NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.08
Volume:	264.902
LogP:	3.748
LogD:	3.216
LogS:	-5.623
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	1.92
Fsp3:	0.125
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:	-4.714
MDCK Permeability:	1.971953133761417e-05
Pgp-inhibitor:	0.366
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	98.1795654296875%
Volume Distribution (VD):	0.494
Pgp-substrate:	1.2884423732757568%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.618
CYP2C19-substrate:	0.175
CYP2C9-inhibitor:	0.656
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.528
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	4.865
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.789
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.613
Skin Sensitization:	0.08
Carcinogencity:	0.949
Eye Corrosion:	0.004
Eye Irritation:	0.967
Respiratory Toxicity:	0.098

Download Data

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

Natural Product: NPC57552

Natural Product ID:	NPC57552
*Common Name:**	1-Methoxy-2-Methyl-Anthraquinone
IUPAC Name:	1-methoxy-2-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	MZFYROVNJMBHPG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O3/c1-9-7-8-12-13(16(9)19-2)15(18)11-6-4-3-5-10(11)14(12)17/h3-8H,1-2H3
SMILES:	Cc1ccc2c(C(=O)c3ccccc3C2=O)c1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL41178
PubChem CID:	3534338
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
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22860454]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO20880	Conocybe siliginea	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32816486]
NPO30535	Morinda umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4192	Gynochthodes umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20572	Vepris louisii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30535	Morinda umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20364	Ophelia bicornis	Species	Opheliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4192	Gynochthodes umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21199	Alangium platanifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20822	Asperula odora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15980	Croton penduliflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20880	Conocybe siliginea	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20064	Litsea konishii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19956	Pulveroboletus retipes	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20572	Vepris louisii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8020	Lychnophora columnaris	Species	Asteraceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	>	60000.0	nM	PMID[550687]

☑ 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 NPC57552 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	430
0.1-0.2	1791
0.2-0.3	4184
0.3-0.4	11512
0.4-0.5	6846
0.5-0.6	5140
0.6-0.7	8503
0.7-0.8	4011
0.8-0.85	222
0.85-0.9	47
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9606	High Similarity	NPC1249
0.9242	High Similarity	NPC1268
0.9194	High Similarity	NPC182646
0.9104	High Similarity	NPC124365
0.9077	High Similarity	NPC470406
0.9037	High Similarity	NPC69755
0.9015	High Similarity	NPC141934
0.8976	High Similarity	NPC474264
0.8976	High Similarity	NPC177925
0.8971	High Similarity	NPC53016
0.8968	High Similarity	NPC56332
0.8955	High Similarity	NPC223336
0.8906	High Similarity	NPC45537
0.8862	High Similarity	NPC171023
0.8855	High Similarity	NPC183103
0.8841	High Similarity	NPC49282
0.8832	High Similarity	NPC167663
0.8824	High Similarity	NPC149780
0.8819	High Similarity	NPC142956
0.8779	High Similarity	NPC164295
0.8777	High Similarity	NPC300540
0.876	High Similarity	NPC428300
