NPASS Compound

Structure

NPC473458 OpenBabel07101719142D 34 39 0 0 1 0 0 0 0 0999 V2000 2.8323 -0.6613 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 -0.1561 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 -2.5938 -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 0.9179 -0.9138 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 0.4804 -0.6613 0.0000 C 0 0 0 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 -2.5490 -1.2433 0.0000 C 0 0 1 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 2.0938 -1.0876 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 13 1 0 0 0 0 5 15 1 0 0 0 0 6 10 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 25 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 32 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 26 1 0 0 0 0 16 21 1 6 0 0 0 16 27 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 7 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:	1.063
LogD:	0.988
LogS:	-3.937
# 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:	6.443
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:	-5.313
MDCK Permeability:	2.756004687398672e-05
Pgp-inhibitor:	0.324
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.469
Plasma Protein Binding (PPB):	36.65076446533203%
Volume Distribution (VD):	0.699
Pgp-substrate:	65.33689880371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.773
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	2.77
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.566
Human Hepatotoxicity (H-HT):	0.651
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.139
Rat Oral Acute Toxicity:	0.986
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.38
Carcinogencity:	0.928
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC473458

Natural Product ID:	NPC473458
*Common Name:**	Kopsiloscine E
IUPAC Name:	n.a.
Synonyms:	Kopsiloscine E
Standard InCHIKey:	FELVAZDUIFIGTH-HCIKLWIJSA-N
Standard InCHI:	InChI=1S/C24H30N2O8/c1-32-13-4-5-15-14(12-13)22-9-11-25-10-6-16(27)21(17(22)25)7-8-23(22,26(15)20(30)34-3)24(31,18(21)28)19(29)33-2/h4-5,12,16-18,27-28,31H,6-11H2,1-3H3/t16-,17-,18-,21-,22+,23-,24+/m0/s1
SMILES:	COC1=CC2=C(C=C1)N(C34C25CCN6C5C(CC3)(C(CC6)O)C(C4(C(=O)OC)O)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL438158
PubChem CID:	44445382
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[508339]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[508339]

☑ 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 NPC473458 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	1643
0.2-0.3	3865
0.3-0.4	10348
0.4-0.5	14216
0.5-0.6	10536
0.6-0.7	1494
0.7-0.8	203
0.8-0.85	11
0.85-0.9	4
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC471513
0.9652	High Similarity	NPC288110
0.9238	High Similarity	NPC477397
0.9175	High Similarity	NPC222046
0.9078	High Similarity	NPC477395
0.8995	High Similarity	NPC477393
0.8914	High Similarity	NPC477396
0.8856	High Similarity	NPC471512
0.8779	High Similarity	NPC477394
0.8702	High Similarity	NPC127996
0.8557	High Similarity	NPC221687
0.8491	Intermediate Similarity	NPC234772
0.8424	Intermediate Similarity	NPC473375
0.8424	Intermediate Similarity	NPC97100
0.8419	Intermediate Similarity	NPC318525
0.8419	Intermediate Similarity	NPC10653
0.8178	Intermediate Similarity	NPC291173
0.8133	Intermediate Similarity	NPC476220
0.8133	Intermediate Similarity	NPC160113
0.8093	Intermediate Similarity	NPC159815
0.8086	Intermediate Similarity	NPC138830
0.8066	Intermediate Similarity	NPC195787
0.8066	Intermediate Similarity	NPC246140
0.8018	Intermediate Similarity	NPC19175
0.7991	Intermediate Similarity	NPC77777
0.7991	Intermediate Similarity	NPC476258
0.7991	Intermediate Similarity	NPC304837
