NPASS Compound

Structure

NPC471653 OpenBabel07101719522D 39 40 0 0 0 0 0 0 0 0999 V2000 13.6929 1.7096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9210 3.7507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.9582 0.3427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5827 5.2370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3765 0.4312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3685 1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6711 1.5017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9428 3.5428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3328 0.0154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9865 3.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9840 -0.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3110 -0.1925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2956 4.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6637 -0.7277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 2.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7930 -1.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0704 -1.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0164 -1.2630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2951 -1.7242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6370 -0.2460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9801 0.5506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2737 4.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6855 -0.5198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6994 1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4291 -1.2242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0383 -1.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5155 -1.6309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3479 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7065 -1.0431 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2614 -0.6810 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4110 -2.6255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2433 -2.0823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6315 -0.1415 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 7 2 0 0 0 0 2 8 2 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 24 2 0 0 0 0 13 25 2 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 34 1 0 0 0 0 17 35 1 0 0 0 0 18 26 2 0 0 0 0 18 30 1 0 0 0 0 19 27 2 0 0 0 0 19 31 1 0 0 0 0 20 28 1 0 0 0 0 20 30 2 0 0 0 0 21 29 1 0 0 0 0 21 31 2 0 0 0 0 22 28 2 0 0 0 0 22 38 1 0 0 0 0 23 29 2 0 0 0 0 23 39 1 0 0 0 0 28 32 1 0 0 0 0 29 33 1 0 0 0 0 30 38 1 0 0 0 0 31 39 1 0 0 0 0 32 34 2 3 0 0 0 32 36 1 0 0 0 0 33 35 2 3 0 0 0 33 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.31
Volume:	587.728
LogP:	6.505
LogD:	4.821
LogS:	-4.087
# Rotatable Bonds:	18
TPSA:	84.48
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.17
Synthetic Accessibility Score:	3.7
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
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:	-5.278
MDCK Permeability:	3.728016963577829e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.631
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	99.73453521728516%
Volume Distribution (VD):	2.732
Pgp-substrate:	1.8699493408203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.404
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.588
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.549
CYP2D6-substrate:	0.375
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	5.79
Half-life (T1/2):	0.479

ADMET: Toxicity

hERG Blockers:	0.551
Human Hepatotoxicity (H-HT):	0.584
Drug-inuced Liver Injury (DILI):	0.421
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.251
Carcinogencity:	0.777
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.357

Download Data

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

Natural Product: NPC471653

Natural Product ID:	NPC471653
*Common Name:**	N,N'-(Propane-1,3-Diyl)Bis(5-((1E,5Z)-2,6-Dimethylocta-1,5,7-Trienyl)Furan-3-Carboxamide)
IUPAC Name:	5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]-N-[3-[[5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]furan-3-carbonyl]amino]propyl]furan-3-carboxamide
Synonyms:
Standard InCHIKey:	HLOHLOSTEKPYDT-LJZFPECVSA-N
Standard InCHI:	InChI=1S/C33H42N2O4/c1-7-24(3)12-9-14-26(5)18-30-20-28(22-38-30)32(36)34-16-11-17-35-33(37)29-21-31(39-23-29)19-27(6)15-10-13-25(4)8-2/h7-8,12-13,18-23H,1-2,9-11,14-17H2,3-6H3,(H,34,36)(H,35,37)/b24-12-,25-13-,26-18+,27-19+
SMILES:	CC(=CC1=CC(=CO1)C(=O)NCCCNC(=O)C2=COC(=C2)C=C(C)CCC=C(C)C=C)CCC=C(C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087069
PubChem CID:	72544149
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO32605	sinularia kavarattiensis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24144848]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	59000.0	nM	PMID[505150]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	57700.0	nM	PMID[505150]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	73400.0	nM	PMID[505150]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	69700.0	nM	PMID[505150]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	41300.0	nM	PMID[505150]

