NPASS Compound

Structure

CID144051 OpenBabel06191715502D 23 24 0 0 0 0 0 0 0 0999 V2000 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -3.4641 -0.0000 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 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 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 0.0000 -0.0000 0.0000 C 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 -6.0622 1.5000 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 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 7 1 0 0 0 0 4 12 2 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 17 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.13
Volume:	328.267
LogP:	3.504
LogD:	3.394
LogS:	-4.963
# Rotatable Bonds:	7
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.794
Synthetic Accessibility Score:	1.954
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.802
MDCK Permeability:	2.798806417558808e-05
Pgp-inhibitor:	0.379
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	92.94430541992188%
Volume Distribution (VD):	0.625
Pgp-substrate:	2.6494140625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.851
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.538

ADMET: Excretion

Clearance (CL):	11.061
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.276
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.662
AMES Toxicity:	0.2
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.472
Skin Sensitization:	0.754
Carcinogencity:	0.163
Eye Corrosion:	0.004
Eye Irritation:	0.732
Respiratory Toxicity:	0.791

Download Data

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

Natural Product: NPC144051

Natural Product ID:	NPC144051
*Common Name:**	1-(2-Hydroxy-4,6-Dimethoxyphenyl)-3-(4-Methoxyphenyl)Propan-1-One
IUPAC Name:	1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	KGFYDIZALLKOLQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H20O5/c1-21-13-7-4-12(5-8-13)6-9-15(19)18-16(20)10-14(22-2)11-17(18)23-3/h4-5,7-8,10-11,20H,6,9H2,1-3H3
SMILES:	COc1ccc(cc1)CCC(=O)c1c(cc(cc1OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523190
PubChem CID:	270057
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
NPO583	Goniothalamus gardneri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO583	Goniothalamus gardneri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO583	Goniothalamus gardneri	Species	Annonaceae	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
GI50	8
IC50	1

Activity Type	# Activity
Cell Line	8
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50	>	197000.0	nM	PMID[451706]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	>	197000.0	nM	PMID[451706]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	>	197000.0	nM	PMID[451706]
NPT387	Cell Line	M14	Homo sapiens	GI50	>	197000.0	nM	PMID[451706]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	197000.0	nM	PMID[451706]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	>	197000.0	nM	PMID[451706]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	>	197000.0	nM	PMID[451706]
NPT886	Cell Line	NIH3T3	Mus musculus	GI50	>	197000.0	nM	PMID[451706]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	100000.0	nM	PMID[451706]

☑ 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 NPC144051 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	332
0.1-0.2	1598
0.2-0.3	4308
0.3-0.4	11183
0.4-0.5	6730
0.5-0.6	3909
0.6-0.7	5880
0.7-0.8	5369
0.8-0.85	1977
0.85-0.9	911
0.9-0.95	397
0.95-1	103

