NPASS Compound

Structure

NPC170742 OpenBabel07101718202D 24 25 0 0 1 0 0 0 0 0999 V2000 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 6.9282 -0.0000 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 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 9 1 0 0 0 0 2 5 1 0 0 0 0 2 10 2 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 8 2 0 0 0 0 5 12 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 6 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 23 2 0 0 0 0 15 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.06
Volume:	311.54
LogP:	-0.515
LogD:	-0.463
LogS:	-2.092
# Rotatable Bonds:	4
TPSA:	178.91
# H-Bond Aceptor:	9
# H-Bond Donor:	8
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	3.753
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.507
MDCK Permeability:	3.62813807441853e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	79.22279357910156%
Volume Distribution (VD):	0.618
Pgp-substrate:	17.282865524291992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.324
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	3.997
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.904
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.95
Carcinogencity:	0.011
Eye Corrosion:	0.004
Eye Irritation:	0.914
Respiratory Toxicity:	0.126

Download Data

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

Natural Product: NPC170742

Natural Product ID:	NPC170742
*Common Name:**	Alpha,Beta,3,4,5,2',4',6'-Octahydroxydihydrochalcone
IUPAC Name:	(2R,3R)-2,3-dihydroxy-1-(2,4,6-trihydroxyphenyl)-3-(3,4,5-trihydroxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	ZOKIDPTZJHTZQM-IUODEOHRSA-N
Standard InCHI:	InChI=1S/C15H14O9/c16-6-3-7(17)11(8(18)4-6)14(23)15(24)12(21)5-1-9(19)13(22)10(20)2-5/h1-4,12,15-22,24H/t12-,15-/m1/s1
SMILES:	c1c(cc(c(c1O)O)O)[C@H]([C@H](C(=O)c1c(cc(cc1O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503706
PubChem CID:	3008614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104489]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	128.0	ug.mL-1	PMID[573196]

☑ 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 NPC170742 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	392
0.1-0.2	1612
0.2-0.3	4378
0.3-0.4	11304
0.4-0.5	7404
0.5-0.6	4572
0.6-0.7	6220
0.7-0.8	6049
0.8-0.85	660
0.85-0.9	95
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC175552
0.9313	High Similarity	NPC233056
0.9173	High Similarity	NPC135801
0.9167	High Similarity	NPC26697
0.9098	High Similarity	NPC34070
0.9098	High Similarity	NPC469526
0.9091	High Similarity	NPC102829
0.9091	High Similarity	NPC120488
0.903	High Similarity	NPC478190
0.9023	High Similarity	NPC244441
0.8966	High Similarity	NPC19721
0.8905	High Similarity	NPC264112
0.8905	High Similarity	NPC65005
0.8905	High Similarity	NPC194764
0.8889	High Similarity	NPC17843
0.8881	High Similarity	NPC147757
0.8841	High Similarity	NPC290030
0.8836	High Similarity	NPC36835
0.8836	High Similarity	NPC61506
0.8836	High Similarity	NPC9743
0.8836	High Similarity	NPC240476
0.8836	High Similarity	NPC260491
0.8836	High Similarity	NPC246162
0.8832	High Similarity	NPC283590
0.8832	High Similarity	NPC70859
0.8832	High Similarity	NPC61153
0.8832	High Similarity	NPC130899
0.8797	High Similarity	NPC107672
0.8788	High Similarity	NPC10926
0.8784	High Similarity	NPC250922
0.8776	High Similarity	NPC27532
0.8776	High Similarity	NPC256346
0.8776	High Similarity	NPC325028
0.8776	High Similarity	NPC246328
0.8768	High Similarity	NPC223836
0.8767	High Similarity	NPC227485
