NPASS Compound

Structure

NPC475788 OpenBabel07101718302D 26 28 0 0 1 0 0 0 0 0999 V2000 -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 3.0262 5.1627 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 3.2475 3.7659 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 -1.2910 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 1.5249 3.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4385 4.3537 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.1610 4.1726 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 1.5997 -0.7852 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 2.0317 5.2672 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 8 2 0 0 0 0 2 9 2 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 7 19 1 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 3 1 1 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 6 1 1 0 0 0 11 14 1 0 0 0 0 12 21 1 1 0 0 0 13 15 1 0 0 0 0 13 25 1 6 0 0 0 14 9 1 1 0 0 0 14 16 1 0 0 0 0 15 16 1 0 0 0 0 16 26 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.17
Volume:	362.497
LogP:	0.796
LogD:	1.061
LogS:	-1.974
# Rotatable Bonds:	4
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	5.12
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.61
MDCK Permeability:	0.00014628152712248266
Pgp-inhibitor:	0.001
Pgp-substrate:	0.183
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.834

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	52.016563415527344%
Volume Distribution (VD):	0.451
Pgp-substrate:	52.360008239746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.473
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	4.857
Half-life (T1/2):	0.423

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.662
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.06
Carcinogencity:	0.087
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.761

Download Data

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

Natural Product: NPC475788

Natural Product ID:	NPC475788
*Common Name:**	8-Alpha-O-(2,3-Dihydroxyisobutyryl)11Beta,13-Dihydrodesacylcynaropicrin
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] 2,3-dihydroxy-2-methylpropanoate
Synonyms:
Standard InCHIKey:	XXTSIUYSUUNNEI-HYVDOFMESA-N
Standard InCHI:	InChI=1S/C19H26O7/c1-8-5-13(25-18(23)19(4,24)7-20)15-10(3)17(22)26-16(15)14-9(2)12(21)6-11(8)14/h10-16,20-21,24H,1-2,5-7H2,3-4H3/t10-,11+,12+,13+,14+,15-,16-,19?/m1/s1
SMILES:	OCC(C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1[C@@H](C)C(=O)O3)C(=C)[C@H](C2)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515850
PubChem CID:	44567603
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	>	30.0	uM	PMID[548061]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	uM	PMID[548061]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	30.0	uM	PMID[548061]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30.0	uM	PMID[548061]