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC28753
1.0	High Similarity	NPC18877
1.0	High Similarity	NPC82225
1.0	High Similarity	NPC20560
1.0	High Similarity	NPC159623
1.0	High Similarity	NPC204960
1.0	High Similarity	NPC294593
0.9922	High Similarity	NPC286336
0.9845	High Similarity	NPC13575
0.9844	High Similarity	NPC472365
0.9844	High Similarity	NPC139813
0.9844	High Similarity	NPC175098
0.9844	High Similarity	NPC263670
0.9844	High Similarity	NPC188646
0.9844	High Similarity	NPC192304
0.9844	High Similarity	NPC242294
0.9844	High Similarity	NPC337373
0.9844	High Similarity	NPC312318
0.9844	High Similarity	NPC56031
0.9843	High Similarity	NPC186097
0.9843	High Similarity	NPC475009
0.9843	High Similarity	NPC475008
0.9769	High Similarity	NPC168105
0.9769	High Similarity	NPC66349
0.9769	High Similarity	NPC98115
0.9769	High Similarity	NPC150399
0.9769	High Similarity	NPC249606
0.9769	High Similarity	NPC477242
0.9769	High Similarity	NPC12165
0.9769	High Similarity	NPC186838
0.9769	High Similarity	NPC41461
0.9769	High Similarity	NPC25287
0.9769	High Similarity	NPC477243
0.9769	High Similarity	NPC1486
0.9769	High Similarity	NPC274109
0.9769	High Similarity	NPC477244
0.9767	High Similarity	NPC103842
0.9766	High Similarity	NPC87231
0.9766	High Similarity	NPC205468
0.9766	High Similarity	NPC129132
0.9766	High Similarity	NPC257756
0.9766	High Similarity	NPC212631
0.9695	High Similarity	NPC472419
0.9695	High Similarity	NPC153979
0.9695	High Similarity	NPC317119
0.9692	High Similarity	NPC131039
0.9692	High Similarity	NPC156092
0.9688	High Similarity	NPC262359
0.9688	High Similarity	NPC308037
0.9688	High Similarity	NPC309717
0.9688	High Similarity	NPC128348
0.9688	High Similarity	NPC313618
0.9688	High Similarity	NPC66384
0.9688	High Similarity	NPC112192
0.9688	High Similarity	NPC164236
0.9688	High Similarity	NPC64359
0.9688	High Similarity	NPC189106
0.9621	High Similarity	NPC472368
0.9621	High Similarity	NPC21350
0.9621	High Similarity	NPC124269
0.9621	High Similarity	NPC251681
0.9621	High Similarity	NPC243528
0.9618	High Similarity	NPC473391
0.9618	High Similarity	NPC476333
0.9618	High Similarity	NPC213603
0.9618	High Similarity	NPC472367
0.9618	High Similarity	NPC472364
0.9549	High Similarity	NPC477956
0.9549	High Similarity	NPC470211
0.9549	High Similarity	NPC472366
0.9545	High Similarity	NPC303644
0.9545	High Similarity	NPC188879
0.9545	High Similarity	NPC116632
0.9545	High Similarity	NPC162680
0.9545	High Similarity	NPC7013
0.9545	High Similarity	NPC209560
0.9545	High Similarity	NPC181124
0.9545	High Similarity	NPC294409
0.9538	High Similarity	NPC27643
0.9531	High Similarity	NPC247779
0.9478	High Similarity	NPC172250
0.9478	High Similarity	NPC215311
0.9478	High Similarity	NPC213659
0.9478	High Similarity	NPC6407
0.9478	High Similarity	NPC48624
0.9478	High Similarity	NPC129853
0.9478	High Similarity	NPC159275
0.9478	High Similarity	NPC110228
0.9478	High Similarity	NPC76445
0.9478	High Similarity	NPC265178
0.9478	High Similarity	NPC188243
0.9478	High Similarity	NPC284550
0.9478	High Similarity	NPC241100
0.9478	High Similarity	NPC11056
0.9478	High Similarity	NPC259166
0.9478	High Similarity	NPC219917
0.9478	High Similarity	NPC326109
0.9478	High Similarity	NPC204985
0.9478	High Similarity	NPC144118
