NPASS Compound

Structure

CID120280 OpenBabel06191715472D 22 23 0 0 1 0 0 0 0 0999 V2000 -4.3301 -0.5000 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 -0.5000 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 -5.1962 -0.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 11 2 0 0 0 0 2 6 2 0 0 0 0 2 11 1 0 0 0 0 3 7 2 0 0 0 0 3 11 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 7 1 1 0 0 0 14 17 1 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 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	310.971
LogP:	1.685
LogD:	1.848
LogS:	-2.17
# Rotatable Bonds:	5
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	3.33
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.916
MDCK Permeability:	8.459400305582676e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.147
Human Intestinal Absorption (HIA):	0.073
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.402

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	96.18402099609375%
Volume Distribution (VD):	0.626
Pgp-substrate:	4.042309761047363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.139
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.122
CYP2D6-substrate:	0.437
CYP3A4-inhibitor:	0.637
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	18.081
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.248
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.956
Carcinogencity:	0.551
Eye Corrosion:	0.004
Eye Irritation:	0.31
Respiratory Toxicity:	0.461

Download Data

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

Natural Product: NPC120280

Natural Product ID:	NPC120280
*Common Name:**	Sequirin C
IUPAC Name:	4-[(E,3S,4S)-4,5-dihydroxy-1-(4-hydroxyphenyl)pent-1-en-3-yl]benzene-1,2-diol
Synonyms:	Sequirin C
Standard InCHIKey:	UWWISKPOVFKUES-SITIDLGXSA-N
Standard InCHI:	InChI=1S/C17H18O5/c18-10-17(22)14(12-4-8-15(20)16(21)9-12)7-3-11-1-5-13(19)6-2-11/h1-9,14,17-22H,10H2/b7-3+/t14-,17+/m0/s1
SMILES:	OC[C@H]([C@H](c1ccc(c(c1)O)O)/C=C/c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689216
PubChem CID:	12315463
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226514]
NPO734	Asparagus gobicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO734	Asparagus gobicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO734	Asparagus gobicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5500.0	nM	PMID[465242]

