NPASS Compound

Structure

NPC475058 OpenBabel07101718192D 40 42 0 0 1 0 0 0 0 0999 V2000 1.3837 3.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2894 3.8801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 0.1589 2.2071 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 0.4177 3.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 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 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 2 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 1.7321 -2.0000 0.0000 C 0 0 1 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 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 0.0000 -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 3 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7899 1.8827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 27 1 0 0 0 0 10 38 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 29 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 15 39 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 31 1 1 0 0 0 18 19 1 0 0 0 0 18 32 1 6 0 0 0 19 21 1 0 0 0 0 19 33 1 1 0 0 0 20 34 2 0 0 0 0 20 38 1 0 0 0 0 21 39 1 0 0 0 0 21 40 1 6 0 0 0 22 25 1 0 0 0 0 22 27 1 0 0 0 0 22 35 2 0 0 0 0 23 26 1 0 0 0 0 23 27 1 0 0 0 0 23 36 2 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 40 1 0 0 0 0 27 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.23
Volume:	548.333
LogP:	2.291
LogD:	1.368
LogS:	-3.085
# Rotatable Bonds:	8
TPSA:	220.51
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.132
Synthetic Accessibility Score:	4.703
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.002
MDCK Permeability:	1.1748412362067029e-05
Pgp-inhibitor:	0.17
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.651
20% Bioavailability (F20%):	0.61
30% Bioavailability (F30%):	0.696

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	86.12892150878906%
Volume Distribution (VD):	0.636
Pgp-substrate:	10.12484359741211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.231
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	1.342
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.537
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.603
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.843
Respiratory Toxicity:	0.745

Download Data

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

Natural Product: NPC475058

Natural Product ID:	NPC475058
*Common Name:**	Gallomyrtucommulone B
IUPAC Name:	[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[4-hydroxy-2,2,6,6-tetramethyl-4-(2-methylpropyl)-3,5-dioxocyclohexyl]oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	VKHZSJBPCYWANI-XXZDZOCTSA-N
Standard InCHI:	InChI=1S/C27H38O13/c1-11(2)9-27(37)22(35)25(3,4)24(26(5,6)23(27)36)40-21-19(33)18(32)17(31)15(39-21)10-38-20(34)12-7-13(28)16(30)14(29)8-12/h7-8,11,15,17-19,21,24,28-33,37H,9-10H2,1-6H3/t15-,17-,18+,19-,21+,24?,27?/m1/s1
SMILES:	CC(CC1(O)C(=O)C(C)(C)C(C(C1=O)(C)C)O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494859
PubChem CID:	11664177
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO4570	Myrtus communis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499325]
NPO4570	Myrtus communis	Species	Myrtaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22276775]
NPO4570	Myrtus communis	Species	Myrtaceae	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[545958]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[545958]

