NPASS Compound

Structure

CID228771 OpenBabel06191716022D 25 27 0 0 1 0 0 0 0 0999 V2000 2.5981 -4.5000 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 -2.5981 -0.5000 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 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 -3.0000 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 -0.5000 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 2.5981 -3.5000 0.0000 C 0 0 2 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 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 2.5981 -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 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 13 2 1 1 0 0 0 13 21 1 0 0 0 0 15 16 1 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 20 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.18
Volume:	365.445
LogP:	4.687
LogD:	4.423
LogS:	-5.425
# Rotatable Bonds:	4
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.896
Synthetic Accessibility Score:	3.262
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.846
MDCK Permeability:	1.6991072698147036e-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.781

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	98.17959594726562%
Volume Distribution (VD):	1.071
Pgp-substrate:	2.0681228637695312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.189
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.783
CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.863
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	9.716
Half-life (T1/2):	0.516

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.87
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.081
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.092
Respiratory Toxicity:	0.397

Download Data

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

Natural Product: NPC228771

Natural Product ID:	NPC228771
*Common Name:**	(8R,7'r,8R)-5-Hydroxy-4,3',4'-Trimethoxy-2,7'-Cyclolignan
IUPAC Name:	(5R,6R,7R)-5-(3,4-dimethoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
Synonyms:
Standard InCHIKey:	PLNZSVOTOMAFQW-SQHYZVFZSA-N
Standard InCHI:	InChI=1S/C21H26O4/c1-12-8-15-9-17(22)19(24-4)11-16(15)21(13(12)2)14-6-7-18(23-3)20(10-14)25-5/h6-7,9-13,21-22H,8H2,1-5H3/t12-,13-,21-/m1/s1
SMILES:	COc1cc(ccc1OC)[C@H]1[C@H](C)[C@H](C)Cc2c1cc(OC)c(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564817
PubChem CID:	45269248
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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	30000.0	nM	PMID[546200]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	4500.0	nM	PMID[546200]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	6.7	n.a.	PMID[546200]

