Structure

Physi-Chem Properties

Molecular Weight:  596.47
Volume:  653.062
LogP:  6.636
LogD:  4.649
LogS:  -5.344
# Rotatable Bonds:  26
TPSA:  113.29
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.071
Synthetic Accessibility Score:  4.565
Fsp3:  0.943
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:  -4.93
MDCK Permeability:  6.7681366999750026e-06
Pgp-inhibitor:  0.02
Pgp-substrate:  0.92
Human Intestinal Absorption (HIA):  0.095
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  96.88262939453125%
Volume Distribution (VD):  1.215
Pgp-substrate:  2.378037929534912%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.319
CYP2C19-inhibitor:  0.055
CYP2C19-substrate:  0.049
CYP2C9-inhibitor:  0.091
CYP2C9-substrate:  0.961
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.069
CYP3A4-inhibitor:  0.421
CYP3A4-substrate:  0.046

ADMET: Excretion

Clearance (CL):  10.461
Half-life (T1/2):  0.09

ADMET: Toxicity

hERG Blockers:  0.589
Human Hepatotoxicity (H-HT):  0.401
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.001
Maximum Recommended Daily Dose:  0.851
Skin Sensitization:  0.974
Carcinogencity:  0.1
Eye Corrosion:  0.047
Eye Irritation:  0.088
Respiratory Toxicity:  0.94

Download Data

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

  Natural Product: NPC473775

Natural Product ID:  NPC473775
Common Name*:   Isoannoreticuin
IUPAC Name:   5-[(11S)-5,11-dihydroxy-11-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one
Synonyms:   Isoannoreticuin
Standard InCHIKey:  FGLYVGRJXTUDRE-LVBQAKHDSA-N
Standard InCHI:  InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-14-21-31(38)33-23-24-34(42-33)32(39)22-15-12-13-18-29(37)19-16-17-20-30-26-28(25-27(2)36)35(40)41-30/h28-34,37-39H,3-26H2,1-2H3/t28?,29?,30?,31-,32-,33-,34-/m0/s1
SMILES:  CCCCCCCCCCCCC(C1CCC(O1)C(CCCCCC(CCCCC2CC(C(=O)O2)CC(=O)C)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL451459
PubChem CID:   44584477
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols
          • [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. stem n.a. DOI[10.1021/np50053a043]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[8277309]
NPO9632 Annona reticulata Species Annonaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO9632 Annona reticulata Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9632 Annona reticulata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9632 Annona reticulata 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
NPT168 Cell Line P388 Mus musculus ED50 = 3.6 ug ml-1 PMID[488349]
NPT81 Cell Line A549 Homo sapiens ED50 = 4.0 10'-1 ug/ml PMID[488349]
NPT91 Cell Line KB Homo sapiens ED50 = 6.96 ug ml-1 PMID[488349]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 3.06 ug ml-1 PMID[488349]

