NPASS Compound

Structure

NPC46259 OpenBabel07101718322D 26 32 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 -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 0 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 0.8537 0.9772 0.0000 C 0 0 1 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 0.8986 1.9762 0.0000 O 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 12 2 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 11 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 25 1 0 0 0 0 10 26 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 6 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 17 24 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:	350.13
Volume:	335.917
LogP:	1.819
LogD:	1.899
LogS:	-3.422
# Rotatable Bonds:	0
TPSA:	62.24
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	6.093
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.732
MDCK Permeability:	3.18523780151736e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.258
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.852
Plasma Protein Binding (PPB):	69.77465057373047%
Volume Distribution (VD):	2.39
Pgp-substrate:	26.936965942382812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.487
CYP1A2-substrate:	0.338
CYP2C19-inhibitor:	0.393
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.235
CYP2C9-substrate:	0.573
CYP2D6-inhibitor:	0.929
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.935
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	11.824
Half-life (T1/2):	0.473

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.561
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.43
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.197
Carcinogencity:	0.939
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC46259

Natural Product ID:	NPC46259
*Common Name:**	ZBFUQTFEXPQKQZ-FRYIKTPZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZBFUQTFEXPQKQZ-FRYIKTPZSA-N
Standard InCHI:	InChI=1S/C20H18N2O4/c23-16-17(24)22-13-9-15-14(25-10-26-15)8-11(13)12-2-7-21-6-1-3-19(16)4-5-20(12,22)18(19)21/h1-3,8-9,16,18,23H,4-7,10H2/t16-,18-,19-,20+/m0/s1
SMILES:	C1=C[C@]23CC[C@@]45C(=CCN(C1)[C@@H]34)c1cc3c(cc1N5C(=O)[C@@H]2O)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465857
PubChem CID:	10043462
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
MIC	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	<	1.95	ug.mL-1	PMID[483284]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	=	1.95	ug.mL-1	PMID[483284]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	>	1.95	ug.mL-1	PMID[483284]
NPT3651	Organism	Trichophyton tonsurans	Trichophyton tonsurans	MIC	=	3.9	ug.mL-1	PMID[483284]
NPT4353	Organism	Trichophyton interdigitale	Trichophyton interdigitale	MIC	<	3.9	ug.mL-1	PMID[483284]
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	MIC	=	7.8	ug.mL-1	PMID[483284]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	=	15.6	ug.mL-1	PMID[483284]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	7.8	ug.mL-1	PMID[483284]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	250.0	ug.mL-1	PMID[483284]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	500.0	ug.mL-1	PMID[483284]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	500.0	ug.mL-1	PMID[483284]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500.0	ug.mL-1	PMID[483284]

☑ 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 NPC46259 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	365
0.1-0.2	1826
0.2-0.3	7631
0.3-0.4	10687
0.4-0.5	15274
0.5-0.6	5765
0.6-0.7	985
0.7-0.8	162
0.8-0.85	0
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	NPC82541
0.8019	Intermediate Similarity	NPC127178
0.789	Intermediate Similarity	NPC288110
