NPASS Compound

Structure

NPC28476 OpenBabel07101719252D 32 36 0 0 0 0 0 0 0 0999 V2000 1.3128 1.0927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1788 0.5927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4468 0.5927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6256 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8951 0.5412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2045 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3600 1.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 2.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1598 1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3122 0.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3531 2.0073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3128 1.7802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7629 0.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3128 -0.9073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7854 1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3128 2.6365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8745 1.3959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1788 -0.4073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9509 1.1432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7185 2.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3253 1.1432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3679 1.0466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4468 -0.4073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4211 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9071 2.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9352 2.3316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7894 2.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2695 0.5412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2764 1.4645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1448 3.3094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5712 1.3862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 18 1 0 0 0 0 3 23 2 0 0 0 0 4 5 2 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 9 1 0 0 0 0 6 20 1 0 0 0 0 7 11 2 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 22 2 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 28 2 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 25 27 2 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.15
Volume:	450.949
LogP:	6.717
LogD:	4.249
LogS:	-4.25
# Rotatable Bonds:	0
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.301
Synthetic Accessibility Score:	4.797
Fsp3:	0.071
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:	-5.433
MDCK Permeability:	1.2060229892085772e-05
Pgp-inhibitor:	0.953
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.427
30% Bioavailability (F30%):	0.442

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	101.8334732055664%
Volume Distribution (VD):	0.339
Pgp-substrate:	0.5412506461143494%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.146
CYP2C19-inhibitor:	0.818
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.432
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.312
CYP2D6-substrate:	0.956
CYP3A4-inhibitor:	0.36
CYP3A4-substrate:	0.258

ADMET: Excretion

Clearance (CL):	10.074
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.408
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.121
AMES Toxicity:	0.74
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.971
Carcinogencity:	0.22
Eye Corrosion:	0.003
Eye Irritation:	0.847
Respiratory Toxicity:	0.522

Download Data

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

Natural Product: NPC28476

Natural Product ID:	NPC28476
*Common Name:**	Isoplagiochin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DLWONXBMHBQJCM-PLNGDYQASA-N
Standard InCHI:	InChI=1S/C28H22O4/c29-22-10-13-28-21(17-22)9-6-20-8-12-27(31)25(16-20)24-15-19(7-11-26(24)30)5-4-18-2-1-3-23(14-18)32-28/h1-5,7-8,10-17,29-31H,6,9H2/b5-4-
SMILES:	Oc1ccc2c(c1)CCc1ccc(c(c1)c1cc(/C=Cc3cc(O2)ccc3)ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461451
PubChem CID:	11026227
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO33046	liverworts	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16378374]
NPO32483	Plagiochila fruticosa	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19056262]
NPO32483	Plagiochila fruticosa	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO33046	liverworts	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21652215]
NPO32483	Plagiochila fruticosa	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32479076]

☑ 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

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[496542]
NPT2	Others	Unspecified		IC50	=	50000.0	nM	PMID[496543]

