NPASS Compound

Structure

CID307412 OpenBabel06191716112D 28 30 0 0 1 0 0 0 0 0999 V2000 1.6984 4.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 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 3.5491 1.8090 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 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.9230 0.0000 C 0 0 0 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 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 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 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 2 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 0.3601 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.7891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 3.1043 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 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 11 2 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 22 2 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 14 16 2 0 0 0 0 14 25 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 6 0 0 0 19 21 1 6 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	386.543
LogP:	3.043
LogD:	2.336
LogS:	-3.747
# Rotatable Bonds:	6
TPSA:	92.04
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	3.871
Fsp3:	0.381
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:	-4.71
MDCK Permeability:	4.2776013287948444e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	79.45044708251953%
Volume Distribution (VD):	1.513
Pgp-substrate:	13.98570728302002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.416
CYP1A2-substrate:	0.511
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.257
CYP2C9-inhibitor:	0.845
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.814
CYP2D6-substrate:	0.325
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	4.873
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.972
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.377
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.408
Carcinogencity:	0.791
Eye Corrosion:	0.005
Eye Irritation:	0.049
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC307412

Natural Product ID:	NPC307412
*Common Name:**	[(8S,9R)-8-(2-Acetyloxypropan-2-Yl)-2-Oxo-8,9-Dihydrofuro[2,3-H]Chromen-9-Yl] (Z)-2-Methylbut-2-Enoate
IUPAC Name:	[(8S,9R)-8-(2-acetyloxypropan-2-yl)-2-oxo-8,9-dihydrofuro[2,3-h]chromen-9-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	FFCDTHIJWHJUQJ-JZWAJAMXSA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-6-11(2)20(24)27-18-16-14(25-19(18)21(4,5)28-12(3)22)9-7-13-8-10-15(23)26-17(13)16/h6-10,18-19H,1-5H3/b11-6-/t18-,19+/m1/s1
SMILES:	C/C=C(/C)C(=O)O[C@@H]1c2c(ccc3ccc(=O)oc23)O[C@@H]1C(C)(C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1302068
PubChem CID:	5317013
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002568] Angular furanocoumarins

*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
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10785419]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12568545]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22932311]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23721280]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28093914]
NPO12662	Torilis japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12662	Torilis japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12662	Torilis japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO900	Cnidium monieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12662	Torilis japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15544	Cnidium monnieri	Species	Apiaceae	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
Potency	9

Activity Type	# Activity
Individual Protein	8
