NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.09
Volume:	206.081
LogP:	2.204
LogD:	2.415
LogS:	-2.148
# Rotatable Bonds:	4
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.746
Synthetic Accessibility Score:	2.06
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.458
MDCK Permeability:	2.0963467250112444e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.447
30% Bioavailability (F30%):	0.829

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	90.5250473022461%
Volume Distribution (VD):	0.925
Pgp-substrate:	5.220177173614502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.911
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.339
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.455
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.397

ADMET: Excretion

Clearance (CL):	12.844
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.124
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.77
Carcinogencity:	0.667
Eye Corrosion:	0.225
Eye Irritation:	0.93
Respiratory Toxicity:	0.637

Download Data

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

Natural Product: NPC285289

Natural Product ID:	NPC285289
*Common Name:**	2-Allyl-4,5-Dimethoxyphenol
IUPAC Name:	4,5-dimethoxy-2-prop-2-enylphenol
Synonyms:
Standard InCHIKey:	IHAVVJBEVFMSES-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O3/c1-4-5-8-6-10(13-2)11(14-3)7-9(8)12/h4,6-7,12H,1,5H2,2-3H3
SMILES:	C=CCc1cc(c(cc1O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163202
PubChem CID:	10997884
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
NPO15976	Hypericum calycinum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15649510]
NPO15976	Hypericum calycinum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15976	Hypericum calycinum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20603	Delphinus delphis	Species	Delphinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21215	Tripora divaricata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20603	Delphinus delphis	Species	Delphinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21539	Kalanchoe petitiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20802	Clitocybe inversa	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15976	Hypericum calycinum	Species	Hypericaceae	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
Others	16

Activity Type	# Activity
Individual Protein	1
Organism	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2666	Individual Protein	3-hydroxy-3-methylglutaryl-coenzyme A reductase	Schizosaccharomyces pombe 972h-	IC50	=	78800.0	nM	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-42.39	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-37.78	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-35.96	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-40.08	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-44.22	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	26.49	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-40.67	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-33.45	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-6.83	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-23.2	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-49.79	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-54.11	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-42.98	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-52.07	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-39.67	%	PMID[510020]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-41.77	%	PMID[510020]

