NPASS Compound

Structure

NPC471391 OpenBabel07101719512D 25 27 0 0 0 0 0 0 0 0999 V2000 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 24 1 0 0 0 0 11 25 1 0 0 0 0 13 17 2 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.13
Volume:	345.797
LogP:	2.834
LogD:	3.425
LogS:	-3.581
# Rotatable Bonds:	6
TPSA:	66.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.866
Synthetic Accessibility Score:	2.595
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.722
MDCK Permeability:	1.6677548046573065e-05
Pgp-inhibitor:	0.339
Pgp-substrate:	0.848
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	94.39671325683594%
Volume Distribution (VD):	0.581
Pgp-substrate:	5.901617527008057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.946
CYP2C19-substrate:	0.704
CYP2C9-inhibitor:	0.592
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.925
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.72

ADMET: Excretion

Clearance (CL):	13.59
Half-life (T1/2):	0.54

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.298
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.946
Carcinogencity:	0.895
Eye Corrosion:	0.004
Eye Irritation:	0.61
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC471391

Natural Product ID:	NPC471391
*Common Name:**	Rugosaflavonoid G
IUPAC Name:	2,3-dimethoxy-4-[(E)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-enyl]phenol
Synonyms:
Standard InCHIKey:	QIXCQNYHYZQJRY-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C19H20O6/c1-21-15-9-12(10-16-19(15)25-11-24-16)5-4-6-13-7-8-14(20)18(23-3)17(13)22-2/h4-5,7-10,20H,6,11H2,1-3H3/b5-4+
SMILES:	COc1c(O)ccc(c1OC)C/C=C/c1cc(OC)c2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431349
PubChem CID:	72701898
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	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
IC50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[530967]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[530967]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[530967]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[530967]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[530967]

