NPASS Compound

Structure

CID310338 OpenBabel06191716122D 21 22 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 0.8660 -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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 3 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 -5.1962 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 -6.0622 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 3 2 0 0 0 0 2 21 1 0 0 0 0 3 14 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 9 1 0 0 0 0 5 13 2 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 14 15 1 0 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.13
Volume:	308.05
LogP:	3.482
LogD:	3.457
LogS:	-3.38
# Rotatable Bonds:	5
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.812
Synthetic Accessibility Score:	2.97
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.725
MDCK Permeability:	1.728906499920413e-05
Pgp-inhibitor:	0.102
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	99.93831634521484%
Volume Distribution (VD):	0.604
Pgp-substrate:	0.6704555749893188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.802
CYP2C19-substrate:	0.219
CYP2C9-inhibitor:	0.842
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.757
CYP3A4-substrate:	0.558

ADMET: Excretion

Clearance (CL):	7.821
Half-life (T1/2):	0.802

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.324
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.846
Carcinogencity:	0.483
Eye Corrosion:	0.003
Eye Irritation:	0.119
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC310338

Natural Product ID:	NPC310338
*Common Name:**	3''-Methoxynyasol
IUPAC Name:	4-[(1Z)-1-(4-hydroxyphenyl)penta-1,4-dien-3-yl]-2-methoxyphenol
Synonyms:	3'-Methoxynyasol
Standard InCHIKey:	APVUNYPUJLEPIY-DAXSKMNVSA-N
Standard InCHI:	InChI=1S/C18H18O3/c1-3-14(7-4-13-5-9-16(19)10-6-13)15-8-11-17(20)18(12-15)21-2/h3-12,14,19-20H,1H2,2H3/b7-4-
SMILES:	C=CC(/C=Cc1ccc(cc1)O)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509757
PubChem CID:	25218067
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987058]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	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
Others	1

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	31900.0	nM	PMID[464565]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	22300.0	nM	PMID[464565]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	23400.0	nM	PMID[464565]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	15900.0	nM	PMID[464565]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	23700.0	nM	PMID[464565]
NPT27	Others	Unspecified		CC50	=	24100.0	nM	PMID[464565]

