NPASS Compound

Structure

NPC123704 OpenBabel07101718292D 23 24 0 0 1 0 0 0 0 0999 V2000 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 1.7321 -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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 0.8660 -2.5000 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 -0.0000 -1.0000 0.0000 C 0 0 1 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 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 0.0000 -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 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 8 2 0 0 0 0 4 9 2 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 11 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 9 17 1 0 0 0 0 10 7 1 1 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 18 2 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 14 1 0 0 0 0 13 20 1 1 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 22 1 0 0 0 0 15 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.12
Volume:	310.659
LogP:	-0.347
LogD:	-0.13
LogS:	-0.804
# Rotatable Bonds:	6
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	3.497
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:	-5.805
MDCK Permeability:	8.413723844569176e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.802
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.415
Plasma Protein Binding (PPB):	48.54999923706055%
Volume Distribution (VD):	0.421
Pgp-substrate:	39.44224548339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.27
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	2.956
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.254
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.18
Carcinogencity:	0.101
Eye Corrosion:	0.004
Eye Irritation:	0.099
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC123704

Natural Product ID:	NPC123704
*Common Name:**	Dihydrocinnacasside
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 3-(2-hydroxyphenyl)propanoate
Synonyms:	Dihydrocinnacasside
Standard InCHIKey:	JKAYPNQEJVZOMU-LFHLZQBKSA-N
Standard InCHI:	InChI=1S/C15H20O8/c16-7-10-12(19)13(20)14(21)15(22-10)23-11(18)6-5-8-3-1-2-4-9(8)17/h1-4,10,12-17,19-21H,5-7H2/t10-,12-,13+,14-,15+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC(=O)CCc2ccccc2O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077149
PubChem CID:	44178764
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0001540] Monosaccharides [CHEMONTID:0001498] Hexoses

*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
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[19555125]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	670000.0	nM	PMID[550641]

☑ 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 NPC123704 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	271
0.1-0.2	1050
0.2-0.3	2740
0.3-0.4	7115
0.4-0.5	11297
0.5-0.6	6772
0.6-0.7	11204
0.7-0.8	2093
0.8-0.85	130
0.85-0.9	22
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9134	High Similarity	NPC269421
0.8992	High Similarity	NPC34456
0.8898	High Similarity	NPC469549
0.8806	High Similarity	NPC164599
0.8788	High Similarity	NPC310252
0.8788	High Similarity	NPC84789
0.8788	High Similarity	NPC302583
0.8788	High Similarity	NPC100558
0.8769	High Similarity	NPC114116
0.8682	High Similarity	NPC469705
0.8682	High Similarity	NPC17968
0.8682	High Similarity	NPC470122
0.8672	High Similarity	NPC158673
0.8667	High Similarity	NPC157338
0.8636	High Similarity	NPC123988
0.8571	High Similarity	NPC471345
0.8561	High Similarity	NPC169398
0.856	High Similarity	NPC11724
0.855	High Similarity	NPC471095
0.855	High Similarity	NPC471066
0.8525	High Similarity	NPC148055
0.8492	Intermediate Similarity	NPC52097
0.8485	Intermediate Similarity	NPC164172
0.848	Intermediate Similarity	NPC476872
