NPASS Compound

Structure

NPC112766 OpenBabel07101719132D 25 27 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 -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 22 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 22 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 23 1 0 0 0 0 9 5 1 6 0 0 0 9 10 1 0 0 0 0 9 24 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 2 0 0 0 0 13 21 1 0 0 0 0 14 24 1 0 0 0 0 14 25 1 6 0 0 0 15 23 1 0 0 0 0 15 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.11
Volume:	321.89
LogP:	-0.399
LogD:	-0.201
LogS:	-2.21
# Rotatable Bonds:	4
TPSA:	146.94
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	4.011
Fsp3:	0.533
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:	-5.874
MDCK Permeability:	4.147714207647368e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.673
Human Intestinal Absorption (HIA):	0.383
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.726

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	36.19234848022461%
Volume Distribution (VD):	0.371
Pgp-substrate:	51.522300720214844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.148
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.525
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.282
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.306
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	1.697
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.673
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.406
Carcinogencity:	0.512
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC112766

Natural Product ID:	NPC112766
*Common Name:**	(2R)-7-Methoxy-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-methoxy-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:	PMBZSEOAOIYRMW-XFWGRBSCSA-N
Standard InCHI:	InChI=1S/C15H19NO9/c1-22-6-2-3-7-8(4-6)23-15(13(21)16-7)25-14-12(20)11(19)10(18)9(5-17)24-14/h2-4,9-12,14-15,17-20H,5H2,1H3,(H,16,21)/t9-,10-,11+,12-,14+,15-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2Oc3cc(OC)ccc3N=C2O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487419
PubChem CID:	11035692
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	=	2.8	%	PMID[517963]

☑ 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 NPC112766 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	308
0.1-0.2	2442
0.2-0.3	10668
0.3-0.4	8368
0.4-0.5	12182
0.5-0.6	8078
0.6-0.7	608
0.7-0.8	36
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC70549
0.9444	High Similarity	NPC473769
0.8472	Intermediate Similarity	NPC473987
0.8354	Intermediate Similarity	NPC290069
0.8303	Intermediate Similarity	NPC220560
0.8187	Intermediate Similarity	NPC19023
0.8056	Intermediate Similarity	NPC315632
0.7771	Intermediate Similarity	NPC473874
0.7707	Intermediate Similarity	NPC260601
0.758	Intermediate Similarity	NPC476462
0.7381	Intermediate Similarity	NPC57105
0.7355	Intermediate Similarity	NPC297584
0.7321	Intermediate Similarity	NPC306366
0.7321	Intermediate Similarity	NPC231862
0.7292	Intermediate Similarity	NPC264782
0.7233	Intermediate Similarity	NPC36434
0.7216	Intermediate Similarity	NPC316161
0.7193	Intermediate Similarity	NPC204179
0.7189	Intermediate Similarity	NPC478049
0.7189	Intermediate Similarity	NPC314948
0.7188	Intermediate Similarity	NPC298821
0.7171	Intermediate Similarity	NPC25817
0.716	Intermediate Similarity	NPC63628
0.716	Intermediate Similarity	NPC178466
0.7151	Intermediate Similarity	NPC314861
0.7143	Intermediate Similarity	NPC123761
0.7133	Intermediate Similarity	NPC276195
