NPASS Compound

Structure

NPC469951 OpenBabel07101718312D 23 25 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 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 -5.1962 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 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 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	319.711
LogP:	2.683
LogD:	2.489
LogS:	-4.015
# Rotatable Bonds:	4
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.939
Synthetic Accessibility Score:	2.945
Fsp3:	0.222
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:	-4.816
MDCK Permeability:	1.4194172763382085e-05
Pgp-inhibitor:	0.853
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.678
Plasma Protein Binding (PPB):	84.60064697265625%
Volume Distribution (VD):	1.59
Pgp-substrate:	7.720759391784668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.852
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.821
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.72
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.51
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.836

ADMET: Excretion

Clearance (CL):	5.148
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.676
Human Hepatotoxicity (H-HT):	0.37
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.931
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.521
Carcinogencity:	0.642
Eye Corrosion:	0.003
Eye Irritation:	0.114
Respiratory Toxicity:	0.437

Download Data

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

Natural Product: NPC469951

Natural Product ID:	NPC469951
*Common Name:**	(4R)-3-(3,4-Dimethoxyphenyl)-7-Methoxy-4H-Chromen-4-Ol
IUPAC Name:	(4R)-3-(3,4-dimethoxyphenyl)-7-methoxy-4H-chromen-4-ol
Synonyms:
Standard InCHIKey:	WCBLYLSEIFDBFU-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-20-12-5-6-13-16(9-12)23-10-14(18(13)19)11-4-7-15(21-2)17(8-11)22-3/h4-10,18-19H,1-3H3/t18-/m0/s1
SMILES:	COC1=CC2=C(C=C1)C(C(=CO2)C3=CC(=C(C=C3)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL13298
PubChem CID:	44268644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002602] 7-O-methylated isoflavonoids

*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
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(79)80020-5]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[10328294]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	16.0	ug.mL-1	PMID[488805]

