NPASS Compound

Structure

NPC473375 OpenBabel07101719252D 31 36 0 0 1 0 0 0 0 0999 V2000 -0.8010 2.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7779 4.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4116 -0.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4116 -0.1626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7014 -2.1817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9560 -0.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9560 0.1005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6547 -1.2949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5944 -0.2218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9027 -0.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2227 -1.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9567 -2.6656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5004 -0.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5004 -0.1626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1187 -1.3757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6767 -0.1024 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.3184 1.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0977 3.3784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8634 -0.8919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2608 -1.1461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3092 -0.4256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8997 0.1308 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1654 -2.2626 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 -2.3230 0.5067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1827 1.2191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9663 3.5630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1549 0.9814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0632 2.2740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5035 4.0383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 14 2 0 0 0 0 7 15 2 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 24 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 25 1 0 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 18 27 2 0 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 28 2 0 0 0 0 19 31 1 0 0 0 0 20 8 1 6 0 0 0 21 22 1 1 0 0 0 22 23 1 1 0 0 0 22 25 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.18
Volume:	413.941
LogP:	1.518
LogD:	1.047
LogS:	-3.986
# Rotatable Bonds:	4
TPSA:	99.54
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.51
Synthetic Accessibility Score:	6.357
Fsp3:	0.565
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:	-5.244
MDCK Permeability:	2.1437204850371927e-05
Pgp-inhibitor:	0.155
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.571
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.94
Plasma Protein Binding (PPB):	36.29871368408203%
Volume Distribution (VD):	1.335
Pgp-substrate:	58.754302978515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.171
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.626
CYP3A4-inhibitor:	0.259
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	2.407
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.05
Carcinogencity:	0.952
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.724

Download Data

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

Natural Product: NPC473375

Natural Product ID:	NPC473375
*Common Name:**	Kopsiloscine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HVUPNDMRYTUMME-KRBXGMSDSA-N
Standard InCHI:	InChI=1S/C23H26N2O6/c1-30-18(27)23(29)17(26)20-8-5-12-24-13-11-21(16(20)24)14-6-3-4-7-15(14)25(19(28)31-2)22(21,23)10-9-20/h3-8,16-17,26,29H,9-13H2,1-2H3/t16-,17?,20-,21+,22-,23?/m0/s1
SMILES:	COC(=O)N1c2ccccc2[C@]23[C@@]41CC[C@]1(C(C4(O)C(=O)OC)O)[C@@H]3N(CC2)CC=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403997
PubChem CID:	44445380
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	=	45800.0	nM	PMID[521696]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	42300.0	nM	PMID[521696]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8900.0	nM	PMID[521696]

