NPASS Compound

Structure

CID74817 OpenBabel06191715412D 21 22 0 0 0 0 0 0 0 0999 V2000 -7.7942 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 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 -0.5000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -0.8660 -0.5000 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 -1.7321 0.0000 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 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 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 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 9 2 0 0 0 0 6 12 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 15 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 13 16 2 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.14
Volume:	304.817
LogP:	3.411
LogD:	3.53
LogS:	-3.582
# Rotatable Bonds:	6
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.856
Synthetic Accessibility Score:	1.94
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.811
MDCK Permeability:	1.7088508684537373e-05
Pgp-inhibitor:	0.141
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.895
30% Bioavailability (F30%):	0.23

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	98.47278594970703%
Volume Distribution (VD):	0.908
Pgp-substrate:	1.1400649547576904%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.268
CYP2C9-inhibitor:	0.793
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.933
CYP2D6-substrate:	0.943
CYP3A4-inhibitor:	0.625
CYP3A4-substrate:	0.541

ADMET: Excretion

Clearance (CL):	12.118
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.11
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.407
Skin Sensitization:	0.942
Carcinogencity:	0.093
Eye Corrosion:	0.2
Eye Irritation:	0.963
Respiratory Toxicity:	0.533

Download Data

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

Natural Product: NPC74817

Natural Product ID:	NPC74817
*Common Name:**	4-[3-(2-Hydroxy-4-Methoxyphenyl)Propyl]-2-Methoxyphenol
IUPAC Name:	4-[3-(2-hydroxy-4-methoxyphenyl)propyl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	UDWSABBWZXKLLQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O4/c1-20-14-8-7-13(16(19)11-14)5-3-4-12-6-9-15(18)17(10-12)21-2/h6-11,18-19H,3-5H2,1-2H3
SMILES:	COc1ccc(c(c1)O)CCCc1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1834920
PubChem CID:	14017333
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
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	n.a.	stem	n.a.	PMID[21919533]
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23795891]
NPO12425	Combretum griffithii	Species	Combretaceae	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	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.18	ug.mL-1	PMID[537914]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	3.13	ug.mL-1	PMID[537914]

☑ 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 NPC74817 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	406
0.1-0.2	1775
0.2-0.3	5552
0.3-0.4	13352
0.4-0.5	3892
0.5-0.6	4083
0.6-0.7	6905
0.7-0.8	4981
0.8-0.85	903
0.85-0.9	517
0.9-0.95	254
0.95-1	77

