NPASS Compound

Structure

NPC214406 OpenBabel07101718292D 23 24 0 0 0 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 1.7321 -2.0000 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 5.1962 1.0000 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 -0.8660 -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 0.8660 -1.5000 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 -0.8660 -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 0.8660 -0.5000 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 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 6 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 9 14 2 0 0 0 0 10 11 2 0 0 0 0 10 13 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 2 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.13
Volume:	328.267
LogP:	2.933
LogD:	3.284
LogS:	-3.492
# Rotatable Bonds:	6
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	2.542
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.693
MDCK Permeability:	1.5966013961588033e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.274
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	97.25286102294922%
Volume Distribution (VD):	0.529
Pgp-substrate:	3.1204066276550293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.878
CYP2C19-substrate:	0.613
CYP2C9-inhibitor:	0.659
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.741
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.513

ADMET: Excretion

Clearance (CL):	10.549
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.234
Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.94
Carcinogencity:	0.495
Eye Corrosion:	0.005
Eye Irritation:	0.931
Respiratory Toxicity:	0.309

Download Data

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

Natural Product: NPC214406

Natural Product ID:	NPC214406
*Common Name:**	Dalberatin A
IUPAC Name:	4-[(E)-3-(3-hydroxy-2-methoxyphenyl)prop-2-enyl]-2,3-dimethoxyphenol
Synonyms:
Standard InCHIKey:	IDKTZIKUYHCIQO-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C18H20O5/c1-21-16-12(8-5-9-14(16)19)6-4-7-13-10-11-15(20)18(23-3)17(13)22-2/h4-6,8-11,19-20H,7H2,1-3H3/b6-4+
SMILES:	COc1c(/C=C/Cc2ccc(c(c2OC)OC)O)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461403
PubChem CID:	10448451
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO33059	Dalbergia	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695799]

☑ 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	1
Others	8

Activity Type	# Activity
Cell Line	4
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[490479]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[490479]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[490479]
NPT2	Others	Unspecified		Activity	=	18.5	%	PMID[490479]
NPT2	Others	Unspecified		Activity	=	63.6	%	PMID[490479]
NPT2	Others	Unspecified		Activity	=	85.1	%	PMID[490479]
NPT2	Others	Unspecified		IC50	=	213.0	molar ratio	PMID[490479]

☑ 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 NPC214406 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	402
0.1-0.2	1810
0.2-0.3	5992
0.3-0.4	13244
0.4-0.5	3677
0.5-0.6	4126
0.6-0.7	7033
0.7-0.8	4777
0.8-0.85	866
0.85-0.9	465
0.9-0.95	237
0.95-1	68

