NPASS Compound

Structure

NPC290069 OpenBabel07101718202D 26 28 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 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 1.7321 -2.0000 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 -3.0000 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 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 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 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -0.0000 -2.0000 0.0000 N 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 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -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 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 17 1 0 0 0 0 6 23 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 24 1 0 0 0 0 9 5 1 6 0 0 0 9 10 1 0 0 0 0 9 25 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 1 0 0 0 11 12 1 0 0 0 0 11 19 1 6 0 0 0 12 14 1 0 0 0 0 12 20 1 1 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 13 21 2 0 0 0 0 14 25 1 0 0 0 0 14 26 1 6 0 0 0 15 24 1 0 0 0 0 15 26 1 1 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	373.1
Volume:	330.68
LogP:	-0.55
LogD:	-0.838
LogS:	-1.053
# Rotatable Bonds:	4
TPSA:	158.38
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	4.14
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.044
MDCK Permeability:	6.54104514978826e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.764
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209
Plasma Protein Binding (PPB):	18.45271873474121%
Volume Distribution (VD):	0.312
Pgp-substrate:	58.301788330078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.358
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.288
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.493
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.228
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	2.236
Half-life (T1/2):	0.679

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.824
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.374
Carcinogencity:	0.761
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC290069

Natural Product ID:	NPC290069
*Common Name:**	(2R)-4-Hydroxy-7-Methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-1,4-Benzoxazin-3-One
IUPAC Name:	(2R)-4-hydroxy-7-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4-benzoxazin-3-one
Synonyms:
Standard InCHIKey:	WTGXAWKVZMQEDA-XFWGRBSCSA-N
Standard InCHI:	InChI=1S/C15H19NO10/c1-23-6-2-3-7-8(4-6)24-15(13(21)16(7)22)26-14-12(20)11(19)10(18)9(5-17)25-14/h2-4,9-12,14-15,17-20,22H,5H2,1H3/t9-,10-,11+,12-,14+,15-/m1/s1
SMILES:	COc1ccc2c(c1)O[C@@H](C(=O)N2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519905
PubChem CID:	441563
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:0002207] O-glycosyl compounds

*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
NPO33369.1	coix lachryma-jobi	Under-species	n.a.	n.a.	Roots	n.a.	n.a.	PMID[2453615]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	3.0	%	PMID[544779]

☑ 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 NPC290069 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	329
0.1-0.2	2556
0.2-0.3	10993
0.3-0.4	8444
0.4-0.5	13471
0.5-0.6	6624
0.6-0.7	268
0.7-0.8	7
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC220560
0.8471	Intermediate Similarity	NPC168750
0.8354	Intermediate Similarity	NPC112766
0.8193	Intermediate Similarity	NPC70549
0.7866	Intermediate Similarity	NPC473769
0.7853	Intermediate Similarity	NPC260601
0.773	Intermediate Similarity	NPC476462
0.7674	Intermediate Similarity	NPC19023
0.7421	Intermediate Similarity	NPC314948
0.733	Intermediate Similarity	NPC478049
