NPASS Compound

Structure

NPC214960 OpenBabel07101718192D 25 29 0 0 1 0 0 0 0 0999 V2000 2.1584 -3.5643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3968 -2.1371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1444 -0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2421 -2.4081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0747 -1.1722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1493 -3.4301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0880 -1.9351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5285 -2.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3611 -1.2688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0104 -0.6399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 0.1045 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 2.8025 -1.6180 0.0000 N 0 0 0 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 3.7610 -4.2211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5152 -1.7418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 22 1 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 15 2 0 0 0 0 6 17 2 0 0 0 0 7 18 1 0 0 0 0 9 13 2 0 0 0 0 9 25 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 23 2 0 0 0 0 12 7 1 6 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 14 10 1 6 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 8 1 1 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 1 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.16
Volume:	344.239
LogP:	0.29
LogD:	1.464
LogS:	-3.564
# Rotatable Bonds:	1
TPSA:	58.64
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.848
Synthetic Accessibility Score:	5.813
Fsp3:	0.5
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:	-4.99
MDCK Permeability:	2.2045061996323057e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.279
Human Intestinal Absorption (HIA):	0.188
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.975
Plasma Protein Binding (PPB):	49.61167907714844%
Volume Distribution (VD):	1.574
Pgp-substrate:	71.23251342773438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.369
CYP2C19-inhibitor:	0.451
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.333
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.069
CYP2D6-substrate:	0.546
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.902

ADMET: Excretion

Clearance (CL):	2.71
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.83
Human Hepatotoxicity (H-HT):	0.74
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.898
Rat Oral Acute Toxicity:	0.506
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.616
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC214960

Natural Product ID:	NPC214960
*Common Name:**	JUWMPKQYUSKQSY-TUAIKIEXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JUWMPKQYUSKQSY-TUAIKIEXSA-N
Standard InCHI:	InChI=1S/C20H22N2O3/c1-11(23)13-9-25-10-14-12(13)7-18-20(8-16(14)21-18)15-5-3-4-6-17(15)22(2)19(20)24/h3-6,9,12,14,16,18,21H,7-8,10H2,1-2H3/t12-,14+,16-,18-,20+/m0/s1
SMILES:	CC(=O)C1=COC[C@@H]2[C@H]1C[C@@H]1N[C@H]2C[C@]21c1ccccc1N(C2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338248
PubChem CID:	21604595
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0001878] Beta amino acids 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
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[490016]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[490016]

☑ 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 NPC214960 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	260
0.1-0.2	1223
0.2-0.3	5693
0.3-0.4	20368
0.4-0.5	10281
0.5-0.6	3855
0.6-0.7	827
0.7-0.8	162
0.8-0.85	21
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279527
0.9097	High Similarity	NPC113946
0.8861	High Similarity	NPC472102
0.8861	High Similarity	NPC309531
0.8629	High Similarity	NPC100863
0.8457	Intermediate Similarity	NPC472117
0.8457	Intermediate Similarity	NPC472120