☑ 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 NPC475058 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	390
0.1-0.2	1543
0.2-0.3	3206
0.3-0.4	6610
0.4-0.5	9830
0.5-0.6	7289
0.6-0.7	6457
0.7-0.8	6486
0.8-0.85	848
0.85-0.9	33
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC476017
0.9006	High Similarity	NPC102367
0.9	High Similarity	NPC469418
0.8889	High Similarity	NPC172920
0.8889	High Similarity	NPC156624
0.878	High Similarity	NPC4747
0.878	High Similarity	NPC104275
0.878	High Similarity	NPC49173
0.8779	High Similarity	NPC80360
0.8779	High Similarity	NPC260300
0.8772	High Similarity	NPC469354
0.8758	High Similarity	NPC140151
0.875	High Similarity	NPC92117
0.8728	High Similarity	NPC195114
0.869	High Similarity	NPC475738
0.8688	High Similarity	NPC120621
0.8688	High Similarity	NPC248257
0.8623	High Similarity	NPC477627
0.8616	High Similarity	NPC108455
0.8613	High Similarity	NPC233994
0.8613	High Similarity	NPC211532
0.8588	High Similarity	NPC116745
0.858	High Similarity	NPC306343
0.8571	High Similarity	NPC43123
0.8555	High Similarity	NPC477848
0.8554	High Similarity	NPC472860
0.8553	High Similarity	NPC229036
0.8553	High Similarity	NPC114242
0.8553	High Similarity	NPC50221
0.8547	High Similarity	NPC476772
0.8547	High Similarity	NPC190003
0.8547	High Similarity	NPC175107
0.8538	High Similarity	NPC328321
0.8538	High Similarity	NPC138927
0.8537	High Similarity	NPC44260
0.8537	High Similarity	NPC61152
0.8537	High Similarity	NPC16024
0.8537	High Similarity	NPC205037
0.8537	High Similarity	NPC3746
0.8529	High Similarity	NPC469419
0.8519	High Similarity	NPC75945
0.8519	High Similarity	NPC42464
0.8506	High Similarity	NPC472384
0.8506	High Similarity	NPC198324
0.8506	High Similarity	NPC472382
0.8506	High Similarity	NPC472380
0.8506	High Similarity	NPC472385
0.8506	High Similarity	NPC268533
0.8497	Intermediate Similarity	NPC4390
0.8488	Intermediate Similarity	NPC224462
0.8488	Intermediate Similarity	NPC212748
0.8488	Intermediate Similarity	NPC244776
0.8488	Intermediate Similarity	NPC155763
0.8488	Intermediate Similarity	NPC116864
0.8488	Intermediate Similarity	NPC235260
0.8488	Intermediate Similarity	NPC20505
0.8476	Intermediate Similarity	NPC227485
0.8476	Intermediate Similarity	NPC221249
0.8471	Intermediate Similarity	NPC165720
0.8471	Intermediate Similarity	NPC88243
0.8466	Intermediate Similarity	NPC170203
0.8462	Intermediate Similarity	NPC41009
0.8462	Intermediate Similarity	NPC291957
0.8462	Intermediate Similarity	NPC300537
0.8462	Intermediate Similarity	NPC14030
0.8462	Intermediate Similarity	NPC127782
0.8457	Intermediate Similarity	NPC293626
0.8457	Intermediate Similarity	NPC258044
0.8457	Intermediate Similarity	NPC35167
0.8457	Intermediate Similarity	NPC217387
0.8457	Intermediate Similarity	NPC168584
0.8457	Intermediate Similarity	NPC196127
0.8457	Intermediate Similarity	NPC267680
0.8452	Intermediate Similarity	NPC166277
0.8452	Intermediate Similarity	NPC119125
0.8452	Intermediate Similarity	NPC203020
0.8452	Intermediate Similarity	NPC239966
0.8448	Intermediate Similarity	NPC108202
0.8448	Intermediate Similarity	NPC135277
0.8448	Intermediate Similarity	NPC264735
0.8448	Intermediate Similarity	NPC171706
0.8448	Intermediate Similarity	NPC237435
0.8448	Intermediate Similarity	NPC101191
0.8448	Intermediate Similarity	NPC115760
0.8448	Intermediate Similarity	NPC210094
0.8448	Intermediate Similarity	NPC469438
0.8448	Intermediate Similarity	NPC49344
0.8448	Intermediate Similarity	NPC43211
0.8443	Intermediate Similarity	NPC474010
0.8443	Intermediate Similarity	NPC1913
0.8443	Intermediate Similarity	NPC135222
0.8439	Intermediate Similarity	NPC153755
0.8439	Intermediate Similarity	NPC476405
0.8439	Intermediate Similarity	NPC205076
0.8439	Intermediate Similarity	NPC472386
0.8439	Intermediate Similarity	NPC172807
0.8439	Intermediate Similarity	NPC211594
0.8439	Intermediate Similarity	NPC307518
0.8439	Intermediate Similarity	NPC254540
0.8439	Intermediate Similarity	NPC48773
0.8439	Intermediate Similarity	NPC117260
