NPASS Compound

Structure

NPC21956 OpenBabel07101719522D 48 52 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 -6.9282 2.0000 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 -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 -6.0622 1.5000 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 43 1 0 0 0 0 3 9 2 0 0 0 0 3 16 1 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 7 1 0 0 0 0 5 17 2 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 12 33 1 0 0 0 0 13 16 2 0 0 0 0 13 22 1 0 0 0 0 14 20 2 0 0 0 0 14 45 1 0 0 0 0 15 44 1 0 0 0 0 17 30 1 0 0 0 0 18 34 1 0 0 0 0 19 11 1 6 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 29 1 0 0 0 0 21 22 2 0 0 0 0 21 35 1 0 0 0 0 22 43 1 0 0 0 0 23 15 1 6 0 0 0 23 26 1 0 0 0 0 23 46 1 0 0 0 0 24 36 2 0 0 0 0 24 44 1 0 0 0 0 25 31 1 0 0 0 0 25 33 1 6 0 0 0 26 27 1 0 0 0 0 26 37 1 1 0 0 0 27 28 1 0 0 0 0 27 38 1 6 0 0 0 28 32 1 0 0 0 0 28 47 1 1 0 0 0 29 39 2 0 0 0 0 29 40 1 0 0 0 0 30 41 2 0 0 0 0 30 47 1 0 0 0 0 31 45 1 0 0 0 0 31 48 1 1 0 0 0 32 46 1 0 0 0 0 32 48 1 6 0 0 0 33 1 1 6 0 0 0 33 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	672.21
Volume:	639.394
LogP:	2.779
LogD:	1.691
LogS:	-3.257
# Rotatable Bonds:	12
TPSA:	227.97
# H-Bond Aceptor:	15
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.155
Synthetic Accessibility Score:	4.882
Fsp3:	0.424
Lipinski Rule-of-5:	Rejected
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:	-6.145
MDCK Permeability:	5.356038309400901e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	0.909
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	97.07369232177734%
Volume Distribution (VD):	0.401
Pgp-substrate:	6.574164390563965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.422
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	2.943
Half-life (T1/2):	0.943

ADMET: Toxicity

hERG Blockers:	0.219
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.896
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.524
Carcinogencity:	0.772
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.781

Download Data

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

Natural Product: NPC21956

Natural Product ID:	NPC21956
*Common Name:**	6'-O-Trans-Feruloylnegundoside
IUPAC Name:	(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
Synonyms:
Standard InCHIKey:	WNQDGXDEZSWXSE-PBAPIZBRSA-N
Standard InCHI:	InChI=1S/C33H36O15/c1-33(42)12-11-19-20(29(39)40)14-45-31(25(19)33)48-32-28(47-30(41)17-5-7-18(34)8-6-17)27(38)26(37)23(46-32)15-44-24(36)10-4-16-3-9-21(35)22(13-16)43-2/h3-10,13-14,19,23,25-28,31-32,34-35,37-38,42H,11-12,15H2,1-2H3,(H,39,40)/b10-4+/t19-,23-,25-,26-,27+,28-,31+,32+,33+/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)OC)O)O1)O)O)OC(=O)c1ccc(cc1)O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450385
PubChem CID:	11181450
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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	20.0	%	PMID[495013]

