NPASS Compound

Structure

CID284842 OpenBabel06191716092D 21 24 0 0 1 0 0 0 0 0999 V2000 0.7166 -4.0550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7306 1.2223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4266 -1.4017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4267 -0.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4266 -1.4008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6181 -1.8679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8224 -2.2593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2811 -2.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6177 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3116 -2.6703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6178 -1.8685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4264 -0.4664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6182 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8087 -0.4668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8088 -1.4014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8089 -1.4011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5617 -3.0877 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2497 0.0091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6185 0.9334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 12 19 2 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 6 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.14
Volume:	292.548
LogP:	1.486
LogD:	0.969
LogS:	-1.939
# Rotatable Bonds:	1
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	4.055
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.674
MDCK Permeability:	2.9634133170475252e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.088
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998
Plasma Protein Binding (PPB):	37.29657745361328%
Volume Distribution (VD):	1.986
Pgp-substrate:	66.72937774658203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.157
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.498
CYP2D6-inhibitor:	0.854
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.128
CYP3A4-substrate:	0.864

ADMET: Excretion

Clearance (CL):	9.29
Half-life (T1/2):	0.564

ADMET: Toxicity

hERG Blockers:	0.329
Human Hepatotoxicity (H-HT):	0.636
Drug-inuced Liver Injury (DILI):	0.219
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.932
Carcinogencity:	0.922
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC284842

Natural Product ID:	NPC284842
*Common Name:**	Narwedine
IUPAC Name:	n.a.
Synonyms:	Narwedine
Standard InCHIKey:	QENVUHCAYXAROT-YOEHRIQHSA-N
Standard InCHI:	InChI=1S/C17H19NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,14H,7-10H2,1-2H3/t14-,17-/m0/s1
SMILES:	COc1ccc2c3c1O[C@@H]1[C@@]3(CCN(C2)C)C=CC(=O)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146604
PubChem CID:	10356588
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004128] Galanthamine-type amaryllidaceae 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
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO33437	amaryllidaceae	Family	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921081]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26604	Aralia subcapitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO272	Pittosporum eugenioides	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26604	Aralia subcapitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23091	Halocarpus bidwillii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26154	Erythropodium caribaeorum	Species	Anthothelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26641	Pteroxygonum giraldii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21398	Jasminum laurifolium f. nitidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13480	Stereocaulon dactylophyllum	Species	Stereocaulaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1160	Cell Line	BJ	Homo sapiens	IC50	>	50000.0	nM	PMID[526457]
NPT2468	Cell Line	G-361	Homo sapiens	IC50	>	50000.0	nM	PMID[526457]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[526457]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[526457]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[526457]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	31600.0	nM	PMID[526457]

