NPASS Compound

Structure

CID116519 OpenBabel06191715472D 23 28 0 0 1 0 0 0 0 0999 V2000 1.9429 2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5875 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8690 2.7131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9044 -0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9044 -1.4170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9670 0.2067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9670 -1.9582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1531 0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1786 0.5230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4457 0.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3623 1.1295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7272 0.8324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0295 -0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5168 1.1020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0295 -1.4170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1850 0.9392 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7128 -0.7626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6363 -0.8757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4403 0.9889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.7515 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2045 1.0987 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8844 -0.6630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 22 1 0 0 0 0 3 19 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 13 2 0 0 0 0 7 15 2 0 0 0 0 8 14 1 0 0 0 0 10 23 1 0 0 0 0 11 19 1 0 0 0 0 11 22 1 0 0 0 0 12 10 1 1 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 1 0 0 0 15 21 1 0 0 0 0 16 9 1 1 0 0 0 16 22 1 0 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 19 20 1 6 0 0 0 20 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.17
Volume:	320.739
LogP:	2.698
LogD:	2.753
LogS:	-3.775
# Rotatable Bonds:	1
TPSA:	24.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	6.65
Fsp3:	0.55
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:	-5.109
MDCK Permeability:	3.400425339350477e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.882

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	57.175323486328125%
Volume Distribution (VD):	2.733
Pgp-substrate:	47.30353927612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.777
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.222
CYP2D6-inhibitor:	0.802
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.861
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	8.196
Half-life (T1/2):	0.052

ADMET: Toxicity

hERG Blockers:	0.67
Human Hepatotoxicity (H-HT):	0.441
Drug-inuced Liver Injury (DILI):	0.645
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.563
Carcinogencity:	0.438
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC116519

Natural Product ID:	NPC116519
*Common Name:**	Koumine
IUPAC Name:	n.a.
Synonyms:	Koumine
Standard InCHIKey:	VTLYEMHGPMGUOT-XMHJOAAQSA-N
Standard InCHI:	InChI=1S/C20H22N2O/c1-3-19-11-22(2)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-23-17/h3-7,12,14,16-17H,1,8-11H2,2H3/t12-,14+,16-,17-,19-,20-/m0/s1
SMILES:	C=C[C@]12CN(C)[C@@H]3[C@@H]4[C@H]1C[C@@H](C1=Nc5c([C@]21C3)cccc5)OC4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522743
PubChem CID:	44583834
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643063]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989532]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256496]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	leaves and vine stems	Xishuangbanna Tropical Botanical Garden (XTBG), Chinese Academy of Science (CAS), Mengla County, Yunnan Province, China	2009-OCT	PMID[26103517]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222693]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	EC50	>	100000.0	nM	PMID[535959]