☑ 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 NPC21956 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	353
0.1-0.2	1403
0.2-0.3	2881
0.3-0.4	6267
0.4-0.5	10564
0.5-0.6	6862
0.6-0.7	7655
0.7-0.8	6066
0.8-0.85	551
0.85-0.9	80
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC109990
0.9684	High Similarity	NPC145847
0.9494	High Similarity	NPC179914
0.9437	High Similarity	NPC476011
0.943	High Similarity	NPC187205
0.9313	High Similarity	NPC474936
0.9264	High Similarity	NPC130730
0.9264	High Similarity	NPC301910
0.9187	High Similarity	NPC226759
0.9146	High Similarity	NPC282551
0.908	High Similarity	NPC206815
0.9062	High Similarity	NPC475484
0.9051	High Similarity	NPC158546
0.9051	High Similarity	NPC289021
0.8988	High Similarity	NPC316539
0.8957	High Similarity	NPC478265
0.8957	High Similarity	NPC138993
0.8931	High Similarity	NPC269914
0.8931	High Similarity	NPC478249
0.8929	High Similarity	NPC470685
0.8896	High Similarity	NPC469384
0.8889	High Similarity	NPC471405
0.8882	High Similarity	NPC191046
0.8882	High Similarity	NPC327032
0.8882	High Similarity	NPC194095
0.8875	High Similarity	NPC203664
0.8864	High Similarity	NPC475299
0.8862	High Similarity	NPC208818
0.8855	High Similarity	NPC180586
0.8834	High Similarity	NPC286919
0.8834	High Similarity	NPC472860
0.8834	High Similarity	NPC475663
0.8834	High Similarity	NPC133984
0.8827	High Similarity	NPC10205
0.882	High Similarity	NPC157898
0.8812	High Similarity	NPC475379
0.8805	High Similarity	NPC478234
0.8805	High Similarity	NPC478236
0.8795	High Similarity	NPC100420
0.8793	High Similarity	NPC299855
0.8793	High Similarity	NPC96194
0.8773	High Similarity	NPC478248
0.8765	High Similarity	NPC478232
0.8758	High Similarity	NPC478268
0.8758	High Similarity	NPC267091
0.8758	High Similarity	NPC36130
0.8758	High Similarity	NPC134905
0.875	High Similarity	NPC117346
0.875	High Similarity	NPC240592
0.875	High Similarity	NPC147224
0.8743	High Similarity	NPC475738
0.8743	High Similarity	NPC189704
0.8742	High Similarity	NPC308178
0.8735	High Similarity	NPC246024
0.8728	High Similarity	NPC188217
0.8727	High Similarity	NPC239966
0.8727	High Similarity	NPC203020
0.8713	High Similarity	NPC469354
0.8712	High Similarity	NPC38699
0.8712	High Similarity	NPC131532
0.8704	High Similarity	NPC89693
0.8704	High Similarity	NPC61604
0.8704	High Similarity	NPC229548
0.8704	High Similarity	NPC245615
0.8704	High Similarity	NPC299706
0.8704	High Similarity	NPC137813
0.8704	High Similarity	NPC478241
0.8704	High Similarity	NPC115466
0.8698	High Similarity	NPC266545
0.8698	High Similarity	NPC202428
0.8696	High Similarity	NPC243891
0.8693	High Similarity	NPC475121
0.8693	High Similarity	NPC476067
0.8688	High Similarity	NPC478242
0.8688	High Similarity	NPC111785
0.8688	High Similarity	NPC96599
0.8679	High Similarity	NPC473149
0.8678	High Similarity	NPC473776
0.8678	High Similarity	NPC473205
0.8667	High Similarity	NPC160780
0.8667	High Similarity	NPC289811
0.8663	High Similarity	NPC469397
0.8663	High Similarity	NPC79736
0.8663	High Similarity	NPC67629
0.8659	High Similarity	NPC163635
0.8659	High Similarity	NPC478266
0.8642	High Similarity	NPC478235
0.8642	High Similarity	NPC194705
0.8639	High Similarity	NPC177362
0.8639	High Similarity	NPC298847
0.8639	High Similarity	NPC286809
0.8634	High Similarity	NPC188393
0.8634	High Similarity	NPC69367
0.8634	High Similarity	NPC470934
0.8623	High Similarity	NPC33298
0.8623	High Similarity	NPC148273
0.8623	High Similarity	NPC41009
0.8623	High Similarity	NPC285108
0.8613	High Similarity	NPC267549
0.8608	High Similarity	NPC202391
0.8608	High Similarity	NPC296659
0.8606	High Similarity	NPC1913
0.8605	High Similarity	NPC169645
