NPASS Compound

Structure

NPC206882 OpenBabel07101719252D 28 30 0 0 1 0 0 0 0 0999 V2000 -6.2788 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0659 -0.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2579 1.4565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8958 -1.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0388 -2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4836 -1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0768 -0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7044 -3.2564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4781 -1.2841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6646 0.5430 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 28 1 0 0 0 0 16 9 1 1 0 0 0 16 17 1 0 0 0 0 17 12 1 1 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 15 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.19
Volume:	400.321
LogP:	2.71
LogD:	2.896
LogS:	-3.741
# Rotatable Bonds:	8
TPSA:	66.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	3.247
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.784
MDCK Permeability:	4.1932980821002275e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.187
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.208
Plasma Protein Binding (PPB):	82.64498901367188%
Volume Distribution (VD):	0.555
Pgp-substrate:	6.722489833831787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.223
CYP2C9-substrate:	0.551
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	9.622
Half-life (T1/2):	0.737

ADMET: Toxicity

hERG Blockers:	0.61
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.886
Carcinogencity:	0.13
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.099

Download Data

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

Natural Product: NPC206882

Natural Product ID:	NPC206882
*Common Name:**	(+)-Lariciresinol Dimethyl Ether
IUPAC Name:	[(2S,3R,4R)-2-(3,4-dimethoxyphenyl)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl]methanol
Synonyms:	(+)-Lariciresinol Dimethyl Ether
Standard InCHIKey:	AYWPHVUFQNWITL-PNLZDCPESA-N
Standard InCHI:	InChI=1S/C22H28O6/c1-24-18-7-5-14(10-20(18)26-3)9-16-13-28-22(17(16)12-23)15-6-8-19(25-2)21(11-15)27-4/h5-8,10-11,16-17,22-23H,9,12-13H2,1-4H3/t16-,17-,22+/m0/s1
SMILES:	OC[C@H]1[C@H](CO[C@@H]1c1ccc(c(c1)OC)OC)Cc1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1760590
PubChem CID:	181325
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	trunk	Jeju island, Korea	2005-Dec	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	44420.0	nM	PMID[450169]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	20130.0	nM	PMID[450169]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	25120.0	nM	PMID[450169]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	15400.0	nM	PMID[450169]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	21500.0	nM	PMID[450169]