0.8457	Intermediate Similarity	NPC472101
0.8354	Intermediate Similarity	NPC472106
0.8344	Intermediate Similarity	NPC286871
0.8344	Intermediate Similarity	NPC472121
0.8253	Intermediate Similarity	NPC224970
0.8253	Intermediate Similarity	NPC223595
0.8253	Intermediate Similarity	NPC167724
0.8232	Intermediate Similarity	NPC176983
0.8232	Intermediate Similarity	NPC99632
0.8232	Intermediate Similarity	NPC282339
0.8204	Intermediate Similarity	NPC472118
0.8121	Intermediate Similarity	NPC293458
0.8118	Intermediate Similarity	NPC264482
0.8118	Intermediate Similarity	NPC203202
0.811	Intermediate Similarity	NPC193410
0.8061	Intermediate Similarity	NPC225319
0.8061	Intermediate Similarity	NPC248117
0.8049	Intermediate Similarity	NPC61013
0.8	Intermediate Similarity	NPC96901
0.8	Intermediate Similarity	NPC285622
0.7988	Intermediate Similarity	NPC29285
0.7939	Intermediate Similarity	NPC123241
0.7919	Intermediate Similarity	NPC218594
0.7919	Intermediate Similarity	NPC6974
0.7919	Intermediate Similarity	NPC99043
0.7895	Intermediate Similarity	NPC139085
0.7895	Intermediate Similarity	NPC214626
0.7895	Intermediate Similarity	NPC251212
0.7892	Intermediate Similarity	NPC36495
0.7861	Intermediate Similarity	NPC186669
0.7849	Intermediate Similarity	NPC469726
0.7849	Intermediate Similarity	NPC329338
0.7841	Intermediate Similarity	NPC97584
0.7809	Intermediate Similarity	NPC14994
0.7784	Intermediate Similarity	NPC159963
0.7758	Intermediate Similarity	NPC478076
0.7716	Intermediate Similarity	NPC264589
0.7673	Intermediate Similarity	NPC130251
0.7657	Intermediate Similarity	NPC260075
0.7624	Intermediate Similarity	NPC473298
0.7605	Intermediate Similarity	NPC161827
0.7602	Intermediate Similarity	NPC52059
0.7602	Intermediate Similarity	NPC470069
0.7598	Intermediate Similarity	NPC52262
0.7584	Intermediate Similarity	NPC477159
0.7582	Intermediate Similarity	NPC25401
0.7562	Intermediate Similarity	NPC315051
0.753	Intermediate Similarity	NPC475763
0.7527	Intermediate Similarity	NPC472112
0.7515	Intermediate Similarity	NPC153694
0.7515	Intermediate Similarity	NPC211525
0.7514	Intermediate Similarity	NPC181928
0.7486	Intermediate Similarity	NPC177261
0.7486	Intermediate Similarity	NPC298851
0.7486	Intermediate Similarity	NPC276993
0.7486	Intermediate Similarity	NPC210415
0.7486	Intermediate Similarity	NPC293255
0.7486	Intermediate Similarity	NPC21752
0.7486	Intermediate Similarity	NPC181138
0.7486	Intermediate Similarity	NPC473743
0.7484	Intermediate Similarity	NPC471123
0.7473	Intermediate Similarity	NPC284706
0.7472	Intermediate Similarity	NPC11149
0.7471	Intermediate Similarity	NPC310403
0.7471	Intermediate Similarity	NPC263709
0.7471	Intermediate Similarity	NPC63210
0.7471	Intermediate Similarity	NPC97380
0.7471	Intermediate Similarity	NPC148468
0.7471	Intermediate Similarity	NPC243673
0.7459	Intermediate Similarity	NPC243626
0.7435	Intermediate Similarity	NPC477161
0.7427	Intermediate Similarity	NPC315368
0.7427	Intermediate Similarity	NPC143457
0.7427	Intermediate Similarity	NPC68650
0.7416	Intermediate Similarity	NPC475094
0.7412	Intermediate Similarity	NPC222029
0.7407	Intermediate Similarity	NPC471164
0.7407	Intermediate Similarity	NPC301760
0.7403	Intermediate Similarity	NPC259626
0.7391	Intermediate Similarity	NPC22476
0.7386	Intermediate Similarity	NPC476425
0.7384	Intermediate Similarity	NPC469741
0.738	Intermediate Similarity	NPC162440
0.7366	Intermediate Similarity	NPC230313
0.7365	Intermediate Similarity	NPC473329
0.7363	Intermediate Similarity	NPC473615
0.7348	Intermediate Similarity	NPC2933
0.7348	Intermediate Similarity	NPC258480
0.7337	Intermediate Similarity	NPC22689
0.7337	Intermediate Similarity	NPC105055
0.7326	Intermediate Similarity	NPC201424
0.7326	Intermediate Similarity	NPC474058
0.7322	Intermediate Similarity	NPC229484
0.7321	Intermediate Similarity	NPC243756
0.7317	Intermediate Similarity	NPC469537
