NPASS Compound

Structure

NPC68650 OpenBabel07101718202D 26 29 0 0 1 0 0 0 0 0999 V2000 3.7089 -2.0135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2312 -2.3035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3176 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1211 -1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1266 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 N 0 0 0 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 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 12 1 0 0 0 0 3 12 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 20 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 13 2 0 0 0 0 10 14 2 0 0 0 0 11 21 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 11 1 1 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 12 1 6 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 18 26 2 0 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 21 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.21
Volume:	372.298
LogP:	3.534
LogD:	3.304
LogS:	-4.526
# Rotatable Bonds:	3
TPSA:	61.44
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.821
Synthetic Accessibility Score:	4.325
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.892
MDCK Permeability:	5.135454921401106e-05
Pgp-inhibitor:	0.645
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	89.99520874023438%
Volume Distribution (VD):	0.834
Pgp-substrate:	9.03166389465332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.689
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.525
CYP2C9-substrate:	0.355
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.883
CYP3A4-substrate:	0.602

ADMET: Excretion

Clearance (CL):	2.23
Half-life (T1/2):	0.255

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.091
Skin Sensitization:	0.302
Carcinogencity:	0.123
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.292

Download Data

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

Natural Product: NPC68650

Natural Product ID:	NPC68650
*Common Name:**	Brevicompanine
IUPAC Name:	n.a.
Synonyms:	brevicompanine
Standard InCHIKey:	GFKUCJKLCHSSJN-JRYVEOFUSA-N
Standard InCHI:	InChI=1S/C21H27N3O2/c1-6-20(4,5)21-11-15-17(25)23-16(12(2)3)18(26)24(15)19(21)22-14-10-8-7-9-13(14)21/h6-10,12,15-16,19,22H,1,11H2,2-5H3,(H,23,25)/t15-,16+,19-,21+/m0/s1
SMILES:	C=CC(C)(C)[C@]12C[C@H]3C(=N[C@H](C(C)C)C(=O)N3[C@@H]2Nc2ccccc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472025
PubChem CID:	5325980
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO33398	penicillium brevi-compactum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730251]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	46.0	%	PMID[515836]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	=	212.0	%	PMID[515836]