0.7818	Intermediate Similarity	NPC99724
0.7783	Intermediate Similarity	NPC148124
0.7778	Intermediate Similarity	NPC159815
0.7778	Intermediate Similarity	NPC127996
0.7773	Intermediate Similarity	NPC318525
0.7773	Intermediate Similarity	NPC10653
0.7758	Intermediate Similarity	NPC26928
0.7723	Intermediate Similarity	NPC248903
0.7717	Intermediate Similarity	NPC126556
0.7716	Intermediate Similarity	NPC477393
0.77	Intermediate Similarity	NPC475147
0.7696	Intermediate Similarity	NPC119722
0.765	Intermediate Similarity	NPC477396
0.7647	Intermediate Similarity	NPC222046
0.7644	Intermediate Similarity	NPC473458
0.7615	Intermediate Similarity	NPC10732
0.7604	Intermediate Similarity	NPC269449
0.7585	Intermediate Similarity	NPC473569
0.7565	Intermediate Similarity	NPC291173
0.7561	Intermediate Similarity	NPC102760
0.7558	Intermediate Similarity	NPC475133
0.7556	Intermediate Similarity	NPC231924
0.7512	Intermediate Similarity	NPC204970
0.75	Intermediate Similarity	NPC128476
0.7489	Intermediate Similarity	NPC37957
0.7478	Intermediate Similarity	NPC19175
0.7478	Intermediate Similarity	NPC122886
0.7477	Intermediate Similarity	NPC195636
0.7467	Intermediate Similarity	NPC250960
0.7467	Intermediate Similarity	NPC71539
0.7456	Intermediate Similarity	NPC74216
0.7445	Intermediate Similarity	NPC266994
0.7431	Intermediate Similarity	NPC205926
0.7418	Intermediate Similarity	NPC100863
0.7412	Intermediate Similarity	NPC471513
0.7411	Intermediate Similarity	NPC153923
0.7407	Intermediate Similarity	NPC207971
0.7404	Intermediate Similarity	NPC477395
0.7383	Intermediate Similarity	NPC5374
0.7378	Intermediate Similarity	NPC476069
0.7373	Intermediate Similarity	NPC268077
0.7371	Intermediate Similarity	NPC161804
0.7354	Intermediate Similarity	NPC234772
0.7346	Intermediate Similarity	NPC473004
0.7336	Intermediate Similarity	NPC71124
0.7321	Intermediate Similarity	NPC21425
0.7318	Intermediate Similarity	NPC477160
0.7297	Intermediate Similarity	NPC470482
0.7297	Intermediate Similarity	NPC470481
0.7294	Intermediate Similarity	NPC87714
0.7293	Intermediate Similarity	NPC476436
0.7269	Intermediate Similarity	NPC138830
0.7269	Intermediate Similarity	NPC67904
0.7261	Intermediate Similarity	NPC470480
0.723	Intermediate Similarity	NPC254957
0.7215	Intermediate Similarity	NPC14339
0.7212	Intermediate Similarity	NPC77777
0.7206	Intermediate Similarity	NPC266176
0.7206	Intermediate Similarity	NPC290759
0.7206	Intermediate Similarity	NPC475686
0.7206	Intermediate Similarity	NPC82533
0.7206	Intermediate Similarity	NPC158148
0.7206	Intermediate Similarity	NPC58766
0.7204	Intermediate Similarity	NPC477186
0.7198	Intermediate Similarity	NPC470821
0.7198	Intermediate Similarity	NPC477397
0.7198	Intermediate Similarity	NPC474470
0.7196	Intermediate Similarity	NPC243626
0.7196	Intermediate Similarity	NPC230313
0.7181	Intermediate Similarity	NPC219397
0.7171	Intermediate Similarity	NPC311991
0.7171	Intermediate Similarity	NPC474475
0.717	Intermediate Similarity	NPC174629
0.7169	Intermediate Similarity	NPC473460
0.7164	Intermediate Similarity	NPC97072
0.7164	Intermediate Similarity	NPC215829
0.7162	Intermediate Similarity	NPC168250
0.7149	Intermediate Similarity	NPC476220
0.7149	Intermediate Similarity	NPC160113
0.7143	Intermediate Similarity	NPC473007
0.7137	Intermediate Similarity	NPC476429
0.7136	Intermediate Similarity	NPC477640
0.7136	Intermediate Similarity	NPC22476
0.7136	Intermediate Similarity	NPC225597
0.7136	Intermediate Similarity	NPC470739
0.7105	Intermediate Similarity	NPC108826
0.7104	Intermediate Similarity	NPC477161
0.7097	Intermediate Similarity	NPC23080
0.7097	Intermediate Similarity	NPC193906
0.7089	Intermediate Similarity	NPC473008
0.7067	Intermediate Similarity	NPC287152
0.7044	Intermediate Similarity	NPC24954