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124452
1.0	High Similarity	NPC324112
1.0	High Similarity	NPC236791
1.0	High Similarity	NPC159968
1.0	High Similarity	NPC282000
1.0	High Similarity	NPC169474
1.0	High Similarity	NPC293054
1.0	High Similarity	NPC82679
1.0	High Similarity	NPC246620
0.9917	High Similarity	NPC44748
0.9917	High Similarity	NPC28730
0.9917	High Similarity	NPC78974
0.9917	High Similarity	NPC18924
0.9917	High Similarity	NPC214406
0.9917	High Similarity	NPC223136
0.9917	High Similarity	NPC103823
0.9833	High Similarity	NPC57490
0.9833	High Similarity	NPC251855
0.9833	High Similarity	NPC472093
0.9833	High Similarity	NPC265483
0.9833	High Similarity	NPC82483
0.9833	High Similarity	NPC117214
0.9833	High Similarity	NPC298757
0.9833	High Similarity	NPC475169
0.9833	High Similarity	NPC234400
0.9833	High Similarity	NPC116907
0.9833	High Similarity	NPC105925
0.9833	High Similarity	NPC299584
0.9833	High Similarity	NPC208950
0.9833	High Similarity	NPC221077
0.9833	High Similarity	NPC60885
0.9833	High Similarity	NPC17943
0.9833	High Similarity	NPC193544
0.9833	High Similarity	NPC233410
0.9833	High Similarity	NPC203133
0.9756	High Similarity	NPC234488
0.9756	High Similarity	NPC311680
0.9756	High Similarity	NPC299221
0.9756	High Similarity	NPC126836
0.9756	High Similarity	NPC51840
0.9754	High Similarity	NPC154866
0.9754	High Similarity	NPC28765
0.9675	High Similarity	NPC58164
0.9675	High Similarity	NPC10225
0.9675	High Similarity	NPC212015
0.9672	High Similarity	NPC127587
0.9672	High Similarity	NPC252131
0.9672	High Similarity	NPC236760
0.9672	High Similarity	NPC266555
0.9667	High Similarity	NPC136319
0.9667	High Similarity	NPC228922
0.9667	High Similarity	NPC233526
0.9667	High Similarity	NPC282496
0.9667	High Similarity	NPC121115
0.9667	High Similarity	NPC95168
0.9667	High Similarity	NPC197757
0.96	High Similarity	NPC6451
0.9593	High Similarity	NPC206615
0.9593	High Similarity	NPC266691
0.9593	High Similarity	NPC98631
0.9593	High Similarity	NPC470213
0.9593	High Similarity	NPC186843
0.959	High Similarity	NPC223953
0.959	High Similarity	NPC76451
0.9583	High Similarity	NPC71579
0.9583	High Similarity	NPC41562
0.9583	High Similarity	NPC262253
0.9583	High Similarity	NPC473411
0.9524	High Similarity	NPC32778
0.9524	High Similarity	NPC475840
0.952	High Similarity	NPC45715
0.952	High Similarity	NPC474356
0.952	High Similarity	NPC12275
0.952	High Similarity	NPC232275
0.9516	High Similarity	NPC170844
0.9516	High Similarity	NPC476968
0.9512	High Similarity	NPC210355
0.95	High Similarity	NPC75713
0.9449	High Similarity	NPC317380
0.9444	High Similarity	NPC202762
0.9444	High Similarity	NPC86655
0.9444	High Similarity	NPC127624
0.944	High Similarity	NPC192687
0.944	High Similarity	NPC224157
0.9426	High Similarity	NPC206487
0.9426	High Similarity	NPC5796
0.9417	High Similarity	NPC166759
0.9375	High Similarity	NPC158142
0.9375	High Similarity	NPC94750
0.9375	High Similarity	NPC474206
0.9375	High Similarity	NPC200557
0.9375	High Similarity	NPC121812
0.9375	High Similarity	NPC69029
0.9375	High Similarity	NPC470356
0.9375	High Similarity	NPC10314
0.9375	High Similarity	NPC112939
0.9375	High Similarity	NPC294884
0.9375	High Similarity	NPC313081
0.9375	High Similarity	NPC108198
0.9375	High Similarity	NPC112246
