NPASS Compound

Structure

NPC120982 OpenBabel07101718302D 24 25 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 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 -3.4641 -3.0000 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 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -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 -6.0622 -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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 13 1 0 0 0 0 4 15 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 15 20 1 1 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	348.2
LogP:	2.949
LogD:	2.928
LogS:	-3.272
# Rotatable Bonds:	8
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	2.703
Fsp3:	0.368
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:	-5.188
MDCK Permeability:	1.3970920917927288e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.359
Human Intestinal Absorption (HIA):	0.859
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	96.5054702758789%
Volume Distribution (VD):	0.736
Pgp-substrate:	3.695615768432617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.674
CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.584
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.605
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.815
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.155
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	19.041
Half-life (T1/2):	0.921

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.657
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.969
Carcinogencity:	0.128
Eye Corrosion:	0.067
Eye Irritation:	0.959
Respiratory Toxicity:	0.185

Download Data

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

Natural Product: NPC120982

Natural Product ID:	NPC120982
*Common Name:**	(3R)-1,7-Bis-(3,4-Dihydroxyphenyl)-3-Heptanol
IUPAC Name:	4-[(5R)-7-(3,4-dihydroxyphenyl)-5-hydroxyheptyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	KCWHZHZEQUHBCW-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C19H24O5/c20-15(8-5-14-7-10-17(22)19(24)12-14)4-2-1-3-13-6-9-16(21)18(23)11-13/h6-7,9-12,15,20-24H,1-5,8H2/t15-/m1/s1
SMILES:	O[C@@H](CCc1ccc(c(c1)O)O)CCCCc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464363
PubChem CID:	10088141
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO32876	alnus hirsuta f. sibirica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465614]
NPO23108	Pinus flexilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834165]
NPO23108	Pinus flexilis	Species	Pinaceae	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	3

Activity Type	# Activity
Cell Line	3
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	IC50	=	1.6	ug.mL-1	PMID[491477]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	90.0	%	PMID[491478]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	86.4	%	PMID[491478]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	84.6	%	PMID[491478]

