NPASS Compound

Structure

CID144419 OpenBabel06191715502D 23 23 0 0 1 0 0 0 0 0999 V2000 9.5916 4.2644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1848 5.1780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1903 5.2825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6025 4.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6080 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0202 3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0257 3.8735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4379 3.0645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4434 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8556 2.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8611 2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2733 1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8968 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4901 2.6736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8913 1.6555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 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 3 1 0 0 0 0 2 15 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 14 1 1 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.23
Volume:	355.875
LogP:	6.725
LogD:	4.579
LogS:	-3.641
# Rotatable Bonds:	13
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.447
Synthetic Accessibility Score:	2.542
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.08
MDCK Permeability:	3.0093533496255986e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.232
30% Bioavailability (F30%):	0.862

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	100.2530288696289%
Volume Distribution (VD):	0.867
Pgp-substrate:	1.5804837942123413%

ADMET: Metabolism

CYP1A2-inhibitor:	0.235
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.249
CYP2C9-substrate:	0.672
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	2.262
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.438
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.84
Carcinogencity:	0.064
Eye Corrosion:	0.041
Eye Irritation:	0.654
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC144419

Natural Product ID:	NPC144419
*Common Name:**	(+)-Lichesterinic Acid
IUPAC Name:	(2R)-4-methyl-5-oxo-2-tridecyl-2H-furan-3-carboxylic acid
Synonyms:
Standard InCHIKey:	SLQVVNFTCYVCPB-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C19H32O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-17(18(20)21)15(2)19(22)23-16/h16H,3-14H2,1-2H3,(H,20,21)/t16-/m1/s1
SMILES:	CCCCCCCCCCCCC[C@@H]1C(=C(C)C(=O)O1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3318191
PubChem CID:	21116528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[22233034]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561895]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6513	Vernonia condensata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4633	Calypogeia integristipula	Species	Calypogeiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2777	Cirsium brevistylum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5786	Desmodium oxyphyllum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	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
IC50	2
MIC	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	72000.0	nM	PMID[473692]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[473692]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	90.0	ug.mL-1	PMID[473693]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	4.69	ug.mL-1	PMID[473693]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MBC=>99	=	18.75	ug ml-1	PMID[473693]