☑ 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 NPC228771 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	354
0.1-0.2	1672
0.2-0.3	3957
0.3-0.4	12541
0.4-0.5	6012
0.5-0.6	5234
0.6-0.7	8593
0.7-0.8	3315
0.8-0.85	706
0.85-0.9	258
0.9-0.95	42
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC29008
1.0	High Similarity	NPC266705
0.9832	High Similarity	NPC9067
0.9752	High Similarity	NPC307050
0.9752	High Similarity	NPC277458
0.958	High Similarity	NPC30462
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
0.944	High Similarity	NPC227002
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
0.9291	High Similarity	NPC311256
0.9291	High Similarity	NPC471942
0.9286	High Similarity	NPC14224
0.9286	High Similarity	NPC161958
0.9256	High Similarity	NPC85488
0.9237	High Similarity	NPC293619
0.9219	High Similarity	NPC313081
0.918	High Similarity	NPC317769
0.918	High Similarity	NPC31344
0.918	High Similarity	NPC280704
0.9134	High Similarity	NPC228843
0.912	High Similarity	NPC201069
0.9091	High Similarity	NPC207613
0.907	High Similarity	NPC108198
0.907	High Similarity	NPC294884
0.907	High Similarity	NPC10314
0.907	High Similarity	NPC69029
0.907	High Similarity	NPC158142
0.907	High Similarity	NPC200557
0.904	High Similarity	NPC106511
0.9032	High Similarity	NPC148627
0.9016	High Similarity	NPC54872
0.9016	High Similarity	NPC184651
0.9016	High Similarity	NPC470212
0.9016	High Similarity	NPC324571
0.9016	High Similarity	NPC262156
0.9016	High Similarity	NPC473853
0.9016	High Similarity	NPC312675
0.9016	High Similarity	NPC343720
0.9016	High Similarity	NPC113865
0.9008	High Similarity	NPC184613
0.9	High Similarity	NPC202846
0.9	High Similarity	NPC474040
0.9	High Similarity	NPC143139
0.8992	High Similarity	NPC141023
0.8992	High Similarity	NPC125649
0.8992	High Similarity	NPC209199
0.8984	High Similarity	NPC321502
0.896	High Similarity	NPC274356
0.896	High Similarity	NPC17837
0.896	High Similarity	NPC304630
0.8931	High Similarity	NPC56329
0.8931	High Similarity	NPC242715
0.8923	High Similarity	NPC241241
0.8908	High Similarity	NPC47194
0.8898	High Similarity	NPC165106
0.8889	High Similarity	NPC5428
0.8889	High Similarity	NPC165045
0.8889	High Similarity	NPC127587
0.8889	High Similarity	NPC118533
0.8889	High Similarity	NPC21563
0.888	High Similarity	NPC17348
0.8872	High Similarity	NPC29599
0.8871	High Similarity	NPC471693
0.8864	High Similarity	NPC275061
0.8864	High Similarity	NPC29868
0.8864	High Similarity	NPC230124
0.8864	High Similarity	NPC212942
0.8864	High Similarity	NPC6300
0.8864	High Similarity	NPC220344
0.8864	High Similarity	NPC79622
0.8864	High Similarity	NPC114171
0.8864	High Similarity	NPC243996
0.8864	High Similarity	NPC132804
0.8855	High Similarity	NPC30632
0.8852	High Similarity	NPC103916
0.8846	High Similarity	NPC160697
0.8837	High Similarity	NPC189482
0.8837	High Similarity	NPC73656
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	NPC128208
0.8819	High Similarity	NPC129570
0.8819	High Similarity	NPC23012
0.881	High Similarity	NPC76451
0.8797	High Similarity	NPC12668
0.8797	High Similarity	NPC308768
0.8788	High Similarity	NPC230919
0.8788	High Similarity	NPC22902
0.8788	High Similarity	NPC266453
0.8788	High Similarity	NPC200935
0.8779	High Similarity	NPC252343
0.877	High Similarity	NPC24474
0.877	High Similarity	NPC311595
0.8769	High Similarity	NPC227719
0.876	High Similarity	NPC86947
0.876	High Similarity	NPC164386
0.875	High Similarity	NPC475815
0.875	High Similarity	NPC475875
0.875	High Similarity	NPC473264
0.8741	High Similarity	NPC192597
0.8741	High Similarity	NPC229218
0.8741	High Similarity	NPC141817
0.8741	High Similarity	NPC169214
0.8741	High Similarity	NPC176030
0.874	High Similarity	NPC177167
0.8731	High Similarity	NPC82336
0.8731	High Similarity	NPC78987
0.873	High Similarity	NPC233410
0.873	High Similarity	NPC53305
0.873	High Similarity	NPC203133
0.873	High Similarity	NPC472093
0.873	High Similarity	NPC193544
0.873	High Similarity	NPC257589
0.873	High Similarity	NPC117214
0.873	High Similarity	NPC208950
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	NPC298757
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	NPC243759
0.8722	High Similarity	NPC105847
0.8722	High Similarity	NPC132723
0.8722	High Similarity	NPC76032
0.8722	High Similarity	NPC218131
0.872	High Similarity	NPC197757
0.872	High Similarity	NPC228922
0.872	High Similarity	NPC249788
0.8712	High Similarity	NPC68292
0.8712	High Similarity	NPC205442
0.871	High Similarity	NPC127389
0.871	High Similarity	NPC290451
0.8692	High Similarity	NPC303144
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	NPC174495
0.8682	High Similarity	NPC275950
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	NPC181079
0.8682	High Similarity	NPC242807
0.8682	High Similarity	NPC42300
0.8678	High Similarity	NPC9341
0.8678	High Similarity	NPC81067
0.8676	High Similarity	NPC253015
0.8676	High Similarity	NPC471065
0.8672	High Similarity	NPC252307
0.8672	High Similarity	NPC472968
0.8672	High Similarity	NPC245826
0.8672	High Similarity	NPC474178
0.8667	High Similarity	NPC191231
0.8667	High Similarity	NPC175838
0.8667	High Similarity	NPC183709
0.8661	High Similarity	NPC127937
0.8661	High Similarity	NPC156854
0.8661	High Similarity	NPC92207
0.8661	High Similarity	NPC134431
0.8647	High Similarity	NPC266006
0.8647	High Similarity	NPC151656
0.864	High Similarity	NPC41562
0.8629	High Similarity	NPC60962
0.8629	High Similarity	NPC109083
0.8629	High Similarity	NPC224814
0.8629	High Similarity	NPC189844
0.8629	High Similarity	NPC14007
0.8629	High Similarity	NPC269843
0.8626	High Similarity	NPC32778
0.8618	High Similarity	NPC474320
0.8615	High Similarity	NPC40432
0.8615	High Similarity	NPC232275
0.8615	High Similarity	NPC158079
0.8615	High Similarity	NPC15543
0.8615	High Similarity	NPC277804

