NPASS Compound

Structure

NPC470125 OpenBabel07101718192D 42 46 0 0 1 0 0 0 0 0999 V2000 -3.4641 -1.0000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 -6.9282 -1.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 11 1 0 0 0 0 2 15 1 0 0 0 0 3 7 1 0 0 0 0 3 15 2 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 39 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 2 0 0 0 0 14 39 1 0 0 0 0 16 28 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 23 2 0 0 0 0 20 34 1 0 0 0 0 21 23 1 0 0 0 0 21 40 1 0 0 0 0 22 14 1 6 0 0 0 22 24 1 0 0 0 0 22 41 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 1 0 0 0 25 29 1 0 0 0 0 25 36 2 0 0 0 0 26 27 1 0 0 0 0 26 37 1 6 0 0 0 27 30 1 0 0 0 0 27 38 1 1 0 0 0 28 29 2 0 0 0 0 28 40 1 0 0 0 0 29 42 1 0 0 0 0 30 41 1 0 0 0 0 30 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.16
Volume:	558.499
LogP:	2.296
LogD:	2.357
LogS:	-4.507
# Rotatable Bonds:	8
TPSA:	199.51
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.15
Synthetic Accessibility Score:	4.202
Fsp3:	0.233
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.972
MDCK Permeability:	7.006728083069902e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	0.714
Human Intestinal Absorption (HIA):	0.291
20% Bioavailability (F20%):	0.233
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	99.62496185302734%
Volume Distribution (VD):	0.63
Pgp-substrate:	2.4749646186828613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.388
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.665
CYP2D6-inhibitor:	0.651
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	4.196
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.36
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.717
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.952
Carcinogencity:	0.36
Eye Corrosion:	0.003
Eye Irritation:	0.599
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC470125

Natural Product ID:	NPC470125
*Common Name:**	Kaempferol-3-O-Beta-D-(6-E-P-Coumarylglucoside)
IUPAC Name:	5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoxy]methyl]oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	WKMDAUWVMMAWFH-LGASVXPQSA-N
Standard InCHI:	InChI=1S/C30H28O12/c31-17-7-3-15(4-8-17)2-1-11-39-14-22-24(35)26(37)27(38)30(41-22)42-29-25(36)23-20(34)12-19(33)13-21(23)40-28(29)16-5-9-18(32)10-6-16/h1-10,12-13,22,24,26-27,30-35,37-38H,11,14H2/b2-1+/t22-,24-,26+,27-,30+/m1/s1
SMILES:	C1=CC(=CC=C1C=CCOCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1778419
PubChem CID:	54581732
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
NPO21463.1	Aruncus dioicus	Under-species	n.a.	n.a.	aerial parts	n.a.	n.a.	PMID[21546250]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	98.3	ug.mL-1	PMID[504292]
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[504292]

☑ 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 NPC470125 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	452
0.1-0.2	1751
0.2-0.3	4272
0.3-0.4	9879
0.4-0.5	8451
0.5-0.6	4551
0.6-0.7	5786
0.7-0.8	4938
0.8-0.85	1640
0.85-0.9	471
0.9-0.95	406
0.95-1	100