☑ 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 NPC469951 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	389
0.1-0.2	1550
0.2-0.3	4684
0.3-0.4	12559
0.4-0.5	5441
0.5-0.6	4148
0.6-0.7	7120
0.7-0.8	5154
0.8-0.85	890
0.85-0.9	564
0.9-0.95	191
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469963
0.9675	High Similarity	NPC242032
0.952	High Similarity	NPC212015
0.9512	High Similarity	NPC105925
0.944	High Similarity	NPC98631
0.944	High Similarity	NPC186843
0.944	High Similarity	NPC206615
0.944	High Similarity	NPC470213
0.938	High Similarity	NPC61946
0.9375	High Similarity	NPC475840
0.9375	High Similarity	NPC263064
0.9365	High Similarity	NPC170844
0.9365	High Similarity	NPC476968
0.936	High Similarity	NPC82679
0.936	High Similarity	NPC74817
0.936	High Similarity	NPC236791
0.936	High Similarity	NPC324112
0.936	High Similarity	NPC169474
0.936	High Similarity	NPC159968
0.936	High Similarity	NPC246620
0.936	High Similarity	NPC293054
0.936	High Similarity	NPC282000
0.936	High Similarity	NPC124452
0.935	High Similarity	NPC282496
0.935	High Similarity	NPC233526
0.9308	High Similarity	NPC306441
0.9308	High Similarity	NPC16435
0.9297	High Similarity	NPC201587
0.9297	High Similarity	NPC253105
0.928	High Similarity	NPC223136
0.928	High Similarity	NPC28730
0.928	High Similarity	NPC78974
0.928	High Similarity	NPC18924
0.928	High Similarity	NPC214406
0.928	High Similarity	NPC223953
0.928	High Similarity	NPC44748
0.928	High Similarity	NPC103823
0.9231	High Similarity	NPC234333
0.9231	High Similarity	NPC260898
0.9231	High Similarity	NPC94750
0.9231	High Similarity	NPC47398
0.9231	High Similarity	NPC121812
0.9231	High Similarity	NPC112246
0.9231	High Similarity	NPC256262
0.9231	High Similarity	NPC474206
0.9231	High Similarity	NPC112939
0.9231	High Similarity	NPC470356
0.9225	High Similarity	NPC168059
0.9225	High Similarity	NPC229442
0.9219	High Similarity	NPC474017
0.9213	High Similarity	NPC210623
0.9213	High Similarity	NPC273295
0.9213	High Similarity	NPC222004
0.9213	High Similarity	NPC226788
0.9213	High Similarity	NPC285339
0.9213	High Similarity	NPC3439
0.9213	High Similarity	NPC190629
0.9213	High Similarity	NPC202582
0.9213	High Similarity	NPC218856
0.9213	High Similarity	NPC470258
0.9206	High Similarity	NPC474119
0.92	High Similarity	NPC82483
0.92	High Similarity	NPC17943
0.92	High Similarity	NPC57490
0.92	High Similarity	NPC203133
0.92	High Similarity	NPC298757
0.92	High Similarity	NPC475169
0.92	High Similarity	NPC251855
0.92	High Similarity	NPC234400
0.92	High Similarity	NPC193544
0.92	High Similarity	NPC221077
0.92	High Similarity	NPC60885
0.92	High Similarity	NPC208950
0.92	High Similarity	NPC117214
0.92	High Similarity	NPC116907
0.92	High Similarity	NPC299584
0.92	High Similarity	NPC265483
0.92	High Similarity	NPC472093
0.92	High Similarity	NPC233410
0.9187	High Similarity	NPC75713
0.9167	High Similarity	NPC471388
0.916	High Similarity	NPC474639
0.916	High Similarity	NPC472334
0.916	High Similarity	NPC230734
0.916	High Similarity	NPC302701
0.916	High Similarity	NPC472336
0.916	High Similarity	NPC269091
0.916	High Similarity	NPC227503
0.9154	High Similarity	NPC317380
0.9141	High Similarity	NPC224157
0.9141	High Similarity	NPC234488
0.9141	High Similarity	NPC311680
0.9141	High Similarity	NPC192687
0.9141	High Similarity	NPC299221
0.9141	High Similarity	NPC472338
0.9141	High Similarity	NPC126836
0.9141	High Similarity	NPC51840
0.9141	High Similarity	NPC91291
0.9134	High Similarity	NPC28765
0.9134	High Similarity	NPC31707
0.9134	High Similarity	NPC154866
0.9106	High Similarity	NPC166759
0.9098	High Similarity	NPC254625
0.9098	High Similarity	NPC475961
0.9091	High Similarity	NPC107551
0.9091	High Similarity	NPC477938
0.9091	High Similarity	NPC103976
0.9091	High Similarity	NPC474282
0.9091	High Similarity	NPC211549
0.9091	High Similarity	NPC326797
0.9091	High Similarity	NPC102904
0.9091	High Similarity	NPC176051
0.9084	High Similarity	NPC472337
0.9084	High Similarity	NPC195022
0.9084	High Similarity	NPC164787
0.9084	High Similarity	NPC151224
0.9077	High Similarity	NPC112237
0.9077	High Similarity	NPC11060
0.9077	High Similarity	NPC58585
0.907	High Similarity	NPC472597
0.907	High Similarity	NPC469613
0.907	High Similarity	NPC470095
0.907	High Similarity	NPC470096
0.907	High Similarity	NPC30043
0.907	High Similarity	NPC469625
0.9062	High Similarity	NPC58164
0.9062	High Similarity	NPC10225
0.9062	High Similarity	NPC190144
0.9055	High Similarity	NPC252131
0.9055	High Similarity	NPC127587
0.9055	High Similarity	NPC236760
0.9055	High Similarity	NPC266555
0.904	High Similarity	NPC136319
0.904	High Similarity	NPC121115
0.904	High Similarity	NPC197757
0.904	High Similarity	NPC228922
0.904	High Similarity	NPC95168
0.904	High Similarity	NPC471693
0.903	High Similarity	NPC471389
0.9024	High Similarity	NPC474565
0.9023	High Similarity	NPC184613
0.9016	High Similarity	NPC474214
0.9016	High Similarity	NPC63083
0.9015	High Similarity	NPC173660
0.9015	High Similarity	NPC162659
0.9015	High Similarity	NPC270456
0.9015	High Similarity	NPC248727
0.9015	High Similarity	NPC470802
0.9015	High Similarity	NPC265433
0.9008	High Similarity	NPC106215
0.9008	High Similarity	NPC478085
0.9008	High Similarity	NPC287745
0.9008	High Similarity	NPC170694
0.9	High Similarity	NPC261619
0.9	High Similarity	NPC7903
0.9	High Similarity	NPC127624
0.9	High Similarity	NPC202762
0.9	High Similarity	NPC185604
0.9	High Similarity	NPC16208
0.9	High Similarity	NPC219876
0.9	High Similarity	NPC470752
0.9	High Similarity	NPC126029
0.9	High Similarity	NPC86655
0.9	High Similarity	NPC35932
0.9	High Similarity	NPC15658
0.9	High Similarity	NPC61477
0.9	High Similarity	NPC160991
0.9	High Similarity	NPC78770
0.9	High Similarity	NPC184447
0.9	High Similarity	NPC6451
0.8992	High Similarity	NPC469614
0.8992	High Similarity	NPC469612
0.8984	High Similarity	NPC252307
0.8984	High Similarity	NPC266691
0.8984	High Similarity	NPC245826
0.8984	High Similarity	NPC474178
0.8976	High Similarity	NPC76451
0.896	High Similarity	NPC270326
0.896	High Similarity	NPC41562
0.896	High Similarity	NPC262253
0.896	High Similarity	NPC71579
0.896	High Similarity	NPC261661
0.896	High Similarity	NPC473411
0.8955	High Similarity	NPC27495
0.8955	High Similarity	NPC184797
0.8955	High Similarity	NPC22317
0.8955	High Similarity	NPC309124
0.8947	High Similarity	NPC86605
0.8947	High Similarity	NPC276490
0.8947	High Similarity	NPC3072
0.8947	High Similarity	NPC46277
0.8947	High Similarity	NPC301765
0.8947	High Similarity	NPC156948
0.8943	High Similarity	NPC474320
0.8939	High Similarity	NPC473413
0.8939	High Similarity	NPC158142
0.8939	High Similarity	NPC294884
0.8939	High Similarity	NPC200557
0.8939	High Similarity	NPC111655
0.8939	High Similarity	NPC108198

