NPASS Compound

Structure

CID286038 OpenBabel06191716092D 22 24 0 0 1 0 0 0 0 0999 V2000 0.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2218 -2.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 0.0570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 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 11 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 21 1 0 0 0 0 5 8 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 13 1 0 0 0 0 11 18 1 1 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 1 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 18 10 1 1 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.17
Volume:	318.83
LogP:	3.503
LogD:	2.952
LogS:	-4.64
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	4.116
Fsp3:	0.611
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.7
MDCK Permeability:	1.6754705939092673e-05
Pgp-inhibitor:	0.931
Pgp-substrate:	0.141
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.257
Plasma Protein Binding (PPB):	90.47034454345703%
Volume Distribution (VD):	1.117
Pgp-substrate:	7.958120346069336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.813
CYP1A2-substrate:	0.821
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.569
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	9.627
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.17
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.26
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.387
Carcinogencity:	0.27
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.632

Download Data

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

Natural Product: NPC286038

Natural Product ID:	NPC286038
*Common Name:**	Filifolinol
IUPAC Name:	methyl (2R,3'R,6'S)-3'-hydroxy-2',2',6'-trimethylspiro[3H-1-benzofuran-2,1'-cyclohexane]-5-carboxylate
Synonyms:	Filifolinol
Standard InCHIKey:	BGEVVKDFAMDZGO-BKGUAONASA-N
Standard InCHI:	InChI=1S/C18H24O4/c1-11-5-8-15(19)17(2,3)18(11)10-13-9-12(16(20)21-4)6-7-14(13)22-18/h6-7,9,11,15,19H,5,8,10H2,1-4H3/t11-,15+,18+/m0/s1
SMILES:	COC(=O)c1ccc2c(c1)C[C@@]1(O2)[C@@H](C)CC[C@H](C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449167
PubChem CID:	44567192
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO28472	Quercus petraea	Species	Fagaceae	Eukaryota	Barks	n.a.	n.a.	PMID[7807126]
NPO28361	Erythrina salviiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28015	Carpesium glossophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28361	Erythrina salviiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28472	Quercus petraea	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28089	Pueraria pseudohirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28250	Dichapetalum guineense	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28742	Pleurotus mutilus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28485	Bursera schlechtendalii	Species	Burseraceae	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
EC50	3
IC50	1
Others	8

Activity Type	# Activity
Organism	11
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	Activity	=	16.82	%	PMID[545777]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	Activity	=	20.0	%	PMID[545777]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	34.6	%	PMID[545777]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	Activity	=	42.4	%	PMID[545777]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	120.2	%	PMID[545777]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	120.9	%	PMID[545777]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	>	100.0	ug.cm'-2	PMID[545777]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	EC50	>	50.0	ug.cm'-2	PMID[545777]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	GI	=	61.0	%	PMID[545777]
NPT21	Organism	Aspergillus niger	Aspergillus niger	GI	=	36.0	%	PMID[545777]
NPT2	Others	Unspecified		IC50	=	2000000.0	nM	PMID[545778]

