NPASS Compound

Structure

NPC472118 OpenBabel07101719132D 23 27 0 0 1 0 0 0 0 0999 V2000 -3.5618 -0.0210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3623 -0.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5744 -1.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5744 -0.2965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7434 -1.7357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7434 0.1832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7632 -1.8240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1279 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2451 -1.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3448 -0.3063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4498 -1.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9125 -1.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3716 -1.4966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4950 -0.8168 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9125 -0.2965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0404 -0.2965 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1279 -1.5525 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5640 -0.7762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0404 -1.2560 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -5.0283 -0.9796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2965 -2.4650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 11 2 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 2 0 0 0 0 6 15 2 0 0 0 0 7 17 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 7 1 6 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 1 0 0 0 17 19 1 6 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 19 8 1 1 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.17
Volume:	320.79
LogP:	2.396
LogD:	2.374
LogS:	-3.089
# Rotatable Bonds:	1
TPSA:	52.57
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.78
Synthetic Accessibility Score:	6.169
Fsp3:	0.526
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:	-5.419
MDCK Permeability:	4.900295607512817e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.084
Human Intestinal Absorption (HIA):	0.936
20% Bioavailability (F20%):	0.344
30% Bioavailability (F30%):	0.757

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	69.46380615234375%
Volume Distribution (VD):	1.721
Pgp-substrate:	29.103458404541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.323
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.506
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.428
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.563
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.732

ADMET: Excretion

Clearance (CL):	11.264
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.398
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.46
Carcinogencity:	0.938
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC472118

Natural Product ID:	NPC472118
*Common Name:**	LQTOLYYQLWIGMJ-STODSUDRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LQTOLYYQLWIGMJ-STODSUDRSA-N
Standard InCHI:	InChI=1S/C19H22N2O2/c1-2-11-9-21-16-8-19(17(21)7-13(11)14(16)10-22)18(23)12-5-3-4-6-15(12)20-19/h2-6,13-14,16-17,20,22H,7-10H2,1H3/b11-2-/t13-,14?,16+,17+,19+/m1/s1
SMILES:	C/C=C1/CN2[C@@H]3C([C@@H]1C[C@H]2[C@]1(C3)Nc2c(C1=O)cccc2)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338241
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000251] Indolizidines

*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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[520355]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[520355]

