NPASS Compound

Structure

NPC195814 OpenBabel07101718232D 38 39 0 0 1 0 0 0 0 0999 V2000 18.1865 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.0526 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 12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4545 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.3205 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 18.1865 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 4.3301 -1.5000 0.0000 C 0 0 0 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 6.9282 -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 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 6.0622 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 23 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 25 2 0 0 0 0 18 20 2 0 0 0 0 18 25 1 0 0 0 0 19 26 2 0 0 0 0 20 26 1 0 0 0 0 21 22 2 0 0 0 0 21 25 1 0 0 0 0 22 32 1 0 0 0 0 24 3 1 6 0 0 0 24 28 1 0 0 0 0 24 37 1 0 0 0 0 26 38 1 0 0 0 0 27 32 2 3 0 0 0 27 33 1 0 0 0 0 28 29 1 0 0 0 0 28 34 1 1 0 0 0 29 30 1 0 0 0 0 29 35 1 6 0 0 0 30 31 1 0 0 0 0 30 36 1 6 0 0 0 31 37 1 0 0 0 0 31 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	531.36
Volume:	575.538
LogP:	6.957
LogD:	4.737
LogS:	-4.935
# Rotatable Bonds:	18
TPSA:	108.58
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.138
Synthetic Accessibility Score:	4.235
Fsp3:	0.677
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.887
MDCK Permeability:	4.341010935604572e-05
Pgp-inhibitor:	0.786
Pgp-substrate:	0.797
Human Intestinal Absorption (HIA):	0.166
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	97.6148452758789%
Volume Distribution (VD):	1.978
Pgp-substrate:	1.2232087850570679%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.407
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.321
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.557
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.368
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	3.396
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.075
AMES Toxicity:	0.375
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.959
Carcinogencity:	0.352
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.634

Download Data

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

Natural Product: NPC195814

Natural Product ID:	NPC195814
*Common Name:**	Myxotyroside A
IUPAC Name:	(Z)-15-methyl-N-[(Z)-2-[4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphenyl]ethenyl]hexadec-2-enamide
Synonyms:
Standard InCHIKey:	OEUGFCRAXXFNAR-SRUKPRNUSA-N
Standard InCHI:	InChI=1S/C31H49NO6/c1-23(2)15-13-11-9-7-5-4-6-8-10-12-14-16-27(33)32-22-21-25-17-19-26(20-18-25)38-31-30(36)29(35)28(34)24(3)37-31/h14,16-24,28-31,34-36H,4-13,15H2,1-3H3,(H,32,33)/b16-14-,22-21-/t24-,28-,29+,30+,31-/m0/s1
SMILES:	CC(C)CCCCCCCCCCC/C=CC(=N/C=Cc1ccc(cc1)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563475
PubChem CID:	25210012
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO33083	myxococcus sp.	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18803421]
NPO33083	myxococcus sp.	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19113894]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7000.0	nM	PMID[531315]

☑ 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 NPC195814 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	192
0.1-0.2	1135
0.2-0.3	3503
0.3-0.4	11394
0.4-0.5	8013
0.5-0.6	10647
0.6-0.7	6701
0.7-0.8	1060
0.8-0.85	42
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8759	High Similarity	NPC139699
0.8759	High Similarity	NPC114659
0.8732	High Similarity	NPC178466
0.8732	High Similarity	NPC63628
0.8529	High Similarity	NPC198798
0.8523	High Similarity	NPC18249
0.8523	High Similarity	NPC10221
0.8523	High Similarity	NPC187028
0.8523	High Similarity	NPC140915
0.8523	High Similarity	NPC305700
0.8523	High Similarity	NPC197741
0.8485	Intermediate Similarity	NPC60589
0.8485	Intermediate Similarity	NPC469708
0.8451	Intermediate Similarity	NPC36434
0.8421	Intermediate Similarity	NPC469412
