NPASS Compound

Structure

NPC217180 OpenBabel07101718242D 31 32 0 0 0 0 0 0 0 0999 V2000 4.4347 -1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4727 0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -5.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -5.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6308 -3.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -4.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -3.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6308 -4.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -3.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -1.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4968 -5.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -3.0055 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 2 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 23 1 0 0 0 0 11 18 2 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 12 24 1 0 0 0 0 13 19 1 0 0 0 0 13 26 1 0 0 0 0 14 21 1 0 0 0 0 14 26 2 0 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 31 1 0 0 0 0 22 27 1 0 0 0 0 23 27 1 0 0 0 0 24 28 2 0 0 0 0 25 29 2 0 0 0 0 26 31 1 0 0 0 0 27 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.23
Volume:	467.231
LogP:	5.619
LogD:	4.154
LogS:	-5.148
# Rotatable Bonds:	9
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.204
Synthetic Accessibility Score:	3.527
Fsp3:	0.296
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.173
MDCK Permeability:	2.5673431082395837e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.073
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	100.9990463256836%
Volume Distribution (VD):	0.308
Pgp-substrate:	0.3556521236896515%

ADMET: Metabolism

CYP1A2-inhibitor:	0.443
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.762
CYP2C19-substrate:	0.392
CYP2C9-inhibitor:	0.789
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	6.215
Half-life (T1/2):	0.937

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.449
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.968
Carcinogencity:	0.141
Eye Corrosion:	0.003
Eye Irritation:	0.273
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC217180

Natural Product ID:	NPC217180
*Common Name:**	5-Oxo-Cystofuranoquinone
IUPAC Name:	2-methyl-6-[(2E,6E,10E)-3,7,11-trimethyl-12-(4-methylfuran-2-yl)-5-oxododeca-2,6,10-trienyl]cyclohexa-2,5-diene-1,4-dione
Synonyms:	5-Oxo-Cystofuranoquinone
Standard InCHIKey:	GWMQARFDFFCDBM-PYGWAEJBSA-N
Standard InCHI:	InChI=1S/C27H32O4/c1-18(7-6-8-19(2)13-26-14-21(4)17-31-26)11-24(28)12-20(3)9-10-23-16-25(29)15-22(5)27(23)30/h8-9,11,14-17H,6-7,10,12-13H2,1-5H3/b18-11+,19-8+,20-9+
SMILES:	C/C(=CC(=O)C/C(=C/CC1=CC(=O)C=C(C1=O)C)/C)/CC/C=C(/Cc1occ(c1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461487
PubChem CID:	11732559
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO8863	Cystoseira crinita	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880316]
NPO8863	Cystoseira crinita	Species	Sargassaceae	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
Others	11

Activity Type	# Activity
NON-MOLECULAR	5
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	1.0	%	PMID[537669]
NPT1	Others	Radical scavenging activity		Activity	=	2.2	%	PMID[537669]
NPT1	Others	Radical scavenging activity		Activity	=	2.9	%	PMID[537669]
NPT1	Others	Radical scavenging activity		Activity	=	8.1	%	PMID[537669]
NPT1	Others	Radical scavenging activity		Activity	=	16.0	%	PMID[537669]
NPT1	Others	Radical scavenging activity		Activity	=	29.0	%	PMID[537669]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	7.6	%	PMID[537669]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	14.2	%	PMID[537669]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	20.2	%	PMID[537669]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	31.4	%	PMID[537669]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	43.3	%	PMID[537669]

