NPASS Compound

Structure

CID15543 OpenBabel06191715342D 30 31 0 0 0 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 2.5981 -1.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 0.8660 -2.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 0.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 30 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 14 1 0 0 0 0 10 18 2 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 19 25 2 0 0 0 0 20 22 1 0 0 0 0 21 27 1 0 0 0 0 22 23 2 0 0 0 0 23 26 1 0 0 0 0 24 26 2 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.25
Volume:	455.208
LogP:	7.021
LogD:	4.277
LogS:	-3.567
# Rotatable Bonds:	9
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.35
Synthetic Accessibility Score:	2.905
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.95
MDCK Permeability:	2.2394213374354877e-05
Pgp-inhibitor:	0.608
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	97.76610565185547%
Volume Distribution (VD):	6.168
Pgp-substrate:	4.315205097198486%

ADMET: Metabolism

CYP1A2-inhibitor:	0.917
CYP1A2-substrate:	0.367
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.689
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.9
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.423
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	15.527
Half-life (T1/2):	0.685

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.821
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.203
Skin Sensitization:	0.955
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.576
Respiratory Toxicity:	0.302

Download Data

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

Natural Product: NPC15543

Natural Product ID:	NPC15543
*Common Name:**	Kazinol J
IUPAC Name:	5-[3-(4-hydroxy-2-methoxyphenyl)propyl]-3,4-bis(3-methylbut-2-enyl)benzene-1,2-diol
Synonyms:	Kazinol J
Standard InCHIKey:	BUWRWZUUCOLPSX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H34O4/c1-17(2)9-13-22-20(15-24(28)26(29)23(22)14-10-18(3)4)8-6-7-19-11-12-21(27)16-25(19)30-5/h9-12,15-16,27-29H,6-8,13-14H2,1-5H3
SMILES:	COc1cc(O)ccc1CCCc1cc(O)c(c(c1CC=C(C)C)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464845
PubChem CID:	21637732
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[11575957]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19046886]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20493686]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917310]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456196]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456196]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456196]

