NPASS Compound

Structure

NPC472598 OpenBabel07101719252D 33 35 0 0 1 0 0 0 0 0999 V2000 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 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 5.1962 2.0000 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 -5.1962 2.0000 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 1.7321 0.0000 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 -2.5981 0.5000 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 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 0.8660 0.5000 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 2.5981 0.5000 0.0000 C 0 0 3 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 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 15 2 0 0 0 0 4 32 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 12 24 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 15 19 1 0 0 0 0 17 20 1 0 0 0 0 17 26 2 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 30 2 0 0 0 0 22 16 1 1 0 0 0 22 33 1 0 0 0 0 23 32 1 0 0 0 0 24 25 2 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.2
Volume:	470.386
LogP:	4.744
LogD:	3.32
LogS:	-3.762
# Rotatable Bonds:	8
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	3.877
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:	-4.933
MDCK Permeability:	9.498435247223824e-06
Pgp-inhibitor:	0.303
Pgp-substrate:	0.824
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.665
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	94.06377410888672%
Volume Distribution (VD):	0.995
Pgp-substrate:	3.627279758453369%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.488
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.836
CYP2D6-substrate:	0.558
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	14.258
Half-life (T1/2):	0.319

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.783
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.786
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.804
Carcinogencity:	0.312
Eye Corrosion:	0.003
Eye Irritation:	0.778
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC472598

Natural Product ID:	NPC472598
*Common Name:**	QOCMJNYAMYAFJX-BPARTEKVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QOCMJNYAMYAFJX-BPARTEKVSA-N
Standard InCHI:	InChI=1S/C26H30O7/c1-14(2)6-5-7-15(3)19(28)11-17-20(29)12-24-25(26(17)31)21(30)13-22(33-24)16-8-9-18(27)23(10-16)32-4/h6,8-10,12,19,22,27-29,31H,3,5,7,11,13H2,1-2,4H3/t19?,22-/m0/s1
SMILES:	COc1cc(ccc1O)[C@@H]1CC(=O)c2c(O1)cc(c(c2O)CC(C(=C)CCC=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3580671
PubChem CID:	n.a.
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
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	<	6500.0	nM	PMID[521217]

☑ 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 NPC472598 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	401
0.1-0.2	1528
0.2-0.3	3885
0.3-0.4	9489
0.4-0.5	8776
0.5-0.6	3256
0.6-0.7	4638
0.7-0.8	5349
0.8-0.85	2899
0.85-0.9	1821
0.9-0.95	540
0.95-1	115

