Structure

Physi-Chem Properties

Molecular Weight:  1166.7
Volume:  1219.155
LogP:  6.766
LogD:  3.267
LogS:  -5.532
# Rotatable Bonds:  19
TPSA:  263.0
# H-Bond Aceptor:  20
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.118
Synthetic Accessibility Score:  6.069
Fsp3:  0.806
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.038
MDCK Permeability:  0.00011550355702638626
Pgp-inhibitor:  1.0
Pgp-substrate:  0.985
Human Intestinal Absorption (HIA):  0.709
20% Bioavailability (F20%):  0.158
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  80.6664047241211%
Volume Distribution (VD):  1.398
Pgp-substrate:  5.4888691902160645%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.0
CYP2C19-inhibitor:  0.0
CYP2C19-substrate:  0.026
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.786
CYP2D6-inhibitor:  0.162
CYP2D6-substrate:  0.023
CYP3A4-inhibitor:  0.199
CYP3A4-substrate:  0.417

ADMET: Excretion

Clearance (CL):  2.057
Half-life (T1/2):  0.083

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.998
Drug-inuced Liver Injury (DILI):  0.887
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.999
Skin Sensitization:  0.998
Carcinogencity:  0.055
Eye Corrosion:  0.97
Eye Irritation:  0.395
Respiratory Toxicity:  0.003

Download Data

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

  Natural Product: NPC477204

Natural Product ID:  NPC477204
Common Name*:   Peracetyl-amantelide A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QTLMTRDVVSPSOZ-RGFDFDFBSA-N
Standard InCHI:  InChI=1S/C62H102O20/c1-41-22-14-35-57(79-48(8)69)39-58(80-49(9)70)36-20-33-55(77-46(6)67)31-18-29-53(75-44(4)65)27-16-25-51(73-42(2)63)23-15-24-52(74-43(3)64)26-17-28-54(76-45(5)66)30-19-32-56(78-47(7)68)34-21-37-59(81-50(10)71)40-60(62(11,12)13)82-61(72)38-41/h38,51-60H,14-37,39-40H2,1-13H3/b41-38-/t51?,52?,53?,54?,55?,56?,57-,58+,59?,60?/m0/s1
SMILES:  [H]/C1=C(C)CCC[C@H](OC(C)=O)C[C@H](OC(C)=O)CCCC(OC(C)=O)CCCC(OC(C)=O)CCCC(OC(C)=O)CCCC(OC(C)=O)CCCC(OC(C)=O)CCCC(OC(C)=O)CCCC(OC(C)=O)CC(C(C)(C)C)OC1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000147] Macrolides and analogues

*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
NPO33603 Gray cyanobacterium Species n.a. n.a. n.a. Two Lovers Point (Puntan dos Amantes), Tumon Bay, Guam 2002-JUN PMID[26204500]

☑ 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 18000 nM PMID[26204500]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 58000 nM PMID[26204500]

