NPASS Compound

Structure

NPC125617 OpenBabel07101718192D 36 38 0 0 0 0 0 0 0 0999 V2000 3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 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 4.2191 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -3.8974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9067 2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 17 2 0 0 0 0 6 10 2 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 18 2 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 27 2 0 0 0 0 13 33 1 0 0 0 0 14 28 2 0 0 0 0 14 34 1 0 0 0 0 15 29 2 0 0 0 0 15 35 1 0 0 0 0 16 30 2 0 0 0 0 16 36 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 23 2 0 0 0 0 21 25 1 0 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 26 2 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.12
Volume:	486.211
LogP:	2.829
LogD:	1.565
LogS:	-4.942
# Rotatable Bonds:	10
TPSA:	145.66
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	2.498
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.905
MDCK Permeability:	2.8438584195100702e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.823
20% Bioavailability (F20%):	0.078
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	80.38236999511719%
Volume Distribution (VD):	0.569
Pgp-substrate:	30.868471145629883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.694
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.893
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.76
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.187
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	0.995
Half-life (T1/2):	0.854

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.002
Drug-inuced Liver Injury (DILI):	0.652
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.101
Skin Sensitization:	0.725
Carcinogencity:	0.119
Eye Corrosion:	0.003
Eye Irritation:	0.67
Respiratory Toxicity:	0.134

Download Data

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

Natural Product: NPC125617

Natural Product ID:	NPC125617
*Common Name:**	2',3',5',6'-Tetracetoxy-4,4''-Dihydroxy-P-Terphenyl
IUPAC Name:	[2,4,5-triacetyloxy-3,6-bis(4-hydroxyphenyl)phenyl] acetate
Synonyms:
Standard InCHIKey:	UMJFGLNAUQKBET-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H22O10/c1-13(27)33-23-21(17-5-9-19(31)10-6-17)25(35-15(3)29)26(36-16(4)30)22(24(23)34-14(2)28)18-7-11-20(32)12-8-18/h5-12,31-32H,1-4H3
SMILES:	CC(=O)Oc1c(OC(=O)C)c(c2ccc(cc2)O)c(c(c1c1ccc(cc1)O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3238006
PubChem CID:	86302374
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002042] Terphenyls [CHEMONTID:0002126] P-terphenyls

*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
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10757716]
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	n.a.	Tibet, China	n.a.	PMID[24645629]
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	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
EC50	1
IC50	3
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	50000.0	nM	PMID[564508]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	34.0	U	PMID[564508]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	50000.0	nM	PMID[564508]
NPT625	Tissue	Liver	Mus musculus	IC50	=	30000.0	nM	PMID[564508]
NPT2	Others	Unspecified		IC50	=	35000.0	nM	PMID[564508]

