NPASS Compound

Structure

NPC471578 OpenBabel07101719152D 21 21 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 -3.4641 1.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -3.8660 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 -1.7321 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 -0.8660 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.1340 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.4019 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 0.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 2 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 -4.9641 -0.4019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 0.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 18 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.19
Volume:	324.516
LogP:	2.816
LogD:	2.759
LogS:	-2.419
# Rotatable Bonds:	7
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	3.755
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.573
MDCK Permeability:	2.3246613636729307e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.462
Plasma Protein Binding (PPB):	92.05809783935547%
Volume Distribution (VD):	2.212
Pgp-substrate:	6.036942481994629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.246
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.313
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.257
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	10.902
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.687
Maximum Recommended Daily Dose:	0.518
Skin Sensitization:	0.793
Carcinogencity:	0.173
Eye Corrosion:	0.006
Eye Irritation:	0.146
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC471578

Natural Product ID:	NPC471578
*Common Name:**	12,13-Diolbakuchiol
IUPAC Name:	(E,6S)-6-ethenyl-8-(4-hydroxyphenyl)-2,6-dimethyloct-7-ene-2,3-diol
Synonyms:	12,13-Diolbakuchiol
Standard InCHIKey:	QIXGHNLALDUHDP-AVNQGEAYSA-N
Standard InCHI:	InChI=1S/C18H26O3/c1-5-18(4,13-11-16(20)17(2,3)21)12-10-14-6-8-15(19)9-7-14/h5-10,12,16,19-21H,1,11,13H2,2-4H3/b12-10+/t16?,18-/m0/s1
SMILES:	CC(C)(C(CCC(C)(C=C)C=CC1=CC=C(C=C1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL261315
PubChem CID:	24882418
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18359631]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25710081]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3069958]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[8759164]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
EC50	7
IC50	4
Others	6

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	8
Others	1
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[547843]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[547843]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	>	52083.3	nM	PMID[547844]
NPT80	Cell Line	Raji	Homo sapiens	EC50	>	26041.7	nM	PMID[547844]
NPT15	Cell Line	Jurkat	Homo sapiens	EC50	>	49019.6	nM	PMID[547844]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	>	36630.0	nM	PMID[547844]
NPT71	Cell Line	HEK293	Homo sapiens	EC50	>	36630.0	nM	PMID[547844]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-30.0	%	PMID[547842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-89.0	%	PMID[547842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-100.0	%	PMID[547842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-16.0	%	PMID[547842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-99.0	%	PMID[547842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-83.0	%	PMID[547842]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[547843]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[547843]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	36630.0	nM	PMID[547844]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	43478.3	nM	PMID[547844]

☑ 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 NPC471578 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	219
0.1-0.2	1299
0.2-0.3	4084
0.3-0.4	12998
0.4-0.5	7785
0.5-0.6	10502
0.6-0.7	4659
0.7-0.8	996
0.8-0.85	129
0.85-0.9	23
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC101025
0.9286	High Similarity	NPC62351
0.9149	High Similarity	NPC270547
