NPASS Compound

Structure

NPC136761 OpenBabel07101718322D 43 47 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 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 -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 -1.5000 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 -4.3301 2.5000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 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 6.9282 -2.0000 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 -3.4641 3.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 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 4.5000 0.0000 C 0 0 1 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 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 -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 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 5.1962 -3.0000 0.0000 O 0 0 0 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 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 -2.5981 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 11 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 13 2 0 0 0 0 7 28 1 0 0 0 0 8 29 1 0 0 0 0 9 24 1 0 0 0 0 10 30 1 0 0 0 0 11 39 1 0 0 0 0 12 16 2 0 0 0 0 12 31 1 0 0 0 0 13 16 1 0 0 0 0 13 40 1 0 0 0 0 14 7 1 6 0 0 0 14 17 1 0 0 0 0 14 41 1 0 0 0 0 15 8 1 6 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 32 1 1 0 0 0 18 21 1 0 0 0 0 18 33 1 1 0 0 0 19 22 1 0 0 0 0 19 34 2 0 0 0 0 20 23 1 0 0 0 0 20 35 1 6 0 0 0 21 25 1 0 0 0 0 21 36 1 6 0 0 0 22 24 2 0 0 0 0 22 37 1 0 0 0 0 23 26 1 0 0 0 0 23 38 1 1 0 0 0 24 40 1 0 0 0 0 25 27 1 0 0 0 0 25 43 1 1 0 0 0 26 41 1 0 0 0 0 26 43 1 6 0 0 0 27 39 1 6 0 0 0 27 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.15
Volume:	552.318
LogP:	-0.484
LogD:	-0.351
LogS:	-2.783
# Rotatable Bonds:	7
TPSA:	269.43
# H-Bond Aceptor:	16
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.133
Synthetic Accessibility Score:	4.674
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.533
MDCK Permeability:	2.2785065084462985e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.97
Human Intestinal Absorption (HIA):	0.895
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.104
Plasma Protein Binding (PPB):	84.9355697631836%
Volume Distribution (VD):	0.7
Pgp-substrate:	13.029755592346191%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	1.219
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.429
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.834
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.274
Carcinogencity:	0.107
Eye Corrosion:	0.003
Eye Irritation:	0.047
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC136761

Natural Product ID:	NPC136761
*Common Name:**	Kaempferol 4'-O-Beta-D-Glucopyranosyl-(1->2)-Beta-D-Glucopyranoside
IUPAC Name:	2-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]-3,5,7-trihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	LKCFMVKTPNASKS-KWERPHBTSA-N
Standard InCHI:	InChI=1S/C27H30O16/c28-7-14-17(32)20(35)23(38)26(41-14)43-25-21(36)18(33)15(8-29)42-27(25)39-11-3-1-9(2-4-11)24-22(37)19(34)16-12(31)5-10(30)6-13(16)40-24/h1-6,14-15,17-18,20-21,23,25-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,23-,25-,26+,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2)c2oc3cc(O)cc(c3c(=O)c2O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2336773
PubChem CID:	71720752
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	=	458.2	ng/ml	PMID[564535]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1078.0	mg/dl	PMID[564535]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	113.1	mg/dl	PMID[564535]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	10.91	mg kg-1	PMID[564535]

☑ 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 NPC136761 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	463
