NPASS Compound

Structure

CID199023 OpenBabel06191715592D 25 25 0 0 0 0 0 0 0 0999 V2000 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 22 1 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 20 2 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.21
Volume:	382.558
LogP:	4.424
LogD:	3.823
LogS:	-4.651
# Rotatable Bonds:	10
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	2.655
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.641
MDCK Permeability:	1.6550860891584307e-05
Pgp-inhibitor:	0.437
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.323
30% Bioavailability (F30%):	0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.44
Plasma Protein Binding (PPB):	90.56206512451172%
Volume Distribution (VD):	1.646
Pgp-substrate:	10.882981300354004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.916
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.724
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.42
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.312
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.581
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	8.962
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.647
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.954
Carcinogencity:	0.051
Eye Corrosion:	0.004
Eye Irritation:	0.264
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC199023

Natural Product ID:	NPC199023
*Common Name:**	Nelumol A
IUPAC Name:	(E)-3-[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]-3,5-dimethoxyphenyl]prop-2-en-1-ol
Synonyms:	Geranyloxy Sinapyl Alcohol; Nelumol A
Standard InCHIKey:	MWNIFFJAKKQUJF-NRHDHWSESA-N
Standard InCHI:	InChI=1S/C21H30O4/c1-16(2)8-6-9-17(3)11-13-25-21-19(23-4)14-18(10-7-12-22)15-20(21)24-5/h7-8,10-11,14-15,22H,6,9,12-13H2,1-5H3/b10-7+,17-11+
SMILES:	OC/C=C/c1cc(OC)c(c(c1)OC)OC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464449
PubChem CID:	6439446
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088436]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7123	Aria intermedia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	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	9
Others	9
Potency	13

Activity Type	# Activity
Cell Line	8
Individual Protein	16
NON-MOLECULAR	4
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	34000.0	nM	PMID[448496]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6700.0	nM	PMID[448496]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3000.0	nM	PMID[448496]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PMID[448497]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	17782.8	nM	PMID[448497]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	76000.0	nM	PMID[448498]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	40000.0	nM	PMID[448498]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	72000.0	nM	PMID[448498]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	38000.0	nM	PMID[448498]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[448497]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[448497]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.05	n.a.	PMID[448499]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.044	n.a.	PMID[448499]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.223	n.a.	PMID[448499]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.577	n.a.	PMID[448499]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.86	n.a.	PMID[448499]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	4.072	n.a.	PMID[448499]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	10.86	n.a.	PMID[448499]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[448497]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	1000.0	nM	PMID[448497]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[448497]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[448497]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[448497]