0.8936	High Similarity	NPC98772
0.8854	High Similarity	NPC325292
0.8854	High Similarity	NPC138117
0.883	High Similarity	NPC104216
0.8788	High Similarity	NPC51333
0.8788	High Similarity	NPC78119
0.8788	High Similarity	NPC132078
0.8788	High Similarity	NPC216468
0.8763	High Similarity	NPC27323
0.8763	High Similarity	NPC316301
0.875	High Similarity	NPC155908
0.8723	High Similarity	NPC184169
0.87	High Similarity	NPC213730
0.8687	High Similarity	NPC474073
0.8673	High Similarity	NPC313650
0.8646	High Similarity	NPC300017
0.8641	High Similarity	NPC477814
0.8614	High Similarity	NPC7686
0.8614	High Similarity	NPC91461
0.8614	High Similarity	NPC40258
0.86	High Similarity	NPC128723
0.86	High Similarity	NPC131587
0.86	High Similarity	NPC92730
0.8571	High Similarity	NPC62258
0.8571	High Similarity	NPC55617
0.8544	High Similarity	NPC154899
0.8544	High Similarity	NPC233396
0.8542	High Similarity	NPC242240
0.8542	High Similarity	NPC318325
0.8542	High Similarity	NPC177420
0.8542	High Similarity	NPC123273
0.8542	High Similarity	NPC280347
0.8515	High Similarity	NPC294741
0.8515	High Similarity	NPC225506
0.8511	High Similarity	NPC248817
0.8505	High Similarity	NPC228425
0.85	High Similarity	NPC225464
0.8491	Intermediate Similarity	NPC120982
0.8491	Intermediate Similarity	NPC226401
0.8491	Intermediate Similarity	NPC79793
0.8491	Intermediate Similarity	NPC44732
0.8491	Intermediate Similarity	NPC174096
0.8491	Intermediate Similarity	NPC147634
0.8485	Intermediate Similarity	NPC26244
0.8468	Intermediate Similarity	NPC163036
0.8462	Intermediate Similarity	NPC92623
0.8462	Intermediate Similarity	NPC135464
0.8454	Intermediate Similarity	NPC300478
0.8454	Intermediate Similarity	NPC55561
0.8447	Intermediate Similarity	NPC120719
0.844	Intermediate Similarity	NPC474486
0.8438	Intermediate Similarity	NPC113460
0.8438	Intermediate Similarity	NPC25493
0.8431	Intermediate Similarity	NPC110764
0.8431	Intermediate Similarity	NPC472585
0.8421	Intermediate Similarity	NPC197783
0.8416	Intermediate Similarity	NPC122005
0.8416	Intermediate Similarity	NPC252821
0.8411	Intermediate Similarity	NPC187583
0.8411	Intermediate Similarity	NPC308689
0.8411	Intermediate Similarity	NPC257430
0.8411	Intermediate Similarity	NPC179002
0.8404	Intermediate Similarity	NPC265146
0.8404	Intermediate Similarity	NPC124436
0.84	Intermediate Similarity	NPC132271
0.84	Intermediate Similarity	NPC292730
0.84	Intermediate Similarity	NPC473388
0.84	Intermediate Similarity	NPC216520
0.84	Intermediate Similarity	NPC82664
0.8396	Intermediate Similarity	NPC473524
0.8384	Intermediate Similarity	NPC151715
0.8384	Intermediate Similarity	NPC152415
0.8367	Intermediate Similarity	NPC304541
0.8351	Intermediate Similarity	NPC258219
0.835	Intermediate Similarity	NPC196479
0.8349	Intermediate Similarity	NPC12656
0.8333	Intermediate Similarity	NPC23167
0.8316	Intermediate Similarity	NPC175313
0.8302	Intermediate Similarity	NPC262365
0.8302	Intermediate Similarity	NPC317305
0.83	Intermediate Similarity	NPC107522
0.8288	Intermediate Similarity	NPC320864
0.8283	Intermediate Similarity	NPC162314
0.8283	Intermediate Similarity	NPC3358
0.8283	Intermediate Similarity	NPC210497
0.8283	Intermediate Similarity	NPC94139
0.8283	Intermediate Similarity	NPC306884
0.8283	Intermediate Similarity	NPC147284
0.8283	Intermediate Similarity	NPC55903
0.8269	Intermediate Similarity	NPC12278
0.8265	Intermediate Similarity	NPC192
0.8265	Intermediate Similarity	NPC312304
0.8241	Intermediate Similarity	NPC470355
0.8241	Intermediate Similarity	NPC139946
0.8208	Intermediate Similarity	NPC61033
0.8208	Intermediate Similarity	NPC474352
0.8208	Intermediate Similarity	NPC305603
0.8198	Intermediate Similarity	NPC474358
0.8198	Intermediate Similarity	NPC257540
0.8198	Intermediate Similarity	NPC154511
0.8198	Intermediate Similarity	NPC137496
0.8198	Intermediate Similarity	NPC474387
0.8198	Intermediate Similarity	NPC247858
0.8182	Intermediate Similarity	NPC306074
0.8182	Intermediate Similarity	NPC120280
0.8182	Intermediate Similarity	NPC45040
0.8182	Intermediate Similarity	NPC204210
0.8182	Intermediate Similarity	NPC473137
0.8173	Intermediate Similarity	NPC235762
