NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	189.04
Volume:	185.952
LogP:	1.623
LogD:	1.267
LogS:	-2.79
# Rotatable Bonds:	1
TPSA:	70.16
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	1.885
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.166
MDCK Permeability:	4.43354792878381e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.304
Plasma Protein Binding (PPB):	45.63111877441406%
Volume Distribution (VD):	0.258
Pgp-substrate:	38.67306900024414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.16
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.034

ADMET: Excretion

Clearance (CL):	3.566
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.472
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.787
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.398
Carcinogencity:	0.089
Eye Corrosion:	0.004
Eye Irritation:	0.956
Respiratory Toxicity:	0.196

Download Data

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

Natural Product: NPC164340

Natural Product ID:	NPC164340
*Common Name:**	1-Oxo-2H-Isoquinoline-4-Carboxylic Acid
IUPAC Name:	1-oxo-2H-isoquinoline-4-carboxylic acid
Synonyms:
Standard InCHIKey:	IMEDZEDITFIMAK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H7NO3/c12-9-7-4-2-1-3-6(7)8(5-11-9)10(13)14/h1-5H,(H,11,12)(H,13,14)
SMILES:	c1ccc2c(c1)c(cnc2O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1483323
PubChem CID:	643161
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002054] Isoquinolones and derivatives

*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
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21381697]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	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
Potency	4

Activity Type	# Activity
Individual Protein	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[504431]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[504431]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[504431]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	369.6	nM	PMID[504431]

