NPASS Compound

Structure

NPC9067 OpenBabel07101718242D 24 26 0 0 1 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 0.0000 -3.0000 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 -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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 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 -0.8660 -1.5000 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 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 -0.0000 -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 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -3.4641 1.0000 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 11 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 12 2 1 1 0 0 0 12 20 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 13 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	345.512
LogP:	3.987
LogD:	3.65
LogS:	-3.931
# Rotatable Bonds:	3
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.883
Synthetic Accessibility Score:	3.345
Fsp3:	0.3
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:	-4.918
MDCK Permeability:	1.4096530321694445e-05
Pgp-inhibitor:	0.254
Pgp-substrate:	0.663
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	98.0995101928711%
Volume Distribution (VD):	0.867
Pgp-substrate:	2.475733757019043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.474
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.634
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.807
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.389
CYP2D6-substrate:	0.71
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.849

ADMET: Excretion

Clearance (CL):	10.27
Half-life (T1/2):	0.601

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.399
Drug-inuced Liver Injury (DILI):	0.778
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.929
Carcinogencity:	0.137
Eye Corrosion:	0.004
Eye Irritation:	0.561
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC9067

Natural Product ID:	NPC9067
*Common Name:**	4',5-O-Didemethylcyclogalgravin
IUPAC Name:	(5R,6S)-5-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6-dihydronaphthalen-2-ol
Synonyms:
Standard InCHIKey:	HUMKWBMQEFNYGB-MPBGBICISA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-11-7-14-8-17(22)19(24-4)10-15(14)20(12(11)2)13-5-6-16(21)18(9-13)23-3/h5-10,12,20-22H,1-4H3/t12-,20-/m1/s1
SMILES:	COc1cc(ccc1O)[C@H]1[C@H](C)C(=Cc2c1cc(OC)c(c2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3290510
PubChem CID:	50900853
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO19979	Schisandra glaucescens	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[23373215]
NPO19979	Schisandra glaucescens	Species	Schisandraceae	Eukaryota	fruit	n.a.	n.a.	PMID[24927000]
NPO19979	Schisandra glaucescens	Species	Schisandraceae	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	2
Others	4

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	37460.0	nM	PMID[498522]
NPT1	Others	Radical scavenging activity		IC50	=	83390.0	nM	PMID[498522]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	58.6	%	PMID[498522]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	60.7	%	PMID[498522]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	62.1	%	PMID[498522]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	65.2	%	PMID[498522]