☑ 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 NPC473375 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	264
0.1-0.2	1288
0.2-0.3	3196
0.3-0.4	15712
0.4-0.5	17357
0.5-0.6	4004
0.6-0.7	767
0.7-0.8	92
0.8-0.85	9
0.85-0.9	4
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC97100
0.9714	High Similarity	NPC221687
0.9392	High Similarity	NPC471512
0.8827	High Similarity	NPC52262
0.8724	High Similarity	NPC288110
0.8724	High Similarity	NPC222046
0.8424	Intermediate Similarity	NPC473458
0.8325	Intermediate Similarity	NPC127996
0.8244	Intermediate Similarity	NPC471513
0.8182	Intermediate Similarity	NPC225319
0.7971	Intermediate Similarity	NPC477394
0.7853	Intermediate Similarity	NPC105055
0.7853	Intermediate Similarity	NPC22689
0.7833	Intermediate Similarity	NPC282339
0.7833	Intermediate Similarity	NPC99632
0.782	Intermediate Similarity	NPC477397
0.7706	Intermediate Similarity	NPC477395
0.7704	Intermediate Similarity	NPC90967
0.7636	Intermediate Similarity	NPC477393
0.7592	Intermediate Similarity	NPC97584
0.7568	Intermediate Similarity	NPC477396
0.754	Intermediate Similarity	NPC139085
0.754	Intermediate Similarity	NPC251212
0.754	Intermediate Similarity	NPC214626
0.75	Intermediate Similarity	NPC475489
0.746	Intermediate Similarity	NPC476441
0.7398	Intermediate Similarity	NPC473298
0.7366	Intermediate Similarity	NPC472106
0.7351	Intermediate Similarity	NPC472117
0.7337	Intermediate Similarity	NPC34717
0.733	Intermediate Similarity	NPC186669
0.7297	Intermediate Similarity	NPC201424
0.7296	Intermediate Similarity	NPC181928
0.7277	Intermediate Similarity	NPC10653
0.7277	Intermediate Similarity	NPC318525
0.7268	Intermediate Similarity	NPC477159
0.7268	Intermediate Similarity	NPC329833
0.7264	Intermediate Similarity	NPC162440
0.7263	Intermediate Similarity	NPC476425
0.726	Intermediate Similarity	NPC475316
0.726	Intermediate Similarity	NPC473486
0.7258	Intermediate Similarity	NPC293458
0.7258	Intermediate Similarity	NPC472101
0.7258	Intermediate Similarity	NPC472120
0.7254	Intermediate Similarity	NPC11149
0.724	Intermediate Similarity	NPC260075
0.7216	Intermediate Similarity	NPC476428
0.7215	Intermediate Similarity	NPC35390
0.7215	Intermediate Similarity	NPC470631
0.7215	Intermediate Similarity	NPC473781
0.7204	Intermediate Similarity	NPC315368
0.7202	Intermediate Similarity	NPC99043
0.7202	Intermediate Similarity	NPC321211
0.7202	Intermediate Similarity	NPC218594
0.719	Intermediate Similarity	NPC159815
0.7189	Intermediate Similarity	NPC123241
0.7186	Intermediate Similarity	NPC25401
0.717	Intermediate Similarity	NPC234772
0.7157	Intermediate Similarity	NPC138830
0.7136	Intermediate Similarity	NPC5630
0.7128	Intermediate Similarity	NPC313757
0.7122	Intermediate Similarity	NPC232600
0.7121	Intermediate Similarity	NPC14994
0.7112	Intermediate Similarity	NPC472102
0.7112	Intermediate Similarity	NPC309531
0.7109	Intermediate Similarity	NPC119722
0.7107	Intermediate Similarity	NPC476095
0.71	Intermediate Similarity	NPC203628
0.7098	Intermediate Similarity	NPC264482
0.7098	Intermediate Similarity	NPC203202
0.7098	Intermediate Similarity	NPC129624
0.7097	Intermediate Similarity	NPC113946
0.7092	Intermediate Similarity	NPC159963
0.7085	Intermediate Similarity	NPC284706
0.7073	Intermediate Similarity	NPC67904
0.7072	Intermediate Similarity	NPC264589
0.7071	Intermediate Similarity	NPC282092
0.7059	Intermediate Similarity	NPC36495
0.7056	Intermediate Similarity	NPC126556
0.7044	Intermediate Similarity	NPC303214
0.7035	Intermediate Similarity	NPC285841
0.7033	Intermediate Similarity	NPC212799
0.7021	Intermediate Similarity	NPC248117
0.702	Intermediate Similarity	NPC322621
0.7019	Intermediate Similarity	NPC87714
0.7019	Intermediate Similarity	NPC475147
0.7014	Intermediate Similarity	NPC234999
0.7005	Intermediate Similarity	NPC61013
0.7	Intermediate Similarity	NPC470480
0.6995	Remote Similarity	NPC96901
0.699	Remote Similarity	NPC127178
0.6979	Remote Similarity	NPC469915
0.6977	Remote Similarity	NPC473837
0.6974	Remote Similarity	NPC476326