☑ 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 NPC125617 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	367
0.1-0.2	1667
0.2-0.3	4559
0.3-0.4	12003
0.4-0.5	6127
0.5-0.6	3930
0.6-0.7	6554
0.7-0.8	6432
0.8-0.85	853
0.85-0.9	183
0.9-0.95	17
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC275125
0.9856	High Similarity	NPC170239
0.9856	High Similarity	NPC97937
0.9716	High Similarity	NPC113790
0.9448	High Similarity	NPC476154
0.9384	High Similarity	NPC7178
0.9384	High Similarity	NPC62903
0.932	High Similarity	NPC292385
0.932	High Similarity	NPC125709
0.932	High Similarity	NPC155015
0.932	High Similarity	NPC142479
0.9203	High Similarity	NPC111655
0.9071	High Similarity	NPC6262
0.9071	High Similarity	NPC90615
0.9071	High Similarity	NPC73535
0.9071	High Similarity	NPC476171
0.9071	High Similarity	NPC272157
0.9071	High Similarity	NPC201145
0.9071	High Similarity	NPC25111
0.9067	High Similarity	NPC36077
0.9021	High Similarity	NPC7439
0.9021	High Similarity	NPC110067
0.9021	High Similarity	NPC91492
0.9021	High Similarity	NPC256555
0.9021	High Similarity	NPC34245
0.9007	High Similarity	NPC36354
0.9	High Similarity	NPC114155
0.9	High Similarity	NPC300846
0.9	High Similarity	NPC476639
0.8993	High Similarity	NPC474600
0.8954	High Similarity	NPC476200
0.8954	High Similarity	NPC192258
0.8954	High Similarity	NPC55121
0.8954	High Similarity	NPC174311
0.8944	High Similarity	NPC295719
0.8944	High Similarity	NPC34431
0.8944	High Similarity	NPC165026
0.8944	High Similarity	NPC73505
0.8929	High Similarity	NPC283009
0.8929	High Similarity	NPC252095
0.8929	High Similarity	NPC261873
0.8865	High Similarity	NPC205442
0.8865	High Similarity	NPC286843
0.8865	High Similarity	NPC173660
0.8859	High Similarity	NPC163598
0.8859	High Similarity	NPC264875
0.8859	High Similarity	NPC120774
0.8857	High Similarity	NPC103967
0.8836	High Similarity	NPC475896
0.8819	High Similarity	NPC175838
0.8803	High Similarity	NPC48956
0.8803	High Similarity	NPC38874
0.8803	High Similarity	NPC105493
0.8803	High Similarity	NPC266006
0.88	High Similarity	NPC78809
0.8794	High Similarity	NPC311430
0.8794	High Similarity	NPC224941
0.8794	High Similarity	NPC195022
0.8794	High Similarity	NPC234865
0.8786	High Similarity	NPC474810
0.8786	High Similarity	NPC269528
0.8784	High Similarity	NPC176903
0.8784	High Similarity	NPC30688
0.8767	High Similarity	NPC292256
0.8741	High Similarity	NPC471388
0.8741	High Similarity	NPC25966
0.8741	High Similarity	NPC22517
0.8741	High Similarity	NPC212942
0.8741	High Similarity	NPC79622
0.8741	High Similarity	NPC245207
0.8741	High Similarity	NPC29868
0.8741	High Similarity	NPC127218
0.8741	High Similarity	NPC319647
0.8725	High Similarity	NPC21184
0.8725	High Similarity	NPC294522
0.8725	High Similarity	NPC120426
0.8725	High Similarity	NPC205727
0.8714	High Similarity	NPC218884
0.8707	High Similarity	NPC40222
0.8707	High Similarity	NPC268515
0.8705	High Similarity	NPC192687
0.8705	High Similarity	NPC224157
0.8696	High Similarity	NPC474651
0.8696	High Similarity	NPC474623
0.8681	High Similarity	NPC308768
0.8681	High Similarity	NPC20520
0.8681	High Similarity	NPC61783
0.8681	High Similarity	NPC27495
0.8681	High Similarity	NPC12668
0.8671	High Similarity	NPC102904
0.8671	High Similarity	NPC474886
0.8671	High Similarity	NPC326797
0.8671	High Similarity	NPC276490
0.8671	High Similarity	NPC103976
0.8671	High Similarity	NPC476279
0.8671	High Similarity	NPC474282