☑ 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 NPC284842 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	285
0.1-0.2	1329
0.2-0.3	4161
0.3-0.4	11607
0.4-0.5	6043
0.5-0.6	9163
0.6-0.7	9352
0.7-0.8	726
0.8-0.85	20
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8812	High Similarity	NPC40389
0.8812	High Similarity	NPC78359
0.8812	High Similarity	NPC315707
0.8812	High Similarity	NPC148014
0.8812	High Similarity	NPC65490
0.8696	High Similarity	NPC129603
0.8589	High Similarity	NPC18402
0.8485	Intermediate Similarity	NPC293871
0.8485	Intermediate Similarity	NPC124433
0.8286	Intermediate Similarity	NPC214629
0.8182	Intermediate Similarity	NPC180756
0.8182	Intermediate Similarity	NPC323443
0.8095	Intermediate Similarity	NPC153631
0.8084	Intermediate Similarity	NPC118804
0.8011	Intermediate Similarity	NPC115906
0.7977	Intermediate Similarity	NPC67978
0.7977	Intermediate Similarity	NPC303581
0.7886	Intermediate Similarity	NPC308267
0.7853	Intermediate Similarity	NPC27887
0.7849	Intermediate Similarity	NPC124657
0.7836	Intermediate Similarity	NPC476569
0.7831	Intermediate Similarity	NPC476579
0.7802	Intermediate Similarity	NPC63152
0.7791	Intermediate Similarity	NPC130926
0.7791	Intermediate Similarity	NPC2770
0.7791	Intermediate Similarity	NPC39103
0.7784	Intermediate Similarity	NPC46744
0.7784	Intermediate Similarity	NPC70290
0.7784	Intermediate Similarity	NPC73020
0.7784	Intermediate Similarity	NPC215098
0.7784	Intermediate Similarity	NPC124302
0.7784	Intermediate Similarity	NPC14622
0.7772	Intermediate Similarity	NPC174783
0.7759	Intermediate Similarity	NPC470324
0.7759	Intermediate Similarity	NPC86469
0.774	Intermediate Similarity	NPC35680
0.7725	Intermediate Similarity	NPC119669
0.7714	Intermediate Similarity	NPC75958
0.7714	Intermediate Similarity	NPC474708
0.7701	Intermediate Similarity	NPC226652
0.7701	Intermediate Similarity	NPC120671
0.7701	Intermediate Similarity	NPC314100
0.7701	Intermediate Similarity	NPC72788
0.7697	Intermediate Similarity	NPC121400
0.7692	Intermediate Similarity	NPC160193
0.7692	Intermediate Similarity	NPC78733
0.767	Intermediate Similarity	NPC227683
0.7665	Intermediate Similarity	NPC223125
0.7661	Intermediate Similarity	NPC106786
0.7657	Intermediate Similarity	NPC475845
0.7647	Intermediate Similarity	NPC147091
0.7647	Intermediate Similarity	NPC57512
0.7647	Intermediate Similarity	NPC133817
0.7647	Intermediate Similarity	NPC476443
0.7644	Intermediate Similarity	NPC476002
0.764	Intermediate Similarity	NPC241704
0.764	Intermediate Similarity	NPC222524
0.764	Intermediate Similarity	NPC474470
0.7633	Intermediate Similarity	NPC470708
0.763	Intermediate Similarity	NPC59567
0.7619	Intermediate Similarity	NPC202771
0.7619	Intermediate Similarity	NPC119818
0.7619	Intermediate Similarity	NPC328700
0.7619	Intermediate Similarity	NPC2173
0.7619	Intermediate Similarity	NPC67346
0.7609	Intermediate Similarity	NPC196231
0.76	Intermediate Similarity	NPC57812
0.76	Intermediate Similarity	NPC474324
0.7596	Intermediate Similarity	NPC208890
0.7596	Intermediate Similarity	NPC141440
0.7593	Intermediate Similarity	NPC314682
0.7586	Intermediate Similarity	NPC247972
0.7586	Intermediate Similarity	NPC231198
0.7581	Intermediate Similarity	NPC477258
0.7574	Intermediate Similarity	NPC223124
0.7574	Intermediate Similarity	NPC148898
0.7574	Intermediate Similarity	NPC476580
0.7569	Intermediate Similarity	NPC102760
0.7566	Intermediate Similarity	NPC311781
0.7564	Intermediate Similarity	NPC172403
0.756	Intermediate Similarity	NPC274026
0.7558	Intermediate Similarity	NPC59028
0.7558	Intermediate Similarity	NPC92191
0.7557	Intermediate Similarity	NPC83198
0.7557	Intermediate Similarity	NPC290759
0.7557	Intermediate Similarity	NPC204908
0.7557	Intermediate Similarity	NPC158148
0.7557	Intermediate Similarity	NPC82533
0.7557	Intermediate Similarity	NPC266176
0.7556	Intermediate Similarity	NPC32154
0.7546	Intermediate Similarity	NPC188163
0.7546	Intermediate Similarity	NPC213206
0.7546	Intermediate Similarity	NPC474915
0.7546	Intermediate Similarity	NPC328750
0.7545	Intermediate Similarity	NPC37144
0.7545	Intermediate Similarity	NPC59907
0.7541	Intermediate Similarity	NPC477259
