NPASS Compound

Structure

CID322424 OpenBabel06191716162D 22 25 0 0 1 0 0 0 0 0999 V2000 -0.9183 2.4073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4763 -0.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4763 1.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4871 0.2074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4654 0.2074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4654 1.3495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4871 1.3495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4009 -0.1455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6874 0.9462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2541 1.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3240 0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2704 0.7785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2857 -0.2662 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.7797 0.6568 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1407 1.6710 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2857 1.8231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6118 2.8103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3705 -0.5460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9460 1.9774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4009 1.7025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1093 -1.0205 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 4 1 0 0 0 0 2 5 2 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 1 0 0 0 8 21 1 0 0 0 0 9 10 1 1 0 0 0 9 14 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 11 1 6 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 15 19 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	359.96
Volume:	286.874
LogP:	2.26
LogD:	2.032
LogS:	-3.849
# Rotatable Bonds:	1
TPSA:	88.1
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	5.991
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	8.77154616318876e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.287
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	73.22584533691406%
Volume Distribution (VD):	0.781
Pgp-substrate:	19.363571166992188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.298
CYP1A2-substrate:	0.445
CYP2C19-inhibitor:	0.76
CYP2C19-substrate:	0.581
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.607
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.803

ADMET: Excretion

Clearance (CL):	10.73
Half-life (T1/2):	0.565

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.882
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.329
Skin Sensitization:	0.592
Carcinogencity:	0.946
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC322424

Natural Product ID:	NPC322424
*Common Name:**	Aspirochlorine
IUPAC Name:	n.a.
Synonyms:	Aspirochlorine
Standard InCHIKey:	XMFSSFONDVHNFO-AUTRQRHGSA-N
Standard InCHI:	InChI=1S/C12H9ClN2O5S2/c1-19-15-10(17)9-14-11(18)12(15)8(21-22-9)4-2-5(13)6(16)3-7(4)20-12/h2-3,8-9,16H,1H3,(H,14,18)/t8-,9-,12-/m0/s1
SMILES:	CON1C(=O)C2NC(=O)C13C(C4=CC(=C(C=C4O3)O)Cl)SS2
Synthetic Gene Cluster:	BGC0001123;
ChEMBL Identifier:	CHEMBL470243
PubChem CID:	44559211
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124785]
NPO1072	Aspergillus oryzae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20797856]
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]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24738739]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31050424]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4207788]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4629903]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7528269]
NPO1072	Aspergillus oryzae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23756	Aspergillus flavus	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
IC50	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	580.0	nM	PMID[533701]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	28.0	nM	PMID[533701]
NPT27	Others	Unspecified		Ratio IC50	=	20.0	n.a.	PMID[533701]

