NPASS Compound

Structure

CID289911 OpenBabel06191716092D 29 30 0 0 1 0 0 0 0 0999 V2000 -4.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1810 -1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9242 -2.5057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5823 -1.0276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5878 -0.9230 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 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7902 -2.0057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 18 2 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 22 2 0 0 0 0 17 28 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 25 27 2 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.25
Volume:	440.549
LogP:	5.87
LogD:	5.113
LogS:	-4.52
# Rotatable Bonds:	11
TPSA:	66.74
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	3.519
Fsp3:	0.44
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:	-4.884
MDCK Permeability:	2.543689879530575e-05
Pgp-inhibitor:	0.781
Pgp-substrate:	0.101
Human Intestinal Absorption (HIA):	0.283
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	96.97074890136719%
Volume Distribution (VD):	2.169
Pgp-substrate:	0.6186778545379639%

ADMET: Metabolism

CYP1A2-inhibitor:	0.603
CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.751
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.845
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	5.046
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.247
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.522
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.717
Carcinogencity:	0.246
Eye Corrosion:	0.005
Eye Irritation:	0.495
Respiratory Toxicity:	0.864

Download Data

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

Natural Product: NPC289911

Natural Product ID:	NPC289911
*Common Name:**	Variabilin
IUPAC Name:	(5Z)-5-[(6E,10E)-13-(furan-3-yl)-2,6,10-trimethyltrideca-6,10-dienylidene]-4-hydroxy-3-methylfuran-2-one
Synonyms:	Variabilin
Standard InCHIKey:	HPVSJNGZYYDDMU-FECKPXKMSA-N
Standard InCHI:	InChI=1S/C25H34O4/c1-18(8-5-9-19(2)11-7-13-22-14-15-28-17-22)10-6-12-20(3)16-23-24(26)21(4)25(27)29-23/h8,11,14-17,20,26H,5-7,9-10,12-13H2,1-4H3/b18-8+,19-11+,23-16-
SMILES:	C/C(=CCC/C(=C/CCc1cocc1)/C)/CCCC(/C=C/1OC(=O)C(=C1O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463244
PubChem CID:	54678431
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO2611	Dalbergia variabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2611	Dalbergia variabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2611	Dalbergia variabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2611	Dalbergia variabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	5

Activity Type	# Activity
Individual Protein	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	<	25.0	%	PMID[482808]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	49.9	%	PMID[482808]
NPT1106	Organism	Human poliovirus 1	Human poliovirus 1	IZ	=	4.0	mm	PMID[482809]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IZ	=	4.0	mm	PMID[482809]
NPT27	Others	Unspecified		IZ	=	1.0	mm	PMID[482809]