☑ 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 NPC472118 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	231
0.1-0.2	1140
0.2-0.3	4669
0.3-0.4	20044
0.4-0.5	11976
0.5-0.6	3658
0.6-0.7	858
0.7-0.8	107
0.8-0.85	8
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8405	Intermediate Similarity	NPC472102
0.8405	Intermediate Similarity	NPC309531
0.8242	Intermediate Similarity	NPC472101
0.8242	Intermediate Similarity	NPC472120
0.8204	Intermediate Similarity	NPC279527
0.8204	Intermediate Similarity	NPC214960
0.8144	Intermediate Similarity	NPC472106
0.8061	Intermediate Similarity	NPC113946
0.8024	Intermediate Similarity	NPC472117
0.7931	Intermediate Similarity	NPC475094
0.7904	Intermediate Similarity	NPC36495
0.7829	Intermediate Similarity	NPC218594
0.7829	Intermediate Similarity	NPC99043
0.7778	Intermediate Similarity	NPC478075
0.7733	Intermediate Similarity	NPC224970
0.7733	Intermediate Similarity	NPC223595
0.7733	Intermediate Similarity	NPC167724
0.773	Intermediate Similarity	NPC264589
0.7706	Intermediate Similarity	NPC282339
0.7706	Intermediate Similarity	NPC99632
0.7692	Intermediate Similarity	NPC193410
0.7654	Intermediate Similarity	NPC97584
0.7647	Intermediate Similarity	NPC248117
0.7633	Intermediate Similarity	NPC61013
0.7614	Intermediate Similarity	NPC264482
0.7614	Intermediate Similarity	NPC203202
0.7613	Intermediate Similarity	NPC209389
0.7602	Intermediate Similarity	NPC293458
0.7572	Intermediate Similarity	NPC472115
0.7572	Intermediate Similarity	NPC472114
0.756	Intermediate Similarity	NPC478076
0.7545	Intermediate Similarity	NPC475763
0.7544	Intermediate Similarity	NPC474058
0.7514	Intermediate Similarity	NPC476441
0.75	Intermediate Similarity	NPC176983
0.75	Intermediate Similarity	NPC472121
0.75	Intermediate Similarity	NPC286871
0.75	Intermediate Similarity	NPC177261
0.7457	Intermediate Similarity	NPC138293
0.7457	Intermediate Similarity	NPC113056
0.743	Intermediate Similarity	NPC6974
0.7427	Intermediate Similarity	NPC123241
0.7418	Intermediate Similarity	NPC52262
0.7407	Intermediate Similarity	NPC106118
0.7399	Intermediate Similarity	NPC85651
0.7368	Intermediate Similarity	NPC29285
0.736	Intermediate Similarity	NPC329338
0.736	Intermediate Similarity	NPC469726
0.7345	Intermediate Similarity	NPC355
0.7345	Intermediate Similarity	NPC292265
0.7341	Intermediate Similarity	NPC225319
0.7337	Intermediate Similarity	NPC14994
0.7321	Intermediate Similarity	NPC237649
0.7321	Intermediate Similarity	NPC300596
0.732	Intermediate Similarity	NPC472538
0.7317	Intermediate Similarity	NPC471164
0.7308	Intermediate Similarity	NPC159963
0.7308	Intermediate Similarity	NPC477159
0.7293	Intermediate Similarity	NPC15840
0.7282	Intermediate Similarity	NPC270241
0.7278	Intermediate Similarity	NPC186669
0.7268	Intermediate Similarity	NPC225400
0.7267	Intermediate Similarity	NPC162417
0.7267	Intermediate Similarity	NPC316104
0.7263	Intermediate Similarity	NPC470548
0.7255	Intermediate Similarity	NPC122886
0.7231	Intermediate Similarity	NPC470786
0.7231	Intermediate Similarity	NPC471155
0.7222	Intermediate Similarity	NPC471743
0.7211	Intermediate Similarity	NPC472541
0.7211	Intermediate Similarity	NPC472542
0.7207	Intermediate Similarity	NPC285622
0.7207	Intermediate Similarity	NPC476425
0.7204	Intermediate Similarity	NPC284706
0.7179	Intermediate Similarity	NPC254698
0.7173	Intermediate Similarity	NPC100863
0.7166	Intermediate Similarity	NPC472112
0.7158	Intermediate Similarity	NPC472116
0.7158	Intermediate Similarity	NPC476428
0.7158	Intermediate Similarity	NPC472539
0.7158	Intermediate Similarity	NPC470787
0.7158	Intermediate Similarity	NPC472540
0.7152	Intermediate Similarity	NPC315051
0.7151	Intermediate Similarity	NPC318183
0.7143	Intermediate Similarity	NPC315368
0.7143	Intermediate Similarity	NPC68650
0.7128	Intermediate Similarity	NPC25401
0.712	Intermediate Similarity	NPC90967
0.712	Intermediate Similarity	NPC470317
0.7119	Intermediate Similarity	NPC470069
0.7119	Intermediate Similarity	NPC52059
