Structure

Physi-Chem Properties

Molecular Weight:  486.38
Volume:  533.665
LogP:  5.353
LogD:  4.831
LogS:  -4.935
# Rotatable Bonds:  7
TPSA:  58.64
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.407
Synthetic Accessibility Score:  4.762
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.816
MDCK Permeability:  1.2310569218243472e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.222
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.148
30% Bioavailability (F30%):  0.751

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.162
Plasma Protein Binding (PPB):  67.41454315185547%
Volume Distribution (VD):  1.136
Pgp-substrate:  16.57627296447754%

ADMET: Metabolism

CYP1A2-inhibitor:  0.223
CYP1A2-substrate:  0.467
CYP2C19-inhibitor:  0.276
CYP2C19-substrate:  0.933
CYP2C9-inhibitor:  0.472
CYP2C9-substrate:  0.07
CYP2D6-inhibitor:  0.84
CYP2D6-substrate:  0.907
CYP3A4-inhibitor:  0.918
CYP3A4-substrate:  0.657

ADMET: Excretion

Clearance (CL):  4.409
Half-life (T1/2):  0.143

ADMET: Toxicity

hERG Blockers:  0.862
Human Hepatotoxicity (H-HT):  0.575
Drug-inuced Liver Injury (DILI):  0.811
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.931
Maximum Recommended Daily Dose:  0.023
Skin Sensitization:  0.952
Carcinogencity:  0.286
Eye Corrosion:  0.931
Eye Irritation:  0.057
Respiratory Toxicity:  0.965

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

  Natural Product: NPC36497

Natural Product ID:  NPC36497
Common Name*:   Acetic Acid (1S,6R,7R,10R,11S,12S,15S,16S)-17-((S)-1-Dimethylamino-Ethyl)-10,13-Dimethyl-3-(3-Methyl-But-2-Enoylamino)-Hexadecahydro-Cyclopenta[A]Phenanthren-4-Yl Ester
IUPAC Name:   [(3S,4R,5R,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-3-(3-methylbut-2-enoylamino)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate
Synonyms:  
Standard InCHIKey:  MTGALPCIDMQJOU-HHUFISPXSA-N
Standard InCHI:  InChI=1S/C30H50N2O3/c1-18(2)17-27(34)31-26-14-16-30(6)24-13-15-29(5)22(19(3)32(7)8)11-12-23(29)21(24)9-10-25(30)28(26)35-20(4)33/h17,19,21-26,28H,9-16H2,1-8H3,(H,31,34)/t19-,21-,22+,23-,24-,25-,26-,28+,29+,30+/m0/s1
SMILES:  CC(=CC(=N[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC[C@H]2[C@H]1OC(=O)C)[C@H](C)N(C)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL146254
PubChem CID:   44364908
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001194] Oxosteroids
          • [CHEMONTID:0003060] 16-oxosteroids

*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
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[14584959]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[14643329]
NPO26156 Mahurea palustris Species Calophyllaceae Eukaryota leaves French Guiana 1996-OCT PMID[16038535]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[9548847]
NPO26204 Arisaema curvatum Species Araceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26204 Arisaema curvatum Species Araceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26673 Casearia ilicifolia Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26156 Mahurea palustris Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26204 Arisaema curvatum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26471 Lenormandia smithiae Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26423 Scaevola racemigera Species Goodeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26446 Lecanora frustulosa Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23047 Streptomyces griseoviridis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26372 Sarcandra hainanensis Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25707 Euchaeta russelli Species Euchaetidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18582 Cosmospora butyri Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23214 Drosera congolana Species Droseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26556 Pterocephalus pinardi Species Caprifoliaceae 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
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica IC50 = 8500.0 nM PMID[490812]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Ki = 17600.0 nM PMID[490812]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 = 2300.0 nM PMID[490812]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens Ki = 2580.0 nM PMID[490812]