0.7229	Intermediate Similarity	NPC476475
0.7079	Intermediate Similarity	NPC320064
0.7012	Intermediate Similarity	NPC473987
0.6881	Remote Similarity	NPC308392
0.6707	Remote Similarity	NPC25817
0.6646	Remote Similarity	NPC217854
0.6646	Remote Similarity	NPC315632
0.6634	Remote Similarity	NPC311357
0.6627	Remote Similarity	NPC298845
0.662	Remote Similarity	NPC148124
0.6618	Remote Similarity	NPC471736
0.6598	Remote Similarity	NPC262725
0.6587	Remote Similarity	NPC37074
0.6574	Remote Similarity	NPC248903
0.6573	Remote Similarity	NPC99724
0.6564	Remote Similarity	NPC276195
0.6561	Remote Similarity	NPC314702
0.6548	Remote Similarity	NPC247146
0.6528	Remote Similarity	NPC26928
0.6527	Remote Similarity	NPC469622
0.6527	Remote Similarity	NPC189589
0.6522	Remote Similarity	NPC306366
0.6506	Remote Similarity	NPC221090
0.6497	Remote Similarity	NPC97004
0.6497	Remote Similarity	NPC136951
0.6497	Remote Similarity	NPC473874
0.6497	Remote Similarity	NPC161155
0.6494	Remote Similarity	NPC36434
0.6485	Remote Similarity	NPC152722
0.6481	Remote Similarity	NPC228907
0.6471	Remote Similarity	NPC60756
0.6468	Remote Similarity	NPC472191
0.6461	Remote Similarity	NPC97282
0.6457	Remote Similarity	NPC298821
0.6446	Remote Similarity	NPC192810
0.6442	Remote Similarity	NPC153365
0.6433	Remote Similarity	NPC287780
0.6425	Remote Similarity	NPC257266
0.642	Remote Similarity	NPC123761
0.6417	Remote Similarity	NPC204179
0.6398	Remote Similarity	NPC57105
0.6394	Remote Similarity	NPC257728
0.6391	Remote Similarity	NPC469621
0.6374	Remote Similarity	NPC208769
0.6373	Remote Similarity	NPC287152
0.6364	Remote Similarity	NPC477160
0.6364	Remote Similarity	NPC292143
0.6364	Remote Similarity	NPC139506
0.6358	Remote Similarity	NPC60982
0.6344	Remote Similarity	NPC231862
0.6335	Remote Similarity	NPC142319
0.6331	Remote Similarity	NPC171533
0.6329	Remote Similarity	NPC470484
0.6325	Remote Similarity	NPC57751
0.6307	Remote Similarity	NPC124149
0.6301	Remote Similarity	NPC297584
0.6289	Remote Similarity	NPC49353
0.6286	Remote Similarity	NPC185778
0.6286	Remote Similarity	NPC470236
0.6286	Remote Similarity	NPC238243
0.6273	Remote Similarity	NPC264782
0.6272	Remote Similarity	NPC12308
0.627	Remote Similarity	NPC315257
0.6264	Remote Similarity	NPC294166
0.6264	Remote Similarity	NPC115022
0.6257	Remote Similarity	NPC63628
0.6257	Remote Similarity	NPC178466
0.625	Remote Similarity	NPC103409
0.625	Remote Similarity	NPC3293
0.625	Remote Similarity	NPC40664
0.625	Remote Similarity	NPC197723
0.625	Remote Similarity	NPC164857
0.625	Remote Similarity	NPC165482
0.625	Remote Similarity	NPC138350
0.625	Remote Similarity	NPC108826
0.6238	Remote Similarity	NPC279401
0.6238	Remote Similarity	NPC79293
0.6229	Remote Similarity	NPC188555
0.6229	Remote Similarity	NPC130496
0.6221	Remote Similarity	NPC218003
0.6221	Remote Similarity	NPC295970
0.622	Remote Similarity	NPC9248
0.6215	Remote Similarity	NPC262328
0.6215	Remote Similarity	NPC87777
0.6211	Remote Similarity	NPC314861
0.6207	Remote Similarity	NPC85799
0.6207	Remote Similarity	NPC26080
0.6207	Remote Similarity	NPC162093
0.6207	Remote Similarity	NPC165686
0.6207	Remote Similarity	NPC303422
0.6199	Remote Similarity	NPC198798
0.6199	Remote Similarity	NPC140750
0.6183	Remote Similarity	NPC305700
0.6183	Remote Similarity	NPC187028
0.6183	Remote Similarity	NPC140915
0.6183	Remote Similarity	NPC18249
0.6183	Remote Similarity	NPC10221
0.6183	Remote Similarity	NPC197741
0.6174	Remote Similarity	NPC472434
0.6171	Remote Similarity	NPC49074
0.6158	Remote Similarity	NPC471825
0.6157	Remote Similarity	NPC124300
0.6149	Remote Similarity	NPC121376
0.6149	Remote Similarity	NPC475067
0.6147	Remote Similarity	NPC310618
0.6145	Remote Similarity	NPC210478