0.7308	Intermediate Similarity	NPC473007
0.7305	Intermediate Similarity	NPC242000
0.7303	Intermediate Similarity	NPC476441
0.7301	Intermediate Similarity	NPC186284
0.7301	Intermediate Similarity	NPC22082
0.7299	Intermediate Similarity	NPC471124
0.7297	Intermediate Similarity	NPC203628
0.7293	Intermediate Similarity	NPC256288
0.7284	Intermediate Similarity	NPC469560
0.7283	Intermediate Similarity	NPC292675
0.7273	Intermediate Similarity	NPC34717
0.7267	Intermediate Similarity	NPC471122
0.7267	Intermediate Similarity	NPC276085
0.7263	Intermediate Similarity	NPC138830
0.7263	Intermediate Similarity	NPC67904
0.7258	Intermediate Similarity	NPC472113
0.7243	Intermediate Similarity	NPC5630
0.7232	Intermediate Similarity	NPC355
0.7219	Intermediate Similarity	NPC66936
0.7202	Intermediate Similarity	NPC329833
0.7196	Intermediate Similarity	NPC90967
0.7173	Intermediate Similarity	NPC475489
0.7166	Intermediate Similarity	NPC473004
0.7158	Intermediate Similarity	NPC218733
0.7158	Intermediate Similarity	NPC138615
0.7158	Intermediate Similarity	NPC265642
0.7158	Intermediate Similarity	NPC132874
0.7151	Intermediate Similarity	NPC13367
0.7151	Intermediate Similarity	NPC473008
0.7151	Intermediate Similarity	NPC470548
0.7143	Intermediate Similarity	NPC316104
0.7143	Intermediate Similarity	NPC303214
0.7143	Intermediate Similarity	NPC162417
0.7118	Intermediate Similarity	NPC154602
0.7114	Intermediate Similarity	NPC77777
0.7113	Intermediate Similarity	NPC87714
0.7108	Intermediate Similarity	NPC308197
0.709	Intermediate Similarity	NPC221687
0.7081	Intermediate Similarity	NPC66210
0.7076	Intermediate Similarity	NPC122106
0.7072	Intermediate Similarity	NPC476326
0.7066	Intermediate Similarity	NPC472103
0.7062	Intermediate Similarity	NPC472115
0.7062	Intermediate Similarity	NPC472114
0.7059	Intermediate Similarity	NPC473569
0.7059	Intermediate Similarity	NPC314333
0.7056	Intermediate Similarity	NPC475097
0.7047	Intermediate Similarity	NPC232600
0.7045	Intermediate Similarity	NPC138293
0.7045	Intermediate Similarity	NPC113056
0.7031	Intermediate Similarity	NPC106118
0.7022	Intermediate Similarity	NPC475248
0.7022	Intermediate Similarity	NPC63047
0.701	Intermediate Similarity	NPC1464
0.7005	Intermediate Similarity	NPC63199
0.7005	Intermediate Similarity	NPC196251
0.7005	Intermediate Similarity	NPC111602
0.7005	Intermediate Similarity	NPC102338
0.6995	Remote Similarity	NPC128265
0.6995	Remote Similarity	NPC312870
0.6995	Remote Similarity	NPC199851
0.6995	Remote Similarity	NPC294909
0.6995	Remote Similarity	NPC254240
0.699	Remote Similarity	NPC195787
0.699	Remote Similarity	NPC246140
0.699	Remote Similarity	NPC122886
0.6983	Remote Similarity	NPC469915
0.6973	Remote Similarity	NPC245741
0.6968	Remote Similarity	NPC329858
0.6963	Remote Similarity	NPC245916
0.6963	Remote Similarity	NPC473375
0.6963	Remote Similarity	NPC97100
0.6959	Remote Similarity	NPC471512
0.6959	Remote Similarity	NPC318086
0.6957	Remote Similarity	NPC476428
0.6954	Remote Similarity	NPC469536
0.6949	Remote Similarity	NPC313757
0.6947	Remote Similarity	NPC472210
0.6947	Remote Similarity	NPC269886
0.6947	Remote Similarity	NPC472295
0.6947	Remote Similarity	NPC247735
0.6947	Remote Similarity	NPC81802
0.6941	Remote Similarity	NPC212799
0.6939	Remote Similarity	NPC475147
0.6937	Remote Similarity	NPC209389
0.6935	Remote Similarity	NPC307396
0.6935	Remote Similarity	NPC322621
0.6923	Remote Similarity	NPC260900
0.6923	Remote Similarity	NPC129624
0.6919	Remote Similarity	NPC285192
0.6906	Remote Similarity	NPC242269
0.6902	Remote Similarity	NPC286994
0.6902	Remote Similarity	NPC15840
0.6901	Remote Similarity	NPC109787
0.6898	Remote Similarity	NPC282092
0.6897	Remote Similarity	NPC126556
0.6897	Remote Similarity	NPC471197
0.6895	Remote Similarity	NPC204970

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 NPC214960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	494