☑ 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 NPC68650 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	242
0.1-0.2	1415
0.2-0.3	13115
0.3-0.4	18950
0.4-0.5	4746
0.5-0.6	3023
0.6-0.7	1109
0.7-0.8	92
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8963	High Similarity	NPC307396
0.848	Intermediate Similarity	NPC276430
0.8242	Intermediate Similarity	NPC355
0.8146	Intermediate Similarity	NPC106118
0.8084	Intermediate Similarity	NPC285622
0.7838	Intermediate Similarity	NPC472538
0.7818	Intermediate Similarity	NPC309531
0.7818	Intermediate Similarity	NPC472102
0.7805	Intermediate Similarity	NPC222029
0.7784	Intermediate Similarity	NPC225400
0.7746	Intermediate Similarity	NPC91179
0.7742	Intermediate Similarity	NPC471155
0.7742	Intermediate Similarity	NPC470786
0.7735	Intermediate Similarity	NPC471199
0.7701	Intermediate Similarity	NPC270241
0.7701	Intermediate Similarity	NPC71238
0.7697	Intermediate Similarity	NPC104345
0.7651	Intermediate Similarity	NPC276085
0.764	Intermediate Similarity	NPC213629
0.7579	Intermediate Similarity	NPC54981
0.7545	Intermediate Similarity	NPC471122
0.75	Intermediate Similarity	NPC66936
0.7486	Intermediate Similarity	NPC17059
0.7472	Intermediate Similarity	NPC259626
0.7471	Intermediate Similarity	NPC471124
0.7456	Intermediate Similarity	NPC472117
0.7452	Intermediate Similarity	NPC471123
0.7436	Intermediate Similarity	NPC248601
0.7427	Intermediate Similarity	NPC279527
0.7427	Intermediate Similarity	NPC214960
0.7416	Intermediate Similarity	NPC2933
0.7409	Intermediate Similarity	NPC471663
0.7394	Intermediate Similarity	NPC295548
0.7378	Intermediate Similarity	NPC109787
0.7362	Intermediate Similarity	NPC264589
0.736	Intermediate Similarity	NPC256288
0.7354	Intermediate Similarity	NPC473376
0.7333	Intermediate Similarity	NPC318086
0.7318	Intermediate Similarity	NPC228835
0.7312	Intermediate Similarity	NPC171317
0.7273	Intermediate Similarity	NPC293917
0.7257	Intermediate Similarity	NPC242269
0.7251	Intermediate Similarity	NPC286871
0.7251	Intermediate Similarity	NPC472101
0.7251	Intermediate Similarity	NPC472120
0.7249	Intermediate Similarity	NPC471436
0.7247	Intermediate Similarity	NPC39822
0.7239	Intermediate Similarity	NPC472103
0.7238	Intermediate Similarity	NPC94752
0.7238	Intermediate Similarity	NPC473615
0.7235	Intermediate Similarity	NPC36495
0.7222	Intermediate Similarity	NPC165495
0.7219	Intermediate Similarity	NPC473640
0.7219	Intermediate Similarity	NPC285469
0.7211	Intermediate Similarity	NPC477179
0.7208	Intermediate Similarity	NPC471197
0.7205	Intermediate Similarity	NPC130251
0.7198	Intermediate Similarity	NPC229484
0.7197	Intermediate Similarity	NPC476687
0.7197	Intermediate Similarity	NPC476685
0.7197	Intermediate Similarity	NPC476689
0.7196	Intermediate Similarity	NPC475506
0.7186	Intermediate Similarity	NPC475763
0.7181	Intermediate Similarity	NPC100321
0.7173	Intermediate Similarity	NPC477181
0.7173	Intermediate Similarity	NPC254850
0.7173	Intermediate Similarity	NPC477178
0.7173	Intermediate Similarity	NPC477180
0.7172	Intermediate Similarity	NPC471198
0.7168	Intermediate Similarity	NPC472106
0.7166	Intermediate Similarity	NPC472542
0.7166	Intermediate Similarity	NPC472541
0.716	Intermediate Similarity	NPC186284
0.716	Intermediate Similarity	NPC301760
0.716	Intermediate Similarity	NPC22082
0.7158	Intermediate Similarity	NPC155143
0.7158	Intermediate Similarity	NPC292675
0.7151	Intermediate Similarity	NPC472121
0.715	Intermediate Similarity	NPC471950
0.715	Intermediate Similarity	NPC285192
0.715	Intermediate Similarity	NPC471945
0.7143	Intermediate Similarity	NPC474926
0.7143	Intermediate Similarity	NPC472118
0.7143	Intermediate Similarity	NPC469560
0.7135	Intermediate Similarity	NPC477173
0.7135	Intermediate Similarity	NPC477174
0.7135	Intermediate Similarity	NPC470490
0.7128	Intermediate Similarity	NPC320968
0.7125	Intermediate Similarity	NPC267508
0.712	Intermediate Similarity	NPC128582
0.7113	Intermediate Similarity	NPC471946
