NPASS Compound

Structure

NPC70549 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 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 3.4641 0.0000 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 -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 2 2 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 22 1 0 0 0 0 8 4 1 6 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 1 0 0 0 10 11 1 0 0 0 0 10 19 1 6 0 0 0 11 13 1 0 0 0 0 11 20 1 1 0 0 0 12 14 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 23 1 0 0 0 0 13 24 1 6 0 0 0 14 22 1 0 0 0 0 14 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	310.324
LogP:	1.576
LogD:	1.073
LogS:	-2.544
# Rotatable Bonds:	2
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.548
Synthetic Accessibility Score:	4.662
Fsp3:	0.706
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:	-4.654
MDCK Permeability:	7.392820407403633e-05
Pgp-inhibitor:	0.198
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.136
30% Bioavailability (F30%):	0.169

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.73
Plasma Protein Binding (PPB):	57.73892593383789%
Volume Distribution (VD):	1.283
Pgp-substrate:	40.9710807800293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.732
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.662
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	5.464
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.767
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.08
Carcinogencity:	0.172
Eye Corrosion:	0.199
Eye Irritation:	0.362
Respiratory Toxicity:	0.095

Download Data

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

Natural Product: NPC70549

Natural Product ID:	NPC70549
*Common Name:**	(2R)-7-Hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-4H-1,4-Benzoxazin-3-One
IUPAC Name:	(2R)-7-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-1,4-benzoxazin-3-one
Synonyms:
Standard InCHIKey:	VUFDXOACUHDTLI-TWTZXXGESA-N
Standard InCHI:	InChI=1S/C14H17NO9/c16-4-8-9(18)10(19)11(20)13(23-8)24-14-12(21)15-6-2-1-5(17)3-7(6)22-14/h1-3,8-11,13-14,16-20H,4H2,(H,15,21)/t8-,9-,10+,11-,13+,14-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2Oc3cc(O)ccc3N=C2O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485821
PubChem CID:	44559797
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	=	2.0	%	PMID[519050]