☑ 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 NPC322424 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	352
0.1-0.2	3209
0.2-0.3	13936
0.3-0.4	6081
0.4-0.5	12577
0.5-0.6	6466
0.6-0.7	74
0.7-0.8	0
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
0.9602	High Similarity	NPC475702
0.6822	Remote Similarity	NPC477665
0.6716	Remote Similarity	NPC474498
0.6573	Remote Similarity	NPC477666
0.6538	Remote Similarity	NPC471563
0.6505	Remote Similarity	NPC29531
0.6497	Remote Similarity	NPC269383
0.6497	Remote Similarity	NPC151030
0.6435	Remote Similarity	NPC194699
0.6435	Remote Similarity	NPC219350
0.6409	Remote Similarity	NPC25539
0.6393	Remote Similarity	NPC277306
0.6393	Remote Similarity	NPC469442
0.6355	Remote Similarity	NPC271958
0.6355	Remote Similarity	NPC134413
0.6355	Remote Similarity	NPC263507
0.6355	Remote Similarity	NPC45112
0.6351	Remote Similarity	NPC473371
0.635	Remote Similarity	NPC49315
0.6318	Remote Similarity	NPC92235
0.6296	Remote Similarity	NPC313414
0.6281	Remote Similarity	NPC208280
0.6268	Remote Similarity	NPC51047
0.6263	Remote Similarity	NPC254700
0.6256	Remote Similarity	NPC469444
0.6244	Remote Similarity	NPC469445
0.6238	Remote Similarity	NPC227778
0.6233	Remote Similarity	NPC469443
0.6225	Remote Similarity	NPC107283
0.6214	Remote Similarity	NPC86678
0.621	Remote Similarity	NPC220060
0.619	Remote Similarity	NPC223384
0.6188	Remote Similarity	NPC182257
0.6161	Remote Similarity	NPC470728
0.615	Remote Similarity	NPC296898
0.615	Remote Similarity	NPC264938
0.6143	Remote Similarity	NPC474661
0.6143	Remote Similarity	NPC475919
0.6126	Remote Similarity	NPC9373
0.6126	Remote Similarity	NPC14390
0.6126	Remote Similarity	NPC189908
0.6122	Remote Similarity	NPC323336
0.6122	Remote Similarity	NPC475557
0.6122	Remote Similarity	NPC326349
0.6117	Remote Similarity	NPC32064
0.6108	Remote Similarity	NPC204908
0.6108	Remote Similarity	NPC68850
0.6108	Remote Similarity	NPC83198
0.6108	Remote Similarity	NPC474881
0.61	Remote Similarity	NPC179250
0.61	Remote Similarity	NPC50380
0.6098	Remote Similarity	NPC289743
0.6098	Remote Similarity	NPC110374
0.6098	Remote Similarity	NPC474051
0.6089	Remote Similarity	NPC196091
0.6089	Remote Similarity	NPC471568
0.6089	Remote Similarity	NPC473693
0.6085	Remote Similarity	NPC477526
0.608	Remote Similarity	NPC329837
0.6077	Remote Similarity	NPC138083
0.6067	Remote Similarity	NPC187868
0.6066	Remote Similarity	NPC295287
0.6062	Remote Similarity	NPC115144
0.6062	Remote Similarity	NPC277857
0.6056	Remote Similarity	NPC318805
0.6056	Remote Similarity	NPC41122
0.605	Remote Similarity	NPC472923
0.6048	Remote Similarity	NPC471801
0.6044	Remote Similarity	NPC326027
0.6043	Remote Similarity	NPC313694
0.6043	Remote Similarity	NPC242159
0.6041	Remote Similarity	NPC56635
0.604	Remote Similarity	NPC186617
0.604	Remote Similarity	NPC469505
0.6039	Remote Similarity	NPC1291
0.6039	Remote Similarity	NPC115343
0.603	Remote Similarity	NPC306366
0.6029	Remote Similarity	NPC45072
0.6027	Remote Similarity	NPC326333
0.6022	Remote Similarity	NPC2363
0.602	Remote Similarity	NPC127402
0.602	Remote Similarity	NPC123011
0.602	Remote Similarity	NPC469479
0.602	Remote Similarity	NPC256689
0.6019	Remote Similarity	NPC152680
0.6019	Remote Similarity	NPC232872
0.6019	Remote Similarity	NPC190783
0.6019	Remote Similarity	NPC474902
0.6019	Remote Similarity	NPC232386
0.601	Remote Similarity	NPC87363
0.6009	Remote Similarity	NPC473407
0.6009	Remote Similarity	NPC473378
0.6	Remote Similarity	NPC161144
0.6	Remote Similarity	NPC471849
0.6	Remote Similarity	NPC471165
0.6	Remote Similarity	NPC471848