0.1-0.2	1793
0.2-0.3	4352
0.3-0.4	10073
0.4-0.5	8378
0.5-0.6	4674
0.6-0.7	5785
0.7-0.8	5133
0.8-0.85	1138
0.85-0.9	412
0.9-0.95	421
0.95-1	75

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC170052
0.9934	High Similarity	NPC135846
0.9934	High Similarity	NPC297987
0.9934	High Similarity	NPC64305
0.9868	High Similarity	NPC304741
0.9868	High Similarity	NPC470405
0.9868	High Similarity	NPC187379
0.9868	High Similarity	NPC471079
0.9804	High Similarity	NPC181465
0.9804	High Similarity	NPC473438
0.9804	High Similarity	NPC249281
0.9804	High Similarity	NPC265885
0.9804	High Similarity	NPC163242
0.9804	High Similarity	NPC246943
0.9804	High Similarity	NPC173582
0.9804	High Similarity	NPC139320
0.9804	High Similarity	NPC116458
0.9804	High Similarity	NPC476215
0.9804	High Similarity	NPC276377
0.9804	High Similarity	NPC253788
0.9804	High Similarity	NPC215710
0.9801	High Similarity	NPC307938
0.9801	High Similarity	NPC203500
0.9801	High Similarity	NPC323593
0.9742	High Similarity	NPC292929
0.9742	High Similarity	NPC287889
0.9742	High Similarity	NPC289667
0.9742	High Similarity	NPC135358
0.9742	High Similarity	NPC76831
0.974	High Similarity	NPC240306
0.9737	High Similarity	NPC77672
0.9737	High Similarity	NPC473512
0.9737	High Similarity	NPC108831
0.9737	High Similarity	NPC182634
0.9737	High Similarity	NPC54802
0.9737	High Similarity	NPC65003
0.9737	High Similarity	NPC129827
0.9737	High Similarity	NPC133671
0.9737	High Similarity	NPC44931
0.9737	High Similarity	NPC78263
0.9737	High Similarity	NPC135391
0.9737	High Similarity	NPC197304
0.9679	High Similarity	NPC203145
0.9679	High Similarity	NPC476470
0.9679	High Similarity	NPC32641
0.9679	High Similarity	NPC221342
0.9679	High Similarity	NPC142142
0.9679	High Similarity	NPC11432
0.9679	High Similarity	NPC12013
0.9679	High Similarity	NPC256188
0.9679	High Similarity	NPC64425
0.9679	High Similarity	NPC477613
0.9679	High Similarity	NPC186816
0.9679	High Similarity	NPC189564
0.9675	High Similarity	NPC470125
0.9673	High Similarity	NPC473634
0.9673	High Similarity	NPC41121
0.9673	High Similarity	NPC320283
0.9673	High Similarity	NPC111929
0.9673	High Similarity	NPC22062
0.9673	High Similarity	NPC472459
0.9673	High Similarity	NPC138811
0.9669	High Similarity	NPC29763
0.9669	High Similarity	NPC83283
0.9669	High Similarity	NPC143851
0.9669	High Similarity	NPC39360
0.9669	High Similarity	NPC210003
0.9613	High Similarity	NPC298171
0.9613	High Similarity	NPC244875
0.9613	High Similarity	NPC475382
0.961	High Similarity	NPC153342
0.961	High Similarity	NPC473623
0.9605	High Similarity	NPC169248
0.9605	High Similarity	NPC97052
0.9605	High Similarity	NPC26195
0.9605	High Similarity	NPC95090
0.9605	High Similarity	NPC72649
0.9605	High Similarity	NPC27408
0.9605	High Similarity	NPC39351
0.9551	High Similarity	NPC311850
0.9551	High Similarity	NPC80068
0.9551	High Similarity	NPC473644
0.9548	High Similarity	NPC101636
0.9548	High Similarity	NPC282169
0.9548	High Similarity	NPC129217
0.9548	High Similarity	NPC159579
0.9548	High Similarity	NPC48093
0.9548	High Similarity	NPC47923
0.9548	High Similarity	NPC303913
0.9548	High Similarity	NPC85707
0.9548	High Similarity	NPC259957
0.9548	High Similarity	NPC224530
0.9548	High Similarity	NPC216496
0.9542	High Similarity	NPC206378
0.9542	High Similarity	NPC473657
0.9542	High Similarity	NPC170475
0.9542	High Similarity	NPC295613
0.9497	High Similarity	NPC254855
0.9497	High Similarity	NPC175429
0.9497	High Similarity	NPC138990
0.9497	High Similarity	NPC156869
0.9497	High Similarity	NPC470712
0.9497	High Similarity	NPC29958
0.9497	High Similarity	NPC209550
0.9497	High Similarity	NPC285197
0.9497	High Similarity	NPC136042
0.9497	High Similarity	NPC277532
0.9497	High Similarity	NPC164704
0.9497	High Similarity	NPC259896
0.9497	High Similarity	NPC67105