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474055
0.9933	High Similarity	NPC291878
0.9933	High Similarity	NPC278778
0.9933	High Similarity	NPC35038
0.9933	High Similarity	NPC195796
0.9868	High Similarity	NPC282009
0.9868	High Similarity	NPC287328
0.9867	High Similarity	NPC27337
0.9867	High Similarity	NPC291508
0.9866	High Similarity	NPC321779
0.9866	High Similarity	NPC477503
0.9866	High Similarity	NPC45849
0.9866	High Similarity	NPC200761
0.9866	High Similarity	NPC470327
0.9803	High Similarity	NPC471499
0.9803	High Similarity	NPC472634
0.9803	High Similarity	NPC26326
0.9803	High Similarity	NPC472632
0.9803	High Similarity	NPC474038
0.9801	High Similarity	NPC22192
0.98	High Similarity	NPC472626
0.98	High Similarity	NPC470328
0.98	High Similarity	NPC209614
0.9799	High Similarity	NPC18727
0.9799	High Similarity	NPC192083
0.9799	High Similarity	NPC213896
0.9739	High Similarity	NPC476247
0.9739	High Similarity	NPC474034
0.9739	High Similarity	NPC472635
0.9739	High Similarity	NPC474033
0.9737	High Similarity	NPC118256
0.9737	High Similarity	NPC472624
0.9737	High Similarity	NPC472630
0.9737	High Similarity	NPC470326
0.9737	High Similarity	NPC36217
0.9737	High Similarity	NPC174953
0.9737	High Similarity	NPC472631
0.9737	High Similarity	NPC475784
0.9737	High Similarity	NPC119209
0.9737	High Similarity	NPC192686
0.9735	High Similarity	NPC223787
0.9733	High Similarity	NPC226025
0.9732	High Similarity	NPC219582
0.9732	High Similarity	NPC236637
0.9732	High Similarity	NPC106976
0.9732	High Similarity	NPC302950
0.9675	High Similarity	NPC472625
0.9675	High Similarity	NPC124038
0.9673	High Similarity	NPC142252
0.9673	High Similarity	NPC471210
0.9671	High Similarity	NPC250214
0.9671	High Similarity	NPC53545
0.9671	High Similarity	NPC95936
0.9671	High Similarity	NPC117418
0.9671	High Similarity	NPC473990
0.9669	High Similarity	NPC320825
0.9669	High Similarity	NPC13858
0.9669	High Similarity	NPC326037
0.9667	High Similarity	NPC298692
0.9667	High Similarity	NPC74924
0.961	High Similarity	NPC201800
0.9608	High Similarity	NPC321399
0.9605	High Similarity	NPC471479
0.9605	High Similarity	NPC473272
0.9605	High Similarity	NPC52530
0.9605	High Similarity	NPC471515
0.9605	High Similarity	NPC474208
0.9605	High Similarity	NPC156057
0.9605	High Similarity	NPC471209
0.9605	High Similarity	NPC475267
0.9605	High Similarity	NPC474836
0.9605	High Similarity	NPC162869
0.9605	High Similarity	NPC284820
0.9605	High Similarity	NPC48208
0.9605	High Similarity	NPC78225
0.9603	High Similarity	NPC230149
0.9603	High Similarity	NPC57674
0.9603	High Similarity	NPC168247
0.9603	High Similarity	NPC117992
0.9603	High Similarity	NPC152951
0.96	High Similarity	NPC471982
0.96	High Similarity	NPC472912
0.9597	High Similarity	NPC338131
0.9551	High Similarity	NPC471213
0.9548	High Similarity	NPC186686
0.9545	High Similarity	NPC266314
0.9545	High Similarity	NPC134783
0.9545	High Similarity	NPC158188
0.9545	High Similarity	NPC471211
0.9545	High Similarity	NPC289771
0.9545	High Similarity	NPC471212
0.9542	High Similarity	NPC210459
0.9539	High Similarity	NPC250922
0.9539	High Similarity	NPC255106
0.9539	High Similarity	NPC235165
0.9539	High Similarity	NPC191146
0.9539	High Similarity	NPC68093
0.9539	High Similarity	NPC471500
0.9536	High Similarity	NPC33051