NPT2	Others	Unspecified		Potency	=	16360.1	nM	PMID[448497]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	42000.0	nM	PMID[448498]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39000.0	nM	PMID[448498]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	80.0	%	PMID[448498]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	17.0	%	PMID[448498]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[448497]

☑ 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 NPC199023 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	374
0.1-0.2	1736
0.2-0.3	6235
0.3-0.4	13296
0.4-0.5	3696
0.5-0.6	5050
0.6-0.7	8294
0.7-0.8	3142
0.8-0.85	599
0.85-0.9	229
0.9-0.95	43
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9262	High Similarity	NPC202582
0.9262	High Similarity	NPC3439
0.9262	High Similarity	NPC218856
0.9262	High Similarity	NPC222004
0.9262	High Similarity	NPC470258
0.9262	High Similarity	NPC190629
0.9262	High Similarity	NPC210623
0.9262	High Similarity	NPC285339
0.9262	High Similarity	NPC273295
0.9262	High Similarity	NPC226788
0.9256	High Similarity	NPC474119
0.9231	High Similarity	NPC229401
0.9224	High Similarity	NPC63083
0.9204	High Similarity	NPC165646
0.9187	High Similarity	NPC472338
0.916	High Similarity	NPC270326
0.916	High Similarity	NPC261661
0.9153	High Similarity	NPC472596
0.9153	High Similarity	NPC166759
0.9115	High Similarity	NPC203924
0.9115	High Similarity	NPC55300
0.9113	High Similarity	NPC469625
0.9113	High Similarity	NPC472597
0.9113	High Similarity	NPC469613
0.9113	High Similarity	NPC30043
0.9098	High Similarity	NPC210355
0.9083	High Similarity	NPC108545
0.9076	High Similarity	NPC49341
0.9068	High Similarity	NPC474565
0.9052	High Similarity	NPC123948
0.904	High Similarity	NPC5423
0.904	High Similarity	NPC184447
0.904	High Similarity	NPC160991
0.904	High Similarity	NPC7903
0.904	High Similarity	NPC16208
0.904	High Similarity	NPC35932
0.9032	High Similarity	NPC469612
0.9032	High Similarity	NPC469614
0.9	High Similarity	NPC262253
0.9	High Similarity	NPC71579
0.9	High Similarity	NPC473411
0.8974	High Similarity	NPC259638
0.8968	High Similarity	NPC49074
0.8968	High Similarity	NPC475840
0.8957	High Similarity	NPC204120
0.8938	High Similarity	NPC165386
0.8934	High Similarity	NPC27352
0.8926	High Similarity	NPC282496
0.8926	High Similarity	NPC233526
0.8926	High Similarity	NPC220598
0.8926	High Similarity	NPC165375
0.8917	High Similarity	NPC145780
0.8898	High Similarity	NPC170694
0.8898	High Similarity	NPC310854
0.8898	High Similarity	NPC309744
0.8889	High Similarity	NPC162093
0.8889	High Similarity	NPC193067
0.8889	High Similarity	NPC470752
0.8871	High Similarity	NPC186843
0.8871	High Similarity	NPC98631
0.8871	High Similarity	NPC206615
0.8871	High Similarity	NPC470213
0.8862	High Similarity	NPC127604
0.8852	High Similarity	NPC122792
0.8852	High Similarity	NPC228972
0.8852	High Similarity	NPC109822
0.8852	High Similarity	NPC48990
0.8852	High Similarity	NPC94276
0.8852	High Similarity	NPC293701
0.8852	High Similarity	NPC114901
0.8843	High Similarity	NPC71090
0.8843	High Similarity	NPC288238
0.8828	High Similarity	NPC472337
0.8828	High Similarity	NPC61946
0.8824	High Similarity	NPC475961
0.8824	High Similarity	NPC135961
0.8824	High Similarity	NPC254625
0.8824	High Similarity	NPC20674
0.8819	High Similarity	NPC229442
0.8819	High Similarity	NPC168059
0.8819	High Similarity	NPC263064
0.881	High Similarity	NPC470095
0.881	High Similarity	NPC470096
0.881	High Similarity	NPC309787
0.88	High Similarity	NPC48315
0.88	High Similarity	NPC469951
0.88	High Similarity	NPC170844
0.88	High Similarity	NPC476968
0.88	High Similarity	NPC469963
0.879	High Similarity	NPC242032
0.879	High Similarity	NPC183181
0.879	High Similarity	NPC111247
0.879	High Similarity	NPC41706
0.879	High Similarity	NPC319625
0.879	High Similarity	NPC163332
0.879	High Similarity	NPC118787
0.879	High Similarity	NPC470699
0.879	High Similarity	NPC147821
0.879	High Similarity	NPC292056
0.878	High Similarity	NPC299584