☑ 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 NPC164340 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	424
0.1-0.2	2989
0.2-0.3	11932
0.3-0.4	6458
0.4-0.5	15864
0.5-0.6	3519
0.6-0.7	1325
0.7-0.8	177
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9521	High Similarity	NPC44354
0.8807	High Similarity	NPC146724
0.8712	High Similarity	NPC113812
0.838	Intermediate Similarity	NPC56170
0.821	Intermediate Similarity	NPC167400
0.8197	Intermediate Similarity	NPC90229
0.8021	Intermediate Similarity	NPC155792
0.7898	Intermediate Similarity	NPC303225
0.7889	Intermediate Similarity	NPC207851
0.7876	Intermediate Similarity	NPC309845
0.7818	Intermediate Similarity	NPC159630
0.7818	Intermediate Similarity	NPC230085
0.7811	Intermediate Similarity	NPC312860
0.7784	Intermediate Similarity	NPC273532
0.7765	Intermediate Similarity	NPC263455
0.776	Intermediate Similarity	NPC278434
0.7714	Intermediate Similarity	NPC41717
0.7701	Intermediate Similarity	NPC97367
0.7679	Intermediate Similarity	NPC112741
0.7672	Intermediate Similarity	NPC474916
0.7663	Intermediate Similarity	NPC206186
0.7629	Intermediate Similarity	NPC193238
0.7602	Intermediate Similarity	NPC107287
0.76	Intermediate Similarity	NPC473057
0.7598	Intermediate Similarity	NPC139763
0.7584	Intermediate Similarity	NPC249614
0.7562	Intermediate Similarity	NPC74360
0.7561	Intermediate Similarity	NPC114310
0.7525	Intermediate Similarity	NPC111732
0.7514	Intermediate Similarity	NPC194040
0.75	Intermediate Similarity	NPC171787
0.7487	Intermediate Similarity	NPC83111
0.7459	Intermediate Similarity	NPC282103
0.7458	Intermediate Similarity	NPC471178
0.7449	Intermediate Similarity	NPC183777
0.7444	Intermediate Similarity	NPC191310
0.7435	Intermediate Similarity	NPC329024
0.7432	Intermediate Similarity	NPC271792
0.7423	Intermediate Similarity	NPC57398
0.7396	Intermediate Similarity	NPC317672
0.7396	Intermediate Similarity	NPC59033
0.7366	Intermediate Similarity	NPC295158
0.735	Intermediate Similarity	NPC219087
0.735	Intermediate Similarity	NPC476467
0.7347	Intermediate Similarity	NPC472259
0.734	Intermediate Similarity	NPC183805
0.7337	Intermediate Similarity	NPC317010
0.7327	Intermediate Similarity	NPC42678
0.7327	Intermediate Similarity	NPC477909
0.7327	Intermediate Similarity	NPC477907
0.7323	Intermediate Similarity	NPC63041
0.732	Intermediate Similarity	NPC213308
0.7318	Intermediate Similarity	NPC108469
0.7317	Intermediate Similarity	NPC253314
0.7317	Intermediate Similarity	NPC322488
0.7306	Intermediate Similarity	NPC320748
0.7306	Intermediate Similarity	NPC324245
0.7304	Intermediate Similarity	NPC216428
0.7292	Intermediate Similarity	NPC109922
0.7291	Intermediate Similarity	NPC27041
0.7289	Intermediate Similarity	NPC29702
0.7288	Intermediate Similarity	NPC322644
0.7286	Intermediate Similarity	NPC472550
0.7286	Intermediate Similarity	NPC472752
0.7286	Intermediate Similarity	NPC48042
0.7286	Intermediate Similarity	NPC304179
0.7273	Intermediate Similarity	NPC246381
0.7268	Intermediate Similarity	NPC476419
0.7268	Intermediate Similarity	NPC280714
0.7268	Intermediate Similarity	NPC276657
0.7263	Intermediate Similarity	NPC114974
0.7263	Intermediate Similarity	NPC138370
0.7259	Intermediate Similarity	NPC289086
0.7255	Intermediate Similarity	NPC62367
0.7247	Intermediate Similarity	NPC124542
0.7247	Intermediate Similarity	NPC59779
0.7247	Intermediate Similarity	NPC471177
0.7233	Intermediate Similarity	NPC477912
0.7231	Intermediate Similarity	NPC315491
0.7231	Intermediate Similarity	NPC45459
0.7231	Intermediate Similarity	NPC79223
0.7222	Intermediate Similarity	NPC309498
0.722	Intermediate Similarity	NPC301368
0.722	Intermediate Similarity	NPC84815
0.7209	Intermediate Similarity	NPC302159
0.7207	Intermediate Similarity	NPC265100
0.7206	Intermediate Similarity	NPC471016
0.7194	Intermediate Similarity	NPC32451
0.7194	Intermediate Similarity	NPC328559
0.7192	Intermediate Similarity	NPC237740
0.7188	Intermediate Similarity	NPC45850
0.7178	Intermediate Similarity	NPC472553
0.7172	Intermediate Similarity	NPC12944
0.7172	Intermediate Similarity	NPC25442
0.7157	Intermediate Similarity	NPC470306
