NPASS Compound

Structure

NPC264482 OpenBabel07101718272D 26 30 0 0 1 0 0 0 0 0999 V2000 0.0000 -2.9102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6802 -3.8803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1735 3.3354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0687 -1.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1500 0.0346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0207 -1.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1833 0.6866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6802 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4928 -0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9226 0.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 -2.4252 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6802 -0.9701 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0540 -0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1353 0.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 -1.4551 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8537 -0.1476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3047 -0.2810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9701 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4900 1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9226 -1.2699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0542 0.6122 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.4427 1.8679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6802 -2.9102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8554 2.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 15 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 23 1 0 0 0 0 11 23 1 0 0 0 0 12 1 1 6 0 0 0 12 25 1 0 0 0 0 13 8 1 1 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 12 1 6 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 6 0 0 0 19 23 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.19
Volume:	364.172
LogP:	2.211
LogD:	2.418
LogS:	-3.231
# Rotatable Bonds:	4
TPSA:	51.13
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	5.746
Fsp3:	0.619
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:	-4.787
MDCK Permeability:	3.576189556042664e-05
Pgp-inhibitor:	0.668
Pgp-substrate:	0.925
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.692
30% Bioavailability (F30%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	52.996307373046875%
Volume Distribution (VD):	1.841
Pgp-substrate:	62.00857162475586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.732
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.829
CYP3A4-inhibitor:	0.215
CYP3A4-substrate:	0.792

ADMET: Excretion

Clearance (CL):	10.288
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.717
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.439
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.905
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.143
Carcinogencity:	0.202
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC264482

Natural Product ID:	NPC264482
*Common Name:**	LTOOPESWVADEAE-NMAQRDEPSA-N
IUPAC Name:	n.a.
Synonyms:	19(R)-Methoxytubotaiwine
Standard InCHIKey:	LTOOPESWVADEAE-NMAQRDEPSA-N
Standard InCHI:	InChI=1S/C21H26N2O3/c1-12(25-2)16-13-8-10-23-11-9-21(19(16)23)14-6-4-5-7-15(14)22-18(21)17(13)20(24)26-3/h4-7,12-13,16,19,22H,8-11H2,1-3H3/t12-,13+,16+,19-,21-/m1/s1
SMILES:	CO[C@@H]([C@H]1[C@@H]2CCN3[C@H]1[C@]1(C(=C2C(=O)OC)Nc2c1cccc2)CC3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400176
PubChem CID:	23627132
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos alkaloids

*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
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665953]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	Yunnan, China	n.a.	PMID[19133778]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31241923]
NPO2700	Kopsia arborea	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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

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[564521]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[564521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[564521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27100.0	nM	PMID[564521]