☑ 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 NPC120280 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	328
0.1-0.2	1393
0.2-0.3	3962
0.3-0.4	12601
0.4-0.5	6848
0.5-0.6	7828
0.6-0.7	6731
0.7-0.8	2604
0.8-0.85	316
0.85-0.9	69
0.9-0.95	6
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC120982
0.9623	High Similarity	NPC226401
0.9623	High Similarity	NPC79793
0.9623	High Similarity	NPC174096
0.9623	High Similarity	NPC147634
0.9533	High Similarity	NPC187583
0.9533	High Similarity	NPC179002
0.9533	High Similarity	NPC257430
0.9528	High Similarity	NPC55617
0.9528	High Similarity	NPC62258
0.9358	High Similarity	NPC471485
0.9346	High Similarity	NPC254833
0.9346	High Similarity	NPC228343
0.9151	High Similarity	NPC239291
0.9138	High Similarity	NPC473451
0.9057	High Similarity	NPC471511
0.9057	High Similarity	NPC12278
0.8983	High Similarity	NPC148627
0.8898	High Similarity	NPC257682
0.8898	High Similarity	NPC146355
0.8898	High Similarity	NPC131747
0.8879	High Similarity	NPC323810
0.887	High Similarity	NPC470215
0.887	High Similarity	NPC109371
0.887	High Similarity	NPC470214
0.8868	High Similarity	NPC110764
0.886	High Similarity	NPC200988
0.886	High Similarity	NPC175799
0.886	High Similarity	NPC610
0.886	High Similarity	NPC145023
0.8833	High Similarity	NPC165045
0.8833	High Similarity	NPC118533
0.8829	High Similarity	NPC268032
0.8814	High Similarity	NPC471693
0.8793	High Similarity	NPC34634
0.8793	High Similarity	NPC472071
0.8793	High Similarity	NPC265454
0.8783	High Similarity	NPC86198
0.8774	High Similarity	NPC294741
0.8774	High Similarity	NPC223393
0.8761	High Similarity	NPC12656
0.8761	High Similarity	NPC473137
0.8739	High Similarity	NPC44732
0.8729	High Similarity	NPC471794
0.8729	High Similarity	NPC85488
0.8718	High Similarity	NPC470414
0.8718	High Similarity	NPC207613
0.8716	High Similarity	NPC477814
0.8707	High Similarity	NPC70084
0.8692	High Similarity	NPC91461
0.8692	High Similarity	NPC7686
0.8692	High Similarity	NPC40258
0.8689	High Similarity	NPC475875
0.8679	High Similarity	NPC132078
0.8679	High Similarity	NPC131587
0.8679	High Similarity	NPC78119
0.8679	High Similarity	NPC51333
0.8679	High Similarity	NPC216468
0.8678	High Similarity	NPC5428
0.8661	High Similarity	NPC308689
0.8661	High Similarity	NPC297657
0.8655	High Similarity	NPC280704
0.8644	High Similarity	NPC473853
0.8644	High Similarity	NPC470212
0.8644	High Similarity	NPC324571
0.8644	High Similarity	NPC54872
0.8644	High Similarity	NPC113865
0.8644	High Similarity	NPC343720
0.8644	High Similarity	NPC262156
0.8644	High Similarity	NPC184651
0.8644	High Similarity	NPC312675
0.8632	High Similarity	NPC475245
0.8632	High Similarity	NPC56214
0.8632	High Similarity	NPC165133
0.8632	High Similarity	NPC117780
0.8632	High Similarity	NPC227217
0.8632	High Similarity	NPC242885
0.8632	High Similarity	NPC95614
0.8632	High Similarity	NPC232316
0.8621	High Similarity	NPC144343
0.8618	High Similarity	NPC257582
0.8618	High Similarity	NPC153739
0.8618	High Similarity	NPC242807
0.8618	High Similarity	NPC187998
0.8618	High Similarity	NPC42300
0.8618	High Similarity	NPC145305
0.8618	High Similarity	NPC92164
0.8618	High Similarity	NPC64201
0.8618	High Similarity	NPC241522
0.8618	High Similarity	NPC77040
0.8618	High Similarity	NPC174495
0.8611	High Similarity	NPC196479
0.8607	High Similarity	NPC184733
0.8607	High Similarity	NPC45774
0.8607	High Similarity	NPC282703
0.8607	High Similarity	NPC11258
0.8607	High Similarity	NPC21867
0.8607	High Similarity	NPC129570
0.8607	High Similarity	NPC128208
0.8598	High Similarity	NPC213730
0.8585	High Similarity	NPC109955
0.8571	High Similarity	NPC86900
0.8559	High Similarity	NPC98305
0.8559	High Similarity	NPC58427
0.8559	High Similarity	NPC114392
