NPASS Compound

Structure

CID144557 OpenBabel06191715502D 39 42 0 0 1 0 0 0 0 0999 V2000 -7.6713 2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5374 2.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5374 0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0933 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6713 1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4034 2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0933 3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4034 1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5933 2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 1.3309 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0733 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2694 2.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5933 4.3776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2694 0.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5933 2.6456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 -0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 2.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 2.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7614 2.5032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 1.3443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 0.8309 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 1 5 2 0 0 0 0 1 12 1 0 0 0 0 2 7 2 0 0 0 0 2 13 1 0 0 0 0 3 6 2 0 0 0 0 3 14 1 0 0 0 0 4 8 2 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 13 22 2 0 0 0 0 15 18 2 0 0 0 0 15 28 1 0 0 0 0 16 19 2 0 0 0 0 16 29 1 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 20 10 1 6 0 0 0 20 26 1 0 0 0 0 20 38 1 0 0 0 0 21 33 2 0 0 0 0 21 38 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 6 0 0 0 24 14 1 1 0 0 0 24 39 1 0 0 0 0 25 39 1 0 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 27 36 2 0 0 0 0 27 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.11
Volume:	512.531
LogP:	1.951
LogD:	3.568
LogS:	-4.061
# Rotatable Bonds:	9
TPSA:	211.28
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	4.025
Fsp3:	0.148
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.403
MDCK Permeability:	6.330449195957044e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.79

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	97.22480010986328%
Volume Distribution (VD):	0.387
Pgp-substrate:	4.058462142944336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.641
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	8.008
Half-life (T1/2):	0.953

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.546
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.945
Carcinogencity:	0.228
Eye Corrosion:	0.003
Eye Irritation:	0.7
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC144557

Natural Product ID:	NPC144557
*Common Name:**	Lithospermic Acid
IUPAC Name:	(2S,3S)-4-[(E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
Synonyms:	Lithospermic Acid
Standard InCHIKey:	UJZQBMQZMKFSRV-RGKBJLTCSA-N
Standard InCHI:	InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/p-2/b8-4+/t20-,23+,24-/m1/s1
SMILES:	c1cc(c(cc1C[C@H](C(=O)O)OC(=O)/C=C/c1ccc(c2c1[C@@H]([C@@H](c1ccc(c(c1)O)[O-])O2)C(=O)O)O)O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518243
PubChem CID:	6441498
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s11418-007-0221-0]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027757]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502328]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17157006]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17217287]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19217780]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20674349]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25590529]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3373224]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7775984]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24697	Lycopus virginicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6532	Lithospermum ruderale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11945	Echium vulgare	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11945	Echium vulgare	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24697	Lycopus virginicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6532	Lithospermum ruderale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24697	Lycopus virginicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6532	Lithospermum ruderale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20297	Arnebia guttata	Species	Boraginaceae	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	3
Ki	5
Others	5

Activity Type	# Activity
Cell Line	4
Individual Protein	6
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	121.0	%	PMID[505362]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	151.0	%	PMID[505362]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	21.7	%	PMID[505362]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	55.0	%	PMID[505362]
NPT40	Individual Protein	72 kDa type IV collagenase	Rattus norvegicus	IC50	=	10200.0	nM	PMID[505364]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	>	10000.0	nM	PMID[505365]
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	101.2	nM	PMID[505365]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1000.0	nM	PMID[505363]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	4.3	n.a.	PMID[505363]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	>	10000.0	nM	PMID[505365]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	268.3	nM	PMID[505365]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	4.8	nM	PMID[505365]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[505366]