0.8723	High Similarity	NPC472904
0.8722	High Similarity	NPC8745
0.8714	High Similarity	NPC472903
0.8712	High Similarity	NPC13238
0.8696	High Similarity	NPC129752
0.869	High Similarity	NPC188679
0.869	High Similarity	NPC321011
0.869	High Similarity	NPC294852
0.8686	High Similarity	NPC139074
0.8686	High Similarity	NPC213485
0.8686	High Similarity	NPC40524
0.8681	High Similarity	NPC169749
0.8671	High Similarity	NPC38065
0.8671	High Similarity	NPC242893
0.8658	High Similarity	NPC320825
0.8658	High Similarity	NPC201837
0.8658	High Similarity	NPC326037
0.8658	High Similarity	NPC13858
0.8657	High Similarity	NPC156539
0.8652	High Similarity	NPC203063
0.863	High Similarity	NPC1612
0.863	High Similarity	NPC183959
0.8626	High Similarity	NPC242895
0.8621	High Similarity	NPC476463
0.8621	High Similarity	NPC21835
0.8609	High Similarity	NPC470326
0.8601	High Similarity	NPC287722
0.8601	High Similarity	NPC238629
0.86	High Similarity	NPC52530
0.8593	High Similarity	NPC247250
0.8593	High Similarity	NPC767
0.8581	High Similarity	NPC323626
0.8581	High Similarity	NPC324233
0.8562	High Similarity	NPC218569
0.8562	High Similarity	NPC218490
0.8562	High Similarity	NPC119059
0.8561	High Similarity	NPC133909
0.8561	High Similarity	NPC32032
0.8553	High Similarity	NPC471499
0.8553	High Similarity	NPC289771
0.8552	High Similarity	NPC20791
0.8552	High Similarity	NPC179271
0.8543	High Similarity	NPC22192
0.8542	High Similarity	NPC471906
0.8542	High Similarity	NPC244691
0.854	High Similarity	NPC475042
0.8533	High Similarity	NPC471500
0.8531	High Similarity	NPC301178
0.8531	High Similarity	NPC284556
0.8523	High Similarity	NPC141212
0.8514	High Similarity	NPC28274
0.8514	High Similarity	NPC204515
0.8514	High Similarity	NPC133953
0.8514	High Similarity	NPC50403
0.8503	High Similarity	NPC87125
0.8503	High Similarity	NPC270465
0.8493	Intermediate Similarity	NPC188074
0.8493	Intermediate Similarity	NPC74881
0.8493	Intermediate Similarity	NPC125449
0.8493	Intermediate Similarity	NPC51443
0.8487	Intermediate Similarity	NPC287328
0.8487	Intermediate Similarity	NPC263449
0.8487	Intermediate Similarity	NPC470183
0.8487	Intermediate Similarity	NPC282009
0.8487	Intermediate Similarity	NPC471744
0.8485	Intermediate Similarity	NPC224273
0.8485	Intermediate Similarity	NPC45438
0.8485	Intermediate Similarity	NPC19174
0.8485	Intermediate Similarity	NPC143427
0.8485	Intermediate Similarity	NPC73532
0.8485	Intermediate Similarity	NPC267552
0.8485	Intermediate Similarity	NPC115159
0.8485	Intermediate Similarity	NPC156139
0.8477	Intermediate Similarity	NPC471515
0.8477	Intermediate Similarity	NPC471479
0.8472	Intermediate Similarity	NPC175013
0.8472	Intermediate Similarity	NPC471417
0.8472	Intermediate Similarity	NPC254659
0.8467	Intermediate Similarity	NPC321779
0.8456	Intermediate Similarity	NPC219582
0.8456	Intermediate Similarity	NPC302950
0.8456	Intermediate Similarity	NPC123886
0.8456	Intermediate Similarity	NPC106976
0.8456	Intermediate Similarity	NPC236637
0.8451	Intermediate Similarity	NPC190457
0.8446	Intermediate Similarity	NPC77858
0.8446	Intermediate Similarity	NPC149127
0.8446	Intermediate Similarity	NPC10467
0.8446	Intermediate Similarity	NPC280295
0.8446	Intermediate Similarity	NPC286342
0.8446	Intermediate Similarity	NPC188871
0.8435	Intermediate Similarity	NPC80710
0.8435	Intermediate Similarity	NPC166036
0.8435	Intermediate Similarity	NPC203747
0.8435	Intermediate Similarity	NPC238279
0.8435	Intermediate Similarity	NPC203077
0.8435	Intermediate Similarity	NPC139364
