NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	203.06
Volume:	203.248
LogP:	1.92
LogD:	1.832
LogS:	-2.935
# Rotatable Bonds:	2
TPSA:	59.16
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	1.866
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.722
MDCK Permeability:	1.4088638636167161e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.069
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.813

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.645
Plasma Protein Binding (PPB):	52.93888854980469%
Volume Distribution (VD):	0.66
Pgp-substrate:	30.55047607421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.802
CYP2C19-inhibitor:	0.628
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.822
CYP2D6-inhibitor:	0.118
CYP2D6-substrate:	0.346
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	8.317
Half-life (T1/2):	0.854

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.571
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.545
Carcinogencity:	0.091
Eye Corrosion:	0.006
Eye Irritation:	0.92
Respiratory Toxicity:	0.084

Download Data

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

Natural Product: NPC44354

Natural Product ID:	NPC44354
*Common Name:**	Methyl 1-Oxo-2H-Isoquinoline-4-Carboxylate
IUPAC Name:	methyl 1-oxo-2H-isoquinoline-4-carboxylate
Synonyms:
Standard InCHIKey:	HLIJPUALSQELGB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H9NO3/c1-15-11(14)9-6-12-10(13)8-5-3-2-4-7(8)9/h2-6H,1H3,(H,12,13)
SMILES:	COC(=O)c1cnc(c2ccccc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1697952
PubChem CID:	641184
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.	n.a.	n.a.		Database[Phenol-Explorer]
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.	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	11

Activity Type	# Activity
Individual Protein	9
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[522270]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[522270]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[522270]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[522270]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[522270]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	177827.9	nM	PMID[522270]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[522270]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[522270]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[522270]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	15003.0	nM	PMID[522270]

