NPASS Compound

Structure

NPC152812 OpenBabel07101718332D 28 30 0 0 1 0 0 0 0 0999 V2000 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 2 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 25 2 0 0 0 0 15 21 1 0 0 0 0 15 26 2 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 19 21 1 0 0 0 0 20 24 1 6 0 0 0 21 24 1 6 0 0 0 22 24 1 6 0 0 0 22 28 1 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 24 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.18
Volume:	409.424
LogP:	3.482
LogD:	2.923
LogS:	-4.433
# Rotatable Bonds:	6
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	4.449
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.693
MDCK Permeability:	1.7145717720268294e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.078
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	57.161170959472656%
Volume Distribution (VD):	2.013
Pgp-substrate:	40.491886138916016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	7.527
Half-life (T1/2):	0.302

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.857
Drug-inuced Liver Injury (DILI):	0.182
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.961
Carcinogencity:	0.386
Eye Corrosion:	0.988
Eye Irritation:	0.981
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: NPC152812

Natural Product ID:	NPC152812
*Common Name:**	Paxidal
IUPAC Name:	[(1R,3S,4aS,8R,8aS)-7,8-diformyl-3,8a-dimethyl-4-methylidene-1,2,3,4a,5,8-hexahydronaphthalen-1-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	RIGSJIIZCIKSKY-PKCWWXAYSA-N
Standard InCHI:	InChI=1S/C24H26O4/c1-16-13-22(28-23(27)12-9-18-7-5-4-6-8-18)24(3)20(17(16)2)11-10-19(14-25)21(24)15-26/h4-10,12,14-16,20-22H,2,11,13H2,1,3H3/b12-9+/t16-,20-,21-,22+,24-/m0/s1
SMILES:	O=C[C@H]1C(=CC[C@@H]2[C@]1(C)[C@H](OC(=O)/C=C/c1ccccc1)C[C@@H](C2=C)C)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252767
PubChem CID:	11682335
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO12007	Pseudowintera axillaris	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16417306]
NPO12007	Pseudowintera axillaris	Species	Winteraceae	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
Others	16

Activity Type	# Activity
Organism	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT827	Organism	Mycosphaerella graminicola	Mycosphaerella graminicola	Inhibition	=	0.0	%	PMID[569864]
NPT827	Organism	Mycosphaerella graminicola	Mycosphaerella graminicola	Inhibition	=	7.0	%	PMID[569864]
NPT6576	Organism	Puccinia graminis f. tritici	Puccinia graminis f. tritici	Inhibition	=	0.0	%	PMID[569864]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	0.0	%	PMID[569864]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	23.0	%	PMID[569864]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	51.0	%	PMID[569864]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	18.0	%	PMID[569864]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	57.0	%	PMID[569864]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	9.0	%	PMID[569864]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	69.0	%	PMID[569864]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	0.0	%	PMID[569864]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	18.0	%	PMID[569864]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	17.0	%	PMID[569864]

☑ 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 NPC152812 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	253
0.1-0.2	1127
0.2-0.3	1915
0.3-0.4	5682
0.4-0.5	10579
0.5-0.6	17587
0.6-0.7	4807
0.7-0.8	725
0.8-0.85	17
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9397	High Similarity	NPC12881
0.9397	High Similarity	NPC140118
0.8607	High Similarity	NPC470818
0.8583	High Similarity	NPC194970
0.8387	Intermediate Similarity	NPC473423
0.832	Intermediate Similarity	NPC195224
0.8293	Intermediate Similarity	NPC469742
0.824	Intermediate Similarity	NPC171007
0.824	Intermediate Similarity	NPC190849
0.8235	Intermediate Similarity	NPC470820
0.8205	Intermediate Similarity	NPC128368
0.8125	Intermediate Similarity	NPC472418
