NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	452.26
Volume:	475.757
LogP:	5.289
LogD:	5.057
LogS:	-3.504
# Rotatable Bonds:	13
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	4.336
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	1.9935901946155354e-05
Pgp-inhibitor:	0.634
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.444
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	96.75052642822266%
Volume Distribution (VD):	1.925
Pgp-substrate:	1.617795467376709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.387
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.62
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.089

ADMET: Excretion

Clearance (CL):	4.54
Half-life (T1/2):	0.032

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.732
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.93
Carcinogencity:	0.659
Eye Corrosion:	0.959
Eye Irritation:	0.791
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC477038

Natural Product ID:	NPC477038
*Common Name:**	[amino(dimethylamino)methylidene]azanium (5E)-2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-en-1-yl sulfate
IUPAC Name:	[(E)-2-[3-(furan-3-yl)propyl]-6-methyl-8-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]oct-5-enyl] sulfate
Synonyms:
Standard InCHIKey:	GCCDIQCRJHCDFR-RVGQIHGBSA-M
Standard InCHI:	InChI=1S/C25H40O5S/c1-20(14-16-25(4)21(2)9-6-10-22(25)3)8-5-11-23(19-30-31(26,27)28)12-7-13-24-15-17-29-18-24/h8-9,15,17-18,22-23H,5-7,10-14,16,19H2,1-4H3,(H,26,27,28)/p-1/b20-8+/t22-,23?,25-/m1/s1
SMILES:	C[C@@H]1CCC=C([C@@]1(C)CC/C(=C/CCC(CCCC2=COC=C2)COS(=O)(=O)[O-])/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484213
PubChem CID:	91934922
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
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]

☑ 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
MIC	6

Activity Type	# Activity
Individual Protein	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	185500	nM	PMID[18824352]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	185500	nM	PMID[18824352]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100	ug/ml	PMID[18824352]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	6.25	ug/ml	PMID[18824352]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100	ug/ml	PMID[18824352]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	25	ug/ml	PMID[18824352]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100	ug/ml	PMID[18824352]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100	ug/ml	PMID[18824352]

☑ 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 NPC477038 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	163
0.1-0.2	1203
0.2-0.3	4730
0.3-0.4	13291
0.4-0.5	12495
0.5-0.6	10015
0.6-0.7	670
0.7-0.8	120
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477965
0.9828	High Similarity	NPC317217
0.9667	High Similarity	NPC477039
0.9667	High Similarity	NPC477123
0.9667	High Similarity	NPC477966
0.9504	High Similarity	NPC477040
0.935	High Similarity	NPC476925
0.9328	High Similarity	NPC477967
0.9187	High Similarity	NPC476917
0.9187	High Similarity	NPC327527
0.8898	High Similarity	NPC150895
0.8871	High Similarity	NPC23086
0.8833	High Similarity	NPC243704
0.88	High Similarity	NPC83178
0.879	High Similarity	NPC179354
0.878	High Similarity	NPC16922
0.873	High Similarity	NPC207294
0.873	High Similarity	NPC112706
0.872	High Similarity	NPC46536
0.872	High Similarity	NPC138139
0.8672	High Similarity	NPC89133
0.8595	High Similarity	NPC144745
0.8595	High Similarity	NPC208906
0.8571	High Similarity	NPC74612
0.8527	High Similarity	NPC61788
0.8492	Intermediate Similarity	NPC471074
0.8492	Intermediate Similarity	NPC473885
0.8462	Intermediate Similarity	NPC471817
0.8413	Intermediate Similarity	NPC243269
