NPASS Compound

Structure

NPC100420 OpenBabel07101718322D 41 44 0 0 1 0 0 0 0 0999 V2000 1.0067 7.2481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9845 5.5545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2114 3.0142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3681 -1.7576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6626 -0.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0290 3.8610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4096 -1.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5178 6.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8693 1.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8693 0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5178 4.7077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3646 1.5475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0067 3.8610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5178 1.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5628 1.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0225 1.5475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1757 3.0142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0067 5.5545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3646 2.5253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3245 -1.5543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9648 0.5732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7161 1.5475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0225 2.5253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1757 1.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7161 -0.4081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5628 0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3289 2.5253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7161 2.5253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9724 0.1022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3977 0.8932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5178 3.0142 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3289 1.5475 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9788 -2.2810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9212 0.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7161 -1.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5628 3.0142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4096 -0.4081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6267 -0.6244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3105 1.2998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8693 3.0142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 7 37 1 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 31 1 0 0 0 0 15 22 2 0 0 0 0 15 26 1 0 0 0 0 16 23 1 0 0 0 0 16 24 2 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 19 31 1 6 0 0 0 20 33 2 0 0 0 0 20 38 1 0 0 0 0 21 34 2 0 0 0 0 21 39 1 0 0 0 0 22 28 1 0 0 0 0 23 40 1 6 0 0 0 24 29 1 0 0 0 0 24 32 1 0 0 0 0 25 26 2 0 0 0 0 25 35 1 0 0 0 0 26 37 1 0 0 0 0 27 31 1 1 0 0 0 27 32 1 0 0 0 0 28 36 2 0 0 0 0 28 40 1 0 0 0 0 29 38 1 6 0 0 0 29 41 1 0 0 0 0 30 32 1 6 0 0 0 30 39 1 0 0 0 0 30 41 1 0 0 0 0 31 6 1 1 0 0 0 32 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.27
Volume:	583.186
LogP:	4.221
LogD:	3.058
LogS:	-4.788
# Rotatable Bonds:	11
TPSA:	117.59
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	5.477
Fsp3:	0.531
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.79
MDCK Permeability:	6.918372673681006e-05
Pgp-inhibitor:	0.833
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.174

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.188
Plasma Protein Binding (PPB):	96.53511047363281%
Volume Distribution (VD):	1.511
Pgp-substrate:	9.340134620666504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.716
CYP2C19-substrate:	0.169
CYP2C9-inhibitor:	0.726
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.668
CYP2D6-substrate:	0.495
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.467

ADMET: Excretion

Clearance (CL):	3.105
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.85
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.98
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.682
