NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.04
Volume:	256.63
LogP:	3.504
LogD:	2.829
LogS:	-5.609
# Rotatable Bonds:	0
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.674
Synthetic Accessibility Score:	2.327
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.778
MDCK Permeability:	2.18955992750125e-05
Pgp-inhibitor:	0.692
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.837

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.138
Plasma Protein Binding (PPB):	99.12308502197266%
Volume Distribution (VD):	0.482
Pgp-substrate:	1.6061116456985474%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.713
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.658
CYP2C9-substrate:	0.754
CYP2D6-inhibitor:	0.893
CYP2D6-substrate:	0.383
CYP3A4-inhibitor:	0.827
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	14.093
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.894
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.199
Carcinogencity:	0.951
Eye Corrosion:	0.004
Eye Irritation:	0.962
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC37220

Natural Product ID:	NPC37220
*Common Name:**	5-Hydroxy-1,2-Methylenedioxy-Anthraquinone
IUPAC Name:	7-hydroxynaphtho[3,2-g][1,3]benzodioxole-6,11-dione
Synonyms:
Standard InCHIKey:	KSOSMCYIAOHPFJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H8O5/c16-9-3-1-2-7-11(9)13(17)8-4-5-10-15(20-6-19-10)12(8)14(7)18/h1-5,16H,6H2
SMILES:	c1cc2c(c(c1)O)C(=O)c1ccc3c(c1C2=O)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520325
PubChem CID:	14479676
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15917	Monilinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26859	Solanum curtipes	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2868	Perna viridis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO861	Siphonaria funiculata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13446	Stachys recta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11734	Chara corallina	Species	Characeae	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
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[497429]
NPT2	Others	Unspecified		Inhibition	=	79.5	%	PMID[497429]
NPT2	Others	Unspecified		Inhibition	=	53.8	%	PMID[497429]
NPT2	Others	Unspecified		Inhibition	=	36.5	%	PMID[497429]
NPT2	Others	Unspecified		Inhibition	=	28.0	%	PMID[497429]

☑ 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 NPC37220 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	419
0.1-0.2	1937
0.2-0.3	4151
0.3-0.4	10633
0.4-0.5	7384
0.5-0.6	3525
0.6-0.7	6981
0.7-0.8	7254
0.8-0.85	365
0.85-0.9	42
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9648	High Similarity	NPC229787
0.931	High Similarity	NPC160777
0.931	High Similarity	NPC73416
0.9028	High Similarity	NPC223336
0.8973	High Similarity	NPC125134
0.8973	High Similarity	NPC137920
0.8973	High Similarity	NPC86455
0.894	High Similarity	NPC473201
0.894	High Similarity	NPC118427
0.894	High Similarity	NPC302783
0.8904	High Similarity	NPC84273
0.8882	High Similarity	NPC312338
0.8882	High Similarity	NPC149889
0.8882	High Similarity	NPC164912
0.8836	High Similarity	NPC28398
0.8831	High Similarity	NPC109765
0.8816	High Similarity	NPC144283
0.8797	High Similarity	NPC474301
0.8784	High Similarity	NPC46880
0.8774	High Similarity	NPC202495
0.8758	High Similarity	NPC104728
0.8758	High Similarity	NPC35544
0.8725	High Similarity	NPC327052
0.8716	High Similarity	NPC141817
0.8716	High Similarity	NPC176030
0.8716	High Similarity	NPC169214
0.8716	High Similarity	NPC229218
0.8716	High Similarity	NPC192597
0.8654	High Similarity	NPC178976
0.8627	High Similarity	NPC234152