0.9478	High Similarity	NPC80962
0.9474	High Similarity	NPC471620
0.9474	High Similarity	NPC90665
0.9474	High Similarity	NPC279668
0.9474	High Similarity	NPC278323
0.9474	High Similarity	NPC309154
0.9474	High Similarity	NPC55162
0.9474	High Similarity	NPC12175
0.947	High Similarity	NPC473887
0.947	High Similarity	NPC29353
0.947	High Similarity	NPC127447
0.947	High Similarity	NPC194281
0.947	High Similarity	NPC13408
0.947	High Similarity	NPC231772
0.947	High Similarity	NPC240593
0.947	High Similarity	NPC234133
0.947	High Similarity	NPC124784
0.947	High Similarity	NPC47815
0.9462	High Similarity	NPC15834
0.9462	High Similarity	NPC215875
0.9453	High Similarity	NPC211120
0.9453	High Similarity	NPC212379
0.9453	High Similarity	NPC69235
0.9449	High Similarity	NPC305518
0.9449	High Similarity	NPC128428
0.9407	High Similarity	NPC126534
0.9407	High Similarity	NPC55832
0.9407	High Similarity	NPC268204
0.9407	High Similarity	NPC282300
0.9407	High Similarity	NPC469404
0.9407	High Similarity	NPC232021
0.9407	High Similarity	NPC470087
0.9407	High Similarity	NPC321980
0.9407	High Similarity	NPC26238
0.9407	High Similarity	NPC52789
0.9407	High Similarity	NPC110969
0.9407	High Similarity	NPC26051
0.9407	High Similarity	NPC40118
0.9407	High Similarity	NPC49108
0.9407	High Similarity	NPC470089
0.9403	High Similarity	NPC220062
0.9403	High Similarity	NPC222342
0.9403	High Similarity	NPC78913
0.9403	High Similarity	NPC55018
0.9403	High Similarity	NPC216978
0.9403	High Similarity	NPC109232
0.9403	High Similarity	NPC225153
0.9403	High Similarity	NPC301217
0.9403	High Similarity	NPC20709
0.9403	High Similarity	NPC53181
0.9403	High Similarity	NPC140890
0.9403	High Similarity	NPC217186
0.9403	High Similarity	NPC18260
0.9403	High Similarity	NPC295384
0.9403	High Similarity	NPC96565
0.9403	High Similarity	NPC265871
0.9403	High Similarity	NPC274784
0.9403	High Similarity	NPC150648
0.9403	High Similarity	NPC283429
0.9403	High Similarity	NPC310135
0.9403	High Similarity	NPC303633
0.9403	High Similarity	NPC329203
0.9398	High Similarity	NPC250266
0.9398	High Similarity	NPC266597
0.9394	High Similarity	NPC39426
0.9394	High Similarity	NPC234560
0.9389	High Similarity	NPC16197
0.938	High Similarity	NPC84772
0.9375	High Similarity	NPC80694
0.9375	High Similarity	NPC475017
0.9375	High Similarity	NPC186098
0.9338	High Similarity	NPC228504
0.9338	High Similarity	NPC324134
0.9338	High Similarity	NPC182852
0.9338	High Similarity	NPC167624
0.9338	High Similarity	NPC10937
0.9338	High Similarity	NPC220998
0.9338	High Similarity	NPC40833
0.9338	High Similarity	NPC37496
0.9338	High Similarity	NPC64915
0.9338	High Similarity	NPC227579
0.9338	High Similarity	NPC11561
0.9338	High Similarity	NPC265040
0.9338	High Similarity	NPC76372
0.9338	High Similarity	NPC1089
0.9338	High Similarity	NPC161506
0.9338	High Similarity	NPC107572
0.9338	High Similarity	NPC78
0.9338	High Similarity	NPC166482
0.9338	High Similarity	NPC324436
0.9338	High Similarity	NPC66515
0.9338	High Similarity	NPC328164
0.9338	High Similarity	NPC297600
0.9338	High Similarity	NPC177354
0.9338	High Similarity	NPC306829
0.9338	High Similarity	NPC125855
0.9338	High Similarity	NPC32739
0.9338	High Similarity	NPC296917
0.9338	High Similarity	NPC223500
0.9338	High Similarity	NPC148757
0.9338	High Similarity	NPC226636