0.6142	Remote Similarity	NPC116096
0.6141	Remote Similarity	NPC114659
0.6141	Remote Similarity	NPC139699
0.614	Remote Similarity	NPC233559
0.6131	Remote Similarity	NPC226712
0.613	Remote Similarity	NPC291609
0.6129	Remote Similarity	NPC195120
0.6129	Remote Similarity	NPC87560
0.6126	Remote Similarity	NPC473458
0.6126	Remote Similarity	NPC471513
0.6122	Remote Similarity	NPC316161
0.612	Remote Similarity	NPC107120
0.612	Remote Similarity	NPC74320
0.6119	Remote Similarity	NPC217294
0.6117	Remote Similarity	NPC301163
0.6114	Remote Similarity	NPC299144
0.6111	Remote Similarity	NPC108674
0.6111	Remote Similarity	NPC257095
0.6111	Remote Similarity	NPC215512
0.6111	Remote Similarity	NPC314656
0.6111	Remote Similarity	NPC273932
0.6111	Remote Similarity	NPC288349
0.6111	Remote Similarity	NPC89686
0.6111	Remote Similarity	NPC476442
0.6108	Remote Similarity	NPC287294
0.6108	Remote Similarity	NPC469708
0.6108	Remote Similarity	NPC60589
0.6102	Remote Similarity	NPC320259
0.6095	Remote Similarity	NPC476142
0.6094	Remote Similarity	NPC470971
0.6093	Remote Similarity	NPC217903
0.6092	Remote Similarity	NPC474491
0.6092	Remote Similarity	NPC262606
0.6092	Remote Similarity	NPC470079
0.6089	Remote Similarity	NPC98777
0.6089	Remote Similarity	NPC212770
0.6087	Remote Similarity	NPC471764
0.6087	Remote Similarity	NPC87950
0.6087	Remote Similarity	NPC220408
0.6083	Remote Similarity	NPC477828
0.608	Remote Similarity	NPC215833
0.608	Remote Similarity	NPC69513
0.6077	Remote Similarity	NPC128337
0.6077	Remote Similarity	NPC49542
0.6077	Remote Similarity	NPC139976
0.6077	Remote Similarity	NPC84207
0.6077	Remote Similarity	NPC5253
0.6077	Remote Similarity	NPC230718
0.6073	Remote Similarity	NPC118154
0.6073	Remote Similarity	NPC70172
0.6073	Remote Similarity	NPC157983
0.6071	Remote Similarity	NPC469412
0.6071	Remote Similarity	NPC198734
0.6071	Remote Similarity	NPC269242
0.6071	Remote Similarity	NPC477397
0.6069	Remote Similarity	NPC198487
0.6069	Remote Similarity	NPC146540
0.6067	Remote Similarity	NPC203230
0.6067	Remote Similarity	NPC242028
0.6067	Remote Similarity	NPC104167
0.6066	Remote Similarity	NPC226722
0.6066	Remote Similarity	NPC85624
0.6062	Remote Similarity	NPC329717
0.6061	Remote Similarity	NPC314025
0.6057	Remote Similarity	NPC208022
0.6056	Remote Similarity	NPC195814
0.6052	Remote Similarity	NPC477396
0.6047	Remote Similarity	NPC116178
0.6047	Remote Similarity	NPC203168
0.6045	Remote Similarity	NPC13745
0.6045	Remote Similarity	NPC48863
0.6045	Remote Similarity	NPC251981
0.6045	Remote Similarity	NPC118189
0.6044	Remote Similarity	NPC116922
0.6034	Remote Similarity	NPC472435
0.6034	Remote Similarity	NPC59324
0.6034	Remote Similarity	NPC477393
0.6034	Remote Similarity	NPC65530
0.6034	Remote Similarity	NPC134260
0.603	Remote Similarity	NPC244554
0.603	Remote Similarity	NPC314213
0.6028	Remote Similarity	NPC219664
0.6023	Remote Similarity	NPC287429
0.6022	Remote Similarity	NPC210192

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 NPC290069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	724
0.2-0.3	1288
0.3-0.4	2729
0.4-0.5	2894
0.5-0.6	1221
0.6-0.7	93
0.7-0.8	6
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
0.7778	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2241	Approved
0.7326	Intermediate Similarity	NPD1678	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD822	Approved
0.72	Intermediate Similarity	NPD4201	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8330	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD5582	Discontinued
0.6686	Remote Similarity	NPD1422	Approved
0.6667	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6034	Phase 2
