NPASS Compound

Structure

CID254625 OpenBabel06191716052D 24 25 0 0 0 0 0 0 0 0999 V2000 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -0.0000 1.0000 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 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	348.2
LogP:	3.002
LogD:	3.339
LogS:	-4.025
# Rotatable Bonds:	8
TPSA:	46.15
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	1.811
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.89
MDCK Permeability:	2.9328119126148522e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.962
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.164
30% Bioavailability (F30%):	0.595

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	77.80113983154297%
Volume Distribution (VD):	0.71
Pgp-substrate:	6.310206413269043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.652
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.843
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.565
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.102
CYP2D6-substrate:	0.95
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	9.554
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.332
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.702
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.928
Carcinogencity:	0.059
Eye Corrosion:	0.022
Eye Irritation:	0.149
Respiratory Toxicity:	0.046

Download Data

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

Natural Product: NPC254625

Natural Product ID:	NPC254625
*Common Name:**	5-(3,4-Dimethoxyphenethyl)-1,2,3-Trimethoxybenzene
IUPAC Name:	5-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3-trimethoxybenzene
Synonyms:
Standard InCHIKey:	XKKZNLRWNSUNBW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H24O5/c1-20-15-9-8-13(10-16(15)21-2)6-7-14-11-17(22-3)19(24-5)18(12-14)23-4/h8-12H,6-7H2,1-5H3
SMILES:	COc1ccc(CCc2cc(c(c(c2)OC)OC)OC)cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL307158
PubChem CID:	3086528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16268553]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[16724831]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715978]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19228038]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[20141173]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407005]
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3404149]
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3598594]
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3668557]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO326	Pittosporum brevicalyx	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15662	Ligustrum ovalifolium	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4581	Ungernia victoris	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15280	Sideritis grandiflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1575	Mikania luetzelburgii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6178	Solanum euacanthum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13053	Corydalis conspersa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3894	Dendrobium nobile	Species	Orchidaceae	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	8
Others	4

Activity Type	# Activity
Cell Line	6
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	15000.0	nM	PMID[486699]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	15000.0	nM	PMID[486699]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	15000.0	nM	PMID[486699]
NPT2735	Cell Line	RAW	Mus musculus	IC50	=	48200.0	nM	PMID[486700]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	20000.0	nM	PMID[486701]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	25.0	%	PMID[486701]
NPT2	Others	Unspecified		IC50	=	15000.0	nM	PMID[486699]
NPT1	Others	Radical scavenging activity		IC50	>	200000.0	nM	PMID[486700]
NPT2	Others	Unspecified		Inhibition	=	37.0	%	PMID[486701]
NPT2	Others	Unspecified		Inhibition	=	63.0	%	PMID[486701]
NPT2	Others	Unspecified		Inhibition	=	88.0	%	PMID[486701]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[486701]