0.2-0.3	742
0.3-0.4	1423
0.4-0.5	3404
0.5-0.6	2481
0.6-0.7	422
0.7-0.8	18
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
0.7273	Intermediate Similarity	NPD5918	Discontinued
0.7208	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5183	Approved
0.7175	Intermediate Similarity	NPD5186	Approved
0.7152	Intermediate Similarity	NPD6768	Approved
0.7135	Intermediate Similarity	NPD2790	Discontinued
0.711	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4499	Approved
0.7048	Intermediate Similarity	NPD6566	Discontinued
0.7039	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5185	Approved
0.7037	Intermediate Similarity	NPD5182	Approved
0.7037	Intermediate Similarity	NPD5184	Approved
0.7012	Intermediate Similarity	NPD6342	Discontinued
0.7	Intermediate Similarity	NPD5942	Approved
0.7	Intermediate Similarity	NPD5941	Approved
0.7	Intermediate Similarity	NPD5997	Discontinued
0.6995	Remote Similarity	NPD4501	Approved
0.6995	Remote Similarity	NPD4500	Approved
0.6988	Remote Similarity	NPD3625	Discontinued
0.6971	Remote Similarity	NPD4393	Approved
0.6971	Remote Similarity	NPD33	Approved
0.6954	Remote Similarity	NPD1663	Discontinued
0.6949	Remote Similarity	NPD3790	Phase 2
0.6927	Remote Similarity	NPD2037	Approved
0.6923	Remote Similarity	NPD5931	Phase 3
0.6923	Remote Similarity	NPD5933	Phase 3
0.6923	Remote Similarity	NPD5932	Phase 3
0.6914	Remote Similarity	NPD8630	Approved
0.6909	Remote Similarity	NPD6358	Phase 2
0.6905	Remote Similarity	NPD2820	Phase 3
0.6902	Remote Similarity	NPD4329	Approved
0.6902	Remote Similarity	NPD4330	Approved
0.6865	Remote Similarity	NPD3471	Approved
0.6865	Remote Similarity	NPD3470	Approved
0.6864	Remote Similarity	NPD7487	Discontinued
0.6851	Remote Similarity	NPD2431	Approved
0.6851	Remote Similarity	NPD2432	Approved
0.6845	Remote Similarity	NPD2365	Approved
0.6839	Remote Similarity	NPD4120	Approved
0.6839	Remote Similarity	NPD4121	Phase 3
0.6833	Remote Similarity	NPD2454	Approved
0.6833	Remote Similarity	NPD2455	Approved
0.6832	Remote Similarity	NPD4549	Discontinued
0.6824	Remote Similarity	NPD6017	Discontinued
0.6805	Remote Similarity	NPD5024	Approved
0.6802	Remote Similarity	NPD979	Approved
0.68	Remote Similarity	NPD5743	Approved
0.68	Remote Similarity	NPD5741	Approved
0.68	Remote Similarity	NPD5742	Approved
0.6796	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3792	Approved
0.679	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5748	Phase 2
0.6755	Remote Similarity	NPD6557	Phase 2
0.6754	Remote Similarity	NPD8240	Discontinued
0.6747	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1802	Approved
0.6744	Remote Similarity	NPD1801	Approved
0.6742	Remote Similarity	NPD7600	Phase 2
0.6737	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6805	Discontinued
0.6732	Remote Similarity	NPD5181	Approved
0.6732	Remote Similarity	NPD5179	Approved
0.6732	Remote Similarity	NPD5180	Approved
0.6709	Remote Similarity	NPD1123	Approved
0.6709	Remote Similarity	NPD1124	Approved
0.6706	Remote Similarity	NPD4430	Phase 2
0.6705	Remote Similarity	NPD7072	Phase 2
0.6703	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2791	Discontinued
0.6686	Remote Similarity	NPD2010	Phase 3
0.6685	Remote Similarity	NPD7599	Phase 2
0.6667	Remote Similarity	NPD951	Approved
0.6667	Remote Similarity	NPD3782	Discontinued
0.6667	Remote Similarity	NPD3828	Approved
0.6667	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5504	Discontinued
0.6648	Remote Similarity	NPD2506	Approved
0.6648	Remote Similarity	NPD2404	Discontinued
0.6647	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7854	Phase 2
0.6625	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2994	Approved
0.6616	Remote Similarity	NPD6238	Discontinued
0.6615	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4682	Phase 2
0.6609	Remote Similarity	NPD7528	Approved
