NPASS Compound

Structure

CID299180 OpenBabel06191716102D 32 36 0 0 0 0 0 0 0 0999 V2000 -0.4470 -2.7049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -3.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7249 -0.5331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6630 -2.5083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5339 -2.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9426 0.1875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1569 -0.9651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4488 -2.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4667 -2.1754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9197 -2.4460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6798 -2.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4261 0.3207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6808 -1.5296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5495 -0.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2396 -3.9003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9197 -1.2241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6808 -2.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1604 -0.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5495 -3.3707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 -1.5296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4488 -1.5296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 -2.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1569 -2.7049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4470 -0.9651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.5331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1363 -1.7721 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 2.0433 -3.5674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2022 -1.0946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7231 -1.9073 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7729 0.3993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7335 -4.0970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 17 1 0 0 0 0 2 19 1 0 0 0 0 3 7 1 0 0 0 0 3 18 1 0 0 0 0 4 9 2 0 0 0 0 4 19 1 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 21 2 0 0 0 0 9 23 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 17 2 0 0 0 0 13 24 1 0 0 0 0 14 18 2 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 28 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 20 22 1 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 23 28 2 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:	424.17
Volume:	453.585
LogP:	6.37
LogD:	4.206
LogS:	-3.392
# Rotatable Bonds:	0
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	4.495
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.265
MDCK Permeability:	1.1426753189880401e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.222
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	100.7260513305664%
Volume Distribution (VD):	0.408
Pgp-substrate:	0.7973452210426331%

ADMET: Metabolism

CYP1A2-inhibitor:	0.918
CYP1A2-substrate:	0.172
CYP2C19-inhibitor:	0.851
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.838
CYP2D6-substrate:	0.949
CYP3A4-inhibitor:	0.324
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	11.141
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.139
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.418
Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.957
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.903
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC299180

Natural Product ID:	NPC299180
*Common Name:**	Isoplagiochin D
IUPAC Name:	n.a.
Synonyms:	Isoplagiochin D
Standard InCHIKey:	ZVVCUSDMHMVYJD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H24O4/c29-21-8-10-22-20(16-21)7-3-18-6-12-27(31)25(14-18)24-13-17(5-11-26(24)30)1-2-19-4-9-23(22)28(32)15-19/h4-6,8-16,29-32H,1-3,7H2
SMILES:	Oc1ccc2c(c1)CCc1ccc(c(c1)c1cc(CCc3ccc2c(O)c3)ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515207
PubChem CID:	11732630
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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]
NPO33046	liverworts	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21652215]