☑ 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 NPC285289 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	385
0.1-0.2	1982
0.2-0.3	6617
0.3-0.4	12980
0.4-0.5	3572
0.5-0.6	4471
0.6-0.7	7852
0.7-0.8	3829
0.8-0.85	597
0.85-0.9	329
0.9-0.95	81
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC183446
0.9407	High Similarity	NPC270326
0.9397	High Similarity	NPC20674
0.9397	High Similarity	NPC308217
0.9391	High Similarity	NPC52464
0.9391	High Similarity	NPC304208
0.9344	High Similarity	NPC58164
0.9344	High Similarity	NPC190144
0.9344	High Similarity	NPC10225
0.9268	High Similarity	NPC311680
0.9268	High Similarity	NPC299221
0.9268	High Similarity	NPC234488
0.9268	High Similarity	NPC224157
0.9268	High Similarity	NPC51840
0.9268	High Similarity	NPC192687
0.9256	High Similarity	NPC112596
0.9244	High Similarity	NPC135414
0.9244	High Similarity	NPC246967
0.9244	High Similarity	NPC474864
0.9224	High Similarity	NPC259638
0.9194	High Similarity	NPC12275
0.9194	High Similarity	NPC45715
0.9194	High Similarity	NPC474356
0.9174	High Similarity	NPC105925
0.9174	High Similarity	NPC234400
0.9174	High Similarity	NPC60885
0.9145	High Similarity	NPC474612
0.9138	High Similarity	NPC193067
0.912	High Similarity	NPC6451
0.9106	High Similarity	NPC19694
0.9106	High Similarity	NPC63179
0.9106	High Similarity	NPC266691
0.9098	High Similarity	NPC78974
0.9098	High Similarity	NPC245060
0.9098	High Similarity	NPC223953
0.9098	High Similarity	NPC223136
0.9098	High Similarity	NPC18924
0.9098	High Similarity	NPC28730
0.9098	High Similarity	NPC103823
0.9098	High Similarity	NPC214406
0.9098	High Similarity	NPC44748
0.9043	High Similarity	NPC204120
0.904	High Similarity	NPC232275
0.9032	High Similarity	NPC45824
0.9024	High Similarity	NPC266555
0.9024	High Similarity	NPC293054
0.9024	High Similarity	NPC246620
0.9024	High Similarity	NPC169474
0.9024	High Similarity	NPC282000
0.9024	High Similarity	NPC124452
0.9024	High Similarity	NPC159968
0.9024	High Similarity	NPC324112
0.9024	High Similarity	NPC236791
0.9024	High Similarity	NPC82679
0.9024	High Similarity	NPC74817
0.9016	High Similarity	NPC82483
0.9016	High Similarity	NPC299584
0.9016	High Similarity	NPC265483
0.9008	High Similarity	NPC165375
0.9008	High Similarity	NPC233526
0.9008	High Similarity	NPC282496
0.9008	High Similarity	NPC220598
0.9	High Similarity	NPC75713
0.9	High Similarity	NPC49341
0.8992	High Similarity	NPC229401
0.8983	High Similarity	NPC63083
0.8976	High Similarity	NPC106215
0.896	High Similarity	NPC220935
0.896	High Similarity	NPC214860
0.8952	High Similarity	NPC154866
0.8934	High Similarity	NPC283170
0.8934	High Similarity	NPC5796
0.8934	High Similarity	NPC92869
0.8934	High Similarity	NPC191768
0.8934	High Similarity	NPC206487
0.8926	High Similarity	NPC41562
0.8926	High Similarity	NPC264885
0.8926	High Similarity	NPC194626
0.8917	High Similarity	NPC166759
0.8906	High Similarity	NPC195022
0.8906	High Similarity	NPC472337
0.8906	High Similarity	NPC111655
0.888	High Similarity	NPC158477
0.8871	High Similarity	NPC216836
0.8871	High Similarity	NPC242032
0.887	High Similarity	NPC203924
0.8862	High Similarity	NPC475169
0.8862	High Similarity	NPC233410
0.8862	High Similarity	NPC221077
0.8862	High Similarity	NPC116907
0.8862	High Similarity	NPC472093
0.8862	High Similarity	NPC298757
0.8862	High Similarity	NPC117214
0.8862	High Similarity	NPC203133
0.8862	High Similarity	NPC251855