0.9375	High Similarity	NPC256262
0.937	High Similarity	NPC471390
0.937	High Similarity	NPC229442
0.937	High Similarity	NPC168059
0.937	High Similarity	NPC471391
0.9365	High Similarity	NPC15543
0.9365	High Similarity	NPC474017
0.936	High Similarity	NPC190144
0.936	High Similarity	NPC469963
0.936	High Similarity	NPC469951
0.9355	High Similarity	NPC242032
0.9355	High Similarity	NPC470699
0.9344	High Similarity	NPC84086
0.9333	High Similarity	NPC61516
0.9333	High Similarity	NPC232084
0.9333	High Similarity	NPC247364
0.9333	High Similarity	NPC474565
0.9333	High Similarity	NPC10932
0.9302	High Similarity	NPC227503
0.9302	High Similarity	NPC474639
0.9302	High Similarity	NPC270456
0.9302	High Similarity	NPC472336
0.9302	High Similarity	NPC162659
0.9302	High Similarity	NPC472334
0.9302	High Similarity	NPC306441
0.9302	High Similarity	NPC143139
0.9302	High Similarity	NPC265433
0.9302	High Similarity	NPC202846
0.9302	High Similarity	NPC16435
0.9302	High Similarity	NPC248727
0.9302	High Similarity	NPC230734
0.9297	High Similarity	NPC7515
0.9297	High Similarity	NPC289258
0.9297	High Similarity	NPC555
0.9297	High Similarity	NPC56764
0.9297	High Similarity	NPC209199
0.9297	High Similarity	NPC276026
0.9297	High Similarity	NPC206737
0.9297	High Similarity	NPC469659
0.9297	High Similarity	NPC125649
0.9297	High Similarity	NPC188378
0.9291	High Similarity	NPC201587
0.9291	High Similarity	NPC253105
0.9286	High Similarity	NPC472338
0.9286	High Similarity	NPC214860
0.9286	High Similarity	NPC91291
0.9274	High Similarity	NPC181361
0.9274	High Similarity	NPC112596
0.9268	High Similarity	NPC228972
0.9268	High Similarity	NPC122792
0.9268	High Similarity	NPC183446
0.925	High Similarity	NPC254625
0.925	High Similarity	NPC226629
0.925	High Similarity	NPC20674
0.925	High Similarity	NPC475961
0.9231	High Similarity	NPC25111
0.9231	High Similarity	NPC6262
0.9231	High Similarity	NPC103976
0.9231	High Similarity	NPC73535
0.9231	High Similarity	NPC107551
0.9231	High Similarity	NPC102904
0.9231	High Similarity	NPC176051
0.9231	High Similarity	NPC474282
0.9231	High Similarity	NPC56329
0.9231	High Similarity	NPC201145
0.9231	High Similarity	NPC326797
0.9231	High Similarity	NPC272157
0.9231	High Similarity	NPC276490
0.9231	High Similarity	NPC90615
0.9231	High Similarity	NPC211549
0.9231	High Similarity	NPC242715
0.9225	High Similarity	NPC240279
0.9225	High Similarity	NPC180602
0.9225	High Similarity	NPC214853
0.9225	High Similarity	NPC151224
0.9225	High Similarity	NPC234333
0.9225	High Similarity	NPC55239
0.9225	High Similarity	NPC260898
0.9225	High Similarity	NPC61946
0.9225	High Similarity	NPC47398
0.9225	High Similarity	NPC472337
0.9225	High Similarity	NPC241241
0.9219	High Similarity	NPC158331
0.9219	High Similarity	NPC11060
0.9219	High Similarity	NPC36661
0.9213	High Similarity	NPC470095
0.9213	High Similarity	NPC472597
0.9213	High Similarity	NPC470096
0.9206	High Similarity	NPC45824
0.92	High Similarity	NPC21563
0.9187	High Similarity	NPC471693
0.918	High Similarity	NPC49341
0.918	High Similarity	NPC476633
0.9167	High Similarity	NPC470626
0.916	High Similarity	NPC220344
0.916	High Similarity	NPC127218
0.916	High Similarity	NPC319647
0.916	High Similarity	NPC243996
0.916	High Similarity	NPC260741
0.916	High Similarity	NPC79622

