NPASS Compound

Structure

NPC61449 OpenBabel06302216222D 100 99 0 0 1 0 0 0 0 0999 V2000 0.1340 2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 2.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 6.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 6.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 8.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 9.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 10.3923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 11.2583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 12.1244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 12.9904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 13.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 14.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8301 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6962 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5622 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4282 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2942 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1603 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0263 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8923 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7583 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6244 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4904 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.3564 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.2224 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 1.6340 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 2.6340 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 2.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 3.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 4.1340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5000 5.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 5.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 6.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 7.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7679 7.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7679 8.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9019 8.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9019 9.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0359 10.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0359 11.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8301 11.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8301 12.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6962 13.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6962 14.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5622 14.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5622 15.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4282 16.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4282 17.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2942 17.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2942 18.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1603 19.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 4.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 5.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 5.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 5.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0000 6.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 6.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5000 7.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 7.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0000 8.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 8.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5000 9.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 9.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0000 10.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0000 10.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5000 11.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5000 11.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.0000 11.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.0000 11.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 1 52 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 8 9 1 0 0 0 0 10 9 1 6 0 0 0 10 11 1 0 0 0 0 10 32 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 28 29 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 32 33 1 0 0 0 0 33 34 2 0 0 0 0 33 35 1 0 0 0 0 35 36 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 38 39 1 0 0 0 0 39 40 1 0 0 0 0 40 41 1 0 0 0 0 41 42 1 0 0 0 0 42 43 1 0 0 0 0 43 44 1 0 0 0 0 44 45 1 0 0 0 0 45 46 1 0 0 0 0 46 47 1 0 0 0 0 47 48 1 0 0 0 0 48 49 1 0 0 0 0 49 50 1 0 0 0 0 50 51 1 0 0 0 0 52 53 1 0 0 0 0 53 54 1 0 0 0 0 54 55 1 0 0 0 0 54 56 2 0 0 0 0 54 57 1 0 0 0 0 57 58 1 0 0 0 0 59 58 1 1 0 0 0 59 60 1 0 0 0 0 59 81 1 0 0 0 0 60 61 1 0 0 0 0 61 62 1 0 0 0 0 62 63 2 0 0 0 0 62 64 1 0 0 0 0 64 65 1 0 0 0 0 65 66 1 0 0 0 0 66 67 1 0 0 0 0 67 68 1 0 0 0 0 68 69 1 0 0 0 0 69 70 1 0 0 0 0 70 71 1 0 0 0 0 71 72 1 0 0 0 0 72 73 1 0 0 0 0 73 74 1 0 0 0 0 74 75 1 0 0 0 0 75 76 1 0 0 0 0 76 77 1 0 0 0 0 77 78 1 0 0 0 0 78 79 1 0 0 0 0 79 80 1 0 0 0 0 81 82 1 0 0 0 0 82 83 2 0 0 0 0 82 84 1 0 0 0 0 84 85 1 0 0 0 0 85 86 1 0 0 0 0 86 87 1 0 0 0 0 87 88 1 0 0 0 0 88 89 1 0 0 0 0 89 90 1 0 0 0 0 90 91 1 0 0 0 0 91 92 1 0 0 0 0 92 93 1 0 0 0 0 93 94 1 0 0 0 0 94 95 1 0 0 0 0 95 96 1 0 0 0 0 96 97 1 0 0 0 0 97 98 1 0 0 0 0 98 99 1 0 0 0 0 99100 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1465.1
Volume:	1588.074
LogP:	21.952
LogD:	5.53
LogS:	-5.872
# Rotatable Bonds:	86
TPSA:	230.63
# H-Bond Aceptor:	17
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.026
Synthetic Accessibility Score:	5.303
Fsp3:	0.951
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:	-5.396
MDCK Permeability:	3.3224768714035235e-08
Pgp-inhibitor:	0.0
Pgp-substrate:	0.514
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	121.71222686767578%
Volume Distribution (VD):	1.203
Pgp-substrate:	0.12453744560480118%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	1.21
Half-life (T1/2):	0.001

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.998
Carcinogencity:	0.038
Eye Corrosion:	0.126
Eye Irritation:	0.577
Respiratory Toxicity:	0.128

Download Data

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

Natural Product: NPC61449

Natural Product ID:	NPC61449
*Common Name:**	XVTUQDWPJJBEHJ-KZCWQMDCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XVTUQDWPJJBEHJ-KZCWQMDCSA-N
Standard InCHI:	InChI=1S/C81H158O17P2/c1-5-9-13-17-21-25-29-33-37-41-45-49-53-57-61-65-78(83)91-71-76(97-80(85)67-63-59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)73-95-99(87,88)93-69-75(82)70-94-100(89,90)96-74-77(98-81(86)68-64-60-56-52-48-44-40-36-32-28-24-20-16-12-8-4)72-92-79(84)66-62-58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h75-77,82H,5-74H2,1-4H3,(H,87,88)(H,89,90)/t76-,77-/m1/s1
SMILES:	CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCC(COP(=O)(O)OC[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)O)OC(=O)CCCCCCCCCCCCCCCCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	449005
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000256] Glycerophospholipids [CHEMONTID:0003389] Glycerophosphoglycerophosphoglycerols [CHEMONTID:0001233] Cardiolipins

*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
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	DOI[10.1021/jf970571j]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[240326]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[USDA]

☑ 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
NPO16230	NPC61449	Raw	Fruit	0.5	0.4	0.6	mg/100g	Database [DUKE]

☑ 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

☑ 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 NPC61449 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	999
0.1-0.2	7444
0.2-0.3	18365
0.3-0.4	11260
0.4-0.5	3885
0.5-0.6	611
0.6-0.7	109
0.7-0.8	20
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID

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 NPC61449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1375
0.1-0.2	4665
0.2-0.3	2099
0.3-0.4	712
0.4-0.5	247
0.5-0.6	42
0.6-0.7	5
0.7-0.8	3
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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