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC78974
1.0	High Similarity	NPC103823
1.0	High Similarity	NPC18924
1.0	High Similarity	NPC44748
1.0	High Similarity	NPC223136
1.0	High Similarity	NPC28730
0.9917	High Similarity	NPC236791
0.9917	High Similarity	NPC324112
0.9917	High Similarity	NPC293054
0.9917	High Similarity	NPC159968
0.9917	High Similarity	NPC124452
0.9917	High Similarity	NPC246620
0.9917	High Similarity	NPC82679
0.9917	High Similarity	NPC282000
0.9917	High Similarity	NPC169474
0.9917	High Similarity	NPC74817
0.9916	High Similarity	NPC234400
0.9916	High Similarity	NPC60885
0.9916	High Similarity	NPC265483
0.9916	High Similarity	NPC299584
0.9916	High Similarity	NPC82483
0.9754	High Similarity	NPC10225
0.9754	High Similarity	NPC58164
0.975	High Similarity	NPC203133
0.975	High Similarity	NPC208950
0.975	High Similarity	NPC233410
0.975	High Similarity	NPC105925
0.975	High Similarity	NPC298757
0.975	High Similarity	NPC117214
0.975	High Similarity	NPC116907
0.975	High Similarity	NPC193544
0.975	High Similarity	NPC251855
0.975	High Similarity	NPC17943
0.975	High Similarity	NPC472093
0.975	High Similarity	NPC221077
0.975	High Similarity	NPC475169
0.975	High Similarity	NPC57490
0.9748	High Similarity	NPC95168
0.9675	High Similarity	NPC234488
0.9675	High Similarity	NPC126836
0.9675	High Similarity	NPC51840
0.9675	High Similarity	NPC299221
0.9675	High Similarity	NPC311680
0.9672	High Similarity	NPC28765
0.9672	High Similarity	NPC154866
0.9664	High Similarity	NPC473411
0.9664	High Similarity	NPC71579
0.9664	High Similarity	NPC262253
0.9593	High Similarity	NPC212015
0.959	High Similarity	NPC236760
0.959	High Similarity	NPC252131
0.959	High Similarity	NPC127587
0.959	High Similarity	NPC210355
0.959	High Similarity	NPC266555
0.9583	High Similarity	NPC121115
0.9583	High Similarity	NPC282496
0.9583	High Similarity	NPC197757
0.9583	High Similarity	NPC233526
0.9583	High Similarity	NPC136319
0.9583	High Similarity	NPC228922
0.958	High Similarity	NPC75713
0.952	High Similarity	NPC6451
0.9512	High Similarity	NPC206615
0.9512	High Similarity	NPC470213
0.9512	High Similarity	NPC186843
0.9512	High Similarity	NPC266691
0.9512	High Similarity	NPC98631
0.9508	High Similarity	NPC223953
0.9508	High Similarity	NPC76451
0.95	High Similarity	NPC41562
0.9496	High Similarity	NPC166759
0.9444	High Similarity	NPC229442
0.9444	High Similarity	NPC168059
0.9444	High Similarity	NPC471390
0.9444	High Similarity	NPC471391
0.9444	High Similarity	NPC475840
0.9444	High Similarity	NPC32778
0.944	High Similarity	NPC232275
0.944	High Similarity	NPC45715
0.944	High Similarity	NPC474356
0.944	High Similarity	NPC12275
0.9435	High Similarity	NPC476968
0.9435	High Similarity	NPC170844
0.9412	High Similarity	NPC247364
0.9412	High Similarity	NPC232084
0.9412	High Similarity	NPC474565
0.9412	High Similarity	NPC61516
0.9412	High Similarity	NPC10932
0.937	High Similarity	NPC317380
0.9365	High Similarity	NPC202762
0.9365	High Similarity	NPC86655
0.9365	High Similarity	NPC127624
0.936	High Similarity	NPC224157
0.936	High Similarity	NPC472338
0.936	High Similarity	NPC91291
0.936	High Similarity	NPC192687
0.936	High Similarity	NPC214860
0.9344	High Similarity	NPC228972
0.9344	High Similarity	NPC206487
0.9344	High Similarity	NPC183446