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 NPC228771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	989
0.2-0.3	1377
0.3-0.4	2772
0.4-0.5	1810
0.5-0.6	1013
0.6-0.7	675
0.7-0.8	167
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8984	High Similarity	NPD3619	Clinical (unspecified phase)
0.8984	High Similarity	NPD3620	Phase 2
0.8898	High Similarity	NPD5283	Phase 1
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
0.8092	Intermediate Similarity	NPD4624	Approved
0.8074	Intermediate Similarity	NPD3657	Discovery
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)
0.7941	Intermediate Similarity	NPD5735	Approved
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
0.7863	Intermediate Similarity	NPD5327	Phase 3
0.7846	Intermediate Similarity	NPD3092	Approved
0.7829	Intermediate Similarity	NPD4626	Approved
0.7812	Intermediate Similarity	NPD3091	Approved
0.7803	Intermediate Similarity	NPD1283	Approved
0.7801	Intermediate Similarity	NPD6674	Discontinued
0.7797	Intermediate Similarity	NPD3020	Approved
0.7778	Intermediate Similarity	NPD7095	Approved
0.7754	Intermediate Similarity	NPD4097	Suspended
0.7752	Intermediate Similarity	NPD1651	Approved
0.7748	Intermediate Similarity	NPD6234	Discontinued
0.7744	Intermediate Similarity	NPD3094	Phase 2
0.7737	Intermediate Similarity	NPD4140	Approved
0.7724	Intermediate Similarity	NPD2684	Approved
0.7721	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7157	Approved
0.771	Intermediate Similarity	NPD3705	Approved
0.7704	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD5241	Discontinued
0.7687	Intermediate Similarity	NPD6584	Phase 3
0.7664	Intermediate Similarity	NPD2674	Phase 3
0.7661	Intermediate Similarity	NPD5451	Approved
0.7651	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD4625	Phase 3
0.763	Intermediate Similarity	NPD2861	Phase 2
0.7626	Intermediate Similarity	NPD6353	Approved
0.7626	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
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
0.7609	Intermediate Similarity	NPD1558	Phase 1
0.7606	Intermediate Similarity	NPD7037	Approved
0.7594	Intermediate Similarity	NPD1669	Approved
0.7594	Intermediate Similarity	NPD2982	Phase 2
0.7594	Intermediate Similarity	NPD2983	Phase 2
0.7591	Intermediate Similarity	NPD3145	Approved
0.7591	Intermediate Similarity	NPD3144	Approved
0.7576	Intermediate Similarity	NPD1281	Approved
0.7566	Intermediate Similarity	NPD7831	Phase 2
0.7566	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7833	Phase 2
0.7557	Intermediate Similarity	NPD3095	Discontinued
0.7557	Intermediate Similarity	NPD6516	Phase 2
0.7557	Intermediate Similarity	NPD5846	Approved
0.7557	Intermediate Similarity	NPD4059	Approved
0.7557	Intermediate Similarity	NPD3019	Approved
0.7552	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD2860	Approved
0.7542	Intermediate Similarity	NPD2859	Approved
0.7519	Intermediate Similarity	NPD2233	Approved
0.7519	Intermediate Similarity	NPD2230	Approved
0.7519	Intermediate Similarity	NPD2232	Approved
0.7519	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD3018	Phase 2
0.75	Intermediate Similarity	NPD2342	Discontinued
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD4093	Discontinued
0.7481	Intermediate Similarity	NPD5691	Approved
0.748	Intermediate Similarity	NPD5535	Approved
0.748	Intermediate Similarity	NPD7635	Approved
0.7466	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7041	Phase 2
0.7464	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD6582	Phase 2
0.7463	Intermediate Similarity	NPD6583	Phase 3
0.7458	Intermediate Similarity	NPD2934	Approved
0.7458	Intermediate Similarity	NPD9296	Approved
0.7458	Intermediate Similarity	NPD2933	Approved
0.7448	Intermediate Similarity	NPD5084	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