☑ 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 NPC9067 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	341
0.1-0.2	1614
0.2-0.3	4248
0.3-0.4	13012
0.4-0.5	5260
0.5-0.6	5314
0.6-0.7	8533
0.7-0.8	3282
0.8-0.85	694
0.85-0.9	340
0.9-0.95	41
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9832	High Similarity	NPC266705
0.9832	High Similarity	NPC228771
0.9832	High Similarity	NPC29008
0.9746	High Similarity	NPC30462
0.959	High Similarity	NPC277458
0.959	High Similarity	NPC307050
0.9492	High Similarity	NPC227217
0.9492	High Similarity	NPC232316
0.9492	High Similarity	NPC242885
0.9492	High Similarity	NPC117780
0.9492	High Similarity	NPC95614
0.9492	High Similarity	NPC165133
0.9492	High Similarity	NPC56214
0.9407	High Similarity	NPC310338
0.9407	High Similarity	NPC281298
0.9333	High Similarity	NPC160380
0.9333	High Similarity	NPC38996
0.9322	High Similarity	NPC470626
0.9286	High Similarity	NPC227002
0.9256	High Similarity	NPC85488
0.9237	High Similarity	NPC293619
0.918	High Similarity	NPC31344
0.918	High Similarity	NPC280704
0.918	High Similarity	NPC317769
0.9141	High Similarity	NPC311256
0.9141	High Similarity	NPC471942
0.9141	High Similarity	NPC209199
0.9134	High Similarity	NPC14224
0.9134	High Similarity	NPC161958
0.9091	High Similarity	NPC207613
0.907	High Similarity	NPC313081
0.9068	High Similarity	NPC47194
0.904	High Similarity	NPC106511
0.9032	High Similarity	NPC148627
0.9016	High Similarity	NPC54872
0.9016	High Similarity	NPC470212
0.9016	High Similarity	NPC324571
0.9016	High Similarity	NPC262156
0.9016	High Similarity	NPC473853
0.9016	High Similarity	NPC343720
0.9016	High Similarity	NPC113865
0.9016	High Similarity	NPC312675
0.9016	High Similarity	NPC184651
0.9	High Similarity	NPC474040
0.8984	High Similarity	NPC228843
0.8968	High Similarity	NPC201069
0.896	High Similarity	NPC274356
0.8923	High Similarity	NPC10314
0.8923	High Similarity	NPC108198
0.8923	High Similarity	NPC294884
0.8923	High Similarity	NPC69029
0.8923	High Similarity	NPC158142
0.8923	High Similarity	NPC200557
0.8898	High Similarity	NPC165106
0.8889	High Similarity	NPC5428
0.8889	High Similarity	NPC127587
0.8889	High Similarity	NPC165045
0.8889	High Similarity	NPC118533
0.8889	High Similarity	NPC21563
0.8872	High Similarity	NPC78987
0.8872	High Similarity	NPC82336
0.8871	High Similarity	NPC471693
0.8864	High Similarity	NPC184613
0.8855	High Similarity	NPC143139
0.8855	High Similarity	NPC202846
0.8846	High Similarity	NPC125649
0.8846	High Similarity	NPC141023
0.8837	High Similarity	NPC321502
0.8828	High Similarity	NPC126836
0.8819	High Similarity	NPC184733
0.8819	High Similarity	NPC21867
0.8819	High Similarity	NPC282703
0.8819	High Similarity	NPC45774
0.8819	High Similarity	NPC11258
0.8819	High Similarity	NPC129570
0.8819	High Similarity	NPC23012
0.8819	High Similarity	NPC128208
0.881	High Similarity	NPC76451
0.881	High Similarity	NPC17837
0.881	High Similarity	NPC304630
0.8788	High Similarity	NPC56329
0.8788	High Similarity	NPC242715
0.8779	High Similarity	NPC241241
0.877	High Similarity	NPC24474
0.877	High Similarity	NPC311595
0.876	High Similarity	NPC164386
0.876	High Similarity	NPC86947
0.875	High Similarity	NPC475815
0.875	High Similarity	NPC475875
0.875	High Similarity	NPC473264
0.8731	High Similarity	NPC29599
0.873	High Similarity	NPC233410
0.873	High Similarity	NPC53305
0.873	High Similarity	NPC472093
0.873	High Similarity	NPC17348
0.873	High Similarity	NPC193544
