NPASS Compound

Structure

NPC471513 OpenBabel07101719522D 34 39 0 0 1 0 0 0 0 0999 V2000 1.6564 1.3755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4004 3.6207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7469 4.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3554 -0.6613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9179 -0.9138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3554 -0.1561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5938 -2.0948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5309 -0.2129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8668 -0.0137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2138 -1.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8788 -2.5594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3230 -2.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4804 -0.6613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9179 0.0965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5490 -1.2433 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4804 -0.1561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0741 -1.3210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6100 -0.0983 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4753 2.6079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0540 3.2439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7892 -0.8564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2504 -1.1005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2969 -0.4087 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8638 0.1256 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1190 -2.1725 0.0000 N 0 0 3 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 -3.2640 -0.7787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2305 0.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3051 2.4117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8881 3.4211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1089 0.9423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9179 0.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2303 3.4246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4834 3.8775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 34 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 12 25 1 0 0 0 0 13 16 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 32 1 0 0 0 0 15 21 1 6 0 0 0 15 27 1 0 0 0 0 16 26 1 0 0 0 0 17 21 1 1 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 6 0 0 0 18 24 1 0 0 0 0 18 28 1 0 0 0 0 19 24 1 0 0 0 0 19 29 2 0 0 0 0 19 33 1 0 0 0 0 20 26 1 0 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 8 1 1 0 0 0 22 23 1 1 0 0 0 23 24 1 1 0 0 0 23 26 1 0 0 0 0 24 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.2
Volume:	451.454
LogP:	0.984
LogD:	0.764
LogS:	-3.918
# Rotatable Bonds:	5
TPSA:	129.0
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	6.473
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.304
MDCK Permeability:	2.9939821615698747e-05
Pgp-inhibitor:	0.349
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.515
Plasma Protein Binding (PPB):	31.9323673248291%
Volume Distribution (VD):	0.749
Pgp-substrate:	65.86007690429688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.529
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.939

ADMET: Excretion

Clearance (CL):	2.681
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.556
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.359
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.398
Carcinogencity:	0.94
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC471513

Natural Product ID:	NPC471513
*Common Name:**	Kopsiloscine F
IUPAC Name:	n.a.
Synonyms:	Kopsiloscine F
Standard InCHIKey:	GDGFOGDXGVRMOU-FFYLJQLVSA-N
Standard InCHI:	InChI=1S/C24H30N2O8/c1-32-14-6-4-5-13-16(14)26(20(30)34-3)23-9-8-21(18(28)24(23,31)19(29)33-2)15(27)7-11-25-12-10-22(13,23)17(21)25/h4-6,15,17-18,27-28,31H,7-12H2,1-3H3/t15-,17-,18-,21-,22+,23-,24+/m0/s1
SMILES:	COC(=O)N1c2c(OC)cccc2[C@]23[C@@]41CC[C@@]1([C@@H]([C@@]4(O)C(=O)OC)O)[C@@H]3N(CC2)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253773
PubChem CID:	44445383