0.7042	Intermediate Similarity	NPC230098
0.7033	Intermediate Similarity	NPC85613
0.7033	Intermediate Similarity	NPC5167
0.7029	Intermediate Similarity	NPC476258
0.7029	Intermediate Similarity	NPC304837
0.7027	Intermediate Similarity	NPC246140
0.7027	Intermediate Similarity	NPC195787
0.7017	Intermediate Similarity	NPC184680
0.7009	Intermediate Similarity	NPC471561
0.7005	Intermediate Similarity	NPC162653
0.7004	Intermediate Similarity	NPC189661
0.7	Intermediate Similarity	NPC15919
0.6987	Remote Similarity	NPC151171
0.6987	Remote Similarity	NPC470784
0.6987	Remote Similarity	NPC474183
0.6987	Remote Similarity	NPC470785
0.6978	Remote Similarity	NPC476651
0.6977	Remote Similarity	NPC203628
0.6976	Remote Similarity	NPC247972
0.6975	Remote Similarity	NPC154922
0.6971	Remote Similarity	NPC469722
0.6968	Remote Similarity	NPC473005
0.6967	Remote Similarity	NPC474745
0.6967	Remote Similarity	NPC244554
0.6965	Remote Similarity	NPC78733
0.696	Remote Similarity	NPC473006
0.6952	Remote Similarity	NPC39822
0.6948	Remote Similarity	NPC83511
0.693	Remote Similarity	NPC5630
0.693	Remote Similarity	NPC55470
0.6927	Remote Similarity	NPC97100
0.6927	Remote Similarity	NPC320104
0.6927	Remote Similarity	NPC473375
0.6923	Remote Similarity	NPC232600
0.692	Remote Similarity	NPC478075
0.6919	Remote Similarity	NPC474325
0.6913	Remote Similarity	NPC87560
0.6913	Remote Similarity	NPC195120
0.6908	Remote Similarity	NPC100566
0.6908	Remote Similarity	NPC190332
0.6908	Remote Similarity	NPC181653
0.6905	Remote Similarity	NPC304675
0.6893	Remote Similarity	NPC231198
0.6888	Remote Similarity	NPC49583
0.6885	Remote Similarity	NPC120239
0.6881	Remote Similarity	NPC221687
0.688	Remote Similarity	NPC115588
0.6878	Remote Similarity	NPC70172
0.6872	Remote Similarity	NPC237044
0.6872	Remote Similarity	NPC287588
0.6869	Remote Similarity	NPC116007
0.6869	Remote Similarity	NPC475981
0.6869	Remote Similarity	NPC474746
0.6854	Remote Similarity	NPC179704
0.6849	Remote Similarity	NPC303214
0.6842	Remote Similarity	NPC474708
0.684	Remote Similarity	NPC294790
0.684	Remote Similarity	NPC118633
0.684	Remote Similarity	NPC303658
0.684	Remote Similarity	NPC148693
0.6835	Remote Similarity	NPC302001
0.6833	Remote Similarity	NPC267414
0.6831	Remote Similarity	NPC113455
0.683	Remote Similarity	NPC470484
0.6827	Remote Similarity	NPC303374
0.6818	Remote Similarity	NPC472191
0.6818	Remote Similarity	NPC24228
0.681	Remote Similarity	NPC65403
0.6809	Remote Similarity	NPC477394
0.6808	Remote Similarity	NPC149285
0.6806	Remote Similarity	NPC477259
0.6806	Remote Similarity	NPC169387
0.6802	Remote Similarity	NPC474427
0.6794	Remote Similarity	NPC475845
0.6792	Remote Similarity	NPC283810
0.6791	Remote Similarity	NPC262725
0.6789	Remote Similarity	NPC63152
0.6787	Remote Similarity	NPC17677
0.6781	Remote Similarity	NPC157983
0.6781	Remote Similarity	NPC118154
0.6777	Remote Similarity	NPC2314
0.6774	Remote Similarity	NPC474904
0.6774	Remote Similarity	NPC474059
0.6771	Remote Similarity	NPC471489
0.6763	Remote Similarity	NPC476569
0.6763	Remote Similarity	NPC218614
0.6759	Remote Similarity	NPC9867
0.6758	Remote Similarity	NPC470485
0.6756	Remote Similarity	NPC473422
0.6747	Remote Similarity	NPC189079
0.6746	Remote Similarity	NPC474324
0.6746	Remote Similarity	NPC57812
0.6746	Remote Similarity	NPC252960
0.6745	Remote Similarity	NPC187678
0.6744	Remote Similarity	NPC249405
0.6742	Remote Similarity	NPC475713
0.6742	Remote Similarity	NPC474432
0.6741	Remote Similarity	NPC1464
0.6741	Remote Similarity	NPC475747
0.674	Remote Similarity	NPC317709
0.674	Remote Similarity	NPC329329
0.6731	Remote Similarity	NPC306669
0.673	Remote Similarity	NPC476441
0.6716	Remote Similarity	NPC93593
0.6714	Remote Similarity	NPC477185