☑ 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 NPC206882 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	335
0.1-0.2	1204
0.2-0.3	3137
0.3-0.4	8541
0.4-0.5	10705
0.5-0.6	4687
0.6-0.7	9878
0.7-0.8	3064
0.8-0.85	743
0.85-0.9	307
0.9-0.95	59
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
0.9835	High Similarity	NPC470084
0.9675	High Similarity	NPC257582
0.9675	High Similarity	NPC242807
0.9675	High Similarity	NPC64201
0.9675	High Similarity	NPC153739
0.9675	High Similarity	NPC92164
0.9675	High Similarity	NPC145305
0.9675	High Similarity	NPC77040
0.9675	High Similarity	NPC241522
0.9675	High Similarity	NPC42300
0.9675	High Similarity	NPC174495
0.9675	High Similarity	NPC187998
0.9597	High Similarity	NPC277804
0.9593	High Similarity	NPC475875
0.958	High Similarity	NPC126935
0.958	High Similarity	NPC216929
0.958	High Similarity	NPC312713
0.958	High Similarity	NPC65933
0.958	High Similarity	NPC57268
0.958	High Similarity	NPC172676
0.952	High Similarity	NPC230219
0.9512	High Similarity	NPC282703
0.9512	High Similarity	NPC184733
0.9512	High Similarity	NPC11258
0.9512	High Similarity	NPC45774
0.9512	High Similarity	NPC129570
0.9512	High Similarity	NPC128208
0.9512	High Similarity	NPC21867
0.9504	High Similarity	NPC18449
0.9504	High Similarity	NPC34902
0.9504	High Similarity	NPC121783
0.9444	High Similarity	NPC26394
0.944	High Similarity	NPC7171
0.944	High Similarity	NPC27843
0.944	High Similarity	NPC228346
0.944	High Similarity	NPC161557
0.944	High Similarity	NPC158079
0.944	High Similarity	NPC115207
0.944	High Similarity	NPC40432
0.9431	High Similarity	NPC165045
0.9431	High Similarity	NPC118533
0.937	High Similarity	NPC287745
0.9365	High Similarity	NPC207400
0.9365	High Similarity	NPC181049
0.935	High Similarity	NPC50683
0.935	High Similarity	NPC112571
0.935	High Similarity	NPC285725
0.9291	High Similarity	NPC158331
0.9274	High Similarity	NPC5428
0.9268	High Similarity	NPC148627
0.9244	High Similarity	NPC474214
0.9244	High Similarity	NPC474040
0.9225	High Similarity	NPC29799
0.9225	High Similarity	NPC177160
0.9225	High Similarity	NPC477939
0.9225	High Similarity	NPC10737
0.9225	High Similarity	NPC156502
0.9225	High Similarity	NPC209985
0.9225	High Similarity	NPC54743
0.9225	High Similarity	NPC263367
0.9219	High Similarity	NPC244983
0.9219	High Similarity	NPC47181
0.9219	High Similarity	NPC67247
0.9219	High Similarity	NPC326095
0.9213	High Similarity	NPC204215
0.9213	High Similarity	NPC104077
0.9213	High Similarity	NPC147616
0.9213	High Similarity	NPC4940
0.9213	High Similarity	NPC175067
0.9213	High Similarity	NPC259742
0.9213	High Similarity	NPC219671
0.92	High Similarity	NPC252307
0.92	High Similarity	NPC222127
0.92	High Similarity	NPC82862
0.92	High Similarity	NPC474178
0.92	High Similarity	NPC245826
0.9194	High Similarity	NPC186845
0.9194	High Similarity	NPC88297
0.9194	High Similarity	NPC9891
0.9187	High Similarity	NPC109822
0.9187	High Similarity	NPC94276
0.918	High Similarity	NPC71090
0.9167	High Similarity	NPC474320
0.9154	High Similarity	NPC477938
0.9147	High Similarity	NPC99572
0.9147	High Similarity	NPC126409
0.9147	High Similarity	NPC101624
0.9147	High Similarity	NPC93783
0.9147	High Similarity	NPC184938
0.9147	High Similarity	NPC18576
0.9141	High Similarity	NPC196937
0.9134	High Similarity	NPC474017
0.912	High Similarity	NPC473093
0.912	High Similarity	NPC147821
0.912	High Similarity	NPC8050