0.8397	Intermediate Similarity	NPC218838
0.8385	Intermediate Similarity	NPC298190
0.8306	Intermediate Similarity	NPC473969
0.8295	Intermediate Similarity	NPC26532
0.8293	Intermediate Similarity	NPC312525
0.8293	Intermediate Similarity	NPC217180
0.8293	Intermediate Similarity	NPC212918
0.8279	Intermediate Similarity	NPC28054
0.8271	Intermediate Similarity	NPC158525
0.8271	Intermediate Similarity	NPC92941
0.8271	Intermediate Similarity	NPC476947
0.8258	Intermediate Similarity	NPC471006
0.8258	Intermediate Similarity	NPC470740
0.8254	Intermediate Similarity	NPC36255
0.8231	Intermediate Similarity	NPC59502
0.8226	Intermediate Similarity	NPC87466
0.8217	Intermediate Similarity	NPC246392
0.8217	Intermediate Similarity	NPC290955
0.8209	Intermediate Similarity	NPC146872
0.8203	Intermediate Similarity	NPC71274
0.8203	Intermediate Similarity	NPC303010
0.8203	Intermediate Similarity	NPC230979
0.8203	Intermediate Similarity	NPC75557
0.8189	Intermediate Similarity	NPC272899
0.8182	Intermediate Similarity	NPC473982
0.8175	Intermediate Similarity	NPC97566
0.8162	Intermediate Similarity	NPC90953
0.8154	Intermediate Similarity	NPC279877
0.8151	Intermediate Similarity	NPC471521
0.8151	Intermediate Similarity	NPC473356
0.8148	Intermediate Similarity	NPC470742
0.8148	Intermediate Similarity	NPC310830
0.8145	Intermediate Similarity	NPC131801
0.814	Intermediate Similarity	NPC329922
0.814	Intermediate Similarity	NPC81912
0.814	Intermediate Similarity	NPC329694
0.814	Intermediate Similarity	NPC474260
0.813	Intermediate Similarity	NPC205523
0.8125	Intermediate Similarity	NPC118853
0.8125	Intermediate Similarity	NPC188377
0.8125	Intermediate Similarity	NPC130275
0.8125	Intermediate Similarity	NPC65735
0.8125	Intermediate Similarity	NPC83115
0.811	Intermediate Similarity	NPC471549
0.811	Intermediate Similarity	NPC473379
0.8102	Intermediate Similarity	NPC67003
0.8102	Intermediate Similarity	NPC56197
0.8099	Intermediate Similarity	NPC105249
0.8092	Intermediate Similarity	NPC120836
0.8092	Intermediate Similarity	NPC223063
0.8092	Intermediate Similarity	NPC208389
0.8088	Intermediate Similarity	NPC236532
0.8088	Intermediate Similarity	NPC220094
0.8083	Intermediate Similarity	NPC177331
0.8077	Intermediate Similarity	NPC95567
0.8077	Intermediate Similarity	NPC474830
0.8077	Intermediate Similarity	NPC476016
0.8077	Intermediate Similarity	NPC319140
0.8074	Intermediate Similarity	NPC46896
0.8065	Intermediate Similarity	NPC45536
0.8062	Intermediate Similarity	NPC474829
0.8047	Intermediate Similarity	NPC476351
0.8033	Intermediate Similarity	NPC1811
0.8033	Intermediate Similarity	NPC26157
0.8015	Intermediate Similarity	NPC215109
0.8015	Intermediate Similarity	NPC329707
0.8015	Intermediate Similarity	NPC474438
0.8015	Intermediate Similarity	NPC474279
0.8015	Intermediate Similarity	NPC42400
0.8015	Intermediate Similarity	NPC170604
0.7986	Intermediate Similarity	NPC121158
0.7971	Intermediate Similarity	NPC90296
0.7969	Intermediate Similarity	NPC283284
0.7969	Intermediate Similarity	NPC289911
0.7956	Intermediate Similarity	NPC476943
0.7956	Intermediate Similarity	NPC472376
0.7955	Intermediate Similarity	NPC198904
0.7951	Intermediate Similarity	NPC277525
0.7943	Intermediate Similarity	NPC185456
0.7929	Intermediate Similarity	NPC476946
0.7923	Intermediate Similarity	NPC471559
0.7914	Intermediate Similarity	NPC205765
0.791	Intermediate Similarity	NPC471995
0.7907	Intermediate Similarity	NPC475818
0.7899	Intermediate Similarity	NPC202260
0.7895	Intermediate Similarity	NPC21460
0.7891	Intermediate Similarity	NPC474136
0.7891	Intermediate Similarity	NPC1848
0.7883	Intermediate Similarity	NPC307401
0.7874	Intermediate Similarity	NPC137710
0.7872	Intermediate Similarity	NPC238843
0.7872	Intermediate Similarity	NPC199044
