NPASS Compound

Structure

CID103647 OpenBabel06191715452D 32 36 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0981 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 25 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 21 32 2 0 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 23 28 1 1 0 0 0 23 29 1 0 0 0 0 24 26 1 6 0 0 0 24 30 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	499.598
LogP:	5.871
LogD:	4.387
LogS:	-4.84
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	4.939
Fsp3:	0.967
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:	-5.01
MDCK Permeability:	9.360790500068106e-06
Pgp-inhibitor:	0.735
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.903
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.399
Plasma Protein Binding (PPB):	92.65506744384766%
Volume Distribution (VD):	1.338
Pgp-substrate:	1.777092695236206%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.5
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.849

ADMET: Excretion

Clearance (CL):	16.762
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.556
Human Hepatotoxicity (H-HT):	0.387
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.373
Skin Sensitization:	0.801
Carcinogencity:	0.448
Eye Corrosion:	0.022
Eye Irritation:	0.015
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC103647

Natural Product ID:	NPC103647
*Common Name:**	3-Oxo-29-Hydroxyfriedelane
IUPAC Name:	(4R,4aS,6aS,6aS,6bR,8aS,11R,12aR,14aS,14bS)-11-(hydroxymethyl)-4,4a,6a,6b,8a,11,14a-heptamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
Synonyms:
Standard InCHIKey:	NAOCHKKFDYTOII-MGIZKUGISA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-20-21(32)8-9-22-27(20,4)11-10-23-28(22,5)15-17-30(7)24-18-25(2,19-31)12-13-26(24,3)14-16-29(23,30)6/h20,22-24,31H,8-19H2,1-7H3/t20-,22+,23-,24+,25+,26+,27+,28-,29+,30-/m0/s1
SMILES:	C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@@](C)(CC[C@]3(C)CC[C@]12C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516320
PubChem CID:	14108943
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0040-4039(99)00339-1]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10746886]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10757717]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	PMID[10757718]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843583]
NPO6683	Salacia petenensis	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[11270725]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12943781]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951446]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	stems	Thailand	n.a.	PMID[14510595]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[14738381]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738381]
NPO25232	Peperomia heyneana	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17291043]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791477]
NPO1207	Microtropis triflora	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17972583]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[23252270]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2534610]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[535601]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8328267]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Phytochemistry, 2000, 53, 715-722.]