☑ 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 NPC289911 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	227
0.1-0.2	1281
0.2-0.3	4349
0.3-0.4	10209
0.4-0.5	10116
0.5-0.6	10938
0.6-0.7	5130
0.7-0.8	375
0.8-0.85	36
0.85-0.9	19
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC283284
0.9912	High Similarity	NPC474136
0.9744	High Similarity	NPC71274
0.9744	High Similarity	NPC75557
0.9741	High Similarity	NPC476351
0.9741	High Similarity	NPC475818
0.95	High Similarity	NPC474279
0.95	High Similarity	NPC474438
0.9496	High Similarity	NPC329694
0.9496	High Similarity	NPC474260
0.9496	High Similarity	NPC329922
0.9496	High Similarity	NPC81912
0.9483	High Similarity	NPC474817
0.9391	High Similarity	NPC131801
0.9256	High Similarity	NPC476016
0.9231	High Similarity	NPC473969
0.9098	High Similarity	NPC474830
0.9048	High Similarity	NPC288209
0.8957	High Similarity	NPC26157
0.8957	High Similarity	NPC1811
0.8934	High Similarity	NPC474829
0.8898	High Similarity	NPC208906
0.8898	High Similarity	NPC144745
0.887	High Similarity	NPC105249
0.8837	High Similarity	NPC215109
0.8837	High Similarity	NPC170604
0.8828	High Similarity	NPC14650
0.878	High Similarity	NPC471559
0.8772	High Similarity	NPC471521
0.8772	High Similarity	NPC473356
0.874	High Similarity	NPC97740
0.8667	High Similarity	NPC187547
0.8667	High Similarity	NPC21831
0.8661	High Similarity	NPC17681
0.864	High Similarity	NPC473355
0.864	High Similarity	NPC471554
0.864	High Similarity	NPC471573
0.864	High Similarity	NPC471501
0.8607	High Similarity	NPC1848
0.8595	High Similarity	NPC4898
0.8594	High Similarity	NPC45358
0.8548	High Similarity	NPC243269
0.8537	High Similarity	NPC471549
0.8537	High Similarity	NPC473379
0.8534	High Similarity	NPC177331
0.8527	High Similarity	NPC474407
0.8527	High Similarity	NPC474426
0.8527	High Similarity	NPC474425
0.8492	Intermediate Similarity	NPC137570
0.8387	Intermediate Similarity	NPC263870
0.8333	Intermediate Similarity	NPC303217
0.8264	Intermediate Similarity	NPC28054
0.8254	Intermediate Similarity	NPC188377
0.8254	Intermediate Similarity	NPC65735
0.8254	Intermediate Similarity	NPC118853
0.8248	Intermediate Similarity	NPC307346
0.8248	Intermediate Similarity	NPC218712
0.8248	Intermediate Similarity	NPC267004
0.8248	Intermediate Similarity	NPC261733
0.8148	Intermediate Similarity	NPC107571
0.814	Intermediate Similarity	NPC112706
0.814	Intermediate Similarity	NPC207294
0.813	Intermediate Similarity	NPC217180
0.813	Intermediate Similarity	NPC312525
0.8125	Intermediate Similarity	NPC138139
0.8125	Intermediate Similarity	NPC46536
0.8095	Intermediate Similarity	NPC477967
0.8092	Intermediate Similarity	NPC89133
0.8062	Intermediate Similarity	NPC83178
0.8047	Intermediate Similarity	NPC179354
0.8031	Intermediate Similarity	NPC16922
0.8	Intermediate Similarity	NPC473268
0.7985	Intermediate Similarity	NPC159786
0.7984	Intermediate Similarity	NPC227660
0.7969	Intermediate Similarity	NPC477965
0.7969	Intermediate Similarity	NPC477038
0.7967	Intermediate Similarity	NPC205523
0.7953	Intermediate Similarity	NPC317217
0.792	Intermediate Similarity	NPC243704
0.7903	Intermediate Similarity	NPC45536
0.7895	Intermediate Similarity	NPC471545
0.7895	Intermediate Similarity	NPC471817
0.7895	Intermediate Similarity	NPC473344
0.7895	Intermediate Similarity	NPC471544
0.7883	Intermediate Similarity	NPC90953
0.7846	Intermediate Similarity	NPC23086
0.7846	Intermediate Similarity	NPC74612
0.7836	Intermediate Similarity	NPC470740
0.7823	Intermediate Similarity	NPC150895
0.782	Intermediate Similarity	NPC298190
0.782	Intermediate Similarity	NPC136340
0.7786	Intermediate Similarity	NPC254198
0.7786	Intermediate Similarity	NPC319140
0.7786	Intermediate Similarity	NPC95567
0.7786	Intermediate Similarity	NPC80635
0.7778	Intermediate Similarity	NPC254958
0.7778	Intermediate Similarity	NPC291619
0.7761	Intermediate Similarity	NPC473982
0.776	Intermediate Similarity	NPC476031
0.776	Intermediate Similarity	NPC476014
0.7746	Intermediate Similarity	NPC104924