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 NPC144051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	976
0.2-0.3	1453
0.3-0.4	2619
0.4-0.5	1924
0.5-0.6	1237
0.6-0.7	433
0.7-0.8	138
0.8-0.85	44
0.85-0.9	8
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9688	High Similarity	NPD1240	Approved
0.9538	High Similarity	NPD1607	Approved
0.9394	High Similarity	NPD1510	Phase 2
0.9254	High Similarity	NPD1552	Clinical (unspecified phase)
0.9254	High Similarity	NPD1550	Clinical (unspecified phase)
0.9203	High Similarity	NPD4378	Clinical (unspecified phase)
0.9185	High Similarity	NPD1549	Phase 2
0.8929	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD2796	Approved
0.875	High Similarity	NPD4380	Phase 2
0.8723	High Similarity	NPD6799	Approved
0.8699	High Similarity	NPD2393	Clinical (unspecified phase)
0.869	High Similarity	NPD7411	Suspended
0.8676	High Similarity	NPD6651	Approved
0.8639	High Similarity	NPD8443	Clinical (unspecified phase)
0.8633	High Similarity	NPD970	Clinical (unspecified phase)
0.863	High Similarity	NPD1934	Approved
0.8592	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD2801	Approved
0.8523	High Similarity	NPD7075	Discontinued
0.8519	High Similarity	NPD6859	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD6599	Discontinued
0.8489	Intermediate Similarity	NPD2935	Discontinued
0.8472	Intermediate Similarity	NPD1512	Approved
0.8456	Intermediate Similarity	NPD3882	Suspended
0.8446	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD7819	Suspended
0.84	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD3750	Approved
0.838	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6801	Discontinued
0.8357	Intermediate Similarity	NPD1551	Phase 2
0.831	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD2800	Approved
0.8261	Intermediate Similarity	NPD943	Approved
0.8212	Intermediate Similarity	NPD7768	Phase 2
0.8194	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD2654	Approved
0.8169	Intermediate Similarity	NPD2344	Approved
0.8158	Intermediate Similarity	NPD3749	Approved
0.8151	Intermediate Similarity	NPD2532	Approved
0.8151	Intermediate Similarity	NPD2533	Approved
0.8151	Intermediate Similarity	NPD2534	Approved
0.8148	Intermediate Similarity	NPD1203	Approved
0.8146	Intermediate Similarity	NPD3817	Phase 2
0.8141	Intermediate Similarity	NPD7473	Discontinued
0.8117	Intermediate Similarity	NPD6959	Discontinued
0.8088	Intermediate Similarity	NPD2798	Approved
0.806	Intermediate Similarity	NPD3972	Approved
0.8056	Intermediate Similarity	NPD1243	Approved
0.8041	Intermediate Similarity	NPD5403	Approved
0.8038	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3748	Approved
0.8028	Intermediate Similarity	NPD2799	Discontinued
0.7987	Intermediate Similarity	NPD7074	Phase 3
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7971	Intermediate Similarity	NPD6832	Phase 2
0.7945	Intermediate Similarity	NPD2309	Approved
0.7939	Intermediate Similarity	NPD9493	Approved
0.7937	Intermediate Similarity	NPD5953	Discontinued
0.7926	Intermediate Similarity	NPD9717	Approved
0.7925	Intermediate Similarity	NPD7286	Phase 2
0.7925	Intermediate Similarity	NPD7054	Approved
0.7919	Intermediate Similarity	NPD920	Approved
0.7905	Intermediate Similarity	NPD5401	Approved
0.7891	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4628	Phase 3
0.7875	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD3268	Approved
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD422	Phase 1
0.7852	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6100	Approved
0.7847	Intermediate Similarity	NPD6099	Approved
0.7842	Intermediate Similarity	NPD4908	Phase 1
0.784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7390	Discontinued
0.7826	Intermediate Similarity	NPD6797	Phase 2
0.7821	Intermediate Similarity	NPD5494	Approved
0.782	Intermediate Similarity	NPD9545	Approved
0.782	Intermediate Similarity	NPD1548	Phase 1
0.78	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7033	Discontinued
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7754	Intermediate Similarity	NPD2797	Approved
0.773	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2313	Discontinued