0.9344	High Similarity	NPC5796
0.9344	High Similarity	NPC122792
0.9328	High Similarity	NPC226629
0.9328	High Similarity	NPC20674
0.9297	High Similarity	NPC470356
0.9297	High Similarity	NPC94750
0.9297	High Similarity	NPC472337
0.9297	High Similarity	NPC313081
0.9297	High Similarity	NPC474206
0.9297	High Similarity	NPC158142
0.9297	High Similarity	NPC69029
0.9297	High Similarity	NPC108198
0.9297	High Similarity	NPC200557
0.9297	High Similarity	NPC112246
0.9297	High Similarity	NPC121812
0.9297	High Similarity	NPC112939
0.9297	High Similarity	NPC10314
0.9297	High Similarity	NPC256262
0.9297	High Similarity	NPC294884
0.9291	High Similarity	NPC36661
0.9286	High Similarity	NPC470096
0.9286	High Similarity	NPC470095
0.9286	High Similarity	NPC474017
0.9286	High Similarity	NPC15543
0.9286	High Similarity	NPC472597
0.928	High Similarity	NPC45824
0.928	High Similarity	NPC469951
0.928	High Similarity	NPC469963
0.928	High Similarity	NPC190144
0.9274	High Similarity	NPC242032
0.9274	High Similarity	NPC470699
0.9262	High Similarity	NPC84086
0.9256	High Similarity	NPC49341
0.9225	High Similarity	NPC16435
0.9225	High Similarity	NPC227503
0.9225	High Similarity	NPC474639
0.9225	High Similarity	NPC230734
0.9225	High Similarity	NPC202846
0.9225	High Similarity	NPC472334
0.9225	High Similarity	NPC162659
0.9225	High Similarity	NPC265433
0.9225	High Similarity	NPC248727
0.9225	High Similarity	NPC472336
0.9225	High Similarity	NPC270456
0.9225	High Similarity	NPC143139
0.9225	High Similarity	NPC306441
0.9219	High Similarity	NPC469659
0.9219	High Similarity	NPC125649
0.9219	High Similarity	NPC555
0.9219	High Similarity	NPC7515
0.9219	High Similarity	NPC56764
0.9219	High Similarity	NPC209199
0.9219	High Similarity	NPC188378
0.9219	High Similarity	NPC276026
0.9219	High Similarity	NPC206737
0.9219	High Similarity	NPC289258
0.9213	High Similarity	NPC35932
0.9213	High Similarity	NPC253105
0.9213	High Similarity	NPC201587
0.9213	High Similarity	NPC160991
0.9213	High Similarity	NPC184447
0.9213	High Similarity	NPC7903
0.9213	High Similarity	NPC16208
0.9194	High Similarity	NPC181361
0.9194	High Similarity	NPC112596
0.9167	High Similarity	NPC254625
0.9167	High Similarity	NPC475961
0.916	High Similarity	NPC259638
0.9154	High Similarity	NPC272157
0.9154	High Similarity	NPC107551
0.9154	High Similarity	NPC25111
0.9154	High Similarity	NPC474282
0.9154	High Similarity	NPC276490
0.9154	High Similarity	NPC326797
0.9154	High Similarity	NPC176051
0.9154	High Similarity	NPC73535
0.9154	High Similarity	NPC6262
0.9154	High Similarity	NPC242715
0.9154	High Similarity	NPC211549
0.9154	High Similarity	NPC201145
0.9154	High Similarity	NPC102904
0.9154	High Similarity	NPC90615
0.9154	High Similarity	NPC103976
0.9154	High Similarity	NPC56329
0.9147	High Similarity	NPC61946
0.9147	High Similarity	NPC240279
0.9147	High Similarity	NPC180602
0.9147	High Similarity	NPC260898
0.9147	High Similarity	NPC234333
0.9147	High Similarity	NPC241241
0.9147	High Similarity	NPC47398
0.9147	High Similarity	NPC55239
0.9147	High Similarity	NPC151224
0.9147	High Similarity	NPC214853
0.9141	High Similarity	NPC158331
0.9141	High Similarity	NPC11060
0.9127	High Similarity	NPC202582
0.9127	High Similarity	NPC3439
0.9127	High Similarity	NPC218856
0.9127	High Similarity	NPC226788

