NPASS Compound

Structure

NPC82541 OpenBabel07101718182D 25 31 0 0 1 0 0 0 0 0999 V2000 0.5345 1.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6341 -0.7863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2506 1.3627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0007 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3428 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1212 1.2373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7333 -0.0543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3085 -1.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3085 0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8537 0.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0402 -0.5826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6848 -0.9426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.1651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6848 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9321 -0.9426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9321 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1916 0.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5129 0.4134 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4878 0.6359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4233 -0.5826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2228 0.4796 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5615 1.3521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6169 -1.1651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6169 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 2 13 1 0 0 0 0 4 5 1 0 0 0 0 4 19 1 0 0 0 0 6 21 1 0 0 0 0 7 21 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 20 1 6 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 22 1 0 0 0 0 17 23 2 0 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 3 1 1 0 0 0 20 5 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.15
Volume:	329.763
LogP:	2.44
LogD:	2.035
LogS:	-4.21
# Rotatable Bonds:	0
TPSA:	42.01
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.683
Synthetic Accessibility Score:	5.697
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.851
MDCK Permeability:	2.8254924473003484e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.529
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.863
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	56.88694763183594%
Volume Distribution (VD):	1.974
Pgp-substrate:	38.048614501953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.617
CYP1A2-substrate:	0.626
CYP2C19-inhibitor:	0.214
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.526
CYP2D6-inhibitor:	0.893
CYP2D6-substrate:	0.441
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.866

ADMET: Excretion

Clearance (CL):	14.361
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.291
Carcinogencity:	0.965
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC82541

Natural Product ID:	NPC82541
*Common Name:**	Schizozygine
IUPAC Name:	n.a.
Synonyms:	Schizozygine
Standard InCHIKey:	DTBOGXTYLFTPCH-XCXWGBRNSA-N
Standard InCHI:	InChI=1S/C20H20N2O3/c23-17-10-19-3-1-6-21-7-2-13-12-8-15-16(25-11-24-15)9-14(12)22(17)20(13,5-4-19)18(19)21/h1,3,8-9,13,18H,2,4-7,10-11H2/t13-,18-,19-,20+/m0/s1
SMILES:	O=C1C[C@]23C=CCN4[C@@H]3[C@@]3(N1c1cc5OCOc5cc1[C@@H]3CC4)CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516864
PubChem CID:	26204194
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003763] Schizozygine alkaloids

*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
NPO32657	schizozygia coffaeoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975502]

☑ 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	12

Activity Type	# Activity
Individual Protein	1
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[521296]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT3651	Organism	Trichophyton tonsurans	Trichophyton tonsurans	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT4353	Organism	Trichophyton interdigitale	Trichophyton interdigitale	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	500.0	ug.mL-1	PMID[521297]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500.0	ug.mL-1	PMID[521297]

