NPASS Compound

Structure

NPC470124 OpenBabel07101718192D 24 25 0 0 1 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -5.1962 -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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -4.3301 -2.5000 0.0000 C 0 0 3 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 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 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 -3.4641 0.0000 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 -4.3301 -1.5000 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 1 8 1 0 0 0 0 2 8 1 0 0 0 0 3 4 1 0 0 0 0 3 9 2 0 0 0 0 4 10 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 22 1 0 0 0 0 9 15 1 0 0 0 0 10 23 1 0 0 0 0 11 6 1 6 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 1 0 0 0 13 14 1 0 0 0 0 13 19 1 6 0 0 0 14 16 1 0 0 0 0 14 20 1 1 0 0 0 15 21 2 0 0 0 0 15 23 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:	344.15
Volume:	330.592
LogP:	-0.142
LogD:	-0.636
LogS:	-1.129
# Rotatable Bonds:	5
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	4.796
Fsp3:	0.688
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:	-5.559
MDCK Permeability:	0.0001722935412544757
Pgp-inhibitor:	0.002
Pgp-substrate:	0.934
Human Intestinal Absorption (HIA):	0.834
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.264
Plasma Protein Binding (PPB):	35.905921936035156%
Volume Distribution (VD):	0.547
Pgp-substrate:	39.15964126586914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.245
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	2.213
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.557
AMES Toxicity:	0.82
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.129
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC470124

Natural Product ID:	NPC470124
*Common Name:**	Aruncide A
IUPAC Name:	2-(2-methylprop-1-enyl)-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
Synonyms:	aruncide A
Standard InCHIKey:	MKXVLYPJBLBGIO-LQPVRJLZSA-N
Standard InCHI:	InChI=1S/C16H24O8/c1-8(2)5-10-4-3-9(15(21)23-10)7-22-16-14(20)13(19)12(18)11(6-17)24-16/h3,5,10-14,16-20H,4,6-7H2,1-2H3/t10?,11-,12-,13+,14-,16-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OCC2=CCC(OC2=O)C=C(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1778414
PubChem CID:	54587609
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[540358]
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[540358]

☑ 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 NPC470124 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	176
0.1-0.2	1967
0.2-0.3	6006
0.3-0.4	13675
0.4-0.5	12003
0.5-0.6	6582
0.6-0.7	1957
0.7-0.8	277
0.8-0.85	34
0.85-0.9	17
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC475037
0.881	High Similarity	NPC475034
0.869	High Similarity	NPC475035
0.8675	High Similarity	NPC251026
0.8659	High Similarity	NPC163362
0.8659	High Similarity	NPC127295
0.8605	High Similarity	NPC118077
0.8605	High Similarity	NPC475186
0.8571	High Similarity	NPC142111
0.8571	High Similarity	NPC473315
0.8554	High Similarity	NPC469469
0.8523	High Similarity	NPC303451
0.8523	High Similarity	NPC6414
0.8523	High Similarity	NPC473311
0.8471	Intermediate Similarity	NPC473308
0.8471	Intermediate Similarity	NPC266718
0.8409	Intermediate Similarity	NPC285588
0.8333	Intermediate Similarity	NPC472196
0.8333	Intermediate Similarity	NPC61201
0.8333	Intermediate Similarity	NPC238090
0.8333	Intermediate Similarity	NPC472195
0.8315	Intermediate Similarity	NPC118078
0.8315	Intermediate Similarity	NPC327253
0.8295	Intermediate Similarity	NPC470137
0.8276	Intermediate Similarity	NPC208473
0.8242	Intermediate Similarity	NPC159698
0.8222	Intermediate Similarity	NPC110072
0.8222	Intermediate Similarity	NPC9447
0.8222	Intermediate Similarity	NPC477749
