NPASS Compound

Structure

CID23817 OpenBabel06191715352D 35 37 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 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 3.0000 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 5.1962 2.0000 0.0000 C 0 0 0 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 6.9282 3.0000 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 6.9282 2.0000 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 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 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 -1.7321 -0.0000 0.0000 C 0 0 2 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 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -2.5981 0.5000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 9 1 0 0 0 0 3 14 2 0 0 0 0 4 7 1 0 0 0 0 4 15 2 0 0 0 0 5 8 2 0 0 0 0 5 15 1 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 27 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 29 2 0 0 0 0 20 34 1 0 0 0 0 21 13 1 6 0 0 0 21 23 1 0 0 0 0 21 35 1 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 31 1 1 0 0 0 24 25 1 0 0 0 0 24 32 1 6 0 0 0 25 26 1 0 0 0 0 25 33 1 1 0 0 0 26 34 1 6 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.19
Volume:	487.967
LogP:	3.086
LogD:	1.983
LogS:	-3.613
# Rotatable Bonds:	8
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.186
Synthetic Accessibility Score:	4.003
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
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:	-5.967
MDCK Permeability:	5.1940551202278584e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	0.951
Human Intestinal Absorption (HIA):	0.245
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	98.6531753540039%
Volume Distribution (VD):	0.76
Pgp-substrate:	3.1747303009033203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.221
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.491
CYP2D6-inhibitor:	0.551
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.089

ADMET: Excretion

Clearance (CL):	9.405
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.703
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.935
Carcinogencity:	0.509
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.12

Download Data

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

Natural Product: NPC23817

Natural Product ID:	NPC23817
*Common Name:**	3'-(3-Methyl-2-Butenyl)-4'-O-Beta-D-Glucopyranosyl-4,2'-Dihydroxychalcone
IUPAC Name:	(E)-1-[2-hydroxy-3-(3-methylbut-2-enyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	HNRQFWQDRYQVNP-BAOGALEJSA-N
Standard InCHI:	InChI=1S/C26H30O9/c1-14(2)3-9-18-20(34-26-25(33)24(32)23(31)21(13-27)35-26)12-10-17(22(18)30)19(29)11-6-15-4-7-16(28)8-5-15/h3-8,10-12,21,23-28,30-33H,9,13H2,1-2H3/b11-6+/t21-,23-,24+,25-,26-/m1/s1
SMILES:	CC(=CCc1c(ccc(C(=O)/C=C/c2ccc(cc2)O)c1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453027
PubChem CID:	10096911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-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
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.263	mM	PMID[533577]