☑ 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 NPC473775 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
1.0 High Similarity NPC473699
1.0 High Similarity NPC475260
1.0 High Similarity NPC51249
1.0 High Similarity NPC474100
1.0 High Similarity NPC475232
0.9306 High Similarity NPC475616
0.863 High Similarity NPC228411
0.859 High Similarity NPC473791
0.8571 High Similarity NPC82315
0.8481 Intermediate Similarity NPC475206
0.8429 Intermediate Similarity NPC286842
0.7945 Intermediate Similarity NPC28526
0.7941 Intermediate Similarity NPC470363
0.7917 Intermediate Similarity NPC469925
0.7746 Intermediate Similarity NPC314103
0.7619 Intermediate Similarity NPC314364
0.7606 Intermediate Similarity NPC235788
0.7595 Intermediate Similarity NPC470014
0.7532 Intermediate Similarity NPC215030
0.7529 Intermediate Similarity NPC177629
0.7529 Intermediate Similarity NPC58219
0.7471 Intermediate Similarity NPC469627
0.7468 Intermediate Similarity NPC474003
0.7442 Intermediate Similarity NPC92974
0.7439 Intermediate Similarity NPC164289
0.7439 Intermediate Similarity NPC242771
0.7439 Intermediate Similarity NPC311642
0.7439 Intermediate Similarity NPC100366
0.7436 Intermediate Similarity NPC217725
0.7412 Intermediate Similarity NPC186148
0.7333 Intermediate Similarity NPC319007
0.7326 Intermediate Similarity NPC476435
0.7308 Intermediate Similarity NPC125164
0.7262 Intermediate Similarity NPC3464
0.7262 Intermediate Similarity NPC474780
0.7262 Intermediate Similarity NPC475963
0.7262 Intermediate Similarity NPC151176
0.7215 Intermediate Similarity NPC179922
0.7215 Intermediate Similarity NPC81052
0.7209 Intermediate Similarity NPC179659
0.7209 Intermediate Similarity NPC51662
0.7206 Intermediate Similarity NPC53463
0.7206 Intermediate Similarity NPC469937
0.7206 Intermediate Similarity NPC23155
0.7206 Intermediate Similarity NPC320588
0.7195 Intermediate Similarity NPC200446
0.7179 Intermediate Similarity NPC291228
0.7179 Intermediate Similarity NPC308096
0.7176 Intermediate Similarity NPC329749
0.7176 Intermediate Similarity NPC476715
0.7159 Intermediate Similarity NPC478004
0.7159 Intermediate Similarity NPC158388
0.7159 Intermediate Similarity NPC65359
0.7159 Intermediate Similarity NPC478003
0.7143 Intermediate Similarity NPC470268
0.7093 Intermediate Similarity NPC476717
0.7093 Intermediate Similarity NPC475019
0.7093 Intermediate Similarity NPC474949
0.7079 Intermediate Similarity NPC208886
0.7079 Intermediate Similarity NPC12172
0.7073 Intermediate Similarity NPC209995
0.7059 Intermediate Similarity NPC291310
0.7051 Intermediate Similarity NPC184550
0.7051 Intermediate Similarity NPC185419
0.7045 Intermediate Similarity NPC173926
0.7045 Intermediate Similarity NPC474951
0.7037 Intermediate Similarity NPC214030
0.7037 Intermediate Similarity NPC83108
0.7024 Intermediate Similarity NPC212340
0.7024 Intermediate Similarity NPC102156
0.7024 Intermediate Similarity NPC148740
0.7011 Intermediate Similarity NPC190753
0.7 Intermediate Similarity NPC179746
0.7 Intermediate Similarity NPC81419
0.6989 Remote Similarity NPC274695
0.6986 Remote Similarity NPC469923
0.6977 Remote Similarity NPC47958
0.6977 Remote Similarity NPC304509
0.6977 Remote Similarity NPC149725
0.6977 Remote Similarity NPC478111
0.6966 Remote Similarity NPC472146
0.6966 Remote Similarity NPC470114
0.6966 Remote Similarity NPC185529
0.6957 Remote Similarity NPC475785
0.6951 Remote Similarity NPC218817
0.6951 Remote Similarity NPC469495
0.6951 Remote Similarity NPC11796
0.6933 Remote Similarity NPC157518
0.6933 Remote Similarity NPC469926
0.6933 Remote Similarity NPC476330
0.6932 Remote Similarity NPC53158
0.6932 Remote Similarity NPC471221
0.6932 Remote Similarity NPC470009