☑ 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 NPC471653 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	168
0.1-0.2	2350
0.2-0.3	8386
0.3-0.4	9926
0.4-0.5	8688
0.5-0.6	11559
0.6-0.7	1596
0.7-0.8	21
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7941	Intermediate Similarity	NPC270807
0.7941	Intermediate Similarity	NPC174915
0.7721	Intermediate Similarity	NPC244862
0.7721	Intermediate Similarity	NPC67345
0.7554	Intermediate Similarity	NPC263870
0.7518	Intermediate Similarity	NPC21831
0.7518	Intermediate Similarity	NPC187547
0.7448	Intermediate Similarity	NPC477645
0.7383	Intermediate Similarity	NPC473268
0.7297	Intermediate Similarity	NPC106247
0.7248	Intermediate Similarity	NPC159786
0.7234	Intermediate Similarity	NPC1848
0.7214	Intermediate Similarity	NPC4898
0.7203	Intermediate Similarity	NPC118853
0.7194	Intermediate Similarity	NPC217180
0.7194	Intermediate Similarity	NPC312525
0.7111	Intermediate Similarity	NPC177331
0.7105	Intermediate Similarity	NPC472376
0.7101	Intermediate Similarity	NPC292036
0.7099	Intermediate Similarity	NPC473193
0.708	Intermediate Similarity	NPC26157
0.708	Intermediate Similarity	NPC1811
0.705	Intermediate Similarity	NPC205523
0.705	Intermediate Similarity	NPC28054
0.7037	Intermediate Similarity	NPC473194
0.7025	Intermediate Similarity	NPC308799
0.6993	Remote Similarity	NPC474136
0.6986	Remote Similarity	NPC216810
0.6981	Remote Similarity	NPC113428
0.6981	Remote Similarity	NPC61284
0.698	Remote Similarity	NPC136340
0.6963	Remote Similarity	NPC140688
0.695	Remote Similarity	NPC131801
0.6944	Remote Similarity	NPC289911
0.6944	Remote Similarity	NPC283284
0.6943	Remote Similarity	NPC261733
0.6943	Remote Similarity	NPC218712
0.6943	Remote Similarity	NPC471647
0.6943	Remote Similarity	NPC267004
0.6943	Remote Similarity	NPC471646
0.6943	Remote Similarity	NPC307346
0.6928	Remote Similarity	NPC278832
0.6928	Remote Similarity	NPC64157
0.6923	Remote Similarity	NPC474817
0.6897	Remote Similarity	NPC476351
0.6897	Remote Similarity	NPC475818
0.6879	Remote Similarity	NPC254198
0.6879	Remote Similarity	NPC474987
0.6879	Remote Similarity	NPC76844
0.6855	Remote Similarity	NPC104924
0.6853	Remote Similarity	NPC473969
0.6846	Remote Similarity	NPC146316
0.6821	Remote Similarity	NPC473982
0.6818	Remote Similarity	NPC170604
0.6818	Remote Similarity	NPC186626
0.6818	Remote Similarity	NPC215109
0.681	Remote Similarity	NPC471649
0.6809	Remote Similarity	NPC11821
0.6803	Remote Similarity	NPC71274
0.6803	Remote Similarity	NPC75557
0.6797	Remote Similarity	NPC265793
0.6788	Remote Similarity	NPC471521
0.6788	Remote Similarity	NPC473356
0.6788	Remote Similarity	NPC474542
0.6783	Remote Similarity	NPC254958
0.6783	Remote Similarity	NPC291619
0.6779	Remote Similarity	NPC474438
0.6779	Remote Similarity	NPC474279
0.6776	Remote Similarity	NPC169766
0.6776	Remote Similarity	NPC474425
0.6776	Remote Similarity	NPC474426
0.6776	Remote Similarity	NPC474407
0.6774	Remote Similarity	NPC130976
0.6767	Remote Similarity	NPC156768
0.6759	Remote Similarity	NPC79557
0.6757	Remote Similarity	NPC81912
0.6757	Remote Similarity	NPC329694
0.6757	Remote Similarity	NPC329922
0.6757	Remote Similarity	NPC474260
0.6739	Remote Similarity	NPC209111
0.6731	Remote Similarity	NPC107571
0.6713	Remote Similarity	NPC144745
0.6713	Remote Similarity	NPC208906
0.6712	Remote Similarity	NPC471549
0.6712	Remote Similarity	NPC473379
0.6711	Remote Similarity	NPC45358
0.6711	Remote Similarity	NPC95567
0.6711	Remote Similarity	NPC97740
0.6711	Remote Similarity	NPC319140
0.6707	Remote Similarity	NPC474378
0.6707	Remote Similarity	NPC474219
0.6705	Remote Similarity	NPC128683
0.6689	Remote Similarity	NPC21460
0.6689	Remote Similarity	NPC238309