☑ 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 NPC70549 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	354
0.1-0.2	2758
0.2-0.3	10942
0.3-0.4	7898
0.4-0.5	11717
0.5-0.6	8298
0.6-0.7	693
0.7-0.8	30
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC112766
0.9247	High Similarity	NPC473769
0.8414	Intermediate Similarity	NPC473987
0.8193	Intermediate Similarity	NPC290069
0.8144	Intermediate Similarity	NPC220560
0.8025	Intermediate Similarity	NPC19023
0.8	Intermediate Similarity	NPC315632
0.7722	Intermediate Similarity	NPC473874
0.7547	Intermediate Similarity	NPC260601
0.744	Intermediate Similarity	NPC57105
0.7421	Intermediate Similarity	NPC476462
0.7381	Intermediate Similarity	NPC306366
0.7278	Intermediate Similarity	NPC231862
0.7273	Intermediate Similarity	NPC316161
0.7251	Intermediate Similarity	NPC204179
0.7243	Intermediate Similarity	NPC478049
0.7197	Intermediate Similarity	NPC297584
0.7151	Intermediate Similarity	NPC314948
0.7143	Intermediate Similarity	NPC298845
0.7124	Intermediate Similarity	NPC221090
0.7123	Intermediate Similarity	NPC264782
0.7117	Intermediate Similarity	NPC178466
0.7117	Intermediate Similarity	NPC63628
0.7105	Intermediate Similarity	NPC152722
0.7097	Intermediate Similarity	NPC37074
0.7081	Intermediate Similarity	NPC36434
0.7075	Intermediate Similarity	NPC142319
0.7059	Intermediate Similarity	NPC192810
0.7037	Intermediate Similarity	NPC298821
0.7032	Intermediate Similarity	NPC189589
0.7032	Intermediate Similarity	NPC469622
0.7025	Intermediate Similarity	NPC208022
0.7013	Intermediate Similarity	NPC25817
0.7011	Intermediate Similarity	NPC314861
0.7	Intermediate Similarity	NPC10875
0.7	Intermediate Similarity	NPC10730
0.6994	Remote Similarity	NPC123761
0.6974	Remote Similarity	NPC276195
0.6962	Remote Similarity	NPC60756
0.6951	Remote Similarity	NPC168750
0.6948	Remote Similarity	NPC217854
0.6943	Remote Similarity	NPC471736
0.6933	Remote Similarity	NPC314113
0.6933	Remote Similarity	NPC9248
0.6928	Remote Similarity	NPC57751
0.6918	Remote Similarity	NPC287780
0.6899	Remote Similarity	NPC218003
0.689	Remote Similarity	NPC195814
0.6887	Remote Similarity	NPC228907
0.6879	Remote Similarity	NPC469621
0.6875	Remote Similarity	NPC165686
0.6875	Remote Similarity	NPC26080
0.6875	Remote Similarity	NPC303422
0.6875	Remote Similarity	NPC85799
0.6872	Remote Similarity	NPC168153
0.6872	Remote Similarity	NPC308392
0.6867	Remote Similarity	NPC161155
0.6867	Remote Similarity	NPC136951
0.6867	Remote Similarity	NPC97004
0.6864	Remote Similarity	NPC114659
0.6864	Remote Similarity	NPC139699
0.6859	Remote Similarity	NPC12308
0.6855	Remote Similarity	NPC208769
0.6855	Remote Similarity	NPC313466
0.6835	Remote Similarity	NPC247146
0.6832	Remote Similarity	NPC294166
0.6832	Remote Similarity	NPC115022
0.6832	Remote Similarity	NPC60982
0.6826	Remote Similarity	NPC97282
0.6813	Remote Similarity	NPC121376
0.6793	Remote Similarity	NPC313886
0.679	Remote Similarity	NPC130496
0.679	Remote Similarity	NPC188555
0.6748	Remote Similarity	NPC238243
0.6735	Remote Similarity	NPC255721
0.6721	Remote Similarity	NPC314025
0.6712	Remote Similarity	NPC76327
0.671	Remote Similarity	NPC226712
0.6709	Remote Similarity	NPC171533
0.6707	Remote Similarity	NPC3293
0.6707	Remote Similarity	NPC197723
0.6707	Remote Similarity	NPC165482
0.6707	Remote Similarity	NPC242028
0.6707	Remote Similarity	NPC138350
0.6707	Remote Similarity	NPC40664
0.6707	Remote Similarity	NPC203230
0.6705	Remote Similarity	NPC197741
0.6705	Remote Similarity	NPC10221
0.6705	Remote Similarity	NPC18249
0.6705	Remote Similarity	NPC305700
0.6705	Remote Similarity	NPC140915
0.6705	Remote Similarity	NPC187028
0.6701	Remote Similarity	NPC311357
0.6686	Remote Similarity	NPC235628
