NPASS Compound

Structure

NPC218685 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 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 -3.4641 0.0000 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 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 -2.5981 -2.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 0.8660 -2.5000 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 -0.8660 -1.5000 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 7 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 17 2 0 0 0 0 8 21 1 0 0 0 0 9 10 2 0 0 0 0 10 22 1 0 0 0 0 11 6 1 6 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 1 0 0 0 13 14 1 0 0 0 0 13 19 1 6 0 0 0 14 15 1 0 0 0 0 14 20 1 1 0 0 0 15 22 1 6 0 0 0 15 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.12
Volume:	310.659
LogP:	-0.164
LogD:	0.052
LogS:	-1.513
# Rotatable Bonds:	5
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	3.424
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.643
MDCK Permeability:	4.28606836067047e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.064
Human Intestinal Absorption (HIA):	0.742
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.407
Plasma Protein Binding (PPB):	40.48596954345703%
Volume Distribution (VD):	0.476
Pgp-substrate:	31.37635040283203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.146
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.638
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.482
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.621
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	2.913
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.422
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.077
Carcinogencity:	0.092
Eye Corrosion:	0.005
Eye Irritation:	0.301
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC218685

Natural Product ID:	NPC218685
*Common Name:**	Paeonolide
IUPAC Name:	1-[4-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
Synonyms:	Paeonolide
Standard InCHIKey:	AVIUTYMRHHBXPB-UXXRCYHCSA-N
Standard InCHI:	InChI=1S/C15H20O8/c1-7(17)9-4-3-8(21-2)5-10(9)22-15-14(20)13(19)12(18)11(6-16)23-15/h3-5,11-16,18-20H,6H2,1-2H3/t11-,12-,13+,14-,15-/m1/s1
SMILES:	CC(=O)c1ccc(cc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079881
PubChem CID:	442924
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	50000.0	nM	PMID[474246]
NPT35	Others	n.a.		IC50	>	500000.0	nM	PMID[474246]

☑ 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 NPC218685 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	355
0.1-0.2	1421
0.2-0.3	3608
0.3-0.4	8724
0.4-0.5	9815
0.5-0.6	4234
0.6-0.7	5764
0.7-0.8	6145
0.8-0.85	2102
0.85-0.9	451
0.9-0.95	65
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC213723
0.9722	High Similarity	NPC23253
0.9718	High Similarity	NPC23084
0.965	High Similarity	NPC199335
0.9524	High Similarity	NPC99233
0.9521	High Similarity	NPC259767
0.9521	High Similarity	NPC88484
0.9517	High Similarity	NPC106025
0.9517	High Similarity	NPC191154
0.9517	High Similarity	NPC477240
0.9517	High Similarity	NPC214454
0.9459	High Similarity	NPC45165
0.9456	High Similarity	NPC106625
0.9452	High Similarity	NPC134819
0.9452	High Similarity	NPC190217
0.9396	High Similarity	NPC23817
0.9396	High Similarity	NPC43638
0.9392	High Similarity	NPC95090
0.9392	High Similarity	NPC27408
0.9388	High Similarity	NPC259182
0.9388	High Similarity	NPC121001
0.9333	High Similarity	NPC73511
0.9333	High Similarity	NPC43761
0.9329	High Similarity	NPC473657
0.9329	High Similarity	NPC170475
0.9329	High Similarity	NPC265480
0.9329	High Similarity	NPC127406
0.9329	High Similarity	NPC149368
0.9329	High Similarity	NPC295613
0.9329	High Similarity	NPC206378
0.9324	High Similarity	NPC268950
0.9324	High Similarity	NPC211158
0.9324	High Similarity	NPC39360
0.9324	High Similarity	NPC108706
0.9324	High Similarity	NPC78021
0.9324	High Similarity	NPC83283
0.9324	High Similarity	NPC29763
0.9324	High Similarity	NPC210003
0.9324	High Similarity	NPC143851
0.9324	High Similarity	NPC87304
0.9267	High Similarity	NPC60966
0.9267	High Similarity	NPC197896
0.9267	High Similarity	NPC156457
0.9267	High Similarity	NPC6985
0.9267	High Similarity	NPC182634
0.9267	High Similarity	NPC44931
0.9267	High Similarity	NPC313163
