NPASS Compound

Structure

NPC475570 OpenBabel07101718192D 41 46 0 0 1 0 0 0 0 0999 V2000 8.2994 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9593 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3304 4.1841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2888 4.1841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3091 -2.2674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3508 -2.2674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 -0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 1.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9796 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8096 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1294 1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9796 2.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6395 2.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1294 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9796 1.9167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6599 -0.9583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4898 0.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6395 1.9167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2994 1.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4695 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8096 3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 0.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3198 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6599 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8096 1.4375 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2994 2.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2994 0.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4695 -0.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4792 -1.7883 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 7.4695 1.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 9 10 1 0 0 0 0 9 22 2 0 0 0 0 10 25 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 32 1 0 0 0 0 13 15 1 0 0 0 0 13 31 1 0 0 0 0 14 16 1 0 0 0 0 15 34 1 0 0 0 0 17 21 2 0 0 0 0 17 27 1 0 0 0 0 18 23 1 0 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 19 29 1 0 0 0 0 20 33 1 0 0 0 0 20 40 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 34 1 6 0 0 0 24 30 1 0 0 0 0 24 33 1 1 0 0 0 25 32 1 1 0 0 0 25 33 1 0 0 0 0 26 34 1 1 0 0 0 26 41 1 0 0 0 0 27 36 2 0 0 0 0 27 41 1 0 0 0 0 28 37 2 0 0 0 0 28 38 1 0 0 0 0 30 35 1 0 0 0 0 31 32 1 1 0 0 0 32 8 1 1 0 0 0 33 14 1 6 0 0 0 34 28 1 1 0 0 0 35 16 1 1 0 0 0 35 39 1 0 0 0 0 35 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.38
Volume:	604.773
LogP:	6.511
LogD:	4.553
LogS:	-5.18
# Rotatable Bonds:	4
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	6.475
Fsp3:	0.829
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.501
MDCK Permeability:	1.7154981833300553e-05
Pgp-inhibitor:	0.15
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.784
Plasma Protein Binding (PPB):	92.4456787109375%
Volume Distribution (VD):	1.113
Pgp-substrate:	5.511085510253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.492
CYP2C19-inhibitor:	0.325
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.687
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.472

ADMET: Excretion

Clearance (CL):	5.367
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.405
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.396
Carcinogencity:	0.539
Eye Corrosion:	0.102
Eye Irritation:	0.044