☑ 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 NPC144557 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	394
0.1-0.2	1475
0.2-0.3	3336
0.3-0.4	7718
0.4-0.5	10034
0.5-0.6	4308
0.6-0.7	5448
0.7-0.8	7753
0.8-0.85	2055
0.85-0.9	162
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC272750
0.9935	High Similarity	NPC134047
0.9935	High Similarity	NPC173729
0.9935	High Similarity	NPC223006
0.9684	High Similarity	NPC186100
0.9684	High Similarity	NPC216403
0.9684	High Similarity	NPC41494
0.9062	High Similarity	NPC469889
0.9038	High Similarity	NPC267091
0.9032	High Similarity	NPC221091
0.9032	High Similarity	NPC259576
0.9	High Similarity	NPC472961
0.9	High Similarity	NPC472962
0.8974	High Similarity	NPC243891
0.8974	High Similarity	NPC300329
0.8951	High Similarity	NPC45943
0.8889	High Similarity	NPC160378
0.8882	High Similarity	NPC301089
0.8876	High Similarity	NPC475996
0.8868	High Similarity	NPC80489
0.8827	High Similarity	NPC216916
0.8797	High Similarity	NPC476434
0.8795	High Similarity	NPC91043
0.8779	High Similarity	NPC475360
0.8765	High Similarity	NPC53889
0.8765	High Similarity	NPC170203
0.8758	High Similarity	NPC160512
0.8758	High Similarity	NPC156818
0.8758	High Similarity	NPC38779
0.8758	High Similarity	NPC289322
0.8758	High Similarity	NPC68324
0.8758	High Similarity	NPC114179
0.8743	High Similarity	NPC247964
0.8743	High Similarity	NPC476370
0.8742	High Similarity	NPC44730
0.8742	High Similarity	NPC295646
0.8727	High Similarity	NPC477517
0.8718	High Similarity	NPC143892
0.8718	High Similarity	NPC221383
0.8718	High Similarity	NPC299090
0.8718	High Similarity	NPC283081
0.8712	High Similarity	NPC112418
0.8704	High Similarity	NPC87317
0.8698	High Similarity	NPC296018
0.8698	High Similarity	NPC154741
0.8696	High Similarity	NPC104983
0.8696	High Similarity	NPC300845
0.8696	High Similarity	NPC88803
0.8696	High Similarity	NPC291948
0.8696	High Similarity	NPC250436
0.8693	High Similarity	NPC38473
0.869	High Similarity	NPC476374
0.869	High Similarity	NPC316539
0.8683	High Similarity	NPC102277
0.8683	High Similarity	NPC180768
0.8683	High Similarity	NPC279209
0.8675	High Similarity	NPC215802
0.8675	High Similarity	NPC167231
0.8662	High Similarity	NPC472969
0.8659	High Similarity	NPC164937
0.8659	High Similarity	NPC144843
0.8659	High Similarity	NPC471745
0.8659	High Similarity	NPC22324
0.865	High Similarity	NPC471744
0.865	High Similarity	NPC24164
0.8647	High Similarity	NPC476773
0.8642	High Similarity	NPC143328
0.8636	High Similarity	NPC67467
0.8634	High Similarity	NPC300757
0.8634	High Similarity	NPC180901
0.8625	High Similarity	NPC131121
0.8623	High Similarity	NPC280493
0.8621	High Similarity	NPC205721
0.8614	High Similarity	NPC43065
0.8614	High Similarity	NPC472452
0.8608	High Similarity	NPC476394
0.8608	High Similarity	NPC98809
0.8606	High Similarity	NPC89131
0.8599	High Similarity	NPC229264
0.8596	High Similarity	NPC244903
0.859	High Similarity	NPC53884
0.859	High Similarity	NPC258671
0.859	High Similarity	NPC223185
0.8589	High Similarity	NPC471750
0.8588	High Similarity	NPC473713
0.858	High Similarity	NPC470896
0.858	High Similarity	NPC227062
0.858	High Similarity	NPC473275
0.858	High Similarity	NPC318432
0.858	High Similarity	NPC150227
0.858	High Similarity	NPC54928
0.8571	High Similarity	NPC201814
0.8571	High Similarity	NPC477299
0.8571	High Similarity	NPC469888
0.8571	High Similarity	NPC72249
0.8563	High Similarity	NPC469521
0.8563	High Similarity	NPC298847
0.8563	High Similarity	NPC150131
0.8563	High Similarity	NPC311912
0.8563	High Similarity	NPC269625
0.8562	High Similarity	NPC270268
0.8562	High Similarity	NPC246566
0.8562	High Similarity	NPC95498