0.8438	Intermediate Similarity	NPC121573
0.8438	Intermediate Similarity	NPC22176
0.8438	Intermediate Similarity	NPC190587
0.8438	Intermediate Similarity	NPC226738
0.843	Intermediate Similarity	NPC229687
0.843	Intermediate Similarity	NPC52382
0.843	Intermediate Similarity	NPC183036
0.843	Intermediate Similarity	NPC476771
0.843	Intermediate Similarity	NPC270578
0.8421	Intermediate Similarity	NPC13481
0.8421	Intermediate Similarity	NPC207575
0.8421	Intermediate Similarity	NPC277174
0.8421	Intermediate Similarity	NPC73855
0.8421	Intermediate Similarity	NPC328940
0.8421	Intermediate Similarity	NPC113968
0.8421	Intermediate Similarity	NPC135599
0.8418	Intermediate Similarity	NPC313452
0.8418	Intermediate Similarity	NPC470447
0.8418	Intermediate Similarity	NPC470446
0.8418	Intermediate Similarity	NPC470445
0.8418	Intermediate Similarity	NPC36138
0.8418	Intermediate Similarity	NPC470449
0.8412	Intermediate Similarity	NPC94777
0.8412	Intermediate Similarity	NPC470898
0.8412	Intermediate Similarity	NPC88043
0.8402	Intermediate Similarity	NPC311803
0.8402	Intermediate Similarity	NPC25389
0.8402	Intermediate Similarity	NPC266365
0.8402	Intermediate Similarity	NPC472859
0.84	Intermediate Similarity	NPC144097
0.84	Intermediate Similarity	NPC475054
0.84	Intermediate Similarity	NPC257714
0.84	Intermediate Similarity	NPC61904
0.84	Intermediate Similarity	NPC89127
0.84	Intermediate Similarity	NPC471669
0.8393	Intermediate Similarity	NPC287872
0.8393	Intermediate Similarity	NPC160780
0.8393	Intermediate Similarity	NPC74319
0.8393	Intermediate Similarity	NPC289811
0.8391	Intermediate Similarity	NPC21666
0.8391	Intermediate Similarity	NPC42773
0.8391	Intermediate Similarity	NPC24043
0.8391	Intermediate Similarity	NPC101026
0.8391	Intermediate Similarity	NPC45522
0.8391	Intermediate Similarity	NPC175230
0.8391	Intermediate Similarity	NPC172033
0.8391	Intermediate Similarity	NPC88560
0.8391	Intermediate Similarity	NPC169977
0.8382	Intermediate Similarity	NPC21190
0.8382	Intermediate Similarity	NPC72249
0.8382	Intermediate Similarity	NPC22195
0.8382	Intermediate Similarity	NPC206123
0.8382	Intermediate Similarity	NPC84265
0.8382	Intermediate Similarity	NPC282987
0.8382	Intermediate Similarity	NPC245014
0.8382	Intermediate Similarity	NPC105511
0.8382	Intermediate Similarity	NPC44558
0.8382	Intermediate Similarity	NPC183357
0.8382	Intermediate Similarity	NPC470272
0.8382	Intermediate Similarity	NPC474434
0.8382	Intermediate Similarity	NPC34287
0.8382	Intermediate Similarity	NPC149011
0.8382	Intermediate Similarity	NPC471416
0.8382	Intermediate Similarity	NPC204937
0.838	Intermediate Similarity	NPC475360
0.8373	Intermediate Similarity	NPC281703
0.8373	Intermediate Similarity	NPC125487
0.8372	Intermediate Similarity	NPC229729
0.8372	Intermediate Similarity	NPC265530
0.8372	Intermediate Similarity	NPC52550
0.8372	Intermediate Similarity	NPC107009
0.8372	Intermediate Similarity	NPC48640
0.8372	Intermediate Similarity	NPC226304
0.8372	Intermediate Similarity	NPC92565
0.8372	Intermediate Similarity	NPC325555
0.8372	Intermediate Similarity	NPC317489
0.8372	Intermediate Similarity	NPC160156
0.8372	Intermediate Similarity	NPC45400
0.8372	Intermediate Similarity	NPC223424
0.8372	Intermediate Similarity	NPC149244
0.8372	Intermediate Similarity	NPC84362
0.8372	Intermediate Similarity	NPC173637
0.8372	Intermediate Similarity	NPC477502
0.8372	Intermediate Similarity	NPC127546
0.8371	Intermediate Similarity	NPC470455
0.8371	Intermediate Similarity	NPC470416
0.8371	Intermediate Similarity	NPC470451
0.8371	Intermediate Similarity	NPC148710
0.8363	Intermediate Similarity	NPC471788
0.8363	Intermediate Similarity	NPC277205
0.8363	Intermediate Similarity	NPC55786
0.8363	Intermediate Similarity	NPC240431
0.8363	Intermediate Similarity	NPC19388
0.8363	Intermediate Similarity	NPC180586
0.8362	Intermediate Similarity	NPC188217
0.8362	Intermediate Similarity	NPC315221
0.8354	Intermediate Similarity	NPC12006
0.8353	Intermediate Similarity	NPC473043
0.8353	Intermediate Similarity	NPC148273

