NPASS Compound

Structure

NPC475925 OpenBabel07101718182D 26 28 0 0 1 0 0 0 0 0999 V2000 3.4565 5.7550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8370 3.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9297 -0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2410 1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4385 4.3537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2560 3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6923 2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7340 5.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5430 5.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2371 2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2946 0.9705 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6978 2.1115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9002 1.0288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5068 2.5457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5249 3.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2910 1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4769 1.5461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3232 0.9463 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9999 0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8385 6.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 0.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7159 4.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5997 -0.7852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 2.9524 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 9 1 0 0 0 0 2 10 2 0 0 0 0 3 11 2 0 0 0 0 5 9 2 0 0 0 0 5 16 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 4 1 1 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 7 1 1 0 0 0 13 17 1 0 0 0 0 14 22 1 1 0 0 0 15 18 1 0 0 0 0 15 25 1 6 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 19 26 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	368.366
LogP:	1.096
LogD:	1.42
LogS:	-2.524
# Rotatable Bonds:	5
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.077
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.941
MDCK Permeability:	0.00011349318810971454
Pgp-inhibitor:	0.001
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.146
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.806

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	63.18206787109375%
Volume Distribution (VD):	1.29
Pgp-substrate:	49.800235748291016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.225
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.302
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	11.598
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.155
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.661
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.519
Carcinogencity:	0.119
Eye Corrosion:	0.024
Eye Irritation:	0.022
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC475925

Natural Product ID:	NPC475925
*Common Name:**	8-Alpha-(4-Hydroxysenecioyloxy)Dehydrozaluzanin C
IUPAC Name:	[(3R,3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] (Z)-4-hydroxy-3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	DTHPKFOZPQHUHF-LRIMPVSOSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-9(8-21)5-16(23)25-15-6-10(2)13-7-14(22)11(3)17(13)19-18(15)12(4)20(24)26-19/h5,12-15,17-19,21-22H,2-3,6-8H2,1,4H3/b9-5-/t12-,13+,14+,15+,17+,18-,19-/m1/s1
SMILES:	CC1C2C(CC(=C)C3CC(C(=C)C3C2OC1=O)O)OC(=O)C=C(C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518708
PubChem CID:	44567545
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[18314958]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2291	Saussurea pulchella	Species	Asteraceae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	8.22	uM	PMID[469142]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	2.49	uM	PMID[469142]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	1.53	uM	PMID[469142]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	3.82	uM	PMID[469142]

