NPASS Compound

Structure

NPC210355 OpenBabel07101719132D 24 25 0 0 0 0 0 0 0 0999 V2000 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -2.5981 -0.5000 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 3.4641 -2.0000 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 4.3301 -0.5000 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 4.3301 -1.5000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 1 5 2 0 0 0 0 2 6 2 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 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 15 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	351.432
LogP:	4.624
LogD:	3.683
LogS:	-5.461
# Rotatable Bonds:	8
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	2.409
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.607
MDCK Permeability:	2.002254950639326e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.799
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	99.99740600585938%
Volume Distribution (VD):	0.639
Pgp-substrate:	1.6266170740127563%

ADMET: Metabolism

CYP1A2-inhibitor:	0.941
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.894
CYP2C19-substrate:	0.62
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.773
CYP2D6-substrate:	0.943
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.771

ADMET: Excretion

Clearance (CL):	11.689
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.011
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.949
Carcinogencity:	0.861
Eye Corrosion:	0.004
Eye Irritation:	0.302
Respiratory Toxicity:	0.214

Download Data

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

Natural Product: NPC210355

Natural Product ID:	NPC210355
*Common Name:**	2-Methoxy-6-(2-Methoxy-4-Prop-2-Enylphenoxy)-4-Prop-2-Enylphenol
IUPAC Name:	2-methoxy-6-(2-methoxy-4-prop-2-enylphenoxy)-4-prop-2-enylphenol
Synonyms:
Standard InCHIKey:	IHJFUBOOWFHEMB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-5-7-14-9-10-16(17(11-14)22-3)24-19-13-15(8-6-2)12-18(23-4)20(19)21/h5-6,9-13,21H,1-2,7-8H2,3-4H3
SMILES:	C=CCc1ccc(c(c1)OC)Oc1cc(CC=C)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577778
PubChem CID:	154407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO32850	nectandra leucantha	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25835647]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6
Others	5

Activity Type	# Activity
Cell Line	3
Organism	3
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	CC50	>	200000.0	nM	PMID[486704]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	=	78800.0	nM	PMID[486705]
NPT1383	Cell Line	A2058	Homo sapiens	IC50	>	100000.0	nM	PMID[486705]
NPT27	Others	Unspecified		CC50	>	293800.0	nM	PMID[486703]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	11.0	n.a.	PMID[486703]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	26700.0	nM	PMID[486703]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	2.3	n.a.	PMID[486704]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	86500.0	nM	PMID[486704]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	38600.0	nM	PMID[486704]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[486705]
NPT2	Others	Unspecified		Ratio IC50	>	1.1	n.a.	PMID[486705]

☑ 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 NPC210355 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	386
0.1-0.2	1682
0.2-0.3	5604
0.3-0.4	13379
0.4-0.5	3820
0.5-0.6	4329
0.6-0.7	6873
0.7-0.8	4905
0.8-0.85	934
0.85-0.9	504
0.9-0.95	238
0.95-1	43