Carcinogencity:	0.745
Eye Corrosion:	0.021
Eye Irritation:	0.261
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC100420

Natural Product ID:	NPC100420
*Common Name:**	Casearborin B
IUPAC Name:	[(1S,3R,5R,6aS,7R,8R,10aS)-1,3-diacetyloxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] 4-hydroxy-3-methoxybenzoate
Synonyms:
Standard InCHIKey:	HSCLLTPGIBCIBD-DZHOVOBOSA-N
Standard InCHI:	InChI=1S/C32H40O9/c1-8-18(2)11-13-31(6)19(3)12-14-32-24(29(38-20(4)33)41-30(32)39-21(5)34)16-23(17-27(31)32)40-28(36)22-9-10-25(35)26(15-22)37-7/h8-11,15-16,19,23,27,29-30,35H,1,12-14,17H2,2-7H3/b18-11+/t19-,23+,27+,29+,30-,31-,32-/m1/s1
SMILES:	C=C/C(=C/C[C@]1(C)[C@H](C)CC[C@@]23C(=C[C@@H](C[C@@H]12)OC(=O)c1ccc(c(c1)OC)O)[C@@H](OC(=O)C)O[C@H]3OC(=O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505172
PubChem CID:	5352095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO28776	Casearia arborea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843580]
NPO28776	Casearia arborea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT390	Cell Line	LOX IMVI	Homo sapiens	IC50	=	290.0	nM	PMID[522552]
NPT374	Cell Line	SF-539	Homo sapiens	IC50	=	290.0	nM	PMID[522552]

☑ 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 NPC100420 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	351
0.1-0.2	1337
0.2-0.3	2739
0.3-0.4	5530
0.4-0.5	9714
0.5-0.6	7829
0.6-0.7	7315
0.7-0.8	7288
0.8-0.85	514
0.85-0.9	77
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9152	High Similarity	NPC469438
0.9152	High Similarity	NPC469354
0.9057	High Similarity	NPC226759
0.9048	High Similarity	NPC188217
0.9	High Similarity	NPC68619
0.8976	High Similarity	NPC316539
0.8974	High Similarity	NPC162569
0.8974	High Similarity	NPC35160
0.8961	High Similarity	NPC208293
0.8909	High Similarity	NPC202428
0.8909	High Similarity	NPC266545
0.8902	High Similarity	NPC200726
0.8869	High Similarity	NPC475054
0.8869	High Similarity	NPC469397
0.8868	High Similarity	NPC62051
0.8861	High Similarity	NPC267091
0.8861	High Similarity	NPC124842
0.8854	High Similarity	NPC267469
0.8854	High Similarity	NPC87630
0.8854	High Similarity	NPC179128
0.8854	High Similarity	NPC116292
0.8848	High Similarity	NPC177362
0.8831	High Similarity	NPC469615
0.8797	High Similarity	NPC243891
0.8795	High Similarity	NPC21956
0.8774	High Similarity	NPC469683
0.8758	High Similarity	NPC471405
0.875	High Similarity	NPC191046
0.875	High Similarity	NPC194095
0.875	High Similarity	NPC327032
0.8743	High Similarity	NPC475299
0.8743	High Similarity	NPC472803
0.8727	High Similarity	NPC475738
0.8727	High Similarity	NPC474301
0.872	High Similarity	NPC41009
0.8704	High Similarity	NPC4747
0.8704	High Similarity	NPC472860
0.8704	High Similarity	NPC104275
0.8696	High Similarity	NPC10205
0.869	High Similarity	NPC469773
0.869	High Similarity	NPC469776
0.869	High Similarity	NPC148185
0.869	High Similarity	NPC469777
0.869	High Similarity	NPC469778
0.869	High Similarity	NPC135334
0.869	High Similarity	NPC469774
0.869	High Similarity	NPC469772
0.869	High Similarity	NPC32723
0.869	High Similarity	NPC100925
0.869	High Similarity	NPC469775
0.869	High Similarity	NPC295941
0.8688	High Similarity	NPC61604
0.8688	High Similarity	NPC245615
0.8688	High Similarity	NPC299706
0.8688	High Similarity	NPC115466
0.8671	High Similarity	NPC96194
0.8671	High Similarity	NPC299855
0.8667	High Similarity	NPC100425
0.8659	High Similarity	NPC477627
0.865	High Similarity	NPC76211
0.865	High Similarity	NPC179914
0.8625	High Similarity	NPC36130
0.8625	High Similarity	NPC134905
0.8621	High Similarity	NPC189704
0.8614	High Similarity	NPC180586
0.8606	High Similarity	NPC476011
0.8606	High Similarity	NPC145847
0.8599	High Similarity	NPC320734
0.8599	High Similarity	NPC258856
0.8598	High Similarity	NPC239966
0.8598	High Similarity	NPC203020
0.8596	High Similarity	NPC80360
0.8596	High Similarity	NPC469418
0.8596	High Similarity	NPC260300
0.859	High Similarity	NPC46880
0.8589	High Similarity	NPC133984
0.8589	High Similarity	NPC187205
0.858	High Similarity	NPC156624
0.858	High Similarity	NPC38699
0.858	High Similarity	NPC172920
0.8571	High Similarity	NPC476067
0.8571	High Similarity	NPC137813
0.8571	High Similarity	NPC157898
