NPASS Compound

Structure

NPC220560 OpenBabel07101718282D 27 29 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 -0.8660 -3.5000 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 3.4641 -0.0000 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 -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 24 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 18 1 0 0 0 0 7 23 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 25 1 0 0 0 0 10 6 1 6 0 0 0 10 11 1 0 0 0 0 10 26 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 1 0 0 0 12 13 1 0 0 0 0 12 20 1 6 0 0 0 13 15 1 0 0 0 0 13 21 1 1 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 26 1 0 0 0 0 15 27 1 6 0 0 0 16 25 1 0 0 0 0 16 27 1 1 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.12
Volume:	347.976
LogP:	-0.36
LogD:	-0.261
LogS:	-1.819
# Rotatable Bonds:	5
TPSA:	147.38
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	4.182
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.693
MDCK Permeability:	6.246279372135177e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.56
Human Intestinal Absorption (HIA):	0.835
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.746

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	23.654144287109375%
Volume Distribution (VD):	0.318
Pgp-substrate:	51.02903366088867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.738
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.277
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	1.993
Half-life (T1/2):	0.64

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.876
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.315
Carcinogencity:	0.895
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC220560

Natural Product ID:	NPC220560
*Common Name:**	(2R)-4,7-Dimethoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-1,4-Benzoxazin-3-One
IUPAC Name:	(2R)-4,7-dimethoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4-benzoxazin-3-one
Synonyms:
Standard InCHIKey:	UOASSFRPBORTCT-FFNJBFJXSA-N
Standard InCHI:	InChI=1S/C16H21NO10/c1-23-7-3-4-8-9(5-7)25-16(14(22)17(8)24-2)27-15-13(21)12(20)11(19)10(6-18)26-15/h3-5,10-13,15-16,18-21H,6H2,1-2H3/t10-,11-,12+,13-,15+,16-/m1/s1
SMILES:	COc1ccc2c(c1)O[C@@H](C(=O)N2OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487616
PubChem CID:	11079589
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	=	4.6	%	PMID[529659]

☑ 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 NPC220560 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	NPC290069
0.8418	Intermediate Similarity	NPC168750
0.8303	Intermediate Similarity	NPC112766
0.8144	Intermediate Similarity	NPC70549
0.7818	Intermediate Similarity	NPC473769
0.7805	Intermediate Similarity	NPC260601
0.7683	Intermediate Similarity	NPC476462
0.763	Intermediate Similarity	NPC19023
0.7474	Intermediate Similarity	NPC314948
0.7382	Intermediate Similarity	NPC478049
0.7186	Intermediate Similarity	NPC476475
0.7135	Intermediate Similarity	NPC320064
0.697	Remote Similarity	NPC473987
0.6931	Remote Similarity	NPC308392
0.6768	Remote Similarity	NPC25817
0.6707	Remote Similarity	NPC217854
0.6687	Remote Similarity	NPC298845
0.6683	Remote Similarity	NPC311357
0.6667	Remote Similarity	NPC471736
0.6667	Remote Similarity	NPC148124
0.6649	Remote Similarity	NPC262725
0.6647	Remote Similarity	NPC37074
0.662	Remote Similarity	NPC248903
0.662	Remote Similarity	NPC99724
0.6607	Remote Similarity	NPC247146
0.6606	Remote Similarity	NPC314702
0.6606	Remote Similarity	NPC315632