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003755] Aspidofractine 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
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17939738]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	leaf and stem-bark	Pahang, Malaysia	1996-JUL	PMID[18078327]
NPO19270	Kopsia singapurensis	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	3

Activity Type	# Activity
Cell Line	1
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[483079]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[483079]

☑ 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 NPC471513 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	369
0.1-0.2	1642
0.2-0.3	3887
0.3-0.4	10425
0.4-0.5	14246
0.5-0.6	10448
0.6-0.7	1490
0.7-0.8	169
0.8-0.85	9
0.85-0.9	2
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC473458
0.9517	High Similarity	NPC477397
0.9458	High Similarity	NPC222046
0.9363	High Similarity	NPC288110
0.9346	High Similarity	NPC477395
0.9259	High Similarity	NPC477393
0.9174	High Similarity	NPC477396
0.9048	High Similarity	NPC477394
0.867	High Similarity	NPC471512
0.8524	High Similarity	NPC127996
0.8374	Intermediate Similarity	NPC221687
0.8325	Intermediate Similarity	NPC246140
0.8325	Intermediate Similarity	NPC195787
0.8318	Intermediate Similarity	NPC234772
0.8244	Intermediate Similarity	NPC473375
0.8244	Intermediate Similarity	NPC97100
0.8165	Intermediate Similarity	NPC10653
0.8165	Intermediate Similarity	NPC318525
0.8018	Intermediate Similarity	NPC291173
0.7974	Intermediate Similarity	NPC476220
0.7974	Intermediate Similarity	NPC160113
0.7946	Intermediate Similarity	NPC470480
0.7925	Intermediate Similarity	NPC1464
0.7909	Intermediate Similarity	NPC77777
0.7857	Intermediate Similarity	NPC19175
0.7845	Intermediate Similarity	NPC469452
0.7844	Intermediate Similarity	NPC159815
0.7835	Intermediate Similarity	NPC476258
0.7835	Intermediate Similarity	NPC304837
0.783	Intermediate Similarity	NPC138830
0.7783	Intermediate Similarity	NPC195636
0.7783	Intermediate Similarity	NPC154922
0.7778	Intermediate Similarity	NPC329932
0.7778	Intermediate Similarity	NPC231924
0.7759	Intermediate Similarity	NPC469450
0.7723	Intermediate Similarity	NPC128476
0.7716	Intermediate Similarity	NPC301501
0.7692	Intermediate Similarity	NPC113455
0.7692	Intermediate Similarity	NPC469451
0.7685	Intermediate Similarity	NPC470484
0.7685	Intermediate Similarity	NPC87714
0.7679	Intermediate Similarity	NPC476069
0.7672	Intermediate Similarity	NPC131977
0.7669	Intermediate Similarity	NPC120239
0.7664	Intermediate Similarity	NPC67904
0.763	Intermediate Similarity	NPC470485
0.7606	Intermediate Similarity	NPC161804
0.7565	Intermediate Similarity	NPC223242
0.7542	Intermediate Similarity	NPC469722
0.7536	Intermediate Similarity	NPC470483
0.7534	Intermediate Similarity	NPC189661
0.7523	Intermediate Similarity	NPC10732
0.7523	Intermediate Similarity	NPC66909
0.7511	Intermediate Similarity	NPC269449
0.75	Intermediate Similarity	NPC127178
0.75	Intermediate Similarity	NPC474427
0.75	Intermediate Similarity	NPC139373
0.7488	Intermediate Similarity	NPC138615
0.7488	Intermediate Similarity	NPC218733
0.7488	Intermediate Similarity	NPC105055
0.7488	Intermediate Similarity	NPC265642
0.7488	Intermediate Similarity	NPC22689
0.7488	Intermediate Similarity	NPC132874
0.7465	Intermediate Similarity	NPC201055
0.7465	Intermediate Similarity	NPC64576
0.7465	Intermediate Similarity	NPC254045
0.7465	Intermediate Similarity	NPC151470
0.7444	Intermediate Similarity	NPC470482
0.7444	Intermediate Similarity	NPC119722
0.7444	Intermediate Similarity	NPC470481
0.7412	Intermediate Similarity	NPC46259
0.7406	Intermediate Similarity	NPC474059
0.7393	Intermediate Similarity	NPC21425
0.7389	Intermediate Similarity	NPC126556
0.7387	Intermediate Similarity	NPC477160
0.738	Intermediate Similarity	NPC148124
0.7364	Intermediate Similarity	NPC475147
0.7361	Intermediate Similarity	NPC475713
0.7361	Intermediate Similarity	NPC474432
0.7359	Intermediate Similarity	NPC476436
0.735	Intermediate Similarity	NPC475316
0.735	Intermediate Similarity	NPC473486
0.7346	Intermediate Similarity	NPC262725
0.7336	Intermediate Similarity	NPC99724
