approved
0.5714 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3200 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5684 Remote Similarity NPD1447 Phase 3
0.5684 Remote Similarity NPD1446 Phase 3
0.5682 Remote Similarity NPD1779 Approved
0.5682 Remote Similarity NPD1780 Approved
0.5676 Remote Similarity NPD8959 Approved
0.5652 Remote Similarity NPD3202 Approved
0.5652 Remote Similarity NPD3208 Approved
0.5652 Remote Similarity NPD3209 Approved
0.5652 Remote Similarity NPD3201 Approved
0.5652 Remote Similarity NPD3207 Approved
0.5652 Remote Similarity NPD3203 Approved
0.5616 Remote Similarity NPD885 Approved
0.5616 Remote Similarity NPD884 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