NPASS Compound

Structure

CID41121 OpenBabel06191715372D 31 34 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 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 -3.4641 4.0000 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 -4.3301 -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 -2.5981 2.5000 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 -4.3301 -1.5000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 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 -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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -3.4641 1.0000 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 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 1 1 1 0 0 0 8 15 1 0 0 0 0 8 29 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 6 0 0 0 16 20 1 0 0 0 0 16 26 2 0 0 0 0 17 18 1 0 0 0 0 17 27 1 1 0 0 0 18 21 1 0 0 0 0 18 28 1 1 0 0 0 19 20 2 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 29 1 0 0 0 0 21 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.11
Volume:	404.357
LogP:	1.789
LogD:	1.586
LogS:	-3.994
# Rotatable Bonds:	3
TPSA:	170.05
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	3.883
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.027
MDCK Permeability:	9.014125680550933e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	93.18669891357422%
Volume Distribution (VD):	0.774
Pgp-substrate:	7.673054218292236%

ADMET: Metabolism

CYP1A2-inhibitor:	0.607
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.355
CYP2C9-substrate:	0.796
CYP2D6-inhibitor:	0.547
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	6.504
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.785
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.206
Carcinogencity:	0.265
Eye Corrosion:	0.003
Eye Irritation:	0.673
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC41121

Natural Product ID:	NPC41121
*Common Name:**	Kaempferol-3-O-Rhamnoside
IUPAC Name:	5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	SOSLMHZOJATCCP-QBWVUYDZSA-N
Standard InCHI:	InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m1/s1
SMILES:	Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515798
PubChem CID:	5318763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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
NPO40537	Koelreuteria henryi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350096]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28344	Rubus xanthocarpus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18817	Platycarpha glomerata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4940	Peyrousea umbellata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27913	Ageratina tomentella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28001	Zeora sordida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28120	Anisopappus pinnatifidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27221	Prosopis spicigera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27722	Caralluma stalagmifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9061	Euthamia graminifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19583	Ficus nervosa	Species	Moraceae	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	5

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT366	Individual Protein	Quinone reductase 2	Homo sapiens	IC50	=	3840.0	nM	PMID[520830]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	15200.0	nM	PMID[520833]
NPT2	Others	Unspecified		IC50	=	400.0	ug.mL-1	PMID[520829]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	64.7	ug.mL-1	PMID[520831]
NPT2	Others	Unspecified		IC50	=	4100.0	nM	PMID[520833]

☑ 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 NPC41121 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	407
0.1-0.2	1724
0.2-0.3	4072
0.3-0.4	9705
0.4-0.5	8599
0.5-0.6	4492
0.6-0.7	5714
0.7-0.8	4682
0.8-0.85	2069
0.85-0.9	708
0.9-0.95	389
0.95-1	136

