NPASS Compound

Structure

NPC67658 OpenBabel07101718192D 26 27 0 0 0 0 0 0 0 0999 V2000 7.7372 -5.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6032 -3.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 -2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 -2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8712 -2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8712 -3.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0052 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0052 -2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 0.0878 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.8968 -1.7601 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 2.0878 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 7.7372 -4.4122 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 -0.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 7 1 0 0 0 0 3 9 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 22 1 0 0 0 0 8 24 1 0 0 0 0 9 26 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 15 2 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.93
Volume:	395.374
LogP:	4.288
LogD:	3.772
LogS:	-5.629
# Rotatable Bonds:	10
TPSA:	57.36
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	2.555
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.824
MDCK Permeability:	1.5163934222073294e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	95.41976928710938%
Volume Distribution (VD):	1.988
Pgp-substrate:	4.1565399169921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.727
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.561
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.861
CYP3A4-substrate:	0.471

ADMET: Excretion

Clearance (CL):	2.803
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.97
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.374
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.67
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.51
Carcinogencity:	0.265
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.681

Download Data

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

Natural Product: NPC67658

Natural Product ID:	NPC67658
*Common Name:**	Agelanesin C
IUPAC Name:	4,5-dibromo-N-[3-[2-bromo-4-[2-(dimethylamino)ethyl]phenoxy]propyl]-1H-pyrrole-2-carboxamide
Synonyms:	Agelanesin C
Standard InCHIKey:	GUGUXLUNDIQBBZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H22Br3N3O2/c1-24(2)8-6-12-4-5-16(13(19)10-12)26-9-3-7-22-18(25)15-11-14(20)17(21)23-15/h4-5,10-11,23H,3,6-9H2,1-2H3,(H,22,25)
SMILES:	CN(CCc1ccc(c(c1)Br)OCCCNC(=O)c1[nH]c(c(c1)Br)Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598108
PubChem CID:	46232060
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO33334	agelas sponges	Species	Agelasidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20061160]

☑ 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	1
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	0.8	%	PMID[521540]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	16760.0	nM	PMID[521540]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	36000.0	nM	PMID[521540]

