NPASS Compound

Structure

CID107197 OpenBabel06191715452D 40 43 0 0 1 0 0 0 0 0999 V2000 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 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 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -1.7321 -3.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 2 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 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 2 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 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 1 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 -2.5981 -0.5000 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 1.7321 -3.0000 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 26 1 0 0 0 0 2 26 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 1 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 10 36 1 0 0 0 0 11 23 2 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 40 1 0 0 0 0 14 9 1 1 0 0 0 14 17 1 0 0 0 0 14 37 1 0 0 0 0 15 10 1 1 0 0 0 15 18 1 0 0 0 0 15 38 1 0 0 0 0 16 28 2 0 0 0 0 16 29 1 0 0 0 0 17 19 1 0 0 0 0 17 30 1 6 0 0 0 18 20 1 0 0 0 0 18 31 1 6 0 0 0 19 21 1 0 0 0 0 19 32 1 1 0 0 0 20 22 1 0 0 0 0 20 33 1 1 0 0 0 21 24 1 0 0 0 0 21 34 1 6 0 0 0 22 25 1 0 0 0 0 22 35 1 6 0 0 0 23 39 1 0 0 0 0 24 36 1 1 0 0 0 24 37 1 0 0 0 0 25 38 1 0 0 0 0 25 39 1 1 0 0 0 26 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.37
Volume:	625.403
LogP:	6.157
LogD:	4.16
LogS:	-5.28
# Rotatable Bonds:	14
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	5.157
Fsp3:	0.743
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	1.586776488693431e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.752
30% Bioavailability (F30%):	0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.384
Plasma Protein Binding (PPB):	93.35672760009766%
Volume Distribution (VD):	1.424
Pgp-substrate:	2.4849984645843506%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.25
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.602
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	8.264
Half-life (T1/2):	0.365

ADMET: Toxicity

hERG Blockers:	0.899
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.668
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.712
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.844
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC107197

Natural Product ID:	NPC107197
*Common Name:**	Omubioside
IUPAC Name:	3-[2,2-dimethyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-6-yl]propanoic acid
Synonyms:	omubioside
Standard InCHIKey:	NQAQCZORTDQVFT-LMYULTQQSA-N
Standard InCHI:	InChI=1S/C26H36O14/c1-26(2)8-7-12-13(40-26)5-3-11(4-6-16(28)29)23(12)39-25-22(35)20(33)18(31)15(38-25)10-36-24-21(34)19(32)17(30)14(9-27)37-24/h3,5,7-8,14-15,17-22,24-25,27,30-35H,4,6,9-10H2,1-2H3,(H,28,29)/t14-,15-,17-,18-,19+,20+,21-,22-,24-,25+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(CCC(=O)O)ccc4c3C=CC(O4)(C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928406
PubChem CID:	56602471
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[21985060]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21985060]
NPO1762	Citropsis articulata	Species	Rutaceae	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	2
IC50	2

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	50.0	ug.mL-1	PMID[566521]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	>	100.0	ug.mL-1	PMID[566521]
NPT633	Organism	Leishmania donovani	Leishmania donovani	EC50	>	125.0	ug.mL-1	PMID[566521]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	>	125.0	ug.mL-1	PMID[566521]

