NPASS Compound

Structure

NPC472556 OpenBabel07101719252D 42 46 0 0 1 0 0 0 0 0999 V2000 0.8476 3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7199 -0.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4894 -0.8476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 -2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3904 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3904 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3904 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 -2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4850 0.0506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7930 0.7427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7812 1.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1910 -0.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4304 0.3039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3904 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 3.4255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7585 1.1664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 1.4681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8476 0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5428 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8476 4.4043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3745 1.9270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9787 -1.6952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0118 0.2210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 2 0 0 0 0 2 32 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 32 1 0 0 0 0 19 22 2 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 40 1 0 0 0 0 21 25 1 0 0 0 0 21 33 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 35 1 6 0 0 0 26 32 1 1 0 0 0 26 33 1 0 0 0 0 27 36 2 0 0 0 0 27 40 1 0 0 0 0 28 29 1 0 0 0 0 28 33 1 1 0 0 0 28 41 1 0 0 0 0 29 34 1 6 0 0 0 29 42 1 0 0 0 0 30 37 2 0 0 0 0 30 41 1 0 0 0 0 31 38 2 0 0 0 0 31 42 1 0 0 0 0 32 34 1 6 0 0 0 33 3 1 1 0 0 0 34 4 1 1 0 0 0 34 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.24
Volume:	592.522
LogP:	3.945
LogD:	2.944
LogS:	-4.376
# Rotatable Bonds:	8
TPSA:	126.43
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	4.934
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.105
MDCK Permeability:	1.6168496586033143e-05
Pgp-inhibitor:	0.926
Pgp-substrate:	0.317
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.897
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.8
Plasma Protein Binding (PPB):	99.80879974365234%
Volume Distribution (VD):	1.065
Pgp-substrate:	3.544963836669922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.484
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.645
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.627
CYP2C9-substrate:	0.867
CYP2D6-inhibitor:	0.962
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	10.398
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.477
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.313
Carcinogencity:	0.134
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.422

Download Data

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

Natural Product: NPC472556

Natural Product ID:	NPC472556
*Common Name:**	INDRXXKQJAKWRM-OMAAXZSASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	INDRXXKQJAKWRM-OMAAXZSASA-N
Standard InCHI:	InChI=1S/C34H36O8/c1-21-25(35)15-16-26-32(2,18-17-22-19-27(36)40-20-22)34(4,39)29(42-31(38)24-13-9-6-10-14-24)28(33(21,26)3)41-30(37)23-11-7-5-8-12-23/h5-14,17-19,25-26,28-29,35,39H,1,15-16,20H2,2-4H3/b18-17+/t25-,26+,28-,29-,32+,33-,34-/m0/s1
SMILES:	CC1(C2CCC(C(=C)C2(C(C(C1(C)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)C)O)C=CC5=CC(=O)OC5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577092
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	<	50.0	%	PMID[517614]

