NPASS Compound

Structure

CID105249 OpenBabel06191715452D 24 25 0 0 0 0 0 0 0 0999 V2000 -6.6723 1.3685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2453 -0.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0724 -1.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4994 0.5551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6272 -1.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9678 -0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2634 -1.7961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6904 -0.0327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5408 -1.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4130 0.1483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5227 -0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2220 1.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1730 2.0451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1730 0.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7769 0.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3498 -1.3893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2220 0.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7608 1.2361 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 19 1 0 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.2
Volume:	365.211
LogP:	5.662
LogD:	5.254
LogS:	-4.508
# Rotatable Bonds:	10
TPSA:	46.51
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	3.25
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.854
MDCK Permeability:	2.6546129447524436e-05
Pgp-inhibitor:	0.081
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.597
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.693

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	95.79398345947266%
Volume Distribution (VD):	1.261
Pgp-substrate:	0.44547566771507263%

ADMET: Metabolism

CYP1A2-inhibitor:	0.745
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.776
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.61
CYP2C9-substrate:	0.698
CYP2D6-inhibitor:	0.885
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.404
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	7.748
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.71
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.177
Carcinogencity:	0.216
Eye Corrosion:	0.025
Eye Irritation:	0.421
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC105249

Natural Product ID:	NPC105249
*Common Name:**	Furospongolide
IUPAC Name:	3-[(4E,8E)-11-(furan-3-yl)-4,8-dimethylundeca-4,8-dienyl]-2H-furan-5-one
Synonyms:	Furospongolide
Standard InCHIKey:	WCHKEOQZUQGPSS-ZTRBTYSCSA-N
Standard InCHI:	InChI=1S/C21H28O3/c1-17(8-4-10-19-12-13-23-15-19)6-3-7-18(2)9-5-11-20-14-21(22)24-16-20/h7-8,12-15H,3-6,9-11,16H2,1-2H3/b17-8+,18-7+
SMILES:	C/C(=CCCc1ccoc1)/CC/C=C(C)/CCCC1=CC(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077108
PubChem CID:	21637526
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO33257	lendenfeldia sp.	Species	Thorectidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17958396]
NPO33257	lendenfeldia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18989978]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548580]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31095383]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	14
Others	4

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	1
PROTEIN FAMILY	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	14000.0	nM	PMID[538397]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	29000.0	nM	PMID[538397]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30000.0	nM	PMID[538397]
NPT396	Cell Line	T47D	Homo sapiens	IC50	>	30000.0	nM	PMID[538397]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	30000.0	nM	PMID[538397]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30000.0	nM	PMID[538397]
NPT396	Cell Line	T47D	Homo sapiens	Inhibition	=	26.0	%	PMID[538397]
NPT396	Cell Line	T47D	Homo sapiens	Inhibition	=	38.0	%	PMID[538397]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	2900.0	nM	PMID[538397]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	10900.0	nM	PMID[538397]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	30000.0	nM	PMID[538397]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity ratio	=	10.0	n.a.	PMID[538397]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	Inhibition	=	97.0	%	PMID[538397]