0.7872	Intermediate Similarity	NPC142113
0.7857	Intermediate Similarity	NPC52412
0.7857	Intermediate Similarity	NPC473152
0.7852	Intermediate Similarity	NPC474407
0.7852	Intermediate Similarity	NPC474426
0.7852	Intermediate Similarity	NPC474425
0.7842	Intermediate Similarity	NPC148374
0.7832	Intermediate Similarity	NPC471174
0.7832	Intermediate Similarity	NPC302987
0.7829	Intermediate Similarity	NPC263870
0.7817	Intermediate Similarity	NPC5676
0.7812	Intermediate Similarity	NPC474817
0.7803	Intermediate Similarity	NPC471501
0.7803	Intermediate Similarity	NPC473355
0.7803	Intermediate Similarity	NPC137570
0.7803	Intermediate Similarity	NPC471573
0.7803	Intermediate Similarity	NPC471554
0.7801	Intermediate Similarity	NPC80635
0.7801	Intermediate Similarity	NPC470741
0.7801	Intermediate Similarity	NPC267632
0.7801	Intermediate Similarity	NPC243577
0.7801	Intermediate Similarity	NPC223415
0.7786	Intermediate Similarity	NPC300098
0.7786	Intermediate Similarity	NPC290193
0.7762	Intermediate Similarity	NPC470999
0.7762	Intermediate Similarity	NPC346
0.7762	Intermediate Similarity	NPC471292
0.7754	Intermediate Similarity	NPC186626
0.7752	Intermediate Similarity	NPC79557
0.7746	Intermediate Similarity	NPC251865
0.7746	Intermediate Similarity	NPC476944
0.773	Intermediate Similarity	NPC263337
0.7724	Intermediate Similarity	NPC234494
0.7724	Intermediate Similarity	NPC470998
0.7721	Intermediate Similarity	NPC293253
0.7714	Intermediate Similarity	NPC201370
0.7714	Intermediate Similarity	NPC473983
0.771	Intermediate Similarity	NPC178382
0.7708	Intermediate Similarity	NPC216755
0.7708	Intermediate Similarity	NPC476938
0.7708	Intermediate Similarity	NPC476937
0.7708	Intermediate Similarity	NPC255414
0.7708	Intermediate Similarity	NPC250228
0.7704	Intermediate Similarity	NPC17681
0.7671	Intermediate Similarity	NPC196846
0.7671	Intermediate Similarity	NPC470997
0.7664	Intermediate Similarity	NPC471998
0.766	Intermediate Similarity	NPC20500
0.7655	Intermediate Similarity	NPC476942
0.7655	Intermediate Similarity	NPC471007
0.7655	Intermediate Similarity	NPC476941
0.7647	Intermediate Similarity	NPC473344
0.7647	Intermediate Similarity	NPC45358
0.7647	Intermediate Similarity	NPC97740
0.7647	Intermediate Similarity	NPC471544
0.7639	Intermediate Similarity	NPC276676
0.7626	Intermediate Similarity	NPC473268
0.7619	Intermediate Similarity	NPC272590
0.7603	Intermediate Similarity	NPC69647
0.7603	Intermediate Similarity	NPC125182
0.7603	Intermediate Similarity	NPC472654
0.7603	Intermediate Similarity	NPC471001
0.76	Intermediate Similarity	NPC22678
0.7586	Intermediate Similarity	NPC10088
0.7586	Intermediate Similarity	NPC470941
0.7586	Intermediate Similarity	NPC71821
0.7578	Intermediate Similarity	NPC227660
0.7574	Intermediate Similarity	NPC477645
0.7571	Intermediate Similarity	NPC471996
0.7569	Intermediate Similarity	NPC56731
0.7569	Intermediate Similarity	NPC34056
0.7568	Intermediate Similarity	NPC246164
0.7568	Intermediate Similarity	NPC470996
0.7568	Intermediate Similarity	NPC33938
0.7568	Intermediate Similarity	NPC469503
0.7551	Intermediate Similarity	NPC212257
0.7551	Intermediate Similarity	NPC159927
0.7551	Intermediate Similarity	NPC46551
0.7551	Intermediate Similarity	NPC469335

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 NPC477038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	703
0.2-0.3	1531
0.3-0.4	3113
0.4-0.5	2623
0.5-0.6	1019
0.6-0.7	41
0.7-0.8	0
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
0.7351	Intermediate Similarity	NPD5760	Phase 2
0.7351	Intermediate Similarity	NPD5761	Phase 2
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1241	Discontinued
0.6985	Remote Similarity	NPD3972	Approved
0.6929	Remote Similarity	NPD6832	Phase 2
0.6887	Remote Similarity	NPD6273	Approved
