NPASS Compound

Structure

NPC473221 OpenBabel07101719252D 31 33 0 0 0 0 0 0 0 0999 V2000 0.7183 1.0378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0661 -1.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7062 -2.1581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2957 -1.2935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2479 -2.4227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3746 -0.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2957 -0.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2044 -2.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0661 0.2298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7118 -2.3076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7062 0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2981 -1.9777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2479 0.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1448 -1.1838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0756 -0.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1560 -1.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3411 -0.6876 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5482 -0.1438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1560 -0.5056 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 -2.3385 -0.6157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2561 0.8126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 25 26 2 0 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.26
Volume:	466.584
LogP:	7.758
LogD:	4.734
LogS:	-3.427
# Rotatable Bonds:	1
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	3.948
Fsp3:	0.481
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.175
MDCK Permeability:	1.6970974684227258e-05
Pgp-inhibitor:	0.382
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	100.33246612548828%
Volume Distribution (VD):	3.2
Pgp-substrate:	0.5581995248794556%

ADMET: Metabolism

CYP1A2-inhibitor:	0.797
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.901
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.426
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.269
CYP3A4-substrate:	0.058

ADMET: Excretion

Clearance (CL):	3.095
Half-life (T1/2):	0.319

ADMET: Toxicity

hERG Blockers:	0.196
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.47
AMES Toxicity:	0.192
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.958
Carcinogencity:	0.02
Eye Corrosion:	0.004
Eye Irritation:	0.928
Respiratory Toxicity:	0.755

Download Data

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

Natural Product: NPC473221

Natural Product ID:	NPC473221
*Common Name:**	ZYGGJLPOXFHXPT-HWKANZROSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZYGGJLPOXFHXPT-HWKANZROSA-N
Standard InCHI:	InChI=1S/C27H36O4/c1-31-25-19-22(28)18-21-15-13-11-9-7-5-3-2-4-6-8-10-12-14-20-16-23(29)27(26(21)25)24(30)17-20/h3,5,16-19,28-30H,2,4,6-15H2,1H3/b5-3+
SMILES:	COc1cc(O)cc2c1c1c(O)cc(cc1O)CCCCCCC/C=C/CCCCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL373843
PubChem CID:	44419739
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8945	Grevillea robusta	Species	Proteaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	29300.0	nM	PMID[458380]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	27900.0	nM	PMID[458380]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	29100.0	nM	PMID[458380]

