NPASS Compound

Structure

NPC474659 OpenBabel07101718222D 25 29 0 0 1 0 0 0 0 0999 V2000 -2.6270 -2.4119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2051 -0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2051 -1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6327 -3.2478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5741 -2.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0925 -0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0925 -1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7967 -0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7967 -1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3884 -0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0484 -1.6173 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3884 -1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 -0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 -1.8262 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.1302 -2.6012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9898 -1.2800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -0.0995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9599 -0.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -1.9266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5009 0.8001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 -2.8262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0715 -2.9386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9751 0.8754 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 2 3 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 16 1 0 0 0 0 5 20 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 8 1 1 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 1 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 25 1 0 0 0 0 20 1 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	339.826
LogP:	1.512
LogD:	1.508
LogS:	-3.819
# Rotatable Bonds:	0
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	4.57
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.105
MDCK Permeability:	5.6419294196530245e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.801
20% Bioavailability (F20%):	0.852
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	79.0206069946289%
Volume Distribution (VD):	2.546
Pgp-substrate:	24.292720794677734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.094
CYP1A2-substrate:	0.703
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.625
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.212
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.345

ADMET: Excretion

Clearance (CL):	8.989
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.432
AMES Toxicity:	0.849
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.91
Carcinogencity:	0.911
Eye Corrosion:	0.003
Eye Irritation:	0.362
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC474659

Natural Product ID:	NPC474659
*Common Name:**	Xestosaprol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QBIVTXOPBMJYTJ-HLEOHGGJSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-20-5-4-16(23)12-8-25-19(17(12)20)18(24)11-6-9-10(7-13(11)20)15(22)3-2-14(9)21/h6-7,12,15-16,22-23H,2-5,8H2,1H3/t12-,15?,16-,20-/m0/s1
SMILES:	O[C@H]1CC[C@@]2(C3=C(OC[C@@H]13)C(=O)c1c2cc2C(O)CCC(=O)c2c1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478749
PubChem CID:	23427323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO32714	xestospongia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843588]
NPO32714	xestospongia	Genus	Petrosiidae	Eukaryota	n.a.	South Pacific	n.a.	PMID[20634081]

☑ 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	6
MIC	1
Others	2

Activity Type	# Activity
Cell Line	3
Individual Protein	2
Organism	2
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	MIC	=	12.5	ug.mL-1	PMID[527131]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	34.9	%	PMID[527131]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	30.1	%	PMID[527131]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	1000000.0	nM	PMID[527132]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	58000.0	nM	PMID[527132]
NPT2	Others	Unspecified		IC50	>	30000.0	nM	PMID[527132]
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	>	30000.0	nM	PMID[527132]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	>	29000.0	nM	PMID[527132]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	29000.0	nM	PMID[527132]