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 NPC46259 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	616
0.2-0.3	953
0.3-0.4	1981
0.4-0.5	3187
0.5-0.6	1899
0.6-0.7	295
0.7-0.8	7
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
0.7488	Intermediate Similarity	NPD5582	Discontinued
0.7376	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7280	Phase 3
0.726	Intermediate Similarity	NPD7281	Phase 3
0.7195	Intermediate Similarity	NPD4859	Phase 1
0.7085	Intermediate Similarity	NPD3592	Approved
0.7085	Intermediate Similarity	NPD3591	Approved
0.7064	Intermediate Similarity	NPD4885	Approved
0.7022	Intermediate Similarity	NPD683	Approved
0.7	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5071	Phase 2
0.6906	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5561	Approved
0.6826	Remote Similarity	NPD5562	Approved
0.6824	Remote Similarity	NPD7805	Phase 3
0.682	Remote Similarity	NPD6625	Approved
0.681	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4846	Phase 2
0.6792	Remote Similarity	NPD6297	Approved
0.6787	Remote Similarity	NPD6877	Discontinued
0.678	Remote Similarity	NPD7186	Phase 3
0.6771	Remote Similarity	NPD6238	Discontinued
0.6771	Remote Similarity	NPD3416	Discontinued
0.6762	Remote Similarity	NPD6517	Phase 3
0.6753	Remote Similarity	NPD8149	Discontinued
0.6744	Remote Similarity	NPD6853	Approved
0.6744	Remote Similarity	NPD6851	Approved
0.6737	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3983	Phase 3
0.6727	Remote Similarity	NPD6493	Phase 3
0.6715	Remote Similarity	NPD4796	Discontinued
0.6714	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3437	Discontinued
0.6699	Remote Similarity	NPD1743	Approved
0.6699	Remote Similarity	NPD19	Approved
0.6699	Remote Similarity	NPD1742	Approved
0.6698	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5313	Approved
0.6698	Remote Similarity	NPD5600	Discontinued
0.6698	Remote Similarity	NPD5312	Approved
0.6696	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6644	Discontinued
0.6667	Remote Similarity	NPD3441	Approved
0.6667	Remote Similarity	NPD3442	Approved
0.6667	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4420	Approved
0.6624	Remote Similarity	NPD3912	Discontinued
0.6624	Remote Similarity	NPD7820	Phase 3
0.6612	Remote Similarity	NPD6723	Discontinued
0.6608	Remote Similarity	NPD4040	Phase 1
0.6602	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD8027	Approved
0.6593	Remote Similarity	NPD5006	Approved
0.6593	Remote Similarity	NPD5005	Approved
0.6591	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD5457	Discontinued
0.6571	Remote Similarity	NPD6457	Approved
0.6567	Remote Similarity	NPD7559	Phase 2
0.6556	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7225	Discontinued
0.655	Remote Similarity	NPD7263	Phase 2
0.6545	Remote Similarity	NPD2845	Phase 2
0.6545	Remote Similarity	NPD2843	Phase 2
0.6541	Remote Similarity	NPD8460	Approved
0.6541	Remote Similarity	NPD8459	Approved
0.654	Remote Similarity	NPD5186	Approved
0.654	Remote Similarity	NPD4166	Phase 2
0.654	Remote Similarity	NPD5183	Approved
0.6532	Remote Similarity	NPD3631	Phase 3
0.653	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5519	Discontinued
0.6522	Remote Similarity	NPD5658	Approved
0.6522	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD2973	Approved
0.6518	Remote Similarity	NPD2974	Approved
0.6518	Remote Similarity	NPD2975	Approved
0.6515	Remote Similarity	NPD8427	Approved
0.6515	Remote Similarity	NPD8465	Approved
0.6515	Remote Similarity	NPD8429	Approved
0.6515	Remote Similarity	NPD8467	Approved
0.6515	Remote Similarity	NPD8428	Approved
0.6515	Remote Similarity	NPD8466	Approved
0.6513	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6997	Phase 2
0.6512	Remote Similarity	NPD3885	Approved
