NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	259.12
Volume:	272.432
LogP:	1.109
LogD:	1.778
LogS:	-2.257
# Rotatable Bonds:	5
TPSA:	72.72
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	1.879
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.145
MDCK Permeability:	1.1317923053866252e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.477
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	54.43259048461914%
Volume Distribution (VD):	1.434
Pgp-substrate:	40.43531036376953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.264
CYP1A2-substrate:	0.726
CYP2C19-inhibitor:	0.314
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.775
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	20.969
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.355
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.784
Maximum Recommended Daily Dose:	0.576
Skin Sensitization:	0.954
Carcinogencity:	0.062
Eye Corrosion:	0.031
Eye Irritation:	0.055
Respiratory Toxicity:	0.272

Download Data

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

Natural Product: NPC318965

Natural Product ID:	NPC318965
*Common Name:**	Norbelladine
IUPAC Name:	4-[[2-(4-hydroxyphenyl)ethylamino]methyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	YJYUDTAJVLORNV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H17NO3/c17-13-4-1-11(2-5-13)7-8-16-10-12-3-6-14(18)15(19)9-12/h1-6,9,16-19H,7-8,10H2
SMILES:	C1=CC(=CC=C1CCNCC2=CC(=C(C=C2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359303
PubChem CID:	416247
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004121] Norbelladine-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
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18356045]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	Turkey	n.a.	PMID[19299148]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	stem	n.a.	PMID[20066175]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25061748]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	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
Others	4

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	51.0	%	PMID[521822]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	25.0	%	PMID[521822]
NPT35	Others	n.a.		Activity	=	33.0	%	PMID[521822]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	Inhibition	=	23.0	%	PMID[521822]

☑ 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 NPC318965 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	282
0.1-0.2	2758
0.2-0.3	13124
0.3-0.4	4750
0.4-0.5	11740
0.5-0.6	7675
0.6-0.7	2004
0.7-0.8	319
0.8-0.85	22
0.85-0.9	10
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9077	High Similarity	NPC219233
0.9077	High Similarity	NPC211468
0.9077	High Similarity	NPC170170
0.9008	High Similarity	NPC323123
0.9	High Similarity	NPC85276
0.8906	High Similarity	NPC302171
0.8906	High Similarity	NPC300020
0.8906	High Similarity	NPC33338
0.8655	High Similarity	NPC146422
0.8385	Intermediate Similarity	NPC271808
0.8372	Intermediate Similarity	NPC236347
0.8372	Intermediate Similarity	NPC323775
0.831	Intermediate Similarity	NPC76213
0.831	Intermediate Similarity	NPC277669
0.8306	Intermediate Similarity	NPC283468
0.824	Intermediate Similarity	NPC122009
0.8201	Intermediate Similarity	NPC294249
0.8194	Intermediate Similarity	NPC2295
0.8194	Intermediate Similarity	NPC477564
0.8175	Intermediate Similarity	NPC268572
0.8169	Intermediate Similarity	NPC207824
0.8169	Intermediate Similarity	NPC60538
0.811	Intermediate Similarity	NPC169207
0.811	Intermediate Similarity	NPC115627
0.811	Intermediate Similarity	NPC118522
0.8065	Intermediate Similarity	NPC142599
0.803	Intermediate Similarity	NPC172403
0.7956	Intermediate Similarity	NPC301050
0.7956	Intermediate Similarity	NPC131204
0.7907	Intermediate Similarity	NPC284078
0.7902	Intermediate Similarity	NPC191376
0.7902	Intermediate Similarity	NPC179825
0.7902	Intermediate Similarity	NPC321505
0.7899	Intermediate Similarity	NPC68055