☑ 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 NPC107197 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	338
0.1-0.2	1315
0.2-0.3	3053
0.3-0.4	6960
0.4-0.5	10075
0.5-0.6	6706
0.6-0.7	6683
0.7-0.8	6944
0.8-0.85	552
0.85-0.9	69
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9379	High Similarity	NPC469700
0.9116	High Similarity	NPC87950
0.9116	High Similarity	NPC471764
0.898	High Similarity	NPC85624
0.8944	High Similarity	NPC34456
0.8919	High Similarity	NPC74320
0.8919	High Similarity	NPC107120
0.8859	High Similarity	NPC296377
0.8854	High Similarity	NPC124155
0.8854	High Similarity	NPC257566
0.8846	High Similarity	NPC101636
0.8839	High Similarity	NPC43761
0.8831	High Similarity	NPC295613
0.8831	High Similarity	NPC17521
0.8831	High Similarity	NPC473657
0.8824	High Similarity	NPC108706
0.8824	High Similarity	NPC268950
0.8824	High Similarity	NPC211158
0.8824	High Similarity	NPC78021
0.8824	High Similarity	NPC87304
0.8808	High Similarity	NPC100818
0.8803	High Similarity	NPC269421
0.88	High Similarity	NPC169510
0.8792	High Similarity	NPC474044
0.879	High Similarity	NPC190450
0.879	High Similarity	NPC298171
0.879	High Similarity	NPC44947
0.8766	High Similarity	NPC470604
0.8766	High Similarity	NPC470605
0.8766	High Similarity	NPC470603
0.875	High Similarity	NPC213723
0.8734	High Similarity	NPC183672
0.8726	High Similarity	NPC47923
0.8725	High Similarity	NPC226722
0.8718	High Similarity	NPC138811
0.8718	High Similarity	NPC473634
0.8718	High Similarity	NPC470607
0.8718	High Similarity	NPC22062
0.8716	High Similarity	NPC116922
0.8716	High Similarity	NPC469367
0.871	High Similarity	NPC206378
0.871	High Similarity	NPC127406
0.871	High Similarity	NPC45165
0.8696	High Similarity	NPC76047
0.8679	High Similarity	NPC294722
0.8679	High Similarity	NPC475979
0.8675	High Similarity	NPC472339
0.8671	High Similarity	NPC131745
0.8671	High Similarity	NPC259834
0.8662	High Similarity	NPC271270
0.8662	High Similarity	NPC142860
0.8662	High Similarity	NPC472320
0.8662	High Similarity	NPC473623
0.8662	High Similarity	NPC97285
0.8662	High Similarity	NPC246469
0.8658	High Similarity	NPC177597
0.8658	High Similarity	NPC225445
0.8654	High Similarity	NPC473512
0.8654	High Similarity	NPC129827
0.8654	High Similarity	NPC44931
0.8654	High Similarity	NPC23817
0.8654	High Similarity	NPC43638
0.8654	High Similarity	NPC470606
0.8654	High Similarity	NPC65003
0.8649	High Similarity	NPC128337
0.8649	High Similarity	NPC84207
0.8649	High Similarity	NPC5253
0.8649	High Similarity	NPC139976
0.8649	High Similarity	NPC230718
0.8649	High Similarity	NPC49542
0.8645	High Similarity	NPC27408
0.8645	High Similarity	NPC26195
0.8645	High Similarity	NPC95090
0.8645	High Similarity	NPC39351
0.8645	High Similarity	NPC169248
0.8645	High Similarity	NPC72649
0.8645	High Similarity	NPC97052
0.8639	High Similarity	NPC312881
0.8634	High Similarity	NPC5319
0.863	High Similarity	NPC87777
0.863	High Similarity	NPC471069
0.863	High Similarity	NPC262328
0.863	High Similarity	NPC471068
0.8627	High Similarity	NPC38775
0.8627	High Similarity	NPC191154
0.8625	High Similarity	NPC262222
0.8625	High Similarity	NPC298666
0.8625	High Similarity	NPC68592
0.8625	High Similarity	NPC64425
0.8616	High Similarity	NPC179198
0.8616	High Similarity	NPC66087
0.8616	High Similarity	NPC278419
0.8616	High Similarity	NPC121703
0.8608	High Similarity	NPC129217
0.8608	High Similarity	NPC224530
0.8608	High Similarity	NPC48093
0.8608	High Similarity	NPC303913
0.8608	High Similarity	NPC259957
0.8608	High Similarity	NPC216496
0.8608	High Similarity	NPC85707