0.8421	Intermediate Similarity	NPC198734
0.8421	Intermediate Similarity	NPC269242
0.8392	Intermediate Similarity	NPC298821
0.8333	Intermediate Similarity	NPC123761
0.8309	Intermediate Similarity	NPC287429
0.8296	Intermediate Similarity	NPC476142
0.8288	Intermediate Similarity	NPC97004
0.8288	Intermediate Similarity	NPC136951
0.8288	Intermediate Similarity	NPC161155
0.8267	Intermediate Similarity	NPC474560
0.8231	Intermediate Similarity	NPC97282
0.8156	Intermediate Similarity	NPC471953
0.8143	Intermediate Similarity	NPC26653
0.8143	Intermediate Similarity	NPC248355
0.8143	Intermediate Similarity	NPC270849
0.8134	Intermediate Similarity	NPC256369
0.8108	Intermediate Similarity	NPC313414
0.8088	Intermediate Similarity	NPC226712
0.8085	Intermediate Similarity	NPC80600
0.8085	Intermediate Similarity	NPC262606
0.8085	Intermediate Similarity	NPC472024
0.8071	Intermediate Similarity	NPC302378
0.8015	Intermediate Similarity	NPC83279
0.8014	Intermediate Similarity	NPC97326
0.8014	Intermediate Similarity	NPC295970
0.8014	Intermediate Similarity	NPC166040
0.7986	Intermediate Similarity	NPC470510
0.7986	Intermediate Similarity	NPC187194
0.7986	Intermediate Similarity	NPC476411
0.7971	Intermediate Similarity	NPC212176
0.7947	Intermediate Similarity	NPC471032
0.7947	Intermediate Similarity	NPC470935
0.7945	Intermediate Similarity	NPC470413
0.7945	Intermediate Similarity	NPC262328
0.7945	Intermediate Similarity	NPC138738
0.7945	Intermediate Similarity	NPC87777
0.7931	Intermediate Similarity	NPC79957
0.7919	Intermediate Similarity	NPC185307
0.7919	Intermediate Similarity	NPC470950
0.7917	Intermediate Similarity	NPC115022
0.7917	Intermediate Similarity	NPC49074
0.7917	Intermediate Similarity	NPC294166
0.7917	Intermediate Similarity	NPC25821
0.7914	Intermediate Similarity	NPC95733
0.7914	Intermediate Similarity	NPC62101
0.791	Intermediate Similarity	NPC148055
0.791	Intermediate Similarity	NPC175771
0.7902	Intermediate Similarity	NPC65942
0.7902	Intermediate Similarity	NPC248307
0.7902	Intermediate Similarity	NPC9912
0.7902	Intermediate Similarity	NPC121376
0.7895	Intermediate Similarity	NPC313193
0.7887	Intermediate Similarity	NPC307110
0.7877	Intermediate Similarity	NPC40664
0.7877	Intermediate Similarity	NPC197723
0.7877	Intermediate Similarity	NPC3293
0.7877	Intermediate Similarity	NPC52277
0.7877	Intermediate Similarity	NPC475628
0.7877	Intermediate Similarity	NPC199459
0.7877	Intermediate Similarity	NPC177035
0.7877	Intermediate Similarity	NPC164857
0.7877	Intermediate Similarity	NPC138350
0.7877	Intermediate Similarity	NPC165482
0.7872	Intermediate Similarity	NPC291449
0.7872	Intermediate Similarity	NPC41331
0.7867	Intermediate Similarity	NPC129417
0.7867	Intermediate Similarity	NPC283995
0.7867	Intermediate Similarity	NPC470235
0.7862	Intermediate Similarity	NPC48863
0.7862	Intermediate Similarity	NPC251981
0.7862	Intermediate Similarity	NPC35731
0.7862	Intermediate Similarity	NPC13745
0.7857	Intermediate Similarity	NPC12308
0.7852	Intermediate Similarity	NPC476356
0.7852	Intermediate Similarity	NPC246947
0.7847	Intermediate Similarity	NPC303422
0.7847	Intermediate Similarity	NPC85799
0.7847	Intermediate Similarity	NPC162093
0.7847	Intermediate Similarity	NPC26080
0.7847	Intermediate Similarity	NPC165686
0.7838	Intermediate Similarity	NPC106944
0.7836	Intermediate Similarity	NPC303370
0.7832	Intermediate Similarity	NPC474491
0.7826	Intermediate Similarity	NPC469686
0.7823	Intermediate Similarity	NPC304152
0.7817	Intermediate Similarity	NPC246974
0.7817	Intermediate Similarity	NPC147247
0.7815	Intermediate Similarity	NPC43508
0.7815	Intermediate Similarity	NPC279298
0.7815	Intermediate Similarity	NPC22150
0.7815	Intermediate Similarity	NPC38041
0.7815	Intermediate Similarity	NPC476301
0.781	Intermediate Similarity	NPC282409
0.781	Intermediate Similarity	NPC263835
0.781	Intermediate Similarity	NPC469702
0.7808	Intermediate Similarity	NPC470236
0.7808	Intermediate Similarity	NPC238243
0.7803	Intermediate Similarity	NPC166837