☑ 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 NPC477204 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
0.9306 High Similarity NPC477203
0.9167 High Similarity NPC477202
0.8649 High Similarity NPC469880
0.8472 Intermediate Similarity NPC469660
0.8108 Intermediate Similarity NPC477084
0.8101 Intermediate Similarity NPC184208
0.8101 Intermediate Similarity NPC8538
0.8082 Intermediate Similarity NPC269841
0.8056 Intermediate Similarity NPC472266
0.8025 Intermediate Similarity NPC78673
0.8025 Intermediate Similarity NPC186155
0.8025 Intermediate Similarity NPC160517
0.8 Intermediate Similarity NPC222244
0.8 Intermediate Similarity NPC16349
0.8 Intermediate Similarity NPC123908
0.8 Intermediate Similarity NPC10080
0.7952 Intermediate Similarity NPC199382
0.7875 Intermediate Similarity NPC315731
0.7848 Intermediate Similarity NPC139712
0.7831 Intermediate Similarity NPC61527
0.7792 Intermediate Similarity NPC327041
0.7792 Intermediate Similarity NPC285840
0.7763 Intermediate Similarity NPC477085
0.775 Intermediate Similarity NPC469802
0.7746 Intermediate Similarity NPC217940
0.7714 Intermediate Similarity NPC252851
0.7714 Intermediate Similarity NPC158368
0.7714 Intermediate Similarity NPC226872
0.7714 Intermediate Similarity NPC154908
0.7654 Intermediate Similarity NPC475944
0.7632 Intermediate Similarity NPC475762
0.7632 Intermediate Similarity NPC477087
0.7632 Intermediate Similarity NPC477086
0.7619 Intermediate Similarity NPC261253
0.7619 Intermediate Similarity NPC474045
0.7619 Intermediate Similarity NPC186332
0.7619 Intermediate Similarity NPC137253
0.7619 Intermediate Similarity NPC47220
0.76 Intermediate Similarity NPC101622
0.7595 Intermediate Similarity NPC84360
0.7586 Intermediate Similarity NPC206679
0.7586 Intermediate Similarity NPC476084
0.7586 Intermediate Similarity NPC476075
0.7586 Intermediate Similarity NPC114172
0.7586 Intermediate Similarity NPC471324
0.7532 Intermediate Similarity NPC327383
0.7532 Intermediate Similarity NPC185186
0.7532 Intermediate Similarity NPC329914
0.7531 Intermediate Similarity NPC474510
0.7531 Intermediate Similarity NPC474739
0.7528 Intermediate Similarity NPC300710
0.75 Intermediate Similarity NPC474005
0.75 Intermediate Similarity NPC159092
0.75 Intermediate Similarity NPC474816
0.75 Intermediate Similarity NPC209135
0.75 Intermediate Similarity NPC4299
0.75 Intermediate Similarity NPC109406
0.747 Intermediate Similarity NPC170377
0.747 Intermediate Similarity NPC474193
0.747 Intermediate Similarity NPC474809
0.747 Intermediate Similarity NPC12283
0.7467 Intermediate Similarity NPC276290
0.7444 Intermediate Similarity NPC255410
0.7439 Intermediate Similarity NPC471552
0.7439 Intermediate Similarity NPC473339
0.7436 Intermediate Similarity NPC474758
0.7429 Intermediate Similarity NPC23418
0.7416 Intermediate Similarity NPC159698
0.7416 Intermediate Similarity NPC140277
0.7412 Intermediate Similarity NPC102996
0.7407 Intermediate Similarity NPC471299
0.7407 Intermediate Similarity NPC477088
0.7407 Intermediate Similarity NPC325869
0.7386 Intermediate Similarity NPC473944
0.7375 Intermediate Similarity NPC262747
0.7363 Intermediate Similarity NPC100912
0.7363 Intermediate Similarity NPC311241
0.7363 Intermediate Similarity NPC120299
0.7363 Intermediate Similarity NPC475446
0.7349 Intermediate Similarity NPC471218
0.7349 Intermediate Similarity NPC471298
0.7326 Intermediate Similarity NPC476600
0.7326 Intermediate Similarity NPC102640
0.7317 Intermediate Similarity NPC133226
0.7317 Intermediate Similarity NPC470147
0.7308 Intermediate Similarity NPC329890
0.7303 Intermediate Similarity NPC472196
0.7303 Intermediate Similarity NPC472195
0.7303 Intermediate Similarity NPC238090
0.7294 Intermediate Similarity NPC99395
0.7294 Intermediate Similarity NPC242233
0.7294 Intermediate Similarity NPC197903
0.7294 Intermediate Similarity NPC471494
0.7283 Intermediate Similarity NPC72647
0.7283 Intermediate Similarity NPC107806
0.7283 Intermediate Similarity NPC475653
0.7273 Intermediate Similarity NPC177668
0.7273 Intermediate Similarity NPC37929
0.7273 Intermediate Similarity NPC476012