☑ 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 NPC217180 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	287
0.1-0.2	1894
0.2-0.3	4964
0.3-0.4	11697
0.4-0.5	7504
0.5-0.6	9295
0.6-0.7	6291
0.7-0.8	669
0.8-0.85	79
0.85-0.9	14
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC312525
0.9817	High Similarity	NPC205523
0.885	High Similarity	NPC22678
0.8793	High Similarity	NPC227660
0.875	High Similarity	NPC118853
0.8718	High Similarity	NPC243704
0.8678	High Similarity	NPC473885
0.8678	High Similarity	NPC471074
0.8649	High Similarity	NPC42471
0.8644	High Similarity	NPC473969
0.8632	High Similarity	NPC131801
0.8621	High Similarity	NPC28054
0.8559	High Similarity	NPC21831
0.8559	High Similarity	NPC187547
0.8547	High Similarity	NPC476014
0.8547	High Similarity	NPC476031
0.85	High Similarity	NPC97566
0.8492	Intermediate Similarity	NPC473982
0.8487	Intermediate Similarity	NPC137710
0.8443	Intermediate Similarity	NPC65735
0.8443	Intermediate Similarity	NPC188377
0.843	Intermediate Similarity	NPC317217
0.8403	Intermediate Similarity	NPC206007
0.84	Intermediate Similarity	NPC59502
0.839	Intermediate Similarity	NPC79202
0.839	Intermediate Similarity	NPC59035
0.839	Intermediate Similarity	NPC474987
0.8376	Intermediate Similarity	NPC292036
0.8364	Intermediate Similarity	NPC156768
0.8333	Intermediate Similarity	NPC471521
0.8333	Intermediate Similarity	NPC473356
0.8319	Intermediate Similarity	NPC208906
0.8319	Intermediate Similarity	NPC144745
0.8308	Intermediate Similarity	NPC64157
0.8308	Intermediate Similarity	NPC215109
0.8308	Intermediate Similarity	NPC278832
0.8308	Intermediate Similarity	NPC170604
0.8293	Intermediate Similarity	NPC477965
0.8293	Intermediate Similarity	NPC477038
0.8279	Intermediate Similarity	NPC477967
0.8276	Intermediate Similarity	NPC105249
0.8268	Intermediate Similarity	NPC477645
0.825	Intermediate Similarity	NPC254958
0.825	Intermediate Similarity	NPC291619
0.824	Intermediate Similarity	NPC141059
0.8235	Intermediate Similarity	NPC45536
0.8226	Intermediate Similarity	NPC71274
0.8226	Intermediate Similarity	NPC75557
0.822	Intermediate Similarity	NPC252004
0.8211	Intermediate Similarity	NPC476351
0.8197	Intermediate Similarity	NPC1848
0.8182	Intermediate Similarity	NPC4898
0.8175	Intermediate Similarity	NPC329707
0.8168	Intermediate Similarity	NPC473268
0.816	Intermediate Similarity	NPC329922
0.816	Intermediate Similarity	NPC216810
0.816	Intermediate Similarity	NPC81912
0.816	Intermediate Similarity	NPC329694
0.816	Intermediate Similarity	NPC83301
0.816	Intermediate Similarity	NPC474260
0.8154	Intermediate Similarity	NPC265793
0.8151	Intermediate Similarity	NPC150895
0.813	Intermediate Similarity	NPC289911
0.813	Intermediate Similarity	NPC471549
0.813	Intermediate Similarity	NPC473379
0.813	Intermediate Similarity	NPC283284
0.8125	Intermediate Similarity	NPC136340
0.8125	Intermediate Similarity	NPC475092
0.8103	Intermediate Similarity	NPC177331
0.8099	Intermediate Similarity	NPC87466
0.8095	Intermediate Similarity	NPC474830
0.8095	Intermediate Similarity	NPC184391
0.808	Intermediate Similarity	NPC474829
0.808	Intermediate Similarity	NPC471559
0.8077	Intermediate Similarity	NPC106247
0.8065	Intermediate Similarity	NPC475818
0.8062	Intermediate Similarity	NPC15083
0.8051	Intermediate Similarity	NPC1811
0.8051	Intermediate Similarity	NPC26157
0.8049	Intermediate Similarity	NPC115859
0.8049	Intermediate Similarity	NPC474136
0.8033	Intermediate Similarity	NPC67345
0.8033	Intermediate Similarity	NPC244862
0.8031	Intermediate Similarity	NPC26532
0.8031	Intermediate Similarity	NPC477123
0.8031	Intermediate Similarity	NPC474438
0.8031	Intermediate Similarity	NPC474279
0.8031	Intermediate Similarity	NPC477966
0.8031	Intermediate Similarity	NPC477039
0.803	Intermediate Similarity	NPC307401
0.8016	Intermediate Similarity	NPC470858
0.8015	Intermediate Similarity	NPC209858
0.8	Intermediate Similarity	NPC11799
0.8	Intermediate Similarity	NPC141252
0.8	Intermediate Similarity	NPC146316
0.8	Intermediate Similarity	NPC178382
0.8	Intermediate Similarity	NPC470740
0.7985	Intermediate Similarity	NPC473983
0.7985	Intermediate Similarity	NPC201370