☑ 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 NPC310338 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	1778
0.2-0.3	4747
0.3-0.4	13624
0.4-0.5	4362
0.5-0.6	5770
0.6-0.7	8098
0.7-0.8	2911
0.8-0.85	678
0.85-0.9	303
0.9-0.95	79
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC281298
0.9911	High Similarity	NPC95614
0.9911	High Similarity	NPC165133
0.9911	High Similarity	NPC227217
0.9911	High Similarity	NPC232316
0.9911	High Similarity	NPC242885
0.9911	High Similarity	NPC117780
0.9911	High Similarity	NPC56214
0.9737	High Similarity	NPC160380
0.9737	High Similarity	NPC38996
0.9732	High Similarity	NPC470626
0.9652	High Similarity	NPC85488
0.9643	High Similarity	NPC293619
0.9569	High Similarity	NPC317769
0.9569	High Similarity	NPC280704
0.9569	High Similarity	NPC31344
0.9478	High Similarity	NPC207613
0.9407	High Similarity	NPC9067
0.9407	High Similarity	NPC228771
0.9407	High Similarity	NPC148627
0.9407	High Similarity	NPC29008
0.9407	High Similarity	NPC266705
0.9397	High Similarity	NPC470212
0.9397	High Similarity	NPC324571
0.9397	High Similarity	NPC113865
0.9397	High Similarity	NPC262156
0.9397	High Similarity	NPC54872
0.9397	High Similarity	NPC184651
0.9397	High Similarity	NPC343720
0.9397	High Similarity	NPC312675
0.9397	High Similarity	NPC473853
0.9386	High Similarity	NPC474040
0.9328	High Similarity	NPC274356
0.9316	High Similarity	NPC30462
0.9298	High Similarity	NPC86947
0.9298	High Similarity	NPC164386
0.9286	High Similarity	NPC165106
0.9279	High Similarity	NPC156840
0.9279	High Similarity	NPC8547
0.9279	High Similarity	NPC257124
0.9279	High Similarity	NPC173746
0.925	High Similarity	NPC5428
0.925	High Similarity	NPC118533
0.925	High Similarity	NPC165045
0.925	High Similarity	NPC127587
0.9237	High Similarity	NPC249788
0.9237	High Similarity	NPC471693
0.9231	High Similarity	NPC127389
0.9231	High Similarity	NPC290451
0.9174	High Similarity	NPC307050
0.9174	High Similarity	NPC277458
0.9174	High Similarity	NPC184733
0.9174	High Similarity	NPC282703
0.9174	High Similarity	NPC21867
0.9174	High Similarity	NPC45774
0.9174	High Similarity	NPC11258
0.9174	High Similarity	NPC129570
0.9174	High Similarity	NPC128208
0.9167	High Similarity	NPC76451
0.9153	High Similarity	NPC41562
0.9138	High Similarity	NPC311595
0.9138	High Similarity	NPC24474
0.9123	High Similarity	NPC47194
0.9123	High Similarity	NPC475815
0.9123	High Similarity	NPC473264
0.9099	High Similarity	NPC233731
0.9099	High Similarity	NPC36108
0.9099	High Similarity	NPC7097
0.9099	High Similarity	NPC246358
0.9098	High Similarity	NPC475875
0.9091	High Similarity	NPC21563
0.9091	High Similarity	NPC106511
0.9083	High Similarity	NPC475169
0.9083	High Similarity	NPC17943
0.9083	High Similarity	NPC208950
0.9083	High Similarity	NPC257589
0.9083	High Similarity	NPC193544
0.9083	High Similarity	NPC116907
0.9083	High Similarity	NPC251855
0.9083	High Similarity	NPC221077
0.9083	High Similarity	NPC233410
0.9083	High Similarity	NPC298757
0.9083	High Similarity	NPC203133
0.9083	High Similarity	NPC117214
0.9083	High Similarity	NPC53305
0.9083	High Similarity	NPC472093
0.9083	High Similarity	NPC57490
0.9076	High Similarity	NPC228922
0.9076	High Similarity	NPC197757
0.9052	High Similarity	NPC474214
0.9043	High Similarity	NPC81067
0.9043	High Similarity	NPC9341
0.9024	High Similarity	NPC77040
0.9024	High Similarity	NPC174495
0.9024	High Similarity	NPC181079
0.9024	High Similarity	NPC153739