0.873	High Similarity	NPC257589
0.873	High Similarity	NPC117214
0.873	High Similarity	NPC208950
0.873	High Similarity	NPC203133
0.873	High Similarity	NPC298757
0.873	High Similarity	NPC116907
0.873	High Similarity	NPC221077
0.873	High Similarity	NPC57490
0.873	High Similarity	NPC251855
0.873	High Similarity	NPC17943
0.873	High Similarity	NPC475169
0.8729	High Similarity	NPC156840
0.8729	High Similarity	NPC257124
0.8729	High Similarity	NPC8547
0.8729	High Similarity	NPC173746
0.8722	High Similarity	NPC114171
0.8722	High Similarity	NPC243996
0.8722	High Similarity	NPC79622
0.8722	High Similarity	NPC230124
0.8722	High Similarity	NPC132804
0.8722	High Similarity	NPC275061
0.8722	High Similarity	NPC212942
0.8722	High Similarity	NPC6300
0.8722	High Similarity	NPC220344
0.8722	High Similarity	NPC29868
0.872	High Similarity	NPC197757
0.872	High Similarity	NPC228922
0.872	High Similarity	NPC249788
0.8712	High Similarity	NPC30632
0.871	High Similarity	NPC127389
0.871	High Similarity	NPC290451
0.8702	High Similarity	NPC160697
0.8699	High Similarity	NPC103916
0.8692	High Similarity	NPC189482
0.8692	High Similarity	NPC73656
0.8689	High Similarity	NPC474214
0.8682	High Similarity	NPC257582
0.8682	High Similarity	NPC92164
0.8682	High Similarity	NPC77040
0.8682	High Similarity	NPC241522
0.8682	High Similarity	NPC242807
0.8682	High Similarity	NPC174495
0.8682	High Similarity	NPC275950
0.8682	High Similarity	NPC181079
0.8682	High Similarity	NPC64201
0.8682	High Similarity	NPC143483
0.8682	High Similarity	NPC173308
0.8682	High Similarity	NPC187998
0.8682	High Similarity	NPC153739
0.8682	High Similarity	NPC145305
0.8682	High Similarity	NPC42300
0.8678	High Similarity	NPC9341
0.8678	High Similarity	NPC81067
0.8672	High Similarity	NPC252307
0.8672	High Similarity	NPC472968
0.8672	High Similarity	NPC245826
0.8672	High Similarity	NPC474178
0.8661	High Similarity	NPC127937
0.8661	High Similarity	NPC92207
0.8657	High Similarity	NPC308768
0.8657	High Similarity	NPC12668
0.8647	High Similarity	NPC230919
0.8647	High Similarity	NPC22902
0.8647	High Similarity	NPC200935
0.8647	High Similarity	NPC266453
0.864	High Similarity	NPC41562
0.8636	High Similarity	NPC252343
0.8629	High Similarity	NPC60962
0.8629	High Similarity	NPC14007
0.8629	High Similarity	NPC109083
0.8629	High Similarity	NPC224814
0.8629	High Similarity	NPC189844
0.8629	High Similarity	NPC269843
0.8626	High Similarity	NPC227719
0.8626	High Similarity	NPC32778
0.8618	High Similarity	NPC474320
0.8615	High Similarity	NPC40432
0.8615	High Similarity	NPC158079
0.8615	High Similarity	NPC15543
0.8615	High Similarity	NPC277804
0.8615	High Similarity	NPC7171
0.8615	High Similarity	NPC115207
0.8615	High Similarity	NPC232275
0.8615	High Similarity	NPC161557
0.8615	High Similarity	NPC27843
0.8615	High Similarity	NPC474017
0.8615	High Similarity	NPC228346
0.8615	High Similarity	NPC476345
0.8603	High Similarity	NPC192597
0.8603	High Similarity	NPC229218
0.8603	High Similarity	NPC176030
0.8603	High Similarity	NPC141817
0.8603	High Similarity	NPC169214
0.8594	High Similarity	NPC74817
0.8594	High Similarity	NPC282000
0.8594	High Similarity	NPC293054
0.8594	High Similarity	NPC246620
0.8594	High Similarity	NPC252131
0.8594	High Similarity	NPC82679
0.8594	High Similarity	NPC324112
0.8594	High Similarity	NPC159968
0.8594	High Similarity	NPC177167
0.8594	High Similarity	NPC236791
0.8594	High Similarity	NPC124452

