NPASS Compound

Structure

NPC114808 OpenBabel07101719142D 32 36 0 0 1 0 0 0 0 0999 V2000 -5.1369 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6369 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6088 -0.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1463 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1463 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2802 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2802 0.5000 0.0000 C 0 0 0 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 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 -5.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 1.8660 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 -4.1369 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4142 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4142 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7071 0.7071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0898 -2.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3244 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 27 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 2 0 0 0 0 9 21 2 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 17 2 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 18 28 1 6 0 0 0 19 14 1 6 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 29 1 0 0 0 0 22 30 2 0 0 0 0 23 26 1 1 0 0 0 23 27 1 0 0 0 0 24 26 1 1 0 0 0 24 32 1 0 0 0 0 25 28 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 26 3 1 1 0 0 0 27 28 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	435.28
Volume:	471.61
LogP:	6.568
LogD:	4.656
LogS:	-7.05
# Rotatable Bonds:	1
TPSA:	55.4
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	4.648
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.998
MDCK Permeability:	2.5543529773131013e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.506
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	93.24346160888672%
Volume Distribution (VD):	0.871
Pgp-substrate:	3.3871710300445557%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.67
CYP2C19-inhibitor:	0.711
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.55
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.352
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.784

ADMET: Excretion

Clearance (CL):	17.42
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.384
Human Hepatotoxicity (H-HT):	0.84
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.538
Rat Oral Acute Toxicity:	0.856
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.77
Carcinogencity:	0.398
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC114808

Natural Product ID:	NPC114808
*Common Name:**	Asporyzin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WPOJQZPWCWZDGM-VSUSBFIXSA-N
Standard InCHI:	InChI=1S/C28H37NO3/c1-17(2)14-19-16-26(3)23-11-10-18-15-22(30)20-8-6-7-9-21(20)29-25(31)28(18,5)27(23,4)13-12-24(26)32-19/h6-9,14,18-19,23-24H,10-13,15-16H2,1-5H3,(H,29,31)/t18-,19-,23-,24-,26-,27-,28+/m0/s1
SMILES:	CC(=C[C@H]1C[C@@]2(C)[C@@H]3CC[C@H]4CC(=O)c5ccccc5N=C([C@]4(C)[C@@]3(C)CC[C@@H]2O1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1258864
PubChem CID:	52947705
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076576]
NPO1072	Aspergillus oryzae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20797856]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	Melia azedarach	n.a.	n.a.	PMID[21353539]
NPO1072	Aspergillus oryzae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22026385]
NPO1072	Aspergillus oryzae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24116376]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24183988]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33180497]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988601]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1072	Aspergillus oryzae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	13.7	%	PMID[513167]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	61.9	%	PMID[513167]