0.912	High Similarity	NPC473092
0.912	High Similarity	NPC118787
0.912	High Similarity	NPC98745
0.912	High Similarity	NPC292056
0.912	High Similarity	NPC242032
0.912	High Similarity	NPC163332
0.912	High Similarity	NPC41706
0.912	High Similarity	NPC183181
0.912	High Similarity	NPC111247
0.912	High Similarity	NPC319625
0.9106	High Similarity	NPC31344
0.9106	High Similarity	NPC317769
0.9106	High Similarity	NPC280704
0.9106	High Similarity	NPC473451
0.9106	High Similarity	NPC471693
0.9077	High Similarity	NPC77861
0.9077	High Similarity	NPC471988
0.907	High Similarity	NPC16485
0.907	High Similarity	NPC187616
0.907	High Similarity	NPC193026
0.907	High Similarity	NPC471942
0.907	High Similarity	NPC49603
0.9062	High Similarity	NPC106739
0.9062	High Similarity	NPC471505
0.9062	High Similarity	NPC18842
0.9048	High Similarity	NPC281864
0.9048	High Similarity	NPC54321
0.9048	High Similarity	NPC226862
0.9048	High Similarity	NPC165128
0.9048	High Similarity	NPC328682
0.9048	High Similarity	NPC57119
0.9048	High Similarity	NPC158471
0.904	High Similarity	NPC58607
0.904	High Similarity	NPC178284
0.904	High Similarity	NPC191037
0.9032	High Similarity	NPC114901
0.9032	High Similarity	NPC293701
0.9032	High Similarity	NPC48990
0.9024	High Similarity	NPC85488
0.9008	High Similarity	NPC281780
0.9008	High Similarity	NPC469981
0.9008	High Similarity	NPC185908
0.9008	High Similarity	NPC135961
0.9	High Similarity	NPC142547
0.9	High Similarity	NPC236522
0.9	High Similarity	NPC24490
0.9	High Similarity	NPC135777
0.9	High Similarity	NPC174191
0.9	High Similarity	NPC34103
0.9	High Similarity	NPC165155
0.9	High Similarity	NPC141765
0.8984	High Similarity	NPC227160
0.8984	High Similarity	NPC82111
0.8976	High Similarity	NPC86030
0.8976	High Similarity	NPC190629
0.8976	High Similarity	NPC285339
0.8976	High Similarity	NPC273295
0.8976	High Similarity	NPC170844
0.8976	High Similarity	NPC210623
0.8976	High Similarity	NPC218856
0.8976	High Similarity	NPC226788
0.8976	High Similarity	NPC202582
0.8976	High Similarity	NPC476968
0.8976	High Similarity	NPC5851
0.8976	High Similarity	NPC470258
0.8976	High Similarity	NPC222004
0.8976	High Similarity	NPC3439
0.8968	High Similarity	NPC474119
0.896	High Similarity	NPC194519
0.8947	High Similarity	NPC471414
0.8947	High Similarity	NPC87725
0.8947	High Similarity	NPC472711
0.8947	High Similarity	NPC263261
0.8943	High Similarity	NPC54872
0.8943	High Similarity	NPC324571
0.8943	High Similarity	NPC262156
0.8943	High Similarity	NPC343720
0.8943	High Similarity	NPC312675
0.8943	High Similarity	NPC470804
0.8943	High Similarity	NPC476343
0.8943	High Similarity	NPC473853
0.8943	High Similarity	NPC113865
0.8943	High Similarity	NPC470212
0.8943	High Similarity	NPC184651
0.8939	High Similarity	NPC193666
0.8939	High Similarity	NPC260842
0.8939	High Similarity	NPC123526
0.8939	High Similarity	NPC156376
0.8939	High Similarity	NPC88640
0.8923	High Similarity	NPC478085
0.8917	High Similarity	NPC81067
0.8917	High Similarity	NPC9341
0.8915	High Similarity	NPC201587
0.8915	High Similarity	NPC253105
0.8915	High Similarity	NPC7744
0.8906	High Similarity	NPC271208
0.8906	High Similarity	NPC173308
0.8906	High Similarity	NPC237169
0.8906	High Similarity	NPC143483
0.8906	High Similarity	NPC181079
0.8906	High Similarity	NPC233224
0.8906	High Similarity	NPC470624
0.8898	High Similarity	NPC98631
0.8898	High Similarity	NPC186843
0.8898	High Similarity	NPC72529