0.7273 Intermediate Similarity NPC64234
0.7262 Intermediate Similarity NPC471297
0.7253 Intermediate Similarity NPC209297
0.7253 Intermediate Similarity NPC475380
0.7253 Intermediate Similarity NPC194132
0.725 Intermediate Similarity NPC188860
0.725 Intermediate Similarity NPC301525
0.7241 Intermediate Similarity NPC69713
0.7241 Intermediate Similarity NPC106332
0.7237 Intermediate Similarity NPC475760
0.7229 Intermediate Similarity NPC471325
0.7222 Intermediate Similarity NPC161998
0.7222 Intermediate Similarity NPC477722
0.7209 Intermediate Similarity NPC204048
0.7209 Intermediate Similarity NPC469676
0.7195 Intermediate Similarity NPC5908
0.7195 Intermediate Similarity NPC180725
0.7195 Intermediate Similarity NPC86971
0.7195 Intermediate Similarity NPC469690
0.7195 Intermediate Similarity NPC469620
0.7195 Intermediate Similarity NPC80471
0.7195 Intermediate Similarity NPC470149
0.7195 Intermediate Similarity NPC470148
0.7195 Intermediate Similarity NPC110373
0.7191 Intermediate Similarity NPC221282
0.7179 Intermediate Similarity NPC84038
0.7179 Intermediate Similarity NPC257618
0.7174 Intermediate Similarity NPC475332
0.7162 Intermediate Similarity NPC34883
0.716 Intermediate Similarity NPC474026
0.716 Intermediate Similarity NPC233071
0.716 Intermediate Similarity NPC97516
0.7159 Intermediate Similarity NPC133450
0.7158 Intermediate Similarity NPC473816
0.7158 Intermediate Similarity NPC475367
0.7158 Intermediate Similarity NPC474581
0.7143 Intermediate Similarity NPC232812
0.7143 Intermediate Similarity NPC96663
0.7143 Intermediate Similarity NPC151481
0.7143 Intermediate Similarity NPC323251
0.7126 Intermediate Similarity NPC316138
0.7126 Intermediate Similarity NPC478144
0.7126 Intermediate Similarity NPC471796
0.7126 Intermediate Similarity NPC313658
0.7125 Intermediate Similarity NPC228978
0.7111 Intermediate Similarity NPC320089
0.7111 Intermediate Similarity NPC7349
0.7108 Intermediate Similarity NPC472470
0.7105 Intermediate Similarity NPC193029
0.7105 Intermediate Similarity NPC473357
0.7093 Intermediate Similarity NPC120398
0.7093 Intermediate Similarity NPC329615
0.7093 Intermediate Similarity NPC474547
0.7093 Intermediate Similarity NPC474013
0.7093 Intermediate Similarity NPC477013
0.7093 Intermediate Similarity NPC329838
0.7093 Intermediate Similarity NPC11804
0.7093 Intermediate Similarity NPC477014
0.7093 Intermediate Similarity NPC471567
0.7089 Intermediate Similarity NPC476489
0.7089 Intermediate Similarity NPC474705
0.7089 Intermediate Similarity NPC476490
0.7083 Intermediate Similarity NPC474267
0.7079 Intermediate Similarity NPC475748
0.7079 Intermediate Similarity NPC3952
0.7073 Intermediate Similarity NPC184737
0.7073 Intermediate Similarity NPC128276
0.7073 Intermediate Similarity NPC248775
0.7073 Intermediate Similarity NPC471220
0.7073 Intermediate Similarity NPC23187
0.7065 Intermediate Similarity NPC173329
0.7065 Intermediate Similarity NPC288350
0.7059 Intermediate Similarity NPC170286
0.7059 Intermediate Similarity NPC318468
0.7059 Intermediate Similarity NPC475947
0.7059 Intermediate Similarity NPC311070
0.7059 Intermediate Similarity NPC161045
0.7059 Intermediate Similarity NPC231601
0.7053 Intermediate Similarity NPC473596
0.7051 Intermediate Similarity NPC476037
0.7045 Intermediate Similarity NPC40376
0.7045 Intermediate Similarity NPC93411
0.7045 Intermediate Similarity NPC233551
0.7045 Intermediate Similarity NPC280621
0.7045 Intermediate Similarity NPC48338
0.7045 Intermediate Similarity NPC473905
0.7045 Intermediate Similarity NPC20339
0.7045 Intermediate Similarity NPC89001
0.7045 Intermediate Similarity NPC21208
0.7045 Intermediate Similarity NPC320458
0.7037 Intermediate Similarity NPC27205
0.7033 Intermediate Similarity NPC281775
0.7033 Intermediate Similarity NPC256368
0.7033 Intermediate Similarity NPC105490
0.7024 Intermediate Similarity NPC25554
0.7024 Intermediate Similarity NPC170303
0.7024 Intermediate Similarity NPC112868
0.7021 Intermediate Similarity NPC13743
0.7021 Intermediate Similarity NPC98813
0.7013 Intermediate Similarity NPC310210
0.7013 Intermediate Similarity NPC218477