☑ 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 NPC82541 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	485
0.1-0.2	2032
0.2-0.3	8366
0.3-0.4	10066
0.4-0.5	15993
0.5-0.6	4498
0.6-0.7	1101
0.7-0.8	148
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.915	High Similarity	NPC46259
0.8299	Intermediate Similarity	NPC473569
0.8204	Intermediate Similarity	NPC159815
0.8109	Intermediate Similarity	NPC127178
0.8039	Intermediate Similarity	NPC475147
0.801	Intermediate Similarity	NPC21425
0.7934	Intermediate Similarity	NPC10653
0.7934	Intermediate Similarity	NPC318525
0.7885	Intermediate Similarity	NPC475133
0.7857	Intermediate Similarity	NPC10732
0.7833	Intermediate Similarity	NPC71124
0.7794	Intermediate Similarity	NPC5374
0.7793	Intermediate Similarity	NPC126556
0.7773	Intermediate Similarity	NPC119722
0.7756	Intermediate Similarity	NPC67904
0.7756	Intermediate Similarity	NPC138830
0.7745	Intermediate Similarity	NPC100863
0.7727	Intermediate Similarity	NPC102760
0.7706	Intermediate Similarity	NPC231924
0.7678	Intermediate Similarity	NPC269449
0.7673	Intermediate Similarity	NPC473004
0.7671	Intermediate Similarity	NPC476436
0.7644	Intermediate Similarity	NPC207971
0.7635	Intermediate Similarity	NPC254957
0.7615	Intermediate Similarity	NPC71539
0.7615	Intermediate Similarity	NPC250960
0.7608	Intermediate Similarity	NPC268077
0.7586	Intermediate Similarity	NPC204970
0.755	Intermediate Similarity	NPC473007
0.7537	Intermediate Similarity	NPC22476
0.7523	Intermediate Similarity	NPC74216
0.7512	Intermediate Similarity	NPC230313
0.7511	Intermediate Similarity	NPC266994
0.75	Intermediate Similarity	NPC476429
0.7465	Intermediate Similarity	NPC195636
0.7461	Intermediate Similarity	NPC24954
0.7438	Intermediate Similarity	NPC477186
0.7432	Intermediate Similarity	NPC26928
0.7427	Intermediate Similarity	NPC243626
0.7409	Intermediate Similarity	NPC128476
0.7409	Intermediate Similarity	NPC99724
0.7404	Intermediate Similarity	NPC23080
0.7404	Intermediate Similarity	NPC193906
0.7402	Intermediate Similarity	NPC473008
0.7399	Intermediate Similarity	NPC248903
0.7397	Intermediate Similarity	NPC288110
0.7383	Intermediate Similarity	NPC168250
0.7376	Intermediate Similarity	NPC148124
0.7364	Intermediate Similarity	NPC476069
0.7361	Intermediate Similarity	NPC127996
0.7356	Intermediate Similarity	NPC161804
0.735	Intermediate Similarity	NPC85613
0.735	Intermediate Similarity	NPC5167
0.7346	Intermediate Similarity	NPC473005
0.7327	Intermediate Similarity	NPC473006
0.7324	Intermediate Similarity	NPC477161
0.7281	Intermediate Similarity	NPC470482
0.7281	Intermediate Similarity	NPC476220
0.7281	Intermediate Similarity	NPC470481
0.7281	Intermediate Similarity	NPC160113
0.7268	Intermediate Similarity	NPC169387
0.7268	Intermediate Similarity	NPC477259
0.7257	Intermediate Similarity	NPC470821
0.7256	Intermediate Similarity	NPC205926
0.7255	Intermediate Similarity	NPC83511
0.7253	Intermediate Similarity	NPC477393
0.7233	Intermediate Similarity	NPC174629
0.7232	Intermediate Similarity	NPC19175
0.7215	Intermediate Similarity	NPC55470
0.7202	Intermediate Similarity	NPC472098
0.7202	Intermediate Similarity	NPC78733
0.7191	Intermediate Similarity	NPC477396
0.7182	Intermediate Similarity	NPC234772
0.7178	Intermediate Similarity	NPC287588
0.7176	Intermediate Similarity	NPC317709
0.7176	Intermediate Similarity	NPC329329
0.7174	Intermediate Similarity	NPC291173
0.7171	Intermediate Similarity	NPC116007
0.7168	Intermediate Similarity	NPC473458
0.7165	Intermediate Similarity	NPC234392
0.7165	Intermediate Similarity	NPC31311
0.7162	Intermediate Similarity	NPC37957
0.7162	Intermediate Similarity	NPC222046
0.7162	Intermediate Similarity	NPC108826
0.7157	Intermediate Similarity	NPC179704
0.7155	Intermediate Similarity	NPC476258
0.7155	Intermediate Similarity	NPC304837
0.7143	Intermediate Similarity	NPC477160
0.7129	Intermediate Similarity	NPC287152
0.7122	Intermediate Similarity	NPC249405
0.7116	Intermediate Similarity	NPC14339