0.6687	Remote Similarity	NPC105381
0.6687	Remote Similarity	NPC469642
0.6687	Remote Similarity	NPC10302
0.6667	Remote Similarity	NPC22248
0.6667	Remote Similarity	NPC267632
0.6667	Remote Similarity	NPC67654
0.6667	Remote Similarity	NPC263676
0.6647	Remote Similarity	NPC160015
0.6647	Remote Similarity	NPC247677
0.6646	Remote Similarity	NPC205765
0.6645	Remote Similarity	NPC17681
0.6643	Remote Similarity	NPC105249
0.6643	Remote Similarity	NPC45536
0.6643	Remote Similarity	NPC476031
0.6643	Remote Similarity	NPC476014
0.6642	Remote Similarity	NPC42471
0.6624	Remote Similarity	NPC474615
0.6623	Remote Similarity	NPC288209
0.6622	Remote Similarity	NPC65735
0.6622	Remote Similarity	NPC188377
0.6607	Remote Similarity	NPC269495
0.6607	Remote Similarity	NPC260902
0.6607	Remote Similarity	NPC116639
0.6607	Remote Similarity	NPC296957
0.6606	Remote Similarity	NPC156244
0.6603	Remote Similarity	NPC286130
0.6603	Remote Similarity	NPC471316
0.6601	Remote Similarity	NPC471953
0.66	Remote Similarity	NPC474830
0.66	Remote Similarity	NPC141059
0.66	Remote Similarity	NPC476016
0.6599	Remote Similarity	NPC323118
0.6597	Remote Similarity	NPC227660
0.6596	Remote Similarity	NPC22678
0.6593	Remote Similarity	NPC217226
0.6588	Remote Similarity	NPC471651
0.6588	Remote Similarity	NPC304387
0.6585	Remote Similarity	NPC226644
0.6585	Remote Similarity	NPC37226
0.6581	Remote Similarity	NPC92941
0.6581	Remote Similarity	NPC14650
0.6577	Remote Similarity	NPC474829
0.6568	Remote Similarity	NPC476350
0.6568	Remote Similarity	NPC476349
0.6568	Remote Similarity	NPC40583
0.6565	Remote Similarity	NPC233791
0.6565	Remote Similarity	NPC265461
0.6562	Remote Similarity	NPC476946
0.6556	Remote Similarity	NPC329707
0.6554	Remote Similarity	NPC311219
0.6552	Remote Similarity	NPC206007
0.655	Remote Similarity	NPC261184
0.6549	Remote Similarity	NPC311987
0.6548	Remote Similarity	NPC221992
0.6543	Remote Similarity	NPC346
0.6543	Remote Similarity	NPC98926
0.6543	Remote Similarity	NPC475864
0.6538	Remote Similarity	NPC303217
0.6536	Remote Similarity	NPC475092
0.6533	Remote Similarity	NPC83301
0.6533	Remote Similarity	NPC4164
0.6529	Remote Similarity	NPC472781
0.6529	Remote Similarity	NPC472782
0.6527	Remote Similarity	NPC1477
0.6527	Remote Similarity	NPC213608
0.6527	Remote Similarity	NPC122365
0.6522	Remote Similarity	NPC476310
0.6522	Remote Similarity	NPC313414
0.6522	Remote Similarity	NPC476164
0.6519	Remote Similarity	NPC188879
0.651	Remote Similarity	NPC243269
0.6509	Remote Similarity	NPC474611
0.6507	Remote Similarity	NPC137710
0.6507	Remote Similarity	NPC256369
0.6506	Remote Similarity	NPC116604
0.6506	Remote Similarity	NPC170169
0.6503	Remote Similarity	NPC250228
0.6497	Remote Similarity	NPC470742
0.6491	Remote Similarity	NPC472783
0.6491	Remote Similarity	NPC472780
0.649	Remote Similarity	NPC473355
0.649	Remote Similarity	NPC184391
0.649	Remote Similarity	NPC471501
0.649	Remote Similarity	NPC137570
0.649	Remote Similarity	NPC471554
0.649	Remote Similarity	NPC471573
0.6488	Remote Similarity	NPC198490
0.6486	Remote Similarity	NPC477967
0.6485	Remote Similarity	NPC317492
0.6485	Remote Similarity	NPC39929
0.6485	Remote Similarity	NPC296030
0.6481	Remote Similarity	NPC302181
0.6481	Remote Similarity	NPC195920
0.6478	Remote Similarity	NPC473681
0.6478	Remote Similarity	NPC201370
0.6478	Remote Similarity	NPC218204
0.6478	Remote Similarity	NPC282973
0.6478	Remote Similarity	NPC61157
0.6478	Remote Similarity	NPC124269
0.6478	Remote Similarity	NPC473983
0.6475	Remote Similarity	NPC219969
0.6471	Remote Similarity	NPC71205
0.6467	Remote Similarity	NPC471559
0.6467	Remote Similarity	NPC4012
0.6467	Remote Similarity	NPC142308
0.6467	Remote Similarity	NPC5871