0.8712	High Similarity	NPC474340
0.8705	High Similarity	NPC478019
0.8682	High Similarity	NPC474737
0.8676	High Similarity	NPC470407
0.8667	High Similarity	NPC301341
0.8667	High Similarity	NPC186647
0.8667	High Similarity	NPC284184
0.8657	High Similarity	NPC22222
0.8657	High Similarity	NPC281513
0.864	High Similarity	NPC201284
0.8636	High Similarity	NPC239134
0.8636	High Similarity	NPC205360
0.8636	High Similarity	NPC301717
0.8633	High Similarity	NPC93241
0.8633	High Similarity	NPC27798
0.8615	High Similarity	NPC298884
0.8593	High Similarity	NPC232996
0.8582	High Similarity	NPC190648
0.8582	High Similarity	NPC478018
0.8582	High Similarity	NPC56433
0.8582	High Similarity	NPC126767
0.8582	High Similarity	NPC245584
0.8582	High Similarity	NPC289042
0.8582	High Similarity	NPC312929
0.8582	High Similarity	NPC118027
0.8561	High Similarity	NPC117674
0.855	High Similarity	NPC48248
0.855	High Similarity	NPC282923
0.8531	High Similarity	NPC255641
0.8531	High Similarity	NPC290954
0.8521	High Similarity	NPC472056
0.8521	High Similarity	NPC474107
0.8519	High Similarity	NPC217914
0.8516	High Similarity	NPC300274
0.8511	High Similarity	NPC281398
0.8496	Intermediate Similarity	NPC477412
0.8485	Intermediate Similarity	NPC146647
0.8485	Intermediate Similarity	NPC34414
0.8473	Intermediate Similarity	NPC470841
0.8472	Intermediate Similarity	NPC118427
0.8472	Intermediate Similarity	NPC473201
0.8472	Intermediate Similarity	NPC302783
0.845	Intermediate Similarity	NPC375356
0.8444	Intermediate Similarity	NPC274876
0.844	Intermediate Similarity	NPC160777
0.844	Intermediate Similarity	NPC73416
0.8429	Intermediate Similarity	NPC66593
0.8429	Intermediate Similarity	NPC163948
0.8421	Intermediate Similarity	NPC55949
0.8421	Intermediate Similarity	NPC199253
0.8421	Intermediate Similarity	NPC31799
0.8421	Intermediate Similarity	NPC136588
0.8414	Intermediate Similarity	NPC164912
0.8409	Intermediate Similarity	NPC125887
0.8406	Intermediate Similarity	NPC477408
0.8403	Intermediate Similarity	NPC294646
0.8403	Intermediate Similarity	NPC147735
0.8403	Intermediate Similarity	NPC470568
0.8403	Intermediate Similarity	NPC474660
0.8385	Intermediate Similarity	NPC173978
0.8385	Intermediate Similarity	NPC470162
0.8385	Intermediate Similarity	NPC470163
0.8385	Intermediate Similarity	NPC75432
0.8382	Intermediate Similarity	NPC95485
0.8382	Intermediate Similarity	NPC88065
0.8382	Intermediate Similarity	NPC89504
0.8372	Intermediate Similarity	NPC307174
0.837	Intermediate Similarity	NPC115458
0.837	Intermediate Similarity	NPC225051
0.8369	Intermediate Similarity	NPC193703
0.8369	Intermediate Similarity	NPC21599
0.8369	Intermediate Similarity	NPC19896
0.8369	Intermediate Similarity	NPC229787
0.8358	Intermediate Similarity	NPC205992
0.8356	Intermediate Similarity	NPC208806
0.8346	Intermediate Similarity	NPC54243
0.8346	Intermediate Similarity	NPC35744
0.8346	Intermediate Similarity	NPC99731
0.8345	Intermediate Similarity	NPC470569
0.8345	Intermediate Similarity	NPC144283
0.8333	Intermediate Similarity	NPC233707
0.8321	Intermediate Similarity	NPC471670
0.8321	Intermediate Similarity	NPC224657
0.8321	Intermediate Similarity	NPC103540
0.8299	Intermediate Similarity	NPC226656
0.8299	Intermediate Similarity	NPC3898
0.8299	Intermediate Similarity	NPC66508
0.8296	Intermediate Similarity	NPC58685
0.8296	Intermediate Similarity	NPC70622
0.8295	Intermediate Similarity	NPC314329
0.8288	Intermediate Similarity	NPC154683
0.8288	Intermediate Similarity	NPC40356
0.8288	Intermediate Similarity	NPC24232
0.8276	Intermediate Similarity	NPC144010
0.8276	Intermediate Similarity	NPC473466
0.8273	Intermediate Similarity	NPC26924
0.8268	Intermediate Similarity	NPC32298
0.8261	Intermediate Similarity	NPC471542
0.8258	Intermediate Similarity	NPC96915
0.8252	Intermediate Similarity	NPC60389
0.8252	Intermediate Similarity	NPC211565