0.6587	Remote Similarity	NPC469622
0.6587	Remote Similarity	NPC189589
0.6574	Remote Similarity	NPC26928
0.6554	Remote Similarity	NPC161155
0.6554	Remote Similarity	NPC136951
0.6554	Remote Similarity	NPC97004
0.6543	Remote Similarity	NPC228907
0.6529	Remote Similarity	NPC60756
0.6524	Remote Similarity	NPC276195
0.6517	Remote Similarity	NPC472191
0.6517	Remote Similarity	NPC97282
0.6491	Remote Similarity	NPC287780
0.649	Remote Similarity	NPC153365
0.6486	Remote Similarity	NPC306366
0.6473	Remote Similarity	NPC257266
0.6471	Remote Similarity	NPC204179
0.6467	Remote Similarity	NPC221090
0.6461	Remote Similarity	NPC473874
0.6457	Remote Similarity	NPC36434
0.645	Remote Similarity	NPC469621
0.6446	Remote Similarity	NPC152722
0.6442	Remote Similarity	NPC257728
0.6433	Remote Similarity	NPC208769
0.642	Remote Similarity	NPC298821
0.6417	Remote Similarity	NPC139506
0.6417	Remote Similarity	NPC292143
0.6416	Remote Similarity	NPC60982
0.6411	Remote Similarity	NPC477160
0.6407	Remote Similarity	NPC192810
0.6391	Remote Similarity	NPC171533
0.6386	Remote Similarity	NPC57751
0.6384	Remote Similarity	NPC123761
0.6377	Remote Similarity	NPC470484
0.6364	Remote Similarity	NPC57105
0.6364	Remote Similarity	NPC124149
0.6343	Remote Similarity	NPC470236
0.6343	Remote Similarity	NPC238243
0.6343	Remote Similarity	NPC185778
0.634	Remote Similarity	NPC49353
0.634	Remote Similarity	NPC287152
0.6324	Remote Similarity	NPC315257
0.6322	Remote Similarity	NPC115022
0.6322	Remote Similarity	NPC294166
0.6313	Remote Similarity	NPC63628
0.6313	Remote Similarity	NPC178466
0.631	Remote Similarity	NPC231862
0.6307	Remote Similarity	NPC40664
0.6307	Remote Similarity	NPC138350
0.6307	Remote Similarity	NPC164857
0.6307	Remote Similarity	NPC3293
0.6307	Remote Similarity	NPC197723
0.6307	Remote Similarity	NPC165482
0.6296	Remote Similarity	NPC108826
0.6296	Remote Similarity	NPC142319
0.6286	Remote Similarity	NPC130496
0.6286	Remote Similarity	NPC188555
0.6279	Remote Similarity	NPC218003
0.6279	Remote Similarity	NPC295970
0.6271	Remote Similarity	NPC262328
0.6271	Remote Similarity	NPC87777
0.6264	Remote Similarity	NPC85799
0.6264	Remote Similarity	NPC165686
0.6264	Remote Similarity	NPC303422
0.6264	Remote Similarity	NPC297584
0.6264	Remote Similarity	NPC26080
0.6264	Remote Similarity	NPC162093
0.6263	Remote Similarity	NPC314861
0.6257	Remote Similarity	NPC140750
0.6237	Remote Similarity	NPC10221
0.6237	Remote Similarity	NPC140915
0.6237	Remote Similarity	NPC18249
0.6237	Remote Similarity	NPC305700
0.6237	Remote Similarity	NPC197741
0.6237	Remote Similarity	NPC187028
0.6235	Remote Similarity	NPC12308
0.6235	Remote Similarity	NPC264782
0.6229	Remote Similarity	NPC49074
0.6217	Remote Similarity	NPC472434
0.6215	Remote Similarity	NPC103409
0.6207	Remote Similarity	NPC475067
0.6207	Remote Similarity	NPC471825
0.6207	Remote Similarity	NPC79293
0.6207	Remote Similarity	NPC121376
0.6207	Remote Similarity	NPC279401
0.6201	Remote Similarity	NPC124300
0.6201	Remote Similarity	NPC210478
0.6199	Remote Similarity	NPC233559
0.6196	Remote Similarity	NPC114659
0.6196	Remote Similarity	NPC139699
0.6193	Remote Similarity	NPC116096
0.619	Remote Similarity	NPC310618
0.6182	Remote Similarity	NPC9248
0.6175	Remote Similarity	NPC87560
0.6175	Remote Similarity	NPC74320
0.6175	Remote Similarity	NPC195120
0.6175	Remote Similarity	NPC107120
0.6174	Remote Similarity	NPC291609
0.6171	Remote Similarity	NPC471513
0.6171	Remote Similarity	NPC473458
0.617	Remote Similarity	NPC301163
