NPASS Compound

Structure

NPC472625 OpenBabel07101718292D 33 36 0 0 1 0 0 0 0 0999 V2000 3.9533 -1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1780 -0.1378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 -0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5050 0.3105 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 -6.0622 -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 0 0 0 0 0 0 0 0 0 0 1.8320 0.7588 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2121 -0.3966 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 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 -0.8660 0.5000 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 -2.5981 0.5000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 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 -1.7321 3.0000 0.0000 O 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 -5.1962 2.0000 0.0000 O 0 0 0 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 -3.4641 -0.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 31 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 26 1 0 0 0 0 11 26 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 33 1 0 0 0 0 19 31 1 0 0 0 0 20 21 2 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 29 2 0 0 0 0 24 25 1 0 0 0 0 24 30 1 1 0 0 0 25 15 1 6 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.18
Volume:	461.83
LogP:	5.792
LogD:	3.265
LogS:	-3.351
# Rotatable Bonds:	5
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	3.553
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.855
MDCK Permeability:	1.4193300557963084e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	92.97895050048828%
Volume Distribution (VD):	0.639
Pgp-substrate:	10.022726058959961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.457
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.483
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.712
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.529
CYP2D6-substrate:	0.301
CYP3A4-inhibitor:	0.23
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	4.816
Half-life (T1/2):	0.413

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.324
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.516
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.342
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC472625

Natural Product ID:	NPC472625
*Common Name:**	KQYSCOBBQXGSPJ-LHJLODMPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KQYSCOBBQXGSPJ-LHJLODMPSA-N
Standard InCHI:	InChI=1S/C26H28O7/c1-14(2)6-5-10-26(3)11-9-16-18(33-26)13-20-21(22(16)28)23(29)24(30)25(32-20)15-7-8-17(27)19(12-15)31-4/h6-9,11-13,24-25,27-28,30H,5,10H2,1-4H3/t24-,25+,26?/m0/s1
SMILES:	COc1cc(ccc1O)[C@H]1Oc2cc3OC(C)(CCC=C(C)C)C=Cc3c(c2C(=O)[C@@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581345
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10000.0	nM	PMID[531326]

☑ 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 NPC472625 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	411
0.1-0.2	1634
0.2-0.3	4074
0.3-0.4	10022
0.4-0.5	8094
0.5-0.6	3607
0.6-0.7	4813
0.7-0.8	5475
0.8-0.85	2726
0.85-0.9	1424
0.9-0.95	363
0.95-1	54