0.8862	High Similarity	NPC193544
0.8862	High Similarity	NPC17943
0.8862	High Similarity	NPC208950
0.8862	High Similarity	NPC57490
0.886	High Similarity	NPC165386
0.8852	High Similarity	NPC228922
0.8852	High Similarity	NPC95168
0.8852	High Similarity	NPC121115
0.8852	High Similarity	NPC197757
0.8837	High Similarity	NPC205442
0.8837	High Similarity	NPC173660
0.8837	High Similarity	NPC472334
0.8837	High Similarity	NPC472336
0.8833	High Similarity	NPC177475
0.8833	High Similarity	NPC148615
0.8833	High Similarity	NPC10932
0.8833	High Similarity	NPC232084
0.8833	High Similarity	NPC474565
0.8833	High Similarity	NPC61516
0.8833	High Similarity	NPC247364
0.8833	High Similarity	NPC35071
0.8819	High Similarity	NPC202762
0.8819	High Similarity	NPC86655
0.8814	High Similarity	NPC203113
0.8814	High Similarity	NPC221049
0.881	High Similarity	NPC229231
0.881	High Similarity	NPC126836
0.88	High Similarity	NPC28765
0.877	High Similarity	NPC262253
0.877	High Similarity	NPC473411
0.877	High Similarity	NPC211231
0.877	High Similarity	NPC71579
0.8769	High Similarity	NPC73535
0.8769	High Similarity	NPC326797
0.8769	High Similarity	NPC201145
0.8769	High Similarity	NPC25111
0.8769	High Similarity	NPC6262
0.8769	High Similarity	NPC474282
0.8769	High Similarity	NPC102904
0.8769	High Similarity	NPC176051
0.8769	High Similarity	NPC272157
0.8769	High Similarity	NPC276490
0.8769	High Similarity	NPC90615
0.8769	High Similarity	NPC103976
0.8769	High Similarity	NPC107551
0.875	High Similarity	NPC226629
0.875	High Similarity	NPC105554
0.875	High Similarity	NPC269528
0.875	High Similarity	NPC168059
0.875	High Similarity	NPC135961
0.875	High Similarity	NPC229442
0.875	High Similarity	NPC181969
0.875	High Similarity	NPC320987
0.874	High Similarity	NPC82503
0.873	High Similarity	NPC212015
0.873	High Similarity	NPC469963
0.873	High Similarity	NPC469951
0.873	High Similarity	NPC476968
0.873	High Similarity	NPC170844
0.872	High Similarity	NPC252131
0.872	High Similarity	NPC50368
0.872	High Similarity	NPC236760
0.872	High Similarity	NPC127587
0.872	High Similarity	NPC210355
0.8707	High Similarity	NPC156840
0.8707	High Similarity	NPC257124
0.8707	High Similarity	NPC8547
0.8707	High Similarity	NPC173746
0.8707	High Similarity	NPC195873
0.8702	High Similarity	NPC471388
0.8702	High Similarity	NPC25966
0.8702	High Similarity	NPC29868
0.8702	High Similarity	NPC292882
0.8702	High Similarity	NPC212942
0.8702	High Similarity	NPC245207
0.8702	High Similarity	NPC127218
0.8702	High Similarity	NPC319647
0.8702	High Similarity	NPC79622
0.8699	High Similarity	NPC238810
0.8699	High Similarity	NPC84086
0.8699	High Similarity	NPC136319
0.8692	High Similarity	NPC476639
0.8692	High Similarity	NPC197166
0.8692	High Similarity	NPC114155
0.8692	High Similarity	NPC300846
0.8689	High Similarity	NPC470804
0.8682	High Similarity	NPC310854
0.8682	High Similarity	NPC160697
0.8682	High Similarity	NPC103967
0.8672	High Similarity	NPC127624
0.8672	High Similarity	NPC161203
0.8667	High Similarity	NPC255675
0.8661	High Similarity	NPC91291
0.8655	High Similarity	NPC150624
0.8655	High Similarity	NPC141090
0.8651	High Similarity	NPC226331
0.8651	High Similarity	NPC46274
0.8651	High Similarity	NPC186843
0.8651	High Similarity	NPC470213
0.8651	High Similarity	NPC98631
0.8651	High Similarity	NPC206615
0.864	High Similarity	NPC473960
0.864	High Similarity	NPC476006
0.864	High Similarity	NPC76451
0.8636	High Similarity	NPC27495