☑ 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 NPC23817 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	376
0.1-0.2	1442
0.2-0.3	3407
0.3-0.4	8334
0.4-0.5	10039
0.5-0.6	4298
0.6-0.7	5200
0.7-0.8	5539
0.8-0.85	2572
0.85-0.9	1247
0.9-0.95	221
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC99233
0.9799	High Similarity	NPC106625
0.9737	High Similarity	NPC472320
0.9735	High Similarity	NPC43638
0.9732	High Similarity	NPC88484
0.9732	High Similarity	NPC121001
0.9732	High Similarity	NPC259767
0.9732	High Similarity	NPC259182
0.9671	High Similarity	NPC73511
0.9669	High Similarity	NPC127406
0.9669	High Similarity	NPC170475
0.9669	High Similarity	NPC206378
0.9667	High Similarity	NPC87304
0.9667	High Similarity	NPC268950
0.9667	High Similarity	NPC108706
0.9667	High Similarity	NPC211158
0.9667	High Similarity	NPC78021
0.961	High Similarity	NPC44947
0.961	High Similarity	NPC259834
0.961	High Similarity	NPC190450
0.961	High Similarity	NPC131745
0.9605	High Similarity	NPC156457
0.9605	High Similarity	NPC258035
0.9605	High Similarity	NPC313163
0.9605	High Similarity	NPC197896
0.9605	High Similarity	NPC161749
0.9605	High Similarity	NPC6985
0.9603	High Similarity	NPC470604
0.9603	High Similarity	NPC97052
0.9603	High Similarity	NPC470603
0.9603	High Similarity	NPC95090
0.9603	High Similarity	NPC72649
0.9603	High Similarity	NPC27408
0.9603	High Similarity	NPC169248
0.9603	High Similarity	NPC26195
0.9603	High Similarity	NPC470605
0.9603	High Similarity	NPC39351
0.9548	High Similarity	NPC183672
0.9548	High Similarity	NPC179198
0.9548	High Similarity	NPC124155
0.9548	High Similarity	NPC257566
0.9548	High Similarity	NPC66087
0.9548	High Similarity	NPC278419
0.9545	High Similarity	NPC47923
0.9545	High Similarity	NPC303913
0.9539	High Similarity	NPC265480
0.9539	High Similarity	NPC45165
0.9539	High Similarity	NPC149368
0.9536	High Similarity	NPC210003
0.9536	High Similarity	NPC39360
0.9536	High Similarity	NPC83283
0.9536	High Similarity	NPC29763
0.9536	High Similarity	NPC143851
0.9481	High Similarity	NPC246469
0.9481	High Similarity	NPC142860
0.9481	High Similarity	NPC271479
0.9481	High Similarity	NPC200708
0.9481	High Similarity	NPC271270
0.9481	High Similarity	NPC97285
0.9481	High Similarity	NPC153342
0.9477	High Similarity	NPC65003
0.9477	High Similarity	NPC182634
0.9477	High Similarity	NPC470606
0.9477	High Similarity	NPC60966
0.9477	High Similarity	NPC108831
0.9477	High Similarity	NPC473512
0.9477	High Similarity	NPC44931
0.9477	High Similarity	NPC129827
0.9467	High Similarity	NPC213723
0.9467	High Similarity	NPC477240
0.9467	High Similarity	NPC214454
0.9467	High Similarity	NPC38775
0.9467	High Similarity	NPC191154
0.9467	High Similarity	NPC106025
0.9463	High Similarity	NPC199335
0.9416	High Similarity	NPC41121
0.9416	High Similarity	NPC320283
0.9416	High Similarity	NPC472459
0.9416	High Similarity	NPC470607
0.9416	High Similarity	NPC111929
0.9416	High Similarity	NPC138811
0.9416	High Similarity	NPC43761
0.9416	High Similarity	NPC308265
0.9416	High Similarity	NPC473634
0.9416	High Similarity	NPC22062
0.9412	High Similarity	NPC203500
0.9412	High Similarity	NPC323593
0.9412	High Similarity	NPC307938
0.9404	High Similarity	NPC244577
0.9404	High Similarity	NPC263384
0.9404	High Similarity	NPC134819
0.9404	High Similarity	NPC471676
0.9404	High Similarity	NPC472422
0.9404	High Similarity	NPC190217
0.9404	High Similarity	NPC472420
0.94	High Similarity	NPC89442