0.8611	High Similarity	NPC294226
0.8609	High Similarity	NPC88345
0.8599	High Similarity	NPC62518
0.8599	High Similarity	NPC215375
0.859	High Similarity	NPC14561
0.859	High Similarity	NPC77807
0.859	High Similarity	NPC5379
0.8589	High Similarity	NPC199357
0.8571	High Similarity	NPC118332
0.8562	High Similarity	NPC141934
0.8562	High Similarity	NPC324929
0.8544	High Similarity	NPC225624
0.8544	High Similarity	NPC285973
0.8543	High Similarity	NPC224687
0.8543	High Similarity	NPC478019
0.8535	High Similarity	NPC37543
0.8535	High Similarity	NPC167595
0.8535	High Similarity	NPC199463
0.8493	Intermediate Similarity	NPC95485
0.8493	Intermediate Similarity	NPC89504
0.8493	Intermediate Similarity	NPC88065
0.8491	Intermediate Similarity	NPC295009
0.8491	Intermediate Similarity	NPC94155
0.8491	Intermediate Similarity	NPC260640
0.8491	Intermediate Similarity	NPC162668
0.8491	Intermediate Similarity	NPC311740
0.8481	Intermediate Similarity	NPC68619
0.8477	Intermediate Similarity	NPC19896
0.8471	Intermediate Similarity	NPC213401
0.8471	Intermediate Similarity	NPC279605
0.8467	Intermediate Similarity	NPC11314
0.8467	Intermediate Similarity	NPC69755
0.8462	Intermediate Similarity	NPC107109
0.8452	Intermediate Similarity	NPC78505
0.8442	Intermediate Similarity	NPC134293
0.8431	Intermediate Similarity	NPC58373
0.8428	Intermediate Similarity	NPC84571
0.8389	Intermediate Similarity	NPC1268
0.8367	Intermediate Similarity	NPC258502
0.8355	Intermediate Similarity	NPC309169
0.8355	Intermediate Similarity	NPC196941
0.8354	Intermediate Similarity	NPC478223
0.8344	Intermediate Similarity	NPC475770
0.8344	Intermediate Similarity	NPC234331
0.8333	Intermediate Similarity	NPC26386
0.8333	Intermediate Similarity	NPC472838
0.8333	Intermediate Similarity	NPC306011
0.8323	Intermediate Similarity	NPC469575
0.8323	Intermediate Similarity	NPC116838
0.8323	Intermediate Similarity	NPC261322
0.8323	Intermediate Similarity	NPC22130
0.8323	Intermediate Similarity	NPC198796
0.8322	Intermediate Similarity	NPC61398
0.8322	Intermediate Similarity	NPC286683
0.8322	Intermediate Similarity	NPC416
0.8313	Intermediate Similarity	NPC269906
0.8312	Intermediate Similarity	NPC125449
0.8312	Intermediate Similarity	NPC126767
0.8312	Intermediate Similarity	NPC52692
0.8312	Intermediate Similarity	NPC118027
0.8312	Intermediate Similarity	NPC188074
0.8312	Intermediate Similarity	NPC312929
0.8312	Intermediate Similarity	NPC289042
0.8312	Intermediate Similarity	NPC56433
0.8312	Intermediate Similarity	NPC245584
0.8312	Intermediate Similarity	NPC190648
0.8303	Intermediate Similarity	NPC469506
0.8302	Intermediate Similarity	NPC474990
0.8301	Intermediate Similarity	NPC296575
0.8293	Intermediate Similarity	NPC222455
0.8291	Intermediate Similarity	NPC38898
0.8289	Intermediate Similarity	NPC66593
0.8289	Intermediate Similarity	NPC53016
0.8282	Intermediate Similarity	NPC29160
0.828	Intermediate Similarity	NPC3744
0.828	Intermediate Similarity	NPC137125
0.828	Intermediate Similarity	NPC153008
0.828	Intermediate Similarity	NPC474993
0.828	Intermediate Similarity	NPC148497
0.8278	Intermediate Similarity	NPC124365
0.8274	Intermediate Similarity	NPC212290
0.8272	Intermediate Similarity	NPC110257
0.8272	Intermediate Similarity	NPC470178
0.8269	Intermediate Similarity	NPC290954
0.8269	Intermediate Similarity	NPC255641
0.8269	Intermediate Similarity	NPC295977
0.8269	Intermediate Similarity	NPC58310
0.8264	Intermediate Similarity	NPC234175
0.8261	Intermediate Similarity	NPC239890
0.8261	Intermediate Similarity	NPC209411
0.8258	Intermediate Similarity	NPC24193
0.8258	Intermediate Similarity	NPC127827
0.8255	Intermediate Similarity	NPC147418