0.697	Remote Similarity	NPC245741
0.6968	Remote Similarity	NPC193410
0.6965	Remote Similarity	NPC474059
0.6963	Remote Similarity	NPC472114
0.6963	Remote Similarity	NPC214960
0.6963	Remote Similarity	NPC279527
0.6963	Remote Similarity	NPC472115
0.6952	Remote Similarity	NPC29285
0.6939	Remote Similarity	NPC6974
0.6935	Remote Similarity	NPC478076
0.6933	Remote Similarity	NPC291173
0.6927	Remote Similarity	NPC224970
0.6927	Remote Similarity	NPC167724
0.6927	Remote Similarity	NPC223595
0.6927	Remote Similarity	NPC46259
0.6923	Remote Similarity	NPC1464
0.6919	Remote Similarity	NPC154602
0.6912	Remote Similarity	NPC223590
0.6907	Remote Similarity	NPC285622
0.6907	Remote Similarity	NPC473743
0.6895	Remote Similarity	NPC286871
0.6887	Remote Similarity	NPC475133
0.6882	Remote Similarity	NPC285381
0.6881	Remote Similarity	NPC140311
0.6872	Remote Similarity	NPC13367
0.6869	Remote Similarity	NPC475778
0.6866	Remote Similarity	NPC77777
0.6866	Remote Similarity	NPC473815
0.6854	Remote Similarity	NPC269449
0.6847	Remote Similarity	NPC22476
0.6828	Remote Similarity	NPC243756
0.6828	Remote Similarity	NPC475763
0.6825	Remote Similarity	NPC195787
0.6825	Remote Similarity	NPC211525
0.6825	Remote Similarity	NPC104345
0.6825	Remote Similarity	NPC246140
0.6825	Remote Similarity	NPC153694
0.6823	Remote Similarity	NPC471124
0.6823	Remote Similarity	NPC52059
0.6823	Remote Similarity	NPC470069
0.6821	Remote Similarity	NPC298851
0.6821	Remote Similarity	NPC181138
0.6821	Remote Similarity	NPC21752
0.6821	Remote Similarity	NPC210415
0.6821	Remote Similarity	NPC276993
0.6821	Remote Similarity	NPC293255
0.6818	Remote Similarity	NPC106593
0.6812	Remote Similarity	NPC265642
0.6812	Remote Similarity	NPC138615
0.6812	Remote Similarity	NPC218733
0.6812	Remote Similarity	NPC132874
0.6809	Remote Similarity	NPC473297
0.6796	Remote Similarity	NPC22082
0.6796	Remote Similarity	NPC186284
0.6791	Remote Similarity	NPC122106
0.6789	Remote Similarity	NPC310403
0.6789	Remote Similarity	NPC97380
0.6789	Remote Similarity	NPC471122
0.6789	Remote Similarity	NPC243673
0.6789	Remote Similarity	NPC263709
0.6789	Remote Similarity	NPC148468
0.6789	Remote Similarity	NPC63210
0.6787	Remote Similarity	NPC473667
0.6786	Remote Similarity	NPC475097
0.678	Remote Similarity	NPC470485
0.6768	Remote Similarity	NPC475094
0.6763	Remote Similarity	NPC475559
0.6763	Remote Similarity	NPC302548
0.6757	Remote Similarity	NPC19175
0.6747	Remote Similarity	NPC260909
0.674	Remote Similarity	NPC160113
0.674	Remote Similarity	NPC476220
0.6721	Remote Similarity	NPC237901
0.6721	Remote Similarity	NPC195788
0.6719	Remote Similarity	NPC176983
0.6713	Remote Similarity	NPC10732
0.671	Remote Similarity	NPC469722
0.6701	Remote Similarity	NPC469726
0.6701	Remote Similarity	NPC329338
0.67	Remote Similarity	NPC21425
0.6697	Remote Similarity	NPC128476
0.6683	Remote Similarity	NPC470483
0.6682	Remote Similarity	NPC231924
0.6682	Remote Similarity	NPC162730
0.6667	Remote Similarity	NPC249150
0.6667	Remote Similarity	NPC475427
0.6667	Remote Similarity	NPC79129
0.6667	Remote Similarity	NPC81654
0.6667	Remote Similarity	NPC195461
0.6667	Remote Similarity	NPC313985
0.6667	Remote Similarity	NPC33507
0.6667	Remote Similarity	NPC49196
0.6667	Remote Similarity	NPC73644
0.6667	Remote Similarity	NPC195636
0.665	Remote Similarity	NPC473880
0.665	Remote Similarity	NPC286994
0.6638	Remote Similarity	NPC469452
0.6638	Remote Similarity	NPC154922
0.6633	Remote Similarity	NPC472118
0.6632	Remote Similarity	NPC161827
0.6632	Remote Similarity	NPC476231
0.6632	Remote Similarity	NPC469741
0.6623	Remote Similarity	NPC304837
0.6623	Remote Similarity	NPC476258
0.6615	Remote Similarity	NPC278887
0.6604	Remote Similarity	NPC475223

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 NPC473375 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	496
0.2-0.3	724
0.3-0.4	2147
0.4-0.5	3825
0.5-0.6	1661
0.6-0.7	129
0.7-0.8	3
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
0.6834	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7962	Phase 2