0.6884	Remote Similarity	NPD1876	Approved
0.6803	Remote Similarity	NPD1471	Phase 3
0.6788	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2799	Discontinued
0.6779	Remote Similarity	NPD4628	Phase 3
0.6769	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2344	Approved
0.6687	Remote Similarity	NPD6765	Approved
0.6687	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD2798	Approved
0.6642	Remote Similarity	NPD7157	Approved
0.6619	Remote Similarity	NPD9717	Approved
0.6615	Remote Similarity	NPD2182	Approved
0.66	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2797	Approved
0.6588	Remote Similarity	NPD8434	Phase 2
0.6575	Remote Similarity	NPD6355	Discontinued
0.6569	Remote Similarity	NPD5585	Approved
0.6556	Remote Similarity	NPD7003	Approved
0.6556	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1019	Discontinued
0.6522	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD920	Approved
0.6513	Remote Similarity	NPD2309	Approved
0.6507	Remote Similarity	NPD3142	Approved
0.6507	Remote Similarity	NPD3140	Approved
0.6489	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2313	Discontinued
0.6483	Remote Similarity	NPD3268	Approved
0.6479	Remote Similarity	NPD3266	Approved
0.6479	Remote Similarity	NPD3267	Approved
0.6475	Remote Similarity	NPD3026	Approved
0.6475	Remote Similarity	NPD3023	Approved
0.6471	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2346	Discontinued
0.6462	Remote Similarity	NPD3134	Approved
0.6454	Remote Similarity	NPD5327	Phase 3
0.6443	Remote Similarity	NPD3748	Approved
0.6438	Remote Similarity	NPD4062	Phase 3
0.6433	Remote Similarity	NPD6785	Approved
0.6433	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6784	Approved
0.6433	Remote Similarity	NPD7458	Discontinued
0.6418	Remote Similarity	NPD7843	Approved
0.6414	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD17	Approved
0.64	Remote Similarity	NPD2531	Phase 2
0.64	Remote Similarity	NPD2796	Approved
0.6395	Remote Similarity	NPD4307	Phase 2
0.6395	Remote Similarity	NPD2979	Phase 3
0.6392	Remote Similarity	NPD6599	Discontinued
0.6387	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1608	Approved
0.6375	Remote Similarity	NPD7819	Suspended
0.6364	Remote Similarity	NPD6362	Approved
0.6364	Remote Similarity	NPD2684	Approved
0.6364	Remote Similarity	NPD7440	Discontinued
0.6364	Remote Similarity	NPD1203	Approved
0.6358	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6005	Phase 3
0.6358	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6004	Phase 3
0.6358	Remote Similarity	NPD6002	Phase 3
0.6357	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD3496	Discontinued
0.6351	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.634	Remote Similarity	NPD3750	Approved
0.634	Remote Similarity	NPD4110	Phase 3
0.634	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4359	Approved
0.6333	Remote Similarity	NPD4308	Phase 3
0.6331	Remote Similarity	NPD5691	Approved
0.6331	Remote Similarity	NPD1651	Approved
0.6331	Remote Similarity	NPD3024	Approved
0.6331	Remote Similarity	NPD3025	Approved
0.6319	Remote Similarity	NPD5647	Approved
0.6312	Remote Similarity	NPD1281	Approved
0.6312	Remote Similarity	NPD6280	Approved
0.6312	Remote Similarity	NPD6279	Approved
0.6308	Remote Similarity	NPD164	Approved
0.6306	Remote Similarity	NPD3873	Phase 3
0.6306	Remote Similarity	NPD3869	Phase 3
0.6299	Remote Similarity	NPD3887	Approved
0.6294	Remote Similarity	NPD1283	Approved
0.6294	Remote Similarity	NPD8651	Approved
0.6291	Remote Similarity	NPD1551	Phase 2
0.6291	Remote Similarity	NPD2935	Discontinued
0.6291	Remote Similarity	NPD4476	Approved
0.6291	Remote Similarity	NPD4477	Approved
0.6288	Remote Similarity	NPD1358	Approved
0.6286	Remote Similarity	NPD1778	Approved
0.6284	Remote Similarity	NPD4140	Approved