0.7801	Intermediate Similarity	NPC156944
0.78	Intermediate Similarity	NPC46092
0.78	Intermediate Similarity	NPC116922
0.7793	Intermediate Similarity	NPC69513
0.7793	Intermediate Similarity	NPC215833
0.7785	Intermediate Similarity	NPC472711
0.7785	Intermediate Similarity	NPC210192
0.7785	Intermediate Similarity	NPC108674
0.7778	Intermediate Similarity	NPC274732
0.7778	Intermediate Similarity	NPC475067
0.7763	Intermediate Similarity	NPC112861
0.7762	Intermediate Similarity	NPC218003
0.7761	Intermediate Similarity	NPC157338
0.7755	Intermediate Similarity	NPC37468
0.7754	Intermediate Similarity	NPC469703
0.7754	Intermediate Similarity	NPC160854
0.7754	Intermediate Similarity	NPC201402
0.7754	Intermediate Similarity	NPC476448
0.7754	Intermediate Similarity	NPC469704
0.7754	Intermediate Similarity	NPC469548
0.7754	Intermediate Similarity	NPC476445
0.7748	Intermediate Similarity	NPC471667
0.7748	Intermediate Similarity	NPC471063
0.7748	Intermediate Similarity	NPC177597
0.7748	Intermediate Similarity	NPC79429
0.7748	Intermediate Similarity	NPC217635
0.7748	Intermediate Similarity	NPC225445
0.7746	Intermediate Similarity	NPC99798
0.7746	Intermediate Similarity	NPC157740
0.774	Intermediate Similarity	NPC470881
0.774	Intermediate Similarity	NPC264956
0.774	Intermediate Similarity	NPC188555
0.774	Intermediate Similarity	NPC471029
0.774	Intermediate Similarity	NPC130496
0.7733	Intermediate Similarity	NPC128337
0.7733	Intermediate Similarity	NPC230718
0.7733	Intermediate Similarity	NPC84207
0.7733	Intermediate Similarity	NPC60249
0.7733	Intermediate Similarity	NPC469559
0.7733	Intermediate Similarity	NPC189115
0.7733	Intermediate Similarity	NPC5253
0.7733	Intermediate Similarity	NPC139976
0.7733	Intermediate Similarity	NPC49542
0.773	Intermediate Similarity	NPC170583
0.773	Intermediate Similarity	NPC71105
0.773	Intermediate Similarity	NPC152186
0.773	Intermediate Similarity	NPC207541
0.773	Intermediate Similarity	NPC29477
0.773	Intermediate Similarity	NPC246133
0.773	Intermediate Similarity	NPC182147
0.7724	Intermediate Similarity	NPC252833
0.7724	Intermediate Similarity	NPC299144
0.7714	Intermediate Similarity	NPC211218
0.7712	Intermediate Similarity	NPC31325
0.7712	Intermediate Similarity	NPC224674
0.7712	Intermediate Similarity	NPC213074
0.7712	Intermediate Similarity	NPC275284
0.7712	Intermediate Similarity	NPC114505
0.7712	Intermediate Similarity	NPC15956
0.7712	Intermediate Similarity	NPC39657
0.7712	Intermediate Similarity	NPC97240
0.7712	Intermediate Similarity	NPC193473
0.7703	Intermediate Similarity	NPC134260
0.7703	Intermediate Similarity	NPC124149
0.7698	Intermediate Similarity	NPC55608
0.7697	Intermediate Similarity	NPC475096
0.7697	Intermediate Similarity	NPC18979
0.7692	Intermediate Similarity	NPC146540
0.7692	Intermediate Similarity	NPC40377
0.7687	Intermediate Similarity	NPC101624
0.7687	Intermediate Similarity	NPC55040
0.7687	Intermediate Similarity	NPC184938
0.7682	Intermediate Similarity	NPC473044
0.7682	Intermediate Similarity	NPC477898
0.7682	Intermediate Similarity	NPC113680
0.7682	Intermediate Similarity	NPC469367
0.7682	Intermediate Similarity	NPC278961
0.7676	Intermediate Similarity	NPC251466
0.7671	Intermediate Similarity	NPC215037
0.7671	Intermediate Similarity	NPC6836
0.7671	Intermediate Similarity	NPC132895
0.7667	Intermediate Similarity	NPC76871
0.7667	Intermediate Similarity	NPC273932
0.7667	Intermediate Similarity	NPC257095
0.7667	Intermediate Similarity	NPC469661
0.7667	Intermediate Similarity	NPC89686
0.766	Intermediate Similarity	NPC300955

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 NPC195814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	607
0.2-0.3	1010
0.3-0.4	2618
0.4-0.5	2529
0.5-0.6	1543
0.6-0.7	661
0.7-0.8	38
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8102	Intermediate Similarity	NPD3685	Discontinued
0.8088	Intermediate Similarity	NPD1091	Approved
0.7755	Intermediate Similarity	NPD4108	Discontinued
0.7483	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD7843	Approved