0.7105	Intermediate Similarity	NPC217854
0.7078	Intermediate Similarity	NPC298845
0.707	Intermediate Similarity	NPC208022
0.7059	Intermediate Similarity	NPC221090
0.7041	Intermediate Similarity	NPC10875
0.7041	Intermediate Similarity	NPC10730
0.7039	Intermediate Similarity	NPC152722
0.7032	Intermediate Similarity	NPC37074
0.7012	Intermediate Similarity	NPC161155
0.7012	Intermediate Similarity	NPC97004
0.7012	Intermediate Similarity	NPC136951
0.6995	Remote Similarity	NPC308392
0.6994	Remote Similarity	NPC168750
0.6993	Remote Similarity	NPC192810
0.6987	Remote Similarity	NPC247146
0.697	Remote Similarity	NPC97282
0.6968	Remote Similarity	NPC189589
0.6968	Remote Similarity	NPC469622
0.6933	Remote Similarity	NPC228907
0.6933	Remote Similarity	NPC195814
0.6905	Remote Similarity	NPC139699
0.6905	Remote Similarity	NPC114659
0.6899	Remote Similarity	NPC60756
0.6892	Remote Similarity	NPC142319
0.6871	Remote Similarity	NPC314113
0.6859	Remote Similarity	NPC171533
0.6855	Remote Similarity	NPC287780
0.6816	Remote Similarity	NPC168153
0.6815	Remote Similarity	NPC469621
0.6804	Remote Similarity	NPC471736
0.6795	Remote Similarity	NPC12308
0.6792	Remote Similarity	NPC208769
0.6792	Remote Similarity	NPC313466
0.677	Remote Similarity	NPC60982
0.677	Remote Similarity	NPC115022
0.677	Remote Similarity	NPC294166
0.6755	Remote Similarity	NPC9248
0.6753	Remote Similarity	NPC57751
0.6744	Remote Similarity	NPC305700
0.6744	Remote Similarity	NPC197741
0.6744	Remote Similarity	NPC18249
0.6744	Remote Similarity	NPC140915
0.6744	Remote Similarity	NPC187028
0.6744	Remote Similarity	NPC10221
0.6739	Remote Similarity	NPC313886
0.6736	Remote Similarity	NPC311357
0.673	Remote Similarity	NPC218003
0.6709	Remote Similarity	NPC198798
0.6708	Remote Similarity	NPC165686
0.6708	Remote Similarity	NPC162093
0.6708	Remote Similarity	NPC26080
0.6708	Remote Similarity	NPC303422
0.6708	Remote Similarity	NPC85799
0.6687	Remote Similarity	NPC470236
0.6687	Remote Similarity	NPC474491
0.6687	Remote Similarity	NPC238243
0.6685	Remote Similarity	NPC315631
0.6667	Remote Similarity	NPC49074
0.6667	Remote Similarity	NPC255721
0.6667	Remote Similarity	NPC314025
0.6646	Remote Similarity	NPC138350
0.6646	Remote Similarity	NPC475067
0.6646	Remote Similarity	NPC103409
0.6646	Remote Similarity	NPC3293
0.6646	Remote Similarity	NPC40664
0.6646	Remote Similarity	NPC165482
0.6646	Remote Similarity	NPC197723
0.6646	Remote Similarity	NPC121376
0.6646	Remote Similarity	NPC164857
0.6645	Remote Similarity	NPC226712
0.6644	Remote Similarity	NPC76327
0.663	Remote Similarity	NPC314213
0.663	Remote Similarity	NPC314656
0.6629	Remote Similarity	NPC320064
0.6629	Remote Similarity	NPC235628
0.6626	Remote Similarity	NPC188555
0.6626	Remote Similarity	NPC130496
0.6625	Remote Similarity	NPC295970
0.6623	Remote Similarity	NPC60589
0.6623	Remote Similarity	NPC469708
0.6611	Remote Similarity	NPC225381
0.6606	Remote Similarity	NPC262328
0.6606	Remote Similarity	NPC124149
0.6606	Remote Similarity	NPC87777
0.6605	Remote Similarity	NPC299144
0.6595	Remote Similarity	NPC315913
0.6592	Remote Similarity	NPC198741
0.6585	Remote Similarity	NPC185778
0.6584	Remote Similarity	NPC262606
0.6581	Remote Similarity	NPC269242
0.6581	Remote Similarity	NPC198734
0.6581	Remote Similarity	NPC469412
0.6573	Remote Similarity	NPC127362
0.657	Remote Similarity	NPC184161
0.6569	Remote Similarity	NPC108826
0.6566	Remote Similarity	NPC98777
0.6566	Remote Similarity	NPC212770
0.6564	Remote Similarity	NPC215833
