NPASS Compound

Structure

NPC109990 OpenBabel07101719522D 47 51 0 0 1 0 0 0 0 0999 V2000 3.3412 -0.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 2.5981 4.5000 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 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 2.5981 -2.5000 0.0000 C 0 0 2 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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 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 2.0000 0.0000 C 0 0 1 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 1.7321 -4.0000 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 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2923 -0.5219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 2 0 0 0 0 3 15 1 0 0 0 0 4 6 1 0 0 0 0 4 16 2 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 11 32 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 13 44 1 0 0 0 0 14 43 1 0 0 0 0 16 29 1 0 0 0 0 17 33 1 0 0 0 0 18 10 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 28 1 0 0 0 0 20 21 2 0 0 0 0 20 34 1 0 0 0 0 21 35 1 0 0 0 0 22 14 1 6 0 0 0 22 25 1 0 0 0 0 22 45 1 0 0 0 0 23 36 2 0 0 0 0 23 43 1 0 0 0 0 24 30 1 0 0 0 0 24 32 1 6 0 0 0 25 26 1 0 0 0 0 25 37 1 1 0 0 0 26 27 1 0 0 0 0 26 38 1 6 0 0 0 27 31 1 0 0 0 0 27 46 1 1 0 0 0 28 39 2 0 0 0 0 28 40 1 0 0 0 0 29 41 2 0 0 0 0 29 46 1 0 0 0 0 30 44 1 0 0 0 0 30 47 1 1 0 0 0 31 45 1 0 0 0 0 31 47 1 6 0 0 0 32 1 1 6 0 0 0 32 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	658.19
Volume:	622.098
LogP:	2.554
LogD:	1.251
LogS:	-3.046
# Rotatable Bonds:	11
TPSA:	238.97
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	4.913
Fsp3:	0.406
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.271
MDCK Permeability:	4.70119048259221e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.878
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	97.38640594482422%
Volume Distribution (VD):	0.389
Pgp-substrate:	5.04600715637207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.388
CYP2C9-substrate:	0.107
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	3.149
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.173
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.627
Carcinogencity:	0.705
Eye Corrosion:	0.003
Eye Irritation:	0.058
Respiratory Toxicity:	0.619

Download Data

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

Natural Product: NPC109990

Natural Product ID:	NPC109990
*Common Name:**	6'-O-Trans-Caffeoylnegundoside
IUPAC Name:	(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
Synonyms:
Standard InCHIKey:	LZVBQYSONKTXFG-XYYTZZQVSA-N
Standard InCHI:	InChI=1S/C32H34O15/c1-32(42)11-10-18-19(28(39)40)13-44-30(24(18)32)47-31-27(46-29(41)16-4-6-17(33)7-5-16)26(38)25(37)22(45-31)14-43-23(36)9-3-15-2-8-20(34)21(35)12-15/h2-9,12-13,18,22,24-27,30-31,33-35,37-38,42H,10-11,14H2,1H3,(H,39,40)/b9-3+/t18-,22-,24-,25-,26+,27-,30+,31+,32+/m1/s1
SMILES:	C[C@@]1(CC[C@@H]2C(=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)O)O)O1)O)O)OC(=O)c1ccc(cc1)O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464100
PubChem CID:	11181364
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO6184	Vitex altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620243]
NPO6184	Vitex altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6184	Vitex altissima	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
IC50	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24300.0	nM	PMID[473884]
NPT1	Others	Radical scavenging activity		IC50	=	15200.0	nM	PMID[473884]

☑ 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 NPC109990 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	343
0.1-0.2	1313
0.2-0.3	2758
0.3-0.4	5792
0.4-0.5	10419
0.5-0.6	7921
0.6-0.7	8667
0.7-0.8	5046
0.8-0.85	368
0.85-0.9	58
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC145847