0.7541	Intermediate Similarity	NPC169387
0.7541	Intermediate Similarity	NPC230098
0.754	Intermediate Similarity	NPC66909
0.753	Intermediate Similarity	NPC473934
0.7527	Intermediate Similarity	NPC474746
0.7527	Intermediate Similarity	NPC475981
0.7527	Intermediate Similarity	NPC116007
0.7526	Intermediate Similarity	NPC97086
0.7526	Intermediate Similarity	NPC43069
0.7526	Intermediate Similarity	NPC140577
0.7516	Intermediate Similarity	NPC7018
0.7515	Intermediate Similarity	NPC218575
0.7515	Intermediate Similarity	NPC8337
0.7515	Intermediate Similarity	NPC85747
0.7514	Intermediate Similarity	NPC249274
0.75	Intermediate Similarity	NPC51681
0.7486	Intermediate Similarity	NPC18306
0.7486	Intermediate Similarity	NPC306669
0.7485	Intermediate Similarity	NPC476144
0.7485	Intermediate Similarity	NPC16107
0.7485	Intermediate Similarity	NPC106295
0.7485	Intermediate Similarity	NPC476151
0.7485	Intermediate Similarity	NPC244112
0.7485	Intermediate Similarity	NPC51957
0.7485	Intermediate Similarity	NPC210437
0.7472	Intermediate Similarity	NPC477640
0.7472	Intermediate Similarity	NPC65403
0.7472	Intermediate Similarity	NPC470739
0.7472	Intermediate Similarity	NPC225597
0.7471	Intermediate Similarity	NPC82285
0.7471	Intermediate Similarity	NPC133011
0.7459	Intermediate Similarity	NPC474745
0.7459	Intermediate Similarity	NPC244554
0.7458	Intermediate Similarity	NPC58766
0.7458	Intermediate Similarity	NPC475686
0.7453	Intermediate Similarity	NPC37065
0.7446	Intermediate Similarity	NPC162694
0.744	Intermediate Similarity	NPC475959
0.744	Intermediate Similarity	NPC7467
0.7435	Intermediate Similarity	NPC232533
0.7435	Intermediate Similarity	NPC243483
0.743	Intermediate Similarity	NPC152680
0.743	Intermediate Similarity	NPC190783
0.743	Intermediate Similarity	NPC232386
0.7421	Intermediate Similarity	NPC280399
0.7421	Intermediate Similarity	NPC233961
0.7421	Intermediate Similarity	NPC339621
0.7419	Intermediate Similarity	NPC319549
0.7419	Intermediate Similarity	NPC226708
0.7416	Intermediate Similarity	NPC474475
0.7414	Intermediate Similarity	NPC97072
0.7414	Intermediate Similarity	NPC205167
0.7414	Intermediate Similarity	NPC135006
0.7414	Intermediate Similarity	NPC215829
0.7414	Intermediate Similarity	NPC475780
0.7405	Intermediate Similarity	NPC166979
0.7403	Intermediate Similarity	NPC474325
0.7403	Intermediate Similarity	NPC21885
0.7399	Intermediate Similarity	NPC476572
0.7396	Intermediate Similarity	NPC103379
0.7396	Intermediate Similarity	NPC477565
0.7396	Intermediate Similarity	NPC470088
0.7389	Intermediate Similarity	NPC49353
0.7389	Intermediate Similarity	NPC304675
0.7386	Intermediate Similarity	NPC225774
0.7386	Intermediate Similarity	NPC3375
0.7386	Intermediate Similarity	NPC255607
0.7384	Intermediate Similarity	NPC169742
0.7384	Intermediate Similarity	NPC216459
0.7384	Intermediate Similarity	NPC99659
0.7384	Intermediate Similarity	NPC325871
0.7384	Intermediate Similarity	NPC41178
0.7384	Intermediate Similarity	NPC138487
0.7382	Intermediate Similarity	NPC64576
0.7382	Intermediate Similarity	NPC201055
0.7382	Intermediate Similarity	NPC151470
0.7382	Intermediate Similarity	NPC254045
0.738	Intermediate Similarity	NPC94499
0.7365	Intermediate Similarity	NPC15743
0.7365	Intermediate Similarity	NPC185838
0.7363	Intermediate Similarity	NPC99723
0.7349	Intermediate Similarity	NPC128019
0.7349	Intermediate Similarity	NPC136860
0.7349	Intermediate Similarity	NPC476567
0.7348	Intermediate Similarity	NPC237044
0.7345	Intermediate Similarity	NPC24264
0.7345	Intermediate Similarity	NPC476432
0.7345	Intermediate Similarity	NPC219341
0.7344	Intermediate Similarity	NPC286135
0.7341	Intermediate Similarity	NPC477132
0.7341	Intermediate Similarity	NPC477133
0.7341	Intermediate Similarity	NPC146288
0.7337	Intermediate Similarity	NPC83511
0.7333	Intermediate Similarity	NPC4669
0.7333	Intermediate Similarity	NPC2314
0.733	Intermediate Similarity	NPC320104
0.733	Intermediate Similarity	NPC218614
0.7329	Intermediate Similarity	NPC160692
0.7322	Intermediate Similarity	NPC298339
0.7318	Intermediate Similarity	NPC311991
0.7316	Intermediate Similarity	NPC83019
0.7316	Intermediate Similarity	NPC293624
0.731	Intermediate Similarity	NPC81733

