Structure

Physi-Chem Properties

Molecular Weight:  390.15
Volume:  359.548
LogP:  -0.91
LogD:  -0.032
LogS:  -1.314
# Rotatable Bonds:  5
TPSA:  155.14
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.34
Synthetic Accessibility Score:  4.985
Fsp3:  0.824
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.244
MDCK Permeability:  0.00013815407874062657
Pgp-inhibitor:  0.002
Pgp-substrate:  0.952
Human Intestinal Absorption (HIA):  0.964
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.225
Plasma Protein Binding (PPB):  22.285839080810547%
Volume Distribution (VD):  0.336
Pgp-substrate:  61.879478454589844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.069
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.456
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.043
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.08
CYP3A4-inhibitor:  0.026
CYP3A4-substrate:  0.075

ADMET: Excretion

Clearance (CL):  1.395
Half-life (T1/2):  0.879

ADMET: Toxicity

hERG Blockers:  0.046
Human Hepatotoxicity (H-HT):  0.275
Drug-inuced Liver Injury (DILI):  0.083
AMES Toxicity:  0.061
Rat Oral Acute Toxicity:  0.149
Maximum Recommended Daily Dose:  0.021
Skin Sensitization:  0.12
Carcinogencity:  0.93
Eye Corrosion:  0.003
Eye Irritation:  0.025
Respiratory Toxicity:  0.724

Download Data

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

  Natural Product: NPC50464

Natural Product ID:  NPC50464
Common Name*:   [(1R,4As,5S,7R,7Ar)-5-Hydroxy-7-Methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-4A,5,6,7A-Tetrahydro-1H-Cyclopenta[C]Pyran-7-Yl] Acetate
IUPAC Name:   [(1R,4aS,5S,7R,7aR)-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-7-yl] acetate
Synonyms:  
Standard InCHIKey:  FLOXQRMTDDOZKF-POQLYTHUSA-N
Standard InCHI:  InChI=1S/C17H26O10/c1-7(19)27-17(2)5-9(20)8-3-4-24-15(11(8)17)26-16-14(23)13(22)12(21)10(6-18)25-16/h3-4,8-16,18,20-23H,5-6H2,1-2H3/t8-,9+,10-,11+,12-,13+,14-,15-,16+,17-/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2OC=C[C@H]3[C@@H]2[C@](C)(OC(=O)C)C[C@@H]3O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL605532
PubChem CID:   46227125
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO33377 teucrium chamaedris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19674906]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.3 n.a. PMID[558997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.7 n.a. PMID[558997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.8 n.a. PMID[558997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 38900.0 nM PMID[558997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 44200.0 nM PMID[558997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 52200.0 nM PMID[558997]
NPT1 Others Radical scavenging activity IC50 > 300000.0 nM PMID[558997]