☑ 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 NPC116519 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	350
0.1-0.2	1598
0.2-0.3	6536
0.3-0.4	21690
0.4-0.5	9025
0.5-0.6	3090
0.6-0.7	350
0.7-0.8	50
0.8-0.85	3
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC477156
0.9375	High Similarity	NPC477157
0.8936	High Similarity	NPC477155
0.88	High Similarity	NPC477158
0.8662	High Similarity	NPC243162
0.8052	Intermediate Similarity	NPC473297
0.7947	Intermediate Similarity	NPC472100
0.7762	Intermediate Similarity	NPC478079
0.7673	Intermediate Similarity	NPC469461
0.7626	Intermediate Similarity	NPC264580
0.7607	Intermediate Similarity	NPC469462
0.7582	Intermediate Similarity	NPC472103
0.7485	Intermediate Similarity	NPC475420
0.7484	Intermediate Similarity	NPC264589
0.7333	Intermediate Similarity	NPC278887
0.7262	Intermediate Similarity	NPC473880
0.7195	Intermediate Similarity	NPC225319
0.7168	Intermediate Similarity	NPC19679
0.716	Intermediate Similarity	NPC473743
0.716	Intermediate Similarity	NPC139085
0.716	Intermediate Similarity	NPC214626
0.716	Intermediate Similarity	NPC161827
0.716	Intermediate Similarity	NPC251212
0.7158	Intermediate Similarity	NPC52801
0.7152	Intermediate Similarity	NPC99632
0.7152	Intermediate Similarity	NPC469735
0.7152	Intermediate Similarity	NPC282339
0.711	Intermediate Similarity	NPC475962
0.7091	Intermediate Similarity	NPC143457
0.7086	Intermediate Similarity	NPC476095
0.7081	Intermediate Similarity	NPC475763
0.7081	Intermediate Similarity	NPC206592
0.7076	Intermediate Similarity	NPC320147
0.7073	Intermediate Similarity	NPC211525
0.7073	Intermediate Similarity	NPC153694
0.7048	Intermediate Similarity	NPC472121
0.703	Intermediate Similarity	NPC310403
0.703	Intermediate Similarity	NPC148468
0.703	Intermediate Similarity	NPC63210
0.703	Intermediate Similarity	NPC97380
0.703	Intermediate Similarity	NPC263709
0.703	Intermediate Similarity	NPC243673
0.7025	Intermediate Similarity	NPC311330
0.7012	Intermediate Similarity	NPC29285
0.7006	Intermediate Similarity	NPC285841
0.7	Intermediate Similarity	NPC212799
0.7	Intermediate Similarity	NPC469740
0.6988	Remote Similarity	NPC81229
0.6988	Remote Similarity	NPC255229
0.6977	Remote Similarity	NPC24594
0.6977	Remote Similarity	NPC472122
0.6964	Remote Similarity	NPC52059
0.6964	Remote Similarity	NPC470069
0.6959	Remote Similarity	NPC21752
0.6959	Remote Similarity	NPC181138
0.6959	Remote Similarity	NPC298851
0.6959	Remote Similarity	NPC293255
0.6959	Remote Similarity	NPC210415
0.6959	Remote Similarity	NPC276993
0.6954	Remote Similarity	NPC187827
0.6954	Remote Similarity	NPC472105
0.6919	Remote Similarity	NPC475097
0.6905	Remote Similarity	NPC469541
0.6901	Remote Similarity	NPC126492
0.6893	Remote Similarity	NPC52262
0.6893	Remote Similarity	NPC469460
0.6893	Remote Similarity	NPC472209
0.6875	Remote Similarity	NPC472104
0.6867	Remote Similarity	NPC113946
0.6864	Remote Similarity	NPC472106
0.686	Remote Similarity	NPC96901
0.6839	Remote Similarity	NPC260075
0.6833	Remote Similarity	NPC22689
0.6833	Remote Similarity	NPC105055
0.6821	Remote Similarity	NPC189812
0.6821	Remote Similarity	NPC329688
0.6821	Remote Similarity	NPC13367
0.6806	Remote Similarity	NPC126066
0.68	Remote Similarity	NPC133261
0.6788	Remote Similarity	NPC478076
0.678	Remote Similarity	NPC472109
0.678	Remote Similarity	NPC472108
0.678	Remote Similarity	NPC139291
0.678	Remote Similarity	NPC472110
0.6746	Remote Similarity	NPC472120
0.6746	Remote Similarity	NPC176983
0.6746	Remote Similarity	NPC472101
0.6744	Remote Similarity	NPC469915
0.6743	Remote Similarity	NPC326575
0.674	Remote Similarity	NPC95783
0.6712	Remote Similarity	NPC192209
0.6704	Remote Similarity	NPC79062
0.6704	Remote Similarity	NPC472107