0.6667	Remote Similarity	NPC140750
0.6667	Remote Similarity	NPC59324
0.6667	Remote Similarity	NPC87777
0.6667	Remote Similarity	NPC262328
0.6667	Remote Similarity	NPC225381
0.6667	Remote Similarity	NPC65530
0.6667	Remote Similarity	NPC124149
0.6648	Remote Similarity	NPC315631
0.6648	Remote Similarity	NPC198741
0.6646	Remote Similarity	NPC262606
0.6646	Remote Similarity	NPC185778
0.6645	Remote Similarity	NPC269242
0.6629	Remote Similarity	NPC127362
0.6628	Remote Similarity	NPC184161
0.6627	Remote Similarity	NPC212770
0.6627	Remote Similarity	NPC98777
0.6626	Remote Similarity	NPC49074
0.6625	Remote Similarity	NPC40377
0.6606	Remote Similarity	NPC103409
0.6606	Remote Similarity	NPC164857
0.6605	Remote Similarity	NPC475067
0.6604	Remote Similarity	NPC233559
0.6595	Remote Similarity	NPC314656
0.6595	Remote Similarity	NPC314213
0.6582	Remote Similarity	NPC159101
0.6581	Remote Similarity	NPC60589
0.6581	Remote Similarity	NPC469708
0.6566	Remote Similarity	NPC134260
0.6564	Remote Similarity	NPC162093
0.6564	Remote Similarity	NPC299144
0.6562	Remote Similarity	NPC198798
0.6559	Remote Similarity	NPC315913
0.6548	Remote Similarity	NPC273932
0.6548	Remote Similarity	NPC89686
0.6548	Remote Similarity	NPC210192
0.6548	Remote Similarity	NPC469661
0.6548	Remote Similarity	NPC257095
0.6545	Remote Similarity	NPC470236
0.6543	Remote Similarity	NPC470079
0.6543	Remote Similarity	NPC474491
0.6541	Remote Similarity	NPC470510
0.6538	Remote Similarity	NPC469412
0.6538	Remote Similarity	NPC198734
0.6536	Remote Similarity	NPC19555
0.6524	Remote Similarity	NPC132895
0.6522	Remote Similarity	NPC198487
0.6509	Remote Similarity	NPC5253
0.6509	Remote Similarity	NPC472353
0.6509	Remote Similarity	NPC49542
0.6509	Remote Similarity	NPC139976
0.6509	Remote Similarity	NPC475084
0.6509	Remote Similarity	NPC469559
0.6509	Remote Similarity	NPC189115
0.6509	Remote Similarity	NPC128337
0.6509	Remote Similarity	NPC230718
0.6509	Remote Similarity	NPC84207
0.6508	Remote Similarity	NPC295287
0.6506	Remote Similarity	NPC104167
0.6503	Remote Similarity	NPC166168
0.6497	Remote Similarity	NPC320064
0.6491	Remote Similarity	NPC226722
0.6486	Remote Similarity	NPC115343
0.6486	Remote Similarity	NPC1291
0.6485	Remote Similarity	NPC87696
0.6485	Remote Similarity	NPC48863
0.6485	Remote Similarity	NPC13745
0.6485	Remote Similarity	NPC251981
0.6484	Remote Similarity	NPC182257
0.6481	Remote Similarity	NPC295970
0.648	Remote Similarity	NPC214368
0.6478	Remote Similarity	NPC287429
0.6471	Remote Similarity	NPC469829
0.6471	Remote Similarity	NPC473044
0.6471	Remote Similarity	NPC252169
0.6467	Remote Similarity	NPC110374
0.6467	Remote Similarity	NPC289743
0.6463	Remote Similarity	NPC470270
0.6456	Remote Similarity	NPC108826
0.645	Remote Similarity	NPC215512
0.645	Remote Similarity	NPC476442
0.6441	Remote Similarity	NPC291359
0.6433	Remote Similarity	NPC25292
0.6433	Remote Similarity	NPC469313
0.6433	Remote Similarity	NPC76176
0.6433	Remote Similarity	NPC168579
0.6433	Remote Similarity	NPC473045
0.6433	Remote Similarity	NPC138227
0.6433	Remote Similarity	NPC225445
0.6429	Remote Similarity	NPC310894
0.6424	Remote Similarity	NPC215833
0.6424	Remote Similarity	NPC69513
0.6421	Remote Similarity	NPC217294
0.6421	Remote Similarity	NPC474661
0.6421	Remote Similarity	NPC475919
0.642	Remote Similarity	NPC146540
0.6417	Remote Similarity	NPC469831
0.6416	Remote Similarity	NPC41844
0.6416	Remote Similarity	NPC476744
0.6407	Remote Similarity	NPC166180
0.6395	Remote Similarity	NPC475096
0.6389	Remote Similarity	NPC50380
0.6389	Remote Similarity	NPC179250
0.6386	Remote Similarity	NPC107478
0.638	Remote Similarity	NPC97326
0.638	Remote Similarity	NPC248355
0.638	Remote Similarity	NPC166040