0.8605	High Similarity	NPC469438
0.8605	High Similarity	NPC84482
0.8596	High Similarity	NPC235575
0.8589	High Similarity	NPC229354
0.8589	High Similarity	NPC44730
0.8588	High Similarity	NPC197708
0.8588	High Similarity	NPC658
0.858	High Similarity	NPC200726
0.8571	High Similarity	NPC35924
0.8571	High Similarity	NPC199172
0.8571	High Similarity	NPC476394
0.8571	High Similarity	NPC100425
0.8571	High Similarity	NPC98809
0.8563	High Similarity	NPC25389
0.8563	High Similarity	NPC108191
0.8563	High Similarity	NPC93685
0.8563	High Similarity	NPC311803
0.8563	High Similarity	NPC472859
0.8554	High Similarity	NPC76211
0.8553	High Similarity	NPC34927
0.8553	High Similarity	NPC34587
0.8553	High Similarity	NPC476382
0.8553	High Similarity	NPC100998
0.8553	High Similarity	NPC252292
0.8547	High Similarity	NPC195972
0.8545	High Similarity	NPC11411
0.8539	High Similarity	NPC71385
0.8539	High Similarity	NPC230670
0.8538	High Similarity	NPC43434
0.8538	High Similarity	NPC472129
0.8537	High Similarity	NPC469888
0.8529	High Similarity	NPC229729
0.8519	High Similarity	NPC158635
0.8519	High Similarity	NPC205054
0.8519	High Similarity	NPC229882
0.8509	High Similarity	NPC472969
0.8503	High Similarity	NPC166277
0.8503	High Similarity	NPC289346
0.8503	High Similarity	NPC119125
0.85	High Similarity	NPC473867
0.8494	Intermediate Similarity	NPC49173
0.8494	Intermediate Similarity	NPC104275
0.8494	Intermediate Similarity	NPC4747
0.8492	Intermediate Similarity	NPC112708
0.8491	Intermediate Similarity	NPC473281
0.8491	Intermediate Similarity	NPC77922
0.8491	Intermediate Similarity	NPC110063
0.8491	Intermediate Similarity	NPC251062
0.8491	Intermediate Similarity	NPC184464
0.8488	Intermediate Similarity	NPC261254
0.8488	Intermediate Similarity	NPC5786
0.8488	Intermediate Similarity	NPC148185
0.8488	Intermediate Similarity	NPC102851
0.8485	Intermediate Similarity	NPC172920
0.8485	Intermediate Similarity	NPC156624
0.8481	Intermediate Similarity	NPC140502
0.848	Intermediate Similarity	NPC472133
0.8466	Intermediate Similarity	NPC140151
0.8462	Intermediate Similarity	NPC45943
0.8462	Intermediate Similarity	NPC227297
0.8457	Intermediate Similarity	NPC94871
0.8457	Intermediate Similarity	NPC476398
0.8457	Intermediate Similarity	NPC259347
0.8457	Intermediate Similarity	NPC473427
0.8457	Intermediate Similarity	NPC306890
0.8457	Intermediate Similarity	NPC471030
0.8457	Intermediate Similarity	NPC471062
0.8457	Intermediate Similarity	NPC470933
0.8457	Intermediate Similarity	NPC476386
0.8448	Intermediate Similarity	NPC473713
0.8448	Intermediate Similarity	NPC472723
0.8447	Intermediate Similarity	NPC232992
0.8444	Intermediate Similarity	NPC473711
0.8443	Intermediate Similarity	NPC478269
0.8443	Intermediate Similarity	NPC287872
0.8443	Intermediate Similarity	NPC74319
0.8443	Intermediate Similarity	NPC469654
0.8439	Intermediate Similarity	NPC175230
0.8439	Intermediate Similarity	NPC163165
0.8439	Intermediate Similarity	NPC172033
0.8439	Intermediate Similarity	NPC88560
0.8439	Intermediate Similarity	NPC472993
0.8438	Intermediate Similarity	NPC216819
0.8438	Intermediate Similarity	NPC262182
0.8438	Intermediate Similarity	NPC83743
0.8438	Intermediate Similarity	NPC287615
0.8434	Intermediate Similarity	NPC228357
0.8434	Intermediate Similarity	NPC478055
0.843	Intermediate Similarity	NPC51326
0.843	Intermediate Similarity	NPC212748
0.843	Intermediate Similarity	NPC231194
0.8428	Intermediate Similarity	NPC478250
0.8428	Intermediate Similarity	NPC186296
0.8421	Intermediate Similarity	NPC116745
0.8415	Intermediate Similarity	NPC289438
0.8412	Intermediate Similarity	NPC311830
0.8412	Intermediate Similarity	NPC22832