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC472338
0.975	High Similarity	NPC122792
0.975	High Similarity	NPC228972
0.9677	High Similarity	NPC472597
0.9672	High Similarity	NPC470699
0.9669	High Similarity	NPC221077
0.9669	High Similarity	NPC251855
0.9669	High Similarity	NPC57490
0.9669	High Similarity	NPC233410
0.9669	High Similarity	NPC116907
0.9669	High Similarity	NPC298757
0.9669	High Similarity	NPC117214
0.9669	High Similarity	NPC208950
0.9669	High Similarity	NPC193544
0.9669	High Similarity	NPC475169
0.9669	High Similarity	NPC472093
0.9669	High Similarity	NPC203133
0.9669	High Similarity	NPC17943
0.96	High Similarity	NPC35932
0.96	High Similarity	NPC184447
0.96	High Similarity	NPC7903
0.96	High Similarity	NPC16208
0.96	High Similarity	NPC160991
0.959	High Similarity	NPC18924
0.959	High Similarity	NPC181361
0.959	High Similarity	NPC28730
0.959	High Similarity	NPC78974
0.959	High Similarity	NPC214406
0.959	High Similarity	NPC103823
0.959	High Similarity	NPC44748
0.959	High Similarity	NPC223136
0.9583	High Similarity	NPC71579
0.9583	High Similarity	NPC262253
0.9583	High Similarity	NPC473411
0.9524	High Similarity	NPC168059
0.9524	High Similarity	NPC475840
0.9524	High Similarity	NPC229442
0.9516	High Similarity	NPC470258
0.9516	High Similarity	NPC190629
0.9516	High Similarity	NPC285339
0.9516	High Similarity	NPC222004
0.9516	High Similarity	NPC226788
0.9516	High Similarity	NPC218856
0.9516	High Similarity	NPC202582
0.9516	High Similarity	NPC273295
0.9516	High Similarity	NPC210623
0.9516	High Similarity	NPC3439
0.9512	High Similarity	NPC282000
0.9512	High Similarity	NPC324112
0.9512	High Similarity	NPC169474
0.9512	High Similarity	NPC127587
0.9512	High Similarity	NPC236791
0.9512	High Similarity	NPC124452
0.9512	High Similarity	NPC474119
0.9512	High Similarity	NPC246620
0.9512	High Similarity	NPC74817
0.9512	High Similarity	NPC159968
0.9512	High Similarity	NPC293054
0.9512	High Similarity	NPC82679
0.9508	High Similarity	NPC234400
0.9508	High Similarity	NPC82483
0.9508	High Similarity	NPC265483
0.9508	High Similarity	NPC60885
0.9508	High Similarity	NPC299584
0.9504	High Similarity	NPC197757
0.9504	High Similarity	NPC282496
0.9504	High Similarity	NPC136319
0.9504	High Similarity	NPC228922
0.9504	High Similarity	NPC233526
0.95	High Similarity	NPC145780
0.9449	High Similarity	NPC317380
0.9449	High Similarity	NPC170694
0.9449	High Similarity	NPC310854
0.9444	High Similarity	NPC202762
0.9444	High Similarity	NPC86655
0.9444	High Similarity	NPC127624
0.9444	High Similarity	NPC470752
0.944	High Similarity	NPC91291
0.944	High Similarity	NPC214860
0.9435	High Similarity	NPC98631
0.9435	High Similarity	NPC206615
0.9435	High Similarity	NPC186843
0.9435	High Similarity	NPC470213
0.9431	High Similarity	NPC76451
0.9421	High Similarity	NPC41562
0.9417	High Similarity	NPC166759
0.9417	High Similarity	NPC472596
0.9375	High Similarity	NPC94750
0.9375	High Similarity	NPC474206
0.9375	High Similarity	NPC121812
0.9375	High Similarity	NPC470356
0.9375	High Similarity	NPC472337
0.9375	High Similarity	NPC112939
0.9375	High Similarity	NPC112246
0.937	High Similarity	NPC36661
0.9365	High Similarity	NPC469625
0.9365	High Similarity	NPC30043
0.9365	High Similarity	NPC469613
0.9365	High Similarity	NPC309787
