NPASS Compound

Structure

NPC83178 OpenBabel07101718332D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3914 1.1088 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8228 -0.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5176 -0.1741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8569 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9716 0.7169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3735 0.9701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5299 -0.0176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2645 1.4240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 12 23 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 19 1 6 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 2 1 6 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	4.329
LogD:	3.974
LogS:	-4.086
# Rotatable Bonds:	4
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.775
Synthetic Accessibility Score:	4.335
Fsp3:	0.65
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:	-5.325
MDCK Permeability:	1.7258284060517326e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	93.50731658935547%
Volume Distribution (VD):	1.414
Pgp-substrate:	3.2044007778167725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.445
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.652
CYP2C9-substrate:	0.685
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.631
CYP3A4-substrate:	0.39

ADMET: Excretion

Clearance (CL):	5.608
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.357
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.82
Maximum Recommended Daily Dose:	0.262
Skin Sensitization:	0.053
Carcinogencity:	0.899
Eye Corrosion:	0.51
Eye Irritation:	0.292
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC83178

Natural Product ID:	NPC83178
*Common Name:**	5-[2-(Furan-3-Yl)Ethyl]-1,5,6-Trimethyl-1,2,3,4,5,6,7,8-Octahydronaphthalene-1-Carboxylic Acid
IUPAC Name:	(1S,5S,6R)-5-[2-(furan-3-yl)ethyl]-1,5,6-trimethyl-2,3,4,6,7,8-hexahydronaphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	QSCGVVYGWUHJIU-UAOJZALGSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-14-6-7-17-16(5-4-10-20(17,3)18(21)22)19(14,2)11-8-15-9-12-23-13-15/h9,12-14H,4-8,10-11H2,1-3H3,(H,21,22)/t14-,19+,20+/m1/s1
SMILES:	C[C@@H]1CCC2=C(CCC[C@]2(C)C(=O)O)[C@@]1(C)CCc1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481833
PubChem CID:	11404306
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15679308]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	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	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[513632]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	<	12.5	ug.mL-1	PMID[513632]

☑ 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 NPC83178 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	218
0.1-0.2	1323
0.2-0.3	3197
0.3-0.4	7474
0.4-0.5	12492
0.5-0.6	10943
0.6-0.7	6310
0.7-0.8	570
0.8-0.85	115
0.85-0.9	42
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9752	High Similarity	NPC112706
0.9752	High Similarity	NPC207294
0.9587	High Similarity	NPC138139
0.9587	High Similarity	NPC46536
0.9426	High Similarity	NPC23086
0.9339	High Similarity	NPC16922
0.9256	High Similarity	NPC477967
0.9206	High Similarity	NPC89133
0.9206	High Similarity	NPC298190
0.9187	High Similarity	NPC179354
0.912	High Similarity	NPC477039
0.9113	High Similarity	NPC74612
0.9106	High Similarity	NPC243269
0.9106	High Similarity	NPC130275
0.9055	High Similarity	NPC61788
0.9	High Similarity	NPC144745
0.9	High Similarity	NPC208906
0.8968	High Similarity	NPC477123
0.8968	High Similarity	NPC477966
0.8939	High Similarity	NPC90953
0.8923	High Similarity	NPC92941
0.8915	High Similarity	NPC470740
0.8915	High Similarity	NPC218838