0.7424	Intermediate Similarity	NPD2932	Approved
0.7424	Intermediate Similarity	NPD2667	Approved
0.7424	Intermediate Similarity	NPD2668	Approved
0.7413	Intermediate Similarity	NPD5763	Approved
0.7413	Intermediate Similarity	NPD5762	Approved
0.7413	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7228	Approved
0.74	Intermediate Similarity	NPD7028	Phase 2
0.7394	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4108	Discontinued
0.7379	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9494	Approved
0.7372	Intermediate Similarity	NPD5736	Approved
0.7372	Intermediate Similarity	NPD6232	Discontinued
0.7357	Intermediate Similarity	NPD2979	Phase 3
0.7357	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2438	Suspended
0.7342	Intermediate Similarity	NPD7473	Discontinued
0.7338	Intermediate Similarity	NPD6798	Discontinued
0.7338	Intermediate Similarity	NPD5718	Phase 2
0.7333	Intermediate Similarity	NPD4749	Approved
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
0.7299	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2286	Discontinued
0.7286	Intermediate Similarity	NPD8032	Phase 2
0.728	Intermediate Similarity	NPD968	Approved
0.7279	Intermediate Similarity	NPD8651	Approved
0.7279	Intermediate Similarity	NPD2922	Phase 1
0.7278	Intermediate Similarity	NPD27	Approved
0.7278	Intermediate Similarity	NPD2489	Approved
0.726	Intermediate Similarity	NPD7003	Approved
0.7252	Intermediate Similarity	NPD7340	Approved
0.7241	Intermediate Similarity	NPD2808	Discontinued
0.7239	Intermediate Similarity	NPD3847	Discontinued
0.7234	Intermediate Similarity	NPD3110	Approved
0.7234	Intermediate Similarity	NPD3109	Approved
0.7222	Intermediate Similarity	NPD2161	Phase 2
0.7219	Intermediate Similarity	NPD4005	Discontinued
0.7214	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4538	Approved
0.7203	Intermediate Similarity	NPD4536	Approved
0.7203	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7199	Phase 2
0.7192	Intermediate Similarity	NPD4162	Approved
0.719	Intermediate Similarity	NPD1934	Approved
0.719	Intermediate Similarity	NPD288	Approved
0.7185	Intermediate Similarity	NPD1611	Approved
0.7181	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4584	Approved
0.7172	Intermediate Similarity	NPD7266	Discontinued
0.7167	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6233	Phase 2
0.7163	Intermediate Similarity	NPD6663	Approved
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	NPD3051	Approved
0.7152	Intermediate Similarity	NPD4010	Discontinued
0.7143	Intermediate Similarity	NPD5929	Approved
0.7143	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2801	Approved
0.7133	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD2238	Phase 2
0.7111	Intermediate Similarity	NPD3023	Approved
0.7111	Intermediate Similarity	NPD3026	Approved
0.7107	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2969	Approved
0.7107	Intermediate Similarity	NPD844	Approved
0.7107	Intermediate Similarity	NPD2970	Approved
0.7103	Intermediate Similarity	NPD2531	Phase 2
0.7103	Intermediate Similarity	NPD2935	Discontinued
0.7101	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3025	Approved
0.709	Intermediate Similarity	NPD3024	Approved
0.7089	Intermediate Similarity	NPD8127	Discontinued
0.7087	Intermediate Similarity	NPD290	Approved
0.7083	Intermediate Similarity	NPD7097	Phase 1
0.7075	Intermediate Similarity	NPD4236	Phase 3
0.7075	Intermediate Similarity	NPD4237	Approved
0.7067	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7124	Phase 2
0.7045	Intermediate Similarity	NPD6387	Discontinued
0.7042	Intermediate Similarity	NPD7265	Discontinued
0.7042	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1751	Approved
0.7037	Intermediate Similarity	NPD5844	Phase 1

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