☑ 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 NPC44354 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	340
0.1-0.2	2288
0.2-0.3	9343
0.3-0.4	7378
0.4-0.5	15734
0.5-0.6	5885
0.6-0.7	1422
0.7-0.8	298
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9521	High Similarity	NPC164340
0.8424	Intermediate Similarity	NPC146724
0.8304	Intermediate Similarity	NPC113812
0.8216	Intermediate Similarity	NPC56170
0.8041	Intermediate Similarity	NPC193238
0.7969	Intermediate Similarity	NPC155792
0.7965	Intermediate Similarity	NPC107287
0.796	Intermediate Similarity	NPC74360
0.7941	Intermediate Similarity	NPC112741
0.7933	Intermediate Similarity	NPC249614
0.7889	Intermediate Similarity	NPC191310
0.7853	Intermediate Similarity	NPC90229
0.7849	Intermediate Similarity	NPC194040
0.7824	Intermediate Similarity	NPC167400
0.7796	Intermediate Similarity	NPC282103
0.775	Intermediate Similarity	NPC476467
0.7742	Intermediate Similarity	NPC207851
0.7723	Intermediate Similarity	NPC42678
0.7723	Intermediate Similarity	NPC477909
0.7723	Intermediate Similarity	NPC477907
0.7708	Intermediate Similarity	NPC109922
0.7696	Intermediate Similarity	NPC216428
0.7688	Intermediate Similarity	NPC48042
0.7688	Intermediate Similarity	NPC304179
0.7688	Intermediate Similarity	NPC472550
0.768	Intermediate Similarity	NPC280714
0.765	Intermediate Similarity	NPC309845
0.7647	Intermediate Similarity	NPC62367
0.7638	Intermediate Similarity	NPC63041
0.7629	Intermediate Similarity	NPC320748
0.7629	Intermediate Similarity	NPC324245
0.7621	Intermediate Similarity	NPC477912
0.7614	Intermediate Similarity	NPC263455
0.761	Intermediate Similarity	NPC84815
0.761	Intermediate Similarity	NPC301368
0.76	Intermediate Similarity	NPC472752
0.7598	Intermediate Similarity	NPC471016
0.7592	Intermediate Similarity	NPC138370
0.7577	Intermediate Similarity	NPC329024
0.7576	Intermediate Similarity	NPC289086
0.7574	Intermediate Similarity	NPC472553
0.7574	Intermediate Similarity	NPC111732
0.7571	Intermediate Similarity	NPC246381
0.7569	Intermediate Similarity	NPC41717
0.7558	Intermediate Similarity	NPC159630
0.7558	Intermediate Similarity	NPC230085
0.7554	Intermediate Similarity	NPC303225
0.7551	Intermediate Similarity	NPC79223
0.7549	Intermediate Similarity	NPC477910
0.7549	Intermediate Similarity	NPC470306
0.7538	Intermediate Similarity	NPC309498
0.7526	Intermediate Similarity	NPC206186
0.7513	Intermediate Similarity	NPC32451
0.7513	Intermediate Similarity	NPC328559
0.7512	Intermediate Similarity	NPC477908
0.7512	Intermediate Similarity	NPC475408
0.7512	Intermediate Similarity	NPC6981
0.7512	Intermediate Similarity	NPC206343
0.7512	Intermediate Similarity	NPC328154
0.7512	Intermediate Similarity	NPC471014
0.75	Intermediate Similarity	NPC4421
0.75	Intermediate Similarity	NPC127720
0.75	Intermediate Similarity	NPC228331
0.75	Intermediate Similarity	NPC319128
0.75	Intermediate Similarity	NPC127026
0.7488	Intermediate Similarity	NPC280473
0.7488	Intermediate Similarity	NPC323551
0.7477	Intermediate Similarity	NPC182222
0.7476	Intermediate Similarity	NPC294579
0.7476	Intermediate Similarity	NPC144779
0.7476	Intermediate Similarity	NPC148860
0.7464	Intermediate Similarity	NPC471980
0.7463	Intermediate Similarity	NPC470190
0.7459	Intermediate Similarity	NPC139763
0.7459	Intermediate Similarity	NPC473057
0.7459	Intermediate Similarity	NPC97367
0.7458	Intermediate Similarity	NPC312860
0.7452	Intermediate Similarity	NPC253314
0.7451	Intermediate Similarity	NPC51008
0.7451	Intermediate Similarity	NPC41724
0.7449	Intermediate Similarity	NPC59033
0.7449	Intermediate Similarity	NPC474916
0.7449	Intermediate Similarity	NPC317672
0.7446	Intermediate Similarity	NPC273532
0.7441	Intermediate Similarity	NPC124029
0.7441	Intermediate Similarity	NPC14116
0.7441	Intermediate Similarity	NPC285411
0.7441	Intermediate Similarity	NPC211920
0.744	Intermediate Similarity	NPC472555
0.7437	Intermediate Similarity	NPC317572
0.7435	Intermediate Similarity	NPC278434
0.7429	Intermediate Similarity	NPC233727
0.7429	Intermediate Similarity	NPC477902
0.7416	Intermediate Similarity	NPC477911
0.7415	Intermediate Similarity	NPC264674
0.7413	Intermediate Similarity	NPC156044
0.7409	Intermediate Similarity	NPC107123
