NPASS Compound

Structure

CID23253 OpenBabel06191715352D 32 34 0 0 1 0 0 0 0 0999 V2000 5.3007 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 5.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 4.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2007 0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3917 0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 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 4.4347 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 28 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 29 1 0 0 0 0 7 20 1 0 0 0 0 7 21 1 0 0 0 0 8 20 1 0 0 0 0 8 30 1 0 0 0 0 9 11 1 0 0 0 0 9 22 2 0 0 0 0 10 28 1 0 0 0 0 11 12 2 0 0 0 0 12 31 1 0 0 0 0 13 6 1 6 0 0 0 13 14 1 0 0 0 0 13 32 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 1 0 0 0 15 16 1 0 0 0 0 15 24 1 6 0 0 0 16 18 1 0 0 0 0 16 25 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 17 26 1 0 0 0 0 18 31 1 6 0 0 0 18 32 1 0 0 0 0 19 29 1 6 0 0 0 19 30 1 0 0 0 0 20 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.16
Volume:	423.744
LogP:	-0.389
LogD:	-0.543
LogS:	-2.276
# Rotatable Bonds:	8
TPSA:	184.6
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	4.359
Fsp3:	0.65
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.41
MDCK Permeability:	3.65462910849601e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.917
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.208
Plasma Protein Binding (PPB):	32.30226516723633%
Volume Distribution (VD):	0.448
Pgp-substrate:	34.59578323364258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.277
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	1.376
Half-life (T1/2):	0.723

ADMET: Toxicity

hERG Blockers:	0.298
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.555
AMES Toxicity:	0.3
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.207
Carcinogencity:	0.08
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC23253

Natural Product ID:	NPC23253
*Common Name:**	Paeonoside
IUPAC Name:	1-[2-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-methoxyphenyl]ethanone
Synonyms:	Paeonoside
Standard InCHIKey:	IRLNKOAURQPXIQ-LTRJMQNCSA-N
Standard InCHI:	InChI=1S/C20H28O12/c1-9(22)11-4-3-10(28-2)5-12(11)31-18-16(25)15(24)14(23)13(32-18)6-29-19-17(26)20(27,7-21)8-30-19/h3-5,13-19,21,23-27H,6-8H2,1-2H3/t13-,14-,15+,16-,17+,18-,19-,20-/m1/s1
SMILES:	COc1ccc(c(c1)O[C@@H]1O[C@H](CO[C@@H]2OC[C@]([C@H]2O)(O)CO)[C@H]([C@@H]([C@H]1O)O)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079882
PubChem CID:	46883331
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	4
Others	4

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1000000.0	nM	PMID[548552]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	50000.0	nM	PMID[548551]
NPT35	Others	n.a.		IC50	>	500000.0	nM	PMID[548551]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	20500.0	nM	PMID[548552]
NPT2	Others	Unspecified		Ratio IC50	=	48.8	n.a.	PMID[548552]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Inhibition	=	73.0	%	PMID[548552]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	68.0	%	PMID[548552]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	23.0	%	PMID[548552]

