NPASS Compound

Structure

NPC9447 OpenBabel07101719132D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.4190 -2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3916 0.1293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 -2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6485 -0.5398 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8564 -1.5180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1132 -2.1871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1622 -1.8781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9543 -0.9000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3427 -0.1797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8074 -1.8270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3212 -3.1653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 -2.5472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 1.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 -0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6974 -0.2308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 6 1 0 0 0 0 3 6 2 0 0 0 0 4 17 1 0 0 0 0 5 22 1 0 0 0 0 7 3 1 6 0 0 0 7 14 1 0 0 0 0 7 23 1 0 0 0 0 8 4 1 6 0 0 0 8 11 1 0 0 0 0 8 24 1 0 0 0 0 9 5 1 6 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 1 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 16 1 0 0 0 0 13 20 1 1 0 0 0 14 25 1 1 0 0 0 15 21 2 0 0 0 0 15 25 1 0 0 0 0 16 22 1 6 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.14
Volume:	333.462
LogP:	-0.088
LogD:	-0.454
LogS:	-1.113
# Rotatable Bonds:	5
TPSA:	134.91
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	4.769
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.924
MDCK Permeability:	0.00011744697985704988
Pgp-inhibitor:	0.225
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.937
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	33.04179382324219%
Volume Distribution (VD):	0.632
Pgp-substrate:	42.905513763427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	1.671
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.508
Drug-inuced Liver Injury (DILI):	0.509
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.103
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.078
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC9447

Natural Product ID:	NPC9447
*Common Name:**	Aruncide C
IUPAC Name:	(1S,2R,4R,5S)-4-(2-methylprop-1-enyl)-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,6-dioxabicyclo[3.2.0]heptan-7-one
Synonyms:	aruncide C
Standard InCHIKey:	SYRQWOHSFOHYCI-RDRHTQILSA-N
Standard InCHI:	InChI=1S/C16H24O9/c1-6(2)3-7-14-10(15(21)25-14)9(23-7)5-22-16-13(20)12(19)11(18)8(4-17)24-16/h3,7-14,16-20H,4-5H2,1-2H3/t7-,8-,9+,10+,11-,12+,13-,14-,16-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@@H]2O[C@@H]([C@@H]3[C@H]2C(=O)O3)C=C(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1778416
PubChem CID:	54585601
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
NPO21463.1	Aruncus dioicus	Under-species	n.a.	n.a.	aerial parts	n.a.	n.a.	PMID[21546250]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[525479]
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[525479]

☑ 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 NPC9447 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	178
0.1-0.2	1412
0.2-0.3	5537
0.3-0.4	13232
0.4-0.5	11316
0.5-0.6	7496
0.6-0.7	3161
0.7-0.8	354
0.8-0.85	8
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC137368
0.871	High Similarity	NPC306041
0.8511	High Similarity	NPC54731
0.8478	Intermediate Similarity	NPC472199
0.8298	Intermediate Similarity	NPC472198
0.828	Intermediate Similarity	NPC472197
0.8265	Intermediate Similarity	NPC310804
0.8265	Intermediate Similarity	NPC261117
0.8242	Intermediate Similarity	NPC475037
0.8222	Intermediate Similarity	NPC470124
0.8191	Intermediate Similarity	NPC61201
0.8172	Intermediate Similarity	NPC303451
0.8172	Intermediate Similarity	NPC6414
0.8163	Intermediate Similarity	NPC298255
0.8163	Intermediate Similarity	NPC28304
0.8132	Intermediate Similarity	NPC478112
0.8111	Intermediate Similarity	NPC266718
0.8081	Intermediate Similarity	NPC250545
0.8061	Intermediate Similarity	NPC306344
0.8061	Intermediate Similarity	NPC22149
0.8061	Intermediate Similarity	NPC255677