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 NPC9067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	993
0.2-0.3	1399
0.3-0.4	2729
0.4-0.5	1836
0.5-0.6	1009
0.6-0.7	679
0.7-0.8	175
0.8-0.85	8
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8898	High Similarity	NPD5283	Phase 1
0.8837	High Similarity	NPD3619	Clinical (unspecified phase)
0.8837	High Similarity	NPD3620	Phase 2
0.8729	High Similarity	NPD228	Approved
0.8559	High Similarity	NPD3022	Approved
0.8559	High Similarity	NPD3021	Approved
0.8462	Intermediate Similarity	NPD3027	Phase 3
0.8425	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD4060	Phase 1
0.7985	Intermediate Similarity	NPD5110	Phase 2
0.7985	Intermediate Similarity	NPD5111	Phase 2
0.7985	Intermediate Similarity	NPD5109	Approved
0.797	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD4624	Approved
0.7941	Intermediate Similarity	NPD3657	Discovery
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD5536	Phase 2
0.7868	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD4626	Approved
0.781	Intermediate Similarity	NPD5735	Approved
0.7803	Intermediate Similarity	NPD1283	Approved
0.7797	Intermediate Similarity	NPD3020	Approved
0.7752	Intermediate Similarity	NPD1651	Approved
0.7727	Intermediate Similarity	NPD5327	Phase 3
0.7724	Intermediate Similarity	NPD2684	Approved
0.7717	Intermediate Similarity	NPD7157	Approved
0.771	Intermediate Similarity	NPD3092	Approved
0.771	Intermediate Similarity	NPD3705	Approved
0.7676	Intermediate Similarity	NPD6674	Discontinued
0.7674	Intermediate Similarity	NPD3091	Approved
0.7664	Intermediate Similarity	NPD2674	Phase 3
0.7647	Intermediate Similarity	NPD4625	Phase 3
0.7647	Intermediate Similarity	NPD7095	Approved
0.7632	Intermediate Similarity	NPD6234	Discontinued
0.763	Intermediate Similarity	NPD2861	Phase 2
0.7626	Intermediate Similarity	NPD4097	Suspended
0.7622	Intermediate Similarity	NPD6331	Phase 2
0.7622	Intermediate Similarity	NPD8166	Discontinued
0.7619	Intermediate Similarity	NPD7843	Approved
0.7615	Intermediate Similarity	NPD1357	Approved
0.7612	Intermediate Similarity	NPD3094	Phase 2
0.7609	Intermediate Similarity	NPD4140	Approved
0.7609	Intermediate Similarity	NPD1558	Phase 1
0.7594	Intermediate Similarity	NPD2982	Phase 2
0.7594	Intermediate Similarity	NPD1669	Approved
0.7594	Intermediate Similarity	NPD2983	Phase 2
0.7591	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD3145	Approved
0.7591	Intermediate Similarity	NPD3144	Approved
0.7576	Intermediate Similarity	NPD1281	Approved
0.7574	Intermediate Similarity	NPD4908	Phase 1
0.7569	Intermediate Similarity	NPD5241	Discontinued
0.7557	Intermediate Similarity	NPD2932	Approved
0.7556	Intermediate Similarity	NPD6584	Phase 3
0.7552	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD2860	Approved
0.7542	Intermediate Similarity	NPD2859	Approved
0.7533	Intermediate Similarity	NPD37	Approved
0.752	Intermediate Similarity	NPD5451	Approved
0.7519	Intermediate Similarity	NPD2230	Approved
0.7519	Intermediate Similarity	NPD2233	Approved
0.7519	Intermediate Similarity	NPD2232	Approved
0.7519	Intermediate Similarity	NPD2981	Phase 2
0.7517	Intermediate Similarity	NPD7028	Phase 2
0.75	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6353	Approved
0.75	Intermediate Similarity	NPD3018	Phase 2
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7037	Approved
0.7481	Intermediate Similarity	NPD5691	Approved
0.748	Intermediate Similarity	NPD7635	Approved
0.7463	Intermediate Similarity	NPD4749	Approved
0.7458	Intermediate Similarity	NPD2934	Approved
0.7458	Intermediate Similarity	NPD9296	Approved
0.7458	Intermediate Similarity	NPD2933	Approved
0.7451	Intermediate Similarity	NPD7831	Phase 2
0.7451	Intermediate Similarity	NPD7833	Phase 2
0.7451	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6896	Approved
0.7447	Intermediate Similarity	NPD6895	Approved
0.7444	Intermediate Similarity	NPD1610	Phase 2
0.7442	Intermediate Similarity	NPD6671	Approved
0.7431	Intermediate Similarity	NPD3060	Approved
0.7426	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD2667	Approved
0.7424	Intermediate Similarity	NPD3095	Discontinued
0.7424	Intermediate Similarity	NPD5846	Approved
0.7424	Intermediate Similarity	NPD4059	Approved
0.7424	Intermediate Similarity	NPD6516	Phase 2
0.7424	Intermediate Similarity	NPD2668	Approved