☑ 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 NPC23253 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	350
0.1-0.2	1330
0.2-0.3	3227
0.3-0.4	7852
0.4-0.5	10594
0.5-0.6	4978
0.6-0.7	5816
0.7-0.8	6797
0.8-0.85	1525
0.85-0.9	197
0.9-0.95	29
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC218685
0.9658	High Similarity	NPC213723
0.9597	High Similarity	NPC149368
0.9597	High Similarity	NPC265480
0.9521	High Similarity	NPC199335
0.9467	High Similarity	NPC17521
0.9452	High Similarity	NPC23084
0.9408	High Similarity	NPC200708
0.9404	High Similarity	NPC122809
0.94	High Similarity	NPC99233
0.9396	High Similarity	NPC259767
0.9396	High Similarity	NPC88484
0.9392	High Similarity	NPC214454
0.9392	High Similarity	NPC106025
0.9392	High Similarity	NPC191154
0.9392	High Similarity	NPC477240
0.9342	High Similarity	NPC470607
0.9338	High Similarity	NPC45165
0.9333	High Similarity	NPC106625
0.9329	High Similarity	NPC134819
0.9329	High Similarity	NPC190217
0.9286	High Similarity	NPC150164
0.9276	High Similarity	NPC23817
0.9276	High Similarity	NPC470606
0.9276	High Similarity	NPC43638
0.9272	High Similarity	NPC95090
0.9272	High Similarity	NPC27408
0.9267	High Similarity	NPC259182
0.9267	High Similarity	NPC121001
0.9216	High Similarity	NPC73511
0.9216	High Similarity	NPC43761
0.9211	High Similarity	NPC127406
0.9211	High Similarity	NPC295613
0.9211	High Similarity	NPC473657
0.9211	High Similarity	NPC170475
0.9211	High Similarity	NPC206378
0.9205	High Similarity	NPC87304
0.9205	High Similarity	NPC78021
0.9205	High Similarity	NPC210003
0.9205	High Similarity	NPC83283
0.9205	High Similarity	NPC143851
0.9205	High Similarity	NPC39360
0.9205	High Similarity	NPC29763
0.9205	High Similarity	NPC268950
0.9205	High Similarity	NPC211158
0.9205	High Similarity	NPC108706
0.9195	High Similarity	NPC88886
0.9195	High Similarity	NPC104172
0.9184	High Similarity	NPC474044
0.9167	High Similarity	NPC72016
0.915	High Similarity	NPC313163
0.915	High Similarity	NPC6985
0.915	High Similarity	NPC258035
0.915	High Similarity	NPC197896
0.915	High Similarity	NPC60966
0.915	High Similarity	NPC161749
0.915	High Similarity	NPC288084
0.915	High Similarity	NPC156457
0.915	High Similarity	NPC129827
0.915	High Similarity	NPC65003
0.915	High Similarity	NPC473512
0.915	High Similarity	NPC108831
0.915	High Similarity	NPC44931
0.915	High Similarity	NPC182634
0.9145	High Similarity	NPC470605
0.9145	High Similarity	NPC470604
0.9145	High Similarity	NPC97052
0.9145	High Similarity	NPC169248
0.9145	High Similarity	NPC26195
0.9145	High Similarity	NPC72649
0.9145	High Similarity	NPC39351
0.9145	High Similarity	NPC470603
0.9103	High Similarity	NPC471286
0.9097	High Similarity	NPC303913
0.9091	High Similarity	NPC472459
0.9091	High Similarity	NPC138811
0.9091	High Similarity	NPC473634
0.9091	High Similarity	NPC22062
0.9091	High Similarity	NPC279732
0.9091	High Similarity	NPC41121
0.9091	High Similarity	NPC111929
0.9091	High Similarity	NPC320283
0.9085	High Similarity	NPC203500
0.9085	High Similarity	NPC323593
0.9085	High Similarity	NPC307938
0.9057	High Similarity	NPC212748
0.9038	High Similarity	NPC93215
0.9032	High Similarity	NPC187379
0.9032	High Similarity	NPC473623
0.9032	High Similarity	NPC97285
0.9032	High Similarity	NPC142860
0.9032	High Similarity	NPC271479
0.9032	High Similarity	NPC472320
0.9032	High Similarity	NPC246469
0.9032	High Similarity	NPC153342
0.9032	High Similarity	NPC271270