0.9747	High Similarity	NPC21956
0.9675	High Similarity	NPC187205
0.9295	High Similarity	NPC475484
0.9286	High Similarity	NPC289021
0.9286	High Similarity	NPC158546
0.9241	High Similarity	NPC179914
0.9187	High Similarity	NPC476011
0.9182	High Similarity	NPC138993
0.9062	High Similarity	NPC474936
0.9032	High Similarity	NPC478236
0.9032	High Similarity	NPC478234
0.9018	High Similarity	NPC130730
0.9018	High Similarity	NPC301910
0.8974	High Similarity	NPC117346
0.8974	High Similarity	NPC240592
0.8938	High Similarity	NPC226759
0.891	High Similarity	NPC96599
0.8902	High Similarity	NPC282551
0.8861	High Similarity	NPC478235
0.8861	High Similarity	NPC194705
0.8854	High Similarity	NPC69367
0.8834	High Similarity	NPC206815
0.8831	High Similarity	NPC296659
0.8831	High Similarity	NPC202391
0.8805	High Similarity	NPC229354
0.875	High Similarity	NPC316539
0.8718	High Similarity	NPC473867
0.8712	High Similarity	NPC478265
0.871	High Similarity	NPC473281
0.871	High Similarity	NPC251062
0.871	High Similarity	NPC184464
0.871	High Similarity	NPC77922
0.8704	High Similarity	NPC4747
0.8704	High Similarity	NPC49173
0.8704	High Similarity	NPC104275
0.8696	High Similarity	NPC156624
0.8696	High Similarity	NPC172920
0.869	High Similarity	NPC470685
0.8688	High Similarity	NPC157898
0.8679	High Similarity	NPC475379
0.8679	High Similarity	NPC140151
0.8679	High Similarity	NPC478249
0.8679	High Similarity	NPC269914
0.865	High Similarity	NPC469384
0.8645	High Similarity	NPC186296
0.8645	High Similarity	NPC478250
0.8642	High Similarity	NPC471405
0.8636	High Similarity	NPC475299
0.8634	High Similarity	NPC194095
0.8634	High Similarity	NPC478232
0.8634	High Similarity	NPC191046
0.8634	High Similarity	NPC327032
0.8625	High Similarity	NPC203664
0.8623	High Similarity	NPC208818
0.8616	High Similarity	NPC35097
0.8614	High Similarity	NPC180586
0.8598	High Similarity	NPC208676
0.8598	High Similarity	NPC130489
0.8589	High Similarity	NPC475663
0.8589	High Similarity	NPC133984
0.8589	High Similarity	NPC472860
0.8589	High Similarity	NPC286919
0.8588	High Similarity	NPC171706
0.8581	High Similarity	NPC296643
0.858	High Similarity	NPC203757
0.858	High Similarity	NPC10205
0.8571	High Similarity	NPC257847
0.8563	High Similarity	NPC299855
0.8563	High Similarity	NPC96194
0.8554	High Similarity	NPC100420
0.8553	High Similarity	NPC92117
0.8553	High Similarity	NPC161955
0.8544	High Similarity	NPC473149
0.8544	High Similarity	NPC18789
0.8528	High Similarity	NPC475378
0.8528	High Similarity	NPC478248
0.8519	High Similarity	NPC472128
0.8519	High Similarity	NPC472127
0.8516	High Similarity	NPC159387
0.8516	High Similarity	NPC154262
0.8516	High Similarity	NPC7518
0.8516	High Similarity	NPC137501
0.8514	High Similarity	NPC189704
0.8509	High Similarity	NPC267091
0.8509	High Similarity	NPC478268
0.8509	High Similarity	NPC134905
0.8509	High Similarity	NPC106818
0.8509	High Similarity	NPC36130
0.8503	High Similarity	NPC475738
0.85	High Similarity	NPC147224
0.8497	Intermediate Similarity	NPC188217
0.8494	Intermediate Similarity	NPC246024
0.8491	Intermediate Similarity	NPC23677
0.8491	Intermediate Similarity	NPC248257
0.8491	Intermediate Similarity	NPC473138
0.8491	Intermediate Similarity	NPC120621
0.8491	Intermediate Similarity	NPC28776
0.8491	Intermediate Similarity	NPC308178
0.8491	Intermediate Similarity	NPC120728
0.8488	Intermediate Similarity	NPC469418
0.8488	Intermediate Similarity	NPC80360
0.8488	Intermediate Similarity	NPC260300
0.8485	Intermediate Similarity	NPC239966
0.8485	Intermediate Similarity	NPC203020
0.848	Intermediate Similarity	NPC469354
0.8471	Intermediate Similarity	NPC141455
0.8471	Intermediate Similarity	NPC300894
0.8471	Intermediate Similarity	NPC196063
0.8471	Intermediate Similarity	NPC296954
0.8466	Intermediate Similarity	NPC131532
0.8466	Intermediate Similarity	NPC476067