0.8833	High Similarity	NPC150895
0.8819	High Similarity	NPC477040
0.88	High Similarity	NPC477038
0.88	High Similarity	NPC477965
0.8797	High Similarity	NPC202260
0.879	High Similarity	NPC317217
0.879	High Similarity	NPC36255
0.8788	High Similarity	NPC470742
0.8779	High Similarity	NPC158525
0.877	High Similarity	NPC243704
0.875	High Similarity	NPC120836
0.875	High Similarity	NPC223063
0.874	High Similarity	NPC290955
0.874	High Similarity	NPC246392
0.8731	High Similarity	NPC148374
0.8722	High Similarity	NPC220094
0.8722	High Similarity	NPC236532
0.872	High Similarity	NPC272899
0.8712	High Similarity	NPC146872
0.8682	High Similarity	NPC476925
0.8672	High Similarity	NPC327527
0.8672	High Similarity	NPC26532
0.8672	High Similarity	NPC476917
0.8651	High Similarity	NPC83115
0.8647	High Similarity	NPC310830
0.8636	High Similarity	NPC476947
0.8626	High Similarity	NPC471006
0.8605	High Similarity	NPC208389
0.8603	High Similarity	NPC121158
0.8583	High Similarity	NPC303010
0.8583	High Similarity	NPC230979
0.8571	High Similarity	NPC46896
0.854	High Similarity	NPC267632
0.8537	High Similarity	NPC212918
0.8527	High Similarity	NPC279877
0.8507	High Similarity	NPC307401
0.8504	High Similarity	NPC65735
0.8504	High Similarity	NPC188377
0.8489	Intermediate Similarity	NPC346
0.8478	Intermediate Similarity	NPC476944
0.8478	Intermediate Similarity	NPC251865
0.8462	Intermediate Similarity	NPC59502
0.8456	Intermediate Similarity	NPC56197
0.845	Intermediate Similarity	NPC95567
0.845	Intermediate Similarity	NPC476016
0.845	Intermediate Similarity	NPC319140
0.8444	Intermediate Similarity	NPC476943
0.8438	Intermediate Similarity	NPC471074
0.8438	Intermediate Similarity	NPC473885
0.8438	Intermediate Similarity	NPC474829
0.843	Intermediate Similarity	NPC26157
0.843	Intermediate Similarity	NPC1811
0.8429	Intermediate Similarity	NPC471174
0.8429	Intermediate Similarity	NPC250228
0.8421	Intermediate Similarity	NPC471998
0.8409	Intermediate Similarity	NPC471817
0.8406	Intermediate Similarity	NPC470741
0.8385	Intermediate Similarity	NPC474279
0.8385	Intermediate Similarity	NPC329707
0.8385	Intermediate Similarity	NPC474438
0.8372	Intermediate Similarity	NPC329694
0.8372	Intermediate Similarity	NPC81912
0.8372	Intermediate Similarity	NPC329922
0.8372	Intermediate Similarity	NPC474260
0.837	Intermediate Similarity	NPC42400
0.8369	Intermediate Similarity	NPC476941
0.8369	Intermediate Similarity	NPC476942
0.8359	Intermediate Similarity	NPC118853
0.8347	Intermediate Similarity	NPC105249
0.8321	Intermediate Similarity	NPC67003
0.8321	Intermediate Similarity	NPC198904
0.8321	Intermediate Similarity	NPC90296
0.832	Intermediate Similarity	NPC87466
0.831	Intermediate Similarity	NPC234494
0.8308	Intermediate Similarity	NPC474830
0.8298	Intermediate Similarity	NPC255414
0.8298	Intermediate Similarity	NPC216755
0.8298	Intermediate Similarity	NPC476938
0.8298	Intermediate Similarity	NPC476937
0.8295	Intermediate Similarity	NPC71274
0.8295	Intermediate Similarity	NPC471559
0.8295	Intermediate Similarity	NPC75557
0.8271	Intermediate Similarity	NPC473982
0.8271	Intermediate Similarity	NPC471995
0.8268	Intermediate Similarity	NPC97566
0.8264	Intermediate Similarity	NPC44577
0.8261	Intermediate Similarity	NPC205765
0.8254	Intermediate Similarity	NPC473969
0.8252	Intermediate Similarity	NPC470997
0.825	Intermediate Similarity	NPC473356
0.825	Intermediate Similarity	NPC471521
0.8235	Intermediate Similarity	NPC170604
0.8235	Intermediate Similarity	NPC215109
0.8235	Intermediate Similarity	NPC186626
0.8214	Intermediate Similarity	NPC199044
0.8214	Intermediate Similarity	NPC142113
0.8214	Intermediate Similarity	NPC238843
0.8209	Intermediate Similarity	NPC474425
0.8209	Intermediate Similarity	NPC474407