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC475570

Natural Product ID:	NPC475570
*Common Name:**	Lantanilic Acid
IUPAC Name:	n.a.
Synonyms:	Lantanilic Acid
Standard InCHIKey:	HGMVESCHSMFWDD-FFHSXQEQSA-N
Standard InCHI:	InChI=1S/C35H52O6/c1-21(2)17-27(36)41-26-19-29(3,4)18-23-22-9-10-25-32(8,31(22,7)13-15-34(23,26)28(37)38)12-11-24-30(5,6)35(39)16-14-33(24,25)20-40-35/h9,17,23-26,39H,10-16,18-20H2,1-8H3,(H,37,38)/t23-,24-,25-,26+,31+,32+,33+,34-,35+/m0/s1
SMILES:	CC(=CC(=O)O[C@@H]1CC(C)(C)C[C@@H]2[C@]1(CC[C@@]1(C2=CC[C@H]2[C@@]1(C)CC[C@@H]1[C@@]32CC[C@](C1(C)C)(OC3)O)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508444
PubChem CID:	44584761
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO6442	Lippia turbinata	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170663]
NPO6442	Lippia turbinata	Species	Verbenaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	128000.0	nM	PMID[515700]

☑ 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 NPC475570 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	251
0.1-0.2	1515
0.2-0.3	4465
0.3-0.4	8693
0.4-0.5	13201
0.5-0.6	6800
0.6-0.7	4994
0.7-0.8	2018
0.8-0.85	669
0.85-0.9	80
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC473483
0.9388	High Similarity	NPC475156
0.9388	High Similarity	NPC473576
0.9245	High Similarity	NPC44170
0.9151	High Similarity	NPC110861
0.91	High Similarity	NPC476888
0.91	High Similarity	NPC93744
0.9065	High Similarity	NPC268954
0.901	High Similarity	NPC40918
0.901	High Similarity	NPC476890
0.8922	High Similarity	NPC476889
0.8878	High Similarity	NPC474963
0.88	High Similarity	NPC26413
0.8774	High Similarity	NPC472666
0.8687	High Similarity	NPC78580
0.8687	High Similarity	NPC23621
0.8687	High Similarity	NPC184006
0.8679	High Similarity	NPC476759
0.8614	High Similarity	NPC158347
0.86	High Similarity	NPC23241
0.86	High Similarity	NPC195715
0.8585	High Similarity	NPC300614
0.8585	High Similarity	NPC90946
0.8585	High Similarity	NPC476765
0.8571	High Similarity	NPC476127
0.8571	High Similarity	NPC476150
0.8558	High Similarity	NPC95899
0.8515	High Similarity	NPC98874
0.8515	High Similarity	NPC317573
0.8505	High Similarity	NPC31522
0.85	High Similarity	NPC91010
0.85	High Similarity	NPC74751
0.8496	Intermediate Similarity	NPC170084
0.8496	Intermediate Similarity	NPC476204
0.8476	Intermediate Similarity	NPC476764
0.8476	Intermediate Similarity	NPC476763
0.8468	Intermediate Similarity	NPC474483
0.8468	Intermediate Similarity	NPC473405
0.8448	Intermediate Similarity	NPC470516
0.844	Intermediate Similarity	NPC1046
0.844	Intermediate Similarity	NPC90952
0.844	Intermediate Similarity	NPC277769
0.844	Intermediate Similarity	NPC80843
0.8431	Intermediate Similarity	NPC476878
0.8431	Intermediate Similarity	NPC476879
0.8426	Intermediate Similarity	NPC476766
0.8416	Intermediate Similarity	NPC148523
0.8416	Intermediate Similarity	NPC474727
0.84	Intermediate Similarity	NPC86368
0.84	Intermediate Similarity	NPC169343
0.8396	Intermediate Similarity	NPC476762
0.8396	Intermediate Similarity	NPC476760
0.8396	Intermediate Similarity	NPC476761
0.8393	Intermediate Similarity	NPC471548
0.8384	Intermediate Similarity	NPC113989
0.8384	Intermediate Similarity	NPC120840
0.8381	Intermediate Similarity	NPC471208
0.8381	Intermediate Similarity	NPC478057
0.8376	Intermediate Similarity	NPC23020
0.8376	Intermediate Similarity	NPC472268
0.8376	Intermediate Similarity	NPC112492
0.8376	Intermediate Similarity	NPC472270
0.8376	Intermediate Similarity	NPC472269