0.7964	Intermediate Similarity	NPC128476
0.7945	Intermediate Similarity	NPC195636
0.7937	Intermediate Similarity	NPC231924
0.786	Intermediate Similarity	NPC154922
0.785	Intermediate Similarity	NPC87714
0.7838	Intermediate Similarity	NPC476069
0.783	Intermediate Similarity	NPC67904
0.7821	Intermediate Similarity	NPC120239
0.7788	Intermediate Similarity	NPC470480
0.7768	Intermediate Similarity	NPC469452
0.7768	Intermediate Similarity	NPC113455
0.7763	Intermediate Similarity	NPC10732
0.7757	Intermediate Similarity	NPC1464
0.7752	Intermediate Similarity	NPC269449
0.7746	Intermediate Similarity	NPC127178
0.7702	Intermediate Similarity	NPC329932
0.7692	Intermediate Similarity	NPC189661
0.7682	Intermediate Similarity	NPC469450
0.7682	Intermediate Similarity	NPC119722
0.7656	Intermediate Similarity	NPC105055
0.7656	Intermediate Similarity	NPC22689
0.7644	Intermediate Similarity	NPC46259
0.7644	Intermediate Similarity	NPC21425
0.7639	Intermediate Similarity	NPC301501
0.7623	Intermediate Similarity	NPC126556
0.7617	Intermediate Similarity	NPC469451
0.7617	Intermediate Similarity	NPC469722
0.7611	Intermediate Similarity	NPC148124
0.7604	Intermediate Similarity	NPC475147
0.7604	Intermediate Similarity	NPC470484
0.7597	Intermediate Similarity	NPC131977
0.7571	Intermediate Similarity	NPC474059
0.7566	Intermediate Similarity	NPC99724
0.7555	Intermediate Similarity	NPC248903
0.7545	Intermediate Similarity	NPC477160
0.7523	Intermediate Similarity	NPC66909
0.7512	Intermediate Similarity	NPC474077
0.7511	Intermediate Similarity	NPC26928
0.7511	Intermediate Similarity	NPC476436
0.75	Intermediate Similarity	NPC473486
0.75	Intermediate Similarity	NPC475316
0.7489	Intermediate Similarity	NPC223242
0.7466	Intermediate Similarity	NPC475133
0.7465	Intermediate Similarity	NPC201055
0.7465	Intermediate Similarity	NPC64576
0.7465	Intermediate Similarity	NPC470485
0.7465	Intermediate Similarity	NPC254045
0.7465	Intermediate Similarity	NPC151470
0.7464	Intermediate Similarity	NPC52262
0.7457	Intermediate Similarity	NPC470631
0.7457	Intermediate Similarity	NPC35390
0.7457	Intermediate Similarity	NPC473781
0.7442	Intermediate Similarity	NPC161804
0.7425	Intermediate Similarity	NPC139373
0.7419	Intermediate Similarity	NPC474427
0.7391	Intermediate Similarity	NPC122886
0.7383	Intermediate Similarity	NPC260909
0.7376	Intermediate Similarity	NPC478075
0.7371	Intermediate Similarity	NPC470483
0.7362	Intermediate Similarity	NPC195788
0.7362	Intermediate Similarity	NPC237901
0.735	Intermediate Similarity	NPC476429
0.7342	Intermediate Similarity	NPC151171
0.7327	Intermediate Similarity	NPC265642
0.7327	Intermediate Similarity	NPC218733
0.7327	Intermediate Similarity	NPC138615
0.7327	Intermediate Similarity	NPC132874
0.7327	Intermediate Similarity	NPC17677
0.7324	Intermediate Similarity	NPC5630
0.7306	Intermediate Similarity	NPC471489
0.729	Intermediate Similarity	NPC22476
0.7289	Intermediate Similarity	NPC470481
0.7289	Intermediate Similarity	NPC470482
0.7281	Intermediate Similarity	NPC474432
0.7281	Intermediate Similarity	NPC475713
0.7281	Intermediate Similarity	NPC90967
0.7248	Intermediate Similarity	NPC100863
0.7248	Intermediate Similarity	NPC193906
0.7248	Intermediate Similarity	NPC23080
0.7238	Intermediate Similarity	NPC475816
0.7228	Intermediate Similarity	NPC225319
0.7227	Intermediate Similarity	NPC232600
0.7209	Intermediate Similarity	NPC25401
0.7207	Intermediate Similarity	NPC268077
0.7203	Intermediate Similarity	NPC474192
0.7203	Intermediate Similarity	NPC475720
0.7195	Intermediate Similarity	NPC475747
0.7181	Intermediate Similarity	NPC217903
0.7174	Intermediate Similarity	NPC223590
0.7174	Intermediate Similarity	NPC219397
0.717	Intermediate Similarity	NPC97584