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC111929
1.0	High Similarity	NPC472459
1.0	High Similarity	NPC320283
0.9933	High Similarity	NPC78263
0.9933	High Similarity	NPC108831
0.9933	High Similarity	NPC54802
0.9933	High Similarity	NPC77672
0.9933	High Similarity	NPC197304
0.9933	High Similarity	NPC135391
0.9933	High Similarity	NPC182634
0.9933	High Similarity	NPC133671
0.9868	High Similarity	NPC216496
0.9868	High Similarity	NPC276377
0.9868	High Similarity	NPC473438
0.9868	High Similarity	NPC246943
0.9868	High Similarity	NPC265885
0.9868	High Similarity	NPC48093
0.9868	High Similarity	NPC249281
0.9868	High Similarity	NPC163242
0.9868	High Similarity	NPC129217
0.9868	High Similarity	NPC224530
0.9868	High Similarity	NPC476215
0.9868	High Similarity	NPC116458
0.9868	High Similarity	NPC181465
0.9868	High Similarity	NPC139320
0.9868	High Similarity	NPC259957
0.9868	High Similarity	NPC253788
0.9868	High Similarity	NPC215710
0.9868	High Similarity	NPC159579
0.9868	High Similarity	NPC85707
0.9868	High Similarity	NPC173582
0.9867	High Similarity	NPC323593
0.9867	High Similarity	NPC203500
0.9867	High Similarity	NPC307938
0.9804	High Similarity	NPC150164
0.9804	High Similarity	NPC240306
0.9804	High Similarity	NPC27942
0.9803	High Similarity	NPC470405
0.9803	High Similarity	NPC187379
0.9803	High Similarity	NPC153342
0.9803	High Similarity	NPC471079
0.9803	High Similarity	NPC304741
0.98	High Similarity	NPC27408
0.98	High Similarity	NPC95090
0.974	High Similarity	NPC179198
0.974	High Similarity	NPC278419
0.974	High Similarity	NPC121703
0.974	High Similarity	NPC66087
0.9739	High Similarity	NPC64305
0.9739	High Similarity	NPC470125
0.9739	High Similarity	NPC297987
0.9739	High Similarity	NPC170052
0.9739	High Similarity	NPC135846
0.9739	High Similarity	NPC282169
0.9737	High Similarity	NPC104677
0.9733	High Similarity	NPC210003
0.9733	High Similarity	NPC39360
0.9733	High Similarity	NPC143851
0.9733	High Similarity	NPC29763
0.9733	High Similarity	NPC83283
0.9677	High Similarity	NPC72016
0.9675	High Similarity	NPC131745
0.9673	High Similarity	NPC136761
0.9671	High Similarity	NPC6985
0.9671	High Similarity	NPC288084
0.9671	High Similarity	NPC60966
0.9671	High Similarity	NPC65003
0.9671	High Similarity	NPC473512
0.9671	High Similarity	NPC44931
0.9671	High Similarity	NPC129827
0.9615	High Similarity	NPC203145
0.9615	High Similarity	NPC477613
0.9615	High Similarity	NPC32641
0.9615	High Similarity	NPC221342
0.9615	High Similarity	NPC476470
0.9615	High Similarity	NPC142142
0.9615	High Similarity	NPC11432
0.9615	High Similarity	NPC12013
0.9615	High Similarity	NPC256188
0.9615	High Similarity	NPC186816
0.9615	High Similarity	NPC64425
0.9615	High Similarity	NPC189564
0.9613	High Similarity	NPC183672
0.9608	High Similarity	NPC473634
0.9608	High Similarity	NPC138811
0.9608	High Similarity	NPC73511
0.9608	High Similarity	NPC22062
0.9605	High Similarity	NPC206378
0.9603	High Similarity	NPC106625
0.9554	High Similarity	NPC127546
0.9554	High Similarity	NPC317489
0.9554	High Similarity	NPC173637
0.9554	High Similarity	NPC223424
0.9554	High Similarity	NPC84362
0.9554	High Similarity	NPC52550
0.9551	High Similarity	NPC135358
0.9551	High Similarity	NPC76831
0.9551	High Similarity	NPC19240
0.9551	High Similarity	NPC287889
0.9551	High Similarity	NPC129264