0.8022	Intermediate Similarity	NPC475034
0.8	Intermediate Similarity	NPC472195
0.8	Intermediate Similarity	NPC238090
0.8	Intermediate Similarity	NPC320089
0.8	Intermediate Similarity	NPC472196
0.7979	Intermediate Similarity	NPC118078
0.7935	Intermediate Similarity	NPC278283
0.7921	Intermediate Similarity	NPC86095
0.7917	Intermediate Similarity	NPC159698
0.7912	Intermediate Similarity	NPC475035
0.79	Intermediate Similarity	NPC222062
0.79	Intermediate Similarity	NPC195510
0.79	Intermediate Similarity	NPC13171
0.7872	Intermediate Similarity	NPC478110
0.7865	Intermediate Similarity	NPC163362
0.7865	Intermediate Similarity	NPC127295
0.7857	Intermediate Similarity	NPC472290
0.7835	Intermediate Similarity	NPC170204
0.7835	Intermediate Similarity	NPC469543
0.7826	Intermediate Similarity	NPC470658
0.7822	Intermediate Similarity	NPC197541
0.7822	Intermediate Similarity	NPC234304
0.7822	Intermediate Similarity	NPC267869
0.7822	Intermediate Similarity	NPC284929
0.7822	Intermediate Similarity	NPC118761
0.78	Intermediate Similarity	NPC4637
0.78	Intermediate Similarity	NPC98859
0.7789	Intermediate Similarity	NPC473311
0.7789	Intermediate Similarity	NPC474232
0.7789	Intermediate Similarity	NPC117596
0.7767	Intermediate Similarity	NPC474285
0.7767	Intermediate Similarity	NPC254538
0.7755	Intermediate Similarity	NPC241911
0.7753	Intermediate Similarity	NPC321728
0.7745	Intermediate Similarity	NPC474917
0.7732	Intermediate Similarity	NPC294293
0.7717	Intermediate Similarity	NPC32676
0.7708	Intermediate Similarity	NPC472126
0.7708	Intermediate Similarity	NPC477749
0.7708	Intermediate Similarity	NPC472125
0.7708	Intermediate Similarity	NPC472124
0.77	Intermediate Similarity	NPC244878
0.7692	Intermediate Similarity	NPC11383
0.7692	Intermediate Similarity	NPC475960
0.7692	Intermediate Similarity	NPC474959
0.7692	Intermediate Similarity	NPC310450
0.7692	Intermediate Similarity	NPC475046
0.7684	Intermediate Similarity	NPC104129
0.7684	Intermediate Similarity	NPC477748
0.7684	Intermediate Similarity	NPC249408
0.7677	Intermediate Similarity	NPC304445
0.7677	Intermediate Similarity	NPC236580
0.7664	Intermediate Similarity	NPC264153
0.7653	Intermediate Similarity	NPC101051
0.7653	Intermediate Similarity	NPC471142
0.764	Intermediate Similarity	NPC133377
0.7634	Intermediate Similarity	NPC477746
0.7634	Intermediate Similarity	NPC477747
0.7629	Intermediate Similarity	NPC471483
0.7629	Intermediate Similarity	NPC320552
0.7624	Intermediate Similarity	NPC20673
0.7624	Intermediate Similarity	NPC473332
0.7614	Intermediate Similarity	NPC229655
0.7609	Intermediate Similarity	NPC286770
0.7609	Intermediate Similarity	NPC284472
0.7609	Intermediate Similarity	NPC229799
0.7604	Intermediate Similarity	NPC327253
0.7604	Intermediate Similarity	NPC473619
0.7604	Intermediate Similarity	NPC307699
0.7604	Intermediate Similarity	NPC202886
0.76	Intermediate Similarity	NPC472015
0.76	Intermediate Similarity	NPC471144
0.76	Intermediate Similarity	NPC151093
0.76	Intermediate Similarity	NPC203627
0.7579	Intermediate Similarity	NPC470137
0.7576	Intermediate Similarity	NPC477921
0.7573	Intermediate Similarity	NPC469869
0.7556	Intermediate Similarity	NPC99651
0.7553	Intermediate Similarity	NPC469910
0.7551	Intermediate Similarity	NPC256368
0.7551	Intermediate Similarity	NPC2003
0.7551	Intermediate Similarity	NPC25701
0.7549	Intermediate Similarity	NPC471599
0.7528	Intermediate Similarity	NPC110813
0.7527	Intermediate Similarity	NPC288471
0.7526	Intermediate Similarity	NPC473321
0.7525	Intermediate Similarity	NPC475949
0.7525	Intermediate Similarity	NPC473146
0.7525	Intermediate Similarity	NPC324667
0.7523	Intermediate Similarity	NPC277583
0.75	Intermediate Similarity	NPC266842
0.75	Intermediate Similarity	NPC251026
0.7476	Intermediate Similarity	NPC474165
0.7476	Intermediate Similarity	NPC151516
0.7476	Intermediate Similarity	NPC4620
0.7476	Intermediate Similarity	NPC69171
0.7475	Intermediate Similarity	NPC471141
0.7475	Intermediate Similarity	NPC477922
0.7475	Intermediate Similarity	NPC36954
0.7453	Intermediate Similarity	NPC315836
0.7453	Intermediate Similarity	NPC313668
0.7451	Intermediate Similarity	NPC198992
0.7451	Intermediate Similarity	NPC219038
0.7451	Intermediate Similarity	NPC67296