0.8608	High Similarity	NPC159579
0.86	High Similarity	NPC469701
0.8599	High Similarity	NPC73511
0.859	High Similarity	NPC170475
0.8581	High Similarity	NPC143851
0.8581	High Similarity	NPC39360
0.8581	High Similarity	NPC152771
0.8581	High Similarity	NPC215512
0.8581	High Similarity	NPC287286
0.8581	High Similarity	NPC83283
0.8581	High Similarity	NPC80098
0.8581	High Similarity	NPC195357
0.8581	High Similarity	NPC476442
0.8581	High Similarity	NPC29763
0.8581	High Similarity	NPC106625
0.8581	High Similarity	NPC210003
0.858	High Similarity	NPC138990
0.858	High Similarity	NPC277532
0.858	High Similarity	NPC175429
0.858	High Similarity	NPC209550
0.8571	High Similarity	NPC471072
0.8571	High Similarity	NPC23253
0.8571	High Similarity	NPC134819
0.8571	High Similarity	NPC471070
0.8571	High Similarity	NPC471071
0.8571	High Similarity	NPC250488
0.8562	High Similarity	NPC103116
0.8562	High Similarity	NPC103409
0.8562	High Similarity	NPC104172
0.8562	High Similarity	NPC72016
0.8562	High Similarity	NPC88886
0.8553	High Similarity	NPC240306
0.8553	High Similarity	NPC475382
0.8553	High Similarity	NPC27942
0.8553	High Similarity	NPC472876
0.8553	High Similarity	NPC244875
0.8553	High Similarity	NPC218685
0.8552	High Similarity	NPC471029
0.8544	High Similarity	NPC153342
0.8544	High Similarity	NPC187379
0.8544	High Similarity	NPC200708
0.8537	High Similarity	NPC63105
0.8535	High Similarity	NPC122809
0.8535	High Similarity	NPC313163
0.8535	High Similarity	NPC108831
0.8535	High Similarity	NPC161749
0.8535	High Similarity	NPC182634
0.8535	High Similarity	NPC60966
0.8535	High Similarity	NPC197896
0.8535	High Similarity	NPC156457
0.8535	High Similarity	NPC258035
0.8533	High Similarity	NPC471028
0.8526	High Similarity	NPC99233
0.8516	High Similarity	NPC256141
0.8516	High Similarity	NPC121001
0.8516	High Similarity	NPC259182
0.8506	High Similarity	NPC106025
0.8506	High Similarity	NPC477240
0.8506	High Similarity	NPC214454
0.8503	High Similarity	NPC155963
0.8503	High Similarity	NPC232246
0.8503	High Similarity	NPC153818
0.85	High Similarity	NPC311850
0.85	High Similarity	NPC473644
0.8497	Intermediate Similarity	NPC199335
0.8491	Intermediate Similarity	NPC476215
0.8491	Intermediate Similarity	NPC249281
0.8491	Intermediate Similarity	NPC477629
0.8491	Intermediate Similarity	NPC163242
0.8491	Intermediate Similarity	NPC173582
0.8491	Intermediate Similarity	NPC270675
0.8491	Intermediate Similarity	NPC282169
0.8491	Intermediate Similarity	NPC473438
0.8491	Intermediate Similarity	NPC246943
0.8491	Intermediate Similarity	NPC276377
0.8491	Intermediate Similarity	NPC181465
0.8491	Intermediate Similarity	NPC139320
0.8491	Intermediate Similarity	NPC195685
0.8491	Intermediate Similarity	NPC472994
0.8491	Intermediate Similarity	NPC116458
0.8491	Intermediate Similarity	NPC210961
0.8491	Intermediate Similarity	NPC477628
0.8491	Intermediate Similarity	NPC215710
0.8491	Intermediate Similarity	NPC253788
0.8491	Intermediate Similarity	NPC265885
0.8487	Intermediate Similarity	NPC474302
0.8485	Intermediate Similarity	NPC325176
0.8481	Intermediate Similarity	NPC308265
0.8481	Intermediate Similarity	NPC320283
0.8481	Intermediate Similarity	NPC41121
0.8481	Intermediate Similarity	NPC472459
0.8481	Intermediate Similarity	NPC111929
0.8481	Intermediate Similarity	NPC104677
0.8476	Intermediate Similarity	NPC208668
0.8471	Intermediate Similarity	NPC203500
0.8471	Intermediate Similarity	NPC165483
0.8471	Intermediate Similarity	NPC307938
0.8471	Intermediate Similarity	NPC323593
0.8466	Intermediate Similarity	NPC210808
0.8466	Intermediate Similarity	NPC78734