0.9536	High Similarity	NPC49402
0.9536	High Similarity	NPC273462
0.9536	High Similarity	NPC70433
0.9536	High Similarity	NPC227337
0.9487	High Similarity	NPC300053
0.9487	High Similarity	NPC475888
0.9487	High Similarity	NPC108433
0.9487	High Similarity	NPC472277
0.9487	High Similarity	NPC62261
0.9487	High Similarity	NPC293319
0.9484	High Similarity	NPC211107
0.9484	High Similarity	NPC474150
0.9484	High Similarity	NPC474162
0.9484	High Similarity	NPC472964
0.9481	High Similarity	NPC299436
0.9481	High Similarity	NPC328102
0.9481	High Similarity	NPC470183
0.9481	High Similarity	NPC472902
0.9481	High Similarity	NPC263449
0.9477	High Similarity	NPC472910
0.9477	High Similarity	NPC52889
0.9477	High Similarity	NPC67876
0.9477	High Similarity	NPC472911
0.9477	High Similarity	NPC36852
0.9477	High Similarity	NPC129684
0.9477	High Similarity	NPC472913
0.9477	High Similarity	NPC222814
0.9477	High Similarity	NPC262286
0.9477	High Similarity	NPC472914
0.9477	High Similarity	NPC299520
0.9477	High Similarity	NPC99597
0.9477	High Similarity	NPC96167
0.9477	High Similarity	NPC245758
0.9477	High Similarity	NPC470402
0.9477	High Similarity	NPC210084
0.9474	High Similarity	NPC234255
0.9474	High Similarity	NPC37392
0.9474	High Similarity	NPC256925
0.9474	High Similarity	NPC67396
0.947	High Similarity	NPC240476
0.947	High Similarity	NPC36835
0.947	High Similarity	NPC323626
0.947	High Similarity	NPC260979
0.947	High Similarity	NPC9743
0.947	High Similarity	NPC61506
0.947	High Similarity	NPC477231
0.947	High Similarity	NPC324233
0.947	High Similarity	NPC260491
0.947	High Similarity	NPC257648
0.947	High Similarity	NPC246162
0.9467	High Similarity	NPC88804
0.9467	High Similarity	NPC3825
0.9463	High Similarity	NPC294852
0.9463	High Similarity	NPC321011
0.9463	High Similarity	NPC476342
0.9463	High Similarity	NPC188679
0.943	High Similarity	NPC475212
0.9427	High Similarity	NPC119589
0.9427	High Similarity	NPC43319
0.9423	High Similarity	NPC205265
0.9423	High Similarity	NPC474240
0.9423	High Similarity	NPC7483
0.9423	High Similarity	NPC472281
0.9423	High Similarity	NPC18100
0.9419	High Similarity	NPC66618
0.9419	High Similarity	NPC288131
0.9419	High Similarity	NPC84324
0.9419	High Similarity	NPC305987
0.9419	High Similarity	NPC165970
0.9419	High Similarity	NPC349525
0.9419	High Similarity	NPC308992
0.9419	High Similarity	NPC103201
0.9419	High Similarity	NPC473106
0.9419	High Similarity	NPC113163
0.9416	High Similarity	NPC204879
0.9416	High Similarity	NPC172202
0.9416	High Similarity	NPC85121
0.9416	High Similarity	NPC184755
0.9416	High Similarity	NPC284127
0.9416	High Similarity	NPC74178
0.9416	High Similarity	NPC476410
0.9412	High Similarity	NPC472455
0.9412	High Similarity	NPC208152
0.9412	High Similarity	NPC78492
0.9412	High Similarity	NPC472916
0.9412	High Similarity	NPC24640
0.9412	High Similarity	NPC138243
0.9412	High Similarity	NPC471985
0.9408	High Similarity	NPC469550
0.9408	High Similarity	NPC256346
0.9408	High Similarity	NPC325028
0.9408	High Similarity	NPC27532
0.9408	High Similarity	NPC246328
0.9404	High Similarity	NPC244577
0.9404	High Similarity	NPC278476
0.9404	High Similarity	NPC319910
0.9404	High Similarity	NPC472422
0.9404	High Similarity	NPC471677
0.9404	High Similarity	NPC263384
0.9404	High Similarity	NPC471676
0.9404	High Similarity	NPC256406

