NPASS Compound

Structure

CID169913 OpenBabel06191715542D 32 34 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 0.0000 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.0000 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 0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 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 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 5.5000 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 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 2 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 18 2 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 19 21 1 0 0 0 0 20 24 1 0 0 0 0 21 26 1 1 0 0 0 22 23 1 0 0 0 0 22 32 1 6 0 0 0 23 26 1 6 0 0 0 23 27 1 0 0 0 0 24 29 2 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 30 2 0 0 0 0 25 31 1 0 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.26
Volume:	475.375
LogP:	4.326
LogD:	3.896
LogS:	-4.412
# Rotatable Bonds:	8
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	4.254
Fsp3:	0.556
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:	-5.275
MDCK Permeability:	2.8273669158807024e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.096
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	97.31014251708984%
Volume Distribution (VD):	0.209
Pgp-substrate:	1.9481463432312012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.845
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	1.877
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.753
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.95
Carcinogencity:	0.026
Eye Corrosion:	0.004
Eye Irritation:	0.903
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC169913

Natural Product ID:	NPC169913
*Common Name:**	Scoparic Acid A
IUPAC Name:	(1R,4aR,5R,8R,8aR)-8-benzoyloxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	GIQOHSBJFWWSAH-ZYEVQTAUSA-N
Standard InCHI:	InChI=1S/C27H36O5/c1-18(13-16-28)11-12-21-19(2)17-22(32-24(29)20-9-6-5-7-10-20)23-26(21,3)14-8-15-27(23,4)25(30)31/h5-7,9-10,13,21-23,28H,2,8,11-12,14-17H2,1,3-4H3,(H,30,31)/b18-13+/t21-,22-,23-,26-,27-/m1/s1
SMILES:	C/C(=CCO)/CC[C@@H]1C(=C)C[C@H]([C@@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478591
PubChem CID:	44584621
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	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	1
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT608	Individual Protein	Beta-glucuronidase	Bos taurus	IC50	=	6800.0	nM	PMID[538008]
NPT608	Individual Protein	Beta-glucuronidase	Bos taurus	Inhibition	=	5.0	%	PMID[538008]
NPT608	Individual Protein	Beta-glucuronidase	Bos taurus	Km	=	14300000.0	nM	PMID[538008]
NPT1618	Individual Protein	Peroxisome proliferator-activated receptor gamma	Mus musculus	EC50	>	100000.0	nM	PMID[538009]

☑ 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 NPC169913 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	243
0.1-0.2	1017
0.2-0.3	1901
0.3-0.4	4307
0.4-0.5	8861
0.5-0.6	12544
0.6-0.7	11598
0.7-0.8	1888
0.8-0.85	295
0.85-0.9	35
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC275576
0.937	High Similarity	NPC477896
0.937	High Similarity	NPC477893
0.9194	High Similarity	NPC470753
0.9194	High Similarity	NPC473220
0.9141	High Similarity	NPC203486
0.9141	High Similarity	NPC126516
0.9141	High Similarity	NPC329913
0.9141	High Similarity	NPC48929
0.9113	High Similarity	NPC470765
0.9	High Similarity	NPC472372
0.9	High Similarity	NPC472374
0.8881	High Similarity	NPC477894
0.8828	High Similarity	NPC147561
0.8797	High Similarity	NPC90614
0.8797	High Similarity	NPC100913
0.8797	High Similarity	NPC275592
0.878	High Similarity	NPC473243
0.876	High Similarity	NPC470278
0.876	High Similarity	NPC72915
0.8741	High Similarity	NPC477468
0.8731	High Similarity	NPC97947
0.8731	High Similarity	NPC118080