0.6	Remote Similarity	NPC85381
0.6	Remote Similarity	NPC164608
0.6	Remote Similarity	NPC184933
0.6	Remote Similarity	NPC193334
0.6	Remote Similarity	NPC59827
0.6	Remote Similarity	NPC119291
0.5991	Remote Similarity	NPC50548
0.5991	Remote Similarity	NPC323662
0.5989	Remote Similarity	NPC253574
0.5989	Remote Similarity	NPC98179
0.5982	Remote Similarity	NPC476662
0.5981	Remote Similarity	NPC314213
0.5981	Remote Similarity	NPC477568
0.5979	Remote Similarity	NPC324081
0.5979	Remote Similarity	NPC476989
0.5978	Remote Similarity	NPC97432
0.5978	Remote Similarity	NPC52247
0.5978	Remote Similarity	NPC190454
0.5972	Remote Similarity	NPC276120
0.597	Remote Similarity	NPC202839
0.597	Remote Similarity	NPC66678
0.597	Remote Similarity	NPC18402
0.5962	Remote Similarity	NPC174122
0.5962	Remote Similarity	NPC64140
0.5961	Remote Similarity	NPC470936
0.5959	Remote Similarity	NPC314743
0.5957	Remote Similarity	NPC33986
0.5952	Remote Similarity	NPC315913
0.5951	Remote Similarity	NPC234053
0.595	Remote Similarity	NPC206736
0.595	Remote Similarity	NPC78359
0.595	Remote Similarity	NPC129603
0.595	Remote Similarity	NPC148014
0.595	Remote Similarity	NPC65490
0.595	Remote Similarity	NPC40389
0.595	Remote Similarity	NPC195766
0.595	Remote Similarity	NPC315707
0.5947	Remote Similarity	NPC189724
0.5947	Remote Similarity	NPC212850
0.5947	Remote Similarity	NPC83289
0.5947	Remote Similarity	NPC86087
0.5945	Remote Similarity	NPC234318
0.5945	Remote Similarity	NPC144314
0.5943	Remote Similarity	NPC4910
0.5943	Remote Similarity	NPC329731
0.5942	Remote Similarity	NPC228040
0.5939	Remote Similarity	NPC474560
0.5936	Remote Similarity	NPC163557
0.5936	Remote Similarity	NPC476661
0.5936	Remote Similarity	NPC475654
0.5934	Remote Similarity	NPC207179
0.5934	Remote Similarity	NPC278552
0.5934	Remote Similarity	NPC29477
0.5934	Remote Similarity	NPC167571
0.5933	Remote Similarity	NPC314025
0.5932	Remote Similarity	NPC74821
0.5931	Remote Similarity	NPC90984
0.593	Remote Similarity	NPC287757
0.593	Remote Similarity	NPC150670
0.593	Remote Similarity	NPC107602
0.593	Remote Similarity	NPC319320
0.5926	Remote Similarity	NPC20829
0.5926	Remote Similarity	NPC262585
0.5926	Remote Similarity	NPC475843
0.5926	Remote Similarity	NPC18189
0.5924	Remote Similarity	NPC471802
0.5924	Remote Similarity	NPC222572
0.5924	Remote Similarity	NPC87224
0.5924	Remote Similarity	NPC315542
0.5922	Remote Similarity	NPC26108
0.5917	Remote Similarity	NPC477527
0.5916	Remote Similarity	NPC123761
0.5915	Remote Similarity	NPC234069
0.5914	Remote Similarity	NPC307123
0.5914	Remote Similarity	NPC247018
0.5914	Remote Similarity	NPC470392
0.5914	Remote Similarity	NPC162801
0.5914	Remote Similarity	NPC97870
0.5911	Remote Similarity	NPC319774
0.5911	Remote Similarity	NPC197125
0.5909	Remote Similarity	NPC473778
0.5907	Remote Similarity	NPC97004
0.5907	Remote Similarity	NPC136951
0.5907	Remote Similarity	NPC161155
0.5904	Remote Similarity	NPC117048
0.5904	Remote Similarity	NPC92830
0.5904	Remote Similarity	NPC124085
0.5899	Remote Similarity	NPC295259
0.5899	Remote Similarity	NPC149962
0.5895	Remote Similarity	NPC36434
0.5895	Remote Similarity	NPC299583
0.5894	Remote Similarity	NPC231371
0.5894	Remote Similarity	NPC129578
0.5892	Remote Similarity	NPC246991
0.5892	Remote Similarity	NPC49583
0.5887	Remote Similarity	NPC274268
0.5885	Remote Similarity	NPC188618
0.5885	Remote Similarity	NPC266741
0.5882	Remote Similarity	NPC105541
0.588	Remote Similarity	NPC328763
0.588	Remote Similarity	NPC471803
0.588	Remote Similarity	NPC471338
0.588	Remote Similarity	NPC474678
0.588	Remote Similarity	NPC471804

