NPASS Compound

Structure

NPC472419 OpenBabel07101719142D 26 27 0 0 0 0 0 0 0 0999 V2000 2.5981 -2.5000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -6.0622 0.5000 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 -0.8660 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 0.0000 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 -4.3301 0.5000 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 -0.8660 0.5000 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 -1.7321 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 0.8660 1.5000 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 -6.9282 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 0.8660 -1.5000 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 1.7321 2.0000 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 26 1 0 0 0 0 4 7 1 0 0 0 0 4 14 2 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 15 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 18 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 19 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 23 2 0 0 0 0 19 24 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.13
Volume:	372.246
LogP:	3.587
LogD:	2.928
LogS:	-4.199
# Rotatable Bonds:	7
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	2.58
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.743
MDCK Permeability:	1.8492370145395398e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	99.47474670410156%
Volume Distribution (VD):	0.414
Pgp-substrate:	0.8559231758117676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.878
CYP1A2-substrate:	0.674
CYP2C19-inhibitor:	0.798
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.435
CYP2D6-substrate:	0.736
CYP3A4-inhibitor:	0.589
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	11.839
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.673
AMES Toxicity:	0.704
Rat Oral Acute Toxicity:	0.825
Maximum Recommended Daily Dose:	0.492
Skin Sensitization:	0.911
Carcinogencity:	0.594
Eye Corrosion:	0.003
Eye Irritation:	0.489
Respiratory Toxicity:	0.753

Download Data

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

Natural Product: NPC472419

Natural Product ID:	NPC472419
*Common Name:**	MYWUHPGPXHNDRC-UXBLZVDNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MYWUHPGPXHNDRC-UXBLZVDNSA-N
Standard InCHI:	InChI=1S/C21H20O5/c1-13(2)19(24)12-17-20(26-3)11-9-16(21(17)25)18(23)10-6-14-4-7-15(22)8-5-14/h4-11,22,25H,1,12H2,2-3H3/b10-6+
SMILES:	CC(=C)C(=O)CC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3402548
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

*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
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21056	Angelica keiskei	Species	Apiaceae	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
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	85.17	%	PMID[468056]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	0.82	ug.mL-1	PMID[468056]

☑ 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 NPC472419 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	351
0.1-0.2	1545
0.2-0.3	4043
0.3-0.4	10322
0.4-0.5	7931
0.5-0.6	3651
0.6-0.7	5921
0.7-0.8	5270
0.8-0.85	2125
0.85-0.9	969
0.9-0.95	490
0.95-1	79

