NPASS Compound

Structure

NPC187379 OpenBabel07101719512D 42 46 0 0 1 0 0 0 0 0999 V2000 3.4641 -4.0000 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 -3.4641 2.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 3.4641 -3.0000 0.0000 C 0 0 1 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 -6.9282 5.0000 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 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 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 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 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 -6.0622 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 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 -5.1962 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 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 -6.0622 0.5000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -5.1962 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 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 14 2 0 0 0 0 8 38 1 0 0 0 0 9 1 1 6 0 0 0 9 17 1 0 0 0 0 9 39 1 0 0 0 0 10 25 1 0 0 0 0 11 28 1 0 0 0 0 12 40 1 0 0 0 0 13 16 2 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 41 1 0 0 0 0 15 8 1 1 0 0 0 15 18 1 0 0 0 0 15 42 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 30 1 1 0 0 0 18 21 1 0 0 0 0 18 31 1 6 0 0 0 19 22 1 0 0 0 0 19 32 2 0 0 0 0 20 23 1 0 0 0 0 20 33 1 6 0 0 0 21 24 1 0 0 0 0 21 34 1 1 0 0 0 22 25 2 0 0 0 0 22 35 1 0 0 0 0 23 26 1 0 0 0 0 23 36 1 6 0 0 0 24 27 1 0 0 0 0 24 37 1 6 0 0 0 25 41 1 0 0 0 0 26 38 1 1 0 0 0 26 39 1 0 0 0 0 27 40 1 1 0 0 0 27 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.16
Volume:	543.527
LogP:	0.345
LogD:	-0.15
LogS:	-3.394
# Rotatable Bonds:	6
TPSA:	249.2
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.159
Synthetic Accessibility Score:	4.671
Fsp3:	0.444
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:	-6.487
MDCK Permeability:	2.347303416172508e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.829
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	88.45126342773438%
Volume Distribution (VD):	0.775
Pgp-substrate:	9.529308319091797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.118
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.282
Half-life (T1/2):	0.645

ADMET: Toxicity

hERG Blockers:	0.241
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.833
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.87
Carcinogencity:	0.179
Eye Corrosion:	0.003
Eye Irritation:	0.124
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC187379

Natural Product ID:	NPC187379
*Common Name:**	Kaempferol 4'-O-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	3,5,7-trihydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms:
Standard InCHIKey:	NTBNRFPZTCXMTF-QETNVOEASA-N
Standard InCHI:	InChI=1S/C27H30O15/c1-9-17(30)20(33)23(36)26(39-9)38-8-15-18(31)21(34)24(37)27(42-15)40-12-4-2-10(3-5-12)25-22(35)19(32)16-13(29)6-11(28)7-14(16)41-25/h2-7,9,15,17-18,20-21,23-24,26-31,33-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,23+,24+,26+,27+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3ccc(cc3)c3c(c(=O)c4c(cc(cc4o3)O)O)O)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2336772
PubChem CID:	71600048
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17473466]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23357036]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24634069]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	239.2	ng/ml	PMID[455987]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	521.4	mg/dl	PMID[455987]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	105.13	mg/dl	PMID[455987]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	8.47	mg kg-1	PMID[455987]

☑ 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 NPC187379 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	433
0.1-0.2	1738
0.2-0.3	4147
0.3-0.4	9795
0.4-0.5	8645
0.5-0.6	4751
0.6-0.7	5830
0.7-0.8	5165
0.8-0.85	1252
0.85-0.9	433
0.9-0.95	415
0.95-1	93