0.7168	Intermediate Similarity	NPC82541
0.7162	Intermediate Similarity	NPC473837
0.7155	Intermediate Similarity	NPC251071
0.7143	Intermediate Similarity	NPC94499
0.7143	Intermediate Similarity	NPC140311
0.7143	Intermediate Similarity	NPC218594
0.7143	Intermediate Similarity	NPC99043
0.7143	Intermediate Similarity	NPC203972
0.7137	Intermediate Similarity	NPC116178
0.713	Intermediate Similarity	NPC203628
0.713	Intermediate Similarity	NPC14339
0.7129	Intermediate Similarity	NPC129624
0.7124	Intermediate Similarity	NPC25961
0.7117	Intermediate Similarity	NPC286135
0.7104	Intermediate Similarity	NPC475489
0.7103	Intermediate Similarity	NPC262725
0.7103	Intermediate Similarity	NPC474746
0.7103	Intermediate Similarity	NPC475981
0.7098	Intermediate Similarity	NPC476500
0.7097	Intermediate Similarity	NPC204970
0.7097	Intermediate Similarity	NPC196231
0.7097	Intermediate Similarity	NPC473004
0.7089	Intermediate Similarity	NPC115906
0.7085	Intermediate Similarity	NPC207971
0.7082	Intermediate Similarity	NPC106593
0.708	Intermediate Similarity	NPC476496
0.7078	Intermediate Similarity	NPC162653
0.7078	Intermediate Similarity	NPC303214
0.707	Intermediate Similarity	NPC14994
0.7056	Intermediate Similarity	NPC182853
0.7051	Intermediate Similarity	NPC473667
0.7048	Intermediate Similarity	NPC264482
0.7048	Intermediate Similarity	NPC203202
0.7045	Intermediate Similarity	NPC472191
0.7042	Intermediate Similarity	NPC159963
0.7039	Intermediate Similarity	NPC118189
0.7037	Intermediate Similarity	NPC230098
0.7037	Intermediate Similarity	NPC477186
0.7035	Intermediate Similarity	NPC94687
0.7035	Intermediate Similarity	NPC106840
0.7035	Intermediate Similarity	NPC476495
0.7033	Intermediate Similarity	NPC214626
0.7033	Intermediate Similarity	NPC251212
0.7033	Intermediate Similarity	NPC139085
0.7032	Intermediate Similarity	NPC243626
0.7031	Intermediate Similarity	NPC321166
0.7028	Intermediate Similarity	NPC474470
0.7028	Intermediate Similarity	NPC478080
0.7018	Intermediate Similarity	NPC220241
0.7018	Intermediate Similarity	NPC295479
0.7014	Intermediate Similarity	NPC293624
0.7005	Intermediate Similarity	NPC473298
0.7	Intermediate Similarity	NPC311991
0.6995	Remote Similarity	NPC148693
0.6995	Remote Similarity	NPC118633
0.6995	Remote Similarity	NPC294790
0.6991	Remote Similarity	NPC326895
0.6988	Remote Similarity	NPC329982
0.6986	Remote Similarity	NPC78284
0.6983	Remote Similarity	NPC87560
0.6983	Remote Similarity	NPC195120
0.6982	Remote Similarity	NPC5374
0.6977	Remote Similarity	NPC248642
0.6971	Remote Similarity	NPC33507
0.6966	Remote Similarity	NPC76478
0.6963	Remote Similarity	NPC474745
0.6963	Remote Similarity	NPC220961
0.696	Remote Similarity	NPC207873
0.696	Remote Similarity	NPC100573
0.6959	Remote Similarity	NPC320088
0.6957	Remote Similarity	NPC473006
0.6957	Remote Similarity	NPC268223
0.6957	Remote Similarity	NPC70172
0.6955	Remote Similarity	NPC34717
0.6955	Remote Similarity	NPC230313
0.6953	Remote Similarity	NPC37957
0.6953	Remote Similarity	NPC475609
0.6948	Remote Similarity	NPC189079
0.6947	Remote Similarity	NPC80472
0.6944	Remote Similarity	NPC156576
0.6942	Remote Similarity	NPC99632
0.6942	Remote Similarity	NPC282339

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 NPC473458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	591
0.2-0.3	876
0.3-0.4	2157
0.4-0.5	3097
0.5-0.6	1884
0.6-0.7	295
0.7-0.8	33
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
0.7477	Intermediate Similarity	NPD5582	Discontinued
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
0.7383	Intermediate Similarity	NPD8459	Approved
0.7383	Intermediate Similarity	NPD8460	Approved
0.7364	Intermediate Similarity	NPD4582	Approved