0.7157	Intermediate Similarity	NPC477910
0.7151	Intermediate Similarity	NPC471997
0.715	Intermediate Similarity	NPC202812
0.7135	Intermediate Similarity	NPC471448
0.7129	Intermediate Similarity	NPC328154
0.7122	Intermediate Similarity	NPC206343
0.7122	Intermediate Similarity	NPC477908
0.7122	Intermediate Similarity	NPC471014
0.7122	Intermediate Similarity	NPC475408
0.7122	Intermediate Similarity	NPC6981
0.7121	Intermediate Similarity	NPC317572
0.712	Intermediate Similarity	NPC144381
0.7115	Intermediate Similarity	NPC127720
0.7115	Intermediate Similarity	NPC127026
0.7108	Intermediate Similarity	NPC319128
0.7108	Intermediate Similarity	NPC4421
0.7108	Intermediate Similarity	NPC228331
0.7104	Intermediate Similarity	NPC252590
0.7103	Intermediate Similarity	NPC182222
0.71	Intermediate Similarity	NPC156044
0.7098	Intermediate Similarity	NPC473821
0.7097	Intermediate Similarity	NPC67659
0.7095	Intermediate Similarity	NPC148860
0.7094	Intermediate Similarity	NPC110182
0.7094	Intermediate Similarity	NPC280473
0.7094	Intermediate Similarity	NPC323551
0.7088	Intermediate Similarity	NPC70949
0.7087	Intermediate Similarity	NPC294579
0.7087	Intermediate Similarity	NPC144779
0.7081	Intermediate Similarity	NPC471980
0.7079	Intermediate Similarity	NPC470020
0.7077	Intermediate Similarity	NPC78767
0.7077	Intermediate Similarity	NPC473814
0.7077	Intermediate Similarity	NPC74153
0.7065	Intermediate Similarity	NPC470190
0.7062	Intermediate Similarity	NPC285411
0.7062	Intermediate Similarity	NPC93390
0.7062	Intermediate Similarity	NPC14116
0.7062	Intermediate Similarity	NPC135950
0.7062	Intermediate Similarity	NPC211920
0.7062	Intermediate Similarity	NPC124029
0.7059	Intermediate Similarity	NPC51008
0.7059	Intermediate Similarity	NPC236668
0.7059	Intermediate Similarity	NPC41724
0.7059	Intermediate Similarity	NPC325705
0.7059	Intermediate Similarity	NPC52831
0.7053	Intermediate Similarity	NPC472555
0.705	Intermediate Similarity	NPC175602
0.7048	Intermediate Similarity	NPC233727
0.7048	Intermediate Similarity	NPC477902
0.7045	Intermediate Similarity	NPC107123
0.7043	Intermediate Similarity	NPC219848
0.7043	Intermediate Similarity	NPC111275
0.7039	Intermediate Similarity	NPC80681
0.7039	Intermediate Similarity	NPC246658
0.7033	Intermediate Similarity	NPC477911
0.7031	Intermediate Similarity	NPC154339
0.7028	Intermediate Similarity	NPC311196
0.7028	Intermediate Similarity	NPC134384
0.7024	Intermediate Similarity	NPC264674
0.7024	Intermediate Similarity	NPC146976
0.7015	Intermediate Similarity	NPC88008
0.7014	Intermediate Similarity	NPC473506
0.7011	Intermediate Similarity	NPC253810
0.701	Intermediate Similarity	NPC103230
0.7009	Intermediate Similarity	NPC207686
0.7005	Intermediate Similarity	NPC473089
0.7005	Intermediate Similarity	NPC75600
0.7005	Intermediate Similarity	NPC256268
0.7005	Intermediate Similarity	NPC473115
0.7005	Intermediate Similarity	NPC212768
0.7005	Intermediate Similarity	NPC6576
0.7005	Intermediate Similarity	NPC187494
0.7005	Intermediate Similarity	NPC103361
0.7005	Intermediate Similarity	NPC158020
0.7	Intermediate Similarity	NPC250807
0.7	Intermediate Similarity	NPC57797
0.7	Intermediate Similarity	NPC241025
0.7	Intermediate Similarity	NPC76565
0.7	Intermediate Similarity	NPC229893
0.6995	Remote Similarity	NPC78020
0.6995	Remote Similarity	NPC124086
0.6995	Remote Similarity	NPC116622
0.6994	Remote Similarity	NPC151489
0.6991	Remote Similarity	NPC477549
0.699	Remote Similarity	NPC156704
0.699	Remote Similarity	NPC207531
0.6984	Remote Similarity	NPC243058
0.6981	Remote Similarity	NPC475601
0.6981	Remote Similarity	NPC87152
0.6981	Remote Similarity	NPC228377
0.6981	Remote Similarity	NPC475631
0.6981	Remote Similarity	NPC328186
0.6981	Remote Similarity	NPC475600
0.6981	Remote Similarity	NPC122968
0.6981	Remote Similarity	NPC476110
0.6981	Remote Similarity	NPC477787
0.6977	Remote Similarity	NPC60553
0.6974	Remote Similarity	NPC276517
0.6967	Remote Similarity	NPC473850
0.6967	Remote Similarity	NPC475137
0.6967	Remote Similarity	NPC475498
0.6963	Remote Similarity	NPC150698
0.6963	Remote Similarity	NPC96801
0.6963	Remote Similarity	NPC477906