0.9497	High Similarity	NPC67326
0.9497	High Similarity	NPC255157
0.9494	High Similarity	NPC275454
0.949	High Similarity	NPC205824
0.949	High Similarity	NPC129264
0.949	High Similarity	NPC85751
0.949	High Similarity	NPC139060
0.949	High Similarity	NPC19240
0.9487	High Similarity	NPC27942
0.9487	High Similarity	NPC259834
0.9487	High Similarity	NPC150164
0.9487	High Similarity	NPC131745
0.9487	High Similarity	NPC44947
0.9484	High Similarity	NPC246469
0.9484	High Similarity	NPC142860
0.9484	High Similarity	NPC271270
0.9484	High Similarity	NPC97285
0.9481	High Similarity	NPC313163
0.9481	High Similarity	NPC161749
0.9481	High Similarity	NPC197896
0.9481	High Similarity	NPC258035
0.9481	High Similarity	NPC288084
0.9481	High Similarity	NPC6985
0.9481	High Similarity	NPC122809
0.9481	High Similarity	NPC156457
0.9481	High Similarity	NPC60966
0.9474	High Similarity	NPC121001
0.9474	High Similarity	NPC88484
0.9474	High Similarity	NPC259767
0.9474	High Similarity	NPC259182
0.9437	High Similarity	NPC470714
0.9437	High Similarity	NPC470716
0.9437	High Similarity	NPC155877
0.9437	High Similarity	NPC470715
0.9437	High Similarity	NPC134532
0.9437	High Similarity	NPC471748
0.9437	High Similarity	NPC26230
0.9437	High Similarity	NPC471725
0.9437	High Similarity	NPC60735
0.9437	High Similarity	NPC33054
0.9437	High Similarity	NPC203259
0.9437	High Similarity	NPC176740
0.9437	High Similarity	NPC474522
0.9434	High Similarity	NPC227508
0.9434	High Similarity	NPC5319
0.943	High Similarity	NPC8856
0.943	High Similarity	NPC298666
0.943	High Similarity	NPC68592
0.943	High Similarity	NPC262222
0.9427	High Similarity	NPC278419
0.9427	High Similarity	NPC257566
0.9427	High Similarity	NPC179198
0.9427	High Similarity	NPC124155
0.9427	High Similarity	NPC66087
0.9427	High Similarity	NPC121703
0.9427	High Similarity	NPC183672
0.9423	High Similarity	NPC210961
0.9423	High Similarity	NPC477629
0.9423	High Similarity	NPC472994
0.9423	High Similarity	NPC195685
0.9423	High Similarity	NPC270675
0.9423	High Similarity	NPC477628
0.9419	High Similarity	NPC308265
0.9419	High Similarity	NPC104677
0.9419	High Similarity	NPC73511
0.9416	High Similarity	NPC261866
0.9412	High Similarity	NPC106625
0.9375	High Similarity	NPC95866
0.9367	High Similarity	NPC277205
0.9367	High Similarity	NPC72016
0.9363	High Similarity	NPC190450
0.9363	High Similarity	NPC472876
0.9359	High Similarity	NPC472320
0.9359	High Similarity	NPC271479
0.9359	High Similarity	NPC200708
0.9351	High Similarity	NPC99233
0.9342	High Similarity	NPC191154
0.9321	High Similarity	NPC19108
0.9321	High Similarity	NPC476472
0.9321	High Similarity	NPC253685
0.9321	High Similarity	NPC473327
0.9321	High Similarity	NPC16194
0.9321	High Similarity	NPC220173
0.9321	High Similarity	NPC294815
0.9313	High Similarity	NPC86008
0.9308	High Similarity	NPC118284
0.9308	High Similarity	NPC21100
0.9308	High Similarity	NPC281131
0.9308	High Similarity	NPC197285
0.9308	High Similarity	NPC210073

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 NPC136761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	925
0.2-0.3	1926
0.3-0.4	2802
0.4-0.5	1861
0.5-0.6	857
0.6-0.7	240
0.7-0.8	105
0.8-0.85	15
0.85-0.9	6
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD4381	Clinical (unspecified phase)
0.9437	High Similarity	NPD6797	Phase 2
0.9434	High Similarity	NPD7804	Clinical (unspecified phase)
0.9379	High Similarity	NPD7251	Discontinued
0.9321	High Similarity	NPD7808	Phase 3
0.9255	High Similarity	NPD7472	Approved
0.9193	High Similarity	NPD7054	Approved
0.9018	High Similarity	NPD7074	Phase 3
0.897	High Similarity	NPD4338	Clinical (unspecified phase)
0.8846	High Similarity	NPD4380	Phase 2
0.878	High Similarity	NPD3818	Discontinued
0.8773	High Similarity	NPD6167	Clinical (unspecified phase)
0.8773	High Similarity	NPD6168	Clinical (unspecified phase)