0.8473	Intermediate Similarity	NPC476407
0.8467	Intermediate Similarity	NPC478250
0.845	Intermediate Similarity	NPC288416
0.8417	Intermediate Similarity	NPC474465
0.84	Intermediate Similarity	NPC469702
0.84	Intermediate Similarity	NPC282409
0.8385	Intermediate Similarity	NPC146540
0.8374	Intermediate Similarity	NPC175771
0.837	Intermediate Similarity	NPC65262
0.837	Intermediate Similarity	NPC101686
0.837	Intermediate Similarity	NPC469364
0.8361	Intermediate Similarity	NPC313193
0.8345	Intermediate Similarity	NPC475528
0.8333	Intermediate Similarity	NPC469703
0.8333	Intermediate Similarity	NPC469548
0.8333	Intermediate Similarity	NPC476445
0.8333	Intermediate Similarity	NPC469704
0.8333	Intermediate Similarity	NPC201402
0.8333	Intermediate Similarity	NPC160854
0.8333	Intermediate Similarity	NPC476448
0.8333	Intermediate Similarity	NPC281798
0.8295	Intermediate Similarity	NPC83218
0.8295	Intermediate Similarity	NPC126991
0.8286	Intermediate Similarity	NPC212808
0.8286	Intermediate Similarity	NPC474268
0.8286	Intermediate Similarity	NPC143246
0.8286	Intermediate Similarity	NPC475539
0.8286	Intermediate Similarity	NPC119773
0.8273	Intermediate Similarity	NPC77922
0.8273	Intermediate Similarity	NPC296659
0.8273	Intermediate Similarity	NPC202391
0.8273	Intermediate Similarity	NPC473281
0.8268	Intermediate Similarity	NPC55608
0.8268	Intermediate Similarity	NPC469686
0.8268	Intermediate Similarity	NPC266045
0.8261	Intermediate Similarity	NPC31081
0.8261	Intermediate Similarity	NPC148080
0.8261	Intermediate Similarity	NPC469623
0.8261	Intermediate Similarity	NPC245219
0.8252	Intermediate Similarity	NPC475407
0.8235	Intermediate Similarity	NPC469696
0.8231	Intermediate Similarity	NPC471157
0.8231	Intermediate Similarity	NPC252114
0.8222	Intermediate Similarity	NPC158325
0.8222	Intermediate Similarity	NPC103398
0.8222	Intermediate Similarity	NPC180171
0.8203	Intermediate Similarity	NPC471067
0.8195	Intermediate Similarity	NPC478255
0.8195	Intermediate Similarity	NPC235294
0.8195	Intermediate Similarity	NPC46137
0.8188	Intermediate Similarity	NPC80098
0.8175	Intermediate Similarity	NPC324262
0.8175	Intermediate Similarity	NPC31745
0.8175	Intermediate Similarity	NPC62800
0.8175	Intermediate Similarity	NPC220936
0.8168	Intermediate Similarity	NPC471881
0.8168	Intermediate Similarity	NPC156692
0.8168	Intermediate Similarity	NPC173150
0.8168	Intermediate Similarity	NPC35288
0.8168	Intermediate Similarity	NPC45224
0.8168	Intermediate Similarity	NPC106677
0.8168	Intermediate Similarity	NPC471882
0.8162	Intermediate Similarity	NPC472132
0.8156	Intermediate Similarity	NPC473867
0.8156	Intermediate Similarity	NPC291153
0.8148	Intermediate Similarity	NPC471029
0.8143	Intermediate Similarity	NPC194938
0.814	Intermediate Similarity	NPC232454
0.814	Intermediate Similarity	NPC470907
0.814	Intermediate Similarity	NPC178449
0.8129	Intermediate Similarity	NPC296643
0.8129	Intermediate Similarity	NPC65833
0.8125	Intermediate Similarity	NPC226712
0.8112	Intermediate Similarity	NPC96599
0.8106	Intermediate Similarity	NPC232880
0.8106	Intermediate Similarity	NPC225307
0.8099	Intermediate Similarity	NPC470330
0.8099	Intermediate Similarity	NPC469700
0.8092	Intermediate Similarity	NPC476022
0.8092	Intermediate Similarity	NPC61181
0.8092	Intermediate Similarity	NPC474945
0.8085	Intermediate Similarity	NPC108455
0.8082	Intermediate Similarity	NPC209393
0.8082	Intermediate Similarity	NPC205172
0.8077	Intermediate Similarity	NPC57607
0.806	Intermediate Similarity	NPC225384
0.806	Intermediate Similarity	NPC138777
0.806	Intermediate Similarity	NPC246869
0.8056	Intermediate Similarity	NPC100818
0.8056	Intermediate Similarity	NPC240592
0.8056	Intermediate Similarity	NPC107197
0.8056	Intermediate Similarity	NPC117346
0.8045	Intermediate Similarity	NPC229784