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC168105
0.9924	High Similarity	NPC186838
0.9924	High Similarity	NPC1486
0.9924	High Similarity	NPC274109
0.9924	High Similarity	NPC477242
0.9924	High Similarity	NPC150399
0.9924	High Similarity	NPC41461
0.9924	High Similarity	NPC66349
0.9924	High Similarity	NPC249606
0.9924	High Similarity	NPC12165
0.9924	High Similarity	NPC477243
0.9924	High Similarity	NPC25287
0.9924	High Similarity	NPC477244
0.9924	High Similarity	NPC98115
0.985	High Similarity	NPC477956
0.9848	High Similarity	NPC317119
0.9848	High Similarity	NPC153979
0.9847	High Similarity	NPC156092
0.9847	High Similarity	NPC131039
0.9847	High Similarity	NPC13575
0.9774	High Similarity	NPC21350
0.9771	High Similarity	NPC286336
0.9771	High Similarity	NPC103842
0.9704	High Similarity	NPC55832
0.9704	High Similarity	NPC268204
0.9704	High Similarity	NPC52789
0.9704	High Similarity	NPC26051
0.9701	High Similarity	NPC470211
0.9701	High Similarity	NPC472366
0.9695	High Similarity	NPC294593
0.9695	High Similarity	NPC192304
0.9695	High Similarity	NPC312318
0.9695	High Similarity	NPC263670
0.9695	High Similarity	NPC472365
0.9695	High Similarity	NPC20560
0.9695	High Similarity	NPC82225
0.9695	High Similarity	NPC204960
0.9695	High Similarity	NPC175098
0.9695	High Similarity	NPC337373
0.9695	High Similarity	NPC188646
0.9695	High Similarity	NPC242294
0.9695	High Similarity	NPC56031
0.9695	High Similarity	NPC27643
0.9695	High Similarity	NPC18877
0.9695	High Similarity	NPC159623
0.9695	High Similarity	NPC144051
0.9695	High Similarity	NPC139813
0.9695	High Similarity	NPC28753
0.963	High Similarity	NPC204985
0.963	High Similarity	NPC253822
0.963	High Similarity	NPC219917
0.963	High Similarity	NPC172250
0.963	High Similarity	NPC326109
0.963	High Similarity	NPC101366
0.963	High Similarity	NPC80962
0.963	High Similarity	NPC144118
0.963	High Similarity	NPC259166
0.963	High Similarity	NPC11056
0.963	High Similarity	NPC213659
0.963	High Similarity	NPC48624
0.963	High Similarity	NPC215311
0.9627	High Similarity	NPC471620
0.9627	High Similarity	NPC251681
0.9627	High Similarity	NPC243528
0.9618	High Similarity	NPC212631
0.9618	High Similarity	NPC257756
0.9618	High Similarity	NPC129132
0.9618	High Similarity	NPC205468
0.9618	High Similarity	NPC87231
0.9559	High Similarity	NPC469404
0.9559	High Similarity	NPC110969
0.9559	High Similarity	NPC470089
0.9559	High Similarity	NPC470087
0.9559	High Similarity	NPC321980
0.9556	High Similarity	NPC295384
0.9556	High Similarity	NPC283429
0.9542	High Similarity	NPC186097
0.9542	High Similarity	NPC475008
0.9542	High Similarity	NPC262359
0.9542	High Similarity	NPC164236
0.9542	High Similarity	NPC128348
0.9542	High Similarity	NPC308037
0.9542	High Similarity	NPC66384
0.9542	High Similarity	NPC64359
0.9542	High Similarity	NPC475009
0.9542	High Similarity	NPC112192
0.9542	High Similarity	NPC189106
0.9542	High Similarity	NPC313618
0.9542	High Similarity	NPC309717
0.9493	High Similarity	NPC234629
0.9493	High Similarity	NPC476055
0.9493	High Similarity	NPC311741
0.9489	High Similarity	NPC11561
0.9489	High Similarity	NPC226636
0.9485	High Similarity	NPC270883
0.9485	High Similarity	NPC241100
0.9485	High Similarity	NPC261227
0.9485	High Similarity	NPC69769
0.9485	High Similarity	NPC159275