0.8173	Intermediate Similarity	NPC471228
0.8155	Intermediate Similarity	NPC211885
0.8155	Intermediate Similarity	NPC174911
0.8148	Intermediate Similarity	NPC63345
0.8148	Intermediate Similarity	NPC46844
0.8137	Intermediate Similarity	NPC109955
0.8137	Intermediate Similarity	NPC475078
0.8137	Intermediate Similarity	NPC77492
0.8125	Intermediate Similarity	NPC150837
0.8125	Intermediate Similarity	NPC164386
0.8125	Intermediate Similarity	NPC477136
0.8119	Intermediate Similarity	NPC274678
0.8119	Intermediate Similarity	NPC286006
0.8119	Intermediate Similarity	NPC222146
0.8119	Intermediate Similarity	NPC144682
0.8113	Intermediate Similarity	NPC53740
0.8108	Intermediate Similarity	NPC147179
0.81	Intermediate Similarity	NPC181709
0.8095	Intermediate Similarity	NPC475225
0.8095	Intermediate Similarity	NPC323810
0.8087	Intermediate Similarity	NPC77569
0.8087	Intermediate Similarity	NPC142198
0.8081	Intermediate Similarity	NPC47950
0.8077	Intermediate Similarity	NPC252105
0.807	Intermediate Similarity	NPC223451
0.8061	Intermediate Similarity	NPC19680
0.8061	Intermediate Similarity	NPC27974
0.8058	Intermediate Similarity	NPC299762
0.8058	Intermediate Similarity	NPC33675
0.8058	Intermediate Similarity	NPC171843
0.8056	Intermediate Similarity	NPC254833
0.8056	Intermediate Similarity	NPC228343
0.8053	Intermediate Similarity	NPC164649
0.8053	Intermediate Similarity	NPC48342
0.8037	Intermediate Similarity	NPC66834
0.8037	Intermediate Similarity	NPC251306
0.8036	Intermediate Similarity	NPC477137
0.8036	Intermediate Similarity	NPC38893
0.8036	Intermediate Similarity	NPC219112
0.8036	Intermediate Similarity	NPC308311
0.8036	Intermediate Similarity	NPC308828
0.802	Intermediate Similarity	NPC128062
0.802	Intermediate Similarity	NPC76938
0.802	Intermediate Similarity	NPC289769
0.8019	Intermediate Similarity	NPC138942
0.8019	Intermediate Similarity	NPC47284
0.8018	Intermediate Similarity	NPC268160
0.8	Intermediate Similarity	NPC108497
0.8	Intermediate Similarity	NPC477802
0.8	Intermediate Similarity	NPC477801
0.8	Intermediate Similarity	NPC192596
0.8	Intermediate Similarity	NPC168829
0.7982	Intermediate Similarity	NPC321252
0.7982	Intermediate Similarity	NPC475018
0.7982	Intermediate Similarity	NPC311595
0.7982	Intermediate Similarity	NPC252544
0.7982	Intermediate Similarity	NPC24474
0.7982	Intermediate Similarity	NPC470215
0.7982	Intermediate Similarity	NPC109371
0.7982	Intermediate Similarity	NPC470214
0.7981	Intermediate Similarity	NPC129373
0.7981	Intermediate Similarity	NPC248396
0.7981	Intermediate Similarity	NPC48730
0.7981	Intermediate Similarity	NPC223393
0.7981	Intermediate Similarity	NPC72729
0.798	Intermediate Similarity	NPC70436
0.7965	Intermediate Similarity	NPC200988
0.7965	Intermediate Similarity	NPC145023
0.7965	Intermediate Similarity	NPC610
0.7965	Intermediate Similarity	NPC175799
0.7963	Intermediate Similarity	NPC201959
0.7961	Intermediate Similarity	NPC201967
0.7961	Intermediate Similarity	NPC152097
0.7959	Intermediate Similarity	NPC307235
0.7959	Intermediate Similarity	NPC407
0.7946	Intermediate Similarity	NPC35797
0.7946	Intermediate Similarity	NPC192948
0.7944	Intermediate Similarity	NPC19149
0.7944	Intermediate Similarity	NPC155072
0.7944	Intermediate Similarity	NPC113457
0.7944	Intermediate Similarity	NPC310456
0.7941	Intermediate Similarity	NPC32714
0.7941	Intermediate Similarity	NPC8392
0.7938	Intermediate Similarity	NPC286904
0.7928	Intermediate Similarity	NPC176730
0.7928	Intermediate Similarity	NPC123175
0.7925	Intermediate Similarity	NPC52087
0.7925	Intermediate Similarity	NPC79672

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 NPC471578 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	894
0.2-0.3	1595
0.3-0.4	3028
0.4-0.5	1843
0.5-0.6	1115
0.6-0.7	402
0.7-0.8	56
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8763	High Similarity	NPD1432	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD2860	Approved
0.8485	Intermediate Similarity	NPD2859	Approved
0.8416	Intermediate Similarity	NPD3020	Approved
0.8404	Intermediate Similarity	NPD111	Approved
0.8384	Intermediate Similarity	NPD2933	Approved
0.8384	Intermediate Similarity	NPD2934	Approved