0.6609	Remote Similarity	NPD4942	Approved
0.6608	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3422	Phase 3
0.6595	Remote Similarity	NPD5466	Approved
0.6595	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3423	Phase 2
0.6591	Remote Similarity	NPD3248	Phase 1
0.6585	Remote Similarity	NPD5131	Approved
0.6582	Remote Similarity	NPD7572	Phase 2
0.658	Remote Similarity	NPD5042	Phase 1
0.6575	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3170	Approved
0.6566	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5993	Phase 1
0.6561	Remote Similarity	NPD2115	Approved
0.6561	Remote Similarity	NPD2117	Pre-registration
0.6561	Remote Similarity	NPD5990	Approved
0.6561	Remote Similarity	NPD2116	Approved
0.6561	Remote Similarity	NPD5991	Approved
0.6559	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3468	Approved
0.6552	Remote Similarity	NPD7088	Discontinued
0.655	Remote Similarity	NPD7205	Discontinued
0.6548	Remote Similarity	NPD6073	Approved
0.6548	Remote Similarity	NPD5071	Phase 2
0.6548	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6878	Phase 2
0.6543	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6879	Phase 2
0.6543	Remote Similarity	NPD1036	Approved
0.6538	Remote Similarity	NPD5430	Discontinued
0.6533	Remote Similarity	NPD6321	Discontinued
0.6532	Remote Similarity	NPD7295	Approved
0.6524	Remote Similarity	NPD1781	Discontinued
0.6524	Remote Similarity	NPD5600	Discontinued
0.6522	Remote Similarity	NPD7795	Phase 2
0.6519	Remote Similarity	NPD6343	Approved
0.6519	Remote Similarity	NPD7220	Approved
0.6519	Remote Similarity	NPD6345	Approved
0.6519	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5426	Phase 3
0.6515	Remote Similarity	NPD7308	Discontinued
0.6514	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5318	Discontinued
0.6509	Remote Similarity	NPD2670	Approved
0.65	Remote Similarity	NPD2427	Approved
0.65	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2946	Phase 2
0.6497	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3399	Approved
0.6495	Remote Similarity	NPD3884	Discontinued
0.6494	Remote Similarity	NPD4041	Approved
0.6491	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4461	Discontinued
0.6489	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5263	Approved
0.6482	Remote Similarity	NPD4600	Approved
0.6482	Remote Similarity	NPD4601	Approved
0.648	Remote Similarity	NPD7105	Phase 1
0.6478	Remote Similarity	NPD3032	Approved
0.6478	Remote Similarity	NPD3031	Approved
0.6478	Remote Similarity	NPD3030	Approved
0.6477	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2435	Approved
0.6473	Remote Similarity	NPD5293	Phase 2
0.6471	Remote Similarity	NPD7254	Discontinued
0.6471	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6176	Phase 1
0.6467	Remote Similarity	NPD6457	Approved
0.6467	Remote Similarity	NPD2950	Approved
0.6467	Remote Similarity	NPD2949	Approved
0.6462	Remote Similarity	NPD5937	Approved
0.6461	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD3989	Phase 3
0.645	Remote Similarity	NPD5725	Approved
0.6446	Remote Similarity	NPD6489	Phase 3
0.6446	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5578	Approved
0.6441	Remote Similarity	NPD7606	Phase 3
0.644	Remote Similarity	NPD4412	Phase 2
0.6436	Remote Similarity	NPD3947	Discontinued
0.6433	Remote Similarity	NPD1323	Discontinued
0.6425	Remote Similarity	NPD6483	Approved
0.6425	Remote Similarity	NPD6484	Approved
0.6422	Remote Similarity	NPD4082	Approved
0.6422	Remote Similarity	NPD2510	Approved
0.6422	Remote Similarity	NPD2509	Approved
0.6421	Remote Similarity	NPD3990	Phase 3
0.6417	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD5526	Phase 2
0.6416	Remote Similarity	NPD7082	Approved
0.6415	Remote Similarity	NPD6995	Phase 1
0.6413	Remote Similarity	NPD5823	Approved
0.6413	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6295	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