☑ 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 NPC475925 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	220
0.1-0.2	1355
0.2-0.3	5319
0.3-0.4	12519
0.4-0.5	11737
0.5-0.6	7232
0.6-0.7	3359
0.7-0.8	800
0.8-0.85	84
0.85-0.9	58
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC217983
0.9419	High Similarity	NPC207114
0.9333	High Similarity	NPC18019
0.9333	High Similarity	NPC24956
0.9205	High Similarity	NPC19087
0.9186	High Similarity	NPC64153
0.9186	High Similarity	NPC187661
0.9101	High Similarity	NPC184063
0.9091	High Similarity	NPC38392
0.9059	High Similarity	NPC128246
0.9011	High Similarity	NPC304886
0.8989	High Similarity	NPC297474
0.8989	High Similarity	NPC54065
0.8953	High Similarity	NPC224386
0.8953	High Similarity	NPC194859
0.8936	High Similarity	NPC171759
0.8936	High Similarity	NPC150923
0.8901	High Similarity	NPC477131
0.8901	High Similarity	NPC323008
0.8901	High Similarity	NPC470013
0.8901	High Similarity	NPC262133
0.8901	High Similarity	NPC470010
0.8901	High Similarity	NPC198853
0.8889	High Similarity	NPC133888
0.8889	High Similarity	NPC35959
0.8889	High Similarity	NPC29821
0.8889	High Similarity	NPC171360
0.8889	High Similarity	NPC57304
0.8889	High Similarity	NPC293001
0.8889	High Similarity	NPC63193
0.8876	High Similarity	NPC155935
0.8876	High Similarity	NPC215556
0.8824	High Similarity	NPC126248
0.8817	High Similarity	NPC161493
0.8804	High Similarity	NPC170120
0.8804	High Similarity	NPC213698
0.8804	High Similarity	NPC67584
0.8804	High Similarity	NPC52044
0.8778	High Similarity	NPC216284
0.8778	High Similarity	NPC35809
0.8764	High Similarity	NPC79549
0.8721	High Similarity	NPC246076
0.871	High Similarity	NPC213078
0.8696	High Similarity	NPC127019
0.8681	High Similarity	NPC133698
0.8681	High Similarity	NPC131209
0.8646	High Similarity	NPC86077
0.8621	High Similarity	NPC111409
0.8617	High Similarity	NPC108475
0.8617	High Similarity	NPC170143
0.8617	High Similarity	NPC213947
0.8617	High Similarity	NPC474313
0.8602	High Similarity	NPC472873
0.8602	High Similarity	NPC476053
0.8587	High Similarity	NPC258216
0.8571	High Similarity	NPC54737
0.8539	High Similarity	NPC56593
0.8539	High Similarity	NPC304558
0.8526	High Similarity	NPC221615
0.8511	High Similarity	NPC126156
0.8511	High Similarity	NPC142529
0.8511	High Similarity	NPC91771
0.8478	Intermediate Similarity	NPC155215
0.8462	Intermediate Similarity	NPC295312
0.8444	Intermediate Similarity	NPC118601
0.8444	Intermediate Similarity	NPC24728
0.8427	Intermediate Similarity	NPC300082
0.8427	Intermediate Similarity	NPC204105
0.8427	Intermediate Similarity	NPC284534
0.8421	Intermediate Similarity	NPC471150
0.8404	Intermediate Similarity	NPC163228
0.8387	Intermediate Similarity	NPC228451
0.8387	Intermediate Similarity	NPC475788
0.8387	Intermediate Similarity	NPC475838
0.8387	Intermediate Similarity	NPC135776
0.8387	Intermediate Similarity	NPC125674
0.8384	Intermediate Similarity	NPC166115
0.8384	Intermediate Similarity	NPC243998
0.837	Intermediate Similarity	NPC37607
0.837	Intermediate Similarity	NPC129419
0.837	Intermediate Similarity	NPC301969
0.837	Intermediate Similarity	NPC475855
0.8352	Intermediate Similarity	NPC91248
0.8352	Intermediate Similarity	NPC178875
0.8352	Intermediate Similarity	NPC471149
0.8333	Intermediate Similarity	NPC475461
0.8333	Intermediate Similarity	NPC305475
0.8333	Intermediate Similarity	NPC236692
0.8333	Intermediate Similarity	NPC309757
0.8317	Intermediate Similarity	NPC59489
0.8317	Intermediate Similarity	NPC139838
0.8298	Intermediate Similarity	NPC474247
0.8298	Intermediate Similarity	NPC474338
0.8298	Intermediate Similarity	NPC473331
0.8295	Intermediate Similarity	NPC89555
0.8261	Intermediate Similarity	NPC472872
0.8261	Intermediate Similarity	NPC268298
0.8261	Intermediate Similarity	NPC283409
0.8261	Intermediate Similarity	NPC32922
0.8242	Intermediate Similarity	NPC160138
0.8242	Intermediate Similarity	NPC237540
0.8229	Intermediate Similarity	NPC236580