☑ 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 NPC475788 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	256
0.1-0.2	1875
0.2-0.3	6316
0.3-0.4	14907
0.4-0.5	9061
0.5-0.6	7278
0.6-0.7	2524
0.7-0.8	397
0.8-0.85	69
0.85-0.9	11
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC474313
0.9	High Similarity	NPC184063
0.8953	High Similarity	NPC128246
0.8889	High Similarity	NPC19087
0.8778	High Similarity	NPC38392
0.8721	High Similarity	NPC126248
0.8673	High Similarity	NPC44004
0.8667	High Similarity	NPC207114
0.8667	High Similarity	NPC217983
0.8667	High Similarity	NPC53158
0.8617	High Similarity	NPC476009
0.8617	High Similarity	NPC474297
0.8526	High Similarity	NPC311904
0.8526	High Similarity	NPC471150
0.8523	High Similarity	NPC111409
0.8511	High Similarity	NPC475900
0.8511	High Similarity	NPC472873
0.8444	Intermediate Similarity	NPC187661
0.8404	Intermediate Similarity	NPC473331
0.8387	Intermediate Similarity	NPC475925
0.837	Intermediate Similarity	NPC215556
0.8333	Intermediate Similarity	NPC304445
0.8333	Intermediate Similarity	NPC236580
0.8317	Intermediate Similarity	NPC117604
0.8316	Intermediate Similarity	NPC163228
0.8283	Intermediate Similarity	NPC473148
0.828	Intermediate Similarity	NPC216284
0.828	Intermediate Similarity	NPC297474
0.828	Intermediate Similarity	NPC54065
0.8265	Intermediate Similarity	NPC67296
0.8261	Intermediate Similarity	NPC79549
0.8242	Intermediate Similarity	NPC304558
0.8229	Intermediate Similarity	NPC91771
0.8229	Intermediate Similarity	NPC142529
0.8222	Intermediate Similarity	NPC224386
0.8222	Intermediate Similarity	NPC194859
0.8218	Intermediate Similarity	NPC26617
0.8191	Intermediate Similarity	NPC469627
0.8191	Intermediate Similarity	NPC133888
0.8191	Intermediate Similarity	NPC63193
0.8191	Intermediate Similarity	NPC57304
0.8191	Intermediate Similarity	NPC29821
0.8191	Intermediate Similarity	NPC293001
0.8191	Intermediate Similarity	NPC35959
0.8191	Intermediate Similarity	NPC171360
0.8182	Intermediate Similarity	NPC474747
0.8182	Intermediate Similarity	NPC156658
0.8182	Intermediate Similarity	NPC258965
0.8172	Intermediate Similarity	NPC155935
0.8163	Intermediate Similarity	NPC471381
0.8163	Intermediate Similarity	NPC186861
0.8144	Intermediate Similarity	NPC261372
0.8144	Intermediate Similarity	NPC181151
0.8144	Intermediate Similarity	NPC58267
0.8144	Intermediate Similarity	NPC263674
0.8137	Intermediate Similarity	NPC68248
0.8125	Intermediate Similarity	NPC476053
0.8105	Intermediate Similarity	NPC258216
0.8105	Intermediate Similarity	NPC473273
0.8105	Intermediate Similarity	NPC60386
0.8105	Intermediate Similarity	NPC308656
0.8105	Intermediate Similarity	NPC473234
0.8105	Intermediate Similarity	NPC473263
0.81	Intermediate Similarity	NPC475871
0.81	Intermediate Similarity	NPC475945
0.8085	Intermediate Similarity	NPC35809
0.8085	Intermediate Similarity	NPC65359
0.8081	Intermediate Similarity	NPC150923
0.8061	Intermediate Similarity	NPC45125
0.8061	Intermediate Similarity	NPC249171
0.8061	Intermediate Similarity	NPC49833
0.8041	Intermediate Similarity	NPC76862
0.8041	Intermediate Similarity	NPC158416
0.8041	Intermediate Similarity	NPC39859
0.8041	Intermediate Similarity	NPC470883
0.8021	Intermediate Similarity	NPC198853
0.8	Intermediate Similarity	NPC246076
0.8	Intermediate Similarity	NPC80144
0.8	Intermediate Similarity	NPC155215
0.8	Intermediate Similarity	NPC86077
0.7978	Intermediate Similarity	NPC51507
0.7957	Intermediate Similarity	NPC186148
0.7957	Intermediate Similarity	NPC118601
0.7957	Intermediate Similarity	NPC190753
0.7941	Intermediate Similarity	NPC54737
0.7938	Intermediate Similarity	NPC170120
0.7938	Intermediate Similarity	NPC213698
0.7935	Intermediate Similarity	NPC284534
0.7935	Intermediate Similarity	NPC204105
0.7935	Intermediate Similarity	NPC300082
0.7917	Intermediate Similarity	NPC153590
0.7917	Intermediate Similarity	NPC200237
0.79	Intermediate Similarity	NPC474742
0.79	Intermediate Similarity	NPC171759
0.7895	Intermediate Similarity	NPC246173
0.7895	Intermediate Similarity	NPC474323
0.7895	Intermediate Similarity	NPC206614
0.7872	Intermediate Similarity	NPC178875
0.7872	Intermediate Similarity	NPC58219