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC474038
0.9805	High Similarity	NPC118256
0.9805	High Similarity	NPC119209
0.9805	High Similarity	NPC282009
0.9805	High Similarity	NPC287328
0.9805	High Similarity	NPC475784
0.9805	High Similarity	NPC192686
0.9745	High Similarity	NPC471213
0.9742	High Similarity	NPC26326
0.9742	High Similarity	NPC472632
0.9742	High Similarity	NPC471499
0.9742	High Similarity	NPC289771
0.974	High Similarity	NPC22192
0.9682	High Similarity	NPC62261
0.9679	High Similarity	NPC474033
0.9679	High Similarity	NPC474034
0.9677	High Similarity	NPC470326
0.9677	High Similarity	NPC174953
0.9675	High Similarity	NPC27337
0.9675	High Similarity	NPC472598
0.9675	High Similarity	NPC284820
0.9675	High Similarity	NPC473272
0.9675	High Similarity	NPC474055
0.9618	High Similarity	NPC186686
0.9615	High Similarity	NPC471210
0.9615	High Similarity	NPC472634
0.9613	High Similarity	NPC53545
0.9613	High Similarity	NPC117418
0.9613	High Similarity	NPC473990
0.961	High Similarity	NPC278778
0.961	High Similarity	NPC326037
0.961	High Similarity	NPC13858
0.961	High Similarity	NPC320825
0.961	High Similarity	NPC291878
0.961	High Similarity	NPC195796
0.961	High Similarity	NPC35038
0.9554	High Similarity	NPC474150
0.9554	High Similarity	NPC474162
0.9554	High Similarity	NPC472635
0.9554	High Similarity	NPC476247
0.9551	High Similarity	NPC472631
0.9551	High Similarity	NPC472630
0.9551	High Similarity	NPC472624
0.9551	High Similarity	NPC470183
0.9548	High Similarity	NPC52530
0.9548	High Similarity	NPC471515
0.9548	High Similarity	NPC471479
0.9548	High Similarity	NPC52889
0.9548	High Similarity	NPC67876
0.9548	High Similarity	NPC291508
0.9548	High Similarity	NPC471209
0.9545	High Similarity	NPC321779
0.9545	High Similarity	NPC304207
0.9545	High Similarity	NPC45849
0.9545	High Similarity	NPC470327
0.9545	High Similarity	NPC48579
0.9545	High Similarity	NPC200761
0.9545	High Similarity	NPC477503
0.9545	High Similarity	NPC217706
0.9545	High Similarity	NPC207809
0.9545	High Similarity	NPC259710
0.95	High Similarity	NPC165456
0.9497	High Similarity	NPC43319
0.9494	High Similarity	NPC124038
0.949	High Similarity	NPC142252
0.949	High Similarity	NPC134783
0.949	High Similarity	NPC471211
0.949	High Similarity	NPC173137
0.949	High Similarity	NPC471212
0.9487	High Similarity	NPC74178
0.9487	High Similarity	NPC204879
0.9487	High Similarity	NPC184755
0.9484	High Similarity	NPC470328
0.9484	High Similarity	NPC471500
0.9484	High Similarity	NPC471985
0.9484	High Similarity	NPC209614
0.9484	High Similarity	NPC472626
0.9484	High Similarity	NPC250922
0.9481	High Similarity	NPC18727
0.9481	High Similarity	NPC192083
0.9481	High Similarity	NPC180301
0.9481	High Similarity	NPC213896
0.9481	High Similarity	NPC248793
0.9481	High Similarity	NPC74924
0.9441	High Similarity	NPC102277
0.9441	High Similarity	NPC279209
0.9437	High Similarity	NPC218226
0.9437	High Similarity	NPC158761
0.9437	High Similarity	NPC260266
0.9434	High Similarity	NPC224280
0.9434	High Similarity	NPC7688
0.9434	High Similarity	NPC125039
0.9434	High Similarity	NPC7154
0.9434	High Similarity	NPC293319
0.9434	High Similarity	NPC58223
0.9434	High Similarity	NPC475888
0.9434	High Similarity	NPC36
0.9434	High Similarity	NPC36916
0.9434	High Similarity	NPC470457
0.9434	High Similarity	NPC72787