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[459658]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	31622.8	nM	PMID[459658]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	145.8	nM	PMID[459658]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[459658]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[459658]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[459658]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[459658]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	5858.4	nM	PMID[459658]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	5323.3	nM	PMID[459658]

☑ 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 NPC307412 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	410
0.1-0.2	1678
0.2-0.3	4209
0.3-0.4	9470
0.4-0.5	9017
0.5-0.6	4076
0.6-0.7	5950
0.7-0.8	5676
0.8-0.85	1636
0.85-0.9	372
0.9-0.95	156
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC55149
0.9921	High Similarity	NPC7526
0.9921	High Similarity	NPC222036
0.9843	High Similarity	NPC14248
0.9692	High Similarity	NPC283331
0.969	High Similarity	NPC166672
0.969	High Similarity	NPC267412
0.969	High Similarity	NPC164269
0.969	High Similarity	NPC74655
0.969	High Similarity	NPC287182
0.969	High Similarity	NPC100986
0.969	High Similarity	NPC260265
0.969	High Similarity	NPC47163
0.969	High Similarity	NPC84894
0.969	High Similarity	NPC18804
0.969	High Similarity	NPC195343
0.969	High Similarity	NPC319859
0.969	High Similarity	NPC198381
0.969	High Similarity	NPC127888
0.9615	High Similarity	NPC471625
0.9615	High Similarity	NPC86892
0.9615	High Similarity	NPC281241
0.9615	High Similarity	NPC472424
0.9615	High Similarity	NPC471909
0.9612	High Similarity	NPC318400
0.9612	High Similarity	NPC167111
0.9612	High Similarity	NPC207002
0.9612	High Similarity	NPC133956
0.9612	High Similarity	NPC296624
0.9612	High Similarity	NPC471910
0.9542	High Similarity	NPC471630
0.9542	High Similarity	NPC177281
0.9542	High Similarity	NPC476455
0.9542	High Similarity	NPC128529
0.9542	High Similarity	NPC160727
0.9542	High Similarity	NPC149320
0.9542	High Similarity	NPC55615
0.9542	High Similarity	NPC283019
0.947	High Similarity	NPC155963
0.9466	High Similarity	NPC33986
0.9466	High Similarity	NPC469675
0.9398	High Similarity	NPC211110
0.9398	High Similarity	NPC151946
0.9389	High Similarity	NPC253574
0.9389	High Similarity	NPC98179
0.938	High Similarity	NPC80170
0.937	High Similarity	NPC188327
0.937	High Similarity	NPC234109
0.9328	High Similarity	NPC312881
0.9318	High Similarity	NPC472525
0.9302	High Similarity	NPC168710
0.9259	High Similarity	NPC152771
0.9259	High Similarity	NPC195357
0.9259	High Similarity	NPC287286
0.9254	High Similarity	NPC279573
0.9248	High Similarity	NPC26954
0.9248	High Similarity	NPC38099
0.9242	High Similarity	NPC62366
0.9242	High Similarity	NPC224475
0.9242	High Similarity	NPC213173
0.9242	High Similarity	NPC180716
0.9225	High Similarity	NPC472519
0.9225	High Similarity	NPC199204
0.9213	High Similarity	NPC73413
0.9213	High Similarity	NPC201667
0.9179	High Similarity	NPC153818
0.9179	High Similarity	NPC232246
0.9167	High Similarity	NPC31849
0.9167	High Similarity	NPC163557
0.9141	High Similarity	NPC471828
0.9141	High Similarity	NPC471827
0.9134	High Similarity	NPC109675
0.9134	High Similarity	NPC472518
0.9134	High Similarity	NPC273772
0.9124	High Similarity	NPC183646
0.9124	High Similarity	NPC119640
0.9104	High Similarity	NPC224543
0.9104	High Similarity	NPC78746
0.9104	High Similarity	NPC188380
0.9098	High Similarity	NPC50896
0.9098	High Similarity	NPC326600
0.9098	High Similarity	NPC204353
0.9077	High Similarity	NPC185066
0.907	High Similarity	NPC471826
0.9062	High Similarity	NPC27671
0.9058	High Similarity	NPC476457
0.9055	High Similarity	NPC96286
0.9055	High Similarity	NPC248429
0.9037	High Similarity	NPC294456
0.9037	High Similarity	NPC212124
0.9037	High Similarity	NPC184861