☑ 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 NPC286038 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	302
0.1-0.2	1255
0.2-0.3	2588
0.3-0.4	5479
0.4-0.5	10924
0.5-0.6	6486
0.6-0.7	6005
0.7-0.8	8532
0.8-0.85	1073
0.85-0.9	49
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC66991
0.9122	High Similarity	NPC48671
0.9054	High Similarity	NPC140133
0.8986	High Similarity	NPC212257
0.8947	High Similarity	NPC123153
0.8828	High Similarity	NPC184053
0.8786	High Similarity	NPC470976
0.8786	High Similarity	NPC470977
0.8786	High Similarity	NPC196979
0.8766	High Similarity	NPC472299
0.8766	High Similarity	NPC218818
0.8766	High Similarity	NPC4950
0.8759	High Similarity	NPC155552
0.8758	High Similarity	NPC194499
0.8758	High Similarity	NPC304692
0.8733	High Similarity	NPC146014
0.8714	High Similarity	NPC183348
0.8714	High Similarity	NPC282230
0.871	High Similarity	NPC79571
0.8693	High Similarity	NPC41880
0.8693	High Similarity	NPC104736
0.8671	High Similarity	NPC255787
0.8667	High Similarity	NPC211625
0.8667	High Similarity	NPC146388
0.8662	High Similarity	NPC308156
0.8652	High Similarity	NPC15083
0.8645	High Similarity	NPC8389
0.8645	High Similarity	NPC239118
0.8643	High Similarity	NPC66246
0.8643	High Similarity	NPC170546
0.8636	High Similarity	NPC88007
0.8636	High Similarity	NPC195954
0.8636	High Similarity	NPC477674
0.8618	High Similarity	NPC121615
0.8618	High Similarity	NPC473131
0.8618	High Similarity	NPC470675
0.8618	High Similarity	NPC294511
0.8609	High Similarity	NPC228842
0.86	High Similarity	NPC14875
0.8599	High Similarity	NPC473022
0.859	High Similarity	NPC18986
0.8582	High Similarity	NPC109778
0.8582	High Similarity	NPC327457
0.8582	High Similarity	NPC86774
0.8581	High Similarity	NPC140952
0.8581	High Similarity	NPC474611
0.8581	High Similarity	NPC158542
0.8571	High Similarity	NPC263337
0.8571	High Similarity	NPC121158
0.8562	High Similarity	NPC114880
0.8553	High Similarity	NPC321896
0.8553	High Similarity	NPC291742
0.8553	High Similarity	NPC476185
0.8552	High Similarity	NPC131198
0.8544	High Similarity	NPC100849
0.8543	High Similarity	NPC125182
0.8543	High Similarity	NPC69647
0.8542	High Similarity	NPC61499
0.8535	High Similarity	NPC92589
0.8535	High Similarity	NPC283209
0.8533	High Similarity	NPC255414
0.8523	High Similarity	NPC213900
0.8516	High Similarity	NPC7059
0.8516	High Similarity	NPC470625
0.8516	High Similarity	NPC81405
0.8514	High Similarity	NPC243577
0.8514	High Similarity	NPC469579
0.8511	High Similarity	NPC939
0.8506	High Similarity	NPC477669
0.8503	High Similarity	NPC51181
0.8503	High Similarity	NPC138149
0.85	High Similarity	NPC121104
0.85	High Similarity	NPC37512
0.8497	Intermediate Similarity	NPC474772
0.8497	Intermediate Similarity	NPC305965
0.8497	Intermediate Similarity	NPC472423
0.8497	Intermediate Similarity	NPC290671
0.8497	Intermediate Similarity	NPC474744
0.8493	Intermediate Similarity	NPC307883
0.8493	Intermediate Similarity	NPC23870
0.8491	Intermediate Similarity	NPC41689
0.8487	Intermediate Similarity	NPC116292
0.8487	Intermediate Similarity	NPC87630
0.8487	Intermediate Similarity	NPC179128
0.8487	Intermediate Similarity	NPC267469
0.8477	Intermediate Similarity	NPC300988
0.8477	Intermediate Similarity	NPC477483
0.8477	Intermediate Similarity	NPC10990
0.8477	Intermediate Similarity	NPC325032
0.8471	Intermediate Similarity	NPC472618
0.8471	Intermediate Similarity	NPC68848
0.8467	Intermediate Similarity	NPC117716
0.8467	Intermediate Similarity	NPC470673
0.8467	Intermediate Similarity	NPC470674
0.8462	Intermediate Similarity	NPC196448
0.8456	Intermediate Similarity	NPC251865
0.8452	Intermediate Similarity	NPC477671
0.8452	Intermediate Similarity	NPC159692
0.8452	Intermediate Similarity	NPC300757
0.8452	Intermediate Similarity	NPC180901
0.8452	Intermediate Similarity	NPC477687
0.8447	Intermediate Similarity	NPC472619
0.8446	Intermediate Similarity	NPC20631
0.8446	Intermediate Similarity	NPC470856