☑ 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 NPC144419 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	195
0.1-0.2	1946
0.2-0.3	7027
0.3-0.4	16499
0.4-0.5	9729
0.5-0.6	5097
0.6-0.7	1767
0.7-0.8	415
0.8-0.85	9
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC47653
0.8378	Intermediate Similarity	NPC469414
0.8378	Intermediate Similarity	NPC329826
0.8219	Intermediate Similarity	NPC84038
0.8148	Intermediate Similarity	NPC469483
0.8108	Intermediate Similarity	NPC474705
0.8056	Intermediate Similarity	NPC218477
0.7901	Intermediate Similarity	NPC163093
0.7875	Intermediate Similarity	NPC473780
0.7875	Intermediate Similarity	NPC65930
0.7875	Intermediate Similarity	NPC94875
0.7875	Intermediate Similarity	NPC475159
0.7875	Intermediate Similarity	NPC11332
0.7875	Intermediate Similarity	NPC73310
0.7875	Intermediate Similarity	NPC329829
0.7875	Intermediate Similarity	NPC180363
0.7875	Intermediate Similarity	NPC145914
0.7875	Intermediate Similarity	NPC473712
0.7875	Intermediate Similarity	NPC473529
0.7875	Intermediate Similarity	NPC131002
0.7821	Intermediate Similarity	NPC93763
0.7821	Intermediate Similarity	NPC108816
0.7805	Intermediate Similarity	NPC470755
0.7805	Intermediate Similarity	NPC477013
0.7805	Intermediate Similarity	NPC477014
0.7805	Intermediate Similarity	NPC120398
0.7805	Intermediate Similarity	NPC471567
0.7792	Intermediate Similarity	NPC256640
0.7792	Intermediate Similarity	NPC16279
0.7792	Intermediate Similarity	NPC205615
0.7778	Intermediate Similarity	NPC475947
0.7778	Intermediate Similarity	NPC144415
0.7778	Intermediate Similarity	NPC253801
0.7763	Intermediate Similarity	NPC227396
0.7763	Intermediate Similarity	NPC177030
0.7733	Intermediate Similarity	NPC186531
0.7711	Intermediate Similarity	NPC261721
0.7711	Intermediate Similarity	NPC477015
0.7683	Intermediate Similarity	NPC156804
0.7683	Intermediate Similarity	NPC31086
0.7683	Intermediate Similarity	NPC158756
0.7662	Intermediate Similarity	NPC260396
0.7654	Intermediate Similarity	NPC85772
0.7647	Intermediate Similarity	NPC14901
0.7647	Intermediate Similarity	NPC130359
0.7639	Intermediate Similarity	NPC282760
0.7619	Intermediate Similarity	NPC72513
0.7619	Intermediate Similarity	NPC178215
0.7606	Intermediate Similarity	NPC68110
0.76	Intermediate Similarity	NPC475113
0.76	Intermediate Similarity	NPC299932
0.76	Intermediate Similarity	NPC67183
0.7595	Intermediate Similarity	NPC102065
0.7595	Intermediate Similarity	NPC315765
0.7595	Intermediate Similarity	NPC85743
0.759	Intermediate Similarity	NPC39167
0.759	Intermediate Similarity	NPC9678
0.759	Intermediate Similarity	NPC292809
0.759	Intermediate Similarity	NPC182383
0.759	Intermediate Similarity	NPC473671
0.759	Intermediate Similarity	NPC223871
0.759	Intermediate Similarity	NPC103284
0.759	Intermediate Similarity	NPC202055
0.759	Intermediate Similarity	NPC110710
0.759	Intermediate Similarity	NPC475268
0.759	Intermediate Similarity	NPC231009
0.759	Intermediate Similarity	NPC283085
0.759	Intermediate Similarity	NPC77871
0.759	Intermediate Similarity	NPC132496
0.759	Intermediate Similarity	NPC66346
0.759	Intermediate Similarity	NPC68303
0.759	Intermediate Similarity	NPC329615
0.759	Intermediate Similarity	NPC473651
0.759	Intermediate Similarity	NPC107986
0.759	Intermediate Similarity	NPC473478
0.759	Intermediate Similarity	NPC307126
0.759	Intermediate Similarity	NPC473156
0.759	Intermediate Similarity	NPC477018
0.759	Intermediate Similarity	NPC82795
0.759	Intermediate Similarity	NPC100921
0.759	Intermediate Similarity	NPC39279
0.759	Intermediate Similarity	NPC286338
0.759	Intermediate Similarity	NPC261380
0.759	Intermediate Similarity	NPC235809
0.759	Intermediate Similarity	NPC319036
0.759	Intermediate Similarity	NPC470400
0.759	Intermediate Similarity	NPC473669
0.759	Intermediate Similarity	NPC329838
0.759	Intermediate Similarity	NPC25764
0.759	Intermediate Similarity	NPC1083
0.759	Intermediate Similarity	NPC322529
0.7564	Intermediate Similarity	NPC238554
0.7564	Intermediate Similarity	NPC225022
0.7561	Intermediate Similarity	NPC229799
0.7561	Intermediate Similarity	NPC169575
0.7561	Intermediate Similarity	NPC286770
0.7561	Intermediate Similarity	NPC40746