0.9037	High Similarity	NPC225106
0.9037	High Similarity	NPC14697
0.9037	High Similarity	NPC281014
0.9015	High Similarity	NPC29734
0.9	High Similarity	NPC296377
0.8993	High Similarity	NPC76657
0.8947	High Similarity	NPC194277
0.8939	High Similarity	NPC113098
0.8936	High Similarity	NPC169510
0.8921	High Similarity	NPC471824
0.8915	High Similarity	NPC291899
0.8915	High Similarity	NPC111347
0.8898	High Similarity	NPC180006
0.8898	High Similarity	NPC235190
0.8898	High Similarity	NPC163200
0.8897	High Similarity	NPC471068
0.8897	High Similarity	NPC471069
0.8881	High Similarity	NPC469449
0.8872	High Similarity	NPC267336
0.8872	High Similarity	NPC272650
0.8857	High Similarity	NPC85624
0.8857	High Similarity	NPC469701
0.8837	High Similarity	NPC154176
0.8837	High Similarity	NPC173350
0.8837	High Similarity	NPC290605
0.8837	High Similarity	NPC50720
0.8832	High Similarity	NPC471072
0.8832	High Similarity	NPC471071
0.8832	High Similarity	NPC471070
0.8832	High Similarity	NPC270256
0.8828	High Similarity	NPC144418
0.8806	High Similarity	NPC469956
0.8806	High Similarity	NPC19157
0.8797	High Similarity	NPC19242
0.8788	High Similarity	NPC139595
0.8788	High Similarity	NPC157212
0.8788	High Similarity	NPC293642
0.8788	High Similarity	NPC60704
0.876	High Similarity	NPC13007
0.876	High Similarity	NPC150214
0.876	High Similarity	NPC257188
0.8741	High Similarity	NPC472522
0.8741	High Similarity	NPC469952
0.8741	High Similarity	NPC55147
0.8741	High Similarity	NPC241341
0.8741	High Similarity	NPC233018
0.8741	High Similarity	NPC54503
0.8741	High Similarity	NPC36437
0.8741	High Similarity	NPC469955
0.874	High Similarity	NPC281356
0.874	High Similarity	NPC298796
0.8732	High Similarity	NPC87950
0.8732	High Similarity	NPC471764
0.8712	High Similarity	NPC243688
0.8712	High Similarity	NPC289316
0.8712	High Similarity	NPC121740
0.8712	High Similarity	NPC258567
0.8712	High Similarity	NPC224774
0.8692	High Similarity	NPC315807
0.8686	High Similarity	NPC167517
0.8667	High Similarity	NPC319969
0.8667	High Similarity	NPC175159
0.8667	High Similarity	NPC137669
0.8667	High Similarity	NPC123954
0.8662	High Similarity	NPC171656
0.8661	High Similarity	NPC152306
0.8661	High Similarity	NPC265547
0.8661	High Similarity	NPC96705
0.8652	High Similarity	NPC471763
0.8647	High Similarity	NPC469453
0.8643	High Similarity	NPC470856
0.8636	High Similarity	NPC101894
0.8636	High Similarity	NPC163248
0.8623	High Similarity	NPC306365
0.8613	High Similarity	NPC229128
0.8593	High Similarity	NPC472517
0.8571	High Similarity	NPC279851
0.8571	High Similarity	NPC472523
0.8571	High Similarity	NPC476442
0.8571	High Similarity	NPC300611
0.8571	High Similarity	NPC215512
0.8571	High Similarity	NPC472520
0.8562	High Similarity	NPC470264
0.8561	High Similarity	NPC93219
0.8561	High Similarity	NPC202594
0.8561	High Similarity	NPC232692
0.8561	High Similarity	NPC307883
0.8561	High Similarity	NPC244495
0.8552	High Similarity	NPC103116
0.8551	High Similarity	NPC286843
0.855	High Similarity	NPC143725
0.854	High Similarity	NPC309953
0.854	High Similarity	NPC147030
0.854	High Similarity	NPC131950
0.8531	High Similarity	NPC205361
0.8531	High Similarity	NPC294365
0.8519	High Similarity	NPC240722
0.8519	High Similarity	NPC244799
0.8519	High Similarity	NPC476399
0.8519	High Similarity	NPC32463
0.8504	High Similarity	NPC128633
0.8496	Intermediate Similarity	NPC127604
0.8489	Intermediate Similarity	NPC131198
0.8489	Intermediate Similarity	NPC20796
0.8478	Intermediate Similarity	NPC311430
0.8478	Intermediate Similarity	NPC61499
0.8478	Intermediate Similarity	NPC472521
0.8478	Intermediate Similarity	NPC224941
0.8478	Intermediate Similarity	NPC234865

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 NPC307412 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	957
0.2-0.3	1767
0.3-0.4	2660