☑ 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 NPC28476 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	456
0.1-0.2	2141
0.2-0.3	5710
0.3-0.4	13101
0.4-0.5	3904
0.5-0.6	5221
0.6-0.7	9324
0.7-0.8	2533
0.8-0.85	280
0.85-0.9	24
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133407
0.9048	High Similarity	NPC210655
0.8939	High Similarity	NPC20520
0.8939	High Similarity	NPC61783
0.8846	High Similarity	NPC71372
0.881	High Similarity	NPC134431
0.881	High Similarity	NPC156854
0.88	High Similarity	NPC61685
0.8692	High Similarity	NPC189482
0.8692	High Similarity	NPC73656
0.8672	High Similarity	NPC47288
0.8651	High Similarity	NPC248557
0.8636	High Similarity	NPC125579
0.8629	High Similarity	NPC129176
0.8607	High Similarity	NPC299180
0.8595	High Similarity	NPC473718
0.8583	High Similarity	NPC141003
0.8583	High Similarity	NPC35344
0.8561	High Similarity	NPC184269
0.8561	High Similarity	NPC141023
0.855	High Similarity	NPC303144
0.8548	High Similarity	NPC103916
0.8538	High Similarity	NPC254000
0.8525	High Similarity	NPC69539
0.8516	High Similarity	NPC17837
0.8516	High Similarity	NPC304630
0.8496	Intermediate Similarity	NPC258780
0.8485	Intermediate Similarity	NPC211352
0.8473	Intermediate Similarity	NPC282508
0.8473	Intermediate Similarity	NPC153019
0.8468	Intermediate Similarity	NPC51341
0.8455	Intermediate Similarity	NPC238176
0.8455	Intermediate Similarity	NPC187993
0.8433	Intermediate Similarity	NPC133463
0.8433	Intermediate Similarity	NPC472647
0.8433	Intermediate Similarity	NPC141717
0.8433	Intermediate Similarity	NPC206525
0.8433	Intermediate Similarity	NPC170328
0.8433	Intermediate Similarity	NPC472648
0.8433	Intermediate Similarity	NPC472649
0.8433	Intermediate Similarity	NPC191462
0.8409	Intermediate Similarity	NPC289624
0.8409	Intermediate Similarity	NPC27578
0.8374	Intermediate Similarity	NPC261973
0.837	Intermediate Similarity	NPC71465
0.837	Intermediate Similarity	NPC472646
0.837	Intermediate Similarity	NPC48956
0.8358	Intermediate Similarity	NPC15109
0.8358	Intermediate Similarity	NPC11727
0.8358	Intermediate Similarity	NPC37410
0.8347	Intermediate Similarity	NPC474920
0.8346	Intermediate Similarity	NPC138940
0.8333	Intermediate Similarity	NPC45663
0.8333	Intermediate Similarity	NPC212559
0.8321	Intermediate Similarity	NPC471518
0.8321	Intermediate Similarity	NPC471519
0.832	Intermediate Similarity	NPC471449
0.832	Intermediate Similarity	NPC32152
0.8305	Intermediate Similarity	NPC54765
0.8296	Intermediate Similarity	NPC471522
0.8293	Intermediate Similarity	NPC301321
0.8284	Intermediate Similarity	NPC256307
0.8284	Intermediate Similarity	NPC66840
0.8279	Intermediate Similarity	NPC322239
0.8268	Intermediate Similarity	NPC48623
0.8268	Intermediate Similarity	NPC168707
0.8261	Intermediate Similarity	NPC186033
0.8254	Intermediate Similarity	NPC474131
0.8254	Intermediate Similarity	NPC232295
0.8248	Intermediate Similarity	NPC182509
0.8248	Intermediate Similarity	NPC174787
0.8248	Intermediate Similarity	NPC213607
0.8248	Intermediate Similarity	NPC273623
0.8244	Intermediate Similarity	NPC53986
0.8244	Intermediate Similarity	NPC38664
0.8244	Intermediate Similarity	NPC176590
0.8244	Intermediate Similarity	NPC471064
0.8235	Intermediate Similarity	NPC470308
0.8235	Intermediate Similarity	NPC470307
0.8203	Intermediate Similarity	NPC150026
0.8203	Intermediate Similarity	NPC46586
0.8203	Intermediate Similarity	NPC302211
0.8203	Intermediate Similarity	NPC204535
0.8197	Intermediate Similarity	NPC98372
0.8195	Intermediate Similarity	NPC118683
0.8195	Intermediate Similarity	NPC244888
0.8195	Intermediate Similarity	NPC293203
0.8195	Intermediate Similarity	NPC211413
0.8195	Intermediate Similarity	NPC164804
0.8195	Intermediate Similarity	NPC471517
0.8195	Intermediate Similarity	NPC8899
0.8195	Intermediate Similarity	NPC160623
0.8195	Intermediate Similarity	NPC473309
0.8195	Intermediate Similarity	NPC68205
0.8189	Intermediate Similarity	NPC100108
0.8189	Intermediate Similarity	NPC277798
0.8188	Intermediate Similarity	NPC100482
0.8188	Intermediate Similarity	NPC277331
0.8182	Intermediate Similarity	NPC93962