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 NPC469951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	897
0.2-0.3	1776
0.3-0.4	2729
0.4-0.5	1638
0.5-0.6	918
0.6-0.7	684
0.7-0.8	156
0.8-0.85	10
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9365	High Similarity	NPD3027	Phase 3
0.9	High Similarity	NPD1612	Clinical (unspecified phase)
0.9	High Similarity	NPD1613	Approved
0.8692	High Similarity	NPD1529	Clinical (unspecified phase)
0.8615	High Similarity	NPD1530	Clinical (unspecified phase)
0.8615	High Similarity	NPD3018	Phase 2
0.845	Intermediate Similarity	NPD2983	Phase 2
0.845	Intermediate Similarity	NPD2982	Phase 2
0.8413	Intermediate Similarity	NPD1548	Phase 1
0.8409	Intermediate Similarity	NPD4908	Phase 1
0.8372	Intermediate Similarity	NPD2981	Phase 2
0.8306	Intermediate Similarity	NPD5283	Phase 1
0.8295	Intermediate Similarity	NPD1610	Phase 2
0.8284	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1934	Approved
0.8041	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD228	Approved
0.7985	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4005	Discontinued
0.7943	Intermediate Similarity	NPD3540	Phase 1
0.7941	Intermediate Similarity	NPD4625	Phase 3
0.7926	Intermediate Similarity	NPD2861	Phase 2
0.7895	Intermediate Similarity	NPD4749	Approved
0.7891	Intermediate Similarity	NPD1653	Approved
0.7883	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD4966	Approved
0.7881	Intermediate Similarity	NPD4967	Phase 2
0.7881	Intermediate Similarity	NPD4965	Approved
0.7872	Intermediate Similarity	NPD3539	Phase 1
0.7867	Intermediate Similarity	NPD2801	Approved
0.7867	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD5177	Phase 3
0.7829	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1357	Approved
0.777	Intermediate Similarity	NPD3620	Phase 2
0.777	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6166	Phase 2
0.7756	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5124	Phase 1
0.7708	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3060	Approved
0.7697	Intermediate Similarity	NPD3817	Phase 2
0.7677	Intermediate Similarity	NPD7199	Phase 2
0.7676	Intermediate Similarity	NPD1510	Phase 2
0.7667	Intermediate Similarity	NPD4380	Phase 2
0.7662	Intermediate Similarity	NPD6234	Discontinued
0.7658	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3882	Suspended
0.7634	Intermediate Similarity	NPD5536	Phase 2
0.763	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4357	Discontinued
0.7619	Intermediate Similarity	NPD1511	Approved
0.7619	Intermediate Similarity	NPD7213	Phase 3
0.7619	Intermediate Similarity	NPD2684	Approved
0.7619	Intermediate Similarity	NPD7212	Phase 2
0.7612	Intermediate Similarity	NPD1091	Approved
0.7612	Intermediate Similarity	NPD3705	Approved
0.7612	Intermediate Similarity	NPD422	Phase 1
0.761	Intermediate Similarity	NPD5844	Phase 1
0.761	Intermediate Similarity	NPD7054	Approved
0.7586	Intermediate Similarity	NPD4237	Approved
0.7586	Intermediate Similarity	NPD6674	Discontinued
0.7586	Intermediate Similarity	NPD1652	Phase 2
0.7586	Intermediate Similarity	NPD4236	Phase 3
0.7574	Intermediate Similarity	NPD8651	Approved
0.7568	Intermediate Similarity	NPD7447	Phase 1
0.7562	Intermediate Similarity	NPD7472	Approved
0.7562	Intermediate Similarity	NPD7074	Phase 3
0.7561	Intermediate Similarity	NPD846	Approved
0.7561	Intermediate Similarity	NPD940	Approved
0.7559	Intermediate Similarity	NPD3022	Approved
0.7559	Intermediate Similarity	NPD3021	Approved
0.7551	Intermediate Similarity	NPD7124	Phase 2
0.755	Intermediate Similarity	NPD4678	Approved
0.755	Intermediate Similarity	NPD4675	Approved
0.754	Intermediate Similarity	NPD290	Approved
0.7519	Intermediate Similarity	NPD7843	Approved
0.7518	Intermediate Similarity	NPD4060	Phase 1
0.7518	Intermediate Similarity	NPD2238	Phase 2
0.7517	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2796	Approved
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4538	Approved
0.7481	Intermediate Similarity	NPD7157	Approved
0.748	Intermediate Similarity	NPD1242	Phase 1
0.7468	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7266	Discontinued