☑ 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 NPC472556 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	295
0.1-0.2	1070
0.2-0.3	2213
0.3-0.4	4157
0.4-0.5	8476
0.5-0.6	10761
0.6-0.7	12570
0.7-0.8	2669
0.8-0.85	221
0.85-0.9	126
0.9-0.95	104
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.971	High Similarity	NPC174982
0.971	High Similarity	NPC472571
0.971	High Similarity	NPC96903
0.971	High Similarity	NPC473088
0.971	High Similarity	NPC472575
0.971	High Similarity	NPC470159
0.971	High Similarity	NPC476973
0.971	High Similarity	NPC171525
0.971	High Similarity	NPC158663
0.971	High Similarity	NPC472568
0.971	High Similarity	NPC470157
0.971	High Similarity	NPC177940
0.971	High Similarity	NPC471104
0.971	High Similarity	NPC184817
0.971	High Similarity	NPC200471
0.971	High Similarity	NPC469349
0.971	High Similarity	NPC472572
0.971	High Similarity	NPC70403
0.971	High Similarity	NPC29704
0.9638	High Similarity	NPC241951
0.9638	High Similarity	NPC125106
0.9638	High Similarity	NPC70716
0.9638	High Similarity	NPC11685
0.9638	High Similarity	NPC476974
0.9638	High Similarity	NPC188865
0.9638	High Similarity	NPC470152
0.9638	High Similarity	NPC472573
0.9638	High Similarity	NPC25768
0.9638	High Similarity	NPC475759
0.9638	High Similarity	NPC57628
0.9638	High Similarity	NPC472570
0.9638	High Similarity	NPC472569
0.9638	High Similarity	NPC475122
0.9638	High Similarity	NPC95265
0.9638	High Similarity	NPC163719
0.9638	High Similarity	NPC95810
0.9565	High Similarity	NPC91703
0.9565	High Similarity	NPC163087
0.9562	High Similarity	NPC224491
0.9507	High Similarity	NPC470153
0.9504	High Similarity	NPC476975
0.9504	High Similarity	NPC266265
0.9504	High Similarity	NPC301556
0.9504	High Similarity	NPC270590
0.9504	High Similarity	NPC92293
0.9504	High Similarity	NPC471101
0.9489	High Similarity	NPC472547
0.9437	High Similarity	NPC473214
0.9437	High Similarity	NPC470245
0.9433	High Similarity	NPC281717
0.942	High Similarity	NPC87448
0.942	High Similarity	NPC16912
0.942	High Similarity	NPC291599
0.942	High Similarity	NPC97947
0.942	High Similarity	NPC27377
0.942	High Similarity	NPC41481
0.942	High Similarity	NPC472576
0.942	High Similarity	NPC118080
0.9366	High Similarity	NPC473215
0.9362	High Similarity	NPC474935
0.9362	High Similarity	NPC473602
0.9348	High Similarity	NPC473060
0.9348	High Similarity	NPC100913
0.9348	High Similarity	NPC476094
0.9348	High Similarity	NPC275592
0.9348	High Similarity	NPC473081
0.9348	High Similarity	NPC211137
0.9348	High Similarity	NPC90614
0.9348	High Similarity	NPC4341
0.9348	High Similarity	NPC184747
0.9348	High Similarity	NPC473112
0.9348	High Similarity	NPC43241
0.9348	High Similarity	NPC473758
0.9348	High Similarity	NPC147880
0.9348	High Similarity	NPC171207
0.9348	High Similarity	NPC473085
0.9348	High Similarity	NPC97667
0.9348	High Similarity	NPC473109
0.9348	High Similarity	NPC200592
0.9348	High Similarity	NPC48017
0.9348	High Similarity	NPC473613
0.9343	High Similarity	NPC39549
0.9306	High Similarity	NPC477905
0.9275	High Similarity	NPC214550
0.9275	High Similarity	NPC475652
0.9275	High Similarity	NPC210591
0.927	High Similarity	NPC472545
0.927	High Similarity	NPC472551
0.9214	High Similarity	NPC472546
0.9214	High Similarity	NPC34012
0.9203	High Similarity	NPC183122
0.9203	High Similarity	NPC283375
0.9172	High Similarity	NPC472548
0.9167	High Similarity	NPC7095
0.9149	High Similarity	NPC177340
0.9149	High Similarity	NPC191082