☑ 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 NPC105249 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	248
0.1-0.2	1852
0.2-0.3	5395
0.3-0.4	11772
0.4-0.5	9575
0.5-0.6	10905
0.6-0.7	2557
0.7-0.8	313
0.8-0.85	50
0.85-0.9	19
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9519	High Similarity	NPC471521
0.9519	High Similarity	NPC473356
0.9273	High Similarity	NPC131801
0.9167	High Similarity	NPC26157
0.9167	High Similarity	NPC1811
0.9107	High Similarity	NPC473969
0.9099	High Similarity	NPC144745
0.9099	High Similarity	NPC208906
0.8957	High Similarity	NPC476351
0.8947	High Similarity	NPC474136
0.8938	High Similarity	NPC4898
0.8919	High Similarity	NPC28054
0.8889	High Similarity	NPC177331
0.887	High Similarity	NPC289911
0.887	High Similarity	NPC283284
0.886	High Similarity	NPC474817
0.8803	High Similarity	NPC71274
0.8803	High Similarity	NPC75557
0.8793	High Similarity	NPC475818
0.8729	High Similarity	NPC329922
0.8729	High Similarity	NPC329694
0.8729	High Similarity	NPC474260
0.8729	High Similarity	NPC81912
0.8684	High Similarity	NPC187547
0.8684	High Similarity	NPC21831
0.8655	High Similarity	NPC476016
0.8632	High Similarity	NPC16922
0.8621	High Similarity	NPC1848
0.8583	High Similarity	NPC474438
0.8583	High Similarity	NPC474279
0.8559	High Similarity	NPC65735
0.8559	High Similarity	NPC243269
0.8559	High Similarity	NPC188377
0.8522	High Similarity	NPC243704
0.85	High Similarity	NPC137570
0.8487	Intermediate Similarity	NPC474829
0.8487	Intermediate Similarity	NPC471559
0.8487	Intermediate Similarity	NPC179354
0.8435	Intermediate Similarity	NPC227660
0.8421	Intermediate Similarity	NPC205523
0.8421	Intermediate Similarity	NPC150895
0.8417	Intermediate Similarity	NPC46536
0.8417	Intermediate Similarity	NPC74612
0.8417	Intermediate Similarity	NPC138139
0.8348	Intermediate Similarity	NPC45536
0.8347	Intermediate Similarity	NPC319140
0.8347	Intermediate Similarity	NPC471554
0.8347	Intermediate Similarity	NPC473355
0.8347	Intermediate Similarity	NPC471501
0.8347	Intermediate Similarity	NPC95567
0.8347	Intermediate Similarity	NPC471573
0.8347	Intermediate Similarity	NPC83178
0.8347	Intermediate Similarity	NPC474830
0.8279	Intermediate Similarity	NPC207294
0.8279	Intermediate Similarity	NPC112706
0.8276	Intermediate Similarity	NPC312525
0.8276	Intermediate Similarity	NPC217180
0.8235	Intermediate Similarity	NPC477967
0.8235	Intermediate Similarity	NPC471549
0.8235	Intermediate Similarity	NPC317217
0.8235	Intermediate Similarity	NPC473379
0.8226	Intermediate Similarity	NPC298190
0.8226	Intermediate Similarity	NPC17681
0.819	Intermediate Similarity	NPC476031
0.819	Intermediate Similarity	NPC476014
0.816	Intermediate Similarity	NPC97740
0.816	Intermediate Similarity	NPC45358
0.8115	Intermediate Similarity	NPC216810
0.811	Intermediate Similarity	NPC14650
0.8099	Intermediate Similarity	NPC477965
0.8099	Intermediate Similarity	NPC477038
0.8099	Intermediate Similarity	NPC118853
0.8083	Intermediate Similarity	NPC263870
0.808	Intermediate Similarity	NPC89133
0.808	Intermediate Similarity	NPC475092
0.8036	Intermediate Similarity	NPC140688
0.8031	Intermediate Similarity	NPC288209
0.8017	Intermediate Similarity	NPC292036
0.8016	Intermediate Similarity	NPC471817
0.8	Intermediate Similarity	NPC79557
0.8	Intermediate Similarity	NPC21460
0.8	Intermediate Similarity	NPC22678
0.7984	Intermediate Similarity	NPC170604
0.7984	Intermediate Similarity	NPC215109
0.7983	Intermediate Similarity	NPC137710
0.7983	Intermediate Similarity	NPC244862
0.7983	Intermediate Similarity	NPC67345
0.7969	Intermediate Similarity	NPC92941
0.7967	Intermediate Similarity	NPC23086
0.7953	Intermediate Similarity	NPC474426
0.7953	Intermediate Similarity	NPC474425
0.7953	Intermediate Similarity	NPC470740
0.7953	Intermediate Similarity	NPC474407
0.7946	Intermediate Similarity	NPC42471
0.7937	Intermediate Similarity	NPC136340
0.7934	Intermediate Similarity	NPC36255
0.7907	Intermediate Similarity	NPC146872
0.7899	Intermediate Similarity	NPC254958
0.7899	Intermediate Similarity	NPC293424
0.7899	Intermediate Similarity	NPC291619
