NPASS Compound

Structure

NPC1848 OpenBabel07101719252D 31 31 0 0 1 0 0 0 0 0999 V2000 -0.7701 -8.8304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2349 -10.4777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8658 -3.6818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4895 -0.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2420 -6.6162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7738 2.5983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3795 -2.3435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7557 -5.2779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1716 -3.3216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7068 -4.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3305 -2.0345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5478 -6.2561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7953 -0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9241 -9.1905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0831 -7.9034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0270 -9.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9147 -3.9908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5385 -1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2910 -6.9252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1320 -8.2124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9328 3.8855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3889 -7.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 23 2 0 0 0 0 13 14 1 0 0 0 0 13 22 2 0 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 24 28 2 0 0 0 0 24 31 1 0 0 0 0 25 27 1 0 0 0 0 26 29 2 0 0 0 0 27 14 1 1 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	483.697
LogP:	6.411
LogD:	4.946
LogS:	-5.387
# Rotatable Bonds:	15
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	3.745
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.631
MDCK Permeability:	2.850729833880905e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.551
30% Bioavailability (F30%):	0.655

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.356
Plasma Protein Binding (PPB):	93.01699829101562%
Volume Distribution (VD):	1.447
Pgp-substrate:	3.0151031017303467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.553
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.945
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.112
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.759
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	7.17
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.794
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.644
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.591
Carcinogencity:	0.539
Eye Corrosion:	0.826
Eye Irritation:	0.686
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC1848

Natural Product ID:	NPC1848
*Common Name:**	4-Acetoxy-9-Deoxoidiadione
IUPAC Name:	[(1S,3E,7E,11E)-1-(furan-3-yl)-4,8,12,16-tetramethyl-14-oxoheptadeca-3,7,11-trienyl] acetate
Synonyms:
Standard InCHIKey:	IRBWUUAXBAPQRQ-RWWDORIESA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-20(2)17-26(29)18-23(5)12-8-10-21(3)9-7-11-22(4)13-14-27(31-24(6)28)25-15-16-30-19-25/h9,12-13,15-16,19-20,27H,7-8,10-11,14,17-18H2,1-6H3/b21-9+,22-13+,23-12+/t27-/m0/s1
SMILES:	CC(C)CC(=O)C/C(=C/CC/C(=C/CC/C(=C/C[C@@H](c1ccoc1)OC(=O)C)/C)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485665
PubChem CID:	11293295
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
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	31.6	ug.mL-1	PMID[494247]

☑ 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 NPC1848 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	265
0.1-0.2	1436
0.2-0.3	4930
0.3-0.4	10651
0.4-0.5	10013
0.5-0.6	9795
0.6-0.7	4994
0.7-0.8	524
0.8-0.85	69
0.85-0.9	17
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9237	High Similarity	NPC263870
0.9138	High Similarity	NPC131801
0.8983	High Similarity	NPC473969