0.8253	Intermediate Similarity	NPC98776
0.8252	Intermediate Similarity	NPC177925
0.825	Intermediate Similarity	NPC125713
0.8247	Intermediate Similarity	NPC39361
0.8247	Intermediate Similarity	NPC12377
0.8239	Intermediate Similarity	NPC301897
0.8235	Intermediate Similarity	NPC142165
0.8231	Intermediate Similarity	NPC52407
0.8228	Intermediate Similarity	NPC244371
0.8228	Intermediate Similarity	NPC478213
0.8228	Intermediate Similarity	NPC54179
0.8228	Intermediate Similarity	NPC474000
0.8217	Intermediate Similarity	NPC70320
0.8217	Intermediate Similarity	NPC288316
0.8217	Intermediate Similarity	NPC75377
0.8212	Intermediate Similarity	NPC203063
0.821	Intermediate Similarity	NPC212099
0.821	Intermediate Similarity	NPC125991
0.821	Intermediate Similarity	NPC56735
0.821	Intermediate Similarity	NPC61594
0.821	Intermediate Similarity	NPC101116
0.8205	Intermediate Similarity	NPC478219
0.8205	Intermediate Similarity	NPC237441
0.8205	Intermediate Similarity	NPC69430
0.8205	Intermediate Similarity	NPC472837
0.8205	Intermediate Similarity	NPC264550
0.8205	Intermediate Similarity	NPC139293
0.8205	Intermediate Similarity	NPC200060
0.8205	Intermediate Similarity	NPC264289
0.8205	Intermediate Similarity	NPC195763
0.8205	Intermediate Similarity	NPC142876
0.8205	Intermediate Similarity	NPC333691
0.8205	Intermediate Similarity	NPC40290
0.8204	Intermediate Similarity	NPC146803
0.8199	Intermediate Similarity	NPC65784
0.8199	Intermediate Similarity	NPC185617
0.8199	Intermediate Similarity	NPC78944
0.8199	Intermediate Similarity	NPC47623
0.8194	Intermediate Similarity	NPC181464
0.8194	Intermediate Similarity	NPC252208
0.8193	Intermediate Similarity	NPC178737
0.8193	Intermediate Similarity	NPC223375
0.8193	Intermediate Similarity	NPC260263
0.8193	Intermediate Similarity	NPC475825
0.8187	Intermediate Similarity	NPC296044
0.8187	Intermediate Similarity	NPC167098
0.8187	Intermediate Similarity	NPC310206
0.8182	Intermediate Similarity	NPC225351
0.8182	Intermediate Similarity	NPC99613
0.8182	Intermediate Similarity	NPC163130
0.8182	Intermediate Similarity	NPC165979
0.8182	Intermediate Similarity	NPC49487
0.8176	Intermediate Similarity	NPC45404
0.8176	Intermediate Similarity	NPC478238
0.817	Intermediate Similarity	NPC46161
0.817	Intermediate Similarity	NPC239608
0.817	Intermediate Similarity	NPC254659
0.817	Intermediate Similarity	NPC50954
0.817	Intermediate Similarity	NPC119663
0.817	Intermediate Similarity	NPC287722
0.8169	Intermediate Similarity	NPC375356
0.8165	Intermediate Similarity	NPC68882
0.8165	Intermediate Similarity	NPC295646
0.8163	Intermediate Similarity	NPC50763
0.816	Intermediate Similarity	NPC147596
0.8158	Intermediate Similarity	NPC104956
0.8155	Intermediate Similarity	NPC475233
0.8153	Intermediate Similarity	NPC294646
0.8153	Intermediate Similarity	NPC472279
0.8153	Intermediate Similarity	NPC151473
0.8153	Intermediate Similarity	NPC85131
0.8153	Intermediate Similarity	NPC29231
0.8153	Intermediate Similarity	NPC147735
0.8153	Intermediate Similarity	NPC470568
0.8153	Intermediate Similarity	NPC156953
0.8151	Intermediate Similarity	NPC477694
0.8151	Intermediate Similarity	NPC117609

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 NPC37220 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	1002
0.2-0.3	1560
0.3-0.4	2703
0.4-0.5	1867
0.5-0.6	1037
0.6-0.7	428
0.7-0.8	143
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8282	Intermediate Similarity	NPD7473	Discontinued
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.8117	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1470	Approved
0.7975	Intermediate Similarity	NPD7458	Discontinued
0.7962	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2344	Approved