0.8731	High Similarity	NPC87448
0.8731	High Similarity	NPC291599
0.8731	High Similarity	NPC27377
0.8731	High Similarity	NPC41481
0.8731	High Similarity	NPC472576
0.8672	High Similarity	NPC115797
0.8672	High Similarity	NPC51448
0.8667	High Similarity	NPC182869
0.8657	High Similarity	NPC171207
0.8657	High Similarity	NPC472547
0.8657	High Similarity	NPC97667
0.8651	High Similarity	NPC12881
0.8651	High Similarity	NPC140118
0.8647	High Similarity	NPC39549
0.8613	High Similarity	NPC472556
0.8603	High Similarity	NPC91703
0.8603	High Similarity	NPC163087
0.8594	High Similarity	NPC5486
0.8593	High Similarity	NPC16912
0.8583	High Similarity	NPC128368
0.8582	High Similarity	NPC9905
0.8571	High Similarity	NPC472545
0.8571	High Similarity	NPC472551
0.8561	High Similarity	NPC474608
0.856	High Similarity	NPC50872
0.855	High Similarity	NPC472394
0.854	High Similarity	NPC241951
0.854	High Similarity	NPC38696
0.854	High Similarity	NPC475122
0.854	High Similarity	NPC470152
0.854	High Similarity	NPC475759
0.8529	High Similarity	NPC192658
0.8529	High Similarity	NPC34012
0.8519	High Similarity	NPC87934
0.8519	High Similarity	NPC162613
0.8516	High Similarity	NPC137416
0.8512	High Similarity	NPC153053
0.8504	High Similarity	NPC307139
0.8496	Intermediate Similarity	NPC195647
0.8496	Intermediate Similarity	NPC66761
0.8496	Intermediate Similarity	NPC472577
0.8496	Intermediate Similarity	NPC291638
0.8496	Intermediate Similarity	NPC17877
0.8485	Intermediate Similarity	NPC472656
0.8478	Intermediate Similarity	NPC470157
0.8478	Intermediate Similarity	NPC470159
0.8478	Intermediate Similarity	NPC96903
0.8478	Intermediate Similarity	NPC158663
0.8478	Intermediate Similarity	NPC174982
0.8478	Intermediate Similarity	NPC184817
0.8478	Intermediate Similarity	NPC171525
0.8478	Intermediate Similarity	NPC177940
0.8478	Intermediate Similarity	NPC476973
0.8478	Intermediate Similarity	NPC469349
0.8478	Intermediate Similarity	NPC471104
0.8478	Intermediate Similarity	NPC29704
0.8478	Intermediate Similarity	NPC473088
0.8478	Intermediate Similarity	NPC70403
0.8478	Intermediate Similarity	NPC472571
0.8478	Intermediate Similarity	NPC472568
0.8478	Intermediate Similarity	NPC127857
0.8478	Intermediate Similarity	NPC472575
0.8478	Intermediate Similarity	NPC200471
0.8478	Intermediate Similarity	NPC472572
0.8467	Intermediate Similarity	NPC95449
0.8456	Intermediate Similarity	NPC266374
0.8456	Intermediate Similarity	NPC224491
0.845	Intermediate Similarity	NPC253681
0.8429	Intermediate Similarity	NPC250046
0.8429	Intermediate Similarity	NPC60509
0.8429	Intermediate Similarity	NPC81698
0.8425	Intermediate Similarity	NPC182333
0.8425	Intermediate Similarity	NPC273336
0.8417	Intermediate Similarity	NPC473602
0.8409	Intermediate Similarity	NPC238370
0.8406	Intermediate Similarity	NPC95810
0.8406	Intermediate Similarity	NPC25768
0.8406	Intermediate Similarity	NPC57628
0.8406	Intermediate Similarity	NPC188865
0.8406	Intermediate Similarity	NPC476974
0.8406	Intermediate Similarity	NPC472573
0.8406	Intermediate Similarity	NPC125106
0.8406	Intermediate Similarity	NPC34943
0.8406	Intermediate Similarity	NPC163719
0.8406	Intermediate Similarity	NPC11685
0.8406	Intermediate Similarity	NPC472569
0.8406	Intermediate Similarity	NPC70716
0.8406	Intermediate Similarity	NPC95265
0.8406	Intermediate Similarity	NPC472570
0.8403	Intermediate Similarity	NPC469636
0.8397	Intermediate Similarity	NPC472388
0.8387	Intermediate Similarity	NPC45794
0.8372	Intermediate Similarity	NPC476599
0.837	Intermediate Similarity	NPC183122
0.837	Intermediate Similarity	NPC249817
0.837	Intermediate Similarity	NPC283375
0.837	Intermediate Similarity	NPC475373
0.8369	Intermediate Similarity	NPC165260
0.8369	Intermediate Similarity	NPC7095
0.8369	Intermediate Similarity	NPC161239
0.8369	Intermediate Similarity	NPC198455