☑ 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 NPC473221 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	376
0.1-0.2	1676
0.2-0.3	4333
0.3-0.4	12840
0.4-0.5	5427
0.5-0.6	4102
0.6-0.7	7688
0.7-0.8	5003
0.8-0.85	783
0.85-0.9	380
0.9-0.95	84
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC82299
0.9508	High Similarity	NPC105031
0.9431	High Similarity	NPC170485
0.9417	High Similarity	NPC102639
0.935	High Similarity	NPC278955
0.935	High Similarity	NPC113495
0.935	High Similarity	NPC105718
0.928	High Similarity	NPC38017
0.928	High Similarity	NPC215300
0.9268	High Similarity	NPC228503
0.9268	High Similarity	NPC138248
0.9262	High Similarity	NPC18128
0.9262	High Similarity	NPC77789
0.925	High Similarity	NPC184302
0.9219	High Similarity	NPC469610
0.9213	High Similarity	NPC8899
0.9213	High Similarity	NPC282508
0.92	High Similarity	NPC53781
0.918	High Similarity	NPC476633
0.9167	High Similarity	NPC190514
0.9154	High Similarity	NPC206525
0.9154	High Similarity	NPC191462
0.9154	High Similarity	NPC472648
0.9154	High Similarity	NPC170328
0.9154	High Similarity	NPC472649
0.9154	High Similarity	NPC472647
0.9154	High Similarity	NPC133463
0.9141	High Similarity	NPC469611
0.9091	High Similarity	NPC273623
0.9084	High Similarity	NPC266006
0.9084	High Similarity	NPC472646
0.9084	High Similarity	NPC71465
0.9083	High Similarity	NPC474933
0.9083	High Similarity	NPC195466
0.9083	High Similarity	NPC244816
0.9083	High Similarity	NPC219070
0.9083	High Similarity	NPC127894
0.9083	High Similarity	NPC50521
0.9083	High Similarity	NPC69261
0.9083	High Similarity	NPC221549
0.9083	High Similarity	NPC470760
0.9083	High Similarity	NPC33270
0.9083	High Similarity	NPC15860
0.9083	High Similarity	NPC470759
0.9077	High Similarity	NPC258780
0.9077	High Similarity	NPC37410
0.9062	High Similarity	NPC15543
0.9062	High Similarity	NPC473309
0.9062	High Similarity	NPC471517
0.9062	High Similarity	NPC160623
0.9055	High Similarity	NPC471519
0.9055	High Similarity	NPC471518
0.9048	High Similarity	NPC46978
0.9008	High Similarity	NPC202846
0.9008	High Similarity	NPC143139
0.9008	High Similarity	NPC205442
0.9	High Similarity	NPC115808
0.9	High Similarity	NPC114064
0.9	High Similarity	NPC85292
0.9	High Similarity	NPC54507
0.9	High Similarity	NPC150624
0.9	High Similarity	NPC229147
0.9	High Similarity	NPC141090
0.9	High Similarity	NPC203113
0.8984	High Similarity	NPC126836
0.8984	High Similarity	NPC254000
0.8968	High Similarity	NPC223953
0.8947	High Similarity	NPC12668
0.8947	High Similarity	NPC308768
0.8939	High Similarity	NPC56329
0.8939	High Similarity	NPC242715
0.8939	High Similarity	NPC35550
0.8931	High Similarity	NPC158142
0.8931	High Similarity	NPC294884
0.8931	High Similarity	NPC200557
0.8931	High Similarity	NPC69029
0.8931	High Similarity	NPC111655
0.8931	High Similarity	NPC10314
0.8931	High Similarity	NPC108198
0.8923	High Similarity	NPC32778
0.8917	High Similarity	NPC167934
0.8917	High Similarity	NPC808
0.8917	High Similarity	NPC464
0.8917	High Similarity	NPC185541
0.8917	High Similarity	NPC53906
0.8915	High Similarity	NPC472590
0.8906	High Similarity	NPC16577
0.8889	High Similarity	NPC293801
0.8889	High Similarity	NPC105925
0.888	High Similarity	NPC474160
0.8872	High Similarity	NPC220344
0.8872	High Similarity	NPC132804
0.8872	High Similarity	NPC243996
0.8872	High Similarity	NPC218131
0.8872	High Similarity	NPC212942
0.8872	High Similarity	NPC243759