☑ 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 NPC264482 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	235
0.1-0.2	989
0.2-0.3	3391
0.3-0.4	12680
0.4-0.5	19040
0.5-0.6	5198
0.6-0.7	954
0.7-0.8	161
0.8-0.85	27
0.85-0.9	6
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC203202
0.9627	High Similarity	NPC6974
0.9627	High Similarity	NPC218594
0.9627	High Similarity	NPC99043
0.9451	High Similarity	NPC159963
0.9444	High Similarity	NPC186669
0.9363	High Similarity	NPC248117
0.9299	High Similarity	NPC193410
0.929	High Similarity	NPC25401
0.9236	High Similarity	NPC61013
0.9226	High Similarity	NPC14994
0.9193	High Similarity	NPC223595
0.9193	High Similarity	NPC167724
0.9193	High Similarity	NPC224970
0.9162	High Similarity	NPC97584
0.8994	High Similarity	NPC123241
0.8944	High Similarity	NPC293458
0.882	High Similarity	NPC36495
0.8743	High Similarity	NPC329338
0.8743	High Similarity	NPC469726
0.8598	High Similarity	NPC99632
0.8598	High Similarity	NPC282339
0.8361	Intermediate Similarity	NPC1464
0.827	Intermediate Similarity	NPC87714
0.8226	Intermediate Similarity	NPC195787
0.8226	Intermediate Similarity	NPC246140
0.8204	Intermediate Similarity	NPC225319
0.814	Intermediate Similarity	NPC139085
0.814	Intermediate Similarity	NPC214626
0.814	Intermediate Similarity	NPC251212
0.8118	Intermediate Similarity	NPC279527
0.8118	Intermediate Similarity	NPC214960
0.8111	Intermediate Similarity	NPC22476
0.8111	Intermediate Similarity	NPC203628
0.8073	Intermediate Similarity	NPC189661
0.8056	Intermediate Similarity	NPC5630
0.8	Intermediate Similarity	NPC260075
0.7988	Intermediate Similarity	NPC472102
0.7988	Intermediate Similarity	NPC474058
0.7988	Intermediate Similarity	NPC309531
0.7949	Intermediate Similarity	NPC77777
0.7944	Intermediate Similarity	NPC181928
0.7935	Intermediate Similarity	NPC303214
0.7933	Intermediate Similarity	NPC52262
0.7931	Intermediate Similarity	NPC21752
0.7931	Intermediate Similarity	NPC276993
0.7931	Intermediate Similarity	NPC298851
0.7931	Intermediate Similarity	NPC210415
0.7931	Intermediate Similarity	NPC293255
0.7931	Intermediate Similarity	NPC181138
0.787	Intermediate Similarity	NPC113946
0.7857	Intermediate Similarity	NPC105055
0.7857	Intermediate Similarity	NPC22689
0.7849	Intermediate Similarity	NPC138615
0.7849	Intermediate Similarity	NPC265642
0.7849	Intermediate Similarity	NPC218733
0.7849	Intermediate Similarity	NPC132874
0.7836	Intermediate Similarity	NPC472120
0.7836	Intermediate Similarity	NPC472101
0.7819	Intermediate Similarity	NPC232600
0.7806	Intermediate Similarity	NPC195636
0.776	Intermediate Similarity	NPC473298
0.7758	Intermediate Similarity	NPC264589
0.7733	Intermediate Similarity	NPC472117
0.7727	Intermediate Similarity	NPC96901
0.7692	Intermediate Similarity	NPC478076
0.7688	Intermediate Similarity	NPC34717
0.7688	Intermediate Similarity	NPC476069
0.7679	Intermediate Similarity	NPC475763
0.7679	Intermediate Similarity	NPC243756
0.765	Intermediate Similarity	NPC128476
0.7647	Intermediate Similarity	NPC223242
0.7647	Intermediate Similarity	NPC161827
0.7644	Intermediate Similarity	NPC472106
0.7627	Intermediate Similarity	NPC285622
0.7614	Intermediate Similarity	NPC472118
0.7606	Intermediate Similarity	NPC90967
0.7604	Intermediate Similarity	NPC475147
0.7573	Intermediate Similarity	NPC139373
0.7539	Intermediate Similarity	NPC471512
0.7537	Intermediate Similarity	NPC19175
0.7529	Intermediate Similarity	NPC286871
0.7515	Intermediate Similarity	NPC473329
0.7514	Intermediate Similarity	NPC63210
0.7514	Intermediate Similarity	NPC97380
0.7514	Intermediate Similarity	NPC148468
0.7514	Intermediate Similarity	NPC243673
0.7514	Intermediate Similarity	NPC310403
0.7514	Intermediate Similarity	NPC263709
0.7474	Intermediate Similarity	NPC100863
0.7449	Intermediate Similarity	NPC475133
0.7443	Intermediate Similarity	NPC470069
0.7443	Intermediate Similarity	NPC52059
0.743	Intermediate Similarity	NPC476425
0.7429	Intermediate Similarity	NPC176983
0.7429	Intermediate Similarity	NPC472121
0.7429	Intermediate Similarity	NPC131977