NPO11783	Lepidozia incurvata	Species	Lepidoziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6570	Cinnamomum philippinense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25173	Phebalium squamulosum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3179	Eria bicolor	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2233	Salvia dugesii	Species	Lamiaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	1
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14320.0	nM	PMID[508131]
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	>	60.0	%	PMID[508132]
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	>	80.0	%	PMID[508132]

☑ 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 NPC299180 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	426
0.1-0.2	2072
0.2-0.3	5347
0.3-0.4	12598
0.4-0.5	5832
0.5-0.6	8816
0.6-0.7	5976
0.7-0.8	1406
0.8-0.85	182
0.85-0.9	31
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9633	High Similarity	NPC322239
0.9375	High Similarity	NPC261973
0.9364	High Similarity	NPC46940
0.9279	High Similarity	NPC321589
0.9279	High Similarity	NPC715
0.9273	High Similarity	NPC95716
0.9266	High Similarity	NPC314187
0.9027	High Similarity	NPC195922
0.8919	High Similarity	NPC58865
0.8829	High Similarity	NPC11554
0.8807	High Similarity	NPC288411
0.8761	High Similarity	NPC151537
0.8761	High Similarity	NPC260323
0.8761	High Similarity	NPC176279
0.8739	High Similarity	NPC151477
0.8729	High Similarity	NPC69006
0.8727	High Similarity	NPC138942
0.8716	High Similarity	NPC168829
0.8707	High Similarity	NPC471668
0.8696	High Similarity	NPC249270
0.8684	High Similarity	NPC250323
0.8673	High Similarity	NPC296683
0.8673	High Similarity	NPC141782
0.8667	High Similarity	NPC71094
0.8649	High Similarity	NPC271274
0.8649	High Similarity	NPC54765
0.8644	High Similarity	NPC126002
0.8644	High Similarity	NPC151197
0.8644	High Similarity	NPC93071
0.8644	High Similarity	NPC176893
0.8636	High Similarity	NPC238696
0.8632	High Similarity	NPC470760
0.8621	High Similarity	NPC35797
0.8621	High Similarity	NPC192948
0.8607	High Similarity	NPC28476
0.8607	High Similarity	NPC133407
0.8571	High Similarity	NPC103916
0.8559	High Similarity	NPC117115
0.8547	High Similarity	NPC115808
0.8547	High Similarity	NPC38893
0.8547	High Similarity	NPC477137
0.8547	High Similarity	NPC92
0.8547	High Similarity	NPC308311
0.8547	High Similarity	NPC469663
0.8547	High Similarity	NPC308828
0.8547	High Similarity	NPC219112
0.8537	High Similarity	NPC145659
0.8537	High Similarity	NPC9292
0.8534	High Similarity	NPC268160
0.8512	High Similarity	NPC176208
0.8512	High Similarity	NPC120172
0.8509	High Similarity	NPC13482
0.8509	High Similarity	NPC132720
0.8496	Intermediate Similarity	NPC262365
0.8496	Intermediate Similarity	NPC95344
0.8487	Intermediate Similarity	NPC469644
0.8482	Intermediate Similarity	NPC21594
0.8475	Intermediate Similarity	NPC477136
0.8475	Intermediate Similarity	NPC304510
0.8475	Intermediate Similarity	NPC172219
0.8462	Intermediate Similarity	NPC147179
0.845	Intermediate Similarity	NPC472648
0.845	Intermediate Similarity	NPC472647
0.845	Intermediate Similarity	NPC191462
0.845	Intermediate Similarity	NPC206525
0.845	Intermediate Similarity	NPC472649
0.845	Intermediate Similarity	NPC133463
0.845	Intermediate Similarity	NPC170328
0.8443	Intermediate Similarity	NPC12824
0.8435	Intermediate Similarity	NPC77772
0.8435	Intermediate Similarity	NPC308689
0.8413	Intermediate Similarity	NPC472369
0.8403	Intermediate Similarity	NPC469609
0.8403	Intermediate Similarity	NPC471671
0.8387	Intermediate Similarity	NPC35341
0.8387	Intermediate Similarity	NPC283508
0.8385	Intermediate Similarity	NPC472646
0.8385	Intermediate Similarity	NPC71465
0.8378	Intermediate Similarity	NPC233827
0.8376	Intermediate Similarity	NPC107240
0.8374	Intermediate Similarity	NPC224342
0.8374	Intermediate Similarity	NPC97578
0.8372	Intermediate Similarity	NPC258780
0.8372	Intermediate Similarity	NPC37410
0.8349	Intermediate Similarity	NPC32674
0.8349	Intermediate Similarity	NPC156313
0.8348	Intermediate Similarity	NPC44732
0.8347	Intermediate Similarity	NPC71870
0.8347	Intermediate Similarity	NPC129176
0.8346	Intermediate Similarity	NPC282508
0.8319	Intermediate Similarity	NPC16030
0.8305	Intermediate Similarity	NPC246760
0.8305	Intermediate Similarity	NPC469719