NPT22368	ORGANISM	Zika virus	Zika virus	EC50	=	18000.0	nM	PMID[513168]

☑ 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 NPC114808 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	222
0.1-0.2	1010
0.2-0.3	2306
0.3-0.4	6044
0.4-0.5	20831
0.5-0.6	10799
0.6-0.7	1438
0.7-0.8	42
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
0.8477	Intermediate Similarity	NPC470579
0.7785	Intermediate Similarity	NPC316746
0.7412	Intermediate Similarity	NPC469915
0.7213	Intermediate Similarity	NPC21483
0.7213	Intermediate Similarity	NPC198205
0.7189	Intermediate Similarity	NPC112752
0.7189	Intermediate Similarity	NPC311054
0.7143	Intermediate Similarity	NPC314287
0.7135	Intermediate Similarity	NPC198390
0.7128	Intermediate Similarity	NPC475223
0.7125	Intermediate Similarity	NPC316202
0.7091	Intermediate Similarity	NPC470274
0.709	Intermediate Similarity	NPC475448
0.709	Intermediate Similarity	NPC246983
0.7074	Intermediate Similarity	NPC136573
0.7074	Intermediate Similarity	NPC176371
0.7059	Intermediate Similarity	NPC107828
0.7059	Intermediate Similarity	NPC90358
0.7035	Intermediate Similarity	NPC52059
0.7035	Intermediate Similarity	NPC470069
0.7027	Intermediate Similarity	NPC476212
0.7027	Intermediate Similarity	NPC476205
0.7027	Intermediate Similarity	NPC476256
0.7027	Intermediate Similarity	NPC476206
0.7027	Intermediate Similarity	NPC259791
0.7027	Intermediate Similarity	NPC476129
0.7027	Intermediate Similarity	NPC476207
0.7027	Intermediate Similarity	NPC476257
0.6989	Remote Similarity	NPC476218
0.6989	Remote Similarity	NPC108804
0.6968	Remote Similarity	NPC116057
0.6928	Remote Similarity	NPC237649
0.6928	Remote Similarity	NPC300596
0.6918	Remote Similarity	NPC126516
0.6918	Remote Similarity	NPC329913
0.6903	Remote Similarity	NPC470753
0.6903	Remote Similarity	NPC473220
0.6883	Remote Similarity	NPC325013
0.6867	Remote Similarity	NPC212799
0.6859	Remote Similarity	NPC122235
0.6839	Remote Similarity	NPC275576
0.6839	Remote Similarity	NPC470765
0.6836	Remote Similarity	NPC181138
0.6836	Remote Similarity	NPC96901
0.6836	Remote Similarity	NPC276993
0.6836	Remote Similarity	NPC21752
0.6836	Remote Similarity	NPC298851
0.6836	Remote Similarity	NPC210415
0.6836	Remote Similarity	NPC293255
0.6821	Remote Similarity	NPC472121
0.6813	Remote Similarity	NPC203486
0.6802	Remote Similarity	NPC97380
0.6802	Remote Similarity	NPC63210
0.6802	Remote Similarity	NPC243673
0.6802	Remote Similarity	NPC148468
0.6802	Remote Similarity	NPC263709
0.6802	Remote Similarity	NPC310403
0.6795	Remote Similarity	NPC169913
0.6774	Remote Similarity	NPC453583
0.6774	Remote Similarity	NPC324251
0.6774	Remote Similarity	NPC70340
0.6774	Remote Similarity	NPC275170
0.6774	Remote Similarity	NPC475336
0.6774	Remote Similarity	NPC472694
0.6774	Remote Similarity	NPC474926
0.6774	Remote Similarity	NPC471629
0.6774	Remote Similarity	NPC206211
0.6774	Remote Similarity	NPC473300
0.6774	Remote Similarity	NPC473400
0.6774	Remote Similarity	NPC317882
0.6774	Remote Similarity	NPC472693
0.6774	Remote Similarity	NPC306001
0.6774	Remote Similarity	NPC471754
0.677	Remote Similarity	NPC208725
0.6769	Remote Similarity	NPC470280
0.6766	Remote Similarity	NPC94602
0.6763	Remote Similarity	NPC315368
0.6757	Remote Similarity	NPC477998
0.6752	Remote Similarity	NPC472413
0.6749	Remote Similarity	NPC106593
0.6748	Remote Similarity	NPC239770
0.6738	Remote Similarity	NPC33372
0.6738	Remote Similarity	NPC67246
0.6733	Remote Similarity	NPC140311
0.6724	Remote Similarity	NPC476750
0.6722	Remote Similarity	NPC474081
0.6716	Remote Similarity	NPC473667
0.671	Remote Similarity	NPC226794
0.6708	Remote Similarity	NPC48929
0.6707	Remote Similarity	NPC473541
0.6688	Remote Similarity	NPC39818