0.9267	High Similarity	NPC161749
0.9267	High Similarity	NPC258035
0.9267	High Similarity	NPC108831
0.9267	High Similarity	NPC473512
0.9267	High Similarity	NPC65003
0.9267	High Similarity	NPC129827
0.9262	High Similarity	NPC470605
0.9262	High Similarity	NPC26195
0.9262	High Similarity	NPC470604
0.9262	High Similarity	NPC169248
0.9262	High Similarity	NPC97052
0.9262	High Similarity	NPC470603
0.9262	High Similarity	NPC72649
0.9262	High Similarity	NPC39351
0.9214	High Similarity	NPC294470
0.9211	High Similarity	NPC303913
0.9205	High Similarity	NPC22062
0.9205	High Similarity	NPC41121
0.9205	High Similarity	NPC472459
0.9205	High Similarity	NPC320283
0.9205	High Similarity	NPC111929
0.9205	High Similarity	NPC473634
0.9205	High Similarity	NPC138811
0.92	High Similarity	NPC203500
0.92	High Similarity	NPC307938
0.92	High Similarity	NPC17521
0.92	High Similarity	NPC323593
0.9172	High Similarity	NPC474044
0.9145	High Similarity	NPC271479
0.9145	High Similarity	NPC472320
0.9145	High Similarity	NPC153342
0.9145	High Similarity	NPC187379
0.9145	High Similarity	NPC473623
0.9145	High Similarity	NPC200708
0.9145	High Similarity	NPC142860
0.9145	High Similarity	NPC97285
0.9145	High Similarity	NPC246469
0.9145	High Similarity	NPC271270
0.9139	High Similarity	NPC135391
0.9139	High Similarity	NPC78263
0.9139	High Similarity	NPC122809
0.9139	High Similarity	NPC470606
0.9139	High Similarity	NPC197304
0.9139	High Similarity	NPC133671
0.9139	High Similarity	NPC77672
0.9139	High Similarity	NPC54802
0.9122	High Similarity	NPC38775
0.9097	High Similarity	NPC150023
0.9091	High Similarity	NPC79908
0.9085	High Similarity	NPC159579
0.9085	High Similarity	NPC249281
0.9085	High Similarity	NPC477628
0.9085	High Similarity	NPC246943
0.9085	High Similarity	NPC181465
0.9085	High Similarity	NPC85707
0.9085	High Similarity	NPC224530
0.9085	High Similarity	NPC163242
0.9085	High Similarity	NPC216496
0.9085	High Similarity	NPC210961
0.9085	High Similarity	NPC139320
0.9085	High Similarity	NPC473438
0.9085	High Similarity	NPC215710
0.9085	High Similarity	NPC265885
0.9085	High Similarity	NPC477629
0.9085	High Similarity	NPC182045
0.9085	High Similarity	NPC472994
0.9085	High Similarity	NPC101636
0.9085	High Similarity	NPC195685
0.9085	High Similarity	NPC259957
0.9085	High Similarity	NPC116458
0.9085	High Similarity	NPC276377
0.9085	High Similarity	NPC173582
0.9085	High Similarity	NPC253788
0.9085	High Similarity	NPC270675
0.9085	High Similarity	NPC129217
0.9085	High Similarity	NPC48093
0.9085	High Similarity	NPC476215
0.9079	High Similarity	NPC470607
0.9079	High Similarity	NPC308265
0.9073	High Similarity	NPC261866
0.9054	High Similarity	NPC88886
0.9054	High Similarity	NPC104172
0.9032	High Similarity	NPC139060
0.9026	High Similarity	NPC240306
0.9026	High Similarity	NPC298171
0.9026	High Similarity	NPC127782
0.9026	High Similarity	NPC300537
0.9026	High Similarity	NPC472876
0.9026	High Similarity	NPC44947
0.9026	High Similarity	NPC475382
0.9026	High Similarity	NPC150164
0.9026	High Similarity	NPC190450
0.9026	High Similarity	NPC27942
0.9026	High Similarity	NPC259834
0.9026	High Similarity	NPC131745
0.9026	High Similarity	NPC244875
0.902	High Similarity	NPC470405
0.902	High Similarity	NPC110349
0.902	High Similarity	NPC471079
0.902	High Similarity	NPC136761
0.902	High Similarity	NPC304741
0.9013	High Similarity	NPC288084
0.8968	High Similarity	NPC278419
0.8968	High Similarity	NPC179198
0.8968	High Similarity	NPC257566
0.8968	High Similarity	NPC473644
0.8968	High Similarity	NPC88023
0.8968	High Similarity	NPC88043
0.8968	High Similarity	NPC121703
0.8968	High Similarity	NPC168822
0.8968	High Similarity	NPC80068
0.8968	High Similarity	NPC124155
0.8968	High Similarity	NPC243930
0.8968	High Similarity	NPC66087
0.8968	High Similarity	NPC183672
0.8968	High Similarity	NPC19709
0.8968	High Similarity	NPC309025
0.8968	High Similarity	NPC311850
0.8961	High Similarity	NPC64305
0.8961	High Similarity	NPC170052
0.8961	High Similarity	NPC297987
0.8961	High Similarity	NPC282169
0.8961	High Similarity	NPC47923
0.8961	High Similarity	NPC135846
0.8961	High Similarity	NPC470125
0.8954	High Similarity	NPC279732
0.8954	High Similarity	NPC104677
0.8919	High Similarity	NPC302989
0.8917	High Similarity	NPC116745