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 NPC74817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	974
0.2-0.3	1795
0.3-0.4	2756
0.4-0.5	1594
0.5-0.6	893
0.6-0.7	630
0.7-0.8	132
0.8-0.85	11
0.85-0.9	3
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9516	High Similarity	NPD3027	Phase 3
0.9127	High Similarity	NPD1529	Clinical (unspecified phase)
0.9048	High Similarity	NPD1530	Clinical (unspecified phase)
0.8992	High Similarity	NPD1612	Clinical (unspecified phase)
0.8992	High Similarity	NPD1613	Approved
0.875	High Similarity	NPD3018	Phase 2
0.8583	High Similarity	NPD2982	Phase 2
0.8583	High Similarity	NPD228	Approved
0.8583	High Similarity	NPD2983	Phase 2
0.8504	High Similarity	NPD2981	Phase 2
0.8443	Intermediate Similarity	NPD5283	Phase 1
0.8397	Intermediate Similarity	NPD4908	Phase 1
0.8295	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD1610	Phase 2
0.8271	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD1548	Phase 1
0.8151	Intermediate Similarity	NPD1934	Approved
0.8115	Intermediate Similarity	NPD3022	Approved
0.8115	Intermediate Similarity	NPD3021	Approved
0.8095	Intermediate Similarity	NPD2801	Approved
0.806	Intermediate Similarity	NPD4625	Phase 3
0.8058	Intermediate Similarity	NPD3540	Phase 1
0.8015	Intermediate Similarity	NPD4749	Approved
0.7987	Intermediate Similarity	NPD3882	Suspended
0.7986	Intermediate Similarity	NPD3539	Phase 1
0.7973	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1558	Phase 1
0.7879	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1511	Approved
0.7836	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD846	Approved
0.7833	Intermediate Similarity	NPD940	Approved
0.7778	Intermediate Similarity	NPD2861	Phase 2
0.7763	Intermediate Similarity	NPD6234	Discontinued
0.7755	Intermediate Similarity	NPD1653	Approved
0.7754	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD4060	Phase 1
0.7754	Intermediate Similarity	NPD3620	Phase 2
0.7752	Intermediate Similarity	NPD5536	Phase 2
0.775	Intermediate Similarity	NPD1242	Phase 1
0.7748	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6166	Phase 2
0.7742	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1512	Approved
0.7737	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD422	Phase 1
0.7724	Intermediate Similarity	NPD4357	Discontinued
0.7708	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD4750	Phase 3
0.7667	Intermediate Similarity	NPD37	Approved
0.7655	Intermediate Similarity	NPD7124	Phase 2
0.7626	Intermediate Similarity	NPD1240	Approved
0.7613	Intermediate Similarity	NPD6232	Discontinued
0.76	Intermediate Similarity	NPD2684	Approved
0.7597	Intermediate Similarity	NPD6671	Approved
0.7594	Intermediate Similarity	NPD3705	Approved
0.7584	Intermediate Similarity	NPD4005	Discontinued
0.7582	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3060	Approved
0.7566	Intermediate Similarity	NPD3817	Phase 2
0.7554	Intermediate Similarity	NPD2674	Phase 3
0.7548	Intermediate Similarity	NPD7199	Phase 2
0.7547	Intermediate Similarity	NPD7074	Phase 3
0.7535	Intermediate Similarity	NPD1510	Phase 2
0.7533	Intermediate Similarity	NPD4678	Approved
0.7533	Intermediate Similarity	NPD4675	Approved
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.7518	Intermediate Similarity	NPD1607	Approved
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4966	Approved
0.7516	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD7843	Approved
0.7484	Intermediate Similarity	NPD7054	Approved
0.7483	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7473	Discontinued
0.7468	Intermediate Similarity	NPD4055	Discovery
0.7466	Intermediate Similarity	NPD2219	Phase 1
0.7465	Intermediate Similarity	NPD6111	Discontinued
0.7463	Intermediate Similarity	NPD1091	Approved
0.7462	Intermediate Similarity	NPD7157	Approved
0.7452	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5177	Phase 3
0.7438	Intermediate Similarity	NPD7472	Approved
0.7432	Intermediate Similarity	NPD7447	Phase 1
0.7432	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7266	Discontinued
0.7426	Intermediate Similarity	NPD8651	Approved
0.7426	Intermediate Similarity	NPD2922	Phase 1
0.7421	Intermediate Similarity	NPD7228	Approved
0.7417	Intermediate Similarity	NPD4380	Phase 2
0.7417	Intermediate Similarity	NPD2860	Approved