0.9485	High Similarity	NPC172986
0.9481	High Similarity	NPC309154
0.9481	High Similarity	NPC472368
0.9481	High Similarity	NPC90665
0.9481	High Similarity	NPC12175
0.9481	High Similarity	NPC55162
0.9481	High Similarity	NPC124269
0.9481	High Similarity	NPC278323
0.9481	High Similarity	NPC279668
0.9478	High Similarity	NPC24394
0.9478	High Similarity	NPC473391
0.9478	High Similarity	NPC472367
0.9478	High Similarity	NPC472364
0.9478	High Similarity	NPC476333
0.9478	High Similarity	NPC213603
0.9474	High Similarity	NPC164136
0.947	High Similarity	NPC15834
0.947	High Similarity	NPC215875
0.942	High Similarity	NPC221432
0.942	High Similarity	NPC175504
0.942	High Similarity	NPC166138
0.942	High Similarity	NPC475705
0.942	High Similarity	NPC257097
0.942	High Similarity	NPC91560
0.942	High Similarity	NPC310130
0.942	High Similarity	NPC106985
0.942	High Similarity	NPC75049
0.942	High Similarity	NPC39329
0.942	High Similarity	NPC117836
0.942	High Similarity	NPC149026
0.942	High Similarity	NPC245482
0.942	High Similarity	NPC150408
0.942	High Similarity	NPC143896
0.942	High Similarity	NPC68104
0.942	High Similarity	NPC169591
0.942	High Similarity	NPC476178
0.942	High Similarity	NPC301751
0.942	High Similarity	NPC164980
0.942	High Similarity	NPC51887
0.942	High Similarity	NPC18585
0.9416	High Similarity	NPC282300
0.9416	High Similarity	NPC49108
0.9416	High Similarity	NPC156590
0.9416	High Similarity	NPC205006
0.9416	High Similarity	NPC26238
0.9416	High Similarity	NPC103362
0.9416	High Similarity	NPC118840
0.9416	High Similarity	NPC147688
0.9416	High Similarity	NPC3188
0.9416	High Similarity	NPC64908
0.9412	High Similarity	NPC303633
0.9412	High Similarity	NPC217186
0.9412	High Similarity	NPC18260
0.9412	High Similarity	NPC96565
0.9412	High Similarity	NPC220062
0.9412	High Similarity	NPC78913
0.9412	High Similarity	NPC53181
0.9412	High Similarity	NPC55018
0.9412	High Similarity	NPC216978
0.9412	High Similarity	NPC301217
0.9407	High Similarity	NPC303644
0.9407	High Similarity	NPC209560
0.9407	High Similarity	NPC162680
0.9407	High Similarity	NPC23870
0.9407	High Similarity	NPC188879
0.9407	High Similarity	NPC116632
0.9407	High Similarity	NPC181124
0.9407	High Similarity	NPC7013
0.9407	High Similarity	NPC294409
0.9398	High Similarity	NPC16197
0.9389	High Similarity	NPC84772
0.9389	High Similarity	NPC247779
0.9353	High Similarity	NPC197252
0.9353	High Similarity	NPC473013
0.9353	High Similarity	NPC209040
0.9353	High Similarity	NPC236766
0.9353	High Similarity	NPC473015
0.9353	High Similarity	NPC328623
0.9348	High Similarity	NPC66515
0.9348	High Similarity	NPC161506
0.9348	High Similarity	NPC32739
0.9348	High Similarity	NPC324436
0.9348	High Similarity	NPC148545
0.9348	High Similarity	NPC297600
0.9348	High Similarity	NPC328164
0.9348	High Similarity	NPC76338
0.9348	High Similarity	NPC194432
0.9348	High Similarity	NPC306829
0.9348	High Similarity	NPC144499
0.9348	High Similarity	NPC148757
0.9348	High Similarity	NPC177354
0.9348	High Similarity	NPC125855
0.9348	High Similarity	NPC324134
0.9348	High Similarity	NPC296917
0.9348	High Similarity	NPC166934
0.9348	High Similarity	NPC76372
0.9348	High Similarity	NPC220998
0.9348	High Similarity	NPC182852
0.9348	High Similarity	NPC64915
0.9348	High Similarity	NPC37496
0.9348	High Similarity	NPC40833