0.6687	Remote Similarity	NPC311330
0.6687	Remote Similarity	NPC153007
0.6686	Remote Similarity	NPC477156
0.6686	Remote Similarity	NPC477157
0.6685	Remote Similarity	NPC49184
0.6667	Remote Similarity	NPC475607
0.6667	Remote Similarity	NPC327699
0.6667	Remote Similarity	NPC265513
0.6667	Remote Similarity	NPC147561
0.6667	Remote Similarity	NPC183722
0.6667	Remote Similarity	NPC475128
0.6647	Remote Similarity	NPC116519
0.6647	Remote Similarity	NPC153694
0.6647	Remote Similarity	NPC211525
0.6646	Remote Similarity	NPC472656
0.6646	Remote Similarity	NPC90693
0.6646	Remote Similarity	NPC64897
0.6632	Remote Similarity	NPC242662
0.6632	Remote Similarity	NPC321072
0.6632	Remote Similarity	NPC215892
0.6632	Remote Similarity	NPC191193
0.6631	Remote Similarity	NPC471623
0.6631	Remote Similarity	NPC206967
0.6628	Remote Similarity	NPC161827
0.6625	Remote Similarity	NPC470278
0.6625	Remote Similarity	NPC42423
0.6625	Remote Similarity	NPC72915
0.6625	Remote Similarity	NPC471334
0.6611	Remote Similarity	NPC475594
0.661	Remote Similarity	NPC278887
0.6606	Remote Similarity	NPC97667
0.6606	Remote Similarity	NPC100913
0.6606	Remote Similarity	NPC90614
0.6606	Remote Similarity	NPC171207
0.6606	Remote Similarity	NPC275592
0.6604	Remote Similarity	NPC477432
0.6604	Remote Similarity	NPC314431
0.6602	Remote Similarity	NPC245756
0.6601	Remote Similarity	NPC202015
0.6601	Remote Similarity	NPC476645
0.6598	Remote Similarity	NPC123019
0.6597	Remote Similarity	NPC208553
0.6597	Remote Similarity	NPC181964
0.6597	Remote Similarity	NPC471606
0.6595	Remote Similarity	NPC132751
0.6593	Remote Similarity	NPC472331
0.6593	Remote Similarity	NPC274002
0.6593	Remote Similarity	NPC474041
0.6593	Remote Similarity	NPC126515
0.6593	Remote Similarity	NPC475761
0.6592	Remote Similarity	NPC355
0.6587	Remote Similarity	NPC262216
0.6584	Remote Similarity	NPC473837
0.6582	Remote Similarity	NPC58827
0.6582	Remote Similarity	NPC190849
0.6582	Remote Similarity	NPC72473
0.6582	Remote Similarity	NPC307437
0.6582	Remote Similarity	NPC171007
0.6579	Remote Similarity	NPC61651
0.6575	Remote Similarity	NPC172170
0.6575	Remote Similarity	NPC471743
0.6566	Remote Similarity	NPC291599
0.6566	Remote Similarity	NPC118080
0.6566	Remote Similarity	NPC477155
0.6566	Remote Similarity	NPC87448
0.6566	Remote Similarity	NPC41481
0.6566	Remote Similarity	NPC97947
0.6566	Remote Similarity	NPC16912
0.6566	Remote Similarity	NPC472576
0.6566	Remote Similarity	NPC27377
0.6564	Remote Similarity	NPC477896
0.6564	Remote Similarity	NPC477893
0.6562	Remote Similarity	NPC473490
0.6562	Remote Similarity	NPC475138
0.6562	Remote Similarity	NPC473558
0.6559	Remote Similarity	NPC288854
0.6558	Remote Similarity	NPC472680
0.6558	Remote Similarity	NPC161956
0.6558	Remote Similarity	NPC258531
0.6558	Remote Similarity	NPC472679
0.6558	Remote Similarity	NPC112373
0.6554	Remote Similarity	NPC71205
0.6554	Remote Similarity	NPC253738
0.6548	Remote Similarity	NPC260194
0.6545	Remote Similarity	NPC315051
0.6545	Remote Similarity	NPC243162
0.6541	Remote Similarity	NPC150863
0.6541	Remote Similarity	NPC97584
0.6541	Remote Similarity	NPC101372
0.6538	Remote Similarity	NPC9475
0.6538	Remote Similarity	NPC315406
0.6536	Remote Similarity	NPC476749
0.6536	Remote Similarity	NPC472118
0.6524	Remote Similarity	NPC472372
0.6524	Remote Similarity	NPC472374
0.6524	Remote Similarity	NPC472551
0.6524	Remote Similarity	NPC472545
0.6522	Remote Similarity	NPC472692
0.6522	Remote Similarity	NPC472682
0.652	Remote Similarity	NPC301368
0.652	Remote Similarity	NPC84815
0.652	Remote Similarity	NPC223590
0.6516	Remote Similarity	NPC257490
0.6516	Remote Similarity	NPC472981
0.6516	Remote Similarity	NPC103292
0.6505	Remote Similarity	NPC52262
0.6503	Remote Similarity	NPC310662
0.6503	Remote Similarity	NPC99043
0.6503	Remote Similarity	NPC474608