0.7881	Intermediate Similarity	NPC29601
0.7874	Intermediate Similarity	NPC137096
0.7868	Intermediate Similarity	NPC160692
0.7863	Intermediate Similarity	NPC318777
0.7863	Intermediate Similarity	NPC13020
0.7863	Intermediate Similarity	NPC140359
0.7847	Intermediate Similarity	NPC135538
0.7847	Intermediate Similarity	NPC476571
0.7847	Intermediate Similarity	NPC246587
0.7847	Intermediate Similarity	NPC428
0.7847	Intermediate Similarity	NPC24233
0.7847	Intermediate Similarity	NPC147390
0.7797	Intermediate Similarity	NPC125732
0.7794	Intermediate Similarity	NPC208757
0.7793	Intermediate Similarity	NPC477565
0.7793	Intermediate Similarity	NPC103379
0.7786	Intermediate Similarity	NPC298486
0.777	Intermediate Similarity	NPC253429
0.7762	Intermediate Similarity	NPC185838
0.7731	Intermediate Similarity	NPC223393
0.7718	Intermediate Similarity	NPC160931
0.7718	Intermediate Similarity	NPC37205
0.7712	Intermediate Similarity	NPC35627
0.7712	Intermediate Similarity	NPC81247
0.7712	Intermediate Similarity	NPC476573
0.7686	Intermediate Similarity	NPC471511
0.7664	Intermediate Similarity	NPC93882
0.7664	Intermediate Similarity	NPC130595
0.7655	Intermediate Similarity	NPC476151
0.7647	Intermediate Similarity	NPC121275
0.7647	Intermediate Similarity	NPC284183
0.7647	Intermediate Similarity	NPC4138
0.763	Intermediate Similarity	NPC251571
0.763	Intermediate Similarity	NPC16031
0.763	Intermediate Similarity	NPC161593
0.763	Intermediate Similarity	NPC145888
0.7623	Intermediate Similarity	NPC239291
0.7619	Intermediate Similarity	NPC151895
0.7619	Intermediate Similarity	NPC192768
0.7619	Intermediate Similarity	NPC220858
0.7619	Intermediate Similarity	NPC88249
0.7619	Intermediate Similarity	NPC97221
0.7609	Intermediate Similarity	NPC6854
0.7609	Intermediate Similarity	NPC285078
0.7609	Intermediate Similarity	NPC313737
0.7594	Intermediate Similarity	NPC217277
0.7591	Intermediate Similarity	NPC255550
0.7591	Intermediate Similarity	NPC308885
0.7583	Intermediate Similarity	NPC155847
0.7583	Intermediate Similarity	NPC289381
0.7581	Intermediate Similarity	NPC96224
0.7581	Intermediate Similarity	NPC24101
0.7578	Intermediate Similarity	NPC10286
0.7578	Intermediate Similarity	NPC213
0.7574	Intermediate Similarity	NPC155838
0.7569	Intermediate Similarity	NPC125852
0.7563	Intermediate Similarity	NPC109955
0.7557	Intermediate Similarity	NPC252817
0.7554	Intermediate Similarity	NPC218530
0.7536	Intermediate Similarity	NPC214869
0.7533	Intermediate Similarity	NPC278799
0.7533	Intermediate Similarity	NPC207757
0.7533	Intermediate Similarity	NPC54379
0.7533	Intermediate Similarity	NPC110416
0.7533	Intermediate Similarity	NPC2413
0.7533	Intermediate Similarity	NPC193949
0.7533	Intermediate Similarity	NPC276588
0.7533	Intermediate Similarity	NPC172765
0.7533	Intermediate Similarity	NPC127674
0.7533	Intermediate Similarity	NPC189266
0.7533	Intermediate Similarity	NPC5238
0.7533	Intermediate Similarity	NPC469817
0.7533	Intermediate Similarity	NPC249797
0.7533	Intermediate Similarity	NPC204828
0.7533	Intermediate Similarity	NPC39701
0.7533	Intermediate Similarity	NPC184026
0.7533	Intermediate Similarity	NPC295691
0.752	Intermediate Similarity	NPC254833
0.752	Intermediate Similarity	NPC62258
0.752	Intermediate Similarity	NPC55617
0.752	Intermediate Similarity	NPC228343
0.752	Intermediate Similarity	NPC172046
0.7518	Intermediate Similarity	NPC35961
0.7518	Intermediate Similarity	NPC195749
0.7518	Intermediate Similarity	NPC160193
0.7518	Intermediate Similarity	NPC52029
0.7516	Intermediate Similarity	NPC475215
0.7516	Intermediate Similarity	NPC108434
0.7468	Intermediate Similarity	NPC477020
0.7468	Intermediate Similarity	NPC66341
0.7468	Intermediate Similarity	NPC192135
0.7464	Intermediate Similarity	NPC114102
0.7464	Intermediate Similarity	NPC326599
0.7464	Intermediate Similarity	NPC329595
0.746	Intermediate Similarity	NPC174096
0.746	Intermediate Similarity	NPC147634
0.746	Intermediate Similarity	NPC226401
0.746	Intermediate Similarity	NPC120982