0.9551	High Similarity	NPC292929
0.9551	High Similarity	NPC139060
0.9551	High Similarity	NPC289667
0.9551	High Similarity	NPC85751
0.9551	High Similarity	NPC205824
0.9548	High Similarity	NPC259834
0.9545	High Similarity	NPC473623
0.9542	High Similarity	NPC313163
0.9542	High Similarity	NPC156457
0.9542	High Similarity	NPC122809
0.9542	High Similarity	NPC258035
0.9542	High Similarity	NPC197896
0.9542	High Similarity	NPC161749
0.9539	High Similarity	NPC72649
0.9539	High Similarity	NPC97052
0.9539	High Similarity	NPC169248
0.9539	High Similarity	NPC99233
0.9539	High Similarity	NPC26195
0.9539	High Similarity	NPC39351
0.9536	High Similarity	NPC88484
0.9536	High Similarity	NPC121001
0.9536	High Similarity	NPC259182
0.9536	High Similarity	NPC259767
0.9533	High Similarity	NPC191154
0.9494	High Similarity	NPC120099
0.9494	High Similarity	NPC223747
0.9494	High Similarity	NPC225434
0.9494	High Similarity	NPC5319
0.9494	High Similarity	NPC219904
0.9494	High Similarity	NPC203050
0.949	High Similarity	NPC118284
0.949	High Similarity	NPC145038
0.949	High Similarity	NPC179950
0.949	High Similarity	NPC73855
0.949	High Similarity	NPC281131
0.949	High Similarity	NPC277174
0.949	High Similarity	NPC253662
0.949	High Similarity	NPC308404
0.949	High Similarity	NPC113968
0.949	High Similarity	NPC274618
0.949	High Similarity	NPC88789
0.949	High Similarity	NPC276222
0.949	High Similarity	NPC328940
0.949	High Similarity	NPC56077
0.949	High Similarity	NPC135599
0.9487	High Similarity	NPC80068
0.9484	High Similarity	NPC303913
0.9484	High Similarity	NPC101636
0.9477	High Similarity	NPC473657
0.9477	High Similarity	NPC295613
0.9477	High Similarity	NPC45165
0.9477	High Similarity	NPC261866
0.9477	High Similarity	NPC127406
0.9477	High Similarity	NPC170475
0.947	High Similarity	NPC134819
0.9434	High Similarity	NPC175429
0.9434	High Similarity	NPC209550
0.9434	High Similarity	NPC116864
0.9434	High Similarity	NPC277532
0.9434	High Similarity	NPC95866
0.9434	High Similarity	NPC138990
0.9434	High Similarity	NPC206123
0.9434	High Similarity	NPC244776
0.943	High Similarity	NPC325555
0.943	High Similarity	NPC265530
0.943	High Similarity	NPC226304
0.9427	High Similarity	NPC277205
0.9427	High Similarity	NPC19388
0.9427	High Similarity	NPC55786
0.9427	High Similarity	NPC240431
0.9423	High Similarity	NPC475382
0.9423	High Similarity	NPC298171
0.9423	High Similarity	NPC244875
0.9423	High Similarity	NPC44947
0.9419	High Similarity	NPC271270
0.9419	High Similarity	NPC97285
0.9419	High Similarity	NPC246469
0.9419	High Similarity	NPC142860
0.9416	High Similarity	NPC23817
0.9416	High Similarity	NPC43638
0.94	High Similarity	NPC199335
0.9375	High Similarity	NPC221288
0.9375	High Similarity	NPC217822
0.9375	High Similarity	NPC176740
0.9375	High Similarity	NPC33054
0.9375	High Similarity	NPC134532
0.9375	High Similarity	NPC101399
0.9375	High Similarity	NPC155877
0.9375	High Similarity	NPC190003
0.9375	High Similarity	NPC153755
0.9375	High Similarity	NPC11847
0.9375	High Similarity	NPC471725
0.9375	High Similarity	NPC474522
0.9375	High Similarity	NPC175107
0.9375	High Similarity	NPC245452
0.9375	High Similarity	NPC203259
0.9375	High Similarity	NPC471748
0.9371	High Similarity	NPC270578
0.9371	High Similarity	NPC52382
0.9367	High Similarity	NPC197285