0.8119	Intermediate Similarity	NPD1809	Phase 2
0.8087	Intermediate Similarity	NPD3092	Approved
0.8056	Intermediate Similarity	NPD3021	Approved
0.8056	Intermediate Similarity	NPD3022	Approved
0.8053	Intermediate Similarity	NPD3091	Approved
0.7981	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2684	Approved
0.7946	Intermediate Similarity	NPD7157	Approved
0.7941	Intermediate Similarity	NPD844	Approved
0.7905	Intermediate Similarity	NPD940	Approved
0.7905	Intermediate Similarity	NPD846	Approved
0.7815	Intermediate Similarity	NPD3094	Phase 2
0.7768	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD845	Approved
0.7692	Intermediate Similarity	NPD288	Approved
0.7679	Intermediate Similarity	NPD7843	Approved
0.7672	Intermediate Similarity	NPD1357	Approved
0.7642	Intermediate Similarity	NPD1242	Phase 1
0.7611	Intermediate Similarity	NPD2229	Approved
0.7611	Intermediate Similarity	NPD2234	Approved
0.7611	Intermediate Similarity	NPD2228	Approved
0.7607	Intermediate Similarity	NPD3095	Discontinued
0.7589	Intermediate Similarity	NPD228	Approved
0.7568	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD290	Approved
0.7479	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4059	Approved
0.7368	Intermediate Similarity	NPD9294	Approved
0.735	Intermediate Similarity	NPD16	Approved
0.735	Intermediate Similarity	NPD856	Approved
0.7315	Intermediate Similarity	NPD3028	Approved
0.7311	Intermediate Similarity	NPD2932	Approved
0.7311	Intermediate Similarity	NPD3019	Approved
0.7311	Intermediate Similarity	NPD9381	Approved
0.7311	Intermediate Similarity	NPD9384	Approved
0.7297	Intermediate Similarity	NPD1445	Approved
0.7297	Intermediate Similarity	NPD1444	Approved
0.728	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD9610	Approved
0.7273	Intermediate Similarity	NPD9608	Approved
0.7258	Intermediate Similarity	NPD5736	Approved
0.7257	Intermediate Similarity	NPD4750	Phase 3
0.7244	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3620	Phase 2
0.7241	Intermediate Similarity	NPD9618	Approved
0.7241	Intermediate Similarity	NPD9614	Approved
0.7236	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4103	Phase 2
0.7234	Intermediate Similarity	NPD9087	Approved
0.7217	Intermediate Similarity	NPD9377	Approved
0.7217	Intermediate Similarity	NPD9379	Approved
0.7213	Intermediate Similarity	NPD4659	Approved
0.7213	Intermediate Similarity	NPD9622	Approved
0.7203	Intermediate Similarity	NPD317	Approved
0.7203	Intermediate Similarity	NPD318	Approved
0.7182	Intermediate Similarity	NPD9500	Approved
0.7179	Intermediate Similarity	NPD6671	Approved
0.7167	Intermediate Similarity	NPD4589	Approved
0.7143	Intermediate Similarity	NPD968	Approved
0.7143	Intermediate Similarity	NPD3134	Approved
0.7131	Intermediate Similarity	NPD2561	Approved
0.7131	Intermediate Similarity	NPD2562	Approved
0.7113	Intermediate Similarity	NPD9088	Approved
0.7105	Intermediate Similarity	NPD1792	Phase 2
0.7094	Intermediate Similarity	NPD1791	Approved
0.7094	Intermediate Similarity	NPD1793	Approved
0.7094	Intermediate Similarity	NPD2629	Approved
0.708	Intermediate Similarity	NPD1358	Approved
0.7073	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD821	Approved
0.7069	Intermediate Similarity	NPD7635	Approved
0.7059	Intermediate Similarity	NPD9613	Approved
0.7059	Intermediate Similarity	NPD9616	Approved
0.7059	Intermediate Similarity	NPD9615	Approved
0.7054	Intermediate Similarity	NPD5735	Approved
0.7043	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD9620	Approved
0.704	Intermediate Similarity	NPD9619	Approved
0.704	Intermediate Similarity	NPD9621	Approved
0.7031	Intermediate Similarity	NPD6663	Approved
0.7027	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5846	Approved
0.7025	Intermediate Similarity	NPD2667	Approved
0.7025	Intermediate Similarity	NPD2668	Approved
0.7025	Intermediate Similarity	NPD6516	Phase 2
0.7025	Intermediate Similarity	NPD1751	Approved
0.7016	Intermediate Similarity	NPD8651	Approved
0.7009	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD316	Approved
0.6972	Remote Similarity	NPD9273	Approved
0.6972	Remote Similarity	NPD9495	Approved