0.663	Remote Similarity	NPD4255	Phase 1
0.6628	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD789	Phase 2
0.6597	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD5847	Phase 1
0.6561	Remote Similarity	NPD5938	Phase 3
0.6526	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD254	Approved
0.6503	Remote Similarity	NPD1769	Discontinued
0.65	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4428	Discontinued
0.6491	Remote Similarity	NPD1393	Approved
0.6491	Remote Similarity	NPD756	Suspended
0.6471	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD4205	Phase 3
0.6448	Remote Similarity	NPD1440	Discontinued
0.6425	Remote Similarity	NPD7263	Phase 2
0.6425	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2114	Discontinued
0.6425	Remote Similarity	NPD7583	Approved
0.6408	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1212	Approved
0.6394	Remote Similarity	NPD7585	Approved
0.6354	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7126	Discontinued
0.6343	Remote Similarity	NPD204	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6184	Discontinued
0.6335	Remote Similarity	NPD5858	Discontinued
0.6318	Remote Similarity	NPD5150	Phase 2
0.6318	Remote Similarity	NPD7125	Discontinued
0.6313	Remote Similarity	NPD4587	Phase 3
0.6311	Remote Similarity	NPD2498	Approved
0.6269	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD7584	Approved
0.6267	Remote Similarity	NPD6298	Discontinued
0.6263	Remote Similarity	NPD6379	Discontinued
0.625	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD7223	Discontinued
0.6227	Remote Similarity	NPD7224	Discontinued
0.6215	Remote Similarity	NPD3454	Phase 3
0.6212	Remote Similarity	NPD4586	Phase 3
0.6203	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7476	Discontinued
0.6172	Remote Similarity	NPD6644	Discontinued
0.615	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5719	Approved
0.6131	Remote Similarity	NPD1091	Approved
0.6127	Remote Similarity	NPD7256	Discontinued
0.6124	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD4003	Phase 3
0.6105	Remote Similarity	NPD8031	Discontinued
0.6103	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD2200	Suspended
0.6099	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD3778	Approved
0.6085	Remote Similarity	NPD3556	Approved
0.6085	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD3558	Approved
0.6085	Remote Similarity	NPD6063	Approved
0.6085	Remote Similarity	NPD1012	Discontinued
0.6085	Remote Similarity	NPD3560	Approved
0.6085	Remote Similarity	NPD3557	Approved
0.6081	Remote Similarity	NPD5640	Discontinued
0.6069	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4598	Approved
0.6056	Remote Similarity	NPD4597	Approved
0.6048	Remote Similarity	NPD6669	Phase 2
0.6048	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD850	Approved
0.6047	Remote Similarity	NPD849	Approved
0.6047	Remote Similarity	NPD9723	Approved
0.6047	Remote Similarity	NPD848	Approved
0.6042	Remote Similarity	NPD2904	Discontinued
0.6042	Remote Similarity	NPD5677	Discontinued
0.6033	Remote Similarity	NPD3536	Discontinued
0.6032	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD2215	Approved
0.6031	Remote Similarity	NPD2216	Approved
0.6021	Remote Similarity	NPD3453	Discontinued
0.602	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6550	Discontinued
0.6011	Remote Similarity	NPD980	Clinical (unspecified phase)
0.601	Remote Similarity	NPD2843	Phase 2
0.601	Remote Similarity	NPD1880	Phase 3
0.601	Remote Similarity	NPD2845	Phase 2
0.601	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7262	Phase 1
0.6	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4604	Approved
0.599	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4605	Approved