0.7364	Intermediate Similarity	NPD4583	Approved
0.7362	Intermediate Similarity	NPD8467	Approved
0.7362	Intermediate Similarity	NPD8466	Approved
0.7362	Intermediate Similarity	NPD8465	Approved
0.7359	Intermediate Similarity	NPD7186	Phase 3
0.7318	Intermediate Similarity	NPD4002	Approved
0.7318	Intermediate Similarity	NPD4004	Approved
0.7248	Intermediate Similarity	NPD8426	Approved
0.7248	Intermediate Similarity	NPD8425	Approved
0.7246	Intermediate Similarity	NPD6625	Approved
0.7227	Intermediate Similarity	NPD8427	Approved
0.7227	Intermediate Similarity	NPD8428	Approved
0.7227	Intermediate Similarity	NPD8429	Approved
0.7155	Intermediate Similarity	NPD6997	Phase 2
0.713	Intermediate Similarity	NPD2488	Approved
0.713	Intermediate Similarity	NPD2490	Approved
0.7126	Intermediate Similarity	NPD8363	Approved
0.7126	Intermediate Similarity	NPD8364	Approved
0.7089	Intermediate Similarity	NPD2968	Approved
0.7089	Intermediate Similarity	NPD2971	Approved
0.7083	Intermediate Similarity	NPD7048	Phase 3
0.707	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7805	Phase 3
0.7029	Intermediate Similarity	NPD6723	Discontinued
0.7028	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7821	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5600	Discontinued
0.7009	Intermediate Similarity	NPD7497	Discontinued
0.6978	Remote Similarity	NPD4040	Phase 1
0.6966	Remote Similarity	NPD7907	Approved
0.6959	Remote Similarity	NPD7906	Approved
0.6955	Remote Similarity	NPD7560	Approved
0.6953	Remote Similarity	NPD2899	Discontinued
0.6952	Remote Similarity	NPD8489	Phase 1
0.6937	Remote Similarity	NPD4420	Approved
0.6916	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7262	Phase 1
0.6907	Remote Similarity	NPD7820	Phase 3
0.6906	Remote Similarity	NPD6874	Approved
0.6897	Remote Similarity	NPD7047	Phase 3
0.6889	Remote Similarity	NPD5006	Approved
0.6889	Remote Similarity	NPD5005	Approved
0.688	Remote Similarity	NPD4111	Phase 1
0.688	Remote Similarity	NPD4665	Approved
0.6854	Remote Similarity	NPD5313	Approved
0.6854	Remote Similarity	NPD5312	Approved
0.6847	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6238	Discontinued
0.6835	Remote Similarity	NPD4663	Approved
0.683	Remote Similarity	NPD5608	Approved
0.683	Remote Similarity	NPD5609	Approved
0.6826	Remote Similarity	NPD5860	Discontinued
0.6814	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4859	Phase 1
0.6787	Remote Similarity	NPD7296	Approved
0.6784	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3437	Discontinued
0.6777	Remote Similarity	NPD3051	Approved
0.6774	Remote Similarity	NPD4577	Approved
0.6774	Remote Similarity	NPD4578	Approved
0.6774	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7956	Approved
0.6745	Remote Similarity	NPD7955	Approved
0.6744	Remote Similarity	NPD7803	Approved
0.674	Remote Similarity	NPD3057	Approved
0.6739	Remote Similarity	NPD7302	Phase 3
0.6739	Remote Similarity	NPD7300	Phase 3
0.6735	Remote Similarity	NPD4846	Phase 2
0.673	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3983	Phase 3
0.6727	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4107	Approved
0.6724	Remote Similarity	NPD4493	Discontinued
0.6724	Remote Similarity	NPD5676	Approved
0.6719	Remote Similarity	NPD7708	Approved
0.6714	Remote Similarity	NPD4481	Phase 3
0.6711	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4668	Phase 2
0.6709	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8461	Discontinued
0.6696	Remote Similarity	NPD3416	Discontinued
0.6695	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3912	Discontinued
0.6694	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6716	Phase 1
0.6682	Remote Similarity	NPD5610	Approved
0.6682	Remote Similarity	NPD5938	Phase 3