0.9396	High Similarity	NPC218685
0.9396	High Similarity	NPC23084
0.9371	High Similarity	NPC76047
0.9359	High Similarity	NPC93215
0.9359	High Similarity	NPC127782
0.9359	High Similarity	NPC472876
0.9359	High Similarity	NPC300537
0.9355	High Similarity	NPC187379
0.9355	High Similarity	NPC473623
0.9355	High Similarity	NPC306978
0.9351	High Similarity	NPC135391
0.9351	High Similarity	NPC77672
0.9351	High Similarity	NPC197304
0.9351	High Similarity	NPC78263
0.9351	High Similarity	NPC54802
0.9351	High Similarity	NPC133671
0.9351	High Similarity	NPC122809
0.9342	High Similarity	NPC161881
0.9342	High Similarity	NPC10807
0.9342	High Similarity	NPC244583
0.9342	High Similarity	NPC150123
0.9342	High Similarity	NPC56232
0.9342	High Similarity	NPC35567
0.9342	High Similarity	NPC171651
0.9342	High Similarity	NPC243171
0.9308	High Similarity	NPC5319
0.9304	High Similarity	NPC178851
0.9299	High Similarity	NPC471286
0.9295	High Similarity	NPC265885
0.9295	High Similarity	NPC477629
0.9295	High Similarity	NPC249281
0.9295	High Similarity	NPC116458
0.9295	High Similarity	NPC173582
0.9295	High Similarity	NPC270675
0.9295	High Similarity	NPC159579
0.9295	High Similarity	NPC215710
0.9295	High Similarity	NPC101636
0.9295	High Similarity	NPC210961
0.9295	High Similarity	NPC129217
0.9295	High Similarity	NPC163242
0.9295	High Similarity	NPC139320
0.9295	High Similarity	NPC216496
0.9295	High Similarity	NPC224530
0.9295	High Similarity	NPC48093
0.9295	High Similarity	NPC85707
0.9295	High Similarity	NPC181465
0.9295	High Similarity	NPC253788
0.9295	High Similarity	NPC476215
0.9295	High Similarity	NPC195685
0.9295	High Similarity	NPC473438
0.9295	High Similarity	NPC276377
0.9295	High Similarity	NPC477628
0.9295	High Similarity	NPC472994
0.9295	High Similarity	NPC259957
0.9295	High Similarity	NPC246943
0.9286	High Similarity	NPC261866
0.9286	High Similarity	NPC473657
0.9286	High Similarity	NPC295613
0.9286	High Similarity	NPC17521
0.9281	High Similarity	NPC7989
0.9281	High Similarity	NPC293286
0.9281	High Similarity	NPC472583
0.9281	High Similarity	NPC223701
0.9276	High Similarity	NPC318424
0.9276	High Similarity	NPC278476
0.9276	High Similarity	NPC254412
0.9276	High Similarity	NPC209846
0.9276	High Similarity	NPC319910
0.9276	High Similarity	NPC262038
0.9276	High Similarity	NPC23253
0.9276	High Similarity	NPC477897
0.9276	High Similarity	NPC262039
0.9276	High Similarity	NPC328740
0.9276	High Similarity	NPC289774
0.9276	High Similarity	NPC471677
0.9272	High Similarity	NPC472628
0.9267	High Similarity	NPC472627
0.925	High Similarity	NPC78734
0.925	High Similarity	NPC150767
0.9245	High Similarity	NPC477502
0.9245	High Similarity	NPC229729
0.9241	High Similarity	NPC139060
0.9241	High Similarity	NPC165720
0.9236	High Similarity	NPC475382
0.9236	High Similarity	NPC27942
0.9236	High Similarity	NPC240306
0.9236	High Similarity	NPC150164
0.9236	High Similarity	NPC298171
0.9231	High Similarity	NPC304741
0.9231	High Similarity	NPC470405
0.9231	High Similarity	NPC471079
0.9231	High Similarity	NPC136761
0.9226	High Similarity	NPC288084
0.9221	High Similarity	NPC477958
0.9221	High Similarity	NPC304745
0.9221	High Similarity	NPC92395
0.9221	High Similarity	NPC111341
0.9221	High Similarity	NPC470681
0.9221	High Similarity	NPC87404
0.9216	High Similarity	NPC473996
0.9216	High Similarity	NPC475790
0.9216	High Similarity	NPC217149
0.9216	High Similarity	NPC166067
0.9216	High Similarity	NPC216035