0.8045	Intermediate Similarity	NPC253595
0.8045	Intermediate Similarity	NPC477294
0.8045	Intermediate Similarity	NPC477293
0.8043	Intermediate Similarity	NPC126739
0.8043	Intermediate Similarity	NPC197666
0.8042	Intermediate Similarity	NPC23084
0.8042	Intermediate Similarity	NPC140722
0.8042	Intermediate Similarity	NPC92054
0.8042	Intermediate Similarity	NPC302989
0.8042	Intermediate Similarity	NPC4958
0.8042	Intermediate Similarity	NPC83975
0.803	Intermediate Similarity	NPC476873
0.803	Intermediate Similarity	NPC103533
0.8029	Intermediate Similarity	NPC294470
0.8029	Intermediate Similarity	NPC166180
0.8028	Intermediate Similarity	NPC474044
0.8028	Intermediate Similarity	NPC473147
0.8027	Intermediate Similarity	NPC3449
0.8015	Intermediate Similarity	NPC68517
0.8015	Intermediate Similarity	NPC90318
0.8015	Intermediate Similarity	NPC287597
0.8015	Intermediate Similarity	NPC886
0.8015	Intermediate Similarity	NPC470510
0.8015	Intermediate Similarity	NPC34293
0.8014	Intermediate Similarity	NPC63304
0.8014	Intermediate Similarity	NPC229036
0.8	Intermediate Similarity	NPC289021
0.8	Intermediate Similarity	NPC474620
0.8	Intermediate Similarity	NPC212176
0.8	Intermediate Similarity	NPC138798
0.8	Intermediate Similarity	NPC140151
0.8	Intermediate Similarity	NPC158546
0.7986	Intermediate Similarity	NPC199335
0.7986	Intermediate Similarity	NPC478234
0.7986	Intermediate Similarity	NPC478236
0.7985	Intermediate Similarity	NPC289415
0.7985	Intermediate Similarity	NPC17567
0.7985	Intermediate Similarity	NPC319995
0.7973	Intermediate Similarity	NPC283480
0.7973	Intermediate Similarity	NPC127406
0.7973	Intermediate Similarity	NPC148323
0.7972	Intermediate Similarity	NPC474422
0.7972	Intermediate Similarity	NPC473149
0.797	Intermediate Similarity	NPC40377
0.7956	Intermediate Similarity	NPC233350
0.7956	Intermediate Similarity	NPC212729
0.7956	Intermediate Similarity	NPC182217
0.7956	Intermediate Similarity	NPC70680
0.7956	Intermediate Similarity	NPC263829
0.7951	Intermediate Similarity	NPC326187
0.7945	Intermediate Similarity	NPC478235
0.7943	Intermediate Similarity	NPC293154
0.7939	Intermediate Similarity	NPC244454
0.7939	Intermediate Similarity	NPC85565
0.7931	Intermediate Similarity	NPC104172
0.7931	Intermediate Similarity	NPC88886
0.7931	Intermediate Similarity	NPC182350
0.7929	Intermediate Similarity	NPC64664
0.7929	Intermediate Similarity	NPC79908
0.7926	Intermediate Similarity	NPC254819
0.7926	Intermediate Similarity	NPC473777
0.7926	Intermediate Similarity	NPC219677
0.7923	Intermediate Similarity	NPC469927
0.7919	Intermediate Similarity	NPC208651
0.7919	Intermediate Similarity	NPC206641
0.7919	Intermediate Similarity	NPC43638
0.7917	Intermediate Similarity	NPC218685
0.7917	Intermediate Similarity	NPC120728
0.7914	Intermediate Similarity	NPC220942
0.791	Intermediate Similarity	NPC97326
0.7907	Intermediate Similarity	NPC269242
0.7905	Intermediate Similarity	NPC82190
0.7905	Intermediate Similarity	NPC192219
0.7905	Intermediate Similarity	NPC174599
0.7903	Intermediate Similarity	NPC48525
0.7899	Intermediate Similarity	NPC470572
0.7895	Intermediate Similarity	NPC231607
0.7895	Intermediate Similarity	NPC79715
0.7895	Intermediate Similarity	NPC469687
0.7895	Intermediate Similarity	NPC264900
0.7895	Intermediate Similarity	NPC108659
0.7891	Intermediate Similarity	NPC121001
0.7891	Intermediate Similarity	NPC259767

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 NPC123704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	716
0.2-0.3	1522
0.3-0.4	2845
0.4-0.5	2093
0.5-0.6	1258
0.6-0.7	462
0.7-0.8	31
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
0.8125	Intermediate Similarity	NPD1091	Approved
0.7786	Intermediate Similarity	NPD7266	Discontinued
0.7698	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8455	Phase 2