☑ 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 NPC36497 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
0.9412 High Similarity NPC72753
0.9231 High Similarity NPC80834
0.9231 High Similarity NPC469968
0.9135 High Similarity NPC66862
0.8972 High Similarity NPC165396
0.8407 Intermediate Similarity NPC242692
0.8333 Intermediate Similarity NPC472458
0.8302 Intermediate Similarity NPC55462
0.8019 Intermediate Similarity NPC471083
0.7966 Intermediate Similarity NPC237286
0.7838 Intermediate Similarity NPC472359
0.7732 Intermediate Similarity NPC257962
0.7568 Intermediate Similarity NPC25340
0.7523 Intermediate Similarity NPC50815
0.7522 Intermediate Similarity NPC472313
0.7456 Intermediate Similarity NPC474459
0.7455 Intermediate Similarity NPC474583
0.7426 Intermediate Similarity NPC152684
0.7391 Intermediate Similarity NPC56796
0.7391 Intermediate Similarity NPC474452
0.7387 Intermediate Similarity NPC119329
0.7364 Intermediate Similarity NPC247060
0.7321 Intermediate Similarity NPC86906
0.7222 Intermediate Similarity NPC476903
0.7143 Intermediate Similarity NPC90538
0.708 Intermediate Similarity NPC470596
0.7009 Intermediate Similarity NPC79238
0.699 Remote Similarity NPC175419
0.6897 Remote Similarity NPC470595
0.6893 Remote Similarity NPC323180
0.6875 Remote Similarity NPC275686
0.6857 Remote Similarity NPC321340
0.6857 Remote Similarity NPC119633
0.6857 Remote Similarity NPC171698
0.6857 Remote Similarity NPC270957
0.6847 Remote Similarity NPC292819
0.6847 Remote Similarity NPC4834
0.6842 Remote Similarity NPC241879
0.6762 Remote Similarity NPC75810
0.6761 Remote Similarity NPC275839
0.6752 Remote Similarity NPC159367
0.6748 Remote Similarity NPC35037
0.6724 Remote Similarity NPC258130
0.6724 Remote Similarity NPC195841
0.6724 Remote Similarity NPC233256
0.6699 Remote Similarity NPC109533
0.6698 Remote Similarity NPC323958
0.6696 Remote Similarity NPC45365
0.6696 Remote Similarity NPC293299
0.6612 Remote Similarity NPC478137
0.6609 Remote Similarity NPC476755
0.6609 Remote Similarity NPC152718
0.6602 Remote Similarity NPC206735
0.6598 Remote Similarity NPC245223
0.6555 Remote Similarity NPC218602
0.6549 Remote Similarity NPC240650
0.6549 Remote Similarity NPC140300
0.6547 Remote Similarity NPC473922
0.6542 Remote Similarity NPC166458
0.6542 Remote Similarity NPC168231
0.6529 Remote Similarity NPC477291
0.65 Remote Similarity NPC328052
0.6486 Remote Similarity NPC38232
0.6486 Remote Similarity NPC93027
0.6466 Remote Similarity NPC226509
0.646 Remote Similarity NPC289140
0.6457 Remote Similarity NPC469943
0.6444 Remote Similarity NPC132847
0.6441 Remote Similarity NPC230677
0.6435 Remote Similarity NPC239768
0.6435 Remote Similarity NPC128698
0.6429 Remote Similarity NPC470593
0.6429 Remote Similarity NPC280710
0.6429 Remote Similarity NPC470594
0.6429 Remote Similarity NPC243985
0.6415 Remote Similarity NPC139206
0.6415 Remote Similarity NPC5280
0.64 Remote Similarity NPC470276
0.64 Remote Similarity NPC9714
0.6396 Remote Similarity NPC110923
0.6396 Remote Similarity NPC74296
0.6396 Remote Similarity NPC177641
0.6393 Remote Similarity NPC124358
0.6389 Remote Similarity NPC474970
0.6387 Remote Similarity NPC169375
0.6381 Remote Similarity NPC192456
0.6381 Remote Similarity NPC90150
0.6378 Remote Similarity NPC476504
0.6372 Remote Similarity NPC311164
0.6372 Remote Similarity NPC272732
0.6372 Remote Similarity NPC84383
0.6364 Remote Similarity NPC63511
0.6364 Remote Similarity NPC262858
0.6364 Remote Similarity NPC472240
0.6356 Remote Similarity NPC469958
0.6346 Remote Similarity NPC47808
0.6346 Remote Similarity NPC305835