0.8365	Intermediate Similarity	NPC471075
0.8364	Intermediate Similarity	NPC475208
0.8364	Intermediate Similarity	NPC238935
0.8349	Intermediate Similarity	NPC31839
0.8305	Intermediate Similarity	NPC477196
0.83	Intermediate Similarity	NPC77099
0.83	Intermediate Similarity	NPC966
0.83	Intermediate Similarity	NPC285184
0.83	Intermediate Similarity	NPC228784
0.83	Intermediate Similarity	NPC155120
0.83	Intermediate Similarity	NPC324341
0.83	Intermediate Similarity	NPC288833
0.83	Intermediate Similarity	NPC282616
0.83	Intermediate Similarity	NPC60755
0.83	Intermediate Similarity	NPC470590
0.8288	Intermediate Similarity	NPC470953
0.8288	Intermediate Similarity	NPC164389
0.8288	Intermediate Similarity	NPC475486
0.8286	Intermediate Similarity	NPC165250
0.8286	Intermediate Similarity	NPC476769
0.8283	Intermediate Similarity	NPC30522
0.8273	Intermediate Similarity	NPC194951
0.8273	Intermediate Similarity	NPC48249
0.8273	Intermediate Similarity	NPC12046
0.8273	Intermediate Similarity	NPC4573
0.8273	Intermediate Similarity	NPC471967
0.8269	Intermediate Similarity	NPC476299
0.8269	Intermediate Similarity	NPC476767
0.8269	Intermediate Similarity	NPC117685
0.8269	Intermediate Similarity	NPC474012
0.8257	Intermediate Similarity	NPC59804
0.8257	Intermediate Similarity	NPC242611
0.8257	Intermediate Similarity	NPC174679
0.8257	Intermediate Similarity	NPC29069
0.8257	Intermediate Similarity	NPC475296
0.8257	Intermediate Similarity	NPC127056
0.8257	Intermediate Similarity	NPC269095
0.8257	Intermediate Similarity	NPC474589
0.8257	Intermediate Similarity	NPC56713
0.8257	Intermediate Similarity	NPC136877
0.8257	Intermediate Similarity	NPC164194
0.8257	Intermediate Similarity	NPC78046
0.8257	Intermediate Similarity	NPC270667
0.8257	Intermediate Similarity	NPC279554
0.8257	Intermediate Similarity	NPC90856
0.8252	Intermediate Similarity	NPC89225
0.8246	Intermediate Similarity	NPC476962
0.8241	Intermediate Similarity	NPC325054
0.8241	Intermediate Similarity	NPC275539
0.8241	Intermediate Similarity	NPC189075
0.8235	Intermediate Similarity	NPC222951
0.8235	Intermediate Similarity	NPC311178
0.8235	Intermediate Similarity	NPC300655
0.8235	Intermediate Similarity	NPC43589
0.8235	Intermediate Similarity	NPC477197
0.8224	Intermediate Similarity	NPC88349
0.8224	Intermediate Similarity	NPC475611
0.822	Intermediate Similarity	NPC477078
0.822	Intermediate Similarity	NPC477191
0.822	Intermediate Similarity	NPC477075
0.822	Intermediate Similarity	NPC477192
0.822	Intermediate Similarity	NPC329923
0.822	Intermediate Similarity	NPC475281
0.822	Intermediate Similarity	NPC477194
0.822	Intermediate Similarity	NPC477193
0.8218	Intermediate Similarity	NPC472303
0.8218	Intermediate Similarity	NPC272075
0.8218	Intermediate Similarity	NPC214756
0.8218	Intermediate Similarity	NPC295643
0.8214	Intermediate Similarity	NPC75287
0.8214	Intermediate Similarity	NPC51465
0.8214	Intermediate Similarity	NPC291903
0.8214	Intermediate Similarity	NPC305267
0.8214	Intermediate Similarity	NPC26626
0.8214	Intermediate Similarity	NPC37134
0.8214	Intermediate Similarity	NPC288205
0.8214	Intermediate Similarity	NPC476992
0.8208	Intermediate Similarity	NPC180204
0.8208	Intermediate Similarity	NPC291154
0.8205	Intermediate Similarity	NPC297950
0.82	Intermediate Similarity	NPC474728
0.82	Intermediate Similarity	NPC198818
0.82	Intermediate Similarity	NPC172361
0.82	Intermediate Similarity	NPC86372
0.8198	Intermediate Similarity	NPC157441
0.819	Intermediate Similarity	NPC204812