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 NPC472419 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	959
0.2-0.3	1453
0.3-0.4	2606
0.4-0.5	1965
0.5-0.6	1221
0.6-0.7	422
0.7-0.8	149
0.8-0.85	36
0.85-0.9	11
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9542	High Similarity	NPD1240	Approved
0.9398	High Similarity	NPD1607	Approved
0.9259	High Similarity	NPD1510	Phase 2
0.9214	High Similarity	NPD4378	Clinical (unspecified phase)
0.9078	High Similarity	NPD7410	Clinical (unspecified phase)
0.9058	High Similarity	NPD1549	Phase 2
0.8986	High Similarity	NPD1552	Clinical (unspecified phase)
0.8986	High Similarity	NPD1550	Clinical (unspecified phase)
0.8897	High Similarity	NPD4380	Phase 2
0.8836	High Similarity	NPD7411	Suspended
0.8777	High Similarity	NPD2796	Approved
0.8716	High Similarity	NPD2393	Clinical (unspecified phase)
0.8696	High Similarity	NPD6651	Approved
0.8667	High Similarity	NPD7075	Discontinued
0.8658	High Similarity	NPD8443	Clinical (unspecified phase)
0.8643	High Similarity	NPD2935	Discontinued
0.8611	High Similarity	NPD6799	Approved
0.8591	High Similarity	NPD7819	Suspended
0.8591	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD6801	Discontinued
0.8477	Intermediate Similarity	NPD3882	Suspended
0.8467	Intermediate Similarity	NPD2801	Approved
0.8462	Intermediate Similarity	NPD2800	Approved
0.8462	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1934	Approved
0.8392	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD6599	Discontinued
0.8356	Intermediate Similarity	NPD1511	Approved
0.8355	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.831	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD2799	Discontinued
0.8301	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD2534	Approved
0.8299	Intermediate Similarity	NPD2533	Approved
0.8299	Intermediate Similarity	NPD2532	Approved
0.8286	Intermediate Similarity	NPD943	Approved
0.828	Intermediate Similarity	NPD7473	Discontinued
0.8276	Intermediate Similarity	NPD3750	Approved
0.8273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1551	Phase 2
0.8243	Intermediate Similarity	NPD1512	Approved
0.8207	Intermediate Similarity	NPD1243	Approved
0.8194	Intermediate Similarity	NPD2344	Approved
0.8188	Intermediate Similarity	NPD920	Approved
0.8187	Intermediate Similarity	NPD5953	Discontinued
0.8182	Intermediate Similarity	NPD3749	Approved
0.8176	Intermediate Similarity	NPD7286	Phase 2
0.8141	Intermediate Similarity	NPD6959	Discontinued
0.8077	Intermediate Similarity	NPD5494	Approved
0.8063	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD1203	Approved
0.8041	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7987	Intermediate Similarity	NPD6166	Phase 2
0.7987	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2798	Approved
0.7973	Intermediate Similarity	NPD2309	Approved
0.7959	Intermediate Similarity	NPD2654	Approved
0.7956	Intermediate Similarity	NPD3972	Approved
0.7947	Intermediate Similarity	NPD5403	Approved
0.7935	Intermediate Similarity	NPD3817	Phase 2
0.7931	Intermediate Similarity	NPD3748	Approved
0.7885	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6832	Phase 2
0.7867	Intermediate Similarity	NPD7390	Discontinued
0.7866	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD3226	Approved
0.7836	Intermediate Similarity	NPD9493	Approved
0.7826	Intermediate Similarity	NPD9717	Approved
0.7815	Intermediate Similarity	NPD5401	Approved
0.7805	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7054	Approved
0.7721	Intermediate Similarity	NPD9545	Approved
0.7712	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5402	Approved
0.7703	Intermediate Similarity	NPD2346	Discontinued
0.7702	Intermediate Similarity	NPD3926	Phase 2
0.7688	Intermediate Similarity	NPD1247	Approved
0.7683	Intermediate Similarity	NPD7472	Approved
0.7673	Intermediate Similarity	NPD919	Approved
0.766	Intermediate Similarity	NPD1164	Approved
0.766	Intermediate Similarity	NPD1470	Approved
0.764	Intermediate Similarity	NPD5711	Approved
0.764	Intermediate Similarity	NPD5710	Approved
0.7639	Intermediate Similarity	NPD3268	Approved
0.7636	Intermediate Similarity	NPD6797	Phase 2
0.7635	Intermediate Similarity	NPD6099	Approved