☑ 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 NPC15543 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	418
0.1-0.2	1721
0.2-0.3	4721
0.3-0.4	13061
0.4-0.5	4877
0.5-0.6	3964
0.6-0.7	6967
0.7-0.8	5467
0.8-0.85	820
0.85-0.9	482
0.9-0.95	185
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC126836
0.9444	High Similarity	NPC28765
0.9389	High Similarity	NPC242715
0.9389	High Similarity	NPC56329
0.9385	High Similarity	NPC313081
0.9385	High Similarity	NPC69029
0.9385	High Similarity	NPC10314
0.9385	High Similarity	NPC294884
0.9385	High Similarity	NPC108198
0.9385	High Similarity	NPC158142
0.9385	High Similarity	NPC241241
0.9385	High Similarity	NPC200557
0.938	High Similarity	NPC32778
0.9365	High Similarity	NPC324112
0.9365	High Similarity	NPC74817
0.9365	High Similarity	NPC159968
0.9365	High Similarity	NPC169474
0.9365	High Similarity	NPC236791
0.9365	High Similarity	NPC293054
0.9365	High Similarity	NPC252131
0.9365	High Similarity	NPC246620
0.9365	High Similarity	NPC124452
0.9365	High Similarity	NPC82679
0.9365	High Similarity	NPC282000
0.9355	High Similarity	NPC136319
0.9318	High Similarity	NPC32630
0.9318	High Similarity	NPC220344
0.9318	High Similarity	NPC132804
0.9318	High Similarity	NPC243996
0.9318	High Similarity	NPC275061
0.9313	High Similarity	NPC143139
0.9313	High Similarity	NPC202846
0.9313	High Similarity	NPC30632
0.9308	High Similarity	NPC209199
0.9308	High Similarity	NPC125649
0.9291	High Similarity	NPC154866
0.9286	High Similarity	NPC18924
0.9286	High Similarity	NPC78974
0.9286	High Similarity	NPC214406
0.9286	High Similarity	NPC28730
0.9286	High Similarity	NPC223136
0.9286	High Similarity	NPC103823
0.9286	High Similarity	NPC44748
0.9248	High Similarity	NPC308768
0.9248	High Similarity	NPC12668
0.9242	High Similarity	NPC266453
0.9242	High Similarity	NPC22902
0.9242	High Similarity	NPC230919
0.9242	High Similarity	NPC200935
0.9237	High Similarity	NPC256262
0.9213	High Similarity	NPC127587
0.9213	High Similarity	NPC266555
0.9206	High Similarity	NPC117214
0.9206	High Similarity	NPC203133
0.9206	High Similarity	NPC475169
0.9206	High Similarity	NPC60885
0.9206	High Similarity	NPC82483
0.9206	High Similarity	NPC208950
0.9206	High Similarity	NPC234400
0.9206	High Similarity	NPC233410
0.9206	High Similarity	NPC105925
0.9206	High Similarity	NPC193544
0.9206	High Similarity	NPC17943
0.9206	High Similarity	NPC299584
0.9206	High Similarity	NPC298757
0.9206	High Similarity	NPC57490
0.9206	High Similarity	NPC105031
0.9206	High Similarity	NPC251855
0.9206	High Similarity	NPC116907
0.9206	High Similarity	NPC265483
0.9206	High Similarity	NPC221077
0.9206	High Similarity	NPC472093
0.92	High Similarity	NPC84086
0.9194	High Similarity	NPC237667
0.9194	High Similarity	NPC476633
0.9179	High Similarity	NPC265075
0.9173	High Similarity	NPC212942
0.9173	High Similarity	NPC29868
0.9173	High Similarity	NPC79622
0.9173	High Similarity	NPC243759
0.9173	High Similarity	NPC218131
0.9173	High Similarity	NPC184613
0.9173	High Similarity	NPC105847
0.9167	High Similarity	NPC234952
0.916	High Similarity	NPC188378
0.916	High Similarity	NPC276026
0.916	High Similarity	NPC469659
0.916	High Similarity	NPC555
0.916	High Similarity	NPC7515
0.916	High Similarity	NPC289258
0.916	High Similarity	NPC56764
0.916	High Similarity	NPC160697
0.916	High Similarity	NPC206737
0.9154	High Similarity	NPC14224
0.9154	High Similarity	NPC6451
0.9154	High Similarity	NPC161958