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 NPC107197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	821
0.2-0.3	1681
0.3-0.4	2658
0.4-0.5	1998
0.5-0.6	1095
0.6-0.7	475
0.7-0.8	131
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8634	High Similarity	NPD7804	Clinical (unspecified phase)
0.8581	High Similarity	NPD8455	Phase 2
0.8535	High Similarity	NPD4381	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7054	Approved
0.8242	Intermediate Similarity	NPD7472	Approved
0.8242	Intermediate Similarity	NPD7074	Phase 3
0.8228	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8165	Intermediate Similarity	NPD6801	Discontinued
0.8153	Intermediate Similarity	NPD4380	Phase 2
0.8144	Intermediate Similarity	NPD7251	Discontinued
0.8108	Intermediate Similarity	NPD5124	Phase 1
0.8108	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7808	Phase 3
0.8084	Intermediate Similarity	NPD6797	Phase 2
0.8037	Intermediate Similarity	NPD7199	Phase 2
0.8012	Intermediate Similarity	NPD7228	Approved
0.8	Intermediate Similarity	NPD7097	Phase 1
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7411	Suspended
0.7929	Intermediate Similarity	NPD6559	Discontinued
0.7911	Intermediate Similarity	NPD1653	Approved
0.7904	Intermediate Similarity	NPD3818	Discontinued
0.7902	Intermediate Similarity	NPD1091	Approved
0.7901	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7819	Suspended
0.7875	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1652	Phase 2
0.7831	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7033	Discontinued
0.7826	Intermediate Similarity	NPD37	Approved
0.7824	Intermediate Similarity	NPD7240	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.7785	Intermediate Similarity	NPD6798	Discontinued
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6799	Approved
0.7751	Intermediate Similarity	NPD5844	Phase 1
0.7736	Intermediate Similarity	NPD5403	Approved
0.773	Intermediate Similarity	NPD3817	Phase 2
0.773	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5401	Approved
0.7722	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7679	Intermediate Similarity	NPD6166	Phase 2
0.7679	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3787	Discontinued
0.7663	Intermediate Similarity	NPD7583	Approved
0.7632	Intermediate Similarity	NPD6355	Discontinued
0.7628	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7585	Approved
0.7616	Intermediate Similarity	NPD6233	Phase 2
0.7613	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1934	Approved
0.7593	Intermediate Similarity	NPD6599	Discontinued
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7564	Intermediate Similarity	NPD1549	Phase 2
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2796	Approved
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD6674	Discontinued
0.7515	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7584	Approved
0.7471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7768	Phase 2
0.7468	Intermediate Similarity	NPD3750	Approved
0.7456	Intermediate Similarity	NPD7229	Phase 3
0.7452	Intermediate Similarity	NPD2424	Discontinued
0.7451	Intermediate Similarity	NPD1613	Approved
0.7451	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5494	Approved
0.7436	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD6100	Approved
0.7423	Intermediate Similarity	NPD7458	Discontinued
0.7417	Intermediate Similarity	NPD4908	Phase 1
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7414	Intermediate Similarity	NPD7685	Pre-registration
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6959	Discontinued
0.7389	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6004	Phase 3
0.7389	Intermediate Similarity	NPD6002	Phase 3
0.7389	Intermediate Similarity	NPD6005	Phase 3
0.7389	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3751	Discontinued
0.7375	Intermediate Similarity	NPD5058	Phase 3