☑ 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 NPC474659 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	272
0.1-0.2	1153
0.2-0.3	2353
0.3-0.4	5664
0.4-0.5	11769
0.5-0.6	11728
0.6-0.7	8581
0.7-0.8	1153
0.8-0.85	18
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.969	High Similarity	NPC23894
0.9	High Similarity	NPC478165
0.9	High Similarity	NPC478162
0.8921	High Similarity	NPC478164
0.8794	High Similarity	NPC478160
0.8603	High Similarity	NPC310662
0.8542	High Similarity	NPC478163
0.8489	Intermediate Similarity	NPC475957
0.8321	Intermediate Similarity	NPC472981
0.8288	Intermediate Similarity	NPC5568
0.8271	Intermediate Similarity	NPC51079
0.8201	Intermediate Similarity	NPC203486
0.8201	Intermediate Similarity	NPC78307
0.8175	Intermediate Similarity	NPC49272
0.8168	Intermediate Similarity	NPC476645
0.8154	Intermediate Similarity	NPC323440
0.8154	Intermediate Similarity	NPC222968
0.8154	Intermediate Similarity	NPC80605
0.8146	Intermediate Similarity	NPC478159
0.8146	Intermediate Similarity	NPC478161
0.8134	Intermediate Similarity	NPC85511
0.8106	Intermediate Similarity	NPC238861
0.8106	Intermediate Similarity	NPC77000
0.8088	Intermediate Similarity	NPC169913
0.8088	Intermediate Similarity	NPC474106
0.8029	Intermediate Similarity	NPC51448
0.8029	Intermediate Similarity	NPC115797
0.8015	Intermediate Similarity	NPC275576
0.8014	Intermediate Similarity	NPC202225
0.8014	Intermediate Similarity	NPC212207
0.8	Intermediate Similarity	NPC328107
0.7985	Intermediate Similarity	NPC269923
0.7985	Intermediate Similarity	NPC167323
0.7969	Intermediate Similarity	NPC471188
0.7969	Intermediate Similarity	NPC471189
0.7961	Intermediate Similarity	NPC469966
0.7959	Intermediate Similarity	NPC245522
0.7959	Intermediate Similarity	NPC114513
0.7956	Intermediate Similarity	NPC81135
0.7955	Intermediate Similarity	NPC318173
0.7945	Intermediate Similarity	NPC248068
0.7943	Intermediate Similarity	NPC329913
0.7943	Intermediate Similarity	NPC126516
0.7943	Intermediate Similarity	NPC477139
0.7939	Intermediate Similarity	NPC469843
0.7933	Intermediate Similarity	NPC474310
0.7929	Intermediate Similarity	NPC471851
0.7926	Intermediate Similarity	NPC65627
0.7914	Intermediate Similarity	NPC262819
0.7914	Intermediate Similarity	NPC171460
0.791	Intermediate Similarity	NPC144547
0.7902	Intermediate Similarity	NPC38158
0.7883	Intermediate Similarity	NPC476599
0.7883	Intermediate Similarity	NPC236405
0.7867	Intermediate Similarity	NPC101043
0.7867	Intermediate Similarity	NPC306799
0.7852	Intermediate Similarity	NPC136878
0.7852	Intermediate Similarity	NPC143685
0.7847	Intermediate Similarity	NPC119542
0.7846	Intermediate Similarity	NPC241851
0.7846	Intermediate Similarity	NPC326664
0.7843	Intermediate Similarity	NPC88958
0.7838	Intermediate Similarity	NPC29932
0.7836	Intermediate Similarity	NPC472679
0.7836	Intermediate Similarity	NPC988
0.7836	Intermediate Similarity	NPC472680
0.7836	Intermediate Similarity	NPC289432
0.7832	Intermediate Similarity	NPC309056
0.7826	Intermediate Similarity	NPC473220
0.7826	Intermediate Similarity	NPC470753
0.7823	Intermediate Similarity	NPC308572
0.7817	Intermediate Similarity	NPC48929
0.781	Intermediate Similarity	NPC295664
0.781	Intermediate Similarity	NPC181334
0.7808	Intermediate Similarity	NPC472546
0.7808	Intermediate Similarity	NPC182869
0.7786	Intermediate Similarity	NPC471832
0.7786	Intermediate Similarity	NPC93181
0.7786	Intermediate Similarity	NPC215419
0.7778	Intermediate Similarity	NPC471670
0.7778	Intermediate Similarity	NPC39549
0.7778	Intermediate Similarity	NPC474311
0.7778	Intermediate Similarity	NPC282793
0.777	Intermediate Similarity	NPC78364
0.777	Intermediate Similarity	NPC84672
0.777	Intermediate Similarity	NPC316553
0.777	Intermediate Similarity	NPC72667
0.777	Intermediate Similarity	NPC69424
0.777	Intermediate Similarity	NPC176130
0.7769	Intermediate Similarity	NPC143768
0.7769	Intermediate Similarity	NPC470253
0.7755	Intermediate Similarity	NPC91703
0.7754	Intermediate Similarity	NPC470765
0.7752	Intermediate Similarity	NPC474057
0.7752	Intermediate Similarity	NPC265513
0.774	Intermediate Similarity	NPC224491
0.7737	Intermediate Similarity	NPC318067