0.8248	Intermediate Similarity	NPC22644
0.8248	Intermediate Similarity	NPC283088
0.8248	Intermediate Similarity	NPC80035
0.8243	Intermediate Similarity	NPC279605
0.8239	Intermediate Similarity	NPC472836
0.8239	Intermediate Similarity	NPC48762
0.8239	Intermediate Similarity	NPC308006
0.8239	Intermediate Similarity	NPC189650
0.8235	Intermediate Similarity	NPC53896
0.8235	Intermediate Similarity	NPC52407
0.8231	Intermediate Similarity	NPC107109
0.8222	Intermediate Similarity	NPC279596
0.8222	Intermediate Similarity	NPC244699
0.8219	Intermediate Similarity	NPC145830
0.8214	Intermediate Similarity	NPC315578
0.8214	Intermediate Similarity	NPC109007
0.8207	Intermediate Similarity	NPC70764
0.8207	Intermediate Similarity	NPC329933
0.8201	Intermediate Similarity	NPC475104
0.8194	Intermediate Similarity	NPC71055
0.8194	Intermediate Similarity	NPC34802
0.8188	Intermediate Similarity	NPC67197
0.8188	Intermediate Similarity	NPC474813
0.8188	Intermediate Similarity	NPC272268
0.8188	Intermediate Similarity	NPC155211
0.8188	Intermediate Similarity	NPC178976
0.8182	Intermediate Similarity	NPC34482
0.8182	Intermediate Similarity	NPC2771
0.8175	Intermediate Similarity	NPC324117
0.8175	Intermediate Similarity	NPC50924
0.8169	Intermediate Similarity	NPC215451
0.8169	Intermediate Similarity	NPC277369
0.816	Intermediate Similarity	NPC279916
0.8148	Intermediate Similarity	NPC198305
0.8148	Intermediate Similarity	NPC7569
0.8148	Intermediate Similarity	NPC278787
0.814	Intermediate Similarity	NPC206778
0.814	Intermediate Similarity	NPC285829
0.8138	Intermediate Similarity	NPC192069
0.8133	Intermediate Similarity	NPC324736
0.8129	Intermediate Similarity	NPC290601
0.8129	Intermediate Similarity	NPC245923
0.8125	Intermediate Similarity	NPC147250
0.8125	Intermediate Similarity	NPC470570
0.8121	Intermediate Similarity	NPC5379
0.8121	Intermediate Similarity	NPC77807
0.8121	Intermediate Similarity	NPC14561
0.812	Intermediate Similarity	NPC3224
0.8116	Intermediate Similarity	NPC258502
0.8112	Intermediate Similarity	NPC309169
0.8112	Intermediate Similarity	NPC89664
0.8112	Intermediate Similarity	NPC196941
0.8112	Intermediate Similarity	NPC274085
0.8112	Intermediate Similarity	NPC290038
0.8108	Intermediate Similarity	NPC179170
0.8108	Intermediate Similarity	NPC214632
0.8106	Intermediate Similarity	NPC68756
0.8106	Intermediate Similarity	NPC152525
0.8099	Intermediate Similarity	NPC182255
0.8099	Intermediate Similarity	NPC329493
0.8099	Intermediate Similarity	NPC49108
0.8099	Intermediate Similarity	NPC94076
0.8095	Intermediate Similarity	NPC39819
0.8088	Intermediate Similarity	NPC474517
0.8088	Intermediate Similarity	NPC141549
0.8088	Intermediate Similarity	NPC72669
0.8082	Intermediate Similarity	NPC472298
0.8082	Intermediate Similarity	NPC80370
0.8082	Intermediate Similarity	NPC37220
0.8079	Intermediate Similarity	NPC284495
0.8077	Intermediate Similarity	NPC144547
0.8074	Intermediate Similarity	NPC206028
0.8071	Intermediate Similarity	NPC265181
0.8071	Intermediate Similarity	NPC13715
0.8071	Intermediate Similarity	NPC4214
0.8069	Intermediate Similarity	NPC478163
0.8069	Intermediate Similarity	NPC119767

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 NPC57552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	992
0.2-0.3	1212
0.3-0.4	2622
0.4-0.5	2091
0.5-0.6	1193
0.6-0.7	506
0.7-0.8	103
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD2346	Discontinued
0.8462	Intermediate Similarity	NPD3226	Approved
0.8397	Intermediate Similarity	NPD2798	Approved
0.8346	Intermediate Similarity	NPD1651	Approved
0.8321	Intermediate Similarity	NPD1470	Approved
0.8295	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD2313	Discontinued
0.8244	Intermediate Similarity	NPD1876	Approved
0.8154	Intermediate Similarity	NPD1281	Approved
0.8154	Intermediate Similarity	NPD1201	Approved
