NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.1
Volume:	217.507
LogP:	0.844
LogD:	1.373
LogS:	-1.815
# Rotatable Bonds:	5
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	1.897
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.386
MDCK Permeability:	2.255014805996325e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.134
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.33
Plasma Protein Binding (PPB):	49.47758102416992%
Volume Distribution (VD):	1.098
Pgp-substrate:	22.29349136352539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.679
CYP1A2-substrate:	0.896
CYP2C19-inhibitor:	0.103
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.678
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	11.293
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.925
Carcinogencity:	0.054
Eye Corrosion:	0.583
Eye Irritation:	0.944
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC49341

Natural Product ID:	NPC49341
*Common Name:**	4-(3-Hydroxypropyl)-2,6-Dimethoxyphenol
IUPAC Name:	4-(3-hydroxypropyl)-2,6-dimethoxyphenol
Synonyms:
Standard InCHIKey:	PHOPGVYKZWPIGA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h6-7,12-13H,3-5H2,1-2H3
SMILES:	COc1cc(CCCO)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3793371
PubChem CID:	529893
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643020]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27276091]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9124	Inula japonica	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	1
Others	6

Activity Type	# Activity
Individual Protein	1
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	>	20000.0	nM	PMID[467837]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	37.7	%	PMID[467838]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	1.23	%	PMID[467838]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	9.32	%	PMID[467838]
NPT2	Others	Unspecified		Percent Effect	=	16.94	%	PMID[467839]
NPT2	Others	Unspecified		Percent Effect	=	-6.776	%	PMID[467839]
NPT2	Others	Unspecified		Percent Effect	=	25.33	%	PMID[467839]

☑ 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 NPC49341 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	355
0.1-0.2	1685
0.2-0.3	5923
0.3-0.4	13297
0.4-0.5	4086
0.5-0.6	4764
0.6-0.7	7883
0.7-0.8	3522
0.8-0.85	703
0.85-0.9	331
0.9-0.95	141
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC220598
0.9828	High Similarity	NPC165375
0.9652	High Similarity	NPC229401
0.9649	High Similarity	NPC63083
0.9565	High Similarity	NPC20674
0.9474	High Similarity	NPC193067
0.9421	High Similarity	NPC206615
0.9421	High Similarity	NPC470213
0.9421	High Similarity	NPC98631
0.9421	High Similarity	NPC186843
0.9391	High Similarity	NPC259638
0.9344	High Similarity	NPC170844
0.9344	High Similarity	NPC476968
0.9333	High Similarity	NPC203133
0.9333	High Similarity	NPC221077
0.9333	High Similarity	NPC193544
0.9333	High Similarity	NPC116907
0.9333	High Similarity	NPC17943
0.9333	High Similarity	NPC298757
0.9333	High Similarity	NPC251855
0.9333	High Similarity	NPC233410
0.9333	High Similarity	NPC472093
0.9333	High Similarity	NPC117214
0.9333	High Similarity	NPC208950
0.9333	High Similarity	NPC475169
0.9333	High Similarity	NPC57490
0.9328	High Similarity	NPC197757
0.9328	High Similarity	NPC228922
0.9322	High Similarity	NPC470804
0.9316	High Similarity	NPC148615
0.9316	High Similarity	NPC35071
0.9316	High Similarity	NPC177475
0.931	High Similarity	NPC255675
0.9304	High Similarity	NPC221049