0.8209	Intermediate Similarity	NPC293253
0.8209	Intermediate Similarity	NPC474426
0.8201	Intermediate Similarity	NPC52412
0.8201	Intermediate Similarity	NPC263337
0.8194	Intermediate Similarity	NPC272590
0.8182	Intermediate Similarity	NPC69647
0.8182	Intermediate Similarity	NPC177331
0.8182	Intermediate Similarity	NPC125182
0.8182	Intermediate Similarity	NPC195325
0.8182	Intermediate Similarity	NPC472654
0.8175	Intermediate Similarity	NPC472376
0.8156	Intermediate Similarity	NPC185456
0.8154	Intermediate Similarity	NPC300098
0.8154	Intermediate Similarity	NPC290193
0.8143	Intermediate Similarity	NPC243577
0.8143	Intermediate Similarity	NPC476946
0.8143	Intermediate Similarity	NPC223415
0.814	Intermediate Similarity	NPC475818
0.814	Intermediate Similarity	NPC476351
0.8138	Intermediate Similarity	NPC246164
0.8138	Intermediate Similarity	NPC33938
0.8138	Intermediate Similarity	NPC469503
0.8125	Intermediate Similarity	NPC212257
0.8125	Intermediate Similarity	NPC228842
0.812	Intermediate Similarity	NPC21460
0.8112	Intermediate Similarity	NPC93666
0.8099	Intermediate Similarity	NPC471292
0.8095	Intermediate Similarity	NPC131801
0.8082	Intermediate Similarity	NPC178932
0.8082	Intermediate Similarity	NPC30222
0.8082	Intermediate Similarity	NPC57998
0.808	Intermediate Similarity	NPC28054
0.8062	Intermediate Similarity	NPC289911
0.8062	Intermediate Similarity	NPC471549
0.8062	Intermediate Similarity	NPC283284
0.8062	Intermediate Similarity	NPC473379
0.8047	Intermediate Similarity	NPC474817
0.8042	Intermediate Similarity	NPC10088
0.8042	Intermediate Similarity	NPC302987
0.8031	Intermediate Similarity	NPC187547
0.8031	Intermediate Similarity	NPC21831
0.803	Intermediate Similarity	NPC473355
0.803	Intermediate Similarity	NPC471573
0.803	Intermediate Similarity	NPC471554
0.803	Intermediate Similarity	NPC471501
0.8028	Intermediate Similarity	NPC5676
0.8028	Intermediate Similarity	NPC247221
0.8027	Intermediate Similarity	NPC155939
0.8027	Intermediate Similarity	NPC35000
0.8027	Intermediate Similarity	NPC214541
0.8027	Intermediate Similarity	NPC92979
0.8027	Intermediate Similarity	NPC141538
0.8027	Intermediate Similarity	NPC44675
0.8027	Intermediate Similarity	NPC281258
0.8027	Intermediate Similarity	NPC296807
0.8027	Intermediate Similarity	NPC264943
0.8027	Intermediate Similarity	NPC469336
0.8014	Intermediate Similarity	NPC294511
0.8014	Intermediate Similarity	NPC476939
0.8014	Intermediate Similarity	NPC268905
0.8014	Intermediate Similarity	NPC75906
0.8014	Intermediate Similarity	NPC121615
0.8014	Intermediate Similarity	NPC472672
0.8014	Intermediate Similarity	NPC476940
0.8	Intermediate Similarity	NPC20500
0.7986	Intermediate Similarity	NPC474722
0.7984	Intermediate Similarity	NPC474136
0.7984	Intermediate Similarity	NPC79557
0.7972	Intermediate Similarity	NPC262198
0.7972	Intermediate Similarity	NPC276676
0.7959	Intermediate Similarity	NPC98206
0.7959	Intermediate Similarity	NPC34421
0.7959	Intermediate Similarity	NPC253201
0.7959	Intermediate Similarity	NPC237259
0.7959	Intermediate Similarity	NPC302054
0.7959	Intermediate Similarity	NPC282445
0.7958	Intermediate Similarity	NPC137295
0.7943	Intermediate Similarity	NPC473152

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 NPC83178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	986
0.2-0.3	1811
0.3-0.4	2635
0.4-0.5	2202
0.5-0.6	1024
0.6-0.7	275
0.7-0.8	12
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
0.7986	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6273	Approved
0.755	Intermediate Similarity	NPD5761	Phase 2
0.755	Intermediate Similarity	NPD5760	Phase 2
0.7448	Intermediate Similarity	NPD4628	Phase 3
0.7343	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD6765	Approved
0.7178	Intermediate Similarity	NPD6764	Approved