0.819	Intermediate Similarity	NPC473160
0.819	Intermediate Similarity	NPC235142
0.8182	Intermediate Similarity	NPC108748
0.8182	Intermediate Similarity	NPC30397
0.8182	Intermediate Similarity	NPC297208
0.8182	Intermediate Similarity	NPC164419
0.8182	Intermediate Similarity	NPC179434
0.8182	Intermediate Similarity	NPC211798
0.8182	Intermediate Similarity	NPC235841
0.8182	Intermediate Similarity	NPC473481
0.8173	Intermediate Similarity	NPC58942
0.8173	Intermediate Similarity	NPC471966
0.8173	Intermediate Similarity	NPC164349
0.8173	Intermediate Similarity	NPC260149
0.8167	Intermediate Similarity	NPC183816
0.8167	Intermediate Similarity	NPC475177
0.8167	Intermediate Similarity	NPC477195
0.8167	Intermediate Similarity	NPC322904
0.8167	Intermediate Similarity	NPC476776
0.8167	Intermediate Similarity	NPC196874
0.8167	Intermediate Similarity	NPC473679
0.8167	Intermediate Similarity	NPC324933
0.8167	Intermediate Similarity	NPC319719
0.8167	Intermediate Similarity	NPC233223
0.8167	Intermediate Similarity	NPC475444
0.8165	Intermediate Similarity	NPC57362
0.8165	Intermediate Similarity	NPC204407
0.8165	Intermediate Similarity	NPC167383
0.8165	Intermediate Similarity	NPC306746
0.8165	Intermediate Similarity	NPC237503
0.8165	Intermediate Similarity	NPC137917
0.8158	Intermediate Similarity	NPC77689
0.8158	Intermediate Similarity	NPC473636
0.8158	Intermediate Similarity	NPC476960
0.8155	Intermediate Similarity	NPC472806
0.8155	Intermediate Similarity	NPC234993
0.8155	Intermediate Similarity	NPC134072
0.8155	Intermediate Similarity	NPC167193
0.8155	Intermediate Similarity	NPC242848
0.8151	Intermediate Similarity	NPC252289
0.8151	Intermediate Similarity	NPC265841
0.8151	Intermediate Similarity	NPC1314
0.8151	Intermediate Similarity	NPC305793
0.8151	Intermediate Similarity	NPC252657
0.8151	Intermediate Similarity	NPC11577
0.8151	Intermediate Similarity	NPC273878
0.8151	Intermediate Similarity	NPC477077
0.8151	Intermediate Similarity	NPC477079
0.8151	Intermediate Similarity	NPC9470
0.8151	Intermediate Similarity	NPC244296
0.8151	Intermediate Similarity	NPC107536

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 NPC475570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	1740
0.2-0.3	3688
0.3-0.4	2277
0.4-0.5	770
0.5-0.6	257
0.6-0.7	155
0.7-0.8	31
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD7748	Approved
0.8252	Intermediate Similarity	NPD7902	Approved
0.8173	Intermediate Similarity	NPD7638	Approved
0.8119	Intermediate Similarity	NPD7515	Phase 2
0.8095	Intermediate Similarity	NPD7640	Approved
0.8095	Intermediate Similarity	NPD7639	Approved
0.8034	Intermediate Similarity	NPD8328	Phase 3
0.7961	Intermediate Similarity	NPD7900	Approved
0.7961	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6686	Approved
0.7705	Intermediate Similarity	NPD7319	Approved
0.7672	Intermediate Similarity	NPD7115	Discovery
0.7672	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8294	Approved
0.7627	Intermediate Similarity	NPD8377	Approved
0.7603	Intermediate Similarity	NPD7507	Approved
0.7565	Intermediate Similarity	NPD8133	Approved
0.7563	Intermediate Similarity	NPD8380	Approved
0.7563	Intermediate Similarity	NPD8335	Approved
0.7563	Intermediate Similarity	NPD8379	Approved
0.7563	Intermediate Similarity	NPD8378	Approved
0.7563	Intermediate Similarity	NPD8296	Approved
0.7563	Intermediate Similarity	NPD8033	Approved
0.7522	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4225	Approved
0.7455	Intermediate Similarity	NPD7632	Discontinued