0.4-0.5	1867
0.5-0.6	1040
0.6-0.7	358
0.7-0.8	119
0.8-0.85	29
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8467	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD5124	Phase 1
0.8258	Intermediate Similarity	NPD422	Phase 1
0.8182	Intermediate Similarity	NPD1652	Phase 2
0.8163	Intermediate Similarity	NPD920	Approved
0.8102	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1243	Approved
0.8027	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1296	Phase 2
0.7986	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD2796	Approved
0.7961	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD3748	Approved
0.7895	Intermediate Similarity	NPD6801	Discontinued
0.7871	Intermediate Similarity	NPD919	Approved
0.7862	Intermediate Similarity	NPD2424	Discontinued
0.7838	Intermediate Similarity	NPD6799	Approved
0.7806	Intermediate Similarity	NPD7075	Discontinued
0.7795	Intermediate Similarity	NPD1358	Approved
0.7761	Intermediate Similarity	NPD5691	Approved
0.7748	Intermediate Similarity	NPD1653	Approved
0.7733	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5494	Approved
0.7667	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6599	Discontinued
0.7647	Intermediate Similarity	NPD4380	Phase 2
0.7638	Intermediate Similarity	NPD9697	Approved
0.7635	Intermediate Similarity	NPD3750	Approved
0.7635	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5535	Approved
0.7613	Intermediate Similarity	NPD7819	Suspended
0.7597	Intermediate Similarity	NPD7411	Suspended
0.7593	Intermediate Similarity	NPD5844	Phase 1
0.7589	Intermediate Similarity	NPD6832	Phase 2
0.7589	Intermediate Similarity	NPD4908	Phase 1
0.7578	Intermediate Similarity	NPD3134	Approved
0.7569	Intermediate Similarity	NPD6355	Discontinued
0.7568	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5403	Approved
0.7564	Intermediate Similarity	NPD3817	Phase 2
0.7556	Intermediate Similarity	NPD1548	Phase 1
0.7551	Intermediate Similarity	NPD6002	Phase 3
0.7551	Intermediate Similarity	NPD6005	Phase 3
0.7551	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6004	Phase 3
0.7551	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5401	Approved
0.7534	Intermediate Similarity	NPD7033	Discontinued
0.7518	Intermediate Similarity	NPD3496	Discontinued
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.75	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7468	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7097	Phase 1
0.7464	Intermediate Similarity	NPD1610	Phase 2
0.7455	Intermediate Similarity	NPD6559	Discontinued
0.7452	Intermediate Similarity	NPD5402	Approved
0.7451	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4626	Approved
0.7438	Intermediate Similarity	NPD1247	Approved
0.7434	Intermediate Similarity	NPD2534	Approved
0.7434	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2533	Approved
0.7434	Intermediate Similarity	NPD2532	Approved
0.7429	Intermediate Similarity	NPD8651	Approved
0.7429	Intermediate Similarity	NPD3225	Approved
0.7413	Intermediate Similarity	NPD3027	Phase 3
0.7383	Intermediate Similarity	NPD1549	Phase 2
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7361	Intermediate Similarity	NPD3268	Approved
0.7343	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1091	Approved
0.7338	Intermediate Similarity	NPD1611	Approved
0.7329	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4340	Discontinued
0.7328	Intermediate Similarity	NPD2684	Approved
0.7325	Intermediate Similarity	NPD1934	Approved
0.7325	Intermediate Similarity	NPD37	Approved
0.7324	Intermediate Similarity	NPD1019	Discontinued
0.7317	Intermediate Similarity	NPD3818	Discontinued
0.7315	Intermediate Similarity	NPD5762	Approved
0.7315	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5763	Approved
0.7313	Intermediate Similarity	NPD1241	Discontinued