☑ 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 NPC471391 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	382
0.1-0.2	1848
0.2-0.3	5598
0.3-0.4	13009
0.4-0.5	4295
0.5-0.6	4394
0.6-0.7	7466
0.7-0.8	4263
0.8-0.85	923
0.85-0.9	405
0.9-0.95	101
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471390
0.9683	High Similarity	NPC228769
0.9683	High Similarity	NPC470633
0.9606	High Similarity	NPC63574
0.9606	High Similarity	NPC184814
0.9545	High Similarity	NPC284464
0.947	High Similarity	NPC30951
0.947	High Similarity	NPC6369
0.9444	High Similarity	NPC78974
0.9444	High Similarity	NPC18924
0.9444	High Similarity	NPC223136
0.9444	High Similarity	NPC214406
0.9444	High Similarity	NPC103823
0.9444	High Similarity	NPC28730
0.9444	High Similarity	NPC44748
0.9385	High Similarity	NPC112237
0.937	High Similarity	NPC82679
0.937	High Similarity	NPC74817
0.937	High Similarity	NPC236791
0.937	High Similarity	NPC324112
0.937	High Similarity	NPC169474
0.937	High Similarity	NPC246620
0.937	High Similarity	NPC293054
0.937	High Similarity	NPC282000
0.937	High Similarity	NPC159968
0.937	High Similarity	NPC124452
0.9365	High Similarity	NPC60885
0.9365	High Similarity	NPC299584
0.9365	High Similarity	NPC82483
0.9365	High Similarity	NPC234400
0.9365	High Similarity	NPC265483
0.9318	High Similarity	NPC197166
0.9259	High Similarity	NPC184684
0.9259	High Similarity	NPC41782
0.9259	High Similarity	NPC133934
0.9259	High Similarity	NPC184641
0.9259	High Similarity	NPC191231
0.9248	High Similarity	NPC474039
0.9237	High Similarity	NPC58585
0.9225	High Similarity	NPC58164
0.9225	High Similarity	NPC10225
0.9213	High Similarity	NPC298757
0.9213	High Similarity	NPC57490
0.9213	High Similarity	NPC251855
0.9213	High Similarity	NPC116907
0.9213	High Similarity	NPC221077
0.9213	High Similarity	NPC193544
0.9213	High Similarity	NPC472093
0.9213	High Similarity	NPC117214
0.9213	High Similarity	NPC475169
0.9213	High Similarity	NPC208950
0.9213	High Similarity	NPC233410
0.9213	High Similarity	NPC105925
0.9213	High Similarity	NPC203133
0.9213	High Similarity	NPC17943
0.9206	High Similarity	NPC95168
0.9191	High Similarity	NPC81638
0.9179	High Similarity	NPC9068
0.9173	High Similarity	NPC25695
0.9173	High Similarity	NPC172818
0.9154	High Similarity	NPC51840
0.9154	High Similarity	NPC126836
0.9154	High Similarity	NPC234488
0.9154	High Similarity	NPC311680
0.9154	High Similarity	NPC299221
0.9147	High Similarity	NPC28765
0.9147	High Similarity	NPC154866
0.9127	High Similarity	NPC473411
0.9127	High Similarity	NPC71579
0.9127	High Similarity	NPC262253
0.9124	High Similarity	NPC73467
0.9124	High Similarity	NPC121661
0.9111	High Similarity	NPC177868
0.9091	High Similarity	NPC196937
0.9077	High Similarity	NPC212015
0.907	High Similarity	NPC210355
0.907	High Similarity	NPC266555
0.907	High Similarity	NPC236760
0.907	High Similarity	NPC252131
0.907	High Similarity	NPC127587
0.9058	High Similarity	NPC307466
0.9058	High Similarity	NPC166506
0.9058	High Similarity	NPC189239
0.9058	High Similarity	NPC110763
0.9058	High Similarity	NPC197352
0.9055	High Similarity	NPC282496
0.9055	High Similarity	NPC136319
0.9055	High Similarity	NPC121115
0.9055	High Similarity	NPC228922
0.9055	High Similarity	NPC233526
0.9055	High Similarity	NPC197757
0.9051	High Similarity	NPC255566
0.9051	High Similarity	NPC474808
0.9051	High Similarity	NPC298317
0.9048	High Similarity	NPC75713
0.9037	High Similarity	NPC292487