0.8171	Intermediate Similarity	NPC326661
0.8152	Intermediate Similarity	NPC170204
0.8152	Intermediate Similarity	NPC469543
0.8132	Intermediate Similarity	NPC320552
0.809	Intermediate Similarity	NPC137368
0.8072	Intermediate Similarity	NPC475711
0.8072	Intermediate Similarity	NPC474026
0.8043	Intermediate Similarity	NPC294293
0.8021	Intermediate Similarity	NPC201191
0.8	Intermediate Similarity	NPC22149
0.8	Intermediate Similarity	NPC477748
0.8	Intermediate Similarity	NPC306344
0.8	Intermediate Similarity	NPC255677
0.7976	Intermediate Similarity	NPC477314
0.7917	Intermediate Similarity	NPC298255
0.7917	Intermediate Similarity	NPC28304
0.7912	Intermediate Similarity	NPC117596
0.7912	Intermediate Similarity	NPC202886
0.7882	Intermediate Similarity	NPC180725
0.7879	Intermediate Similarity	NPC474285
0.7879	Intermediate Similarity	NPC254538
0.7872	Intermediate Similarity	NPC306041
0.7849	Intermediate Similarity	NPC256368
0.7835	Intermediate Similarity	NPC13171
0.7835	Intermediate Similarity	NPC310804
0.7835	Intermediate Similarity	NPC261117
0.7835	Intermediate Similarity	NPC195510
0.7835	Intermediate Similarity	NPC222062
0.7826	Intermediate Similarity	NPC472124
0.7826	Intermediate Similarity	NPC472125
0.7826	Intermediate Similarity	NPC472199
0.7826	Intermediate Similarity	NPC472126
0.7816	Intermediate Similarity	NPC474959
0.7816	Intermediate Similarity	NPC11383
0.7816	Intermediate Similarity	NPC475046
0.7816	Intermediate Similarity	NPC310450
0.7805	Intermediate Similarity	NPC132938
0.7791	Intermediate Similarity	NPC470147
0.7791	Intermediate Similarity	NPC133226
0.7766	Intermediate Similarity	NPC101051
0.7765	Intermediate Similarity	NPC248775
0.7765	Intermediate Similarity	NPC133377
0.7755	Intermediate Similarity	NPC234304
0.7755	Intermediate Similarity	NPC197541
0.7755	Intermediate Similarity	NPC284929
0.7755	Intermediate Similarity	NPC118761
0.7755	Intermediate Similarity	NPC267869
0.7738	Intermediate Similarity	NPC229655
0.7727	Intermediate Similarity	NPC229799
0.7727	Intermediate Similarity	NPC286770
0.7727	Intermediate Similarity	NPC284472
0.7717	Intermediate Similarity	NPC307699
0.7711	Intermediate Similarity	NPC472174
0.7701	Intermediate Similarity	NPC280367
0.7684	Intermediate Similarity	NPC241911
0.7677	Intermediate Similarity	NPC86095
0.7674	Intermediate Similarity	NPC179933
0.7674	Intermediate Similarity	NPC470149
0.7674	Intermediate Similarity	NPC470148
0.766	Intermediate Similarity	NPC472198
0.7653	Intermediate Similarity	NPC250545
0.7647	Intermediate Similarity	NPC110813
0.764	Intermediate Similarity	NPC288471
0.7634	Intermediate Similarity	NPC469410
0.759	Intermediate Similarity	NPC477311
0.759	Intermediate Similarity	NPC477303
0.7576	Intermediate Similarity	NPC197736
0.7556	Intermediate Similarity	NPC73166
0.7553	Intermediate Similarity	NPC471483
0.7553	Intermediate Similarity	NPC320089
0.7551	Intermediate Similarity	NPC2313
0.7551	Intermediate Similarity	NPC154132
0.7551	Intermediate Similarity	NPC57586
0.7551	Intermediate Similarity	NPC471637
0.7551	Intermediate Similarity	NPC475655
0.7551	Intermediate Similarity	NPC198992
0.7551	Intermediate Similarity	NPC475157
0.7528	Intermediate Similarity	NPC44261
0.7527	Intermediate Similarity	NPC270908
0.7527	Intermediate Similarity	NPC177668
0.7527	Intermediate Similarity	NPC65665
0.7527	Intermediate Similarity	NPC231710
0.7527	Intermediate Similarity	NPC216826
0.7527	Intermediate Similarity	NPC120021
0.7527	Intermediate Similarity	NPC470573
0.75	Intermediate Similarity	NPC472173
0.75	Intermediate Similarity	NPC473605
0.75	Intermediate Similarity	NPC477308
0.75	Intermediate Similarity	NPC475241
0.75	Intermediate Similarity	NPC477312
0.75	Intermediate Similarity	NPC477313
0.75	Intermediate Similarity	NPC477305
0.75	Intermediate Similarity	NPC477315