0.5988	Remote Similarity	NPD9376	Approved
0.5981	Remote Similarity	NPD4496	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6104	Discontinued
0.5978	Remote Similarity	NPD3260	Discontinued
0.5973	Remote Similarity	NPD7805	Phase 3
0.5969	Remote Similarity	NPD1191	Discontinued
0.5968	Remote Similarity	NPD3627	Approved
0.5962	Remote Similarity	NPD6877	Discontinued
0.5961	Remote Similarity	NPD1898	Discontinued
0.596	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD4943	Phase 2
0.5959	Remote Similarity	NPD4944	Phase 2
0.5957	Remote Similarity	NPD3296	Phase 1
0.5955	Remote Similarity	NPD2899	Discontinued
0.5951	Remote Similarity	NPD4324	Phase 2
0.5951	Remote Similarity	NPD4325	Phase 2
0.5949	Remote Similarity	NPD2388	Discontinued
0.5944	Remote Similarity	NPD1725	Approved
0.5931	Remote Similarity	NPD6136	Phase 2
0.5928	Remote Similarity	NPD2249	Approved
0.5928	Remote Similarity	NPD2247	Approved
0.5922	Remote Similarity	NPD6636	Phase 3
0.5921	Remote Similarity	NPD6625	Approved
0.5919	Remote Similarity	NPD3912	Discontinued
0.5918	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD8461	Discontinued
0.5912	Remote Similarity	NPD7753	Approved
0.5912	Remote Similarity	NPD3656	Approved
0.5912	Remote Similarity	NPD7752	Approved
0.5911	Remote Similarity	NPD4515	Suspended
0.5905	Remote Similarity	NPD6519	Phase 2
0.59	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7534	Approved
0.5893	Remote Similarity	NPD7533	Approved
0.5892	Remote Similarity	NPD7212	Phase 2
0.5892	Remote Similarity	NPD7213	Phase 3
0.5891	Remote Similarity	NPD6045	Phase 3
0.5888	Remote Similarity	NPD7043	Discontinued
0.5882	Remote Similarity	NPD7326	Phase 3
0.5882	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD3885	Approved
0.5879	Remote Similarity	NPD795	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD3580	Discontinued
0.5877	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6604	Discontinued
0.5873	Remote Similarity	NPD3538	Suspended
0.587	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3153	Approved
0.5862	Remote Similarity	NPD3154	Approved
0.5859	Remote Similarity	NPD3369	Phase 2
0.5857	Remote Similarity	NPD6874	Approved
0.5856	Remote Similarity	NPD3391	Approved
0.5856	Remote Similarity	NPD3437	Discontinued
0.5855	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5113	Approved
0.5854	Remote Similarity	NPD5114	Approved
0.5854	Remote Similarity	NPD5112	Approved
0.5853	Remote Similarity	NPD4206	Approved
0.5852	Remote Similarity	NPD6723	Discontinued
0.5852	Remote Similarity	NPD1314	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD1653	Approved
0.5847	Remote Similarity	NPD965	Approved
0.5846	Remote Similarity	NPD6457	Approved
0.5846	Remote Similarity	NPD3511	Discontinued
0.5845	Remote Similarity	NPD4679	Discontinued
0.5845	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD5295	Discontinued
0.5829	Remote Similarity	NPD3793	Phase 3
0.5829	Remote Similarity	NPD5542	Phase 2
0.5825	Remote Similarity	NPD5994	Discontinued
0.582	Remote Similarity	NPD6357	Discontinued
0.5813	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD4433	Discontinued
0.5811	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD2995	Approved
0.5796	Remote Similarity	NPD7186	Phase 3
0.5795	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7891	Discontinued
0.5792	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4675	Approved
0.5789	Remote Similarity	NPD4678	Approved
0.5787	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6283	Phase 2
0.5775	Remote Similarity	NPD7447	Phase 1
0.5771	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD8067	Phase 3

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