0.7846	Intermediate Similarity	NPC470742
0.784	Intermediate Similarity	NPC476917
0.784	Intermediate Similarity	NPC477040
0.784	Intermediate Similarity	NPC477123
0.784	Intermediate Similarity	NPC327527
0.784	Intermediate Similarity	NPC477966
0.784	Intermediate Similarity	NPC477039
0.7818	Intermediate Similarity	NPC156768
0.7805	Intermediate Similarity	NPC130275
0.7805	Intermediate Similarity	NPC83115
0.7786	Intermediate Similarity	NPC236532
0.776	Intermediate Similarity	NPC141059
0.775	Intermediate Similarity	NPC206007
0.7742	Intermediate Similarity	NPC471074
0.7742	Intermediate Similarity	NPC473885
0.7742	Intermediate Similarity	NPC230979
0.7727	Intermediate Similarity	NPC90953
0.7717	Intermediate Similarity	NPC476925
0.7712	Intermediate Similarity	NPC252004
0.771	Intermediate Similarity	NPC307401
0.771	Intermediate Similarity	NPC186626
0.771	Intermediate Similarity	NPC310830
0.771	Intermediate Similarity	NPC42400
0.7692	Intermediate Similarity	NPC159786
0.768	Intermediate Similarity	NPC83301
0.7674	Intermediate Similarity	NPC471006
0.7669	Intermediate Similarity	NPC56197
0.7667	Intermediate Similarity	NPC212918
0.7656	Intermediate Similarity	NPC61788
0.7652	Intermediate Similarity	NPC476943
0.7652	Intermediate Similarity	NPC220094
0.7647	Intermediate Similarity	NPC11821
0.7642	Intermediate Similarity	NPC174915
0.7642	Intermediate Similarity	NPC270807
0.7638	Intermediate Similarity	NPC208389
0.7634	Intermediate Similarity	NPC303217
0.763	Intermediate Similarity	NPC223415
0.76	Intermediate Similarity	NPC221798
0.7597	Intermediate Similarity	NPC471545
0.7597	Intermediate Similarity	NPC473982
0.7597	Intermediate Similarity	NPC471544
0.7597	Intermediate Similarity	NPC473344
0.7594	Intermediate Similarity	NPC202260
0.7583	Intermediate Similarity	NPC76844
0.7583	Intermediate Similarity	NPC474987
0.7574	Intermediate Similarity	NPC261733
0.7574	Intermediate Similarity	NPC218712
0.7574	Intermediate Similarity	NPC307346
0.7574	Intermediate Similarity	NPC267004
0.7565	Intermediate Similarity	NPC151530
0.7565	Intermediate Similarity	NPC157473
0.7561	Intermediate Similarity	NPC97566
0.7561	Intermediate Similarity	NPC115859
0.754	Intermediate Similarity	NPC52035
0.7538	Intermediate Similarity	NPC218838
0.7538	Intermediate Similarity	NPC293253
0.7521	Intermediate Similarity	NPC217423
0.7521	Intermediate Similarity	NPC45104
0.7519	Intermediate Similarity	NPC282230
0.7519	Intermediate Similarity	NPC183348
0.75	Intermediate Similarity	NPC470741
0.75	Intermediate Similarity	NPC120836
0.75	Intermediate Similarity	NPC267632
0.75	Intermediate Similarity	NPC59502
0.75	Intermediate Similarity	NPC198904
0.75	Intermediate Similarity	NPC80635
0.75	Intermediate Similarity	NPC223063
0.7481	Intermediate Similarity	NPC20500
0.7481	Intermediate Similarity	NPC106247
0.748	Intermediate Similarity	NPC230951
0.7479	Intermediate Similarity	NPC53953
0.7478	Intermediate Similarity	NPC176971
0.7463	Intermediate Similarity	NPC474615
0.7463	Intermediate Similarity	NPC107571
0.7462	Intermediate Similarity	NPC15083
0.7462	Intermediate Similarity	NPC196979
0.7462	Intermediate Similarity	NPC470977
0.7462	Intermediate Similarity	NPC470976
0.7459	Intermediate Similarity	NPC87466
0.7458	Intermediate Similarity	NPC277525
0.7458	Intermediate Similarity	NPC57879
0.7458	Intermediate Similarity	NPC54626
0.7455	Intermediate Similarity	NPC146316
0.7445	Intermediate Similarity	NPC199044
0.7445	Intermediate Similarity	NPC238843
0.7445	Intermediate Similarity	NPC251865
0.7444	Intermediate Similarity	NPC286130
0.7442	Intermediate Similarity	NPC66246
0.7442	Intermediate Similarity	NPC170546
0.744	Intermediate Similarity	NPC69403
0.744	Intermediate Similarity	NPC272899
0.744	Intermediate Similarity	NPC291189
0.7438	Intermediate Similarity	NPC470860
0.7438	Intermediate Similarity	NPC59035
0.7438	Intermediate Similarity	NPC316062
0.7438	Intermediate Similarity	NPC79202
0.7426	Intermediate Similarity	NPC121158
0.7424	Intermediate Similarity	NPC158525
0.7424	Intermediate Similarity	NPC476947
0.7407	Intermediate Similarity	NPC148374