☑ 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 NPC67658 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	438
0.1-0.2	5440
0.2-0.3	11842
0.3-0.4	8707
0.4-0.5	11496
0.5-0.6	3665
0.6-0.7	1045
0.7-0.8	58
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC50562
0.9596	High Similarity	NPC175150
0.9596	High Similarity	NPC243633
0.9154	High Similarity	NPC168209
0.787	Intermediate Similarity	NPC323969
0.7623	Intermediate Similarity	NPC194740
0.7611	Intermediate Similarity	NPC33064
0.7489	Intermediate Similarity	NPC305984
0.7376	Intermediate Similarity	NPC303658
0.7345	Intermediate Similarity	NPC304307
0.7345	Intermediate Similarity	NPC124920
0.7345	Intermediate Similarity	NPC34580
0.7345	Intermediate Similarity	NPC118559
0.7336	Intermediate Similarity	NPC284888
0.733	Intermediate Similarity	NPC223189
0.7313	Intermediate Similarity	NPC66777
0.7313	Intermediate Similarity	NPC100547
0.7313	Intermediate Similarity	NPC471762
0.7304	Intermediate Similarity	NPC245055
0.7293	Intermediate Similarity	NPC196718
0.7285	Intermediate Similarity	NPC322064
0.7281	Intermediate Similarity	NPC322135
0.7281	Intermediate Similarity	NPC223409
0.7281	Intermediate Similarity	NPC95240
0.7269	Intermediate Similarity	NPC261251
0.7249	Intermediate Similarity	NPC14288
0.7225	Intermediate Similarity	NPC214142
0.7217	Intermediate Similarity	NPC200553
0.7217	Intermediate Similarity	NPC54803
0.7217	Intermediate Similarity	NPC102593
0.7217	Intermediate Similarity	NPC321592
0.7198	Intermediate Similarity	NPC272549
0.7198	Intermediate Similarity	NPC162002
0.7162	Intermediate Similarity	NPC477979
0.7156	Intermediate Similarity	NPC249583
0.7155	Intermediate Similarity	NPC174489
0.7137	Intermediate Similarity	NPC122436
0.7136	Intermediate Similarity	NPC74153
0.713	Intermediate Similarity	NPC152768
0.713	Intermediate Similarity	NPC115595
0.713	Intermediate Similarity	NPC295898
0.713	Intermediate Similarity	NPC148183
0.7125	Intermediate Similarity	NPC181081
0.7124	Intermediate Similarity	NPC198503
0.7118	Intermediate Similarity	NPC157931
0.7118	Intermediate Similarity	NPC257851
0.7094	Intermediate Similarity	NPC26641
0.709	Intermediate Similarity	NPC216369
0.7078	Intermediate Similarity	NPC4687
0.7078	Intermediate Similarity	NPC321428
0.7078	Intermediate Similarity	NPC270918
0.7069	Intermediate Similarity	NPC279189
0.7067	Intermediate Similarity	NPC295158
0.7064	Intermediate Similarity	NPC82472
0.7064	Intermediate Similarity	NPC101350
0.7056	Intermediate Similarity	NPC78767
0.7056	Intermediate Similarity	NPC473814
0.7034	Intermediate Similarity	NPC37152
0.7032	Intermediate Similarity	NPC472287
0.7032	Intermediate Similarity	NPC472286
0.7031	Intermediate Similarity	NPC21638
0.7031	Intermediate Similarity	NPC260041
0.7021	Intermediate Similarity	NPC235685
0.7021	Intermediate Similarity	NPC184680
0.7004	Intermediate Similarity	NPC472099
0.6996	Remote Similarity	NPC308137
0.6996	Remote Similarity	NPC310211
0.6995	Remote Similarity	NPC473821
0.6992	Remote Similarity	NPC470784
0.6992	Remote Similarity	NPC470785
0.6986	Remote Similarity	NPC241025
0.6978	Remote Similarity	NPC74969
0.6965	Remote Similarity	NPC2414
0.6963	Remote Similarity	NPC93390
0.6955	Remote Similarity	NPC45190
0.6955	Remote Similarity	NPC82053
0.6953	Remote Similarity	NPC260434
0.6951	Remote Similarity	NPC87413
0.6951	Remote Similarity	NPC146418
0.6938	Remote Similarity	NPC84478
0.6936	Remote Similarity	NPC475635
0.693	Remote Similarity	NPC150239
0.692	Remote Similarity	NPC264176
0.6916	Remote Similarity	NPC473041
0.6897	Remote Similarity	NPC478078
0.6891	Remote Similarity	NPC477590
0.6891	Remote Similarity	NPC477585
0.6891	Remote Similarity	NPC477588
0.6891	Remote Similarity	NPC477586
0.6878	Remote Similarity	NPC300156
0.6872	Remote Similarity	NPC169402