0.8435	Intermediate Similarity	NPC254702
0.8435	Intermediate Similarity	NPC19545
0.8435	Intermediate Similarity	NPC287395
0.8435	Intermediate Similarity	NPC183655
0.8435	Intermediate Similarity	NPC3036
0.8435	Intermediate Similarity	NPC194653
0.8435	Intermediate Similarity	NPC471907
0.8431	Intermediate Similarity	NPC308992
0.8431	Intermediate Similarity	NPC112418
0.8421	Intermediate Similarity	NPC117418
0.8421	Intermediate Similarity	NPC53545
0.8414	Intermediate Similarity	NPC142165
0.8414	Intermediate Similarity	NPC95751
0.8414	Intermediate Similarity	NPC279121
0.8411	Intermediate Similarity	NPC474638
0.8409	Intermediate Similarity	NPC248363
0.8409	Intermediate Similarity	NPC146642
0.8409	Intermediate Similarity	NPC297186
0.8403	Intermediate Similarity	NPC291078
0.8403	Intermediate Similarity	NPC474961
0.8403	Intermediate Similarity	NPC137649
0.84	Intermediate Similarity	NPC192083
0.84	Intermediate Similarity	NPC298692
0.84	Intermediate Similarity	NPC162351
0.84	Intermediate Similarity	NPC213896
0.84	Intermediate Similarity	NPC74924
0.84	Intermediate Similarity	NPC58382
0.84	Intermediate Similarity	NPC472211
0.84	Intermediate Similarity	NPC18727
0.84	Intermediate Similarity	NPC250557
0.8394	Intermediate Similarity	NPC92624
0.8389	Intermediate Similarity	NPC252933
0.8389	Intermediate Similarity	NPC205046
0.8389	Intermediate Similarity	NPC54394
0.8389	Intermediate Similarity	NPC45291
0.8389	Intermediate Similarity	NPC200740
0.8389	Intermediate Similarity	NPC260895
0.8389	Intermediate Similarity	NPC19980
0.8389	Intermediate Similarity	NPC304295
0.8389	Intermediate Similarity	NPC125062
0.8389	Intermediate Similarity	NPC59162
0.8387	Intermediate Similarity	NPC7154
0.8387	Intermediate Similarity	NPC125039
0.8387	Intermediate Similarity	NPC72787
0.8387	Intermediate Similarity	NPC36
0.8387	Intermediate Similarity	NPC470457
0.8387	Intermediate Similarity	NPC7688
0.8387	Intermediate Similarity	NPC58223
0.8387	Intermediate Similarity	NPC36916
0.8382	Intermediate Similarity	NPC214620
0.8378	Intermediate Similarity	NPC142876
0.8378	Intermediate Similarity	NPC139293
0.8378	Intermediate Similarity	NPC264289
0.8378	Intermediate Similarity	NPC195351
0.8378	Intermediate Similarity	NPC105512
0.8378	Intermediate Similarity	NPC69430
0.8378	Intermediate Similarity	NPC333691
0.8378	Intermediate Similarity	NPC40290
0.8378	Intermediate Similarity	NPC264550
0.8378	Intermediate Similarity	NPC200060
0.8378	Intermediate Similarity	NPC195763
0.8378	Intermediate Similarity	NPC171916
0.8378	Intermediate Similarity	NPC38545
0.8377	Intermediate Similarity	NPC211107
0.8377	Intermediate Similarity	NPC471745
0.8367	Intermediate Similarity	NPC95864
0.8367	Intermediate Similarity	NPC108406

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 NPC170742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	924
0.2-0.3	1853
0.3-0.4	2967
0.4-0.5	1701
0.5-0.6	959
0.6-0.7	282
0.7-0.8	74
0.8-0.85	11
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9173	High Similarity	NPD943	Approved
0.8768	High Similarity	NPD651	Clinical (unspecified phase)
0.8552	High Similarity	NPD1512	Approved
0.8456	Intermediate Similarity	NPD1934	Approved
0.8414	Intermediate Similarity	NPD1511	Approved
0.84	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6166	Phase 2
0.8387	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD3882	Suspended
0.8148	Intermediate Similarity	NPD9269	Phase 2
0.8112	Intermediate Similarity	NPD1510	Phase 2
0.8112	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD4380	Phase 2