0.9147	High Similarity	NPC311680
0.9147	High Similarity	NPC299221
0.9147	High Similarity	NPC234488
0.9147	High Similarity	NPC51840
0.9134	High Similarity	NPC223953
0.9134	High Similarity	NPC76451
0.9118	High Similarity	NPC50250
0.9118	High Similarity	NPC473845
0.9113	High Similarity	NPC102639
0.9111	High Similarity	NPC175838
0.9111	High Similarity	NPC183709
0.9104	High Similarity	NPC472092
0.9104	High Similarity	NPC472090
0.9104	High Similarity	NPC472091
0.9104	High Similarity	NPC234568
0.9104	High Similarity	NPC198038
0.9098	High Similarity	NPC35550
0.9098	High Similarity	NPC151656
0.9098	High Similarity	NPC266006
0.9091	High Similarity	NPC180602
0.9091	High Similarity	NPC55239
0.9091	High Similarity	NPC473413
0.9091	High Similarity	NPC240279
0.9091	High Similarity	NPC214853
0.9077	High Similarity	NPC12275
0.9077	High Similarity	NPC45715
0.9077	High Similarity	NPC232275
0.9077	High Similarity	NPC474356
0.907	High Similarity	NPC10225
0.907	High Similarity	NPC212015
0.907	High Similarity	NPC58164
0.9062	High Similarity	NPC473221
0.9062	High Similarity	NPC236760
0.9062	High Similarity	NPC21563
0.9055	High Similarity	NPC113495
0.9048	High Similarity	NPC121115
0.9048	High Similarity	NPC53567
0.9048	High Similarity	NPC228922
0.9048	High Similarity	NPC233526
0.9048	High Similarity	NPC197757
0.9048	High Similarity	NPC95168
0.9048	High Similarity	NPC282496
0.9044	High Similarity	NPC474104
0.9037	High Similarity	NPC71046
0.9037	High Similarity	NPC472089
0.903	High Similarity	NPC230124
0.903	High Similarity	NPC471183
0.903	High Similarity	NPC114171
0.903	High Similarity	NPC260741
0.903	High Similarity	NPC6300
0.903	High Similarity	NPC70682
0.9023	High Similarity	NPC133025
0.9023	High Similarity	NPC205442
0.9	High Similarity	NPC224157
0.9	High Similarity	NPC192687
0.9	High Similarity	NPC254000
0.8992	High Similarity	NPC186843
0.8992	High Similarity	NPC98631
0.8992	High Similarity	NPC266691
0.8992	High Similarity	NPC470213
0.8992	High Similarity	NPC206615
0.8984	High Similarity	NPC170485
0.8984	High Similarity	NPC82299
0.8978	High Similarity	NPC469795
0.8978	High Similarity	NPC473108
0.8976	High Similarity	NPC5796
0.8976	High Similarity	NPC206487
0.8971	High Similarity	NPC472088
0.8971	High Similarity	NPC470917
0.8971	High Similarity	NPC472087
0.8968	High Similarity	NPC71579
0.8968	High Similarity	NPC473411
0.8968	High Similarity	NPC262253
0.8968	High Similarity	NPC41562
0.8963	High Similarity	NPC295719
0.8963	High Similarity	NPC34431
0.8963	High Similarity	NPC165026
0.8963	High Similarity	NPC109240
0.8963	High Similarity	NPC73505
0.8963	High Similarity	NPC266650
0.8955	High Similarity	NPC301765
0.8955	High Similarity	NPC46277
0.8955	High Similarity	NPC156948
0.8955	High Similarity	NPC86605
0.8955	High Similarity	NPC3072
0.8952	High Similarity	NPC217174
0.8952	High Similarity	NPC226629
0.8939	High Similarity	NPC475840
0.8939	High Similarity	NPC11060
0.8931	High Similarity	NPC282508
0.8931	High Similarity	NPC469907
0.8931	High Similarity	NPC474017
0.8923	High Similarity	NPC190144
0.8923	High Similarity	NPC476968
0.8923	High Similarity	NPC170844
0.8921	High Similarity	NPC262297
0.8915	High Similarity	NPC470699
0.8915	High Similarity	NPC210355
0.8905	High Similarity	NPC469630
0.8897	High Similarity	NPC19158
0.8897	High Similarity	NPC263261
0.8897	High Similarity	NPC35216
0.8897	High Similarity	NPC87725
0.8889	High Similarity	NPC75713