0.8446	Intermediate Similarity	NPC93640
0.8442	Intermediate Similarity	NPC10429
0.8442	Intermediate Similarity	NPC285623
0.8442	Intermediate Similarity	NPC273483
0.8442	Intermediate Similarity	NPC44606
0.8442	Intermediate Similarity	NPC271681
0.844	Intermediate Similarity	NPC2401
0.8438	Intermediate Similarity	NPC125465
0.8435	Intermediate Similarity	NPC473988
0.8435	Intermediate Similarity	NPC67003
0.8431	Intermediate Similarity	NPC472421
0.8431	Intermediate Similarity	NPC158866
0.8431	Intermediate Similarity	NPC474735
0.8428	Intermediate Similarity	NPC277618
0.8428	Intermediate Similarity	NPC121995
0.8428	Intermediate Similarity	NPC120012
0.8428	Intermediate Similarity	NPC91288
0.8425	Intermediate Similarity	NPC14697
0.8425	Intermediate Similarity	NPC24394
0.8421	Intermediate Similarity	NPC37139
0.8421	Intermediate Similarity	NPC168085
0.8418	Intermediate Similarity	NPC285567
0.8418	Intermediate Similarity	NPC469889
0.8411	Intermediate Similarity	NPC71821
0.8411	Intermediate Similarity	NPC477955
0.84	Intermediate Similarity	NPC71739
0.84	Intermediate Similarity	NPC471305
0.84	Intermediate Similarity	NPC260152
0.84	Intermediate Similarity	NPC184702
0.84	Intermediate Similarity	NPC470932
0.84	Intermediate Similarity	NPC5676
0.8397	Intermediate Similarity	NPC474738
0.8397	Intermediate Similarity	NPC321372
0.8397	Intermediate Similarity	NPC474609
0.8397	Intermediate Similarity	NPC109967
0.8397	Intermediate Similarity	NPC78554
0.8397	Intermediate Similarity	NPC129053
0.8397	Intermediate Similarity	NPC477675
0.8397	Intermediate Similarity	NPC475797
0.8397	Intermediate Similarity	NPC4547
0.8397	Intermediate Similarity	NPC469936
0.8389	Intermediate Similarity	NPC474385
0.8389	Intermediate Similarity	NPC229916
0.8387	Intermediate Similarity	NPC75310
0.8387	Intermediate Similarity	NPC472799
0.8378	Intermediate Similarity	NPC37206
0.8377	Intermediate Similarity	NPC148945
0.8377	Intermediate Similarity	NPC472580
0.8377	Intermediate Similarity	NPC204561
0.8377	Intermediate Similarity	NPC477672
0.8377	Intermediate Similarity	NPC78835
0.8377	Intermediate Similarity	NPC309512
0.8377	Intermediate Similarity	NPC316960
0.8377	Intermediate Similarity	NPC209142
0.8377	Intermediate Similarity	NPC317715
0.8377	Intermediate Similarity	NPC477673
0.8377	Intermediate Similarity	NPC312549
0.8367	Intermediate Similarity	NPC62735
0.8367	Intermediate Similarity	NPC202260
0.8366	Intermediate Similarity	NPC473016
0.8366	Intermediate Similarity	NPC88886
0.8366	Intermediate Similarity	NPC164205
0.8366	Intermediate Similarity	NPC296030
0.8366	Intermediate Similarity	NPC104236
0.8366	Intermediate Similarity	NPC104172
0.8366	Intermediate Similarity	NPC35160
0.8366	Intermediate Similarity	NPC291049
0.8366	Intermediate Similarity	NPC162569
0.8366	Intermediate Similarity	NPC233267
0.8366	Intermediate Similarity	NPC474305
0.8366	Intermediate Similarity	NPC317492
0.8366	Intermediate Similarity	NPC471114
0.8366	Intermediate Similarity	NPC39929
0.8365	Intermediate Similarity	NPC475106
0.8357	Intermediate Similarity	NPC165556
0.8357	Intermediate Similarity	NPC470858
0.8356	Intermediate Similarity	NPC283331
0.8355	Intermediate Similarity	NPC17101
0.8355	Intermediate Similarity	NPC142863
0.8355	Intermediate Similarity	NPC19747
0.8355	Intermediate Similarity	NPC474108
0.8355	Intermediate Similarity	NPC177995
0.8355	Intermediate Similarity	NPC77903
0.8354	Intermediate Similarity	NPC49009
0.8354	Intermediate Similarity	NPC188649
0.8345	Intermediate Similarity	NPC213122
0.8344	Intermediate Similarity	NPC473015
0.8344	Intermediate Similarity	NPC134621
0.8344	Intermediate Similarity	NPC472620
0.8344	Intermediate Similarity	NPC131579
0.8344	Intermediate Similarity	NPC131568
0.8344	Intermediate Similarity	NPC124780
0.8344	Intermediate Similarity	NPC271288
0.8344	Intermediate Similarity	NPC87486
0.8344	Intermediate Similarity	NPC269495
0.8344	Intermediate Similarity	NPC209040