0.746	Intermediate Similarity	NPC79793
0.7459	Intermediate Similarity	NPC196479
0.7452	Intermediate Similarity	NPC109925
0.7452	Intermediate Similarity	NPC26240
0.7452	Intermediate Similarity	NPC69712
0.7452	Intermediate Similarity	NPC477562
0.744	Intermediate Similarity	NPC153690
0.744	Intermediate Similarity	NPC233835
0.7426	Intermediate Similarity	NPC322366
0.7413	Intermediate Similarity	NPC314682
0.741	Intermediate Similarity	NPC88667
0.741	Intermediate Similarity	NPC149379
0.7402	Intermediate Similarity	NPC257430
0.7402	Intermediate Similarity	NPC179002
0.7402	Intermediate Similarity	NPC297657
0.7402	Intermediate Similarity	NPC187583
0.74	Intermediate Similarity	NPC82285
0.74	Intermediate Similarity	NPC133011
0.7395	Intermediate Similarity	NPC107522
0.7394	Intermediate Similarity	NPC193528
0.7381	Intermediate Similarity	NPC145638
0.7381	Intermediate Similarity	NPC290566
0.7377	Intermediate Similarity	NPC110764
0.7376	Intermediate Similarity	NPC6913
0.7372	Intermediate Similarity	NPC153990
0.7361	Intermediate Similarity	NPC474915
0.7361	Intermediate Similarity	NPC328750
0.7361	Intermediate Similarity	NPC188163
0.7361	Intermediate Similarity	NPC323204
0.7361	Intermediate Similarity	NPC213206
0.736	Intermediate Similarity	NPC176527
0.7357	Intermediate Similarity	NPC267237
0.7355	Intermediate Similarity	NPC131587
0.7338	Intermediate Similarity	NPC27410
0.7338	Intermediate Similarity	NPC166014
0.7328	Intermediate Similarity	NPC120075
0.7317	Intermediate Similarity	NPC178902
0.7302	Intermediate Similarity	NPC34864
0.7302	Intermediate Similarity	NPC114392
0.7302	Intermediate Similarity	NPC105727
0.7302	Intermediate Similarity	NPC58427
0.7299	Intermediate Similarity	NPC301713
0.7299	Intermediate Similarity	NPC321561
0.729	Intermediate Similarity	NPC60186
0.7284	Intermediate Similarity	NPC474507
0.728	Intermediate Similarity	NPC477814
0.728	Intermediate Similarity	NPC231705
0.7273	Intermediate Similarity	NPC111485
0.7267	Intermediate Similarity	NPC173416
0.7267	Intermediate Similarity	NPC476577
0.7267	Intermediate Similarity	NPC148709
0.7266	Intermediate Similarity	NPC262641
0.7266	Intermediate Similarity	NPC280382
0.7266	Intermediate Similarity	NPC268032
0.7258	Intermediate Similarity	NPC120719
0.7258	Intermediate Similarity	NPC12278
0.7255	Intermediate Similarity	NPC170503
0.7255	Intermediate Similarity	NPC147091
0.7255	Intermediate Similarity	NPC126519
0.7255	Intermediate Similarity	NPC203784
0.725	Intermediate Similarity	NPC274678
0.7246	Intermediate Similarity	NPC186898
0.7244	Intermediate Similarity	NPC124433
0.7244	Intermediate Similarity	NPC71266
0.7244	Intermediate Similarity	NPC293871
0.7244	Intermediate Similarity	NPC1229
0.7233	Intermediate Similarity	NPC152212
0.7231	Intermediate Similarity	NPC120280

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 NPC318965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	776
0.2-0.3	1117
0.3-0.4	1672
0.4-0.5	3169
0.5-0.6	1695
0.6-0.7	451
0.7-0.8	83
0.8-0.85	10
0.85-0.9	10
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9262	High Similarity	NPD5310	Approved
0.9262	High Similarity	NPD5311	Approved
0.9187	High Similarity	NPD3055	Approved
0.9187	High Similarity	NPD3053	Approved
0.8931	High Similarity	NPD1632	Clinical (unspecified phase)
0.8828	High Similarity	NPD2028	Clinical (unspecified phase)
0.8692	High Similarity	NPD3062	Approved
0.8692	High Similarity	NPD3061	Approved
0.8692	High Similarity	NPD3059	Approved
0.8676	High Similarity	NPD3845	Phase 1
0.8655	High Similarity	NPD9379	Approved
0.8655	High Similarity	NPD9377	Approved
0.8561	High Similarity	NPD5314	Approved
0.854	High Similarity	NPD2422	Clinical (unspecified phase)
0.8504	High Similarity	NPD9634	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD601	Approved
0.8397	Intermediate Similarity	NPD598	Approved
0.8397	Intermediate Similarity	NPD597	Approved
0.8372	Intermediate Similarity	NPD9619	Approved
0.8372	Intermediate Similarity	NPD9620	Approved