0.8571	High Similarity	NPC44730
0.8571	High Similarity	NPC475121
0.8563	High Similarity	NPC469419
0.8555	High Similarity	NPC473205
0.8555	High Similarity	NPC473776
0.8554	High Similarity	NPC45943
0.8554	High Similarity	NPC109990
0.8554	High Similarity	NPC120012
0.8553	High Similarity	NPC478242
0.8547	High Similarity	NPC195114
0.8547	High Similarity	NPC108191
0.8547	High Similarity	NPC93685
0.8545	High Similarity	NPC469889
0.8544	High Similarity	NPC24257
0.8544	High Similarity	NPC153620
0.8538	High Similarity	NPC473713
0.8538	High Similarity	NPC79736
0.8538	High Similarity	NPC67629
0.8537	High Similarity	NPC160780
0.8537	High Similarity	NPC469384
0.8537	High Similarity	NPC289811
0.8528	High Similarity	NPC109765
0.8528	High Similarity	NPC163635
0.8528	High Similarity	NPC228357
0.8512	High Similarity	NPC311912
0.8509	High Similarity	NPC478268
0.8509	High Similarity	NPC203664
0.85	High Similarity	NPC158635
0.85	High Similarity	NPC12854
0.85	High Similarity	NPC237441
0.85	High Similarity	NPC205054
0.85	High Similarity	NPC229882
0.8494	Intermediate Similarity	NPC76687
0.8494	Intermediate Similarity	NPC246024
0.8491	Intermediate Similarity	NPC472969
0.8488	Intermediate Similarity	NPC267549
0.8485	Intermediate Similarity	NPC239818
0.8485	Intermediate Similarity	NPC474936
0.8485	Intermediate Similarity	NPC218471
0.8483	Intermediate Similarity	NPC476358
0.8481	Intermediate Similarity	NPC473867
0.8481	Intermediate Similarity	NPC75295
0.848	Intermediate Similarity	NPC193377
0.8476	Intermediate Similarity	NPC202495
0.8476	Intermediate Similarity	NPC286919
0.8476	Intermediate Similarity	NPC1913
0.8476	Intermediate Similarity	NPC475663
0.8462	Intermediate Similarity	NPC88557
0.8457	Intermediate Similarity	NPC131121
0.8457	Intermediate Similarity	NPC308555
0.8452	Intermediate Similarity	NPC469458
0.8452	Intermediate Similarity	NPC88176
0.8452	Intermediate Similarity	NPC130730
0.8452	Intermediate Similarity	NPC469396
0.8452	Intermediate Similarity	NPC301910
0.8452	Intermediate Similarity	NPC469459
0.8452	Intermediate Similarity	NPC149002
0.8447	Intermediate Similarity	NPC118033
0.8438	Intermediate Similarity	NPC476394
0.8438	Intermediate Similarity	NPC98809
0.8438	Intermediate Similarity	NPC111785
0.8434	Intermediate Similarity	NPC266365
0.8434	Intermediate Similarity	NPC293568
0.8434	Intermediate Similarity	NPC117943
0.8434	Intermediate Similarity	NPC472859
0.8434	Intermediate Similarity	NPC216916
0.8434	Intermediate Similarity	NPC311803
0.8434	Intermediate Similarity	NPC25389
0.843	Intermediate Similarity	NPC196771
0.8421	Intermediate Similarity	NPC195972
0.8418	Intermediate Similarity	NPC230670
0.8418	Intermediate Similarity	NPC71385
0.8415	Intermediate Similarity	NPC471968
0.8415	Intermediate Similarity	NPC478055
0.8412	Intermediate Similarity	NPC180768
0.8405	Intermediate Similarity	NPC305710
0.8405	Intermediate Similarity	NPC469888
0.8402	Intermediate Similarity	NPC298847
0.8397	Intermediate Similarity	NPC28398
0.8395	Intermediate Similarity	NPC289438
0.8395	Intermediate Similarity	NPC475579
0.8395	Intermediate Similarity	NPC476434
0.8395	Intermediate Similarity	NPC473773
0.8391	Intermediate Similarity	NPC170203
0.8391	Intermediate Similarity	NPC102367
0.8385	Intermediate Similarity	NPC327962
0.8385	Intermediate Similarity	NPC474305
0.8385	Intermediate Similarity	NPC261322
0.8383	Intermediate Similarity	NPC148273
0.8383	Intermediate Similarity	NPC285108
0.8383	Intermediate Similarity	NPC22130
0.8383	Intermediate Similarity	NPC116838
0.8383	Intermediate Similarity	NPC33298
0.8383	Intermediate Similarity	NPC22324
0.8375	Intermediate Similarity	NPC470757
0.8373	Intermediate Similarity	NPC268718
0.8373	Intermediate Similarity	NPC21046
0.8373	Intermediate Similarity	NPC166277
0.8373	Intermediate Similarity	NPC91634
0.8373	Intermediate Similarity	NPC119125
0.8373	Intermediate Similarity	NPC150943
0.8372	Intermediate Similarity	NPC473630
0.8371	Intermediate Similarity	NPC112708
0.8364	Intermediate Similarity	NPC143328
0.8363	Intermediate Similarity	NPC471181
0.8363	Intermediate Similarity	NPC477617
0.8354	Intermediate Similarity	NPC131532
0.8354	Intermediate Similarity	NPC300757
0.8354	Intermediate Similarity	NPC254163