0.6703	Remote Similarity	NPC162440
0.6702	Remote Similarity	NPC87755
0.6689	Remote Similarity	NPC325013
0.6667	Remote Similarity	NPC476425
0.6667	Remote Similarity	NPC472123
0.6667	Remote Similarity	NPC132847
0.6648	Remote Similarity	NPC245741
0.6647	Remote Similarity	NPC114808
0.6632	Remote Similarity	NPC475422
0.663	Remote Similarity	NPC203972
0.6626	Remote Similarity	NPC470579
0.6621	Remote Similarity	NPC470550
0.6595	Remote Similarity	NPC221687
0.6592	Remote Similarity	NPC98197
0.6592	Remote Similarity	NPC256288
0.6591	Remote Similarity	NPC264482
0.6591	Remote Similarity	NPC203202
0.659	Remote Similarity	NPC154293
0.6575	Remote Similarity	NPC282092
0.6575	Remote Similarity	NPC66210
0.6568	Remote Similarity	NPC104345
0.6561	Remote Similarity	NPC313352
0.6561	Remote Similarity	NPC184437
0.6556	Remote Similarity	NPC258480
0.6556	Remote Similarity	NPC2933
0.6552	Remote Similarity	NPC187036
0.655	Remote Similarity	NPC472117
0.6548	Remote Similarity	NPC251936
0.6538	Remote Similarity	NPC181928
0.6532	Remote Similarity	NPC98187
0.6531	Remote Similarity	NPC475602
0.6526	Remote Similarity	NPC474077
0.6526	Remote Similarity	NPC162730
0.6522	Remote Similarity	NPC28510
0.6519	Remote Similarity	NPC259626
0.6508	Remote Similarity	NPC79129
0.6508	Remote Similarity	NPC313985
0.6508	Remote Similarity	NPC138830
0.6508	Remote Similarity	NPC67904
0.6508	Remote Similarity	NPC81654
0.6508	Remote Similarity	NPC195461
0.6508	Remote Similarity	NPC49196
0.6508	Remote Similarity	NPC249150
0.6497	Remote Similarity	NPC476441
0.6491	Remote Similarity	NPC309531
0.6491	Remote Similarity	NPC472102
0.6491	Remote Similarity	NPC248117
0.6484	Remote Similarity	NPC473615
0.6484	Remote Similarity	NPC291759
0.6481	Remote Similarity	NPC470925
0.648	Remote Similarity	NPC300688
0.648	Remote Similarity	NPC15840
0.6467	Remote Similarity	NPC469501
0.6467	Remote Similarity	NPC469470
0.6467	Remote Similarity	NPC33421
0.6467	Remote Similarity	NPC473298
0.6464	Remote Similarity	NPC165201
0.6464	Remote Similarity	NPC472119
0.6461	Remote Similarity	NPC211997
0.6457	Remote Similarity	NPC257354
0.6456	Remote Similarity	NPC90693
0.6456	Remote Similarity	NPC64897
0.6456	Remote Similarity	NPC325568
0.6454	Remote Similarity	NPC474695
0.6453	Remote Similarity	NPC286871
0.6453	Remote Similarity	NPC85651
0.6452	Remote Similarity	NPC295478
0.6452	Remote Similarity	NPC259098
0.6452	Remote Similarity	NPC197680
0.6448	Remote Similarity	NPC21425
0.6448	Remote Similarity	NPC229484
0.6442	Remote Similarity	NPC473922
0.644	Remote Similarity	NPC474116
0.6438	Remote Similarity	NPC296163
0.6437	Remote Similarity	NPC279527
0.6437	Remote Similarity	NPC214960
0.6436	Remote Similarity	NPC106593
0.6433	Remote Similarity	NPC53044
0.6433	Remote Similarity	NPC193410
0.6432	Remote Similarity	NPC472097
0.6429	Remote Similarity	NPC133591
0.6429	Remote Similarity	NPC278097
0.6425	Remote Similarity	NPC6093
0.6424	Remote Similarity	NPC475915
0.642	Remote Similarity	NPC158129
0.642	Remote Similarity	NPC22082
0.642	Remote Similarity	NPC186284
0.6418	Remote Similarity	NPC140311
0.6413	Remote Similarity	NPC292675
0.6413	Remote Similarity	NPC217294
0.641	Remote Similarity	NPC124802
0.641	Remote Similarity	NPC9856
0.6407	Remote Similarity	NPC318086
0.6404	Remote Similarity	NPC473667
0.6404	Remote Similarity	NPC134586
0.6402	Remote Similarity	NPC50503
0.64	Remote Similarity	NPC317430
0.6398	Remote Similarity	NPC472113
0.6395	Remote Similarity	NPC205652
0.6393	Remote Similarity	NPC207033
0.6393	Remote Similarity	NPC38823
0.6387	Remote Similarity	NPC471512
0.6384	Remote Similarity	NPC471294
0.6384	Remote Similarity	NPC97525
0.6383	Remote Similarity	NPC473375
0.6383	Remote Similarity	NPC97100
0.6383	Remote Similarity	NPC231342

