NPASS Compound

Structure

NPC144343 OpenBabel07101718322D 28 29 0 0 0 0 0 0 0 0999 V2000 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 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 3.4641 2.0000 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 4.3301 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 0.0000 0.0000 C 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 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 5 1 0 0 0 0 4 6 1 0 0 0 0 5 16 2 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 17 2 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 23 2 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.2
Volume:	417.98
LogP:	5.963
LogD:	4.268
LogS:	-3.036
# Rotatable Bonds:	7
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	2.853
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.222
MDCK Permeability:	2.2268577595241368e-05
Pgp-inhibitor:	0.914
Pgp-substrate:	0.825
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.83
30% Bioavailability (F30%):	0.788

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	100.46503448486328%
Volume Distribution (VD):	0.802
Pgp-substrate:	0.4773661494255066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.413
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.64
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.898
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.18
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	12.421
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.797
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.732
Skin Sensitization:	0.969
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.915
Respiratory Toxicity:	0.522

Download Data

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

Natural Product: NPC144343

Natural Product ID:	NPC144343
*Common Name:**	Pawhuskin C
IUPAC Name:	5-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-2-[(2E)-3,7-dimethylocta-2,6-dienyl]benzene-1,3-diol
Synonyms:	Pawhuskin C
Standard InCHIKey:	YCBBOXBZWZTLGR-MZYNZGBKSA-N
Standard InCHI:	InChI=1S/C24H28O4/c1-16(2)5-4-6-17(3)7-11-20-22(26)14-19(15-23(20)27)9-8-18-10-12-21(25)24(28)13-18/h5,7-10,12-15,25-28H,4,6,11H2,1-3H3/b9-8+,17-7+
SMILES:	C/C(=CCc1c(O)cc(cc1O)/C=C/c1ccc(c(c1)O)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476923
PubChem CID:	11394888
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
NPO6957	Dalea purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738380]
NPO6957	Dalea purpurea	Species	Fabaceae	Eukaryota	Stems; Roots	n.a.	n.a.	PMID[8882432]
NPO6957	Dalea purpurea	Species	Fabaceae	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
Ki	1
Others	3

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Ke	>	10.0	uM	PMID[572887]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Ke	>	10.0	uM	PMID[572887]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Ke	>	10.0	uM	PMID[572887]
NPT2	Others	Unspecified		Ki	=	4200.0	nM	PMID[572886]