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 NPC23817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	847
0.2-0.3	1676
0.3-0.4	2633
0.4-0.5	1984
0.5-0.6	1099
0.6-0.7	376
0.7-0.8	158
0.8-0.85	34
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD4381	Clinical (unspecified phase)
0.9308	High Similarity	NPD7804	Clinical (unspecified phase)
0.9211	High Similarity	NPD4380	Phase 2
0.9103	High Similarity	NPD7075	Discontinued
0.9018	High Similarity	NPD6559	Discontinued
0.9012	High Similarity	NPD7074	Phase 3
0.9006	High Similarity	NPD3818	Discontinued
0.8968	High Similarity	NPD6801	Discontinued
0.8951	High Similarity	NPD7054	Approved
0.891	High Similarity	NPD2393	Clinical (unspecified phase)
0.891	High Similarity	NPD7096	Clinical (unspecified phase)
0.8896	High Similarity	NPD7472	Approved
0.8859	High Similarity	NPD1549	Phase 2
0.8841	High Similarity	NPD6797	Phase 2
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.8788	High Similarity	NPD7251	Discontinued
0.8782	High Similarity	NPD7411	Suspended
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8735	High Similarity	NPD7808	Phase 3
0.8726	High Similarity	NPD1934	Approved
0.8636	High Similarity	NPD7410	Clinical (unspecified phase)
0.8623	High Similarity	NPD4338	Clinical (unspecified phase)
0.8616	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD6799	Approved
0.8553	High Similarity	NPD7819	Suspended
0.8537	High Similarity	NPD6168	Clinical (unspecified phase)
0.8537	High Similarity	NPD6166	Phase 2
0.8537	High Similarity	NPD6167	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD2796	Approved
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8408	Intermediate Similarity	NPD5403	Approved
0.8389	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD2801	Approved
0.8313	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD5401	Approved
0.8278	Intermediate Similarity	NPD1607	Approved
0.8272	Intermediate Similarity	NPD3817	Phase 2
0.8242	Intermediate Similarity	NPD6959	Discontinued
0.8229	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD3882	Suspended
0.8217	Intermediate Similarity	NPD1511	Approved
0.8194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5494	Approved
0.816	Intermediate Similarity	NPD5402	Approved
0.8142	Intermediate Similarity	NPD7584	Approved
0.814	Intermediate Similarity	NPD8312	Approved
0.814	Intermediate Similarity	NPD8313	Approved
0.8113	Intermediate Similarity	NPD1512	Approved
0.811	Intermediate Similarity	NPD7768	Phase 2
0.8059	Intermediate Similarity	NPD5844	Phase 1
0.8025	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4628	Phase 3
0.7988	Intermediate Similarity	NPD8455	Phase 2
0.7976	Intermediate Similarity	NPD6232	Discontinued
0.7965	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7473	Discontinued
0.7912	Intermediate Similarity	NPD6780	Approved
0.7912	Intermediate Similarity	NPD6777	Approved
0.7912	Intermediate Similarity	NPD6779	Approved
0.7912	Intermediate Similarity	NPD6781	Approved
0.7912	Intermediate Similarity	NPD6778	Approved
0.7912	Intermediate Similarity	NPD6782	Approved
0.7912	Intermediate Similarity	NPD6776	Approved
0.7911	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7885	Intermediate Similarity	NPD1551	Phase 2
0.7861	Intermediate Similarity	NPD5953	Discontinued
0.7849	Intermediate Similarity	NPD7286	Phase 2
0.7848	Intermediate Similarity	NPD2800	Approved
0.7845	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD3749	Approved
0.784	Intermediate Similarity	NPD920	Approved
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6651	Approved
0.7791	Intermediate Similarity	NPD1653	Approved
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7784	Intermediate Similarity	NPD7435	Discontinued
0.7766	Intermediate Similarity	NPD8151	Discontinued
0.7744	Intermediate Similarity	NPD7458	Discontinued
0.7742	Intermediate Similarity	NPD1933	Approved
0.7736	Intermediate Similarity	NPD1243	Approved
0.7716	Intermediate Similarity	NPD2534	Approved
0.7716	Intermediate Similarity	NPD2533	Approved
0.7716	Intermediate Similarity	NPD2532	Approved
0.7716	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD7585	Approved
0.7707	Intermediate Similarity	NPD2799	Discontinued
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7696	Phase 3
0.7688	Intermediate Similarity	NPD7697	Approved
0.7688	Intermediate Similarity	NPD7698	Approved
0.7673	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.766	Intermediate Similarity	NPD7583	Approved
0.7651	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1091	Approved
0.7647	Intermediate Similarity	NPD7870	Phase 2
0.7647	Intermediate Similarity	NPD7871	Phase 2
0.7647	Intermediate Similarity	NPD6832	Phase 2
0.7637	Intermediate Similarity	NPD6534	Approved
0.7637	Intermediate Similarity	NPD6535	Approved
0.7636	Intermediate Similarity	NPD3226	Approved
0.7634	Intermediate Similarity	NPD6823	Phase 2
0.7619	Intermediate Similarity	NPD7701	Phase 2
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD37	Approved
0.7595	Intermediate Similarity	NPD3748	Approved
0.7595	Intermediate Similarity	NPD7033	Discontinued
0.7592	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7783	Phase 2
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7588	Intermediate Similarity	NPD919	Approved
0.7586	Intermediate Similarity	NPD7228	Approved
0.7574	Intermediate Similarity	NPD4966	Approved
0.7574	Intermediate Similarity	NPD4965	Approved
0.7574	Intermediate Similarity	NPD4967	Phase 2
0.7566	Intermediate Similarity	NPD1203	Approved
0.7564	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1613	Approved
0.7548	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD4360	Phase 2
0.7541	Intermediate Similarity	NPD4363	Phase 3
0.7539	Intermediate Similarity	NPD7874	Approved
0.7539	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.7516	Intermediate Similarity	NPD2798	Approved
0.7514	Intermediate Similarity	NPD7699	Phase 2
0.7514	Intermediate Similarity	NPD7700	Phase 2
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD7801	Approved
0.7452	Intermediate Similarity	NPD943	Approved
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6798	Discontinued
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7414	Intermediate Similarity	NPD3926	Phase 2
0.7407	Intermediate Similarity	NPD1652	Phase 2
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7391	Intermediate Similarity	NPD6212	Phase 3
0.7391	Intermediate Similarity	NPD7266	Discontinued
0.7391	Intermediate Similarity	NPD6213	Phase 3
0.7391	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8320	Phase 1
0.7368	Intermediate Similarity	NPD9717	Approved
0.7368	Intermediate Similarity	NPD8319	Approved
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2424	Discontinued
0.734	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7325	Intermediate Similarity	NPD3268	Approved
0.7321	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2309	Approved
0.7308	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD1610	Phase 2
0.7296	Intermediate Similarity	NPD230	Phase 1
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4661	Approved
0.7289	Intermediate Similarity	NPD4662	Approved
0.7278	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7263	Intermediate Similarity	NPD3823	Discontinued
0.7261	Intermediate Similarity	NPD3027	Phase 3
0.7257	Intermediate Similarity	NPD5711	Approved
0.7257	Intermediate Similarity	NPD5710	Approved
0.7244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD7240	Approved
0.7219	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4361	Phase 2
0.7212	Intermediate Similarity	NPD6190	Approved
0.7208	Intermediate Similarity	NPD7930	Approved
0.7207	Intermediate Similarity	NPD1729	Discontinued
0.7205	Intermediate Similarity	NPD7097	Phase 1
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD447	Suspended
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7169	Intermediate Similarity	NPD5058	Phase 3
0.7164	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD9545	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