NPASS Compound

Structure

NPC215060 OpenBabel07101718222D 39 43 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -0.8660 -0.5000 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 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 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 2 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 5.1962 -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 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 34 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 15 2 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 23 2 0 0 0 0 13 25 2 0 0 0 0 13 35 1 0 0 0 0 14 24 2 0 0 0 0 14 33 1 0 0 0 0 15 24 1 0 0 0 0 15 34 1 0 0 0 0 16 9 1 6 0 0 0 16 19 1 0 0 0 0 16 37 1 0 0 0 0 17 10 1 6 0 0 0 17 22 1 0 0 0 0 17 36 1 0 0 0 0 18 29 2 0 0 0 0 18 38 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 31 1 6 0 0 0 21 26 1 0 0 0 0 21 32 1 1 0 0 0 22 12 1 1 0 0 0 22 35 1 0 0 0 0 23 25 1 0 0 0 0 23 38 1 0 0 0 0 24 39 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 26 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.15
Volume:	508.651
LogP:	0.153
LogD:	0.056
LogS:	-3.952
# Rotatable Bonds:	7
TPSA:	186.74
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.246
Synthetic Accessibility Score:	4.423
Fsp3:	0.423
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.2
MDCK Permeability:	3.765567817026749e-05
Pgp-inhibitor:	0.154
Pgp-substrate:	0.773
Human Intestinal Absorption (HIA):	0.287
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	60.719017028808594%
Volume Distribution (VD):	0.696
Pgp-substrate:	19.83759307861328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.548
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.328
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.265
CYP3A4-inhibitor:	0.139
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	2.929
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.367
Human Hepatotoxicity (H-HT):	0.677
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.098
Carcinogencity:	0.599
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.004

Download Data

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

Natural Product: NPC215060

Natural Product ID:	NPC215060
*Common Name:**	Daphneticin 4''-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3R)-3-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2-(hydroxymethyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
Synonyms:
Standard InCHIKey:	UFNILYRCPSTPHP-BPCUWKSQSA-N
Standard InCHI:	InChI=1S/C26H28O13/c1-33-14-7-12(8-15(34-2)24(14)39-26-21(32)20(31)19(30)16(9-27)37-26)22-17(10-28)36-25-13(35-22)5-3-11-4-6-18(29)38-23(11)25/h3-8,16-17,19-22,26-28,30-32H,9-10H2,1-2H3/t16-,17-,19-,20+,21-,22-,26+/m1/s1
SMILES:	OC[C@H]1Oc2c(O[C@@H]1c1cc(OC)c(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)ccc1c2oc(=O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575616
PubChem CID:	45482326
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0002545] Coumarinolignans

*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
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	163000.0	nM	PMID[547717]