0.7984	Intermediate Similarity	NPC282230
0.7984	Intermediate Similarity	NPC263870
0.7984	Intermediate Similarity	NPC183348
0.7983	Intermediate Similarity	NPC53953
0.797	Intermediate Similarity	NPC130976
0.797	Intermediate Similarity	NPC472376
0.7969	Intermediate Similarity	NPC50583
0.7969	Intermediate Similarity	NPC208389
0.7967	Intermediate Similarity	NPC246214
0.7966	Intermediate Similarity	NPC54626
0.7966	Intermediate Similarity	NPC57879
0.7953	Intermediate Similarity	NPC476016
0.7953	Intermediate Similarity	NPC473355
0.7953	Intermediate Similarity	NPC290955
0.7953	Intermediate Similarity	NPC471554
0.7953	Intermediate Similarity	NPC137570
0.7953	Intermediate Similarity	NPC471501
0.7953	Intermediate Similarity	NPC471573
0.7953	Intermediate Similarity	NPC246392
0.7951	Intermediate Similarity	NPC293424
0.7937	Intermediate Similarity	NPC179354
0.7934	Intermediate Similarity	NPC76844
0.7934	Intermediate Similarity	NPC316062
0.7923	Intermediate Similarity	NPC470976
0.7923	Intermediate Similarity	NPC470977
0.7923	Intermediate Similarity	NPC196979
0.7923	Intermediate Similarity	NPC471817
0.792	Intermediate Similarity	NPC16922
0.791	Intermediate Similarity	NPC202260
0.7907	Intermediate Similarity	NPC66246
0.7907	Intermediate Similarity	NPC170546
0.7903	Intermediate Similarity	NPC79557
0.7891	Intermediate Similarity	NPC476917
0.7891	Intermediate Similarity	NPC279877
0.7891	Intermediate Similarity	NPC477040
0.7891	Intermediate Similarity	NPC327527
0.7879	Intermediate Similarity	NPC159786
0.7874	Intermediate Similarity	NPC23086
0.7869	Intermediate Similarity	NPC469954
0.7863	Intermediate Similarity	NPC293253
0.7857	Intermediate Similarity	NPC243269
0.7852	Intermediate Similarity	NPC148374
0.7851	Intermediate Similarity	NPC11821
0.7826	Intermediate Similarity	NPC56731
0.7823	Intermediate Similarity	NPC474817
0.782	Intermediate Similarity	NPC303217
0.7818	Intermediate Similarity	NPC233791
0.7815	Intermediate Similarity	NPC23332
0.7812	Intermediate Similarity	NPC83178
0.7812	Intermediate Similarity	NPC95567
0.7812	Intermediate Similarity	NPC319140
0.7805	Intermediate Similarity	NPC152159
0.7778	Intermediate Similarity	NPC233707
0.7778	Intermediate Similarity	NPC219969
0.7769	Intermediate Similarity	NPC476925
0.7769	Intermediate Similarity	NPC21460
0.7752	Intermediate Similarity	NPC207294
0.7752	Intermediate Similarity	NPC112706
0.7744	Intermediate Similarity	NPC324117
0.7737	Intermediate Similarity	NPC263337
0.7734	Intermediate Similarity	NPC46536
0.7734	Intermediate Similarity	NPC74612
0.7734	Intermediate Similarity	NPC473626
0.7734	Intermediate Similarity	NPC138139
0.7731	Intermediate Similarity	NPC183648
0.7727	Intermediate Similarity	NPC471006
0.7721	Intermediate Similarity	NPC282973
0.7714	Intermediate Similarity	NPC71821
0.771	Intermediate Similarity	NPC89133
0.771	Intermediate Similarity	NPC61788
0.771	Intermediate Similarity	NPC298190
0.771	Intermediate Similarity	NPC17681
0.7698	Intermediate Similarity	NPC245522
0.7698	Intermediate Similarity	NPC469642
0.7698	Intermediate Similarity	NPC270807
0.7698	Intermediate Similarity	NPC174915
0.7698	Intermediate Similarity	NPC114513
0.7698	Intermediate Similarity	NPC314329
0.7692	Intermediate Similarity	NPC298087
0.7687	Intermediate Similarity	NPC204592
0.7687	Intermediate Similarity	NPC146872
0.768	Intermediate Similarity	NPC230951
0.766	Intermediate Similarity	NPC93666
0.7656	Intermediate Similarity	NPC221798
0.7652	Intermediate Similarity	NPC97740
0.7652	Intermediate Similarity	NPC279596
0.7652	Intermediate Similarity	NPC473344
0.7652	Intermediate Similarity	NPC217226
0.7652	Intermediate Similarity	NPC471544
0.7652	Intermediate Similarity	NPC45358
0.7647	Intermediate Similarity	NPC474615
0.7647	Intermediate Similarity	NPC107571
0.7642	Intermediate Similarity	NPC470860
0.7634	Intermediate Similarity	NPC939
0.7634	Intermediate Similarity	NPC45947
0.7634	Intermediate Similarity	NPC238309
0.763	Intermediate Similarity	NPC286130
0.7627	Intermediate Similarity	NPC140688
0.7626	Intermediate Similarity	NPC218712
0.7626	Intermediate Similarity	NPC307346
0.7626	Intermediate Similarity	NPC261733