0.9026	High Similarity	NPC197304
0.9026	High Similarity	NPC54802
0.9026	High Similarity	NPC77672
0.9026	High Similarity	NPC78263
0.9026	High Similarity	NPC135391
0.9026	High Similarity	NPC133671
0.9007	High Similarity	NPC38775
0.9	High Similarity	NPC235575
0.8981	High Similarity	NPC121703
0.8981	High Similarity	NPC183672
0.8974	High Similarity	NPC129217
0.8974	High Similarity	NPC215710
0.8974	High Similarity	NPC181465
0.8974	High Similarity	NPC163242
0.8974	High Similarity	NPC265885
0.8974	High Similarity	NPC182045
0.8974	High Similarity	NPC210961
0.8974	High Similarity	NPC224530
0.8974	High Similarity	NPC477628
0.8974	High Similarity	NPC472994
0.8974	High Similarity	NPC276377
0.8974	High Similarity	NPC473438
0.8974	High Similarity	NPC270675
0.8974	High Similarity	NPC259957
0.8974	High Similarity	NPC85707
0.8974	High Similarity	NPC216496
0.8974	High Similarity	NPC249281
0.8974	High Similarity	NPC476215
0.8974	High Similarity	NPC173582
0.8974	High Similarity	NPC159579
0.8974	High Similarity	NPC253788
0.8974	High Similarity	NPC477629
0.8974	High Similarity	NPC116458
0.8974	High Similarity	NPC48093
0.8974	High Similarity	NPC101636
0.8974	High Similarity	NPC246943
0.8974	High Similarity	NPC195685
0.8974	High Similarity	NPC139320
0.8973	High Similarity	NPC79908
0.8968	High Similarity	NPC308265
0.8961	High Similarity	NPC261866
0.8958	High Similarity	NPC294470
0.8947	High Similarity	NPC472423
0.8947	High Similarity	NPC318424
0.8947	High Similarity	NPC474772
0.8947	High Similarity	NPC474744
0.8931	High Similarity	NPC48640
0.8931	High Similarity	NPC149244
0.8924	High Similarity	NPC139060
0.8924	High Similarity	NPC294722
0.8924	High Similarity	NPC475979
0.8917	High Similarity	NPC244875
0.8917	High Similarity	NPC475382
0.8917	High Similarity	NPC27942
0.8917	High Similarity	NPC131745
0.8917	High Similarity	NPC240306
0.8917	High Similarity	NPC44947
0.8917	High Similarity	NPC127782
0.8917	High Similarity	NPC300537
0.8917	High Similarity	NPC472876
0.8917	High Similarity	NPC259834
0.8917	High Similarity	NPC190450
0.8917	High Similarity	NPC298171
0.891	High Similarity	NPC110349
0.891	High Similarity	NPC471079
0.891	High Similarity	NPC304741
0.891	High Similarity	NPC136761
0.891	High Similarity	NPC306978
0.891	High Similarity	NPC470405
0.8889	High Similarity	NPC473996
0.8882	High Similarity	NPC472421
0.8882	High Similarity	NPC245452
0.8882	High Similarity	NPC261254
0.8875	High Similarity	NPC473202
0.8867	High Similarity	NPC474302
0.8867	High Similarity	NPC469700
0.8861	High Similarity	NPC19709
0.8861	High Similarity	NPC311850
0.8861	High Similarity	NPC124155
0.8861	High Similarity	NPC88023
0.8861	High Similarity	NPC88043
0.8861	High Similarity	NPC91288
0.8861	High Similarity	NPC168822
0.8861	High Similarity	NPC473644
0.8861	High Similarity	NPC243930
0.8861	High Similarity	NPC66087
0.8861	High Similarity	NPC257566
0.8861	High Similarity	NPC80068
0.8861	High Similarity	NPC309025
0.8861	High Similarity	NPC179198
0.8861	High Similarity	NPC278419
0.8854	High Similarity	NPC47923
0.8854	High Similarity	NPC135846
0.8854	High Similarity	NPC170052
0.8854	High Similarity	NPC282169
0.8854	High Similarity	NPC64305
0.8854	High Similarity	NPC297987
0.8854	High Similarity	NPC470125
0.8851	High Similarity	NPC150023
0.8846	High Similarity	NPC104677
0.8834	High Similarity	NPC325176
0.8824	High Similarity	NPC244577
0.8824	High Similarity	NPC250488
0.8824	High Similarity	NPC472636