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 NPC164340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	666
0.2-0.3	902
0.3-0.4	1131
0.4-0.5	3407
0.5-0.6	2117
0.6-0.7	618
0.7-0.8	35
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.821	Intermediate Similarity	NPD9074	Approved
0.821	Intermediate Similarity	NPD9075	Approved
0.8187	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD107	Approved
0.7784	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD9271	Approved
0.7634	Intermediate Similarity	NPD2336	Approved
0.7569	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2896	Discontinued
0.75	Intermediate Similarity	NPD5088	Discontinued
0.7474	Intermediate Similarity	NPD2307	Discontinued
0.7473	Intermediate Similarity	NPD4948	Discontinued
0.7471	Intermediate Similarity	NPD820	Phase 3
0.741	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1173	Approved
0.7263	Intermediate Similarity	NPD925	Approved
0.7263	Intermediate Similarity	NPD926	Approved
0.7231	Intermediate Similarity	NPD484	Approved
0.7228	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2317	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3813	Approved
0.7191	Intermediate Similarity	NPD2511	Approved
0.7172	Intermediate Similarity	NPD5901	Discontinued
0.7168	Intermediate Similarity	NPD1270	Approved
0.7157	Intermediate Similarity	NPD5490	Discontinued
0.7143	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1483	Discontinued
0.7127	Intermediate Similarity	NPD424	Approved
0.7127	Intermediate Similarity	NPD425	Approved
0.7121	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1213	Phase 3
0.7112	Intermediate Similarity	NPD3178	Discontinued
0.7093	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4845	Discontinued
0.7059	Intermediate Similarity	NPD9510	Approved
0.7047	Intermediate Similarity	NPD6665	Discontinued
0.703	Intermediate Similarity	NPD6529	Discontinued
0.7021	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD1631	Approved
0.7006	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2831	Approved
0.7	Intermediate Similarity	NPD944	Approved
0.7	Intermediate Similarity	NPD6987	Phase 1
0.6995	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5100	Phase 3
0.698	Remote Similarity	NPD2510	Approved
0.698	Remote Similarity	NPD2509	Approved
0.6976	Remote Similarity	NPD3243	Approved
0.6976	Remote Similarity	NPD3794	Approved
0.6976	Remote Similarity	NPD3795	Approved
0.6966	Remote Similarity	NPD2809	Approved
0.6965	Remote Similarity	NPD7010	Phase 3
0.6957	Remote Similarity	NPD1575	Approved
0.6957	Remote Similarity	NPD4989	Phase 2
0.6957	Remote Similarity	NPD1573	Approved
0.6954	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6791	Phase 2
0.6927	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7069	Discontinued
0.6923	Remote Similarity	NPD1926	Approved
0.6915	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD9080	Approved
0.6909	Remote Similarity	NPD9284	Approved
0.6905	Remote Similarity	NPD4923	Phase 1
0.6902	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3925	Approved
0.6884	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD750	Phase 2
0.6878	Remote Similarity	NPD4417	Approved
0.6872	Remote Similarity	NPD4376	Phase 3
0.6859	Remote Similarity	NPD721	Approved
0.6851	Remote Similarity	NPD1630	Approved
0.6845	Remote Similarity	NPD482	Approved
0.6845	Remote Similarity	NPD9690	Approved
0.6839	Remote Similarity	NPD9363	Approved
0.6839	Remote Similarity	NPD9364	Phase 2
0.6837	Remote Similarity	NPD4551	Phase 2
0.6835	Remote Similarity	NPD3006	Discontinued
0.6834	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6999	Discontinued
0.6832	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7396	Approved
0.6832	Remote Similarity	NPD3947	Discontinued
0.6825	Remote Similarity	NPD4301	Approved
0.6821	Remote Similarity	NPD1649	Discontinued
0.6818	Remote Similarity	NPD1842	Approved
0.6811	Remote Similarity	NPD2781	Approved
0.6809	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2094	Phase 2
0.6806	Remote Similarity	NPD2092	Phase 2