0.7427	Intermediate Similarity	NPC122106
0.7421	Intermediate Similarity	NPC162440
0.7411	Intermediate Similarity	NPC269449
0.7396	Intermediate Similarity	NPC312870
0.7396	Intermediate Similarity	NPC294909
0.7396	Intermediate Similarity	NPC199851
0.7396	Intermediate Similarity	NPC128265
0.7396	Intermediate Similarity	NPC254240
0.7393	Intermediate Similarity	NPC301501
0.7371	Intermediate Similarity	NPC201424
0.7358	Intermediate Similarity	NPC469450
0.7358	Intermediate Similarity	NPC469732
0.7356	Intermediate Similarity	NPC153694
0.7356	Intermediate Similarity	NPC211525
0.7348	Intermediate Similarity	NPC476441
0.7337	Intermediate Similarity	NPC119722
0.7316	Intermediate Similarity	NPC221687
0.7311	Intermediate Similarity	NPC151171
0.7306	Intermediate Similarity	NPC138830
0.7306	Intermediate Similarity	NPC67904
0.7303	Intermediate Similarity	NPC472114
0.7303	Intermediate Similarity	NPC472115
0.7299	Intermediate Similarity	NPC469536
0.7299	Intermediate Similarity	NPC29285
0.729	Intermediate Similarity	NPC469451
0.729	Intermediate Similarity	NPC469452
0.7289	Intermediate Similarity	NPC130251
0.7277	Intermediate Similarity	NPC245916
0.7273	Intermediate Similarity	NPC21425
0.7267	Intermediate Similarity	NPC154602
0.7258	Intermediate Similarity	NPC472209
0.7245	Intermediate Similarity	NPC329833
0.7222	Intermediate Similarity	NPC469915
0.7222	Intermediate Similarity	NPC329932
0.7219	Intermediate Similarity	NPC190945
0.7217	Intermediate Similarity	NPC291173
0.7213	Intermediate Similarity	NPC476326
0.7209	Intermediate Similarity	NPC469722
0.7209	Intermediate Similarity	NPC318086
0.7189	Intermediate Similarity	NPC475962
0.7166	Intermediate Similarity	NPC49184
0.7135	Intermediate Similarity	NPC469741
0.7135	Intermediate Similarity	NPC19692
0.7135	Intermediate Similarity	NPC220151
0.7128	Intermediate Similarity	NPC475489
0.7115	Intermediate Similarity	NPC115588
0.7115	Intermediate Similarity	NPC231924
0.7108	Intermediate Similarity	NPC126556
0.7098	Intermediate Similarity	NPC97100
0.7098	Intermediate Similarity	NPC473375
0.7097	Intermediate Similarity	NPC476428
0.7081	Intermediate Similarity	NPC321211
0.7074	Intermediate Similarity	NPC322621
0.7059	Intermediate Similarity	NPC234772
0.7056	Intermediate Similarity	NPC154922
0.7056	Intermediate Similarity	NPC162730
0.7053	Intermediate Similarity	NPC196251
0.7053	Intermediate Similarity	NPC63199
0.7053	Intermediate Similarity	NPC111602
0.7053	Intermediate Similarity	NPC102338
0.7049	Intermediate Similarity	NPC177261
0.7048	Intermediate Similarity	NPC473458
0.7045	Intermediate Similarity	NPC473297
0.7041	Intermediate Similarity	NPC301760
0.7029	Intermediate Similarity	NPC285381
0.7018	Intermediate Similarity	NPC472103
0.7016	Intermediate Similarity	NPC329858
0.7011	Intermediate Similarity	NPC475097
0.7006	Intermediate Similarity	NPC36836
0.7006	Intermediate Similarity	NPC63370
0.6983	Remote Similarity	NPC315368
0.6973	Remote Similarity	NPC320147
0.697	Remote Similarity	NPC474116
0.6963	Remote Similarity	NPC316405
0.6959	Remote Similarity	NPC469537
0.6959	Remote Similarity	NPC243626
0.6957	Remote Similarity	NPC473743
0.695	Remote Similarity	NPC477161
0.6943	Remote Similarity	NPC55493
0.6936	Remote Similarity	NPC472100
0.6927	Remote Similarity	NPC314333
0.6927	Remote Similarity	NPC471122
0.6927	Remote Similarity	NPC474059
0.6923	Remote Similarity	NPC278887
0.6905	Remote Similarity	NPC471123
0.6895	Remote Similarity	NPC113455
0.6895	Remote Similarity	NPC469460
0.6895	Remote Similarity	NPC259626
0.6887	Remote Similarity	NPC471513
0.6884	Remote Similarity	NPC137589
0.6878	Remote Similarity	NPC477159
0.6878	Remote Similarity	NPC234078
0.6878	Remote Similarity	NPC221100
0.6875	Remote Similarity	NPC288110
0.6875	Remote Similarity	NPC314223
0.6872	Remote Similarity	NPC230313
0.6872	Remote Similarity	NPC222029
0.6868	Remote Similarity	NPC475420
0.6865	Remote Similarity	NPC307640
0.6859	Remote Similarity	NPC473615
0.6857	Remote Similarity	NPC242000
0.6856	Remote Similarity	NPC472113
0.6851	Remote Similarity	NPC85651