0.8305	Intermediate Similarity	NPC84999
0.8304	Intermediate Similarity	NPC272029
0.8291	Intermediate Similarity	NPC317869
0.8291	Intermediate Similarity	NPC117846
0.8288	Intermediate Similarity	NPC51015
0.8281	Intermediate Similarity	NPC303144
0.8281	Intermediate Similarity	NPC73656
0.8281	Intermediate Similarity	NPC189482
0.8276	Intermediate Similarity	NPC470770
0.8276	Intermediate Similarity	NPC266937
0.8276	Intermediate Similarity	NPC322753
0.8268	Intermediate Similarity	NPC254000
0.8264	Intermediate Similarity	NPC135467
0.8264	Intermediate Similarity	NPC260832
0.8258	Intermediate Similarity	NPC273623
0.8235	Intermediate Similarity	NPC141001
0.822	Intermediate Similarity	NPC471534
0.822	Intermediate Similarity	NPC12656
0.822	Intermediate Similarity	NPC473137
0.8214	Intermediate Similarity	NPC168393
0.8205	Intermediate Similarity	NPC471179
0.8205	Intermediate Similarity	NPC286222
0.8205	Intermediate Similarity	NPC177962
0.8205	Intermediate Similarity	NPC43525
0.8205	Intermediate Similarity	NPC62867
0.8205	Intermediate Similarity	NPC302371
0.8203	Intermediate Similarity	NPC72669
0.8203	Intermediate Similarity	NPC474517
0.8197	Intermediate Similarity	NPC259703
0.8197	Intermediate Similarity	NPC32322
0.8174	Intermediate Similarity	NPC233835
0.8167	Intermediate Similarity	NPC25648
0.8165	Intermediate Similarity	NPC274678
0.8158	Intermediate Similarity	NPC67250
0.8154	Intermediate Similarity	NPC141023
0.8154	Intermediate Similarity	NPC71372
0.8145	Intermediate Similarity	NPC471187
0.8142	Intermediate Similarity	NPC254965
0.8142	Intermediate Similarity	NPC327811
0.8142	Intermediate Similarity	NPC323810
0.8136	Intermediate Similarity	NPC263753
0.813	Intermediate Similarity	NPC162935
0.813	Intermediate Similarity	NPC249340
0.8125	Intermediate Similarity	NPC12221
0.812	Intermediate Similarity	NPC225679
0.812	Intermediate Similarity	NPC165770
0.812	Intermediate Similarity	NPC476632
0.812	Intermediate Similarity	NPC469912
0.812	Intermediate Similarity	NPC4493
0.8115	Intermediate Similarity	NPC475245
0.811	Intermediate Similarity	NPC38017
0.811	Intermediate Similarity	NPC215300
0.811	Intermediate Similarity	NPC471064
0.8106	Intermediate Similarity	NPC62272
0.8103	Intermediate Similarity	NPC202647
0.8099	Intermediate Similarity	NPC154030
0.8092	Intermediate Similarity	NPC472370
0.8091	Intermediate Similarity	NPC82664
0.8091	Intermediate Similarity	NPC292730
0.8091	Intermediate Similarity	NPC132271
0.8091	Intermediate Similarity	NPC216520
0.8087	Intermediate Similarity	NPC320439
0.808	Intermediate Similarity	NPC61685
0.8077	Intermediate Similarity	NPC473665
0.8073	Intermediate Similarity	NPC128062
0.8073	Intermediate Similarity	NPC76938
0.8073	Intermediate Similarity	NPC151715
0.807	Intermediate Similarity	NPC47284
0.8065	Intermediate Similarity	NPC11250
0.8065	Intermediate Similarity	NPC297057
0.806	Intermediate Similarity	NPC131379
0.8053	Intermediate Similarity	NPC108497
0.8051	Intermediate Similarity	NPC228988
0.8051	Intermediate Similarity	NPC228425
0.8051	Intermediate Similarity	NPC166995
0.8049	Intermediate Similarity	NPC241001
0.8047	Intermediate Similarity	NPC276238
0.8047	Intermediate Similarity	NPC471519
0.8047	Intermediate Similarity	NPC471518
0.8036	Intermediate Similarity	NPC211885
0.8036	Intermediate Similarity	NPC225506
0.8036	Intermediate Similarity	NPC72729
0.8034	Intermediate Similarity	NPC224870
0.8033	Intermediate Similarity	NPC121866
0.8031	Intermediate Similarity	NPC53781
0.8018	Intermediate Similarity	NPC79241
0.8018	Intermediate Similarity	NPC6597
0.8018	Intermediate Similarity	NPC77492
0.8015	Intermediate Similarity	NPC287604
0.8015	Intermediate Similarity	NPC161964
0.8015	Intermediate Similarity	NPC472262
0.8	Intermediate Similarity	NPC53740
0.8	Intermediate Similarity	NPC26244
0.8	Intermediate Similarity	NPC183709
0.8	Intermediate Similarity	NPC474486
0.8	Intermediate Similarity	NPC32714
0.8	Intermediate Similarity	NPC228843
0.7984	Intermediate Similarity	NPC39029
0.7984	Intermediate Similarity	NPC154696
0.7984	Intermediate Similarity	NPC253627
0.7984	Intermediate Similarity	NPC237667
0.7983	Intermediate Similarity	NPC35344
0.7983	Intermediate Similarity	NPC261343
0.7983	Intermediate Similarity	NPC141003