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 NPC116519 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	595
0.2-0.3	792
0.3-0.4	1739
0.4-0.5	3880
0.5-0.6	1810
0.6-0.7	113
0.7-0.8	4
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
0.7203	Intermediate Similarity	NPD2210	Approved
0.7203	Intermediate Similarity	NPD2212	Approved
0.7161	Intermediate Similarity	NPD6789	Approved
0.7097	Intermediate Similarity	NPD6606	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2658	Approved
0.7021	Intermediate Similarity	NPD3147	Approved
0.7021	Intermediate Similarity	NPD3148	Approved
0.7021	Intermediate Similarity	NPD3150	Approved
0.7021	Intermediate Similarity	NPD3149	Approved
0.7021	Intermediate Similarity	NPD2659	Approved
0.6994	Remote Similarity	NPD4121	Phase 3
0.6994	Remote Similarity	NPD4120	Approved
0.6981	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5631	Phase 3
0.6951	Remote Similarity	NPD5743	Approved
0.6951	Remote Similarity	NPD5741	Approved
0.6951	Remote Similarity	NPD5742	Approved
0.695	Remote Similarity	NPD1764	Approved
0.695	Remote Similarity	NPD1762	Approved
0.6852	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6025	Phase 1
0.6811	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7461	Approved
0.6772	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7522	Discontinued
0.669	Remote Similarity	NPD2622	Approved
0.6685	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2679	Approved
0.6667	Remote Similarity	NPD2678	Approved
0.6667	Remote Similarity	NPD5185	Approved
0.6667	Remote Similarity	NPD5184	Approved
0.6667	Remote Similarity	NPD5182	Approved
0.6646	Remote Similarity	NPD6301	Phase 2
0.6643	Remote Similarity	NPD2039	Approved
0.6643	Remote Similarity	NPD2038	Approved
0.663	Remote Similarity	NPD4951	Discontinued
0.6629	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4116	Approved
0.6608	Remote Similarity	NPD6635	Approved
0.6607	Remote Similarity	NPD6026	Approved
0.6605	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7487	Discontinued
0.6561	Remote Similarity	NPD7200	Approved
0.6558	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7474	Suspended
0.6526	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD4600	Approved
0.6508	Remote Similarity	NPD4601	Approved
0.6503	Remote Similarity	NPD7633	Discontinued
0.6494	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7418	Discontinued
0.6474	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1001	Discontinued
0.6471	Remote Similarity	NPD6320	Approved
0.6467	Remote Similarity	NPD8353	Approved
0.6467	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD8355	Approved
0.6456	Remote Similarity	NPD3110	Approved
0.6456	Remote Similarity	NPD3109	Approved
0.6447	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2913	Approved
0.6438	Remote Similarity	NPD2914	Approved
0.6434	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5913	Phase 3
0.6429	Remote Similarity	NPD2840	Approved
0.6429	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6069	Approved
0.6419	Remote Similarity	NPD6070	Approved
0.6413	Remote Similarity	NPD7233	Approved
0.6413	Remote Similarity	NPD7234	Approved
0.6412	Remote Similarity	NPD2789	Approved
0.641	Remote Similarity	NPD2606	Approved
0.641	Remote Similarity	NPD3594	Approved
0.641	Remote Similarity	NPD2605	Approved
0.641	Remote Similarity	NPD3595	Approved
0.6402	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5599	Discontinued
0.6395	Remote Similarity	NPD5629	Discontinued
0.6392	Remote Similarity	NPD8118	Discontinued
0.6391	Remote Similarity	NPD6357	Discontinued
0.6391	Remote Similarity	NPD8354	Approved
0.6386	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6281	Approved
0.6369	Remote Similarity	NPD6489	Phase 3
0.6369	Remote Similarity	NPD5156	Approved
0.6369	Remote Similarity	NPD7606	Phase 3
0.6369	Remote Similarity	NPD5155	Approved
0.6364	Remote Similarity	NPD6300	Approved