0.6866	Remote Similarity	NPC472284
0.6858	Remote Similarity	NPC116238
0.6856	Remote Similarity	NPC225279
0.6849	Remote Similarity	NPC471944
0.6845	Remote Similarity	NPC37268
0.6842	Remote Similarity	NPC247803
0.6842	Remote Similarity	NPC46561
0.6834	Remote Similarity	NPC142688
0.6826	Remote Similarity	NPC280799
0.6825	Remote Similarity	NPC476423
0.6822	Remote Similarity	NPC92111
0.6822	Remote Similarity	NPC243716
0.6812	Remote Similarity	NPC208084
0.6812	Remote Similarity	NPC288987
0.6807	Remote Similarity	NPC477589
0.6807	Remote Similarity	NPC477587
0.6804	Remote Similarity	NPC329747
0.68	Remote Similarity	NPC187501
0.6796	Remote Similarity	NPC80528
0.6795	Remote Similarity	NPC311906
0.6789	Remote Similarity	NPC72211
0.6788	Remote Similarity	NPC308571
0.6783	Remote Similarity	NPC54066
0.6781	Remote Similarity	NPC24370
0.6781	Remote Similarity	NPC319232
0.678	Remote Similarity	NPC473186
0.6776	Remote Similarity	NPC76748
0.6774	Remote Similarity	NPC77061
0.6769	Remote Similarity	NPC96321
0.6769	Remote Similarity	NPC174576
0.6759	Remote Similarity	NPC307963
0.6758	Remote Similarity	NPC18487
0.6758	Remote Similarity	NPC477004
0.6756	Remote Similarity	NPC471304
0.6756	Remote Similarity	NPC113369
0.6756	Remote Similarity	NPC269367
0.6748	Remote Similarity	NPC477255
0.6745	Remote Similarity	NPC133003
0.6741	Remote Similarity	NPC39679
0.6741	Remote Similarity	NPC475910
0.674	Remote Similarity	NPC471080
0.674	Remote Similarity	NPC469592
0.6736	Remote Similarity	NPC316224
0.6735	Remote Similarity	NPC296085
0.673	Remote Similarity	NPC176127
0.6729	Remote Similarity	NPC296527
0.6724	Remote Similarity	NPC470501
0.6724	Remote Similarity	NPC220851
0.6724	Remote Similarity	NPC144452
0.6723	Remote Similarity	NPC39370
0.6723	Remote Similarity	NPC97902
0.6716	Remote Similarity	NPC27296
0.6711	Remote Similarity	NPC174758
0.671	Remote Similarity	NPC174760
0.671	Remote Similarity	NPC128115
0.67	Remote Similarity	NPC474236
0.6697	Remote Similarity	NPC70259
0.6697	Remote Similarity	NPC232727
0.6697	Remote Similarity	NPC102592
0.6697	Remote Similarity	NPC79356
0.6694	Remote Similarity	NPC303374
0.6682	Remote Similarity	NPC472861
0.6682	Remote Similarity	NPC184932
0.6682	Remote Similarity	NPC19342
0.6681	Remote Similarity	NPC470502
0.6681	Remote Similarity	NPC60621
0.6667	Remote Similarity	NPC39500
0.6667	Remote Similarity	NPC298436
0.6667	Remote Similarity	NPC138370
0.6667	Remote Similarity	NPC179287
0.6667	Remote Similarity	NPC206148
0.6667	Remote Similarity	NPC474688
0.6667	Remote Similarity	NPC6786
0.6667	Remote Similarity	NPC269270
0.6653	Remote Similarity	NPC244543
0.6652	Remote Similarity	NPC478141
0.6652	Remote Similarity	NPC27041
0.6652	Remote Similarity	NPC121772
0.6651	Remote Similarity	NPC205934
0.6651	Remote Similarity	NPC43787
0.665	Remote Similarity	NPC71629
0.664	Remote Similarity	NPC258048
0.6639	Remote Similarity	NPC131486
0.6638	Remote Similarity	NPC14686
0.6638	Remote Similarity	NPC16066
0.6637	Remote Similarity	NPC162484
0.6636	Remote Similarity	NPC127085
0.6636	Remote Similarity	NPC63571
0.6635	Remote Similarity	NPC247980
0.6634	Remote Similarity	NPC474383
0.6626	Remote Similarity	NPC91868
0.6626	Remote Similarity	NPC63971
0.6625	Remote Similarity	NPC477549
0.6624	Remote Similarity	NPC470503
0.6623	Remote Similarity	NPC472098
0.6623	Remote Similarity	NPC118940
0.6623	Remote Similarity	NPC469717
0.6623	Remote Similarity	NPC469594
0.6622	Remote Similarity	NPC9635
0.6622	Remote Similarity	NPC183777
0.6621	Remote Similarity	NPC251090
0.6621	Remote Similarity	NPC13880
0.662	Remote Similarity	NPC324091
0.6612	Remote Similarity	NPC475816
0.6611	Remote Similarity	NPC473105
0.6611	Remote Similarity	NPC323752
0.661	Remote Similarity	NPC187145
0.6608	Remote Similarity	NPC123839
0.6607	Remote Similarity	NPC285558