☑ 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 NPC120982 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	301
0.1-0.2	1450
0.2-0.3	4649
0.3-0.4	13442
0.4-0.5	5825
0.5-0.6	8270
0.6-0.7	6101
0.7-0.8	2253
0.8-0.85	304
0.85-0.9	73
0.9-0.95	18
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC147634
1.0	High Similarity	NPC79793
1.0	High Similarity	NPC226401
1.0	High Similarity	NPC174096
0.9903	High Similarity	NPC179002
0.9903	High Similarity	NPC257430
0.9903	High Similarity	NPC187583
0.9902	High Similarity	NPC62258
0.9902	High Similarity	NPC55617
0.9623	High Similarity	NPC120280
0.9412	High Similarity	NPC471511
0.9333	High Similarity	NPC228343
0.9333	High Similarity	NPC254833
0.9216	High Similarity	NPC110764
0.9189	High Similarity	NPC109371
0.9189	High Similarity	NPC470214
0.9189	High Similarity	NPC470215
0.9182	High Similarity	NPC145023
0.9182	High Similarity	NPC200988
0.9182	High Similarity	NPC175799
0.9182	High Similarity	NPC610
0.9167	High Similarity	NPC471485
0.9135	High Similarity	NPC239291
0.9118	High Similarity	NPC223393
0.9118	High Similarity	NPC294741
0.9107	High Similarity	NPC34634
0.9107	High Similarity	NPC265454
0.9099	High Similarity	NPC86198
0.9038	High Similarity	NPC12278
0.9029	High Similarity	NPC40258
0.9029	High Similarity	NPC91461
0.9029	High Similarity	NPC7686
0.9027	High Similarity	NPC207613
0.902	High Similarity	NPC78119
0.902	High Similarity	NPC132078
0.902	High Similarity	NPC131587
0.902	High Similarity	NPC216468
0.902	High Similarity	NPC51333
0.9018	High Similarity	NPC70084
0.8981	High Similarity	NPC297657
0.8947	High Similarity	NPC54872
0.8947	High Similarity	NPC470212
0.8947	High Similarity	NPC324571
0.8947	High Similarity	NPC262156
0.8947	High Similarity	NPC343720
0.8947	High Similarity	NPC312675
0.8947	High Similarity	NPC473853
0.8947	High Similarity	NPC113865
0.8947	High Similarity	NPC184651
0.8942	High Similarity	NPC196479
0.8932	High Similarity	NPC213730
0.8922	High Similarity	NPC109955
0.8889	High Similarity	NPC44732
0.887	High Similarity	NPC86900
0.8868	High Similarity	NPC477814
0.886	High Similarity	NPC98305
0.8857	High Similarity	NPC323810
0.8807	High Similarity	NPC308689
0.8807	High Similarity	NPC268032
0.8793	High Similarity	NPC471693
0.8793	High Similarity	NPC473451
0.8783	High Similarity	NPC290451
0.8783	High Similarity	NPC127389
0.8761	High Similarity	NPC470626
0.8725	High Similarity	NPC274678
0.8707	High Similarity	NPC85488
0.8704	High Similarity	NPC233835
0.8696	High Similarity	NPC470849
0.8696	High Similarity	NPC470848
0.8684	High Similarity	NPC24474
0.8684	High Similarity	NPC263386
0.8684	High Similarity	NPC141791
0.8684	High Similarity	NPC311595
0.8679	High Similarity	NPC120719
0.8673	High Similarity	NPC164386
0.8673	High Similarity	NPC293619
0.8644	High Similarity	NPC148627
0.8632	High Similarity	NPC280704
0.8627	High Similarity	NPC151715
0.8627	High Similarity	NPC76938
0.8609	High Similarity	NPC227217
0.8609	High Similarity	NPC242885
0.8609	High Similarity	NPC95614
0.8609	High Similarity	NPC232316
0.8609	High Similarity	NPC165133
0.8609	High Similarity	NPC472071
0.8609	High Similarity	NPC117780
0.8609	High Similarity	NPC56214
0.8598	High Similarity	NPC233396
0.8598	High Similarity	NPC154899
0.8596	High Similarity	NPC474214
0.8596	High Similarity	NPC144343
0.8585	High Similarity	NPC477801
0.8585	High Similarity	NPC477802
0.8584	High Similarity	NPC61062
0.8584	High Similarity	NPC299252
0.8584	High Similarity	NPC277394
0.8571	High Similarity	NPC12656
0.8571	High Similarity	NPC473137
0.8571	High Similarity	NPC94179
0.8559	High Similarity	NPC146355
0.8559	High Similarity	NPC51698
0.8559	High Similarity	NPC131747
0.8559	High Similarity	NPC257682
0.8558	High Similarity	NPC474073