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8818	Rohdea wattii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26370	Iryanthera juruensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24417	Centaurea hololeuca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1207	Microtropis triflora	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27395	Mandragora officinarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25232	Peperomia heyneana	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15755	Thymbra spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8499	Osmerus mordax	Species	Osmeridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16903	Chisocheton siamensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14034	Salvia coulteri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13859	Senecio flavus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25293	Beaumontia brevituba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27107	Coleus coerulescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13710	Lyophyllum shimeji	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6683	Salacia petenensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26578	Astragalus pamirensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	98000.0	nM	PMID[550289]

☑ 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 NPC103647 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	389
0.1-0.2	3871
0.2-0.3	16888
0.3-0.4	9785
0.4-0.5	5159
0.5-0.6	4478
0.6-0.7	1712
0.7-0.8	352
0.8-0.85	37
0.85-0.9	6
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180777
1.0	High Similarity	NPC260319
1.0	High Similarity	NPC2568
0.9545	High Similarity	NPC290058
0.9403	High Similarity	NPC477229
0.9403	High Similarity	NPC68426
0.9403	High Similarity	NPC282905
0.9265	High Similarity	NPC130011
0.9265	High Similarity	NPC168511
0.9265	High Similarity	NPC159325
0.913	High Similarity	NPC267753
0.9091	High Similarity	NPC31187
0.9091	High Similarity	NPC100917
0.9091	High Similarity	NPC281203
0.9091	High Similarity	NPC469724
0.9	High Similarity	NPC108840
0.8841	High Similarity	NPC81759
0.8806	High Similarity	NPC474954
0.875	High Similarity	NPC26029
0.8696	High Similarity	NPC247195
0.8592	High Similarity	NPC97534
0.8592	High Similarity	NPC174964
0.8592	High Similarity	NPC195155
0.8529	High Similarity	NPC475977
0.8529	High Similarity	NPC473225
0.8493	Intermediate Similarity	NPC472608
0.8472	Intermediate Similarity	NPC5767
0.8472	Intermediate Similarity	NPC475742
0.8429	Intermediate Similarity	NPC151018
0.8429	Intermediate Similarity	NPC58057
0.8429	Intermediate Similarity	NPC320549
0.8429	Intermediate Similarity	NPC156277
0.8406	Intermediate Similarity	NPC213178
0.8406	Intermediate Similarity	NPC6120
0.8406	Intermediate Similarity	NPC131892
0.8406	Intermediate Similarity	NPC327728
0.8406	Intermediate Similarity	NPC324607
0.8406	Intermediate Similarity	NPC321732
0.84	Intermediate Similarity	NPC50658
0.8356	Intermediate Similarity	NPC221420
0.8356	Intermediate Similarity	NPC23884
0.831	Intermediate Similarity	NPC475230
0.831	Intermediate Similarity	NPC232112
0.831	Intermediate Similarity	NPC310766
0.8286	Intermediate Similarity	NPC476731
0.8286	Intermediate Similarity	NPC108131
0.8243	Intermediate Similarity	NPC31031
0.8243	Intermediate Similarity	NPC243594
0.8194	Intermediate Similarity	NPC472854
0.8194	Intermediate Similarity	NPC254340
0.8169	Intermediate Similarity	NPC473267
0.8169	Intermediate Similarity	NPC89310
0.8158	Intermediate Similarity	NPC3915
0.8158	Intermediate Similarity	NPC280781
0.8158	Intermediate Similarity	NPC476071
0.8158	Intermediate Similarity	NPC48756
0.8143	Intermediate Similarity	NPC469941
0.8143	Intermediate Similarity	NPC252032
0.8143	Intermediate Similarity	NPC476734
0.8143	Intermediate Similarity	NPC319671
0.8133	Intermediate Similarity	NPC201459
0.8116	Intermediate Similarity	NPC472984
0.8108	Intermediate Similarity	NPC112463
0.8108	Intermediate Similarity	NPC298168
0.8108	Intermediate Similarity	NPC143133
0.8095	Intermediate Similarity	NPC307063
0.8082	Intermediate Similarity	NPC125767
0.8082	Intermediate Similarity	NPC273366
0.8082	Intermediate Similarity	NPC179858
0.8082	Intermediate Similarity	NPC21220
0.8077	Intermediate Similarity	NPC25037