0.7561	Intermediate Similarity	NPC284472
0.7558	Intermediate Similarity	NPC473448
0.7534	Intermediate Similarity	NPC248125
0.7531	Intermediate Similarity	NPC325031
0.7531	Intermediate Similarity	NPC471325
0.7529	Intermediate Similarity	NPC89001
0.7529	Intermediate Similarity	NPC233551
0.7529	Intermediate Similarity	NPC20339
0.7529	Intermediate Similarity	NPC48338
0.7529	Intermediate Similarity	NPC21208
0.7529	Intermediate Similarity	NPC40376
0.7529	Intermediate Similarity	NPC320458
0.7529	Intermediate Similarity	NPC280621
0.7529	Intermediate Similarity	NPC475819
0.7529	Intermediate Similarity	NPC473905
0.7529	Intermediate Similarity	NPC476805
0.75	Intermediate Similarity	NPC134807
0.75	Intermediate Similarity	NPC132940
0.75	Intermediate Similarity	NPC114694
0.75	Intermediate Similarity	NPC142117
0.75	Intermediate Similarity	NPC62118
0.75	Intermediate Similarity	NPC469910
0.75	Intermediate Similarity	NPC279267
0.75	Intermediate Similarity	NPC171174
0.75	Intermediate Similarity	NPC134885
0.75	Intermediate Similarity	NPC477010
0.75	Intermediate Similarity	NPC293136
0.75	Intermediate Similarity	NPC475461
0.75	Intermediate Similarity	NPC241360
0.75	Intermediate Similarity	NPC25703
0.75	Intermediate Similarity	NPC240695
0.75	Intermediate Similarity	NPC473840
0.75	Intermediate Similarity	NPC219652
0.75	Intermediate Similarity	NPC103523
0.75	Intermediate Similarity	NPC204686
0.75	Intermediate Similarity	NPC308412
0.75	Intermediate Similarity	NPC69082
0.75	Intermediate Similarity	NPC305475
0.75	Intermediate Similarity	NPC219498
0.75	Intermediate Similarity	NPC47937
0.75	Intermediate Similarity	NPC134865
0.75	Intermediate Similarity	NPC107717
0.75	Intermediate Similarity	NPC473687
0.75	Intermediate Similarity	NPC232555
0.75	Intermediate Similarity	NPC282815
0.75	Intermediate Similarity	NPC469632
0.75	Intermediate Similarity	NPC231096
0.75	Intermediate Similarity	NPC19841
0.75	Intermediate Similarity	NPC112685
0.75	Intermediate Similarity	NPC210218
0.75	Intermediate Similarity	NPC309211
0.75	Intermediate Similarity	NPC475581
0.7471	Intermediate Similarity	NPC6099
0.7471	Intermediate Similarity	NPC114345
0.7471	Intermediate Similarity	NPC472814
0.7471	Intermediate Similarity	NPC303230
0.7471	Intermediate Similarity	NPC177037
0.7468	Intermediate Similarity	NPC125365
0.7468	Intermediate Similarity	NPC474818
0.7468	Intermediate Similarity	NPC7563
0.7468	Intermediate Similarity	NPC176329
0.7468	Intermediate Similarity	NPC51809
0.7468	Intermediate Similarity	NPC49302
0.7468	Intermediate Similarity	NPC116177
0.7468	Intermediate Similarity	NPC24827
0.7468	Intermediate Similarity	NPC320630
0.7468	Intermediate Similarity	NPC228902
0.7467	Intermediate Similarity	NPC494
0.7467	Intermediate Similarity	NPC475004
0.7467	Intermediate Similarity	NPC470436
0.7444	Intermediate Similarity	NPC53844
0.7442	Intermediate Similarity	NPC477017
0.7442	Intermediate Similarity	NPC477016
0.7442	Intermediate Similarity	NPC139418
0.7442	Intermediate Similarity	NPC280612
0.7439	Intermediate Similarity	NPC11383
0.7439	Intermediate Similarity	NPC310450
0.7439	Intermediate Similarity	NPC471296
0.7439	Intermediate Similarity	NPC474959
0.7439	Intermediate Similarity	NPC475046
0.7436	Intermediate Similarity	NPC329852
0.7416	Intermediate Similarity	NPC473334
0.7416	Intermediate Similarity	NPC476487
0.7416	Intermediate Similarity	NPC476488
0.7412	Intermediate Similarity	NPC258068
0.7412	Intermediate Similarity	NPC476583
0.7412	Intermediate Similarity	NPC470401
0.7412	Intermediate Similarity	NPC154097
0.7412	Intermediate Similarity	NPC473649
0.7412	Intermediate Similarity	NPC473995
0.7412	Intermediate Similarity	NPC20533
0.7412	Intermediate Similarity	NPC477012
0.7412	Intermediate Similarity	NPC159750
0.7386	Intermediate Similarity	NPC469692
0.7386	Intermediate Similarity	NPC115021
0.7386	Intermediate Similarity	NPC469645
0.7381	Intermediate Similarity	NPC255307
0.7375	Intermediate Similarity	NPC267231
0.7375	Intermediate Similarity	NPC473471
0.7375	Intermediate Similarity	NPC128276
0.7375	Intermediate Similarity	NPC127526
0.7375	Intermediate Similarity	NPC279214
0.7375	Intermediate Similarity	NPC221095