☑ 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 NPC215060 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	408
0.1-0.2	1808
0.2-0.3	4396
0.3-0.4	9792
0.4-0.5	8459
0.5-0.6	4477
0.6-0.7	5670
0.7-0.8	5606
0.8-0.85	1262
0.85-0.9	578
0.9-0.95	238
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476352
0.9722	High Similarity	NPC93924
0.9653	High Similarity	NPC52740
0.9589	High Similarity	NPC114740
0.9527	High Similarity	NPC150442
0.9467	High Similarity	NPC284810
0.9459	High Similarity	NPC169404
0.9459	High Similarity	NPC176186
0.9459	High Similarity	NPC53587
0.9452	High Similarity	NPC96294
0.9384	High Similarity	NPC15577
0.932	High Similarity	NPC187398
0.932	High Similarity	NPC476348
0.9262	High Similarity	NPC213197
0.9257	High Similarity	NPC106138
0.9252	High Similarity	NPC476347
0.9252	High Similarity	NPC41844
0.92	High Similarity	NPC470264
0.9195	High Similarity	NPC120426
0.9195	High Similarity	NPC21184
0.9195	High Similarity	NPC294522
0.9195	High Similarity	NPC205727
0.9184	High Similarity	NPC199928
0.9128	High Similarity	NPC30688
0.9128	High Similarity	NPC313334
0.9128	High Similarity	NPC206264
0.9128	High Similarity	NPC212670
0.9128	High Similarity	NPC176903
0.9122	High Similarity	NPC87950
0.9122	High Similarity	NPC471764
0.9116	High Similarity	NPC226722
0.9073	High Similarity	NPC120774
0.9073	High Similarity	NPC264875
0.9073	High Similarity	NPC163598
0.906	High Similarity	NPC478237
0.9054	High Similarity	NPC125755
0.9048	High Similarity	NPC292443
0.9048	High Similarity	NPC232228
0.8993	High Similarity	NPC473480
0.8993	High Similarity	NPC15538
0.8993	High Similarity	NPC232992
0.8986	High Similarity	NPC161700
0.8986	High Similarity	NPC476382
0.8986	High Similarity	NPC277867
0.8986	High Similarity	NPC85624
0.8986	High Similarity	NPC100998
0.8986	High Similarity	NPC34587
0.8986	High Similarity	NPC252292
0.8986	High Similarity	NPC34927
0.898	High Similarity	NPC478239
0.8958	High Similarity	NPC103409
0.8947	High Similarity	NPC302610
0.8926	High Similarity	NPC476865
0.8919	High Similarity	NPC168579
0.8919	High Similarity	NPC469313
0.8919	High Similarity	NPC76176
0.8919	High Similarity	NPC138227
0.8912	High Similarity	NPC140502
0.8912	High Similarity	NPC157816
0.8912	High Similarity	NPC473873
0.8912	High Similarity	NPC473792
0.8912	High Similarity	NPC475084
0.8904	High Similarity	NPC210478
0.8874	High Similarity	NPC306890
0.8874	High Similarity	NPC470933
0.8874	High Similarity	NPC471062
0.8874	High Similarity	NPC476386
0.8874	High Similarity	NPC473427
0.8874	High Similarity	NPC259347
0.8874	High Similarity	NPC94871
0.8874	High Similarity	NPC476398
0.8867	High Similarity	NPC296377
0.8861	High Similarity	NPC121290
0.8859	High Similarity	NPC476869
0.8859	High Similarity	NPC476868
0.8859	High Similarity	NPC476450
0.8859	High Similarity	NPC476866
0.8859	High Similarity	NPC476864
0.8859	High Similarity	NPC475096
0.8851	High Similarity	NPC37793
0.8846	High Similarity	NPC173726
0.8846	High Similarity	NPC241600
0.8844	High Similarity	NPC476442
0.8844	High Similarity	NPC215512
0.8844	High Similarity	NPC300611
0.8844	High Similarity	NPC186406
0.8831	High Similarity	NPC8712
0.8828	High Similarity	NPC37468
0.8827	High Similarity	NPC163165
0.8816	High Similarity	NPC257970
0.8816	High Similarity	NPC476871
0.8816	High Similarity	NPC470927
0.8808	High Similarity	NPC280945
0.8808	High Similarity	NPC169510
0.8805	High Similarity	NPC475497