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 NPC67658 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	734
0.2-0.3	865
0.3-0.4	1441
0.4-0.5	2926
0.5-0.6	2434
0.6-0.7	499
0.7-0.8	16
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
0.7523	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5632	Approved
0.7352	Intermediate Similarity	NPD3945	Discontinued
0.7318	Intermediate Similarity	NPD5293	Phase 2
0.7273	Intermediate Similarity	NPD7853	Phase 2
0.7232	Intermediate Similarity	NPD7180	Phase 3
0.7227	Intermediate Similarity	NPD5866	Approved
0.7205	Intermediate Similarity	NPD5479	Discontinued
0.7168	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7994	Phase 2
0.7106	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD3263	Phase 3
0.7056	Intermediate Similarity	NPD1659	Phase 1
0.7045	Intermediate Similarity	NPD6376	Discontinued
0.7042	Intermediate Similarity	NPD4558	Phase 2
0.7032	Intermediate Similarity	NPD8403	Phase 1
0.7018	Intermediate Similarity	NPD5513	Phase 2
0.7004	Intermediate Similarity	NPD1996	Discontinued
0.7004	Intermediate Similarity	NPD6242	Discontinued
0.6996	Remote Similarity	NPD4885	Approved
0.6991	Remote Similarity	NPD1768	Approved
0.6987	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6209	Approved
0.6936	Remote Similarity	NPD2951	Discontinued
0.691	Remote Similarity	NPD4952	Phase 3
0.6903	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7467	Discontinued
0.6886	Remote Similarity	NPD6974	Phase 3
0.6881	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3003	Approved
0.6878	Remote Similarity	NPD4368	Phase 2
0.6878	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5482	Discontinued
0.6851	Remote Similarity	NPD4847	Phase 1
0.6842	Remote Similarity	NPD6568	Discontinued
0.6838	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3825	Phase 3
0.6833	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4373	Phase 2
0.6816	Remote Similarity	NPD5658	Approved
0.681	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4130	Phase 3
0.6802	Remote Similarity	NPD5601	Phase 2
0.6795	Remote Similarity	NPD5559	Phase 2
0.6792	Remote Similarity	NPD5256	Discontinued
0.6791	Remote Similarity	NPD4372	Phase 1
0.6787	Remote Similarity	NPD6176	Phase 1
0.6783	Remote Similarity	NPD8479	Phase 2
0.6781	Remote Similarity	NPD5640	Discontinued
0.6778	Remote Similarity	NPD4313	Approved
0.6778	Remote Similarity	NPD4314	Approved
0.6771	Remote Similarity	NPD1392	Approved
0.6769	Remote Similarity	NPD5948	Phase 2
0.6762	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1038	Approved
0.6759	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD2778	Approved
0.6757	Remote Similarity	NPD3947	Discontinued
0.6756	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD3392	Approved
0.6752	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2510	Approved
0.6741	Remote Similarity	NPD2509	Approved
0.6729	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3396	Approved
0.6728	Remote Similarity	NPD3395	Approved
0.6726	Remote Similarity	NPD5067	Phase 2
0.6726	Remote Similarity	NPD5416	Discontinued
0.6726	Remote Similarity	NPD5066	Phase 2
0.6724	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5014	Discontinued
0.672	Remote Similarity	NPD5116	Phase 1
0.6712	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7031	Phase 1
0.6708	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3569	Discontinued
0.6695	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4322	Discontinued
0.6694	Remote Similarity	NPD6716	Phase 1
0.6682	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4203	Approved
0.6682	Remote Similarity	NPD4204	Approved
0.6681	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4309	Approved
0.6667	Remote Similarity	NPD2779	Approved
0.6667	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6790	Phase 1
0.6651	Remote Similarity	NPD4418	Discontinued
0.6638	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5902	Approved