0.8547	High Similarity	NPC47883
0.8545	High Similarity	NPC473445
0.8545	High Similarity	NPC272722
0.8545	High Similarity	NPC42797
0.8544	High Similarity	NPC236166
0.8544	High Similarity	NPC192568
0.8544	High Similarity	NPC471076
0.8538	High Similarity	NPC98546
0.8538	High Similarity	NPC297807
0.8537	High Similarity	NPC200594
0.8537	High Similarity	NPC24627
0.8537	High Similarity	NPC155101
0.8537	High Similarity	NPC44507
0.8537	High Similarity	NPC47623
0.8529	High Similarity	NPC193377
0.8529	High Similarity	NPC287243
0.8528	High Similarity	NPC299520
0.8528	High Similarity	NPC40920
0.8528	High Similarity	NPC129684
0.8528	High Similarity	NPC223335
0.8528	High Similarity	NPC84935
0.8528	High Similarity	NPC190020
0.8528	High Similarity	NPC471515
0.8528	High Similarity	NPC77679
0.8528	High Similarity	NPC471479
0.8526	High Similarity	NPC304956
0.8526	High Similarity	NPC470130
0.8521	High Similarity	NPC469506
0.8519	High Similarity	NPC79998
0.8519	High Similarity	NPC268008
0.8519	High Similarity	NPC199926
0.8516	High Similarity	NPC253481
0.8516	High Similarity	NPC253722
0.8516	High Similarity	NPC31751
0.8512	High Similarity	NPC88557
0.8509	High Similarity	NPC65591
0.8509	High Similarity	NPC115203
0.8509	High Similarity	NPC474656
0.8509	High Similarity	NPC178574
0.8509	High Similarity	NPC473236
0.8506	High Similarity	NPC288452
0.8506	High Similarity	NPC289690
0.8494	Intermediate Similarity	NPC291977
0.8494	Intermediate Similarity	NPC475985
0.8485	Intermediate Similarity	NPC92589
0.8481	Intermediate Similarity	NPC32058
0.8481	Intermediate Similarity	NPC85734
0.848	Intermediate Similarity	NPC61904
0.848	Intermediate Similarity	NPC144097
0.8476	Intermediate Similarity	NPC195832
0.8476	Intermediate Similarity	NPC228501
0.8476	Intermediate Similarity	NPC469654
0.8476	Intermediate Similarity	NPC55738
0.8471	Intermediate Similarity	NPC82217
0.8471	Intermediate Similarity	NPC216842
0.8471	Intermediate Similarity	NPC476640
0.8471	Intermediate Similarity	NPC474568
0.8471	Intermediate Similarity	NPC163898
0.8466	Intermediate Similarity	NPC295436
0.8466	Intermediate Similarity	NPC474638
0.8466	Intermediate Similarity	NPC471500
0.8466	Intermediate Similarity	NPC163635
0.8466	Intermediate Similarity	NPC265511
0.8466	Intermediate Similarity	NPC478055
0.8466	Intermediate Similarity	NPC165483
0.8462	Intermediate Similarity	NPC476365
0.8462	Intermediate Similarity	NPC149011
0.8462	Intermediate Similarity	NPC477883
0.8462	Intermediate Similarity	NPC204937
0.8457	Intermediate Similarity	NPC25127
0.8457	Intermediate Similarity	NPC125487
0.8457	Intermediate Similarity	NPC287504
0.8457	Intermediate Similarity	NPC281703
0.8452	Intermediate Similarity	NPC186392
0.8452	Intermediate Similarity	NPC283041
0.8452	Intermediate Similarity	NPC48640
0.8452	Intermediate Similarity	NPC260266
0.8452	Intermediate Similarity	NPC149244
0.8452	Intermediate Similarity	NPC473818
0.8452	Intermediate Similarity	NPC100675
0.8447	Intermediate Similarity	NPC75695
0.8447	Intermediate Similarity	NPC93498
0.8447	Intermediate Similarity	NPC163883
0.8443	Intermediate Similarity	NPC471788
0.8443	Intermediate Similarity	NPC36320
0.8443	Intermediate Similarity	NPC472277
0.8443	Intermediate Similarity	NPC7688
0.8443	Intermediate Similarity	NPC326520
0.8443	Intermediate Similarity	NPC36916
0.8443	Intermediate Similarity	NPC125039
0.8443	Intermediate Similarity	NPC7154
0.8443	Intermediate Similarity	NPC142614
0.8443	Intermediate Similarity	NPC45449
0.8443	Intermediate Similarity	NPC72787
0.8443	Intermediate Similarity	NPC58223
0.8443	Intermediate Similarity	NPC36
0.8443	Intermediate Similarity	NPC191930