0.7736	Intermediate Similarity	NPC472784
0.7733	Intermediate Similarity	NPC473215
0.773	Intermediate Similarity	NPC108129
0.773	Intermediate Similarity	NPC27659
0.7721	Intermediate Similarity	NPC293831
0.7721	Intermediate Similarity	NPC369
0.7718	Intermediate Similarity	NPC79627
0.771	Intermediate Similarity	NPC67377
0.771	Intermediate Similarity	NPC196673
0.7708	Intermediate Similarity	NPC472551
0.7708	Intermediate Similarity	NPC472545
0.7704	Intermediate Similarity	NPC105709
0.7704	Intermediate Similarity	NPC133389
0.7704	Intermediate Similarity	NPC473243
0.7704	Intermediate Similarity	NPC183339
0.7704	Intermediate Similarity	NPC234337
0.7698	Intermediate Similarity	NPC254492
0.7692	Intermediate Similarity	NPC254603
0.7687	Intermediate Similarity	NPC471853
0.7682	Intermediate Similarity	NPC470245
0.7682	Intermediate Similarity	NPC473214
0.7682	Intermediate Similarity	NPC478018
0.7671	Intermediate Similarity	NPC230811
0.7671	Intermediate Similarity	NPC472547
0.7671	Intermediate Similarity	NPC476643
0.7671	Intermediate Similarity	NPC173980
0.7667	Intermediate Similarity	NPC474630
0.7667	Intermediate Similarity	NPC478166
0.7664	Intermediate Similarity	NPC273336
0.7664	Intermediate Similarity	NPC182333
0.766	Intermediate Similarity	NPC131684
0.766	Intermediate Similarity	NPC303910
0.7656	Intermediate Similarity	NPC211439
0.7655	Intermediate Similarity	NPC193358
0.7652	Intermediate Similarity	NPC474095
0.7652	Intermediate Similarity	NPC470764
0.7652	Intermediate Similarity	NPC186933
0.7651	Intermediate Similarity	NPC100242
0.7651	Intermediate Similarity	NPC472556
0.7639	Intermediate Similarity	NPC477896
0.7639	Intermediate Similarity	NPC477893
0.7635	Intermediate Similarity	NPC477468
0.7632	Intermediate Similarity	NPC471103
0.7632	Intermediate Similarity	NPC473719
0.7632	Intermediate Similarity	NPC132810
0.7632	Intermediate Similarity	NPC192069
0.763	Intermediate Similarity	NPC204784
0.763	Intermediate Similarity	NPC202015
0.7626	Intermediate Similarity	NPC294050
0.7626	Intermediate Similarity	NPC328997
0.7622	Intermediate Similarity	NPC165612
0.7622	Intermediate Similarity	NPC472656
0.7616	Intermediate Similarity	NPC60509
0.7616	Intermediate Similarity	NPC81698
0.7616	Intermediate Similarity	NPC250046
0.7616	Intermediate Similarity	NPC476975
0.7616	Intermediate Similarity	NPC473403
0.7613	Intermediate Similarity	NPC179170
0.7609	Intermediate Similarity	NPC77691
0.7609	Intermediate Similarity	NPC472681
0.7609	Intermediate Similarity	NPC135062
0.7609	Intermediate Similarity	NPC471187
0.7606	Intermediate Similarity	NPC198305
0.7606	Intermediate Similarity	NPC72915
0.7606	Intermediate Similarity	NPC471334
0.7603	Intermediate Similarity	NPC198621
0.7603	Intermediate Similarity	NPC22676
0.7603	Intermediate Similarity	NPC118366
0.7603	Intermediate Similarity	NPC475482
0.7603	Intermediate Similarity	NPC216940
0.7597	Intermediate Similarity	NPC473670
0.7597	Intermediate Similarity	NPC21410
0.7594	Intermediate Similarity	NPC135730
0.7594	Intermediate Similarity	NPC226093
0.7591	Intermediate Similarity	NPC154696
0.7589	Intermediate Similarity	NPC3009
0.7586	Intermediate Similarity	NPC22644
0.7586	Intermediate Similarity	NPC472372
0.7586	Intermediate Similarity	NPC472374
0.7584	Intermediate Similarity	NPC477209
0.7576	Intermediate Similarity	NPC471721
0.7574	Intermediate Similarity	NPC232958
0.7574	Intermediate Similarity	NPC133302
0.7571	Intermediate Similarity	NPC71610
0.7571	Intermediate Similarity	NPC253681
0.7571	Intermediate Similarity	NPC51292
0.7569	Intermediate Similarity	NPC475346
0.7569	Intermediate Similarity	NPC115458
0.7569	Intermediate Similarity	NPC59459
0.7569	Intermediate Similarity	NPC53896
0.7569	Intermediate Similarity	NPC138472
0.7569	Intermediate Similarity	NPC18982
0.7569	Intermediate Similarity	NPC475457
0.7569	Intermediate Similarity	NPC111845
0.7569	Intermediate Similarity	NPC475627
0.7566	Intermediate Similarity	NPC198455
0.7566	Intermediate Similarity	NPC161239
0.7566	Intermediate Similarity	NPC7095
0.7566	Intermediate Similarity	NPC165260
0.7566	Intermediate Similarity	NPC52692
0.7557	Intermediate Similarity	NPC186128
0.7557	Intermediate Similarity	NPC292834
0.7554	Intermediate Similarity	NPC164014