0.7115	Intermediate Similarity	NPC268534
0.7111	Intermediate Similarity	NPC214626
0.7111	Intermediate Similarity	NPC139085
0.7111	Intermediate Similarity	NPC251212
0.7097	Intermediate Similarity	NPC279385
0.7097	Intermediate Similarity	NPC179605
0.7083	Intermediate Similarity	NPC136002
0.7083	Intermediate Similarity	NPC472103
0.7076	Intermediate Similarity	NPC318086
0.7059	Intermediate Similarity	NPC472323
0.7059	Intermediate Similarity	NPC181928
0.7051	Intermediate Similarity	NPC103292
0.7048	Intermediate Similarity	NPC130251
0.7037	Intermediate Similarity	NPC203628
0.7032	Intermediate Similarity	NPC177684
0.7032	Intermediate Similarity	NPC291962
0.7031	Intermediate Similarity	NPC471199
0.7029	Intermediate Similarity	NPC153694
0.7029	Intermediate Similarity	NPC211525
0.7024	Intermediate Similarity	NPC314287
0.7021	Intermediate Similarity	NPC175474
0.7006	Intermediate Similarity	NPC470301
0.7006	Intermediate Similarity	NPC316202
0.7006	Intermediate Similarity	NPC43477
0.7006	Intermediate Similarity	NPC469741
0.7	Intermediate Similarity	NPC472100
0.7	Intermediate Similarity	NPC307437
0.7	Intermediate Similarity	NPC58827
0.7	Intermediate Similarity	NPC472113
0.7	Intermediate Similarity	NPC72473
0.6995	Remote Similarity	NPC52557
0.699	Remote Similarity	NPC295548
0.699	Remote Similarity	NPC477179
0.6989	Remote Similarity	NPC263709
0.6989	Remote Similarity	NPC310403
0.6989	Remote Similarity	NPC471122
0.6989	Remote Similarity	NPC258480
0.6989	Remote Similarity	NPC97380
0.6989	Remote Similarity	NPC63210
0.6989	Remote Similarity	NPC243673
0.6989	Remote Similarity	NPC148468
0.6987	Remote Similarity	NPC112373
0.6987	Remote Similarity	NPC161956
0.6987	Remote Similarity	NPC258531
0.6984	Remote Similarity	NPC5630
0.6978	Remote Similarity	NPC475097
0.6966	Remote Similarity	NPC313757
0.6963	Remote Similarity	NPC269886
0.6963	Remote Similarity	NPC472295
0.6963	Remote Similarity	NPC247735
0.6963	Remote Similarity	NPC81802
0.6963	Remote Similarity	NPC472210
0.6961	Remote Similarity	NPC248601
0.6961	Remote Similarity	NPC471198
0.6954	Remote Similarity	NPC254850
0.6954	Remote Similarity	NPC477180
0.6954	Remote Similarity	NPC295021
0.6954	Remote Similarity	NPC477178
0.6954	Remote Similarity	NPC477181
0.6951	Remote Similarity	NPC253476
0.695	Remote Similarity	NPC475359
0.695	Remote Similarity	NPC191817
0.6943	Remote Similarity	NPC257490
0.6935	Remote Similarity	NPC471945
0.6935	Remote Similarity	NPC471950
0.6935	Remote Similarity	NPC285192
0.6932	Remote Similarity	NPC222029
0.6927	Remote Similarity	NPC471124
0.6923	Remote Similarity	NPC96901
0.6923	Remote Similarity	NPC472123
0.6919	Remote Similarity	NPC477173
0.6919	Remote Similarity	NPC470490
0.6919	Remote Similarity	NPC477174
0.6912	Remote Similarity	NPC471197
0.6907	Remote Similarity	NPC265642
0.6907	Remote Similarity	NPC138615
0.6907	Remote Similarity	NPC218733
0.6907	Remote Similarity	NPC132874
0.6905	Remote Similarity	NPC471574
0.6902	Remote Similarity	NPC476326
0.6902	Remote Similarity	NPC260075
0.69	Remote Similarity	NPC471946
0.69	Remote Similarity	NPC471951
0.6898	Remote Similarity	NPC472119
0.6895	Remote Similarity	NPC22689
0.6895	Remote Similarity	NPC105055
0.6895	Remote Similarity	NPC473298
0.6895	Remote Similarity	NPC313293
0.6891	Remote Similarity	NPC245916
0.6891	Remote Similarity	NPC303214
0.6889	Remote Similarity	NPC182131
0.6884	Remote Similarity	NPC470488
0.6882	Remote Similarity	NPC113626
0.6872	Remote Similarity	NPC204867
0.6871	Remote Similarity	NPC316746
0.6867	Remote Similarity	NPC471123
0.6854	Remote Similarity	NPC27904
0.6853	Remote Similarity	NPC1464
0.685	Remote Similarity	NPC470491
0.685	Remote Similarity	NPC475259
0.6845	Remote Similarity	NPC472110
0.6845	Remote Similarity	NPC472108
0.6845	Remote Similarity	NPC472109
0.6845	Remote Similarity	NPC159125
0.6845	Remote Similarity	NPC139291
0.6842	Remote Similarity	NPC196251
0.6842	Remote Similarity	NPC111602
0.6842	Remote Similarity	NPC63199
0.6842	Remote Similarity	NPC102338