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 NPC105249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1123
0.2-0.3	2109
0.3-0.4	3007
0.4-0.5	1778
0.5-0.6	745
0.6-0.7	157
0.7-0.8	7
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
0.7364	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1241	Discontinued
0.7328	Intermediate Similarity	NPD3134	Approved
0.7209	Intermediate Similarity	NPD1019	Discontinued
0.7165	Intermediate Similarity	NPD9717	Approved
0.7119	Intermediate Similarity	NPD1358	Approved
0.7083	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5585	Approved
0.6963	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1238	Approved
0.6953	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD9697	Approved
0.6917	Remote Similarity	NPD2182	Approved
0.6905	Remote Similarity	NPD9545	Approved
0.687	Remote Similarity	NPD1203	Approved
0.6838	Remote Similarity	NPD1933	Approved
0.6831	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1778	Approved
0.6772	Remote Similarity	NPD1894	Discontinued
0.6769	Remote Similarity	NPD3972	Approved
0.6765	Remote Similarity	NPD4307	Phase 2
0.6765	Remote Similarity	NPD3142	Approved
0.6765	Remote Similarity	NPD3140	Approved
0.6763	Remote Similarity	NPD1551	Phase 2
0.6759	Remote Similarity	NPD920	Approved
0.6746	Remote Similarity	NPD9493	Approved
0.6744	Remote Similarity	NPD3496	Discontinued
0.6742	Remote Similarity	NPD2797	Approved
0.6738	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4359	Approved
0.6694	Remote Similarity	NPD5535	Approved
0.6693	Remote Similarity	NPD9092	Discovery
0.6691	Remote Similarity	NPD2799	Discontinued
0.669	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6643	Remote Similarity	NPD3887	Approved
0.662	Remote Similarity	NPD1243	Approved
0.6618	Remote Similarity	NPD2313	Discontinued
0.6618	Remote Similarity	NPD411	Approved
0.6617	Remote Similarity	NPD3267	Approved
0.6617	Remote Similarity	NPD3266	Approved
0.66	Remote Similarity	NPD5760	Phase 2
0.66	Remote Similarity	NPD5761	Phase 2
0.6596	Remote Similarity	NPD2344	Approved
0.6594	Remote Similarity	NPD447	Suspended
0.6589	Remote Similarity	NPD5691	Approved
0.6583	Remote Similarity	NPD164	Approved
0.6575	Remote Similarity	NPD6273	Approved
0.6571	Remote Similarity	NPD4308	Phase 3
0.6567	Remote Similarity	NPD2798	Approved
0.6552	Remote Similarity	NPD6799	Approved
0.6525	Remote Similarity	NPD2796	Approved
0.6519	Remote Similarity	NPD9494	Approved
0.6515	Remote Similarity	NPD1608	Approved
0.6504	Remote Similarity	NPD2684	Approved
0.6496	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6798	Discontinued
0.6496	Remote Similarity	NPD3268	Approved
0.6493	Remote Similarity	NPD6362	Approved
0.6483	Remote Similarity	NPD7440	Discontinued
0.6479	Remote Similarity	NPD2353	Approved
0.6479	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD1471	Phase 3
0.6475	Remote Similarity	NPD4622	Approved
0.6475	Remote Similarity	NPD4618	Approved
0.6475	Remote Similarity	NPD6355	Discontinued
0.6463	Remote Similarity	NPD2186	Approved
0.6454	Remote Similarity	NPD3748	Approved
0.6452	Remote Similarity	NPD2067	Discontinued
0.6449	Remote Similarity	NPD4062	Phase 3
0.6449	Remote Similarity	NPD6233	Phase 2
0.6447	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5647	Approved
0.6429	Remote Similarity	NPD919	Approved
0.6419	Remote Similarity	NPD3873	Phase 3
0.6419	Remote Similarity	NPD3869	Phase 3
0.6418	Remote Similarity	NPD3225	Approved
0.6414	Remote Similarity	NPD2309	Approved
0.6408	Remote Similarity	NPD2935	Discontinued
0.6397	Remote Similarity	NPD454	Approved
0.6391	Remote Similarity	NPD1481	Phase 2
0.6383	Remote Similarity	NPD5688	Approved
0.6383	Remote Similarity	NPD5689	Approved
0.6364	Remote Similarity	NPD6002	Phase 3
0.6364	Remote Similarity	NPD9261	Approved
0.6364	Remote Similarity	NPD2346	Discontinued
0.6364	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6004	Phase 3
0.6364	Remote Similarity	NPD6005	Phase 3
0.6364	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3847	Discontinued
0.6339	Remote Similarity	NPD9259	Approved
0.6339	Remote Similarity	NPD9257	Approved
0.6338	Remote Similarity	NPD7033	Discontinued