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC19240
0.9806	High Similarity	NPC129264
0.9806	High Similarity	NPC85751
0.9806	High Similarity	NPC205824
0.9804	High Similarity	NPC304741
0.9804	High Similarity	NPC470405
0.9804	High Similarity	NPC471079
0.9803	High Similarity	NPC135391
0.9803	High Similarity	NPC77672
0.9803	High Similarity	NPC78263
0.9803	High Similarity	NPC133671
0.9803	High Similarity	NPC54802
0.9803	High Similarity	NPC197304
0.9742	High Similarity	NPC80068
0.974	High Similarity	NPC249281
0.974	High Similarity	NPC473438
0.974	High Similarity	NPC64305
0.974	High Similarity	NPC163242
0.974	High Similarity	NPC135846
0.974	High Similarity	NPC276377
0.974	High Similarity	NPC173582
0.974	High Similarity	NPC253788
0.974	High Similarity	NPC265885
0.974	High Similarity	NPC476215
0.974	High Similarity	NPC297987
0.974	High Similarity	NPC246943
0.974	High Similarity	NPC116458
0.974	High Similarity	NPC139320
0.974	High Similarity	NPC170052
0.974	High Similarity	NPC181465
0.974	High Similarity	NPC215710
0.9739	High Similarity	NPC320283
0.9739	High Similarity	NPC41121
0.9739	High Similarity	NPC472459
0.9739	High Similarity	NPC111929
0.9737	High Similarity	NPC323593
0.9737	High Similarity	NPC203500
0.9737	High Similarity	NPC307938
0.9679	High Similarity	NPC139060
0.9677	High Similarity	NPC240306
0.9675	High Similarity	NPC136761
0.9675	High Similarity	NPC187379
0.9673	High Similarity	NPC182634
0.9673	High Similarity	NPC108831
0.9613	High Similarity	NPC472994
0.9613	High Similarity	NPC224530
0.9613	High Similarity	NPC195685
0.9613	High Similarity	NPC210961
0.9613	High Similarity	NPC129217
0.9613	High Similarity	NPC282169
0.9613	High Similarity	NPC270675
0.9613	High Similarity	NPC477628
0.9613	High Similarity	NPC48093
0.9613	High Similarity	NPC259957
0.9613	High Similarity	NPC216496
0.9613	High Similarity	NPC477629
0.9613	High Similarity	NPC159579
0.9613	High Similarity	NPC85707
0.9605	High Similarity	NPC83283
0.9605	High Similarity	NPC210003
0.9605	High Similarity	NPC143851
0.9605	High Similarity	NPC39360
0.9605	High Similarity	NPC29763
0.956	High Similarity	NPC280642
0.956	High Similarity	NPC96605
0.956	High Similarity	NPC218161
0.956	High Similarity	NPC164704
0.956	High Similarity	NPC470712
0.9554	High Similarity	NPC76831
0.9554	High Similarity	NPC292929
0.9554	High Similarity	NPC289667
0.9551	High Similarity	NPC150164
0.9551	High Similarity	NPC27942
0.9548	High Similarity	NPC153342
0.9545	High Similarity	NPC44931
0.9545	High Similarity	NPC473512
0.9545	High Similarity	NPC129827
0.9545	High Similarity	NPC65003
0.9545	High Similarity	NPC288084
0.9542	High Similarity	NPC95090
0.9542	High Similarity	NPC27408
0.95	High Similarity	NPC470714
0.95	High Similarity	NPC221288
0.95	High Similarity	NPC101399
0.95	High Similarity	NPC474522
0.95	High Similarity	NPC217822
0.95	High Similarity	NPC470715
0.95	High Similarity	NPC11847
0.95	High Similarity	NPC470716
0.9494	High Similarity	NPC256188
0.9494	High Similarity	NPC221342
0.9494	High Similarity	NPC203145
0.9494	High Similarity	NPC142142
0.9494	High Similarity	NPC11432
0.9494	High Similarity	NPC64425
0.9494	High Similarity	NPC32641
0.9494	High Similarity	NPC476470
0.9494	High Similarity	NPC477613
0.9494	High Similarity	NPC186816
0.9494	High Similarity	NPC189564