0.7417	Intermediate Similarity	NPD2859	Approved
0.7386	Intermediate Similarity	NPD1465	Phase 2
0.7383	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD290	Approved
0.7377	Intermediate Similarity	NPD3020	Approved
0.7365	Intermediate Similarity	NPD7212	Phase 2
0.7365	Intermediate Similarity	NPD7213	Phase 3
0.7361	Intermediate Similarity	NPD2935	Discontinued
0.7361	Intermediate Similarity	NPD6099	Approved
0.7361	Intermediate Similarity	NPD6100	Approved
0.7357	Intermediate Similarity	NPD5109	Approved
0.7357	Intermediate Similarity	NPD3144	Approved
0.7357	Intermediate Similarity	NPD5111	Phase 2
0.7357	Intermediate Similarity	NPD5110	Phase 2
0.7357	Intermediate Similarity	NPD3145	Approved
0.7333	Intermediate Similarity	NPD2933	Approved
0.7333	Intermediate Similarity	NPD2934	Approved
0.7333	Intermediate Similarity	NPD9296	Approved
0.7329	Intermediate Similarity	NPD6674	Discontinued
0.7329	Intermediate Similarity	NPD4237	Approved
0.7329	Intermediate Similarity	NPD4236	Phase 3
0.7324	Intermediate Similarity	NPD230	Phase 1
0.7319	Intermediate Similarity	NPD6584	Phase 3
0.7317	Intermediate Similarity	NPD8053	Approved
0.7317	Intermediate Similarity	NPD8054	Approved
0.7313	Intermediate Similarity	NPD4626	Approved
0.731	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7095	Approved
0.7284	Intermediate Similarity	NPD6797	Phase 2
0.7279	Intermediate Similarity	NPD3892	Phase 2
0.7279	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD5844	Phase 1
0.7266	Intermediate Similarity	NPD5451	Approved
0.7266	Intermediate Similarity	NPD9494	Approved
0.726	Intermediate Similarity	NPD1549	Phase 2
0.726	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5090	Approved
0.7255	Intermediate Similarity	NPD5089	Approved
0.7254	Intermediate Similarity	NPD2238	Phase 2
0.7248	Intermediate Similarity	NPD6799	Approved
0.7244	Intermediate Similarity	NPD7075	Discontinued
0.7239	Intermediate Similarity	NPD7251	Discontinued
0.7237	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6798	Discontinued
0.7226	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4538	Approved
0.7222	Intermediate Similarity	NPD4536	Approved
0.7222	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1652	Phase 2
0.7203	Intermediate Similarity	NPD5124	Phase 1
0.7203	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD4123	Phase 3
0.7195	Intermediate Similarity	NPD7808	Phase 3
0.7195	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD6516	Phase 2
0.7185	Intermediate Similarity	NPD5846	Approved
0.7179	Intermediate Similarity	NPD6788	Approved
0.7178	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD968	Approved
0.7162	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2978	Approved
0.7161	Intermediate Similarity	NPD2977	Approved
0.7161	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2232	Approved
0.7153	Intermediate Similarity	NPD2233	Approved
0.7153	Intermediate Similarity	NPD4097	Suspended
0.7153	Intermediate Similarity	NPD2230	Approved
0.7152	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3847	Discontinued
0.7131	Intermediate Similarity	NPD844	Approved
0.7124	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2796	Approved
0.7114	Intermediate Similarity	NPD2677	Approved
0.7114	Intermediate Similarity	NPD6190	Approved
0.7113	Intermediate Similarity	NPD5718	Phase 2
0.7103	Intermediate Similarity	NPD6895	Approved
0.7103	Intermediate Similarity	NPD6896	Approved
0.7101	Intermediate Similarity	NPD6583	Phase 3
0.7101	Intermediate Similarity	NPD6582	Phase 2
0.7099	Intermediate Similarity	NPD5535	Approved
0.7095	Intermediate Similarity	NPD4162	Approved
0.7091	Intermediate Similarity	NPD7549	Discontinued
0.7086	Intermediate Similarity	NPD1424	Approved
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6599	Discontinued
0.7075	Intermediate Similarity	NPD5763	Approved
0.7075	Intermediate Similarity	NPD5762	Approved
0.7075	Intermediate Similarity	NPD1375	Discontinued
0.7068	Intermediate Similarity	NPD709	Approved
0.7059	Intermediate Similarity	NPD2668	Approved
0.7059	Intermediate Similarity	NPD2667	Approved
0.7055	Intermediate Similarity	NPD5960	Phase 3
0.7055	Intermediate Similarity	NPD5588	Approved
0.7051	Intermediate Similarity	NPD7819	Suspended
0.705	Intermediate Similarity	NPD6696	Suspended

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