☑ 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 NPC50464 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
0.9535 High Similarity NPC294643
0.9535 High Similarity NPC274274
0.9535 High Similarity NPC473150
0.9529 High Similarity NPC93190
0.9398 High Similarity NPC259296
0.9398 High Similarity NPC98276
0.908 High Similarity NPC22918
0.8966 High Similarity NPC148534
0.8953 High Similarity NPC171484
0.8953 High Similarity NPC149018
0.8851 High Similarity NPC258501
0.8667 High Similarity NPC276298
0.8404 Intermediate Similarity NPC470684
0.8404 Intermediate Similarity NPC470683
0.8191 Intermediate Similarity NPC6765
0.8191 Intermediate Similarity NPC93869
0.8182 Intermediate Similarity NPC127235
0.81 Intermediate Similarity NPC80338
0.81 Intermediate Similarity NPC148270
0.81 Intermediate Similarity NPC197813
0.8085 Intermediate Similarity NPC274588
0.8065 Intermediate Similarity NPC235051
0.798 Intermediate Similarity NPC475928
0.798 Intermediate Similarity NPC37240
0.7959 Intermediate Similarity NPC3488
0.7959 Intermediate Similarity NPC287539
0.7959 Intermediate Similarity NPC216911
0.7917 Intermediate Similarity NPC284063
0.7917 Intermediate Similarity NPC170527
0.7917 Intermediate Similarity NPC161293
0.7879 Intermediate Similarity NPC474730
0.7879 Intermediate Similarity NPC4899
0.7879 Intermediate Similarity NPC177013
0.7879 Intermediate Similarity NPC35185
0.7864 Intermediate Similarity NPC193741
0.7857 Intermediate Similarity NPC244878
0.7857 Intermediate Similarity NPC476211
0.7857 Intermediate Similarity NPC476320
0.7835 Intermediate Similarity NPC86843
0.7822 Intermediate Similarity NPC170432
0.78 Intermediate Similarity NPC329834
0.7778 Intermediate Similarity NPC20673
0.7778 Intermediate Similarity NPC476230
0.7778 Intermediate Similarity NPC27474
0.7766 Intermediate Similarity NPC117596
0.7755 Intermediate Similarity NPC151093
0.7714 Intermediate Similarity NPC475851
0.7714 Intermediate Similarity NPC475924
0.7708 Intermediate Similarity NPC63897
0.77 Intermediate Similarity NPC304163
0.7692 Intermediate Similarity NPC220167
0.7692 Intermediate Similarity NPC136699
0.7684 Intermediate Similarity NPC472124
0.7684 Intermediate Similarity NPC472126
0.7684 Intermediate Similarity NPC472125
0.767 Intermediate Similarity NPC110701
0.7653 Intermediate Similarity NPC472290
0.7653 Intermediate Similarity NPC263674
0.7653 Intermediate Similarity NPC58267
0.7653 Intermediate Similarity NPC261372
0.7624 Intermediate Similarity NPC329704
0.7615 Intermediate Similarity NPC219656
0.7604 Intermediate Similarity NPC280390
0.7604 Intermediate Similarity NPC61201
0.76 Intermediate Similarity NPC219038
0.76 Intermediate Similarity NPC4637
0.76 Intermediate Similarity NPC476228
0.76 Intermediate Similarity NPC98859
0.7579 Intermediate Similarity NPC307699
0.7576 Intermediate Similarity NPC37866
0.7576 Intermediate Similarity NPC157739
0.7551 Intermediate Similarity NPC241911
0.7525 Intermediate Similarity NPC106668
0.7525 Intermediate Similarity NPC471599
0.75 Intermediate Similarity NPC306344
0.75 Intermediate Similarity NPC66504
0.75 Intermediate Similarity NPC255677
0.75 Intermediate Similarity NPC22149
0.7477 Intermediate Similarity NPC233500
0.7475 Intermediate Similarity NPC473555
0.7475 Intermediate Similarity NPC471770
0.7475 Intermediate Similarity NPC278939
0.7451 Intermediate Similarity NPC27687
0.7449 Intermediate Similarity NPC101051
0.7426 Intermediate Similarity NPC28304
0.7426 Intermediate Similarity NPC298255
0.7419 Intermediate Similarity NPC477746
0.7419 Intermediate Similarity NPC477747
0.7411 Intermediate Similarity NPC196130
0.7386 Intermediate Similarity NPC279575
0.7379 Intermediate Similarity NPC86095
0.7374 Intermediate Similarity NPC474297
0.7364 Intermediate Similarity NPC472080
0.7353 Intermediate Similarity NPC154452
0.7353 Intermediate Similarity NPC195510
0.7353 Intermediate Similarity NPC13171
0.7353 Intermediate Similarity NPC261117
0.7353 Intermediate Similarity NPC310804