0.7409	Intermediate Similarity	NPC114974
0.7406	Intermediate Similarity	NPC311196
0.7406	Intermediate Similarity	NPC134384
0.7393	Intermediate Similarity	NPC473506
0.7391	Intermediate Similarity	NPC158020
0.7391	Intermediate Similarity	NPC473115
0.7391	Intermediate Similarity	NPC6576
0.7391	Intermediate Similarity	NPC187494
0.7391	Intermediate Similarity	NPC212768
0.7391	Intermediate Similarity	NPC473089
0.7391	Intermediate Similarity	NPC75600
0.7389	Intermediate Similarity	NPC470020
0.7385	Intermediate Similarity	NPC135950
0.7381	Intermediate Similarity	NPC57797
0.7381	Intermediate Similarity	NPC250807
0.7381	Intermediate Similarity	NPC76565
0.7379	Intermediate Similarity	NPC207531
0.7366	Intermediate Similarity	NPC236668
0.7358	Intermediate Similarity	NPC122968
0.7358	Intermediate Similarity	NPC87152
0.7358	Intermediate Similarity	NPC328186
0.7358	Intermediate Similarity	NPC476110
0.7358	Intermediate Similarity	NPC228377
0.7358	Intermediate Similarity	NPC477787
0.7358	Intermediate Similarity	NPC475600
0.7358	Intermediate Similarity	NPC475631
0.7358	Intermediate Similarity	NPC475601
0.7353	Intermediate Similarity	NPC470189
0.7353	Intermediate Similarity	NPC40919
0.7347	Intermediate Similarity	NPC473053
0.7346	Intermediate Similarity	NPC475498
0.7346	Intermediate Similarity	NPC473850
0.7346	Intermediate Similarity	NPC475137
0.7336	Intermediate Similarity	NPC477906
0.7336	Intermediate Similarity	NPC96801
0.7336	Intermediate Similarity	NPC150698
0.733	Intermediate Similarity	NPC146976
0.7327	Intermediate Similarity	NPC475835
0.7324	Intermediate Similarity	NPC470486
0.7324	Intermediate Similarity	NPC471977
0.7324	Intermediate Similarity	NPC471190
0.7324	Intermediate Similarity	NPC475644
0.7323	Intermediate Similarity	NPC103361
0.7321	Intermediate Similarity	NPC477901
0.7317	Intermediate Similarity	NPC292517
0.7313	Intermediate Similarity	NPC12944
0.7313	Intermediate Similarity	NPC25442
0.7308	Intermediate Similarity	NPC319556
0.7302	Intermediate Similarity	NPC317010
0.73	Intermediate Similarity	NPC57398
0.7295	Intermediate Similarity	NPC62844
0.7295	Intermediate Similarity	NPC193361
0.7291	Intermediate Similarity	NPC171787
0.7286	Intermediate Similarity	NPC477903
0.7277	Intermediate Similarity	NPC146824
0.7268	Intermediate Similarity	NPC220337
0.7268	Intermediate Similarity	NPC469489
0.7264	Intermediate Similarity	NPC26881
0.7256	Intermediate Similarity	NPC316841
0.7256	Intermediate Similarity	NPC475303
0.7256	Intermediate Similarity	NPC292416
0.7256	Intermediate Similarity	NPC473689
0.7256	Intermediate Similarity	NPC475596
0.7252	Intermediate Similarity	NPC475533
0.7251	Intermediate Similarity	NPC235364
0.7251	Intermediate Similarity	NPC477788
0.7245	Intermediate Similarity	NPC230403
0.7245	Intermediate Similarity	NPC289786
0.7245	Intermediate Similarity	NPC103230
0.7243	Intermediate Similarity	NPC475362
0.7241	Intermediate Similarity	NPC183777
0.724	Intermediate Similarity	NPC295158
0.7236	Intermediate Similarity	NPC123395
0.7234	Intermediate Similarity	NPC84347
0.7233	Intermediate Similarity	NPC219087
0.7232	Intermediate Similarity	NPC134637
0.7228	Intermediate Similarity	NPC471178
0.7228	Intermediate Similarity	NPC472259
0.7222	Intermediate Similarity	NPC319880
0.7222	Intermediate Similarity	NPC224928
0.7222	Intermediate Similarity	NPC30456
0.7222	Intermediate Similarity	NPC244839
0.7222	Intermediate Similarity	NPC469748
0.7222	Intermediate Similarity	NPC320324
0.722	Intermediate Similarity	NPC324619
0.722	Intermediate Similarity	NPC475315
0.7216	Intermediate Similarity	NPC183805
0.7212	Intermediate Similarity	NPC30570
0.7211	Intermediate Similarity	NPC271792
0.7209	Intermediate Similarity	NPC114310
0.7206	Intermediate Similarity	NPC266249
0.7198	Intermediate Similarity	NPC165837
0.7189	Intermediate Similarity	NPC238278
0.7189	Intermediate Similarity	NPC237702
0.7189	Intermediate Similarity	NPC108469
0.7183	Intermediate Similarity	NPC477899
0.7183	Intermediate Similarity	NPC477900
0.7179	Intermediate Similarity	NPC83111
0.7156	Intermediate Similarity	NPC475426
0.7156	Intermediate Similarity	NPC327769
0.7156	Intermediate Similarity	NPC475406
0.7156	Intermediate Similarity	NPC35208
0.7149	Intermediate Similarity	NPC210296