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 NPC217180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	1094
0.2-0.3	1607
0.3-0.4	2866
0.4-0.5	1986
0.5-0.6	1030
0.6-0.7	295
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8136	Intermediate Similarity	NPD1241	Discontinued
0.7698	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6832	Phase 2
0.7647	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3972	Approved
0.7462	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1019	Discontinued
0.7385	Intermediate Similarity	NPD1876	Approved
0.7364	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD3140	Approved
0.7333	Intermediate Similarity	NPD3142	Approved
0.7295	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1471	Phase 3
0.7266	Intermediate Similarity	NPD2344	Approved
0.725	Intermediate Similarity	NPD3134	Approved
0.7194	Intermediate Similarity	NPD2796	Approved
0.719	Intermediate Similarity	NPD1358	Approved
0.7172	Intermediate Similarity	NPD920	Approved
0.7165	Intermediate Similarity	NPD9092	Discovery
0.7163	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2798	Approved
0.7133	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2799	Discontinued
0.708	Intermediate Similarity	NPD4307	Phase 2
0.7068	Intermediate Similarity	NPD3267	Approved
0.7068	Intermediate Similarity	NPD1203	Approved
0.7068	Intermediate Similarity	NPD3266	Approved
0.7067	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2309	Approved
0.7063	Intermediate Similarity	NPD3887	Approved
0.7059	Intermediate Similarity	NPD2313	Discontinued
0.7055	Intermediate Similarity	NPD3869	Phase 3
0.7055	Intermediate Similarity	NPD3873	Phase 3
0.7042	Intermediate Similarity	NPD1243	Approved
0.704	Intermediate Similarity	NPD7843	Approved
0.7034	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1933	Approved
0.7	Intermediate Similarity	NPD3748	Approved
0.6993	Remote Similarity	NPD4628	Phase 3
0.6992	Remote Similarity	NPD2182	Approved
0.6992	Remote Similarity	NPD2684	Approved
0.6977	Remote Similarity	NPD9545	Approved
0.6963	Remote Similarity	NPD9494	Approved
0.696	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1551	Phase 2
0.694	Remote Similarity	NPD2797	Approved
0.6934	Remote Similarity	NPD3268	Approved
0.6933	Remote Similarity	NPD6280	Approved
0.6933	Remote Similarity	NPD6279	Approved
0.6923	Remote Similarity	NPD5585	Approved
0.6906	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD5535	Approved
0.6901	Remote Similarity	NPD2353	Approved
0.6901	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5536	Phase 2
0.6891	Remote Similarity	NPD1238	Approved
0.6885	Remote Similarity	NPD9697	Approved
0.6879	Remote Similarity	NPD4308	Phase 3
0.6875	Remote Similarity	NPD7157	Approved
0.687	Remote Similarity	NPD17	Approved
0.687	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1549	Phase 2
0.6849	Remote Similarity	NPD6799	Approved
0.6846	Remote Similarity	NPD1894	Discontinued
0.6822	Remote Similarity	NPD9493	Approved
0.6818	Remote Similarity	NPD919	Approved
0.6818	Remote Similarity	NPD3496	Discontinued
0.6812	Remote Similarity	NPD6798	Discontinued
0.6812	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD411	Approved
0.6803	Remote Similarity	NPD4662	Approved
0.6803	Remote Similarity	NPD4661	Approved
0.6794	Remote Similarity	NPD1651	Approved
0.6786	Remote Similarity	NPD447	Suspended
0.6783	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2346	Discontinued
0.6783	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7440	Discontinued
0.6765	Remote Similarity	NPD5647	Approved
0.6763	Remote Similarity	NPD8032	Phase 2
0.6759	Remote Similarity	NPD3750	Approved
0.6757	Remote Similarity	NPD6273	Approved
0.6742	Remote Similarity	NPD1778	Approved
0.6731	Remote Similarity	NPD1247	Approved
0.6716	Remote Similarity	NPD1608	Approved
0.6714	Remote Similarity	NPD1240	Approved
0.6713	Remote Similarity	NPD2935	Discontinued
0.6712	Remote Similarity	NPD2354	Approved
0.6711	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6362	Approved
0.669	Remote Similarity	NPD2654	Approved