0.6169	Remote Similarity	NPC217294
0.6167	Remote Similarity	NPC273932
0.6167	Remote Similarity	NPC257095
0.6167	Remote Similarity	NPC215512
0.6167	Remote Similarity	NPC89686
0.6167	Remote Similarity	NPC108674
0.6167	Remote Similarity	NPC476442
0.6163	Remote Similarity	NPC198798
0.6162	Remote Similarity	NPC287294
0.6162	Remote Similarity	NPC314656
0.6158	Remote Similarity	NPC320259
0.6154	Remote Similarity	NPC476142
0.6149	Remote Similarity	NPC474491
0.6149	Remote Similarity	NPC470079
0.6149	Remote Similarity	NPC262606
0.6145	Remote Similarity	NPC98777
0.6145	Remote Similarity	NPC212770
0.6141	Remote Similarity	NPC87950
0.6141	Remote Similarity	NPC471764
0.614	Remote Similarity	NPC217903
0.6136	Remote Similarity	NPC215833
0.6136	Remote Similarity	NPC69513
0.6133	Remote Similarity	NPC5253
0.6133	Remote Similarity	NPC230718
0.6133	Remote Similarity	NPC49542
0.6133	Remote Similarity	NPC139976
0.6133	Remote Similarity	NPC84207
0.6133	Remote Similarity	NPC128337
0.6131	Remote Similarity	NPC469412
0.6131	Remote Similarity	NPC198734
0.6129	Remote Similarity	NPC477828
0.6127	Remote Similarity	NPC198487
0.6124	Remote Similarity	NPC104167
0.6124	Remote Similarity	NPC203230
0.6124	Remote Similarity	NPC242028
0.612	Remote Similarity	NPC85624
0.612	Remote Similarity	NPC226722
0.6119	Remote Similarity	NPC157983
0.6119	Remote Similarity	NPC118154
0.6116	Remote Similarity	NPC477397
0.6114	Remote Similarity	NPC329717
0.6111	Remote Similarity	NPC314025
0.6111	Remote Similarity	NPC195814
0.6102	Remote Similarity	NPC251981
0.6102	Remote Similarity	NPC13745
0.6102	Remote Similarity	NPC48863
0.6099	Remote Similarity	NPC116922
0.6095	Remote Similarity	NPC226712
0.6094	Remote Similarity	NPC477396
0.6093	Remote Similarity	NPC116178
0.6093	Remote Similarity	NPC203168
0.6091	Remote Similarity	NPC316161
0.6091	Remote Similarity	NPC118189
0.6089	Remote Similarity	NPC65530
0.6089	Remote Similarity	NPC59324
0.6089	Remote Similarity	NPC134260
0.6083	Remote Similarity	NPC288349
0.6082	Remote Similarity	NPC287429
0.608	Remote Similarity	NPC244554
0.608	Remote Similarity	NPC314213
0.608	Remote Similarity	NPC299144
0.6078	Remote Similarity	NPC477393
0.6077	Remote Similarity	NPC210192
0.6076	Remote Similarity	NPC472435
0.6075	Remote Similarity	NPC219664
0.6071	Remote Similarity	NPC469708
0.6071	Remote Similarity	NPC60589
0.607	Remote Similarity	NPC291759
0.6066	Remote Similarity	NPC177597
0.6066	Remote Similarity	NPC225445
0.6062	Remote Similarity	NPC470971
0.6058	Remote Similarity	NPC267414
0.6058	Remote Similarity	NPC220408

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 NPC220560 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
0.773	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2241	Approved
0.7283	Intermediate Similarity	NPD1678	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4201	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD822	Approved
0.7126	Intermediate Similarity	NPD8330	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5582	Discontinued
0.672	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4255	Phase 1
0.6683	Remote Similarity	NPD6034	Phase 2
0.6683	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1422	Approved
0.6631	Remote Similarity	NPD5847	Phase 1
0.6614	Remote Similarity	NPD5938	Phase 3
0.6579	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD789	Phase 2
0.655	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4428	Discontinued
0.6524	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4205	Phase 3