0.7328	Intermediate Similarity	NPC248903
0.7327	Intermediate Similarity	NPC17677
0.7308	Intermediate Similarity	NPC470631
0.7308	Intermediate Similarity	NPC35390
0.7308	Intermediate Similarity	NPC473781
0.7306	Intermediate Similarity	NPC471489
0.7299	Intermediate Similarity	NPC52262
0.7284	Intermediate Similarity	NPC26928
0.7273	Intermediate Similarity	NPC475747
0.7273	Intermediate Similarity	NPC474077
0.7248	Intermediate Similarity	NPC260909
0.7248	Intermediate Similarity	NPC23080
0.7248	Intermediate Similarity	NPC193906
0.7241	Intermediate Similarity	NPC122886
0.7232	Intermediate Similarity	NPC475133
0.7229	Intermediate Similarity	NPC251071
0.7227	Intermediate Similarity	NPC195788
0.7227	Intermediate Similarity	NPC237901
0.7222	Intermediate Similarity	NPC94499
0.7203	Intermediate Similarity	NPC476429
0.7202	Intermediate Similarity	NPC90967
0.7197	Intermediate Similarity	NPC151171
0.7195	Intermediate Similarity	NPC286135
0.7176	Intermediate Similarity	NPC196231
0.7174	Intermediate Similarity	NPC475609
0.7174	Intermediate Similarity	NPC219397
0.7143	Intermediate Similarity	NPC78284
0.7143	Intermediate Similarity	NPC478075
0.7137	Intermediate Similarity	NPC266994
0.7137	Intermediate Similarity	NPC285254
0.7136	Intermediate Similarity	NPC33507
0.713	Intermediate Similarity	NPC25401
0.713	Intermediate Similarity	NPC22476
0.7112	Intermediate Similarity	NPC76478
0.7103	Intermediate Similarity	NPC474746
0.7103	Intermediate Similarity	NPC475981
0.7098	Intermediate Similarity	NPC476500
0.7091	Intermediate Similarity	NPC100863
0.7091	Intermediate Similarity	NPC293624
0.7089	Intermediate Similarity	NPC115906
0.7087	Intermediate Similarity	NPC473837
0.7083	Intermediate Similarity	NPC5630
0.708	Intermediate Similarity	NPC476496
0.7078	Intermediate Similarity	NPC162653
0.7076	Intermediate Similarity	NPC74216
0.7072	Intermediate Similarity	NPC469732
0.7072	Intermediate Similarity	NPC232600
0.7069	Intermediate Similarity	NPC140311
0.7059	Intermediate Similarity	NPC225319
0.7054	Intermediate Similarity	NPC268077
0.7042	Intermediate Similarity	NPC220961
0.7039	Intermediate Similarity	NPC118189
0.7039	Intermediate Similarity	NPC7560
0.7037	Intermediate Similarity	NPC230098
0.7035	Intermediate Similarity	NPC94687
0.7035	Intermediate Similarity	NPC106840
0.7035	Intermediate Similarity	NPC476495
0.7034	Intermediate Similarity	NPC13249
0.7031	Intermediate Similarity	NPC217903
0.7031	Intermediate Similarity	NPC30749
0.7028	Intermediate Similarity	NPC474470
0.7026	Intermediate Similarity	NPC223590
0.7025	Intermediate Similarity	NPC475816
0.7023	Intermediate Similarity	NPC156576
0.7014	Intermediate Similarity	NPC124302
0.7014	Intermediate Similarity	NPC70290
0.7014	Intermediate Similarity	NPC73020
0.7014	Intermediate Similarity	NPC215098
0.7014	Intermediate Similarity	NPC46744
0.7014	Intermediate Similarity	NPC14622
0.7009	Intermediate Similarity	NPC250960
0.7009	Intermediate Similarity	NPC71539
0.7009	Intermediate Similarity	NPC97584
0.7005	Intermediate Similarity	NPC237579
0.7	Intermediate Similarity	NPC148391
0.7	Intermediate Similarity	NPC311991
0.6995	Remote Similarity	NPC294790
0.6995	Remote Similarity	NPC148693
0.6995	Remote Similarity	NPC118633
0.6991	Remote Similarity	NPC14994
0.6991	Remote Similarity	NPC212123
0.6991	Remote Similarity	NPC326895
0.6991	Remote Similarity	NPC11708
0.6987	Remote Similarity	NPC475720
0.6987	Remote Similarity	NPC116178
0.6987	Remote Similarity	NPC474192
0.6983	Remote Similarity	NPC182853
0.6983	Remote Similarity	NPC87560
0.6983	Remote Similarity	NPC134702
0.6983	Remote Similarity	NPC195120
0.6981	Remote Similarity	NPC99043
0.6981	Remote Similarity	NPC218594
0.6978	Remote Similarity	NPC14339
0.6977	Remote Similarity	NPC248642
0.6976	Remote Similarity	NPC133609
0.6974	Remote Similarity	NPC25961
0.6972	Remote Similarity	NPC203628
0.6967	Remote Similarity	NPC129624
0.6964	Remote Similarity	NPC2173
0.6964	Remote Similarity	NPC202771
0.6964	Remote Similarity	NPC119818
0.6964	Remote Similarity	NPC328700
0.6963	Remote Similarity	NPC474745
0.6963	Remote Similarity	NPC99179
0.6963	Remote Similarity	NPC159963
0.6957	Remote Similarity	NPC114468
0.6957	Remote Similarity	NPC268223