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 NPC286038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	825
0.2-0.3	1491
0.3-0.4	2332
0.4-0.5	2155
0.5-0.6	1275
0.6-0.7	599
0.7-0.8	209
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8699	High Similarity	NPD4628	Phase 3
0.8506	High Similarity	NPD7819	Suspended
0.8503	High Similarity	NPD7421	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD6273	Approved
0.8269	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2799	Discontinued
0.8224	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6599	Discontinued
0.8141	Intermediate Similarity	NPD7411	Suspended
0.8113	Intermediate Similarity	NPD7075	Discontinued
0.811	Intermediate Similarity	NPD5844	Phase 1
0.8105	Intermediate Similarity	NPD2534	Approved
0.8105	Intermediate Similarity	NPD2532	Approved
0.8105	Intermediate Similarity	NPD2533	Approved
0.8089	Intermediate Similarity	NPD6801	Discontinued
0.8079	Intermediate Similarity	NPD3750	Approved
0.8079	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2796	Approved
0.8039	Intermediate Similarity	NPD6799	Approved
0.8014	Intermediate Similarity	NPD1608	Approved
0.8013	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6002	Phase 3
0.8	Intermediate Similarity	NPD6004	Phase 3
0.8	Intermediate Similarity	NPD6005	Phase 3
0.8	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7033	Discontinued
0.7987	Intermediate Similarity	NPD3748	Approved
0.7961	Intermediate Similarity	NPD7003	Approved
0.7947	Intermediate Similarity	NPD1549	Phase 2
0.7941	Intermediate Similarity	NPD8434	Phase 2
0.7937	Intermediate Similarity	NPD7768	Phase 2
0.7933	Intermediate Similarity	NPD2935	Discontinued
0.7925	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6355	Discontinued
0.7901	Intermediate Similarity	NPD5494	Approved
0.7898	Intermediate Similarity	NPD7458	Discontinued
0.7895	Intermediate Similarity	NPD1243	Approved
0.7895	Intermediate Similarity	NPD2800	Approved
0.7888	Intermediate Similarity	NPD3749	Approved
0.7885	Intermediate Similarity	NPD920	Approved
0.7881	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4380	Phase 2
0.7826	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD3764	Approved
0.7818	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6100	Approved
0.7815	Intermediate Similarity	NPD6099	Approved
0.7812	Intermediate Similarity	NPD5760	Phase 2
0.7812	Intermediate Similarity	NPD5761	Phase 2
0.7805	Intermediate Similarity	NPD7229	Phase 3
0.7801	Intermediate Similarity	NPD17	Approved
0.7785	Intermediate Similarity	NPD5124	Phase 1
0.7785	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3226	Approved
0.7763	Intermediate Similarity	NPD2346	Discontinued
0.7756	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1510	Phase 2
0.7744	Intermediate Similarity	NPD7199	Phase 2
0.7744	Intermediate Similarity	NPD8127	Discontinued
0.7724	Intermediate Similarity	NPD2797	Approved
0.7718	Intermediate Similarity	NPD1240	Approved
0.7718	Intermediate Similarity	NPD4140	Approved
0.7716	Intermediate Similarity	NPD3882	Suspended
0.7703	Intermediate Similarity	NPD2313	Discontinued
0.7703	Intermediate Similarity	NPD3268	Approved
0.7697	Intermediate Similarity	NPD4477	Approved
0.7697	Intermediate Similarity	NPD4476	Approved
0.7697	Intermediate Similarity	NPD1551	Phase 2
0.7687	Intermediate Similarity	NPD6832	Phase 2
0.7676	Intermediate Similarity	NPD1778	Approved
0.7669	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD9545	Approved
0.7655	Intermediate Similarity	NPD1283	Approved
0.7654	Intermediate Similarity	NPD3817	Phase 2
0.7647	Intermediate Similarity	NPD2344	Approved
0.7647	Intermediate Similarity	NPD6765	Approved
0.7647	Intermediate Similarity	NPD6764	Approved
0.7647	Intermediate Similarity	NPD6559	Discontinued
0.764	Intermediate Similarity	NPD1934	Approved
0.7639	Intermediate Similarity	NPD3972	Approved
0.7636	Intermediate Similarity	NPD6959	Discontinued
0.7632	Intermediate Similarity	NPD4308	Phase 3
0.7622	Intermediate Similarity	NPD919	Approved
0.7619	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD1607	Approved