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC181465
0.9934	High Similarity	NPC163242
0.9934	High Similarity	NPC476215
0.9934	High Similarity	NPC246943
0.9934	High Similarity	NPC253788
0.9934	High Similarity	NPC173582
0.9934	High Similarity	NPC139320
0.9934	High Similarity	NPC473438
0.9934	High Similarity	NPC215710
0.9934	High Similarity	NPC276377
0.9934	High Similarity	NPC116458
0.9934	High Similarity	NPC249281
0.9934	High Similarity	NPC265885
0.9869	High Similarity	NPC240306
0.9868	High Similarity	NPC304741
0.9868	High Similarity	NPC470405
0.9868	High Similarity	NPC182634
0.9868	High Similarity	NPC136761
0.9868	High Similarity	NPC471079
0.9868	High Similarity	NPC473512
0.9868	High Similarity	NPC65003
0.9868	High Similarity	NPC44931
0.9868	High Similarity	NPC108831
0.9868	High Similarity	NPC129827
0.9804	High Similarity	NPC64305
0.9804	High Similarity	NPC135846
0.9804	High Similarity	NPC297987
0.9804	High Similarity	NPC170052
0.9803	High Similarity	NPC111929
0.9803	High Similarity	NPC473634
0.9803	High Similarity	NPC22062
0.9803	High Similarity	NPC41121
0.9803	High Similarity	NPC320283
0.9803	High Similarity	NPC472459
0.9803	High Similarity	NPC138811
0.9801	High Similarity	NPC307938
0.9801	High Similarity	NPC323593
0.9801	High Similarity	NPC203500
0.9742	High Similarity	NPC135358
0.9742	High Similarity	NPC287889
0.9739	High Similarity	NPC153342
0.9739	High Similarity	NPC473623
0.9737	High Similarity	NPC77672
0.9737	High Similarity	NPC54802
0.9737	High Similarity	NPC197304
0.9737	High Similarity	NPC133671
0.9737	High Similarity	NPC78263
0.9737	High Similarity	NPC135391
0.9735	High Similarity	NPC95090
0.9735	High Similarity	NPC27408
0.9679	High Similarity	NPC203145
0.9679	High Similarity	NPC11432
0.9679	High Similarity	NPC32641
0.9679	High Similarity	NPC12013
0.9679	High Similarity	NPC142142
0.9679	High Similarity	NPC476470
0.9679	High Similarity	NPC221342
0.9679	High Similarity	NPC189564
0.9679	High Similarity	NPC256188
0.9679	High Similarity	NPC64425
0.9679	High Similarity	NPC477613
0.9679	High Similarity	NPC186816
0.9675	High Similarity	NPC48093
0.9675	High Similarity	NPC470125
0.9675	High Similarity	NPC129217
0.9675	High Similarity	NPC101636
0.9675	High Similarity	NPC259957
0.9675	High Similarity	NPC224530
0.9675	High Similarity	NPC216496
0.9675	High Similarity	NPC303913
0.9675	High Similarity	NPC159579
0.9675	High Similarity	NPC85707
0.9671	High Similarity	NPC206378
0.9671	High Similarity	NPC295613
0.9671	High Similarity	NPC473657
0.9669	High Similarity	NPC143851
0.9669	High Similarity	NPC210003
0.9669	High Similarity	NPC83283
0.9669	High Similarity	NPC39360
0.9669	High Similarity	NPC29763
0.9615	High Similarity	NPC289667
0.9615	High Similarity	NPC139060
0.9615	High Similarity	NPC292929
0.9615	High Similarity	NPC76831
0.9613	High Similarity	NPC259834
0.9613	High Similarity	NPC150164
0.9613	High Similarity	NPC131745
0.9613	High Similarity	NPC298171
0.9613	High Similarity	NPC27942
0.9613	High Similarity	NPC244875
0.9613	High Similarity	NPC475382
0.9613	High Similarity	NPC44947
0.961	High Similarity	NPC142860
0.961	High Similarity	NPC271270
0.961	High Similarity	NPC97285
0.961	High Similarity	NPC246469
0.9608	High Similarity	NPC60966
0.9608	High Similarity	NPC6985
0.9605	High Similarity	NPC72649
0.9605	High Similarity	NPC97052