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 NPC322424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	778
0.2-0.3	1594
0.3-0.4	2900
0.4-0.5	2659
0.5-0.6	988
0.6-0.7	32
0.7-0.8	1
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
0.7308	Intermediate Similarity	NPD1715	Phase 1
0.7308	Intermediate Similarity	NPD1714	Approved
0.7286	Intermediate Similarity	NPD6312	Discontinued
0.6649	Remote Similarity	NPD3365	Discontinued
0.6582	Remote Similarity	NPD2517	Approved
0.6579	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD4064	Discontinued
0.6531	Remote Similarity	NPD2516	Approved
0.6485	Remote Similarity	NPD3303	Discontinued
0.6477	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4361	Phase 2
0.6429	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD2219	Phase 1
0.6385	Remote Similarity	NPD5542	Phase 2
0.6373	Remote Similarity	NPD6072	Discontinued
0.6355	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7131	Phase 3
0.6326	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.629	Remote Similarity	NPD2377	Approved
0.629	Remote Similarity	NPD2378	Approved
0.629	Remote Similarity	NPD2376	Approved
0.6281	Remote Similarity	NPD5623	Approved
0.6281	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7213	Phase 3
0.6263	Remote Similarity	NPD7212	Phase 2
0.6262	Remote Similarity	NPD3337	Discontinued
0.623	Remote Similarity	NPD7447	Phase 1
0.623	Remote Similarity	NPD1555	Discontinued
0.6224	Remote Similarity	NPD5772	Approved
0.6224	Remote Similarity	NPD5773	Approved
0.622	Remote Similarity	NPD4435	Approved
0.6193	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD2498	Approved
0.6172	Remote Similarity	NPD4434	Approved
0.617	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD7608	Discontinued
0.6154	Remote Similarity	NPD4678	Approved
0.6154	Remote Similarity	NPD4675	Approved
0.615	Remote Similarity	NPD4363	Phase 3
0.615	Remote Similarity	NPD4360	Phase 2
0.6142	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6447	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6056	Approved
0.6103	Remote Similarity	NPD6057	Approved
0.6098	Remote Similarity	NPD4873	Discontinued
0.6095	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD6034	Phase 2
0.6087	Remote Similarity	NPD5745	Approved
0.6075	Remote Similarity	NPD4771	Phase 2
0.6068	Remote Similarity	NPD3885	Approved
0.6064	Remote Similarity	NPD1725	Approved
0.6062	Remote Similarity	NPD3536	Discontinued
0.6062	Remote Similarity	NPD3985	Discontinued
0.6058	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1652	Phase 2
0.6043	Remote Similarity	NPD2200	Suspended
0.6042	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD4466	Phase 1
0.6021	Remote Similarity	NPD1718	Discontinued
0.602	Remote Similarity	NPD4005	Discontinued
0.6019	Remote Similarity	NPD3933	Discontinued
0.6019	Remote Similarity	NPD3119	Phase 1
0.6019	Remote Similarity	NPD5095	Phase 3
0.6019	Remote Similarity	NPD5096	Phase 3
0.6019	Remote Similarity	NPD3120	Approved
0.601	Remote Similarity	NPD5297	Approved
0.601	Remote Similarity	NPD3007	Approved
0.601	Remote Similarity	NPD2515	Approved
0.6	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD1339	Discontinued
0.599	Remote Similarity	NPD1413	Approved
0.599	Remote Similarity	NPD22	Approved
0.599	Remote Similarity	NPD1414	Approved
0.599	Remote Similarity	NPD2053	Approved
0.5981	Remote Similarity	NPD3819	Phase 2
0.5981	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD422	Phase 1
0.5978	Remote Similarity	NPD5746	Approved
0.5972	Remote Similarity	NPD5565	Discontinued
0.5969	Remote Similarity	NPD1416	Approved
0.5961	Remote Similarity	NPD7485	Phase 3
0.5961	Remote Similarity	NPD7484	Phase 3
0.596	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.596	Remote Similarity	NPD2513	Approved
0.5959	Remote Similarity	NPD6815	Approved
0.5956	Remote Similarity	NPD1285	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD2403	Approved
0.595	Remote Similarity	NPD2563	Approved
0.595	Remote Similarity	NPD2560	Approved
0.5949	Remote Similarity	NPD2183	Approved
0.5949	Remote Similarity	NPD6390	Discontinued
0.5949	Remote Similarity	NPD7303	Discontinued
0.5949	Remote Similarity	NPD2184	Approved