0.6806	Remote Similarity	NPD2095	Phase 2
0.6796	Remote Similarity	NPD5475	Discontinued
0.6796	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD2780	Approved
0.6793	Remote Similarity	NPD2782	Approved
0.6782	Remote Similarity	NPD5513	Phase 2
0.6778	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5827	Discontinued
0.6772	Remote Similarity	NPD6642	Approved
0.6772	Remote Similarity	NPD6641	Approved
0.6771	Remote Similarity	NPD2096	Phase 2
0.6771	Remote Similarity	NPD2091	Phase 2
0.6771	Remote Similarity	NPD1096	Discontinued
0.6763	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3918	Approved
0.6763	Remote Similarity	NPD3917	Approved
0.6762	Remote Similarity	NPD4429	Discontinued
0.6761	Remote Similarity	NPD2803	Discontinued
0.6758	Remote Similarity	NPD5255	Approved
0.6755	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3394	Approved
0.6746	Remote Similarity	NPD3393	Approved
0.6746	Remote Similarity	NPD3389	Approved
0.6744	Remote Similarity	NPD9506	Approved
0.6743	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4889	Approved
0.673	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD272	Approved
0.6721	Remote Similarity	NPD9705	Discontinued
0.6721	Remote Similarity	NPD112	Approved
0.6715	Remote Similarity	NPD3915	Approved
0.6714	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD9382	Approved
0.6703	Remote Similarity	NPD9383	Approved
0.6702	Remote Similarity	NPD2481	Approved
0.6702	Remote Similarity	NPD2479	Phase 3
0.6701	Remote Similarity	NPD5505	Discontinued
0.6699	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3280	Approved
0.6686	Remote Similarity	NPD1625	Approved
0.6685	Remote Similarity	NPD4702	Approved
0.6685	Remote Similarity	NPD2061	Approved
0.6685	Remote Similarity	NPD4703	Approved
0.6683	Remote Similarity	NPD6226	Phase 3
0.6667	Remote Similarity	NPD6446	Discontinued
0.6667	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9362	Approved
0.6667	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD1587	Approved
0.6635	Remote Similarity	NPD5416	Discontinued
0.6634	Remote Similarity	NPD2305	Discontinued
0.6634	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4427	Phase 2
0.6632	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3238	Discontinued
0.663	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.662	Remote Similarity	NPD8479	Phase 2
0.662	Remote Similarity	NPD1996	Discontinued
0.6616	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5022	Discontinued
0.6605	Remote Similarity	NPD6753	Phase 1
0.6605	Remote Similarity	NPD6752	Phase 1
0.6604	Remote Similarity	NPD7878	Phase 2
0.6604	Remote Similarity	NPD3354	Phase 2
0.6604	Remote Similarity	NPD7395	Discontinued
0.6602	Remote Similarity	NPD3371	Approved
0.66	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3321	Discontinued
0.6598	Remote Similarity	NPD6178	Phase 3
0.6597	Remote Similarity	NPD2753	Discontinued
0.6583	Remote Similarity	NPD6361	Phase 2
0.6579	Remote Similarity	NPD4883	Approved
0.6575	Remote Similarity	NPD3262	Approved
0.6574	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7404	Approved
0.657	Remote Similarity	NPD6376	Discontinued
0.657	Remote Similarity	NPD7666	Phase 3
0.657	Remote Similarity	NPD7665	Phase 2
0.6569	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD1229	Phase 2
0.6566	Remote Similarity	NPD5849	Approved
0.6561	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.656	Remote Similarity	NPD2761	Approved
0.6558	Remote Similarity	NPD8356	Approved
0.6557	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7001	Phase 3
0.6553	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8091	Phase 3
0.6548	Remote Similarity	NPD4021	Phase 2
0.6544	Remote Similarity	NPD3263	Phase 3
0.6538	Remote Similarity	NPD4506	Discontinued
0.6538	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD53	Approved
0.6535	Remote Similarity	NPD7778	Approved
0.6535	Remote Similarity	NPD7777	Approved
0.6533	Remote Similarity	NPD6569	Phase 2
0.6533	Remote Similarity	NPD3924	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