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 NPC214406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	968
0.2-0.3	1864
0.3-0.4	2764
0.4-0.5	1557
0.5-0.6	875
0.6-0.7	622
0.7-0.8	125
0.8-0.85	9
0.85-0.9	3
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9435	High Similarity	NPD3027	Phase 3
0.9048	High Similarity	NPD1529	Clinical (unspecified phase)
0.8968	High Similarity	NPD1530	Clinical (unspecified phase)
0.8915	High Similarity	NPD1612	Clinical (unspecified phase)
0.8915	High Similarity	NPD1613	Approved
0.8819	High Similarity	NPD3018	Phase 2
0.8655	High Similarity	NPD228	Approved
0.8651	High Similarity	NPD2982	Phase 2
0.8651	High Similarity	NPD2983	Phase 2
0.8571	High Similarity	NPD2981	Phase 2
0.8361	Intermediate Similarity	NPD5283	Phase 1
0.8359	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD4908	Phase 1
0.832	Intermediate Similarity	NPD1548	Phase 1
0.8203	Intermediate Similarity	NPD1610	Phase 2
0.8195	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD2801	Approved
0.8116	Intermediate Similarity	NPD3540	Phase 1
0.8082	Intermediate Similarity	NPD1934	Approved
0.8043	Intermediate Similarity	NPD3539	Phase 1
0.8041	Intermediate Similarity	NPD3882	Suspended
0.8033	Intermediate Similarity	NPD3021	Approved
0.8033	Intermediate Similarity	NPD3022	Approved
0.7985	Intermediate Similarity	NPD4625	Phase 3
0.7941	Intermediate Similarity	NPD1558	Phase 1
0.7939	Intermediate Similarity	NPD4749	Approved
0.7905	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1511	Approved
0.7815	Intermediate Similarity	NPD1242	Phase 1
0.7812	Intermediate Similarity	NPD5536	Phase 2
0.7808	Intermediate Similarity	NPD1653	Approved
0.7803	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1512	Approved
0.7786	Intermediate Similarity	NPD422	Phase 1
0.7778	Intermediate Similarity	NPD4357	Discontinued
0.7761	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD940	Approved
0.775	Intermediate Similarity	NPD846	Approved
0.7704	Intermediate Similarity	NPD2861	Phase 2
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7682	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD4060	Phase 1
0.7681	Intermediate Similarity	NPD3620	Phase 2
0.7681	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6166	Phase 2
0.7664	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD3705	Approved
0.7639	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3060	Approved
0.7616	Intermediate Similarity	NPD3817	Phase 2
0.7609	Intermediate Similarity	NPD2674	Phase 3
0.76	Intermediate Similarity	NPD4750	Phase 3
0.76	Intermediate Similarity	NPD37	Approved
0.7586	Intermediate Similarity	NPD7124	Phase 2
0.7584	Intermediate Similarity	NPD4675	Approved
0.7584	Intermediate Similarity	NPD4678	Approved
0.7557	Intermediate Similarity	NPD1357	Approved
0.7554	Intermediate Similarity	NPD1240	Approved
0.7548	Intermediate Similarity	NPD6232	Discontinued
0.7532	Intermediate Similarity	NPD7054	Approved
0.752	Intermediate Similarity	NPD2684	Approved
0.7519	Intermediate Similarity	NPD1091	Approved
0.7519	Intermediate Similarity	NPD6671	Approved
0.7517	Intermediate Similarity	NPD4005	Discontinued
0.7517	Intermediate Similarity	NPD2219	Phase 1
0.7516	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7074	Phase 3
0.7484	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD7472	Approved
0.7483	Intermediate Similarity	NPD7266	Discontinued
0.7481	Intermediate Similarity	NPD2922	Phase 1
0.7468	Intermediate Similarity	NPD3818	Discontinued
0.7465	Intermediate Similarity	NPD1510	Phase 2
0.7451	Intermediate Similarity	NPD4966	Approved
0.7451	Intermediate Similarity	NPD4965	Approved
0.7451	Intermediate Similarity	NPD4967	Phase 2
0.7447	Intermediate Similarity	NPD1607	Approved
0.744	Intermediate Similarity	NPD290	Approved
0.7432	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD943	Approved
0.7422	Intermediate Similarity	NPD7843	Approved
0.7415	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3145	Approved
0.741	Intermediate Similarity	NPD3144	Approved
0.7405	Intermediate Similarity	NPD7473	Discontinued
0.7403	Intermediate Similarity	NPD4055	Discovery
0.7395	Intermediate Similarity	NPD2933	Approved
0.7395	Intermediate Similarity	NPD9296	Approved
0.7395	Intermediate Similarity	NPD2934	Approved
0.7394	Intermediate Similarity	NPD6111	Discontinued
0.7389	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7157	Approved
0.7383	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4237	Approved