0.9024	High Similarity	NPC242807
0.9024	High Similarity	NPC145305
0.9024	High Similarity	NPC275950
0.9024	High Similarity	NPC42300
0.9024	High Similarity	NPC173308
0.9024	High Similarity	NPC257582
0.9024	High Similarity	NPC241522
0.9024	High Similarity	NPC92164
0.9024	High Similarity	NPC187998
0.9024	High Similarity	NPC64201
0.9009	High Similarity	NPC75440
0.9009	High Similarity	NPC201959
0.9008	High Similarity	NPC127937
0.9008	High Similarity	NPC92207
0.9008	High Similarity	NPC17837
0.9008	High Similarity	NPC304630
0.9	High Similarity	NPC5796
0.9	High Similarity	NPC206487
0.8983	High Similarity	NPC60962
0.8983	High Similarity	NPC224814
0.8983	High Similarity	NPC269843
0.8983	High Similarity	NPC109083
0.8983	High Similarity	NPC189844
0.8983	High Similarity	NPC14007
0.8974	High Similarity	NPC474320
0.8952	High Similarity	NPC27843
0.8952	High Similarity	NPC40432
0.8952	High Similarity	NPC115207
0.8952	High Similarity	NPC476345
0.8952	High Similarity	NPC161557
0.8952	High Similarity	NPC232275
0.8952	High Similarity	NPC474017
0.8952	High Similarity	NPC277804
0.8952	High Similarity	NPC45715
0.8952	High Similarity	NPC228346
0.8952	High Similarity	NPC474356
0.8952	High Similarity	NPC7171
0.8952	High Similarity	NPC12275
0.8952	High Similarity	NPC158079
0.8938	High Similarity	NPC195873
0.8938	High Similarity	NPC139617
0.8938	High Similarity	NPC78918
0.8934	High Similarity	NPC169474
0.8934	High Similarity	NPC293054
0.8934	High Similarity	NPC82679
0.8934	High Similarity	NPC246620
0.8934	High Similarity	NPC324112
0.8934	High Similarity	NPC124452
0.8934	High Similarity	NPC159968
0.8934	High Similarity	NPC282000
0.8934	High Similarity	NPC236791
0.8934	High Similarity	NPC74817
0.8929	High Similarity	NPC254833
0.8929	High Similarity	NPC228343
0.8926	High Similarity	NPC194519
0.8926	High Similarity	NPC234400
0.8926	High Similarity	NPC60885
0.8917	High Similarity	NPC136319
0.8917	High Similarity	NPC282496
0.8917	High Similarity	NPC233526
0.8908	High Similarity	NPC476343
0.8908	High Similarity	NPC201777
0.888	High Similarity	NPC207400
0.888	High Similarity	NPC6451
0.888	High Similarity	NPC106739
0.888	High Similarity	NPC227002
0.888	High Similarity	NPC471505
0.888	High Similarity	NPC181049
0.8879	High Similarity	NPC221049
0.8871	High Similarity	NPC126836
0.8871	High Similarity	NPC143483
0.8862	High Similarity	NPC226661
0.8862	High Similarity	NPC206615
0.8862	High Similarity	NPC472968
0.8862	High Similarity	NPC186843
0.8862	High Similarity	NPC252307
0.8862	High Similarity	NPC154866
0.8862	High Similarity	NPC245826
0.8862	High Similarity	NPC470213
0.8862	High Similarity	NPC470084
0.8862	High Similarity	NPC474178
0.8862	High Similarity	NPC98631
0.8852	High Similarity	NPC214406
0.8852	High Similarity	NPC18924
0.8852	High Similarity	NPC44748
0.8852	High Similarity	NPC90128
0.8852	High Similarity	NPC120225
0.8852	High Similarity	NPC178284
0.8852	High Similarity	NPC78974
0.8852	High Similarity	NPC179777
0.8852	High Similarity	NPC303680
0.8852	High Similarity	NPC223136
0.8852	High Similarity	NPC84076
0.8852	High Similarity	NPC58607
0.8852	High Similarity	NPC191037
0.8852	High Similarity	NPC213552
0.8852	High Similarity	NPC28730
0.8852	High Similarity	NPC103823
0.885	High Similarity	NPC137685
0.8843	High Similarity	NPC293701
0.8843	High Similarity	NPC114901
0.8843	High Similarity	NPC48990
0.8833	High Similarity	NPC262253
0.8833	High Similarity	NPC71579