0.811	Intermediate Similarity	NPC225103
0.8099	Intermediate Similarity	NPC89324
0.8095	Intermediate Similarity	NPC169913
0.8077	Intermediate Similarity	NPC329913
0.8062	Intermediate Similarity	NPC80599
0.8047	Intermediate Similarity	NPC473443
0.8047	Intermediate Similarity	NPC472388
0.8033	Intermediate Similarity	NPC470814
0.8033	Intermediate Similarity	NPC202015
0.8033	Intermediate Similarity	NPC204784
0.8017	Intermediate Similarity	NPC84129
0.8016	Intermediate Similarity	NPC275576
0.8016	Intermediate Similarity	NPC473082
0.8	Intermediate Similarity	NPC472656
0.7984	Intermediate Similarity	NPC470278
0.7984	Intermediate Similarity	NPC472361
0.7967	Intermediate Similarity	NPC473243
0.7953	Intermediate Similarity	NPC473220
0.7953	Intermediate Similarity	NPC470753
0.7939	Intermediate Similarity	NPC471911
0.7939	Intermediate Similarity	NPC4242
0.7939	Intermediate Similarity	NPC126516
0.7939	Intermediate Similarity	NPC203486
0.7937	Intermediate Similarity	NPC472694
0.7937	Intermediate Similarity	NPC472693
0.7937	Intermediate Similarity	NPC295664
0.7923	Intermediate Similarity	NPC209851
0.7923	Intermediate Similarity	NPC472394
0.7923	Intermediate Similarity	NPC475493
0.7907	Intermediate Similarity	NPC475138
0.7907	Intermediate Similarity	NPC147561
0.7903	Intermediate Similarity	NPC473439
0.7903	Intermediate Similarity	NPC50872
0.7903	Intermediate Similarity	NPC300827
0.7895	Intermediate Similarity	NPC184109
0.7891	Intermediate Similarity	NPC115797
0.7891	Intermediate Similarity	NPC51448
0.7879	Intermediate Similarity	NPC477896
0.7879	Intermediate Similarity	NPC477893
0.7874	Intermediate Similarity	NPC470765
0.7874	Intermediate Similarity	NPC470816
0.7869	Intermediate Similarity	NPC61651
0.7863	Intermediate Similarity	NPC15850
0.7863	Intermediate Similarity	NPC472437
0.7857	Intermediate Similarity	NPC328107
0.784	Intermediate Similarity	NPC473749
0.7823	Intermediate Similarity	NPC474223
0.7823	Intermediate Similarity	NPC474222
0.7823	Intermediate Similarity	NPC475827
0.7823	Intermediate Similarity	NPC475804
0.7815	Intermediate Similarity	NPC280789
0.7812	Intermediate Similarity	NPC253681
0.7812	Intermediate Similarity	NPC51292
0.7795	Intermediate Similarity	NPC473083
0.7788	Intermediate Similarity	NPC221825
0.7786	Intermediate Similarity	NPC471880
0.7778	Intermediate Similarity	NPC470007
0.7778	Intermediate Similarity	NPC12016
0.7769	Intermediate Similarity	NPC473869
0.7768	Intermediate Similarity	NPC226041
0.776	Intermediate Similarity	NPC311175
0.776	Intermediate Similarity	NPC37641
0.7744	Intermediate Similarity	NPC473216
0.7744	Intermediate Similarity	NPC473399
0.7737	Intermediate Similarity	NPC477468
0.7734	Intermediate Similarity	NPC476599
0.7724	Intermediate Similarity	NPC45794
0.7717	Intermediate Similarity	NPC307139
0.7717	Intermediate Similarity	NPC51079
0.7717	Intermediate Similarity	NPC472373
0.7717	Intermediate Similarity	NPC470815
0.7712	Intermediate Similarity	NPC40178
0.7712	Intermediate Similarity	NPC469636
0.7705	Intermediate Similarity	NPC476476
0.7698	Intermediate Similarity	NPC70973
0.7698	Intermediate Similarity	NPC293831
0.7698	Intermediate Similarity	NPC369
0.7687	Intermediate Similarity	NPC472545
0.7687	Intermediate Similarity	NPC472374
0.7687	Intermediate Similarity	NPC477874
0.7687	Intermediate Similarity	NPC472372
0.7687	Intermediate Similarity	NPC173569
0.7687	Intermediate Similarity	NPC472551
0.7686	Intermediate Similarity	NPC307651
0.768	Intermediate Similarity	NPC133389
0.768	Intermediate Similarity	NPC77000
0.768	Intermediate Similarity	NPC183339
0.768	Intermediate Similarity	NPC238861
0.768	Intermediate Similarity	NPC234337
0.7669	Intermediate Similarity	NPC474608
0.7669	Intermediate Similarity	NPC48929
0.7667	Intermediate Similarity	NPC270699
0.7667	Intermediate Similarity	NPC82899
0.7664	Intermediate Similarity	NPC63737
0.7664	Intermediate Similarity	NPC172311
0.7661	Intermediate Similarity	NPC254233
0.7656	Intermediate Similarity	NPC471758
0.7647	Intermediate Similarity	NPC196246