0.731	Intermediate Similarity	NPD6233	Phase 2
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7297	Intermediate Similarity	NPD2799	Discontinued
0.7297	Intermediate Similarity	NPD1510	Phase 2
0.7297	Intermediate Similarity	NPD4308	Phase 3
0.7296	Intermediate Similarity	NPD4967	Phase 2
0.7296	Intermediate Similarity	NPD4965	Approved
0.7296	Intermediate Similarity	NPD3882	Suspended
0.7296	Intermediate Similarity	NPD4966	Approved
0.7292	Intermediate Similarity	NPD4625	Phase 3
0.7285	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3749	Approved
0.7241	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2313	Discontinued
0.7239	Intermediate Similarity	NPD7843	Approved
0.7234	Intermediate Similarity	NPD4749	Approved
0.7233	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7199	Phase 2
0.7219	Intermediate Similarity	NPD2800	Approved
0.7214	Intermediate Similarity	NPD3705	Approved
0.7206	Intermediate Similarity	NPD7157	Approved
0.7205	Intermediate Similarity	NPD6234	Discontinued
0.7202	Intermediate Similarity	NPD7549	Discontinued
0.72	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1778	Approved
0.719	Intermediate Similarity	NPD6667	Approved
0.719	Intermediate Similarity	NPD6666	Approved
0.7181	Intermediate Similarity	NPD5588	Approved
0.7172	Intermediate Similarity	NPD7095	Approved
0.7171	Intermediate Similarity	NPD7466	Approved
0.717	Intermediate Similarity	NPD8455	Phase 2
0.717	Intermediate Similarity	NPD2801	Approved
0.7163	Intermediate Similarity	NPD9717	Approved
0.7153	Intermediate Similarity	NPD3018	Phase 2
0.7153	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7134	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6032	Approved
0.7133	Intermediate Similarity	NPD2438	Suspended
0.7125	Intermediate Similarity	NPD2415	Discontinued
0.7124	Intermediate Similarity	NPD3887	Approved
0.7122	Intermediate Similarity	NPD5585	Approved
0.7121	Intermediate Similarity	NPD290	Approved
0.7117	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD4538	Approved
0.7114	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4536	Approved
0.7105	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5536	Phase 2
0.7095	Intermediate Similarity	NPD447	Suspended
0.7095	Intermediate Similarity	NPD1933	Approved
0.7075	Intermediate Similarity	NPD4062	Phase 3
0.7073	Intermediate Similarity	NPD6232	Discontinued
0.7071	Intermediate Similarity	NPD17	Approved
0.7047	Intermediate Similarity	NPD1607	Approved
0.7047	Intermediate Similarity	NPD6653	Approved
0.7042	Intermediate Similarity	NPD2981	Phase 2
0.7032	Intermediate Similarity	NPD1511	Approved
0.7032	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3926	Phase 2
0.7027	Intermediate Similarity	NPD2979	Phase 3
0.702	Intermediate Similarity	NPD4477	Approved
0.702	Intermediate Similarity	NPD4476	Approved
0.7019	Intermediate Similarity	NPD4288	Approved
0.7019	Intermediate Similarity	NPD5353	Approved
0.7014	Intermediate Similarity	NPD1203	Approved
0.7007	Intermediate Similarity	NPD7985	Registered
0.6993	Remote Similarity	NPD2983	Phase 2
0.6993	Remote Similarity	NPD2982	Phase 2
0.6988	Remote Similarity	NPD6166	Phase 2
0.6988	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5953	Discontinued
0.698	Remote Similarity	NPD230	Phase 1
0.6978	Remote Similarity	NPD7644	Approved
0.6972	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7286	Phase 2
0.6964	Remote Similarity	NPD7054	Approved
0.6959	Remote Similarity	NPD8032	Phase 2
0.6957	Remote Similarity	NPD1465	Phase 2
0.6957	Remote Similarity	NPD6671	Approved
0.6954	Remote Similarity	NPD5960	Phase 3
0.6948	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4110	Phase 3
0.6946	Remote Similarity	NPD7473	Discontinued
0.6944	Remote Similarity	NPD6696	Suspended
0.6943	Remote Similarity	NPD1512	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