0.8544	High Similarity	NPC107522
0.8544	High Similarity	NPC26244
0.8544	High Similarity	NPC32714
0.8534	High Similarity	NPC470414
0.8532	High Similarity	NPC262365
0.8532	High Similarity	NPC58427
0.8532	High Similarity	NPC105727
0.8532	High Similarity	NPC34864
0.8532	High Similarity	NPC114392
0.8522	High Similarity	NPC281298
0.8522	High Similarity	NPC474320
0.8522	High Similarity	NPC310338
0.8519	High Similarity	NPC135464
0.8519	High Similarity	NPC92623
0.8509	High Similarity	NPC277588
0.85	High Similarity	NPC79715
0.85	High Similarity	NPC165045
0.85	High Similarity	NPC264900
0.85	High Similarity	NPC108659
0.85	High Similarity	NPC118533
0.85	High Similarity	NPC231607
0.8491	Intermediate Similarity	NPC471578
0.8491	Intermediate Similarity	NPC101025
0.8487	Intermediate Similarity	NPC194519
0.8475	Intermediate Similarity	NPC31344
0.8475	Intermediate Similarity	NPC317769
0.8462	Intermediate Similarity	NPC38996
0.8462	Intermediate Similarity	NPC132271
0.8462	Intermediate Similarity	NPC292730
0.8462	Intermediate Similarity	NPC147654
0.8462	Intermediate Similarity	NPC473388
0.8462	Intermediate Similarity	NPC160380
0.8462	Intermediate Similarity	NPC472271
0.8462	Intermediate Similarity	NPC216520
0.8462	Intermediate Similarity	NPC82664
0.8448	Intermediate Similarity	NPC475245
0.8448	Intermediate Similarity	NPC223451
0.844	Intermediate Similarity	NPC176527
0.8435	Intermediate Similarity	NPC474040
0.8435	Intermediate Similarity	NPC275519
0.8435	Intermediate Similarity	NPC309434
0.8431	Intermediate Similarity	NPC45040
0.843	Intermediate Similarity	NPC206615
0.843	Intermediate Similarity	NPC186843
0.843	Intermediate Similarity	NPC245826
0.843	Intermediate Similarity	NPC252307
0.843	Intermediate Similarity	NPC470213
0.843	Intermediate Similarity	NPC98631
0.843	Intermediate Similarity	NPC474178
0.8417	Intermediate Similarity	NPC58607
0.8417	Intermediate Similarity	NPC191037
0.8417	Intermediate Similarity	NPC178284
0.8403	Intermediate Similarity	NPC293701
0.8403	Intermediate Similarity	NPC48990
0.8403	Intermediate Similarity	NPC114901
0.839	Intermediate Similarity	NPC321402
0.839	Intermediate Similarity	NPC471794
0.8378	Intermediate Similarity	NPC63345
0.8378	Intermediate Similarity	NPC475018
0.8376	Intermediate Similarity	NPC24125
0.8362	Intermediate Similarity	NPC191866
0.8362	Intermediate Similarity	NPC217174
0.8362	Intermediate Similarity	NPC268572
0.8361	Intermediate Similarity	NPC475875
0.8361	Intermediate Similarity	NPC184092
0.8361	Intermediate Similarity	NPC476968
0.8361	Intermediate Similarity	NPC212015
0.8361	Intermediate Similarity	NPC170844
0.835	Intermediate Similarity	NPC325292
0.835	Intermediate Similarity	NPC138117
0.8349	Intermediate Similarity	NPC19149
0.8348	Intermediate Similarity	NPC86947
0.8348	Intermediate Similarity	NPC278652
0.8347	Intermediate Similarity	NPC147821
0.8347	Intermediate Similarity	NPC5428
0.8347	Intermediate Similarity	NPC183181
0.8347	Intermediate Similarity	NPC111247
0.8347	Intermediate Similarity	NPC163332
0.8347	Intermediate Similarity	NPC292056
0.8347	Intermediate Similarity	NPC41706
0.8347	Intermediate Similarity	NPC319625
0.8347	Intermediate Similarity	NPC118787
0.8333	Intermediate Similarity	NPC300017
0.8333	Intermediate Similarity	NPC52087
0.8333	Intermediate Similarity	NPC192
0.8333	Intermediate Similarity	NPC474486
0.8333	Intermediate Similarity	NPC472893
0.8319	Intermediate Similarity	NPC136319
0.8319	Intermediate Similarity	NPC264558
0.8305	Intermediate Similarity	NPC266045
0.8305	Intermediate Similarity	NPC237667
0.8305	Intermediate Similarity	NPC476343
0.8304	Intermediate Similarity	NPC177576
0.8302	Intermediate Similarity	NPC92730
0.8293	Intermediate Similarity	NPC257582