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 NPC114808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	553
0.2-0.3	758
0.3-0.4	1233
0.4-0.5	3830
0.5-0.6	2438
0.6-0.7	158
0.7-0.8	4
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
0.7338	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6414	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1593	Approved
0.7095	Intermediate Similarity	NPD7546	Discontinued
0.7011	Intermediate Similarity	NPD7795	Phase 2
0.6994	Remote Similarity	NPD7487	Discontinued
0.6951	Remote Similarity	NPD7295	Approved
0.6919	Remote Similarity	NPD8146	Phase 2
0.6883	Remote Similarity	NPD1574	Approved
0.6882	Remote Similarity	NPD2672	Discontinued
0.6829	Remote Similarity	NPD7082	Approved
0.6788	Remote Similarity	NPD7259	Approved
0.6786	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1036	Approved
0.6761	Remote Similarity	NPD2821	Approved
0.6758	Remote Similarity	NPD7962	Phase 2
0.6747	Remote Similarity	NPD6017	Discontinued
0.6726	Remote Similarity	NPD4888	Discontinued
0.6703	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5086	Approved
0.6647	Remote Similarity	NPD7606	Phase 3
0.6631	Remote Similarity	NPD8360	Approved
0.6631	Remote Similarity	NPD8361	Approved
0.6631	Remote Similarity	NPD8435	Approved
0.6606	Remote Similarity	NPD6789	Approved
0.6597	Remote Similarity	NPD8485	Approved
0.6576	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5811	Approved
0.6568	Remote Similarity	NPD7478	Approved
0.6561	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5937	Approved
0.6552	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1625	Approved
0.6516	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7236	Approved
0.6495	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7600	Phase 2
0.6471	Remote Similarity	NPD7610	Discontinued
0.645	Remote Similarity	NPD6185	Discontinued
0.6448	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD3965	Phase 1
0.6443	Remote Similarity	NPD6874	Approved
0.6437	Remote Similarity	NPD1514	Discontinued
0.6432	Remote Similarity	NPD6104	Discontinued
0.6429	Remote Similarity	NPD2820	Phase 3
0.6429	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1532	Approved
0.642	Remote Similarity	NPD7599	Phase 2
0.6417	Remote Similarity	NPD8407	Phase 2
0.6416	Remote Similarity	NPD7239	Suspended
0.6416	Remote Similarity	NPD3399	Approved
0.6412	Remote Similarity	NPD4041	Approved
0.6412	Remote Similarity	NPD4607	Approved
0.6409	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2836	Approved
0.6396	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD1626	Approved
0.638	Remote Similarity	NPD7713	Phase 3
0.6374	Remote Similarity	NPD5997	Discontinued
0.6374	Remote Similarity	NPD6758	Approved
0.6374	Remote Similarity	NPD3352	Approved
0.6373	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5430	Discontinued
0.6369	Remote Similarity	NPD2923	Approved
0.6369	Remote Similarity	NPD2365	Approved
0.6369	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD181	Approved
0.6358	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD7179	Phase 2
0.6328	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD2670	Approved
0.6316	Remote Similarity	NPD2792	Approved
0.6312	Remote Similarity	NPD9567	Approved
0.6312	Remote Similarity	NPD552	Approved
0.6312	Remote Similarity	NPD553	Approved
0.6306	Remote Similarity	NPD5770	Phase 3
0.6303	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD7569	Approved
0.6302	Remote Similarity	NPD7570	Approved
0.6301	Remote Similarity	NPD4513	Discontinued
0.63	Remote Similarity	NPD6296	Discontinued
0.6294	Remote Similarity	NPD2435	Approved
0.628	Remote Similarity	NPD7961	Discontinued
0.628	Remote Similarity	NPD1541	Approved
0.628	Remote Similarity	NPD1527	Phase 2
0.6279	Remote Similarity	NPD8165	Discontinued
0.6279	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7011	Discontinued
0.627	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6287	Discontinued