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 NPC15543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	981
0.2-0.3	1657
0.3-0.4	2782
0.4-0.5	1670
0.5-0.6	890
0.6-0.7	656
0.7-0.8	137
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8923	High Similarity	NPD3027	Phase 3
0.8702	High Similarity	NPD1529	Clinical (unspecified phase)
0.8626	High Similarity	NPD1530	Clinical (unspecified phase)
0.8582	High Similarity	NPD1612	Clinical (unspecified phase)
0.8582	High Similarity	NPD1613	Approved
0.8496	Intermediate Similarity	NPD4625	Phase 3
0.8433	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD4908	Phase 1
0.8209	Intermediate Similarity	NPD3018	Phase 2
0.8168	Intermediate Similarity	NPD1610	Phase 2
0.8134	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD2983	Phase 2
0.8045	Intermediate Similarity	NPD2982	Phase 2
0.8043	Intermediate Similarity	NPD4060	Phase 1
0.8031	Intermediate Similarity	NPD5283	Phase 1
0.8016	Intermediate Similarity	NPD228	Approved
0.8	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3022	Approved
0.8	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD1548	Phase 1
0.797	Intermediate Similarity	NPD2981	Phase 2
0.791	Intermediate Similarity	NPD4749	Approved
0.7899	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6234	Discontinued
0.7786	Intermediate Similarity	NPD3620	Phase 2
0.7786	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6232	Discontinued
0.7744	Intermediate Similarity	NPD4626	Approved
0.7722	Intermediate Similarity	NPD7473	Discontinued
0.7697	Intermediate Similarity	NPD1934	Approved
0.7697	Intermediate Similarity	NPD37	Approved
0.7681	Intermediate Similarity	NPD2861	Phase 2
0.7647	Intermediate Similarity	NPD2801	Approved
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1511	Approved
0.7603	Intermediate Similarity	NPD6674	Discontinued
0.7591	Intermediate Similarity	NPD8651	Approved
0.7591	Intermediate Similarity	NPD6696	Suspended
0.7586	Intermediate Similarity	NPD3540	Phase 1
0.7586	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD846	Approved
0.7581	Intermediate Similarity	NPD940	Approved
0.7578	Intermediate Similarity	NPD4750	Phase 3
0.7562	Intermediate Similarity	NPD7228	Approved
0.7552	Intermediate Similarity	NPD4097	Suspended
0.7548	Intermediate Similarity	NPD4965	Approved
0.7548	Intermediate Similarity	NPD3882	Suspended
0.7548	Intermediate Similarity	NPD4966	Approved
0.7548	Intermediate Similarity	NPD4967	Phase 2
0.7533	Intermediate Similarity	NPD1512	Approved
0.7532	Intermediate Similarity	NPD7819	Suspended
0.7517	Intermediate Similarity	NPD6099	Approved
0.7517	Intermediate Similarity	NPD3539	Phase 1
0.7517	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD4005	Discontinued
0.75	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD1242	Phase 1
0.7468	Intermediate Similarity	NPD7199	Phase 2
0.7467	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7124	Phase 2
0.7436	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3750	Approved
0.7432	Intermediate Similarity	NPD3892	Phase 2
0.7415	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1240	Approved
0.7413	Intermediate Similarity	NPD1558	Phase 1
0.7407	Intermediate Similarity	NPD1651	Approved
0.7407	Intermediate Similarity	NPD5691	Approved
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD7635	Approved
0.74	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7041	Phase 2
0.7397	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD1669	Approved
0.7389	Intermediate Similarity	NPD4055	Discovery
0.7383	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7157	Approved
0.7361	Intermediate Similarity	NPD5735	Approved
0.7351	Intermediate Similarity	NPD7447	Phase 1
0.7349	Intermediate Similarity	NPD8053	Approved
0.7349	Intermediate Similarity	NPD8054	Approved
0.7347	Intermediate Similarity	NPD5762	Approved
0.7347	Intermediate Similarity	NPD5763	Approved
0.7338	Intermediate Similarity	NPD4380	Phase 2
0.7338	Intermediate Similarity	NPD1283	Approved
0.7329	Intermediate Similarity	NPD1510	Phase 2
0.7329	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6166	Phase 2
0.7329	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1653	Approved
0.7315	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1607	Approved
0.7308	Intermediate Similarity	NPD1465	Phase 2
