NPASS Compound

Structure

NPC476247 OpenBabel07101718222D 33 36 0 0 1 0 0 0 0 0999 V2000 -4.3301 -0.5000 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 4.3301 -0.5000 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 3.4641 0.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 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 -1.7321 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 -3.0000 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 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 16 25 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 19 28 2 0 0 0 0 20 24 1 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 26 2 0 0 0 0 25 33 1 0 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.15
Volume:	456.557
LogP:	3.906
LogD:	3.484
LogS:	-4.295
# Rotatable Bonds:	6
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	3.449
Fsp3:	0.192
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.012
MDCK Permeability:	9.619328920962289e-06
Pgp-inhibitor:	0.142
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	100.14371490478516%
Volume Distribution (VD):	0.439
Pgp-substrate:	0.9758386015892029%

ADMET: Metabolism

CYP1A2-inhibitor:	0.457
CYP1A2-substrate:	0.802
CYP2C19-inhibitor:	0.609
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.875
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.617
CYP2D6-substrate:	0.735
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.573

ADMET: Excretion

Clearance (CL):	7.964
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.583
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.206
Skin Sensitization:	0.827
Carcinogencity:	0.688
Eye Corrosion:	0.003
Eye Irritation:	0.583
Respiratory Toxicity:	0.303

Download Data

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

Natural Product: NPC476247

Natural Product ID:	NPC476247
*Common Name:**	8-[(E)-4-Phenylprop-2-En-1-One]-2-(3-Methoxyl-4-Hydroxyphenyl)-3,4-Dihydro-2H-2-Benzopyran-5-Methoxyl-3,7-Diol
IUPAC Name:	(E)-1-[3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-3,4-dihydro-2H-chromen-8-yl]-3-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	DOVZXLLTBZQJDB-CSKARUKUSA-N
Standard InCHI:	InChI=1S/C26H24O7/c1-31-22-14-20(29)24(19(28)10-8-15-6-4-3-5-7-15)26-17(22)13-21(30)25(33-26)16-9-11-18(27)23(12-16)32-2/h3-12,14,21,25,27,29-30H,13H2,1-2H3/b10-8+
SMILES:	COC1=C(C=CC(=C1)C2C(CC3=C(C=C(C(=C3O2)C(=O)C=CC4=CC=CC=C4)O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558296
PubChem CID:	44188970
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins

*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
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757720]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593279]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	China	n.a.	PMID[19278239]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	Ywar Taw village, Shan State of Myanmar	2006-Dec	PMID[19572611]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	6400.0	nM	PMID[568864]

☑ 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 NPC476247 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	418
0.1-0.2	1588
0.2-0.3	3860
0.3-0.4	9526
0.4-0.5	8790
0.5-0.6	3310
0.6-0.7	4734
0.7-0.8	5166
0.8-0.85	2748
0.85-0.9	2006
0.9-0.95	497
0.95-1	54