0.885	High Similarity	NPC471521
0.885	High Similarity	NPC473356
0.871	High Similarity	NPC319140
0.871	High Similarity	NPC95567
0.8689	High Similarity	NPC475818
0.8655	High Similarity	NPC208906
0.8655	High Similarity	NPC144745
0.8651	High Similarity	NPC21460
0.8621	High Similarity	NPC105249
0.8607	High Similarity	NPC289911
0.8607	High Similarity	NPC283284
0.8605	High Similarity	NPC92941
0.8595	High Similarity	NPC474817
0.8594	High Similarity	NPC474425
0.8594	High Similarity	NPC474407
0.8594	High Similarity	NPC474426
0.8583	High Similarity	NPC136340
0.8571	High Similarity	NPC45536
0.855	High Similarity	NPC476943
0.855	High Similarity	NPC220094
0.8547	High Similarity	NPC26157
0.8547	High Similarity	NPC1811
0.8525	High Similarity	NPC474136
0.8512	High Similarity	NPC244862
0.8512	High Similarity	NPC67345
0.848	Intermediate Similarity	NPC329694
0.848	Intermediate Similarity	NPC474260
0.848	Intermediate Similarity	NPC329922
0.848	Intermediate Similarity	NPC81912
0.848	Intermediate Similarity	NPC216810
0.8473	Intermediate Similarity	NPC310830
0.8473	Intermediate Similarity	NPC470742
0.8413	Intermediate Similarity	NPC474830
0.8413	Intermediate Similarity	NPC476016
0.8413	Intermediate Similarity	NPC137570
0.84	Intermediate Similarity	NPC474829
0.84	Intermediate Similarity	NPC71274
0.84	Intermediate Similarity	NPC75557
0.8387	Intermediate Similarity	NPC476351
0.8372	Intermediate Similarity	NPC471817
0.8361	Intermediate Similarity	NPC4898
0.8333	Intermediate Similarity	NPC28054
0.8321	Intermediate Similarity	NPC159786
0.8309	Intermediate Similarity	NPC142113
0.8308	Intermediate Similarity	NPC470740
0.8279	Intermediate Similarity	NPC187547
0.8279	Intermediate Similarity	NPC21831
0.8276	Intermediate Similarity	NPC140688
0.8268	Intermediate Similarity	NPC471554
0.8268	Intermediate Similarity	NPC471501
0.8268	Intermediate Similarity	NPC471573
0.8268	Intermediate Similarity	NPC473355
0.8258	Intermediate Similarity	NPC146872
0.8254	Intermediate Similarity	NPC471559
0.825	Intermediate Similarity	NPC292036
0.8235	Intermediate Similarity	NPC267632
0.8226	Intermediate Similarity	NPC79557
0.8203	Intermediate Similarity	NPC474438
0.8203	Intermediate Similarity	NPC474279
0.8197	Intermediate Similarity	NPC312525
0.8197	Intermediate Similarity	NPC217180
0.8195	Intermediate Similarity	NPC473268
0.8195	Intermediate Similarity	NPC186626
0.8175	Intermediate Similarity	NPC65735
0.8175	Intermediate Similarity	NPC188377
0.816	Intermediate Similarity	NPC471549
0.816	Intermediate Similarity	NPC174915
0.816	Intermediate Similarity	NPC473379
0.816	Intermediate Similarity	NPC270807
0.8154	Intermediate Similarity	NPC17681
0.8136	Intermediate Similarity	NPC177331
0.8134	Intermediate Similarity	NPC236532
0.813	Intermediate Similarity	NPC243704
0.811	Intermediate Similarity	NPC179354
0.8106	Intermediate Similarity	NPC288209
0.8106	Intermediate Similarity	NPC106247
0.8102	Intermediate Similarity	NPC223415
0.8102	Intermediate Similarity	NPC470741
0.8095	Intermediate Similarity	NPC16922
0.8092	Intermediate Similarity	NPC45358
0.8092	Intermediate Similarity	NPC97740
0.8088	Intermediate Similarity	NPC20500
0.8074	Intermediate Similarity	NPC474615
0.806	Intermediate Similarity	NPC42400
0.8058	Intermediate Similarity	NPC262198
0.8049	Intermediate Similarity	NPC227660
0.8043	Intermediate Similarity	NPC476944
0.8033	Intermediate Similarity	NPC205523
0.8031	Intermediate Similarity	NPC243269
0.8016	Intermediate Similarity	NPC317217
0.8015	Intermediate Similarity	NPC298190
0.8015	Intermediate Similarity	NPC282973
0.8014	Intermediate Similarity	NPC329180
0.8	Intermediate Similarity	NPC470941
0.7958	Intermediate Similarity	NPC469335
0.7958	Intermediate Similarity	NPC46551
0.7958	Intermediate Similarity	NPC196864
0.7958	Intermediate Similarity	NPC159927
0.7958	Intermediate Similarity	NPC477404
0.7943	Intermediate Similarity	NPC113428
0.7943	Intermediate Similarity	NPC61284
0.7929	Intermediate Similarity	NPC346
0.7926	Intermediate Similarity	NPC286130