0.8229	Intermediate Similarity	NPC477949
0.8229	Intermediate Similarity	NPC311904
0.8229	Intermediate Similarity	NPC304445
0.8222	Intermediate Similarity	NPC255307
0.8222	Intermediate Similarity	NPC78089
0.8222	Intermediate Similarity	NPC165162
0.8202	Intermediate Similarity	NPC245665
0.82	Intermediate Similarity	NPC223450
0.8191	Intermediate Similarity	NPC200237
0.8191	Intermediate Similarity	NPC473263
0.8191	Intermediate Similarity	NPC308656
0.8191	Intermediate Similarity	NPC475912
0.8191	Intermediate Similarity	NPC60386
0.8191	Intermediate Similarity	NPC473273
0.8191	Intermediate Similarity	NPC473234
0.8173	Intermediate Similarity	NPC273242
0.8172	Intermediate Similarity	NPC179394
0.8172	Intermediate Similarity	NPC144133
0.8163	Intermediate Similarity	NPC67296
0.8144	Intermediate Similarity	NPC249171
0.8144	Intermediate Similarity	NPC49833
0.8144	Intermediate Similarity	NPC187268
0.8144	Intermediate Similarity	NPC141191
0.8132	Intermediate Similarity	NPC107787
0.8132	Intermediate Similarity	NPC470242
0.8132	Intermediate Similarity	NPC67493
0.8125	Intermediate Similarity	NPC230800
0.8125	Intermediate Similarity	NPC279621
0.8125	Intermediate Similarity	NPC474297
0.8119	Intermediate Similarity	NPC26617
0.8111	Intermediate Similarity	NPC191476
0.8111	Intermediate Similarity	NPC476804
0.8111	Intermediate Similarity	NPC165287
0.8111	Intermediate Similarity	NPC114979
0.81	Intermediate Similarity	NPC203659
0.81	Intermediate Similarity	NPC100487
0.8095	Intermediate Similarity	NPC121816
0.8085	Intermediate Similarity	NPC286341
0.8085	Intermediate Similarity	NPC191339
0.8081	Intermediate Similarity	NPC80144
0.8068	Intermediate Similarity	NPC156658
0.8068	Intermediate Similarity	NPC51507
0.8068	Intermediate Similarity	NPC258965
0.8065	Intermediate Similarity	NPC4986
0.8065	Intermediate Similarity	NPC168679
0.8065	Intermediate Similarity	NPC12872
0.8065	Intermediate Similarity	NPC212664
0.8061	Intermediate Similarity	NPC186861
0.8061	Intermediate Similarity	NPC471381
0.8061	Intermediate Similarity	NPC70865
0.8041	Intermediate Similarity	NPC181151
0.8041	Intermediate Similarity	NPC169205
0.8022	Intermediate Similarity	NPC235792
0.8021	Intermediate Similarity	NPC270013
0.8021	Intermediate Similarity	NPC14961
0.8021	Intermediate Similarity	NPC36954
0.8021	Intermediate Similarity	NPC220221
0.8021	Intermediate Similarity	NPC469873
0.8	Intermediate Similarity	NPC473148
0.8	Intermediate Similarity	NPC473390
0.8	Intermediate Similarity	NPC131669
0.8	Intermediate Similarity	NPC110989
0.8	Intermediate Similarity	NPC40746
0.8	Intermediate Similarity	NPC124881
0.8	Intermediate Similarity	NPC179746
0.8	Intermediate Similarity	NPC475945
0.8	Intermediate Similarity	NPC153590
0.8	Intermediate Similarity	NPC169575
0.8	Intermediate Similarity	NPC475871
0.8	Intermediate Similarity	NPC250315
0.8	Intermediate Similarity	NPC81419
0.798	Intermediate Similarity	NPC477950
0.7979	Intermediate Similarity	NPC469368
0.7979	Intermediate Similarity	NPC473448
0.7978	Intermediate Similarity	NPC470241
0.7978	Intermediate Similarity	NPC52861
0.7959	Intermediate Similarity	NPC474213
0.7959	Intermediate Similarity	NPC45125
0.7957	Intermediate Similarity	NPC202672
0.7957	Intermediate Similarity	NPC224652
0.7957	Intermediate Similarity	NPC476805
0.7938	Intermediate Similarity	NPC476315
0.7938	Intermediate Similarity	NPC185553
0.7935	Intermediate Similarity	NPC284902
0.7935	Intermediate Similarity	NPC162071
0.7935	Intermediate Similarity	NPC150755
0.7925	Intermediate Similarity	NPC471380
0.7917	Intermediate Similarity	NPC167219
0.7917	Intermediate Similarity	NPC81386
0.7917	Intermediate Similarity	NPC474035
0.7912	Intermediate Similarity	NPC472958
0.7912	Intermediate Similarity	NPC141193
0.7912	Intermediate Similarity	NPC16887
0.7912	Intermediate Similarity	NPC37005
0.7912	Intermediate Similarity	NPC96259
0.7912	Intermediate Similarity	NPC472957
0.7912	Intermediate Similarity	NPC156485