0.7742	Intermediate Similarity	NPC292036
0.7737	Intermediate Similarity	NPC186626
0.7734	Intermediate Similarity	NPC79557
0.7727	Intermediate Similarity	NPC477966
0.7727	Intermediate Similarity	NPC477123
0.7727	Intermediate Similarity	NPC477039
0.7727	Intermediate Similarity	NPC477040
0.7721	Intermediate Similarity	NPC92941
0.7721	Intermediate Similarity	NPC476947
0.771	Intermediate Similarity	NPC216810
0.7708	Intermediate Similarity	NPC234494
0.7704	Intermediate Similarity	NPC218838
0.7687	Intermediate Similarity	NPC475092
0.7676	Intermediate Similarity	NPC34056
0.7674	Intermediate Similarity	NPC174915
0.7674	Intermediate Similarity	NPC270807
0.7671	Intermediate Similarity	NPC33938
0.7664	Intermediate Similarity	NPC146872
0.7647	Intermediate Similarity	NPC106247
0.7638	Intermediate Similarity	NPC293424
0.7626	Intermediate Similarity	NPC202260
0.7612	Intermediate Similarity	NPC21460
0.7612	Intermediate Similarity	NPC476925
0.7609	Intermediate Similarity	NPC470742
0.7606	Intermediate Similarity	NPC137295
0.7603	Intermediate Similarity	NPC140688
0.7594	Intermediate Similarity	NPC327527
0.7594	Intermediate Similarity	NPC476917
0.7589	Intermediate Similarity	NPC121158
0.7586	Intermediate Similarity	NPC69647
0.7586	Intermediate Similarity	NPC125182
0.7581	Intermediate Similarity	NPC22678
0.7578	Intermediate Similarity	NPC244862
0.7578	Intermediate Similarity	NPC67345
0.7576	Intermediate Similarity	NPC88403
0.7571	Intermediate Similarity	NPC56197
0.7569	Intermediate Similarity	NPC255414
0.7557	Intermediate Similarity	NPC130275
0.7556	Intermediate Similarity	NPC477645
0.7556	Intermediate Similarity	NPC61788
0.7554	Intermediate Similarity	NPC236532
0.7552	Intermediate Similarity	NPC195920
0.7551	Intermediate Similarity	NPC121615
0.7551	Intermediate Similarity	NPC474219
0.7551	Intermediate Similarity	NPC294511
0.7551	Intermediate Similarity	NPC474378
0.7538	Intermediate Similarity	NPC36255
0.7538	Intermediate Similarity	NPC272487
0.7537	Intermediate Similarity	NPC120836
0.7537	Intermediate Similarity	NPC223063
0.7537	Intermediate Similarity	NPC208389
0.7535	Intermediate Similarity	NPC476946
0.7535	Intermediate Similarity	NPC22248
0.7535	Intermediate Similarity	NPC267632
0.7534	Intermediate Similarity	NPC228842
0.7534	Intermediate Similarity	NPC470997
0.7519	Intermediate Similarity	NPC474476
0.7519	Intermediate Similarity	NPC290955
0.7517	Intermediate Similarity	NPC7388
0.75	Intermediate Similarity	NPC34421
0.75	Intermediate Similarity	NPC471074
0.75	Intermediate Similarity	NPC230979
0.75	Intermediate Similarity	NPC221798
0.75	Intermediate Similarity	NPC253201
0.75	Intermediate Similarity	NPC346
0.75	Intermediate Similarity	NPC302054
0.75	Intermediate Similarity	NPC98206
0.75	Intermediate Similarity	NPC237259
0.75	Intermediate Similarity	NPC473885
0.7483	Intermediate Similarity	NPC251865
0.7483	Intermediate Similarity	NPC476944
0.7482	Intermediate Similarity	NPC64157
0.7482	Intermediate Similarity	NPC310830
0.7482	Intermediate Similarity	NPC307401
0.7482	Intermediate Similarity	NPC42400
0.7482	Intermediate Similarity	NPC278832
0.7481	Intermediate Similarity	NPC238309
0.748	Intermediate Similarity	NPC76844
0.748	Intermediate Similarity	NPC474987
0.7467	Intermediate Similarity	NPC472777
0.7467	Intermediate Similarity	NPC472776
0.7467	Intermediate Similarity	NPC472778
0.7463	Intermediate Similarity	NPC279877
0.7463	Intermediate Similarity	NPC329707
0.7463	Intermediate Similarity	NPC26532
0.745	Intermediate Similarity	NPC155939
0.745	Intermediate Similarity	NPC141538
0.745	Intermediate Similarity	NPC296807
0.7448	Intermediate Similarity	NPC71821
0.7448	Intermediate Similarity	NPC216755
0.7448	Intermediate Similarity	NPC250228
0.7448	Intermediate Similarity	NPC471174
0.7447	Intermediate Similarity	NPC148374
0.7447	Intermediate Similarity	NPC282973
0.7444	Intermediate Similarity	NPC52035
0.7442	Intermediate Similarity	NPC137710
0.7432	Intermediate Similarity	NPC44577
0.7432	Intermediate Similarity	NPC472672
0.7432	Intermediate Similarity	NPC268905