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 NPC44354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	649
0.2-0.3	872
0.3-0.4	1078
0.4-0.5	3131
0.5-0.6	2446
0.6-0.7	701
0.7-0.8	53
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8239	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.8032	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD9271	Approved
0.7912	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD820	Phase 3
0.7824	Intermediate Similarity	NPD9074	Approved
0.7824	Intermediate Similarity	NPD9075	Approved
0.7588	Intermediate Similarity	NPD107	Approved
0.7568	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5088	Discontinued
0.75	Intermediate Similarity	NPD2336	Approved
0.7431	Intermediate Similarity	NPD1483	Discontinued
0.7401	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2307	Discontinued
0.734	Intermediate Similarity	NPD6529	Discontinued
0.7317	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2831	Approved
0.7291	Intermediate Similarity	NPD2509	Approved
0.7291	Intermediate Similarity	NPD2510	Approved
0.7277	Intermediate Similarity	NPD7010	Phase 3
0.7273	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2896	Discontinued
0.7254	Intermediate Similarity	NPD4948	Discontinued
0.7243	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7069	Discontinued
0.7225	Intermediate Similarity	NPD1926	Approved
0.7202	Intermediate Similarity	NPD3006	Discontinued
0.7198	Intermediate Similarity	NPD3794	Approved
0.7198	Intermediate Similarity	NPD3795	Approved
0.7184	Intermediate Similarity	NPD4417	Approved
0.7183	Intermediate Similarity	NPD3925	Approved
0.7168	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2511	Approved
0.7158	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1173	Approved
0.7157	Intermediate Similarity	NPD4551	Phase 2
0.7143	Intermediate Similarity	NPD3947	Discontinued
0.7143	Intermediate Similarity	NPD7396	Approved
0.7135	Intermediate Similarity	NPD925	Approved
0.7135	Intermediate Similarity	NPD926	Approved
0.713	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4923	Phase 1
0.7114	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4376	Phase 3
0.7105	Intermediate Similarity	NPD6641	Approved
0.7105	Intermediate Similarity	NPD6642	Approved
0.7095	Intermediate Similarity	NPD4989	Phase 2
0.7062	Intermediate Similarity	NPD4429	Discontinued
0.7048	Intermediate Similarity	NPD5490	Discontinued
0.7042	Intermediate Similarity	NPD4301	Approved
0.7039	Intermediate Similarity	NPD1270	Approved
0.7031	Intermediate Similarity	NPD9510	Approved
0.703	Intermediate Similarity	NPD484	Approved
0.703	Intermediate Similarity	NPD4491	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2317	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5475	Discontinued
0.7014	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5513	Phase 2
0.6995	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3178	Discontinued
0.6976	Remote Similarity	NPD5901	Discontinued
0.6974	Remote Similarity	NPD4889	Approved
0.6967	Remote Similarity	NPD3393	Approved
0.6967	Remote Similarity	NPD3389	Approved
0.6967	Remote Similarity	NPD3394	Approved
0.6966	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3813	Approved
0.6939	Remote Similarity	NPD4375	Approved
0.6923	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4506	Discontinued
0.6919	Remote Similarity	NPD1213	Phase 3
0.6919	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3280	Approved
0.6916	Remote Similarity	NPD8479	Phase 2
0.6916	Remote Similarity	NPD1996	Discontinued
0.6915	Remote Similarity	NPD424	Approved
0.6915	Remote Similarity	NPD425	Approved
0.6901	Remote Similarity	NPD3354	Phase 2
0.69	Remote Similarity	NPD6361	Phase 2
0.6898	Remote Similarity	NPD1631	Approved
0.6895	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5022	Discontinued
0.6893	Remote Similarity	NPD944	Approved
0.6893	Remote Similarity	NPD6987	Phase 1
0.6881	Remote Similarity	NPD4845	Discontinued
0.6881	Remote Similarity	NPD1229	Phase 2
0.6879	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5100	Phase 3
0.6869	Remote Similarity	NPD6770	Approved