0.7116	Intermediate Similarity	NPC87714
0.7115	Intermediate Similarity	NPC203628
0.71	Intermediate Similarity	NPC154922
0.7098	Intermediate Similarity	NPC210148
0.7098	Intermediate Similarity	NPC233029
0.7094	Intermediate Similarity	NPC283810
0.7083	Intermediate Similarity	NPC303374
0.7081	Intermediate Similarity	NPC63152
0.7077	Intermediate Similarity	NPC146288
0.7072	Intermediate Similarity	NPC305984
0.7067	Intermediate Similarity	NPC5630
0.7065	Intermediate Similarity	NPC474708
0.7062	Intermediate Similarity	NPC477258
0.7056	Intermediate Similarity	NPC97072
0.7056	Intermediate Similarity	NPC215829
0.7048	Intermediate Similarity	NPC302001
0.7047	Intermediate Similarity	NPC478076
0.7045	Intermediate Similarity	NPC264176
0.704	Intermediate Similarity	NPC77777
0.7035	Intermediate Similarity	NPC247972
0.7035	Intermediate Similarity	NPC231198
0.7028	Intermediate Similarity	NPC24228
0.7028	Intermediate Similarity	NPC272706
0.7026	Intermediate Similarity	NPC138487
0.7026	Intermediate Similarity	NPC93593
0.7026	Intermediate Similarity	NPC216459
0.7026	Intermediate Similarity	NPC41178
0.702	Intermediate Similarity	NPC70172
0.7015	Intermediate Similarity	NPC475845
0.7009	Intermediate Similarity	NPC153923
0.7004	Intermediate Similarity	NPC115588
0.7004	Intermediate Similarity	NPC120239
0.6995	Remote Similarity	NPC223125
0.6991	Remote Similarity	NPC473460
0.6986	Remote Similarity	NPC312531
0.6981	Remote Similarity	NPC303214
0.698	Remote Similarity	NPC311991
0.6965	Remote Similarity	NPC474324
0.6965	Remote Similarity	NPC57812
0.6964	Remote Similarity	NPC195120
0.6964	Remote Similarity	NPC87560
0.6949	Remote Similarity	NPC477395
0.6949	Remote Similarity	NPC113455
0.6946	Remote Similarity	NPC65403
0.6943	Remote Similarity	NPC471513
0.6943	Remote Similarity	NPC470480
0.6938	Remote Similarity	NPC230098
0.6933	Remote Similarity	NPC219397
0.6931	Remote Similarity	NPC477185
0.6931	Remote Similarity	NPC476425
0.6931	Remote Similarity	NPC241055
0.693	Remote Similarity	NPC122886
0.6927	Remote Similarity	NPC222524
0.6923	Remote Similarity	NPC223124
0.6923	Remote Similarity	NPC148898
0.6919	Remote Similarity	NPC315498
0.6919	Remote Similarity	NPC477080
0.6919	Remote Similarity	NPC230942
0.6912	Remote Similarity	NPC477187
0.6905	Remote Similarity	NPC474904
0.6901	Remote Similarity	NPC162653
0.69	Remote Similarity	NPC476569
0.69	Remote Similarity	NPC320104
0.6898	Remote Similarity	NPC232600
0.6898	Remote Similarity	NPC295676
0.6895	Remote Similarity	NPC308943
0.6895	Remote Similarity	NPC478075
0.6891	Remote Similarity	NPC475959
0.6887	Remote Similarity	NPC203972
0.6884	Remote Similarity	NPC267414
0.6878	Remote Similarity	NPC476651
0.6866	Remote Similarity	NPC306669
0.6863	Remote Similarity	NPC476441
0.686	Remote Similarity	NPC27887
0.686	Remote Similarity	NPC474745
0.6847	Remote Similarity	NPC290759
0.6847	Remote Similarity	NPC475686
0.6847	Remote Similarity	NPC158148
0.6847	Remote Similarity	NPC82533
0.6847	Remote Similarity	NPC58766
0.6847	Remote Similarity	NPC266176
0.6845	Remote Similarity	NPC39822
0.6845	Remote Similarity	NPC474470
0.6838	Remote Similarity	NPC253675
0.6837	Remote Similarity	NPC17677
0.6834	Remote Similarity	NPC106786
0.6833	Remote Similarity	NPC471561
0.683	Remote Similarity	NPC189661
0.6829	Remote Similarity	NPC285941
0.6828	Remote Similarity	NPC157983
0.6828	Remote Similarity	NPC472099
0.6828	Remote Similarity	NPC118154
0.6825	Remote Similarity	NPC22689
0.6825	Remote Similarity	NPC105055
0.682	Remote Similarity	NPC471489
0.6816	Remote Similarity	NPC59567
0.6814	Remote Similarity	NPC474475
0.6814	Remote Similarity	NPC303658
0.6814	Remote Similarity	NPC75958
0.6812	Remote Similarity	NPC15919
0.6812	Remote Similarity	NPC474325
0.6809	Remote Similarity	NPC28641
0.6809	Remote Similarity	NPC194359
0.6809	Remote Similarity	NPC225745
0.6806	Remote Similarity	NPC212163
0.6804	Remote Similarity	NPC244606
0.6804	Remote Similarity	NPC156728
0.6798	Remote Similarity	NPC471604
0.6798	Remote Similarity	NPC85482