0.6689	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6599	Discontinued
0.6688	Remote Similarity	NPD6808	Phase 2
0.6667	Remote Similarity	NPD4618	Approved
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD164	Approved
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4622	Approved
0.6667	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD4359	Approved
0.6667	Remote Similarity	NPD5760	Phase 2
0.6645	Remote Similarity	NPD7411	Suspended
0.6644	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2186	Approved
0.6643	Remote Similarity	NPD6233	Phase 2
0.6643	Remote Similarity	NPD1510	Phase 2
0.6643	Remote Similarity	NPD4062	Phase 3
0.664	Remote Similarity	NPD290	Approved
0.6625	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1607	Approved
0.6619	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7317	Phase 3
0.6601	Remote Similarity	NPD7577	Discontinued
0.6601	Remote Similarity	NPD6844	Discontinued
0.66	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5403	Approved
0.6596	Remote Similarity	NPD2979	Phase 3
0.6593	Remote Similarity	NPD1481	Phase 2
0.6582	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3882	Suspended
0.6577	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5401	Approved
0.6575	Remote Similarity	NPD2800	Approved
0.6573	Remote Similarity	NPD5689	Approved
0.6573	Remote Similarity	NPD5688	Approved
0.6571	Remote Similarity	NPD3764	Approved
0.6567	Remote Similarity	NPD3847	Discontinued
0.6566	Remote Similarity	NPD8434	Phase 2
0.6564	Remote Similarity	NPD6764	Approved
0.6564	Remote Similarity	NPD6559	Discontinued
0.6564	Remote Similarity	NPD6765	Approved
0.6561	Remote Similarity	NPD5494	Approved
0.656	Remote Similarity	NPD968	Approved
0.6552	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6005	Phase 3
0.6552	Remote Similarity	NPD6002	Phase 3
0.6552	Remote Similarity	NPD6004	Phase 3
0.6552	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3926	Phase 2
0.6538	Remote Similarity	NPD7075	Discontinued
0.6536	Remote Similarity	NPD5890	Approved
0.6536	Remote Similarity	NPD5889	Approved
0.6533	Remote Similarity	NPD5049	Phase 3
0.6531	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7033	Discontinued
0.6519	Remote Similarity	NPD6287	Discontinued
0.6519	Remote Similarity	NPD1281	Approved
0.6519	Remote Similarity	NPD1535	Discovery
0.6516	Remote Similarity	NPD7318	Phase 3
0.6516	Remote Similarity	NPD2296	Approved
0.6516	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7458	Discontinued
0.6513	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2649	Approved
0.6513	Remote Similarity	NPD2651	Approved
0.6512	Remote Similarity	NPD821	Approved
0.6507	Remote Similarity	NPD2424	Discontinued
0.6503	Remote Similarity	NPD6653	Approved
0.65	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD3225	Approved
0.6494	Remote Similarity	NPD6801	Discontinued
0.6489	Remote Similarity	NPD6671	Approved
0.6489	Remote Similarity	NPD2557	Approved
0.6486	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4476	Approved
0.6483	Remote Similarity	NPD4477	Approved
0.6475	Remote Similarity	NPD454	Approved
0.6474	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7768	Phase 2
0.6458	Remote Similarity	NPD743	Approved
0.6457	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD1296	Phase 2
0.6452	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD9261	Approved
0.6447	Remote Similarity	NPD957	Approved
0.6444	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3596	Phase 2
0.6438	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3749	Approved
0.6429	Remote Similarity	NPD2614	Approved
0.6423	Remote Similarity	NPD5327	Phase 3
0.642	Remote Similarity	NPD2163	Approved
0.6419	Remote Similarity	NPD7003	Approved
0.6419	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4110	Phase 3
0.6418	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5262	Discontinued
0.6407	Remote Similarity	NPD6785	Approved
0.6407	Remote Similarity	NPD6784	Approved
0.6406	Remote Similarity	NPD5451	Approved

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