0.7982	Intermediate Similarity	NPC271440
0.7982	Intermediate Similarity	NPC475225
0.797	Intermediate Similarity	NPC266006

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 NPC299180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	1065
0.2-0.3	1188
0.3-0.4	3037
0.4-0.5	1842
0.5-0.6	1178
0.6-0.7	378
0.7-0.8	68
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9083	High Similarity	NPD2342	Discontinued
0.8684	High Similarity	NPD7635	Approved
0.8417	Intermediate Similarity	NPD2286	Discontinued
0.8136	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD3020	Approved
0.8106	Intermediate Similarity	NPD5404	Approved
0.8106	Intermediate Similarity	NPD5408	Approved
0.8106	Intermediate Similarity	NPD5406	Approved
0.8106	Intermediate Similarity	NPD5405	Approved
0.8	Intermediate Similarity	NPD2860	Approved
0.8	Intermediate Similarity	NPD844	Approved
0.8	Intermediate Similarity	NPD2859	Approved
0.7951	Intermediate Similarity	NPD3091	Approved
0.7949	Intermediate Similarity	NPD3021	Approved
0.7949	Intermediate Similarity	NPD3022	Approved
0.7928	Intermediate Similarity	NPD288	Approved
0.7917	Intermediate Similarity	NPD497	Approved
0.7909	Intermediate Similarity	NPD2933	Approved
0.7909	Intermediate Similarity	NPD2934	Approved
0.7857	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD498	Approved
0.7833	Intermediate Similarity	NPD495	Approved
0.7833	Intermediate Similarity	NPD496	Approved
0.7826	Intermediate Similarity	NPD7390	Discontinued
0.7823	Intermediate Similarity	NPD3019	Approved
0.7823	Intermediate Similarity	NPD4059	Approved
0.7742	Intermediate Similarity	NPD4093	Discontinued
0.7734	Intermediate Similarity	NPD3094	Phase 2
0.7719	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3092	Approved
0.768	Intermediate Similarity	NPD3095	Discontinued
0.768	Intermediate Similarity	NPD2932	Approved
0.7679	Intermediate Similarity	NPD1809	Phase 2
0.7658	Intermediate Similarity	NPD845	Approved
0.7647	Intermediate Similarity	NPD4750	Phase 3
0.7643	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4625	Phase 3
0.7597	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD1201	Approved
0.754	Intermediate Similarity	NPD4626	Approved
0.7462	Intermediate Similarity	NPD1470	Approved
0.7444	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD1242	Phase 1
0.7368	Intermediate Similarity	NPD5155	Approved
0.7368	Intermediate Similarity	NPD5156	Approved
0.7357	Intermediate Similarity	NPD7003	Approved
0.7353	Intermediate Similarity	NPD4097	Suspended
0.735	Intermediate Similarity	NPD940	Approved
0.735	Intermediate Similarity	NPD846	Approved
0.7348	Intermediate Similarity	NPD5736	Approved
0.7344	Intermediate Similarity	NPD3023	Approved
0.7344	Intermediate Similarity	NPD3026	Approved
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.7323	Intermediate Similarity	NPD1651	Approved
0.7323	Intermediate Similarity	NPD3024	Approved
0.7323	Intermediate Similarity	NPD3025	Approved
0.7299	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2606	Approved
0.7293	Intermediate Similarity	NPD2605	Approved
0.7293	Intermediate Similarity	NPD3595	Approved
0.7293	Intermediate Similarity	NPD3594	Approved
0.7293	Intermediate Similarity	NPD4908	Phase 1
0.7288	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1611	Approved
0.7266	Intermediate Similarity	NPD1751	Approved
0.7266	Intermediate Similarity	NPD4589	Approved
0.7252	Intermediate Similarity	NPD1283	Approved
0.7246	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5303	Approved
0.7244	Intermediate Similarity	NPD5304	Approved
0.7236	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2861	Phase 2
0.7214	Intermediate Similarity	NPD7037	Approved
0.7213	Intermediate Similarity	NPD1792	Phase 2
0.7203	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2420	Approved
0.7203	Intermediate Similarity	NPD2421	Approved
0.7203	Intermediate Similarity	NPD7041	Phase 2
0.7188	Intermediate Similarity	NPD5691	Approved
0.7185	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4624	Approved
0.7143	Intermediate Similarity	NPD6671	Approved
0.7132	Intermediate Similarity	NPD6663	Approved
0.7121	Intermediate Similarity	NPD6696	Suspended
0.712	Intermediate Similarity	NPD1398	Phase 1
0.712	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2229	Approved