0.8872	High Similarity	NPC275061
0.8872	High Similarity	NPC29868
0.8872	High Similarity	NPC79622
0.8872	High Similarity	NPC105847
0.8864	High Similarity	NPC30632
0.8855	High Similarity	NPC188378
0.8855	High Similarity	NPC206737
0.8855	High Similarity	NPC555
0.8855	High Similarity	NPC289258
0.8855	High Similarity	NPC469659
0.8855	High Similarity	NPC7515
0.8855	High Similarity	NPC56764
0.8855	High Similarity	NPC125649
0.8855	High Similarity	NPC160697
0.8855	High Similarity	NPC276026
0.8852	High Similarity	NPC63010
0.8852	High Similarity	NPC131118
0.8846	High Similarity	NPC102256
0.8837	High Similarity	NPC192687
0.8837	High Similarity	NPC224157
0.8833	High Similarity	NPC228287
0.8833	High Similarity	NPC180508
0.8833	High Similarity	NPC276737
0.8833	High Similarity	NPC22610
0.8828	High Similarity	NPC154866
0.8819	High Similarity	NPC26879
0.8819	High Similarity	NPC230479
0.8819	High Similarity	NPC283049
0.8819	High Similarity	NPC50315
0.8815	High Similarity	NPC175838
0.881	High Similarity	NPC270030
0.88	High Similarity	NPC74137
0.8797	High Similarity	NPC266453
0.8797	High Similarity	NPC6262
0.8797	High Similarity	NPC90615
0.8797	High Similarity	NPC200935
0.8797	High Similarity	NPC151656
0.8797	High Similarity	NPC73535
0.8797	High Similarity	NPC230919
0.8797	High Similarity	NPC25111
0.8797	High Similarity	NPC22902
0.8797	High Similarity	NPC201145
0.8797	High Similarity	NPC272157
0.879	High Similarity	NPC277798
0.879	High Similarity	NPC129176
0.879	High Similarity	NPC100108
0.8788	High Similarity	NPC180602
0.8788	High Similarity	NPC55239
0.8788	High Similarity	NPC214853
0.8788	High Similarity	NPC313081
0.8788	High Similarity	NPC240279
0.8788	High Similarity	NPC241241
0.876	High Similarity	NPC93962
0.876	High Similarity	NPC190144
0.875	High Similarity	NPC74817
0.875	High Similarity	NPC246620
0.875	High Similarity	NPC82679
0.875	High Similarity	NPC124452
0.875	High Similarity	NPC266555
0.875	High Similarity	NPC236791
0.875	High Similarity	NPC324112
0.875	High Similarity	NPC236760
0.875	High Similarity	NPC293054
0.875	High Similarity	NPC169474
0.875	High Similarity	NPC282000
0.875	High Similarity	NPC159968
0.8741	High Similarity	NPC472089
0.8741	High Similarity	NPC265075
0.8731	High Similarity	NPC184613
0.8731	High Similarity	NPC471183
0.873	High Similarity	NPC282496
0.873	High Similarity	NPC233526
0.873	High Similarity	NPC136319
0.873	High Similarity	NPC84086
0.8722	High Similarity	NPC114155
0.8722	High Similarity	NPC133025
0.8722	High Similarity	NPC234952
0.8722	High Similarity	NPC476639
0.8722	High Similarity	NPC300846
0.8712	High Similarity	NPC209199
0.8712	High Similarity	NPC473107
0.8702	High Similarity	NPC6451
0.8702	High Similarity	NPC218884
0.8692	High Similarity	NPC51840
0.8692	High Similarity	NPC299221
0.8692	High Similarity	NPC311680
0.8692	High Similarity	NPC234488
0.8686	High Similarity	NPC473845
0.8682	High Similarity	NPC149008
0.8682	High Similarity	NPC283114
0.8682	High Similarity	NPC53986
0.8682	High Similarity	NPC38664
0.8682	High Similarity	NPC207702
0.8676	High Similarity	NPC470917
0.8676	High Similarity	NPC472088
0.8676	High Similarity	NPC183709
0.8676	High Similarity	NPC472087
0.8672	High Similarity	NPC78974
0.8672	High Similarity	NPC223136
0.8672	High Similarity	NPC18924
0.8672	High Similarity	NPC103823
0.8672	High Similarity	NPC28730
0.8672	High Similarity	NPC44748
0.8672	High Similarity	NPC214406