0.9268	High Similarity	NPC472338
0.9256	High Similarity	NPC103823
0.9256	High Similarity	NPC214406
0.9256	High Similarity	NPC44748
0.9256	High Similarity	NPC76451
0.9256	High Similarity	NPC18924
0.9256	High Similarity	NPC78974
0.9256	High Similarity	NPC223136
0.9256	High Similarity	NPC28730
0.925	High Similarity	NPC183446
0.9244	High Similarity	NPC262253
0.9244	High Similarity	NPC41562
0.9244	High Similarity	NPC473411
0.9244	High Similarity	NPC71579
0.9231	High Similarity	NPC320987
0.9231	High Similarity	NPC135961
0.9231	High Similarity	NPC181969
0.9194	High Similarity	NPC470096
0.9194	High Similarity	NPC472597
0.9194	High Similarity	NPC470095
0.9194	High Similarity	NPC474017
0.9187	High Similarity	NPC212015
0.918	High Similarity	NPC124452
0.918	High Similarity	NPC82679
0.918	High Similarity	NPC210355
0.918	High Similarity	NPC127587
0.918	High Similarity	NPC236791
0.918	High Similarity	NPC324112
0.918	High Similarity	NPC169474
0.918	High Similarity	NPC293054
0.918	High Similarity	NPC246620
0.918	High Similarity	NPC74817
0.918	High Similarity	NPC159968
0.918	High Similarity	NPC282000
0.9174	High Similarity	NPC234400
0.9174	High Similarity	NPC60885
0.9174	High Similarity	NPC299584
0.9174	High Similarity	NPC82483
0.9174	High Similarity	NPC265483
0.9167	High Similarity	NPC282496
0.9167	High Similarity	NPC136319
0.9167	High Similarity	NPC233526
0.916	High Similarity	NPC476343
0.9153	High Similarity	NPC61516
0.9153	High Similarity	NPC10932
0.9153	High Similarity	NPC247364
0.9153	High Similarity	NPC232084
0.912	High Similarity	NPC35932
0.912	High Similarity	NPC7903
0.912	High Similarity	NPC16208
0.912	High Similarity	NPC160991
0.912	High Similarity	NPC253105
0.912	High Similarity	NPC201587
0.912	High Similarity	NPC184447
0.9106	High Similarity	NPC154866
0.9106	High Similarity	NPC28765
0.9091	High Similarity	NPC206487
0.9091	High Similarity	NPC5796
0.9083	High Similarity	NPC270326
0.9083	High Similarity	NPC209567
0.9076	High Similarity	NPC166759
0.9076	High Similarity	NPC199023
0.9068	High Similarity	NPC24474
0.9068	High Similarity	NPC311595
0.9068	High Similarity	NPC226629
0.9048	High Similarity	NPC475840
0.9043	High Similarity	NPC204120
0.904	High Similarity	NPC309787
0.9032	High Similarity	NPC226788
0.9032	High Similarity	NPC285339
0.9032	High Similarity	NPC470258
0.9032	High Similarity	NPC10225
0.9032	High Similarity	NPC48315
0.9032	High Similarity	NPC218856
0.9032	High Similarity	NPC210623
0.9032	High Similarity	NPC190629
0.9032	High Similarity	NPC58164
0.9032	High Similarity	NPC273295
0.9032	High Similarity	NPC202582
0.9032	High Similarity	NPC3439
0.9032	High Similarity	NPC222004
0.9024	High Similarity	NPC266555
0.9024	High Similarity	NPC252131
0.9024	High Similarity	NPC474119
0.9016	High Similarity	NPC271985
0.9016	High Similarity	NPC105925
0.9008	High Similarity	NPC84086
0.9008	High Similarity	NPC121115
0.9008	High Similarity	NPC95168
0.9008	High Similarity	NPC471693
0.9008	High Similarity	NPC238810
0.9	High Similarity	NPC145780
0.9	High Similarity	NPC285289
0.8992	High Similarity	NPC474565
0.8976	High Similarity	NPC107478
0.8976	High Similarity	NPC326095
0.8976	High Similarity	NPC310854
0.8976	High Similarity	NPC244983
0.8976	High Similarity	NPC287745
0.8976	High Similarity	NPC170694
0.8968	High Similarity	NPC470270
0.8968	High Similarity	NPC470752
0.8968	High Similarity	NPC204215
0.8968	High Similarity	NPC175067
0.896	High Similarity	NPC126836
0.896	High Similarity	NPC469614
0.896	High Similarity	NPC299221
0.896	High Similarity	NPC469612