0.6331	Remote Similarity	NPD4870	Approved
0.6331	Remote Similarity	NPD8032	Phase 2
0.6328	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1535	Discovery
0.6316	Remote Similarity	NPD1281	Approved
0.6316	Remote Similarity	NPD6280	Approved
0.6316	Remote Similarity	NPD6279	Approved
0.6312	Remote Similarity	NPD6653	Approved
0.6309	Remote Similarity	NPD5403	Approved
0.6308	Remote Similarity	NPD5536	Phase 2
0.6306	Remote Similarity	NPD6808	Phase 2
0.6301	Remote Similarity	NPD2354	Approved
0.6299	Remote Similarity	NPD7843	Approved
0.6294	Remote Similarity	NPD4477	Approved
0.6294	Remote Similarity	NPD4476	Approved
0.6291	Remote Similarity	NPD6599	Discontinued
0.629	Remote Similarity	NPD290	Approved
0.6288	Remote Similarity	NPD4626	Approved
0.6286	Remote Similarity	NPD2979	Phase 3
0.6284	Remote Similarity	NPD5401	Approved
0.6259	Remote Similarity	NPD3764	Approved
0.625	Remote Similarity	NPD7411	Suspended
0.6239	Remote Similarity	NPD1202	Approved
0.6233	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7003	Approved
0.6233	Remote Similarity	NPD3750	Approved
0.6232	Remote Similarity	NPD2614	Approved
0.6225	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.621	Remote Similarity	NPD968	Approved
0.6207	Remote Similarity	NPD2897	Discontinued
0.62	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6765	Approved
0.6196	Remote Similarity	NPD6764	Approved
0.6194	Remote Similarity	NPD422	Phase 1
0.6187	Remote Similarity	NPD5163	Phase 2
0.6187	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD2239	Approved
0.6181	Remote Similarity	NPD2240	Approved
0.6176	Remote Similarity	NPD1283	Approved
0.6174	Remote Similarity	NPD4662	Approved
0.6174	Remote Similarity	NPD4661	Approved
0.6172	Remote Similarity	NPD821	Approved
0.6169	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD7819	Suspended
0.6169	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.616	Remote Similarity	NPD9267	Approved
0.616	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.616	Remote Similarity	NPD9263	Approved
0.616	Remote Similarity	NPD9264	Approved
0.6159	Remote Similarity	NPD957	Approved
0.6154	Remote Similarity	NPD7157	Approved
0.6149	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD5889	Approved
0.6144	Remote Similarity	NPD5890	Approved
0.6143	Remote Similarity	NPD1296	Phase 2
0.6138	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD5049	Phase 3
0.6122	Remote Similarity	NPD4110	Phase 3
0.6122	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD9256	Approved
0.6121	Remote Similarity	NPD9258	Approved
0.6111	Remote Similarity	NPD74	Approved
0.6111	Remote Similarity	NPD9266	Approved
0.6104	Remote Similarity	NPD6801	Discontinued
0.6101	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6559	Discontinued
0.6096	Remote Similarity	NPD1549	Phase 2
0.6096	Remote Similarity	NPD5958	Discontinued
0.6096	Remote Similarity	NPD4534	Discontinued
0.6094	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD1670	Discontinued
0.6093	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.609	Remote Similarity	NPD1651	Approved
0.609	Remote Similarity	NPD7768	Phase 2
0.6087	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD6287	Discontinued
0.6071	Remote Similarity	NPD5746	Approved
0.6071	Remote Similarity	NPD7095	Approved
0.6071	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD2438	Suspended
0.6069	Remote Similarity	NPD2531	Phase 2
0.6058	Remote Similarity	NPD2198	Approved
0.6058	Remote Similarity	NPD2199	Approved
0.6056	Remote Similarity	NPD4140	Approved
0.6056	Remote Similarity	NPD1240	Approved
0.6054	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD3749	Approved
0.6051	Remote Similarity	NPD7075	Discontinued
0.6048	Remote Similarity	NPD6784	Approved
0.6048	Remote Similarity	NPD6785	Approved
0.6043	Remote Similarity	NPD2237	Approved
0.6042	Remote Similarity	NPD7097	Phase 1
0.6042	Remote Similarity	NPD743	Approved
0.6039	Remote Similarity	NPD958	Approved
0.6039	Remote Similarity	NPD6386	Approved
0.6039	Remote Similarity	NPD6385	Approved
0.6038	Remote Similarity	NPD1247	Approved
0.6031	Remote Similarity	NPD2557	Approved
0.6028	Remote Similarity	NPD3374	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