0.7919	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD3882	Suspended
0.7862	Intermediate Similarity	NPD3226	Approved
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.7829	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1510	Phase 2
0.7826	Intermediate Similarity	NPD1934	Approved
0.7826	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD2801	Approved
0.7778	Intermediate Similarity	NPD1201	Approved
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7771	Intermediate Similarity	NPD1511	Approved
0.7756	Intermediate Similarity	NPD2309	Approved
0.7755	Intermediate Similarity	NPD2798	Approved
0.7727	Intermediate Similarity	NPD1471	Phase 3
0.7706	Intermediate Similarity	NPD7074	Phase 3
0.7703	Intermediate Similarity	NPD9494	Approved
0.7702	Intermediate Similarity	NPD7028	Phase 2
0.7697	Intermediate Similarity	NPD1607	Approved
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4965	Approved
0.7683	Intermediate Similarity	NPD4966	Approved
0.7682	Intermediate Similarity	NPD1240	Approved
0.7682	Intermediate Similarity	NPD943	Approved
0.7673	Intermediate Similarity	NPD1512	Approved
0.7669	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5494	Approved
0.7647	Intermediate Similarity	NPD7054	Approved
0.7644	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3749	Approved
0.7636	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD447	Suspended
0.7632	Intermediate Similarity	NPD1933	Approved
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7472	Approved
0.7597	Intermediate Similarity	NPD2799	Discontinued
0.7572	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1549	Phase 2
0.7561	Intermediate Similarity	NPD1465	Phase 2
0.7561	Intermediate Similarity	NPD7819	Suspended
0.755	Intermediate Similarity	NPD2313	Discontinued
0.755	Intermediate Similarity	NPD3764	Approved
0.7544	Intermediate Similarity	NPD5844	Phase 1
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7483	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7808	Phase 3
0.7471	Intermediate Similarity	NPD6166	Phase 2
0.7471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7003	Approved
0.7457	Intermediate Similarity	NPD6797	Phase 2
0.7432	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7251	Discontinued
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3926	Phase 2
0.741	Intermediate Similarity	NPD3817	Phase 2
0.7405	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3751	Discontinued
0.7384	Intermediate Similarity	NPD7228	Approved
0.7383	Intermediate Similarity	NPD1876	Approved
0.7383	Intermediate Similarity	NPD1283	Approved
0.7381	Intermediate Similarity	NPD919	Approved
0.7372	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3750	Approved
0.7358	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6781	Approved
0.7337	Intermediate Similarity	NPD6778	Approved
0.7337	Intermediate Similarity	NPD6779	Approved
0.7337	Intermediate Similarity	NPD6780	Approved
0.7337	Intermediate Similarity	NPD6777	Approved
0.7337	Intermediate Similarity	NPD6776	Approved
0.7337	Intermediate Similarity	NPD6782	Approved
0.7333	Intermediate Similarity	NPD1203	Approved
0.7325	Intermediate Similarity	NPD5406	Approved
0.7325	Intermediate Similarity	NPD5408	Approved
0.7325	Intermediate Similarity	NPD5405	Approved
0.7325	Intermediate Similarity	NPD5404	Approved
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.7297	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1247	Approved
0.7294	Intermediate Similarity	NPD6959	Discontinued
0.7284	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4628	Phase 3
0.7248	Intermediate Similarity	NPD3972	Approved
