NPASS Compound

Natural Product: NPC479651

Natural Product ID	NPC479651
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VLODYJFIBXTMIL-SCDNXBIHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 81 85 0 0 0 0 0 0 0 0999 V2000 3.8897 -0.9893 1.3929 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3023 -1.0833 0.0731 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7800 -0.0291 -0.8675 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2362 -0.0079 -1.1877 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1931 0.1998 -0.1108 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9652 1.3153 -0.0523 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8080 2.3300 -1.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9145 1.4967 1.0374 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6238 2.5196 1.0929 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0524 0.5445 2.0322 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8657 -1.3794 -0.1121 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3891 -2.6949 0.4336 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1055 -2.5962 0.5880 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4503 -1.2821 -0.0263 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7200 -1.4233 -1.4885 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6802 -0.6492 0.5776 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8062 -1.6339 0.4334 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1600 -0.9774 0.6975 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3134 0.0892 -0.3357 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6854 0.7189 -0.1450 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7664 1.5184 1.1198 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6904 -0.4026 -0.1326 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8864 1.6306 -1.3003 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9069 2.2593 -1.4993 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7697 1.7788 -2.2673 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5174 2.0970 -1.4540 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2264 1.0869 -0.3981 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7274 1.6257 0.8907 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8766 0.6715 -0.0130 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7446 1.2662 -0.7697 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6126 0.7881 -0.5538 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8048 -0.4486 0.2677 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8886 -0.0364 1.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4860 -2.6873 1.9380 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9361 -3.0998 1.6125 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3730 -0.0167 1.6583 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1855 -1.2827 2.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6832 -1.7465 1.5181 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7783 -2.0318 -0.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2786 -0.2756 -1.8628 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4734 0.9994 -0.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4553 0.8087 -1.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5160 -0.9374 -1.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4063 -0.4840 0.6977 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1750 1.9192 -2.0915 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4276 3.2115 -0.8475 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7689 2.6974 -1.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4272 0.8085 2.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7952 -1.5042 -1.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5736 -3.5373 -0.3021 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6323 -3.4354 0.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7342 -1.0631 -1.8031 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0217 -0.9388 -2.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7362 -2.5192 -1.7391 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5836 -0.5243 1.6921 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7149 -2.4194 1.2432 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8314 -2.1812 -0.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9165 -1.7653 0.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2014 -0.6099 1.7310 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3732 -0.4357 -1.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8094 1.8601 1.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1214 2.3977 1.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5179 0.9285 2.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7000 -0.0814 -0.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7872 -0.8308 0.8832 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3827 -1.1941 -0.8773 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9265 2.6520 -2.9448 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6319 0.8970 -2.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7486 3.0862 -0.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7239 2.2964 -2.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3912 2.6725 0.9250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1463 1.2265 1.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7844 2.3852 -0.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0249 1.2172 -1.8670 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1138 0.6213 -1.5279 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2289 1.5940 -0.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8608 -0.8741 2.3936 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0792 0.6468 2.0274 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8102 0.6082 1.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4141 -3.6378 2.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7033 -3.7235 1.4607 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 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 2 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 27 26 1 6 27 28 1 0 29 28 1 1 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 1 13 34 1 0 12 35 1 0 32 11 1 0 32 14 1 0 29 16 1 0 27 19 1 0 29 27 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 6 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 7 45 1 0 7 46 1 0 7 47 1 0 10 48 1 0 11 49 1 6 12 50 1 6 13 51 1 6 15 52 1 0 15 53 1 0 15 54 1 0 16 55 1 1 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 6 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 22 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 26 70 1 0 28 71 1 0 28 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 35 81 1 0 M END

Standard InCHIKey	VLODYJFIBXTMIL-SCDNXBIHSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-17(8-7-9-18(2)25(34)35)22-23(32)24(33)28(6)20-11-10-19-26(3,4)21(31)12-13-29(19)16-30(20,29)15-14-27(22,28)5/h9,17,19-20,22-24,32-33H,7-8,10-16H2,1-6H3,(H,34,35)/b18-9+/t17-,19+,20+,22+,23-,24-,27-,28-,29-,30+/m1/s1
SMILES	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1[C@H]([C@H]([C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)C(=O)CC[C@]54C[C@@]35CC[C@]12C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	3.043 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.721 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.808 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	25.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.453	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.858	Fsp³:	0.867
MCE-18:	140.679 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.75	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.253	Promiscuous compounds:	0.277

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.56	MDCK Permeability:	-5.105
Pgp-inhibitor:	0.104	Pgp-substrate:	0.005
PAMPA:	0.981 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.077	30% Bioavailability (F30%):	0.141
50% Bioavailability (F50%):	0.83

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.891
Plasma Protein Binding (PPB):	82.65%	Volume Distribution (VD):	-0.343
Fu:	16.872% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.04
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.022	CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.902	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.97
HLM stability:	0.11 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.927

Half-life (T1/2):

1.452

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.097
Human Hepatotoxicity (H-HT):	0.584	Drug-induced Liver Injury (DILI):	0.058
AMES Toxicity:	0.074	Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.541	Skin Sensitization:	0.78
Carcinogencity:	0.146	Eye Corrosion:	0.0
Eye Irritation:	0.064	Respiratory Toxicity:	0.776
Drug-induced Neurotoxicity:	0.019	Ototoxicity:	0.94
Hematotoxicity:	0.3	Drug-induced Nephrotoxicity:	0.752
Genotoxicity:	0.471	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.006	Hek293 Cytotoxicity:	0.024
BCF:	0.806 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.973 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.583 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.485 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19435338]
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31557016]
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6329	Abies chensiensis	Species	Pinaceae	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
MIC	4

Activity Type	# Activity
Organism	4

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	40.0	ug.mL-1	PMID[31557016]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	40.0	ug.mL-1	PMID[31557016]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	40.0	ug.mL-1	PMID[31557016]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	40.0	ug.mL-1	PMID[31557016]

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 NPC479651 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	22867
0.1-0.2	24318
0.2-0.3	2400
0.3-0.4	204
0.4-0.5	52
0.5-0.6	13
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	Natural Product ID
0.7273	Intermediate Similarity	NPC479655
0.7273	Intermediate Similarity	NPC479652
0.6615	Remote Similarity	NPC16287
0.6	Remote Similarity	NPC23217
0.5775	Remote Similarity	NPC29152
0.5556	Remote Similarity	NPC476174
0.5352	Remote Similarity	NPC479654
0.5352	Remote Similarity	NPC479656
0.52	Remote Similarity	NPC479657
0.5139	Remote Similarity	NPC476293
0.5139	Remote Similarity	NPC60350
0.507	Remote Similarity	NPC110923
0.507	Remote Similarity	NPC74296
0.5068	Remote Similarity	NPC181743
0.5068	Remote Similarity	NPC178025
0.5067	Remote Similarity	NPC156546
0.5065	Remote Similarity	NPC483394

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6300
0.1-0.2	2780
0.2-0.3	70
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
		NPD

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