0.8092	Intermediate Similarity	NPD3972	Approved
0.8071	Intermediate Similarity	NPD1471	Phase 3
0.8058	Intermediate Similarity	NPD2799	Discontinued
0.8028	Intermediate Similarity	NPD7003	Approved
0.8	Intermediate Similarity	NPD2935	Discontinued
0.797	Intermediate Similarity	NPD1283	Approved
0.7929	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2344	Approved
0.7817	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD5691	Approved
0.7786	Intermediate Similarity	NPD1607	Approved
0.7748	Intermediate Similarity	NPD7819	Suspended
0.7746	Intermediate Similarity	NPD2796	Approved
0.7742	Intermediate Similarity	NPD6232	Discontinued
0.7737	Intermediate Similarity	NPD6832	Phase 2
0.7727	Intermediate Similarity	NPD4626	Approved
0.7727	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7473	Discontinued
0.7643	Intermediate Similarity	NPD4307	Phase 2
0.7643	Intermediate Similarity	NPD1240	Approved
0.7643	Intermediate Similarity	NPD2979	Phase 3
0.7622	Intermediate Similarity	NPD5408	Approved
0.7622	Intermediate Similarity	NPD5405	Approved
0.7622	Intermediate Similarity	NPD5406	Approved
0.7622	Intermediate Similarity	NPD5404	Approved
0.7603	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2309	Approved
0.7582	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1510	Phase 2
0.7552	Intermediate Similarity	NPD3748	Approved
0.7517	Intermediate Similarity	NPD6273	Approved
0.7483	Intermediate Similarity	NPD7458	Discontinued
0.7481	Intermediate Similarity	NPD1611	Approved
0.7466	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1933	Approved
0.7462	Intermediate Similarity	NPD1241	Discontinued
0.7452	Intermediate Similarity	NPD6959	Discontinued
0.745	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2534	Approved
0.745	Intermediate Similarity	NPD2532	Approved
0.745	Intermediate Similarity	NPD2533	Approved
0.745	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD8032	Phase 2
0.7431	Intermediate Similarity	NPD4308	Phase 3
0.7391	Intermediate Similarity	NPD1203	Approved
0.7391	Intermediate Similarity	NPD3266	Approved
0.7391	Intermediate Similarity	NPD3267	Approved
0.7389	Intermediate Similarity	NPD5494	Approved
0.7379	Intermediate Similarity	NPD2438	Suspended
0.7379	Intermediate Similarity	NPD2531	Phase 2
0.7376	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD17	Approved
0.7299	Intermediate Similarity	NPD9717	Approved
0.7297	Intermediate Similarity	NPD3750	Approved
0.7297	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD9493	Approved
0.729	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1549	Phase 2
0.7273	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD7411	Suspended
0.7273	Intermediate Similarity	NPD5951	Approved
0.7273	Intermediate Similarity	NPD8312	Approved
0.7267	Intermediate Similarity	NPD7390	Discontinued
0.7266	Intermediate Similarity	NPD2797	Approved
0.726	Intermediate Similarity	NPD1551	Phase 2
0.7254	Intermediate Similarity	NPD3764	Approved
0.7244	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5536	Phase 2
0.723	Intermediate Similarity	NPD1243	Approved
0.7226	Intermediate Similarity	NPD6844	Discontinued
0.7226	Intermediate Similarity	NPD6280	Approved
0.7226	Intermediate Similarity	NPD6279	Approved
0.7222	Intermediate Similarity	NPD447	Suspended
0.7214	Intermediate Similarity	NPD1019	Discontinued
0.7211	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4380	Phase 2
0.7208	Intermediate Similarity	NPD6599	Discontinued
0.7197	Intermediate Similarity	NPD7768	Phase 2
0.7183	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7008	Discontinued
0.7179	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1608	Approved
0.7165	Intermediate Similarity	NPD164	Approved
0.7161	Intermediate Similarity	NPD5889	Approved
0.7161	Intermediate Similarity	NPD5890	Approved