0.8466	Intermediate Similarity	NPC38699
0.8466	Intermediate Similarity	NPC475121
0.8462	Intermediate Similarity	NPC202428
0.8462	Intermediate Similarity	NPC266545
0.8457	Intermediate Similarity	NPC229548
0.8457	Intermediate Similarity	NPC3746
0.8457	Intermediate Similarity	NPC299706
0.8457	Intermediate Similarity	NPC205037
0.8457	Intermediate Similarity	NPC16024
0.8457	Intermediate Similarity	NPC44260
0.8457	Intermediate Similarity	NPC115466
0.8457	Intermediate Similarity	NPC137813
0.8457	Intermediate Similarity	NPC478241
0.8457	Intermediate Similarity	NPC89693
0.8457	Intermediate Similarity	NPC61604
0.8457	Intermediate Similarity	NPC245615
0.8457	Intermediate Similarity	NPC61152
0.8457	Intermediate Similarity	NPC87403
0.8452	Intermediate Similarity	NPC469458
0.8452	Intermediate Similarity	NPC88176
0.8452	Intermediate Similarity	NPC469419
0.8452	Intermediate Similarity	NPC469396
0.8452	Intermediate Similarity	NPC469459
0.8452	Intermediate Similarity	NPC149002
0.8448	Intermediate Similarity	NPC473776
0.8448	Intermediate Similarity	NPC473205
0.8447	Intermediate Similarity	NPC243891
0.8447	Intermediate Similarity	NPC474620
0.8442	Intermediate Similarity	NPC84789
0.8442	Intermediate Similarity	NPC302583
0.8442	Intermediate Similarity	NPC100558
0.8442	Intermediate Similarity	NPC310252
0.8439	Intermediate Similarity	NPC198902
0.8439	Intermediate Similarity	NPC195114
0.8438	Intermediate Similarity	NPC75945
0.8438	Intermediate Similarity	NPC478242
0.8438	Intermediate Similarity	NPC111785
0.843	Intermediate Similarity	NPC469397
0.843	Intermediate Similarity	NPC67629
0.843	Intermediate Similarity	NPC79736
0.8424	Intermediate Similarity	NPC160780
0.8424	Intermediate Similarity	NPC289811
0.8421	Intermediate Similarity	NPC195972
0.8415	Intermediate Similarity	NPC478266
0.8415	Intermediate Similarity	NPC163635
0.8408	Intermediate Similarity	NPC293154
0.8408	Intermediate Similarity	NPC105005
0.8402	Intermediate Similarity	NPC286809
0.8402	Intermediate Similarity	NPC298847
0.8402	Intermediate Similarity	NPC177362
0.8397	Intermediate Similarity	NPC476385
0.8397	Intermediate Similarity	NPC476377
0.8397	Intermediate Similarity	NPC134405
0.8397	Intermediate Similarity	NPC47471
0.8391	Intermediate Similarity	NPC102367
0.8387	Intermediate Similarity	NPC64141
0.8387	Intermediate Similarity	NPC321638
0.8387	Intermediate Similarity	NPC328273
0.8387	Intermediate Similarity	NPC197316
0.8387	Intermediate Similarity	NPC321184
0.8387	Intermediate Similarity	NPC68092
0.8387	Intermediate Similarity	NPC476383
0.8387	Intermediate Similarity	NPC81515
0.8387	Intermediate Similarity	NPC89105
0.8387	Intermediate Similarity	NPC171134
0.8387	Intermediate Similarity	NPC472350
0.8385	Intermediate Similarity	NPC470934
0.8385	Intermediate Similarity	NPC188393
0.8383	Intermediate Similarity	NPC291957
0.8383	Intermediate Similarity	NPC41009
0.8383	Intermediate Similarity	NPC148273
0.8383	Intermediate Similarity	NPC285108
0.8383	Intermediate Similarity	NPC14030
0.8383	Intermediate Similarity	NPC33298
0.8382	Intermediate Similarity	NPC267549
0.8377	Intermediate Similarity	NPC471345
0.8373	Intermediate Similarity	NPC289346
0.8372	Intermediate Similarity	NPC469438
0.8372	Intermediate Similarity	NPC169645
0.8372	Intermediate Similarity	NPC84482
0.8365	Intermediate Similarity	NPC119773
0.8365	Intermediate Similarity	NPC143246
0.8365	Intermediate Similarity	NPC474268
0.8365	Intermediate Similarity	NPC229505
0.8365	Intermediate Similarity	NPC475539
0.8364	Intermediate Similarity	NPC238419
0.8364	Intermediate Similarity	NPC329997
0.8364	Intermediate Similarity	NPC1913

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 NPC109990 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	775
0.2-0.3	1640
0.3-0.4	2628
0.4-0.5	2223
0.5-0.6	1167
0.6-0.7	354
0.7-0.8	70
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9325	High Similarity	NPD7685	Pre-registration