0.7353 Intermediate Similarity NPC222062
0.7345 Intermediate Similarity NPC219804
0.734 Intermediate Similarity NPC470657
0.7333 Intermediate Similarity NPC170595
0.7333 Intermediate Similarity NPC295980
0.7327 Intermediate Similarity NPC317019
0.7327 Intermediate Similarity NPC473146
0.73 Intermediate Similarity NPC304445
0.73 Intermediate Similarity NPC236580
0.7282 Intermediate Similarity NPC118761
0.7282 Intermediate Similarity NPC197541
0.7282 Intermediate Similarity NPC234304
0.7282 Intermediate Similarity NPC284929
0.7282 Intermediate Similarity NPC267869
0.7273 Intermediate Similarity NPC291709
0.7273 Intermediate Similarity NPC241407
0.7264 Intermediate Similarity NPC208307
0.7263 Intermediate Similarity NPC31349
0.7255 Intermediate Similarity NPC21064
0.7255 Intermediate Similarity NPC121072
0.7245 Intermediate Similarity NPC470187
0.7245 Intermediate Similarity NPC474835
0.7238 Intermediate Similarity NPC470169
0.7238 Intermediate Similarity NPC470170
0.7234 Intermediate Similarity NPC470658
0.7228 Intermediate Similarity NPC469918
0.7228 Intermediate Similarity NPC96399
0.7228 Intermediate Similarity NPC117066
0.7228 Intermediate Similarity NPC469919
0.7228 Intermediate Similarity NPC223700
0.7216 Intermediate Similarity NPC216826
0.7216 Intermediate Similarity NPC270908
0.7216 Intermediate Similarity NPC470573
0.7216 Intermediate Similarity NPC231710
0.7216 Intermediate Similarity NPC120021
0.7216 Intermediate Similarity NPC65665
0.7184 Intermediate Similarity NPC250545
0.7156 Intermediate Similarity NPC287075
0.7143 Intermediate Similarity NPC473199
0.713 Intermediate Similarity NPC114188
0.713 Intermediate Similarity NPC470748
0.7129 Intermediate Similarity NPC153559
0.7129 Intermediate Similarity NPC76486
0.7115 Intermediate Similarity NPC197736
0.7113 Intermediate Similarity NPC299527
0.7113 Intermediate Similarity NPC104129
0.7113 Intermediate Similarity NPC477748
0.7113 Intermediate Similarity NPC249408
0.7097 Intermediate Similarity NPC20072
0.7094 Intermediate Similarity NPC145287
0.7094 Intermediate Similarity NPC163783
0.7091 Intermediate Similarity NPC106446
0.7087 Intermediate Similarity NPC67296
0.7083 Intermediate Similarity NPC316629
0.7075 Intermediate Similarity NPC470166
0.7065 Intermediate Similarity NPC100697
0.7059 Intermediate Similarity NPC90819
0.7059 Intermediate Similarity NPC124181
0.7059 Intermediate Similarity NPC473307
0.7059 Intermediate Similarity NPC249171
0.7059 Intermediate Similarity NPC49833
0.7054 Intermediate Similarity NPC475357
0.7045 Intermediate Similarity NPC470660
0.7045 Intermediate Similarity NPC470659
0.7041 Intermediate Similarity NPC327253
0.7041 Intermediate Similarity NPC303451
0.7041 Intermediate Similarity NPC202886
0.7041 Intermediate Similarity NPC6414
0.7037 Intermediate Similarity NPC106760
0.7027 Intermediate Similarity NPC477031
0.7019 Intermediate Similarity NPC94919
0.7009 Intermediate Similarity NPC38217
0.7009 Intermediate Similarity NPC472988
0.7 Intermediate Similarity NPC256368
0.7 Intermediate Similarity NPC96736
0.7 Intermediate Similarity NPC178949
0.7 Intermediate Similarity NPC144068
0.6991 Remote Similarity NPC5883
0.6991 Remote Similarity NPC44899
0.6991 Remote Similarity NPC29639
0.6991 Remote Similarity NPC304260
0.699 Remote Similarity NPC130792
0.699 Remote Similarity NPC91497
0.6989 Remote Similarity NPC216941
0.6981 Remote Similarity NPC474569
0.6981 Remote Similarity NPC165405
0.6975 Remote Similarity NPC276047
0.6975 Remote Similarity NPC267733
0.697 Remote Similarity NPC48463
0.697 Remote Similarity NPC472197
0.697 Remote Similarity NPC472199
0.697 Remote Similarity NPC477749
0.6964 Remote Similarity NPC203862
0.6961 Remote Similarity NPC91197
0.6961 Remote Similarity NPC96597
0.6961 Remote Similarity NPC476612
0.6961 Remote Similarity NPC155319
0.6961 Remote Similarity NPC125551
0.6961 Remote Similarity NPC347923
0.6961 Remote Similarity NPC239547
0.6961 Remote Similarity NPC476057
0.6961 Remote Similarity NPC476613