0.8077	Intermediate Similarity	NPC34984
0.8077	Intermediate Similarity	NPC105895
0.806	Intermediate Similarity	NPC290791
0.806	Intermediate Similarity	NPC292419
0.8052	Intermediate Similarity	NPC310989
0.8028	Intermediate Similarity	NPC477929
0.8	Intermediate Similarity	NPC478228
0.8	Intermediate Similarity	NPC127798
0.7975	Intermediate Similarity	NPC62572
0.7973	Intermediate Similarity	NPC472487
0.7973	Intermediate Similarity	NPC472486
0.7945	Intermediate Similarity	NPC280026
0.7945	Intermediate Similarity	NPC133922
0.7945	Intermediate Similarity	NPC167702
0.7922	Intermediate Similarity	NPC271572
0.7922	Intermediate Similarity	NPC103754
0.7922	Intermediate Similarity	NPC474484
0.7922	Intermediate Similarity	NPC474870
0.7887	Intermediate Similarity	NPC178541
0.7867	Intermediate Similarity	NPC475031
0.7867	Intermediate Similarity	NPC149249
0.7867	Intermediate Similarity	NPC472746
0.7867	Intermediate Similarity	NPC264602
0.7857	Intermediate Similarity	NPC204233
0.7848	Intermediate Similarity	NPC180834
0.7838	Intermediate Similarity	NPC159789
0.7838	Intermediate Similarity	NPC24014
0.7838	Intermediate Similarity	NPC472311
0.7838	Intermediate Similarity	NPC212733
0.7838	Intermediate Similarity	NPC27349
0.7821	Intermediate Similarity	NPC61107
0.7821	Intermediate Similarity	NPC289486
0.7821	Intermediate Similarity	NPC30583
0.7778	Intermediate Similarity	NPC477850
0.7763	Intermediate Similarity	NPC185465
0.775	Intermediate Similarity	NPC274724
0.775	Intermediate Similarity	NPC133954
0.7746	Intermediate Similarity	NPC475893
0.7746	Intermediate Similarity	NPC470956
0.7746	Intermediate Similarity	NPC469987
0.7733	Intermediate Similarity	NPC4209
0.7722	Intermediate Similarity	NPC269684
0.7722	Intermediate Similarity	NPC472743
0.7722	Intermediate Similarity	NPC175410
0.7722	Intermediate Similarity	NPC475726
0.7714	Intermediate Similarity	NPC42060
0.7703	Intermediate Similarity	NPC477930
0.7692	Intermediate Similarity	NPC328264
0.7671	Intermediate Similarity	NPC469940
0.7671	Intermediate Similarity	NPC478227
0.7662	Intermediate Similarity	NPC52951
0.7662	Intermediate Similarity	NPC320144
0.7662	Intermediate Similarity	NPC476812
0.7654	Intermediate Similarity	NPC187545
0.7654	Intermediate Similarity	NPC74363
0.7654	Intermediate Similarity	NPC213412
0.7654	Intermediate Similarity	NPC475862
0.7639	Intermediate Similarity	NPC64466
0.7639	Intermediate Similarity	NPC474962
0.7632	Intermediate Similarity	NPC207010
0.7632	Intermediate Similarity	NPC317913
0.7632	Intermediate Similarity	NPC106078
0.7632	Intermediate Similarity	NPC477918
0.7632	Intermediate Similarity	NPC476811
0.7632	Intermediate Similarity	NPC477919
0.7632	Intermediate Similarity	NPC180199
0.7625	Intermediate Similarity	NPC474482
0.7625	Intermediate Similarity	NPC474233
0.7625	Intermediate Similarity	NPC475745
0.7625	Intermediate Similarity	NPC237938
0.7625	Intermediate Similarity	NPC474996
0.7625	Intermediate Similarity	NPC219535
0.7606	Intermediate Similarity	NPC41542
0.7595	Intermediate Similarity	NPC268040
0.7571	Intermediate Similarity	NPC80463
0.7571	Intermediate Similarity	NPC260116
0.7571	Intermediate Similarity	NPC19311
0.7571	Intermediate Similarity	NPC230047
0.7571	Intermediate Similarity	NPC469791
0.7568	Intermediate Similarity	NPC36310
0.7564	Intermediate Similarity	NPC470609
0.7564	Intermediate Similarity	NPC261616
0.7564	Intermediate Similarity	NPC18955
0.7561	Intermediate Similarity	NPC73064
0.7561	Intermediate Similarity	NPC173089
0.7561	Intermediate Similarity	NPC158141
0.7532	Intermediate Similarity	NPC476810
0.7532	Intermediate Similarity	NPC324700
0.7532	Intermediate Similarity	NPC34046
0.7532	Intermediate Similarity	NPC476732
0.7532	Intermediate Similarity	NPC171426
0.7532	Intermediate Similarity	NPC80089
0.7532	Intermediate Similarity	NPC224802