☑ 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 NPC254625 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	483
0.1-0.2	1903
0.2-0.3	6095
0.3-0.4	13379
0.4-0.5	3419
0.5-0.6	5186
0.6-0.7	8005
0.7-0.8	3185
0.8-0.85	645
0.85-0.9	303
0.9-0.95	84
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475961
0.9737	High Similarity	NPC477886
0.973	High Similarity	NPC123948
0.9649	High Similarity	NPC472596
0.9646	High Similarity	NPC15805
0.9569	High Similarity	NPC282496
0.9569	High Similarity	NPC233526
0.9483	High Similarity	NPC261661
0.9459	High Similarity	NPC204120
0.9407	High Similarity	NPC221077
0.9407	High Similarity	NPC233410
0.9407	High Similarity	NPC203133
0.9407	High Similarity	NPC57490
0.9407	High Similarity	NPC117214
0.9407	High Similarity	NPC193544
0.9407	High Similarity	NPC475169
0.9407	High Similarity	NPC472093
0.9407	High Similarity	NPC105925
0.9407	High Similarity	NPC17943
0.9407	High Similarity	NPC251855
0.9407	High Similarity	NPC298757
0.9407	High Similarity	NPC208950
0.9407	High Similarity	NPC116907
0.9328	High Similarity	NPC112571
0.9328	High Similarity	NPC285725
0.9328	High Similarity	NPC50683
0.931	High Similarity	NPC166759
0.9279	High Similarity	NPC203924
0.925	High Similarity	NPC236791
0.925	High Similarity	NPC324112
0.925	High Similarity	NPC169474
0.925	High Similarity	NPC246620
0.925	High Similarity	NPC293054
0.925	High Similarity	NPC282000
0.925	High Similarity	NPC159968
0.925	High Similarity	NPC124452
0.925	High Similarity	NPC82679
0.925	High Similarity	NPC242032
0.925	High Similarity	NPC74817
0.925	High Similarity	NPC127587
0.9237	High Similarity	NPC136319
0.9237	High Similarity	NPC197757
0.9237	High Similarity	NPC228922
0.9224	High Similarity	NPC474565
0.9189	High Similarity	NPC2682
0.9174	High Similarity	NPC82862
0.9174	High Similarity	NPC206615
0.9174	High Similarity	NPC98631
0.9174	High Similarity	NPC470213
0.9174	High Similarity	NPC222127
0.9174	High Similarity	NPC31707
0.9174	High Similarity	NPC186843
0.9167	High Similarity	NPC76451
0.9167	High Similarity	NPC9891
0.9167	High Similarity	NPC88297
0.9167	High Similarity	NPC78974
0.9167	High Similarity	NPC223136
0.9167	High Similarity	NPC28730
0.9167	High Similarity	NPC18924
0.9167	High Similarity	NPC186845
0.9167	High Similarity	NPC103823
0.9167	High Similarity	NPC214406
0.9167	High Similarity	NPC44748
0.9167	High Similarity	NPC223953
0.9153	High Similarity	NPC473411
0.9153	High Similarity	NPC41562
0.9153	High Similarity	NPC71579
0.9153	High Similarity	NPC262253
0.9138	High Similarity	NPC308217
0.9115	High Similarity	NPC165106
0.9099	High Similarity	NPC165386
0.9099	High Similarity	NPC82016
0.9098	High Similarity	NPC474227
0.9098	High Similarity	NPC469951
0.9098	High Similarity	NPC469963
0.9098	High Similarity	NPC170844
0.9098	High Similarity	NPC476968
0.9091	High Similarity	NPC473092
0.9091	High Similarity	NPC471986
0.9091	High Similarity	NPC210355
0.9091	High Similarity	NPC189248
0.9091	High Similarity	NPC474119
0.9091	High Similarity	NPC202904
0.9091	High Similarity	NPC473093
0.9091	High Similarity	NPC8050
0.9083	High Similarity	NPC265483
0.9083	High Similarity	NPC299584
0.9083	High Similarity	NPC60885
0.9083	High Similarity	NPC82483
0.9083	High Similarity	NPC234400
0.9068	High Similarity	NPC75713
0.9052	High Similarity	NPC63083
0.9024	High Similarity	NPC224157
0.9024	High Similarity	NPC192687
0.9024	High Similarity	NPC311680
0.9024	High Similarity	NPC126836