0.8917	High Similarity	NPC135345
0.8917	High Similarity	NPC229729
0.891	High Similarity	NPC311830
0.891	High Similarity	NPC85751
0.891	High Similarity	NPC205824
0.891	High Similarity	NPC165720
0.891	High Similarity	NPC475497
0.891	High Similarity	NPC129264
0.891	High Similarity	NPC22832
0.891	High Similarity	NPC475979
0.891	High Similarity	NPC135358
0.891	High Similarity	NPC19240
0.891	High Similarity	NPC72016
0.891	High Similarity	NPC284277
0.891	High Similarity	NPC475366
0.891	High Similarity	NPC294722
0.891	High Similarity	NPC287889
0.8903	High Similarity	NPC473043
0.8903	High Similarity	NPC189142
0.8903	High Similarity	NPC77660
0.8873	High Similarity	NPC212729
0.8861	High Similarity	NPC229687
0.8861	High Similarity	NPC61791
0.8859	High Similarity	NPC10097

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 NPC218685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	836
0.2-0.3	1772
0.3-0.4	2648
0.4-0.5	1957
0.5-0.6	1076
0.6-0.7	375
0.7-0.8	149
0.8-0.85	35
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9267	High Similarity	NPD4381	Clinical (unspecified phase)
0.8742	High Similarity	NPD7804	Clinical (unspecified phase)
0.8742	High Similarity	NPD7054	Approved
0.8716	High Similarity	NPD6799	Approved
0.8688	High Similarity	NPD7472	Approved
0.8688	High Similarity	NPD7074	Phase 3
0.8679	High Similarity	NPD3818	Discontinued
0.8634	High Similarity	NPD6797	Phase 2
0.863	High Similarity	NPD1549	Phase 2
0.8618	High Similarity	NPD4380	Phase 2
0.858	High Similarity	NPD7251	Discontinued
0.8571	High Similarity	NPD7096	Clinical (unspecified phase)
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8528	High Similarity	NPD7808	Phase 3
0.8526	High Similarity	NPD7075	Discontinued
0.8506	High Similarity	NPD6801	Discontinued
0.8466	Intermediate Similarity	NPD6559	Discontinued
0.8415	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1934	Approved
0.8377	Intermediate Similarity	NPD6599	Discontinued
0.8367	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8301	Intermediate Similarity	NPD5403	Approved
0.8289	Intermediate Similarity	NPD5401	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8276	Intermediate Similarity	NPD1240	Approved
0.8217	Intermediate Similarity	NPD7819	Suspended
0.821	Intermediate Similarity	NPD6166	Phase 2
0.821	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1510	Phase 2
0.817	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1607	Approved
0.8146	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD3882	Suspended
0.8105	Intermediate Similarity	NPD1511	Approved
0.8101	Intermediate Similarity	NPD2801	Approved
0.8052	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5402	Approved
0.8014	Intermediate Similarity	NPD1091	Approved
0.8014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1512	Approved
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7898	Intermediate Similarity	NPD1653	Approved
0.7895	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.7853	Intermediate Similarity	NPD5494	Approved
0.7834	Intermediate Similarity	NPD920	Approved
0.7771	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.7733	Intermediate Similarity	NPD1933	Approved
0.7727	Intermediate Similarity	NPD1243	Approved
0.7727	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1652	Phase 2
0.7722	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD9717	Approved
0.7707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6959	Discontinued
0.7692	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3751	Discontinued
0.7654	Intermediate Similarity	NPD8455	Phase 2
0.7651	Intermediate Similarity	NPD3787	Discontinued
0.765	Intermediate Similarity	NPD7584	Approved
0.7647	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5844	Phase 1
0.7616	Intermediate Similarity	NPD8312	Approved
0.7616	Intermediate Similarity	NPD8313	Approved
0.7613	Intermediate Similarity	NPD2800	Approved
0.759	Intermediate Similarity	NPD7199	Phase 2
0.7576	Intermediate Similarity	NPD919	Approved
0.7566	Intermediate Similarity	NPD6651	Approved
0.7564	Intermediate Similarity	NPD3750	Approved
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.7551	Intermediate Similarity	NPD1203	Approved
0.7515	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD1247	Approved