0.7912	Intermediate Similarity	NPC115786

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 NPC475925 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	2076
0.2-0.3	3811
0.3-0.4	2153
0.4-0.5	527
0.5-0.6	294
0.6-0.7	40
0.7-0.8	19
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8119	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1695	Approved
0.7935	Intermediate Similarity	NPD4249	Approved
0.7849	Intermediate Similarity	NPD4250	Approved
0.7849	Intermediate Similarity	NPD4251	Approved
0.7835	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6371	Approved
0.7609	Intermediate Similarity	NPD5362	Discontinued
0.7604	Intermediate Similarity	NPD6698	Approved
0.7604	Intermediate Similarity	NPD46	Approved
0.7604	Intermediate Similarity	NPD5785	Approved
0.757	Intermediate Similarity	NPD6053	Discontinued
0.7473	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5363	Approved
0.7447	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7154	Phase 3
0.7353	Intermediate Similarity	NPD7639	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7312	Intermediate Similarity	NPD4269	Approved
0.7312	Intermediate Similarity	NPD4270	Approved
0.7283	Intermediate Similarity	NPD4819	Approved
0.7283	Intermediate Similarity	NPD4821	Approved
0.7283	Intermediate Similarity	NPD4820	Approved
0.7283	Intermediate Similarity	NPD4822	Approved
0.7255	Intermediate Similarity	NPD7638	Approved
0.7253	Intermediate Similarity	NPD4268	Approved
0.7253	Intermediate Similarity	NPD4271	Approved
0.7188	Intermediate Similarity	NPD5786	Approved
0.7128	Intermediate Similarity	NPD6435	Approved
0.7097	Intermediate Similarity	NPD4252	Approved
0.7071	Intermediate Similarity	NPD7838	Discovery
0.7053	Intermediate Similarity	NPD5332	Approved
0.7053	Intermediate Similarity	NPD5331	Approved
0.703	Intermediate Similarity	NPD5282	Discontinued
0.7021	Intermediate Similarity	NPD4790	Discontinued
0.7021	Intermediate Similarity	NPD5369	Approved
0.7	Intermediate Similarity	NPD7983	Approved
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD4225	Approved
0.6915	Remote Similarity	NPD5368	Approved
0.6907	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6686	Approved
0.6847	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7632	Discontinued
0.6697	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD5344	Discontinued
0.6602	Remote Similarity	NPD6399	Phase 3
0.6598	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1694	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6529	Remote Similarity	NPD7507	Approved
0.6509	Remote Similarity	NPD6083	Phase 2
0.6509	Remote Similarity	NPD6084	Phase 2
0.6486	Remote Similarity	NPD6412	Phase 2
0.6476	Remote Similarity	NPD5695	Phase 3
0.6449	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD7839	Suspended
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6389	Remote Similarity	NPD6648	Approved
0.6373	Remote Similarity	NPD6903	Approved
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6372	Approved
0.6371	Remote Similarity	NPD7319	Approved
0.6339	Remote Similarity	NPD5701	Approved
0.6339	Remote Similarity	NPD5697	Approved
0.6337	Remote Similarity	NPD6684	Approved
0.6337	Remote Similarity	NPD5330	Approved
0.6337	Remote Similarity	NPD7146	Approved
0.6337	Remote Similarity	NPD6409	Approved
0.6337	Remote Similarity	NPD7521	Approved
0.6337	Remote Similarity	NPD7334	Approved
0.6333	Remote Similarity	NPD8513	Phase 3
0.6333	Remote Similarity	NPD8517	Approved
0.6333	Remote Similarity	NPD8516	Approved
0.6333	Remote Similarity	NPD8515	Approved
0.6316	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3133	Approved
0.63	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3665	Phase 1
0.63	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3666	Approved
0.6283	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD6899	Approved
0.6261	Remote Similarity	NPD6650	Approved
0.6261	Remote Similarity	NPD6649	Approved
0.6228	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD6014	Approved