0.6953	Remote Similarity	NPC37957
0.6951	Remote Similarity	NPC226652
0.6951	Remote Similarity	NPC120671
0.6951	Remote Similarity	NPC314100
0.6951	Remote Similarity	NPC475489
0.6951	Remote Similarity	NPC72788
0.6948	Remote Similarity	NPC189079
0.6947	Remote Similarity	NPC80472
0.6943	Remote Similarity	NPC82541

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 NPC471513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	591
0.2-0.3	925
0.3-0.4	2239
0.4-0.5	3060
0.5-0.6	1803
0.6-0.7	285
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
0.7523	Intermediate Similarity	NPD2973	Approved
0.7523	Intermediate Similarity	NPD2974	Approved
0.7523	Intermediate Similarity	NPD2975	Approved
0.7465	Intermediate Similarity	NPD3450	Approved
0.7465	Intermediate Similarity	NPD2494	Approved
0.7465	Intermediate Similarity	NPD2493	Approved
0.7465	Intermediate Similarity	NPD3452	Approved
0.7419	Intermediate Similarity	NPD4580	Approved
0.7393	Intermediate Similarity	NPD6625	Approved
0.7364	Intermediate Similarity	NPD4582	Approved
0.7364	Intermediate Similarity	NPD4583	Approved
0.7318	Intermediate Similarity	NPD4002	Approved
0.7318	Intermediate Similarity	NPD4004	Approved
0.7315	Intermediate Similarity	NPD5582	Discontinued
0.7248	Intermediate Similarity	NPD8460	Approved
0.7248	Intermediate Similarity	NPD8459	Approved
0.7229	Intermediate Similarity	NPD6997	Phase 2
0.7227	Intermediate Similarity	NPD8465	Approved
0.7227	Intermediate Similarity	NPD8466	Approved
0.7227	Intermediate Similarity	NPD8467	Approved
0.721	Intermediate Similarity	NPD7186	Phase 3
0.7155	Intermediate Similarity	NPD7048	Phase 3
0.713	Intermediate Similarity	NPD2488	Approved
0.713	Intermediate Similarity	NPD2490	Approved
0.7115	Intermediate Similarity	NPD8426	Approved
0.7115	Intermediate Similarity	NPD8425	Approved
0.7109	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2899	Discontinued
0.7093	Intermediate Similarity	NPD8428	Approved
0.7093	Intermediate Similarity	NPD8429	Approved
0.7093	Intermediate Similarity	NPD8427	Approved
0.7089	Intermediate Similarity	NPD2968	Approved
0.7089	Intermediate Similarity	NPD2971	Approved
0.7014	Intermediate Similarity	NPD4420	Approved
0.7009	Intermediate Similarity	NPD7497	Discontinued
0.6992	Remote Similarity	NPD8364	Approved
0.6992	Remote Similarity	NPD8363	Approved
0.6978	Remote Similarity	NPD4040	Phase 1
0.697	Remote Similarity	NPD7047	Phase 3
0.6966	Remote Similarity	NPD7805	Phase 3
0.6966	Remote Similarity	NPD7907	Approved
0.6964	Remote Similarity	NPD5005	Approved
0.6964	Remote Similarity	NPD5006	Approved
0.6959	Remote Similarity	NPD7906	Approved
0.6938	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5860	Discontinued
0.6892	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6723	Discontinued
0.688	Remote Similarity	NPD4111	Phase 1
0.688	Remote Similarity	NPD4665	Approved
0.6878	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1945	Phase 1
0.6869	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5313	Approved
0.6854	Remote Similarity	NPD5312	Approved
0.6847	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4596	Phase 1
0.6835	Remote Similarity	NPD4663	Approved
0.6827	Remote Similarity	NPD8489	Phase 1
0.6816	Remote Similarity	NPD7560	Approved
0.6812	Remote Similarity	NPD2906	Approved
0.6812	Remote Similarity	NPD2907	Approved
0.6812	Remote Similarity	NPD4859	Phase 1
0.681	Remote Similarity	NPD4455	Discontinued
0.6797	Remote Similarity	NPD5676	Approved
0.6797	Remote Similarity	NPD4493	Discontinued
0.6787	Remote Similarity	NPD7296	Approved
0.6784	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD3051	Approved
0.6776	Remote Similarity	NPD5600	Discontinued
0.6774	Remote Similarity	NPD4577	Approved
0.6774	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4578	Approved
0.6772	Remote Similarity	NPD8461	Discontinued
0.677	Remote Similarity	NPD6238	Discontinued
0.6767	Remote Similarity	NPD4494	Approved
0.6767	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD4492	Approved
0.6765	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7820	Phase 3
0.6761	Remote Similarity	NPD6716	Phase 1
0.6761	Remote Similarity	NPD5938	Phase 3
0.6759	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6874	Approved