0.7449	Intermediate Similarity	NPC475912
0.7449	Intermediate Similarity	NPC476300
0.7447	Intermediate Similarity	NPC21469
0.7426	Intermediate Similarity	NPC187268
0.7426	Intermediate Similarity	NPC169468
0.7426	Intermediate Similarity	NPC307517
0.7426	Intermediate Similarity	NPC198422
0.7426	Intermediate Similarity	NPC40182
0.7426	Intermediate Similarity	NPC81483
0.7426	Intermediate Similarity	NPC249171
0.7426	Intermediate Similarity	NPC61630
0.7426	Intermediate Similarity	NPC49833
0.7423	Intermediate Similarity	NPC270908
0.7423	Intermediate Similarity	NPC231710
0.7423	Intermediate Similarity	NPC65665
0.7423	Intermediate Similarity	NPC470573
0.7423	Intermediate Similarity	NPC120021
0.7423	Intermediate Similarity	NPC216826
0.7419	Intermediate Similarity	NPC142111
0.7419	Intermediate Similarity	NPC170286
0.7419	Intermediate Similarity	NPC116543
0.7419	Intermediate Similarity	NPC52923
0.7419	Intermediate Similarity	NPC473315
0.7404	Intermediate Similarity	NPC220964
0.7404	Intermediate Similarity	NPC475676
0.74	Intermediate Similarity	NPC474297
0.74	Intermediate Similarity	NPC256230
0.74	Intermediate Similarity	NPC473859
0.7396	Intermediate Similarity	NPC475819
0.7396	Intermediate Similarity	NPC473715
0.7396	Intermediate Similarity	NPC476803
0.7391	Intermediate Similarity	NPC469469
0.7391	Intermediate Similarity	NPC280367
0.7383	Intermediate Similarity	NPC46407
0.7383	Intermediate Similarity	NPC235014
0.7379	Intermediate Similarity	NPC201191
0.7379	Intermediate Similarity	NPC183571
0.7374	Intermediate Similarity	NPC475927
0.7374	Intermediate Similarity	NPC475832
0.7374	Intermediate Similarity	NPC71589
0.7358	Intermediate Similarity	NPC135015
0.7358	Intermediate Similarity	NPC217921
0.7358	Intermediate Similarity	NPC392
0.7358	Intermediate Similarity	NPC48548
0.7358	Intermediate Similarity	NPC177524
0.7358	Intermediate Similarity	NPC219900
0.7358	Intermediate Similarity	NPC128795
0.7353	Intermediate Similarity	NPC469402
0.7347	Intermediate Similarity	NPC184463
0.7347	Intermediate Similarity	NPC30515
0.7345	Intermediate Similarity	NPC469812
0.7345	Intermediate Similarity	NPC170880
0.7345	Intermediate Similarity	NPC183353
0.734	Intermediate Similarity	NPC158756
0.734	Intermediate Similarity	NPC473308
0.734	Intermediate Similarity	NPC212363
0.7339	Intermediate Similarity	NPC293658
0.7339	Intermediate Similarity	NPC474410
0.7333	Intermediate Similarity	NPC476740
0.7333	Intermediate Similarity	NPC476738
0.7333	Intermediate Similarity	NPC239961
0.7327	Intermediate Similarity	NPC471462
0.7327	Intermediate Similarity	NPC474194
0.7327	Intermediate Similarity	NPC218064
0.7327	Intermediate Similarity	NPC40812
0.7315	Intermediate Similarity	NPC126897
0.7315	Intermediate Similarity	NPC297945
0.7308	Intermediate Similarity	NPC473148
0.7308	Intermediate Similarity	NPC309398
0.7303	Intermediate Similarity	NPC473948
0.73	Intermediate Similarity	NPC475659
0.73	Intermediate Similarity	NPC14961
0.73	Intermediate Similarity	NPC270013
0.7292	Intermediate Similarity	NPC118077
0.7292	Intermediate Similarity	NPC475186

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 NPC9447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1826
0.2-0.3	4086
0.3-0.4	2130
0.4-0.5	690
0.5-0.6	207
0.6-0.7	65
0.7-0.8	2
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
0.7604	Intermediate Similarity	NPD6698	Approved
0.7604	Intermediate Similarity	NPD46	Approved
0.7358	Intermediate Similarity	NPD6686	Approved
0.7345	Intermediate Similarity	NPD8516	Approved
0.7345	Intermediate Similarity	NPD8517	Approved
0.7345	Intermediate Similarity	NPD8515	Approved
0.7345	Intermediate Similarity	NPD8513	Phase 3
0.7315	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7983	Approved
0.6944	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7838	Discovery
0.6762	Remote Similarity	NPD4225	Approved
0.6752	Remote Similarity	NPD8444	Approved
0.675	Remote Similarity	NPD8074	Phase 3
0.6731	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD8451	Approved
0.6639	Remote Similarity	NPD7829	Approved
0.6639	Remote Similarity	NPD7642	Approved
0.6639	Remote Similarity	NPD7830	Approved
0.6612	Remote Similarity	NPD8448	Approved
0.6607	Remote Similarity	NPD6371	Approved
0.66	Remote Similarity	NPD4251	Approved