0.6228	Remote Similarity	NPD6012	Approved
0.6218	Remote Similarity	NPD7328	Approved
0.6218	Remote Similarity	NPD7327	Approved
0.6214	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6695	Phase 3
0.6198	Remote Similarity	NPD8033	Approved
0.619	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD8035	Phase 2
0.619	Remote Similarity	NPD5281	Approved
0.619	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD5284	Approved
0.6179	Remote Similarity	NPD7492	Approved
0.6176	Remote Similarity	NPD3618	Phase 1
0.6174	Remote Similarity	NPD7290	Approved
0.6174	Remote Similarity	NPD7102	Approved
0.6174	Remote Similarity	NPD6883	Approved
0.6168	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7516	Approved
0.6154	Remote Similarity	NPD5370	Suspended
0.6154	Remote Similarity	NPD4632	Approved
0.6154	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD8133	Approved
0.614	Remote Similarity	NPD6011	Approved
0.6129	Remote Similarity	NPD6616	Approved
0.6126	Remote Similarity	NPD5211	Phase 2
0.6121	Remote Similarity	NPD6847	Approved
0.6121	Remote Similarity	NPD6617	Approved
0.6121	Remote Similarity	NPD6869	Approved
0.6121	Remote Similarity	NPD8130	Phase 1
0.6116	Remote Similarity	NPD6319	Approved
0.6116	Remote Similarity	NPD8294	Approved
0.6116	Remote Similarity	NPD8377	Approved
0.6116	Remote Similarity	NPD6059	Approved
0.6116	Remote Similarity	NPD6054	Approved
0.6111	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5209	Approved
0.61	Remote Similarity	NPD3667	Approved
0.6095	Remote Similarity	NPD5207	Approved
0.6092	Remote Similarity	NPD3198	Approved
0.608	Remote Similarity	NPD7078	Approved
0.608	Remote Similarity	NPD8293	Discontinued
0.608	Remote Similarity	NPD8074	Phase 3
0.6068	Remote Similarity	NPD8297	Approved
0.6068	Remote Similarity	NPD6882	Approved
0.6066	Remote Similarity	NPD8378	Approved
0.6066	Remote Similarity	NPD8380	Approved
0.6066	Remote Similarity	NPD6016	Approved
0.6066	Remote Similarity	NPD8335	Approved
0.6066	Remote Similarity	NPD8379	Approved
0.6066	Remote Similarity	NPD6015	Approved
0.6066	Remote Similarity	NPD8296	Approved
0.6058	Remote Similarity	NPD6672	Approved
0.6058	Remote Similarity	NPD5737	Approved
0.6055	Remote Similarity	NPD7902	Approved
0.6055	Remote Similarity	NPD4755	Approved
0.6053	Remote Similarity	NPD6685	Approved
0.6053	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6110	Phase 1
0.6038	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6420	Discontinued
0.6032	Remote Similarity	NPD7736	Approved
0.602	Remote Similarity	NPD4802	Phase 2
0.602	Remote Similarity	NPD4238	Approved
0.6019	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD5210	Approved
0.6018	Remote Similarity	NPD5141	Approved
0.6016	Remote Similarity	NPD6370	Approved
0.6016	Remote Similarity	NPD5988	Approved
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8273	Phase 1
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4202	Approved
0.598	Remote Similarity	NPD4786	Approved
0.5969	Remote Similarity	NPD6845	Suspended
0.5963	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7750	Discontinued
0.5962	Remote Similarity	NPD7524	Approved
0.596	Remote Similarity	NPD6929	Approved
0.5946	Remote Similarity	NPD4700	Approved
0.5946	Remote Similarity	NPD4696	Approved
0.5946	Remote Similarity	NPD5285	Approved
0.5946	Remote Similarity	NPD5286	Approved
0.5935	Remote Similarity	NPD5983	Phase 2
0.5935	Remote Similarity	NPD7503	Approved
0.5935	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7748	Approved
0.5926	Remote Similarity	NPD6001	Approved
0.5922	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4756	Discovery
0.5917	Remote Similarity	NPD6274	Approved
0.59	Remote Similarity	NPD6930	Phase 2
0.59	Remote Similarity	NPD6931	Approved
0.5888	Remote Similarity	NPD7515	Phase 2
0.5882	Remote Similarity	NPD6005	Phase 3
0.5882	Remote Similarity	NPD6004	Phase 3
0.5882	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6006	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