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 NPC310338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	1039
0.2-0.3	1430
0.3-0.4	2727
0.4-0.5	1796
0.5-0.6	981
0.6-0.7	687
0.7-0.8	152
0.8-0.85	10
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD5283	Phase 1
0.9279	High Similarity	NPD228	Approved
0.8929	High Similarity	NPD3022	Approved
0.8929	High Similarity	NPD3021	Approved
0.879	High Similarity	NPD3027	Phase 3
0.876	High Similarity	NPD4379	Clinical (unspecified phase)
0.8583	High Similarity	NPD3619	Clinical (unspecified phase)
0.8583	High Similarity	NPD3620	Phase 2
0.8306	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD3020	Approved
0.819	Intermediate Similarity	NPD2684	Approved
0.8182	Intermediate Similarity	NPD5536	Phase 2
0.8154	Intermediate Similarity	NPD4060	Phase 1
0.8125	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2674	Phase 3
0.8049	Intermediate Similarity	NPD1357	Approved
0.8047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD2859	Approved
0.8018	Intermediate Similarity	NPD2860	Approved
0.8017	Intermediate Similarity	NPD7157	Approved
0.8015	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1613	Approved
0.8015	Intermediate Similarity	NPD1558	Phase 1
0.8	Intermediate Similarity	NPD5110	Phase 2
0.8	Intermediate Similarity	NPD3144	Approved
0.8	Intermediate Similarity	NPD3145	Approved
0.8	Intermediate Similarity	NPD5111	Phase 2
0.8	Intermediate Similarity	NPD5109	Approved
0.7928	Intermediate Similarity	NPD2933	Approved
0.7928	Intermediate Similarity	NPD2934	Approved
0.7928	Intermediate Similarity	NPD9296	Approved
0.7917	Intermediate Similarity	NPD7843	Approved
0.7907	Intermediate Similarity	NPD2861	Phase 2
0.7874	Intermediate Similarity	NPD2982	Phase 2
0.7874	Intermediate Similarity	NPD2983	Phase 2
0.7869	Intermediate Similarity	NPD6671	Approved
0.784	Intermediate Similarity	NPD2667	Approved
0.784	Intermediate Similarity	NPD2668	Approved
0.7829	Intermediate Similarity	NPD6584	Phase 3
0.7815	Intermediate Similarity	NPD5451	Approved
0.7795	Intermediate Similarity	NPD2232	Approved
0.7795	Intermediate Similarity	NPD2981	Phase 2
0.7795	Intermediate Similarity	NPD2233	Approved
0.7795	Intermediate Similarity	NPD2230	Approved
0.7786	Intermediate Similarity	NPD7095	Approved
0.7769	Intermediate Similarity	NPD3018	Phase 2
0.7769	Intermediate Similarity	NPD9494	Approved
0.7754	Intermediate Similarity	NPD6331	Phase 2
0.7717	Intermediate Similarity	NPD3705	Approved
0.7717	Intermediate Similarity	NPD1610	Phase 2
0.7712	Intermediate Similarity	NPD968	Approved
0.771	Intermediate Similarity	NPD4908	Phase 1
0.771	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6896	Approved
0.7704	Intermediate Similarity	NPD6895	Approved
0.7698	Intermediate Similarity	NPD5846	Approved
0.7698	Intermediate Similarity	NPD4626	Approved
0.7698	Intermediate Similarity	NPD6516	Phase 2
0.7692	Intermediate Similarity	NPD4624	Approved
0.7681	Intermediate Similarity	NPD3060	Approved
0.7674	Intermediate Similarity	NPD1283	Approved
0.7647	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD4110	Phase 3
0.7619	Intermediate Similarity	NPD1651	Approved
0.7611	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1669	Approved
0.7597	Intermediate Similarity	NPD6582	Phase 2
0.7597	Intermediate Similarity	NPD6583	Phase 3
0.7594	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5718	Phase 2
0.7591	Intermediate Similarity	NPD2161	Phase 2
0.7571	Intermediate Similarity	NPD5241	Discontinued
0.7556	Intermediate Similarity	NPD3657	Discovery
0.7556	Intermediate Similarity	NPD6355	Discontinued
0.7556	Intermediate Similarity	NPD5735	Approved
0.7554	Intermediate Similarity	NPD5177	Phase 3
0.7538	Intermediate Similarity	NPD2922	Phase 1
0.75	Intermediate Similarity	NPD290	Approved
0.75	Intermediate Similarity	NPD3847	Discontinued
0.7481	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5535	Approved
0.7478	Intermediate Similarity	NPD288	Approved
0.7465	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD4749	Approved
0.7462	Intermediate Similarity	NPD5327	Phase 3
0.7442	Intermediate Similarity	NPD3092	Approved
0.7442	Intermediate Similarity	NPD1281	Approved
0.744	Intermediate Similarity	NPD709	Approved
0.7429	Intermediate Similarity	NPD4162	Approved
0.7413	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1548	Phase 1
0.7402	Intermediate Similarity	NPD3091	Approved
0.7391	Intermediate Similarity	NPD844	Approved
0.7388	Intermediate Similarity	NPD4625	Phase 3