0.8354	Intermediate Similarity	NPC475484
0.8354	Intermediate Similarity	NPC473090
0.8354	Intermediate Similarity	NPC180901
0.8353	Intermediate Similarity	NPC658
0.8353	Intermediate Similarity	NPC117911
0.8353	Intermediate Similarity	NPC197708
0.8344	Intermediate Similarity	NPC310661
0.8344	Intermediate Similarity	NPC105827

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 NPC100420 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	820
0.2-0.3	1638
0.3-0.4	2520
0.4-0.5	2185
0.5-0.6	1098
0.6-0.7	474
0.7-0.8	108
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8547	High Similarity	NPD8055	Clinical (unspecified phase)
0.8529	High Similarity	NPD7685	Pre-registration
0.8424	Intermediate Similarity	NPD6234	Discontinued
0.8302	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD3818	Discontinued
0.8294	Intermediate Similarity	NPD7228	Approved
0.8232	Intermediate Similarity	NPD37	Approved
0.8193	Intermediate Similarity	NPD4966	Approved
0.8193	Intermediate Similarity	NPD4967	Phase 2
0.8193	Intermediate Similarity	NPD4965	Approved
0.8113	Intermediate Similarity	NPD4628	Phase 3
0.8037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8127	Discontinued
0.8	Intermediate Similarity	NPD8166	Discontinued
0.7989	Intermediate Similarity	NPD7074	Phase 3
0.7976	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7458	Discontinued
0.7931	Intermediate Similarity	NPD7054	Approved
0.7919	Intermediate Similarity	NPD7473	Discontinued
0.7886	Intermediate Similarity	NPD7472	Approved
0.7877	Intermediate Similarity	NPD8434	Phase 2
0.7853	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6232	Discontinued
0.7812	Intermediate Similarity	NPD7266	Discontinued
0.7809	Intermediate Similarity	NPD8313	Approved
0.7809	Intermediate Similarity	NPD8312	Approved
0.7802	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7240	Approved
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7784	Intermediate Similarity	NPD7028	Phase 2
0.7753	Intermediate Similarity	NPD7808	Phase 3
0.7727	Intermediate Similarity	NPD5844	Phase 1
0.7701	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD1934	Approved
0.7661	Intermediate Similarity	NPD3882	Suspended
0.7647	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1465	Phase 2
0.764	Intermediate Similarity	NPD6797	Phase 2
0.7622	Intermediate Similarity	NPD6190	Approved
0.7616	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD230	Phase 1
0.7569	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD9494	Approved
0.7561	Intermediate Similarity	NPD4110	Phase 3
0.7561	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6273	Approved
0.7544	Intermediate Similarity	NPD2801	Approved
0.7544	Intermediate Similarity	NPD7819	Suspended
0.7542	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5494	Approved
0.7528	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7487	Intermediate Similarity	NPD7680	Approved
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.746	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6166	Phase 2
0.7458	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1653	Approved
0.7442	Intermediate Similarity	NPD8455	Phase 2
0.7427	Intermediate Similarity	NPD6386	Approved
0.7427	Intermediate Similarity	NPD6385	Approved
0.7421	Intermediate Similarity	NPD3764	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7799	Discontinued
0.7368	Intermediate Similarity	NPD4380	Phase 2
0.7358	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3620	Phase 2
0.731	Intermediate Similarity	NPD3226	Approved
0.7306	Intermediate Similarity	NPD7435	Discontinued
0.7297	Intermediate Similarity	NPD8150	Discontinued
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD3705	Approved
0.7289	Intermediate Similarity	NPD6674	Discontinued
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7246	Intermediate Similarity	NPD7003	Approved
0.7231	Intermediate Similarity	NPD7999	Approved
0.7229	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1511	Approved
0.7212	Intermediate Similarity	NPD2935	Discontinued
0.72	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5353	Approved
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8407	Phase 2