0.9365	High Similarity	NPC470095
0.9365	High Similarity	NPC470096
0.936	High Similarity	NPC10225
0.936	High Similarity	NPC476968
0.936	High Similarity	NPC58164
0.936	High Similarity	NPC170844
0.936	High Similarity	NPC45824
0.9355	High Similarity	NPC111247
0.9355	High Similarity	NPC163332
0.9355	High Similarity	NPC319625
0.9355	High Similarity	NPC41706
0.9355	High Similarity	NPC292056
0.9355	High Similarity	NPC118787
0.9355	High Similarity	NPC147821
0.9355	High Similarity	NPC183181
0.935	High Similarity	NPC194519
0.935	High Similarity	NPC105925
0.9344	High Similarity	NPC95168
0.9333	High Similarity	NPC247364
0.9333	High Similarity	NPC61516
0.9333	High Similarity	NPC232084
0.9333	High Similarity	NPC474565
0.9333	High Similarity	NPC10932
0.9302	High Similarity	NPC227503
0.9302	High Similarity	NPC474639
0.9302	High Similarity	NPC230734
0.9302	High Similarity	NPC472336
0.9302	High Similarity	NPC162659
0.9302	High Similarity	NPC270456
0.9302	High Similarity	NPC472334
0.9302	High Similarity	NPC306441
0.9302	High Similarity	NPC265433
0.9302	High Similarity	NPC16435
0.9302	High Similarity	NPC248727
0.9291	High Similarity	NPC131128
0.9291	High Similarity	NPC201587
0.9291	High Similarity	NPC474134
0.9291	High Similarity	NPC253105
0.9286	High Similarity	NPC126836
0.9286	High Similarity	NPC469614
0.9286	High Similarity	NPC234488
0.9286	High Similarity	NPC469612
0.9286	High Similarity	NPC299221
0.9286	High Similarity	NPC311680
0.9286	High Similarity	NPC51840
0.928	High Similarity	NPC28765
0.928	High Similarity	NPC154866
0.9274	High Similarity	NPC178284
0.9274	High Similarity	NPC58607
0.9274	High Similarity	NPC191037
0.9268	High Similarity	NPC206487
0.9268	High Similarity	NPC5796
0.9268	High Similarity	NPC114901
0.9268	High Similarity	NPC293701
0.9268	High Similarity	NPC48990
0.9262	High Similarity	NPC261661
0.925	High Similarity	NPC20674
0.925	High Similarity	NPC226629
0.9231	High Similarity	NPC103976
0.9231	High Similarity	NPC107551
0.9231	High Similarity	NPC102904
0.9231	High Similarity	NPC176051
0.9231	High Similarity	NPC474282
0.9231	High Similarity	NPC326797
0.9231	High Similarity	NPC276490
0.9231	High Similarity	NPC211549
0.9225	High Similarity	NPC151224
0.9225	High Similarity	NPC234333
0.9225	High Similarity	NPC260898
0.9225	High Similarity	NPC61946
0.9225	High Similarity	NPC47398
0.9219	High Similarity	NPC36490
0.9219	High Similarity	NPC158331
0.9219	High Similarity	NPC11060
0.9213	High Similarity	NPC474017
0.9206	High Similarity	NPC212015
0.9206	High Similarity	NPC5851
0.9206	High Similarity	NPC86030
0.92	High Similarity	NPC236760
0.92	High Similarity	NPC252131
0.92	High Similarity	NPC216836
0.92	High Similarity	NPC266555
0.9187	High Similarity	NPC84086
0.9187	High Similarity	NPC121115
0.918	High Similarity	NPC49341
0.918	High Similarity	NPC75713
0.916	High Similarity	NPC319647
0.916	High Similarity	NPC260741
0.916	High Similarity	NPC127218
0.916	High Similarity	NPC70682
0.916	High Similarity	NPC25966
0.916	High Similarity	NPC245207
0.916	High Similarity	NPC22517
0.916	High Similarity	NPC55947
0.9154	High Similarity	NPC302701
0.9154	High Similarity	NPC269091
0.9147	High Similarity	NPC287745
0.9147	High Similarity	NPC256307
0.9147	High Similarity	NPC66840
0.9147	High Similarity	NPC106215
0.9147	High Similarity	NPC111635