0.896	High Similarity	NPC234488
0.896	High Similarity	NPC311680
0.896	High Similarity	NPC51840
0.8952	High Similarity	NPC109275
0.8943	High Similarity	NPC223953
0.8943	High Similarity	NPC112596
0.8943	High Similarity	NPC473960
0.8943	High Similarity	NPC181361
0.8934	High Similarity	NPC228972
0.8934	High Similarity	NPC122792
0.8926	High Similarity	NPC135414
0.8926	High Similarity	NPC246967
0.8906	High Similarity	NPC256262
0.8906	High Similarity	NPC47398
0.8906	High Similarity	NPC234333
0.8906	High Similarity	NPC260898
0.8906	High Similarity	NPC472337
0.8898	High Similarity	NPC229442
0.8898	High Similarity	NPC164386
0.8898	High Similarity	NPC168059
0.8898	High Similarity	NPC158331
0.8889	High Similarity	NPC30043
0.8889	High Similarity	NPC469625
0.8889	High Similarity	NPC469613
0.888	High Similarity	NPC45824
0.888	High Similarity	NPC469951
0.888	High Similarity	NPC158477
0.888	High Similarity	NPC469963
0.8871	High Similarity	NPC165045
0.8871	High Similarity	NPC183181
0.8871	High Similarity	NPC111247
0.8871	High Similarity	NPC118533
0.8871	High Similarity	NPC5428
0.8871	High Similarity	NPC236760
0.8871	High Similarity	NPC163332
0.8871	High Similarity	NPC118787
0.8871	High Similarity	NPC470699
0.8871	High Similarity	NPC319625
0.8871	High Similarity	NPC41706
0.8871	High Similarity	NPC147821
0.8871	High Similarity	NPC292056
0.8871	High Similarity	NPC242032
0.887	High Similarity	NPC203924
0.887	High Similarity	NPC156840
0.887	High Similarity	NPC257124
0.887	High Similarity	NPC78918
0.887	High Similarity	NPC173746
0.887	High Similarity	NPC8547
0.887	High Similarity	NPC139617
0.8862	High Similarity	NPC148627
0.8862	High Similarity	NPC194519
0.8862	High Similarity	NPC300326
0.8862	High Similarity	NPC58279
0.886	High Similarity	NPC165386
0.8843	High Similarity	NPC262156
0.8843	High Similarity	NPC470212
0.8843	High Similarity	NPC324571
0.8843	High Similarity	NPC54872

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 NPC49341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	950
0.2-0.3	2204
0.3-0.4	2699
0.4-0.5	1491
0.5-0.6	850
0.6-0.7	547
0.7-0.8	86
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9344	High Similarity	NPD3027	Phase 3
0.887	High Similarity	NPD228	Approved
0.8672	High Similarity	NPD1613	Approved
0.8672	High Similarity	NPD1612	Clinical (unspecified phase)
0.8571	High Similarity	NPD1530	Clinical (unspecified phase)
0.8504	High Similarity	NPD1529	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD2982	Phase 2
0.8254	Intermediate Similarity	NPD2983	Phase 2
0.8175	Intermediate Similarity	NPD2981	Phase 2
0.814	Intermediate Similarity	NPD3018	Phase 2
0.8	Intermediate Similarity	NPD1357	Approved
0.7969	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3705	Approved
0.7951	Intermediate Similarity	NPD5283	Phase 1
0.792	Intermediate Similarity	NPD1548	Phase 1
0.7836	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD3620	Phase 2
0.7833	Intermediate Similarity	NPD2684	Approved
0.7832	Intermediate Similarity	NPD1653	Approved
0.7812	Intermediate Similarity	NPD1610	Phase 2
0.7803	Intermediate Similarity	NPD4908	Phase 1
0.7786	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7724	Intermediate Similarity	NPD7843	Approved
0.7704	Intermediate Similarity	NPD1558	Phase 1
0.7692	Intermediate Similarity	NPD4749	Approved
0.7687	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7157	Approved
0.766	Intermediate Similarity	NPD2219	Phase 1
0.763	Intermediate Similarity	NPD2674	Phase 3
0.7627	Intermediate Similarity	NPD846	Approved