0.6923 Remote Similarity NPC470424
0.6914 Remote Similarity NPC474020
0.6897 Remote Similarity NPC80700
0.6897 Remote Similarity NPC469626
0.6897 Remote Similarity NPC476015
0.6897 Remote Similarity NPC474762
0.6897 Remote Similarity NPC475491
0.6897 Remote Similarity NPC92139
0.6889 Remote Similarity NPC30515
0.6889 Remote Similarity NPC184463
0.6875 Remote Similarity NPC477867
0.6866 Remote Similarity NPC305182
0.686 Remote Similarity NPC115995
0.686 Remote Similarity NPC477434
0.6854 Remote Similarity NPC471459
0.6854 Remote Similarity NPC67653
0.6854 Remote Similarity NPC307411
0.6849 Remote Similarity NPC469921
0.6842 Remote Similarity NPC241949
0.6842 Remote Similarity NPC315525
0.6842 Remote Similarity NPC135043
0.6835 Remote Similarity NPC470243
0.6818 Remote Similarity NPC239938
0.6812 Remote Similarity NPC72722
0.68 Remote Similarity NPC476702
0.6795 Remote Similarity NPC475062
0.6786 Remote Similarity NPC103634
0.6786 Remote Similarity NPC51507
0.6782 Remote Similarity NPC21469
0.6782 Remote Similarity NPC51267
0.6778 Remote Similarity NPC476004
0.6778 Remote Similarity NPC474761
0.6778 Remote Similarity NPC51004
0.6778 Remote Similarity NPC206614
0.6778 Remote Similarity NPC474323
0.6774 Remote Similarity NPC158416
0.6774 Remote Similarity NPC475765
0.6774 Remote Similarity NPC470883
0.6774 Remote Similarity NPC76862
0.6774 Remote Similarity NPC39859
0.6757 Remote Similarity NPC469922
0.6747 Remote Similarity NPC252483
0.6747 Remote Similarity NPC191345
0.6747 Remote Similarity NPC3852
0.6744 Remote Similarity NPC217559
0.6744 Remote Similarity NPC292458
0.6744 Remote Similarity NPC268578
0.6744 Remote Similarity NPC157328
0.6742 Remote Similarity NPC476708
0.6742 Remote Similarity NPC202672
0.6739 Remote Similarity NPC470423
0.6739 Remote Similarity NPC190294
0.6716 Remote Similarity NPC26253
0.6705 Remote Similarity NPC477010
0.6705 Remote Similarity NPC228593
0.6705 Remote Similarity NPC235196
0.6705 Remote Similarity NPC470657
0.6703 Remote Similarity NPC475878
0.6703 Remote Similarity NPC329952
0.6702 Remote Similarity NPC328562
0.6702 Remote Similarity NPC472145
0.6702 Remote Similarity NPC323421
0.6667 Remote Similarity NPC245029
0.6667 Remote Similarity NPC200580
0.6667 Remote Similarity NPC475900
0.6667 Remote Similarity NPC470191
0.6667 Remote Similarity NPC36954
0.6667 Remote Similarity NPC269267
0.6667 Remote Similarity NPC280612
0.6667 Remote Similarity NPC473564
0.6667 Remote Similarity NPC31302
0.6667 Remote Similarity NPC474032
0.6632 Remote Similarity NPC472144
0.663 Remote Similarity NPC273579
0.663 Remote Similarity NPC476300
0.663 Remote Similarity NPC162205
0.663 Remote Similarity NPC295204
0.663 Remote Similarity NPC212486
0.663 Remote Similarity NPC475912
0.663 Remote Similarity NPC288240
0.6629 Remote Similarity NPC473649
0.6629 Remote Similarity NPC470920
0.6629 Remote Similarity NPC159750
0.6629 Remote Similarity NPC248602
0.6629 Remote Similarity NPC470401
0.6629 Remote Similarity NPC154097
0.6629 Remote Similarity NPC31349
0.6627 Remote Similarity NPC70996
0.6618 Remote Similarity NPC55678
0.6596 Remote Similarity NPC163685
0.6596 Remote Similarity NPC31645
0.6596 Remote Similarity NPC476009
0.6593 Remote Similarity NPC313670
0.6593 Remote Similarity NPC88337
0.6593 Remote Similarity NPC475211
0.6591 Remote Similarity NPC100921
0.6591 Remote Similarity NPC473350
0.6591 Remote Similarity NPC477445
0.6591 Remote Similarity NPC477018
0.6588 Remote Similarity NPC134227
0.6588 Remote Similarity NPC472948
0.6588 Remote Similarity NPC474981
0.6585 Remote Similarity NPC179858
0.6582 Remote Similarity NPC98711
0.6567 Remote Similarity NPC106872
0.6567 Remote Similarity NPC477878
0.6567 Remote Similarity NPC324793