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 NPC206882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	767
0.2-0.3	1573
0.3-0.4	2623
0.4-0.5	2003
0.5-0.6	1050
0.6-0.7	678
0.7-0.8	172
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8976	High Similarity	NPD3027	Phase 3
0.8824	High Similarity	NPD5283	Phase 1
0.8492	Intermediate Similarity	NPD3705	Approved
0.8346	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1613	Approved
0.8244	Intermediate Similarity	NPD2861	Phase 2
0.8129	Intermediate Similarity	NPD4236	Phase 3
0.8129	Intermediate Similarity	NPD4237	Approved
0.811	Intermediate Similarity	NPD1357	Approved
0.8077	Intermediate Similarity	NPD2983	Phase 2
0.8077	Intermediate Similarity	NPD2982	Phase 2
0.8074	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD3620	Phase 2
0.8049	Intermediate Similarity	NPD228	Approved
0.8045	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2981	Phase 2
0.797	Intermediate Similarity	NPD3018	Phase 2
0.797	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD37	Approved
0.7951	Intermediate Similarity	NPD2684	Approved
0.7937	Intermediate Similarity	NPD7157	Approved
0.7919	Intermediate Similarity	NPD4967	Phase 2
0.7919	Intermediate Similarity	NPD4965	Approved
0.7919	Intermediate Similarity	NPD4966	Approved
0.791	Intermediate Similarity	NPD4908	Phase 1
0.7886	Intermediate Similarity	NPD3022	Approved
0.7886	Intermediate Similarity	NPD3021	Approved
0.7872	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6674	Discontinued
0.7842	Intermediate Similarity	NPD5588	Approved
0.784	Intermediate Similarity	NPD7843	Approved
0.7817	Intermediate Similarity	NPD6331	Phase 2
0.7817	Intermediate Similarity	NPD4110	Phase 3
0.7817	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5536	Phase 2
0.7803	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4536	Approved
0.777	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4538	Approved
0.7762	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD5735	Approved
0.7746	Intermediate Similarity	NPD3060	Approved
0.773	Intermediate Similarity	NPD1375	Discontinued
0.7708	Intermediate Similarity	NPD5058	Phase 3
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7681	Intermediate Similarity	NPD4060	Phase 1
0.7681	Intermediate Similarity	NPD2238	Phase 2
0.7669	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD5109	Approved
0.7664	Intermediate Similarity	NPD5111	Phase 2
0.7664	Intermediate Similarity	NPD5110	Phase 2
0.766	Intermediate Similarity	NPD2161	Phase 2
0.7626	Intermediate Similarity	NPD3657	Discovery
0.7626	Intermediate Similarity	NPD6355	Discontinued
0.7622	Intermediate Similarity	NPD5177	Phase 3
0.7616	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD8651	Approved
0.7606	Intermediate Similarity	NPD5762	Approved
0.7606	Intermediate Similarity	NPD5763	Approved
0.7606	Intermediate Similarity	NPD7266	Discontinued
0.7597	Intermediate Similarity	NPD7199	Phase 2
0.7589	Intermediate Similarity	NPD5960	Phase 3
0.7581	Intermediate Similarity	NPD290	Approved
0.7554	Intermediate Similarity	NPD1558	Phase 1
0.7554	Intermediate Similarity	NPD4140	Approved
0.7551	Intermediate Similarity	NPD52	Approved
0.7551	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7526	Approved
0.7551	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD5327	Phase 3
0.7519	Intermediate Similarity	NPD1091	Approved
0.7518	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2677	Approved
0.7517	Intermediate Similarity	NPD4005	Discontinued
0.7516	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5846	Approved
0.75	Intermediate Similarity	NPD2560	Approved
0.75	Intermediate Similarity	NPD5126	Approved
0.75	Intermediate Similarity	NPD5125	Phase 3
0.75	Intermediate Similarity	NPD4162	Approved
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2563	Approved
0.75	Intermediate Similarity	NPD6516	Phase 2
0.7483	Intermediate Similarity	NPD4123	Phase 3
0.7483	Intermediate Similarity	NPD1934	Approved
0.7482	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1548	Phase 1
0.7468	Intermediate Similarity	NPD7228	Approved
0.7466	Intermediate Similarity	NPD7124	Phase 2
0.7465	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7095	Approved
0.7463	Intermediate Similarity	NPD1608	Approved
0.7463	Intermediate Similarity	NPD2235	Phase 2
0.7463	Intermediate Similarity	NPD2231	Phase 2
0.7459	Intermediate Similarity	NPD291	Approved
0.7448	Intermediate Similarity	NPD4628	Phase 3
