NPASS Compound

Structure

NPC471499 OpenBabel07101719522D 34 36 0 0 1 0 0 0 0 0999 V2000 -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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 1.7321 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 -5.1962 1.0000 0.0000 C 0 0 0 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 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 -5.1962 0.0000 0.0000 C 0 0 3 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 -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 -0.8660 -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 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 -0.0000 -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 1 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 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 -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 -2.0000 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 13 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 33 1 0 0 0 0 5 8 1 0 0 0 0 5 14 2 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 16 19 1 0 0 0 0 16 23 2 0 0 0 0 17 27 1 0 0 0 0 18 20 2 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 33 1 0 0 0 0 21 22 2 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 31 2 0 0 0 0 25 26 1 0 0 0 0 25 32 1 1 0 0 0 26 15 1 6 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.19
Volume:	479.176
LogP:	3.476
LogD:	2.664
LogS:	-3.537
# Rotatable Bonds:	8
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	4.094
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.667
MDCK Permeability:	6.122766990301898e-06
Pgp-inhibitor:	0.09
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.191
20% Bioavailability (F20%):	0.733
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	96.22167205810547%
Volume Distribution (VD):	0.661
Pgp-substrate:	3.544337272644043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.105
CYP2C9-inhibitor:	0.546
CYP2C9-substrate:	0.742
CYP2D6-inhibitor:	0.629
CYP2D6-substrate:	0.341
CYP3A4-inhibitor:	0.377
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	7.722
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.312
Drug-inuced Liver Injury (DILI):	0.615
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.365
Skin Sensitization:	0.419
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.195

Download Data

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

Natural Product: NPC471499

Natural Product ID:	NPC471499
*Common Name:**	Tomentodiplacol
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-6-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dienyl]-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	Tomentodiplacol
Standard InCHIKey:	IMLYVWIWEAZRNK-ACNRMZSJSA-N
Standard InCHI:	InChI=1S/C26H30O8/c1-13(2)17(27)9-6-14(3)5-8-16-19(29)12-21-22(23(16)30)24(31)25(32)26(34-21)15-7-10-18(28)20(11-15)33-4/h5,7,10-12,17,25-30,32H,1,6,8-9H2,2-4H3/b14-5+/t17?,25-,26+/m0/s1
SMILES:	CC(=C)C(CCC(=CCC1=C(C2=C(C=C1O)OC(C(C2=O)O)C3=CC(=C(C=C3)O)OC)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253151
PubChem CID:	23626478
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	2.0	n.a.	PMID[458536]

☑ 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 NPC471499 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	416
0.1-0.2	1571
0.2-0.3	3971
0.3-0.4	9660
0.4-0.5	8502
0.5-0.6	3495
0.6-0.7	4668
0.7-0.8	5297
0.8-0.85	2859
0.85-0.9	1772
0.9-0.95	396
0.95-1	90