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 NPC472598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	911
0.2-0.3	1754
0.3-0.4	2607
0.4-0.5	1798
0.5-0.6	983
0.6-0.7	540
0.7-0.8	148
0.8-0.85	33
0.85-0.9	19
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9799	High Similarity	NPD2393	Clinical (unspecified phase)
0.9732	High Similarity	NPD1934	Approved
0.9363	High Similarity	NPD6168	Clinical (unspecified phase)
0.9363	High Similarity	NPD6167	Clinical (unspecified phase)
0.9363	High Similarity	NPD6166	Phase 2
0.9281	High Similarity	NPD2801	Approved
0.913	High Similarity	NPD7074	Phase 3
0.9085	High Similarity	NPD4380	Phase 2
0.9068	High Similarity	NPD7054	Approved
0.9067	High Similarity	NPD1511	Approved
0.9038	High Similarity	NPD3882	Suspended
0.9012	High Similarity	NPD7472	Approved
0.9006	High Similarity	NPD3818	Discontinued
0.8947	High Similarity	NPD1512	Approved
0.8882	High Similarity	NPD4378	Clinical (unspecified phase)
0.8868	High Similarity	NPD5494	Approved
0.8861	High Similarity	NPD7075	Discontinued
0.8854	High Similarity	NPD3817	Phase 2
0.8841	High Similarity	NPD6797	Phase 2
0.8797	High Similarity	NPD4868	Clinical (unspecified phase)
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.879	High Similarity	NPD7096	Clinical (unspecified phase)
0.8788	High Similarity	NPD7251	Discontinued
0.8742	High Similarity	NPD4381	Clinical (unspecified phase)
0.8735	High Similarity	NPD7808	Phase 3
0.8735	High Similarity	NPD4338	Clinical (unspecified phase)
0.8733	High Similarity	NPD1549	Phase 2
0.8616	High Similarity	NPD8443	Clinical (unspecified phase)
0.8608	High Similarity	NPD6801	Discontinued
0.8606	High Similarity	NPD5844	Phase 1
0.8606	High Similarity	NPD7804	Clinical (unspecified phase)
0.8553	High Similarity	NPD7819	Suspended
0.8528	High Similarity	NPD6232	Discontinued
0.8485	Intermediate Similarity	NPD7473	Discontinued
0.8477	Intermediate Similarity	NPD2796	Approved
0.8466	Intermediate Similarity	NPD6959	Discontinued
0.8452	Intermediate Similarity	NPD6559	Discontinued
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8397	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD6799	Approved
0.8267	Intermediate Similarity	NPD1240	Approved
0.821	Intermediate Similarity	NPD1465	Phase 2
0.8188	Intermediate Similarity	NPD3027	Phase 3
0.816	Intermediate Similarity	NPD5402	Approved
0.8158	Intermediate Similarity	NPD1607	Approved
0.8146	Intermediate Similarity	NPD943	Approved
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD1247	Approved
0.8121	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD919	Approved
0.8095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5403	Approved
0.8054	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2800	Approved
0.7937	Intermediate Similarity	NPD2534	Approved
0.7937	Intermediate Similarity	NPD2532	Approved
0.7937	Intermediate Similarity	NPD2533	Approved
0.7937	Intermediate Similarity	NPD5401	Approved
0.7929	Intermediate Similarity	NPD3926	Phase 2
0.7911	Intermediate Similarity	NPD4628	Phase 3
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD230	Phase 1
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7199	Phase 2
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3750	Approved
0.7798	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD1653	Approved
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7771	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD447	Suspended
0.7738	Intermediate Similarity	NPD3749	Approved
0.773	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD6651	Approved
0.7688	Intermediate Similarity	NPD7228	Approved
0.7688	Intermediate Similarity	NPD3751	Discontinued
0.7679	Intermediate Similarity	NPD4967	Phase 2
0.7679	Intermediate Similarity	NPD4966	Approved
0.7679	Intermediate Similarity	NPD4965	Approved
0.7662	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7658	Intermediate Similarity	NPD6100	Approved
0.7658	Intermediate Similarity	NPD6099	Approved
0.7657	Intermediate Similarity	NPD5953	Discontinued
0.7654	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7286	Phase 2
0.764	Intermediate Similarity	NPD6190	Approved
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4363	Phase 3
0.7637	Intermediate Similarity	NPD4360	Phase 2
0.7636	Intermediate Similarity	NPD3226	Approved
0.7628	Intermediate Similarity	NPD1933	Approved
0.7627	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD8313	Approved
0.7625	Intermediate Similarity	NPD1243	Approved
0.7616	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2346	Discontinued
0.7607	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2799	Discontinued
0.7595	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD9494	Approved
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2313	Discontinued
0.7546	Intermediate Similarity	NPD7390	Discontinued
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7484	Intermediate Similarity	NPD3748	Approved
0.7474	Intermediate Similarity	NPD7584	Approved
0.7469	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5710	Approved
0.7457	Intermediate Similarity	NPD5711	Approved
0.7453	Intermediate Similarity	NPD2424	Discontinued
0.744	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7425	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7405	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5124	Phase 1
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7396	Intermediate Similarity	NPD8151	Discontinued
0.7394	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4625	Phase 3
0.7353	Intermediate Similarity	NPD8455	Phase 2
0.7338	Intermediate Similarity	NPD1203	Approved
0.7325	Intermediate Similarity	NPD6798	Discontinued
0.7317	Intermediate Similarity	NPD2309	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD5242	Approved
0.7312	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4361	Phase 2
0.731	Intermediate Similarity	NPD5353	Approved
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7301	Intermediate Similarity	NPD1652	Phase 2
0.7301	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6844	Discontinued
0.7284	Intermediate Similarity	NPD7266	Discontinued
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7263	Intermediate Similarity	NPD3823	Discontinued
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7233	Intermediate Similarity	NPD4060	Phase 1
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7697	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7225	Intermediate Similarity	NPD7698	Approved
0.7222	Intermediate Similarity	NPD7240	Approved
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7215	Intermediate Similarity	NPD3268	Approved
0.7215	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8127	Discontinued
0.7195	Intermediate Similarity	NPD6674	Discontinued
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD4661	Approved
0.7186	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD2798	Approved
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.717	Intermediate Similarity	NPD6233	Phase 2
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7127	Intermediate Similarity	NPD7038	Approved
0.7127	Intermediate Similarity	NPD7039	Approved
0.7115	Intermediate Similarity	NPD2797	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