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 NPC289911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	951
0.2-0.3	2056
0.3-0.4	2910
0.4-0.5	1869
0.5-0.6	925
0.6-0.7	222
0.7-0.8	8
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
0.7376	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7218	Intermediate Similarity	NPD9717	Approved
0.7177	Intermediate Similarity	NPD1358	Approved
0.7154	Intermediate Similarity	NPD9092	Discovery
0.7153	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7132	Intermediate Similarity	NPD5647	Approved
0.7097	Intermediate Similarity	NPD3134	Approved
0.6972	Remote Similarity	NPD6653	Approved
0.6957	Remote Similarity	NPD9494	Approved
0.6934	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1203	Approved
0.6934	Remote Similarity	NPD2797	Approved
0.6929	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD447	Suspended
0.6899	Remote Similarity	NPD7843	Approved
0.6884	Remote Similarity	NPD1019	Discontinued
0.6883	Remote Similarity	NPD5761	Phase 2
0.6883	Remote Similarity	NPD5760	Phase 2
0.6875	Remote Similarity	NPD2799	Discontinued
0.685	Remote Similarity	NPD2684	Approved
0.6846	Remote Similarity	NPD6799	Approved
0.6846	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD9545	Approved
0.6828	Remote Similarity	NPD1551	Phase 2
0.6815	Remote Similarity	NPD3496	Discontinued
0.6809	Remote Similarity	NPD3268	Approved
0.6783	Remote Similarity	NPD1933	Approved
0.6761	Remote Similarity	NPD6233	Phase 2
0.6761	Remote Similarity	NPD4062	Phase 3
0.6759	Remote Similarity	NPD4308	Phase 3
0.6744	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7157	Approved
0.6733	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2354	Approved
0.6711	Remote Similarity	NPD5403	Approved
0.6711	Remote Similarity	NPD3887	Approved
0.6692	Remote Similarity	NPD9493	Approved
0.6691	Remote Similarity	NPD6362	Approved
0.669	Remote Similarity	NPD411	Approved
0.669	Remote Similarity	NPD2313	Discontinued
0.6688	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD7440	Discontinued
0.6646	Remote Similarity	NPD7075	Discontinued
0.6645	Remote Similarity	NPD6273	Approved
0.6643	Remote Similarity	NPD2798	Approved
0.6642	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7458	Discontinued
0.662	Remote Similarity	NPD7095	Approved
0.6618	Remote Similarity	NPD1778	Approved
0.6603	Remote Similarity	NPD6801	Discontinued
0.6601	Remote Similarity	NPD920	Approved
0.6599	Remote Similarity	NPD2935	Discontinued
0.6597	Remote Similarity	NPD4307	Phase 2
0.6597	Remote Similarity	NPD4060	Phase 1
0.6594	Remote Similarity	NPD1608	Approved
0.6593	Remote Similarity	NPD1894	Discontinued
0.6579	Remote Similarity	NPD5401	Approved
0.6575	Remote Similarity	NPD7097	Phase 1
0.6573	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3266	Approved
0.6571	Remote Similarity	NPD3267	Approved
0.6566	Remote Similarity	NPD6765	Approved
0.6566	Remote Similarity	NPD6764	Approved
0.6566	Remote Similarity	NPD6559	Discontinued
0.6556	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2353	Approved
0.6554	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2067	Discontinued
0.6536	Remote Similarity	NPD5049	Phase 3
0.6533	Remote Similarity	NPD4110	Phase 3
0.6533	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7033	Discontinued
0.6516	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5535	Approved
0.6512	Remote Similarity	NPD290	Approved
0.651	Remote Similarity	NPD5958	Discontinued
0.6503	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3225	Approved
0.65	Remote Similarity	NPD919	Approved
0.65	Remote Similarity	NPD1876	Approved
0.6496	Remote Similarity	NPD17	Approved
0.649	Remote Similarity	NPD2309	Approved
0.6486	Remote Similarity	NPD2239	Approved
0.6486	Remote Similarity	NPD2240	Approved
0.6484	Remote Similarity	NPD9697	Approved
0.6475	Remote Similarity	NPD1481	Phase 2
0.6475	Remote Similarity	NPD3972	Approved