  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 NPC477204 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
0.7778 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7838 Discovery
0.7273 Intermediate Similarity NPD6698 Approved
0.7273 Intermediate Similarity NPD46 Approved
0.7125 Intermediate Similarity NPD8039 Approved
0.6977 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6933 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6744 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6744 Remote Similarity NPD5209 Approved
0.6737 Remote Similarity NPD7638 Approved
0.6737 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7639 Approved
0.6667 Remote Similarity NPD7640 Approved
0.663 Remote Similarity NPD7983 Approved
0.6535 Remote Similarity NPD6686 Approved
0.6517 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6495 Remote Similarity NPD6648 Approved
0.6436 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5344 Discontinued
0.6429 Remote Similarity NPD6927 Phase 3
0.6413 Remote Similarity NPD6051 Approved
0.6344 Remote Similarity NPD5785 Approved
0.6333 Remote Similarity NPD1694 Approved
0.6333 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6292 Remote Similarity NPD7154 Phase 3
0.6277 Remote Similarity NPD7637 Suspended
0.625 Remote Similarity NPD6371 Approved
0.6237 Remote Similarity NPD1695 Approved
0.6224 Remote Similarity NPD4225 Approved
0.6196 Remote Similarity NPD4251 Approved
0.6196 Remote Similarity NPD4250 Approved
0.6186 Remote Similarity NPD7839 Suspended
0.6136 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6092 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6087 Remote Similarity NPD7521 Approved
0.6087 Remote Similarity NPD4249 Approved
0.6087 Remote Similarity NPD7334 Approved
0.6087 Remote Similarity NPD6409 Approved
0.6087 Remote Similarity NPD7146 Approved
0.6087 Remote Similarity NPD5330 Approved
0.6087 Remote Similarity NPD6684 Approved
0.6082 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6042 Remote Similarity NPD5778 Approved
0.6042 Remote Similarity NPD5779 Approved
0.604 Remote Similarity NPD7632 Discontinued
0.6036 Remote Similarity NPD8377 Approved
0.6036 Remote Similarity NPD8294 Approved
0.6026 Remote Similarity NPD4191 Approved
0.6026 Remote Similarity NPD4192 Approved
0.6026 Remote Similarity NPD4194 Approved
0.6026 Remote Similarity NPD4193 Approved
0.6 Remote Similarity NPD7327 Approved
0.6 Remote Similarity NPD7328 Approved
0.5982 Remote Similarity NPD8380 Approved
0.5982 Remote Similarity NPD8378 Approved
0.5982 Remote Similarity NPD8379 Approved
0.5982 Remote Similarity NPD8033 Approved
0.5982 Remote Similarity NPD8296 Approved
0.5982 Remote Similarity NPD8335 Approved
0.5979 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5979 Remote Similarity NPD7748 Approved
0.5979 Remote Similarity NPD7900 Approved
0.5962 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5957 Remote Similarity NPD5737 Approved
0.5957 Remote Similarity NPD6672 Approved
0.5957 Remote Similarity NPD6903 Approved
0.5957 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5955 Remote Similarity NPD4822 Approved
0.5955 Remote Similarity NPD4819 Approved
0.5955 Remote Similarity NPD4820 Approved
0.5955 Remote Similarity NPD4821 Approved
0.5946 Remote Similarity NPD7516 Approved
0.5934 Remote Similarity NPD6695 Phase 3
0.5934 Remote Similarity NPD5362 Discontinued
0.5909 Remote Similarity NPD4271 Approved
0.5909 Remote Similarity NPD4268 Approved
0.5888 Remote Similarity NPD8413 Clinical (unspecified phase)
0.587 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5865 Remote Similarity NPD4211 Phase 1
0.5851 Remote Similarity NPD7750 Discontinued
0.5841 Remote Similarity NPD7503 Approved
0.5833 Remote Similarity NPD6053 Discontinued
0.5824 Remote Similarity NPD6435 Approved
0.5816 Remote Similarity NPD5282 Discontinued
0.5806 Remote Similarity NPD5363 Approved
0.58 Remote Similarity NPD7902 Approved
0.5794 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5773 Remote Similarity NPD5693 Phase 1
0.5773 Remote Similarity NPD6411 Approved
0.5761 Remote Similarity NPD5332 Approved
0.5761 Remote Similarity NPD5331 Approved
0.5714 Remote Similarity NPD4790 Discontinued
0.5701 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5696 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5684 Remote Similarity NPD7524 Approved
0.5667 Remote Similarity NPD6929 Approved
0.5663 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5652 Remote Similarity NPD4269 Approved
0.5652 Remote Similarity NPD4270 Approved
0.5644 Remote Similarity NPD6083 Phase 2
0.5644 Remote Similarity NPD6084 Phase 2
0.5641 Remote Similarity NPD7507 Approved
0.5618 Remote Similarity NPD6925 Approved
0.5618 Remote Similarity NPD4756 Discovery
0.5618 Remote Similarity NPD5776 Phase 2
0.5612 Remote Similarity NPD7515 Phase 2
0.5604 Remote Similarity NPD7332 Phase 2
0.5604 Remote Similarity NPD6931 Approved
0.5604 Remote Similarity NPD6930 Phase 2
0.5604 Remote Similarity NPD7514 Phase 3
0.5604 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5604 Remote Similarity NPD5368 Approved
0.56 Remote Similarity NPD5695 Phase 3

  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