0.8773	High Similarity	NPD6166	Phase 2
0.8654	High Similarity	NPD5403	Approved
0.8634	High Similarity	NPD7075	Discontinued
0.8616	High Similarity	NPD6801	Discontinued
0.8553	High Similarity	NPD1550	Clinical (unspecified phase)
0.8553	High Similarity	NPD1552	Clinical (unspecified phase)
0.8526	High Similarity	NPD4378	Clinical (unspecified phase)
0.8526	High Similarity	NPD5401	Approved
0.8497	Intermediate Similarity	NPD1549	Phase 2
0.8462	Intermediate Similarity	NPD6799	Approved
0.8447	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD5402	Approved
0.8395	Intermediate Similarity	NPD3817	Phase 2
0.8385	Intermediate Similarity	NPD1934	Approved
0.8354	Intermediate Similarity	NPD1512	Approved
0.8353	Intermediate Similarity	NPD6559	Discontinued
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1511	Approved
0.8221	Intermediate Similarity	NPD2801	Approved
0.821	Intermediate Similarity	NPD7411	Suspended
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8176	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8129	Intermediate Similarity	NPD2796	Approved
0.8121	Intermediate Similarity	NPD3882	Suspended
0.8121	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD8313	Approved
0.8046	Intermediate Similarity	NPD8312	Approved
0.8036	Intermediate Similarity	NPD6959	Discontinued
0.8034	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD8455	Phase 2
0.7988	Intermediate Similarity	NPD3787	Discontinued
0.7922	Intermediate Similarity	NPD1240	Approved
0.7895	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7819	Suspended
0.7821	Intermediate Similarity	NPD1607	Approved
0.7812	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7584	Approved
0.7765	Intermediate Similarity	NPD5494	Approved
0.773	Intermediate Similarity	NPD6780	Approved
0.773	Intermediate Similarity	NPD6779	Approved
0.773	Intermediate Similarity	NPD6776	Approved
0.773	Intermediate Similarity	NPD6781	Approved
0.773	Intermediate Similarity	NPD6778	Approved
0.773	Intermediate Similarity	NPD6782	Approved
0.773	Intermediate Similarity	NPD6777	Approved
0.7697	Intermediate Similarity	NPD1653	Approved
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7663	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3749	Approved
0.7606	Intermediate Similarity	NPD7696	Phase 3
0.7606	Intermediate Similarity	NPD7435	Discontinued
0.7606	Intermediate Similarity	NPD7697	Approved
0.7606	Intermediate Similarity	NPD7698	Approved
0.7593	Intermediate Similarity	NPD4628	Phase 3
0.7592	Intermediate Similarity	NPD8151	Discontinued
0.7588	Intermediate Similarity	NPD7768	Phase 2
0.7578	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1465	Phase 2
0.7557	Intermediate Similarity	NPD5844	Phase 1
0.755	Intermediate Similarity	NPD1091	Approved
0.7539	Intermediate Similarity	NPD7701	Phase 2
0.7531	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD3748	Approved
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.7471	Intermediate Similarity	NPD6232	Discontinued
0.7459	Intermediate Similarity	NPD6535	Approved
0.7459	Intermediate Similarity	NPD6534	Approved
0.7443	Intermediate Similarity	NPD7473	Discontinued
0.7433	Intermediate Similarity	NPD7700	Phase 2
0.7433	Intermediate Similarity	NPD7699	Phase 2
0.743	Intermediate Similarity	NPD7685	Pre-registration
0.7429	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7783	Phase 2
0.7423	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1933	Approved
0.7414	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD7033	Discontinued
0.7386	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7874	Approved
0.7358	Intermediate Similarity	NPD1613	Approved
0.7358	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7585	Approved
0.7355	Intermediate Similarity	NPD1203	Approved