0.7532	Intermediate Similarity	NPC199965
0.7531	Intermediate Similarity	NPC201655
0.7531	Intermediate Similarity	NPC292553
0.75	Intermediate Similarity	NPC477933
0.75	Intermediate Similarity	NPC477932
0.75	Intermediate Similarity	NPC472744
0.747	Intermediate Similarity	NPC230387
0.747	Intermediate Similarity	NPC474511
0.747	Intermediate Similarity	NPC1753
0.7468	Intermediate Similarity	NPC162632
0.7468	Intermediate Similarity	NPC267691
0.7468	Intermediate Similarity	NPC469745
0.7468	Intermediate Similarity	NPC263272
0.7468	Intermediate Similarity	NPC274050
0.7467	Intermediate Similarity	NPC162164
0.7467	Intermediate Similarity	NPC255168
0.7465	Intermediate Similarity	NPC268736
0.7465	Intermediate Similarity	NPC142712
0.7465	Intermediate Similarity	NPC477931
0.7463	Intermediate Similarity	NPC476735
0.7439	Intermediate Similarity	NPC95594
0.7439	Intermediate Similarity	NPC235341
0.7439	Intermediate Similarity	NPC471737
0.7439	Intermediate Similarity	NPC477579
0.7439	Intermediate Similarity	NPC72638
0.7439	Intermediate Similarity	NPC472738
0.7439	Intermediate Similarity	NPC56588
0.7439	Intermediate Similarity	NPC83242
0.7436	Intermediate Similarity	NPC80891
0.7436	Intermediate Similarity	NPC245029
0.7436	Intermediate Similarity	NPC472310
0.7436	Intermediate Similarity	NPC31302
0.7436	Intermediate Similarity	NPC73013
0.7436	Intermediate Similarity	NPC201276
0.7436	Intermediate Similarity	NPC192744
0.7432	Intermediate Similarity	NPC126642

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 NPC103647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	486
0.1-0.2	3872
0.2-0.3	3391
0.3-0.4	878
0.4-0.5	267
0.5-0.6	202
0.6-0.7	28
0.7-0.8	26
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
0.8551	High Similarity	NPD4245	Approved
0.8551	High Similarity	NPD4789	Approved
0.8551	High Similarity	NPD4244	Approved
0.8429	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD3698	Phase 2
0.8406	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5360	Phase 3
0.8	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD4224	Phase 2
0.7945	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD3703	Phase 2
0.7733	Intermediate Similarity	NPD6117	Approved
0.7671	Intermediate Similarity	NPD6081	Approved
0.7632	Intermediate Similarity	NPD6116	Phase 1
0.7532	Intermediate Similarity	NPD3671	Phase 1
0.7532	Intermediate Similarity	NPD6697	Approved
0.7532	Intermediate Similarity	NPD6115	Approved
0.7532	Intermediate Similarity	NPD6118	Approved
0.7532	Intermediate Similarity	NPD6114	Approved
0.7432	Intermediate Similarity	NPD4758	Discontinued
0.7432	Intermediate Similarity	NPD5777	Approved
0.7317	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4788	Approved
0.7209	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD3702	Approved
0.7089	Intermediate Similarity	NPD5364	Discontinued
0.6988	Remote Similarity	NPD4786	Approved
0.6951	Remote Similarity	NPD3667	Approved
0.6854	Remote Similarity	NPD7748	Approved
0.6786	Remote Similarity	NPD3666	Approved
0.6786	Remote Similarity	NPD3133	Approved
0.6786	Remote Similarity	NPD3665	Phase 1
0.6711	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3617	Approved
0.663	Remote Similarity	NPD7902	Approved
0.6629	Remote Similarity	NPD8035	Phase 2
0.6629	Remote Similarity	NPD8034	Phase 2
0.6628	Remote Similarity	NPD3618	Phase 1
0.6623	Remote Similarity	NPD4787	Phase 1
0.6618	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5328	Approved
0.6591	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7645	Phase 2
0.6444	Remote Similarity	NPD6079	Approved
0.6404	Remote Similarity	NPD4753	Phase 2
0.6389	Remote Similarity	NPD3198	Approved
0.6353	Remote Similarity	NPD4223	Phase 3
0.6353	Remote Similarity	NPD4221	Approved
0.6322	Remote Similarity	NPD5329	Approved
0.631	Remote Similarity	NPD4695	Discontinued
