NPASS Compound

Natural Product: NPC327115

Natural Product ID	NPC327115
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4-Androsten-16Alpha-Ol-3,17Dione
IUPAC Name	(8R,9S,10R,13S,14S,16R)-16-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1908014
PubChem CID	440574
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003568] Androstane steroids [CHEMONTID:0001467] Androgens and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 48 51 0 0 0 0 0 0 0 0999 V2000 2.4081 1.4800 0.8706 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9425 0.0722 0.5010 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7106 -0.9372 1.3031 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2120 -0.7725 1.0959 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5009 -0.3341 -0.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6709 0.0046 -0.5724 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4483 -0.2862 -1.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1914 -0.0879 -0.9470 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0629 -0.0228 -1.8890 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0663 0.8590 -1.4636 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3488 0.9307 -0.0167 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4832 -0.0168 0.8341 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0372 -1.4168 0.8715 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4711 -1.4378 1.3550 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2899 -0.6251 0.4355 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7539 0.7777 0.3964 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7891 1.5047 -0.3738 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0811 0.9078 0.2043 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6681 -0.3323 0.9058 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2830 -1.0002 1.6994 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6295 1.8361 1.1169 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4154 -1.2729 -0.9111 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4543 1.4553 1.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2688 2.1736 -0.0083 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7854 1.8500 1.7086 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4683 -1.9572 0.9336 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4896 -0.7784 2.3616 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6917 -1.7589 1.2555 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6175 -0.0814 1.8694 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6830 -0.4073 -2.3453 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4964 0.3644 -2.8599 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7035 -1.0555 -2.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9727 0.5569 -2.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1618 1.8869 -1.8792 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0273 1.9588 0.3431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3790 0.3810 1.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5575 -1.9517 1.6467 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0974 -1.9879 -0.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8313 -2.5061 1.2894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5231 -1.1404 2.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8257 1.1507 1.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7434 1.3932 -1.4585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7818 2.5944 -0.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8126 0.6761 -0.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6255 1.8734 1.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0538 -2.1940 -0.7523 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4644 -1.6649 -1.3206 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9900 -0.6610 -1.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 18 21 1 0 15 22 1 0 8 2 1 0 12 2 1 0 16 11 1 0 19 15 1 0 1 23 1 0 1 24 1 0 1 25 1 0 3 26 1 0 3 27 1 0 4 28 1 0 4 29 1 0 7 30 1 0 9 31 1 0 9 32 1 0 10 33 1 0 10 34 1 0 11 35 1 0 12 36 1 0 13 37 1 0 13 38 1 0 14 39 1 0 14 40 1 0 16 41 1 0 17 42 1 0 17 43 1 0 18 44 1 0 21 45 1 0 22 46 1 0 22 47 1 0 22 48 1 0 M END

Standard InCHIKey	SSBCZTXGVMMZOT-NBBHSKLNSA-N
Standard InCHI	InChI=1S/C19H26O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h9,13-16,21H,3-8,10H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1
SMILES	CC12CCC(=O)C=C1CCC3C2CCC4(C3CC(C4=O)O)C

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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	Organism Name	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

Activity Type	# Activity
Activity	1
IC50	2

Activity Type	# Activity
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT697	Individual protein	UDP-glucuronosyltransferase 2B7	Homo sapiens	Activity	=	14.0	total picomoles	PMID[10836148]
NPT441	Individual protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	199986.19	nM	PMID[33017749]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC327115 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	17781
0.1-0.2	28344
0.2-0.3	3577
0.3-0.4	102
0.4-0.5	23
0.5-0.6	22
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.66	Remote Similarity	NPC139397
0.6415	Remote Similarity	NPC214043
0.6415	Remote Similarity	NPC227064
0.6415	Remote Similarity	NPC85774
0.6415	Remote Similarity	NPC329043
0.6415	Remote Similarity	NPC58841
0.6415	Remote Similarity	NPC161423
0.6	Remote Similarity	NPC144258
0.5965	Remote Similarity	NPC119416
0.5893	Remote Similarity	NPC237712
0.5849	Remote Similarity	NPC307176
0.5849	Remote Similarity	NPC321874
0.5741	Remote Similarity	NPC2634
0.5741	Remote Similarity	NPC265782
0.5741	Remote Similarity	NPC251929
0.569	Remote Similarity	NPC310010
0.569	Remote Similarity	NPC326627
0.5614	Remote Similarity	NPC20688
0.5536	Remote Similarity	NPC282593
0.5439	Remote Similarity	NPC257176
0.5439	Remote Similarity	NPC35734
0.5439	Remote Similarity	NPC159577
0.5439	Remote Similarity	NPC115023
0.5439	Remote Similarity	NPC602429
0.5345	Remote Similarity	NPC149203
0.5263	Remote Similarity	NPC319899
0.5254	Remote Similarity	NPC249312
0.5254	Remote Similarity	NPC323765
0.5085	Remote Similarity	NPC328539
0.5077	Remote Similarity	NPC111015

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC327115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6578
0.1-0.2	2299
0.2-0.3	178
0.3-0.4	56
0.4-0.5	26
0.5-0.6	9
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6415	Remote Similarity	NPD3666	Phase 4
0.6111	Remote Similarity	NPD4221	Phase 4
0.5849	Remote Similarity	NPD4747	Phase 4
0.5789	Remote Similarity	NPD4693	Phase 3
0.5741	Remote Similarity	NPD4691	Approved
0.569	Remote Similarity	NPD4753	Phase 2
0.5484	Remote Similarity	NPD6083	Phase 4
0.5484	Remote Similarity	NPD6084	Phase 2
0.5439	Remote Similarity	NPD3618	Phase 1
0.5167	Remote Similarity	NPD5330	Phase 4
0.5082	Remote Similarity	NPD5737	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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