☑ 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 NPC144343 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	337
0.1-0.2	1678
0.2-0.3	5201
0.3-0.4	13901
0.4-0.5	4839
0.5-0.6	5379
0.6-0.7	8166
0.7-0.8	2600
0.8-0.85	443
0.85-0.9	128
0.9-0.95	20
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC24125
0.9732	High Similarity	NPC191866
0.9554	High Similarity	NPC277588
0.9478	High Similarity	NPC39029
0.9386	High Similarity	NPC217174
0.9364	High Similarity	NPC268032
0.931	High Similarity	NPC237667
0.9279	High Similarity	NPC166995
0.9237	High Similarity	NPC224342
0.9196	High Similarity	NPC117846
0.9182	High Similarity	NPC19808
0.9182	High Similarity	NPC33728
0.9153	High Similarity	NPC53567
0.9107	High Similarity	NPC43525
0.9091	High Similarity	NPC105727
0.9091	High Similarity	NPC174981
0.9091	High Similarity	NPC58427
0.9091	High Similarity	NPC114392
0.9091	High Similarity	NPC34864
0.9035	High Similarity	NPC472893
0.9018	High Similarity	NPC224527
0.9018	High Similarity	NPC4493
0.9018	High Similarity	NPC225679
0.9018	High Similarity	NPC165770
0.9018	High Similarity	NPC476632
0.9	High Similarity	NPC176527
0.8974	High Similarity	NPC472071
0.8879	High Similarity	NPC470760
0.886	High Similarity	NPC23804
0.886	High Similarity	NPC261343
0.8852	High Similarity	NPC293054
0.8852	High Similarity	NPC236791
0.8852	High Similarity	NPC74817
0.8852	High Similarity	NPC82679
0.8852	High Similarity	NPC236760
0.8852	High Similarity	NPC324112
0.8852	High Similarity	NPC246620
0.8852	High Similarity	NPC159968
0.8852	High Similarity	NPC124452
0.8852	High Similarity	NPC282000
0.8852	High Similarity	NPC169474
0.8839	High Similarity	NPC254833
0.8839	High Similarity	NPC228343
0.8833	High Similarity	NPC136319
0.8829	High Similarity	NPC158253
0.8829	High Similarity	NPC204901
0.8829	High Similarity	NPC232523
0.8818	High Similarity	NPC292452
0.8818	High Similarity	NPC37802
0.8818	High Similarity	NPC474839
0.8814	High Similarity	NPC223451
0.8793	High Similarity	NPC115808
0.8783	High Similarity	NPC107240
0.877	High Similarity	NPC78974
0.877	High Similarity	NPC214406
0.877	High Similarity	NPC18924
0.877	High Similarity	NPC28730
0.877	High Similarity	NPC44748
0.877	High Similarity	NPC103823
0.877	High Similarity	NPC223136
0.875	High Similarity	NPC63698
0.875	High Similarity	NPC61885
0.8739	High Similarity	NPC12640
0.8739	High Similarity	NPC109691
0.8739	High Similarity	NPC470700
0.8739	High Similarity	NPC39664
0.8739	High Similarity	NPC201662
0.8739	High Similarity	NPC302681
0.8739	High Similarity	NPC39097
0.8739	High Similarity	NPC118286
0.8739	High Similarity	NPC99836
0.8727	High Similarity	NPC471511
0.8727	High Similarity	NPC218879
0.8727	High Similarity	NPC30506
0.8727	High Similarity	NPC241891
0.8727	High Similarity	NPC119860
0.8727	High Similarity	NPC244513
0.8727	High Similarity	NPC102216
0.8727	High Similarity	NPC227458
0.871	High Similarity	NPC212015
0.8707	High Similarity	NPC246760
0.8707	High Similarity	NPC84999
0.8699	High Similarity	NPC252131
0.8689	High Similarity	NPC234400
0.8689	High Similarity	NPC203133
0.8689	High Similarity	NPC475169
0.8689	High Similarity	NPC82483
0.8689	High Similarity	NPC472093
0.8689	High Similarity	NPC17943
0.8689	High Similarity	NPC60885
0.8689	High Similarity	NPC105925
0.8689	High Similarity	NPC298757
0.8689	High Similarity	NPC265483
0.8689	High Similarity	NPC33654
0.8689	High Similarity	NPC233410
0.8689	High Similarity	NPC57490
0.8689	High Similarity	NPC116907
0.8689	High Similarity	NPC251855
0.8689	High Similarity	NPC117214
0.8689	High Similarity	NPC299584
0.8689	High Similarity	NPC208950