0.6869	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4021	Phase 2
0.6857	Remote Similarity	NPD5416	Discontinued
0.685	Remote Similarity	NPD6665	Discontinued
0.685	Remote Similarity	NPD3924	Approved
0.685	Remote Similarity	NPD3921	Approved
0.685	Remote Similarity	NPD3922	Approved
0.685	Remote Similarity	NPD3923	Approved
0.6848	Remote Similarity	NPD2809	Approved
0.6837	Remote Similarity	NPD1096	Discontinued
0.6835	Remote Similarity	NPD3263	Phase 3
0.6832	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD3371	Approved
0.6825	Remote Similarity	NPD5866	Approved
0.6824	Remote Similarity	NPD8091	Phase 3
0.6822	Remote Similarity	NPD7395	Discontinued
0.6821	Remote Similarity	NPD3386	Phase 2
0.6818	Remote Similarity	NPD9363	Approved
0.6818	Remote Similarity	NPD6791	Phase 2
0.6818	Remote Similarity	NPD9364	Phase 2
0.6808	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD3259	Approved
0.6804	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7467	Discontinued
0.6792	Remote Similarity	NPD3243	Approved
0.6791	Remote Similarity	NPD7404	Approved
0.6784	Remote Similarity	NPD9284	Approved
0.6783	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2581	Approved
0.6774	Remote Similarity	NPD2582	Approved
0.6771	Remote Similarity	NPD750	Phase 2
0.677	Remote Similarity	NPD6790	Phase 1
0.6766	Remote Similarity	NPD6569	Phase 2
0.6759	Remote Similarity	NPD6242	Discontinued
0.6758	Remote Similarity	NPD5640	Discontinued
0.6754	Remote Similarity	NPD1575	Approved
0.6754	Remote Similarity	NPD1573	Approved
0.6751	Remote Similarity	NPD721	Approved
0.6749	Remote Similarity	NPD6226	Phase 3
0.6741	Remote Similarity	NPD5891	Approved
0.6738	Remote Similarity	NPD1630	Approved
0.6733	Remote Similarity	NPD4526	Approved
0.6733	Remote Similarity	NPD4529	Approved
0.6733	Remote Similarity	NPD4528	Approved
0.6732	Remote Similarity	NPD6999	Discontinued
0.6732	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7885	Phase 2
0.6726	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4373	Phase 2
0.6726	Remote Similarity	NPD7886	Phase 2
0.6716	Remote Similarity	NPD2952	Discontinued
0.6715	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD1649	Discontinued
0.6701	Remote Similarity	NPD749	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3396	Approved
0.67	Remote Similarity	NPD3395	Approved
0.6699	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7470	Discontinued
0.6698	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6276	Discontinued
0.6684	Remote Similarity	NPD9383	Approved
0.6684	Remote Similarity	NPD9382	Approved
0.6683	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5293	Phase 2
0.6682	Remote Similarity	NPD5827	Discontinued
0.6667	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6716	Phase 1
0.6667	Remote Similarity	NPD5512	Phase 3
0.6667	Remote Similarity	NPD2803	Discontinued
0.6667	Remote Similarity	NPD4952	Phase 3
0.6652	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4039	Approved
0.6651	Remote Similarity	NPD32	Approved
0.6651	Remote Similarity	NPD4033	Approved
0.6651	Remote Similarity	NPD4034	Approved
0.6651	Remote Similarity	NPD4036	Approved
0.6651	Remote Similarity	NPD4122	Approved
0.6651	Remote Similarity	NPD31	Approved
0.6651	Remote Similarity	NPD4038	Approved
0.6651	Remote Similarity	NPD4035	Approved
0.6651	Remote Similarity	NPD4037	Approved
0.665	Remote Similarity	NPD4204	Approved
0.665	Remote Similarity	NPD9362	Approved
0.665	Remote Similarity	NPD4203	Approved
0.6649	Remote Similarity	NPD5255	Approved
0.6649	Remote Similarity	NPD482	Approved
0.6638	Remote Similarity	NPD5482	Discontinued
0.6637	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD1842	Approved
0.6629	Remote Similarity	NPD9506	Approved
0.6621	Remote Similarity	NPD8356	Approved
0.662	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD7001	Phase 3
0.6618	Remote Similarity	NPD4427	Phase 2
0.6616	Remote Similarity	NPD2095	Phase 2
0.6616	Remote Similarity	NPD2094	Phase 2
0.6616	Remote Similarity	NPD2092	Phase 2
0.6615	Remote Similarity	NPD2781	Approved
0.6614	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD180	Clinical (unspecified phase)

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