0.7569	Intermediate Similarity	NPD6190	Approved
0.7538	Intermediate Similarity	NPD9545	Approved
0.7464	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7033	Discontinued
0.7383	Intermediate Similarity	NPD1653	Approved
0.7285	Intermediate Similarity	NPD4380	Phase 2
0.7284	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9495	Approved
0.726	Intermediate Similarity	NPD4628	Phase 3
0.725	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7054	Approved
0.7222	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6798	Discontinued
0.7205	Intermediate Similarity	NPD7074	Phase 3
0.7205	Intermediate Similarity	NPD7472	Approved
0.72	Intermediate Similarity	NPD5048	Discontinued
0.7188	Intermediate Similarity	NPD3818	Discontinued
0.7183	Intermediate Similarity	NPD230	Phase 1
0.7181	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6233	Phase 2
0.7161	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD1759	Phase 1
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD969	Suspended
0.7121	Intermediate Similarity	NPD9493	Approved
0.7117	Intermediate Similarity	NPD7251	Discontinued
0.7115	Intermediate Similarity	NPD7075	Discontinued
0.7114	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2629	Approved
0.7089	Intermediate Similarity	NPD7199	Phase 2
0.7086	Intermediate Similarity	NPD5403	Approved
0.7081	Intermediate Similarity	NPD7228	Approved
0.7078	Intermediate Similarity	NPD37	Approved
0.7073	Intermediate Similarity	NPD7808	Phase 3
0.707	Intermediate Similarity	NPD6234	Discontinued
0.7068	Intermediate Similarity	NPD1758	Phase 1
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7055	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4965	Approved
0.7051	Intermediate Similarity	NPD4967	Phase 2
0.7051	Intermediate Similarity	NPD4966	Approved
0.7037	Intermediate Similarity	NPD1778	Approved
0.7031	Intermediate Similarity	NPD74	Approved
0.7031	Intermediate Similarity	NPD9266	Approved
0.703	Intermediate Similarity	NPD8313	Approved
0.703	Intermediate Similarity	NPD8312	Approved
0.7027	Intermediate Similarity	NPD3400	Discontinued
0.7012	Intermediate Similarity	NPD7685	Pre-registration
0.7012	Intermediate Similarity	NPD6559	Discontinued
0.7007	Intermediate Similarity	NPD1549	Phase 2
0.7007	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD6799	Approved
0.6968	Remote Similarity	NPD6801	Discontinued
0.6966	Remote Similarity	NPD7097	Phase 1
0.6959	Remote Similarity	NPD1652	Phase 2
0.6959	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5401	Approved
0.6953	Remote Similarity	NPD9264	Approved
0.6953	Remote Similarity	NPD290	Approved
0.6953	Remote Similarity	NPD9263	Approved
0.6953	Remote Similarity	NPD9267	Approved
0.6941	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3787	Discontinued
0.6934	Remote Similarity	NPD1535	Discovery
0.6929	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5647	Approved
0.6923	Remote Similarity	NPD520	Approved
0.6923	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4062	Phase 3
0.6906	Remote Similarity	NPD3225	Approved
0.6897	Remote Similarity	NPD6653	Approved
0.6894	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1481	Phase 2
0.6884	Remote Similarity	NPD9269	Phase 2
0.6879	Remote Similarity	NPD5402	Approved
0.6875	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1613	Approved
0.6871	Remote Similarity	NPD1551	Phase 2
0.6871	Remote Similarity	NPD9570	Approved
0.6859	Remote Similarity	NPD1934	Approved
0.6857	Remote Similarity	NPD1203	Approved
0.6857	Remote Similarity	NPD2797	Approved
0.6853	Remote Similarity	NPD3268	Approved
0.6825	Remote Similarity	NPD846	Approved
0.6825	Remote Similarity	NPD940	Approved
0.6815	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD422	Phase 1
0.6803	Remote Similarity	NPD1510	Phase 2