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 NPC23253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	789
0.2-0.3	1758
0.3-0.4	2632
0.4-0.5	2064
0.5-0.6	1090
0.6-0.7	363
0.7-0.8	149
0.8-0.85	17
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.915	High Similarity	NPD4381	Clinical (unspecified phase)
0.8812	High Similarity	NPD3818	Discontinued
0.8642	High Similarity	NPD7054	Approved
0.8642	High Similarity	NPD7804	Clinical (unspecified phase)
0.8609	High Similarity	NPD6799	Approved
0.8598	High Similarity	NPD6559	Discontinued
0.8589	High Similarity	NPD7074	Phase 3
0.8589	High Similarity	NPD7472	Approved
0.8537	High Similarity	NPD6797	Phase 2
0.8516	High Similarity	NPD4380	Phase 2
0.8485	Intermediate Similarity	NPD7251	Discontinued
0.8471	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7808	Phase 3
0.8428	Intermediate Similarity	NPD7075	Discontinued
0.8408	Intermediate Similarity	NPD6801	Discontinued
0.84	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1934	Approved
0.828	Intermediate Similarity	NPD6599	Discontinued
0.8267	Intermediate Similarity	NPD2796	Approved
0.825	Intermediate Similarity	NPD3882	Suspended
0.8239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7411	Suspended
0.8205	Intermediate Similarity	NPD5403	Approved
0.8194	Intermediate Similarity	NPD5401	Approved
0.8187	Intermediate Similarity	NPD3817	Phase 2
0.8125	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6166	Phase 2
0.8077	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1240	Approved
0.8052	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2801	Approved
0.7988	Intermediate Similarity	NPD5494	Approved
0.7963	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5402	Approved
0.7961	Intermediate Similarity	NPD1510	Phase 2
0.7947	Intermediate Similarity	NPD1607	Approved
0.7919	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1511	Approved
0.7862	Intermediate Similarity	NPD920	Approved
0.7862	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4628	Phase 3
0.7799	Intermediate Similarity	NPD1512	Approved
0.7793	Intermediate Similarity	NPD1091	Approved
0.7758	Intermediate Similarity	NPD3749	Approved
0.7756	Intermediate Similarity	NPD2800	Approved
0.7756	Intermediate Similarity	NPD1243	Approved
0.774	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7199	Phase 2
0.7722	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3751	Discontinued
0.7702	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3787	Discontinued
0.7677	Intermediate Similarity	NPD1551	Phase 2
0.7676	Intermediate Similarity	NPD7584	Approved
0.7667	Intermediate Similarity	NPD6832	Phase 2
0.7647	Intermediate Similarity	NPD1933	Approved
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2532	Approved
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD6959	Discontinued
0.7605	Intermediate Similarity	NPD919	Approved
0.7576	Intermediate Similarity	NPD8455	Phase 2
0.7572	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5844	Phase 1
0.7543	Intermediate Similarity	NPD8313	Approved
0.7543	Intermediate Similarity	NPD8312	Approved
0.7532	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD1652	Phase 2
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7515	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7485	Intermediate Similarity	NPD7768	Phase 2
0.7484	Intermediate Similarity	NPD3750	Approved
0.7484	Intermediate Similarity	NPD6651	Approved
0.7468	Intermediate Similarity	NPD2424	Discontinued
0.7446	Intermediate Similarity	NPD6778	Approved
0.7446	Intermediate Similarity	NPD6776	Approved
0.7446	Intermediate Similarity	NPD6782	Approved
0.7446	Intermediate Similarity	NPD6777	Approved
0.7446	Intermediate Similarity	NPD6780	Approved
0.7446	Intermediate Similarity	NPD6781	Approved
0.7446	Intermediate Similarity	NPD6779	Approved
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7685	Pre-registration
0.741	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD2344	Approved
0.7389	Intermediate Similarity	NPD2799	Discontinued