0.7424	Intermediate Similarity	NPD3019	Approved
0.7413	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5763	Approved
0.7413	Intermediate Similarity	NPD5762	Approved
0.7407	Intermediate Similarity	NPD8651	Approved
0.7394	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4108	Discontinued
0.7389	Intermediate Similarity	NPD27	Approved
0.7389	Intermediate Similarity	NPD2489	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7386	Intermediate Similarity	NPD4966	Approved
0.7379	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9494	Approved
0.736	Intermediate Similarity	NPD2342	Discontinued
0.7357	Intermediate Similarity	NPD2979	Phase 3
0.7348	Intermediate Similarity	NPD4093	Discontinued
0.7347	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7041	Phase 2
0.7344	Intermediate Similarity	NPD5535	Approved
0.7343	Intermediate Similarity	NPD2438	Suspended
0.7338	Intermediate Similarity	NPD5718	Phase 2
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6583	Phase 3
0.7333	Intermediate Similarity	NPD6582	Phase 2
0.7329	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5177	Phase 3
0.7308	Intermediate Similarity	NPD709	Approved
0.7305	Intermediate Similarity	NPD6355	Discontinued
0.7296	Intermediate Similarity	NPD7228	Approved
0.728	Intermediate Similarity	NPD968	Approved
0.7279	Intermediate Similarity	NPD2922	Phase 1
0.7261	Intermediate Similarity	NPD6232	Discontinued
0.7252	Intermediate Similarity	NPD7340	Approved
0.7246	Intermediate Similarity	NPD5736	Approved
0.7241	Intermediate Similarity	NPD2808	Discontinued
0.7239	Intermediate Similarity	NPD3847	Discontinued
0.7234	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7473	Discontinued
0.7222	Intermediate Similarity	NPD2161	Phase 2
0.7219	Intermediate Similarity	NPD4005	Discontinued
0.7215	Intermediate Similarity	NPD2969	Approved
0.7215	Intermediate Similarity	NPD2970	Approved
0.7214	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6798	Discontinued
0.7203	Intermediate Similarity	NPD4538	Approved
0.7203	Intermediate Similarity	NPD4536	Approved
0.7203	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4162	Approved
0.719	Intermediate Similarity	NPD288	Approved
0.719	Intermediate Similarity	NPD1934	Approved
0.7185	Intermediate Similarity	NPD1611	Approved
0.7181	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4584	Approved
0.7181	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7266	Discontinued
0.7167	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2286	Discontinued
0.7163	Intermediate Similarity	NPD8032	Phase 2
0.7154	Intermediate Similarity	NPD1398	Phase 1
0.7154	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6696	Suspended
0.7152	Intermediate Similarity	NPD4010	Discontinued
0.7143	Intermediate Similarity	NPD5929	Approved
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2801	Approved
0.7134	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3109	Approved
0.7113	Intermediate Similarity	NPD3110	Approved
0.7113	Intermediate Similarity	NPD2238	Phase 2
0.7109	Intermediate Similarity	NPD4750	Phase 3
0.7107	Intermediate Similarity	NPD844	Approved
0.7103	Intermediate Similarity	NPD2531	Phase 2
0.7103	Intermediate Similarity	NPD2935	Discontinued
0.7092	Intermediate Similarity	NPD1039	Discontinued
0.7089	Intermediate Similarity	NPD7199	Phase 2
0.7087	Intermediate Similarity	NPD290	Approved
0.7075	Intermediate Similarity	NPD4236	Phase 3
0.7075	Intermediate Similarity	NPD4237	Approved
0.7063	Intermediate Similarity	NPD2898	Approved
0.7047	Intermediate Similarity	NPD7124	Phase 2
0.7045	Intermediate Similarity	NPD6387	Discontinued
0.7044	Intermediate Similarity	NPD3051	Approved
0.7042	Intermediate Similarity	NPD6233	Phase 2
0.7042	Intermediate Similarity	NPD6663	Approved
0.7042	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1751	Approved
0.7034	Intermediate Similarity	NPD5588	Approved
0.7034	Intermediate Similarity	NPD5960	Phase 3
0.7032	Intermediate Similarity	NPD2978	Approved
0.7032	Intermediate Similarity	NPD2977	Approved
0.703	Intermediate Similarity	NPD7310	Approved
0.703	Intermediate Similarity	NPD7311	Approved
0.703	Intermediate Similarity	NPD7312	Approved
0.703	Intermediate Similarity	NPD7313	Approved
0.7029	Intermediate Similarity	NPD1876	Approved
0.7027	Intermediate Similarity	NPD4628	Phase 3

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