0.6681	Remote Similarity	NPD3298	Approved
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4082	Approved
0.6667	Remote Similarity	NPD5496	Approved
0.6667	Remote Similarity	NPD2969	Approved
0.6667	Remote Similarity	NPD2970	Approved
0.6667	Remote Similarity	NPD2972	Approved
0.6667	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD8404	Phase 2
0.6653	Remote Similarity	NPD7432	Phase 2
0.6653	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD1945	Phase 1
0.6651	Remote Similarity	NPD6457	Approved
0.6639	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5071	Phase 2
0.6635	Remote Similarity	NPD4796	Discontinued
0.6624	Remote Similarity	NPD7301	Phase 3
0.6624	Remote Similarity	NPD7827	Phase 1
0.6624	Remote Similarity	NPD7292	Approved
0.6623	Remote Similarity	NPD7263	Phase 2
0.6623	Remote Similarity	NPD7476	Discontinued
0.6623	Remote Similarity	NPD4482	Phase 3
0.6623	Remote Similarity	NPD4596	Phase 1
0.6621	Remote Similarity	NPD7280	Phase 3
0.6621	Remote Similarity	NPD7281	Phase 3
0.662	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD19	Approved
0.6619	Remote Similarity	NPD1742	Approved
0.6619	Remote Similarity	NPD1743	Approved
0.6613	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8016	Phase 3
0.6613	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5507	Approved
0.6611	Remote Similarity	NPD5506	Approved
0.6609	Remote Similarity	NPD6644	Discontinued
0.6606	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4455	Discontinued
0.6595	Remote Similarity	NPD2907	Approved
0.6595	Remote Similarity	NPD2906	Approved
0.6594	Remote Similarity	NPD3448	Approved
0.6594	Remote Similarity	NPD2491	Approved
0.6593	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8358	Approved
0.6581	Remote Similarity	NPD683	Approved
0.6577	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7797	Approved
0.6571	Remote Similarity	NPD7796	Approved
0.657	Remote Similarity	NPD7224	Discontinued
0.657	Remote Similarity	NPD7223	Discontinued
0.6568	Remote Similarity	NPD4897	Phase 2
0.6562	Remote Similarity	NPD8492	Approved
0.656	Remote Similarity	NPD6517	Phase 3
0.656	Remote Similarity	NPD6297	Approved
0.6558	Remote Similarity	NPD2489	Approved
0.6558	Remote Similarity	NPD27	Approved
0.6557	Remote Similarity	NPD6199	Discontinued
0.6555	Remote Similarity	NPD7293	Approved
0.6553	Remote Similarity	NPD4492	Approved
0.6553	Remote Similarity	NPD4494	Approved
0.6548	Remote Similarity	NPD5488	Discontinued
0.6545	Remote Similarity	NPD7310	Approved
0.6545	Remote Similarity	NPD7312	Approved
0.6545	Remote Similarity	NPD7311	Approved
0.6545	Remote Similarity	NPD7313	Approved
0.6544	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5186	Approved
0.6542	Remote Similarity	NPD5183	Approved
0.6542	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3297	Approved
0.6535	Remote Similarity	NPD7811	Phase 3
0.6535	Remote Similarity	NPD7810	Phase 3
0.6516	Remote Similarity	NPD7309	Approved
0.6516	Remote Similarity	NPD6853	Approved
0.6516	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6851	Approved
0.6514	Remote Similarity	NPD7479	Phase 2
0.6498	Remote Similarity	NPD7559	Phase 2
0.6488	Remote Similarity	NPD7278	Phase 2
0.6488	Remote Similarity	NPD7279	Phase 2
0.6483	Remote Similarity	NPD3888	Discontinued
0.6481	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7922	Phase 1
0.6476	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5928	Phase 1
0.6473	Remote Similarity	NPD2843	Phase 2
0.6473	Remote Similarity	NPD2845	Phase 2
0.6471	Remote Similarity	NPD8149	Discontinued
0.6471	Remote Similarity	NPD8367	Approved
0.6468	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD3893	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