0.878	High Similarity	NPC233410
0.878	High Similarity	NPC82483
0.878	High Similarity	NPC203133
0.878	High Similarity	NPC472093
0.878	High Similarity	NPC194519
0.878	High Similarity	NPC193544
0.878	High Similarity	NPC117214
0.878	High Similarity	NPC208950
0.878	High Similarity	NPC298757
0.878	High Similarity	NPC116907
0.878	High Similarity	NPC221077
0.878	High Similarity	NPC57490
0.878	High Similarity	NPC251855
0.878	High Similarity	NPC17943
0.878	High Similarity	NPC265483
0.878	High Similarity	NPC105925
0.878	High Similarity	NPC475169
0.8761	High Similarity	NPC227894
0.8761	High Similarity	NPC258171
0.876	High Similarity	NPC75713
0.876	High Similarity	NPC16435
0.876	High Similarity	NPC310373
0.876	High Similarity	NPC470804
0.876	High Similarity	NPC472334
0.876	High Similarity	NPC471719
0.876	High Similarity	NPC306441
0.876	High Similarity	NPC472336
0.876	High Similarity	NPC172818
0.876	High Similarity	NPC164857
0.876	High Similarity	NPC25695
0.875	High Similarity	NPC251981
0.875	High Similarity	NPC232084
0.875	High Similarity	NPC247364
0.875	High Similarity	NPC61516
0.875	High Similarity	NPC10932
0.875	High Similarity	NPC317380
0.875	High Similarity	NPC13745
0.875	High Similarity	NPC48863
0.874	High Similarity	NPC201587
0.874	High Similarity	NPC253105
0.874	High Similarity	NPC245120
0.874	High Similarity	NPC299144
0.873	High Similarity	NPC214860
0.873	High Similarity	NPC91291
0.873	High Similarity	NPC220935
0.872	High Similarity	NPC109275
0.872	High Similarity	NPC31707
0.872	High Similarity	NPC210674
0.871	High Similarity	NPC78974
0.871	High Similarity	NPC191037
0.871	High Similarity	NPC18924
0.871	High Similarity	NPC28730
0.871	High Similarity	NPC58607
0.871	High Similarity	NPC244364
0.871	High Similarity	NPC44748
0.871	High Similarity	NPC103823
0.871	High Similarity	NPC223136
0.871	High Similarity	NPC214406
0.871	High Similarity	NPC178284
0.871	High Similarity	NPC181361
0.8699	High Similarity	NPC183446
0.8692	High Similarity	NPC477938
0.8689	High Similarity	NPC194626
0.8682	High Similarity	NPC234333
0.8682	High Similarity	NPC47398
0.8682	High Similarity	NPC121812
0.8682	High Similarity	NPC470356
0.8682	High Similarity	NPC470236
0.8682	High Similarity	NPC260898
0.8682	High Similarity	NPC112939
0.8682	High Similarity	NPC94750
0.8682	High Similarity	NPC195022
0.8682	High Similarity	NPC112246
0.8682	High Similarity	NPC474206
0.8672	High Similarity	NPC132895
0.8672	High Similarity	NPC36661
0.8672	High Similarity	NPC215833
0.8672	High Similarity	NPC69513
0.8672	High Similarity	NPC36490
0.8667	High Similarity	NPC308217
0.8667	High Similarity	NPC226629
0.8661	High Similarity	NPC474017
0.8655	High Similarity	NPC304208
0.8655	High Similarity	NPC52464
0.8651	High Similarity	NPC45824
0.8651	High Similarity	NPC212015
0.8651	High Similarity	NPC86030
0.8651	High Similarity	NPC5851
0.8651	High Similarity	NPC248355
0.864	High Similarity	NPC293054
0.864	High Similarity	NPC169474
0.864	High Similarity	NPC194841
0.864	High Similarity	NPC236791
0.864	High Similarity	NPC282000
0.864	High Similarity	NPC159968
0.864	High Similarity	NPC74817
0.864	High Similarity	NPC127587
0.864	High Similarity	NPC246620
0.864	High Similarity	NPC82679
0.864	High Similarity	NPC124452

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 NPC199023 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	958
0.2-0.3	2195
0.3-0.4	2660
0.4-0.5	1486
0.5-0.6	876
0.6-0.7	557
0.7-0.8	107
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD3027	Phase 3
0.8618	High Similarity	NPD2982	Phase 2
0.8618	High Similarity	NPD2983	Phase 2
0.8537	High Similarity	NPD2981	Phase 2
0.845	Intermediate Similarity	NPD1613	Approved
0.845	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD3018	Phase 2
0.8281	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2684	Approved
0.8203	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD228	Approved
0.8083	Intermediate Similarity	NPD7843	Approved
0.8065	Intermediate Similarity	NPD1357	Approved