0.9024	High Similarity	NPC51840
0.9024	High Similarity	NPC63574
0.9024	High Similarity	NPC299221
0.9024	High Similarity	NPC234488
0.9016	High Similarity	NPC328682
0.9016	High Similarity	NPC28765
0.9016	High Similarity	NPC154866
0.9016	High Similarity	NPC281864
0.9016	High Similarity	NPC207702
0.9016	High Similarity	NPC54321
0.9016	High Similarity	NPC283114
0.9016	High Similarity	NPC149008
0.9016	High Similarity	NPC210674
0.9009	High Similarity	NPC245115
0.9008	High Similarity	NPC244364
0.9	High Similarity	NPC5796
0.9	High Similarity	NPC206487
0.8966	High Similarity	NPC52464
0.8966	High Similarity	NPC474933
0.8966	High Similarity	NPC304208
0.8957	High Similarity	NPC475815
0.8957	High Similarity	NPC473264
0.8957	High Similarity	NPC47194
0.8952	High Similarity	NPC471983
0.8952	High Similarity	NPC474238
0.8952	High Similarity	NPC474017
0.8952	High Similarity	NPC192255
0.8952	High Similarity	NPC149337
0.8943	High Similarity	NPC3439
0.8943	High Similarity	NPC226788
0.8943	High Similarity	NPC218856
0.8943	High Similarity	NPC58164
0.8943	High Similarity	NPC202582
0.8943	High Similarity	NPC470258
0.8943	High Similarity	NPC190144
0.8943	High Similarity	NPC222004
0.8943	High Similarity	NPC10225
0.8943	High Similarity	NPC212015
0.8943	High Similarity	NPC210623
0.8943	High Similarity	NPC273295
0.8943	High Similarity	NPC285339
0.8943	High Similarity	NPC190629
0.8934	High Similarity	NPC266555
0.8934	High Similarity	NPC252131
0.8934	High Similarity	NPC236760
0.8934	High Similarity	NPC470699
0.8919	High Similarity	NPC35543
0.8917	High Similarity	NPC84086
0.8917	High Similarity	NPC121115
0.8917	High Similarity	NPC95168
0.8908	High Similarity	NPC126935
0.8908	High Similarity	NPC216929
0.8908	High Similarity	NPC312713
0.8908	High Similarity	NPC57268
0.8908	High Similarity	NPC172676
0.8908	High Similarity	NPC65933
0.8898	High Similarity	NPC232084
0.8898	High Similarity	NPC10932
0.8898	High Similarity	NPC61516
0.8898	High Similarity	NPC247364
0.8889	High Similarity	NPC474214
0.8889	High Similarity	NPC474612
0.888	High Similarity	NPC253105
0.888	High Similarity	NPC6451
0.888	High Similarity	NPC201587
0.8879	High Similarity	NPC81067
0.8879	High Similarity	NPC9341
0.8879	High Similarity	NPC141090
0.8871	High Similarity	NPC307042
0.8871	High Similarity	NPC470624
0.8871	High Similarity	NPC79184
0.8871	High Similarity	NPC472338
0.8871	High Similarity	NPC237169
0.8871	High Similarity	NPC476399
0.8862	High Similarity	NPC266691
0.8862	High Similarity	NPC474651
0.8862	High Similarity	NPC474623
0.8852	High Similarity	NPC181361
0.885	High Similarity	NPC303521
0.8843	High Similarity	NPC18449
0.8843	High Similarity	NPC122792
0.8843	High Similarity	NPC121783
0.8843	High Similarity	NPC228972
0.8843	High Similarity	NPC34902
0.8824	High Similarity	NPC199023
0.8814	High Similarity	NPC119949
0.8814	High Similarity	NPC226629
0.8814	High Similarity	NPC474320
0.8814	High Similarity	NPC20674
0.881	High Similarity	NPC263064
0.881	High Similarity	NPC136750
0.881	High Similarity	NPC158331
0.881	High Similarity	NPC475840
0.881	High Similarity	NPC32778
0.881	High Similarity	NPC196937
0.881	High Similarity	NPC266848
0.8803	High Similarity	NPC219070
0.8803	High Similarity	NPC470759
0.8803	High Similarity	NPC15860
0.8803	High Similarity	NPC127894
0.88	High Similarity	NPC472597
0.88	High Similarity	NPC30043
0.88	High Similarity	NPC469625
0.88	High Similarity	NPC141493