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 NPC472118 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	481
0.2-0.3	711
0.3-0.4	1537
0.4-0.5	3445
0.5-0.6	2419
0.6-0.7	385
0.7-0.8	14
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
0.7561	Intermediate Similarity	NPD5931	Phase 3
0.7561	Intermediate Similarity	NPD5933	Phase 3
0.7561	Intermediate Similarity	NPD5932	Phase 3
0.7443	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2037	Approved
0.7389	Intermediate Similarity	NPD4329	Approved
0.7389	Intermediate Similarity	NPD4330	Approved
0.7386	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2790	Discontinued
0.7353	Intermediate Similarity	NPD4121	Phase 3
0.7353	Intermediate Similarity	NPD4120	Approved
0.7349	Intermediate Similarity	NPD6017	Discontinued
0.7348	Intermediate Similarity	NPD3470	Approved
0.7348	Intermediate Similarity	NPD3471	Approved
0.7345	Intermediate Similarity	NPD2431	Approved
0.7345	Intermediate Similarity	NPD2432	Approved
0.733	Intermediate Similarity	NPD2455	Approved
0.733	Intermediate Similarity	NPD2454	Approved
0.731	Intermediate Similarity	NPD5742	Approved
0.731	Intermediate Similarity	NPD5743	Approved
0.731	Intermediate Similarity	NPD5741	Approved
0.7289	Intermediate Similarity	NPD5918	Discontinued
0.7278	Intermediate Similarity	NPD3792	Approved
0.7263	Intermediate Similarity	NPD3422	Phase 3
0.7263	Intermediate Similarity	NPD3423	Phase 2
0.7241	Intermediate Similarity	NPD2506	Approved
0.7219	Intermediate Similarity	NPD5504	Discontinued
0.7205	Intermediate Similarity	NPD1527	Phase 2
0.7184	Intermediate Similarity	NPD4393	Approved
0.7184	Intermediate Similarity	NPD33	Approved
0.7168	Intermediate Similarity	NPD951	Approved
0.7143	Intermediate Similarity	NPD5992	Approved
0.7143	Intermediate Similarity	NPD3782	Discontinued
0.7135	Intermediate Similarity	NPD2404	Discontinued
0.7134	Intermediate Similarity	NPD6342	Discontinued
0.7118	Intermediate Similarity	NPD979	Approved
0.7111	Intermediate Similarity	NPD3377	Discontinued
0.7098	Intermediate Similarity	NPD6805	Discontinued
0.7086	Intermediate Similarity	NPD2427	Approved
0.7076	Intermediate Similarity	NPD5748	Phase 2
0.7041	Intermediate Similarity	NPD8115	Approved
0.7041	Intermediate Similarity	NPD8114	Approved
0.7039	Intermediate Similarity	NPD3468	Approved
0.7033	Intermediate Similarity	NPD2083	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3828	Approved
0.7024	Intermediate Similarity	NPD2820	Phase 3
0.7006	Intermediate Similarity	NPD3625	Discontinued
0.6978	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3790	Phase 2
0.6964	Remote Similarity	NPD2365	Approved
0.6947	Remote Similarity	NPD3884	Discontinued
0.6923	Remote Similarity	NPD5024	Approved
0.6919	Remote Similarity	NPD5942	Approved
0.6919	Remote Similarity	NPD5941	Approved
0.6919	Remote Similarity	NPD4888	Discontinued
0.6919	Remote Similarity	NPD4942	Approved
0.6904	Remote Similarity	NPD7205	Discontinued
0.689	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5466	Approved
0.6879	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6566	Discontinued
0.6862	Remote Similarity	NPD6557	Phase 2
0.686	Remote Similarity	NPD7088	Discontinued
0.6848	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4600	Approved
0.6837	Remote Similarity	NPD4601	Approved
0.6836	Remote Similarity	NPD5660	Approved
0.6836	Remote Similarity	NPD5659	Approved
0.6836	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6019	Approved
0.6836	Remote Similarity	NPD6018	Approved
0.6831	Remote Similarity	NPD5997	Discontinued
0.6824	Remote Similarity	NPD1625	Approved
0.6821	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4045	Phase 2
0.6818	Remote Similarity	NPD4042	Phase 2
0.6813	Remote Similarity	NPD2369	Discontinued
0.6807	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7817	Phase 1
0.68	Remote Similarity	NPD1854	Approved
0.6788	Remote Similarity	NPD1541	Approved
0.6766	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6768	Approved
0.6744	Remote Similarity	NPD7295	Approved
0.6736	Remote Similarity	NPD7569	Approved
0.6736	Remote Similarity	NPD7570	Approved
0.6735	Remote Similarity	NPD5197	Approved
0.6735	Remote Similarity	NPD5196	Approved
0.6735	Remote Similarity	NPD5194	Approved