0.7303	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2238	Phase 2
0.7292	Intermediate Similarity	NPD943	Approved
0.7285	Intermediate Similarity	NPD4357	Discontinued
0.728	Intermediate Similarity	NPD3020	Approved
0.7278	Intermediate Similarity	NPD7075	Discontinued
0.7278	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5110	Phase 2
0.7273	Intermediate Similarity	NPD5111	Phase 2
0.7273	Intermediate Similarity	NPD5109	Approved
0.7273	Intermediate Similarity	NPD7843	Approved
0.7261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6111	Discontinued
0.7259	Intermediate Similarity	NPD5536	Phase 2
0.7256	Intermediate Similarity	NPD7074	Phase 3
0.7241	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5124	Phase 1
0.7239	Intermediate Similarity	NPD709	Approved
0.7237	Intermediate Similarity	NPD2532	Approved
0.7237	Intermediate Similarity	NPD2534	Approved
0.7237	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2533	Approved
0.7234	Intermediate Similarity	NPD4624	Approved
0.7231	Intermediate Similarity	NPD2684	Approved
0.723	Intermediate Similarity	NPD7266	Discontinued
0.7215	Intermediate Similarity	NPD7768	Phase 2
0.7205	Intermediate Similarity	NPD7229	Phase 3
0.7203	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7054	Approved
0.7194	Intermediate Similarity	NPD2230	Approved
0.7194	Intermediate Similarity	NPD2233	Approved
0.7194	Intermediate Similarity	NPD2232	Approved
0.7185	Intermediate Similarity	NPD7340	Approved
0.7179	Intermediate Similarity	NPD5090	Approved
0.7179	Intermediate Similarity	NPD6072	Discontinued
0.7179	Intermediate Similarity	NPD5089	Approved
0.7177	Intermediate Similarity	NPD2860	Approved
0.7177	Intermediate Similarity	NPD2859	Approved
0.7171	Intermediate Similarity	NPD7213	Phase 3
0.7171	Intermediate Similarity	NPD7212	Phase 2
0.7163	Intermediate Similarity	NPD3094	Phase 2
0.7154	Intermediate Similarity	NPD2342	Discontinued
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7152	Intermediate Similarity	NPD2677	Approved
0.7152	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7143	Intermediate Similarity	NPD4536	Approved
0.7143	Intermediate Similarity	NPD4538	Approved
0.7143	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7134	Intermediate Similarity	NPD3818	Discontinued
0.7133	Intermediate Similarity	NPD3060	Approved
0.7124	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD230	Phase 1
0.7123	Intermediate Similarity	NPD6355	Discontinued
0.7122	Intermediate Similarity	NPD1611	Approved
0.7122	Intermediate Similarity	NPD1091	Approved
0.7122	Intermediate Similarity	NPD3092	Approved
0.7122	Intermediate Similarity	NPD1281	Approved
0.7115	Intermediate Similarity	NPD4675	Approved
0.7115	Intermediate Similarity	NPD4678	Approved
0.7114	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6584	Phase 3
0.7111	Intermediate Similarity	NPD6387	Discontinued
0.7103	Intermediate Similarity	NPD2674	Phase 3
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7095	Intermediate Similarity	NPD4108	Discontinued
0.7095	Intermediate Similarity	NPD3748	Approved
0.709	Intermediate Similarity	NPD1398	Phase 1
0.7081	Intermediate Similarity	NPD5494	Approved
0.707	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1549	Phase 2
0.7066	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD7251	Discontinued
0.7059	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5451	Approved
0.7039	Intermediate Similarity	NPD2219	Phase 1
0.7032	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1357	Approved
0.7023	Intermediate Similarity	NPD290	Approved
0.702	Intermediate Similarity	NPD5177	Phase 3
0.7007	Intermediate Similarity	NPD3657	Discovery
0.7006	Intermediate Similarity	NPD6797	Phase 2
0.6993	Remote Similarity	NPD6667	Approved
0.6993	Remote Similarity	NPD6666	Approved
0.698	Remote Similarity	NPD5588	Approved
0.698	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.698	Remote Similarity	NPD651	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5960	Phase 3
0.6978	Remote Similarity	NPD2668	Approved
0.6978	Remote Similarity	NPD2667	Approved
0.6975	Remote Similarity	NPD4666	Phase 3
0.6974	Remote Similarity	NPD6331	Phase 2
0.6974	Remote Similarity	NPD7466	Approved
0.6974	Remote Similarity	NPD8166	Discontinued
0.6972	Remote Similarity	NPD2922	Phase 1

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