0.7613	Intermediate Similarity	NPD4110	Phase 3
0.7613	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4060	Phase 1
0.759	Intermediate Similarity	NPD6232	Discontinued
0.7584	Intermediate Similarity	NPD6798	Discontinued
0.7584	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7473	Discontinued
0.7551	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5403	Approved
0.7545	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD8032	Phase 2
0.7532	Intermediate Similarity	NPD5763	Approved
0.7532	Intermediate Similarity	NPD5401	Approved
0.7532	Intermediate Similarity	NPD5762	Approved
0.7531	Intermediate Similarity	NPD37	Approved
0.7517	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD7236	Approved
0.7515	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7177	Discontinued
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD5953	Discontinued
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD5691	Approved
0.7483	Intermediate Similarity	NPD4307	Phase 2
0.7483	Intermediate Similarity	NPD2979	Phase 3
0.7483	Intermediate Similarity	NPD1203	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7471	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6785	Approved
0.7471	Intermediate Similarity	NPD6784	Approved
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2438	Suspended
0.7467	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3887	Approved
0.7452	Intermediate Similarity	NPD2309	Approved
0.7448	Intermediate Similarity	NPD1281	Approved
0.7439	Intermediate Similarity	NPD5402	Approved
0.7434	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2798	Approved
0.7431	Intermediate Similarity	NPD4626	Approved
0.7415	Intermediate Similarity	NPD1876	Approved
0.74	Intermediate Similarity	NPD7095	Approved
0.7396	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6166	Phase 2
0.7396	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2801	Approved
0.7378	Intermediate Similarity	NPD1465	Phase 2
0.7375	Intermediate Similarity	NPD5049	Phase 3
0.7375	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2424	Discontinued
0.7368	Intermediate Similarity	NPD7286	Phase 2
0.7361	Intermediate Similarity	NPD5585	Approved
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1511	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7356	Intermediate Similarity	NPD8312	Approved
0.7351	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2354	Approved
0.7333	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD4908	Phase 1
0.7329	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7326	Intermediate Similarity	NPD7074	Phase 3
0.732	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD1471	Phase 3
0.7305	Intermediate Similarity	NPD1241	Discontinued
0.7305	Intermediate Similarity	NPD6234	Discontinued
0.7303	Intermediate Similarity	NPD6233	Phase 2
0.7297	Intermediate Similarity	NPD8651	Approved
0.7297	Intermediate Similarity	NPD3225	Approved
0.7296	Intermediate Similarity	NPD6667	Approved
0.7296	Intermediate Similarity	NPD6666	Approved
0.7292	Intermediate Similarity	NPD1894	Discontinued
0.7285	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7239	Suspended
0.7278	Intermediate Similarity	NPD6808	Phase 2
0.7267	Intermediate Similarity	NPD7054	Approved
0.7267	Intermediate Similarity	NPD2861	Phase 2
0.7267	Intermediate Similarity	NPD1512	Approved
0.7261	Intermediate Similarity	NPD4534	Discontinued
0.726	Intermediate Similarity	NPD3496	Discontinued
0.7244	Intermediate Similarity	NPD2531	Phase 2
0.7241	Intermediate Similarity	NPD7685	Pre-registration
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7237	Intermediate Similarity	NPD411	Approved
0.7235	Intermediate Similarity	NPD3926	Phase 2
0.7233	Intermediate Similarity	NPD6190	Approved
0.7226	Intermediate Similarity	NPD7097	Phase 1
0.7225	Intermediate Similarity	NPD7472	Approved
0.7222	Intermediate Similarity	NPD7427	Discontinued
0.7219	Intermediate Similarity	NPD1247	Approved
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1610	Phase 2
0.7208	Intermediate Similarity	NPD5735	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