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC287328
0.9934	High Similarity	NPC470326
0.9934	High Similarity	NPC282009
0.9868	High Similarity	NPC22192
0.9803	High Similarity	NPC472598
0.9803	High Similarity	NPC474055
0.9744	High Similarity	NPC471213
0.9742	High Similarity	NPC472625
0.974	High Similarity	NPC289771
0.974	High Similarity	NPC472634
0.974	High Similarity	NPC26326
0.9737	High Similarity	NPC35038
0.9737	High Similarity	NPC320825
0.9737	High Similarity	NPC326037
0.9737	High Similarity	NPC195796
0.9737	High Similarity	NPC13858
0.9737	High Similarity	NPC250922
0.9737	High Similarity	NPC278778
0.9737	High Similarity	NPC291878
0.9677	High Similarity	NPC472635
0.9675	High Similarity	NPC472630
0.9675	High Similarity	NPC472631
0.9673	High Similarity	NPC27337
0.9673	High Similarity	NPC291508
0.9673	High Similarity	NPC471479
0.9673	High Similarity	NPC471515
0.9673	High Similarity	NPC52530
0.9671	High Similarity	NPC477503
0.9671	High Similarity	NPC45849
0.9671	High Similarity	NPC200761
0.9671	High Similarity	NPC470327
0.9671	High Similarity	NPC321779
0.9613	High Similarity	NPC474038
0.9613	High Similarity	NPC472632
0.9613	High Similarity	NPC142252
0.961	High Similarity	NPC117418
0.961	High Similarity	NPC53545
0.9608	High Similarity	NPC209614
0.9608	High Similarity	NPC470328
0.9608	High Similarity	NPC471500
0.9608	High Similarity	NPC472626
0.9605	High Similarity	NPC192083
0.9605	High Similarity	NPC18727
0.9605	High Similarity	NPC213896
0.956	High Similarity	NPC279209
0.956	High Similarity	NPC102277
0.9554	High Similarity	NPC36
0.9554	High Similarity	NPC470457
0.9554	High Similarity	NPC125039
0.9554	High Similarity	NPC62261
0.9554	High Similarity	NPC58223
0.9554	High Similarity	NPC475888
0.9554	High Similarity	NPC36916
0.9554	High Similarity	NPC7154
0.9554	High Similarity	NPC72787
0.9554	High Similarity	NPC7688
0.9551	High Similarity	NPC474034
0.9551	High Similarity	NPC474033
0.9551	High Similarity	NPC476247
0.9551	High Similarity	NPC211107
0.9548	High Similarity	NPC475784
0.9548	High Similarity	NPC263449
0.9548	High Similarity	NPC119209
0.9548	High Similarity	NPC118256
0.9548	High Similarity	NPC472624
0.9548	High Similarity	NPC174953
0.9548	High Similarity	NPC36217
0.9548	High Similarity	NPC470183
0.9548	High Similarity	NPC192686
0.9545	High Similarity	NPC223787
0.9545	High Similarity	NPC67876
0.9542	High Similarity	NPC226025
0.9539	High Similarity	NPC19721
0.9539	High Similarity	NPC240476
0.9539	High Similarity	NPC9743
0.9539	High Similarity	NPC219582
0.9539	High Similarity	NPC106976
0.9539	High Similarity	NPC61506
0.9539	High Similarity	NPC302950
0.9539	High Similarity	NPC36835
0.9539	High Similarity	NPC236637
0.9539	High Similarity	NPC246162
0.9539	High Similarity	NPC260491
0.949	High Similarity	NPC470459
0.949	High Similarity	NPC41301
0.949	High Similarity	NPC124038
0.949	High Similarity	NPC474240
0.9487	High Similarity	NPC308992
0.9487	High Similarity	NPC471211
0.9487	High Similarity	NPC471210
0.9487	High Similarity	NPC158188
0.9487	High Similarity	NPC266314
0.9487	High Similarity	NPC471212
0.9487	High Similarity	NPC112418
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC473990
0.9477	High Similarity	NPC74924
0.9477	High Similarity	NPC298692