0.8361	Intermediate Similarity	NPC307651
0.8359	Intermediate Similarity	NPC77691
0.8358	Intermediate Similarity	NPC471864
0.8358	Intermediate Similarity	NPC473399
0.8358	Intermediate Similarity	NPC473216
0.8357	Intermediate Similarity	NPC132652
0.8357	Intermediate Similarity	NPC217918
0.8357	Intermediate Similarity	NPC473760
0.8347	Intermediate Similarity	NPC82899
0.8347	Intermediate Similarity	NPC270699
0.8347	Intermediate Similarity	NPC321852
0.8345	Intermediate Similarity	NPC125882
0.8345	Intermediate Similarity	NPC311825
0.8345	Intermediate Similarity	NPC92867
0.8321	Intermediate Similarity	NPC225103
0.832	Intermediate Similarity	NPC254233
0.831	Intermediate Similarity	NPC471103
0.831	Intermediate Similarity	NPC470153
0.831	Intermediate Similarity	NPC197037
0.8309	Intermediate Similarity	NPC475482
0.8309	Intermediate Similarity	NPC216940
0.8309	Intermediate Similarity	NPC472371
0.8309	Intermediate Similarity	NPC198621
0.8309	Intermediate Similarity	NPC210591
0.8309	Intermediate Similarity	NPC22676
0.8309	Intermediate Similarity	NPC475652
0.8309	Intermediate Similarity	NPC214550
0.8309	Intermediate Similarity	NPC472395
0.8308	Intermediate Similarity	NPC190849
0.8308	Intermediate Similarity	NPC171007
0.8306	Intermediate Similarity	NPC470820
0.8298	Intermediate Similarity	NPC476975
0.8298	Intermediate Similarity	NPC301556
0.8298	Intermediate Similarity	NPC270590
0.8298	Intermediate Similarity	NPC92293
0.8298	Intermediate Similarity	NPC471101
0.8298	Intermediate Similarity	NPC473215
0.8298	Intermediate Similarity	NPC266265
0.8296	Intermediate Similarity	NPC477874
0.8296	Intermediate Similarity	NPC173569
0.8295	Intermediate Similarity	NPC295664
0.8286	Intermediate Similarity	NPC48599
0.8286	Intermediate Similarity	NPC474935
0.8286	Intermediate Similarity	NPC20255
0.8286	Intermediate Similarity	NPC209592
0.8286	Intermediate Similarity	NPC240115
0.8284	Intermediate Similarity	NPC310662
0.8271	Intermediate Similarity	NPC80599
0.8264	Intermediate Similarity	NPC473632
0.8264	Intermediate Similarity	NPC473670
0.8264	Intermediate Similarity	NPC305912
0.8264	Intermediate Similarity	NPC132599
0.8264	Intermediate Similarity	NPC1082
0.8264	Intermediate Similarity	NPC21410
0.8264	Intermediate Similarity	NPC469730
0.8264	Intermediate Similarity	NPC260818
0.8261	Intermediate Similarity	NPC472546
0.8261	Intermediate Similarity	NPC183540
0.8258	Intermediate Similarity	NPC473443
0.8258	Intermediate Similarity	NPC471832
0.8254	Intermediate Similarity	NPC202015
0.8252	Intermediate Similarity	NPC477905
0.8252	Intermediate Similarity	NPC472548
0.8248	Intermediate Similarity	NPC477904
0.8248	Intermediate Similarity	NPC43241
0.8248	Intermediate Similarity	NPC473758
0.8248	Intermediate Similarity	NPC473109
0.8248	Intermediate Similarity	NPC473613
0.8248	Intermediate Similarity	NPC184747
0.8248	Intermediate Similarity	NPC473081
0.8248	Intermediate Similarity	NPC475400
0.8248	Intermediate Similarity	NPC183270
0.8248	Intermediate Similarity	NPC48017
0.8248	Intermediate Similarity	NPC473060
0.8248	Intermediate Similarity	NPC476094
0.8248	Intermediate Similarity	NPC4341

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 NPC169913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	731
0.2-0.3	1245
0.3-0.4	2398
0.4-0.5	2371
0.5-0.6	1557
0.6-0.7	572
0.7-0.8	54
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD7236	Approved
0.8397	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD7008	Discontinued
0.8182	Intermediate Similarity	NPD7239	Suspended
0.8145	Intermediate Similarity	NPD5951	Approved
0.8145	Intermediate Similarity	NPD2629	Approved
0.8115	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2182	Approved
0.8099	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6273	Approved
0.7769	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD164	Approved