0.7647	Intermediate Similarity	NPC214067
0.7647	Intermediate Similarity	NPC477904
0.7647	Intermediate Similarity	NPC473440
0.7647	Intermediate Similarity	NPC183270
0.7638	Intermediate Similarity	NPC474159
0.7638	Intermediate Similarity	NPC474254
0.7634	Intermediate Similarity	NPC131684
0.7634	Intermediate Similarity	NPC471832
0.763	Intermediate Similarity	NPC249817
0.763	Intermediate Similarity	NPC39549
0.763	Intermediate Similarity	NPC475373
0.7627	Intermediate Similarity	NPC47536
0.7627	Intermediate Similarity	NPC21929
0.7623	Intermediate Similarity	NPC221275
0.7612	Intermediate Similarity	NPC472577
0.7612	Intermediate Similarity	NPC291638
0.7612	Intermediate Similarity	NPC17877
0.7612	Intermediate Similarity	NPC195647
0.7612	Intermediate Similarity	NPC66761
0.7609	Intermediate Similarity	NPC477894
0.7603	Intermediate Similarity	NPC306977
0.7603	Intermediate Similarity	NPC206414
0.7603	Intermediate Similarity	NPC287055
0.7603	Intermediate Similarity	NPC242957
0.7597	Intermediate Similarity	NPC45821
0.7597	Intermediate Similarity	NPC137416
0.7583	Intermediate Similarity	NPC1082
0.7583	Intermediate Similarity	NPC305912
0.7578	Intermediate Similarity	NPC325740
0.7578	Intermediate Similarity	NPC318067
0.7578	Intermediate Similarity	NPC8990
0.7578	Intermediate Similarity	NPC85511
0.7576	Intermediate Similarity	NPC72915
0.7574	Intermediate Similarity	NPC22676
0.7574	Intermediate Similarity	NPC475482
0.7574	Intermediate Similarity	NPC216940
0.7574	Intermediate Similarity	NPC472395
0.7574	Intermediate Similarity	NPC472371
0.7574	Intermediate Similarity	NPC198621
0.7563	Intermediate Similarity	NPC10251
0.7563	Intermediate Similarity	NPC17417
0.7561	Intermediate Similarity	NPC226093
0.7561	Intermediate Similarity	NPC260886
0.7554	Intermediate Similarity	NPC80895
0.7554	Intermediate Similarity	NPC471912
0.7554	Intermediate Similarity	NPC473677
0.7554	Intermediate Similarity	NPC475404
0.7541	Intermediate Similarity	NPC196075
0.7541	Intermediate Similarity	NPC294458
0.754	Intermediate Similarity	NPC476225
0.7538	Intermediate Similarity	NPC5486
0.7537	Intermediate Similarity	NPC310662
0.7536	Intermediate Similarity	NPC182869
0.7536	Intermediate Similarity	NPC475135
0.7521	Intermediate Similarity	NPC470297
0.7521	Intermediate Similarity	NPC329282
0.752	Intermediate Similarity	NPC473860
0.752	Intermediate Similarity	NPC64340
0.7519	Intermediate Similarity	NPC114927
0.7519	Intermediate Similarity	NPC477369
0.7519	Intermediate Similarity	NPC238370
0.7518	Intermediate Similarity	NPC475400
0.7518	Intermediate Similarity	NPC79921
0.7518	Intermediate Similarity	NPC472547
0.75	Intermediate Similarity	NPC182333
0.75	Intermediate Similarity	NPC301946
0.75	Intermediate Similarity	NPC277053
0.75	Intermediate Similarity	NPC283375
0.75	Intermediate Similarity	NPC49272
0.75	Intermediate Similarity	NPC190298
0.75	Intermediate Similarity	NPC93084
0.75	Intermediate Similarity	NPC183122
0.75	Intermediate Similarity	NPC471100
0.75	Intermediate Similarity	NPC471107
0.75	Intermediate Similarity	NPC127857
0.75	Intermediate Similarity	NPC251854
0.75	Intermediate Similarity	NPC242764
0.75	Intermediate Similarity	NPC273336
0.75	Intermediate Similarity	NPC105141
0.7481	Intermediate Similarity	NPC230331
0.7481	Intermediate Similarity	NPC471864
0.748	Intermediate Similarity	NPC472981
0.748	Intermediate Similarity	NPC144547
0.748	Intermediate Similarity	NPC474095
0.748	Intermediate Similarity	NPC470764
0.7479	Intermediate Similarity	NPC20485
0.7479	Intermediate Similarity	NPC56493
0.7466	Intermediate Similarity	NPC25351
0.7464	Intermediate Similarity	NPC224491
0.7462	Intermediate Similarity	NPC473111

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 NPC152812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	814
0.2-0.3	1268
0.3-0.4	2958
0.4-0.5	2312
0.5-0.6	1302
0.6-0.7	239
0.7-0.8	22
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
0.8051	Intermediate Similarity	NPD6858	Approved
0.8051	Intermediate Similarity	NPD7094	Approved