0.9494	High Similarity	NPC12013
0.949	High Similarity	NPC121703
0.949	High Similarity	NPC66087
0.949	High Similarity	NPC179198
0.949	High Similarity	NPC278419
0.9484	High Similarity	NPC22062
0.9484	High Similarity	NPC473634
0.9484	High Similarity	NPC104677
0.9484	High Similarity	NPC138811
0.9437	High Similarity	NPC469344
0.9437	High Similarity	NPC188815
0.943	High Similarity	NPC72016
0.943	High Similarity	NPC287889
0.943	High Similarity	NPC135358
0.9427	High Similarity	NPC472876
0.9427	High Similarity	NPC131745
0.9423	High Similarity	NPC473623
0.9419	High Similarity	NPC60966
0.9419	High Similarity	NPC156457
0.9419	High Similarity	NPC6985
0.9419	High Similarity	NPC122809
0.9419	High Similarity	NPC161749
0.9419	High Similarity	NPC197896
0.9419	High Similarity	NPC258035
0.9419	High Similarity	NPC313163
0.9416	High Similarity	NPC169248
0.9416	High Similarity	NPC97052
0.9416	High Similarity	NPC26195
0.9416	High Similarity	NPC39351
0.9416	High Similarity	NPC72649
0.9412	High Similarity	NPC88484
0.9412	High Similarity	NPC259767
0.9412	High Similarity	NPC121001
0.9412	High Similarity	NPC259182
0.9383	High Similarity	NPC214621
0.9383	High Similarity	NPC34267
0.9383	High Similarity	NPC223426
0.9383	High Similarity	NPC81042
0.9375	High Similarity	NPC5319
0.9371	High Similarity	NPC308404
0.9371	High Similarity	NPC253662
0.9371	High Similarity	NPC88789
0.9371	High Similarity	NPC179950
0.9371	High Similarity	NPC473278
0.9371	High Similarity	NPC276222
0.9371	High Similarity	NPC145038
0.9371	High Similarity	NPC118284
0.9371	High Similarity	NPC274618
0.9371	High Similarity	NPC56077
0.9371	High Similarity	NPC281131
0.9371	High Similarity	NPC260504
0.9371	High Similarity	NPC89809
0.9367	High Similarity	NPC183672
0.9363	High Similarity	NPC47923
0.9363	High Similarity	NPC303913
0.9363	High Similarity	NPC101636
0.9359	High Similarity	NPC73511
0.9355	High Similarity	NPC261866
0.9355	High Similarity	NPC295613
0.9355	High Similarity	NPC473657
0.9355	High Similarity	NPC170475
0.9355	High Similarity	NPC206378
0.9351	High Similarity	NPC106625
0.9325	High Similarity	NPC61904
0.9325	High Similarity	NPC231787
0.9325	High Similarity	NPC144097
0.9317	High Similarity	NPC95866
0.9317	High Similarity	NPC138990
0.9317	High Similarity	NPC259896
0.9317	High Similarity	NPC277532
0.9317	High Similarity	NPC255157
0.9317	High Similarity	NPC92815
0.9317	High Similarity	NPC29958
0.9317	High Similarity	NPC175429
0.9317	High Similarity	NPC254855
0.9317	High Similarity	NPC136042
0.9317	High Similarity	NPC67326
0.9317	High Similarity	NPC209550
0.9317	High Similarity	NPC156869
0.9313	High Similarity	NPC52550
0.9313	High Similarity	NPC173637
0.9313	High Similarity	NPC127546
0.9313	High Similarity	NPC317489
0.9313	High Similarity	NPC84362
0.9313	High Similarity	NPC223424
0.9308	High Similarity	NPC277205
0.9308	High Similarity	NPC19388
0.9308	High Similarity	NPC55786
0.9308	High Similarity	NPC240431
0.9304	High Similarity	NPC259834
0.9304	High Similarity	NPC298171
0.9304	High Similarity	NPC244875
0.9304	High Similarity	NPC475382
0.9304	High Similarity	NPC44947
0.9299	High Similarity	NPC246469
0.9299	High Similarity	NPC97285
0.9299	High Similarity	NPC271270
0.9299	High Similarity	NPC142860
0.929	High Similarity	NPC99233
0.9281	High Similarity	NPC191154