0.7113	Intermediate Similarity	NPC471951
0.7112	Intermediate Similarity	NPC470787
0.7112	Intermediate Similarity	NPC472540
0.7112	Intermediate Similarity	NPC472539
0.7105	Intermediate Similarity	NPC71684
0.7101	Intermediate Similarity	NPC469903
0.7099	Intermediate Similarity	NPC315051
0.7098	Intermediate Similarity	NPC470488
0.7095	Intermediate Similarity	NPC11126
0.7085	Intermediate Similarity	NPC477714
0.7081	Intermediate Similarity	NPC243716
0.7076	Intermediate Similarity	NPC123241
0.7076	Intermediate Similarity	NPC469428
0.7076	Intermediate Similarity	NPC113946
0.7062	Intermediate Similarity	NPC470491
0.7062	Intermediate Similarity	NPC475259
0.7056	Intermediate Similarity	NPC54744
0.7052	Intermediate Similarity	NPC16667
0.7051	Intermediate Similarity	NPC145754
0.7029	Intermediate Similarity	NPC474561
0.7029	Intermediate Similarity	NPC49954
0.7024	Intermediate Similarity	NPC473329
0.7015	Intermediate Similarity	NPC272174
0.701	Intermediate Similarity	NPC54420
0.7006	Intermediate Similarity	NPC212799
0.7006	Intermediate Similarity	NPC254798
0.7	Intermediate Similarity	NPC285926
0.7	Intermediate Similarity	NPC219336
0.7	Intermediate Similarity	NPC14672
0.7	Intermediate Similarity	NPC141050
0.7	Intermediate Similarity	NPC315276
0.6995	Remote Similarity	NPC470489
0.6994	Remote Similarity	NPC243162
0.699	Remote Similarity	NPC475359
0.699	Remote Similarity	NPC191817
0.6977	Remote Similarity	NPC299594
0.697	Remote Similarity	NPC315266
0.6959	Remote Similarity	NPC207726
0.6954	Remote Similarity	NPC99632
0.6954	Remote Similarity	NPC293458
0.6954	Remote Similarity	NPC282339
0.6954	Remote Similarity	NPC176983
0.695	Remote Similarity	NPC477715
0.6944	Remote Similarity	NPC15573
0.6944	Remote Similarity	NPC183662
0.6944	Remote Similarity	NPC64436
0.6944	Remote Similarity	NPC217372
0.6941	Remote Similarity	NPC473002
0.6939	Remote Similarity	NPC478158
0.6939	Remote Similarity	NPC223791
0.6939	Remote Similarity	NPC162860
0.6939	Remote Similarity	NPC107077
0.6936	Remote Similarity	NPC193410
0.6936	Remote Similarity	NPC473003
0.6936	Remote Similarity	NPC469902
0.6919	Remote Similarity	NPC31385
0.6919	Remote Similarity	NPC110602
0.6919	Remote Similarity	NPC75726
0.6919	Remote Similarity	NPC84317
0.6919	Remote Similarity	NPC75634
0.6918	Remote Similarity	NPC130309
0.6914	Remote Similarity	NPC189116
0.6903	Remote Similarity	NPC6975
0.6898	Remote Similarity	NPC117244
0.6898	Remote Similarity	NPC473763
0.6897	Remote Similarity	NPC474896
0.6897	Remote Similarity	NPC143457
0.6897	Remote Similarity	NPC248117
0.6885	Remote Similarity	NPC477159
0.6883	Remote Similarity	NPC202521
0.6882	Remote Similarity	NPC154602
0.6879	Remote Similarity	NPC61013
0.6879	Remote Similarity	NPC469898
0.6872	Remote Similarity	NPC161861
0.6871	Remote Similarity	NPC122553
0.6867	Remote Similarity	NPC469537
0.6866	Remote Similarity	NPC15384
0.6866	Remote Similarity	NPC244425
0.6863	Remote Similarity	NPC31097
0.6857	Remote Similarity	NPC85651
0.6857	Remote Similarity	NPC282231
0.6857	Remote Similarity	NPC476231
0.6855	Remote Similarity	NPC200589
0.6854	Remote Similarity	NPC280548
0.6851	Remote Similarity	NPC14849
0.6851	Remote Similarity	NPC59269
0.6842	Remote Similarity	NPC285381
0.6842	Remote Similarity	NPC117032
0.6839	Remote Similarity	NPC67056
0.6839	Remote Similarity	NPC154478
0.6833	Remote Similarity	NPC470548
0.6833	Remote Similarity	NPC475097
0.6832	Remote Similarity	NPC287401
0.6827	Remote Similarity	NPC477175
0.6827	Remote Similarity	NPC470730
0.6827	Remote Similarity	NPC470729
0.6827	Remote Similarity	NPC477176
0.6826	Remote Similarity	NPC311330
0.6818	Remote Similarity	NPC271734
0.6818	Remote Similarity	NPC200964
0.6818	Remote Similarity	NPC476990
0.6811	Remote Similarity	NPC52262
0.6802	Remote Similarity	NPC478076
0.68	Remote Similarity	NPC225319
0.68	Remote Similarity	NPC279918
0.6798	Remote Similarity	NPC33507
0.6798	Remote Similarity	NPC63751
0.6794	Remote Similarity	NPC475969
0.6794	Remote Similarity	NPC477177