0.8559	High Similarity	NPC34864
0.8559	High Similarity	NPC105727
0.8559	High Similarity	NPC233835
0.8548	High Similarity	NPC277804
0.8548	High Similarity	NPC474017
0.8547	High Similarity	NPC281298
0.8547	High Similarity	NPC310338
0.8547	High Similarity	NPC217174
0.8534	High Similarity	NPC277588
0.8532	High Similarity	NPC120719
0.8525	High Similarity	NPC264900
0.8525	High Similarity	NPC79715
0.8525	High Similarity	NPC108659
0.8525	High Similarity	NPC231607
0.8522	High Similarity	NPC472893
0.8512	High Similarity	NPC194519
0.85	High Similarity	NPC317769
0.85	High Similarity	NPC31344
0.8491	Intermediate Similarity	NPC216520
0.8491	Intermediate Similarity	NPC292730
0.8491	Intermediate Similarity	NPC82664
0.8491	Intermediate Similarity	NPC132271
0.8487	Intermediate Similarity	NPC147654
0.8487	Intermediate Similarity	NPC237667
0.8487	Intermediate Similarity	NPC290451
0.8487	Intermediate Similarity	NPC160380
0.8487	Intermediate Similarity	NPC38996
0.8487	Intermediate Similarity	NPC127389
0.8487	Intermediate Similarity	NPC472271
0.8487	Intermediate Similarity	NPC476343
0.848	Intermediate Similarity	NPC106739
0.8475	Intermediate Similarity	NPC223451
0.8468	Intermediate Similarity	NPC143483
0.8468	Intermediate Similarity	NPC176527
0.8462	Intermediate Similarity	NPC470626
0.8462	Intermediate Similarity	NPC474040
0.8455	Intermediate Similarity	NPC206615
0.8455	Intermediate Similarity	NPC474178
0.8455	Intermediate Similarity	NPC470084
0.8455	Intermediate Similarity	NPC186843
0.8455	Intermediate Similarity	NPC470213
0.8455	Intermediate Similarity	NPC252307
0.8455	Intermediate Similarity	NPC98631
0.8455	Intermediate Similarity	NPC245826
0.8443	Intermediate Similarity	NPC94179
0.8443	Intermediate Similarity	NPC178284
0.8443	Intermediate Similarity	NPC58607
0.8443	Intermediate Similarity	NPC191037
0.843	Intermediate Similarity	NPC293701
0.843	Intermediate Similarity	NPC48990
0.843	Intermediate Similarity	NPC114901
0.8417	Intermediate Similarity	NPC321402
0.8413	Intermediate Similarity	NPC471749
0.8407	Intermediate Similarity	NPC475018
0.8403	Intermediate Similarity	NPC470849
0.8403	Intermediate Similarity	NPC470848
0.8403	Intermediate Similarity	NPC24125
0.84	Intermediate Similarity	NPC7171
0.84	Intermediate Similarity	NPC115207
0.84	Intermediate Similarity	NPC158079
0.84	Intermediate Similarity	NPC228346
0.84	Intermediate Similarity	NPC161557
0.84	Intermediate Similarity	NPC40432
0.84	Intermediate Similarity	NPC27843
0.8396	Intermediate Similarity	NPC274678
0.8393	Intermediate Similarity	NPC262365
0.839	Intermediate Similarity	NPC263386
0.839	Intermediate Similarity	NPC311595
0.839	Intermediate Similarity	NPC141791
0.839	Intermediate Similarity	NPC191866
0.839	Intermediate Similarity	NPC24474
0.8387	Intermediate Similarity	NPC184092
0.8387	Intermediate Similarity	NPC476968
0.8387	Intermediate Similarity	NPC170844
0.8387	Intermediate Similarity	NPC212015
0.8376	Intermediate Similarity	NPC164386
0.8376	Intermediate Similarity	NPC293619
0.8376	Intermediate Similarity	NPC476266
0.8374	Intermediate Similarity	NPC106511
0.8374	Intermediate Similarity	NPC319625
0.8374	Intermediate Similarity	NPC163332
0.8374	Intermediate Similarity	NPC292056
0.8374	Intermediate Similarity	NPC147821
0.8374	Intermediate Similarity	NPC41706
0.8374	Intermediate Similarity	NPC476536
0.8374	Intermediate Similarity	NPC127587
0.8374	Intermediate Similarity	NPC118787
0.8374	Intermediate Similarity	NPC183181
0.8374	Intermediate Similarity	NPC111247
0.8361	Intermediate Similarity	NPC33654
0.8348	Intermediate Similarity	NPC264558
0.8348	Intermediate Similarity	NPC176730
0.8348	Intermediate Similarity	NPC123175
0.8347	Intermediate Similarity	NPC53567
0.8347	Intermediate Similarity	NPC136319