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 NPC254625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	1009
0.2-0.3	1724
0.3-0.4	2714
0.4-0.5	1647
0.5-0.6	951
0.6-0.7	541
0.7-0.8	113
0.8-0.85	10
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9153	High Similarity	NPD2981	Phase 2
0.9115	High Similarity	NPD5283	Phase 1
0.9098	High Similarity	NPD3027	Phase 3
0.9076	High Similarity	NPD2982	Phase 2
0.9076	High Similarity	NPD2983	Phase 2
0.8934	High Similarity	NPD3018	Phase 2
0.8413	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5536	Phase 2
0.8295	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD1613	Approved
0.8258	Intermediate Similarity	NPD3539	Phase 1
0.8222	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD3540	Phase 1
0.8162	Intermediate Similarity	NPD7124	Phase 2
0.8145	Intermediate Similarity	NPD3705	Approved
0.8136	Intermediate Similarity	NPD228	Approved
0.7984	Intermediate Similarity	NPD4908	Phase 1
0.797	Intermediate Similarity	NPD6111	Discontinued
0.7929	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD5109	Approved
0.7863	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD5111	Phase 2
0.7863	Intermediate Similarity	NPD5110	Phase 2
0.7857	Intermediate Similarity	NPD1610	Phase 2
0.7823	Intermediate Similarity	NPD1548	Phase 1
0.7815	Intermediate Similarity	NPD5451	Approved
0.7731	Intermediate Similarity	NPD2684	Approved
0.7714	Intermediate Similarity	NPD4357	Discontinued
0.771	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4005	Discontinued
0.7692	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD2922	Phase 1
0.7667	Intermediate Similarity	NPD3022	Approved
0.7667	Intermediate Similarity	NPD3021	Approved
0.7652	Intermediate Similarity	NPD4625	Phase 3
0.7623	Intermediate Similarity	NPD5535	Approved
0.7623	Intermediate Similarity	NPD7843	Approved
0.7606	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4749	Approved
0.7594	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5718	Phase 2
0.7586	Intermediate Similarity	NPD1242	Phase 1
0.7581	Intermediate Similarity	NPD7157	Approved
0.7574	Intermediate Similarity	NPD6895	Approved
0.7574	Intermediate Similarity	NPD6896	Approved
0.7569	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD37	Approved
0.7534	Intermediate Similarity	NPD1934	Approved
0.7517	Intermediate Similarity	NPD4675	Approved
0.7517	Intermediate Similarity	NPD4678	Approved
0.7483	Intermediate Similarity	NPD2801	Approved
0.7481	Intermediate Similarity	NPD1558	Phase 1
0.748	Intermediate Similarity	NPD1651	Approved
0.748	Intermediate Similarity	NPD1357	Approved
0.7465	Intermediate Similarity	NPD5297	Approved
0.7465	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4055	Discovery
0.7447	Intermediate Similarity	NPD2219	Phase 1
0.7432	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3817	Phase 2
0.7429	Intermediate Similarity	NPD3060	Approved
0.7429	Intermediate Similarity	NPD4237	Approved
0.7429	Intermediate Similarity	NPD4236	Phase 3
0.7426	Intermediate Similarity	NPD3657	Discovery
0.7391	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3882	Suspended
0.7383	Intermediate Similarity	NPD4965	Approved
0.7383	Intermediate Similarity	NPD4966	Approved
0.7383	Intermediate Similarity	NPD4967	Phase 2
0.7383	Intermediate Similarity	NPD6788	Approved
0.7373	Intermediate Similarity	NPD846	Approved
0.7373	Intermediate Similarity	NPD940	Approved
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.7365	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1358	Approved
0.7353	Intermediate Similarity	NPD3620	Phase 2
0.7353	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5494	Approved
0.7338	Intermediate Similarity	NPD2796	Approved
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD422	Phase 1
0.7303	Intermediate Similarity	NPD7199	Phase 2
0.7292	Intermediate Similarity	NPD1424	Approved
0.7287	Intermediate Similarity	NPD17	Approved
0.7287	Intermediate Similarity	NPD6516	Phase 2
0.7287	Intermediate Similarity	NPD5846	Approved
0.7286	Intermediate Similarity	NPD1375	Discontinued
0.7285	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD8651	Approved
0.7259	Intermediate Similarity	NPD7095	Approved
0.7255	Intermediate Similarity	NPD6232	Discontinued
0.7254	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3596	Phase 2