0.7246	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6273	Approved
0.7229	Intermediate Similarity	NPD7411	Suspended
0.7219	Intermediate Similarity	NPD7698	Approved
0.7219	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD7696	Phase 3
0.7219	Intermediate Similarity	NPD7697	Approved
0.7216	Intermediate Similarity	NPD7685	Pre-registration
0.7212	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1651	Approved
0.7202	Intermediate Similarity	NPD5978	Approved
0.7202	Intermediate Similarity	NPD5977	Approved
0.7202	Intermediate Similarity	NPD2296	Approved
0.7202	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5536	Phase 2
0.7181	Intermediate Similarity	NPD7871	Phase 2
0.7181	Intermediate Similarity	NPD7870	Phase 2
0.7181	Intermediate Similarity	NPD1281	Approved
0.717	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.712	Intermediate Similarity	NPD8151	Discontinued
0.7117	Intermediate Similarity	NPD6799	Approved
0.7117	Intermediate Similarity	NPD7390	Discontinued
0.7107	Intermediate Similarity	NPD1551	Phase 2
0.7107	Intermediate Similarity	NPD2796	Approved
0.7105	Intermediate Similarity	NPD1164	Approved
0.7083	Intermediate Similarity	NPD6801	Discontinued
0.7081	Intermediate Similarity	NPD2800	Approved
0.7069	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7701	Phase 2
0.7065	Intermediate Similarity	NPD6535	Approved
0.7065	Intermediate Similarity	NPD6534	Approved
0.7062	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7768	Phase 2
0.7052	Intermediate Similarity	NPD3787	Discontinued
0.7047	Intermediate Similarity	NPD4626	Approved
0.7044	Intermediate Similarity	NPD3748	Approved
0.7022	Intermediate Similarity	NPD7240	Approved
0.702	Intermediate Similarity	NPD9717	Approved
0.7017	Intermediate Similarity	NPD8434	Phase 2
0.7011	Intermediate Similarity	NPD6212	Phase 3
0.7011	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6213	Phase 3
0.7007	Intermediate Similarity	NPD9493	Approved
0.7006	Intermediate Similarity	NPD3620	Phase 2
0.7006	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7874	Approved
0.6995	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8127	Discontinued
0.6988	Remote Similarity	NPD920	Approved
0.6987	Remote Similarity	NPD411	Approved
0.6984	Remote Similarity	NPD6823	Phase 2
0.698	Remote Similarity	NPD1357	Approved
0.6975	Remote Similarity	NPD1243	Approved
0.697	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD230	Phase 1
0.6959	Remote Similarity	NPD7801	Approved
0.6954	Remote Similarity	NPD5710	Approved
0.6954	Remote Similarity	NPD5711	Approved
0.6954	Remote Similarity	NPD3705	Approved
0.6952	Remote Similarity	NPD7699	Phase 2
0.6952	Remote Similarity	NPD7700	Phase 2
0.6951	Remote Similarity	NPD3300	Phase 2
0.6951	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4308	Phase 3
0.6933	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3019	Approved
0.6933	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD8150	Discontinued
0.6918	Remote Similarity	NPD5283	Phase 1
0.6908	Remote Similarity	NPD1608	Approved
0.6901	Remote Similarity	NPD5402	Approved
0.6897	Remote Similarity	NPD228	Approved
0.689	Remote Similarity	NPD6190	Approved
0.6882	Remote Similarity	NPD6280	Approved
0.6882	Remote Similarity	NPD6279	Approved
0.6879	Remote Similarity	NPD6798	Discontinued
0.6879	Remote Similarity	NPD3268	Approved
0.6871	Remote Similarity	NPD6674	Discontinued
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4420	Approved
0.6859	Remote Similarity	NPD6832	Phase 2
0.6855	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6355	Discontinued
0.6835	Remote Similarity	NPD8032	Phase 2

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