0.6341 Remote Similarity NPC106479
0.6339 Remote Similarity NPC476304
0.6321 Remote Similarity NPC472504
0.6316 Remote Similarity NPC276103
0.6316 Remote Similarity NPC54248
0.6306 Remote Similarity NPC312637
0.6286 Remote Similarity NPC304194
0.6283 Remote Similarity NPC474922
0.6283 Remote Similarity NPC476186
0.6273 Remote Similarity NPC160304
0.6273 Remote Similarity NPC34754
0.6263 Remote Similarity NPC124384
0.6262 Remote Similarity NPC471037
0.626 Remote Similarity NPC476498
0.625 Remote Similarity NPC46981
0.625 Remote Similarity NPC476756
0.625 Remote Similarity NPC244982
0.625 Remote Similarity NPC329842
0.624 Remote Similarity NPC28280
0.624 Remote Similarity NPC304646
0.6231 Remote Similarity NPC476503
0.6226 Remote Similarity NPC170303
0.6224 Remote Similarity NPC475578
0.6218 Remote Similarity NPC475239
0.6218 Remote Similarity NPC212874
0.6216 Remote Similarity NPC323156
0.6216 Remote Similarity NPC473647
0.6216 Remote Similarity NPC146554
0.6207 Remote Similarity NPC91604
0.6207 Remote Similarity NPC140685
0.6204 Remote Similarity NPC306951
0.6204 Remote Similarity NPC299963
0.6202 Remote Similarity NPC478138
0.62 Remote Similarity NPC235460
0.619 Remote Similarity NPC153987
0.619 Remote Similarity NPC470275
0.619 Remote Similarity NPC44083
0.6182 Remote Similarity NPC166857
0.6182 Remote Similarity NPC21035
0.6174 Remote Similarity NPC88009
0.6174 Remote Similarity NPC217801
0.6174 Remote Similarity NPC195366
0.6174 Remote Similarity NPC114743
0.6168 Remote Similarity NPC256112
0.6168 Remote Similarity NPC218616
0.6168 Remote Similarity NPC296701
0.6161 Remote Similarity NPC84171
0.6161 Remote Similarity NPC471896
0.6161 Remote Similarity NPC53890
0.6161 Remote Similarity NPC219937
0.6161 Remote Similarity NPC123252
0.6161 Remote Similarity NPC194485
0.616 Remote Similarity NPC470540
0.616 Remote Similarity NPC135431
0.616 Remote Similarity NPC476499
0.6154 Remote Similarity NPC135799
0.6154 Remote Similarity NPC201406
0.6154 Remote Similarity NPC251680
0.6147 Remote Similarity NPC147513
0.6147 Remote Similarity NPC474013
0.6147 Remote Similarity NPC164424
0.614 Remote Similarity NPC473314
0.614 Remote Similarity NPC201725
0.6126 Remote Similarity NPC16377
0.6126 Remote Similarity NPC4309
0.6121 Remote Similarity NPC210337
0.6121 Remote Similarity NPC167419
0.6121 Remote Similarity NPC141401
0.6121 Remote Similarity NPC473537
0.6121 Remote Similarity NPC474164
0.6117 Remote Similarity NPC185536
0.6111 Remote Similarity NPC476927
0.6111 Remote Similarity NPC209252
0.6111 Remote Similarity NPC473742
0.6111 Remote Similarity NPC246956
0.6106 Remote Similarity NPC234335
0.6106 Remote Similarity NPC212948
0.6102 Remote Similarity NPC25177
0.6102 Remote Similarity NPC247701
0.6102 Remote Similarity NPC295110
0.6102 Remote Similarity NPC268829
0.6102 Remote Similarity NPC118275
0.6102 Remote Similarity NPC222875
0.6098 Remote Similarity NPC287764
0.6091 Remote Similarity NPC286153
0.6091 Remote Similarity NPC12774
0.6087 Remote Similarity NPC279974
0.6074 Remote Similarity NPC475472
0.6068 Remote Similarity NPC220111
0.6068 Remote Similarity NPC475249
0.6068 Remote Similarity NPC218107
0.6068 Remote Similarity NPC252564
0.6063 Remote Similarity NPC471120
0.6063 Remote Similarity NPC471117
0.6055 Remote Similarity NPC263974
0.6055 Remote Similarity NPC474047
0.6055 Remote Similarity NPC239362
0.6055 Remote Similarity NPC475509
0.6053 Remote Similarity NPC470224
0.6053 Remote Similarity NPC26046
0.6053 Remote Similarity NPC214697
0.605 Remote Similarity NPC470592
0.605 Remote Similarity NPC176012