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 NPC120982 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	903
0.2-0.3	1507
0.3-0.4	2871
0.4-0.5	1881
0.5-0.6	1111
0.6-0.7	489
0.7-0.8	98
0.8-0.85	8
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD3022	Approved
0.9333	High Similarity	NPD3021	Approved
0.8544	High Similarity	NPD2859	Approved
0.8544	High Similarity	NPD2860	Approved
0.8476	Intermediate Similarity	NPD3020	Approved
0.8447	Intermediate Similarity	NPD2933	Approved
0.8447	Intermediate Similarity	NPD2934	Approved
0.8361	Intermediate Similarity	NPD3027	Phase 3
0.8142	Intermediate Similarity	NPD228	Approved
0.8016	Intermediate Similarity	NPD3061	Approved
0.8016	Intermediate Similarity	NPD3062	Approved
0.8016	Intermediate Similarity	NPD3059	Approved
0.8	Intermediate Similarity	NPD5283	Phase 1
0.8	Intermediate Similarity	NPD3092	Approved
0.7983	Intermediate Similarity	NPD9384	Approved
0.7983	Intermediate Similarity	NPD9381	Approved
0.7966	Intermediate Similarity	NPD3091	Approved
0.7925	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD9379	Approved
0.7913	Intermediate Similarity	NPD9377	Approved
0.7891	Intermediate Similarity	NPD5314	Approved
0.789	Intermediate Similarity	NPD1242	Phase 1
0.7886	Intermediate Similarity	NPD3094	Phase 2
0.7874	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1613	Approved
0.7869	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD844	Approved
0.7805	Intermediate Similarity	NPD5311	Approved
0.7805	Intermediate Similarity	NPD5310	Approved
0.7742	Intermediate Similarity	NPD3055	Approved
0.7742	Intermediate Similarity	NPD3053	Approved
0.7739	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD3620	Phase 2
0.7734	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD9622	Approved
0.7686	Intermediate Similarity	NPD3095	Discontinued
0.7652	Intermediate Similarity	NPD7266	Discontinued
0.7615	Intermediate Similarity	NPD288	Approved
0.7578	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD111	Approved
0.7568	Intermediate Similarity	NPD3028	Approved
0.7568	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD2684	Approved
0.7559	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD9619	Approved
0.754	Intermediate Similarity	NPD9620	Approved
0.754	Intermediate Similarity	NPD9621	Approved
0.7519	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD846	Approved
0.7481	Intermediate Similarity	NPD823	Approved
0.7481	Intermediate Similarity	NPD817	Approved
0.748	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD2342	Discontinued
0.7459	Intermediate Similarity	NPD1357	Approved
0.7458	Intermediate Similarity	NPD7843	Approved
0.7458	Intermediate Similarity	NPD7635	Approved
0.7442	Intermediate Similarity	NPD597	Approved
0.7442	Intermediate Similarity	NPD598	Approved
0.7442	Intermediate Similarity	NPD601	Approved
0.744	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7157	Approved
0.7395	Intermediate Similarity	NPD2229	Approved
0.7395	Intermediate Similarity	NPD2228	Approved
0.7395	Intermediate Similarity	NPD2234	Approved
0.7385	Intermediate Similarity	NPD1136	Approved
0.7385	Intermediate Similarity	NPD1130	Approved
0.7385	Intermediate Similarity	NPD1132	Approved
0.7364	Intermediate Similarity	NPD1809	Phase 2
0.735	Intermediate Similarity	NPD1792	Phase 2
0.735	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD4750	Phase 3
0.7344	Intermediate Similarity	NPD2861	Phase 2
0.7339	Intermediate Similarity	NPD845	Approved
0.7328	Intermediate Similarity	NPD943	Approved
0.7328	Intermediate Similarity	NPD825	Approved
0.7328	Intermediate Similarity	NPD4060	Phase 1
0.7328	Intermediate Similarity	NPD826	Approved
0.7317	Intermediate Similarity	NPD4093	Discontinued
0.7302	Intermediate Similarity	NPD4659	Approved
0.7299	Intermediate Similarity	NPD6190	Approved
0.7295	Intermediate Similarity	NPD5536	Phase 2
0.7279	Intermediate Similarity	NPD3060	Approved
0.7266	Intermediate Similarity	NPD6584	Phase 3
0.7266	Intermediate Similarity	NPD257	Approved
0.7266	Intermediate Similarity	NPD258	Approved
0.7258	Intermediate Similarity	NPD2286	Discontinued
0.7258	Intermediate Similarity	NPD6516	Phase 2
0.7258	Intermediate Similarity	NPD4059	Approved
0.7258	Intermediate Similarity	NPD5846	Approved
0.7258	Intermediate Similarity	NPD2932	Approved