0.6782	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1663	Discontinued
0.6747	Remote Similarity	NPD8460	Approved
0.6747	Remote Similarity	NPD8459	Approved
0.6721	Remote Similarity	NPD8427	Approved
0.6721	Remote Similarity	NPD8465	Approved
0.6721	Remote Similarity	NPD8466	Approved
0.6721	Remote Similarity	NPD8467	Approved
0.6721	Remote Similarity	NPD8429	Approved
0.6721	Remote Similarity	NPD8428	Approved
0.6701	Remote Similarity	NPD3423	Phase 2
0.6701	Remote Similarity	NPD3422	Phase 3
0.6682	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4601	Approved
0.6667	Remote Similarity	NPD4600	Approved
0.6667	Remote Similarity	NPD6805	Discontinued
0.6652	Remote Similarity	NPD7186	Phase 3
0.6649	Remote Similarity	NPD7606	Phase 3
0.6633	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8425	Approved
0.6614	Remote Similarity	NPD8426	Approved
0.6587	Remote Similarity	NPD4602	Approved
0.6562	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8363	Approved
0.6545	Remote Similarity	NPD8364	Approved
0.6528	Remote Similarity	NPD7599	Phase 2
0.6522	Remote Similarity	NPD2093	Discontinued
0.6495	Remote Similarity	NPD7205	Discontinued
0.6495	Remote Similarity	NPD7600	Phase 2
0.6492	Remote Similarity	NPD4120	Approved
0.6492	Remote Similarity	NPD4121	Phase 3
0.6492	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7478	Approved
0.6471	Remote Similarity	NPD7295	Approved
0.6459	Remote Similarity	NPD5610	Approved
0.6458	Remote Similarity	NPD5741	Approved
0.6458	Remote Similarity	NPD5743	Approved
0.6458	Remote Similarity	NPD5742	Approved
0.6452	Remote Similarity	NPD7082	Approved
0.6445	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5504	Discontinued
0.6435	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7487	Discontinued
0.6393	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5609	Approved
0.6385	Remote Similarity	NPD5608	Approved
0.6385	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7300	Phase 3
0.6376	Remote Similarity	NPD7302	Phase 3
0.6368	Remote Similarity	NPD5941	Approved
0.6368	Remote Similarity	NPD5942	Approved
0.6368	Remote Similarity	NPD3828	Approved
0.6364	Remote Similarity	NPD2820	Phase 3
0.6359	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7293	Approved
0.6338	Remote Similarity	NPD4668	Phase 2
0.6336	Remote Similarity	NPD8489	Phase 1
0.6327	Remote Similarity	NPD2506	Approved
0.6324	Remote Similarity	NPD4330	Approved
0.6324	Remote Similarity	NPD4329	Approved
0.6318	Remote Similarity	NPD3377	Discontinued
0.6316	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2365	Approved
0.6301	Remote Similarity	NPD4859	Phase 1
0.6293	Remote Similarity	NPD3470	Approved
0.6293	Remote Similarity	NPD3471	Approved
0.629	Remote Similarity	NPD4493	Discontinued
0.6287	Remote Similarity	NPD5466	Approved
0.6286	Remote Similarity	NPD8240	Discontinued
0.6283	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4430	Phase 2
0.6277	Remote Similarity	NPD5024	Approved
0.6275	Remote Similarity	NPD3782	Discontinued
0.6271	Remote Similarity	NPD7560	Approved
0.6271	Remote Similarity	NPD519	Approved
0.6263	Remote Similarity	NPD6416	Phase 2
0.6261	Remote Similarity	NPD7301	Phase 3
0.6256	Remote Similarity	NPD7105	Phase 1
0.6256	Remote Similarity	NPD5506	Approved
0.6256	Remote Similarity	NPD5507	Approved
0.625	Remote Similarity	NPD6238	Discontinued
0.6244	Remote Similarity	NPD5582	Discontinued
0.6244	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7259	Approved
0.6225	Remote Similarity	NPD3792	Approved
0.6215	Remote Similarity	NPD2974	Approved
0.6215	Remote Similarity	NPD2973	Approved
0.6215	Remote Similarity	NPD2975	Approved
0.6209	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD4897	Phase 2
0.6202	Remote Similarity	NPD6557	Phase 2
0.6199	Remote Similarity	NPD4520	Approved
0.6197	Remote Similarity	NPD5947	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6311	Approved
0.6196	Remote Similarity	NPD5182	Approved
0.6196	Remote Similarity	NPD6309	Approved
0.6196	Remote Similarity	NPD5184	Approved
0.6196	Remote Similarity	NPD6310	Approved