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 NPC120280 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	870
0.2-0.3	1518
0.3-0.4	2912
0.4-0.5	1845
0.5-0.6	1139
0.6-0.7	466
0.7-0.8	94
0.8-0.85	7
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD3022	Approved
0.9346	High Similarity	NPD3021	Approved
0.8505	High Similarity	NPD3020	Approved
0.8387	Intermediate Similarity	NPD3027	Phase 3
0.8224	Intermediate Similarity	NPD2859	Approved
0.8224	Intermediate Similarity	NPD2860	Approved
0.8182	Intermediate Similarity	NPD3092	Approved
0.8131	Intermediate Similarity	NPD2933	Approved
0.8131	Intermediate Similarity	NPD2934	Approved
0.8065	Intermediate Similarity	NPD3094	Phase 2
0.8047	Intermediate Similarity	NPD3059	Approved
0.8047	Intermediate Similarity	NPD3061	Approved
0.8047	Intermediate Similarity	NPD3062	Approved
0.8034	Intermediate Similarity	NPD5283	Phase 1
0.8017	Intermediate Similarity	NPD9384	Approved
0.8017	Intermediate Similarity	NPD9381	Approved
0.8	Intermediate Similarity	NPD3091	Approved
0.7928	Intermediate Similarity	NPD1242	Phase 1
0.7923	Intermediate Similarity	NPD5314	Approved
0.7907	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD1613	Approved
0.7863	Intermediate Similarity	NPD228	Approved
0.7798	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD3620	Phase 2
0.7769	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD9622	Approved
0.7724	Intermediate Similarity	NPD3095	Discontinued
0.7724	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4750	Phase 3
0.7687	Intermediate Similarity	NPD7266	Discontinued
0.7687	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD288	Approved
0.7656	Intermediate Similarity	NPD2861	Phase 2
0.7647	Intermediate Similarity	NPD9377	Approved
0.7647	Intermediate Similarity	NPD9379	Approved
0.7619	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD9620	Approved
0.7578	Intermediate Similarity	NPD9619	Approved
0.7578	Intermediate Similarity	NPD9621	Approved
0.7568	Intermediate Similarity	NPD844	Approved
0.7559	Intermediate Similarity	NPD5310	Approved
0.7559	Intermediate Similarity	NPD5311	Approved
0.7544	Intermediate Similarity	NPD846	Approved
0.7544	Intermediate Similarity	NPD940	Approved
0.7519	Intermediate Similarity	NPD817	Approved
0.7519	Intermediate Similarity	NPD823	Approved
0.7519	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3055	Approved
0.75	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD3053	Approved
0.7481	Intermediate Similarity	NPD598	Approved
0.7481	Intermediate Similarity	NPD601	Approved
0.7481	Intermediate Similarity	NPD597	Approved
0.748	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD4659	Approved
0.746	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2228	Approved
0.7438	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2229	Approved
0.7438	Intermediate Similarity	NPD2234	Approved
0.7424	Intermediate Similarity	NPD1132	Approved
0.7424	Intermediate Similarity	NPD1136	Approved
0.7424	Intermediate Similarity	NPD1130	Approved
0.7395	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD1792	Phase 2
0.7387	Intermediate Similarity	NPD845	Approved
0.7373	Intermediate Similarity	NPD2342	Discontinued
0.7368	Intermediate Similarity	NPD943	Approved
0.7368	Intermediate Similarity	NPD4060	Phase 1
0.7364	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4103	Phase 2
0.736	Intermediate Similarity	NPD4093	Discontinued
0.7338	Intermediate Similarity	NPD6190	Approved
0.7328	Intermediate Similarity	NPD4908	Phase 1
0.7323	Intermediate Similarity	NPD1610	Phase 2
0.7319	Intermediate Similarity	NPD3060	Approved
0.7317	Intermediate Similarity	NPD7157	Approved
0.7311	Intermediate Similarity	NPD2684	Approved
0.7305	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD3028	Approved
0.7302	Intermediate Similarity	NPD3019	Approved
0.7302	Intermediate Similarity	NPD4059	Approved
0.7302	Intermediate Similarity	NPD2932	Approved
0.729	Intermediate Similarity	NPD111	Approved
0.7288	Intermediate Similarity	NPD1444	Approved
0.7288	Intermediate Similarity	NPD1445	Approved
0.7266	Intermediate Similarity	NPD2562	Approved
0.7266	Intermediate Similarity	NPD2561	Approved
0.7266	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD8166	Discontinued
0.7257	Intermediate Similarity	NPD1809	Phase 2