0.7385	Intermediate Similarity	NPD1608	Approved
0.7385	Intermediate Similarity	NPD2235	Phase 2
0.7385	Intermediate Similarity	NPD2231	Phase 2
0.7372	Intermediate Similarity	NPD4097	Suspended
0.7361	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2808	Discontinued
0.7353	Intermediate Similarity	NPD4140	Approved
0.7353	Intermediate Similarity	NPD2238	Phase 2
0.7348	Intermediate Similarity	NPD3055	Approved
0.7348	Intermediate Similarity	NPD3053	Approved
0.7344	Intermediate Similarity	NPD5585	Approved
0.7344	Intermediate Similarity	NPD5691	Approved
0.7339	Intermediate Similarity	NPD821	Approved
0.7339	Intermediate Similarity	NPD9377	Approved
0.7339	Intermediate Similarity	NPD7635	Approved
0.7339	Intermediate Similarity	NPD9379	Approved
0.7333	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.7305	Intermediate Similarity	NPD4237	Approved
0.7305	Intermediate Similarity	NPD6674	Discontinued
0.7305	Intermediate Similarity	NPD4236	Phase 3
0.7297	Intermediate Similarity	NPD1934	Approved
0.7293	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1242	Phase 1
0.7286	Intermediate Similarity	NPD7266	Discontinued
0.7285	Intermediate Similarity	NPD6234	Discontinued
0.728	Intermediate Similarity	NPD2234	Approved
0.728	Intermediate Similarity	NPD2229	Approved
0.728	Intermediate Similarity	NPD2228	Approved
0.7279	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5310	Approved
0.7273	Intermediate Similarity	NPD3134	Approved
0.7273	Intermediate Similarity	NPD5311	Approved
0.7273	Intermediate Similarity	NPD8651	Approved
0.7273	Intermediate Similarity	NPD7124	Phase 2
0.7259	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD8166	Discontinued
0.7254	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2801	Approved
0.7248	Intermediate Similarity	NPD2977	Approved
0.7248	Intermediate Similarity	NPD2978	Approved
0.7246	Intermediate Similarity	NPD6353	Approved
0.7246	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3596	Phase 2
0.7236	Intermediate Similarity	NPD4750	Phase 3
0.7236	Intermediate Similarity	NPD1792	Phase 2
0.7234	Intermediate Similarity	NPD7037	Approved
0.7227	Intermediate Similarity	NPD291	Approved
0.7219	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7831	Phase 2
0.7219	Intermediate Similarity	NPD7833	Phase 2
0.7218	Intermediate Similarity	NPD3094	Phase 2
0.7218	Intermediate Similarity	NPD987	Approved
0.7218	Intermediate Similarity	NPD2797	Approved
0.7217	Intermediate Similarity	NPD845	Approved
0.7214	Intermediate Similarity	NPD2935	Discontinued
0.7213	Intermediate Similarity	NPD1358	Approved
0.7209	Intermediate Similarity	NPD4093	Discontinued
0.7206	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4538	Approved
0.7194	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4536	Approved
0.7194	Intermediate Similarity	NPD6111	Discontinued
0.7183	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD37	Approved
0.7172	Intermediate Similarity	NPD4123	Phase 3
0.7165	Intermediate Similarity	NPD6387	Discontinued
0.7163	Intermediate Similarity	NPD5762	Approved
0.7163	Intermediate Similarity	NPD1375	Discontinued
0.7163	Intermediate Similarity	NPD3540	Phase 1
0.7163	Intermediate Similarity	NPD5763	Approved
0.7162	Intermediate Similarity	NPD7028	Phase 2
0.7154	Intermediate Similarity	NPD2932	Approved
0.7154	Intermediate Similarity	NPD4059	Approved
0.7154	Intermediate Similarity	NPD3019	Approved
0.7154	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD4062	Phase 3
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD4108	Discontinued
0.7133	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4628	Phase 3
0.7132	Intermediate Similarity	NPD6580	Approved
0.7132	Intermediate Similarity	NPD1894	Discontinued
0.7132	Intermediate Similarity	NPD1182	Approved
0.7132	Intermediate Similarity	NPD6581	Approved
0.7131	Intermediate Similarity	NPD1444	Approved
0.7131	Intermediate Similarity	NPD1445	Approved
0.7123	Intermediate Similarity	NPD52	Approved
0.7123	Intermediate Similarity	NPD7526	Approved
0.7123	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6653	Approved
0.7121	Intermediate Similarity	NPD1840	Phase 2
0.7121	Intermediate Similarity	NPD3972	Approved
0.7117	Intermediate Similarity	NPD111	Approved
0.7113	Intermediate Similarity	NPD5958	Discontinued
0.7113	Intermediate Similarity	NPD4534	Discontinued
0.7113	Intermediate Similarity	NPD7153	Discontinued

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