0.6196	Remote Similarity	NPD5185	Approved
0.6195	Remote Similarity	NPD7292	Approved
0.6193	Remote Similarity	NPD2427	Approved
0.6176	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD2493	Approved
0.6175	Remote Similarity	NPD4621	Approved
0.6175	Remote Similarity	NPD3452	Approved
0.6175	Remote Similarity	NPD3450	Approved
0.6175	Remote Similarity	NPD2494	Approved
0.6175	Remote Similarity	NPD4619	Approved
0.6171	Remote Similarity	NPD5860	Discontinued
0.6169	Remote Similarity	NPD2404	Discontinued
0.6169	Remote Similarity	NPD2037	Approved
0.6164	Remote Similarity	NPD3298	Approved
0.6161	Remote Similarity	NPD4499	Approved
0.6161	Remote Similarity	NPD4455	Discontinued
0.6158	Remote Similarity	NPD2575	Approved
0.6157	Remote Similarity	NPD6249	Phase 2
0.6157	Remote Similarity	NPD6248	Phase 2
0.6154	Remote Similarity	NPD4412	Phase 2
0.6154	Remote Similarity	NPD5086	Approved
0.615	Remote Similarity	NPD5430	Discontinued
0.6146	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD8165	Discontinued
0.6142	Remote Similarity	NPD8630	Approved
0.614	Remote Similarity	NPD6206	Phase 1
0.6139	Remote Similarity	NPD7795	Phase 2
0.6136	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD5993	Phase 1
0.6129	Remote Similarity	NPD4580	Approved
0.6128	Remote Similarity	NPD6723	Discontinued
0.6127	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6017	Discontinued
0.6126	Remote Similarity	NPD5835	Phase 3
0.6126	Remote Similarity	NPD5834	Phase 3
0.6121	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD7805	Phase 3
0.6111	Remote Similarity	NPD7778	Approved
0.6111	Remote Similarity	NPD7777	Approved
0.6111	Remote Similarity	NPD6261	Phase 3
0.6111	Remote Similarity	NPD53	Approved
0.6108	Remote Similarity	NPD2431	Approved
0.6108	Remote Similarity	NPD2432	Approved
0.6103	Remote Similarity	NPD8146	Phase 2
0.6096	Remote Similarity	NPD5496	Approved
0.6091	Remote Similarity	NPD2527	Approved
0.6091	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6987	Phase 1
0.6091	Remote Similarity	NPD4583	Approved
0.6091	Remote Similarity	NPD6395	Phase 2
0.6091	Remote Similarity	NPD4582	Approved
0.6089	Remote Similarity	NPD2454	Approved
0.6089	Remote Similarity	NPD2455	Approved
0.6087	Remote Similarity	NPD6995	Phase 1
0.6087	Remote Similarity	NPD6997	Phase 2
0.6087	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6878	Phase 2
0.6087	Remote Similarity	NPD6879	Phase 2
0.6083	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD4082	Approved
0.6079	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD2791	Discontinued
0.6073	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1945	Phase 1
0.6071	Remote Similarity	NPD7595	Discontinued
0.6071	Remote Similarity	NPD2790	Discontinued
0.607	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5600	Discontinued
0.6066	Remote Similarity	NPD6891	Phase 2
0.6066	Remote Similarity	NPD4951	Discontinued
0.6066	Remote Similarity	NPD2613	Approved
0.6066	Remote Similarity	NPD7769	Phase 3
0.6062	Remote Similarity	NPD7707	Approved
0.6058	Remote Similarity	NPD4946	Phase 2
0.6056	Remote Similarity	NPD4370	Phase 3
0.6056	Remote Similarity	NPD6659	Phase 2
0.6047	Remote Similarity	NPD7944	Discontinued
0.6045	Remote Similarity	NPD4004	Approved
0.6045	Remote Similarity	NPD5487	Phase 1
0.6045	Remote Similarity	NPD4002	Approved
0.6044	Remote Similarity	NPD3888	Discontinued
0.6043	Remote Similarity	NPD7688	Phase 1
0.6042	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5823	Approved
0.6038	Remote Similarity	NPD4334	Discontinued
0.6037	Remote Similarity	NPD5194	Approved
0.6037	Remote Similarity	NPD5196	Approved
0.6037	Remote Similarity	NPD5197	Approved
0.6036	Remote Similarity	NPD6518	Discontinued
0.6036	Remote Similarity	NPD4596	Phase 1
0.6034	Remote Similarity	NPD4218	Approved
0.6034	Remote Similarity	NPD2612	Approved
0.6034	Remote Similarity	NPD2608	Approved
0.6034	Remote Similarity	NPD2610	Approved
0.6034	Remote Similarity	NPD3132	Approved
0.6034	Remote Similarity	NPD4215	Approved
0.6034	Remote Similarity	NPD4217	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