0.7389	Intermediate Similarity	NPD3748	Approved
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7368	Intermediate Similarity	NPD6232	Discontinued
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7351	Intermediate Similarity	NPD1203	Approved
0.7346	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2935	Discontinued
0.7341	Intermediate Similarity	NPD7473	Discontinued
0.7326	Intermediate Similarity	NPD7435	Discontinued
0.7318	Intermediate Similarity	NPD8434	Phase 2
0.7308	Intermediate Similarity	NPD447	Suspended
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2798	Approved
0.7303	Intermediate Similarity	NPD1019	Discontinued
0.7302	Intermediate Similarity	NPD7583	Approved
0.7299	Intermediate Similarity	NPD7228	Approved
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.7288	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2403	Approved
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7585	Approved
0.7262	Intermediate Similarity	NPD1465	Phase 2
0.7234	Intermediate Similarity	NPD7698	Approved
0.7234	Intermediate Similarity	NPD7697	Approved
0.7234	Intermediate Similarity	NPD7696	Phase 3
0.7229	Intermediate Similarity	NPD7458	Discontinued
0.7226	Intermediate Similarity	NPD2313	Discontinued
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7225	Intermediate Similarity	NPD8151	Discontinued
0.7222	Intermediate Similarity	NPD2309	Approved
0.72	Intermediate Similarity	NPD422	Phase 1
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6355	Discontinued
0.7196	Intermediate Similarity	NPD7871	Phase 2
0.7196	Intermediate Similarity	NPD7870	Phase 2
0.7195	Intermediate Similarity	NPD4662	Approved
0.7195	Intermediate Similarity	NPD4661	Approved
0.7184	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6823	Phase 2
0.7179	Intermediate Similarity	NPD6233	Phase 2
0.7174	Intermediate Similarity	NPD6535	Approved
0.7174	Intermediate Similarity	NPD6534	Approved
0.7173	Intermediate Similarity	NPD7701	Phase 2
0.7172	Intermediate Similarity	NPD1241	Discontinued
0.7168	Intermediate Similarity	NPD5710	Approved
0.7168	Intermediate Similarity	NPD5711	Approved
0.7162	Intermediate Similarity	NPD9545	Approved
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7783	Phase 2
0.715	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6104	Discontinued
0.7135	Intermediate Similarity	NPD7240	Approved
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD943	Approved
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3226	Approved
0.7125	Intermediate Similarity	NPD6099	Approved
0.7125	Intermediate Similarity	NPD6100	Approved
0.7117	Intermediate Similarity	NPD2354	Approved
0.7117	Intermediate Similarity	NPD3887	Approved
0.7107	Intermediate Similarity	NPD7097	Phase 1
0.7098	Intermediate Similarity	NPD7874	Approved
0.7098	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7266	Discontinued
0.7081	Intermediate Similarity	NPD2346	Discontinued
0.7078	Intermediate Similarity	NPD5647	Approved
0.7073	Intermediate Similarity	NPD5058	Phase 3
0.7062	Intermediate Similarity	NPD7801	Approved
0.7059	Intermediate Similarity	NPD7700	Phase 2
0.7059	Intermediate Similarity	NPD7699	Phase 2
0.7049	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD9493	Approved
0.7025	Intermediate Similarity	NPD3140	Approved
0.7025	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3142	Approved
0.7022	Intermediate Similarity	NPD1729	Discontinued
0.7018	Intermediate Similarity	NPD5353	Approved
0.7013	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6190	Approved
0.7006	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD6844	Discontinued
0.6989	Remote Similarity	NPD4363	Phase 3
0.6989	Remote Similarity	NPD4360	Phase 2
0.6987	Remote Similarity	NPD4908	Phase 1
0.6975	Remote Similarity	NPD6004	Phase 3
0.6975	Remote Similarity	NPD6002	Phase 3
0.6975	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6005	Phase 3
0.6975	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6003	Clinical (unspecified phase)

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