0.773	Intermediate Similarity	NPD7808	Phase 3
0.7721	Intermediate Similarity	NPD1610	Phase 2
0.7677	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD3926	Phase 2
0.7669	Intermediate Similarity	NPD6559	Discontinued
0.7622	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1201	Approved
0.7582	Intermediate Similarity	NPD3226	Approved
0.7569	Intermediate Similarity	NPD230	Phase 1
0.7554	Intermediate Similarity	NPD3225	Approved
0.7554	Intermediate Similarity	NPD1876	Approved
0.7536	Intermediate Similarity	NPD1608	Approved
0.7535	Intermediate Similarity	NPD3027	Phase 3
0.7534	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4308	Phase 3
0.7532	Intermediate Similarity	NPD919	Approved
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3764	Approved
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7448	Intermediate Similarity	NPD1933	Approved
0.7448	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1241	Discontinued
0.7439	Intermediate Similarity	NPD1729	Discontinued
0.7438	Intermediate Similarity	NPD1247	Approved
0.7432	Intermediate Similarity	NPD2346	Discontinued
0.7402	Intermediate Similarity	NPD846	Approved
0.7402	Intermediate Similarity	NPD940	Approved
0.74	Intermediate Similarity	NPD7003	Approved
0.7394	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3847	Discontinued
0.7389	Intermediate Similarity	NPD1465	Phase 2
0.7384	Intermediate Similarity	NPD4363	Phase 3
0.7384	Intermediate Similarity	NPD4360	Phase 2
0.7372	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5405	Approved
0.7365	Intermediate Similarity	NPD5404	Approved
0.7365	Intermediate Similarity	NPD5408	Approved
0.7365	Intermediate Similarity	NPD5406	Approved
0.7361	Intermediate Similarity	NPD6798	Discontinued
0.7361	Intermediate Similarity	NPD411	Approved
0.7357	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6104	Discontinued
0.7343	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4288	Approved
0.7342	Intermediate Similarity	NPD2296	Approved
0.7341	Intermediate Similarity	NPD4361	Phase 2
0.7341	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD447	Suspended
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7328	Intermediate Similarity	NPD9266	Approved
0.7328	Intermediate Similarity	NPD74	Approved
0.7324	Intermediate Similarity	NPD1019	Discontinued
0.732	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD17	Approved
0.7299	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4625	Phase 3
0.7286	Intermediate Similarity	NPD1481	Phase 2
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9494	Approved
0.726	Intermediate Similarity	NPD1613	Approved
0.726	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4307	Phase 2
0.7252	Intermediate Similarity	NPD9263	Approved
0.7252	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9264	Approved
0.7252	Intermediate Similarity	NPD9267	Approved
0.7246	Intermediate Similarity	NPD1651	Approved
0.7237	Intermediate Similarity	NPD2354	Approved
0.7234	Intermediate Similarity	NPD4749	Approved
0.7214	Intermediate Similarity	NPD1535	Discovery
0.7211	Intermediate Similarity	NPD6355	Discontinued
0.7208	Intermediate Similarity	NPD4662	Approved
0.7208	Intermediate Similarity	NPD4661	Approved
0.72	Intermediate Similarity	NPD1471	Phase 3
0.7195	Intermediate Similarity	NPD2403	Approved
0.7183	Intermediate Similarity	NPD1283	Approved
0.7174	Intermediate Similarity	NPD1894	Discontinued
0.7168	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3018	Phase 2
0.7151	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD3142	Approved
0.7143	Intermediate Similarity	NPD3140	Approved
0.7124	Intermediate Similarity	NPD3887	Approved
0.7117	Intermediate Similarity	NPD7199	Phase 2
0.7113	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD37	Approved
0.7107	Intermediate Similarity	NPD6280	Approved
0.7107	Intermediate Similarity	NPD6279	Approved
0.7103	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5536	Phase 2
0.7091	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2353	Approved
0.7083	Intermediate Similarity	NPD6917	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