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 NPC264482 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	454
0.2-0.3	733
0.3-0.4	1152
0.4-0.5	3622
0.5-0.6	2623
0.6-0.7	379
0.7-0.8	29
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
0.7396	Intermediate Similarity	NPD4501	Approved
0.7396	Intermediate Similarity	NPD4500	Approved
0.7235	Intermediate Similarity	NPD4041	Approved
0.7219	Intermediate Similarity	NPD2435	Approved
0.7216	Intermediate Similarity	NPD7114	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7035	Approved
0.7151	Intermediate Similarity	NPD7036	Phase 3
0.7126	Intermediate Similarity	NPD3399	Approved
0.7111	Intermediate Similarity	NPD8003	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8002	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1801	Approved
0.7093	Intermediate Similarity	NPD1802	Approved
0.7079	Intermediate Similarity	NPD7244	Discontinued
0.7049	Intermediate Similarity	NPD5997	Discontinued
0.7024	Intermediate Similarity	NPD3170	Approved
0.7018	Intermediate Similarity	NPD7487	Discontinued
0.7011	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6571	Approved
0.7006	Intermediate Similarity	NPD6570	Approved
0.6988	Remote Similarity	NPD5185	Approved
0.6988	Remote Similarity	NPD5182	Approved
0.6988	Remote Similarity	NPD5184	Approved
0.6968	Remote Similarity	NPD8281	Discontinued
0.6964	Remote Similarity	NPD2670	Approved
0.6954	Remote Similarity	NPD7528	Approved
0.6932	Remote Similarity	NPD2948	Discontinued
0.6927	Remote Similarity	NPD4499	Approved
0.6915	Remote Similarity	NPD3470	Approved
0.6915	Remote Similarity	NPD3471	Approved
0.6893	Remote Similarity	NPD4120	Approved
0.6893	Remote Similarity	NPD4121	Phase 3
0.6885	Remote Similarity	NPD2037	Approved
0.6875	Remote Similarity	NPD7606	Phase 3
0.6862	Remote Similarity	NPD4330	Approved
0.6862	Remote Similarity	NPD4329	Approved
0.6854	Remote Similarity	NPD5743	Approved
0.6854	Remote Similarity	NPD5741	Approved
0.6854	Remote Similarity	NPD5742	Approved
0.6848	Remote Similarity	NPD5183	Approved
0.6848	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5186	Approved
0.6845	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4607	Approved
0.6828	Remote Similarity	NPD3423	Phase 2
0.6828	Remote Similarity	NPD7940	Phase 3
0.6828	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3422	Phase 3
0.6811	Remote Similarity	NPD2431	Approved
0.6811	Remote Similarity	NPD2432	Approved
0.6804	Remote Similarity	NPD5504	Discontinued
0.6802	Remote Similarity	NPD3828	Approved
0.6802	Remote Similarity	NPD2923	Approved
0.68	Remote Similarity	NPD7478	Approved
0.68	Remote Similarity	NPD3352	Approved
0.6793	Remote Similarity	NPD2454	Approved
0.6793	Remote Similarity	NPD2455	Approved
0.6784	Remote Similarity	NPD4601	Approved
0.6784	Remote Similarity	NPD4600	Approved
0.6782	Remote Similarity	NPD6185	Discontinued
0.6755	Remote Similarity	NPD3792	Approved
0.6744	Remote Similarity	NPD3625	Discontinued
0.6725	Remote Similarity	NPD1110	Approved
0.6725	Remote Similarity	NPD1109	Approved
0.6723	Remote Similarity	NPD4513	Discontinued
0.6721	Remote Similarity	NPD8008	Approved
0.6721	Remote Similarity	NPD8007	Approved
0.672	Remote Similarity	NPD7775	Approved
0.672	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6758	Approved
0.6703	Remote Similarity	NPD2506	Approved
0.6702	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6805	Discontinued
0.6686	Remote Similarity	NPD7295	Approved
0.6685	Remote Similarity	NPD5430	Discontinued
0.6667	Remote Similarity	NPD3436	Approved
0.665	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5466	Approved
0.6649	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6770	Approved
0.6634	Remote Similarity	NPD2509	Approved
0.6634	Remote Similarity	NPD2510	Approved
0.6632	Remote Similarity	NPD7881	Approved
0.6632	Remote Similarity	NPD3782	Discontinued
0.6614	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2404	Discontinued
0.6612	Remote Similarity	NPD7600	Phase 2
0.6611	Remote Similarity	NPD2790	Discontinued
0.6609	Remote Similarity	NPD6768	Approved
0.6602	Remote Similarity	NPD4506	Discontinued
0.6601	Remote Similarity	NPD7205	Discontinued
0.6595	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2994	Approved
0.6584	Remote Similarity	NPD6238	Discontinued