0.6564	Remote Similarity	NPC69513
0.6545	Remote Similarity	NPC104167
0.6545	Remote Similarity	NPC203230
0.6545	Remote Similarity	NPC242028
0.6531	Remote Similarity	NPC159101
0.6524	Remote Similarity	NPC13745
0.6524	Remote Similarity	NPC251981
0.6524	Remote Similarity	NPC48863
0.6519	Remote Similarity	NPC287429
0.6506	Remote Similarity	NPC59324
0.6506	Remote Similarity	NPC65530
0.6506	Remote Similarity	NPC134260
0.6505	Remote Similarity	NPC469829
0.65	Remote Similarity	NPC140750
0.6497	Remote Similarity	NPC476142
0.6488	Remote Similarity	NPC89686
0.6488	Remote Similarity	NPC215512
0.6488	Remote Similarity	NPC108674
0.6488	Remote Similarity	NPC210192
0.6488	Remote Similarity	NPC257095
0.6488	Remote Similarity	NPC476442
0.6488	Remote Similarity	NPC273932
0.648	Remote Similarity	NPC19555
0.6478	Remote Similarity	NPC470510
0.6463	Remote Similarity	NPC132895
0.646	Remote Similarity	NPC40377
0.646	Remote Similarity	NPC302378
0.6455	Remote Similarity	NPC475919
0.6455	Remote Similarity	NPC217294
0.6455	Remote Similarity	NPC474661
0.6455	Remote Similarity	NPC295287
0.6452	Remote Similarity	NPC469831
0.645	Remote Similarity	NPC128337
0.645	Remote Similarity	NPC84207
0.645	Remote Similarity	NPC49542
0.645	Remote Similarity	NPC5253
0.645	Remote Similarity	NPC230718
0.645	Remote Similarity	NPC469559
0.645	Remote Similarity	NPC139976
0.645	Remote Similarity	NPC475084
0.645	Remote Similarity	NPC189115
0.6438	Remote Similarity	NPC233559
0.6433	Remote Similarity	NPC226722
0.6433	Remote Similarity	NPC85624
0.6429	Remote Similarity	NPC210478
0.6429	Remote Similarity	NPC214368
0.642	Remote Similarity	NPC248355
0.642	Remote Similarity	NPC166040
0.6412	Remote Similarity	NPC473044
0.6412	Remote Similarity	NPC116922
0.6406	Remote Similarity	NPC279401
0.6406	Remote Similarity	NPC79293
0.6402	Remote Similarity	NPC470270
0.6391	Remote Similarity	NPC469661
0.6384	Remote Similarity	NPC291359
0.638	Remote Similarity	NPC470079
0.638	Remote Similarity	NPC472024
0.638	Remote Similarity	NPC80600
0.6374	Remote Similarity	NPC473045
0.6374	Remote Similarity	NPC177597
0.6374	Remote Similarity	NPC25292
0.6374	Remote Similarity	NPC310894
0.6374	Remote Similarity	NPC225445
0.6358	Remote Similarity	NPC87950
0.6358	Remote Similarity	NPC198487
0.6358	Remote Similarity	NPC146540
0.6358	Remote Similarity	NPC471764
0.6358	Remote Similarity	NPC296377
0.6358	Remote Similarity	NPC476744
0.6353	Remote Similarity	NPC472353
0.6346	Remote Similarity	NPC14950
0.6344	Remote Similarity	NPC1291
0.6344	Remote Similarity	NPC115343
0.6343	Remote Similarity	NPC474560
0.6341	Remote Similarity	NPC166168

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 NPC112766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	742
0.2-0.3	1256
0.3-0.4	2831
0.4-0.5	2729
0.5-0.6	1294
0.6-0.7	108
0.7-0.8	7
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
0.8092	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD254	Approved
0.75	Intermediate Similarity	NPD5788	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1422	Approved
0.7143	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3778	Approved
0.7134	Intermediate Similarity	NPD756	Suspended
0.7069	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1393	Approved
0.7005	Intermediate Similarity	NPD6034	Phase 2
0.6957	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2241	Approved
0.6796	Remote Similarity	NPD6184	Discontinued
0.6742	Remote Similarity	NPD2216	Approved
0.6742	Remote Similarity	NPD2215	Approved
0.6737	Remote Similarity	NPD4604	Approved