  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 NPC473775 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
0.7746 Intermediate Similarity NPD7909 Approved
0.7206 Intermediate Similarity NPD3728 Approved
0.7206 Intermediate Similarity NPD3730 Approved
0.6957 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6944 Remote Similarity NPD3198 Approved
0.6747 Remote Similarity NPD4802 Phase 2
0.6747 Remote Similarity NPD4238 Approved
0.6522 Remote Similarity NPD7983 Approved
0.6479 Remote Similarity NPD615 Clinical (unspecified phase)
0.6437 Remote Similarity NPD6435 Approved
0.6333 Remote Similarity NPD5786 Approved
0.6324 Remote Similarity NPD6125 Clinical (unspecified phase)
0.63 Remote Similarity NPD4057 Clinical (unspecified phase)
0.63 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6282 Remote Similarity NPD9496 Clinical (unspecified phase)
0.6269 Remote Similarity NPD634 Phase 3
0.6263 Remote Similarity NPD8138 Approved
0.6263 Remote Similarity NPD8085 Approved
0.6263 Remote Similarity NPD8139 Approved
0.6263 Remote Similarity NPD8086 Approved
0.6263 Remote Similarity NPD8082 Approved
0.6263 Remote Similarity NPD8083 Approved
0.6263 Remote Similarity NPD8084 Approved
0.625 Remote Similarity NPD229 Approved
0.625 Remote Similarity NPD7345 Approved
0.6238 Remote Similarity NPD8393 Approved
0.6207 Remote Similarity NPD5368 Approved
0.62 Remote Similarity NPD8275 Approved
0.62 Remote Similarity NPD8276 Approved
0.6197 Remote Similarity NPD3186 Phase 1
0.6163 Remote Similarity NPD6114 Approved
0.6163 Remote Similarity NPD6697 Approved
0.6163 Remote Similarity NPD6118 Approved
0.6163 Remote Similarity NPD6115 Approved
0.6139 Remote Similarity NPD8081 Approved
0.6139 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6136 Remote Similarity NPD5369 Approved
0.6119 Remote Similarity NPD2699 Approved
0.6081 Remote Similarity NPD73 Approved
0.6064 Remote Similarity NPD6698 Approved
0.6064 Remote Similarity NPD46 Approved
0.6 Remote Similarity NPD3703 Phase 2
0.6 Remote Similarity NPD1700 Approved
0.6 Remote Similarity NPD8959 Approved
0.593 Remote Similarity NPD6117 Approved
0.5904 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5889 Remote Similarity NPD4270 Approved
0.5889 Remote Similarity NPD4269 Approved
0.5882 Remote Similarity NPD6113 Clinical (unspecified phase)
0.587 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5867 Remote Similarity NPD2267 Suspended
0.5865 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5862 Remote Similarity NPD6116 Phase 1
0.5857 Remote Similarity NPD2266 Phase 2
0.5833 Remote Similarity NPD5777 Approved
0.5824 Remote Similarity NPD5362 Discontinued
0.5824 Remote Similarity NPD7154 Phase 3
0.5816 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5814 Remote Similarity NPD3702 Approved
0.581 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5795 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5773 Remote Similarity NPD5779 Approved
0.5773 Remote Similarity NPD5778 Approved
0.5758 Remote Similarity NPD7839 Suspended
0.5755 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5753 Remote Similarity NPD9010 Approved
0.5753 Remote Similarity NPD65 Approved
0.5753 Remote Similarity NPD9008 Approved
0.5753 Remote Similarity NPD66 Approved
0.5753 Remote Similarity NPD8960 Approved
0.5753 Remote Similarity NPD9011 Approved
0.5753 Remote Similarity NPD9007 Approved
0.5753 Remote Similarity NPD9009 Approved
0.5753 Remote Similarity NPD64 Approved
0.5753 Remote Similarity NPD72 Approved
0.5745 Remote Similarity NPD4250 Approved
0.5745 Remote Similarity NPD4251 Approved
0.5732 Remote Similarity NPD896 Approved
0.5732 Remote Similarity NPD897 Approved
0.5732 Remote Similarity NPD898 Approved
0.5714 Remote Similarity NPD8307 Discontinued
0.5714 Remote Similarity NPD4245 Approved
0.5714 Remote Similarity NPD4244 Approved
0.5714 Remote Similarity NPD8140 Approved
0.5699 Remote Similarity NPD5363 Approved
0.5684 Remote Similarity NPD4264 Clinical (unspecified phase)
0.5679 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5672 Remote Similarity NPD2270 Approved
0.567 Remote Similarity NPD8034 Phase 2
0.567 Remote Similarity NPD8035 Phase 2
0.5667 Remote Similarity NPD4252 Approved
0.5652 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5652 Remote Similarity NPD3669 Approved
0.5648 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5647 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5647 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5647 Remote Similarity NPD6081 Approved
0.5638 Remote Similarity NPD4249 Approved
0.5625 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5625 Remote Similarity NPD6101 Approved
0.5625 Remote Similarity NPD8961 Approved
0.5612 Remote Similarity NPD6399 Phase 3
0.561 Remote Similarity NPD4224 Phase 2
0.5607 Remote Similarity NPD8305 Approved
0.5607 Remote Similarity NPD8306 Approved
0.5604 Remote Similarity NPD1780 Approved
0.5604 Remote Similarity NPD1779 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