0.66	Remote Similarity	NPD4250	Approved
0.6504	Remote Similarity	NPD7319	Approved
0.6465	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8392	Approved
0.6452	Remote Similarity	NPD8391	Approved
0.6452	Remote Similarity	NPD8390	Approved
0.6446	Remote Similarity	NPD8341	Approved
0.6446	Remote Similarity	NPD8299	Approved
0.6446	Remote Similarity	NPD8340	Approved
0.6446	Remote Similarity	NPD8342	Approved
0.6404	Remote Similarity	NPD2204	Approved
0.64	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7507	Approved
0.6392	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6110	Phase 1
0.6356	Remote Similarity	NPD7641	Discontinued
0.6356	Remote Similarity	NPD7328	Approved
0.6356	Remote Similarity	NPD7327	Approved
0.6346	Remote Similarity	NPD7637	Suspended
0.6339	Remote Similarity	NPD6412	Phase 2
0.6333	Remote Similarity	NPD8033	Approved
0.6333	Remote Similarity	NPD896	Approved
0.6333	Remote Similarity	NPD898	Approved
0.6333	Remote Similarity	NPD897	Approved
0.6321	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7516	Approved
0.6293	Remote Similarity	NPD8133	Approved
0.6286	Remote Similarity	NPD5778	Approved
0.6286	Remote Similarity	NPD5779	Approved
0.6271	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD8377	Approved
0.6238	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8328	Phase 3
0.6228	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5282	Discontinued
0.6224	Remote Similarity	NPD4252	Approved
0.62	Remote Similarity	NPD7154	Phase 3
0.6198	Remote Similarity	NPD8378	Approved
0.6198	Remote Similarity	NPD8296	Approved
0.6198	Remote Similarity	NPD8335	Approved
0.6198	Remote Similarity	NPD8380	Approved
0.6198	Remote Similarity	NPD8379	Approved
0.6198	Remote Similarity	NPD7503	Approved
0.6186	Remote Similarity	NPD4268	Approved
0.6186	Remote Similarity	NPD4271	Approved
0.6182	Remote Similarity	NPD5344	Discontinued
0.6154	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4269	Approved
0.61	Remote Similarity	NPD4270	Approved
0.6095	Remote Similarity	NPD5785	Approved
0.6066	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4819	Approved
0.6061	Remote Similarity	NPD4821	Approved
0.6061	Remote Similarity	NPD4822	Approved
0.6061	Remote Similarity	NPD4820	Approved
0.6019	Remote Similarity	NPD5786	Approved
0.6016	Remote Similarity	NPD8080	Discontinued
0.6	Remote Similarity	NPD1695	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD6101	Approved
0.596	Remote Similarity	NPD7329	Approved
0.5946	Remote Similarity	NPD7639	Approved
0.5946	Remote Similarity	NPD7640	Approved
0.5941	Remote Similarity	NPD5209	Approved
0.5935	Remote Similarity	NPD8268	Approved
0.5935	Remote Similarity	NPD8266	Approved
0.5935	Remote Similarity	NPD8269	Approved
0.5935	Remote Similarity	NPD8267	Approved
0.5922	Remote Similarity	NPD5363	Approved
0.5897	Remote Similarity	NPD6421	Discontinued
0.5888	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6411	Approved
0.5882	Remote Similarity	NPD5362	Discontinued
0.5868	Remote Similarity	NPD7115	Discovery
0.5862	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5370	Suspended
0.5833	Remote Similarity	NPD3181	Approved
0.5827	Remote Similarity	NPD8293	Discontinued
0.5812	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6648	Approved
0.5798	Remote Similarity	NPD6053	Discontinued
0.5794	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6435	Approved
0.5781	Remote Similarity	NPD7736	Approved
0.5765	Remote Similarity	NPD894	Approved
0.5765	Remote Similarity	NPD889	Approved
0.5765	Remote Similarity	NPD887	Approved
0.5765	Remote Similarity	NPD895	Approved
0.5763	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.576	Remote Similarity	NPD6370	Approved
0.5738	Remote Similarity	NPD7500	Approved
0.5728	Remote Similarity	NPD5332	Approved
0.5728	Remote Similarity	NPD5331	Approved
0.5714	Remote Similarity	NPD8961	Approved
0.5714	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4790	Discontinued
0.5676	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD7492	Approved
0.5639	Remote Similarity	NPD8415	Approved
0.5625	Remote Similarity	NPD6616	Approved
0.56	Remote Similarity	NPD6319	Approved
0.56	Remote Similarity	NPD6054	Approved
0.56	Remote Similarity	NPD6059	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