0.7372	Intermediate Similarity	NPD3748	Approved
0.7358	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2801	Approved
0.7349	Intermediate Similarity	NPD1465	Phase 2
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1296	Phase 2
0.732	Intermediate Similarity	NPD3268	Approved
0.7316	Intermediate Similarity	NPD7783	Phase 2
0.7316	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD3225	Approved
0.7261	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD1548	Phase 1
0.7251	Intermediate Similarity	NPD6232	Discontinued
0.7233	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7473	Discontinued
0.7222	Intermediate Similarity	NPD1511	Approved
0.7219	Intermediate Similarity	NPD7435	Discontinued
0.7211	Intermediate Similarity	NPD8151	Discontinued
0.7208	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7843	Approved
0.719	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1243	Approved
0.7181	Intermediate Similarity	NPD1610	Phase 2
0.7178	Intermediate Similarity	NPD2534	Approved
0.7178	Intermediate Similarity	NPD2533	Approved
0.7178	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2532	Approved
0.716	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD7095	Approved
0.7134	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD1608	Approved
0.7128	Intermediate Similarity	NPD7680	Approved
0.7124	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3749	Approved
0.7115	Intermediate Similarity	NPD1240	Approved
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7108	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3266	Approved
0.7105	Intermediate Similarity	NPD3267	Approved
0.7099	Intermediate Similarity	NPD6190	Approved
0.7093	Intermediate Similarity	NPD8127	Discontinued
0.7089	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4538	Approved
0.7089	Intermediate Similarity	NPD4536	Approved
0.7089	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6832	Phase 2
0.7076	Intermediate Similarity	NPD919	Approved
0.707	Intermediate Similarity	NPD1933	Approved
0.7063	Intermediate Similarity	NPD5762	Approved
0.7063	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD6778	Approved
0.7059	Intermediate Similarity	NPD6781	Approved
0.7059	Intermediate Similarity	NPD6776	Approved
0.7059	Intermediate Similarity	NPD6780	Approved
0.7059	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD6777	Approved
0.7055	Intermediate Similarity	NPD7157	Approved
0.7047	Intermediate Similarity	NPD1778	Approved
0.7045	Intermediate Similarity	NPD7286	Phase 2
0.7042	Intermediate Similarity	NPD2684	Approved
0.7037	Intermediate Similarity	NPD7696	Phase 3
0.7037	Intermediate Similarity	NPD7697	Approved
0.7037	Intermediate Similarity	NPD7698	Approved
0.7032	Intermediate Similarity	NPD4625	Phase 3
0.7027	Intermediate Similarity	NPD1894	Discontinued
0.7025	Intermediate Similarity	NPD1607	Approved
0.7025	Intermediate Similarity	NPD6653	Approved
0.7025	Intermediate Similarity	NPD6651	Approved
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD4477	Approved
0.7	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD4476	Approved
0.6995	Remote Similarity	NPD7874	Approved
0.6995	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2313	Discontinued
0.6979	Remote Similarity	NPD7701	Phase 2
0.6975	Remote Similarity	NPD2800	Approved
0.6974	Remote Similarity	NPD4749	Approved
0.6972	Remote Similarity	NPD290	Approved
0.6968	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5953	Discontinued
0.6962	Remote Similarity	NPD230	Phase 1
0.6948	Remote Similarity	NPD5647	Approved
0.694	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2799	Discontinued
0.6937	Remote Similarity	NPD4308	Phase 3
0.6937	Remote Similarity	NPD5588	Approved
0.6937	Remote Similarity	NPD5960	Phase 3
0.6933	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD8434	Phase 2

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