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 NPC474659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	825
0.2-0.3	1372
0.3-0.4	2710
0.4-0.5	2424
0.5-0.6	1250
0.6-0.7	314
0.7-0.8	17
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8106	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7236	Approved
0.7867	Intermediate Similarity	NPD7239	Suspended
0.766	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD5951	Approved
0.7574	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7961	Discontinued
0.7535	Intermediate Similarity	NPD7008	Discontinued
0.7481	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7057	Phase 3
0.7405	Intermediate Similarity	NPD7058	Phase 2
0.7388	Intermediate Similarity	NPD2629	Approved
0.7324	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1237	Approved
0.7285	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD6273	Approved
0.7244	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7610	Discontinued
0.7197	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2932	Approved
0.7194	Intermediate Similarity	NPD3019	Approved
0.7163	Intermediate Similarity	NPD4878	Approved
0.7143	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7799	Discontinued
0.7075	Intermediate Similarity	NPD6663	Approved
0.7067	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5736	Approved
0.7025	Intermediate Similarity	NPD7458	Discontinued
0.702	Intermediate Similarity	NPD5405	Approved
0.702	Intermediate Similarity	NPD5404	Approved
0.702	Intermediate Similarity	NPD5408	Approved
0.702	Intermediate Similarity	NPD5406	Approved
0.7014	Intermediate Similarity	NPD1470	Approved
0.6987	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6858	Approved
0.6985	Remote Similarity	NPD7094	Approved
0.6974	Remote Similarity	NPD2346	Discontinued
0.6974	Remote Similarity	NPD1471	Phase 3
0.6963	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4198	Discontinued
0.6953	Remote Similarity	NPD3495	Discontinued
0.6929	Remote Similarity	NPD7009	Phase 2
0.6918	Remote Similarity	NPD3226	Approved
0.6901	Remote Similarity	NPD3023	Approved
0.6901	Remote Similarity	NPD3026	Approved
0.6901	Remote Similarity	NPD4879	Approved
0.6884	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3025	Approved
0.6879	Remote Similarity	NPD3024	Approved
0.6879	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1201	Approved
0.6839	Remote Similarity	NPD4628	Phase 3
0.6839	Remote Similarity	NPD8434	Phase 2
0.6818	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1930	Approved
0.6818	Remote Similarity	NPD1929	Approved
0.6815	Remote Similarity	NPD7390	Discontinued
0.681	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7741	Discontinued
0.6809	Remote Similarity	NPD3091	Approved
0.6779	Remote Similarity	NPD3764	Approved
0.6772	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2067	Discontinued
0.6753	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8150	Discontinued
0.6732	Remote Similarity	NPD2799	Discontinued
0.6718	Remote Similarity	NPD2066	Phase 3
0.6713	Remote Similarity	NPD3095	Discontinued
0.6708	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6959	Discontinued
0.6692	Remote Similarity	NPD6647	Phase 2
0.6692	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2182	Approved
0.669	Remote Similarity	NPD3972	Approved
0.6685	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5844	Phase 1
0.6648	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6765	Approved
0.6647	Remote Similarity	NPD8368	Discontinued
0.6647	Remote Similarity	NPD6764	Approved
0.6646	Remote Similarity	NPD5760	Phase 2
0.6646	Remote Similarity	NPD5761	Phase 2
0.6646	Remote Similarity	NPD3300	Phase 2
0.6645	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8407	Phase 2
0.6626	Remote Similarity	NPD7411	Suspended
0.6624	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3750	Approved
0.6623	Remote Similarity	NPD7714	Approved
0.6623	Remote Similarity	NPD7713	Phase 3
0.6623	Remote Similarity	NPD7305	Phase 1
0.6623	Remote Similarity	NPD7715	Approved