0.7184	Intermediate Similarity	NPD6801	Discontinued
0.7178	Intermediate Similarity	NPD6355	Discontinued
0.7172	Intermediate Similarity	NPD7874	Approved
0.7172	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6663	Approved
0.716	Intermediate Similarity	NPD8032	Phase 2
0.715	Intermediate Similarity	NPD6778	Approved
0.715	Intermediate Similarity	NPD6782	Approved
0.715	Intermediate Similarity	NPD6777	Approved
0.715	Intermediate Similarity	NPD6776	Approved
0.715	Intermediate Similarity	NPD6781	Approved
0.715	Intermediate Similarity	NPD6779	Approved
0.715	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7783	Phase 2
0.7135	Intermediate Similarity	NPD1512	Approved
0.7134	Intermediate Similarity	NPD1608	Approved
0.7128	Intermediate Similarity	NPD7696	Phase 3
0.7128	Intermediate Similarity	NPD7698	Approved
0.7128	Intermediate Similarity	NPD7697	Approved
0.7126	Intermediate Similarity	NPD6873	Phase 2
0.7125	Intermediate Similarity	NPD5736	Approved
0.712	Intermediate Similarity	NPD6764	Approved
0.712	Intermediate Similarity	NPD8368	Discontinued
0.712	Intermediate Similarity	NPD6765	Approved
0.7114	Intermediate Similarity	NPD7930	Approved
0.7111	Intermediate Similarity	NPD5242	Approved
0.7108	Intermediate Similarity	NPD2438	Suspended
0.7097	Intermediate Similarity	NPD1357	Approved
0.7092	Intermediate Similarity	NPD8319	Approved
0.7092	Intermediate Similarity	NPD8320	Phase 1
0.7092	Intermediate Similarity	NPD7870	Phase 2
0.7092	Intermediate Similarity	NPD7871	Phase 2
0.7091	Intermediate Similarity	NPD7097	Phase 1
0.7076	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD447	Suspended
0.7071	Intermediate Similarity	NPD7701	Phase 2
0.7066	Intermediate Similarity	NPD2346	Discontinued
0.7062	Intermediate Similarity	NPD7768	Phase 2
0.705	Intermediate Similarity	NPD7801	Approved
0.7048	Intermediate Similarity	NPD2799	Discontinued
0.7044	Intermediate Similarity	NPD8404	Phase 2
0.7044	Intermediate Similarity	NPD1283	Approved
0.7037	Intermediate Similarity	NPD7095	Approved
0.7029	Intermediate Similarity	NPD7411	Suspended
0.7027	Intermediate Similarity	NPD7039	Approved
0.7027	Intermediate Similarity	NPD7038	Approved
0.7025	Intermediate Similarity	NPD3972	Approved
0.7018	Intermediate Similarity	NPD6799	Approved
0.7012	Intermediate Similarity	NPD2979	Phase 3
0.7012	Intermediate Similarity	NPD4060	Phase 1
0.7012	Intermediate Similarity	NPD4140	Approved
0.7011	Intermediate Similarity	NPD3455	Phase 2
0.7011	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5402	Approved
0.7006	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD6959	Discontinued
0.6995	Remote Similarity	NPD3751	Discontinued
0.699	Remote Similarity	NPD6823	Phase 2
0.6983	Remote Similarity	NPD919	Approved
0.6983	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2800	Approved
0.6978	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1933	Approved
0.6968	Remote Similarity	NPD6785	Approved
0.6968	Remote Similarity	NPD6784	Approved
0.6964	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5762	Approved
0.6964	Remote Similarity	NPD5763	Approved
0.6961	Remote Similarity	NPD5710	Approved
0.6961	Remote Similarity	NPD7229	Phase 3
0.6961	Remote Similarity	NPD5711	Approved
0.6959	Remote Similarity	NPD7699	Phase 2
0.6959	Remote Similarity	NPD7700	Phase 2
0.6959	Remote Similarity	NPD7236	Approved
0.6954	Remote Similarity	NPD7497	Discontinued
0.6952	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1510	Phase 2
0.6943	Remote Similarity	NPD17	Approved
0.6941	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD3926	Phase 2
0.6923	Remote Similarity	NPD1549	Phase 2
0.6918	Remote Similarity	NPD9269	Phase 2
0.6911	Remote Similarity	NPD2488	Approved
0.6911	Remote Similarity	NPD2490	Approved
0.6909	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7907	Approved
0.6904	Remote Similarity	NPD2491	Approved
0.6904	Remote Similarity	NPD3057	Approved
0.6891	Remote Similarity	NPD6534	Approved
0.6891	Remote Similarity	NPD6535	Approved
0.689	Remote Similarity	NPD6798	Discontinued
0.689	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4107	Approved
0.6875	Remote Similarity	NPD7296	Approved
0.6872	Remote Similarity	NPD4420	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