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 NPC284842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	749
0.2-0.3	971
0.3-0.4	2223
0.4-0.5	2428
0.5-0.6	1666
0.6-0.7	754
0.7-0.8	143
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8812	High Similarity	NPD2563	Approved
0.8812	High Similarity	NPD2560	Approved
0.8494	Intermediate Similarity	NPD6071	Discontinued
0.8011	Intermediate Similarity	NPD2968	Approved
0.8011	Intermediate Similarity	NPD2971	Approved
0.7927	Intermediate Similarity	NPD3640	Phase 3
0.7927	Intermediate Similarity	NPD3639	Approved
0.7927	Intermediate Similarity	NPD3641	Approved
0.7861	Intermediate Similarity	NPD4481	Phase 3
0.7811	Intermediate Similarity	NPD5978	Approved
0.7811	Intermediate Similarity	NPD5977	Approved
0.7784	Intermediate Similarity	NPD4420	Approved
0.7759	Intermediate Similarity	NPD2898	Approved
0.7701	Intermediate Similarity	NPD2969	Approved
0.7701	Intermediate Similarity	NPD2970	Approved
0.7701	Intermediate Similarity	NPD4107	Approved
0.7679	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD2488	Approved
0.765	Intermediate Similarity	NPD2490	Approved
0.7644	Intermediate Similarity	NPD3051	Approved
0.7619	Intermediate Similarity	NPD5006	Approved
0.7619	Intermediate Similarity	NPD3057	Approved
0.7619	Intermediate Similarity	NPD5005	Approved
0.7605	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4482	Phase 3
0.7557	Intermediate Similarity	NPD2489	Approved
0.7557	Intermediate Similarity	NPD27	Approved
0.7554	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD2975	Approved
0.754	Intermediate Similarity	NPD2974	Approved
0.754	Intermediate Similarity	NPD2973	Approved
0.7529	Intermediate Similarity	NPD6386	Approved
0.7529	Intermediate Similarity	NPD6385	Approved
0.7528	Intermediate Similarity	NPD5312	Approved
0.7528	Intermediate Similarity	NPD5313	Approved
0.7526	Intermediate Similarity	NPD3533	Approved
0.7526	Intermediate Similarity	NPD2972	Approved
0.7516	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7831	Phase 2
0.7514	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7833	Phase 2
0.75	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4584	Approved
0.7471	Intermediate Similarity	NPD6876	Approved
0.7471	Intermediate Similarity	NPD6875	Approved
0.7469	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4210	Discontinued
0.7447	Intermediate Similarity	NPD5564	Approved
0.7435	Intermediate Similarity	NPD3448	Approved
0.7435	Intermediate Similarity	NPD2491	Approved
0.7427	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4772	Phase 2
0.7427	Intermediate Similarity	NPD7110	Phase 1
0.7427	Intermediate Similarity	NPD4773	Phase 2
0.7421	Intermediate Similarity	NPD4580	Approved
0.7419	Intermediate Similarity	NPD7296	Approved
0.7401	Intermediate Similarity	NPD5242	Approved
0.7396	Intermediate Similarity	NPD6031	Approved
0.7396	Intermediate Similarity	NPD6030	Approved
0.7396	Intermediate Similarity	NPD5976	Discontinued
0.7394	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD3452	Approved
0.7382	Intermediate Similarity	NPD2494	Approved
0.7382	Intermediate Similarity	NPD2493	Approved
0.7382	Intermediate Similarity	NPD3450	Approved
0.7366	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7291	Discontinued
0.7333	Intermediate Similarity	NPD8156	Discontinued
0.7333	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6873	Phase 2
0.7322	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD824	Approved
0.7288	Intermediate Similarity	NPD6107	Approved
0.7278	Intermediate Similarity	NPD8251	Approved
0.7278	Intermediate Similarity	NPD8252	Approved
0.7278	Intermediate Similarity	NPD8099	Discontinued
0.7268	Intermediate Similarity	NPD4583	Approved
0.7268	Intermediate Similarity	NPD4582	Approved
0.725	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7907	Approved
0.7241	Intermediate Similarity	NPD4585	Approved
0.724	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7313	Approved
0.7228	Intermediate Similarity	NPD7312	Approved
0.7228	Intermediate Similarity	NPD7311	Approved
0.7228	Intermediate Similarity	NPD7310	Approved
0.7222	Intermediate Similarity	NPD5676	Approved
0.7222	Intermediate Similarity	NPD3140	Approved
0.7222	Intermediate Similarity	NPD3142	Approved
0.7219	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4002	Approved
0.7216	Intermediate Similarity	NPD4004	Approved