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 NPC210355 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	929
0.2-0.3	1869
0.3-0.4	2708
0.4-0.5	1595
0.5-0.6	880
0.6-0.7	645
0.7-0.8	159
0.8-0.85	13
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.936	High Similarity	NPD3027	Phase 3
0.9127	High Similarity	NPD1529	Clinical (unspecified phase)
0.9048	High Similarity	NPD1530	Clinical (unspecified phase)
0.8992	High Similarity	NPD1612	Clinical (unspecified phase)
0.8992	High Similarity	NPD1613	Approved
0.8583	High Similarity	NPD2982	Phase 2
0.8583	High Similarity	NPD228	Approved
0.8583	High Similarity	NPD2983	Phase 2
0.8504	High Similarity	NPD2981	Phase 2
0.8462	Intermediate Similarity	NPD3018	Phase 2
0.84	Intermediate Similarity	NPD1548	Phase 1
0.8397	Intermediate Similarity	NPD4908	Phase 1
0.8295	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5283	Phase 1
0.8284	Intermediate Similarity	NPD1558	Phase 1
0.8281	Intermediate Similarity	NPD1610	Phase 2
0.8271	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD2801	Approved
0.8151	Intermediate Similarity	NPD1934	Approved
0.8108	Intermediate Similarity	NPD3882	Suspended
0.806	Intermediate Similarity	NPD4625	Phase 3
0.8015	Intermediate Similarity	NPD4749	Approved
0.7973	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1511	Approved
0.7967	Intermediate Similarity	NPD3022	Approved
0.7967	Intermediate Similarity	NPD3021	Approved
0.7891	Intermediate Similarity	NPD4678	Approved
0.7891	Intermediate Similarity	NPD4675	Approved
0.7886	Intermediate Similarity	NPD2684	Approved
0.7877	Intermediate Similarity	NPD1653	Approved
0.7868	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD422	Phase 1
0.7862	Intermediate Similarity	NPD1512	Approved
0.7801	Intermediate Similarity	NPD3540	Phase 1
0.7778	Intermediate Similarity	NPD7843	Approved
0.7778	Intermediate Similarity	NPD2861	Phase 2
0.7754	Intermediate Similarity	NPD4060	Phase 1
0.7752	Intermediate Similarity	NPD5536	Phase 2
0.775	Intermediate Similarity	NPD1242	Phase 1
0.7748	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6166	Phase 2
0.7742	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD7157	Approved
0.773	Intermediate Similarity	NPD3539	Phase 1
0.7727	Intermediate Similarity	NPD3705	Approved
0.7724	Intermediate Similarity	NPD4357	Discontinued
0.7708	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3817	Phase 2
0.7647	Intermediate Similarity	NPD6234	Discontinued
0.7626	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD3620	Phase 2
0.7597	Intermediate Similarity	NPD6671	Approved
0.7595	Intermediate Similarity	NPD7054	Approved
0.7594	Intermediate Similarity	NPD1091	Approved
0.7591	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD968	Approved
0.7574	Intermediate Similarity	NPD6584	Phase 3
0.7569	Intermediate Similarity	NPD3060	Approved
0.7554	Intermediate Similarity	NPD2674	Phase 3
0.7552	Intermediate Similarity	NPD7266	Discontinued
0.7551	Intermediate Similarity	NPD4123	Phase 3
0.7548	Intermediate Similarity	NPD7199	Phase 2
0.7547	Intermediate Similarity	NPD7472	Approved
0.7547	Intermediate Similarity	NPD7074	Phase 3
0.7536	Intermediate Similarity	NPD7095	Approved
0.7534	Intermediate Similarity	NPD7124	Phase 2
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.752	Intermediate Similarity	NPD290	Approved
0.75	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1357	Approved
0.7483	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4005	Discontinued
0.7466	Intermediate Similarity	NPD2219	Phase 1
0.7465	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4538	Approved
0.7465	Intermediate Similarity	NPD4536	Approved
0.7452	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4236	Phase 3
0.7448	Intermediate Similarity	NPD4162	Approved
0.7448	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4237	Approved
0.7447	Intermediate Similarity	NPD230	Phase 1
0.7445	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6516	Phase 2
0.7444	Intermediate Similarity	NPD5846	Approved
0.7434	Intermediate Similarity	NPD37	Approved
0.7432	Intermediate Similarity	NPD7447	Phase 1
0.7432	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD8651	Approved
0.7403	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD4965	Approved
0.7403	Intermediate Similarity	NPD4967	Phase 2
0.7398	Intermediate Similarity	NPD846	Approved