0.7468	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2684	Approved
0.7417	Intermediate Similarity	NPD1375	Discontinued
0.7397	Intermediate Similarity	NPD3180	Approved
0.7397	Intermediate Similarity	NPD3179	Approved
0.7379	Intermediate Similarity	NPD4993	Discontinued
0.7375	Intermediate Similarity	NPD5773	Approved
0.7375	Intermediate Similarity	NPD5772	Approved
0.7372	Intermediate Similarity	NPD7526	Approved
0.7372	Intermediate Similarity	NPD52	Approved
0.7372	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD821	Approved
0.7347	Intermediate Similarity	NPD1048	Approved
0.7346	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6674	Discontinued
0.7319	Intermediate Similarity	NPD7157	Approved
0.7297	Intermediate Similarity	NPD1423	Approved
0.729	Intermediate Similarity	NPD5756	Phase 2
0.729	Intermediate Similarity	NPD5058	Phase 3
0.7278	Intermediate Similarity	NPD7007	Discovery
0.725	Intermediate Similarity	NPD6072	Discontinued
0.7237	Intermediate Similarity	NPD2161	Phase 2
0.7222	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6582	Phase 2
0.7222	Intermediate Similarity	NPD6583	Phase 3
0.7205	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD776	Approved
0.7197	Intermediate Similarity	NPD4123	Phase 3
0.7184	Intermediate Similarity	NPD6842	Approved
0.7184	Intermediate Similarity	NPD6841	Approved
0.7184	Intermediate Similarity	NPD6843	Phase 3
0.7181	Intermediate Similarity	NPD7477	Discontinued
0.7162	Intermediate Similarity	NPD3165	Approved
0.7162	Intermediate Similarity	NPD3166	Approved
0.7162	Intermediate Similarity	NPD3164	Approved
0.7162	Intermediate Similarity	NPD3167	Approved
0.7162	Intermediate Similarity	NPD3027	Phase 3
0.7161	Intermediate Similarity	NPD6331	Phase 2
0.7153	Intermediate Similarity	NPD2231	Phase 2
0.7153	Intermediate Similarity	NPD2235	Phase 2
0.7152	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2238	Phase 2
0.7133	Intermediate Similarity	NPD1613	Approved
0.7123	Intermediate Similarity	NPD1818	Approved
0.7123	Intermediate Similarity	NPD1819	Approved
0.7123	Intermediate Similarity	NPD1820	Approved
0.7123	Intermediate Similarity	NPD1817	Approved
0.7115	Intermediate Similarity	NPD2677	Approved
0.7111	Intermediate Similarity	NPD290	Approved
0.7107	Intermediate Similarity	NPD2122	Discontinued
0.7105	Intermediate Similarity	NPD4536	Approved
0.7105	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7097	Phase 1
0.7105	Intermediate Similarity	NPD4538	Approved
0.7095	Intermediate Similarity	NPD4908	Phase 1
0.7089	Intermediate Similarity	NPD3985	Discontinued
0.7089	Intermediate Similarity	NPD3536	Discontinued
0.7089	Intermediate Similarity	NPD6419	Discontinued
0.7081	Intermediate Similarity	NPD4675	Approved
0.7081	Intermediate Similarity	NPD4678	Approved
0.7078	Intermediate Similarity	NPD7266	Discontinued
0.7075	Intermediate Similarity	NPD6584	Phase 3
0.707	Intermediate Similarity	NPD6667	Approved
0.707	Intermediate Similarity	NPD6666	Approved
0.7055	Intermediate Similarity	NPD8651	Approved
0.7055	Intermediate Similarity	NPD8455	Phase 2
0.7051	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3054	Approved
0.7039	Intermediate Similarity	NPD2157	Approved
0.7039	Intermediate Similarity	NPD3052	Approved
0.7032	Intermediate Similarity	NPD2424	Discontinued
0.7032	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2861	Phase 2
0.7027	Intermediate Similarity	NPD1712	Approved
0.7025	Intermediate Similarity	NPD7213	Phase 3
0.7025	Intermediate Similarity	NPD7212	Phase 2
0.7021	Intermediate Similarity	NPD3596	Phase 2
0.7012	Intermediate Similarity	NPD2415	Discontinued
0.7	Intermediate Similarity	NPD3144	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3145	Approved
0.6993	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1357	Approved
0.6981	Remote Similarity	NPD7447	Phase 1
0.6968	Remote Similarity	NPD3656	Approved
0.6966	Remote Similarity	NPD1610	Phase 2
0.6966	Remote Similarity	NPD3705	Approved
0.6962	Remote Similarity	NPD3122	Phase 3
0.6957	Remote Similarity	NPD1653	Approved