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 NPC144557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	881
0.2-0.3	1703
0.3-0.4	2552
0.4-0.5	1877
0.5-0.6	1028
0.6-0.7	566
0.7-0.8	171
0.8-0.85	24
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD4868	Clinical (unspecified phase)
0.858	High Similarity	NPD3882	Suspended
0.8494	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD3818	Discontinued
0.8443	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6166	Phase 2
0.8405	Intermediate Similarity	NPD3817	Phase 2
0.8382	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6190	Approved
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8314	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8282	Intermediate Similarity	NPD1934	Approved
0.8263	Intermediate Similarity	NPD7199	Phase 2
0.8253	Intermediate Similarity	NPD6234	Discontinued
0.8232	Intermediate Similarity	NPD1465	Phase 2
0.8193	Intermediate Similarity	NPD7075	Discontinued
0.8187	Intermediate Similarity	NPD5844	Phase 1
0.8125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2801	Approved
0.8061	Intermediate Similarity	NPD37	Approved
0.8034	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1512	Approved
0.8024	Intermediate Similarity	NPD4965	Approved
0.8024	Intermediate Similarity	NPD4967	Phase 2
0.8024	Intermediate Similarity	NPD4966	Approved
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD5494	Approved
0.7964	Intermediate Similarity	NPD5402	Approved
0.7952	Intermediate Similarity	NPD6801	Discontinued
0.7943	Intermediate Similarity	NPD7251	Discontinued
0.7931	Intermediate Similarity	NPD7074	Phase 3
0.7922	Intermediate Similarity	NPD6798	Discontinued
0.7919	Intermediate Similarity	NPD7228	Approved
0.7919	Intermediate Similarity	NPD3751	Discontinued
0.7904	Intermediate Similarity	NPD7819	Suspended
0.7901	Intermediate Similarity	NPD6799	Approved
0.7901	Intermediate Similarity	NPD1511	Approved
0.7898	Intermediate Similarity	NPD7808	Phase 3
0.7885	Intermediate Similarity	NPD6355	Discontinued
0.7874	Intermediate Similarity	NPD7054	Approved
0.787	Intermediate Similarity	NPD3749	Approved
0.7853	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8312	Approved
0.7853	Intermediate Similarity	NPD8313	Approved
0.7831	Intermediate Similarity	NPD6599	Discontinued
0.7829	Intermediate Similarity	NPD7472	Approved
0.7826	Intermediate Similarity	NPD4628	Phase 3
0.7821	Intermediate Similarity	NPD4060	Phase 1
0.7821	Intermediate Similarity	NPD8434	Phase 2
0.7791	Intermediate Similarity	NPD3787	Discontinued
0.7771	Intermediate Similarity	NPD3226	Approved
0.7765	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD5403	Approved
0.7758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6233	Phase 2
0.7747	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3926	Phase 2
0.774	Intermediate Similarity	NPD7685	Pre-registration
0.7733	Intermediate Similarity	NPD8127	Discontinued
0.7725	Intermediate Similarity	NPD4380	Phase 2
0.7719	Intermediate Similarity	NPD919	Approved
0.7692	Intermediate Similarity	NPD3764	Approved
0.7679	Intermediate Similarity	NPD7411	Suspended
0.7647	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6559	Discontinued
0.7636	Intermediate Similarity	NPD2533	Approved
0.7636	Intermediate Similarity	NPD5401	Approved
0.7636	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2534	Approved
0.7636	Intermediate Similarity	NPD2532	Approved
0.763	Intermediate Similarity	NPD6959	Discontinued
0.7607	Intermediate Similarity	NPD3750	Approved
0.7593	Intermediate Similarity	NPD1549	Phase 2
0.7593	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7229	Phase 3
0.7571	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD447	Suspended
0.7531	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1247	Approved
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7484	Intermediate Similarity	NPD1613	Approved
0.7484	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2935	Discontinued
0.7444	Intermediate Similarity	NPD7240	Approved
0.7438	Intermediate Similarity	NPD230	Phase 1