0.7212	Intermediate Similarity	NPD4476	Approved
0.7212	Intermediate Similarity	NPD4477	Approved
0.7202	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6895	Approved
0.7195	Intermediate Similarity	NPD6896	Approved
0.7189	Intermediate Similarity	NPD7309	Approved
0.7182	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1424	Approved
0.7174	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7906	Approved
0.716	Intermediate Similarity	NPD7124	Phase 2
0.7151	Intermediate Similarity	NPD3686	Approved
0.7151	Intermediate Similarity	NPD4166	Phase 2
0.7151	Intermediate Similarity	NPD3687	Approved
0.715	Intermediate Similarity	NPD5457	Discontinued
0.7143	Intermediate Similarity	NPD4665	Approved
0.7143	Intermediate Similarity	NPD4111	Phase 1
0.7135	Intermediate Similarity	NPD4578	Approved
0.7135	Intermediate Similarity	NPD4577	Approved
0.7135	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5980	Discovery
0.7127	Intermediate Similarity	NPD3446	Phase 1
0.7126	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6997	Phase 2
0.712	Intermediate Similarity	NPD7039	Approved
0.712	Intermediate Similarity	NPD7038	Approved
0.7119	Intermediate Similarity	NPD1307	Phase 2
0.7119	Intermediate Similarity	NPD1309	Phase 2
0.711	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2651	Approved
0.711	Intermediate Similarity	NPD2649	Approved
0.711	Intermediate Similarity	NPD4017	Approved
0.7104	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6618	Phase 2
0.7093	Intermediate Similarity	NPD7427	Discontinued
0.7092	Intermediate Similarity	NPD4040	Phase 1
0.7086	Intermediate Similarity	NPD5720	Discontinued
0.7083	Intermediate Similarity	NPD4236	Phase 3
0.7083	Intermediate Similarity	NPD4237	Approved
0.7083	Intermediate Similarity	NPD2654	Approved
0.7076	Intermediate Similarity	NPD3146	Approved
0.7076	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6788	Approved
0.7059	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4475	Approved
0.7055	Intermediate Similarity	NPD4474	Approved
0.7045	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7048	Phase 3
0.7041	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4110	Phase 3
0.7039	Intermediate Similarity	NPD5494	Approved
0.7037	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2492	Phase 1
0.703	Intermediate Similarity	NPD2653	Approved
0.7029	Intermediate Similarity	NPD5089	Approved
0.7029	Intermediate Similarity	NPD5090	Approved
0.7022	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4663	Approved
0.7006	Intermediate Similarity	NPD2161	Phase 2
0.7005	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6853	Approved
0.7005	Intermediate Similarity	NPD8053	Approved
0.7005	Intermediate Similarity	NPD8054	Approved
0.7005	Intermediate Similarity	NPD6851	Approved
0.7	Intermediate Similarity	NPD5241	Discontinued
0.6995	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2163	Approved
0.6994	Remote Similarity	NPD5718	Phase 2
0.6989	Remote Similarity	NPD6844	Discontinued
0.6989	Remote Similarity	NPD7248	Discontinued
0.6989	Remote Similarity	NPD6279	Approved
0.6989	Remote Similarity	NPD6280	Approved
0.6988	Remote Similarity	NPD743	Approved
0.6988	Remote Similarity	NPD6111	Discontinued
0.6987	Remote Similarity	NPD3445	Approved
0.6987	Remote Similarity	NPD3444	Approved
0.6987	Remote Similarity	NPD3443	Approved
0.6982	Remote Similarity	NPD4162	Approved
0.6978	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4123	Phase 3
0.6977	Remote Similarity	NPD4662	Approved
0.6977	Remote Similarity	NPD4661	Approved
0.6977	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6297	Approved
0.6964	Remote Similarity	NPD1375	Discontinued
0.6961	Remote Similarity	NPD7315	Approved
0.6959	Remote Similarity	NPD6667	Approved
0.6959	Remote Similarity	NPD6666	Approved
0.6952	Remote Similarity	NPD7280	Phase 3
0.6952	Remote Similarity	NPD7281	Phase 3
0.6949	Remote Similarity	NPD5772	Approved
0.6949	Remote Similarity	NPD5773	Approved
0.6944	Remote Similarity	NPD5677	Discontinued
0.6941	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4466	Phase 1
0.6923	Remote Similarity	NPD2897	Discontinued
0.6923	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5297	Approved
0.6915	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7047	Phase 3
0.691	Remote Similarity	NPD5353	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