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 NPC475058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	942
0.2-0.3	1979
0.3-0.4	2711
0.4-0.5	1913
0.5-0.6	919
0.6-0.7	234
0.7-0.8	104
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8448	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD7251	Discontinued
0.8276	Intermediate Similarity	NPD7074	Phase 3
0.8266	Intermediate Similarity	NPD3818	Discontinued
0.8229	Intermediate Similarity	NPD6797	Phase 2
0.8218	Intermediate Similarity	NPD7054	Approved
0.8171	Intermediate Similarity	NPD7472	Approved
0.8136	Intermediate Similarity	NPD7808	Phase 3
0.8059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6190	Approved
0.8012	Intermediate Similarity	NPD7075	Discontinued
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6166	Phase 2
0.7941	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD230	Phase 1
0.7921	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD1934	Approved
0.7853	Intermediate Similarity	NPD7228	Approved
0.7836	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3817	Phase 2
0.7791	Intermediate Similarity	NPD7266	Discontinued
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.7765	Intermediate Similarity	NPD4380	Phase 2
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.7746	Intermediate Similarity	NPD3882	Suspended
0.7733	Intermediate Similarity	NPD2801	Approved
0.7697	Intermediate Similarity	NPD7473	Discontinued
0.7674	Intermediate Similarity	NPD6801	Discontinued
0.7674	Intermediate Similarity	NPD37	Approved
0.7663	Intermediate Similarity	NPD8150	Discontinued
0.7663	Intermediate Similarity	NPD8434	Phase 2
0.7644	Intermediate Similarity	NPD4965	Approved
0.7644	Intermediate Similarity	NPD4966	Approved
0.7644	Intermediate Similarity	NPD4967	Phase 2
0.7588	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5402	Approved
0.7565	Intermediate Similarity	NPD7435	Discontinued
0.7544	Intermediate Similarity	NPD1653	Approved
0.7529	Intermediate Similarity	NPD7819	Suspended
0.7529	Intermediate Similarity	NPD1512	Approved
0.7528	Intermediate Similarity	NPD6232	Discontinued
0.7526	Intermediate Similarity	NPD8320	Phase 1
0.7526	Intermediate Similarity	NPD8319	Approved
0.7514	Intermediate Similarity	NPD5494	Approved
0.7514	Intermediate Similarity	NPD7411	Suspended
0.7514	Intermediate Similarity	NPD5844	Phase 1
0.7513	Intermediate Similarity	NPD6535	Approved
0.7513	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7486	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6599	Discontinued
0.7429	Intermediate Similarity	NPD1465	Phase 2
0.7423	Intermediate Similarity	NPD943	Approved
0.7412	Intermediate Similarity	NPD6799	Approved
0.7412	Intermediate Similarity	NPD1511	Approved
0.7409	Intermediate Similarity	NPD6780	Approved
0.7409	Intermediate Similarity	NPD6778	Approved
0.7409	Intermediate Similarity	NPD6776	Approved
0.7409	Intermediate Similarity	NPD6782	Approved
0.7409	Intermediate Similarity	NPD6781	Approved
0.7409	Intermediate Similarity	NPD6777	Approved
0.7409	Intermediate Similarity	NPD6779	Approved
0.7405	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD8313	Approved
0.7391	Intermediate Similarity	NPD8368	Discontinued
0.7391	Intermediate Similarity	NPD7240	Approved
0.7374	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3751	Discontinued
0.7337	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD7696	Phase 3
0.7296	Intermediate Similarity	NPD7697	Approved
0.7296	Intermediate Similarity	NPD7698	Approved
0.7293	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5403	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD8407	Phase 2
0.7268	Intermediate Similarity	NPD7799	Discontinued
0.7259	Intermediate Similarity	NPD7870	Phase 2
0.7259	Intermediate Similarity	NPD7871	Phase 2
0.7253	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD3787	Discontinued
0.7236	Intermediate Similarity	NPD7701	Phase 2