0.7425	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2344	Approved
0.7423	Intermediate Similarity	NPD5762	Approved
0.7423	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD5763	Approved
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7407	Intermediate Similarity	NPD1510	Phase 2
0.7405	Intermediate Similarity	NPD7095	Approved
0.7403	Intermediate Similarity	NPD1608	Approved
0.7394	Intermediate Similarity	NPD4110	Phase 3
0.7394	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6273	Approved
0.7362	Intermediate Similarity	NPD2796	Approved
0.7358	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4002	Approved
0.7344	Intermediate Similarity	NPD7435	Discontinued
0.7344	Intermediate Similarity	NPD4004	Approved
0.7342	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3452	Approved
0.733	Intermediate Similarity	NPD3450	Approved
0.733	Intermediate Similarity	NPD2494	Approved
0.733	Intermediate Similarity	NPD2493	Approved
0.7317	Intermediate Similarity	NPD7266	Discontinued
0.7312	Intermediate Similarity	NPD2490	Approved
0.7312	Intermediate Similarity	NPD2488	Approved
0.7306	Intermediate Similarity	NPD4583	Approved
0.7306	Intermediate Similarity	NPD4582	Approved
0.7301	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3748	Approved
0.7296	Intermediate Similarity	NPD3027	Phase 3
0.7289	Intermediate Similarity	NPD8166	Discontinued
0.7278	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD9494	Approved
0.7273	Intermediate Similarity	NPD5958	Discontinued
0.7267	Intermediate Similarity	NPD943	Approved
0.7261	Intermediate Similarity	NPD2797	Approved
0.7256	Intermediate Similarity	NPD1551	Phase 2
0.725	Intermediate Similarity	NPD3268	Approved
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7246	Intermediate Similarity	NPD2309	Approved
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1933	Approved
0.7212	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD17	Approved
0.7206	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4062	Phase 3
0.7188	Intermediate Similarity	NPD6781	Approved
0.7188	Intermediate Similarity	NPD6777	Approved
0.7188	Intermediate Similarity	NPD6778	Approved
0.7188	Intermediate Similarity	NPD6782	Approved
0.7188	Intermediate Similarity	NPD6776	Approved
0.7188	Intermediate Similarity	NPD6780	Approved
0.7188	Intermediate Similarity	NPD6779	Approved
0.7186	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7003	Approved
0.7168	Intermediate Similarity	NPD6385	Approved
0.7168	Intermediate Similarity	NPD6386	Approved
0.7165	Intermediate Similarity	NPD7680	Approved
0.716	Intermediate Similarity	NPD1240	Approved
0.7158	Intermediate Similarity	NPD7038	Approved
0.7158	Intermediate Similarity	NPD7039	Approved
0.7152	Intermediate Similarity	NPD2438	Suspended
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7152	Intermediate Similarity	NPD1203	Approved
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD920	Approved
0.7135	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7177	Discontinued
0.7126	Intermediate Similarity	NPD6674	Discontinued
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7125	Intermediate Similarity	NPD4908	Phase 1
0.7121	Intermediate Similarity	NPD7874	Approved
0.7121	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2974	Approved
0.712	Intermediate Similarity	NPD2973	Approved
0.712	Intermediate Similarity	NPD2975	Approved
0.7119	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3146	Approved
0.7118	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4340	Discontinued
0.7108	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6005	Phase 3
0.7108	Intermediate Similarity	NPD1471	Phase 3
0.7108	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6004	Phase 3
0.7108	Intermediate Similarity	NPD6002	Phase 3
0.7098	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4580	Approved
0.7095	Intermediate Similarity	NPD5711	Approved
0.7095	Intermediate Similarity	NPD5710	Approved
0.7086	Intermediate Similarity	NPD5760	Phase 2
0.7086	Intermediate Similarity	NPD5761	Phase 2

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