0.8671	High Similarity	NPC107551
0.8671	High Similarity	NPC176051
0.8662	High Similarity	NPC201357
0.8662	High Similarity	NPC281521
0.8662	High Similarity	NPC255147
0.8649	High Similarity	NPC15577
0.8649	High Similarity	NPC178129
0.8643	High Similarity	NPC142530
0.8643	High Similarity	NPC147317
0.8633	High Similarity	NPC190144
0.863	High Similarity	NPC477616
0.863	High Similarity	NPC6568
0.8621	High Similarity	NPC471389
0.8618	High Similarity	NPC8712
0.8611	High Similarity	NPC220344
0.8611	High Similarity	NPC132804
0.8611	High Similarity	NPC43500
0.8611	High Similarity	NPC164148
0.8611	High Similarity	NPC243996
0.8611	High Similarity	NPC218131
0.8611	High Similarity	NPC243759
0.8611	High Similarity	NPC105847
0.8611	High Similarity	NPC275061
0.8601	High Similarity	NPC202846
0.8601	High Similarity	NPC248727
0.8601	High Similarity	NPC143139
0.8601	High Similarity	NPC270456
0.8601	High Similarity	NPC265433
0.8601	High Similarity	NPC472336
0.8601	High Similarity	NPC471719
0.8601	High Similarity	NPC472334
0.8601	High Similarity	NPC476698
0.8601	High Similarity	NPC162659
0.8592	High Similarity	NPC106215
0.8592	High Similarity	NPC256307
0.8592	High Similarity	NPC309744
0.8592	High Similarity	NPC66840
0.8591	High Similarity	NPC476348
0.8591	High Similarity	NPC477879
0.8591	High Similarity	NPC187398
0.8591	High Similarity	NPC175976
0.8591	High Similarity	NPC139839
0.8582	High Similarity	NPC127624
0.8582	High Similarity	NPC86655
0.8582	High Similarity	NPC6451
0.8582	High Similarity	NPC474635
0.8582	High Similarity	NPC202762
0.8582	High Similarity	NPC245120
0.8581	High Similarity	NPC150714
0.8581	High Similarity	NPC95652
0.8581	High Similarity	NPC112251
0.8571	High Similarity	NPC214860
0.8571	High Similarity	NPC36732
0.8571	High Similarity	NPC229231
0.8571	High Similarity	NPC311680
0.8571	High Similarity	NPC51840
0.8571	High Similarity	NPC87883
0.8571	High Similarity	NPC299221
0.8571	High Similarity	NPC234488
0.8571	High Similarity	NPC476399
0.8562	High Similarity	NPC469564
0.8562	High Similarity	NPC107161
0.8562	High Similarity	NPC476642
0.8562	High Similarity	NPC472335
0.8562	High Similarity	NPC472332
0.8553	High Similarity	NPC475141
0.8552	High Similarity	NPC160283
0.8552	High Similarity	NPC291101
0.8552	High Similarity	NPC22317
0.8552	High Similarity	NPC254759
0.8552	High Similarity	NPC259519
0.8552	High Similarity	NPC266197
0.8551	High Similarity	NPC223953
0.8542	High Similarity	NPC266453
0.8542	High Similarity	NPC242715
0.8542	High Similarity	NPC230919
0.8542	High Similarity	NPC148835
0.8542	High Similarity	NPC56329
0.8542	High Similarity	NPC76336
0.8542	High Similarity	NPC200935
0.8542	High Similarity	NPC95162
0.8542	High Similarity	NPC139548
0.8542	High Similarity	NPC35550
0.8542	High Similarity	NPC20511
0.8542	High Similarity	NPC151656
0.8542	High Similarity	NPC22902
0.8542	High Similarity	NPC52086
0.8533	High Similarity	NPC476969
0.8531	High Similarity	NPC112246
0.8531	High Similarity	NPC94750
0.8531	High Similarity	NPC69029
0.8531	High Similarity	NPC10314
0.8531	High Similarity	NPC61946
0.8531	High Similarity	NPC470356
0.8531	High Similarity	NPC474206
0.8531	High Similarity	NPC112939
0.8531	High Similarity	NPC472337
0.8531	High Similarity	NPC200557
0.8531	High Similarity	NPC108198
0.8531	High Similarity	NPC158142
0.8531	High Similarity	NPC121812
0.8531	High Similarity	NPC294884
0.8523	High Similarity	NPC476347
0.8523	High Similarity	NPC183083