0.8689	High Similarity	NPC221077
0.8689	High Similarity	NPC193544
0.8684	High Similarity	NPC187583
0.8684	High Similarity	NPC257430
0.8684	High Similarity	NPC179002
0.8678	High Similarity	NPC197757
0.8678	High Similarity	NPC228922
0.8678	High Similarity	NPC121115
0.8673	High Similarity	NPC299568
0.8673	High Similarity	NPC186385
0.8661	High Similarity	NPC54844
0.8655	High Similarity	NPC475245
0.8655	High Similarity	NPC69006
0.8649	High Similarity	NPC246056
0.8649	High Similarity	NPC134829
0.864	High Similarity	NPC126836
0.864	High Similarity	NPC51840
0.864	High Similarity	NPC299221
0.864	High Similarity	NPC474481
0.864	High Similarity	NPC234488
0.864	High Similarity	NPC311680
0.8629	High Similarity	NPC154866
0.8629	High Similarity	NPC28765
0.8621	High Similarity	NPC120280
0.8596	High Similarity	NPC120982
0.8596	High Similarity	NPC475018
0.8596	High Similarity	NPC226401
0.8596	High Similarity	NPC79793
0.8596	High Similarity	NPC147634
0.8596	High Similarity	NPC174096
0.8595	High Similarity	NPC41562
0.8571	High Similarity	NPC232275
0.8571	High Similarity	NPC176893
0.8571	High Similarity	NPC15543
0.8571	High Similarity	NPC248904
0.856	High Similarity	NPC10225
0.856	High Similarity	NPC58164
0.8548	High Similarity	NPC266555
0.8548	High Similarity	NPC127587
0.8545	High Similarity	NPC100340
0.8545	High Similarity	NPC143659
0.8534	High Similarity	NPC263753
0.8527	High Similarity	NPC300846
0.8527	High Similarity	NPC476639
0.8527	High Similarity	NPC114155
0.8525	High Similarity	NPC233526
0.8525	High Similarity	NPC95168
0.8525	High Similarity	NPC282496
0.8525	High Similarity	NPC84086
0.8509	High Similarity	NPC202647
0.8509	High Similarity	NPC55617
0.8509	High Similarity	NPC62258
0.8504	High Similarity	NPC6451
0.8492	Intermediate Similarity	NPC244441
0.8487	Intermediate Similarity	NPC190514
0.8487	Intermediate Similarity	NPC48781
0.8487	Intermediate Similarity	NPC9592
0.8482	Intermediate Similarity	NPC239291
0.848	Intermediate Similarity	NPC206615
0.848	Intermediate Similarity	NPC186843
0.848	Intermediate Similarity	NPC470213
0.848	Intermediate Similarity	NPC266691
0.848	Intermediate Similarity	NPC98631
0.8468	Intermediate Similarity	NPC249828
0.8468	Intermediate Similarity	NPC302219
0.8468	Intermediate Similarity	NPC76451
0.8468	Intermediate Similarity	NPC85479
0.8468	Intermediate Similarity	NPC146798
0.8468	Intermediate Similarity	NPC168303
0.8468	Intermediate Similarity	NPC313030
0.8468	Intermediate Similarity	NPC196479
0.8468	Intermediate Similarity	NPC53051
0.8468	Intermediate Similarity	NPC94351
0.8468	Intermediate Similarity	NPC24404
0.8468	Intermediate Similarity	NPC222522
0.8468	Intermediate Similarity	NPC223953
0.8468	Intermediate Similarity	NPC106396
0.8468	Intermediate Similarity	NPC71002
0.8468	Intermediate Similarity	NPC242342
0.8462	Intermediate Similarity	NPC56329
0.8462	Intermediate Similarity	NPC35550
0.8462	Intermediate Similarity	NPC242715
0.8462	Intermediate Similarity	NPC201145
0.8462	Intermediate Similarity	NPC90615
0.8462	Intermediate Similarity	NPC272157
0.8462	Intermediate Similarity	NPC25111
0.8462	Intermediate Similarity	NPC6262
0.8462	Intermediate Similarity	NPC73535
0.8455	Intermediate Similarity	NPC161571
0.8455	Intermediate Similarity	NPC223393
0.8455	Intermediate Similarity	NPC10588
0.8455	Intermediate Similarity	NPC248573
0.8455	Intermediate Similarity	NPC275053
0.8455	Intermediate Similarity	NPC166761
0.845	Intermediate Similarity	NPC10314
0.845	Intermediate Similarity	NPC158142
0.845	Intermediate Similarity	NPC313081
0.845	Intermediate Similarity	NPC69029
0.845	Intermediate Similarity	NPC108198