0.6621	Remote Similarity	NPD3092	Approved
0.6621	Remote Similarity	NPD6287	Discontinued
0.6599	Remote Similarity	NPD1283	Approved
0.6599	Remote Similarity	NPD1876	Approved
0.6596	Remote Similarity	NPD3317	Approved
0.6587	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2935	Discontinued
0.6579	Remote Similarity	NPD4140	Approved
0.6573	Remote Similarity	NPD8435	Approved
0.6573	Remote Similarity	NPD8361	Approved
0.6573	Remote Similarity	NPD8360	Approved
0.6571	Remote Similarity	NPD8312	Approved
0.6571	Remote Similarity	NPD8313	Approved
0.657	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6599	Discontinued
0.6564	Remote Similarity	NPD4380	Phase 2
0.6562	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2313	Discontinued
0.6556	Remote Similarity	NPD3268	Approved
0.6545	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7819	Suspended
0.6536	Remote Similarity	NPD6355	Discontinued
0.6532	Remote Similarity	NPD4956	Approved
0.6531	Remote Similarity	NPD5157	Phase 1
0.6531	Remote Similarity	NPD5159	Phase 2
0.6531	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD1651	Approved
0.6527	Remote Similarity	NPD7075	Discontinued
0.6519	Remote Similarity	NPD5909	Discontinued
0.6513	Remote Similarity	NPD8032	Phase 2
0.651	Remote Similarity	NPD2798	Approved
0.6509	Remote Similarity	NPD8127	Discontinued
0.6497	Remote Similarity	NPD6784	Approved
0.6497	Remote Similarity	NPD6785	Approved
0.6493	Remote Similarity	NPD1932	Approved
0.6485	Remote Similarity	NPD6801	Discontinued
0.6485	Remote Similarity	NPD37	Approved
0.6483	Remote Similarity	NPD5126	Approved
0.6483	Remote Similarity	NPD5125	Phase 3
0.6478	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6099	Approved
0.6474	Remote Similarity	NPD6100	Approved
0.6474	Remote Similarity	NPD2438	Suspended
0.6471	Remote Similarity	NPD2979	Phase 3
0.6471	Remote Similarity	NPD4060	Phase 1
0.6467	Remote Similarity	NPD4966	Approved
0.6467	Remote Similarity	NPD4965	Approved
0.6467	Remote Similarity	NPD4967	Phase 2
0.646	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5039	Approved
0.6456	Remote Similarity	NPD2800	Approved
0.6454	Remote Similarity	NPD6010	Discontinued
0.6453	Remote Similarity	NPD7473	Discontinued
0.6449	Remote Similarity	NPD2329	Discontinued
0.6448	Remote Similarity	NPD8485	Approved
0.6447	Remote Similarity	NPD6798	Discontinued
0.6429	Remote Similarity	NPD6535	Approved
0.6429	Remote Similarity	NPD6534	Approved
0.641	Remote Similarity	NPD4308	Phase 3
0.641	Remote Similarity	NPD3748	Approved
0.6407	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD5402	Approved
0.6404	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6085	Phase 2
0.64	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD164	Approved
0.6395	Remote Similarity	NPD1281	Approved
0.6395	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD9495	Approved
0.6389	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4097	Suspended
0.6385	Remote Similarity	NPD7631	Approved
0.6382	Remote Similarity	NPD6966	Discovery
0.638	Remote Similarity	NPD5403	Approved
0.6375	Remote Similarity	NPD6190	Approved
0.6374	Remote Similarity	NPD6232	Discontinued
0.637	Remote Similarity	NPD5305	Approved
0.637	Remote Similarity	NPD5306	Approved
0.637	Remote Similarity	NPD4626	Approved
0.6369	Remote Similarity	NPD3882	Suspended
0.6369	Remote Similarity	NPD7768	Phase 2
0.6364	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3620	Phase 2
0.6364	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7028	Phase 2
0.6364	Remote Similarity	NPD5030	Phase 2
0.6353	Remote Similarity	NPD5494	Approved
0.6347	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6780	Approved
0.6344	Remote Similarity	NPD6776	Approved
0.6344	Remote Similarity	NPD6778	Approved
0.6344	Remote Similarity	NPD6782	Approved
0.6344	Remote Similarity	NPD6777	Approved
0.6344	Remote Similarity	NPD6779	Approved
0.6344	Remote Similarity	NPD6781	Approved
0.6336	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2797	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