0.7872	Intermediate Similarity	NPC177629
0.7857	Intermediate Similarity	NPC18019
0.7857	Intermediate Similarity	NPC24956
0.7849	Intermediate Similarity	NPC56593
0.7843	Intermediate Similarity	NPC475676
0.7843	Intermediate Similarity	NPC220964
0.7843	Intermediate Similarity	NPC100487
0.7843	Intermediate Similarity	NPC474741
0.7835	Intermediate Similarity	NPC470013
0.7835	Intermediate Similarity	NPC470010
0.7835	Intermediate Similarity	NPC323008
0.7835	Intermediate Similarity	NPC190294
0.7835	Intermediate Similarity	NPC262133
0.7835	Intermediate Similarity	NPC127019
0.7826	Intermediate Similarity	NPC3464
0.7826	Intermediate Similarity	NPC151176
0.7826	Intermediate Similarity	NPC475963
0.7812	Intermediate Similarity	NPC191339
0.7812	Intermediate Similarity	NPC131209
0.7812	Intermediate Similarity	NPC133698
0.7812	Intermediate Similarity	NPC286341
0.78	Intermediate Similarity	NPC70865
0.7789	Intermediate Similarity	NPC92974
0.7789	Intermediate Similarity	NPC168679
0.7789	Intermediate Similarity	NPC472872
0.7789	Intermediate Similarity	NPC173926
0.7789	Intermediate Similarity	NPC12872
0.7778	Intermediate Similarity	NPC54739
0.7778	Intermediate Similarity	NPC170143
0.7778	Intermediate Similarity	NPC213947
0.7778	Intermediate Similarity	NPC161493
0.7778	Intermediate Similarity	NPC108475
0.7767	Intermediate Similarity	NPC243998
0.7766	Intermediate Similarity	NPC201658
0.7766	Intermediate Similarity	NPC24728
0.7755	Intermediate Similarity	NPC52044
0.7755	Intermediate Similarity	NPC304886
0.7755	Intermediate Similarity	NPC67584
0.7745	Intermediate Similarity	NPC4620
0.7745	Intermediate Similarity	NPC475873
0.7732	Intermediate Similarity	NPC472874
0.7732	Intermediate Similarity	NPC475912
0.7717	Intermediate Similarity	NPC245665
0.7714	Intermediate Similarity	NPC139838
0.7714	Intermediate Similarity	NPC59489
0.7684	Intermediate Similarity	NPC471149
0.7677	Intermediate Similarity	NPC213078
0.767	Intermediate Similarity	NPC203659
0.766	Intermediate Similarity	NPC322922
0.766	Intermediate Similarity	NPC469626
0.766	Intermediate Similarity	NPC236692
0.766	Intermediate Similarity	NPC64153
0.766	Intermediate Similarity	NPC475019
0.766	Intermediate Similarity	NPC470242
0.766	Intermediate Similarity	NPC474949
0.766	Intermediate Similarity	NPC309757
0.766	Intermediate Similarity	NPC475491
0.766	Intermediate Similarity	NPC321812
0.7653	Intermediate Similarity	NPC477131
0.7647	Intermediate Similarity	NPC225353
0.7647	Intermediate Similarity	NPC471148
0.7634	Intermediate Similarity	NPC474780
0.7629	Intermediate Similarity	NPC471747
0.7629	Intermediate Similarity	NPC184463
0.7629	Intermediate Similarity	NPC12172
0.7629	Intermediate Similarity	NPC208886
0.7624	Intermediate Similarity	NPC473146
0.7619	Intermediate Similarity	NPC308191
0.7619	Intermediate Similarity	NPC474664
0.7619	Intermediate Similarity	NPC233379
0.7619	Intermediate Similarity	NPC255082
0.7619	Intermediate Similarity	NPC14862
0.7604	Intermediate Similarity	NPC283409
0.7604	Intermediate Similarity	NPC474951
0.7604	Intermediate Similarity	NPC473564
0.76	Intermediate Similarity	NPC323421
0.76	Intermediate Similarity	NPC328562
0.7596	Intermediate Similarity	NPC179891
0.7596	Intermediate Similarity	NPC223450
0.7596	Intermediate Similarity	NPC474101
0.7579	Intermediate Similarity	NPC179659
0.7576	Intermediate Similarity	NPC14961
0.7576	Intermediate Similarity	NPC167893
0.7576	Intermediate Similarity	NPC270013
0.7576	Intermediate Similarity	NPC36954
0.7573	Intermediate Similarity	NPC124881
0.7573	Intermediate Similarity	NPC110989
0.7553	Intermediate Similarity	NPC329749
0.7551	Intermediate Similarity	NPC212486
0.7551	Intermediate Similarity	NPC469692
0.7551	Intermediate Similarity	NPC469645
0.7551	Intermediate Similarity	NPC179746
0.7551	Intermediate Similarity	NPC81419
0.7549	Intermediate Similarity	NPC201718
0.7549	Intermediate Similarity	NPC47880
0.7549	Intermediate Similarity	NPC164598
0.7549	Intermediate Similarity	NPC474339
0.7549	Intermediate Similarity	NPC185141
0.7549	Intermediate Similarity	NPC128733
0.7549	Intermediate Similarity	NPC110443
0.7549	Intermediate Similarity	NPC133907