0.7252	Intermediate Similarity	NPD5736	Approved
0.7222	Intermediate Similarity	NPD1357	Approved
0.7218	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7843	Approved
0.7185	Intermediate Similarity	NPD5735	Approved
0.7183	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2286	Discontinued
0.7164	Intermediate Similarity	NPD6405	Approved
0.7164	Intermediate Similarity	NPD6407	Approved
0.7154	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2568	Approved
0.7131	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1558	Phase 1
0.7111	Intermediate Similarity	NPD2238	Phase 2
0.7111	Intermediate Similarity	NPD826	Approved
0.7111	Intermediate Similarity	NPD825	Approved
0.7101	Intermediate Similarity	NPD9570	Approved
0.7101	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2982	Phase 2
0.7077	Intermediate Similarity	NPD2983	Phase 2
0.7071	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5536	Phase 2
0.7063	Intermediate Similarity	NPD856	Approved
0.7063	Intermediate Similarity	NPD16	Approved
0.7063	Intermediate Similarity	NPD3645	Discontinued
0.7054	Intermediate Similarity	NPD3705	Approved
0.7045	Intermediate Similarity	NPD6584	Phase 3
0.7045	Intermediate Similarity	NPD258	Approved
0.7045	Intermediate Similarity	NPD257	Approved
0.7037	Intermediate Similarity	NPD6663	Approved
0.7031	Intermediate Similarity	NPD6516	Phase 2
0.7031	Intermediate Similarity	NPD5846	Approved
0.7031	Intermediate Similarity	NPD1751	Approved
0.7023	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5303	Approved
0.7008	Intermediate Similarity	NPD5304	Approved
0.7008	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD968	Approved
0.7	Intermediate Similarity	NPD2231	Phase 2
0.7	Intermediate Similarity	NPD2981	Phase 2
0.7	Intermediate Similarity	NPD2235	Phase 2
0.6992	Remote Similarity	NPD3018	Phase 2
0.6963	Remote Similarity	NPD5110	Phase 2
0.6963	Remote Similarity	NPD5109	Approved
0.6963	Remote Similarity	NPD5111	Phase 2
0.696	Remote Similarity	NPD9614	Approved
0.696	Remote Similarity	NPD9618	Approved
0.6957	Remote Similarity	NPD4536	Approved
0.6957	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4538	Approved
0.695	Remote Similarity	NPD4236	Phase 3
0.695	Remote Similarity	NPD4237	Approved
0.6937	Remote Similarity	NPD9094	Approved
0.6934	Remote Similarity	NPD6355	Discontinued
0.6929	Remote Similarity	NPD318	Approved
0.6929	Remote Similarity	NPD5762	Approved
0.6929	Remote Similarity	NPD5763	Approved
0.6929	Remote Similarity	NPD317	Approved
0.6923	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1201	Approved
0.6917	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2977	Approved
0.6913	Remote Similarity	NPD2978	Approved
0.6912	Remote Similarity	NPD2674	Phase 3
0.6906	Remote Similarity	NPD5960	Phase 3
0.6906	Remote Similarity	NPD7742	Approved
0.6906	Remote Similarity	NPD5588	Approved
0.6906	Remote Similarity	NPD7743	Approved
0.6905	Remote Similarity	NPD6671	Approved
0.6901	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4628	Phase 3
0.6901	Remote Similarity	NPD6331	Phase 2
0.6901	Remote Similarity	NPD4110	Phase 3
0.6899	Remote Similarity	NPD4589	Approved
0.6899	Remote Similarity	NPD2667	Approved
0.6899	Remote Similarity	NPD2668	Approved
0.6894	Remote Similarity	NPD8651	Approved
0.6889	Remote Similarity	NPD7095	Approved
0.687	Remote Similarity	NPD9269	Phase 2
0.687	Remote Similarity	NPD2230	Approved
0.687	Remote Similarity	NPD2233	Approved
0.687	Remote Similarity	NPD2232	Approved
0.6866	Remote Similarity	NPD9569	Approved
0.6861	Remote Similarity	NPD4140	Approved
0.6853	Remote Similarity	NPD5241	Discontinued
0.685	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD37	Approved
0.6846	Remote Similarity	NPD3026	Approved
0.6846	Remote Similarity	NPD3023	Approved
0.6846	Remote Similarity	NPD1934	Approved
0.6842	Remote Similarity	NPD6234	Discontinued
0.6842	Remote Similarity	NPD1470	Approved
0.6838	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3145	Approved
0.6838	Remote Similarity	NPD3144	Approved
0.6831	Remote Similarity	NPD5177	Phase 3
0.6831	Remote Similarity	NPD6674	Discontinued
0.6831	Remote Similarity	NPD4162	Approved
0.6829	Remote Similarity	NPD5451	Approved
0.6825	Remote Similarity	NPD2629	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