0.7241	Intermediate Similarity	NPD1350	Approved
0.7241	Intermediate Similarity	NPD2859	Approved
0.7241	Intermediate Similarity	NPD2860	Approved
0.7241	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1351	Approved
0.7241	Intermediate Similarity	NPD1349	Approved
0.7236	Intermediate Similarity	NPD4750	Phase 3
0.7234	Intermediate Similarity	NPD2808	Discontinued
0.7231	Intermediate Similarity	NPD3847	Discontinued
0.723	Intermediate Similarity	NPD5090	Approved
0.723	Intermediate Similarity	NPD5089	Approved
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7226	Intermediate Similarity	NPD1240	Approved
0.7222	Intermediate Similarity	NPD1511	Approved
0.7209	Intermediate Similarity	NPD5691	Approved
0.7208	Intermediate Similarity	NPD5242	Approved
0.7208	Intermediate Similarity	NPD3926	Phase 2
0.7208	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3020	Approved
0.7197	Intermediate Similarity	NPD5327	Phase 3
0.7197	Intermediate Similarity	NPD1669	Approved
0.7194	Intermediate Similarity	NPD4538	Approved
0.7194	Intermediate Similarity	NPD4536	Approved
0.7194	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5177	Phase 3
0.7183	Intermediate Similarity	NPD4162	Approved
0.7176	Intermediate Similarity	NPD1281	Approved
0.7172	Intermediate Similarity	NPD4123	Phase 3
0.7165	Intermediate Similarity	NPD6671	Approved
0.7164	Intermediate Similarity	NPD6584	Phase 3
0.7161	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6166	Phase 2
0.7155	Intermediate Similarity	NPD2934	Approved
0.7155	Intermediate Similarity	NPD2933	Approved
0.7154	Intermediate Similarity	NPD4626	Approved
0.7154	Intermediate Similarity	NPD2667	Approved
0.7154	Intermediate Similarity	NPD2668	Approved
0.7153	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2674	Phase 3
0.7152	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD1653	Approved
0.7143	Intermediate Similarity	NPD3748	Approved
0.7133	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4585	Approved
0.7133	Intermediate Similarity	NPD7466	Approved
0.7133	Intermediate Similarity	NPD4110	Phase 3
0.7133	Intermediate Similarity	NPD6331	Phase 2
0.7133	Intermediate Similarity	NPD3892	Phase 2
0.7132	Intermediate Similarity	NPD6580	Approved
0.7132	Intermediate Similarity	NPD7534	Approved
0.7132	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7533	Approved
0.7132	Intermediate Similarity	NPD6581	Approved
0.7131	Intermediate Similarity	NPD3134	Approved
0.7123	Intermediate Similarity	NPD1512	Approved
0.7122	Intermediate Similarity	NPD1607	Approved
0.7121	Intermediate Similarity	NPD1608	Approved
0.7115	Intermediate Similarity	NPD7473	Discontinued
0.7103	Intermediate Similarity	NPD6799	Approved
0.7101	Intermediate Similarity	NPD2238	Phase 2
0.7092	Intermediate Similarity	NPD2438	Suspended
0.7077	Intermediate Similarity	NPD5585	Approved
0.7077	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD290	Approved
0.707	Intermediate Similarity	NPD8251	Approved
0.707	Intermediate Similarity	NPD8252	Approved
0.707	Intermediate Similarity	NPD8099	Discontinued
0.7063	Intermediate Similarity	NPD6674	Discontinued
0.7059	Intermediate Similarity	NPD919	Approved
0.7059	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7447	Phase 1
0.7055	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4584	Approved
0.7045	Intermediate Similarity	NPD1091	Approved
0.7042	Intermediate Similarity	NPD7266	Discontinued
0.7037	Intermediate Similarity	NPD4624	Approved
0.7031	Intermediate Similarity	NPD2557	Approved
0.7031	Intermediate Similarity	NPD709	Approved
0.7031	Intermediate Similarity	NPD6387	Discontinued
0.7025	Intermediate Similarity	NPD8156	Discontinued
0.7025	Intermediate Similarity	NPD5844	Phase 1
0.7023	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5960	Phase 3
0.7021	Intermediate Similarity	NPD5588	Approved
0.7015	Intermediate Similarity	NPD1283	Approved
0.7013	Intermediate Similarity	NPD5677	Discontinued
0.7007	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD1182	Approved
0.7	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD2653	Approved
0.7	Intermediate Similarity	NPD3028	Approved
0.6992	Remote Similarity	NPD2232	Approved
0.6992	Remote Similarity	NPD2233	Approved
0.6992	Remote Similarity	NPD3972	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