0.7368	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6412	Phase 2
0.7339	Intermediate Similarity	NPD7736	Approved
0.7311	Intermediate Similarity	NPD7327	Approved
0.7311	Intermediate Similarity	NPD7328	Approved
0.7308	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8513	Phase 3
0.7273	Intermediate Similarity	NPD8515	Approved
0.7273	Intermediate Similarity	NPD8517	Approved
0.7273	Intermediate Similarity	NPD8516	Approved
0.7264	Intermediate Similarity	NPD6411	Approved
0.7264	Intermediate Similarity	NPD8034	Phase 2
0.7264	Intermediate Similarity	NPD8035	Phase 2
0.7257	Intermediate Similarity	NPD7128	Approved
0.7257	Intermediate Similarity	NPD6675	Approved
0.7257	Intermediate Similarity	NPD6402	Approved
0.7257	Intermediate Similarity	NPD5739	Approved
0.725	Intermediate Similarity	NPD7516	Approved
0.7228	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3573	Approved
0.7196	Intermediate Similarity	NPD5778	Approved
0.7196	Intermediate Similarity	NPD6399	Phase 3
0.7196	Intermediate Similarity	NPD5779	Approved
0.7179	Intermediate Similarity	NPD6882	Approved
0.7131	Intermediate Similarity	NPD7503	Approved
0.713	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8293	Discontinued
0.7115	Intermediate Similarity	NPD7146	Approved
0.7115	Intermediate Similarity	NPD6684	Approved
0.7115	Intermediate Similarity	NPD7521	Approved
0.7115	Intermediate Similarity	NPD7334	Approved
0.7115	Intermediate Similarity	NPD6409	Approved
0.7115	Intermediate Similarity	NPD3618	Phase 1
0.7115	Intermediate Similarity	NPD5330	Approved
0.71	Intermediate Similarity	NPD7645	Phase 2
0.7097	Intermediate Similarity	NPD7492	Approved
0.7094	Intermediate Similarity	NPD8130	Phase 1
0.7091	Intermediate Similarity	NPD6084	Phase 2
0.7091	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6101	Approved
0.7075	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5328	Approved
0.7069	Intermediate Similarity	NPD6373	Approved
0.7069	Intermediate Similarity	NPD6372	Approved
0.7049	Intermediate Similarity	NPD6054	Approved
0.7049	Intermediate Similarity	NPD6059	Approved
0.7043	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5701	Approved
0.7043	Intermediate Similarity	NPD5697	Approved
0.704	Intermediate Similarity	NPD6616	Approved
0.7034	Intermediate Similarity	NPD8297	Approved
0.7019	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1694	Approved
0.7009	Intermediate Similarity	NPD6883	Approved
0.7009	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD7290	Approved
0.6984	Remote Similarity	NPD7078	Approved
0.6981	Remote Similarity	NPD5737	Approved
0.6981	Remote Similarity	NPD6672	Approved
0.6981	Remote Similarity	NPD6903	Approved
0.6949	Remote Similarity	NPD6869	Approved
0.6949	Remote Similarity	NPD6649	Approved
0.6949	Remote Similarity	NPD6847	Approved
0.6949	Remote Similarity	NPD6650	Approved
0.6949	Remote Similarity	NPD6617	Approved
0.6944	Remote Similarity	NPD6079	Approved
0.6935	Remote Similarity	NPD6370	Approved
0.6923	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6012	Approved
0.6923	Remote Similarity	NPD6013	Approved
0.6911	Remote Similarity	NPD6319	Approved
0.6909	Remote Similarity	NPD5695	Phase 3
0.6875	Remote Similarity	NPD5696	Approved
0.6855	Remote Similarity	NPD6016	Approved
0.6855	Remote Similarity	NPD6015	Approved
0.6852	Remote Similarity	NPD6698	Approved
0.6852	Remote Similarity	NPD46	Approved
0.6838	Remote Similarity	NPD6011	Approved
0.681	Remote Similarity	NPD6008	Approved