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 NPC475788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	2657
0.2-0.3	3778
0.3-0.4	1597
0.4-0.5	498
0.5-0.6	250
0.6-0.7	52
0.7-0.8	5
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
0.8218	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6371	Approved
0.7292	Intermediate Similarity	NPD4249	Approved
0.7273	Intermediate Similarity	NPD7983	Approved
0.7245	Intermediate Similarity	NPD1695	Approved
0.7216	Intermediate Similarity	NPD4251	Approved
0.7216	Intermediate Similarity	NPD4250	Approved
0.7129	Intermediate Similarity	NPD5282	Discontinued
0.7128	Intermediate Similarity	NPD5369	Approved
0.7059	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4269	Approved
0.7053	Intermediate Similarity	NPD4270	Approved
0.6979	Remote Similarity	NPD5362	Discontinued
0.6939	Remote Similarity	NPD5786	Approved
0.6937	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4821	Approved
0.6842	Remote Similarity	NPD4820	Approved
0.6842	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4822	Approved
0.6842	Remote Similarity	NPD4819	Approved
0.6842	Remote Similarity	NPD4252	Approved
0.6837	Remote Similarity	NPD5363	Approved
0.6832	Remote Similarity	NPD46	Approved
0.6832	Remote Similarity	NPD6698	Approved
0.6804	Remote Similarity	NPD7154	Phase 3
0.6701	Remote Similarity	NPD6435	Approved
0.6699	Remote Similarity	NPD5779	Approved
0.6699	Remote Similarity	NPD5778	Approved
0.6697	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5785	Approved
0.6632	Remote Similarity	NPD4268	Approved
0.6632	Remote Similarity	NPD4271	Approved
0.661	Remote Similarity	NPD6319	Approved
0.6579	Remote Similarity	NPD6053	Discontinued
0.6542	Remote Similarity	NPD4225	Approved
0.6529	Remote Similarity	NPD7492	Approved
0.65	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5368	Approved
0.6475	Remote Similarity	NPD6616	Approved
0.6471	Remote Similarity	NPD6059	Approved
0.6471	Remote Similarity	NPD6054	Approved
0.6465	Remote Similarity	NPD5331	Approved
0.6465	Remote Similarity	NPD5332	Approved
0.6442	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD4790	Discontinued
0.6423	Remote Similarity	NPD7078	Approved
0.6423	Remote Similarity	NPD8293	Discontinued
0.6422	Remote Similarity	NPD1700	Approved
0.6417	Remote Similarity	NPD8517	Approved
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD8513	Phase 3
0.6417	Remote Similarity	NPD8515	Approved
0.6417	Remote Similarity	NPD6015	Approved
0.6417	Remote Similarity	NPD8516	Approved
0.6379	Remote Similarity	NPD8133	Approved
0.6379	Remote Similarity	NPD4632	Approved
0.6371	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6356	Remote Similarity	NPD7115	Discovery
0.6346	Remote Similarity	NPD7838	Discovery
0.6296	Remote Similarity	NPD6083	Phase 2
0.6296	Remote Similarity	NPD6084	Phase 2
0.6289	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4802	Phase 2
0.6289	Remote Similarity	NPD4238	Approved
0.6283	Remote Similarity	NPD6412	Phase 2
0.6262	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5696	Approved
0.6228	Remote Similarity	NPD7320	Approved
0.6228	Remote Similarity	NPD6686	Approved
0.6226	Remote Similarity	NPD6399	Phase 3
0.6214	Remote Similarity	NPD7524	Approved
0.6204	Remote Similarity	NPD7839	Suspended
0.6195	Remote Similarity	NPD6675	Approved
0.6195	Remote Similarity	NPD7128	Approved
0.6195	Remote Similarity	NPD6008	Approved
0.6195	Remote Similarity	NPD5739	Approved
0.6195	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD7319	Approved
0.6182	Remote Similarity	NPD7639	Approved
0.6182	Remote Similarity	NPD7640	Approved
0.6174	Remote Similarity	NPD6373	Approved
0.6174	Remote Similarity	NPD6372	Approved
0.616	Remote Similarity	NPD8074	Phase 3
0.6154	Remote Similarity	NPD8297	Approved
0.614	Remote Similarity	NPD5697	Approved
0.614	Remote Similarity	NPD5701	Approved
0.6132	Remote Similarity	NPD8035	Phase 2
0.6132	Remote Similarity	NPD8034	Phase 2
0.6132	Remote Similarity	NPD6411	Approved
0.6126	Remote Similarity	NPD5344	Discontinued
0.6121	Remote Similarity	NPD4634	Approved
0.6091	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7638	Approved