0.7635	Intermediate Similarity	NPD6100	Approved
0.7626	Intermediate Similarity	NPD422	Phase 1
0.7622	Intermediate Similarity	NPD5844	Phase 1
0.7622	Intermediate Similarity	NPD4908	Phase 1
0.7613	Intermediate Similarity	NPD7458	Discontinued
0.7603	Intermediate Similarity	NPD230	Phase 1
0.7591	Intermediate Similarity	NPD1548	Phase 1
0.759	Intermediate Similarity	NPD7251	Discontinued
0.7576	Intermediate Similarity	NPD1729	Discontinued
0.7568	Intermediate Similarity	NPD7033	Discontinued
0.7568	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7003	Approved
0.7545	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7808	Phase 3
0.7536	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD2797	Approved
0.7517	Intermediate Similarity	NPD5406	Approved
0.7517	Intermediate Similarity	NPD3764	Approved
0.7517	Intermediate Similarity	NPD5408	Approved
0.7517	Intermediate Similarity	NPD5404	Approved
0.7517	Intermediate Similarity	NPD5405	Approved
0.7516	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7465	Intermediate Similarity	NPD1876	Approved
0.745	Intermediate Similarity	NPD4308	Phase 3
0.7429	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1465	Phase 2
0.7414	Intermediate Similarity	NPD4363	Phase 3
0.7414	Intermediate Similarity	NPD4360	Phase 2
0.7399	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2296	Approved
0.7371	Intermediate Similarity	NPD4361	Phase 2
0.7371	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD447	Suspended
0.7365	Intermediate Similarity	NPD5124	Phase 1
0.7365	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1933	Approved
0.7353	Intermediate Similarity	NPD1241	Discontinued
0.7351	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1471	Phase 3
0.7343	Intermediate Similarity	NPD3225	Approved
0.7329	Intermediate Similarity	NPD3027	Phase 3
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7324	Intermediate Similarity	NPD1608	Approved
0.731	Intermediate Similarity	NPD9494	Approved
0.7303	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3267	Approved
0.7292	Intermediate Similarity	NPD3266	Approved
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1651	Approved
0.7279	Intermediate Similarity	NPD411	Approved
0.7279	Intermediate Similarity	NPD1296	Phase 2
0.7278	Intermediate Similarity	NPD6104	Discontinued
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4288	Approved
0.7246	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1019	Discontinued
0.7239	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD9266	Approved
0.7222	Intermediate Similarity	NPD1283	Approved
0.7212	Intermediate Similarity	NPD7229	Phase 3
0.7197	Intermediate Similarity	NPD5049	Phase 3
0.7194	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5890	Approved
0.7188	Intermediate Similarity	NPD5889	Approved
0.7184	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4287	Approved
0.7183	Intermediate Similarity	NPD3847	Discontinued
0.7181	Intermediate Similarity	NPD4307	Phase 2
0.7176	Intermediate Similarity	NPD940	Approved
0.7176	Intermediate Similarity	NPD846	Approved
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9267	Approved
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9263	Approved
0.7164	Intermediate Similarity	NPD9264	Approved
0.7162	Intermediate Similarity	NPD6798	Discontinued
0.7161	Intermediate Similarity	NPD2354	Approved
0.7153	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6279	Approved
0.7134	Intermediate Similarity	NPD4662	Approved
0.7134	Intermediate Similarity	NPD4661	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2403	Approved
0.7125	Intermediate Similarity	NPD6585	Discontinued
0.7113	Intermediate Similarity	NPD4626	Approved
0.7113	Intermediate Similarity	NPD17	Approved
0.7111	Intermediate Similarity	NPD6781	Approved
0.7111	Intermediate Similarity	NPD6777	Approved
0.7111	Intermediate Similarity	NPD6778	Approved
0.7111	Intermediate Similarity	NPD6782	Approved
0.7111	Intermediate Similarity	NPD6780	Approved
0.7111	Intermediate Similarity	NPD6776	Approved
0.7111	Intermediate Similarity	NPD6779	Approved
0.7093	Intermediate Similarity	NPD8312	Approved
0.7093	Intermediate Similarity	NPD8313	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