0.9477	High Similarity	NPC325028
0.9477	High Similarity	NPC246328
0.9477	High Similarity	NPC256346
0.9477	High Similarity	NPC27532
0.9474	High Similarity	NPC254412
0.9474	High Similarity	NPC262038
0.9474	High Similarity	NPC262039
0.9474	High Similarity	NPC319910
0.9474	High Similarity	NPC278476
0.9434	High Similarity	NPC260266
0.9434	High Similarity	NPC158761
0.9434	High Similarity	NPC470456
0.9427	High Similarity	NPC471745
0.9427	High Similarity	NPC201800
0.9423	High Similarity	NPC321399
0.9423	High Similarity	NPC471744
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC473272
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC471209
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC284820
0.9419	High Similarity	NPC475267
0.9416	High Similarity	NPC117992
0.9416	High Similarity	NPC230149
0.9416	High Similarity	NPC304745
0.9416	High Similarity	NPC57674
0.9416	High Similarity	NPC111341
0.9416	High Similarity	NPC133392
0.9416	High Similarity	NPC168247
0.9416	High Similarity	NPC152951
0.9412	High Similarity	NPC243171
0.9412	High Similarity	NPC471982
0.9412	High Similarity	NPC217149
0.9412	High Similarity	NPC157784
0.9412	High Similarity	NPC35567
0.9412	High Similarity	NPC216035
0.9412	High Similarity	NPC171651
0.9412	High Similarity	NPC37684
0.9412	High Similarity	NPC138288
0.9412	High Similarity	NPC472912
0.9412	High Similarity	NPC63187
0.9408	High Similarity	NPC338131
0.9408	High Similarity	NPC105136
0.9375	High Similarity	NPC475212
0.9371	High Similarity	NPC470462
0.9371	High Similarity	NPC119589
0.9367	High Similarity	NPC186686
0.9363	High Similarity	NPC288131
0.9363	High Similarity	NPC173137
0.9363	High Similarity	NPC305987
0.9363	High Similarity	NPC474239
0.9363	High Similarity	NPC134783
0.9363	High Similarity	NPC66618
0.9363	High Similarity	NPC113163
0.9363	High Similarity	NPC84324
0.9363	High Similarity	NPC165970
0.9359	High Similarity	NPC172202
0.9359	High Similarity	NPC284127
0.9359	High Similarity	NPC55738
0.9359	High Similarity	NPC476410
0.9359	High Similarity	NPC152904
0.9359	High Similarity	NPC210459
0.9355	High Similarity	NPC10754
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC474638
0.9355	High Similarity	NPC201837
0.9355	High Similarity	NPC255106
0.9355	High Similarity	NPC235165
0.9355	High Similarity	NPC68093
0.9355	High Similarity	NPC20530
0.9355	High Similarity	NPC215917
0.9351	High Similarity	NPC33051
0.9351	High Similarity	NPC270620
0.9351	High Similarity	NPC141212
0.9351	High Similarity	NPC227337
0.9351	High Similarity	NPC70433
0.9351	High Similarity	NPC49402
0.9351	High Similarity	NPC268193
0.9351	High Similarity	NPC236223
0.9351	High Similarity	NPC179126
0.9351	High Similarity	NPC162351
0.9351	High Similarity	NPC293286
0.9351	High Similarity	NPC78326
0.9351	High Similarity	NPC58382
0.9351	High Similarity	NPC273462
0.9346	High Similarity	NPC54394
0.9346	High Similarity	NPC252933
0.9346	High Similarity	NPC304295
0.9346	High Similarity	NPC28274
0.9346	High Similarity	NPC50403
0.9346	High Similarity	NPC200740
0.9346	High Similarity	NPC205046
0.9346	High Similarity	NPC125062
0.9346	High Similarity	NPC59162
0.9346	High Similarity	NPC133953
0.9313	High Similarity	NPC295082
0.9313	High Similarity	NPC474024