0.7447	Intermediate Similarity	NPD6653	Approved
0.7438	Intermediate Similarity	NPD3020	Approved
0.7434	Intermediate Similarity	NPD5772	Approved
0.7434	Intermediate Similarity	NPD2977	Approved
0.7434	Intermediate Similarity	NPD2978	Approved
0.7434	Intermediate Similarity	NPD5773	Approved
0.7426	Intermediate Similarity	NPD3094	Phase 2
0.7419	Intermediate Similarity	NPD5494	Approved
0.741	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4749	Approved
0.7397	Intermediate Similarity	NPD5241	Discontinued
0.7394	Intermediate Similarity	NPD6895	Approved
0.7394	Intermediate Similarity	NPD6896	Approved
0.7389	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6671	Approved
0.7372	Intermediate Similarity	NPD4624	Approved
0.7372	Intermediate Similarity	NPD6584	Phase 3
0.7372	Intermediate Similarity	NPD8127	Discontinued
0.7368	Intermediate Similarity	NPD2667	Approved
0.7368	Intermediate Similarity	NPD2668	Approved
0.7361	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3540	Phase 1
0.736	Intermediate Similarity	NPD968	Approved
0.7357	Intermediate Similarity	NPD6233	Phase 2
0.7351	Intermediate Similarity	NPD4675	Approved
0.7351	Intermediate Similarity	NPD4678	Approved
0.7348	Intermediate Similarity	NPD1182	Approved
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7338	Intermediate Similarity	NPD3882	Suspended
0.7333	Intermediate Similarity	NPD2232	Approved
0.7333	Intermediate Similarity	NPD3687	Approved
0.7333	Intermediate Similarity	NPD2233	Approved
0.7333	Intermediate Similarity	NPD3686	Approved
0.7333	Intermediate Similarity	NPD1840	Phase 2
0.7333	Intermediate Similarity	NPD2230	Approved
0.7333	Intermediate Similarity	NPD4210	Discontinued
0.7329	Intermediate Similarity	NPD3892	Phase 2
0.7329	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3051	Approved
0.7324	Intermediate Similarity	NPD6353	Approved
0.7323	Intermediate Similarity	NPD5451	Approved
0.732	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4357	Discontinued
0.7293	Intermediate Similarity	NPD5585	Approved
0.7292	Intermediate Similarity	NPD2438	Suspended
0.7292	Intermediate Similarity	NPD3539	Phase 1
0.7287	Intermediate Similarity	NPD5535	Approved
0.7286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6798	Discontinued
0.7284	Intermediate Similarity	NPD7240	Approved
0.7279	Intermediate Similarity	NPD3685	Discontinued
0.7278	Intermediate Similarity	NPD2969	Approved
0.7278	Intermediate Similarity	NPD2970	Approved
0.7273	Intermediate Similarity	NPD6111	Discontinued
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3092	Approved
0.725	Intermediate Similarity	NPD3818	Discontinued
0.7248	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD558	Phase 2
0.7241	Intermediate Similarity	NPD6002	Phase 3
0.7241	Intermediate Similarity	NPD6004	Phase 3
0.7241	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6005	Phase 3
0.7241	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD17	Approved
0.7239	Intermediate Similarity	NPD3095	Discontinued
0.7233	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6166	Phase 2
0.7226	Intermediate Similarity	NPD6696	Suspended
0.7226	Intermediate Similarity	NPD2922	Phase 1
0.7226	Intermediate Similarity	NPD1283	Approved
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7222	Intermediate Similarity	NPD4108	Discontinued
0.7219	Intermediate Similarity	NPD1653	Approved
0.7218	Intermediate Similarity	NPD3091	Approved
0.7215	Intermediate Similarity	NPD6071	Discontinued
0.7211	Intermediate Similarity	NPD4535	Phase 3
0.7208	Intermediate Similarity	NPD2801	Approved
0.7208	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5844	Phase 1
0.72	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2424	Discontinued
0.719	Intermediate Similarity	NPD2860	Approved
0.719	Intermediate Similarity	NPD2859	Approved
0.7185	Intermediate Similarity	NPD3847	Discontinued
0.7183	Intermediate Similarity	NPD2979	Phase 3
0.7181	Intermediate Similarity	NPD1774	Approved
0.7172	Intermediate Similarity	NPD6032	Approved
0.7165	Intermediate Similarity	NPD1358	Approved
0.7164	Intermediate Similarity	NPD1651	Approved
0.7164	Intermediate Similarity	NPD5691	Approved
0.7163	Intermediate Similarity	NPD5718	Phase 2
0.7162	Intermediate Similarity	NPD6190	Approved
0.7161	Intermediate Similarity	NPD3817	Phase 2
0.7154	Intermediate Similarity	NPD821	Approved
0.7153	Intermediate Similarity	NPD1669	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