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC142252
0.9742	High Similarity	NPC474034
0.9742	High Similarity	NPC474033
0.9739	High Similarity	NPC472598
0.9739	High Similarity	NPC291508
0.9739	High Similarity	NPC474055
0.9677	High Similarity	NPC474038
0.9677	High Similarity	NPC158188
0.9677	High Similarity	NPC26326
0.9677	High Similarity	NPC472632
0.9673	High Similarity	NPC278778
0.9673	High Similarity	NPC35038
0.9673	High Similarity	NPC78492
0.9673	High Similarity	NPC208152
0.9673	High Similarity	NPC195796
0.9673	High Similarity	NPC291878
0.9613	High Similarity	NPC287328
0.9613	High Similarity	NPC282009
0.9613	High Similarity	NPC119209
0.9613	High Similarity	NPC475784
0.9613	High Similarity	NPC118256
0.9613	High Similarity	NPC192686
0.9613	High Similarity	NPC174953
0.961	High Similarity	NPC27337
0.9608	High Similarity	NPC470327
0.9608	High Similarity	NPC321779
0.9608	High Similarity	NPC477503
0.9608	High Similarity	NPC45849
0.9608	High Similarity	NPC200761
0.956	High Similarity	NPC475212
0.9554	High Similarity	NPC472625
0.9554	High Similarity	NPC124038
0.9551	High Similarity	NPC113163
0.9551	High Similarity	NPC66618
0.9551	High Similarity	NPC471210
0.9551	High Similarity	NPC288131
0.9551	High Similarity	NPC84324
0.9551	High Similarity	NPC305987
0.9551	High Similarity	NPC472634
0.9551	High Similarity	NPC134783
0.9551	High Similarity	NPC471499
0.9551	High Similarity	NPC165970
0.9548	High Similarity	NPC473990
0.9548	High Similarity	NPC172202
0.9548	High Similarity	NPC22192
0.9548	High Similarity	NPC284127
0.9548	High Similarity	NPC476410
0.9548	High Similarity	NPC117418
0.9548	High Similarity	NPC53545
0.9545	High Similarity	NPC470328
0.9545	High Similarity	NPC209614
0.9545	High Similarity	NPC472626
0.9542	High Similarity	NPC192083
0.9542	High Similarity	NPC18727
0.9542	High Similarity	NPC213896
0.95	High Similarity	NPC279209
0.95	High Similarity	NPC102277
0.9497	High Similarity	NPC243877
0.9497	High Similarity	NPC14662
0.9497	High Similarity	NPC260266
0.9494	High Similarity	NPC7154
0.9494	High Similarity	NPC36
0.9494	High Similarity	NPC125039
0.9494	High Similarity	NPC471788
0.9494	High Similarity	NPC58223
0.9494	High Similarity	NPC36916
0.9494	High Similarity	NPC72787
0.9494	High Similarity	NPC7688
0.949	High Similarity	NPC472635
0.9487	High Similarity	NPC470326
0.9487	High Similarity	NPC472631
0.9487	High Similarity	NPC472630
0.9487	High Similarity	NPC472624
0.9487	High Similarity	NPC101731
0.9487	High Similarity	NPC36217
0.9484	High Similarity	NPC63454
0.9484	High Similarity	NPC284820
0.9484	High Similarity	NPC223787
0.9484	High Similarity	NPC52889
0.9484	High Similarity	NPC52530
0.9484	High Similarity	NPC471209
0.9484	High Similarity	NPC183851
0.9484	High Similarity	NPC473272
0.9481	High Similarity	NPC152951
0.9481	High Similarity	NPC226025
0.9481	High Similarity	NPC168247
0.9481	High Similarity	NPC57674
0.9481	High Similarity	NPC117992
0.9481	High Similarity	NPC230149
0.9477	High Similarity	NPC236637
0.9477	High Similarity	NPC106976
0.9477	High Similarity	NPC219582
0.9477	High Similarity	NPC302950
0.9434	High Similarity	NPC471213
0.943	High Similarity	NPC186686
0.9427	High Similarity	NPC471211
0.9427	High Similarity	NPC289771
0.9427	High Similarity	NPC471212
0.9423	High Similarity	NPC184755
0.9423	High Similarity	NPC250214