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 NPC82541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	638
0.2-0.3	915
0.3-0.4	1910
0.4-0.5	3406
0.5-0.6	1701
0.6-0.7	293
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.75	Intermediate Similarity	NPD4885	Approved
0.7413	Intermediate Similarity	NPD7281	Phase 3
0.7413	Intermediate Similarity	NPD7280	Phase 3
0.736	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD4859	Phase 1
0.7321	Intermediate Similarity	NPD5071	Phase 2
0.7264	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5582	Discontinued
0.7177	Intermediate Similarity	NPD6493	Phase 3
0.7172	Intermediate Similarity	NPD4166	Phase 2
0.717	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5313	Approved
0.7079	Intermediate Similarity	NPD5600	Discontinued
0.7079	Intermediate Similarity	NPD5312	Approved
0.7056	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3639	Approved
0.7031	Intermediate Similarity	NPD3641	Approved
0.7031	Intermediate Similarity	NPD3640	Phase 3
0.703	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD683	Approved
0.6971	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3983	Phase 3
0.695	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4796	Discontinued
0.6919	Remote Similarity	NPD19	Approved
0.6919	Remote Similarity	NPD1743	Approved
0.6919	Remote Similarity	NPD1742	Approved
0.6904	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7225	Discontinued
0.6872	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6457	Approved
0.6864	Remote Similarity	NPD5658	Approved
0.6864	Remote Similarity	NPD8027	Approved
0.6864	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4846	Phase 2
0.6833	Remote Similarity	NPD3592	Approved
0.6833	Remote Similarity	NPD3591	Approved
0.6832	Remote Similarity	NPD5186	Approved
0.6832	Remote Similarity	NPD5183	Approved
0.6828	Remote Similarity	NPD3437	Discontinued
0.6808	Remote Similarity	NPD3631	Phase 3
0.6795	Remote Similarity	NPD6625	Approved
0.6779	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3912	Discontinued
0.6732	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8149	Discontinued
0.6726	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3349	Phase 2
0.6683	Remote Similarity	NPD6297	Approved
0.6682	Remote Similarity	NPD6877	Discontinued
0.6681	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7559	Phase 2
0.6667	Remote Similarity	NPD3416	Discontinued
0.6667	Remote Similarity	NPD6238	Discontinued
0.6667	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4584	Approved
0.6653	Remote Similarity	NPD6723	Discontinued
0.6652	Remote Similarity	NPD5561	Approved
0.6652	Remote Similarity	NPD5562	Approved
0.665	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6618	Phase 2
0.6622	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6107	Approved
0.6606	Remote Similarity	NPD4420	Approved
0.6593	Remote Similarity	NPD3815	Phase 1
0.6593	Remote Similarity	NPD3816	Phase 1
0.6586	Remote Similarity	NPD7956	Approved
0.6586	Remote Similarity	NPD7955	Approved
0.6577	Remote Similarity	NPD6644	Discontinued
0.6577	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5519	Discontinued
0.6561	Remote Similarity	NPD5005	Approved
0.6561	Remote Similarity	NPD5006	Approved
0.6557	Remote Similarity	NPD6851	Approved
0.6557	Remote Similarity	NPD6853	Approved
0.6555	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7479	Phase 2
0.6549	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7291	Discontinued
0.6537	Remote Similarity	NPD7126	Discontinued
0.6533	Remote Similarity	NPD4917	Discontinued
0.6528	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7820	Phase 3
0.6522	Remote Similarity	NPD2898	Approved
0.652	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2968	Approved
0.6509	Remote Similarity	NPD2971	Approved