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 NPC68650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	400
0.2-0.3	748
0.3-0.4	1466
0.4-0.5	3168
0.5-0.6	2673
0.6-0.7	520
0.7-0.8	21
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.848	Intermediate Similarity	NPD8240	Discontinued
0.7707	Intermediate Similarity	NPD3625	Discontinued
0.7665	Intermediate Similarity	NPD5551	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5024	Approved
0.7472	Intermediate Similarity	NPD6557	Phase 2
0.744	Intermediate Similarity	NPD7599	Phase 2
0.7396	Intermediate Similarity	NPD7600	Phase 2
0.7368	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8630	Approved
0.7273	Intermediate Similarity	NPD5941	Approved
0.7273	Intermediate Similarity	NPD5942	Approved
0.7273	Intermediate Similarity	NPD979	Approved
0.7273	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5989	Phase 1
0.7169	Intermediate Similarity	NPD4432	Discontinued
0.7161	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1036	Approved
0.7125	Intermediate Similarity	NPD6102	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6301	Phase 2
0.7063	Intermediate Similarity	NPD2470	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6878	Phase 2
0.7056	Intermediate Similarity	NPD3989	Phase 3
0.7056	Intermediate Similarity	NPD6879	Phase 2
0.7048	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1316	Discontinued
0.7025	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD951	Approved
0.7017	Intermediate Similarity	NPD3990	Phase 3
0.7013	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1344	Phase 2
0.7	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5748	Phase 2
0.6919	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3790	Phase 2
0.6899	Remote Similarity	NPD3040	Approved
0.6889	Remote Similarity	NPD4091	Approved
0.6879	Remote Similarity	NPD2840	Approved
0.6879	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1107	Approved
0.6871	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1108	Approved
0.6864	Remote Similarity	NPD4682	Phase 2
0.6855	Remote Similarity	NPD5263	Approved
0.6851	Remote Similarity	NPD4092	Approved
0.6848	Remote Similarity	NPD2093	Discontinued
0.6842	Remote Similarity	NPD3248	Phase 1
0.6842	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8322	Phase 2
0.6834	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8272	Phase 2
0.6821	Remote Similarity	NPD1663	Discontinued
0.6821	Remote Similarity	NPD2622	Approved
0.6821	Remote Similarity	NPD7105	Phase 1
0.6813	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3072	Approved
0.6795	Remote Similarity	NPD3071	Approved
0.6795	Remote Similarity	NPD3073	Approved
0.6786	Remote Similarity	NPD5060	Phase 1
0.6782	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD750	Phase 2
0.6776	Remote Similarity	NPD6595	Phase 3
0.6772	Remote Similarity	NPD1950	Approved
0.6772	Remote Similarity	NPD1949	Approved
0.677	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5526	Phase 2
0.6758	Remote Similarity	NPD3992	Approved
0.6758	Remote Similarity	NPD3994	Approved
0.6758	Remote Similarity	NPD3996	Approved
0.6758	Remote Similarity	NPD3991	Approved
0.6758	Remote Similarity	NPD3995	Approved
0.6758	Remote Similarity	NPD3993	Approved
0.6754	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4676	Approved
0.675	Remote Similarity	NPD1271	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8076	Discontinued
0.6743	Remote Similarity	NPD4860	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3522	Approved
0.6736	Remote Similarity	NPD7308	Discontinued
0.6731	Remote Similarity	NPD4761	Approved
0.6731	Remote Similarity	NPD4762	Approved
0.673	Remote Similarity	NPD2146	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7091	Discontinued