0.8182	Intermediate Similarity	NPC134360
0.8168	Intermediate Similarity	NPC46978
0.8168	Intermediate Similarity	NPC21563
0.8167	Intermediate Similarity	NPC95344
0.8167	Intermediate Similarity	NPC75440
0.8162	Intermediate Similarity	NPC474610
0.816	Intermediate Similarity	NPC25648
0.8156	Intermediate Similarity	NPC150714
0.8156	Intermediate Similarity	NPC14468
0.8156	Intermediate Similarity	NPC95652
0.8154	Intermediate Similarity	NPC81641
0.8154	Intermediate Similarity	NPC113495
0.8148	Intermediate Similarity	NPC473107
0.8148	Intermediate Similarity	NPC476617
0.8148	Intermediate Similarity	NPC476615
0.8148	Intermediate Similarity	NPC476616
0.8145	Intermediate Similarity	NPC283169
0.814	Intermediate Similarity	NPC261992
0.814	Intermediate Similarity	NPC474130
0.8136	Intermediate Similarity	NPC288411
0.8134	Intermediate Similarity	NPC474134
0.8134	Intermediate Similarity	NPC469611
0.8134	Intermediate Similarity	NPC131128
0.8125	Intermediate Similarity	NPC476633
0.8125	Intermediate Similarity	NPC251259
0.8125	Intermediate Similarity	NPC475839
0.8116	Intermediate Similarity	NPC34431
0.8116	Intermediate Similarity	NPC22317
0.8116	Intermediate Similarity	NPC73505
0.8116	Intermediate Similarity	NPC473049
0.8116	Intermediate Similarity	NPC472794
0.8116	Intermediate Similarity	NPC165026
0.8116	Intermediate Similarity	NPC79372
0.8116	Intermediate Similarity	NPC295719
0.8115	Intermediate Similarity	NPC95716
0.8115	Intermediate Similarity	NPC275627
0.8106	Intermediate Similarity	NPC215300
0.8106	Intermediate Similarity	NPC38017
0.8106	Intermediate Similarity	NPC274717
0.8099	Intermediate Similarity	NPC58190
0.8099	Intermediate Similarity	NPC70409
0.8099	Intermediate Similarity	NPC82917
0.8099	Intermediate Similarity	NPC108811
0.8099	Intermediate Similarity	NPC202742
0.8099	Intermediate Similarity	NPC262911
0.8099	Intermediate Similarity	NPC263940
0.8099	Intermediate Similarity	NPC294558
0.8099	Intermediate Similarity	NPC170103
0.8099	Intermediate Similarity	NPC236202
0.8099	Intermediate Similarity	NPC18185
0.8099	Intermediate Similarity	NPC204770
0.8095	Intermediate Similarity	NPC139047
0.8092	Intermediate Similarity	NPC170485
0.8092	Intermediate Similarity	NPC50315
0.8092	Intermediate Similarity	NPC26879
0.8092	Intermediate Similarity	NPC230479
0.8092	Intermediate Similarity	NPC283049
0.8088	Intermediate Similarity	NPC111655
0.8083	Intermediate Similarity	NPC233320
0.8077	Intermediate Similarity	NPC474237
0.8074	Intermediate Similarity	NPC77196
0.8074	Intermediate Similarity	NPC469610
0.8074	Intermediate Similarity	NPC92805
0.8071	Intermediate Similarity	NPC173203
0.8071	Intermediate Similarity	NPC163508
0.8067	Intermediate Similarity	NPC138942
0.8062	Intermediate Similarity	NPC188997
0.806	Intermediate Similarity	NPC476166
0.806	Intermediate Similarity	NPC236014
0.806	Intermediate Similarity	NPC280653
0.806	Intermediate Similarity	NPC300875
0.806	Intermediate Similarity	NPC228369
0.806	Intermediate Similarity	NPC164574
0.806	Intermediate Similarity	NPC206224
0.806	Intermediate Similarity	NPC472590
0.806	Intermediate Similarity	NPC268917
0.806	Intermediate Similarity	NPC129106
0.806	Intermediate Similarity	NPC118114
0.806	Intermediate Similarity	NPC12875
0.806	Intermediate Similarity	NPC196765
0.806	Intermediate Similarity	NPC207892
0.806	Intermediate Similarity	NPC129784
0.806	Intermediate Similarity	NPC17343
0.806	Intermediate Similarity	NPC150011
0.8058	Intermediate Similarity	NPC472792
0.8058	Intermediate Similarity	NPC472791
0.8051	Intermediate Similarity	NPC168829
0.8049	Intermediate Similarity	NPC46940
0.8047	Intermediate Similarity	NPC131868
0.8045	Intermediate Similarity	NPC96719
0.8045	Intermediate Similarity	NPC222108
0.8045	Intermediate Similarity	NPC16577
0.8043	Intermediate Similarity	NPC24635
0.8043	Intermediate Similarity	NPC55947
0.8042	Intermediate Similarity	NPC227516
0.8042	Intermediate Similarity	NPC20757
0.8031	Intermediate Similarity	NPC121866
0.803	Intermediate Similarity	NPC53781
0.8029	Intermediate Similarity	NPC205442
0.8029	Intermediate Similarity	NPC173660
0.8029	Intermediate Similarity	NPC265515