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 NPC41121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	911
0.2-0.3	1828
0.3-0.4	2729
0.4-0.5	1894
0.5-0.6	962
0.6-0.7	277
0.7-0.8	127
0.8-0.85	23
0.85-0.9	14
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9542	High Similarity	NPD4381	Clinical (unspecified phase)
0.9494	High Similarity	NPD7804	Clinical (unspecified phase)
0.9375	High Similarity	NPD6797	Phase 2
0.9317	High Similarity	NPD7251	Discontinued
0.9259	High Similarity	NPD7808	Phase 3
0.9141	High Similarity	NPD4338	Clinical (unspecified phase)
0.913	High Similarity	NPD7054	Approved
0.9074	High Similarity	NPD7472	Approved
0.8957	High Similarity	NPD7074	Phase 3
0.8924	High Similarity	NPD7075	Discontinued
0.891	High Similarity	NPD6801	Discontinued
0.8903	High Similarity	NPD4380	Phase 2
0.8834	High Similarity	NPD3818	Discontinued
0.8831	High Similarity	NPD5403	Approved
0.8758	High Similarity	NPD6799	Approved
0.8734	High Similarity	NPD7096	Clinical (unspecified phase)
0.8712	High Similarity	NPD6166	Phase 2
0.8712	High Similarity	NPD6168	Clinical (unspecified phase)
0.8712	High Similarity	NPD6167	Clinical (unspecified phase)
0.8701	High Similarity	NPD4378	Clinical (unspecified phase)
0.8701	High Similarity	NPD5401	Approved
0.8679	High Similarity	NPD3817	Phase 2
0.8609	High Similarity	NPD1550	Clinical (unspecified phase)
0.8609	High Similarity	NPD1552	Clinical (unspecified phase)
0.8562	High Similarity	NPD5402	Approved
0.8553	High Similarity	NPD1934	Approved
0.8553	High Similarity	NPD1549	Phase 2
0.8512	High Similarity	NPD6559	Discontinued
0.85	High Similarity	NPD2393	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD6599	Discontinued
0.8408	Intermediate Similarity	NPD1512	Approved
0.8395	Intermediate Similarity	NPD3882	Suspended
0.8385	Intermediate Similarity	NPD2801	Approved
0.8375	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD2796	Approved
0.828	Intermediate Similarity	NPD1511	Approved
0.8235	Intermediate Similarity	NPD1510	Phase 2
0.8182	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1240	Approved
0.8059	Intermediate Similarity	NPD3751	Discontinued
0.8049	Intermediate Similarity	NPD7819	Suspended
0.8036	Intermediate Similarity	NPD3787	Discontinued
0.8023	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1607	Approved
0.7976	Intermediate Similarity	NPD6959	Discontinued
0.7975	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD7584	Approved
0.7901	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3750	Approved
0.7843	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD5494	Approved
0.7784	Intermediate Similarity	NPD8313	Approved
0.7784	Intermediate Similarity	NPD8312	Approved
0.7772	Intermediate Similarity	NPD6777	Approved
0.7772	Intermediate Similarity	NPD6779	Approved
0.7772	Intermediate Similarity	NPD6778	Approved
0.7772	Intermediate Similarity	NPD6776	Approved
0.7772	Intermediate Similarity	NPD6781	Approved
0.7772	Intermediate Similarity	NPD6782	Approved
0.7772	Intermediate Similarity	NPD6780	Approved
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7744	Intermediate Similarity	NPD1653	Approved
0.7742	Intermediate Similarity	NPD7435	Discontinued
0.7738	Intermediate Similarity	NPD7768	Phase 2
0.7736	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8455	Phase 2
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7701	Intermediate Similarity	NPD5844	Phase 1
0.7692	Intermediate Similarity	NPD3749	Approved
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6232	Discontinued
0.7613	Intermediate Similarity	NPD6798	Discontinued
0.76	Intermediate Similarity	NPD1091	Approved
0.7586	Intermediate Similarity	NPD7473	Discontinued
0.758	Intermediate Similarity	NPD1933	Approved
0.7576	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7685	Pre-registration
0.7564	Intermediate Similarity	NPD6233	Phase 2
0.7558	Intermediate Similarity	NPD7199	Phase 2
0.7553	Intermediate Similarity	NPD7696	Phase 3
0.7553	Intermediate Similarity	NPD7698	Approved
0.7553	Intermediate Similarity	NPD7697	Approved
0.7547	Intermediate Similarity	NPD7033	Discontinued
0.7547	Intermediate Similarity	NPD3748	Approved
0.7544	Intermediate Similarity	NPD919	Approved
0.7515	Intermediate Similarity	NPD1465	Phase 2