0.805	Intermediate Similarity	NPD3818	Discontinued
0.8039	Intermediate Similarity	NPD2801	Approved
0.8028	Intermediate Similarity	NPD230	Phase 1
0.8012	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.7963	Intermediate Similarity	NPD7251	Discontinued
0.7958	Intermediate Similarity	NPD1240	Approved
0.795	Intermediate Similarity	NPD7074	Phase 3
0.7945	Intermediate Similarity	NPD1549	Phase 2
0.7935	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7390	Discontinued
0.7914	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7054	Approved
0.7867	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD9268	Approved
0.7847	Intermediate Similarity	NPD1607	Approved
0.784	Intermediate Similarity	NPD7472	Approved
0.7805	Intermediate Similarity	NPD7808	Phase 3
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6190	Approved
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7748	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD1201	Approved
0.7628	Intermediate Similarity	NPD6801	Discontinued
0.7589	Intermediate Similarity	NPD1470	Approved
0.7584	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6232	Discontinued
0.7566	Intermediate Similarity	NPD6799	Approved
0.7561	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7473	Discontinued
0.7532	Intermediate Similarity	NPD5402	Approved
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7466	Intermediate Similarity	NPD1613	Approved
0.7466	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2796	Approved
0.7421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5403	Approved
0.7407	Intermediate Similarity	NPD6959	Discontinued
0.7403	Intermediate Similarity	NPD5401	Approved
0.7389	Intermediate Similarity	NPD6599	Discontinued
0.7379	Intermediate Similarity	NPD3027	Phase 3
0.7358	Intermediate Similarity	NPD7819	Suspended
0.7346	Intermediate Similarity	NPD5494	Approved
0.7343	Intermediate Similarity	NPD1164	Approved
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.7301	Intermediate Similarity	NPD1247	Approved
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD919	Approved
0.7273	Intermediate Similarity	NPD3300	Phase 2
0.7246	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7411	Suspended
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD6559	Discontinued
0.7219	Intermediate Similarity	NPD5404	Approved
0.7219	Intermediate Similarity	NPD5405	Approved
0.7219	Intermediate Similarity	NPD5406	Approved
0.7212	Intermediate Similarity	NPD3926	Phase 2
0.7192	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2532	Approved
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD6651	Approved
0.7123	Intermediate Similarity	NPD9494	Approved
0.7121	Intermediate Similarity	NPD1237	Approved
0.7105	Intermediate Similarity	NPD9570	Approved
0.7089	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2800	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7032	Intermediate Similarity	NPD3750	Approved
0.7023	Intermediate Similarity	NPD1242	Phase 1
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD9493	Approved
0.6985	Remote Similarity	NPD3022	Approved
0.6985	Remote Similarity	NPD3021	Approved
0.6982	Remote Similarity	NPD3751	Discontinued
0.6975	Remote Similarity	NPD37	Approved
0.697	Remote Similarity	NPD6234	Discontinued
0.6964	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9264	Approved
0.6963	Remote Similarity	NPD9267	Approved
0.6963	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9263	Approved
0.6954	Remote Similarity	NPD447	Suspended