0.6481	Remote Similarity	NPD254	Approved
0.648	Remote Similarity	NPD2114	Discontinued
0.6477	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7263	Phase 2
0.6473	Remote Similarity	NPD7583	Approved
0.6467	Remote Similarity	NPD1769	Discontinued
0.6456	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD756	Suspended
0.6453	Remote Similarity	NPD1393	Approved
0.6442	Remote Similarity	NPD7585	Approved
0.6413	Remote Similarity	NPD1440	Discontinued
0.6406	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7126	Discontinued
0.6392	Remote Similarity	NPD6184	Discontinued
0.6387	Remote Similarity	NPD5858	Discontinued
0.6373	Remote Similarity	NPD1212	Approved
0.6368	Remote Similarity	NPD5150	Phase 2
0.6368	Remote Similarity	NPD7125	Discontinued
0.6364	Remote Similarity	NPD4587	Phase 3
0.6359	Remote Similarity	NPD2498	Approved
0.6321	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7584	Approved
0.6316	Remote Similarity	NPD6379	Discontinued
0.6313	Remote Similarity	NPD6298	Discontinued
0.6307	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7223	Discontinued
0.6273	Remote Similarity	NPD7224	Discontinued
0.6271	Remote Similarity	NPD3454	Phase 3
0.6263	Remote Similarity	NPD4586	Phase 3
0.6257	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7476	Discontinued
0.622	Remote Similarity	NPD6644	Discontinued
0.6201	Remote Similarity	NPD5719	Approved
0.62	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7256	Discontinued
0.6172	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4003	Phase 3
0.6158	Remote Similarity	NPD2200	Suspended
0.6158	Remote Similarity	NPD8031	Discontinued
0.6154	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.615	Remote Similarity	NPD3778	Approved
0.6138	Remote Similarity	NPD3558	Approved
0.6138	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD3556	Approved
0.6138	Remote Similarity	NPD6063	Approved
0.6138	Remote Similarity	NPD3557	Approved
0.6138	Remote Similarity	NPD3560	Approved
0.6127	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5640	Discontinued
0.6111	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4597	Approved
0.6111	Remote Similarity	NPD4598	Approved
0.6095	Remote Similarity	NPD6669	Phase 2
0.6095	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1091	Approved
0.6094	Remote Similarity	NPD5677	Discontinued
0.6094	Remote Similarity	NPD2904	Discontinued
0.6087	Remote Similarity	NPD3536	Discontinued
0.6085	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD2215	Approved
0.6082	Remote Similarity	NPD2216	Approved
0.6073	Remote Similarity	NPD3453	Discontinued
0.6071	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6550	Discontinued
0.6066	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD2843	Phase 2
0.6059	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD2845	Phase 2
0.6058	Remote Similarity	NPD1880	Phase 3
0.6056	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1012	Discontinued
0.605	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD7262	Phase 1
0.6041	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD4604	Approved
0.6039	Remote Similarity	NPD4605	Approved
0.6034	Remote Similarity	NPD3260	Discontinued
0.603	Remote Similarity	NPD6104	Discontinued
0.6029	Remote Similarity	NPD4496	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3627	Approved
0.6018	Remote Similarity	NPD7805	Phase 3
0.6012	Remote Similarity	NPD9723	Approved
0.6012	Remote Similarity	NPD850	Approved
0.6012	Remote Similarity	NPD848	Approved
0.6012	Remote Similarity	NPD849	Approved