0.9605	High Similarity	NPC169248
0.9605	High Similarity	NPC26195
0.9605	High Similarity	NPC39351
0.9557	High Similarity	NPC5319
0.9551	High Similarity	NPC66087
0.9551	High Similarity	NPC311850
0.9551	High Similarity	NPC80068
0.9551	High Similarity	NPC278419
0.9551	High Similarity	NPC121703
0.9551	High Similarity	NPC183672
0.9551	High Similarity	NPC179198
0.9551	High Similarity	NPC473644
0.9551	High Similarity	NPC124155
0.9551	High Similarity	NPC257566
0.9548	High Similarity	NPC47923
0.9548	High Similarity	NPC282169
0.9545	High Similarity	NPC104677
0.9545	High Similarity	NPC73511
0.9542	High Similarity	NPC170475
0.9539	High Similarity	NPC106625
0.9497	High Similarity	NPC175429
0.9497	High Similarity	NPC209550
0.9497	High Similarity	NPC277532
0.9497	High Similarity	NPC95866
0.9497	High Similarity	NPC138990
0.9497	High Similarity	NPC67105
0.949	High Similarity	NPC205824
0.949	High Similarity	NPC72016
0.949	High Similarity	NPC85751
0.949	High Similarity	NPC19240
0.949	High Similarity	NPC129264
0.9487	High Similarity	NPC190450
0.9481	High Similarity	NPC313163
0.9481	High Similarity	NPC161749
0.9481	High Similarity	NPC197896
0.9481	High Similarity	NPC258035
0.9481	High Similarity	NPC122809
0.9481	High Similarity	NPC156457
0.9481	High Similarity	NPC288084
0.9477	High Similarity	NPC99233
0.9474	High Similarity	NPC121001
0.9474	High Similarity	NPC88484
0.9474	High Similarity	NPC259767
0.9474	High Similarity	NPC259182
0.947	High Similarity	NPC191154
0.9437	High Similarity	NPC471725
0.9437	High Similarity	NPC155877
0.9437	High Similarity	NPC134532
0.9437	High Similarity	NPC33054
0.9437	High Similarity	NPC203259
0.9437	High Similarity	NPC176740
0.9437	High Similarity	NPC471748
0.9437	High Similarity	NPC474522
0.9434	High Similarity	NPC227508
0.943	High Similarity	NPC68592
0.943	High Similarity	NPC298666
0.943	High Similarity	NPC115674
0.943	High Similarity	NPC262222
0.943	High Similarity	NPC210073
0.9423	High Similarity	NPC472994
0.9423	High Similarity	NPC195685
0.9423	High Similarity	NPC477629
0.9423	High Similarity	NPC270675
0.9423	High Similarity	NPC477628
0.9423	High Similarity	NPC210961
0.9419	High Similarity	NPC308265
0.9416	High Similarity	NPC261866
0.9416	High Similarity	NPC45165
0.9416	High Similarity	NPC127406
0.9408	High Similarity	NPC134819
0.9375	High Similarity	NPC470712
0.9375	High Similarity	NPC285197
0.9375	High Similarity	NPC156869
0.9375	High Similarity	NPC259896
0.9375	High Similarity	NPC188815
0.9375	High Similarity	NPC29958
0.9375	High Similarity	NPC164704
0.9375	High Similarity	NPC254855
0.9375	High Similarity	NPC255157
0.9375	High Similarity	NPC136042
0.9375	High Similarity	NPC67326
0.9371	High Similarity	NPC173637
0.9371	High Similarity	NPC127546
0.9371	High Similarity	NPC317489
0.9371	High Similarity	NPC52550
0.9371	High Similarity	NPC275454
0.9371	High Similarity	NPC84362
0.9371	High Similarity	NPC223424
0.9367	High Similarity	NPC277205
0.9363	High Similarity	NPC472876
0.9359	High Similarity	NPC472320
0.9359	High Similarity	NPC271479
0.9359	High Similarity	NPC200708
0.9355	High Similarity	NPC43638
0.9355	High Similarity	NPC23817
0.9342	High Similarity	NPC213723
0.9338	High Similarity	NPC199335
0.9321	High Similarity	NPC19108
0.9321	High Similarity	NPC476472
0.9321	High Similarity	NPC294815