0.9149	High Similarity	NPC473673
0.9149	High Similarity	NPC270498
0.9149	High Similarity	NPC477894
0.9149	High Similarity	NPC475429
0.9149	High Similarity	NPC147217
0.9149	High Similarity	NPC139067
0.9149	High Similarity	NPC246480
0.9116	High Similarity	NPC106895
0.911	High Similarity	NPC158333
0.911	High Similarity	NPC472022
0.911	High Similarity	NPC265395
0.911	High Similarity	NPC242262
0.911	High Similarity	NPC1173
0.911	High Similarity	NPC256142
0.911	High Similarity	NPC473414
0.911	High Similarity	NPC257213
0.911	High Similarity	NPC472030
0.911	High Similarity	NPC249471
0.911	High Similarity	NPC472005
0.911	High Similarity	NPC237549
0.911	High Similarity	NPC304876
0.9097	High Similarity	NPC250046
0.9097	High Similarity	NPC60509
0.9097	High Similarity	NPC81698
0.9085	High Similarity	NPC51314
0.9085	High Similarity	NPC38696
0.9085	High Similarity	NPC67777
0.9085	High Similarity	NPC470231
0.9085	High Similarity	NPC34943
0.9078	High Similarity	NPC192658
0.9058	High Similarity	NPC472577
0.9058	High Similarity	NPC66761
0.9058	High Similarity	NPC195647
0.9058	High Similarity	NPC291638
0.9058	High Similarity	NPC17877
0.9048	High Similarity	NPC228204
0.9048	High Similarity	NPC26033
0.9048	High Similarity	NPC472549
0.9048	High Similarity	NPC282239
0.9048	High Similarity	NPC112523
0.9048	High Similarity	NPC114410
0.9034	High Similarity	NPC31829
0.9034	High Similarity	NPC112216
0.9034	High Similarity	NPC198455
0.9034	High Similarity	NPC161239
0.9034	High Similarity	NPC469448
0.9034	High Similarity	NPC165260
0.9028	High Similarity	NPC473760
0.9007	High Similarity	NPC266374
0.8993	High Similarity	NPC472372
0.8993	High Similarity	NPC472374
0.8986	High Similarity	NPC48929
0.8986	High Similarity	NPC474608
0.8986	High Similarity	NPC217091
0.898	High Similarity	NPC77719
0.8958	High Similarity	NPC20255
0.8958	High Similarity	NPC48599
0.8958	High Similarity	NPC209592
0.8958	High Similarity	NPC240115
0.8936	High Similarity	NPC87934
0.8936	High Similarity	NPC162613
0.8926	High Similarity	NPC469771
0.8926	High Similarity	NPC472393
0.8921	High Similarity	NPC477893
0.8921	High Similarity	NPC477896
0.8919	High Similarity	NPC132599
0.8919	High Similarity	NPC34066
0.8919	High Similarity	NPC473670
0.8919	High Similarity	NPC473632
0.8919	High Similarity	NPC473611
0.8919	High Similarity	NPC469730
0.8919	High Similarity	NPC21410
0.8889	High Similarity	NPC125882
0.8889	High Similarity	NPC92867
0.8889	High Similarity	NPC127857
0.8889	High Similarity	NPC311825
0.8874	High Similarity	NPC476077
0.8867	High Similarity	NPC471102
0.8865	High Similarity	NPC9905
0.8851	High Similarity	NPC472658
0.8851	High Similarity	NPC472657
0.8844	High Similarity	NPC471103
0.8844	High Similarity	NPC51602
0.8832	High Similarity	NPC147561
0.8828	High Similarity	NPC312393
0.8811	High Similarity	NPC182869
0.8803	High Similarity	NPC183270
0.8803	High Similarity	NPC477904
0.8792	High Similarity	NPC469422
0.8776	High Similarity	NPC254558
0.8767	High Similarity	NPC217918
0.875	High Similarity	NPC477468
0.875	High Similarity	NPC473220
0.875	High Similarity	NPC470753
0.875	High Similarity	NPC95449
0.8742	High Similarity	NPC469399
0.8716	High Similarity	NPC101043
0.8716	High Similarity	NPC197037
0.8716	High Similarity	NPC306799
0.8707	High Similarity	NPC76103
0.8699	High Similarity	NPC478263
0.8684	High Similarity	NPC477623
0.8676	High Similarity	NPC470765
0.8676	High Similarity	NPC275576