0.6507	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD4040	Phase 1
0.6498	Remote Similarity	NPD3441	Approved
0.6498	Remote Similarity	NPD3442	Approved
0.6496	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4154	Approved
0.6481	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5457	Discontinued
0.6468	Remote Similarity	NPD7223	Discontinued
0.6468	Remote Similarity	NPD7224	Discontinued
0.6461	Remote Similarity	NPD6517	Phase 3
0.6457	Remote Similarity	NPD7803	Approved
0.6453	Remote Similarity	NPD5977	Approved
0.6453	Remote Similarity	NPD5978	Approved
0.645	Remote Similarity	NPD4121	Phase 3
0.645	Remote Similarity	NPD4120	Approved
0.6446	Remote Similarity	NPD8016	Phase 3
0.6446	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6321	Discontinued
0.644	Remote Similarity	NPD2492	Phase 1
0.6438	Remote Similarity	NPD7805	Phase 3
0.6438	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7298	Approved
0.6435	Remote Similarity	NPD5025	Approved
0.6418	Remote Similarity	NPD5743	Approved
0.6418	Remote Similarity	NPD5741	Approved
0.6418	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5742	Approved
0.641	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7797	Approved
0.6402	Remote Similarity	NPD7796	Approved
0.6398	Remote Similarity	NPD7186	Phase 3
0.6396	Remote Similarity	NPD6612	Phase 2
0.6396	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4773	Phase 2
0.6386	Remote Similarity	NPD4772	Phase 2
0.6386	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7110	Phase 1
0.6368	Remote Similarity	NPD6357	Discontinued
0.6364	Remote Similarity	NPD6228	Discontinued
0.6352	Remote Similarity	NPD3763	Approved
0.6351	Remote Similarity	NPD3793	Phase 3
0.634	Remote Similarity	NPD6997	Phase 2
0.6335	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5515	Phase 2
0.6333	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2488	Approved
0.633	Remote Similarity	NPD2490	Approved
0.6329	Remote Similarity	NPD7426	Phase 1
0.6321	Remote Similarity	NPD3885	Approved
0.6314	Remote Similarity	NPD7278	Phase 2
0.6314	Remote Similarity	NPD7279	Phase 2
0.6314	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7296	Approved
0.6299	Remote Similarity	NPD7708	Approved
0.6293	Remote Similarity	NPD5967	Approved
0.629	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8358	Approved
0.6288	Remote Similarity	NPD5860	Discontinued
0.6287	Remote Similarity	NPD789	Phase 2
0.6286	Remote Similarity	NPD4481	Phase 3
0.6285	Remote Similarity	NPD8091	Phase 3
0.6284	Remote Similarity	NPD2845	Phase 2
0.6284	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2843	Phase 2
0.6283	Remote Similarity	NPD1294	Discontinued
0.6282	Remote Similarity	NPD2899	Discontinued
0.6282	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6964	Approved
0.6281	Remote Similarity	NPD6963	Approved
0.6279	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7248	Discontinued
0.6275	Remote Similarity	NPD1769	Discontinued
0.6274	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD4082	Approved
0.6267	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD4515	Suspended
0.6264	Remote Similarity	NPD8460	Approved
0.6264	Remote Similarity	NPD8459	Approved
0.6262	Remote Similarity	NPD6788	Approved
0.6256	Remote Similarity	NPD5601	Phase 2
0.6255	Remote Similarity	NPD8364	Approved
0.6255	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD8363	Approved
0.625	Remote Similarity	NPD4897	Phase 2
0.625	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6568	Discontinued
0.6236	Remote Similarity	NPD8467	Approved
0.6236	Remote Similarity	NPD8465	Approved
0.6236	Remote Similarity	NPD8466	Approved
0.6231	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6982	Phase 2
0.623	Remote Similarity	NPD5718	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