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 NPC187379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	919
0.2-0.3	1878
0.3-0.4	2792
0.4-0.5	1906
0.5-0.6	891
0.6-0.7	245
0.7-0.8	108
0.8-0.85	16
0.85-0.9	6
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9557	High Similarity	NPD7804	Clinical (unspecified phase)
0.9481	High Similarity	NPD4381	Clinical (unspecified phase)
0.9437	High Similarity	NPD6797	Phase 2
0.9379	High Similarity	NPD7251	Discontinued
0.9321	High Similarity	NPD7808	Phase 3
0.9313	High Similarity	NPD7054	Approved
0.9255	High Similarity	NPD7472	Approved
0.9136	High Similarity	NPD7074	Phase 3
0.897	High Similarity	NPD4338	Clinical (unspecified phase)
0.8889	High Similarity	NPD6167	Clinical (unspecified phase)
0.8889	High Similarity	NPD6166	Phase 2
0.8889	High Similarity	NPD6168	Clinical (unspecified phase)
0.8846	High Similarity	NPD4380	Phase 2
0.878	High Similarity	NPD3818	Discontinued
0.875	High Similarity	NPD7075	Discontinued
0.8734	High Similarity	NPD6801	Discontinued
0.8654	High Similarity	NPD5403	Approved
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8581	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8553	High Similarity	NPD1550	Clinical (unspecified phase)
0.8553	High Similarity	NPD1552	Clinical (unspecified phase)
0.8526	High Similarity	NPD5401	Approved
0.8509	High Similarity	NPD3817	Phase 2
0.85	High Similarity	NPD1934	Approved
0.8497	Intermediate Similarity	NPD1549	Phase 2
0.8462	Intermediate Similarity	NPD6559	Discontinued
0.8447	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD5402	Approved
0.8354	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8291	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6599	Discontinued
0.8247	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD3882	Suspended
0.8228	Intermediate Similarity	NPD1511	Approved
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8144	Intermediate Similarity	NPD6959	Discontinued
0.8136	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1240	Approved
0.8012	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7819	Suspended
0.7988	Intermediate Similarity	NPD3787	Discontinued
0.7943	Intermediate Similarity	NPD8313	Approved
0.7943	Intermediate Similarity	NPD8312	Approved
0.7935	Intermediate Similarity	NPD1607	Approved
0.7925	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD8455	Phase 2
0.787	Intermediate Similarity	NPD5494	Approved
0.7861	Intermediate Similarity	NPD7584	Approved
0.7826	Intermediate Similarity	NPD6780	Approved
0.7826	Intermediate Similarity	NPD6777	Approved
0.7826	Intermediate Similarity	NPD6779	Approved
0.7826	Intermediate Similarity	NPD6782	Approved
0.7826	Intermediate Similarity	NPD6781	Approved
0.7826	Intermediate Similarity	NPD6778	Approved
0.7826	Intermediate Similarity	NPD6776	Approved
0.7812	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7701	Intermediate Similarity	NPD7698	Approved
0.7701	Intermediate Similarity	NPD7696	Phase 3
0.7701	Intermediate Similarity	NPD7435	Discontinued
0.7701	Intermediate Similarity	NPD7697	Approved
0.7697	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD7768	Phase 2
0.7688	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7657	Intermediate Similarity	NPD5844	Phase 1
0.7647	Intermediate Similarity	NPD3749	Approved
0.764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7701	Phase 2
0.76	Intermediate Similarity	NPD7228	Approved
0.7592	Intermediate Similarity	NPD8151	Discontinued
0.7574	Intermediate Similarity	NPD1465	Phase 2
0.7572	Intermediate Similarity	NPD6232	Discontinued
0.7566	Intermediate Similarity	NPD7870	Phase 2
0.7566	Intermediate Similarity	NPD7871	Phase 2
0.7554	Intermediate Similarity	NPD6534	Approved
0.7554	Intermediate Similarity	NPD6535	Approved
0.755	Intermediate Similarity	NPD1091	Approved
0.7543	Intermediate Similarity	NPD7473	Discontinued
0.7532	Intermediate Similarity	NPD1933	Approved
0.753	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7685	Pre-registration
0.7527	Intermediate Similarity	NPD7699	Phase 2
0.7527	Intermediate Similarity	NPD7700	Phase 2