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 NPC471653 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	710
0.2-0.3	1528
0.3-0.4	2799
0.4-0.5	2770
0.5-0.6	1127
0.6-0.7	82
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
0.6645	Remote Similarity	NPD1048	Approved
0.6588	Remote Similarity	NPD5262	Discontinued
0.6566	Remote Similarity	NPD6844	Discontinued
0.6554	Remote Similarity	NPD9717	Approved
0.6519	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6832	Phase 2
0.6506	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7318	Phase 3
0.6478	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD1986	Approved
0.6463	Remote Similarity	NPD3869	Phase 3
0.6463	Remote Similarity	NPD3873	Phase 3
0.6429	Remote Similarity	NPD7972	Discontinued
0.6424	Remote Similarity	NPD1203	Approved
0.6415	Remote Similarity	NPD2344	Approved
0.6391	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1019	Discontinued
0.637	Remote Similarity	NPD9092	Discovery
0.6369	Remote Similarity	NPD6280	Approved
0.6369	Remote Similarity	NPD6279	Approved
0.6369	Remote Similarity	NPD7317	Phase 3
0.6364	Remote Similarity	NPD7131	Phase 3
0.6358	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD1987	Approved
0.6354	Remote Similarity	NPD1985	Approved
0.6352	Remote Similarity	NPD1551	Phase 2
0.6346	Remote Similarity	NPD3140	Approved
0.6346	Remote Similarity	NPD3142	Approved
0.6341	Remote Similarity	NPD4662	Approved
0.6341	Remote Similarity	NPD4661	Approved
0.6316	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD447	Suspended
0.6303	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3823	Discontinued
0.628	Remote Similarity	NPD4357	Discontinued
0.6279	Remote Similarity	NPD6862	Phase 2
0.6273	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.627	Remote Similarity	NPD3958	Approved
0.6265	Remote Similarity	NPD920	Approved
0.6264	Remote Similarity	NPD6808	Phase 2
0.6263	Remote Similarity	NPD6863	Phase 2
0.6258	Remote Similarity	NPD2309	Approved
0.625	Remote Similarity	NPD5712	Approved
0.625	Remote Similarity	NPD6502	Phase 2
0.6235	Remote Similarity	NPD5760	Phase 2
0.6235	Remote Similarity	NPD5761	Phase 2
0.6234	Remote Similarity	NPD4993	Discontinued
0.6218	Remote Similarity	NPD2313	Discontinued
0.6215	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD2799	Discontinued
0.6183	Remote Similarity	NPD4466	Phase 1
0.6178	Remote Similarity	NPD7477	Discontinued
0.6176	Remote Similarity	NPD7577	Discontinued
0.6173	Remote Similarity	NPD2424	Discontinued
0.6173	Remote Similarity	NPD1549	Phase 2
0.6163	Remote Similarity	NPD3882	Suspended
0.6159	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2935	Discontinued
0.6145	Remote Similarity	NPD1729	Discontinued
0.6145	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD821	Approved
0.6135	Remote Similarity	NPD2654	Approved
0.6129	Remote Similarity	NPD1712	Approved
0.6126	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5890	Approved
0.6118	Remote Similarity	NPD2366	Approved
0.6118	Remote Similarity	NPD5889	Approved
0.6115	Remote Similarity	NPD411	Approved
0.6111	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD1241	Discontinued
0.6089	Remote Similarity	NPD3965	Phase 1
0.6087	Remote Similarity	NPD8434	Phase 2
0.6084	Remote Similarity	NPD6799	Approved
0.6081	Remote Similarity	NPD9493	Approved
0.6078	Remote Similarity	NPD3685	Discontinued
0.6078	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6559	Discontinued
0.6065	Remote Similarity	NPD5647	Approved
0.6062	Remote Similarity	NPD2157	Approved
0.6059	Remote Similarity	NPD4678	Approved
0.6059	Remote Similarity	NPD4675	Approved
0.6056	Remote Similarity	NPD2425	Phase 1
0.6054	Remote Similarity	NPD2792	Approved
0.6049	Remote Similarity	NPD2796	Approved
0.6049	Remote Similarity	NPD6032	Approved
0.6048	Remote Similarity	NPD4123	Phase 3
0.6047	Remote Similarity	NPD7819	Suspended
0.6044	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.604	Remote Similarity	NPD1758	Phase 1
0.6038	Remote Similarity	NPD1240	Approved