0.9423	High Similarity	NPC74178
0.9423	High Similarity	NPC95936
0.9423	High Similarity	NPC204879
0.9419	High Similarity	NPC326037
0.9419	High Similarity	NPC320825
0.9419	High Similarity	NPC13858
0.9416	High Similarity	NPC227337
0.9416	High Similarity	NPC74924
0.9416	High Similarity	NPC273462
0.9416	High Similarity	NPC298692
0.9416	High Similarity	NPC49402
0.9416	High Similarity	NPC70433
0.9416	High Similarity	NPC33051
0.9371	High Similarity	NPC62261
0.9371	High Similarity	NPC293319
0.9371	High Similarity	NPC300053
0.9371	High Similarity	NPC108433
0.9371	High Similarity	NPC472277
0.9371	High Similarity	NPC477840
0.9367	High Similarity	NPC201800
0.9367	High Similarity	NPC474150
0.9367	High Similarity	NPC219927
0.9367	High Similarity	NPC477841
0.9367	High Similarity	NPC472448
0.9367	High Similarity	NPC474162
0.9367	High Similarity	NPC472964
0.9367	High Similarity	NPC220912
0.9367	High Similarity	NPC83922
0.9363	High Similarity	NPC321399
0.9363	High Similarity	NPC472902
0.9363	High Similarity	NPC328102
0.9359	High Similarity	NPC210084
0.9359	High Similarity	NPC471479
0.9359	High Similarity	NPC78071
0.9359	High Similarity	NPC475267
0.9359	High Similarity	NPC48208
0.9359	High Similarity	NPC218313
0.9359	High Similarity	NPC474208
0.9359	High Similarity	NPC262286
0.9359	High Similarity	NPC471515
0.9359	High Similarity	NPC299520
0.9359	High Similarity	NPC36852
0.9359	High Similarity	NPC474681
0.9359	High Similarity	NPC99597
0.9359	High Similarity	NPC129684
0.9359	High Similarity	NPC162869
0.9359	High Similarity	NPC67876
0.9359	High Similarity	NPC156057
0.9359	High Similarity	NPC474836
0.9359	High Similarity	NPC78225
0.9355	High Similarity	NPC234255
0.9355	High Similarity	NPC256925
0.9351	High Similarity	NPC324233
0.9351	High Similarity	NPC471982
0.9351	High Similarity	NPC472912
0.9351	High Similarity	NPC477231
0.9351	High Similarity	NPC323626
0.9351	High Similarity	NPC257648
0.9346	High Similarity	NPC338131
0.9321	High Similarity	NPC271848
0.9321	High Similarity	NPC262580
0.9321	High Similarity	NPC4200
0.9321	High Similarity	NPC81332
0.9321	High Similarity	NPC289396
0.9321	High Similarity	NPC212038
0.9317	High Similarity	NPC288813
0.9313	High Similarity	NPC13481
0.9313	High Similarity	NPC43319
0.9313	High Similarity	NPC119589
0.9313	High Similarity	NPC207575
0.9308	High Similarity	NPC476295
0.9308	High Similarity	NPC18100
0.9308	High Similarity	NPC472281
0.9308	High Similarity	NPC205265
0.9304	High Similarity	NPC29876
0.9304	High Similarity	NPC266314
0.9304	High Similarity	NPC308992
0.9304	High Similarity	NPC167678
0.9304	High Similarity	NPC228383
0.9299	High Similarity	NPC187792
0.9299	High Similarity	NPC210459
0.9295	High Similarity	NPC471985
0.9295	High Similarity	NPC6633
0.9295	High Similarity	NPC472916
0.9295	High Similarity	NPC472455
0.9295	High Similarity	NPC250922
0.9295	High Similarity	NPC191146
0.9295	High Similarity	NPC282307
0.9295	High Similarity	NPC255106
0.9295	High Similarity	NPC170026
0.9295	High Similarity	NPC235165
0.9295	High Similarity	NPC68093
0.9295	High Similarity	NPC138243
0.9295	High Similarity	NPC470600
0.9295	High Similarity	NPC471500
0.9295	High Similarity	NPC133970
0.9295	High Similarity	NPC5322
0.929	High Similarity	NPC256346
0.929	High Similarity	NPC7989
0.929	High Similarity	NPC246328