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7874	Approved
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD7585	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7484	Intermediate Similarity	NPD6832	Phase 2
0.747	Intermediate Similarity	NPD920	Approved
0.7469	Intermediate Similarity	NPD2800	Approved
0.7469	Intermediate Similarity	NPD1652	Phase 2
0.7457	Intermediate Similarity	NPD1247	Approved
0.7448	Intermediate Similarity	NPD8151	Discontinued
0.7443	Intermediate Similarity	NPD7228	Approved
0.7435	Intermediate Similarity	NPD7583	Approved
0.743	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6651	Approved
0.7416	Intermediate Similarity	NPD5953	Discontinued
0.7405	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1613	Approved
0.7405	Intermediate Similarity	NPD4363	Phase 3
0.7405	Intermediate Similarity	NPD4360	Phase 2
0.7403	Intermediate Similarity	NPD1203	Approved
0.7403	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7391	Intermediate Similarity	NPD2935	Discontinued
0.7381	Intermediate Similarity	NPD7458	Discontinued
0.738	Intermediate Similarity	NPD7699	Phase 2
0.738	Intermediate Similarity	NPD7700	Phase 2
0.7378	Intermediate Similarity	NPD6190	Approved
0.7372	Intermediate Similarity	NPD4908	Phase 1
0.7371	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7801	Approved
0.7371	Intermediate Similarity	NPD3926	Phase 2
0.7371	Intermediate Similarity	NPD7783	Phase 2
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1243	Approved
0.7358	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5124	Phase 1
0.7358	Intermediate Similarity	NPD6355	Discontinued
0.7355	Intermediate Similarity	NPD2798	Approved
0.7353	Intermediate Similarity	NPD37	Approved
0.7349	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2534	Approved
0.7349	Intermediate Similarity	NPD2532	Approved
0.7349	Intermediate Similarity	NPD2533	Approved
0.7346	Intermediate Similarity	NPD7266	Discontinued
0.7341	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1548	Phase 1
0.733	Intermediate Similarity	NPD8320	Phase 1
0.733	Intermediate Similarity	NPD8319	Approved
0.7326	Intermediate Similarity	NPD4965	Approved
0.7326	Intermediate Similarity	NPD4967	Phase 2
0.7326	Intermediate Similarity	NPD4966	Approved
0.7316	Intermediate Similarity	NPD6823	Phase 2
0.7289	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD2313	Discontinued
0.7268	Intermediate Similarity	NPD8434	Phase 2
0.7255	Intermediate Similarity	NPD422	Phase 1
0.7246	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2344	Approved
0.7233	Intermediate Similarity	NPD4062	Phase 3
0.7226	Intermediate Similarity	NPD3225	Approved
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.7208	Intermediate Similarity	NPD9717	Approved
0.7193	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD943	Approved
0.7179	Intermediate Similarity	NPD2797	Approved
0.7178	Intermediate Similarity	NPD6100	Approved
0.7178	Intermediate Similarity	NPD6099	Approved
0.7176	Intermediate Similarity	NPD3226	Approved
0.7174	Intermediate Similarity	NPD8150	Discontinued
0.7169	Intermediate Similarity	NPD3887	Approved
0.7169	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7143	Intermediate Similarity	NPD4340	Discontinued
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7129	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3027	Phase 3
0.7089	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7240	Approved
0.7083	Intermediate Similarity	NPD7390	Discontinued
0.7074	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6212	Phase 3
0.7074	Intermediate Similarity	NPD6213	Phase 3
0.7066	Intermediate Similarity	NPD2309	Approved
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7048	Intermediate Similarity	NPD2654	Approved
0.7041	Intermediate Similarity	NPD4662	Approved
0.7041	Intermediate Similarity	NPD4661	Approved
0.7039	Intermediate Similarity	NPD2403	Approved
0.7037	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD447	Suspended
0.703	Intermediate Similarity	NPD2346	Discontinued
0.7012	Intermediate Similarity	NPD4308	Phase 3
0.7012	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4361	Phase 2
0.7	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5049	Phase 3
0.6993	Remote Similarity	NPD9545	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