0.8805	High Similarity	NPC284277
0.8805	High Similarity	NPC475366
0.88	High Similarity	NPC205361
0.88	High Similarity	NPC40222
0.88	High Similarity	NPC99515
0.88	High Similarity	NPC268515
0.88	High Similarity	NPC190714
0.8792	High Similarity	NPC476867
0.8784	High Similarity	NPC189115
0.8784	High Similarity	NPC145319
0.8784	High Similarity	NPC469559
0.8776	High Similarity	NPC202700
0.8767	High Similarity	NPC124149
0.8766	High Similarity	NPC246893
0.8759	High Similarity	NPC470236
0.8759	High Similarity	NPC224941
0.8759	High Similarity	NPC311430
0.8758	High Similarity	NPC473621
0.875	High Similarity	NPC283839
0.875	High Similarity	NPC215833
0.875	High Similarity	NPC69513
0.875	High Similarity	NPC90896
0.8742	High Similarity	NPC227902
0.8734	High Similarity	NPC182045
0.8725	High Similarity	NPC138212
0.8725	High Similarity	NPC252169
0.8716	High Similarity	NPC469661
0.8712	High Similarity	NPC472993
0.8707	High Similarity	NPC100389
0.8707	High Similarity	NPC43500
0.8707	High Similarity	NPC98777
0.8707	High Similarity	NPC164148
0.8707	High Similarity	NPC212770
0.8704	High Similarity	NPC51326
0.8704	High Similarity	NPC231194
0.8701	High Similarity	NPC289967
0.8701	High Similarity	NPC472612
0.8701	High Similarity	NPC472611
0.8699	High Similarity	NPC471719
0.8699	High Similarity	NPC164857
0.8699	High Similarity	NPC166180
0.8693	High Similarity	NPC470934
0.8693	High Similarity	NPC238140
0.8693	High Similarity	NPC100818
0.8693	High Similarity	NPC188393
0.869	High Similarity	NPC13745
0.869	High Similarity	NPC48863
0.869	High Similarity	NPC251981
0.869	High Similarity	NPC187194
0.8688	High Similarity	NPC15358
0.8684	High Similarity	NPC175976
0.8684	High Similarity	NPC270751
0.8681	High Similarity	NPC162093
0.8679	High Similarity	NPC12326
0.8675	High Similarity	NPC107120
0.8675	High Similarity	NPC74320
0.8671	High Similarity	NPC203020
0.8671	High Similarity	NPC110349
0.8671	High Similarity	NPC239966
0.8667	High Similarity	NPC473045
0.8667	High Similarity	NPC25292
0.8667	High Similarity	NPC297342
0.8658	High Similarity	NPC222433
0.8658	High Similarity	NPC265648
0.8658	High Similarity	NPC278469
0.8658	High Similarity	NPC193722
0.865	High Similarity	NPC475155
0.865	High Similarity	NPC38438
0.8642	High Similarity	NPC195257
0.8642	High Similarity	NPC209296
0.8642	High Similarity	NPC61791
0.8639	High Similarity	NPC126206
0.8639	High Similarity	NPC262328
0.8639	High Similarity	NPC59324
0.8639	High Similarity	NPC65530
0.8639	High Similarity	NPC87777
0.8639	High Similarity	NPC78363
0.8634	High Similarity	NPC115674
0.8634	High Similarity	NPC210073
0.8634	High Similarity	NPC59516
0.863	High Similarity	NPC238243
0.863	High Similarity	NPC55040
0.863	High Similarity	NPC185778
0.8627	High Similarity	NPC475250
0.8627	High Similarity	NPC111785
0.8625	High Similarity	NPC243930
0.8625	High Similarity	NPC88023
0.8625	High Similarity	NPC309025
0.8621	High Similarity	NPC49074
0.8621	High Similarity	NPC263064
0.8611	High Similarity	NPC9912
0.8609	High Similarity	NPC469701
0.8608	High Similarity	NPC160780
0.8608	High Similarity	NPC478269
0.8608	High Similarity	NPC289811
0.86	High Similarity	NPC110067
0.86	High Similarity	NPC91492
0.86	High Similarity	NPC473044
0.86	High Similarity	NPC34245
0.86	High Similarity	NPC256555
0.86	High Similarity	NPC7439
0.8599	High Similarity	NPC473323
0.8598	High Similarity	NPC34436
0.8598	High Similarity	NPC219600
0.8598	High Similarity	NPC263119