0.8372	Intermediate Similarity	NPD9621	Approved
0.8333	Intermediate Similarity	NPD1136	Approved
0.8333	Intermediate Similarity	NPD1132	Approved
0.8333	Intermediate Similarity	NPD1130	Approved
0.8284	Intermediate Similarity	NPD817	Approved
0.8284	Intermediate Similarity	NPD823	Approved
0.811	Intermediate Similarity	NPD9384	Approved
0.811	Intermediate Similarity	NPD9381	Approved
0.8062	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD316	Approved
0.7929	Intermediate Similarity	NPD3060	Approved
0.7907	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD9613	Approved
0.7874	Intermediate Similarity	NPD9616	Approved
0.7874	Intermediate Similarity	NPD9615	Approved
0.7863	Intermediate Similarity	NPD9622	Approved
0.7832	Intermediate Similarity	NPD2421	Approved
0.7832	Intermediate Similarity	NPD2420	Approved
0.7786	Intermediate Similarity	NPD2561	Approved
0.7786	Intermediate Similarity	NPD2562	Approved
0.7754	Intermediate Similarity	NPD2568	Approved
0.774	Intermediate Similarity	NPD1969	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1973	Approved
0.774	Intermediate Similarity	NPD1972	Approved
0.7734	Intermediate Similarity	NPD856	Approved
0.7734	Intermediate Similarity	NPD16	Approved
0.7676	Intermediate Similarity	NPD4162	Approved
0.7664	Intermediate Similarity	NPD2674	Phase 3
0.763	Intermediate Similarity	NPD9569	Approved
0.7615	Intermediate Similarity	NPD4093	Discontinued
0.7591	Intermediate Similarity	NPD3144	Approved
0.7591	Intermediate Similarity	NPD3145	Approved
0.7559	Intermediate Similarity	NPD2228	Approved
0.7559	Intermediate Similarity	NPD2234	Approved
0.7559	Intermediate Similarity	NPD2229	Approved
0.7551	Intermediate Similarity	NPD6030	Approved
0.7551	Intermediate Similarity	NPD6031	Approved
0.7541	Intermediate Similarity	NPD9608	Approved
0.7541	Intermediate Similarity	NPD9610	Approved
0.7535	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD3022	Approved
0.752	Intermediate Similarity	NPD3021	Approved
0.752	Intermediate Similarity	NPD1792	Phase 2
0.75	Intermediate Similarity	NPD1793	Approved
0.75	Intermediate Similarity	NPD1791	Approved
0.7483	Intermediate Similarity	NPD2978	Approved
0.7483	Intermediate Similarity	NPD2977	Approved
0.7462	Intermediate Similarity	NPD318	Approved
0.7462	Intermediate Similarity	NPD317	Approved
0.7426	Intermediate Similarity	NPD599	Approved
0.7426	Intermediate Similarity	NPD858	Approved
0.7426	Intermediate Similarity	NPD602	Approved
0.7426	Intermediate Similarity	NPD859	Approved
0.7419	Intermediate Similarity	NPD1444	Approved
0.7419	Intermediate Similarity	NPD1445	Approved
0.7415	Intermediate Similarity	NPD3645	Discontinued
0.7413	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6405	Approved
0.741	Intermediate Similarity	NPD6407	Approved
0.741	Intermediate Similarity	NPD259	Phase 1
0.7405	Intermediate Similarity	NPD5304	Approved
0.7405	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5303	Approved
0.7391	Intermediate Similarity	NPD9536	Phase 1
0.7391	Intermediate Similarity	NPD9537	Phase 1
0.7381	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9618	Approved
0.7364	Intermediate Similarity	NPD9614	Approved
0.7361	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD555	Phase 2
0.7299	Intermediate Similarity	NPD258	Approved
0.7299	Intermediate Similarity	NPD257	Approved
0.7297	Intermediate Similarity	NPD1424	Approved
0.7293	Intermediate Similarity	NPD1751	Approved
0.726	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7153	Discontinued
0.7226	Intermediate Similarity	NPD1131	Approved
0.7226	Intermediate Similarity	NPD1134	Approved
0.7226	Intermediate Similarity	NPD1135	Approved
0.7226	Intermediate Similarity	NPD1133	Approved
0.7226	Intermediate Similarity	NPD1129	Approved
0.7219	Intermediate Similarity	NPD824	Approved
0.7215	Intermediate Similarity	NPD4083	Discontinued
0.7214	Intermediate Similarity	NPD5718	Phase 2
0.7211	Intermediate Similarity	NPD302	Approved
0.7192	Intermediate Similarity	NPD2459	Approved
0.7192	Intermediate Similarity	NPD2460	Phase 3