0.943	High Similarity	NPC211107
0.943	High Similarity	NPC83922
0.943	High Similarity	NPC472448
0.943	High Similarity	NPC78332
0.9427	High Similarity	NPC204290
0.9427	High Similarity	NPC328102
0.9427	High Similarity	NPC263449
0.9427	High Similarity	NPC36217
0.9423	High Similarity	NPC223787
0.9423	High Similarity	NPC218313
0.9423	High Similarity	NPC78071
0.9423	High Similarity	NPC474681
0.9423	High Similarity	NPC237418
0.9419	High Similarity	NPC234255
0.9419	High Similarity	NPC304745
0.9419	High Similarity	NPC111341
0.9419	High Similarity	NPC133392
0.9419	High Similarity	NPC226025
0.9416	High Similarity	NPC63187
0.9416	High Similarity	NPC9743
0.9416	High Similarity	NPC61506
0.9416	High Similarity	NPC260491
0.9416	High Similarity	NPC471982
0.9416	High Similarity	NPC106976
0.9416	High Similarity	NPC240476
0.9416	High Similarity	NPC157784
0.9416	High Similarity	NPC37684
0.9416	High Similarity	NPC302950
0.9416	High Similarity	NPC219582
0.9416	High Similarity	NPC36835
0.9416	High Similarity	NPC236637
0.9416	High Similarity	NPC246162
0.9379	High Similarity	NPC177480
0.9379	High Similarity	NPC288813
0.9379	High Similarity	NPC475212
0.9371	High Similarity	NPC474240
0.9371	High Similarity	NPC41301
0.9371	High Similarity	NPC470459
0.9367	High Similarity	NPC308992
0.9367	High Similarity	NPC288131
0.9367	High Similarity	NPC305987
0.9367	High Similarity	NPC29876
0.9367	High Similarity	NPC158188
0.9367	High Similarity	NPC167678
0.9367	High Similarity	NPC198829
0.9367	High Similarity	NPC66618
0.9367	High Similarity	NPC113163
0.9367	High Similarity	NPC84324
0.9367	High Similarity	NPC165970
0.9363	High Similarity	NPC476410
0.9363	High Similarity	NPC152904
0.9363	High Similarity	NPC95936
0.9363	High Similarity	NPC187792
0.9363	High Similarity	NPC250214
0.9363	High Similarity	NPC55738
0.9363	High Similarity	NPC172202
0.9363	High Similarity	NPC284127
0.9359	High Similarity	NPC133970
0.9359	High Similarity	NPC6633
0.9359	High Similarity	NPC5322
0.9359	High Similarity	NPC474638
0.9359	High Similarity	NPC472455
0.9359	High Similarity	NPC282307
0.9359	High Similarity	NPC170026
0.9355	High Similarity	NPC270620
0.9355	High Similarity	NPC311579
0.9355	High Similarity	NPC27532
0.9355	High Similarity	NPC141212
0.9355	High Similarity	NPC236756
0.9355	High Similarity	NPC223701
0.9355	High Similarity	NPC325028
0.9355	High Similarity	NPC268193
0.9355	High Similarity	NPC246328
0.9355	High Similarity	NPC236223
0.9355	High Similarity	NPC179126
0.9355	High Similarity	NPC7989
0.9355	High Similarity	NPC298692
0.9355	High Similarity	NPC78326
0.9355	High Similarity	NPC472583
0.9355	High Similarity	NPC170492
0.9355	High Similarity	NPC256346
0.9351	High Similarity	NPC319910
0.9351	High Similarity	NPC304295
0.9351	High Similarity	NPC125062
0.9351	High Similarity	NPC205046
0.9351	High Similarity	NPC262038
0.9351	High Similarity	NPC59162
0.9351	High Similarity	NPC278476
0.9351	High Similarity	NPC54394
0.9351	High Similarity	NPC262039
0.9351	High Similarity	NPC252933
0.9351	High Similarity	NPC200740
0.9351	High Similarity	NPC254412
0.9317	High Similarity	NPC295082
0.9317	High Similarity	NPC474024
0.9317	High Similarity	NPC150131
0.9317	High Similarity	NPC8965
0.9317	High Similarity	NPC477154
0.9317	High Similarity	NPC6588
0.9317	High Similarity	NPC117854