0.6502	Remote Similarity	NPD7796	Approved
0.6502	Remote Similarity	NPD7797	Approved
0.65	Remote Similarity	NPD7223	Discontinued
0.65	Remote Similarity	NPD7224	Discontinued
0.6496	Remote Similarity	NPD4897	Phase 2
0.6486	Remote Similarity	NPD7296	Approved
0.6476	Remote Similarity	NPD3452	Approved
0.6476	Remote Similarity	NPD3450	Approved
0.6475	Remote Similarity	NPD8364	Approved
0.6475	Remote Similarity	NPD8363	Approved
0.6466	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5860	Discontinued
0.6466	Remote Similarity	NPD5645	Phase 3
0.6456	Remote Similarity	NPD2899	Discontinued
0.6449	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2488	Approved
0.6441	Remote Similarity	NPD2490	Approved
0.6438	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4580	Approved
0.6429	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD8426	Approved
0.6418	Remote Similarity	NPD8425	Approved
0.6413	Remote Similarity	NPD3634	Approved
0.6413	Remote Similarity	NPD3633	Approved
0.6411	Remote Similarity	NPD7560	Approved
0.6404	Remote Similarity	NPD2493	Approved
0.6404	Remote Similarity	NPD2494	Approved
0.6402	Remote Similarity	NPD2898	Approved
0.64	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5025	Approved
0.6396	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD2971	Approved
0.6393	Remote Similarity	NPD2968	Approved
0.6391	Remote Similarity	NPD3298	Approved
0.639	Remote Similarity	NPD3639	Approved
0.639	Remote Similarity	NPD3640	Phase 3
0.639	Remote Similarity	NPD3641	Approved
0.6389	Remote Similarity	NPD3793	Phase 3
0.6384	Remote Similarity	NPD7262	Phase 1
0.6379	Remote Similarity	NPD4082	Approved
0.6376	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5938	Phase 3
0.6371	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7479	Phase 2
0.6355	Remote Similarity	NPD4083	Discontinued
0.6351	Remote Similarity	NPD3349	Phase 2
0.6348	Remote Similarity	NPD4004	Approved
0.6348	Remote Similarity	NPD4002	Approved
0.6345	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8016	Phase 3
0.6342	Remote Similarity	NPD8255	Phase 2
0.6339	Remote Similarity	NPD3479	Discontinued
0.6338	Remote Similarity	NPD6107	Approved
0.6333	Remote Similarity	NPD6063	Approved
0.6333	Remote Similarity	NPD5506	Approved
0.6333	Remote Similarity	NPD5507	Approved
0.6331	Remote Similarity	NPD6982	Phase 2
0.633	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4120	Approved
0.6329	Remote Similarity	NPD4121	Phase 3
0.6328	Remote Similarity	NPD8463	Approved
0.6327	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.632	Remote Similarity	NPD4583	Approved
0.632	Remote Similarity	NPD4582	Approved
0.6318	Remote Similarity	NPD5496	Approved
0.6318	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD8461	Discontinued
0.6316	Remote Similarity	NPD3297	Approved
0.6313	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD2907	Approved
0.6309	Remote Similarity	NPD2906	Approved
0.6309	Remote Similarity	NPD4154	Approved
0.6306	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4515	Suspended
0.6298	Remote Similarity	NPD5742	Approved
0.6298	Remote Similarity	NPD5741	Approved
0.6298	Remote Similarity	NPD5743	Approved
0.6298	Remote Similarity	NPD4206	Approved
0.6296	Remote Similarity	NPD7426	Phase 1
0.6296	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD5994	Discontinued
0.6295	Remote Similarity	NPD6716	Phase 1
0.6293	Remote Similarity	NPD7955	Approved
0.6293	Remote Similarity	NPD7956	Approved
0.6291	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6612	Phase 2
0.6282	Remote Similarity	NPD4917	Discontinued
0.6281	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7279	Phase 2
0.6281	Remote Similarity	NPD7278	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