0.7192	Intermediate Similarity	NPD2458	Approved
0.719	Intermediate Similarity	NPD7298	Approved
0.7174	Intermediate Similarity	NPD2195	Approved
0.7174	Intermediate Similarity	NPD2194	Approved
0.7164	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2989	Phase 2
0.7133	Intermediate Similarity	NPD3052	Approved
0.7133	Intermediate Similarity	NPD3054	Approved
0.7133	Intermediate Similarity	NPD2986	Phase 2
0.7133	Intermediate Similarity	NPD2653	Approved
0.7122	Intermediate Similarity	NPD3637	Approved
0.7122	Intermediate Similarity	NPD3635	Approved
0.7122	Intermediate Similarity	NPD3636	Approved
0.7115	Intermediate Similarity	NPD7833	Phase 2
0.7115	Intermediate Similarity	NPD7831	Phase 2
0.7115	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD826	Approved
0.7113	Intermediate Similarity	NPD825	Approved
0.7111	Intermediate Similarity	NPD1981	Approved
0.7111	Intermediate Similarity	NPD1980	Approved
0.7111	Intermediate Similarity	NPD1983	Approved
0.7111	Intermediate Similarity	NPD1671	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5137	Approved
0.7103	Intermediate Similarity	NPD9570	Approved
0.7095	Intermediate Similarity	NPD5241	Discontinued
0.7083	Intermediate Similarity	NPD3553	Approved
0.7083	Intermediate Similarity	NPD3554	Approved
0.7083	Intermediate Similarity	NPD3555	Approved
0.7083	Intermediate Similarity	NPD3552	Approved
0.708	Intermediate Similarity	NPD4659	Approved
0.7078	Intermediate Similarity	NPD5720	Discontinued
0.7075	Intermediate Similarity	NPD3638	Discontinued
0.7071	Intermediate Similarity	NPD3594	Approved
0.7071	Intermediate Similarity	NPD3595	Approved
0.7067	Intermediate Similarity	NPD2874	Phase 2
0.7067	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4584	Approved
0.7059	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7451	Discontinued
0.7044	Intermediate Similarity	NPD4010	Discontinued
0.7037	Intermediate Similarity	NPD4873	Discontinued
0.7032	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2934	Approved
0.7025	Intermediate Similarity	NPD2933	Approved
0.7021	Intermediate Similarity	NPD5155	Approved
0.7021	Intermediate Similarity	NPD5156	Approved
0.7007	Intermediate Similarity	NPD4257	Approved
0.7007	Intermediate Similarity	NPD4256	Phase 2
0.6993	Remote Similarity	NPD3455	Phase 2
0.6992	Remote Similarity	NPD9568	Approved
0.6986	Remote Similarity	NPD3156	Discontinued
0.6978	Remote Similarity	NPD4103	Phase 2
0.6978	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5976	Discontinued
0.6972	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2860	Approved
0.6967	Remote Similarity	NPD2859	Approved
0.6966	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6895	Approved
0.6966	Remote Similarity	NPD6896	Approved
0.6954	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6297	Approved
0.695	Remote Similarity	NPD2605	Approved
0.695	Remote Similarity	NPD2606	Approved
0.6944	Remote Similarity	NPD274	Approved
0.6944	Remote Similarity	NPD275	Approved
0.6935	Remote Similarity	NPD3020	Approved
0.6928	Remote Similarity	NPD3687	Approved
0.6928	Remote Similarity	NPD3686	Approved
0.6923	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD829	Discontinued
0.6918	Remote Similarity	NPD1753	Discontinued
0.6913	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2667	Approved
0.6912	Remote Similarity	NPD2668	Approved
0.6901	Remote Similarity	NPD5163	Phase 2
0.6884	Remote Similarity	NPD2235	Phase 2
0.6884	Remote Similarity	NPD2231	Phase 2
0.6883	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4017	Approved
0.688	Remote Similarity	NPD1242	Phase 1
0.6879	Remote Similarity	NPD2563	Approved
0.6879	Remote Similarity	NPD2560	Approved
0.687	Remote Similarity	NPD228	Approved
0.6867	Remote Similarity	NPD5160	Discontinued
0.6867	Remote Similarity	NPD8131	Suspended
0.6852	Remote Similarity	NPD2898	Approved
0.6846	Remote Similarity	NPD5177	Phase 3
0.6842	Remote Similarity	NPD4123	Phase 3

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