0.6754	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3057	Approved
0.6739	Remote Similarity	NPD4082	Approved
0.6726	Remote Similarity	NPD4107	Approved
0.6723	Remote Similarity	NPD8404	Phase 2
0.6714	Remote Similarity	NPD4481	Phase 3
0.6709	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3437	Discontinued
0.6709	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3888	Discontinued
0.6693	Remote Similarity	NPD8492	Approved
0.6682	Remote Similarity	NPD7262	Phase 1
0.6681	Remote Similarity	NPD3893	Discontinued
0.6681	Remote Similarity	NPD6644	Discontinued
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4846	Phase 2
0.6667	Remote Similarity	NPD3472	Approved
0.6667	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2970	Approved
0.6667	Remote Similarity	NPD2969	Approved
0.6667	Remote Similarity	NPD2972	Approved
0.6667	Remote Similarity	NPD4022	Approved
0.664	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6199	Discontinued
0.6625	Remote Similarity	NPD3912	Discontinued
0.6624	Remote Similarity	NPD7827	Phase 1
0.6623	Remote Similarity	NPD4482	Phase 3
0.6621	Remote Similarity	NPD7280	Phase 3
0.6621	Remote Similarity	NPD7281	Phase 3
0.6615	Remote Similarity	NPD7955	Approved
0.6615	Remote Similarity	NPD7803	Approved
0.6615	Remote Similarity	NPD7956	Approved
0.6609	Remote Similarity	NPD3298	Approved
0.6609	Remote Similarity	NPD3372	Discontinued
0.6608	Remote Similarity	NPD5608	Approved
0.6608	Remote Similarity	NPD5609	Approved
0.6601	Remote Similarity	NPD8367	Approved
0.6594	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD3448	Approved
0.6594	Remote Similarity	NPD2491	Approved
0.6591	Remote Similarity	NPD6851	Approved
0.6591	Remote Similarity	NPD6853	Approved
0.6589	Remote Similarity	NPD7708	Approved
0.6577	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4668	Phase 2
0.656	Remote Similarity	NPD6297	Approved
0.6558	Remote Similarity	NPD2489	Approved
0.6558	Remote Similarity	NPD27	Approved
0.6556	Remote Similarity	NPD7279	Phase 2
0.6556	Remote Similarity	NPD7278	Phase 2
0.6555	Remote Similarity	NPD7292	Approved
0.6552	Remote Similarity	NPD7263	Phase 2
0.6545	Remote Similarity	NPD7312	Approved
0.6545	Remote Similarity	NPD7310	Approved
0.6545	Remote Similarity	NPD7311	Approved
0.6545	Remote Similarity	NPD7313	Approved
0.6542	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7810	Phase 3
0.6535	Remote Similarity	NPD7811	Phase 3
0.6532	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5496	Approved
0.6524	Remote Similarity	NPD7300	Phase 3
0.6524	Remote Similarity	NPD7302	Phase 3
0.6524	Remote Similarity	NPD7701	Phase 2
0.652	Remote Similarity	NPD7432	Phase 2
0.6516	Remote Similarity	NPD7309	Approved
0.6502	Remote Similarity	NPD7224	Discontinued
0.6502	Remote Similarity	NPD7223	Discontinued
0.6495	Remote Similarity	NPD3983	Phase 3
0.6495	Remote Similarity	NPD6457	Approved
0.6495	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5071	Phase 2
0.649	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7293	Approved
0.6484	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8016	Phase 3
0.6478	Remote Similarity	NPD3416	Discontinued
0.6478	Remote Similarity	NPD6321	Discontinued
0.6478	Remote Similarity	NPD7922	Phase 1
0.6471	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8067	Phase 3
0.6463	Remote Similarity	NPD3297	Approved
0.646	Remote Similarity	NPD5610	Approved
0.6453	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6517	Phase 3
0.6429	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD3006	Discontinued
0.6422	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7301	Phase 3
0.6414	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5036	Approved
0.641	Remote Similarity	NPD7583	Approved
0.6407	Remote Similarity	NPD7476	Discontinued
0.6407	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5507	Approved
0.6405	Remote Similarity	NPD5506	Approved
0.6402	Remote Similarity	NPD4796	Discontinued
0.6398	Remote Similarity	NPD1769	Discontinued
0.6393	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD8358	Approved
0.6389	Remote Similarity	NPD7315	Approved
0.6389	Remote Similarity	NPD5186	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