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 NPC70549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	775
0.2-0.3	1303
0.3-0.4	2804
0.4-0.5	2715
0.5-0.6	1249
0.6-0.7	91
0.7-0.8	6
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
0.8039	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD254	Approved
0.7342	Intermediate Similarity	NPD5788	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3778	Approved
0.7188	Intermediate Similarity	NPD1422	Approved
0.7059	Intermediate Similarity	NPD6034	Phase 2
0.7	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD756	Suspended
0.6932	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1393	Approved
0.6851	Remote Similarity	NPD6184	Discontinued
0.681	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4604	Approved
0.6789	Remote Similarity	NPD4605	Approved
0.6744	Remote Similarity	NPD3296	Phase 1
0.6725	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD9507	Approved
0.671	Remote Similarity	NPD1091	Approved
0.6707	Remote Similarity	NPD2241	Approved
0.6611	Remote Similarity	NPD2215	Approved
0.6611	Remote Similarity	NPD2216	Approved
0.6579	Remote Similarity	NPD9342	Approved
0.657	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5150	Phase 2
0.6527	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3453	Discontinued
0.6514	Remote Similarity	NPD4255	Phase 1
0.6508	Remote Similarity	NPD1898	Discontinued
0.6506	Remote Similarity	NPD822	Approved
0.6497	Remote Similarity	NPD3558	Approved
0.6497	Remote Similarity	NPD3556	Approved
0.6497	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3560	Approved
0.6497	Remote Similarity	NPD3557	Approved
0.6491	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7125	Discontinued
0.6456	Remote Similarity	NPD522	Approved
0.6444	Remote Similarity	NPD4944	Phase 2
0.6444	Remote Similarity	NPD4943	Phase 2
0.6406	Remote Similarity	NPD4325	Phase 2
0.6406	Remote Similarity	NPD4324	Phase 2
0.6404	Remote Similarity	NPD6063	Approved
0.6387	Remote Similarity	NPD2845	Phase 2
0.6387	Remote Similarity	NPD2843	Phase 2
0.6369	Remote Similarity	NPD3454	Phase 3
0.6364	Remote Similarity	NPD4675	Approved
0.6364	Remote Similarity	NPD6104	Discontinued
0.6364	Remote Similarity	NPD4678	Approved
0.6343	Remote Similarity	NPD1653	Approved
0.6343	Remote Similarity	NPD4003	Phase 3
0.6328	Remote Similarity	NPD1440	Discontinued
0.631	Remote Similarity	NPD7007	Discovery
0.6301	Remote Similarity	NPD2114	Discontinued
0.6287	Remote Similarity	NPD7585	Approved
0.6282	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6045	Phase 3
0.6243	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7583	Approved
0.6238	Remote Similarity	NPD7584	Approved
0.6236	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD2366	Approved
0.6236	Remote Similarity	NPD3236	Phase 3
0.6235	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5582	Discontinued
0.6223	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD789	Phase 2
0.6193	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD556	Approved
0.6183	Remote Similarity	NPD5938	Phase 3
0.6182	Remote Similarity	NPD1314	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3538	Suspended
0.6167	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7263	Phase 2
0.6149	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3656	Approved
0.6126	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5811	Approved
0.6121	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD7213	Phase 3
0.6114	Remote Similarity	NPD7212	Phase 2
0.6095	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6669	Phase 2
0.6082	Remote Similarity	NPD6842	Approved
0.6082	Remote Similarity	NPD6841	Approved
0.6082	Remote Similarity	NPD6843	Phase 3
0.608	Remote Similarity	NPD6877	Discontinued
0.608	Remote Similarity	NPD4123	Phase 3
0.6071	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1613	Approved
0.6066	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD3154	Approved
0.6062	Remote Similarity	NPD3153	Approved
0.6061	Remote Similarity	NPD4993	Discontinued