  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 NPC36497 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
0.7203 Intermediate Similarity NPD7755 Approved
0.7203 Intermediate Similarity NPD7754 Approved
0.7094 Intermediate Similarity NPD8078 Approved
0.7094 Intermediate Similarity NPD8077 Approved
0.6957 Remote Similarity NPD7646 Clinical (unspecified phase)
0.6891 Remote Similarity NPD8298 Phase 2
0.6881 Remote Similarity NPD5771 Approved
0.6875 Remote Similarity NPD8418 Phase 2
0.6842 Remote Similarity NPD7911 Approved
0.6842 Remote Similarity NPD7987 Approved
0.6842 Remote Similarity NPD7912 Approved
0.6842 Remote Similarity NPD7986 Approved
0.6724 Remote Similarity NPD8040 Discontinued
0.6667 Remote Similarity NPD7989 Approved
0.6667 Remote Similarity NPD7990 Approved
0.6581 Remote Similarity NPD6920 Discontinued
0.6471 Remote Similarity NPD6415 Discontinued
0.6429 Remote Similarity NPD5769 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6311 Remote Similarity NPD8143 Approved
0.6311 Remote Similarity NPD8144 Approved
0.6198 Remote Similarity NPD8174 Phase 2
0.6154 Remote Similarity NPD7639 Approved
0.6154 Remote Similarity NPD7640 Approved
0.6154 Remote Similarity NPD6404 Discontinued
0.614 Remote Similarity NPD5707 Approved
0.6124 Remote Similarity NPD6908 Approved
0.6124 Remote Similarity NPD6909 Approved
0.6121 Remote Similarity NPD7919 Phase 3
0.6121 Remote Similarity NPD7920 Phase 3
0.6091 Remote Similarity NPD8308 Discontinued
0.6068 Remote Similarity NPD7638 Approved
0.6068 Remote Similarity NPD8088 Phase 1
0.6053 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5968 Remote Similarity NPD6420 Discontinued
0.5965 Remote Similarity NPD8035 Phase 2
0.5965 Remote Similarity NPD8034 Phase 2
0.5929 Remote Similarity NPD6051 Approved
0.5882 Remote Similarity NPD6914 Discontinued
0.5873 Remote Similarity NPD7336 Phase 2
0.5873 Remote Similarity NPD7335 Phase 2
0.5873 Remote Similarity NPD7337 Clinical (unspecified phase)
0.5833 Remote Similarity NPD7525 Registered
0.5812 Remote Similarity NPD7991 Discontinued
0.578 Remote Similarity NPD1448 Clinical (unspecified phase)
0.5776 Remote Similarity NPD6399 Phase 3
0.5772 Remote Similarity NPD7333 Discontinued
0.5755 Remote Similarity NPD6117 Approved
0.5739 Remote Similarity NPD6701 Clinical (unspecified phase)
0.5739 Remote Similarity NPD6700 Approved
0.5714 Remote Similarity NPD6113 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7625 Phase 1
0.5704 Remote Similarity NPD6334 Approved
0.5704 Remote Similarity NPD6333 Approved
0.5702 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5701 Remote Similarity NPD6116 Phase 1
0.569 Remote Similarity NPD6703 Approved
0.569 Remote Similarity NPD6702 Approved
0.5672 Remote Similarity NPD7122 Discontinued
0.5664 Remote Similarity NPD7521 Approved
0.5664 Remote Similarity NPD7334 Approved
0.5664 Remote Similarity NPD7146 Approved
0.5664 Remote Similarity NPD6684 Approved
0.5664 Remote Similarity NPD6409 Approved
0.5664 Remote Similarity NPD5330 Approved
0.5656 Remote Similarity NPD7632 Discontinued
0.5648 Remote Similarity NPD6115 Approved
0.5648 Remote Similarity NPD6114 Approved
0.5648 Remote Similarity NPD6118 Approved
0.5648 Remote Similarity NPD6697 Approved
0.5645 Remote Similarity NPD6640 Phase 3
0.5635 Remote Similarity NPD6413 Approved
0.5606 Remote Similarity NPD7519 Approved
0.5606 Remote Similarity NPD7518 Approved
0.5606 Remote Similarity NPD7517 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