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 NPC125617 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	955
0.2-0.3	1763
0.3-0.4	2787
0.4-0.5	1656
0.5-0.6	940
0.6-0.7	582
0.7-0.8	137
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD5844	Phase 1
0.8429	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6232	Discontinued
0.8194	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1613	Approved
0.817	Intermediate Similarity	NPD1653	Approved
0.8169	Intermediate Similarity	NPD4908	Phase 1
0.8112	Intermediate Similarity	NPD3027	Phase 3
0.8112	Intermediate Similarity	NPD4625	Phase 3
0.8086	Intermediate Similarity	NPD7473	Discontinued
0.8056	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD37	Approved
0.795	Intermediate Similarity	NPD7199	Phase 2
0.7943	Intermediate Similarity	NPD4749	Approved
0.7937	Intermediate Similarity	NPD6234	Discontinued
0.7929	Intermediate Similarity	NPD422	Phase 1
0.7925	Intermediate Similarity	NPD4966	Approved
0.7925	Intermediate Similarity	NPD4965	Approved
0.7925	Intermediate Similarity	NPD4967	Phase 2
0.7911	Intermediate Similarity	NPD2801	Approved
0.7911	Intermediate Similarity	NPD1465	Phase 2
0.7904	Intermediate Similarity	NPD7549	Discontinued
0.7853	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1611	Approved
0.7801	Intermediate Similarity	NPD1610	Phase 2
0.775	Intermediate Similarity	NPD3817	Phase 2
0.7736	Intermediate Similarity	NPD1934	Approved
0.7724	Intermediate Similarity	NPD2861	Phase 2
0.7724	Intermediate Similarity	NPD3018	Phase 2
0.7712	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4060	Phase 1
0.7697	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6166	Phase 2
0.7697	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1548	Phase 1
0.7628	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7095	Approved
0.7605	Intermediate Similarity	NPD7228	Approved
0.7597	Intermediate Similarity	NPD3750	Approved
0.7591	Intermediate Similarity	NPD5535	Approved
0.7578	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2983	Phase 2
0.7569	Intermediate Similarity	NPD2982	Phase 2
0.7568	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6099	Approved
0.7566	Intermediate Similarity	NPD6100	Approved
0.7564	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1511	Approved
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD2981	Phase 2
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7768	Phase 2
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1512	Approved
0.7466	Intermediate Similarity	NPD2797	Approved
0.745	Intermediate Similarity	NPD6798	Discontinued
0.7429	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6671	Approved
0.7427	Intermediate Similarity	NPD6559	Discontinued
0.7419	Intermediate Similarity	NPD6674	Discontinued
0.7419	Intermediate Similarity	NPD1652	Phase 2
0.7417	Intermediate Similarity	NPD5124	Phase 1
0.7417	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7074	Phase 3
0.741	Intermediate Similarity	NPD6959	Discontinued
0.741	Intermediate Similarity	NPD5283	Phase 1
0.7396	Intermediate Similarity	NPD3818	Discontinued
0.7378	Intermediate Similarity	NPD3882	Suspended
0.7365	Intermediate Similarity	NPD7229	Phase 3
0.7362	Intermediate Similarity	NPD7819	Suspended
0.7361	Intermediate Similarity	NPD3496	Discontinued
0.7353	Intermediate Similarity	NPD7054	Approved
0.7349	Intermediate Similarity	NPD5494	Approved
0.7349	Intermediate Similarity	NPD6746	Phase 2
0.7346	Intermediate Similarity	NPD7411	Suspended
0.7338	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD7075	Discontinued
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD3749	Approved
0.7329	Intermediate Similarity	NPD3226	Approved
0.7317	Intermediate Similarity	NPD5402	Approved
0.731	Intermediate Similarity	NPD7472	Approved
0.7308	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8127	Discontinued
0.7303	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4626	Approved
0.729	Intermediate Similarity	NPD7266	Discontinued
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7279	Intermediate Similarity	NPD3225	Approved