0.6737	Remote Similarity	NPD4605	Approved
0.6706	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3296	Phase 1
0.6667	Remote Similarity	NPD5150	Phase 2
0.6667	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4255	Phase 1
0.6646	Remote Similarity	NPD822	Approved
0.6645	Remote Similarity	NPD1091	Approved
0.6644	Remote Similarity	NPD9507	Approved
0.6627	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7125	Discontinued
0.6543	Remote Similarity	NPD1898	Discontinued
0.6534	Remote Similarity	NPD6063	Approved
0.6526	Remote Similarity	NPD4324	Phase 2
0.6526	Remote Similarity	NPD4325	Phase 2
0.6513	Remote Similarity	NPD9342	Approved
0.6486	Remote Similarity	NPD6104	Discontinued
0.648	Remote Similarity	NPD4943	Phase 2
0.648	Remote Similarity	NPD4944	Phase 2
0.6474	Remote Similarity	NPD4003	Phase 3
0.6461	Remote Similarity	NPD3453	Discontinued
0.6457	Remote Similarity	NPD1440	Discontinued
0.6441	Remote Similarity	NPD3560	Approved
0.6441	Remote Similarity	NPD3556	Approved
0.6441	Remote Similarity	NPD3557	Approved
0.6441	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD3558	Approved
0.6429	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD2843	Phase 2
0.6421	Remote Similarity	NPD2845	Phase 2
0.6407	Remote Similarity	NPD3454	Phase 3
0.64	Remote Similarity	NPD4678	Approved
0.64	Remote Similarity	NPD4675	Approved
0.6392	Remote Similarity	NPD522	Approved
0.6375	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3236	Phase 3
0.6364	Remote Similarity	NPD2366	Approved
0.6344	Remote Similarity	NPD7007	Discovery
0.6344	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2114	Discontinued
0.6333	Remote Similarity	NPD556	Approved
0.6319	Remote Similarity	NPD1314	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD3538	Suspended
0.6304	Remote Similarity	NPD5938	Phase 3
0.6301	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD3656	Approved
0.6269	Remote Similarity	NPD7583	Approved
0.6258	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5582	Discontinued
0.625	Remote Similarity	NPD5811	Approved
0.625	Remote Similarity	NPD789	Phase 2
0.6238	Remote Similarity	NPD7585	Approved
0.623	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6045	Phase 3
0.62	Remote Similarity	NPD6669	Phase 2
0.6198	Remote Similarity	NPD6842	Approved
0.6198	Remote Similarity	NPD6841	Approved
0.6198	Remote Similarity	NPD6843	Phase 3
0.6193	Remote Similarity	NPD1653	Approved
0.6193	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7584	Approved
0.6183	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD3154	Approved
0.6178	Remote Similarity	NPD7533	Approved
0.6178	Remote Similarity	NPD7534	Approved
0.6178	Remote Similarity	NPD3153	Approved
0.6158	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD1769	Discontinued
0.6145	Remote Similarity	NPD7477	Discontinued
0.614	Remote Similarity	NPD5719	Approved
0.6136	Remote Similarity	NPD3627	Approved
0.6114	Remote Similarity	NPD4123	Phase 3
0.6111	Remote Similarity	NPD6877	Discontinued
0.6108	Remote Similarity	NPD7263	Phase 2
0.61	Remote Similarity	NPD7476	Discontinued
0.6098	Remote Similarity	NPD4993	Discontinued
0.6098	Remote Similarity	NPD2250	Discontinued
0.6095	Remote Similarity	NPD2200	Suspended
0.6089	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6379	Discontinued
0.6082	Remote Similarity	NPD1375	Discontinued
0.6081	Remote Similarity	NPD291	Approved
0.6075	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD4206	Approved
0.6067	Remote Similarity	NPD4005	Discontinued