0.6957	Remote Similarity	NPD6669	Phase 2
0.6957	Remote Similarity	NPD3686	Approved
0.6957	Remote Similarity	NPD3687	Approved
0.6954	Remote Similarity	NPD840	Approved
0.6954	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD839	Approved
0.6954	Remote Similarity	NPD2674	Phase 3
0.6954	Remote Similarity	NPD3162	Approved
0.6954	Remote Similarity	NPD3163	Approved
0.6954	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2978	Approved
0.6951	Remote Similarity	NPD2977	Approved
0.6951	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7972	Discontinued
0.6948	Remote Similarity	NPD5960	Phase 3
0.6948	Remote Similarity	NPD5588	Approved
0.6944	Remote Similarity	NPD2667	Approved
0.6944	Remote Similarity	NPD2668	Approved
0.6939	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7153	Discontinued
0.6923	Remote Similarity	NPD6581	Approved
0.6923	Remote Similarity	NPD6580	Approved
0.6908	Remote Similarity	NPD1558	Phase 1
0.6908	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2239	Approved
0.6903	Remote Similarity	NPD2240	Approved
0.6903	Remote Similarity	NPD6032	Approved
0.6903	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1794	Approved
0.6887	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD556	Approved
0.6883	Remote Similarity	NPD7119	Phase 2
0.6879	Remote Similarity	NPD4236	Phase 3
0.6879	Remote Similarity	NPD1652	Phase 2
0.6879	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4237	Approved
0.6879	Remote Similarity	NPD5289	Phase 2
0.6871	Remote Similarity	NPD1669	Approved
0.6867	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5124	Phase 1
0.6863	Remote Similarity	NPD6355	Discontinued
0.6863	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5295	Discontinued
0.6842	Remote Similarity	NPD7265	Discontinued
0.6842	Remote Similarity	NPD6233	Phase 2
0.6839	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4628	Phase 3
0.6831	Remote Similarity	NPD2557	Approved
0.6831	Remote Similarity	NPD6671	Approved
0.6829	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6516	Phase 2
0.6828	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5846	Approved
0.6826	Remote Similarity	NPD5604	Discontinued
0.6821	Remote Similarity	NPD5163	Phase 2
0.6818	Remote Similarity	NPD6653	Approved
0.6815	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1774	Approved
0.681	Remote Similarity	NPD4005	Discontinued
0.6806	Remote Similarity	NPD1548	Phase 1
0.6803	Remote Similarity	NPD2233	Approved
0.6803	Remote Similarity	NPD2230	Approved
0.6803	Remote Similarity	NPD2232	Approved
0.68	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4060	Phase 1
0.6792	Remote Similarity	NPD2219	Phase 1
0.6779	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4098	Discontinued
0.6776	Remote Similarity	NPD6798	Discontinued
0.6776	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4162	Approved
0.6772	Remote Similarity	NPD3060	Approved
0.6772	Remote Similarity	NPD5061	Approved
0.6772	Remote Similarity	NPD5177	Phase 3
0.6772	Remote Similarity	NPD5062	Approved
0.677	Remote Similarity	NPD4739	Approved
0.6768	Remote Similarity	NPD6502	Phase 2
0.6765	Remote Similarity	NPD7315	Approved
0.6763	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6382	Discontinued
0.6755	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5735	Approved
0.6752	Remote Similarity	NPD5762	Approved
0.6752	Remote Similarity	NPD5763	Approved
0.675	Remote Similarity	NPD6815	Approved
0.6748	Remote Similarity	NPD4003	Phase 3
0.6733	Remote Similarity	NPD3691	Phase 2
0.6733	Remote Similarity	NPD3690	Phase 2
0.6733	Remote Similarity	NPD558	Phase 2
0.673	Remote Similarity	NPD7466	Approved
0.6728	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6677	Suspended
0.6724	Remote Similarity	NPD7074	Phase 3
0.6712	Remote Similarity	NPD5126	Approved
0.6712	Remote Similarity	NPD5125	Phase 3
0.6711	Remote Similarity	NPD6179	Discontinued
0.6708	Remote Similarity	NPD6087	Phase 1
0.6707	Remote Similarity	NPD2563	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