0.8387	Intermediate Similarity	NPD7266	Discontinued
0.8333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD7472	Approved
0.8092	Intermediate Similarity	NPD7074	Phase 3
0.8081	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7976	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7808	Phase 3
0.795	Intermediate Similarity	NPD6190	Approved
0.7943	Intermediate Similarity	NPD6797	Phase 2
0.7929	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7228	Approved
0.7853	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7727	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6234	Discontinued
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8312	Approved
0.7611	Intermediate Similarity	NPD8313	Approved
0.761	Intermediate Similarity	NPD230	Phase 1
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD37	Approved
0.7588	Intermediate Similarity	NPD1934	Approved
0.7586	Intermediate Similarity	NPD8127	Discontinued
0.7574	Intermediate Similarity	NPD4380	Phase 2
0.7571	Intermediate Similarity	NPD7799	Discontinued
0.7558	Intermediate Similarity	NPD4965	Approved
0.7558	Intermediate Similarity	NPD4966	Approved
0.7558	Intermediate Similarity	NPD4967	Phase 2
0.7557	Intermediate Similarity	NPD6166	Phase 2
0.7557	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8455	Phase 2
0.7528	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7456	Intermediate Similarity	NPD1653	Approved
0.7455	Intermediate Similarity	NPD8166	Discontinued
0.7442	Intermediate Similarity	NPD1465	Phase 2
0.744	Intermediate Similarity	NPD6273	Approved
0.7414	Intermediate Similarity	NPD7075	Discontinued
0.7412	Intermediate Similarity	NPD7458	Discontinued
0.7403	Intermediate Similarity	NPD7240	Approved
0.7399	Intermediate Similarity	NPD3817	Phase 2
0.7391	Intermediate Similarity	NPD8150	Discontinued
0.7368	Intermediate Similarity	NPD7028	Phase 2
0.7341	Intermediate Similarity	NPD7819	Suspended
0.7341	Intermediate Similarity	NPD2801	Approved
0.7318	Intermediate Similarity	NPD7473	Discontinued
0.7312	Intermediate Similarity	NPD3764	Approved
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8320	Phase 1
0.7268	Intermediate Similarity	NPD8319	Approved
0.7262	Intermediate Similarity	NPD7236	Approved
0.7257	Intermediate Similarity	NPD3882	Suspended
0.7247	Intermediate Similarity	NPD6232	Discontinued
0.7241	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5494	Approved
0.7219	Intermediate Similarity	NPD1511	Approved
0.7216	Intermediate Similarity	NPD7435	Discontinued
0.7204	Intermediate Similarity	NPD8434	Phase 2
0.72	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7930	Approved
0.7184	Intermediate Similarity	NPD6801	Discontinued
0.717	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7239	Suspended
0.7143	Intermediate Similarity	NPD7999	Approved
0.7143	Intermediate Similarity	NPD9545	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7135	Intermediate Similarity	NPD1512	Approved
0.7134	Intermediate Similarity	NPD6653	Approved
0.7128	Intermediate Similarity	NPD7680	Approved
0.7121	Intermediate Similarity	NPD8151	Discontinued
0.7117	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3455	Phase 2
0.7102	Intermediate Similarity	NPD5402	Approved
0.7098	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7874	Approved
0.7085	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7068	Intermediate Similarity	NPD6534	Approved
0.7068	Intermediate Similarity	NPD6535	Approved
0.7062	Intermediate Similarity	NPD6782	Approved
0.7062	Intermediate Similarity	NPD6781	Approved
0.7062	Intermediate Similarity	NPD6780	Approved
0.7062	Intermediate Similarity	NPD6779	Approved
0.7062	Intermediate Similarity	NPD6778	Approved
0.7062	Intermediate Similarity	NPD6777	Approved
0.7062	Intermediate Similarity	NPD6776	Approved
0.7055	Intermediate Similarity	NPD6663	Approved