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 NPC28476 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	422
0.1-0.2	1055
0.2-0.3	1436
0.3-0.4	2723
0.4-0.5	1736
0.5-0.6	1045
0.6-0.7	613
0.7-0.8	115
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.845	Intermediate Similarity	NPD2861	Phase 2
0.8443	Intermediate Similarity	NPD6671	Approved
0.8397	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD4908	Phase 1
0.814	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD4625	Phase 3
0.8	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD968	Approved
0.7984	Intermediate Similarity	NPD1611	Approved
0.7955	Intermediate Similarity	NPD6584	Phase 3
0.7846	Intermediate Similarity	NPD1610	Phase 2
0.784	Intermediate Similarity	NPD1398	Phase 1
0.7836	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6696	Suspended
0.7795	Intermediate Similarity	NPD7340	Approved
0.7787	Intermediate Similarity	NPD2342	Discontinued
0.7761	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5535	Approved
0.776	Intermediate Similarity	NPD7635	Approved
0.773	Intermediate Similarity	NPD7037	Approved
0.7727	Intermediate Similarity	NPD6583	Phase 3
0.7727	Intermediate Similarity	NPD6582	Phase 2
0.7674	Intermediate Similarity	NPD1548	Phase 1
0.7647	Intermediate Similarity	NPD7095	Approved
0.7634	Intermediate Similarity	NPD3496	Discontinued
0.7609	Intermediate Similarity	NPD1613	Approved
0.7609	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4749	Approved
0.7591	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2935	Discontinued
0.7576	Intermediate Similarity	NPD1535	Discovery
0.7559	Intermediate Similarity	NPD5283	Phase 1
0.7557	Intermediate Similarity	NPD6516	Phase 2
0.7557	Intermediate Similarity	NPD4626	Approved
0.7557	Intermediate Similarity	NPD5846	Approved
0.7552	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD5451	Approved
0.7519	Intermediate Similarity	NPD1481	Phase 2
0.75	Intermediate Similarity	NPD3020	Approved
0.7466	Intermediate Similarity	NPD7041	Phase 2
0.7466	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6798	Discontinued
0.7463	Intermediate Similarity	NPD5327	Phase 3
0.7442	Intermediate Similarity	NPD7157	Approved
0.744	Intermediate Similarity	NPD2684	Approved
0.7438	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6233	Phase 2
0.7407	Intermediate Similarity	NPD8651	Approved
0.7395	Intermediate Similarity	NPD2859	Approved
0.7395	Intermediate Similarity	NPD2860	Approved
0.7386	Intermediate Similarity	NPD7768	Phase 2
0.7381	Intermediate Similarity	NPD3021	Approved
0.7381	Intermediate Similarity	NPD3022	Approved
0.7379	Intermediate Similarity	NPD7003	Approved
0.7376	Intermediate Similarity	NPD4097	Suspended
0.7368	Intermediate Similarity	NPD8455	Phase 2
0.7368	Intermediate Similarity	NPD5929	Approved
0.7357	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4140	Approved
0.7353	Intermediate Similarity	NPD2797	Approved
0.7348	Intermediate Similarity	NPD1651	Approved
0.7348	Intermediate Similarity	NPD5691	Approved
0.7344	Intermediate Similarity	NPD7843	Approved
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1669	Approved
0.7333	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7097	Phase 1
0.7311	Intermediate Similarity	NPD2934	Approved
0.7311	Intermediate Similarity	NPD2933	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD709	Approved
0.7308	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD5735	Approved
0.7299	Intermediate Similarity	NPD4624	Approved
0.7297	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2286	Discontinued
0.7279	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD6581	Approved
0.7273	Intermediate Similarity	NPD6580	Approved
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3027	Phase 3
0.7266	Intermediate Similarity	NPD228	Approved
0.7259	Intermediate Similarity	NPD2233	Approved
0.7259	Intermediate Similarity	NPD2230	Approved
0.7259	Intermediate Similarity	NPD2235	Phase 2
0.7259	Intermediate Similarity	NPD2231	Phase 2
0.7259	Intermediate Similarity	NPD2232	Approved
0.7254	Intermediate Similarity	NPD6353	Approved
0.7248	Intermediate Similarity	NPD6090	Discontinued
0.7218	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2313	Discontinued
0.7214	Intermediate Similarity	NPD3268	Approved
0.7203	Intermediate Similarity	NPD4536	Approved