0.791	Intermediate Similarity	NPC14650
0.7907	Intermediate Similarity	NPC74612
0.7907	Intermediate Similarity	NPC138139
0.7907	Intermediate Similarity	NPC46536
0.7891	Intermediate Similarity	NPC477038
0.7891	Intermediate Similarity	NPC118853
0.7891	Intermediate Similarity	NPC477965
0.7886	Intermediate Similarity	NPC150895
0.7879	Intermediate Similarity	NPC89133
0.7874	Intermediate Similarity	NPC477967
0.7872	Intermediate Similarity	NPC476938
0.7872	Intermediate Similarity	NPC308799
0.7872	Intermediate Similarity	NPC221809
0.7872	Intermediate Similarity	NPC476937
0.7872	Intermediate Similarity	NPC250228
0.7868	Intermediate Similarity	NPC472376
0.7857	Intermediate Similarity	NPC195920
0.7846	Intermediate Similarity	NPC83178
0.7842	Intermediate Similarity	NPC476946
0.7842	Intermediate Similarity	NPC254198
0.7832	Intermediate Similarity	NPC476122
0.7832	Intermediate Similarity	NPC156189
0.7826	Intermediate Similarity	NPC205765
0.7823	Intermediate Similarity	NPC476031
0.7823	Intermediate Similarity	NPC476014
0.7817	Intermediate Similarity	NPC476941
0.7817	Intermediate Similarity	NPC476942
0.781	Intermediate Similarity	NPC474722
0.781	Intermediate Similarity	NPC90953
0.7801	Intermediate Similarity	NPC475864
0.7801	Intermediate Similarity	NPC104924
0.7794	Intermediate Similarity	NPC215109
0.7794	Intermediate Similarity	NPC170604
0.7793	Intermediate Similarity	NPC30222
0.7793	Intermediate Similarity	NPC178932
0.7786	Intermediate Similarity	NPC86935
0.7786	Intermediate Similarity	NPC137295
0.7786	Intermediate Similarity	NPC112706
0.7786	Intermediate Similarity	NPC207294
0.7778	Intermediate Similarity	NPC18135
0.7762	Intermediate Similarity	NPC472654
0.7762	Intermediate Similarity	NPC195325
0.7754	Intermediate Similarity	NPC56197
0.7746	Intermediate Similarity	NPC10088
0.774	Intermediate Similarity	NPC35000
0.774	Intermediate Similarity	NPC469850
0.774	Intermediate Similarity	NPC469336
0.774	Intermediate Similarity	NPC281258
0.774	Intermediate Similarity	NPC264943
0.773	Intermediate Similarity	NPC37488
0.7727	Intermediate Similarity	NPC198904
0.7724	Intermediate Similarity	NPC469503
0.7724	Intermediate Similarity	NPC476201
0.7724	Intermediate Similarity	NPC75906
0.7714	Intermediate Similarity	NPC110305
0.7714	Intermediate Similarity	NPC80635
0.7692	Intermediate Similarity	NPC474255
0.7692	Intermediate Similarity	NPC471618
0.7692	Intermediate Similarity	NPC7388
0.7692	Intermediate Similarity	NPC474220
0.7687	Intermediate Similarity	NPC209364
0.7687	Intermediate Similarity	NPC469485
0.7687	Intermediate Similarity	NPC107646
0.7687	Intermediate Similarity	NPC204663
0.7687	Intermediate Similarity	NPC471545
0.7687	Intermediate Similarity	NPC470976
0.7687	Intermediate Similarity	NPC470977
0.7687	Intermediate Similarity	NPC196979
0.7687	Intermediate Similarity	NPC473344
0.7687	Intermediate Similarity	NPC473982
0.7687	Intermediate Similarity	NPC471544
0.7687	Intermediate Similarity	NPC15083
0.7681	Intermediate Similarity	NPC107571
0.768	Intermediate Similarity	NPC76844
0.7676	Intermediate Similarity	NPC471292
0.7676	Intermediate Similarity	NPC276676
0.7676	Intermediate Similarity	NPC62799
0.7671	Intermediate Similarity	NPC282445
0.766	Intermediate Similarity	NPC199044
0.766	Intermediate Similarity	NPC84479
0.766	Intermediate Similarity	NPC238843
0.7652	Intermediate Similarity	NPC477040
0.7652	Intermediate Similarity	NPC327527
0.7652	Intermediate Similarity	NPC476917
0.7652	Intermediate Similarity	NPC477039
0.7652	Intermediate Similarity	NPC477123
0.7652	Intermediate Similarity	NPC477966
0.7643	Intermediate Similarity	NPC473152
0.7643	Intermediate Similarity	NPC121158
0.7642	Intermediate Similarity	NPC22678
0.7639	Intermediate Similarity	NPC470790
0.7639	Intermediate Similarity	NPC475904
0.7639	Intermediate Similarity	NPC474270
0.7639	Intermediate Similarity	NPC470791

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 NPC1848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	1066