0.7769	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7961	Discontinued
0.7692	Intermediate Similarity	NPD7003	Approved
0.7692	Intermediate Similarity	NPD8166	Discontinued
0.7682	Intermediate Similarity	NPD7057	Phase 3
0.7682	Intermediate Similarity	NPD7058	Phase 2
0.7664	Intermediate Similarity	NPD3764	Approved
0.7656	Intermediate Similarity	NPD4198	Discontinued
0.7609	Intermediate Similarity	NPD6663	Approved
0.7606	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD1238	Approved
0.7574	Intermediate Similarity	NPD5736	Approved
0.7569	Intermediate Similarity	NPD4628	Phase 3
0.7541	Intermediate Similarity	NPD6647	Phase 2
0.7541	Intermediate Similarity	NPD1929	Approved
0.7541	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD1930	Approved
0.7519	Intermediate Similarity	NPD6287	Discontinued
0.7517	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7481	Intermediate Similarity	NPD7741	Discontinued
0.748	Intermediate Similarity	NPD1237	Approved
0.748	Intermediate Similarity	NPD5909	Discontinued
0.7465	Intermediate Similarity	NPD2799	Discontinued
0.7422	Intermediate Similarity	NPD7094	Approved
0.7422	Intermediate Similarity	NPD6858	Approved
0.7413	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD2313	Discontinued
0.7379	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6085	Phase 2
0.7361	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7799	Discontinued
0.7343	Intermediate Similarity	NPD7305	Phase 1
0.7313	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD2066	Phase 3
0.7285	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7610	Discontinued
0.7266	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD8127	Discontinued
0.7234	Intermediate Similarity	NPD7714	Approved
0.7234	Intermediate Similarity	NPD7715	Approved
0.7218	Intermediate Similarity	NPD9545	Approved
0.7209	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2067	Discontinued
0.7183	Intermediate Similarity	NPD4140	Approved
0.7178	Intermediate Similarity	NPD8368	Discontinued
0.7176	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2797	Approved
0.7171	Intermediate Similarity	NPD3226	Approved
0.7133	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7122	Intermediate Similarity	NPD2798	Approved
0.7113	Intermediate Similarity	NPD7713	Phase 3
0.7113	Intermediate Similarity	NPD8032	Phase 2
0.7111	Intermediate Similarity	NPD3019	Approved
0.7101	Intermediate Similarity	NPD1283	Approved
0.7099	Intermediate Similarity	NPD6010	Discontinued
0.7097	Intermediate Similarity	NPD7819	Suspended
0.7097	Intermediate Similarity	NPD5760	Phase 2
0.7097	Intermediate Similarity	NPD5761	Phase 2
0.7095	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8360	Approved
0.7083	Intermediate Similarity	NPD8361	Approved
0.7073	Intermediate Similarity	NPD9495	Approved
0.7068	Intermediate Similarity	NPD9493	Approved
0.7066	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8434	Phase 2
0.7063	Intermediate Similarity	NPD2979	Phase 3
0.7059	Intermediate Similarity	NPD9258	Approved
0.7059	Intermediate Similarity	NPD9256	Approved
0.7055	Intermediate Similarity	NPD5406	Approved
0.7055	Intermediate Similarity	NPD5404	Approved
0.7055	Intermediate Similarity	NPD5408	Approved
0.7055	Intermediate Similarity	NPD5405	Approved
0.705	Intermediate Similarity	NPD1470	Approved
0.7048	Intermediate Similarity	NPD8407	Phase 2
0.7042	Intermediate Similarity	NPD3268	Approved
0.7042	Intermediate Similarity	NPD6798	Discontinued
0.704	Intermediate Similarity	NPD1932	Approved
0.7034	Intermediate Similarity	NPD7097	Phase 1
0.7025	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1202	Approved
0.7021	Intermediate Similarity	NPD6832	Phase 2
0.7007	Intermediate Similarity	NPD4807	Approved
0.7007	Intermediate Similarity	NPD4806	Approved
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD7440	Discontinued