0.6726	Remote Similarity	NPD6358	Phase 2
0.6724	Remote Similarity	NPD4682	Phase 2
0.6721	Remote Similarity	NPD5186	Approved
0.6721	Remote Similarity	NPD5183	Approved
0.672	Remote Similarity	NPD4412	Phase 2
0.6706	Remote Similarity	NPD4461	Discontinued
0.67	Remote Similarity	NPD1294	Discontinued
0.6699	Remote Similarity	NPD3393	Approved
0.6699	Remote Similarity	NPD3394	Approved
0.6699	Remote Similarity	NPD3389	Approved
0.6687	Remote Similarity	NPD2950	Approved
0.6687	Remote Similarity	NPD2949	Approved
0.6687	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1626	Approved
0.6685	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7572	Phase 2
0.6684	Remote Similarity	NPD2397	Discontinued
0.6684	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4501	Approved
0.6667	Remote Similarity	NPD4500	Approved
0.6649	Remote Similarity	NPD5937	Approved
0.6649	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7854	Phase 2
0.6648	Remote Similarity	NPD8630	Approved
0.6647	Remote Similarity	NPD5182	Approved
0.6647	Remote Similarity	NPD5185	Approved
0.6647	Remote Similarity	NPD5184	Approved
0.6646	Remote Similarity	NPD4549	Discontinued
0.6631	Remote Similarity	NPD5498	Phase 2
0.6629	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7308	Discontinued
0.6612	Remote Similarity	NPD4645	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7599	Phase 2
0.6608	Remote Similarity	NPD2010	Phase 3
0.6606	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2509	Approved
0.6601	Remote Similarity	NPD2510	Approved
0.6601	Remote Similarity	NPD4082	Approved
0.6599	Remote Similarity	NPD5195	Discontinued
0.6598	Remote Similarity	NPD5042	Phase 1
0.6591	Remote Similarity	NPD1405	Approved
0.659	Remote Similarity	NPD7487	Discontinued
0.6587	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7600	Phase 2
0.6571	Remote Similarity	NPD1802	Approved
0.6571	Remote Similarity	NPD1801	Approved
0.657	Remote Similarity	NPD6512	Approved
0.657	Remote Similarity	NPD6513	Approved
0.657	Remote Similarity	NPD1189	Approved
0.6566	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD1574	Approved
0.6559	Remote Similarity	NPD1660	Phase 2
0.6557	Remote Similarity	NPD5430	Discontinued
0.6553	Remote Similarity	NPD4492	Approved
0.6553	Remote Similarity	NPD4494	Approved
0.655	Remote Similarity	NPD7727	Phase 2
0.6546	Remote Similarity	NPD4499	Approved
0.6545	Remote Similarity	NPD8241	Phase 2
0.6545	Remote Similarity	NPD5923	Phase 1
0.6543	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7795	Phase 2
0.6541	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1575	Approved
0.6541	Remote Similarity	NPD1573	Approved
0.6536	Remote Similarity	NPD7072	Phase 2
0.6532	Remote Similarity	NPD7082	Approved
0.6532	Remote Similarity	NPD6301	Phase 2
0.6529	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7683	Discontinued
0.6528	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD1593	Approved
0.6517	Remote Similarity	NPD3248	Phase 1
0.6513	Remote Similarity	NPD3304	Phase 2
0.6513	Remote Similarity	NPD8240	Discontinued
0.6513	Remote Similarity	NPD4370	Phase 3
0.651	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD3079	Approved
0.6508	Remote Similarity	NPD3078	Approved
0.6508	Remote Similarity	NPD3077	Approved
0.6508	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD3076	Approved
0.6505	Remote Similarity	NPD4493	Discontinued
0.6503	Remote Similarity	NPD5157	Phase 1
0.6503	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5159	Phase 2
0.6502	Remote Similarity	NPD6260	Discontinued
0.65	Remote Similarity	NPD2836	Approved
0.65	Remote Similarity	NPD1663	Discontinued
0.6497	Remote Similarity	NPD4602	Approved
0.6494	Remote Similarity	NPD7259	Approved
0.6494	Remote Similarity	NPD3481	Approved
0.6494	Remote Similarity	NPD4043	Approved
0.6494	Remote Similarity	NPD4046	Approved
0.6491	Remote Similarity	NPD7254	Discontinued
0.6491	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD3170	Approved
0.649	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD168	Phase 1
0.6474	Remote Similarity	NPD6878	Phase 2
0.6474	Remote Similarity	NPD5473	Discontinued
0.6474	Remote Similarity	NPD3989	Phase 3
0.6474	Remote Similarity	NPD6879	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