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 NPC21956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	804
0.2-0.3	1691
0.3-0.4	2577
0.4-0.5	2178
0.5-0.6	1085
0.6-0.7	405
0.7-0.8	99
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9571	High Similarity	NPD7685	Pre-registration
0.8563	High Similarity	NPD8055	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD7054	Approved
0.8324	Intermediate Similarity	NPD7074	Phase 3
0.8324	Intermediate Similarity	NPD7472	Approved
0.8314	Intermediate Similarity	NPD3818	Discontinued
0.8182	Intermediate Similarity	NPD7808	Phase 3
0.8182	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7266	Discontinued
0.8125	Intermediate Similarity	NPD7251	Discontinued
0.8107	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD7228	Approved
0.8098	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6797	Phase 2
0.8059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7199	Phase 2
0.7952	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6234	Discontinued
0.7853	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD1934	Approved
0.7824	Intermediate Similarity	NPD37	Approved
0.7816	Intermediate Similarity	NPD8127	Discontinued
0.7814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4628	Phase 3
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.7784	Intermediate Similarity	NPD6166	Phase 2
0.7784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6190	Approved
0.7753	Intermediate Similarity	NPD5844	Phase 1
0.7735	Intermediate Similarity	NPD8312	Approved
0.7735	Intermediate Similarity	NPD8313	Approved
0.7706	Intermediate Similarity	NPD4380	Phase 2
0.7692	Intermediate Similarity	NPD1653	Approved
0.7674	Intermediate Similarity	NPD8455	Phase 2
0.7674	Intermediate Similarity	NPD1465	Phase 2
0.7674	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3817	Phase 2
0.7624	Intermediate Similarity	NPD7240	Approved
0.7624	Intermediate Similarity	NPD6559	Discontinued
0.7602	Intermediate Similarity	NPD7028	Phase 2
0.7574	Intermediate Similarity	NPD6273	Approved
0.7572	Intermediate Similarity	NPD2801	Approved
0.7544	Intermediate Similarity	NPD7458	Discontinued
0.7543	Intermediate Similarity	NPD7075	Discontinued
0.7542	Intermediate Similarity	NPD7473	Discontinued
0.7486	Intermediate Similarity	NPD3882	Suspended
0.7472	Intermediate Similarity	NPD6232	Discontinued
0.7471	Intermediate Similarity	NPD7819	Suspended
0.7458	Intermediate Similarity	NPD5494	Approved
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7412	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7799	Discontinued
0.7371	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD7680	Approved
0.7333	Intermediate Similarity	NPD7435	Discontinued
0.733	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.7314	Intermediate Similarity	NPD6801	Discontinued
0.7313	Intermediate Similarity	NPD7930	Approved
0.7306	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3027	Phase 3
0.7278	Intermediate Similarity	NPD8166	Discontinued
0.7273	Intermediate Similarity	NPD6653	Approved
0.7267	Intermediate Similarity	NPD9494	Approved
0.7267	Intermediate Similarity	NPD1512	Approved
0.7259	Intermediate Similarity	NPD7999	Approved
0.7257	Intermediate Similarity	NPD6386	Approved
0.7257	Intermediate Similarity	NPD6385	Approved
0.7236	Intermediate Similarity	NPD8151	Discontinued
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7232	Intermediate Similarity	NPD5402	Approved
0.7219	Intermediate Similarity	NPD6674	Discontinued
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7874	Approved
0.7186	Intermediate Similarity	NPD7033	Discontinued
0.7179	Intermediate Similarity	NPD6782	Approved
0.7179	Intermediate Similarity	NPD6779	Approved
0.7179	Intermediate Similarity	NPD6777	Approved
0.7179	Intermediate Similarity	NPD6778	Approved
0.7179	Intermediate Similarity	NPD6781	Approved
0.7179	Intermediate Similarity	NPD6776	Approved
0.7179	Intermediate Similarity	NPD6780	Approved
0.7176	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3750	Approved
0.7176	Intermediate Similarity	NPD4110	Phase 3