  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 NPC50464 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
0.7168 Intermediate Similarity NPD7503 Approved
0.7158 Intermediate Similarity NPD4249 Approved
0.7083 Intermediate Similarity NPD4251 Approved
0.7083 Intermediate Similarity NPD4250 Approved
0.687 Remote Similarity NPD8033 Approved
0.6754 Remote Similarity NPD7327 Approved
0.6754 Remote Similarity NPD7328 Approved
0.6702 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7516 Approved
0.6638 Remote Similarity NPD8377 Approved
0.6638 Remote Similarity NPD8294 Approved
0.6606 Remote Similarity NPD6412 Phase 2
0.6581 Remote Similarity NPD8296 Approved
0.6581 Remote Similarity NPD8335 Approved
0.6581 Remote Similarity NPD8380 Approved
0.6581 Remote Similarity NPD8379 Approved
0.6581 Remote Similarity NPD8378 Approved
0.6549 Remote Similarity NPD8133 Approved
0.6526 Remote Similarity NPD4822 Approved
0.6526 Remote Similarity NPD4821 Approved
0.6526 Remote Similarity NPD4819 Approved
0.6526 Remote Similarity NPD4820 Approved
0.6489 Remote Similarity NPD4268 Approved
0.6489 Remote Similarity NPD4271 Approved
0.6415 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6396 Remote Similarity NPD6686 Approved
0.6392 Remote Similarity NPD6435 Approved
0.6372 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7507 Approved
0.6316 Remote Similarity NPD6053 Discontinued
0.6303 Remote Similarity NPD8513 Phase 3
0.6214 Remote Similarity NPD46 Approved
0.6214 Remote Similarity NPD6698 Approved
0.621 Remote Similarity NPD7319 Approved
0.6186 Remote Similarity NPD5368 Approved
0.6167 Remote Similarity NPD8516 Approved
0.6167 Remote Similarity NPD8517 Approved
0.6167 Remote Similarity NPD8515 Approved
0.6162 Remote Similarity NPD7154 Phase 3
0.6122 Remote Similarity NPD5369 Approved
0.6095 Remote Similarity NPD8171 Discontinued
0.6078 Remote Similarity NPD7524 Approved
0.6058 Remote Similarity NPD7838 Discovery
0.6 Remote Similarity NPD5362 Discontinued
0.6 Remote Similarity NPD7736 Approved
0.6 Remote Similarity NPD7637 Suspended
0.6 Remote Similarity NPD7983 Approved
0.5984 Remote Similarity NPD6370 Approved
0.5982 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5982 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5966 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5966 Remote Similarity NPD6009 Approved
0.595 Remote Similarity NPD6319 Approved
0.5941 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5926 Remote Similarity NPD4792 Clinical (unspecified phase)
0.592 Remote Similarity NPD8293 Discontinued
0.5914 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5897 Remote Similarity NPD6882 Approved
0.5887 Remote Similarity NPD7492 Approved
0.5882 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5877 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5856 Remote Similarity NPD5344 Discontinued
0.5847 Remote Similarity NPD4632 Approved
0.5842 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5842 Remote Similarity NPD3669 Approved
0.5842 Remote Similarity NPD5331 Approved
0.5842 Remote Similarity NPD5332 Approved
0.5842 Remote Similarity NPD6695 Phase 3
0.5841 Remote Similarity NPD8170 Clinical (unspecified phase)
0.584 Remote Similarity NPD6616 Approved
0.582 Remote Similarity NPD6054 Approved
0.58 Remote Similarity NPD4790 Discontinued
0.5794 Remote Similarity NPD7078 Approved
0.5785 Remote Similarity NPD7641 Discontinued
0.5784 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5776 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5772 Remote Similarity NPD6016 Approved
0.5772 Remote Similarity NPD6015 Approved
0.5772 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5763 Remote Similarity NPD8297 Approved
0.576 Remote Similarity NPD8342 Approved
0.576 Remote Similarity NPD8341 Approved
0.576 Remote Similarity NPD8340 Approved
0.576 Remote Similarity NPD8299 Approved
0.5743 Remote Similarity NPD4270 Approved
0.5743 Remote Similarity NPD4269 Approved
0.5741 Remote Similarity NPD5282 Discontinued
0.5726 Remote Similarity NPD8080 Discontinued
0.5726 Remote Similarity NPD5988 Approved
0.5726 Remote Similarity NPD6371 Approved
0.5714 Remote Similarity NPD893 Approved
0.5714 Remote Similarity NPD889 Approved
0.5714 Remote Similarity NPD8451 Approved
0.5714 Remote Similarity NPD890 Clinical (unspecified phase)
0.5714 Remote Similarity NPD892 Phase 3
0.5714 Remote Similarity NPD894 Approved
0.5714 Remote Similarity NPD891 Phase 3
0.5714 Remote Similarity NPD888 Phase 3
0.5714 Remote Similarity NPD895 Approved
0.5714 Remote Similarity NPD6932 Approved
0.5714 Remote Similarity NPD887 Approved
0.57 Remote Similarity NPD4252 Approved
0.5698 Remote Similarity NPD2267 Suspended
0.5691 Remote Similarity NPD6059 Approved
0.568 Remote Similarity NPD7829 Approved
0.568 Remote Similarity NPD7830 Approved
0.5673 Remote Similarity NPD5786 Approved
0.5669 Remote Similarity NPD8074 Phase 3
0.5669 Remote Similarity NPD8448 Approved
0.5663 Remote Similarity NPD905 Approved
0.5663 Remote Similarity NPD904 Phase 3
0.5645 Remote Similarity NPD8444 Approved
0.5636 Remote Similarity NPD7839 Suspended
0.5619 Remote Similarity NPD7750 Discontinued
0.5612 Remote Similarity NPD6933 Approved
0.5607 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5603 Remote Similarity NPD6685 Approved
0.5603 Remote Similarity NPD5697 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