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 NPC472556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	709
0.2-0.3	1402
0.3-0.4	2610
0.4-0.5	2366
0.5-0.6	1317
0.6-0.7	444
0.7-0.8	54
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8133	Intermediate Similarity	NPD7236	Approved
0.8042	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7239	Suspended
0.7927	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7799	Discontinued
0.7793	Intermediate Similarity	NPD7008	Discontinued
0.7778	Intermediate Similarity	NPD8360	Approved
0.7778	Intermediate Similarity	NPD8361	Approved
0.7765	Intermediate Similarity	NPD8434	Phase 2
0.7679	Intermediate Similarity	NPD8368	Discontinued
0.7674	Intermediate Similarity	NPD8435	Approved
0.7669	Intermediate Similarity	NPD8127	Discontinued
0.7661	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD8166	Discontinued
0.7647	Intermediate Similarity	NPD8407	Phase 2
0.7614	Intermediate Similarity	NPD8485	Approved
0.7571	Intermediate Similarity	NPD7741	Discontinued
0.7536	Intermediate Similarity	NPD2629	Approved
0.7531	Intermediate Similarity	NPD7057	Phase 3
0.7531	Intermediate Similarity	NPD7058	Phase 2
0.7516	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8150	Discontinued
0.745	Intermediate Similarity	NPD7961	Discontinued
0.741	Intermediate Similarity	NPD5951	Approved
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7386	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD3764	Approved
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.7372	Intermediate Similarity	NPD6190	Approved
0.7357	Intermediate Similarity	NPD4198	Discontinued
0.7346	Intermediate Similarity	NPD37	Approved
0.7317	Intermediate Similarity	NPD4966	Approved
0.7317	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4965	Approved
0.7317	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD7003	Approved
0.7285	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7228	Approved
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6234	Discontinued
0.7226	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5126	Approved
0.7222	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5125	Phase 3
0.7222	Intermediate Similarity	NPD4380	Phase 2
0.7212	Intermediate Similarity	NPD7768	Phase 2
0.7195	Intermediate Similarity	NPD8455	Phase 2
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7176	Intermediate Similarity	NPD7473	Discontinued
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7075	Discontinued
0.7168	Intermediate Similarity	NPD7685	Pre-registration
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7266	Discontinued
0.711	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6232	Discontinued
0.7101	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5404	Approved
0.7051	Intermediate Similarity	NPD5406	Approved
0.7051	Intermediate Similarity	NPD5408	Approved
0.7051	Intermediate Similarity	NPD5405	Approved
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5402	Approved
0.7043	Intermediate Similarity	NPD8319	Approved
0.7043	Intermediate Similarity	NPD8320	Phase 1
0.7042	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5403	Approved
0.703	Intermediate Similarity	NPD6801	Discontinued
0.7025	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7610	Discontinued
0.7012	Intermediate Similarity	NPD6599	Discontinued
0.6995	Remote Similarity	NPD7699	Phase 2
0.6995	Remote Similarity	NPD7700	Phase 2
0.6993	Remote Similarity	NPD7714	Approved
0.6993	Remote Similarity	NPD6663	Approved
0.6993	Remote Similarity	NPD7715	Approved
0.6989	Remote Similarity	NPD7497	Discontinued
0.6988	Remote Similarity	NPD5761	Phase 2
0.6988	Remote Similarity	NPD5760	Phase 2
0.6981	Remote Similarity	NPD3750	Approved
0.6978	Remote Similarity	NPD2182	Approved
0.6971	Remote Similarity	NPD7240	Approved
0.6971	Remote Similarity	NPD6559	Discontinued
0.697	Remote Similarity	NPD7411	Suspended
0.6964	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5736	Approved
0.6951	Remote Similarity	NPD3226	Approved
0.6939	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6535	Approved
0.6923	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6166	Phase 2
0.6919	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5401	Approved
0.6903	Remote Similarity	NPD230	Phase 1
0.6903	Remote Similarity	NPD6355	Discontinued
0.6901	Remote Similarity	NPD6858	Approved
0.6901	Remote Similarity	NPD7094	Approved
0.6898	Remote Similarity	NPD7435	Discontinued
0.6897	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6287	Discontinued
0.6886	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7074	Phase 3
0.6853	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3817	Phase 2
0.6842	Remote Similarity	NPD7199	Phase 2
0.6842	Remote Similarity	NPD6959	Discontinued
0.6839	Remote Similarity	NPD3818	Discontinued
0.6835	Remote Similarity	NPD2935	Discontinued
0.6829	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1934	Approved
0.6815	Remote Similarity	NPD7097	Phase 1
0.681	Remote Similarity	NPD2533	Approved
0.681	Remote Similarity	NPD2534	Approved
0.681	Remote Similarity	NPD2532	Approved
0.681	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7054	Approved
0.6792	Remote Similarity	NPD2346	Discontinued
0.6788	Remote Similarity	NPD8462	Phase 1
0.6786	Remote Similarity	NPD1465	Phase 2
0.6784	Remote Similarity	NPD5494	Approved
0.678	Remote Similarity	NPD6764	Approved
0.678	Remote Similarity	NPD6765	Approved
0.6774	Remote Similarity	NPD7713	Phase 3
0.6772	Remote Similarity	NPD3748	Approved
0.6771	Remote Similarity	NPD7874	Approved
0.6771	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1238	Approved
0.6761	Remote Similarity	NPD7472	Approved
0.6755	Remote Similarity	NPD6823	Phase 2
0.6753	Remote Similarity	NPD7095	Approved
0.6748	Remote Similarity	NPD6799	Approved
0.6742	Remote Similarity	NPD7808	Phase 3
0.6739	Remote Similarity	NPD1930	Approved
0.6739	Remote Similarity	NPD6647	Phase 2
0.6739	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1929	Approved
0.6738	Remote Similarity	NPD6780	Approved
0.6738	Remote Similarity	NPD6777	Approved
0.6738	Remote Similarity	NPD6778	Approved
0.6738	Remote Similarity	NPD6779	Approved
0.6738	Remote Similarity	NPD6776	Approved
0.6738	Remote Similarity	NPD6781	Approved
0.6738	Remote Similarity	NPD6782	Approved
0.6735	Remote Similarity	NPD8404	Phase 2
0.6735	Remote Similarity	NPD9545	Approved
0.673	Remote Similarity	NPD2438	Suspended
0.672	Remote Similarity	NPD7697	Approved
0.672	Remote Similarity	NPD7698	Approved
0.672	Remote Similarity	NPD7696	Phase 3
0.6719	Remote Similarity	NPD8151	Discontinued
0.671	Remote Similarity	NPD6798	Discontinued
0.6691	Remote Similarity	NPD164	Approved
0.6691	Remote Similarity	NPD5909	Discontinued
0.6691	Remote Similarity	NPD1237	Approved
0.669	Remote Similarity	NPD2067	Discontinued
0.6687	Remote Similarity	NPD6002	Phase 3
0.6687	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5763	Approved
0.6687	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5762	Approved
0.6687	Remote Similarity	NPD6005	Phase 3
0.6687	Remote Similarity	NPD6004	Phase 3
0.6685	Remote Similarity	NPD7251	Discontinued
0.6684	Remote Similarity	NPD7871	Phase 2
0.6684	Remote Similarity	NPD7870	Phase 2
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD7305	Phase 1
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD2799	Discontinued
0.6649	Remote Similarity	NPD7801	Approved
0.6648	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3751	Discontinued

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