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 NPC473221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	989
0.2-0.3	1519
0.3-0.4	2787
0.4-0.5	1709
0.5-0.6	979
0.6-0.7	658
0.7-0.8	153
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD4625	Phase 3
0.8538	High Similarity	NPD4908	Phase 1
0.8527	High Similarity	NPD6917	Clinical (unspecified phase)
0.8473	Intermediate Similarity	NPD3027	Phase 3
0.8438	Intermediate Similarity	NPD4749	Approved
0.8425	Intermediate Similarity	NPD1610	Phase 2
0.8409	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD1548	Phase 1
0.8182	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1613	Approved
0.8148	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD4750	Phase 3
0.8045	Intermediate Similarity	NPD2861	Phase 2
0.7986	Intermediate Similarity	NPD6099	Approved
0.7986	Intermediate Similarity	NPD6100	Approved
0.7984	Intermediate Similarity	NPD4626	Approved
0.7955	Intermediate Similarity	NPD6696	Suspended
0.7943	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD7635	Approved
0.791	Intermediate Similarity	NPD3018	Phase 2
0.7874	Intermediate Similarity	NPD6671	Approved
0.7868	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD846	Approved
0.7833	Intermediate Similarity	NPD940	Approved
0.777	Intermediate Similarity	NPD4097	Suspended
0.777	Intermediate Similarity	NPD1607	Approved
0.7769	Intermediate Similarity	NPD1651	Approved
0.7754	Intermediate Similarity	NPD4060	Phase 1
0.775	Intermediate Similarity	NPD1242	Phase 1
0.7744	Intermediate Similarity	NPD2983	Phase 2
0.7744	Intermediate Similarity	NPD2982	Phase 2
0.7727	Intermediate Similarity	NPD422	Phase 1
0.7727	Intermediate Similarity	NPD6232	Discontinued
0.7717	Intermediate Similarity	NPD5283	Phase 1
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7687	Intermediate Similarity	NPD1283	Approved
0.7669	Intermediate Similarity	NPD2981	Phase 2
0.7639	Intermediate Similarity	NPD3892	Phase 2
0.7639	Intermediate Similarity	NPD3750	Approved
0.7639	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5691	Approved
0.7626	Intermediate Similarity	NPD2238	Phase 2
0.7626	Intermediate Similarity	NPD1240	Approved
0.7622	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD709	Approved
0.7594	Intermediate Similarity	NPD1611	Approved
0.7551	Intermediate Similarity	NPD2532	Approved
0.7551	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7447	Phase 1
0.7551	Intermediate Similarity	NPD2533	Approved
0.7551	Intermediate Similarity	NPD2534	Approved
0.755	Intermediate Similarity	NPD37	Approved
0.7548	Intermediate Similarity	NPD6959	Discontinued
0.7538	Intermediate Similarity	NPD7340	Approved
0.7537	Intermediate Similarity	NPD2230	Approved
0.7537	Intermediate Similarity	NPD2232	Approved
0.7537	Intermediate Similarity	NPD2233	Approved
0.7535	Intermediate Similarity	NPD1510	Phase 2
0.7521	Intermediate Similarity	NPD3020	Approved
0.752	Intermediate Similarity	NPD2342	Discontinued
0.75	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.7481	Intermediate Similarity	NPD1669	Approved
0.7463	Intermediate Similarity	NPD1281	Approved
0.7445	Intermediate Similarity	NPD4624	Approved
0.7442	Intermediate Similarity	NPD1398	Phase 1
0.7422	Intermediate Similarity	NPD228	Approved
0.7419	Intermediate Similarity	NPD6234	Discontinued
0.7417	Intermediate Similarity	NPD844	Approved
0.7417	Intermediate Similarity	NPD2860	Approved
0.7417	Intermediate Similarity	NPD2859	Approved
0.7403	Intermediate Similarity	NPD4965	Approved
0.7403	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD4967	Phase 2
0.7402	Intermediate Similarity	NPD3021	Approved
0.7402	Intermediate Similarity	NPD3022	Approved
0.7389	Intermediate Similarity	NPD7229	Phase 3
0.7386	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2979	Phase 3
0.7375	Intermediate Similarity	NPD5844	Phase 1
0.7365	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7212	Phase 2
0.7365	Intermediate Similarity	NPD7041	Phase 2
0.7365	Intermediate Similarity	NPD7213	Phase 3
0.7355	Intermediate Similarity	NPD288	Approved
0.7353	Intermediate Similarity	NPD5327	Phase 3
0.7333	Intermediate Similarity	NPD2933	Approved
0.7333	Intermediate Similarity	NPD2934	Approved
0.7333	Intermediate Similarity	NPD3705	Approved
0.7329	Intermediate Similarity	NPD6674	Discontinued
0.7328	Intermediate Similarity	NPD7157	Approved
0.7324	Intermediate Similarity	NPD5735	Approved