0.705	Intermediate Similarity	NPD7783	Phase 2
0.705	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7033	Discontinued
0.7041	Intermediate Similarity	NPD7696	Phase 3
0.7041	Intermediate Similarity	NPD3750	Approved
0.7041	Intermediate Similarity	NPD7698	Approved
0.7041	Intermediate Similarity	NPD7497	Discontinued
0.7041	Intermediate Similarity	NPD7697	Approved
0.7037	Intermediate Similarity	NPD3027	Phase 3
0.7029	Intermediate Similarity	NPD7411	Suspended
0.7029	Intermediate Similarity	NPD6386	Approved
0.7029	Intermediate Similarity	NPD6385	Approved
0.7024	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD9494	Approved
0.7019	Intermediate Similarity	NPD5736	Approved
0.7006	Intermediate Similarity	NPD2935	Discontinued
0.7005	Intermediate Similarity	NPD7871	Phase 2
0.7005	Intermediate Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD3751	Discontinued
0.6994	Remote Similarity	NPD5403	Approved
0.6985	Remote Similarity	NPD7585	Approved
0.6985	Remote Similarity	NPD7701	Phase 2
0.6982	Remote Similarity	NPD6674	Discontinued
0.6978	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7768	Phase 2
0.6965	Remote Similarity	NPD7801	Approved
0.6964	Remote Similarity	NPD5762	Approved
0.6964	Remote Similarity	NPD5763	Approved
0.6949	Remote Similarity	NPD5761	Phase 2
0.6949	Remote Similarity	NPD5760	Phase 2
0.6946	Remote Similarity	NPD1510	Phase 2
0.6941	Remote Similarity	NPD4110	Phase 3
0.6941	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7583	Approved
0.6923	Remote Similarity	NPD1549	Phase 2
0.6919	Remote Similarity	NPD6799	Approved
0.6918	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD9269	Phase 2
0.6915	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5353	Approved
0.6909	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1613	Approved
0.6909	Remote Similarity	NPD943	Approved
0.6909	Remote Similarity	NPD3620	Phase 2
0.6909	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6823	Phase 2
0.6886	Remote Similarity	NPD7097	Phase 1
0.6879	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5401	Approved
0.6875	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6599	Discontinued
0.6868	Remote Similarity	NPD3787	Discontinued
0.6867	Remote Similarity	NPD1933	Approved
0.6864	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6004	Phase 3
0.6864	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6005	Phase 3
0.6864	Remote Similarity	NPD6002	Phase 3
0.685	Remote Similarity	NPD7584	Approved
0.6845	Remote Similarity	NPD6765	Approved
0.6845	Remote Similarity	NPD6764	Approved
0.6842	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6213	Phase 3
0.6839	Remote Similarity	NPD6212	Phase 3
0.6833	Remote Similarity	NPD3749	Approved
0.6831	Remote Similarity	NPD5242	Approved
0.6829	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6959	Discontinued
0.681	Remote Similarity	NPD2861	Phase 2
0.6805	Remote Similarity	NPD2796	Approved
0.6788	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2532	Approved
0.6782	Remote Similarity	NPD2534	Approved
0.6782	Remote Similarity	NPD2533	Approved
0.6778	Remote Similarity	NPD7057	Phase 3
0.6778	Remote Similarity	NPD7058	Phase 2
0.6755	Remote Similarity	NPD8368	Discontinued
0.6755	Remote Similarity	NPD7038	Approved
0.6755	Remote Similarity	NPD7039	Approved
0.6748	Remote Similarity	NPD2798	Approved
0.6748	Remote Similarity	NPD5647	Approved
0.6747	Remote Similarity	NPD6233	Phase 2
0.6746	Remote Similarity	NPD3748	Approved
0.6746	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD8407	Phase 2
0.673	Remote Similarity	NPD17	Approved
0.6728	Remote Similarity	NPD1876	Approved
0.6727	Remote Similarity	NPD7095	Approved
0.6723	Remote Similarity	NPD3226	Approved
0.6722	Remote Similarity	NPD5978	Approved
0.6722	Remote Similarity	NPD5977	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