0.9015	High Similarity	NPC471505
0.9015	High Similarity	NPC6451
0.9	High Similarity	NPC266691
0.9	High Similarity	NPC470213
0.9	High Similarity	NPC98631
0.9	High Similarity	NPC186843
0.9	High Similarity	NPC206615
0.8993	High Similarity	NPC252286
0.8993	High Similarity	NPC154971
0.8992	High Similarity	NPC76451
0.8992	High Similarity	NPC223953
0.8992	High Similarity	NPC274356
0.8978	High Similarity	NPC475084
0.8976	High Similarity	NPC41562
0.8968	High Similarity	NPC166759
0.8947	High Similarity	NPC32778
0.8947	High Similarity	NPC158331
0.8947	High Similarity	NPC168059
0.8947	High Similarity	NPC475840
0.8947	High Similarity	NPC229442
0.8939	High Similarity	NPC45715
0.8939	High Similarity	NPC232275
0.8939	High Similarity	NPC474356
0.8939	High Similarity	NPC12275
0.8931	High Similarity	NPC170844
0.8931	High Similarity	NPC476968
0.8921	High Similarity	NPC180953
0.8921	High Similarity	NPC475096
0.8913	High Similarity	NPC12728
0.8913	High Similarity	NPC185071
0.8897	High Similarity	NPC53722
0.8897	High Similarity	NPC290714
0.8897	High Similarity	NPC201404
0.8889	High Similarity	NPC474565
0.8889	High Similarity	NPC61516
0.8889	High Similarity	NPC232084
0.8889	High Similarity	NPC10932
0.8889	High Similarity	NPC247364
0.8881	High Similarity	NPC287745
0.8881	High Similarity	NPC107478
0.8881	High Similarity	NPC317380
0.8872	High Similarity	NPC127624
0.8872	High Similarity	NPC175067
0.8872	High Similarity	NPC202762
0.8872	High Similarity	NPC106739
0.8872	High Similarity	NPC204215
0.8872	High Similarity	NPC86655
0.8865	High Similarity	NPC301961
0.8865	High Similarity	NPC166584
0.8864	High Similarity	NPC472338
0.8864	High Similarity	NPC224157
0.8864	High Similarity	NPC91291
0.8864	High Similarity	NPC192687
0.8864	High Similarity	NPC214860
0.8857	High Similarity	NPC190714
0.8857	High Similarity	NPC125755
0.8857	High Similarity	NPC99515
0.8857	High Similarity	NPC33832
0.8849	High Similarity	NPC187774
0.8849	High Similarity	NPC472713
0.8849	High Similarity	NPC118385
0.8849	High Similarity	NPC473046
0.8849	High Similarity	NPC472712
0.8846	High Similarity	NPC473960
0.8841	High Similarity	NPC230538
0.8841	High Similarity	NPC469559
0.8841	High Similarity	NPC103637
0.8841	High Similarity	NPC229172
0.8841	High Similarity	NPC36531
0.8841	High Similarity	NPC189115
0.8837	High Similarity	NPC5796
0.8837	High Similarity	NPC191768
0.8837	High Similarity	NPC283170
0.8837	High Similarity	NPC183446
0.8837	High Similarity	NPC92869
0.8837	High Similarity	NPC228972
0.8837	High Similarity	NPC206487
0.8837	High Similarity	NPC122792
0.8832	High Similarity	NPC184797
0.8832	High Similarity	NPC109240
0.8832	High Similarity	NPC309124
0.8832	High Similarity	NPC160283
0.8832	High Similarity	NPC254759
0.8824	High Similarity	NPC195196
0.8824	High Similarity	NPC185908
0.8815	High Similarity	NPC474206
0.8815	High Similarity	NPC121812
0.8815	High Similarity	NPC134968
0.8815	High Similarity	NPC99572
0.8815	High Similarity	NPC313081
0.8815	High Similarity	NPC294884
0.8815	High Similarity	NPC200557
0.8815	High Similarity	NPC470356
0.8815	High Similarity	NPC69029
0.8815	High Similarity	NPC472337
0.8815	High Similarity	NPC108198
0.8815	High Similarity	NPC256262
0.8815	High Similarity	NPC158142
0.8815	High Similarity	NPC150534
0.8815	High Similarity	NPC142547
0.8815	High Similarity	NPC101624
0.8815	High Similarity	NPC126409
0.8815	High Similarity	NPC135777
0.8815	High Similarity	NPC112246