0.7235	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4628	Phase 3
0.7235	Intermediate Similarity	NPD8166	Discontinued
0.7235	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD9269	Phase 2
0.7228	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1549	Phase 2
0.7214	Intermediate Similarity	NPD7801	Approved
0.7209	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7182	Intermediate Similarity	NPD1247	Approved
0.7168	Intermediate Similarity	NPD2533	Approved
0.7168	Intermediate Similarity	NPD2532	Approved
0.7168	Intermediate Similarity	NPD2534	Approved
0.7168	Intermediate Similarity	NPD5401	Approved
0.716	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7126	Intermediate Similarity	NPD6651	Approved
0.712	Intermediate Similarity	NPD8360	Approved
0.712	Intermediate Similarity	NPD8361	Approved
0.7108	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2935	Discontinued
0.7095	Intermediate Similarity	NPD5353	Approved
0.7092	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6959	Discontinued
0.7076	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD919	Approved
0.7071	Intermediate Similarity	NPD6823	Phase 2
0.7069	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7783	Phase 2
0.7044	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8435	Approved
0.7015	Intermediate Similarity	NPD7584	Approved
0.7011	Intermediate Similarity	NPD3926	Phase 2
0.701	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6213	Phase 3
0.701	Intermediate Similarity	NPD6212	Phase 3
0.7006	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.6986	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD9268	Approved
0.6978	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2800	Approved
0.6965	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7768	Phase 2
0.695	Remote Similarity	NPD7680	Approved
0.6944	Remote Similarity	NPD8455	Phase 2
0.6941	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3027	Phase 3
0.6923	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD1607	Approved
0.6919	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3226	Approved
0.6905	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1613	Approved
0.6904	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8127	Discontinued
0.6897	Remote Similarity	NPD7585	Approved
0.6884	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7236	Approved
0.6847	Remote Similarity	NPD7583	Approved
0.6839	Remote Similarity	NPD3750	Approved
0.6818	Remote Similarity	NPD7390	Discontinued
0.6813	Remote Similarity	NPD9545	Approved
0.6794	Remote Similarity	NPD8404	Phase 2
0.6789	Remote Similarity	NPD5953	Discontinued
0.6786	Remote Similarity	NPD3764	Approved
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7930	Approved
0.6774	Remote Similarity	NPD5710	Approved
0.6774	Remote Similarity	NPD5711	Approved
0.6772	Remote Similarity	NPD7286	Phase 2
0.6765	Remote Similarity	NPD1933	Approved
0.6765	Remote Similarity	NPD447	Suspended
0.676	Remote Similarity	NPD7239	Suspended
0.6753	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5242	Approved
0.6734	Remote Similarity	NPD8485	Approved
0.6722	Remote Similarity	NPD3455	Phase 2
0.6707	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD9494	Approved
0.6705	Remote Similarity	NPD1551	Phase 2
0.6704	Remote Similarity	NPD920	Approved
0.6686	Remote Similarity	NPD6674	Discontinued
0.6686	Remote Similarity	NPD7097	Phase 1
0.6685	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5760	Phase 2
0.6651	Remote Similarity	NPD4665	Approved
0.6651	Remote Similarity	NPD4111	Phase 1
0.6648	Remote Similarity	NPD6386	Approved
0.6648	Remote Similarity	NPD6385	Approved
0.6648	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2799	Discontinued
0.6614	Remote Similarity	NPD2403	Approved
0.6593	Remote Similarity	NPD7028	Phase 2
0.6592	Remote Similarity	NPD642	Clinical (unspecified phase)

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