0.6721	Remote Similarity	NPD3997	Approved
0.6721	Remote Similarity	NPD3999	Approved
0.6721	Remote Similarity	NPD5775	Approved
0.6721	Remote Similarity	NPD5774	Approved
0.6721	Remote Similarity	NPD3998	Approved
0.6721	Remote Similarity	NPD8386	Phase 2
0.6709	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2143	Discontinued
0.6705	Remote Similarity	NPD4121	Phase 3
0.6705	Remote Similarity	NPD4120	Approved
0.6704	Remote Similarity	NPD3983	Phase 3
0.6704	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7470	Discontinued
0.67	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2659	Approved
0.6689	Remote Similarity	NPD3148	Approved
0.6689	Remote Similarity	NPD2658	Approved
0.6689	Remote Similarity	NPD3147	Approved
0.6689	Remote Similarity	NPD3149	Approved
0.6689	Remote Similarity	NPD3150	Approved
0.6687	Remote Similarity	NPD1781	Discontinued
0.6687	Remote Similarity	NPD4153	Approved
0.6686	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5982	Phase 2
0.6685	Remote Similarity	NPD4796	Discontinued
0.6684	Remote Similarity	NPD5856	Discontinued
0.6683	Remote Similarity	NPD7970	Approved
0.6683	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5581	Approved
0.6667	Remote Similarity	NPD4317	Approved
0.6667	Remote Similarity	NPD1743	Approved
0.6667	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7072	Phase 2
0.6667	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6901	Phase 3
0.6667	Remote Similarity	NPD19	Approved
0.6667	Remote Similarity	NPD2820	Phase 3
0.6667	Remote Similarity	NPD5741	Approved
0.6667	Remote Similarity	NPD2129	Approved
0.6667	Remote Similarity	NPD5743	Approved
0.6667	Remote Similarity	NPD5742	Approved
0.6667	Remote Similarity	NPD7617	Discontinued
0.6667	Remote Similarity	NPD1742	Approved
0.665	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD482	Approved
0.6647	Remote Similarity	NPD3510	Approved
0.6647	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3509	Approved
0.6646	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1762	Approved
0.6623	Remote Similarity	NPD1764	Approved
0.6615	Remote Similarity	NPD7618	Phase 3
0.6615	Remote Similarity	NPD7944	Discontinued
0.6615	Remote Similarity	NPD7619	Phase 3
0.6613	Remote Similarity	NPD2095	Phase 2
0.6613	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2094	Phase 2
0.6613	Remote Similarity	NPD2092	Phase 2
0.6612	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5830	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2365	Approved
0.6606	Remote Similarity	NPD6073	Approved
0.6605	Remote Similarity	NPD1069	Approved
0.6605	Remote Similarity	NPD1070	Approved
0.6604	Remote Similarity	NPD5578	Approved
0.6604	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3227	Phase 2
0.6593	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7824	Approved
0.6587	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7200	Approved
0.6584	Remote Similarity	NPD4175	Approved
0.6584	Remote Similarity	NPD4177	Approved
0.6579	Remote Similarity	NPD4499	Approved
0.6578	Remote Similarity	NPD2096	Phase 2
0.6578	Remote Similarity	NPD2091	Phase 2
0.6577	Remote Similarity	NPD2678	Approved
0.6577	Remote Similarity	NPD2679	Approved
0.6576	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4430	Phase 2
0.6562	Remote Similarity	NPD6900	Discontinued
0.6562	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7210	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3961	Discontinued
0.6561	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7271	Approved
0.655	Remote Similarity	NPD4351	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2088	Approved
0.6548	Remote Similarity	NPD2087	Approved
0.6545	Remote Similarity	NPD5592	Clinical (unspecified phase)

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