0.8033	Intermediate Similarity	NPD7157	Approved
0.8017	Intermediate Similarity	NPD5283	Phase 1
0.8016	Intermediate Similarity	NPD3705	Approved
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7984	Intermediate Similarity	NPD1548	Phase 1
0.7879	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1610	Phase 2
0.7845	Intermediate Similarity	NPD291	Approved
0.7815	Intermediate Similarity	NPD290	Approved
0.7778	Intermediate Similarity	NPD4678	Approved
0.7778	Intermediate Similarity	NPD4675	Approved
0.7762	Intermediate Similarity	NPD1653	Approved
0.776	Intermediate Similarity	NPD5536	Phase 2
0.7752	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD4749	Approved
0.7744	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1091	Approved
0.7681	Intermediate Similarity	NPD3540	Phase 1
0.7612	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3539	Phase 1
0.7606	Intermediate Similarity	NPD4357	Discontinued
0.7597	Intermediate Similarity	NPD422	Phase 1
0.7589	Intermediate Similarity	NPD2219	Phase 1
0.7589	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD7533	Approved
0.7559	Intermediate Similarity	NPD7534	Approved
0.7557	Intermediate Similarity	NPD8651	Approved
0.7556	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1375	Discontinued
0.7551	Intermediate Similarity	NPD1934	Approved
0.7537	Intermediate Similarity	NPD4625	Phase 3
0.7521	Intermediate Similarity	NPD1358	Approved
0.7517	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD1558	Phase 1
0.748	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6111	Discontinued
0.7463	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1242	Phase 1
0.745	Intermediate Similarity	NPD3817	Phase 2
0.745	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4237	Approved
0.7447	Intermediate Similarity	NPD4236	Phase 3
0.7431	Intermediate Similarity	NPD4123	Phase 3
0.7407	Intermediate Similarity	NPD3180	Approved
0.7407	Intermediate Similarity	NPD3179	Approved
0.7398	Intermediate Similarity	NPD556	Approved
0.7397	Intermediate Similarity	NPD3687	Approved
0.7397	Intermediate Similarity	NPD3686	Approved
0.7388	Intermediate Similarity	NPD2861	Phase 2
0.7385	Intermediate Similarity	NPD3496	Discontinued
0.7383	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9365	Approved
0.736	Intermediate Similarity	NPD821	Approved
0.7347	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4005	Discontinued
0.7324	Intermediate Similarity	NPD3060	Approved
0.7324	Intermediate Similarity	NPD4162	Approved
0.7324	Intermediate Similarity	NPD1652	Phase 2
0.7323	Intermediate Similarity	NPD6671	Approved
0.732	Intermediate Similarity	NPD7199	Phase 2
0.7319	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5124	Phase 1
0.7319	Intermediate Similarity	NPD230	Phase 1
0.7315	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD5846	Approved
0.7308	Intermediate Similarity	NPD1778	Approved
0.7308	Intermediate Similarity	NPD6516	Phase 2
0.7295	Intermediate Similarity	NPD968	Approved
0.7295	Intermediate Similarity	NPD3134	Approved
0.7292	Intermediate Similarity	NPD7124	Phase 2
0.729	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6166	Phase 2
0.729	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4965	Approved
0.7285	Intermediate Similarity	NPD4967	Phase 2
0.7285	Intermediate Similarity	NPD4966	Approved
0.726	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9494	Approved
0.725	Intermediate Similarity	NPD846	Approved
0.725	Intermediate Similarity	NPD940	Approved
0.7246	Intermediate Similarity	NPD4060	Phase 1
0.7246	Intermediate Similarity	NPD3620	Phase 2
0.7246	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5297	Approved
0.7241	Intermediate Similarity	NPD1511	Approved
0.7234	Intermediate Similarity	NPD2161	Phase 2
0.7226	Intermediate Similarity	NPD3144	Approved
0.7226	Intermediate Similarity	NPD3145	Approved
0.7214	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4536	Approved
0.7214	Intermediate Similarity	NPD4538	Approved