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7337	Intermediate Similarity	NPD7458	Discontinued
0.7333	Intermediate Similarity	NPD7801	Approved
0.7325	Intermediate Similarity	NPD6832	Phase 2
0.7321	Intermediate Similarity	NPD920	Approved
0.732	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2800	Approved
0.7317	Intermediate Similarity	NPD1652	Phase 2
0.7306	Intermediate Similarity	NPD7583	Approved
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7266	Discontinued
0.7299	Intermediate Similarity	NPD919	Approved
0.7296	Intermediate Similarity	NPD6233	Phase 2
0.7293	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD8319	Approved
0.7292	Intermediate Similarity	NPD8320	Phase 1
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1548	Phase 1
0.7278	Intermediate Similarity	NPD5953	Discontinued
0.7277	Intermediate Similarity	NPD6823	Phase 2
0.7273	Intermediate Similarity	NPD4360	Phase 2
0.7273	Intermediate Similarity	NPD4363	Phase 3
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6651	Approved
0.7263	Intermediate Similarity	NPD7286	Phase 2
0.7243	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2935	Discontinued
0.7238	Intermediate Similarity	NPD7240	Approved
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7232	Intermediate Similarity	NPD3926	Phase 2
0.7229	Intermediate Similarity	NPD6190	Approved
0.7228	Intermediate Similarity	NPD8434	Phase 2
0.7216	Intermediate Similarity	NPD1247	Approved
0.7215	Intermediate Similarity	NPD4908	Phase 1
0.7212	Intermediate Similarity	NPD1243	Approved
0.7209	Intermediate Similarity	NPD37	Approved
0.7205	Intermediate Similarity	NPD5124	Phase 1
0.7205	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2532	Approved
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2533	Approved
0.7202	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD6234	Discontinued
0.7197	Intermediate Similarity	NPD2798	Approved
0.7184	Intermediate Similarity	NPD4966	Approved
0.7184	Intermediate Similarity	NPD4967	Phase 2
0.7184	Intermediate Similarity	NPD4965	Approved
0.7179	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7125	Intermediate Similarity	NPD3268	Approved
0.7125	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7097	Intermediate Similarity	NPD1610	Phase 2
0.7091	Intermediate Similarity	NPD2344	Approved
0.7073	Intermediate Similarity	NPD2799	Discontinued
0.7052	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD9717	Approved
0.7044	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7390	Discontinued
0.7037	Intermediate Similarity	NPD6213	Phase 3
0.7037	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6212	Phase 3
0.7035	Intermediate Similarity	NPD3226	Approved
0.703	Intermediate Similarity	NPD6099	Approved
0.703	Intermediate Similarity	NPD6100	Approved
0.7025	Intermediate Similarity	NPD2797	Approved
0.7012	Intermediate Similarity	NPD7097	Phase 1
0.7011	Intermediate Similarity	NPD6844	Discontinued
0.701	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4340	Discontinued
0.6994	Remote Similarity	NPD230	Phase 1
0.6975	Remote Similarity	NPD4062	Phase 3
0.697	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3027	Phase 3
0.6936	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4288	Approved
0.6923	Remote Similarity	NPD3887	Approved
0.6923	Remote Similarity	NPD2309	Approved
0.6923	Remote Similarity	NPD2354	Approved
0.6905	Remote Similarity	NPD2654	Approved
0.6904	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4661	Approved
0.6901	Remote Similarity	NPD4662	Approved
0.689	Remote Similarity	NPD447	Suspended
0.689	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2346	Discontinued
0.6875	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4361	Phase 2
0.6867	Remote Similarity	NPD4308	Phase 3
0.6864	Remote Similarity	NPD6398	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