0.2-0.3	2254
0.3-0.4	2900
0.4-0.5	1783
0.5-0.6	718
0.6-0.7	177
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
0.7594	Intermediate Similarity	NPD6832	Phase 2
0.7444	Intermediate Similarity	NPD1019	Discontinued
0.7429	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD9717	Approved
0.7267	Intermediate Similarity	NPD5761	Phase 2
0.7267	Intermediate Similarity	NPD5760	Phase 2
0.7194	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2799	Discontinued
0.7016	Intermediate Similarity	NPD3134	Approved
0.6985	Remote Similarity	NPD1203	Approved
0.6978	Remote Similarity	NPD2313	Discontinued
0.695	Remote Similarity	NPD1933	Approved
0.695	Remote Similarity	NPD447	Suspended
0.6934	Remote Similarity	NPD5647	Approved
0.6929	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1241	Discontinued
0.6875	Remote Similarity	NPD2796	Approved
0.6875	Remote Similarity	NPD1551	Phase 2
0.6861	Remote Similarity	NPD3266	Approved
0.6861	Remote Similarity	NPD3267	Approved
0.6861	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1243	Approved
0.6825	Remote Similarity	NPD1358	Approved
0.6779	Remote Similarity	NPD6799	Approved
0.6761	Remote Similarity	NPD4307	Phase 2
0.6759	Remote Similarity	NPD2935	Discontinued
0.6752	Remote Similarity	NPD919	Approved
0.6742	Remote Similarity	NPD9493	Approved
0.6739	Remote Similarity	NPD6362	Approved
0.6739	Remote Similarity	NPD2797	Approved
0.6738	Remote Similarity	NPD411	Approved
0.6738	Remote Similarity	NPD3268	Approved
0.673	Remote Similarity	NPD6808	Phase 2
0.6716	Remote Similarity	NPD5585	Approved
0.6712	Remote Similarity	NPD2346	Discontinued
0.6712	Remote Similarity	NPD1471	Phase 3
0.6712	Remote Similarity	NPD2344	Approved
0.671	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8434	Phase 2
0.6691	Remote Similarity	NPD2798	Approved
0.6645	Remote Similarity	NPD5403	Approved
0.6644	Remote Similarity	NPD3887	Approved
0.6641	Remote Similarity	NPD2182	Approved
0.6623	Remote Similarity	NPD6599	Discontinued
0.6623	Remote Similarity	NPD5401	Approved
0.6622	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6559	Discontinued
0.6604	Remote Similarity	NPD5494	Approved
0.6603	Remote Similarity	NPD7819	Suspended
0.6597	Remote Similarity	NPD6355	Discontinued
0.6582	Remote Similarity	NPD7075	Discontinued
0.6581	Remote Similarity	NPD7411	Suspended
0.6577	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4628	Phase 3
0.6575	Remote Similarity	NPD4308	Phase 3
0.6575	Remote Similarity	NPD7033	Discontinued
0.6575	Remote Similarity	NPD3748	Approved
0.6564	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1247	Approved
0.6561	Remote Similarity	NPD5402	Approved
0.6554	Remote Similarity	NPD1549	Phase 2
0.6552	Remote Similarity	NPD6653	Approved
0.6547	Remote Similarity	NPD1876	Approved
0.6538	Remote Similarity	NPD6801	Discontinued
0.6533	Remote Similarity	NPD2309	Approved
0.6522	Remote Similarity	NPD3972	Approved
0.6503	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD3496	Discontinued
0.6486	Remote Similarity	NPD6004	Phase 3
0.6486	Remote Similarity	NPD6002	Phase 3
0.6486	Remote Similarity	NPD6005	Phase 3
0.6486	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4618	Approved
0.6483	Remote Similarity	NPD4622	Approved
0.6478	Remote Similarity	NPD3749	Approved
0.6475	Remote Similarity	NPD4359	Approved
0.6474	Remote Similarity	NPD5890	Approved
0.6474	Remote Similarity	NPD5889	Approved
0.6471	Remote Similarity	NPD6273	Approved
0.6462	Remote Similarity	NPD2067	Discontinued
0.6458	Remote Similarity	NPD6233	Phase 2
0.6452	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD9092	Discovery
0.6439	Remote Similarity	NPD5535	Approved
0.6433	Remote Similarity	NPD6280	Approved
0.6433	Remote Similarity	NPD6279	Approved
0.6423	Remote Similarity	NPD17	Approved
0.6415	Remote Similarity	NPD7768	Phase 2
0.6414	Remote Similarity	NPD3142	Approved
0.6414	Remote Similarity	NPD3140	Approved
0.6406	Remote Similarity	NPD9697	Approved