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 NPC144419 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	2685
0.2-0.3	3703
0.3-0.4	1796
0.4-0.5	580
0.5-0.6	134
0.6-0.7	47
0.7-0.8	1
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
0.7159	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD7154	Phase 3
0.6977	Remote Similarity	NPD5363	Approved
0.6966	Remote Similarity	NPD6698	Approved
0.6966	Remote Similarity	NPD46	Approved
0.6829	Remote Similarity	NPD4756	Discovery
0.6824	Remote Similarity	NPD4269	Approved
0.6824	Remote Similarity	NPD4270	Approved
0.6786	Remote Similarity	NPD4252	Approved
0.6786	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5362	Discontinued
0.6705	Remote Similarity	NPD5786	Approved
0.6703	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5779	Approved
0.663	Remote Similarity	NPD5778	Approved
0.6628	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5209	Approved
0.6623	Remote Similarity	NPD3704	Approved
0.6622	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3197	Phase 1
0.6548	Remote Similarity	NPD4268	Approved
0.6548	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4271	Approved
0.6512	Remote Similarity	NPD5369	Approved
0.65	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3195	Phase 2
0.6479	Remote Similarity	NPD3196	Approved
0.6479	Remote Similarity	NPD3730	Approved
0.6479	Remote Similarity	NPD4266	Approved
0.6479	Remote Similarity	NPD3728	Approved
0.6479	Remote Similarity	NPD3194	Approved
0.6471	Remote Similarity	NPD6371	Approved
0.6458	Remote Similarity	NPD4225	Approved
0.6437	Remote Similarity	NPD6435	Approved
0.6421	Remote Similarity	NPD7839	Suspended
0.6404	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4820	Approved
0.6395	Remote Similarity	NPD4819	Approved
0.6395	Remote Similarity	NPD4822	Approved
0.6395	Remote Similarity	NPD4821	Approved
0.6386	Remote Similarity	NPD8039	Approved
0.6338	Remote Similarity	NPD3172	Approved
0.6329	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6101	Approved
0.6304	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5370	Suspended
0.6286	Remote Similarity	NPD6927	Phase 3
0.6275	Remote Similarity	NPD6686	Approved
0.6264	Remote Similarity	NPD4251	Approved
0.6264	Remote Similarity	NPD4250	Approved
0.6237	Remote Similarity	NPD7838	Discovery
0.6234	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7639	Approved
0.6224	Remote Similarity	NPD7640	Approved
0.6222	Remote Similarity	NPD1694	Approved
0.6207	Remote Similarity	NPD5368	Approved
0.618	Remote Similarity	NPD5331	Approved
0.618	Remote Similarity	NPD5332	Approved
0.617	Remote Similarity	NPD7637	Suspended
0.617	Remote Similarity	NPD6411	Approved
0.617	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4249	Approved
0.6136	Remote Similarity	NPD4790	Discontinued
0.6122	Remote Similarity	NPD7638	Approved
0.6119	Remote Similarity	NPD2699	Approved
0.6111	Remote Similarity	NPD7115	Discovery
0.61	Remote Similarity	NPD7632	Discontinued
0.6087	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD7341	Phase 2
0.6067	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD28	Approved
0.6056	Remote Similarity	NPD29	Approved
0.6044	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD3732	Approved
0.597	Remote Similarity	NPD9411	Phase 1
0.596	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD69	Approved
0.5921	Remote Similarity	NPD9119	Approved
0.5888	Remote Similarity	NPD6053	Discontinued
0.5876	Remote Similarity	NPD7748	Approved
0.5876	Remote Similarity	NPD5282	Discontinued
0.5859	Remote Similarity	NPD6084	Phase 2
0.5859	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD1376	Discontinued
0.5816	Remote Similarity	NPD5695	Phase 3
0.5806	Remote Similarity	NPD6422	Discontinued
0.5806	Remote Similarity	NPD7521	Approved
0.5806	Remote Similarity	NPD6409	Approved
0.5806	Remote Similarity	NPD6684	Approved
0.5806	Remote Similarity	NPD7334	Approved
0.5806	Remote Similarity	NPD7146	Approved
0.5806	Remote Similarity	NPD5330	Approved
0.5802	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD9118	Approved
0.5789	Remote Similarity	NPD1695	Approved
0.5775	Remote Similarity	NPD3173	Approved
0.5773	Remote Similarity	NPD6399	Phase 3
0.5728	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6109	Phase 1
0.57	Remote Similarity	NPD7902	Approved
0.5686	Remote Similarity	NPD5344	Discontinued
0.5684	Remote Similarity	NPD6903	Approved
0.5684	Remote Similarity	NPD5737	Approved
0.5684	Remote Similarity	NPD6672	Approved
0.5684	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD2270	Approved
0.567	Remote Similarity	NPD7515	Phase 2
0.5644	Remote Similarity	NPD5696	Approved
0.5641	Remote Similarity	NPD3198	Approved
0.5634	Remote Similarity	NPD5343	Approved
0.5634	Remote Similarity	NPD622	Approved
0.5619	Remote Similarity	NPD5739	Approved
0.5619	Remote Similarity	NPD6402	Approved
0.5619	Remote Similarity	NPD7128	Approved
0.5619	Remote Similarity	NPD6675	Approved
0.5614	Remote Similarity	NPD8516	Approved
0.5614	Remote Similarity	NPD8517	Approved
0.5614	Remote Similarity	NPD8513	Phase 3
0.5614	Remote Similarity	NPD8515	Approved
0.56	Remote Similarity	NPD4228	Discovery

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