0.7203	Intermediate Similarity	NPD4538	Approved
0.7203	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6674	Discontinued
0.7183	Intermediate Similarity	NPD6355	Discontinued
0.7181	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7447	Phase 1
0.7181	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6387	Discontinued
0.7174	Intermediate Similarity	NPD3691	Phase 2
0.7174	Intermediate Similarity	NPD3690	Phase 2
0.7172	Intermediate Similarity	NPD7030	Discontinued
0.7172	Intermediate Similarity	NPD2344	Approved
0.7172	Intermediate Similarity	NPD2346	Discontinued
0.7163	Intermediate Similarity	NPD7477	Discontinued
0.7153	Intermediate Similarity	NPD5960	Phase 3
0.7153	Intermediate Similarity	NPD3225	Approved
0.7153	Intermediate Similarity	NPD4108	Discontinued
0.7153	Intermediate Similarity	NPD5588	Approved
0.7143	Intermediate Similarity	NPD1182	Approved
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD4319	Phase 2
0.7133	Intermediate Similarity	NPD2157	Approved
0.7132	Intermediate Similarity	NPD1840	Phase 2
0.7132	Intermediate Similarity	NPD1608	Approved
0.7114	Intermediate Similarity	NPD7212	Phase 2
0.7114	Intermediate Similarity	NPD7213	Phase 3
0.7113	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2979	Phase 3
0.7113	Intermediate Similarity	NPD3620	Phase 2
0.7107	Intermediate Similarity	NPD844	Approved
0.7107	Intermediate Similarity	NPD1809	Phase 2
0.7103	Intermediate Similarity	NPD5408	Approved
0.7103	Intermediate Similarity	NPD4477	Approved
0.7103	Intermediate Similarity	NPD4476	Approved
0.7103	Intermediate Similarity	NPD5405	Approved
0.7103	Intermediate Similarity	NPD5404	Approved
0.7103	Intermediate Similarity	NPD5406	Approved
0.7099	Intermediate Similarity	NPD497	Approved
0.7097	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3443	Approved
0.709	Intermediate Similarity	NPD3445	Approved
0.709	Intermediate Similarity	NPD3444	Approved
0.709	Intermediate Similarity	NPD5585	Approved
0.7087	Intermediate Similarity	NPD290	Approved
0.7086	Intermediate Similarity	NPD7427	Discontinued
0.7083	Intermediate Similarity	NPD7119	Phase 2
0.7083	Intermediate Similarity	NPD845	Approved
0.708	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD821	Approved
0.7068	Intermediate Similarity	NPD7644	Approved
0.7067	Intermediate Similarity	NPD7019	Approved
0.7067	Intermediate Similarity	NPD7020	Approved
0.7063	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7059	Intermediate Similarity	NPD1281	Approved
0.7051	Intermediate Similarity	NPD7773	Phase 2
0.7049	Intermediate Similarity	NPD288	Approved
0.7045	Intermediate Similarity	NPD2557	Approved
0.7042	Intermediate Similarity	NPD4475	Approved
0.7042	Intermediate Similarity	NPD7265	Discontinued
0.7042	Intermediate Similarity	NPD4474	Approved
0.7042	Intermediate Similarity	NPD8032	Phase 2
0.7037	Intermediate Similarity	NPD2667	Approved
0.7037	Intermediate Similarity	NPD2668	Approved
0.7037	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6331	Phase 2
0.7025	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD498	Approved
0.7023	Intermediate Similarity	NPD495	Approved
0.7023	Intermediate Similarity	NPD496	Approved
0.7021	Intermediate Similarity	NPD6179	Discontinued
0.702	Intermediate Similarity	NPD6273	Approved
0.7015	Intermediate Similarity	NPD3091	Approved
0.7015	Intermediate Similarity	NPD1894	Discontinued
0.6993	Remote Similarity	NPD3226	Approved
0.6992	Remote Similarity	NPD3596	Phase 2
0.6986	Remote Similarity	NPD6032	Approved
0.6986	Remote Similarity	NPD6099	Approved
0.6986	Remote Similarity	NPD6100	Approved
0.6985	Remote Similarity	NPD3847	Discontinued
0.698	Remote Similarity	NPD2309	Approved
0.6978	Remote Similarity	NPD4098	Discontinued
0.6972	Remote Similarity	NPD7294	Phase 1
0.6972	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6382	Discontinued
0.6963	Remote Similarity	NPD4093	Discontinued
0.6957	Remote Similarity	NPD6540	Phase 3
0.6957	Remote Similarity	NPD6539	Approved
0.6957	Remote Similarity	NPD6543	Approved
0.6957	Remote Similarity	NPD6542	Approved
0.6947	Remote Similarity	NPD1138	Approved
0.6944	Remote Similarity	NPD5124	Phase 1
0.6944	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5763	Approved
0.6939	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5865	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