0.7448	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7228	Approved
0.7431	Intermediate Similarity	NPD7033	Discontinued
0.7423	Intermediate Similarity	NPD7808	Phase 3
0.7422	Intermediate Similarity	NPD4750	Phase 3
0.7415	Intermediate Similarity	NPD3892	Phase 2
0.7415	Intermediate Similarity	NPD6331	Phase 2
0.7407	Intermediate Similarity	NPD6797	Phase 2
0.7397	Intermediate Similarity	NPD1549	Phase 2
0.7394	Intermediate Similarity	NPD1558	Phase 1
0.7394	Intermediate Similarity	NPD1240	Approved
0.7389	Intermediate Similarity	NPD5494	Approved
0.7376	Intermediate Similarity	NPD6798	Discontinued
0.7375	Intermediate Similarity	NPD7473	Discontinued
0.7372	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4055	Discovery
0.7368	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5241	Discontinued
0.7365	Intermediate Similarity	NPD2219	Phase 1
0.7362	Intermediate Similarity	NPD7251	Discontinued
0.7361	Intermediate Similarity	NPD6111	Discontinued
0.7348	Intermediate Similarity	NPD6671	Approved
0.7338	Intermediate Similarity	NPD6801	Discontinued
0.7338	Intermediate Similarity	NPD6584	Phase 3
0.7333	Intermediate Similarity	NPD6516	Phase 2
0.7333	Intermediate Similarity	NPD5846	Approved
0.7329	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2922	Phase 1
0.7317	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7549	Discontinued
0.731	Intermediate Similarity	NPD5960	Phase 3
0.731	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5588	Approved
0.731	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3750	Approved
0.7292	Intermediate Similarity	NPD1607	Approved
0.729	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5451	Approved
0.7285	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7075	Discontinued
0.726	Intermediate Similarity	NPD6100	Approved
0.726	Intermediate Similarity	NPD6099	Approved
0.7254	Intermediate Similarity	NPD5110	Phase 2
0.7254	Intermediate Similarity	NPD5109	Approved
0.7254	Intermediate Similarity	NPD5111	Phase 2
0.7248	Intermediate Similarity	NPD2677	Approved
0.7244	Intermediate Similarity	NPD2563	Approved
0.7244	Intermediate Similarity	NPD5402	Approved
0.7244	Intermediate Similarity	NPD2560	Approved
0.7237	Intermediate Similarity	NPD5403	Approved
0.7234	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4162	Approved
0.7222	Intermediate Similarity	NPD5735	Approved
0.7222	Intermediate Similarity	NPD3657	Discovery
0.7222	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4123	Phase 3
0.7211	Intermediate Similarity	NPD5762	Approved
0.7211	Intermediate Similarity	NPD5763	Approved
0.7206	Intermediate Similarity	NPD4626	Approved
0.72	Intermediate Similarity	NPD5058	Phase 3
0.7197	Intermediate Similarity	NPD6788	Approved
0.7195	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7095	Approved
0.7181	Intermediate Similarity	NPD4110	Phase 3
0.7181	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4628	Phase 3
0.7179	Intermediate Similarity	NPD7819	Suspended
0.7172	Intermediate Similarity	NPD4097	Suspended
0.7171	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5090	Approved
0.7161	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5089	Approved
0.7154	Intermediate Similarity	NPD2859	Approved
0.7154	Intermediate Similarity	NPD2860	Approved
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD291	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6190	Approved
0.7133	Intermediate Similarity	NPD5718	Phase 2
0.7122	Intermediate Similarity	NPD6582	Phase 2
0.7122	Intermediate Similarity	NPD6583	Phase 3
0.7121	Intermediate Similarity	NPD5535	Approved
0.712	Intermediate Similarity	NPD3020	Approved
0.7105	Intermediate Similarity	NPD5401	Approved
0.7105	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4340	Discontinued
0.7095	Intermediate Similarity	NPD1375	Discontinued
0.7083	Intermediate Similarity	NPD2674	Phase 3
0.7083	Intermediate Similarity	NPD6233	Phase 2
0.7083	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6071	Discontinued
0.7078	Intermediate Similarity	NPD3687	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