0.6276	Remote Similarity	NPD9494	Approved
0.6275	Remote Similarity	NPD1243	Approved
0.6275	Remote Similarity	NPD2800	Approved
0.6259	Remote Similarity	NPD1894	Discontinued
0.6259	Remote Similarity	NPD9545	Approved
0.6259	Remote Similarity	NPD6798	Discontinued
0.6259	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD3764	Approved
0.625	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1933	Approved
0.6242	Remote Similarity	NPD4618	Approved
0.6242	Remote Similarity	NPD4622	Approved
0.6242	Remote Similarity	NPD8127	Discontinued
0.6235	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD8166	Discontinued
0.622	Remote Similarity	NPD919	Approved
0.6218	Remote Similarity	NPD6799	Approved
0.6211	Remote Similarity	NPD7577	Discontinued
0.6209	Remote Similarity	NPD1549	Phase 2
0.62	Remote Similarity	NPD6653	Approved
0.6196	Remote Similarity	NPD7768	Phase 2
0.619	Remote Similarity	NPD7095	Approved
0.6188	Remote Similarity	NPD7028	Phase 2
0.6187	Remote Similarity	NPD9092	Discovery
0.6184	Remote Similarity	NPD2438	Suspended
0.6184	Remote Similarity	NPD6100	Approved
0.6184	Remote Similarity	NPD6099	Approved
0.6182	Remote Similarity	NPD5494	Approved
0.6178	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD4662	Approved
0.6178	Remote Similarity	NPD4661	Approved
0.6178	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5535	Approved
0.6173	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4626	Approved
0.6159	Remote Similarity	NPD5688	Approved
0.6159	Remote Similarity	NPD6387	Discontinued
0.6159	Remote Similarity	NPD5689	Approved
0.6154	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1296	Phase 2
0.6149	Remote Similarity	NPD6873	Phase 2
0.6149	Remote Similarity	NPD411	Approved
0.6149	Remote Similarity	NPD7411	Suspended
0.6145	Remote Similarity	NPD1247	Approved
0.6144	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD2353	Approved
0.6139	Remote Similarity	NPD5049	Phase 3
0.6133	Remote Similarity	NPD447	Suspended
0.6133	Remote Similarity	NPD5735	Approved
0.6125	Remote Similarity	NPD3226	Approved
0.6125	Remote Similarity	NPD2651	Approved
0.6125	Remote Similarity	NPD2649	Approved
0.6124	Remote Similarity	NPD1238	Approved
0.6115	Remote Similarity	NPD9493	Approved
0.6108	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6808	Phase 2
0.6107	Remote Similarity	NPD6233	Phase 2
0.6107	Remote Similarity	NPD4870	Approved
0.6105	Remote Similarity	NPD6559	Discontinued
0.6104	Remote Similarity	NPD4534	Discontinued
0.6101	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD6651	Approved
0.6093	Remote Similarity	NPD6353	Approved
0.609	Remote Similarity	NPD2354	Approved
0.6087	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5712	Approved
0.6076	Remote Similarity	NPD2532	Approved
0.6076	Remote Similarity	NPD2534	Approved
0.6076	Remote Similarity	NPD2533	Approved
0.6076	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD6696	Suspended
0.6067	Remote Similarity	NPD4060	Phase 1
0.6067	Remote Similarity	NPD1240	Approved
0.6061	Remote Similarity	NPD7075	Discontinued
0.6061	Remote Similarity	NPD3749	Approved
0.6056	Remote Similarity	NPD2932	Approved
0.6053	Remote Similarity	NPD7097	Phase 1
0.6051	Remote Similarity	NPD7236	Approved
0.6049	Remote Similarity	NPD6677	Suspended
0.6042	Remote Similarity	NPD1481	Phase 2
0.604	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD5762	Approved
0.6039	Remote Similarity	NPD5763	Approved
0.6037	Remote Similarity	NPD7318	Phase 3
0.6037	Remote Similarity	NPD2296	Approved
0.6036	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD9697	Approved
0.6014	Remote Similarity	NPD2614	Approved
0.6014	Remote Similarity	NPD3847	Discontinued
0.6013	Remote Similarity	NPD1510	Phase 2
0.6013	Remote Similarity	NPD7033	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