0.5946	Remote Similarity	NPD1048	Approved
0.5945	Remote Similarity	NPD5651	Approved
0.5945	Remote Similarity	NPD5652	Approved
0.5945	Remote Similarity	NPD5650	Approved
0.5939	Remote Similarity	NPD2052	Approved
0.5938	Remote Similarity	NPD5481	Discontinued
0.5932	Remote Similarity	NPD1548	Phase 1
0.5928	Remote Similarity	NPD1786	Approved
0.5928	Remote Similarity	NPD1785	Approved
0.5928	Remote Similarity	NPD1787	Approved
0.5928	Remote Similarity	NPD4357	Discontinued
0.5926	Remote Similarity	NPD3260	Discontinued
0.5916	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD6841	Approved
0.5915	Remote Similarity	NPD4113	Discontinued
0.5915	Remote Similarity	NPD6842	Approved
0.5915	Remote Similarity	NPD6843	Phase 3
0.5914	Remote Similarity	NPD1423	Approved
0.5913	Remote Similarity	NPD1716	Phase 3
0.5913	Remote Similarity	NPD5484	Approved
0.5913	Remote Similarity	NPD5485	Approved
0.5911	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD3692	Discontinued
0.5905	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3052	Approved
0.5904	Remote Similarity	NPD3054	Approved
0.59	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4123	Phase 3
0.5897	Remote Similarity	NPD3158	Phase 1
0.5897	Remote Similarity	NPD3157	Approved
0.5891	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6971	Discontinued
0.5888	Remote Similarity	NPD7861	Discontinued
0.5885	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD468	Phase 1
0.587	Remote Similarity	NPD454	Approved
0.5869	Remote Similarity	NPD3065	Discontinued
0.5867	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3111	Phase 1
0.5859	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD7466	Approved
0.5854	Remote Similarity	NPD6071	Discontinued
0.5853	Remote Similarity	NPD4523	Approved
0.5853	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD2122	Discontinued
0.5833	Remote Similarity	NPD6746	Phase 2
0.5833	Remote Similarity	NPD5677	Discontinued
0.5833	Remote Similarity	NPD4666	Phase 3
0.5833	Remote Similarity	NPD3601	Discontinued
0.5829	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD2215	Approved
0.5825	Remote Similarity	NPD2216	Approved
0.5825	Remote Similarity	NPD2388	Discontinued
0.5821	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7811	Phase 3
0.5818	Remote Similarity	NPD7810	Phase 3
0.5816	Remote Similarity	NPD681	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4739	Approved
0.5813	Remote Similarity	NPD8070	Approved
0.581	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD3180	Approved
0.5806	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4590	Approved
0.5806	Remote Similarity	NPD3179	Approved
0.5803	Remote Similarity	NPD4237	Approved
0.5803	Remote Similarity	NPD4236	Phase 3
0.58	Remote Similarity	NPD3778	Approved
0.58	Remote Similarity	NPD5090	Approved
0.58	Remote Similarity	NPD5089	Approved
0.58	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD8164	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD6504	Approved
0.5787	Remote Similarity	NPD6505	Approved
0.5784	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5709	Phase 3
0.5781	Remote Similarity	NPD3656	Approved
0.5775	Remote Similarity	NPD8054	Approved
0.5775	Remote Similarity	NPD8053	Approved
0.5773	Remote Similarity	NPD4535	Phase 3
0.5771	Remote Similarity	NPD5355	Approved
0.5771	Remote Similarity	NPD5356	Approved
0.5769	Remote Similarity	NPD3366	Approved
0.5767	Remote Similarity	NPD779	Phase 2
0.5767	Remote Similarity	NPD4157	Discontinued
0.5762	Remote Similarity	NPD2826	Approved
0.5762	Remote Similarity	NPD2825	Approved
0.5762	Remote Similarity	NPD2827	Approved
0.5759	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.5759	Remote Similarity	NPD5588	Approved
0.5756	Remote Similarity	NPD7129	Suspended
0.5755	Remote Similarity	NPD1361	Discontinued
0.5755	Remote Similarity	NPD4012	Approved
0.5753	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7585	Approved
0.575	Remote Similarity	NPD4972	Discontinued
0.5745	Remote Similarity	NPD829	Discontinued
0.5745	Remote Similarity	NPD2674	Phase 3
0.5745	Remote Similarity	NPD839	Approved

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