0.6967	Remote Similarity	NPD3421	Phase 3
0.696	Remote Similarity	NPD1135	Approved
0.696	Remote Similarity	NPD1131	Approved
0.696	Remote Similarity	NPD1129	Approved
0.696	Remote Similarity	NPD1133	Approved
0.696	Remote Similarity	NPD1134	Approved
0.6957	Remote Similarity	NPD5451	Approved
0.6953	Remote Similarity	NPD597	Approved
0.6953	Remote Similarity	NPD598	Approved
0.6953	Remote Similarity	NPD601	Approved
0.6942	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4093	Discontinued
0.6942	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6582	Phase 2
0.6935	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6583	Phase 3
0.6935	Remote Similarity	NPD3685	Discontinued
0.693	Remote Similarity	NPD2342	Discontinued
0.6905	Remote Similarity	NPD4624	Approved
0.6905	Remote Similarity	NPD6584	Phase 3
0.6899	Remote Similarity	NPD1130	Approved
0.6899	Remote Similarity	NPD1132	Approved
0.6899	Remote Similarity	NPD1136	Approved
0.6894	Remote Similarity	NPD7743	Approved
0.6894	Remote Similarity	NPD7742	Approved
0.6891	Remote Similarity	NPD255	Approved
0.6891	Remote Similarity	NPD256	Approved
0.6891	Remote Similarity	NPD4198	Discontinued
0.6887	Remote Similarity	NPD9365	Approved
0.6885	Remote Similarity	NPD4626	Approved
0.6875	Remote Similarity	NPD7095	Approved
0.6864	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5304	Approved
0.686	Remote Similarity	NPD9545	Approved
0.686	Remote Similarity	NPD5303	Approved
0.6857	Remote Similarity	NPD9295	Approved
0.6852	Remote Similarity	NPD9296	Approved
0.685	Remote Similarity	NPD2861	Phase 2
0.6846	Remote Similarity	NPD4060	Phase 1
0.6846	Remote Similarity	NPD4140	Approved
0.6846	Remote Similarity	NPD3062	Approved
0.6846	Remote Similarity	NPD3061	Approved
0.6846	Remote Similarity	NPD3059	Approved
0.6832	Remote Similarity	NPD9089	Approved
0.6829	Remote Similarity	NPD3143	Discontinued
0.6825	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3055	Approved
0.6825	Remote Similarity	NPD3053	Approved
0.6822	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD475	Phase 2
0.68	Remote Similarity	NPD5327	Phase 3
0.6797	Remote Similarity	NPD4908	Phase 1
0.6786	Remote Similarity	NPD291	Approved
0.6783	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1610	Phase 2
0.6774	Remote Similarity	NPD1091	Approved
0.6772	Remote Similarity	NPD2194	Approved
0.6772	Remote Similarity	NPD3691	Phase 2
0.6772	Remote Similarity	NPD2195	Approved
0.6772	Remote Similarity	NPD3690	Phase 2
0.6772	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6407	Approved
0.6769	Remote Similarity	NPD6405	Approved
0.6765	Remote Similarity	NPD4628	Phase 3
0.6762	Remote Similarity	NPD9094	Approved
0.6748	Remote Similarity	NPD2286	Discontinued
0.6748	Remote Similarity	NPD1778	Approved
0.6746	Remote Similarity	NPD5310	Approved
0.6746	Remote Similarity	NPD5311	Approved
0.6742	Remote Similarity	NPD5314	Approved
0.6742	Remote Similarity	NPD823	Approved
0.6742	Remote Similarity	NPD817	Approved
0.6742	Remote Similarity	NPD6353	Approved
0.6733	Remote Similarity	NPD9093	Approved
0.6721	Remote Similarity	NPD7741	Discontinued
0.6721	Remote Similarity	NPD7330	Discontinued
0.6721	Remote Similarity	NPD1548	Phase 1
0.672	Remote Similarity	NPD2233	Approved
0.672	Remote Similarity	NPD2232	Approved
0.672	Remote Similarity	NPD2235	Phase 2
0.672	Remote Similarity	NPD2230	Approved
0.672	Remote Similarity	NPD3070	Discontinued
0.672	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2231	Phase 2
0.6719	Remote Similarity	NPD3635	Approved
0.6719	Remote Similarity	NPD3636	Approved
0.6719	Remote Similarity	NPD3637	Approved
0.6719	Remote Similarity	NPD9494	Approved
0.6719	Remote Similarity	NPD4208	Discontinued
0.6718	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD826	Approved
0.6718	Remote Similarity	NPD2238	Phase 2
0.6718	Remote Similarity	NPD825	Approved
0.6718	Remote Similarity	NPD1613	Approved
0.6718	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3847	Discontinued
0.6694	Remote Similarity	NPD3026	Approved
0.6694	Remote Similarity	NPD3023	Approved
0.6694	Remote Similarity	NPD2688	Clinical (unspecified phase)

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