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 NPC472625 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	927
0.2-0.3	1816
0.3-0.4	2604
0.4-0.5	1809
0.5-0.6	969
0.6-0.7	467
0.7-0.8	138
0.8-0.85	33
0.85-0.9	10
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD2393	Clinical (unspecified phase)
0.9434	High Similarity	NPD6166	Phase 2
0.9434	High Similarity	NPD6167	Clinical (unspecified phase)
0.9434	High Similarity	NPD6168	Clinical (unspecified phase)
0.9416	High Similarity	NPD1934	Approved
0.9108	High Similarity	NPD2801	Approved
0.9038	High Similarity	NPD4380	Phase 2
0.903	High Similarity	NPD6797	Phase 2
0.9026	High Similarity	NPD1512	Approved
0.9024	High Similarity	NPD7054	Approved
0.8994	High Similarity	NPD3882	Suspended
0.8976	High Similarity	NPD7251	Discontinued
0.897	High Similarity	NPD7472	Approved
0.897	High Similarity	NPD7074	Phase 3
0.8961	High Similarity	NPD4378	Clinical (unspecified phase)
0.8931	High Similarity	NPD3817	Phase 2
0.8922	High Similarity	NPD7808	Phase 3
0.8922	High Similarity	NPD4338	Clinical (unspecified phase)
0.8896	High Similarity	NPD1511	Approved
0.8848	High Similarity	NPD3818	Discontinued
0.882	High Similarity	NPD7075	Discontinued
0.8795	High Similarity	NPD7804	Clinical (unspecified phase)
0.875	High Similarity	NPD7096	Clinical (unspecified phase)
0.8712	High Similarity	NPD5494	Approved
0.8704	High Similarity	NPD4381	Clinical (unspecified phase)
0.8688	High Similarity	NPD6801	Discontinued
0.8642	High Similarity	NPD4868	Clinical (unspecified phase)
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD5844	Phase 1
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD5402	Approved
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8323	Intermediate Similarity	NPD2796	Approved
0.8302	Intermediate Similarity	NPD6799	Approved
0.8293	Intermediate Similarity	NPD7819	Suspended
0.8282	Intermediate Similarity	NPD7411	Suspended
0.8274	Intermediate Similarity	NPD6232	Discontinued
0.8261	Intermediate Similarity	NPD5403	Approved
0.8258	Intermediate Similarity	NPD1510	Phase 2
0.8235	Intermediate Similarity	NPD7473	Discontinued
0.8214	Intermediate Similarity	NPD1247	Approved
0.8208	Intermediate Similarity	NPD6559	Discontinued
0.8204	Intermediate Similarity	NPD919	Approved
0.8137	Intermediate Similarity	NPD5401	Approved
0.8117	Intermediate Similarity	NPD1613	Approved
0.8117	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6599	Discontinued
0.8072	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD1240	Approved
0.7965	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3027	Phase 3
0.7907	Intermediate Similarity	NPD3926	Phase 2
0.7901	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1607	Approved
0.7885	Intermediate Similarity	NPD943	Approved
0.7874	Intermediate Similarity	NPD3751	Discontinued
0.787	Intermediate Similarity	NPD7768	Phase 2
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3787	Discontinued
0.7821	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6190	Approved
0.7719	Intermediate Similarity	NPD3749	Approved
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2800	Approved
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD2534	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.7665	Intermediate Similarity	NPD1653	Approved
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4363	Phase 3
0.7622	Intermediate Similarity	NPD4360	Phase 2
0.761	Intermediate Similarity	NPD230	Phase 1
0.7606	Intermediate Similarity	NPD6779	Approved
0.7606	Intermediate Similarity	NPD6778	Approved
0.7606	Intermediate Similarity	NPD6777	Approved
0.7606	Intermediate Similarity	NPD6782	Approved
0.7606	Intermediate Similarity	NPD6776	Approved
0.7606	Intermediate Similarity	NPD6781	Approved
0.7606	Intermediate Similarity	NPD6780	Approved
0.7606	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD920	Approved
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7685	Pre-registration
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.7578	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6234	Discontinued
0.7571	Intermediate Similarity	NPD7228	Approved
0.7552	Intermediate Similarity	NPD7584	Approved
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6099	Approved
0.7531	Intermediate Similarity	NPD6100	Approved
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1243	Approved
0.75	Intermediate Similarity	NPD5124	Phase 1
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7033	Discontinued
0.7469	Intermediate Similarity	NPD3748	Approved
0.7457	Intermediate Similarity	NPD4967	Phase 2
0.7457	Intermediate Similarity	NPD4966	Approved
0.7457	Intermediate Similarity	NPD4965	Approved
0.7455	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6651	Approved
0.7444	Intermediate Similarity	NPD5953	Discontinued
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7425	Intermediate Similarity	NPD7390	Discontinued
0.7425	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.7412	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD4908	Phase 1
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7697	Approved
0.7391	Intermediate Similarity	NPD1933	Approved
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD2799	Discontinued
0.7362	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7871	Phase 2
0.7358	Intermediate Similarity	NPD7870	Phase 2
0.7349	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD9494	Approved
0.734	Intermediate Similarity	NPD6534	Approved
0.734	Intermediate Similarity	NPD6535	Approved
0.7333	Intermediate Similarity	NPD2424	Discontinued
0.7333	Intermediate Similarity	NPD7701	Phase 2
0.7312	Intermediate Similarity	NPD6798	Discontinued
0.731	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2344	Approved
0.7259	Intermediate Similarity	NPD7874	Approved
0.7259	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4625	Phase 3
0.7247	Intermediate Similarity	NPD5711	Approved
0.7247	Intermediate Similarity	NPD5710	Approved
0.7241	Intermediate Similarity	NPD8455	Phase 2
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7700	Phase 2
0.7225	Intermediate Similarity	NPD7699	Phase 2
0.7222	Intermediate Similarity	NPD7783	Phase 2
0.7222	Intermediate Similarity	NPD7801	Approved
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2493	Approved
0.7202	Intermediate Similarity	NPD2494	Approved
0.7186	Intermediate Similarity	NPD1652	Phase 2
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7178	Intermediate Similarity	NPD6355	Discontinued
0.7169	Intermediate Similarity	NPD7266	Discontinued
0.7167	Intermediate Similarity	NPD2403	Approved
0.7167	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6823	Phase 2
0.716	Intermediate Similarity	NPD6233	Phase 2
0.7158	Intermediate Similarity	NPD3823	Discontinued
0.7157	Intermediate Similarity	NPD7585	Approved
0.7143	Intermediate Similarity	NPD4111	Phase 1
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD4665	Approved
0.712	Intermediate Similarity	NPD7240	Approved
0.7113	Intermediate Similarity	NPD3452	Approved
0.7113	Intermediate Similarity	NPD3450	Approved
0.7111	Intermediate Similarity	NPD5242	Approved
0.711	Intermediate Similarity	NPD7458	Discontinued
0.7107	Intermediate Similarity	NPD7583	Approved
0.7107	Intermediate Similarity	NPD1203	Approved
0.7102	Intermediate Similarity	NPD5353	Approved
0.7101	Intermediate Similarity	NPD2309	Approved
0.7099	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3268	Approved
0.7095	Intermediate Similarity	NPD8127	Discontinued
0.7092	Intermediate Similarity	NPD8319	Approved
0.7092	Intermediate Similarity	NPD8320	Phase 1
0.7092	Intermediate Similarity	NPD4582	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