0.6573	Remote Similarity	NPD5942	Approved
0.6573	Remote Similarity	NPD5941	Approved
0.6573	Remote Similarity	NPD4888	Discontinued
0.6571	Remote Similarity	NPD7082	Approved
0.6571	Remote Similarity	NPD2820	Phase 3
0.657	Remote Similarity	NPD2567	Approved
0.657	Remote Similarity	NPD2569	Approved
0.6562	Remote Similarity	NPD3435	Discontinued
0.6557	Remote Similarity	NPD2427	Approved
0.6552	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3790	Phase 2
0.6534	Remote Similarity	NPD5918	Discontinued
0.6534	Remote Similarity	NPD7259	Approved
0.6532	Remote Similarity	NPD1626	Approved
0.6528	Remote Similarity	NPD7962	Phase 2
0.6526	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3948	Discontinued
0.6524	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3468	Approved
0.6522	Remote Similarity	NPD2115	Approved
0.6522	Remote Similarity	NPD2117	Pre-registration
0.6522	Remote Similarity	NPD2116	Approved
0.6519	Remote Similarity	NPD5086	Approved
0.6517	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2365	Approved
0.6508	Remote Similarity	NPD3377	Discontinued
0.6508	Remote Similarity	NPD7854	Phase 2
0.6503	Remote Similarity	NPD8630	Approved
0.65	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6622	Phase 1
0.6497	Remote Similarity	NPD6017	Discontinued
0.6492	Remote Similarity	NPD5600	Discontinued
0.6489	Remote Similarity	NPD7795	Phase 2
0.6474	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4859	Phase 1
0.6473	Remote Similarity	NPD4082	Approved
0.6465	Remote Similarity	NPD3884	Discontinued
0.6463	Remote Similarity	NPD2946	Phase 2
0.6462	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD4493	Discontinued
0.6448	Remote Similarity	NPD1663	Discontinued
0.6442	Remote Similarity	NPD3030	Approved
0.6442	Remote Similarity	NPD3031	Approved
0.6442	Remote Similarity	NPD3032	Approved
0.6439	Remote Similarity	NPD6176	Phase 1
0.6429	Remote Similarity	NPD4492	Approved
0.6429	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4494	Approved
0.6425	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6566	Discontinued
0.6414	Remote Similarity	NPD5928	Phase 1
0.6414	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4412	Phase 2
0.6409	Remote Similarity	NPD7688	Phase 1
0.6408	Remote Similarity	NPD3947	Discontinued
0.6404	Remote Similarity	NPD5933	Phase 3
0.6404	Remote Similarity	NPD5931	Phase 3
0.6404	Remote Similarity	NPD5932	Phase 3
0.6396	Remote Similarity	NPD6891	Phase 2
0.6389	Remote Similarity	NPD6995	Phase 1
0.6386	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6637	Approved
0.6386	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5024	Approved
0.6384	Remote Similarity	NPD1625	Approved
0.638	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6342	Discontinued
0.6378	Remote Similarity	NPD7599	Phase 2
0.6378	Remote Similarity	NPD6557	Phase 2
0.6374	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD553	Approved
0.6369	Remote Similarity	NPD9567	Approved
0.6369	Remote Similarity	NPD552	Approved
0.6364	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7878	Phase 2
0.6355	Remote Similarity	NPD4668	Phase 2
0.6354	Remote Similarity	NPD1405	Approved
0.6349	Remote Similarity	NPD2844	Phase 3
0.6348	Remote Similarity	NPD2387	Approved
0.6346	Remote Similarity	NPD4596	Phase 1
0.6344	Remote Similarity	NPD4311	Approved
0.634	Remote Similarity	NPD6879	Phase 2
0.634	Remote Similarity	NPD6878	Phase 2
0.634	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD3389	Approved
0.6338	Remote Similarity	NPD3394	Approved
0.6338	Remote Similarity	NPD3393	Approved
0.6337	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD8283	Approved
0.6329	Remote Similarity	NPD56	Approved
0.6329	Remote Similarity	NPD8282	Approved
0.6324	Remote Similarity	NPD6874	Approved
0.6316	Remote Similarity	NPD8399	Phase 1
0.6316	Remote Similarity	NPD1070	Approved
0.6316	Remote Similarity	NPD8423	Phase 2
0.6316	Remote Similarity	NPD6489	Phase 3
0.6316	Remote Similarity	NPD1069	Approved
0.6308	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD7572	Phase 2
0.6303	Remote Similarity	NPD7470	Discontinued
0.63	Remote Similarity	NPD6659	Phase 2
0.63	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD4161	Discontinued

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