0.7379	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5177	Phase 3
0.7379	Intermediate Similarity	NPD4236	Phase 3
0.7376	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7447	Phase 1
0.7361	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7228	Approved
0.7353	Intermediate Similarity	NPD8651	Approved
0.7351	Intermediate Similarity	NPD4380	Phase 2
0.7333	Intermediate Similarity	NPD2859	Approved
0.7333	Intermediate Similarity	NPD2860	Approved
0.7329	Intermediate Similarity	NPD6797	Phase 2
0.732	Intermediate Similarity	NPD1465	Phase 2
0.7319	Intermediate Similarity	NPD9494	Approved
0.731	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7213	Phase 3
0.7297	Intermediate Similarity	NPD6799	Approved
0.7297	Intermediate Similarity	NPD7212	Phase 2
0.7295	Intermediate Similarity	NPD3020	Approved
0.7292	Intermediate Similarity	NPD6100	Approved
0.7292	Intermediate Similarity	NPD6099	Approved
0.7292	Intermediate Similarity	NPD2935	Discontinued
0.7286	Intermediate Similarity	NPD5110	Phase 2
0.7286	Intermediate Similarity	NPD5111	Phase 2
0.7286	Intermediate Similarity	NPD5109	Approved
0.7284	Intermediate Similarity	NPD7251	Discontinued
0.7266	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6674	Discontinued
0.726	Intermediate Similarity	NPD1652	Phase 2
0.7256	Intermediate Similarity	NPD8054	Approved
0.7256	Intermediate Similarity	NPD8053	Approved
0.7248	Intermediate Similarity	NPD4123	Phase 3
0.7246	Intermediate Similarity	NPD6584	Phase 3
0.7241	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7808	Phase 3
0.7239	Intermediate Similarity	NPD4626	Approved
0.7239	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD968	Approved
0.7214	Intermediate Similarity	NPD7095	Approved
0.7211	Intermediate Similarity	NPD3750	Approved
0.7211	Intermediate Similarity	NPD3892	Phase 2
0.7208	Intermediate Similarity	NPD2978	Approved
0.7208	Intermediate Similarity	NPD2977	Approved
0.7205	Intermediate Similarity	NPD5844	Phase 1
0.7192	Intermediate Similarity	NPD1549	Phase 2
0.719	Intermediate Similarity	NPD5090	Approved
0.719	Intermediate Similarity	NPD5089	Approved
0.7188	Intermediate Similarity	NPD5451	Approved
0.7183	Intermediate Similarity	NPD2238	Phase 2
0.7179	Intermediate Similarity	NPD7075	Discontinued
0.7171	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5718	Phase 2
0.7163	Intermediate Similarity	NPD6798	Discontinued
0.7162	Intermediate Similarity	NPD2677	Approved
0.7162	Intermediate Similarity	NPD6190	Approved
0.7161	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4536	Approved
0.7153	Intermediate Similarity	NPD4538	Approved
0.7153	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4162	Approved
0.7133	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5124	Phase 1
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7133	Intermediate Similarity	NPD1424	Approved
0.7121	Intermediate Similarity	NPD709	Approved
0.7117	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6788	Approved
0.7111	Intermediate Similarity	NPD6516	Phase 2
0.7111	Intermediate Similarity	NPD5846	Approved
0.7103	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5494	Approved
0.7086	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4097	Suspended
0.708	Intermediate Similarity	NPD2233	Approved
0.708	Intermediate Similarity	NPD2232	Approved
0.708	Intermediate Similarity	NPD2230	Approved
0.707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5297	Approved
0.7059	Intermediate Similarity	NPD3847	Discontinued
0.7059	Intermediate Similarity	NPD3496	Discontinued
0.7059	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7055	Intermediate Similarity	NPD2796	Approved
0.7049	Intermediate Similarity	NPD844	Approved
0.7047	Intermediate Similarity	NPD5241	Discontinued
0.704	Intermediate Similarity	NPD291	Approved
0.7034	Intermediate Similarity	NPD6895	Approved
0.7034	Intermediate Similarity	NPD6896	Approved
0.703	Intermediate Similarity	NPD7549	Discontinued
0.7029	Intermediate Similarity	NPD6582	Phase 2
0.7029	Intermediate Similarity	NPD6583	Phase 3
0.7023	Intermediate Similarity	NPD5535	Approved
0.702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4340	Discontinued
0.7014	Intermediate Similarity	NPD447	Suspended
0.7013	Intermediate Similarity	NPD6599	Discontinued
0.7007	Intermediate Similarity	NPD1375	Discontinued
0.7007	Intermediate Similarity	NPD5762	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