0.6364	Remote Similarity	NPD6299	Approved
0.6364	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7295	Approved
0.6364	Remote Similarity	NPD7795	Phase 2
0.6364	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1419	Approved
0.6357	Remote Similarity	NPD1417	Approved
0.6346	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3636	Approved
0.6346	Remote Similarity	NPD7582	Discontinued
0.6346	Remote Similarity	NPD3637	Approved
0.6346	Remote Similarity	NPD3635	Approved
0.6344	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6037	Discontinued
0.634	Remote Similarity	NPD478	Approved
0.6337	Remote Similarity	NPD7599	Phase 2
0.6333	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD8401	Approved
0.6331	Remote Similarity	NPD6158	Phase 2
0.6331	Remote Similarity	NPD8402	Approved
0.6331	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD8400	Approved
0.6323	Remote Similarity	NPD6900	Discontinued
0.631	Remote Similarity	NPD6221	Approved
0.631	Remote Similarity	NPD6222	Approved
0.6306	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7600	Phase 2
0.6301	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7478	Approved
0.6279	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD1108	Approved
0.6276	Remote Similarity	NPD1107	Approved
0.6275	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD2475	Phase 2
0.6267	Remote Similarity	NPD7480	Approved
0.6267	Remote Similarity	NPD7481	Approved
0.6258	Remote Similarity	NPD5578	Approved
0.6258	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7479	Phase 2
0.6242	Remote Similarity	NPD7082	Approved
0.6236	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD2882	Phase 1
0.623	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.622	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5179	Approved
0.6216	Remote Similarity	NPD5180	Approved
0.6216	Remote Similarity	NPD5181	Approved
0.6215	Remote Similarity	NPD5862	Discovery
0.6215	Remote Similarity	NPD4640	Approved
0.6215	Remote Similarity	NPD4639	Approved
0.6215	Remote Similarity	NPD4638	Approved
0.6209	Remote Similarity	NPD5579	Approved
0.6209	Remote Similarity	NPD5576	Approved
0.6205	Remote Similarity	NPD7259	Approved
0.6203	Remote Similarity	NPD4499	Approved
0.6203	Remote Similarity	NPD4365	Phase 2
0.6203	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD5997	Discontinued
0.62	Remote Similarity	NPD6660	Discontinued
0.6193	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4572	Approved
0.619	Remote Similarity	NPD4573	Approved
0.619	Remote Similarity	NPD4571	Approved
0.6178	Remote Similarity	NPD7034	Discontinued
0.6173	Remote Similarity	NPD6544	Discontinued
0.617	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5617	Suspended
0.6163	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6227	Discontinued
0.6162	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4702	Approved
0.6154	Remote Similarity	NPD4703	Approved
0.6154	Remote Similarity	NPD4682	Phase 2
0.6154	Remote Similarity	NPD1036	Approved
0.6149	Remote Similarity	NPD4165	Phase 2
0.6149	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD3066	Phase 2
0.6145	Remote Similarity	NPD3975	Discontinued
0.6145	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD2340	Discontinued
0.6143	Remote Similarity	NPD4263	Approved
0.6143	Remote Similarity	NPD4813	Approved
0.6141	Remote Similarity	NPD7962	Phase 2
0.6138	Remote Similarity	NPD5253	Approved
0.6138	Remote Similarity	NPD4115	Approved
0.6138	Remote Similarity	NPD4114	Approved
0.6136	Remote Similarity	NPD3323	Discontinued
0.6135	Remote Similarity	NPD4411	Phase 1
0.6135	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD4734	Approved
0.6127	Remote Similarity	NPD4735	Approved
0.6127	Remote Similarity	NPD2527	Approved
0.6127	Remote Similarity	NPD5716	Approved
0.612	Remote Similarity	NPD6878	Phase 2
0.612	Remote Similarity	NPD6879	Phase 2

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