0.6087	Remote Similarity	NPD6899	Approved
0.6087	Remote Similarity	NPD6881	Approved
0.6083	Remote Similarity	NPD6009	Approved
0.6083	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8273	Phase 1
0.608	Remote Similarity	NPD7507	Approved
0.6078	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6650	Approved
0.6068	Remote Similarity	NPD6649	Approved
0.6068	Remote Similarity	NPD2204	Approved
0.6034	Remote Similarity	NPD6012	Approved
0.6034	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6014	Approved
0.6034	Remote Similarity	NPD6013	Approved
0.6023	Remote Similarity	NPD3198	Approved
0.6016	Remote Similarity	NPD8266	Approved
0.6016	Remote Similarity	NPD8267	Approved
0.6016	Remote Similarity	NPD6921	Approved
0.6016	Remote Similarity	NPD5956	Approved
0.6016	Remote Similarity	NPD8268	Approved
0.6016	Remote Similarity	NPD5983	Phase 2
0.6016	Remote Similarity	NPD8269	Approved
0.5984	Remote Similarity	NPD6033	Approved
0.5983	Remote Similarity	NPD7290	Approved
0.5983	Remote Similarity	NPD6883	Approved
0.5983	Remote Similarity	NPD7102	Approved
0.598	Remote Similarity	NPD6695	Phase 3
0.598	Remote Similarity	NPD6110	Phase 1
0.5948	Remote Similarity	NPD6011	Approved
0.5943	Remote Similarity	NPD4753	Phase 2
0.5943	Remote Similarity	NPD5370	Suspended
0.5932	Remote Similarity	NPD8130	Phase 1
0.5932	Remote Similarity	NPD6847	Approved
0.5932	Remote Similarity	NPD6869	Approved
0.5932	Remote Similarity	NPD6617	Approved
0.5929	Remote Similarity	NPD5211	Phase 2
0.592	Remote Similarity	NPD7604	Phase 2
0.592	Remote Similarity	NPD8328	Phase 3
0.5909	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6882	Approved
0.5882	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD8340	Approved
0.5873	Remote Similarity	NPD8299	Approved
0.5873	Remote Similarity	NPD8342	Approved
0.5873	Remote Similarity	NPD8341	Approved
0.5865	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4755	Approved
0.5847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8080	Discontinued
0.5833	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6336	Discontinued
0.5826	Remote Similarity	NPD5141	Approved
0.582	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5210	Approved
0.5818	Remote Similarity	NPD4629	Approved
0.5798	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7632	Discontinued
0.5772	Remote Similarity	NPD7328	Approved
0.5772	Remote Similarity	NPD7327	Approved
0.5763	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7909	Approved
0.5761	Remote Similarity	NPD3197	Phase 1
0.576	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.576	Remote Similarity	NPD8033	Approved
0.5755	Remote Similarity	NPD7750	Discontinued
0.5752	Remote Similarity	NPD4700	Approved
0.5752	Remote Similarity	NPD5286	Approved
0.5752	Remote Similarity	NPD4696	Approved
0.5752	Remote Similarity	NPD6648	Approved
0.5752	Remote Similarity	NPD5285	Approved
0.5738	Remote Similarity	NPD6274	Approved
0.5728	Remote Similarity	NPD3667	Approved
0.5726	Remote Similarity	NPD6685	Approved
0.5726	Remote Similarity	NPD4522	Approved
0.5726	Remote Similarity	NPD7516	Approved
0.5714	Remote Similarity	NPD6421	Discontinued
0.5703	Remote Similarity	NPD8451	Approved
0.5701	Remote Similarity	NPD6672	Approved
0.5701	Remote Similarity	NPD5737	Approved
0.5701	Remote Similarity	NPD6903	Approved
0.5699	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD5281	Approved
0.5688	Remote Similarity	NPD5693	Phase 1
0.5688	Remote Similarity	NPD5284	Approved
0.5686	Remote Similarity	NPD6931	Approved
0.5686	Remote Similarity	NPD6930	Phase 2
0.5684	Remote Similarity	NPD229	Approved
0.5682	Remote Similarity	NPD6845	Suspended
0.568	Remote Similarity	NPD8294	Approved
0.568	Remote Similarity	NPD8377	Approved
0.5676	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4788	Approved
0.566	Remote Similarity	NPD5330	Approved
0.566	Remote Similarity	NPD7521	Approved
0.566	Remote Similarity	NPD7146	Approved
0.566	Remote Similarity	NPD6098	Approved
0.566	Remote Similarity	NPD7334	Approved
0.566	Remote Similarity	NPD5279	Phase 3

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