0.7627	Intermediate Similarity	NPD940	Approved
0.7623	Intermediate Similarity	NPD3021	Approved
0.7623	Intermediate Similarity	NPD3022	Approved
0.7619	Intermediate Similarity	NPD1934	Approved
0.7603	Intermediate Similarity	NPD290	Approved
0.7594	Intermediate Similarity	NPD9494	Approved
0.7584	Intermediate Similarity	NPD3882	Suspended
0.7568	Intermediate Similarity	NPD2801	Approved
0.7565	Intermediate Similarity	NPD9296	Approved
0.7542	Intermediate Similarity	NPD1242	Phase 1
0.7538	Intermediate Similarity	NPD1091	Approved
0.7538	Intermediate Similarity	NPD422	Phase 1
0.7536	Intermediate Similarity	NPD6111	Discontinued
0.7534	Intermediate Similarity	NPD4005	Discontinued
0.7518	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD3540	Phase 1
0.7483	Intermediate Similarity	NPD6234	Discontinued
0.7479	Intermediate Similarity	NPD291	Approved
0.745	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4357	Discontinued
0.7431	Intermediate Similarity	NPD1511	Approved
0.7429	Intermediate Similarity	NPD3539	Phase 1
0.7426	Intermediate Similarity	NPD3144	Approved
0.7426	Intermediate Similarity	NPD3145	Approved
0.7422	Intermediate Similarity	NPD5536	Phase 2
0.7413	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4236	Phase 3
0.7394	Intermediate Similarity	NPD4237	Approved
0.7376	Intermediate Similarity	NPD7266	Discontinued
0.7365	Intermediate Similarity	NPD4678	Approved
0.7365	Intermediate Similarity	NPD4675	Approved
0.7355	Intermediate Similarity	NPD6166	Phase 2
0.7355	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4625	Phase 3
0.7351	Intermediate Similarity	NPD4965	Approved
0.7351	Intermediate Similarity	NPD4966	Approved
0.7351	Intermediate Similarity	NPD4967	Phase 2
0.7351	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4750	Phase 3
0.7329	Intermediate Similarity	NPD1512	Approved
0.7299	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7261	Intermediate Similarity	NPD7228	Approved
0.7254	Intermediate Similarity	NPD1375	Discontinued
0.7252	Intermediate Similarity	NPD9381	Approved
0.7252	Intermediate Similarity	NPD9384	Approved
0.7246	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7124	Phase 2
0.7239	Intermediate Similarity	NPD8651	Approved
0.7215	Intermediate Similarity	NPD7054	Approved
0.7206	Intermediate Similarity	NPD2861	Phase 2
0.7203	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4060	Phase 1
0.719	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1358	Approved
0.7171	Intermediate Similarity	NPD3817	Phase 2
0.7171	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7472	Approved
0.717	Intermediate Similarity	NPD7074	Phase 3
0.7165	Intermediate Similarity	NPD821	Approved
0.7164	Intermediate Similarity	NPD9622	Approved
0.7164	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7199	Phase 2
0.7153	Intermediate Similarity	NPD6674	Discontinued
0.7152	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6671	Approved
0.7114	Intermediate Similarity	NPD3687	Approved
0.7114	Intermediate Similarity	NPD3686	Approved
0.7113	Intermediate Similarity	NPD1510	Phase 2
0.7105	Intermediate Similarity	NPD2977	Approved
0.7105	Intermediate Similarity	NPD2978	Approved
0.7097	Intermediate Similarity	NPD968	Approved
0.709	Intermediate Similarity	NPD9269	Phase 2
0.7086	Intermediate Similarity	NPD5089	Approved
0.7086	Intermediate Similarity	NPD5090	Approved
0.7075	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2238	Phase 2
0.7071	Intermediate Similarity	NPD1240	Approved