0.7203	Intermediate Similarity	NPD6674	Discontinued
0.7203	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD447	Suspended
0.7185	Intermediate Similarity	NPD6584	Phase 3
0.7179	Intermediate Similarity	NPD9296	Approved
0.7174	Intermediate Similarity	NPD2674	Phase 3
0.7171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3892	Phase 2
0.7153	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4110	Phase 3
0.7152	Intermediate Similarity	NPD5773	Approved
0.7152	Intermediate Similarity	NPD5772	Approved
0.7152	Intermediate Similarity	NPD5844	Phase 1
0.7152	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7526	Approved
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD6653	Approved
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7143	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD52	Approved
0.7143	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7153	Discontinued
0.7124	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1774	Approved
0.7123	Intermediate Similarity	NPD6799	Approved
0.7123	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3021	Approved
0.712	Intermediate Similarity	NPD3022	Approved
0.7115	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7074	Phase 3
0.7107	Intermediate Similarity	NPD7472	Approved
0.7105	Intermediate Similarity	NPD2560	Approved
0.7105	Intermediate Similarity	NPD2563	Approved
0.7103	Intermediate Similarity	NPD2677	Approved
0.7095	Intermediate Similarity	NPD2122	Discontinued
0.7095	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3685	Discontinued
0.7089	Intermediate Similarity	NPD3818	Discontinued
0.7087	Intermediate Similarity	NPD5535	Approved
0.708	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6234	Discontinued
0.7075	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3146	Approved
0.7075	Intermediate Similarity	NPD7447	Phase 1
0.7071	Intermediate Similarity	NPD4340	Discontinued
0.7071	Intermediate Similarity	NPD5735	Approved
0.7063	Intermediate Similarity	NPD7266	Discontinued
0.7059	Intermediate Similarity	NPD3691	Phase 2
0.7059	Intermediate Similarity	NPD3690	Phase 2
0.7045	Intermediate Similarity	NPD4626	Approved
0.7042	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5588	Approved
0.7042	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5960	Phase 3
0.7037	Intermediate Similarity	NPD2922	Phase 1
0.7034	Intermediate Similarity	NPD4628	Phase 3
0.7034	Intermediate Similarity	NPD6331	Phase 2
0.7032	Intermediate Similarity	NPD5494	Approved
0.7029	Intermediate Similarity	NPD7095	Approved
0.7023	Intermediate Similarity	NPD1182	Approved
0.7021	Intermediate Similarity	NPD2653	Approved
0.702	Intermediate Similarity	NPD5090	Approved
0.702	Intermediate Similarity	NPD5089	Approved
0.7007	Intermediate Similarity	NPD7212	Phase 2
0.7007	Intermediate Similarity	NPD7213	Phase 3
0.7	Intermediate Similarity	NPD2238	Phase 2
0.6993	Remote Similarity	NPD2796	Approved
0.6993	Remote Similarity	NPD6100	Approved
0.6993	Remote Similarity	NPD6099	Approved
0.6985	Remote Similarity	NPD1818	Approved
0.6985	Remote Similarity	NPD1820	Approved
0.6985	Remote Similarity	NPD1819	Approved
0.6985	Remote Similarity	NPD1817	Approved
0.6984	Remote Similarity	NPD4750	Phase 3
0.6978	Remote Similarity	NPD5110	Phase 2
0.6978	Remote Similarity	NPD5109	Approved
0.6978	Remote Similarity	NPD5111	Phase 2
0.6975	Remote Similarity	NPD7808	Phase 3
0.697	Remote Similarity	NPD5585	Approved
0.697	Remote Similarity	NPD5691	Approved
0.6966	Remote Similarity	NPD5177	Phase 3
0.6963	Remote Similarity	NPD6583	Phase 3
0.6963	Remote Similarity	NPD6582	Phase 2
0.6963	Remote Similarity	NPD5327	Phase 3
0.6963	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1424	Approved
0.6959	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6797	Phase 2
0.6944	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5762	Approved
0.6944	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5763	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