0.712	Intermediate Similarity	NPD2228	Approved
0.712	Intermediate Similarity	NPD2234	Approved
0.7119	Intermediate Similarity	NPD3028	Approved
0.7109	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD111	Approved
0.709	Intermediate Similarity	NPD3636	Approved
0.709	Intermediate Similarity	NPD3635	Approved
0.709	Intermediate Similarity	NPD3637	Approved
0.7087	Intermediate Similarity	NPD7340	Approved
0.7045	Intermediate Similarity	NPD1669	Approved
0.7023	Intermediate Similarity	NPD1281	Approved
0.7021	Intermediate Similarity	NPD4721	Approved
0.7021	Intermediate Similarity	NPD4725	Approved
0.7021	Intermediate Similarity	NPD4726	Approved
0.7015	Intermediate Similarity	NPD6584	Phase 3
0.7015	Intermediate Similarity	NPD2195	Approved
0.7015	Intermediate Similarity	NPD2194	Approved
0.7014	Intermediate Similarity	NPD3845	Phase 1
0.7008	Intermediate Similarity	NPD709	Approved
0.6984	Remote Similarity	NPD5283	Phase 1
0.6967	Remote Similarity	NPD1444	Approved
0.6967	Remote Similarity	NPD1445	Approved
0.6959	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2979	Phase 3
0.6957	Remote Similarity	NPD3620	Phase 2
0.6957	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6959	Discontinued
0.694	Remote Similarity	NPD1164	Approved
0.6935	Remote Similarity	NPD5451	Approved
0.6934	Remote Similarity	NPD3764	Approved
0.6918	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4749	Approved
0.6917	Remote Similarity	NPD5327	Phase 3
0.6912	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1610	Phase 2
0.6879	Remote Similarity	NPD7742	Approved
0.6879	Remote Similarity	NPD7743	Approved
0.6875	Remote Similarity	NPD8166	Discontinued
0.6875	Remote Similarity	NPD5819	Phase 2
0.6846	Remote Similarity	NPD7330	Discontinued
0.6842	Remote Similarity	NPD2233	Approved
0.6842	Remote Similarity	NPD2232	Approved
0.6842	Remote Similarity	NPD2230	Approved
0.6838	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4140	Approved
0.6831	Remote Similarity	NPD2935	Discontinued
0.6822	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1983	Approved
0.6818	Remote Similarity	NPD1980	Approved
0.6818	Remote Similarity	NPD1981	Approved
0.6812	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6674	Discontinued
0.6797	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5951	Approved
0.6795	Remote Similarity	NPD6232	Discontinued
0.6791	Remote Similarity	NPD6583	Phase 3
0.6791	Remote Similarity	NPD6582	Phase 2
0.6786	Remote Similarity	NPD5735	Approved
0.6783	Remote Similarity	NPD2346	Discontinued
0.6781	Remote Similarity	NPD3300	Phase 2
0.6776	Remote Similarity	NPD5929	Approved
0.6772	Remote Similarity	NPD5535	Approved
0.6767	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6405	Approved
0.6763	Remote Similarity	NPD6407	Approved
0.6761	Remote Similarity	NPD4108	Discontinued
0.6757	Remote Similarity	NPD4319	Phase 2
0.6742	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7095	Approved
0.6739	Remote Similarity	NPD3027	Phase 3
0.6738	Remote Similarity	NPD6353	Approved
0.6738	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD9500	Approved
0.6718	Remote Similarity	NPD1548	Phase 1
0.6714	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1613	Approved
0.6713	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD968	Approved
0.6693	Remote Similarity	NPD228	Approved
0.6691	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3638	Discontinued
0.6689	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3400	Discontinued
0.6644	Remote Similarity	NPD6090	Discontinued
0.6642	Remote Similarity	NPD7451	Discontinued
0.6641	Remote Similarity	NPD9379	Approved
0.6641	Remote Similarity	NPD9377	Approved
0.6626	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3226	Approved
0.6623	Remote Similarity	NPD7458	Discontinued
0.6621	Remote Similarity	NPD4257	Approved
0.6621	Remote Similarity	NPD4256	Phase 2
0.6619	Remote Similarity	NPD7008	Discontinued
0.6618	Remote Similarity	NPD5310	Approved
0.6618	Remote Similarity	NPD5311	Approved
0.6617	Remote Similarity	NPD5846	Approved
0.6617	Remote Similarity	NPD5125	Phase 3
0.6617	Remote Similarity	NPD5126	Approved
0.6617	Remote Similarity	NPD6516	Phase 2
0.6615	Remote Similarity	NPD6387	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data