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 NPC144343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	988
0.2-0.3	1581
0.3-0.4	3007
0.4-0.5	1712
0.5-0.6	1048
0.6-0.7	432
0.7-0.8	58
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD3021	Approved
0.8839	High Similarity	NPD3022	Approved
0.8673	High Similarity	NPD4750	Phase 3
0.8545	High Similarity	NPD940	Approved
0.8545	High Similarity	NPD846	Approved
0.8455	Intermediate Similarity	NPD1242	Phase 1
0.8413	Intermediate Similarity	NPD3027	Phase 3
0.8333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD2860	Approved
0.8091	Intermediate Similarity	NPD844	Approved
0.8091	Intermediate Similarity	NPD2859	Approved
0.8077	Intermediate Similarity	NPD943	Approved
0.8077	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1613	Approved
0.8036	Intermediate Similarity	NPD3020	Approved
0.8	Intermediate Similarity	NPD2934	Approved
0.8	Intermediate Similarity	NPD2933	Approved
0.7857	Intermediate Similarity	NPD288	Approved
0.771	Intermediate Similarity	NPD4625	Phase 3
0.7692	Intermediate Similarity	NPD3018	Phase 2
0.7686	Intermediate Similarity	NPD7635	Approved
0.7656	Intermediate Similarity	NPD4749	Approved
0.7634	Intermediate Similarity	NPD4908	Phase 1
0.7603	Intermediate Similarity	NPD228	Approved
0.7563	Intermediate Similarity	NPD2342	Discontinued
0.7522	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2983	Phase 2
0.7519	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5283	Phase 1
0.746	Intermediate Similarity	NPD1548	Phase 1
0.7455	Intermediate Similarity	NPD9094	Approved
0.7442	Intermediate Similarity	NPD2981	Phase 2
0.7405	Intermediate Similarity	NPD3053	Approved
0.7405	Intermediate Similarity	NPD3094	Phase 2
0.7405	Intermediate Similarity	NPD3055	Approved
0.7398	Intermediate Similarity	NPD9377	Approved
0.7398	Intermediate Similarity	NPD9379	Approved
0.7385	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD3092	Approved
0.7348	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5310	Approved
0.7328	Intermediate Similarity	NPD5311	Approved
0.7319	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9269	Phase 2
0.7304	Intermediate Similarity	NPD1809	Phase 2
0.7297	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD845	Approved
0.7279	Intermediate Similarity	NPD3062	Approved
0.7279	Intermediate Similarity	NPD3061	Approved
0.7279	Intermediate Similarity	NPD3059	Approved
0.7273	Intermediate Similarity	NPD1511	Approved
0.7259	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1934	Approved
0.7214	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7266	Discontinued
0.7209	Intermediate Similarity	NPD9384	Approved
0.7209	Intermediate Similarity	NPD9381	Approved
0.7203	Intermediate Similarity	NPD3028	Approved
0.7188	Intermediate Similarity	NPD3091	Approved
0.7182	Intermediate Similarity	NPD111	Approved
0.7181	Intermediate Similarity	NPD2801	Approved
0.7174	Intermediate Similarity	NPD5314	Approved
0.7174	Intermediate Similarity	NPD2568	Approved
0.7172	Intermediate Similarity	NPD1512	Approved
0.7153	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD9622	Approved
0.7103	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD230	Phase 1
0.7099	Intermediate Similarity	NPD422	Phase 1
0.7092	Intermediate Similarity	NPD3540	Phase 1
0.7087	Intermediate Similarity	NPD6671	Approved
0.7086	Intermediate Similarity	NPD3882	Suspended
0.7077	Intermediate Similarity	NPD2932	Approved
0.7077	Intermediate Similarity	NPD4059	Approved
0.7077	Intermediate Similarity	NPD3019	Approved
0.7077	Intermediate Similarity	NPD2286	Discontinued
0.7063	Intermediate Similarity	NPD2234	Approved
0.7063	Intermediate Similarity	NPD2229	Approved
0.7063	Intermediate Similarity	NPD2228	Approved
0.705	Intermediate Similarity	NPD1607	Approved
0.7045	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2861	Phase 2
0.7031	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4060	Phase 1
0.7029	Intermediate Similarity	NPD1558	Phase 1
0.7029	Intermediate Similarity	NPD3620	Phase 2
0.7021	Intermediate Similarity	NPD6100	Approved
0.7021	Intermediate Similarity	NPD5405	Approved