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 NPC471499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	907
0.2-0.3	1812
0.3-0.4	2588
0.4-0.5	1802
0.5-0.6	983
0.6-0.7	494
0.7-0.8	139
0.8-0.85	32
0.85-0.9	20
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD2393	Clinical (unspecified phase)
0.9554	High Similarity	NPD6167	Clinical (unspecified phase)
0.9554	High Similarity	NPD6168	Clinical (unspecified phase)
0.9554	High Similarity	NPD6166	Phase 2
0.9539	High Similarity	NPD1934	Approved
0.9108	High Similarity	NPD3882	Suspended
0.9103	High Similarity	NPD2801	Approved
0.908	High Similarity	NPD7074	Phase 3
0.9051	High Similarity	NPD7075	Discontinued
0.9045	High Similarity	NPD3817	Phase 2
0.9032	High Similarity	NPD4380	Phase 2
0.9024	High Similarity	NPD6797	Phase 2
0.902	High Similarity	NPD1512	Approved
0.9018	High Similarity	NPD7054	Approved
0.897	High Similarity	NPD7251	Discontinued
0.8963	High Similarity	NPD7472	Approved
0.8957	High Similarity	NPD3818	Discontinued
0.8954	High Similarity	NPD4378	Clinical (unspecified phase)
0.8916	High Similarity	NPD4338	Clinical (unspecified phase)
0.8916	High Similarity	NPD7808	Phase 3
0.8889	High Similarity	NPD1511	Approved
0.8861	High Similarity	NPD7096	Clinical (unspecified phase)
0.8797	High Similarity	NPD6801	Discontinued
0.8788	High Similarity	NPD7804	Clinical (unspecified phase)
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8704	High Similarity	NPD5494	Approved
0.8696	High Similarity	NPD4381	Clinical (unspecified phase)
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD7993	Clinical (unspecified phase)
0.8562	High Similarity	NPD1549	Phase 2
0.8509	High Similarity	NPD7819	Suspended
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8452	Intermediate Similarity	NPD5844	Phase 1
0.8443	Intermediate Similarity	NPD7473	Discontinued
0.8424	Intermediate Similarity	NPD6959	Discontinued
0.8412	Intermediate Similarity	NPD6559	Discontinued
0.8408	Intermediate Similarity	NPD6799	Approved
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8354	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5402	Approved
0.8312	Intermediate Similarity	NPD2796	Approved
0.825	Intermediate Similarity	NPD5403	Approved
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.821	Intermediate Similarity	NPD6599	Discontinued
0.8204	Intermediate Similarity	NPD1247	Approved
0.8193	Intermediate Similarity	NPD919	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8125	Intermediate Similarity	NPD5401	Approved
0.8107	Intermediate Similarity	NPD3926	Phase 2
0.8105	Intermediate Similarity	NPD1240	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD1607	Approved
0.7987	Intermediate Similarity	NPD943	Approved
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7768	Phase 2
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7826	Intermediate Similarity	NPD6190	Approved
0.7812	Intermediate Similarity	NPD2800	Approved
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7758	Intermediate Similarity	NPD1653	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.7717	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7679	Intermediate Similarity	NPD37	Approved
0.7673	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6651	Approved
0.7657	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD3750	Approved
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7647	Intermediate Similarity	NPD4965	Approved
0.764	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7605	Intermediate Similarity	NPD3226	Approved
0.7602	Intermediate Similarity	NPD3749	Approved
0.7598	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD8313	Approved
0.7595	Intermediate Similarity	NPD447	Suspended
0.7594	Intermediate Similarity	NPD6777	Approved
0.7594	Intermediate Similarity	NPD6781	Approved
0.7594	Intermediate Similarity	NPD6778	Approved
0.7594	Intermediate Similarity	NPD6779	Approved
0.7594	Intermediate Similarity	NPD6782	Approved
0.7594	Intermediate Similarity	NPD6780	Approved
0.7594	Intermediate Similarity	NPD6776	Approved
0.759	Intermediate Similarity	NPD920	Approved
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7569	Intermediate Similarity	NPD8434	Phase 2
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7485	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7448	Intermediate Similarity	NPD7584	Approved
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD9494	Approved
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7405	Intermediate Similarity	NPD6798	Discontinued
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7371	Intermediate Similarity	NPD8151	Discontinued
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2344	Approved
0.7346	Intermediate Similarity	NPD7033	Discontinued
0.7346	Intermediate Similarity	NPD3748	Approved
0.7344	Intermediate Similarity	NPD7871	Phase 2
0.7344	Intermediate Similarity	NPD7870	Phase 2
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5711	Approved
0.733	Intermediate Similarity	NPD5710	Approved
0.7326	Intermediate Similarity	NPD8455	Phase 2
0.7326	Intermediate Similarity	NPD6534	Approved
0.7326	Intermediate Similarity	NPD6535	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7317	Intermediate Similarity	NPD2424	Discontinued
0.7312	Intermediate Similarity	NPD4060	Phase 1
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7256	Intermediate Similarity	NPD7266	Discontinued
0.725	Intermediate Similarity	NPD6233	Phase 2
0.7245	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7874	Approved
0.7233	Intermediate Similarity	NPD4625	Phase 3
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7208	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7783	Phase 2
0.7208	Intermediate Similarity	NPD7801	Approved
0.7198	Intermediate Similarity	NPD7240	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7196	Intermediate Similarity	NPD4361	Phase 2
0.7196	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5242	Approved
0.7186	Intermediate Similarity	NPD2309	Approved
0.7184	Intermediate Similarity	NPD5353	Approved
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1652	Phase 2
0.7168	Intermediate Similarity	NPD6844	Discontinued
0.7167	Intermediate Similarity	NPD2163	Approved
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2403	Approved
0.715	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD3823	Discontinued
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7107	Intermediate Similarity	NPD3018	Phase 2
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7098	Intermediate Similarity	NPD2493	Approved
0.7098	Intermediate Similarity	NPD2494	Approved
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD8320	Phase 1
0.7077	Intermediate Similarity	NPD8319	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