0.7164	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7783	Phase 2
0.716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7411	Suspended
0.7157	Intermediate Similarity	NPD7698	Approved
0.7157	Intermediate Similarity	NPD7697	Approved
0.7157	Intermediate Similarity	NPD7497	Discontinued
0.7157	Intermediate Similarity	NPD7696	Phase 3
0.7152	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7135	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD3764	Approved
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5403	Approved
0.7125	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7871	Phase 2
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.7121	Intermediate Similarity	NPD8319	Approved
0.7121	Intermediate Similarity	NPD7870	Phase 2
0.712	Intermediate Similarity	NPD3751	Discontinued
0.7108	Intermediate Similarity	NPD1933	Approved
0.7104	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5762	Approved
0.7101	Intermediate Similarity	NPD5763	Approved
0.71	Intermediate Similarity	NPD7585	Approved
0.71	Intermediate Similarity	NPD7701	Phase 2
0.7095	Intermediate Similarity	NPD7768	Phase 2
0.7093	Intermediate Similarity	NPD7236	Approved
0.7083	Intermediate Similarity	NPD1510	Phase 2
0.7079	Intermediate Similarity	NPD7801	Approved
0.7079	Intermediate Similarity	NPD5761	Phase 2
0.7079	Intermediate Similarity	NPD5760	Phase 2
0.7063	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD1549	Phase 2
0.7052	Intermediate Similarity	NPD6799	Approved
0.705	Intermediate Similarity	NPD7583	Approved
0.7049	Intermediate Similarity	NPD5242	Approved
0.7048	Intermediate Similarity	NPD1613	Approved
0.7048	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7097	Phase 1
0.702	Intermediate Similarity	NPD6823	Phase 2
0.7011	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5401	Approved
0.7006	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6005	Phase 3
0.7	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3787	Discontinued
0.6994	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7699	Phase 2
0.699	Remote Similarity	NPD7700	Phase 2
0.6989	Remote Similarity	NPD7239	Suspended
0.6977	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6764	Approved
0.6968	Remote Similarity	NPD7038	Approved
0.6968	Remote Similarity	NPD6765	Approved
0.6968	Remote Similarity	NPD7039	Approved
0.6965	Remote Similarity	NPD7584	Approved
0.6962	Remote Similarity	NPD9545	Approved
0.6961	Remote Similarity	NPD3749	Approved
0.6951	Remote Similarity	NPD2861	Phase 2
0.6949	Remote Similarity	NPD3455	Phase 2
0.6946	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5978	Approved
0.6944	Remote Similarity	NPD5977	Approved
0.6941	Remote Similarity	NPD2796	Approved
0.694	Remote Similarity	NPD6959	Discontinued
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD919	Approved
0.6923	Remote Similarity	NPD6535	Approved
0.6923	Remote Similarity	NPD6534	Approved
0.6914	Remote Similarity	NPD2533	Approved
0.6914	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD2534	Approved
0.6905	Remote Similarity	NPD447	Suspended
0.6898	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3705	Approved
0.689	Remote Similarity	NPD5647	Approved
0.689	Remote Similarity	NPD2798	Approved
0.6886	Remote Similarity	NPD6663	Approved
0.6886	Remote Similarity	NPD6233	Phase 2
0.6882	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD17	Approved
0.6872	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1876	Approved
0.6867	Remote Similarity	NPD7095	Approved
0.6857	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3226	Approved
0.6848	Remote Similarity	NPD5736	Approved
0.6845	Remote Similarity	NPD4140	Approved
0.6845	Remote Similarity	NPD1240	Approved
0.6842	Remote Similarity	NPD2438	Suspended
0.6829	Remote Similarity	NPD2797	Approved
0.6826	Remote Similarity	NPD3268	Approved
0.6826	Remote Similarity	NPD6798	Discontinued
0.6823	Remote Similarity	NPD6784	Approved
0.6823	Remote Similarity	NPD6785	Approved
0.6807	Remote Similarity	NPD1529	Clinical (unspecified phase)

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