0.7021	Intermediate Similarity	NPD6099	Approved
0.7021	Intermediate Similarity	NPD5408	Approved
0.7021	Intermediate Similarity	NPD5406	Approved
0.7021	Intermediate Similarity	NPD3539	Phase 1
0.7021	Intermediate Similarity	NPD5404	Approved
0.7016	Intermediate Similarity	NPD1792	Phase 2
0.7008	Intermediate Similarity	NPD497	Approved
0.7007	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9268	Approved
0.7	Intermediate Similarity	NPD4093	Discontinued
0.6993	Remote Similarity	NPD6234	Discontinued
0.6993	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1201	Approved
0.6968	Remote Similarity	NPD6232	Discontinued
0.6963	Remote Similarity	NPD9620	Approved
0.6963	Remote Similarity	NPD258	Approved
0.6963	Remote Similarity	NPD257	Approved
0.6963	Remote Similarity	NPD9619	Approved
0.6963	Remote Similarity	NPD9621	Approved
0.6957	Remote Similarity	NPD6405	Approved
0.6957	Remote Similarity	NPD6407	Approved
0.6947	Remote Similarity	NPD4589	Approved
0.6947	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4626	Approved
0.6947	Remote Similarity	NPD3095	Discontinued
0.694	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD496	Approved
0.6929	Remote Similarity	NPD498	Approved
0.6929	Remote Similarity	NPD495	Approved
0.6929	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5304	Approved
0.6923	Remote Similarity	NPD5303	Approved
0.6918	Remote Similarity	NPD2421	Approved
0.6918	Remote Similarity	NPD2420	Approved
0.6911	Remote Similarity	NPD1444	Approved
0.6911	Remote Similarity	NPD1445	Approved
0.6909	Remote Similarity	NPD9089	Approved
0.6906	Remote Similarity	NPD1240	Approved
0.6906	Remote Similarity	NPD1555	Discontinued
0.6905	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD302	Approved
0.6897	Remote Similarity	NPD6190	Approved
0.6889	Remote Similarity	NPD1470	Approved
0.6887	Remote Similarity	NPD37	Approved
0.6884	Remote Similarity	NPD597	Approved
0.6884	Remote Similarity	NPD601	Approved
0.6884	Remote Similarity	NPD598	Approved
0.6879	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6166	Phase 2
0.6879	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1653	Approved
0.6846	Remote Similarity	NPD5536	Phase 2
0.6835	Remote Similarity	NPD1136	Approved
0.6835	Remote Similarity	NPD7473	Discontinued
0.6835	Remote Similarity	NPD1130	Approved
0.6835	Remote Similarity	NPD1132	Approved
0.6831	Remote Similarity	NPD1510	Phase 2
0.6828	Remote Similarity	NPD8166	Discontinued
0.6828	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD9093	Approved
0.6818	Remote Similarity	NPD1751	Approved
0.6809	Remote Similarity	NPD817	Approved
0.6809	Remote Similarity	NPD4097	Suspended
0.6809	Remote Similarity	NPD823	Approved
0.6803	Remote Similarity	NPD4357	Discontinued
0.68	Remote Similarity	NPD2684	Approved
0.6797	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD825	Approved
0.6786	Remote Similarity	NPD826	Approved
0.6783	Remote Similarity	NPD2935	Discontinued
0.6781	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1980	Approved
0.6767	Remote Similarity	NPD1981	Approved
0.6767	Remote Similarity	NPD1983	Approved
0.6759	Remote Similarity	NPD3060	Approved
0.6757	Remote Similarity	NPD7447	Phase 1
0.6757	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4966	Approved
0.6753	Remote Similarity	NPD4967	Phase 2
0.6753	Remote Similarity	NPD4965	Approved
0.675	Remote Similarity	NPD9273	Approved
0.6741	Remote Similarity	NPD4659	Approved
0.6735	Remote Similarity	NPD7124	Phase 2
0.6719	Remote Similarity	NPD7843	Approved
0.6715	Remote Similarity	NPD6584	Phase 3
0.6714	Remote Similarity	NPD2674	Phase 3
0.6712	Remote Similarity	NPD3750	Approved
0.671	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7074	Phase 3
0.6692	Remote Similarity	NPD7157	Approved
0.6691	Remote Similarity	NPD6696	Suspended
0.6691	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD7212	Phase 2
0.6689	Remote Similarity	NPD4005	Discontinued
0.6689	Remote Similarity	NPD7213	Phase 3
0.6688	Remote Similarity	NPD3817	Phase 2
0.6688	Remote Similarity	NPD7199	Phase 2

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