0.6304	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7900	Approved
0.6292	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5279	Phase 3
0.6235	Remote Similarity	NPD4692	Approved
0.6235	Remote Similarity	NPD4139	Approved
0.6224	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3668	Phase 3
0.6207	Remote Similarity	NPD4197	Approved
0.6196	Remote Similarity	NPD4202	Approved
0.6196	Remote Similarity	NPD6399	Phase 3
0.617	Remote Similarity	NPD7614	Phase 1
0.6154	Remote Similarity	NPD6705	Phase 1
0.6118	Remote Similarity	NPD6928	Phase 2
0.6105	Remote Similarity	NPD6084	Phase 2
0.6105	Remote Similarity	NPD6083	Phase 2
0.6067	Remote Similarity	NPD7146	Approved
0.6067	Remote Similarity	NPD4690	Approved
0.6067	Remote Similarity	NPD4138	Approved
0.6067	Remote Similarity	NPD5330	Approved
0.6067	Remote Similarity	NPD4689	Approved
0.6067	Remote Similarity	NPD5205	Approved
0.6067	Remote Similarity	NPD4688	Approved
0.6067	Remote Similarity	NPD7521	Approved
0.6067	Remote Similarity	NPD6409	Approved
0.6067	Remote Similarity	NPD4623	Approved
0.6067	Remote Similarity	NPD6684	Approved
0.6067	Remote Similarity	NPD4519	Discontinued
0.6067	Remote Similarity	NPD4693	Phase 3
0.6067	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7334	Approved
0.6064	Remote Similarity	NPD4629	Approved
0.6064	Remote Similarity	NPD5210	Approved
0.6061	Remote Similarity	NPD385	Approved
0.6061	Remote Similarity	NPD384	Approved
0.6053	Remote Similarity	NPD7909	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6920	Discontinued
0.6	Remote Similarity	NPD5221	Approved
0.5979	Remote Similarity	NPD8418	Phase 2
0.5938	Remote Similarity	NPD5173	Approved
0.5938	Remote Similarity	NPD4755	Approved
0.5934	Remote Similarity	NPD6903	Approved
0.5934	Remote Similarity	NPD6672	Approved
0.5934	Remote Similarity	NPD5737	Approved
0.593	Remote Similarity	NPD7525	Registered
0.5909	Remote Similarity	NPD634	Phase 3
0.5904	Remote Similarity	NPD6942	Approved
0.5904	Remote Similarity	NPD7339	Approved
0.5889	Remote Similarity	NPD5690	Phase 2
0.5889	Remote Similarity	NPD5280	Approved
0.5889	Remote Similarity	NPD4694	Approved
0.5882	Remote Similarity	NPD4776	Phase 2
0.5882	Remote Similarity	NPD4777	Suspended
0.5882	Remote Similarity	NPD6415	Discontinued
0.5875	Remote Similarity	NPD3725	Approved
0.5875	Remote Similarity	NPD3726	Approved
0.5857	Remote Similarity	NPD3186	Phase 1
0.5833	Remote Similarity	NPD7732	Phase 3
0.5833	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4700	Approved
0.5816	Remote Similarity	NPD5285	Approved
0.5816	Remote Similarity	NPD5286	Approved
0.5816	Remote Similarity	NPD4696	Approved
0.5784	Remote Similarity	NPD6412	Phase 2
0.5769	Remote Similarity	NPD7341	Phase 2
0.5758	Remote Similarity	NPD5223	Approved
0.5729	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD6098	Approved
0.57	Remote Similarity	NPD5224	Approved
0.57	Remote Similarity	NPD5211	Phase 2
0.57	Remote Similarity	NPD4633	Approved
0.57	Remote Similarity	NPD5226	Approved
0.57	Remote Similarity	NPD5225	Approved
0.5686	Remote Similarity	NPD5739	Approved
0.5686	Remote Similarity	NPD6402	Approved
0.5686	Remote Similarity	NPD6675	Approved
0.5686	Remote Similarity	NPD7128	Approved
0.5682	Remote Similarity	NPD8028	Phase 2
0.5679	Remote Similarity	NPD4137	Phase 3
0.5672	Remote Similarity	NPD386	Approved
0.5672	Remote Similarity	NPD388	Approved
0.5657	Remote Similarity	NPD7639	Approved
0.5657	Remote Similarity	NPD7640	Approved
0.5652	Remote Similarity	NPD3573	Approved
0.5644	Remote Similarity	NPD4754	Approved
0.5644	Remote Similarity	NPD5175	Approved
0.5644	Remote Similarity	NPD5174	Approved
0.5632	Remote Similarity	NPD4195	Approved
0.561	Remote Similarity	NPD4747	Approved
0.561	Remote Similarity	NPD4691	Approved
0.5607	Remote Similarity	NPD8133	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