0.7067	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6190	Approved
0.7047	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9094	Approved
0.7042	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4536	Approved
0.7042	Intermediate Similarity	NPD4538	Approved
0.7034	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4162	Approved
0.7034	Intermediate Similarity	NPD5177	Phase 3
0.7031	Intermediate Similarity	NPD9379	Approved
0.7031	Intermediate Similarity	NPD9377	Approved
0.7029	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4123	Phase 3
0.7021	Intermediate Similarity	NPD5124	Phase 1
0.7021	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4380	Phase 2
0.7019	Intermediate Similarity	NPD6797	Phase 2
0.7007	Intermediate Similarity	NPD9621	Approved
0.7007	Intermediate Similarity	NPD9620	Approved
0.7007	Intermediate Similarity	NPD9619	Approved
0.7007	Intermediate Similarity	NPD6584	Phase 3
0.7006	Intermediate Similarity	NPD6232	Discontinued
0.6993	Remote Similarity	NPD1465	Phase 2
0.6992	Remote Similarity	NPD1778	Approved
0.6992	Remote Similarity	NPD6516	Phase 2
0.6992	Remote Similarity	NPD4626	Approved
0.6992	Remote Similarity	NPD5846	Approved
0.698	Remote Similarity	NPD1350	Approved
0.698	Remote Similarity	NPD1349	Approved
0.698	Remote Similarity	NPD1351	Approved
0.6978	Remote Similarity	NPD3180	Approved
0.6978	Remote Similarity	NPD3179	Approved
0.6975	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7251	Discontinued
0.6975	Remote Similarity	NPD2934	Approved
0.6975	Remote Similarity	NPD2933	Approved
0.6972	Remote Similarity	NPD6653	Approved
0.6972	Remote Similarity	NPD1607	Approved
0.6962	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5297	Approved
0.6959	Remote Similarity	NPD1774	Approved
0.695	Remote Similarity	NPD943	Approved
0.6944	Remote Similarity	NPD6099	Approved
0.6944	Remote Similarity	NPD6100	Approved
0.6944	Remote Similarity	NPD2161	Phase 2
0.694	Remote Similarity	NPD3496	Discontinued
0.6939	Remote Similarity	NPD5241	Discontinued
0.6939	Remote Similarity	NPD2677	Approved
0.6933	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5109	Approved
0.6929	Remote Similarity	NPD5110	Phase 2
0.6929	Remote Similarity	NPD556	Approved
0.6929	Remote Similarity	NPD598	Approved
0.6929	Remote Similarity	NPD601	Approved
0.6929	Remote Similarity	NPD5111	Phase 2
0.6929	Remote Similarity	NPD597	Approved
0.6917	Remote Similarity	NPD844	Approved
0.6917	Remote Similarity	NPD2859	Approved
0.6917	Remote Similarity	NPD2860	Approved
0.6914	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3157	Approved
0.6913	Remote Similarity	NPD7447	Phase 1
0.6913	Remote Similarity	NPD1424	Approved
0.6913	Remote Similarity	NPD3158	Phase 1
0.6906	Remote Similarity	NPD600	Approved
0.6906	Remote Similarity	NPD596	Approved
0.6901	Remote Similarity	NPD3657	Discovery
0.6901	Remote Similarity	NPD5735	Approved
0.6901	Remote Similarity	NPD447	Suspended
0.6897	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5844	Phase 1
0.6894	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3020	Approved
0.6883	Remote Similarity	NPD5772	Approved
0.6883	Remote Similarity	NPD5773	Approved
0.6879	Remote Similarity	NPD1136	Approved
0.6879	Remote Similarity	NPD840	Approved
0.6879	Remote Similarity	NPD839	Approved
0.6879	Remote Similarity	NPD1132	Approved
0.6879	Remote Similarity	NPD1130	Approved
0.6875	Remote Similarity	NPD5960	Phase 3
0.6875	Remote Similarity	NPD5588	Approved
0.6875	Remote Similarity	NPD7473	Discontinued

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