0.7398	Intermediate Similarity	NPD291	Approved
0.7398	Intermediate Similarity	NPD940	Approved
0.7391	Intermediate Similarity	NPD6797	Phase 2
0.7386	Intermediate Similarity	NPD1465	Phase 2
0.7383	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7212	Phase 2
0.7365	Intermediate Similarity	NPD6799	Approved
0.7365	Intermediate Similarity	NPD7213	Phase 3
0.7364	Intermediate Similarity	NPD5535	Approved
0.7361	Intermediate Similarity	NPD6099	Approved
0.7361	Intermediate Similarity	NPD6100	Approved
0.7357	Intermediate Similarity	NPD3144	Approved
0.7357	Intermediate Similarity	NPD3145	Approved
0.7353	Intermediate Similarity	NPD6583	Phase 3
0.7353	Intermediate Similarity	NPD6582	Phase 2
0.7346	Intermediate Similarity	NPD7251	Discontinued
0.7343	Intermediate Similarity	NPD6111	Discontinued
0.7333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2934	Approved
0.7333	Intermediate Similarity	NPD2933	Approved
0.7333	Intermediate Similarity	NPD9296	Approved
0.7329	Intermediate Similarity	NPD1652	Phase 2
0.7329	Intermediate Similarity	NPD6674	Discontinued
0.7324	Intermediate Similarity	NPD4340	Discontinued
0.7317	Intermediate Similarity	NPD8053	Approved
0.7317	Intermediate Similarity	NPD8054	Approved
0.7312	Intermediate Similarity	NPD7228	Approved
0.731	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1375	Discontinued
0.7305	Intermediate Similarity	NPD6233	Phase 2
0.7305	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7808	Phase 3
0.7301	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5960	Phase 3
0.7292	Intermediate Similarity	NPD5588	Approved
0.7279	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6331	Phase 2
0.7279	Intermediate Similarity	NPD4628	Phase 3
0.7279	Intermediate Similarity	NPD1608	Approved
0.7279	Intermediate Similarity	NPD4110	Phase 3
0.7279	Intermediate Similarity	NPD3892	Phase 2
0.7279	Intermediate Similarity	NPD3750	Approved
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.7273	Intermediate Similarity	NPD2860	Approved
0.7273	Intermediate Similarity	NPD2859	Approved
0.7267	Intermediate Similarity	NPD5844	Phase 1
0.7266	Intermediate Similarity	NPD9494	Approved
0.7266	Intermediate Similarity	NPD4750	Phase 3
0.726	Intermediate Similarity	NPD1549	Phase 2
0.7254	Intermediate Similarity	NPD1240	Approved
0.7244	Intermediate Similarity	NPD7075	Discontinued
0.7244	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3020	Approved
0.7234	Intermediate Similarity	NPD5111	Phase 2
0.7234	Intermediate Similarity	NPD5109	Approved
0.7234	Intermediate Similarity	NPD6798	Discontinued
0.7234	Intermediate Similarity	NPD5110	Phase 2
0.7231	Intermediate Similarity	NPD821	Approved
0.723	Intermediate Similarity	NPD6190	Approved
0.723	Intermediate Similarity	NPD2677	Approved
0.7203	Intermediate Similarity	NPD5124	Phase 1
0.7203	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5735	Approved
0.7203	Intermediate Similarity	NPD6355	Discontinued
0.7192	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4380	Phase 2
0.7183	Intermediate Similarity	NPD4062	Phase 3
0.7181	Intermediate Similarity	NPD5058	Phase 3
0.7178	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2922	Phase 1
0.7172	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1510	Phase 2
0.7171	Intermediate Similarity	NPD3686	Approved
0.7171	Intermediate Similarity	NPD3687	Approved
0.7162	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2978	Approved
0.7161	Intermediate Similarity	NPD2977	Approved
0.7153	Intermediate Similarity	NPD1607	Approved
0.7153	Intermediate Similarity	NPD2231	Phase 2
0.7153	Intermediate Similarity	NPD2235	Phase 2
0.7152	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4055	Discovery
0.7133	Intermediate Similarity	NPD943	Approved
0.7133	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5451	Approved
0.7132	Intermediate Similarity	NPD3496	Discontinued
0.7123	Intermediate Similarity	NPD2796	Approved
0.7123	Intermediate Similarity	NPD1551	Phase 2
0.7123	Intermediate Similarity	NPD2161	Phase 2
0.7113	Intermediate Similarity	NPD5718	Phase 2
0.7095	Intermediate Similarity	NPD5177	Phase 3
0.7091	Intermediate Similarity	NPD7549	Discontinued
0.709	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD447	Suspended
0.708	Intermediate Similarity	NPD1535	Discovery

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