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7486	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7874	Approved
0.7461	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6798	Discontinued
0.7448	Intermediate Similarity	NPD7585	Approved
0.744	Intermediate Similarity	NPD7458	Discontinued
0.7436	Intermediate Similarity	NPD6832	Phase 2
0.7425	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD2800	Approved
0.7423	Intermediate Similarity	NPD7801	Approved
0.7423	Intermediate Similarity	NPD1652	Phase 2
0.7407	Intermediate Similarity	NPD7266	Discontinued
0.7405	Intermediate Similarity	NPD6233	Phase 2
0.7399	Intermediate Similarity	NPD919	Approved
0.7396	Intermediate Similarity	NPD7583	Approved
0.7389	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD8319	Approved
0.7382	Intermediate Similarity	NPD8320	Phase 1
0.7375	Intermediate Similarity	NPD6651	Approved
0.7374	Intermediate Similarity	NPD5953	Discontinued
0.7368	Intermediate Similarity	NPD6823	Phase 2
0.7366	Intermediate Similarity	NPD4360	Phase 2
0.7366	Intermediate Similarity	NPD4363	Phase 3
0.7363	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7286	Phase 2
0.7358	Intermediate Similarity	NPD1613	Approved
0.7358	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1203	Approved
0.7346	Intermediate Similarity	NPD2935	Discontinued
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3926	Phase 2
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.732	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1243	Approved
0.7314	Intermediate Similarity	NPD1247	Approved
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.731	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD2798	Approved
0.7305	Intermediate Similarity	NPD2532	Approved
0.7305	Intermediate Similarity	NPD2534	Approved
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2533	Approved
0.7299	Intermediate Similarity	NPD6234	Discontinued
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1548	Phase 1
0.7283	Intermediate Similarity	NPD4965	Approved
0.7283	Intermediate Similarity	NPD4967	Phase 2
0.7283	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7240	Approved
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7229	Intermediate Similarity	NPD6190	Approved
0.7228	Intermediate Similarity	NPD8434	Phase 2
0.7228	Intermediate Similarity	NPD8150	Discontinued
0.7208	Intermediate Similarity	NPD422	Phase 1
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2344	Approved
0.7179	Intermediate Similarity	NPD3225	Approved
0.7178	Intermediate Similarity	NPD2799	Discontinued
0.7161	Intermediate Similarity	NPD9717	Approved
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD943	Approved
0.7135	Intermediate Similarity	NPD3226	Approved
0.7134	Intermediate Similarity	NPD2797	Approved
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7128	Intermediate Similarity	NPD6213	Phase 3
0.7128	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6212	Phase 3
0.7117	Intermediate Similarity	NPD7097	Phase 1
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7107	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD230	Phase 1
0.7097	Intermediate Similarity	NPD1610	Phase 2
0.7094	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4062	Phase 3
0.7063	Intermediate Similarity	NPD3027	Phase 3
0.7044	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2354	Approved
0.7024	Intermediate Similarity	NPD2309	Approved
0.7024	Intermediate Similarity	NPD3887	Approved
0.7006	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD4661	Approved
0.7	Intermediate Similarity	NPD4662	Approved
0.6994	Remote Similarity	NPD447	Suspended
0.6994	Remote Similarity	NPD4340	Discontinued
0.6994	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2346	Discontinued
0.697	Remote Similarity	NPD4308	Phase 3
0.697	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4361	Phase 2
0.6963	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD9545	Approved
0.6946	Remote Similarity	NPD2424	Discontinued

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