0.75	Intermediate Similarity	NPC475593
0.75	Intermediate Similarity	NPC475375
0.75	Intermediate Similarity	NPC475540
0.75	Intermediate Similarity	NPC476066
0.75	Intermediate Similarity	NPC477304
0.75	Intermediate Similarity	NPC477309
0.75	Intermediate Similarity	NPC297440
0.75	Intermediate Similarity	NPC477316
0.75	Intermediate Similarity	NPC475525
0.75	Intermediate Similarity	NPC473765
0.75	Intermediate Similarity	NPC475164
0.7474	Intermediate Similarity	NPC25701
0.7474	Intermediate Similarity	NPC2003
0.7473	Intermediate Similarity	NPC47937
0.747	Intermediate Similarity	NPC475762
0.7447	Intermediate Similarity	NPC477349
0.7447	Intermediate Similarity	NPC472197
0.7429	Intermediate Similarity	NPC264153
0.7419	Intermediate Similarity	NPC133450
0.7412	Intermediate Similarity	NPC477306
0.7412	Intermediate Similarity	NPC327041
0.7412	Intermediate Similarity	NPC285840
0.74	Intermediate Similarity	NPC309398
0.7381	Intermediate Similarity	NPC327383
0.7381	Intermediate Similarity	NPC185186
0.7375	Intermediate Similarity	NPC147292
0.7374	Intermediate Similarity	NPC98859
0.7374	Intermediate Similarity	NPC4637
0.7374	Intermediate Similarity	NPC219038
0.7368	Intermediate Similarity	NPC475173
0.7368	Intermediate Similarity	NPC473561
0.7368	Intermediate Similarity	NPC473723
0.7368	Intermediate Similarity	NPC473663
0.7363	Intermediate Similarity	NPC477747
0.7363	Intermediate Similarity	NPC182383
0.7363	Intermediate Similarity	NPC477746
0.7363	Intermediate Similarity	NPC471494
0.7349	Intermediate Similarity	NPC474078
0.7349	Intermediate Similarity	NPC202011
0.7347	Intermediate Similarity	NPC472015
0.7347	Intermediate Similarity	NPC307517
0.7347	Intermediate Similarity	NPC169468
0.7347	Intermediate Similarity	NPC61630
0.7347	Intermediate Similarity	NPC40182
0.7347	Intermediate Similarity	NPC81483
0.7347	Intermediate Similarity	NPC198422
0.734	Intermediate Similarity	NPC473904
0.734	Intermediate Similarity	NPC3952
0.7333	Intermediate Similarity	NPC473500
0.7333	Intermediate Similarity	NPC38295
0.7333	Intermediate Similarity	NPC470313
0.7333	Intermediate Similarity	NPC156089
0.732	Intermediate Similarity	NPC54731
0.732	Intermediate Similarity	NPC143446
0.7312	Intermediate Similarity	NPC48338
0.7312	Intermediate Similarity	NPC20339
0.7312	Intermediate Similarity	NPC471756
0.7312	Intermediate Similarity	NPC233551
0.7312	Intermediate Similarity	NPC21208
0.7312	Intermediate Similarity	NPC40376
0.7312	Intermediate Similarity	NPC280621
0.7312	Intermediate Similarity	NPC471755
0.7303	Intermediate Similarity	NPC21693
0.7303	Intermediate Similarity	NPC236649
0.73	Intermediate Similarity	NPC121423
0.73	Intermediate Similarity	NPC471599
0.7292	Intermediate Similarity	NPC477348
0.7292	Intermediate Similarity	NPC163409
0.7292	Intermediate Similarity	NPC238264
0.7292	Intermediate Similarity	NPC477345
0.7292	Intermediate Similarity	NPC44682
0.7284	Intermediate Similarity	NPC201356
0.7283	Intermediate Similarity	NPC311163
0.7282	Intermediate Similarity	NPC219900
0.7282	Intermediate Similarity	NPC392
0.7282	Intermediate Similarity	NPC177524
0.7282	Intermediate Similarity	NPC193765
0.7282	Intermediate Similarity	NPC473807

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 NPC470124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	2286
0.2-0.3	4039
0.3-0.4	1850
0.4-0.5	636
0.5-0.6	155
0.6-0.7	25
0.7-0.8	3
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
0.7347	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD46	Approved
0.734	Intermediate Similarity	NPD6698	Approved
0.7282	Intermediate Similarity	NPD6686	Approved
0.7158	Intermediate Similarity	NPD7838	Discovery
0.6882	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7830	Approved
0.6696	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6606	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1407	Approved