0.7279	Intermediate Similarity	NPD6696	Suspended
0.7278	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3748	Approved
0.7261	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4110	Phase 3
0.7261	Intermediate Similarity	NPD4628	Phase 3
0.726	Intermediate Similarity	NPD1608	Approved
0.7256	Intermediate Similarity	NPD8455	Phase 2
0.7237	Intermediate Similarity	NPD4140	Approved
0.7226	Intermediate Similarity	NPD1551	Phase 2
0.7225	Intermediate Similarity	NPD7240	Approved
0.7215	Intermediate Similarity	NPD6190	Approved
0.7212	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1535	Discovery
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7447	Phase 1
0.7184	Intermediate Similarity	NPD7808	Phase 3
0.7181	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5763	Approved
0.7179	Intermediate Similarity	NPD5762	Approved
0.7179	Intermediate Similarity	NPD3540	Phase 1
0.7172	Intermediate Similarity	NPD1778	Approved
0.7168	Intermediate Similarity	NPD6797	Phase 2
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD5677	Discontinued
0.7143	Intermediate Similarity	NPD228	Approved
0.7134	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7251	Discontinued
0.7125	Intermediate Similarity	NPD6799	Approved
0.7125	Intermediate Similarity	NPD7212	Phase 2
0.7125	Intermediate Similarity	NPD7213	Phase 3
0.7124	Intermediate Similarity	NPD1558	Phase 1
0.7122	Intermediate Similarity	NPD4750	Phase 3
0.7118	Intermediate Similarity	NPD3926	Phase 2
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3539	Phase 1
0.7107	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5691	Approved
0.7097	Intermediate Similarity	NPD7097	Phase 1
0.7091	Intermediate Similarity	NPD6801	Discontinued
0.7086	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD919	Approved
0.7081	Intermediate Similarity	NPD2532	Approved
0.7081	Intermediate Similarity	NPD2534	Approved
0.7081	Intermediate Similarity	NPD2533	Approved
0.7075	Intermediate Similarity	NPD3705	Approved
0.7073	Intermediate Similarity	NPD4675	Approved
0.7073	Intermediate Similarity	NPD4678	Approved
0.7073	Intermediate Similarity	NPD4380	Phase 2
0.707	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6584	Phase 3
0.7059	Intermediate Similarity	NPD3787	Discontinued
0.7055	Intermediate Similarity	NPD3686	Approved
0.7055	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD17	Approved
0.7055	Intermediate Similarity	NPD3687	Approved
0.7051	Intermediate Similarity	NPD7033	Discontinued
0.7047	Intermediate Similarity	NPD1283	Approved
0.7037	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1607	Approved
0.7029	Intermediate Similarity	NPD7039	Approved
0.7029	Intermediate Similarity	NPD7038	Approved
0.7025	Intermediate Similarity	NPD1549	Phase 2
0.7024	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2237	Approved
0.7019	Intermediate Similarity	NPD4357	Discontinued
0.7019	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3620	Phase 2
0.7012	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6032	Approved
0.7006	Intermediate Similarity	NPD8054	Approved
0.7006	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2438	Suspended
0.7006	Intermediate Similarity	NPD8053	Approved
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD3022	Approved
0.7	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD3266	Approved
0.6994	Remote Similarity	NPD5403	Approved
0.6993	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1296	Phase 2
0.6982	Remote Similarity	NPD5709	Phase 3
0.698	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD230	Phase 1
0.6968	Remote Similarity	NPD4340	Discontinued
0.6966	Remote Similarity	NPD5536	Phase 2
0.6966	Remote Similarity	NPD7644	Approved
0.6962	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2346	Discontinued
0.6959	Remote Similarity	NPD1091	Approved
0.6957	Remote Similarity	NPD6667	Approved
0.6957	Remote Similarity	NPD6666	Approved
0.6948	Remote Similarity	NPD8032	Phase 2
0.6946	Remote Similarity	NPD5929	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