0.716	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD2651	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD2649	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7132	Intermediate Similarity	NPD3025	Approved
0.7132	Intermediate Similarity	NPD2342	Discontinued
0.7132	Intermediate Similarity	NPD3024	Approved
0.7124	Intermediate Similarity	NPD920	Approved
0.7122	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7177	Discontinued
0.7117	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1934	Approved
0.7105	Intermediate Similarity	NPD4662	Approved
0.7105	Intermediate Similarity	NPD4661	Approved
0.7105	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6585	Discontinued
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3019	Approved
0.7077	Intermediate Similarity	NPD2182	Approved
0.7073	Intermediate Similarity	NPD5844	Phase 1
0.707	Intermediate Similarity	NPD2801	Approved
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7063	Intermediate Similarity	NPD4625	Phase 3
0.7044	Intermediate Similarity	NPD7075	Discontinued
0.7039	Intermediate Similarity	NPD1511	Approved
0.7039	Intermediate Similarity	NPD6799	Approved
0.7037	Intermediate Similarity	NPD3926	Phase 2
0.7029	Intermediate Similarity	NPD3023	Approved
0.7029	Intermediate Similarity	NPD3026	Approved
0.7027	Intermediate Similarity	NPD6100	Approved
0.7027	Intermediate Similarity	NPD6099	Approved
0.7025	Intermediate Similarity	NPD5402	Approved
0.7025	Intermediate Similarity	NPD5977	Approved
0.7025	Intermediate Similarity	NPD5978	Approved
0.7025	Intermediate Similarity	NPD2296	Approved
0.7013	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5585	Approved
0.7006	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD5327	Phase 3
0.7	Intermediate Similarity	NPD2800	Approved
0.6994	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5401	Approved
0.6986	Remote Similarity	NPD4618	Approved
0.6986	Remote Similarity	NPD4622	Approved
0.6981	Remote Similarity	NPD3882	Suspended
0.6963	Remote Similarity	NPD709	Approved
0.6957	Remote Similarity	NPD2932	Approved
0.6957	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD9261	Approved
0.6948	Remote Similarity	NPD1512	Approved
0.6946	Remote Similarity	NPD6559	Discontinued
0.694	Remote Similarity	NPD5283	Phase 1
0.6939	Remote Similarity	NPD4097	Suspended
0.6933	Remote Similarity	NPD2897	Discontinued
0.6932	Remote Similarity	NPD8285	Discontinued
0.6923	Remote Similarity	NPD9494	Approved
0.6918	Remote Similarity	NPD3817	Phase 2
0.6918	Remote Similarity	NPD4060	Phase 1
0.6918	Remote Similarity	NPD943	Approved
0.6914	Remote Similarity	NPD1247	Approved
0.6903	Remote Similarity	NPD5403	Approved
0.6897	Remote Similarity	NPD6798	Discontinued
0.6897	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD919	Approved
0.6894	Remote Similarity	NPD5451	Approved
0.6893	Remote Similarity	NPD6779	Approved
0.6893	Remote Similarity	NPD6781	Approved
0.6893	Remote Similarity	NPD6782	Approved
0.6893	Remote Similarity	NPD6780	Approved
0.6893	Remote Similarity	NPD6778	Approved
0.6893	Remote Similarity	NPD6777	Approved
0.6893	Remote Similarity	NPD6776	Approved
0.6892	Remote Similarity	NPD5689	Approved
0.6892	Remote Similarity	NPD5688	Approved
0.6884	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5710	Approved
0.6871	Remote Similarity	NPD6808	Phase 2
0.6871	Remote Similarity	NPD5711	Approved
0.6866	Remote Similarity	NPD7635	Approved
0.6866	Remote Similarity	NPD5535	Approved
0.6863	Remote Similarity	NPD3300	Phase 2
0.6861	Remote Similarity	NPD7644	Approved
0.6857	Remote Similarity	NPD6287	Discontinued
0.6853	Remote Similarity	NPD4624	Approved
0.685	Remote Similarity	NPD1238	Approved
0.6842	Remote Similarity	NPD8150	Discontinued
0.6839	Remote Similarity	NPD5049	Phase 3
0.6838	Remote Similarity	NPD6387	Discontinued

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