0.6064	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD7212	Phase 2
0.6057	Remote Similarity	NPD7213	Phase 3
0.6049	Remote Similarity	NPD1158	Phase 2
0.6049	Remote Similarity	NPD3685	Discontinued
0.6047	Remote Similarity	NPD4597	Approved
0.6047	Remote Similarity	NPD4598	Approved
0.6041	Remote Similarity	NPD7256	Discontinued
0.6034	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6296	Discontinued
0.6012	Remote Similarity	NPD965	Approved
0.6012	Remote Similarity	NPD1652	Phase 2
0.601	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2247	Approved
0.6	Remote Similarity	NPD6072	Discontinued
0.6	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2249	Approved
0.6	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6	Remote Similarity	NPD696	Discontinued
0.5989	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1048	Approved
0.5987	Remote Similarity	NPD191	Approved
0.5979	Remote Similarity	NPD4587	Phase 3
0.5974	Remote Similarity	NPD9376	Approved
0.5969	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD5847	Phase 1
0.5965	Remote Similarity	NPD4108	Discontinued
0.5963	Remote Similarity	NPD8067	Phase 3
0.5962	Remote Similarity	NPD6298	Discontinued
0.5956	Remote Similarity	NPD1191	Discontinued
0.5954	Remote Similarity	NPD7153	Discontinued
0.5952	Remote Similarity	NPD840	Approved
0.5952	Remote Similarity	NPD839	Approved
0.5939	Remote Similarity	NPD1160	Phase 2
0.5939	Remote Similarity	NPD3634	Approved
0.5939	Remote Similarity	NPD3633	Approved
0.5938	Remote Similarity	NPD2802	Phase 3
0.5938	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5772	Approved
0.5934	Remote Similarity	NPD5773	Approved
0.5932	Remote Similarity	NPD7498	Phase 1
0.5932	Remote Similarity	NPD7447	Phase 1
0.5932	Remote Similarity	NPD7499	Phase 1
0.5926	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5267	Discontinued
0.5918	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD1613	Approved
0.5917	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD4205	Phase 3
0.5904	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD9365	Approved
0.5897	Remote Similarity	NPD4951	Discontinued
0.5895	Remote Similarity	NPD3965	Phase 1
0.5882	Remote Similarity	NPD654	Phase 3
0.5882	Remote Similarity	NPD9694	Discovery
0.5876	Remote Similarity	NPD4586	Phase 3
0.5867	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.586	Remote Similarity	NPD5677	Discontinued
0.586	Remote Similarity	NPD7129	Suspended
0.586	Remote Similarity	NPD2341	Discontinued
0.5859	Remote Similarity	NPD4740	Approved
0.5851	Remote Similarity	NPD4083	Discontinued
0.585	Remote Similarity	NPD6550	Discontinued
0.5848	Remote Similarity	NPD2224	Approved
0.5848	Remote Similarity	NPD2223	Approved
0.5847	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD850	Approved
0.5843	Remote Similarity	NPD848	Approved
0.5843	Remote Similarity	NPD849	Approved
0.5842	Remote Similarity	NPD6874	Approved
0.5839	Remote Similarity	NPD1798	Approved
0.5839	Remote Similarity	NPD1797	Approved
0.5838	Remote Similarity	NPD4258	Approved
0.5838	Remote Similarity	NPD4055	Discovery
0.5838	Remote Similarity	NPD4259	Approved
0.5838	Remote Similarity	NPD6136	Phase 2
0.5837	Remote Similarity	NPD8461	Discontinued
0.5833	Remote Similarity	NPD3180	Approved
0.5833	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3179	Approved
0.5829	Remote Similarity	NPD2821	Approved
0.5828	Remote Similarity	NPD776	Approved
0.5825	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD286	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