0.6011	Remote Similarity	NPD3296	Phase 1
0.601	Remote Similarity	NPD4944	Phase 2
0.601	Remote Similarity	NPD6877	Discontinued
0.601	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.601	Remote Similarity	NPD1898	Discontinued
0.601	Remote Similarity	NPD4943	Phase 2
0.6	Remote Similarity	NPD2899	Discontinued
0.6	Remote Similarity	NPD2388	Discontinued
0.6	Remote Similarity	NPD4324	Phase 2
0.6	Remote Similarity	NPD4325	Phase 2
0.598	Remote Similarity	NPD6136	Phase 2
0.5979	Remote Similarity	NPD2249	Approved
0.5979	Remote Similarity	NPD2247	Approved
0.5979	Remote Similarity	NPD980	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6636	Phase 3
0.5969	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD7753	Approved
0.5967	Remote Similarity	NPD7752	Approved
0.5967	Remote Similarity	NPD3656	Approved
0.5965	Remote Similarity	NPD6625	Approved
0.5964	Remote Similarity	NPD3912	Discontinued
0.5961	Remote Similarity	NPD4515	Suspended
0.5958	Remote Similarity	NPD8461	Discontinued
0.5952	Remote Similarity	NPD7533	Approved
0.5952	Remote Similarity	NPD6519	Phase 2
0.5952	Remote Similarity	NPD7534	Approved
0.5951	Remote Similarity	NPD9376	Approved
0.595	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7212	Phase 2
0.5946	Remote Similarity	NPD7213	Phase 3
0.5941	Remote Similarity	NPD6045	Phase 3
0.5938	Remote Similarity	NPD1191	Discontinued
0.5935	Remote Similarity	NPD7043	Discontinued
0.5931	Remote Similarity	NPD7326	Phase 3
0.5931	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.593	Remote Similarity	NPD3885	Approved
0.593	Remote Similarity	NPD3580	Discontinued
0.5926	Remote Similarity	NPD3538	Suspended
0.5924	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD6604	Discontinued
0.5924	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD3391	Approved
0.5912	Remote Similarity	NPD1725	Approved
0.5911	Remote Similarity	NPD3153	Approved
0.5911	Remote Similarity	NPD3154	Approved
0.5909	Remote Similarity	NPD3369	Phase 2
0.5907	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6874	Approved
0.5902	Remote Similarity	NPD5112	Approved
0.5902	Remote Similarity	NPD5114	Approved
0.5902	Remote Similarity	NPD5113	Approved
0.5901	Remote Similarity	NPD3437	Discontinued
0.5899	Remote Similarity	NPD4206	Approved
0.5897	Remote Similarity	NPD3511	Discontinued
0.5897	Remote Similarity	NPD6457	Approved
0.5895	Remote Similarity	NPD6723	Discontinued
0.5892	Remote Similarity	NPD5295	Discontinued
0.589	Remote Similarity	NPD4679	Discontinued
0.589	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD3793	Phase 3
0.5877	Remote Similarity	NPD5542	Phase 2
0.5874	Remote Similarity	NPD5994	Discontinued
0.5873	Remote Similarity	NPD6357	Discontinued
0.5864	Remote Similarity	NPD4433	Discontinued
0.5862	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.586	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD2995	Approved
0.585	Remote Similarity	NPD795	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4675	Approved
0.5842	Remote Similarity	NPD4678	Approved
0.5841	Remote Similarity	NPD7891	Discontinued
0.5841	Remote Similarity	NPD7186	Phase 3
0.5833	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6283	Phase 2
0.5829	Remote Similarity	NPD7447	Phase 1
0.5821	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.582	Remote Similarity	NPD1653	Approved
0.5819	Remote Similarity	NPD1314	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD965	Approved
0.5813	Remote Similarity	NPD6338	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