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 NPC470125 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	914
0.2-0.3	1904
0.3-0.4	2747
0.4-0.5	1876
0.5-0.6	890
0.6-0.7	273
0.7-0.8	105
0.8-0.85	25
0.85-0.9	7
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9419	High Similarity	NPD4381	Clinical (unspecified phase)
0.9375	High Similarity	NPD7804	Clinical (unspecified phase)
0.9259	High Similarity	NPD6797	Phase 2
0.9202	High Similarity	NPD7251	Discontinued
0.9146	High Similarity	NPD7808	Phase 3
0.903	High Similarity	NPD4338	Clinical (unspecified phase)
0.9018	High Similarity	NPD7054	Approved
0.8963	High Similarity	NPD7472	Approved
0.8848	High Similarity	NPD7074	Phase 3
0.8834	High Similarity	NPD6166	Phase 2
0.8834	High Similarity	NPD6168	Clinical (unspecified phase)
0.8834	High Similarity	NPD6167	Clinical (unspecified phase)
0.879	High Similarity	NPD4380	Phase 2
0.8727	High Similarity	NPD3818	Discontinued
0.8718	High Similarity	NPD5403	Approved
0.8696	High Similarity	NPD7075	Discontinued
0.8679	High Similarity	NPD6801	Discontinued
0.859	High Similarity	NPD5401	Approved
0.8526	High Similarity	NPD6799	Approved
0.8509	High Similarity	NPD7096	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD5402	Approved
0.8442	Intermediate Similarity	NPD1549	Phase 2
0.8412	Intermediate Similarity	NPD6559	Discontinued
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8354	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1934	Approved
0.8302	Intermediate Similarity	NPD1512	Approved
0.8293	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6599	Discontinued
0.8192	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3882	Suspended
0.8176	Intermediate Similarity	NPD3751	Discontinued
0.8176	Intermediate Similarity	NPD1511	Approved
0.8171	Intermediate Similarity	NPD2801	Approved
0.8155	Intermediate Similarity	NPD3787	Discontinued
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8095	Intermediate Similarity	NPD6959	Discontinued
0.8077	Intermediate Similarity	NPD2796	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD8313	Approved
0.7952	Intermediate Similarity	NPD8455	Phase 2
0.7912	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1240	Approved
0.7844	Intermediate Similarity	NPD7819	Suspended
0.7811	Intermediate Similarity	NPD3749	Approved
0.7784	Intermediate Similarity	NPD6781	Approved
0.7784	Intermediate Similarity	NPD6777	Approved
0.7784	Intermediate Similarity	NPD6780	Approved
0.7784	Intermediate Similarity	NPD6782	Approved
0.7784	Intermediate Similarity	NPD6779	Approved
0.7784	Intermediate Similarity	NPD6776	Approved
0.7784	Intermediate Similarity	NPD6778	Approved
0.7771	Intermediate Similarity	NPD1607	Approved
0.7764	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3750	Approved
0.7754	Intermediate Similarity	NPD7435	Discontinued
0.7751	Intermediate Similarity	NPD7768	Phase 2
0.7725	Intermediate Similarity	NPD7584	Approved
0.7714	Intermediate Similarity	NPD5844	Phase 1
0.7702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1653	Approved
0.763	Intermediate Similarity	NPD6232	Discontinued
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6798	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7619	Intermediate Similarity	NPD7871	Phase 2
0.7619	Intermediate Similarity	NPD7870	Phase 2
0.7616	Intermediate Similarity	NPD5494	Approved
0.76	Intermediate Similarity	NPD7473	Discontinued
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6233	Phase 2
0.7572	Intermediate Similarity	NPD7199	Phase 2
0.7566	Intermediate Similarity	NPD7698	Approved
0.7566	Intermediate Similarity	NPD7696	Phase 3
0.7566	Intermediate Similarity	NPD7697	Approved
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6535	Approved
0.7514	Intermediate Similarity	NPD6534	Approved
0.7513	Intermediate Similarity	NPD7874	Approved
0.7513	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD7701	Phase 2
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7458	Intermediate Similarity	NPD7228	Approved
0.7453	Intermediate Similarity	NPD3748	Approved
0.7443	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD1465	Phase 2
0.7396	Intermediate Similarity	NPD7458	Discontinued
0.7394	Intermediate Similarity	NPD7700	Phase 2
0.7394	Intermediate Similarity	NPD7699	Phase 2
0.7394	Intermediate Similarity	NPD6190	Approved
0.7391	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7685	Pre-registration
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7385	Intermediate Similarity	NPD7801	Approved
0.7375	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD919	Approved
0.7346	Intermediate Similarity	NPD7033	Discontinued
0.7344	Intermediate Similarity	NPD8319	Approved
0.7344	Intermediate Similarity	NPD8320	Phase 1
0.733	Intermediate Similarity	NPD6823	Phase 2
0.7322	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7585	Approved
0.7312	Intermediate Similarity	NPD1613	Approved
0.7312	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3926	Phase 2
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7278	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD2800	Approved
0.7273	Intermediate Similarity	NPD1247	Approved
0.7268	Intermediate Similarity	NPD7583	Approved
0.7267	Intermediate Similarity	NPD37	Approved
0.7262	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6234	Discontinued
0.7253	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4967	Phase 2
0.7241	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD4965	Approved
0.7238	Intermediate Similarity	NPD5953	Discontinued
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7234	Intermediate Similarity	NPD4360	Phase 2
0.7234	Intermediate Similarity	NPD4363	Phase 3
0.7228	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6651	Approved
0.7222	Intermediate Similarity	NPD7286	Phase 2
0.7202	Intermediate Similarity	NPD7390	Discontinued
0.7195	Intermediate Similarity	NPD2935	Discontinued
0.7189	Intermediate Similarity	NPD8150	Discontinued
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.7169	Intermediate Similarity	NPD1243	Approved
0.716	Intermediate Similarity	NPD2532	Approved
0.716	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD2533	Approved
0.716	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD2798	Approved
0.7134	Intermediate Similarity	NPD3225	Approved
0.7104	Intermediate Similarity	NPD7240	Approved
0.7099	Intermediate Similarity	NPD943	Approved
0.7097	Intermediate Similarity	NPD8434	Phase 2
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3226	Approved
0.709	Intermediate Similarity	NPD6213	Phase 3
0.709	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6212	Phase 3
0.7081	Intermediate Similarity	NPD3268	Approved
0.7073	Intermediate Similarity	NPD7097	Phase 1
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4340	Discontinued
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7051	Intermediate Similarity	NPD422	Phase 1
0.7037	Intermediate Similarity	NPD4062	Phase 3
0.703	Intermediate Similarity	NPD2799	Discontinued
0.7011	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD7213	Phase 3
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7212	Phase 2
0.6988	Remote Similarity	NPD6099	Approved
0.6988	Remote Similarity	NPD6100	Approved
0.6982	Remote Similarity	NPD3887	Approved
0.6982	Remote Similarity	NPD2354	Approved
0.6982	Remote Similarity	NPD2309	Approved
0.6981	Remote Similarity	NPD2797	Approved
0.6971	Remote Similarity	NPD6844	Discontinued
0.6954	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD230	Phase 1
0.6931	Remote Similarity	NPD4287	Approved
0.6928	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3027	Phase 3
0.6893	Remote Similarity	NPD4288	Approved
0.6868	Remote Similarity	NPD2403	Approved
0.6864	Remote Similarity	NPD2654	Approved
0.686	Remote Similarity	NPD7447	Phase 1
0.686	Remote Similarity	NPD4662	Approved
0.686	Remote Similarity	NPD4661	Approved
0.6848	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD447	Suspended

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