0.6807	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD5988	Approved
0.6792	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7637	Suspended
0.6789	Remote Similarity	NPD5693	Phase 1
0.6786	Remote Similarity	NPD4755	Approved
0.6762	Remote Similarity	NPD4786	Approved
0.6762	Remote Similarity	NPD3666	Approved
0.6762	Remote Similarity	NPD3133	Approved
0.6762	Remote Similarity	NPD3665	Phase 1
0.6757	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6053	Discontinued
0.6731	Remote Similarity	NPD3667	Approved
0.6727	Remote Similarity	NPD4202	Approved
0.6723	Remote Similarity	NPD4634	Approved
0.6719	Remote Similarity	NPD8074	Phase 3
0.6696	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7732	Phase 3
0.6696	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD5211	Phase 2
0.6696	Remote Similarity	NPD7839	Suspended
0.6696	Remote Similarity	NPD7614	Phase 1
0.6696	Remote Similarity	NPD5221	Approved
0.6696	Remote Similarity	NPD5222	Approved
0.6694	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6637	Remote Similarity	NPD5173	Approved
0.6606	Remote Similarity	NPD4753	Phase 2
0.6606	Remote Similarity	NPD6904	Approved
0.6606	Remote Similarity	NPD6673	Approved
0.6606	Remote Similarity	NPD6080	Approved
0.6606	Remote Similarity	NPD6051	Approved
0.6604	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6274	Approved
0.6585	Remote Similarity	NPD6868	Approved
0.6581	Remote Similarity	NPD5141	Approved
0.6579	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7100	Approved
0.656	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD4633	Approved
0.6552	Remote Similarity	NPD5224	Approved
0.6552	Remote Similarity	NPD5225	Approved
0.6552	Remote Similarity	NPD5226	Approved
0.6545	Remote Similarity	NPD5785	Approved
0.6538	Remote Similarity	NPD6033	Approved
0.6538	Remote Similarity	NPD4695	Discontinued
0.6535	Remote Similarity	NPD8039	Approved
0.6505	Remote Similarity	NPD6115	Approved
0.6505	Remote Similarity	NPD6697	Approved
0.6505	Remote Similarity	NPD6118	Approved
0.6505	Remote Similarity	NPD6114	Approved
0.6496	Remote Similarity	NPD5175	Approved
0.6496	Remote Similarity	NPD5174	Approved
0.6484	Remote Similarity	NPD7604	Phase 2
0.6484	Remote Similarity	NPD6067	Discontinued
0.6481	Remote Similarity	NPD4519	Discontinued
0.6481	Remote Similarity	NPD4623	Approved
0.648	Remote Similarity	NPD6335	Approved
0.6471	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5223	Approved
0.6466	Remote Similarity	NPD5344	Discontinued
0.646	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6908	Approved
0.6457	Remote Similarity	NPD5983	Phase 2
0.6457	Remote Similarity	NPD6921	Approved
0.6457	Remote Similarity	NPD6909	Approved
0.6449	Remote Similarity	NPD3668	Phase 3
0.6446	Remote Similarity	NPD6371	Approved
0.6415	Remote Similarity	NPD4223	Phase 3
0.6415	Remote Similarity	NPD4221	Approved
0.64	Remote Similarity	NPD6317	Approved
0.6389	Remote Similarity	NPD5329	Approved
0.6387	Remote Similarity	NPD4767	Approved
0.6387	Remote Similarity	NPD4768	Approved
0.6385	Remote Similarity	NPD6336	Discontinued
0.6381	Remote Similarity	NPD7525	Registered
0.6379	Remote Similarity	NPD6648	Approved
0.6372	Remote Similarity	NPD5282	Discontinued
0.6372	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD5208	Approved
0.6356	Remote Similarity	NPD4754	Approved
0.6349	Remote Similarity	NPD6314	Approved
0.6349	Remote Similarity	NPD6313	Approved
0.6339	Remote Similarity	NPD5284	Approved
0.6339	Remote Similarity	NPD6050	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