0.6638	Remote Similarity	NPD5903	Approved
0.6638	Remote Similarity	NPD5850	Phase 3
0.6623	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1096	Discontinued
0.6619	Remote Similarity	NPD4072	Approved
0.6619	Remote Similarity	NPD4071	Approved
0.6618	Remote Similarity	NPD5183	Approved
0.6618	Remote Similarity	NPD5186	Approved
0.6609	Remote Similarity	NPD3393	Approved
0.6609	Remote Similarity	NPD3389	Approved
0.6609	Remote Similarity	NPD5612	Discontinued
0.6609	Remote Similarity	NPD3394	Approved
0.6606	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7194	Discontinued
0.6591	Remote Similarity	NPD2952	Discontinued
0.6589	Remote Similarity	NPD4889	Approved
0.6574	Remote Similarity	NPD4021	Phase 2
0.657	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD1638	Discovery
0.6562	Remote Similarity	NPD6991	Approved
0.6561	Remote Similarity	NPD772	Phase 3
0.656	Remote Similarity	NPD6569	Phase 2
0.6557	Remote Similarity	NPD7022	Phase 2
0.6556	Remote Similarity	NPD3006	Discontinued
0.6555	Remote Similarity	NPD5924	Discontinued
0.6549	Remote Similarity	NPD5450	Discontinued
0.6545	Remote Similarity	NPD5512	Phase 3
0.654	Remote Similarity	NPD3259	Approved
0.6538	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4923	Phase 1
0.6533	Remote Similarity	NPD3397	Phase 2
0.6532	Remote Similarity	NPD4548	Discontinued
0.6532	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.653	Remote Similarity	NPD4539	Phase 1
0.6527	Remote Similarity	NPD5139	Phase 1
0.6527	Remote Similarity	NPD1867	Approved
0.6527	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD8106	Phase 2
0.6526	Remote Similarity	NPD3178	Discontinued
0.6525	Remote Similarity	NPD4890	Phase 2
0.6524	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7708	Approved
0.652	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD8311	Discontinued
0.6509	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3507	Phase 2
0.65	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD8289	Discontinued
0.6494	Remote Similarity	NPD3257	Approved
0.6494	Remote Similarity	NPD4897	Phase 2
0.6494	Remote Similarity	NPD5149	Phase 2
0.6494	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7689	Approved
0.6485	Remote Similarity	NPD5022	Discontinued
0.6484	Remote Similarity	NPD7803	Approved
0.6481	Remote Similarity	NPD6985	Discontinued
0.6481	Remote Similarity	NPD4429	Discontinued
0.6481	Remote Similarity	NPD7395	Discontinued
0.6479	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6397	Phase 3
0.6478	Remote Similarity	NPD6202	Discontinued
0.6478	Remote Similarity	NPD7605	Discovery
0.6473	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2290	Phase 3
0.6471	Remote Similarity	NPD2289	Phase 3
0.6468	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6475	Phase 2
0.6466	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7588	Discontinued
0.6459	Remote Similarity	NPD565	Phase 2
0.6454	Remote Similarity	NPD8463	Approved
0.6453	Remote Similarity	NPD2884	Phase 1
0.6453	Remote Similarity	NPD6770	Approved
0.6453	Remote Similarity	NPD3258	Approved
0.6449	Remote Similarity	NPD5271	Approved
0.6449	Remote Similarity	NPD5273	Approved
0.6447	Remote Similarity	NPD7671	Approved
0.6447	Remote Similarity	NPD7672	Approved
0.6444	Remote Similarity	NPD7316	Discontinued
0.6444	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD1630	Approved
0.6438	Remote Similarity	NPD4989	Phase 2
0.6432	Remote Similarity	NPD7797	Approved
0.6432	Remote Similarity	NPD7796	Approved
0.6429	Remote Similarity	NPD4500	Approved
0.6429	Remote Similarity	NPD4501	Approved
0.6429	Remote Similarity	NPD7603	Discontinued
0.6429	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7426	Phase 1
0.6426	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD8102	Discontinued
0.6426	Remote Similarity	NPD4369	Phase 2
0.6425	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD2547	Discontinued
0.6422	Remote Similarity	NPD4334	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