0.6037	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6971	Discontinued
0.6026	Remote Similarity	NPD9494	Approved
0.6024	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7411	Suspended
0.6022	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD7565	Approved
0.6021	Remote Similarity	NPD6874	Approved
0.6013	Remote Similarity	NPD3268	Approved
0.6012	Remote Similarity	NPD2346	Discontinued
0.6012	Remote Similarity	NPD1471	Phase 3
0.6012	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD2186	Approved
0.6012	Remote Similarity	NPD6390	Discontinued
0.6011	Remote Similarity	NPD6894	Phase 1
0.6011	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8161	Suspended
0.6	Remote Similarity	NPD4618	Approved
0.6	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2312	Discontinued
0.6	Remote Similarity	NPD2797	Approved
0.6	Remote Similarity	NPD1759	Phase 1
0.6	Remote Similarity	NPD2649	Approved
0.6	Remote Similarity	NPD2651	Approved
0.6	Remote Similarity	NPD1933	Approved
0.6	Remote Similarity	NPD4622	Approved
0.599	Remote Similarity	NPD5228	Phase 3
0.5989	Remote Similarity	NPD7315	Approved
0.5989	Remote Similarity	NPD6104	Discontinued
0.5988	Remote Similarity	NPD4308	Phase 3
0.5988	Remote Similarity	NPD1510	Phase 2
0.5988	Remote Similarity	NPD6087	Phase 1
0.5978	Remote Similarity	NPD3446	Phase 1
0.5977	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7768	Phase 2
0.5976	Remote Similarity	NPD5403	Approved
0.5975	Remote Similarity	NPD839	Approved
0.5975	Remote Similarity	NPD520	Approved
0.5975	Remote Similarity	NPD840	Approved
0.5974	Remote Similarity	NPD6582	Phase 2
0.5974	Remote Similarity	NPD6583	Phase 3
0.5965	Remote Similarity	NPD6585	Discontinued
0.5964	Remote Similarity	NPD2219	Phase 1
0.5964	Remote Similarity	NPD3692	Discontinued
0.5963	Remote Similarity	NPD1607	Approved
0.5962	Remote Similarity	NPD2798	Approved
0.596	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD3819	Phase 2
0.5955	Remote Similarity	NPD644	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD2801	Approved
0.5954	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2504	Approved
0.5952	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2505	Approved
0.5951	Remote Similarity	NPD4477	Approved
0.5951	Remote Similarity	NPD4476	Approved
0.595	Remote Similarity	NPD4377	Discontinued
0.5949	Remote Similarity	NPD5163	Phase 2
0.5946	Remote Similarity	NPD3154	Approved
0.5946	Remote Similarity	NPD3153	Approved
0.5944	Remote Similarity	NPD2163	Approved
0.5943	Remote Similarity	NPD7075	Discontinued
0.5943	Remote Similarity	NPD3749	Approved
0.5941	Remote Similarity	NPD8404	Phase 2
0.5939	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD3291	Approved
0.5938	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7811	Phase 3
0.5938	Remote Similarity	NPD7810	Phase 3
0.5935	Remote Similarity	NPD2922	Phase 1
0.5935	Remote Similarity	NPD3225	Approved
0.5932	Remote Similarity	NPD1247	Approved
0.5928	Remote Similarity	NPD7440	Discontinued
0.5926	Remote Similarity	NPD5689	Approved
0.5926	Remote Similarity	NPD5688	Approved
0.592	Remote Similarity	NPD5402	Approved
0.592	Remote Similarity	NPD9478	Approved
0.592	Remote Similarity	NPD9479	Approved
0.5912	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4628	Phase 3
0.5897	Remote Similarity	NPD6362	Approved
0.5896	Remote Similarity	NPD1934	Approved
0.5892	Remote Similarity	NPD927	Approved
0.5892	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.589	Remote Similarity	NPD7033	Discontinued
0.5886	Remote Similarity	NPD682	Discontinued
0.5886	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3496	Discontinued
0.5882	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3847	Discontinued
0.5882	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD5557	Phase 1
0.5879	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD9069	Phase 1
0.5876	Remote Similarity	NPD6746	Phase 2
0.5875	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD3579	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data