0.7258	Intermediate Similarity	NPD3019	Approved
0.725	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD968	Approved
0.7241	Intermediate Similarity	NPD1445	Approved
0.7241	Intermediate Similarity	NPD1444	Approved
0.7227	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD8166	Discontinued
0.7222	Intermediate Similarity	NPD2561	Approved
0.7222	Intermediate Similarity	NPD2562	Approved
0.7209	Intermediate Similarity	NPD5736	Approved
0.719	Intermediate Similarity	NPD9614	Approved
0.719	Intermediate Similarity	NPD9618	Approved
0.7188	Intermediate Similarity	NPD4103	Phase 2
0.7188	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6671	Approved
0.713	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6405	Approved
0.7121	Intermediate Similarity	NPD2674	Phase 3
0.7121	Intermediate Similarity	NPD6407	Approved
0.709	Intermediate Similarity	NPD2568	Approved
0.7087	Intermediate Similarity	NPD2231	Phase 2
0.7087	Intermediate Similarity	NPD2235	Phase 2
0.7077	Intermediate Similarity	NPD9569	Approved
0.7068	Intermediate Similarity	NPD1558	Phase 1
0.7059	Intermediate Similarity	NPD9570	Approved
0.7059	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5451	Approved
0.7034	Intermediate Similarity	NPD290	Approved
0.7031	Intermediate Similarity	NPD2983	Phase 2
0.7031	Intermediate Similarity	NPD2982	Phase 2
0.7031	Intermediate Similarity	NPD6583	Phase 3
0.7031	Intermediate Similarity	NPD6582	Phase 2
0.7029	Intermediate Similarity	NPD4162	Approved
0.7023	Intermediate Similarity	NPD4908	Phase 1
0.7021	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3645	Discontinued
0.7016	Intermediate Similarity	NPD9616	Approved
0.7016	Intermediate Similarity	NPD9615	Approved
0.7016	Intermediate Similarity	NPD856	Approved
0.7016	Intermediate Similarity	NPD9613	Approved
0.7016	Intermediate Similarity	NPD16	Approved
0.7015	Intermediate Similarity	NPD555	Phase 2
0.7015	Intermediate Similarity	NPD5735	Approved
0.7008	Intermediate Similarity	NPD1610	Phase 2
0.6992	Remote Similarity	NPD259	Phase 1
0.6992	Remote Similarity	NPD6663	Approved
0.6984	Remote Similarity	NPD1751	Approved
0.6984	Remote Similarity	NPD4589	Approved
0.697	Remote Similarity	NPD7095	Approved
0.6961	Remote Similarity	NPD9294	Approved
0.696	Remote Similarity	NPD5303	Approved
0.696	Remote Similarity	NPD1548	Phase 1
0.696	Remote Similarity	NPD5304	Approved
0.696	Remote Similarity	NPD316	Approved
0.6953	Remote Similarity	NPD2981	Phase 2
0.6947	Remote Similarity	NPD3018	Phase 2
0.6947	Remote Similarity	NPD9494	Approved
0.6944	Remote Similarity	NPD3455	Phase 2
0.6929	Remote Similarity	NPD3847	Discontinued
0.6929	Remote Similarity	NPD3421	Phase 3
0.6929	Remote Similarity	NPD5241	Discontinued
0.6923	Remote Similarity	NPD9610	Approved
0.6923	Remote Similarity	NPD9608	Approved
0.6917	Remote Similarity	NPD6798	Discontinued
0.6917	Remote Similarity	NPD3144	Approved
0.6917	Remote Similarity	NPD5110	Phase 2
0.6917	Remote Similarity	NPD5111	Phase 2
0.6917	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3145	Approved
0.6917	Remote Similarity	NPD5109	Approved
0.6912	Remote Similarity	NPD4536	Approved
0.6912	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4538	Approved
0.6911	Remote Similarity	NPD2629	Approved
0.6906	Remote Similarity	NPD5177	Phase 3
0.6906	Remote Similarity	NPD4236	Phase 3
0.6906	Remote Similarity	NPD4237	Approved
0.6906	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD274	Approved
0.6889	Remote Similarity	NPD6355	Discontinued
0.6889	Remote Similarity	NPD275	Approved
0.6885	Remote Similarity	NPD5535	Approved
0.6881	Remote Similarity	NPD9094	Approved
0.688	Remote Similarity	NPD317	Approved
0.688	Remote Similarity	NPD318	Approved
0.6879	Remote Similarity	NPD3845	Phase 1
0.6879	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3705	Approved
0.6871	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2977	Approved
0.6871	Remote Similarity	NPD2978	Approved
0.6861	Remote Similarity	NPD5960	Phase 3
0.6861	Remote Similarity	NPD7743	Approved
0.6861	Remote Similarity	NPD7742	Approved
0.6861	Remote Similarity	NPD5588	Approved
0.6857	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6331	Phase 2
0.6857	Remote Similarity	NPD4110	Phase 3
0.685	Remote Similarity	NPD2668	Approved
0.685	Remote Similarity	NPD2667	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