0.6949	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7266	Discontinued
0.6923	Remote Similarity	NPD4628	Phase 3
0.6909	Remote Similarity	NPD3749	Approved
0.6901	Remote Similarity	NPD9545	Approved
0.6875	Remote Similarity	NPD920	Approved
0.6871	Remote Similarity	NPD1203	Approved
0.6867	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1243	Approved
0.6857	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4965	Approved
0.6848	Remote Similarity	NPD7768	Phase 2
0.6848	Remote Similarity	NPD4966	Approved
0.6848	Remote Similarity	NPD4967	Phase 2
0.6845	Remote Similarity	NPD3787	Discontinued
0.6842	Remote Similarity	NPD846	Approved
0.6842	Remote Similarity	NPD940	Approved
0.6839	Remote Similarity	NPD2344	Approved
0.6836	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1653	Approved
0.6828	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3400	Discontinued
0.6805	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7199	Phase 2
0.6784	Remote Similarity	NPD7228	Approved
0.6782	Remote Similarity	NPD5026	Approved
0.6782	Remote Similarity	NPD5034	Approved
0.6782	Remote Similarity	NPD36	Approved
0.6782	Remote Similarity	NPD5028	Approved
0.6782	Remote Similarity	NPD4955	Approved
0.6782	Remote Similarity	NPD4954	Approved
0.6778	Remote Similarity	NPD6535	Approved
0.6778	Remote Similarity	NPD6534	Approved
0.6763	Remote Similarity	NPD5953	Discontinued
0.6752	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5035	Approved
0.6739	Remote Similarity	NPD4750	Phase 3
0.6738	Remote Similarity	NPD9281	Approved
0.6724	Remote Similarity	NPD5030	Phase 2
0.6723	Remote Similarity	NPD5038	Approved
0.6723	Remote Similarity	NPD5037	Approved
0.671	Remote Similarity	NPD3748	Approved
0.6709	Remote Similarity	NPD8166	Discontinued
0.6703	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9381	Approved
0.669	Remote Similarity	NPD9384	Approved
0.6687	Remote Similarity	NPD3455	Phase 2
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3226	Approved
0.6686	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6781	Approved
0.6685	Remote Similarity	NPD6780	Approved
0.6685	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6776	Approved
0.6685	Remote Similarity	NPD6777	Approved
0.6685	Remote Similarity	NPD6778	Approved
0.6685	Remote Similarity	NPD6782	Approved
0.6685	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD7700	Phase 2
0.6667	Remote Similarity	NPD5036	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6647	Remote Similarity	NPD5711	Approved
0.6647	Remote Similarity	NPD5710	Approved
0.6647	Remote Similarity	NPD7286	Phase 2
0.6646	Remote Similarity	NPD2654	Approved
0.6645	Remote Similarity	NPD2313	Discontinued
0.6645	Remote Similarity	NPD3764	Approved
0.6629	Remote Similarity	NPD7685	Pre-registration
0.6629	Remote Similarity	NPD8434	Phase 2
0.6623	Remote Similarity	NPD6832	Phase 2
0.6623	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2799	Discontinued
0.6603	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD520	Approved
0.66	Remote Similarity	NPD258	Approved
0.66	Remote Similarity	NPD2798	Approved
0.66	Remote Similarity	NPD257	Approved
0.6599	Remote Similarity	NPD1610	Phase 2
0.6579	Remote Similarity	NPD8151	Discontinued
0.6578	Remote Similarity	NPD7435	Discontinued
0.6558	Remote Similarity	NPD3061	Approved
0.6558	Remote Similarity	NPD3059	Approved
0.6558	Remote Similarity	NPD826	Approved
0.6558	Remote Similarity	NPD3062	Approved
0.6558	Remote Similarity	NPD825	Approved
0.6554	Remote Similarity	NPD8312	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