0.7484	Intermediate Similarity	NPD2532	Approved
0.7484	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD3748	Approved
0.7442	Intermediate Similarity	NPD5953	Discontinued
0.744	Intermediate Similarity	NPD6232	Discontinued
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7427	Intermediate Similarity	NPD7286	Phase 2
0.7419	Intermediate Similarity	NPD2935	Discontinued
0.7418	Intermediate Similarity	NPD6782	Approved
0.7418	Intermediate Similarity	NPD6778	Approved
0.7418	Intermediate Similarity	NPD6776	Approved
0.7418	Intermediate Similarity	NPD6777	Approved
0.7418	Intermediate Similarity	NPD6779	Approved
0.7418	Intermediate Similarity	NPD6780	Approved
0.7418	Intermediate Similarity	NPD6781	Approved
0.7412	Intermediate Similarity	NPD7473	Discontinued
0.7397	Intermediate Similarity	NPD422	Phase 1
0.7396	Intermediate Similarity	NPD3926	Phase 2
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2654	Approved
0.7383	Intermediate Similarity	NPD2798	Approved
0.7376	Intermediate Similarity	NPD1241	Discontinued
0.7361	Intermediate Similarity	NPD9545	Approved
0.7355	Intermediate Similarity	NPD7033	Discontinued
0.7348	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2424	Discontinued
0.732	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1613	Approved
0.732	Intermediate Similarity	NPD943	Approved
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7303	Intermediate Similarity	NPD2313	Discontinued
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7299	Intermediate Similarity	NPD7685	Pre-registration
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7287	Intermediate Similarity	NPD8151	Discontinued
0.7273	Intermediate Similarity	NPD7583	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4661	Approved
0.7267	Intermediate Similarity	NPD4662	Approved
0.7261	Intermediate Similarity	NPD2344	Approved
0.7255	Intermediate Similarity	NPD6233	Phase 2
0.7251	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD4965	Approved
0.7234	Intermediate Similarity	NPD7585	Approved
0.7222	Intermediate Similarity	NPD9493	Approved
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7698	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.72	Intermediate Similarity	NPD6104	Discontinued
0.7195	Intermediate Similarity	NPD3226	Approved
0.719	Intermediate Similarity	NPD411	Approved
0.719	Intermediate Similarity	NPD1296	Phase 2
0.7168	Intermediate Similarity	NPD7228	Approved
0.7166	Intermediate Similarity	NPD7871	Phase 2
0.7166	Intermediate Similarity	NPD7870	Phase 2
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7159	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7151	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6535	Approved
0.7134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.712	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3142	Approved
0.7097	Intermediate Similarity	NPD3140	Approved
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD5353	Approved
0.7081	Intermediate Similarity	NPD2354	Approved
0.7081	Intermediate Similarity	NPD2309	Approved
0.7081	Intermediate Similarity	NPD3887	Approved
0.7078	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD290	Approved
0.707	Intermediate Similarity	NPD7097	Phase 1
0.7068	Intermediate Similarity	NPD7874	Approved
0.7068	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6844	Discontinued
0.7059	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4908	Phase 1
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2403	Approved
0.7049	Intermediate Similarity	NPD4360	Phase 2
0.7049	Intermediate Similarity	NPD4363	Phase 3
0.7047	Intermediate Similarity	NPD1610	Phase 2
0.7039	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5647	Approved
0.7035	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD5710	Approved
0.7032	Intermediate Similarity	NPD4062	Phase 3
0.7031	Intermediate Similarity	NPD7801	Approved
0.7027	Intermediate Similarity	NPD7699	Phase 2
0.7027	Intermediate Similarity	NPD7700	Phase 2
0.7013	Intermediate Similarity	NPD3027	Phase 3
0.7006	Intermediate Similarity	NPD7240	Approved
0.7	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD3972	Approved
0.6993	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9494	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