0.6053	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD9376	Approved
0.6038	Remote Similarity	NPD7533	Approved
0.6038	Remote Similarity	NPD7534	Approved
0.6022	Remote Similarity	NPD1769	Discontinued
0.6012	Remote Similarity	NPD5719	Approved
0.6012	Remote Similarity	NPD7477	Discontinued
0.6011	Remote Similarity	NPD3627	Approved
0.6009	Remote Similarity	NPD8067	Phase 3
0.6	Remote Similarity	NPD6296	Discontinued
0.6	Remote Similarity	NPD2223	Approved
0.6	Remote Similarity	NPD2224	Approved
0.599	Remote Similarity	NPD7476	Discontinued
0.599	Remote Similarity	NPD2802	Phase 3
0.5989	Remote Similarity	NPD7447	Phase 1
0.598	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6379	Discontinued
0.5967	Remote Similarity	NPD6072	Discontinued
0.5967	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD2200	Suspended
0.5964	Remote Similarity	NPD2250	Discontinued
0.5962	Remote Similarity	NPD4206	Approved
0.5957	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD1375	Discontinued
0.5952	Remote Similarity	NPD1048	Approved
0.5949	Remote Similarity	NPD4951	Discontinued
0.5949	Remote Similarity	NPD191	Approved
0.5947	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD4005	Discontinued
0.5938	Remote Similarity	NPD1548	Phase 1
0.5933	Remote Similarity	NPD291	Approved
0.593	Remote Similarity	NPD7256	Discontinued
0.592	Remote Similarity	NPD4597	Approved
0.592	Remote Similarity	NPD4598	Approved
0.5917	Remote Similarity	NPD840	Approved
0.5917	Remote Similarity	NPD839	Approved
0.5915	Remote Similarity	NPD1158	Phase 2
0.5915	Remote Similarity	NPD3685	Discontinued
0.5914	Remote Similarity	NPD7129	Suspended
0.5914	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5773	Approved
0.5902	Remote Similarity	NPD5772	Approved
0.5902	Remote Similarity	NPD6283	Phase 2
0.5889	Remote Similarity	NPD5267	Discontinued
0.5886	Remote Similarity	NPD1652	Phase 2
0.5886	Remote Similarity	NPD965	Approved
0.5885	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2249	Approved
0.5882	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2247	Approved
0.588	Remote Similarity	NPD8461	Discontinued
0.5876	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD696	Discontinued
0.5867	Remote Similarity	NPD4587	Phase 3
0.5862	Remote Similarity	NPD9365	Approved
0.586	Remote Similarity	NPD6298	Discontinued
0.5858	Remote Similarity	NPD3144	Approved
0.5858	Remote Similarity	NPD3145	Approved
0.5855	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5847	Phase 1
0.5848	Remote Similarity	NPD654	Phase 3
0.5848	Remote Similarity	NPD9694	Discovery
0.5838	Remote Similarity	NPD4108	Discontinued
0.5838	Remote Similarity	NPD1191	Discontinued
0.5838	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD3633	Approved
0.5829	Remote Similarity	NPD3634	Approved
0.5829	Remote Similarity	NPD4740	Approved
0.5829	Remote Similarity	NPD7153	Discontinued
0.5825	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD2674	Phase 3
0.582	Remote Similarity	NPD4083	Discontinued
0.5815	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD3052	Approved
0.5814	Remote Similarity	NPD3054	Approved
0.5813	Remote Similarity	NPD6874	Approved
0.5812	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.581	Remote Similarity	NPD3536	Discontinued
0.581	Remote Similarity	NPD7498	Phase 1
0.581	Remote Similarity	NPD7499	Phase 1
0.5808	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD7628	Phase 3
0.5808	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD7630	Phase 3
0.5808	Remote Similarity	NPD6136	Phase 2
0.5808	Remote Similarity	NPD1160	Phase 2
0.58	Remote Similarity	NPD6361	Phase 2
0.5799	Remote Similarity	NPD3027	Phase 3
0.5798	Remote Similarity	NPD2821	Approved
0.5795	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD7546	Discontinued
0.5793	Remote Similarity	NPD1610	Phase 2
0.5792	Remote Similarity	NPD5650	Approved
0.5792	Remote Similarity	NPD4205	Phase 3
0.5792	Remote Similarity	NPD5652	Approved
0.5792	Remote Similarity	NPD7491	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