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 NPC285289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	1029
0.2-0.3	2115
0.3-0.4	2672
0.4-0.5	1468
0.5-0.6	848
0.6-0.7	537
0.7-0.8	97
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.873	High Similarity	NPD3027	Phase 3
0.8707	High Similarity	NPD228	Approved
0.8651	High Similarity	NPD1529	Clinical (unspecified phase)
0.8571	High Similarity	NPD1530	Clinical (unspecified phase)
0.8527	High Similarity	NPD1613	Approved
0.8527	High Similarity	NPD1612	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD3018	Phase 2
0.8211	Intermediate Similarity	NPD1548	Phase 1
0.811	Intermediate Similarity	NPD2983	Phase 2
0.811	Intermediate Similarity	NPD2982	Phase 2
0.8095	Intermediate Similarity	NPD1610	Phase 2
0.8031	Intermediate Similarity	NPD2981	Phase 2
0.7953	Intermediate Similarity	NPD422	Phase 1
0.7931	Intermediate Similarity	NPD846	Approved
0.7931	Intermediate Similarity	NPD940	Approved
0.7832	Intermediate Similarity	NPD1653	Approved
0.7829	Intermediate Similarity	NPD4749	Approved
0.7823	Intermediate Similarity	NPD6671	Approved
0.7808	Intermediate Similarity	NPD2801	Approved
0.7805	Intermediate Similarity	NPD5283	Phase 1
0.7803	Intermediate Similarity	NPD4908	Phase 1
0.7727	Intermediate Similarity	NPD2861	Phase 2
0.7717	Intermediate Similarity	NPD1357	Approved
0.7692	Intermediate Similarity	NPD1242	Phase 1
0.7687	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3705	Approved
0.7652	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD3540	Phase 1
0.7619	Intermediate Similarity	NPD1934	Approved
0.7612	Intermediate Similarity	NPD4625	Phase 3
0.7603	Intermediate Similarity	NPD290	Approved
0.7574	Intermediate Similarity	NPD1558	Phase 1
0.7557	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3539	Phase 1
0.7552	Intermediate Similarity	NPD1511	Approved
0.7542	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD2219	Phase 1
0.7521	Intermediate Similarity	NPD968	Approved
0.748	Intermediate Similarity	NPD4750	Phase 3
0.7448	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1512	Approved
0.7445	Intermediate Similarity	NPD1240	Approved
0.7414	Intermediate Similarity	NPD9296	Approved
0.741	Intermediate Similarity	NPD6111	Discontinued
0.7405	Intermediate Similarity	NPD1091	Approved
0.7398	Intermediate Similarity	NPD2684	Approved
0.7391	Intermediate Similarity	NPD230	Phase 1
0.7372	Intermediate Similarity	NPD2674	Phase 3
0.7368	Intermediate Similarity	NPD6696	Suspended
0.7351	Intermediate Similarity	NPD3882	Suspended
0.7338	Intermediate Similarity	NPD1607	Approved
0.7333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9494	Approved
0.7328	Intermediate Similarity	NPD3496	Discontinued
0.7324	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4357	Discontinued
0.7299	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5536	Phase 2
0.7281	Intermediate Similarity	NPD9295	Approved
0.7279	Intermediate Similarity	NPD596	Approved
0.7279	Intermediate Similarity	NPD600	Approved
0.7267	Intermediate Similarity	NPD37	Approved
0.7266	Intermediate Similarity	NPD447	Suspended
0.7252	Intermediate Similarity	NPD4626	Approved
0.7248	Intermediate Similarity	NPD4675	Approved
0.7248	Intermediate Similarity	NPD4678	Approved
0.7234	Intermediate Similarity	NPD1510	Phase 2
0.7226	Intermediate Similarity	NPD6232	Discontinued
0.7203	Intermediate Similarity	NPD844	Approved
0.72	Intermediate Similarity	NPD3021	Approved
0.72	Intermediate Similarity	NPD3022	Approved
0.7194	Intermediate Similarity	NPD3620	Phase 2
0.7194	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2935	Discontinued
0.7174	Intermediate Similarity	NPD3144	Approved
0.7174	Intermediate Similarity	NPD3145	Approved
0.7171	Intermediate Similarity	NPD3817	Phase 2
0.7165	Intermediate Similarity	NPD7843	Approved
0.7153	Intermediate Similarity	NPD3060	Approved
0.7153	Intermediate Similarity	NPD5177	Phase 3
0.7153	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD1424	Approved
0.7143	Intermediate Similarity	NPD288	Approved
0.7134	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6166	Phase 2
0.7133	Intermediate Similarity	NPD1375	Discontinued
0.7132	Intermediate Similarity	NPD7157	Approved