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 NPC476247 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	921
0.2-0.3	1721
0.3-0.4	2614
0.4-0.5	1826
0.5-0.6	1000
0.6-0.7	491
0.7-0.8	144
0.8-0.85	31
0.85-0.9	25
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9542	High Similarity	NPD2393	Clinical (unspecified phase)
0.9494	High Similarity	NPD6166	Phase 2
0.9494	High Similarity	NPD6167	Clinical (unspecified phase)
0.9494	High Similarity	NPD6168	Clinical (unspecified phase)
0.9477	High Similarity	NPD1934	Approved
0.9097	High Similarity	NPD4380	Phase 2
0.9051	High Similarity	NPD4868	Clinical (unspecified phase)
0.9045	High Similarity	NPD2801	Approved
0.9024	High Similarity	NPD7074	Phase 3
0.8963	High Similarity	NPD7054	Approved
0.8931	High Similarity	NPD3882	Suspended
0.8909	High Similarity	NPD7472	Approved
0.8902	High Similarity	NPD3818	Discontinued
0.8882	High Similarity	NPD5494	Approved
0.8848	High Similarity	NPD5844	Phase 1
0.8831	High Similarity	NPD1511	Approved
0.8758	High Similarity	NPD4381	Clinical (unspecified phase)
0.8758	High Similarity	NPD7075	Discontinued
0.875	High Similarity	NPD8443	Clinical (unspecified phase)
0.8743	High Similarity	NPD6797	Phase 2
0.8718	High Similarity	NPD1512	Approved
0.869	High Similarity	NPD7251	Discontinued
0.8688	High Similarity	NPD7096	Clinical (unspecified phase)
0.8679	High Similarity	NPD7411	Suspended
0.8654	High Similarity	NPD4378	Clinical (unspecified phase)
0.8654	High Similarity	NPD7410	Clinical (unspecified phase)
0.8639	High Similarity	NPD7808	Phase 3
0.8639	High Similarity	NPD4338	Clinical (unspecified phase)
0.8634	High Similarity	NPD3817	Phase 2
0.8631	High Similarity	NPD7993	Clinical (unspecified phase)
0.8627	High Similarity	NPD1549	Phase 2
0.8598	High Similarity	NPD6959	Discontinued
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8545	High Similarity	NPD6232	Discontinued
0.8512	High Similarity	NPD7804	Clinical (unspecified phase)
0.8509	High Similarity	NPD6801	Discontinued
0.8503	High Similarity	NPD7473	Discontinued
0.8471	Intermediate Similarity	NPD6559	Discontinued
0.8457	Intermediate Similarity	NPD7819	Suspended
0.8377	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1510	Phase 2
0.8242	Intermediate Similarity	NPD7768	Phase 2
0.8239	Intermediate Similarity	NPD6799	Approved
0.8232	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD5402	Approved
0.817	Intermediate Similarity	NPD1240	Approved
0.817	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1613	Approved
0.8101	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD5403	Approved
0.8065	Intermediate Similarity	NPD1607	Approved
0.8052	Intermediate Similarity	NPD943	Approved
0.8049	Intermediate Similarity	NPD6599	Discontinued
0.8047	Intermediate Similarity	NPD1247	Approved
0.8036	Intermediate Similarity	NPD919	Approved
0.8034	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD3027	Phase 3
0.7963	Intermediate Similarity	NPD5401	Approved
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7911	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8312	Approved
0.7853	Intermediate Similarity	NPD8313	Approved
0.7845	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7826	Intermediate Similarity	NPD4628	Phase 3
0.7826	Intermediate Similarity	NPD3750	Approved
0.7816	Intermediate Similarity	NPD3751	Discontinued
0.7806	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2800	Approved
0.7744	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD2532	Approved
0.7744	Intermediate Similarity	NPD2534	Approved
0.7742	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6234	Discontinued
0.7714	Intermediate Similarity	NPD7228	Approved
0.7711	Intermediate Similarity	NPD1653	Approved
0.7702	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3787	Discontinued
0.7688	Intermediate Similarity	NPD1551	Phase 2
0.7683	Intermediate Similarity	NPD7390	Discontinued
0.7683	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4908	Phase 1
0.7669	Intermediate Similarity	NPD6190	Approved
0.7665	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3226	Approved
0.7658	Intermediate Similarity	NPD447	Suspended