0.6795	Remote Similarity	NPD7411	Suspended
0.6788	Remote Similarity	NPD5125	Phase 3
0.6788	Remote Similarity	NPD17	Approved
0.6788	Remote Similarity	NPD5126	Approved
0.6774	Remote Similarity	NPD7458	Discontinued
0.6772	Remote Similarity	NPD3817	Phase 2
0.6768	Remote Similarity	NPD3751	Discontinued
0.6765	Remote Similarity	NPD1894	Discontinued
0.6763	Remote Similarity	NPD9717	Approved
0.6759	Remote Similarity	NPD825	Approved
0.6759	Remote Similarity	NPD826	Approved
0.6759	Remote Similarity	NPD1240	Approved
0.6759	Remote Similarity	NPD943	Approved
0.6748	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6166	Phase 2
0.6747	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3764	Approved
0.6731	Remote Similarity	NPD6599	Discontinued
0.6716	Remote Similarity	NPD9281	Approved
0.6715	Remote Similarity	NPD9268	Approved
0.6713	Remote Similarity	NPD6832	Phase 2
0.6712	Remote Similarity	NPD1933	Approved
0.6707	Remote Similarity	NPD7240	Approved
0.669	Remote Similarity	NPD6663	Approved
0.6689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD255	Approved
0.6667	Remote Similarity	NPD256	Approved
0.6645	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6100	Approved
0.6644	Remote Similarity	NPD4060	Phase 1
0.6644	Remote Similarity	NPD6099	Approved
0.6644	Remote Similarity	NPD2935	Discontinued
0.6643	Remote Similarity	NPD5736	Approved
0.6642	Remote Similarity	NPD1548	Phase 1
0.6641	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD9261	Approved
0.6627	Remote Similarity	NPD5844	Phase 1
0.6623	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2625	Approved
0.662	Remote Similarity	NPD2627	Approved
0.662	Remote Similarity	NPD2159	Approved
0.662	Remote Similarity	NPD2160	Approved
0.662	Remote Similarity	NPD2628	Approved
0.662	Remote Similarity	NPD2626	Approved
0.662	Remote Similarity	NPD6362	Approved
0.662	Remote Similarity	NPD1164	Approved
0.6619	Remote Similarity	NPD3496	Discontinued
0.6618	Remote Similarity	NPD9568	Approved
0.6613	Remote Similarity	NPD2933	Approved
0.6613	Remote Similarity	NPD2934	Approved
0.6608	Remote Similarity	NPD8150	Discontinued
0.6604	Remote Similarity	NPD7819	Suspended
0.6604	Remote Similarity	NPD1465	Phase 2
0.6604	Remote Similarity	NPD2801	Approved
0.6601	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5762	Approved
0.66	Remote Similarity	NPD5763	Approved
0.6599	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD447	Suspended
0.6599	Remote Similarity	NPD555	Phase 2
0.6599	Remote Similarity	NPD5124	Phase 1
0.6597	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2067	Discontinued
0.6581	Remote Similarity	NPD1512	Approved
0.6579	Remote Similarity	NPD2575	Approved
0.6579	Remote Similarity	NPD3750	Approved
0.6577	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6535	Approved
0.6571	Remote Similarity	NPD1201	Approved
0.6571	Remote Similarity	NPD1610	Phase 2
0.6571	Remote Similarity	NPD6534	Approved
0.6567	Remote Similarity	NPD7843	Approved
0.6565	Remote Similarity	NPD1358	Approved
0.6562	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.656	Remote Similarity	NPD2859	Approved
0.656	Remote Similarity	NPD2860	Approved
0.656	Remote Similarity	NPD844	Approved
0.6556	Remote Similarity	NPD7435	Discontinued
0.6556	Remote Similarity	NPD2424	Discontinued
0.6547	Remote Similarity	NPD5306	Approved
0.6547	Remote Similarity	NPD5305	Approved
0.6535	Remote Similarity	NPD7798	Approved
0.6533	Remote Similarity	NPD2240	Approved
0.6533	Remote Similarity	NPD2239	Approved
0.6533	Remote Similarity	NPD6032	Approved
0.6532	Remote Similarity	NPD845	Approved
0.6528	Remote Similarity	NPD2861	Phase 2
0.6528	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6232	Discontinued
0.6522	Remote Similarity	NPD3882	Suspended
0.6519	Remote Similarity	NPD8319	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