0.732	Intermediate Similarity	NPD1934	Approved
0.7319	Intermediate Similarity	NPD6584	Phase 3
0.7315	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5762	Approved
0.731	Intermediate Similarity	NPD5763	Approved
0.731	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3540	Phase 1
0.731	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD968	Approved
0.7299	Intermediate Similarity	NPD8651	Approved
0.7292	Intermediate Similarity	NPD3748	Approved
0.729	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD2801	Approved
0.7267	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5451	Approved
0.7261	Intermediate Similarity	NPD6746	Phase 2
0.726	Intermediate Similarity	NPD1549	Phase 2
0.7254	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3620	Phase 2
0.7248	Intermediate Similarity	NPD1511	Approved
0.7248	Intermediate Similarity	NPD7390	Discontinued
0.7246	Intermediate Similarity	NPD3094	Phase 2
0.7244	Intermediate Similarity	NPD4055	Discovery
0.7241	Intermediate Similarity	NPD1551	Phase 2
0.7241	Intermediate Similarity	NPD3539	Phase 1
0.7237	Intermediate Similarity	NPD4005	Discontinued
0.7231	Intermediate Similarity	NPD7843	Approved
0.723	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1091	Approved
0.7205	Intermediate Similarity	NPD7228	Approved
0.7203	Intermediate Similarity	NPD5124	Phase 1
0.7203	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4380	Phase 2
0.7188	Intermediate Similarity	NPD2684	Approved
0.7185	Intermediate Similarity	NPD2668	Approved
0.7185	Intermediate Similarity	NPD1778	Approved
0.7185	Intermediate Similarity	NPD2667	Approved
0.7181	Intermediate Similarity	NPD7124	Phase 2
0.7177	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4108	Discontinued
0.7172	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3091	Approved
0.7163	Intermediate Similarity	NPD7095	Approved
0.7162	Intermediate Similarity	NPD7466	Approved
0.7162	Intermediate Similarity	NPD7003	Approved
0.7153	Intermediate Similarity	NPD6353	Approved
0.7153	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD6090	Discontinued
0.7152	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4140	Approved
0.7132	Intermediate Similarity	NPD3847	Discontinued
0.7132	Intermediate Similarity	NPD3496	Discontinued
0.7123	Intermediate Similarity	NPD2796	Approved
0.7123	Intermediate Similarity	NPD2438	Suspended
0.7122	Intermediate Similarity	NPD2797	Approved
0.7121	Intermediate Similarity	NPD497	Approved
0.7114	Intermediate Similarity	NPD2677	Approved
0.7113	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3445	Approved
0.7111	Intermediate Similarity	NPD3443	Approved
0.7111	Intermediate Similarity	NPD3444	Approved
0.7107	Intermediate Similarity	NPD7199	Phase 2
0.7101	Intermediate Similarity	NPD6583	Phase 3
0.7101	Intermediate Similarity	NPD6582	Phase 2
0.7099	Intermediate Similarity	NPD5535	Approved
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6355	Discontinued
0.708	Intermediate Similarity	NPD3092	Approved
0.7078	Intermediate Similarity	NPD6599	Discontinued
0.707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3882	Suspended
0.7068	Intermediate Similarity	NPD6387	Discontinued
0.7059	Intermediate Similarity	NPD2286	Discontinued
0.7051	Intermediate Similarity	NPD1465	Phase 2
0.7051	Intermediate Similarity	NPD5929	Approved
0.7049	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4628	Phase 3
0.7045	Intermediate Similarity	NPD498	Approved
0.7045	Intermediate Similarity	NPD496	Approved
0.7045	Intermediate Similarity	NPD495	Approved
0.7039	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6559	Discontinued
0.7029	Intermediate Similarity	NPD1840	Phase 2
0.7027	Intermediate Similarity	NPD7037	Approved
0.7025	Intermediate Similarity	NPD3749	Approved
0.7025	Intermediate Similarity	NPD7075	Discontinued
0.702	Intermediate Similarity	NPD4357	Discontinued
0.702	Intermediate Similarity	NPD6087	Phase 1
0.7019	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3226	Approved
0.7013	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5408	Approved
0.7007	Intermediate Similarity	NPD5404	Approved
0.7007	Intermediate Similarity	NPD5406	Approved
0.7007	Intermediate Similarity	NPD5405	Approved
0.7007	Intermediate Similarity	NPD2531	Phase 2
0.7	Intermediate Similarity	NPD4339	Clinical (unspecified phase)

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