0.6994	Remote Similarity	NPD5844	Phase 1
0.6986	Remote Similarity	NPD4308	Phase 3
0.6985	Remote Similarity	NPD5306	Approved
0.6985	Remote Similarity	NPD2932	Approved
0.6985	Remote Similarity	NPD5305	Approved
0.6984	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8435	Approved
0.698	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD2329	Discontinued
0.6972	Remote Similarity	NPD7095	Approved
0.6957	Remote Similarity	NPD3972	Approved
0.6957	Remote Similarity	NPD4878	Approved
0.6953	Remote Similarity	NPD6685	Approved
0.6944	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1088	Approved
0.6933	Remote Similarity	NPD6190	Approved
0.6923	Remote Similarity	NPD37	Approved
0.6912	Remote Similarity	NPD5585	Approved
0.6912	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1989	Approved
0.6908	Remote Similarity	NPD2534	Approved
0.6908	Remote Similarity	NPD2532	Approved
0.6908	Remote Similarity	NPD2533	Approved
0.6906	Remote Similarity	NPD5157	Phase 1
0.6906	Remote Similarity	NPD5159	Phase 2
0.6906	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4967	Phase 2
0.6899	Remote Similarity	NPD4966	Approved
0.6899	Remote Similarity	NPD4965	Approved
0.6899	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD230	Phase 1
0.6892	Remote Similarity	NPD6004	Phase 3
0.6892	Remote Similarity	NPD6005	Phase 3
0.6892	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6002	Phase 3
0.6886	Remote Similarity	NPD8313	Approved
0.6886	Remote Similarity	NPD8312	Approved
0.6884	Remote Similarity	NPD1201	Approved
0.6884	Remote Similarity	NPD1281	Approved
0.688	Remote Similarity	NPD7798	Approved
0.6879	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD5048	Discontinued
0.6871	Remote Similarity	NPD7473	Discontinued
0.6867	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4110	Phase 3
0.6864	Remote Similarity	NPD8150	Discontinued
0.6861	Remote Similarity	NPD5126	Approved
0.6861	Remote Similarity	NPD5125	Phase 3
0.6861	Remote Similarity	NPD4626	Approved
0.6859	Remote Similarity	NPD7411	Suspended
0.6857	Remote Similarity	NPD1876	Approved
0.6857	Remote Similarity	NPD2199	Approved
0.6857	Remote Similarity	NPD2198	Approved
0.6855	Remote Similarity	NPD7075	Discontinued
0.6853	Remote Similarity	NPD6039	Approved
0.6846	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8485	Approved
0.6838	Remote Similarity	NPD3091	Approved
0.6835	Remote Similarity	NPD9717	Approved
0.6835	Remote Similarity	NPD1608	Approved
0.6835	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4060	Phase 1
0.6824	Remote Similarity	NPD4476	Approved
0.6824	Remote Similarity	NPD2438	Suspended
0.6824	Remote Similarity	NPD4477	Approved
0.6812	Remote Similarity	NPD3496	Discontinued
0.6812	Remote Similarity	NPD3026	Approved
0.6812	Remote Similarity	NPD3023	Approved
0.6812	Remote Similarity	NPD4106	Approved
0.6812	Remote Similarity	NPD4136	Approved
0.6812	Remote Similarity	NPD4135	Approved
0.6809	Remote Similarity	NPD1203	Approved
0.6809	Remote Similarity	NPD1164	Approved
0.6797	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4380	Phase 2
0.679	Remote Similarity	NPD6232	Discontinued
0.6788	Remote Similarity	NPD3025	Approved
0.6788	Remote Similarity	NPD5691	Approved
0.6788	Remote Similarity	NPD3024	Approved
0.6781	Remote Similarity	NPD447	Suspended
0.6781	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1086	Approved
0.6777	Remote Similarity	NPD1090	Approved
0.6777	Remote Similarity	NPD1089	Approved
0.6766	Remote Similarity	NPD6764	Approved
0.6766	Remote Similarity	NPD6765	Approved
0.6763	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3748	Approved
0.6755	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6677	Suspended
0.6739	Remote Similarity	NPD3095	Discontinued
0.6738	Remote Similarity	NPD5667	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