0.7174	Intermediate Similarity	NPD2797	Approved
0.7123	Intermediate Similarity	NPD2346	Discontinued
0.7113	Intermediate Similarity	NPD8032	Phase 2
0.7101	Intermediate Similarity	NPD1283	Approved
0.7099	Intermediate Similarity	NPD1241	Discontinued
0.7095	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1608	Approved
0.708	Intermediate Similarity	NPD3972	Approved
0.7066	Intermediate Similarity	NPD8434	Phase 2
0.7063	Intermediate Similarity	NPD4140	Approved
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2313	Discontinued
0.7037	Intermediate Similarity	NPD5585	Approved
0.7027	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6832	Phase 2
0.7014	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD2344	Approved
0.7006	Intermediate Similarity	NPD6785	Approved
0.7006	Intermediate Similarity	NPD6784	Approved
0.7	Intermediate Similarity	NPD2798	Approved
0.7	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4308	Phase 3
0.6985	Remote Similarity	NPD1778	Approved
0.6985	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4110	Phase 3
0.6978	Remote Similarity	NPD1876	Approved
0.6957	Remote Similarity	NPD9717	Approved
0.6948	Remote Similarity	NPD7458	Discontinued
0.6943	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1551	Phase 2
0.6939	Remote Similarity	NPD4476	Approved
0.6939	Remote Similarity	NPD4477	Approved
0.6923	Remote Similarity	NPD3268	Approved
0.6892	Remote Similarity	NPD1471	Phase 3
0.6887	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1281	Approved
0.6867	Remote Similarity	NPD3750	Approved
0.6861	Remote Similarity	NPD17	Approved
0.6846	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1894	Discontinued
0.6828	Remote Similarity	NPD4307	Phase 2
0.6828	Remote Similarity	NPD2979	Phase 3
0.6824	Remote Similarity	NPD2935	Discontinued
0.6821	Remote Similarity	NPD2309	Approved
0.6818	Remote Similarity	NPD920	Approved
0.6809	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1203	Approved
0.6806	Remote Similarity	NPD3764	Approved
0.6797	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6599	Discontinued
0.6791	Remote Similarity	NPD5951	Approved
0.6788	Remote Similarity	NPD5691	Approved
0.6786	Remote Similarity	NPD4359	Approved
0.6779	Remote Similarity	NPD6002	Phase 3
0.6779	Remote Similarity	NPD6005	Phase 3
0.6779	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6004	Phase 3
0.6772	Remote Similarity	NPD7819	Suspended
0.6763	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3748	Approved
0.6755	Remote Similarity	NPD8166	Discontinued
0.6739	Remote Similarity	NPD4626	Approved
0.6736	Remote Similarity	NPD7008	Discontinued
0.6733	Remote Similarity	NPD4534	Discontinued
0.6731	Remote Similarity	NPD3226	Approved
0.6728	Remote Similarity	NPD8127	Discontinued
0.6718	Remote Similarity	NPD2182	Approved
0.6715	Remote Similarity	NPD9545	Approved
0.6692	Remote Similarity	NPD3134	Approved
0.6691	Remote Similarity	NPD3496	Discontinued
0.669	Remote Similarity	NPD411	Approved
0.669	Remote Similarity	NPD6798	Discontinued
0.669	Remote Similarity	NPD3266	Approved
0.669	Remote Similarity	NPD3267	Approved
0.6689	Remote Similarity	NPD1243	Approved
0.6688	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2614	Approved
0.6644	Remote Similarity	NPD6663	Approved
0.6643	Remote Similarity	NPD1019	Discontinued
0.6643	Remote Similarity	NPD5647	Approved
0.6623	Remote Similarity	NPD5958	Discontinued
0.6621	Remote Similarity	NPD7095	Approved
0.6619	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2531	Phase 2
0.66	Remote Similarity	NPD2438	Suspended
0.6599	Remote Similarity	NPD4060	Phase 1
0.6597	Remote Similarity	NPD5736	Approved
0.6584	Remote Similarity	NPD7768	Phase 2
0.6581	Remote Similarity	NPD2533	Approved
0.6581	Remote Similarity	NPD2534	Approved