0.7651	Intermediate Similarity	NPD920	Approved
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD8151	Discontinued
0.7602	Intermediate Similarity	NPD4967	Phase 2
0.7602	Intermediate Similarity	NPD4965	Approved
0.7602	Intermediate Similarity	NPD4966	Approved
0.7598	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.758	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7568	Intermediate Similarity	NPD4360	Phase 2
0.7568	Intermediate Similarity	NPD4363	Phase 3
0.7553	Intermediate Similarity	NPD6780	Approved
0.7553	Intermediate Similarity	NPD6778	Approved
0.7553	Intermediate Similarity	NPD6779	Approved
0.7553	Intermediate Similarity	NPD6776	Approved
0.7553	Intermediate Similarity	NPD6777	Approved
0.7553	Intermediate Similarity	NPD6781	Approved
0.7553	Intermediate Similarity	NPD6782	Approved
0.7547	Intermediate Similarity	NPD1933	Approved
0.7546	Intermediate Similarity	NPD1243	Approved
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.7531	Intermediate Similarity	NPD2346	Discontinued
0.7531	Intermediate Similarity	NPD2344	Approved
0.753	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7516	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD7584	Approved
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7469	Intermediate Similarity	NPD6100	Approved
0.7469	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7468	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7435	Discontinued
0.7396	Intermediate Similarity	NPD7870	Phase 2
0.7396	Intermediate Similarity	NPD7871	Phase 2
0.7394	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6798	Discontinued
0.7353	Intermediate Similarity	NPD7458	Discontinued
0.7349	Intermediate Similarity	NPD2309	Approved
0.7347	Intermediate Similarity	NPD7783	Phase 2
0.7347	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7698	Approved
0.7344	Intermediate Similarity	NPD7696	Phase 3
0.7344	Intermediate Similarity	NPD7697	Approved
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.733	Intermediate Similarity	NPD8127	Discontinued
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6844	Discontinued
0.7317	Intermediate Similarity	NPD7266	Discontinued
0.7301	Intermediate Similarity	NPD7033	Discontinued
0.7292	Intermediate Similarity	NPD6823	Phase 2
0.7288	Intermediate Similarity	NPD5710	Approved
0.7288	Intermediate Similarity	NPD7229	Phase 3
0.7288	Intermediate Similarity	NPD5711	Approved
0.7287	Intermediate Similarity	NPD6534	Approved
0.7287	Intermediate Similarity	NPD6535	Approved
0.7282	Intermediate Similarity	NPD7701	Phase 2
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1203	Approved
0.7256	Intermediate Similarity	NPD5404	Approved
0.7256	Intermediate Similarity	NPD5406	Approved
0.7256	Intermediate Similarity	NPD5405	Approved
0.7256	Intermediate Similarity	NPD5408	Approved
0.7253	Intermediate Similarity	NPD7240	Approved
0.7253	Intermediate Similarity	NPD7039	Approved
0.7253	Intermediate Similarity	NPD7038	Approved
0.7247	Intermediate Similarity	NPD5242	Approved
0.7241	Intermediate Similarity	NPD5353	Approved
0.7233	Intermediate Similarity	NPD6832	Phase 2
0.7229	Intermediate Similarity	NPD6674	Discontinued
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7222	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7549	Discontinued
0.7208	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7874	Approved
0.7205	Intermediate Similarity	NPD6233	Phase 2
0.7198	Intermediate Similarity	NPD3823	Discontinued
0.7188	Intermediate Similarity	NPD4625	Phase 3
0.7176	Intermediate Similarity	NPD6273	Approved
0.7173	Intermediate Similarity	NPD7699	Phase 2
0.7173	Intermediate Similarity	NPD7700	Phase 2
0.7172	Intermediate Similarity	NPD7801	Approved
0.7158	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4361	Phase 2
0.7127	Intermediate Similarity	NPD7177	Discontinued
0.7126	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1652	Phase 2
0.7118	Intermediate Similarity	NPD4661	Approved
0.7118	Intermediate Similarity	NPD4662	Approved
0.7107	Intermediate Similarity	NPD2798	Approved
0.7107	Intermediate Similarity	NPD7585	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