0.6471	Remote Similarity	NPD4661	Approved
0.6471	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4662	Approved
0.6462	Remote Similarity	NPD2182	Approved
0.6458	Remote Similarity	NPD3764	Approved
0.6456	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3847	Discontinued
0.6443	Remote Similarity	NPD5763	Approved
0.6443	Remote Similarity	NPD5762	Approved
0.6443	Remote Similarity	NPD2346	Discontinued
0.6438	Remote Similarity	NPD4340	Discontinued
0.6433	Remote Similarity	NPD7411	Suspended
0.6429	Remote Similarity	NPD4359	Approved
0.6424	Remote Similarity	NPD3750	Approved
0.6424	Remote Similarity	NPD7003	Approved
0.6424	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5402	Approved
0.6412	Remote Similarity	NPD6784	Approved
0.6412	Remote Similarity	NPD6785	Approved
0.6408	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD1535	Discovery
0.64	Remote Similarity	NPD4534	Discontinued
0.6398	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD5536	Phase 2
0.6377	Remote Similarity	NPD4626	Approved
0.6375	Remote Similarity	NPD3882	Suspended
0.6375	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7768	Phase 2
0.637	Remote Similarity	NPD3140	Approved
0.637	Remote Similarity	NPD3142	Approved
0.6358	Remote Similarity	NPD1243	Approved
0.6352	Remote Similarity	NPD7819	Suspended
0.6349	Remote Similarity	NPD1238	Approved
0.6338	Remote Similarity	NPD987	Approved
0.6333	Remote Similarity	NPD1471	Phase 3
0.6329	Remote Similarity	NPD958	Approved
0.6329	Remote Similarity	NPD6677	Suspended
0.6327	Remote Similarity	NPD4622	Approved
0.6327	Remote Similarity	NPD230	Phase 1
0.6327	Remote Similarity	NPD4618	Approved
0.6319	Remote Similarity	NPD2614	Approved
0.6316	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD969	Suspended
0.6312	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD3817	Phase 2
0.6309	Remote Similarity	NPD3748	Approved
0.6304	Remote Similarity	NPD5691	Approved
0.6303	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD8032	Phase 2
0.6291	Remote Similarity	NPD2424	Discontinued
0.6291	Remote Similarity	NPD1549	Phase 2
0.6282	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD1283	Approved
0.6267	Remote Similarity	NPD4477	Approved
0.6267	Remote Similarity	NPD5712	Approved
0.6267	Remote Similarity	NPD6032	Approved
0.6267	Remote Similarity	NPD2796	Approved
0.6267	Remote Similarity	NPD4476	Approved
0.6267	Remote Similarity	NPD2438	Suspended
0.6259	Remote Similarity	NPD2979	Phase 3
0.6258	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.625	Remote Similarity	NPD454	Approved
0.6242	Remote Similarity	NPD5688	Approved
0.6242	Remote Similarity	NPD5689	Approved
0.6235	Remote Similarity	NPD3749	Approved
0.6235	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD1048	Approved
0.6225	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8127	Discontinued
0.6218	Remote Similarity	NPD2186	Approved
0.6212	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD8166	Discontinued
0.6203	Remote Similarity	NPD2649	Approved
0.6203	Remote Similarity	NPD3226	Approved
0.6203	Remote Similarity	NPD2651	Approved
0.6202	Remote Similarity	NPD6647	Phase 2
0.6188	Remote Similarity	NPD1934	Approved
0.6188	Remote Similarity	NPD7577	Discontinued
0.6184	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD2897	Discontinued
0.6184	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD968	Approved
0.6182	Remote Similarity	NPD6808	Phase 2
0.6179	Remote Similarity	NPD9365	Approved
0.6178	Remote Similarity	NPD3869	Phase 3
0.6178	Remote Similarity	NPD3873	Phase 3
0.6176	Remote Similarity	NPD2629	Approved
0.617	Remote Similarity	NPD1281	Approved
0.617	Remote Similarity	NPD1091	Approved
0.617	Remote Similarity	NPD422	Phase 1
0.6164	Remote Similarity	NPD4380	Phase 2
0.6159	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2532	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