0.6265	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD2369	Discontinued
0.6258	Remote Similarity	NPD6039	Approved
0.6257	Remote Similarity	NPD8368	Discontinued
0.625	Remote Similarity	NPD7094	Approved
0.625	Remote Similarity	NPD5466	Approved
0.625	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5617	Suspended
0.625	Remote Similarity	NPD6858	Approved
0.6243	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD4942	Approved
0.6243	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1531	Approved
0.6242	Remote Similarity	NPD5184	Approved
0.6242	Remote Similarity	NPD5185	Approved
0.6242	Remote Similarity	NPD5182	Approved
0.6226	Remote Similarity	NPD6637	Approved
0.6215	Remote Similarity	NPD951	Approved
0.6215	Remote Similarity	NPD2366	Approved
0.6213	Remote Similarity	NPD9477	Approved
0.6209	Remote Similarity	NPD1682	Approved
0.6209	Remote Similarity	NPD1680	Approved
0.6209	Remote Similarity	NPD1681	Approved
0.6209	Remote Similarity	NPD6457	Approved
0.6203	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD7244	Discontinued
0.6196	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4412	Phase 2
0.619	Remote Similarity	NPD3170	Approved
0.6188	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5157	Phase 1
0.6188	Remote Similarity	NPD3252	Approved
0.6188	Remote Similarity	NPD5159	Phase 2
0.6185	Remote Similarity	NPD7088	Discontinued
0.6185	Remote Similarity	NPD1340	Discontinued
0.6176	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD1189	Approved
0.6171	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD1190	Approved
0.6159	Remote Similarity	NPD7008	Discontinued
0.6158	Remote Similarity	NPD3684	Discontinued
0.615	Remote Similarity	NPD3802	Phase 3
0.615	Remote Similarity	NPD6176	Phase 1
0.6149	Remote Similarity	NPD979	Approved
0.6145	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2948	Discontinued
0.6135	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD8007	Approved
0.6133	Remote Similarity	NPD8008	Approved
0.6131	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6570	Approved
0.6124	Remote Similarity	NPD6571	Approved
0.6122	Remote Similarity	NPD4931	Phase 2
0.6121	Remote Similarity	NPD1919	Approved
0.6121	Remote Similarity	NPD1920	Approved
0.612	Remote Similarity	NPD2034	Discontinued
0.6119	Remote Similarity	NPD6987	Phase 1
0.6118	Remote Similarity	NPD3642	Approved
0.6118	Remote Similarity	NPD3643	Approved
0.6118	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3644	Approved
0.6118	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3823	Discontinued
0.6114	Remote Similarity	NPD5748	Phase 2
0.6108	Remote Similarity	NPD6894	Phase 1
0.6107	Remote Similarity	NPD1018	Approved
0.6105	Remote Similarity	NPD3436	Approved
0.6102	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD7035	Approved
0.6099	Remote Similarity	NPD7036	Phase 3
0.6095	Remote Similarity	NPD1109	Approved
0.6095	Remote Similarity	NPD1110	Approved
0.6089	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD168	Phase 1
0.6082	Remote Similarity	NPD167	Phase 2
0.6077	Remote Similarity	NPD4871	Phase 2
0.6076	Remote Similarity	NPD5981	Approved
0.6073	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD8462	Phase 1
0.6065	Remote Similarity	NPD6962	Phase 2
0.6065	Remote Similarity	NPD5951	Approved
0.6064	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5197	Approved
0.6061	Remote Similarity	NPD5196	Approved
0.6061	Remote Similarity	NPD5194	Approved
0.6059	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD5429	Discontinued
0.6058	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5578	Approved
0.6049	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3153	Approved
0.6042	Remote Similarity	NPD3154	Approved
0.6037	Remote Similarity	NPD7084	Phase 3
0.6036	Remote Similarity	NPD3864	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