0.6581	Remote Similarity	NPD2532	Approved
0.6575	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6362	Approved
0.6571	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD9493	Approved
0.6568	Remote Similarity	NPD6559	Discontinued
0.6562	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7236	Approved
0.6558	Remote Similarity	NPD7440	Discontinued
0.6556	Remote Similarity	NPD5763	Approved
0.6556	Remote Similarity	NPD5762	Approved
0.6554	Remote Similarity	NPD447	Suspended
0.6554	Remote Similarity	NPD4622	Approved
0.6554	Remote Similarity	NPD4618	Approved
0.6549	Remote Similarity	NPD5327	Phase 3
0.6547	Remote Similarity	NPD1651	Approved
0.6543	Remote Similarity	NPD3749	Approved
0.6541	Remote Similarity	NPD7411	Suspended
0.6531	Remote Similarity	NPD4062	Phase 3
0.6531	Remote Similarity	NPD4870	Approved
0.6531	Remote Similarity	NPD6233	Phase 2
0.6528	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6799	Approved
0.6513	Remote Similarity	NPD970	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6653	Approved
0.6503	Remote Similarity	NPD919	Approved
0.65	Remote Similarity	NPD2932	Approved
0.6497	Remote Similarity	NPD7427	Discontinued
0.6497	Remote Similarity	NPD3873	Phase 3
0.6497	Remote Similarity	NPD3869	Phase 3
0.6496	Remote Similarity	NPD7157	Approved
0.6494	Remote Similarity	NPD2354	Approved
0.6494	Remote Similarity	NPD3887	Approved
0.649	Remote Similarity	NPD6100	Approved
0.649	Remote Similarity	NPD6099	Approved
0.649	Remote Similarity	NPD2796	Approved
0.6486	Remote Similarity	NPD3142	Approved
0.6486	Remote Similarity	NPD3140	Approved
0.6484	Remote Similarity	NPD1238	Approved
0.6483	Remote Similarity	NPD9494	Approved
0.6479	Remote Similarity	NPD1481	Phase 2
0.6471	Remote Similarity	NPD2800	Approved
0.6467	Remote Similarity	NPD5688	Approved
0.6467	Remote Similarity	NPD5689	Approved
0.6463	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD3847	Discontinued
0.6447	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1933	Approved
0.6443	Remote Similarity	NPD5735	Approved
0.6442	Remote Similarity	NPD7075	Discontinued
0.6433	Remote Similarity	NPD5049	Phase 3
0.6429	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7177	Discontinued
0.6424	Remote Similarity	NPD7033	Discontinued
0.6423	Remote Similarity	NPD2629	Approved
0.6412	Remote Similarity	NPD164	Approved
0.641	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6287	Discontinued
0.6408	Remote Similarity	NPD1535	Discovery
0.6405	Remote Similarity	NPD2897	Discontinued
0.64	Remote Similarity	NPD6353	Approved
0.6398	Remote Similarity	NPD6280	Approved
0.6398	Remote Similarity	NPD6279	Approved
0.6397	Remote Similarity	NPD5535	Approved
0.6391	Remote Similarity	NPD1358	Approved
0.6391	Remote Similarity	NPD5844	Phase 1
0.6389	Remote Similarity	NPD8651	Approved
0.6386	Remote Similarity	NPD6808	Phase 2
0.6383	Remote Similarity	NPD3019	Approved
0.637	Remote Similarity	NPD454	Approved
0.6369	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9697	Approved
0.6358	Remote Similarity	NPD7097	Phase 1
0.6352	Remote Similarity	NPD7239	Suspended
0.6351	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2684	Approved
0.6341	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2353	Approved
0.634	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD1930	Approved
0.6336	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD1929	Approved
0.6335	Remote Similarity	NPD6873	Phase 2
0.6335	Remote Similarity	NPD6677	Suspended
0.6319	Remote Similarity	NPD2296	Approved
0.6319	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2651	Approved
0.6312	Remote Similarity	NPD2649	Approved
0.631	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6917	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