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 NPC215060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	954
0.2-0.3	1995
0.3-0.4	2704
0.4-0.5	1825
0.5-0.6	877
0.6-0.7	284
0.7-0.8	118
0.8-0.85	20
0.85-0.9	3
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9128	High Similarity	NPD1653	Approved
0.8642	High Similarity	NPD7054	Approved
0.8589	High Similarity	NPD7472	Approved
0.8581	High Similarity	NPD7266	Discontinued
0.8476	Intermediate Similarity	NPD7074	Phase 3
0.8434	Intermediate Similarity	NPD7808	Phase 3
0.8424	Intermediate Similarity	NPD6797	Phase 2
0.8373	Intermediate Similarity	NPD7251	Discontinued
0.8323	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD3818	Discontinued
0.8199	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1613	Approved
0.8176	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7228	Approved
0.8105	Intermediate Similarity	NPD1652	Phase 2
0.8075	Intermediate Similarity	NPD3817	Phase 2
0.8049	Intermediate Similarity	NPD7199	Phase 2
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD5844	Phase 1
0.7973	Intermediate Similarity	NPD3027	Phase 3
0.795	Intermediate Similarity	NPD37	Approved
0.7941	Intermediate Similarity	NPD7240	Approved
0.7914	Intermediate Similarity	NPD4967	Phase 2
0.7914	Intermediate Similarity	NPD4966	Approved
0.7914	Intermediate Similarity	NPD4965	Approved
0.7905	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD8455	Phase 2
0.7882	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD5124	Phase 1
0.7881	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6674	Discontinued
0.7844	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1934	Approved
0.7838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.7818	Intermediate Similarity	NPD6234	Discontinued
0.7793	Intermediate Similarity	NPD1091	Approved
0.7791	Intermediate Similarity	NPD7549	Discontinued
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.775	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5402	Approved
0.7683	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD2801	Approved
0.7671	Intermediate Similarity	NPD422	Phase 1
0.764	Intermediate Similarity	NPD5403	Approved
0.763	Intermediate Similarity	NPD7685	Pre-registration
0.7625	Intermediate Similarity	NPD5401	Approved
0.7607	Intermediate Similarity	NPD4380	Phase 2
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5494	Approved
0.755	Intermediate Similarity	NPD4908	Phase 1
0.7545	Intermediate Similarity	NPD7075	Discontinued
0.7515	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD3018	Phase 2
0.7472	Intermediate Similarity	NPD6843	Phase 3
0.7472	Intermediate Similarity	NPD6842	Approved
0.7472	Intermediate Similarity	NPD6841	Approved
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.747	Intermediate Similarity	NPD7819	Suspended
0.7453	Intermediate Similarity	NPD1511	Approved
0.7453	Intermediate Similarity	NPD6799	Approved
0.7451	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.7436	Intermediate Similarity	NPD7097	Phase 1
0.7419	Intermediate Similarity	NPD1933	Approved
0.7412	Intermediate Similarity	NPD8127	Discontinued
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7375	Intermediate Similarity	NPD3750	Approved
0.7362	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1512	Approved
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7411	Suspended
0.7333	Intermediate Similarity	NPD2982	Phase 2
0.7333	Intermediate Similarity	NPD2983	Phase 2
0.7329	Intermediate Similarity	NPD6190	Approved
0.7315	Intermediate Similarity	NPD3705	Approved
0.7315	Intermediate Similarity	NPD1610	Phase 2
0.7297	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3225	Approved
0.7278	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD2981	Phase 2
0.7267	Intermediate Similarity	NPD6232	Discontinued
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7253	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.7238	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7680	Approved
0.7233	Intermediate Similarity	NPD2796	Approved
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7219	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4340	Discontinued
0.7197	Intermediate Similarity	NPD447	Suspended
0.7193	Intermediate Similarity	NPD919	Approved
0.7186	Intermediate Similarity	NPD6599	Discontinued
0.7179	Intermediate Similarity	NPD6233	Phase 2
0.7178	Intermediate Similarity	NPD5058	Phase 3
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7133	Intermediate Similarity	NPD3496	Discontinued
0.7126	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2797	Approved
0.712	Intermediate Similarity	NPD7583	Approved
0.7114	Intermediate Similarity	NPD1357	Approved
0.711	Intermediate Similarity	NPD6959	Discontinued
0.7097	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5536	Phase 2
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD230	Phase 1
0.7086	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7585	Approved
0.7081	Intermediate Similarity	NPD5762	Approved
0.7081	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5763	Approved
0.7076	Intermediate Similarity	NPD7768	Phase 2
0.7066	Intermediate Similarity	NPD3687	Approved
0.7066	Intermediate Similarity	NPD3686	Approved
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7051	Intermediate Similarity	NPD7095	Approved
0.7051	Intermediate Similarity	NPD4625	Phase 3
0.7048	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2424	Discontinued
0.703	Intermediate Similarity	NPD4357	Discontinued
0.703	Intermediate Similarity	NPD7213	Phase 3
0.703	Intermediate Similarity	NPD7212	Phase 2
0.7019	Intermediate Similarity	NPD1551	Phase 2
0.7018	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4536	Approved
0.7	Intermediate Similarity	NPD4538	Approved
0.6994	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4749	Approved
0.6988	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7447	Phase 1
0.6987	Remote Similarity	NPD6832	Phase 2
0.6986	Remote Similarity	NPD5535	Approved
0.6975	Remote Similarity	NPD3540	Phase 1
0.6974	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7783	Phase 2
0.6957	Remote Similarity	NPD1510	Phase 2
0.6951	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7039	Approved
0.6944	Remote Similarity	NPD7038	Approved
0.6939	Remote Similarity	NPD5283	Phase 1
0.6933	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5353	Approved
0.6918	Remote Similarity	NPD4140	Approved
0.6914	Remote Similarity	NPD3539	Phase 1
0.6914	Remote Similarity	NPD6032	Approved
0.6914	Remote Similarity	NPD2935	Discontinued
0.6899	Remote Similarity	NPD1296	Phase 2
0.6894	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4678	Approved
0.6882	Remote Similarity	NPD4675	Approved
0.6875	Remote Similarity	NPD290	Approved
0.6875	Remote Similarity	NPD1358	Approved
0.6875	Remote Similarity	NPD7435	Discontinued
0.6875	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7843	Approved
0.6857	Remote Similarity	NPD5677	Discontinued
0.6856	Remote Similarity	NPD7584	Approved
0.6855	Remote Similarity	NPD4062	Phase 3
0.6852	Remote Similarity	NPD5588	Approved
0.6852	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4308	Phase 3
0.6852	Remote Similarity	NPD5960	Phase 3
0.6846	Remote Similarity	NPD7157	Approved
0.6845	Remote Similarity	NPD6273	Approved
0.6842	Remote Similarity	NPD1778	Approved
0.6839	Remote Similarity	NPD8651	Approved
0.6839	Remote Similarity	NPD6971	Discontinued
0.6839	Remote Similarity	NPD3749	Approved
0.6836	Remote Similarity	NPD5242	Approved
0.6836	Remote Similarity	NPD3926	Phase 2
0.6832	Remote Similarity	NPD6653	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