0.6405	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD2532	Approved
0.6405	Remote Similarity	NPD2534	Approved
0.6405	Remote Similarity	NPD2533	Approved
0.6397	Remote Similarity	NPD9545	Approved
0.6395	Remote Similarity	NPD5688	Approved
0.6395	Remote Similarity	NPD7097	Phase 1
0.6395	Remote Similarity	NPD5689	Approved
0.6389	Remote Similarity	NPD6798	Discontinued
0.6382	Remote Similarity	NPD7440	Discontinued
0.6378	Remote Similarity	NPD9261	Approved
0.6376	Remote Similarity	NPD2353	Approved
0.6376	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3750	Approved
0.6352	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD3817	Phase 2
0.6352	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3226	Approved
0.6345	Remote Similarity	NPD8032	Phase 2
0.6333	Remote Similarity	NPD2424	Discontinued
0.6329	Remote Similarity	NPD6844	Discontinued
0.6328	Remote Similarity	NPD164	Approved
0.6323	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD3882	Suspended
0.6312	Remote Similarity	NPD3225	Approved
0.631	Remote Similarity	NPD6764	Approved
0.631	Remote Similarity	NPD6765	Approved
0.6306	Remote Similarity	NPD6585	Discontinued
0.6304	Remote Similarity	NPD1778	Approved
0.6301	Remote Similarity	NPD2979	Phase 3
0.6301	Remote Similarity	NPD1240	Approved
0.6299	Remote Similarity	NPD4662	Approved
0.6299	Remote Similarity	NPD4661	Approved
0.6294	Remote Similarity	NPD9494	Approved
0.6289	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD1608	Approved
0.628	Remote Similarity	NPD3926	Phase 2
0.6277	Remote Similarity	NPD1894	Discontinued
0.6273	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1238	Approved
0.6265	Remote Similarity	NPD3818	Discontinued
0.625	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5353	Approved
0.6242	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1510	Phase 2
0.6233	Remote Similarity	NPD4870	Approved
0.6233	Remote Similarity	NPD4062	Phase 3
0.6232	Remote Similarity	NPD5691	Approved
0.6228	Remote Similarity	NPD7286	Phase 2
0.6226	Remote Similarity	NPD1934	Approved
0.6225	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD3873	Phase 3
0.6218	Remote Similarity	NPD3869	Phase 3
0.6216	Remote Similarity	NPD1607	Approved
0.6211	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD2354	Approved
0.6204	Remote Similarity	NPD5536	Phase 2
0.6203	Remote Similarity	NPD4380	Phase 2
0.62	Remote Similarity	NPD2438	Suspended
0.6194	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD7843	Approved
0.6194	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD2800	Approved
0.6184	Remote Similarity	NPD2654	Approved
0.6183	Remote Similarity	NPD9264	Approved
0.6183	Remote Similarity	NPD9267	Approved
0.6183	Remote Similarity	NPD9263	Approved
0.6174	Remote Similarity	NPD2567	Approved
0.6174	Remote Similarity	NPD2569	Approved
0.617	Remote Similarity	NPD1481	Phase 2
0.6164	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD3764	Approved
0.6164	Remote Similarity	NPD1296	Phase 2
0.6164	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6784	Approved
0.6163	Remote Similarity	NPD6785	Approved
0.6154	Remote Similarity	NPD2186	Approved
0.6149	Remote Similarity	NPD230	Phase 1
0.6145	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD4110	Phase 3
0.6144	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD3847	Discontinued
0.614	Remote Similarity	NPD8313	Approved
0.614	Remote Similarity	NPD8312	Approved
0.6139	Remote Similarity	NPD7458	Discontinued
0.6136	Remote Similarity	NPD2684	Approved
0.6136	Remote Similarity	NPD74	Approved
0.6136	Remote Similarity	NPD9266	Approved
0.6121	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD1535	Discovery
0.6099	Remote Similarity	NPD1281	Approved
0.6093	Remote Similarity	NPD5712	Approved
0.6093	Remote Similarity	NPD6032	Approved
0.6087	Remote Similarity	NPD7972	Discontinued
0.6087	Remote Similarity	NPD2801	Approved
0.6071	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6385	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