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 NPC471391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	985
0.2-0.3	1913
0.3-0.4	2804
0.4-0.5	1580
0.5-0.6	887
0.6-0.7	550
0.7-0.8	92
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8931	High Similarity	NPD3027	Phase 3
0.8571	High Similarity	NPD1529	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1613	Approved
0.8456	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD3018	Phase 2
0.8195	Intermediate Similarity	NPD2983	Phase 2
0.8195	Intermediate Similarity	NPD2982	Phase 2
0.8182	Intermediate Similarity	NPD3705	Approved
0.8175	Intermediate Similarity	NPD228	Approved
0.8158	Intermediate Similarity	NPD6234	Discontinued
0.812	Intermediate Similarity	NPD2981	Phase 2
0.8092	Intermediate Similarity	NPD1357	Approved
0.8067	Intermediate Similarity	NPD37	Approved
0.8041	Intermediate Similarity	NPD1653	Approved
0.7935	Intermediate Similarity	NPD7199	Phase 2
0.7926	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3818	Discontinued
0.7908	Intermediate Similarity	NPD4965	Approved
0.7908	Intermediate Similarity	NPD4967	Phase 2
0.7908	Intermediate Similarity	NPD4966	Approved
0.7908	Intermediate Similarity	NPD3882	Suspended
0.7907	Intermediate Similarity	NPD5283	Phase 1
0.7899	Intermediate Similarity	NPD4908	Phase 1
0.7891	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1548	Phase 1
0.7852	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7228	Approved
0.7786	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD1091	Approved
0.7778	Intermediate Similarity	NPD2801	Approved
0.775	Intermediate Similarity	NPD7054	Approved
0.7724	Intermediate Similarity	NPD7266	Discontinued
0.7724	Intermediate Similarity	NPD3540	Phase 1
0.7712	Intermediate Similarity	NPD1934	Approved
0.7702	Intermediate Similarity	NPD7472	Approved
0.7702	Intermediate Similarity	NPD7074	Phase 3
0.7662	Intermediate Similarity	NPD2978	Approved
0.7662	Intermediate Similarity	NPD2977	Approved
0.7655	Intermediate Similarity	NPD3539	Phase 1
0.7597	Intermediate Similarity	NPD3021	Approved
0.7597	Intermediate Similarity	NPD3022	Approved
0.7589	Intermediate Similarity	NPD4625	Phase 3
0.7552	Intermediate Similarity	NPD1558	Phase 1
0.7548	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6797	Phase 2
0.7536	Intermediate Similarity	NPD4749	Approved
0.7535	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4357	Discontinued
0.7533	Intermediate Similarity	NPD1511	Approved
0.7518	Intermediate Similarity	NPD422	Phase 1
0.7516	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD6674	Discontinued
0.7455	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7808	Phase 3
0.7452	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2861	Phase 2
0.7434	Intermediate Similarity	NPD1512	Approved
0.7431	Intermediate Similarity	NPD4060	Phase 1
0.7431	Intermediate Similarity	NPD3620	Phase 2
0.7431	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5536	Phase 2
0.7389	Intermediate Similarity	NPD3817	Phase 2
0.7381	Intermediate Similarity	NPD1242	Phase 1
0.7376	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6166	Phase 2
0.7329	Intermediate Similarity	NPD6232	Discontinued
0.7323	Intermediate Similarity	NPD940	Approved
0.7323	Intermediate Similarity	NPD846	Approved
0.7296	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7240	Approved
0.7289	Intermediate Similarity	NPD6559	Discontinued
0.7285	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3060	Approved
0.7267	Intermediate Similarity	NPD4237	Approved
0.7267	Intermediate Similarity	NPD4236	Phase 3
0.7244	Intermediate Similarity	NPD4675	Approved
0.7244	Intermediate Similarity	NPD4678	Approved
0.7241	Intermediate Similarity	NPD2674	Phase 3
0.7237	Intermediate Similarity	NPD5058	Phase 3
0.7237	Intermediate Similarity	NPD7124	Phase 2
0.7208	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4750	Phase 3
0.7195	Intermediate Similarity	NPD7473	Discontinued
0.7192	Intermediate Similarity	NPD1240	Approved
0.7179	Intermediate Similarity	NPD4005	Discontinued
0.7171	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2219	Phase 1
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7133	Intermediate Similarity	NPD1375	Discontinued
0.7132	Intermediate Similarity	NPD6671	Approved
0.7132	Intermediate Similarity	NPD709	Approved
0.7121	Intermediate Similarity	NPD2684	Approved
0.7118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1510	Phase 2
0.7113	Intermediate Similarity	NPD2922	Phase 1
0.7107	Intermediate Similarity	NPD1465	Phase 2
0.7105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1607	Approved
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4055	Discovery
0.7078	Intermediate Similarity	NPD6799	Approved
0.7075	Intermediate Similarity	NPD943	Approved
0.707	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2935	Discontinued
0.7063	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3145	Approved
0.7055	Intermediate Similarity	NPD3144	Approved
0.7047	Intermediate Similarity	NPD6111	Discontinued
0.7045	Intermediate Similarity	NPD290	Approved
0.7039	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5177	Phase 3
0.7039	Intermediate Similarity	NPD1652	Phase 2
0.7037	Intermediate Similarity	NPD7843	Approved
0.7032	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7447	Phase 1
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7025	Intermediate Similarity	NPD4380	Phase 2
0.7025	Intermediate Similarity	NPD7028	Phase 2
0.702	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7157	Approved
0.7007	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7006	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5494	Approved
0.6993	Remote Similarity	NPD3750	Approved
0.6993	Remote Similarity	NPD8651	Approved
0.6993	Remote Similarity	NPD3892	Phase 2
0.6986	Remote Similarity	NPD7095	Approved
0.6984	Remote Similarity	NPD9296	Approved
0.6984	Remote Similarity	NPD2934	Approved
0.6984	Remote Similarity	NPD2933	Approved
0.6982	Remote Similarity	NPD7685	Pre-registration
0.698	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5604	Discontinued
0.6975	Remote Similarity	NPD7075	Discontinued
0.6968	Remote Similarity	NPD7212	Phase 2
0.6968	Remote Similarity	NPD5297	Approved
0.6968	Remote Similarity	NPD7213	Phase 3
0.6966	Remote Similarity	NPD9494	Approved
0.6966	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8054	Approved
0.6959	Remote Similarity	NPD8053	Approved
0.6954	Remote Similarity	NPD6100	Approved
0.6954	Remote Similarity	NPD6099	Approved
0.6948	Remote Similarity	NPD6190	Approved
0.6939	Remote Similarity	NPD5110	Phase 2
0.6939	Remote Similarity	NPD6798	Discontinued
0.6939	Remote Similarity	NPD5109	Approved
0.6939	Remote Similarity	NPD5111	Phase 2
0.6929	Remote Similarity	NPD2860	Approved
0.6929	Remote Similarity	NPD2859	Approved
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4123	Phase 3
0.6918	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1933	Approved
0.6913	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5124	Phase 1
0.6909	Remote Similarity	NPD3787	Discontinued
0.6908	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5762	Approved
0.6908	Remote Similarity	NPD5763	Approved
0.6908	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7680	Approved
0.6903	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3020	Approved
0.6897	Remote Similarity	NPD6584	Phase 3
0.6894	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4108	Discontinued
0.6887	Remote Similarity	NPD5588	Approved
0.6883	Remote Similarity	NPD4110	Phase 3
0.6883	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5126	Approved
0.6879	Remote Similarity	NPD5125	Phase 3
0.6875	Remote Similarity	NPD6696	Suspended
0.6875	Remote Similarity	NPD5090	Approved
0.6875	Remote Similarity	NPD5089	Approved
0.6867	Remote Similarity	NPD2492	Phase 1
0.6867	Remote Similarity	NPD3926	Phase 2
0.6867	Remote Similarity	NPD4097	Suspended
0.6863	Remote Similarity	NPD1549	Phase 2
0.6852	Remote Similarity	NPD2560	Approved
0.6852	Remote Similarity	NPD2563	Approved
0.6846	Remote Similarity	NPD2238	Phase 2
0.6842	Remote Similarity	NPD7549	Discontinued
0.6842	Remote Similarity	NPD1551	Phase 2
0.6842	Remote Similarity	NPD968	Approved
0.6839	Remote Similarity	NPD2677	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