0.6566	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD8516	Approved
0.6522	Remote Similarity	NPD8517	Approved
0.6522	Remote Similarity	NPD8515	Approved
0.6522	Remote Similarity	NPD7503	Approved
0.6505	Remote Similarity	NPD4225	Approved
0.641	Remote Similarity	NPD7642	Approved
0.6404	Remote Similarity	NPD7327	Approved
0.6404	Remote Similarity	NPD7328	Approved
0.6389	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5344	Discontinued
0.6379	Remote Similarity	NPD8033	Approved
0.6348	Remote Similarity	NPD7516	Approved
0.6293	Remote Similarity	NPD8377	Approved
0.6293	Remote Similarity	NPD8294	Approved
0.6281	Remote Similarity	NPD7319	Approved
0.6239	Remote Similarity	NPD8378	Approved
0.6239	Remote Similarity	NPD8296	Approved
0.6239	Remote Similarity	NPD8380	Approved
0.6239	Remote Similarity	NPD8335	Approved
0.6239	Remote Similarity	NPD8379	Approved
0.6239	Remote Similarity	NPD8444	Approved
0.6216	Remote Similarity	NPD6371	Approved
0.6207	Remote Similarity	NPD897	Approved
0.6207	Remote Similarity	NPD898	Approved
0.6207	Remote Similarity	NPD896	Approved
0.6167	Remote Similarity	NPD7507	Approved
0.6167	Remote Similarity	NPD8451	Approved
0.6154	Remote Similarity	NPD7839	Suspended
0.6139	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7641	Discontinued
0.6116	Remote Similarity	NPD8448	Approved
0.6091	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6	Remote Similarity	NPD893	Approved
0.6	Remote Similarity	NPD891	Phase 3
0.6	Remote Similarity	NPD892	Phase 3
0.6	Remote Similarity	NPD7329	Approved
0.6	Remote Similarity	NPD8328	Phase 3
0.6	Remote Similarity	NPD888	Phase 3
0.5984	Remote Similarity	NPD8074	Phase 3
0.5981	Remote Similarity	NPD6648	Approved
0.5968	Remote Similarity	NPD8392	Approved
0.5968	Remote Similarity	NPD8390	Approved
0.5968	Remote Similarity	NPD8391	Approved
0.595	Remote Similarity	NPD8342	Approved
0.595	Remote Similarity	NPD8340	Approved
0.595	Remote Similarity	NPD8341	Approved
0.595	Remote Similarity	NPD8299	Approved
0.5949	Remote Similarity	NPD905	Approved
0.5949	Remote Similarity	NPD904	Phase 3
0.5922	Remote Similarity	NPD7637	Suspended
0.5918	Remote Similarity	NPD6110	Phase 1
0.5875	Remote Similarity	NPD2269	Approved
0.587	Remote Similarity	NPD3181	Approved
0.5865	Remote Similarity	NPD5779	Approved
0.5865	Remote Similarity	NPD5778	Approved
0.5843	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD69	Approved
0.5833	Remote Similarity	NPD9119	Approved
0.5814	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD887	Approved
0.5802	Remote Similarity	NPD895	Approved
0.5802	Remote Similarity	NPD889	Approved
0.5802	Remote Similarity	NPD894	Approved
0.5795	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8080	Discontinued
0.5776	Remote Similarity	NPD8133	Approved
0.5763	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7115	Discovery
0.5763	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4249	Approved
0.5741	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD9118	Approved
0.5702	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD6123	Approved
0.569	Remote Similarity	NPD6429	Approved
0.569	Remote Similarity	NPD6430	Approved
0.569	Remote Similarity	NPD6053	Discontinued
0.5688	Remote Similarity	NPD7639	Approved
0.5688	Remote Similarity	NPD7640	Approved
0.5686	Remote Similarity	NPD4250	Approved
0.5686	Remote Similarity	NPD4251	Approved
0.5673	Remote Similarity	NPD5785	Approved
0.5657	Remote Similarity	NPD5209	Approved
0.5647	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD6109	Phase 1
0.5644	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7500	Approved
0.5625	Remote Similarity	NPD4756	Discovery
0.5612	Remote Similarity	NPD5790	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