0.7686	Intermediate Similarity	NPD6010	Discontinued
0.768	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD5909	Discontinued
0.7583	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD2182	Approved
0.75	Intermediate Similarity	NPD7236	Approved
0.748	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3317	Approved
0.7368	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2067	Discontinued
0.7345	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD2629	Approved
0.7288	Intermediate Similarity	NPD6647	Phase 2
0.7259	Intermediate Similarity	NPD7961	Discontinued
0.7241	Intermediate Similarity	NPD7239	Suspended
0.7239	Intermediate Similarity	NPD7008	Discontinued
0.7236	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3673	Approved
0.7232	Intermediate Similarity	NPD3672	Approved
0.7231	Intermediate Similarity	NPD6637	Approved
0.7227	Intermediate Similarity	NPD164	Approved
0.7217	Intermediate Similarity	NPD1989	Approved
0.72	Intermediate Similarity	NPD5951	Approved
0.7179	Intermediate Similarity	NPD2066	Phase 3
0.7179	Intermediate Similarity	NPD7798	Approved
0.7155	Intermediate Similarity	NPD3495	Discontinued
0.7154	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6287	Discontinued
0.7131	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD8166	Discontinued
0.7094	Intermediate Similarity	NPD5926	Approved
0.708	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1932	Approved
0.7037	Intermediate Similarity	NPD7055	Discontinued
0.7034	Intermediate Similarity	NPD1238	Approved
0.7025	Intermediate Similarity	NPD5048	Discontinued
0.7008	Intermediate Similarity	NPD4198	Discontinued
0.7	Intermediate Similarity	NPD1930	Approved
0.7	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1929	Approved
0.7	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2329	Discontinued
0.6957	Remote Similarity	NPD7631	Approved
0.6908	Remote Similarity	NPD7057	Phase 3
0.6908	Remote Similarity	NPD7058	Phase 2
0.6899	Remote Similarity	NPD6065	Approved
0.6884	Remote Similarity	NPD6663	Approved
0.6879	Remote Similarity	NPD7305	Phase 1
0.687	Remote Similarity	NPD7609	Phase 3
0.6838	Remote Similarity	NPD5736	Approved
0.6814	Remote Similarity	NPD1087	Approved
0.681	Remote Similarity	NPD1088	Approved
0.6786	Remote Similarity	NPD1694	Approved
0.6783	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7610	Discontinued
0.6763	Remote Similarity	NPD8032	Phase 2
0.6759	Remote Similarity	NPD4628	Phase 3
0.6757	Remote Similarity	NPD6273	Approved
0.6718	Remote Similarity	NPD7009	Phase 2
0.6716	Remote Similarity	NPD3972	Approved
0.6714	Remote Similarity	NPD2979	Phase 3
0.6695	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6049	Phase 2
0.6694	Remote Similarity	NPD6685	Approved
0.6691	Remote Similarity	NPD3267	Approved
0.6691	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD1282	Approved
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD4766	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD650	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD1317	Discontinued
0.6667	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3573	Approved
0.6644	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7003	Approved
0.6642	Remote Similarity	NPD1281	Approved
0.6642	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD1089	Approved
0.6638	Remote Similarity	NPD1090	Approved
0.6638	Remote Similarity	NPD1086	Approved
0.6623	Remote Similarity	NPD7458	Discontinued
0.6617	Remote Similarity	NPD17	Approved
0.6617	Remote Similarity	NPD2932	Approved
0.661	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1563	Approved
0.661	Remote Similarity	NPD7900	Approved
0.661	Remote Similarity	NPD1202	Approved
0.6606	Remote Similarity	NPD225	Approved
0.6606	Remote Similarity	NPD227	Approved
0.6597	Remote Similarity	NPD2438	Suspended
0.6594	Remote Similarity	NPD7084	Phase 3
0.6577	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3268	Approved
0.6569	Remote Similarity	NPD2797	Approved
0.6567	Remote Similarity	NPD3023	Approved
0.6567	Remote Similarity	NPD3026	Approved