0.7124	Intermediate Similarity	NPD4965	Approved
0.7124	Intermediate Similarity	NPD4967	Phase 2
0.7124	Intermediate Similarity	NPD4966	Approved
0.7124	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7124	Phase 2
0.7122	Intermediate Similarity	NPD840	Approved
0.7122	Intermediate Similarity	NPD839	Approved
0.7121	Intermediate Similarity	NPD1778	Approved
0.7107	Intermediate Similarity	NPD5844	Phase 1
0.7089	Intermediate Similarity	NPD7473	Discontinued
0.7086	Intermediate Similarity	NPD5090	Approved
0.7086	Intermediate Similarity	NPD5089	Approved
0.7071	Intermediate Similarity	NPD2238	Phase 2
0.7071	Intermediate Similarity	NPD4060	Phase 1
0.7067	Intermediate Similarity	NPD4005	Discontinued
0.7063	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD6099	Approved
0.7049	Intermediate Similarity	NPD291	Approved
0.7034	Intermediate Similarity	NPD4236	Phase 3
0.7034	Intermediate Similarity	NPD4237	Approved
0.7031	Intermediate Similarity	NPD821	Approved
0.7027	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD709	Approved
0.6993	Remote Similarity	NPD1465	Phase 2
0.6992	Remote Similarity	NPD9381	Approved
0.6992	Remote Similarity	NPD9384	Approved
0.6987	Remote Similarity	NPD5494	Approved
0.6985	Remote Similarity	NPD8651	Approved
0.6985	Remote Similarity	NPD2922	Phase 1
0.6977	Remote Similarity	NPD1398	Phase 1
0.6975	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2934	Approved
0.6975	Remote Similarity	NPD2933	Approved
0.6972	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4055	Discovery
0.6966	Remote Similarity	NPD1549	Phase 2
0.6963	Remote Similarity	NPD2232	Approved
0.6963	Remote Similarity	NPD2230	Approved
0.6963	Remote Similarity	NPD2233	Approved
0.6959	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7472	Approved
0.6957	Remote Similarity	NPD7074	Phase 3
0.695	Remote Similarity	NPD943	Approved
0.6943	Remote Similarity	NPD7199	Phase 2
0.6943	Remote Similarity	NPD1247	Approved
0.6937	Remote Similarity	NPD3818	Discontinued
0.6933	Remote Similarity	NPD7549	Discontinued
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.693	Remote Similarity	NPD111	Approved
0.6918	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6674	Discontinued
0.6917	Remote Similarity	NPD2859	Approved
0.6917	Remote Similarity	NPD5691	Approved
0.6917	Remote Similarity	NPD2860	Approved
0.6913	Remote Similarity	NPD7447	Phase 1
0.6913	Remote Similarity	NPD4123	Phase 3
0.6912	Remote Similarity	NPD9622	Approved
0.6908	Remote Similarity	NPD4380	Phase 2
0.6906	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1358	Approved
0.6901	Remote Similarity	NPD5124	Phase 1
0.6901	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD9379	Approved
0.6899	Remote Similarity	NPD9377	Approved
0.6897	Remote Similarity	NPD7266	Discontinued
0.6897	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9094	Approved
0.6889	Remote Similarity	NPD1535	Discovery
0.6887	Remote Similarity	NPD3686	Approved
0.6887	Remote Similarity	NPD3687	Approved
0.6885	Remote Similarity	NPD3020	Approved
0.6884	Remote Similarity	NPD6584	Phase 3
0.6875	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3750	Approved
0.6871	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1349	Approved
0.6867	Remote Similarity	NPD1350	Approved
0.6867	Remote Similarity	NPD1351	Approved
0.6855	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4097	Suspended
0.6846	Remote Similarity	NPD7212	Phase 2
0.6846	Remote Similarity	NPD1774	Approved
0.6846	Remote Similarity	NPD5297	Approved
0.6846	Remote Similarity	NPD7213	Phase 3
0.6842	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2560	Approved
0.6839	Remote Similarity	NPD2563	Approved
0.6839	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1481	Phase 2
0.6838	Remote Similarity	NPD1608	Approved
0.6838	Remote Similarity	NPD9269	Phase 2
0.6832	Remote Similarity	NPD7228	Approved
0.6829	Remote Similarity	NPD7808	Phase 3
0.6828	Remote Similarity	NPD1551	Phase 2
0.6828	Remote Similarity	NPD2161	Phase 2
0.6824	Remote Similarity	NPD2677	Approved
0.6818	Remote Similarity	NPD7340	Approved
0.681	Remote Similarity	NPD6797	Phase 2
0.6809	Remote Similarity	NPD5109	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