0.6566	Remote Similarity	NPD8434	Phase 2
0.6565	Remote Similarity	NPD4576	Approved
0.6565	Remote Similarity	NPD4574	Approved
0.6555	Remote Similarity	NPD1693	Approved
0.6555	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD800	Approved
0.6552	Remote Similarity	NPD5346	Phase 2
0.6552	Remote Similarity	NPD5347	Phase 2
0.6538	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2799	Discontinued
0.6525	Remote Similarity	NPD7713	Phase 3
0.6522	Remote Similarity	NPD7799	Discontinued
0.6522	Remote Similarity	NPD6085	Phase 2
0.6522	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2347	Approved
0.6513	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2607	Approved
0.6497	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5667	Approved
0.6496	Remote Similarity	NPD1283	Approved
0.6493	Remote Similarity	NPD3019	Approved
0.6491	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2531	Phase 2
0.6479	Remote Similarity	NPD4140	Approved
0.6471	Remote Similarity	NPD1608	Approved
0.6466	Remote Similarity	NPD7741	Discontinued
0.6463	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8368	Discontinued
0.646	Remote Similarity	NPD3971	Phase 1
0.6454	Remote Similarity	NPD2313	Discontinued
0.6454	Remote Similarity	NPD3764	Approved
0.6452	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5765	Approved
0.6446	Remote Similarity	NPD1564	Approved
0.6446	Remote Similarity	NPD1565	Approved
0.6446	Remote Similarity	NPD7902	Approved
0.6446	Remote Similarity	NPD1566	Phase 3
0.6441	Remote Similarity	NPD1239	Approved
0.6438	Remote Similarity	NPD1471	Phase 3
0.6434	Remote Similarity	NPD6355	Discontinued
0.6429	Remote Similarity	NPD6832	Phase 2
0.6429	Remote Similarity	NPD226	Approved
0.6429	Remote Similarity	NPD5706	Approved
0.6429	Remote Similarity	NPD5705	Approved
0.6429	Remote Similarity	NPD5704	Approved
0.6423	Remote Similarity	NPD4359	Approved
0.6419	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4110	Phase 3
0.6418	Remote Similarity	NPD1651	Approved
0.6418	Remote Similarity	NPD5981	Approved
0.6415	Remote Similarity	NPD8127	Discontinued
0.6408	Remote Similarity	NPD7714	Approved
0.6408	Remote Similarity	NPD7715	Approved
0.6406	Remote Similarity	NPD1752	Approved
0.6406	Remote Similarity	NPD4233	Approved
0.6406	Remote Similarity	NPD5240	Approved
0.6406	Remote Similarity	NPD4234	Approved
0.6406	Remote Similarity	NPD5237	Approved
0.6406	Remote Similarity	NPD5236	Approved
0.6406	Remote Similarity	NPD5239	Approved
0.6406	Remote Similarity	NPD1756	Approved
0.6406	Remote Similarity	NPD5235	Approved
0.6405	Remote Similarity	NPD3226	Approved
0.6405	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD2798	Approved
0.64	Remote Similarity	NPD1237	Approved
0.6379	Remote Similarity	NPD4793	Discontinued
0.6377	Remote Similarity	NPD2198	Approved
0.6377	Remote Similarity	NPD2199	Approved
0.6377	Remote Similarity	NPD1876	Approved
0.637	Remote Similarity	NPD4199	Phase 3
0.637	Remote Similarity	NPD5305	Approved
0.637	Remote Similarity	NPD1778	Approved
0.637	Remote Similarity	NPD5306	Approved
0.637	Remote Similarity	NPD4626	Approved
0.6364	Remote Similarity	NPD4307	Phase 2
0.6364	Remote Similarity	NPD6764	Approved
0.6364	Remote Similarity	NPD6765	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6357	Remote Similarity	NPD6650	Approved
0.6357	Remote Similarity	NPD6649	Approved
0.635	Remote Similarity	NPD4878	Approved
0.6347	Remote Similarity	NPD8407	Phase 2
0.6346	Remote Similarity	NPD7819	Suspended
0.6343	Remote Similarity	NPD9545	Approved
0.6338	Remote Similarity	NPD6798	Discontinued
0.6336	Remote Similarity	NPD1241	Discontinued
0.6333	Remote Similarity	NPD7748	Approved
0.6331	Remote Similarity	NPD1470	Approved
0.6324	Remote Similarity	NPD4879	Approved
0.6319	Remote Similarity	NPD4622	Approved
0.6319	Remote Similarity	NPD4618	Approved
0.6308	Remote Similarity	NPD6912	Phase 3
0.6304	Remote Similarity	NPD5327	Phase 3
0.6301	Remote Similarity	NPD3748	Approved
0.6299	Remote Similarity	NPD3134	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