NPASS Compound

Structure

NPC475702 OpenBabel07101718312D 24 27 0 0 1 0 0 0 0 0999 V2000 -0.6947 -4.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4500 -1.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4500 -3.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6145 -2.0554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2855 -2.0554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2855 -3.0201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6145 -3.0201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6970 -1.7573 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0658 -1.4669 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8291 -2.5280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1938 -2.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1299 -2.5378 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1210 -1.5730 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.6733 -2.3482 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1480 -3.0046 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1210 -3.5025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5864 -3.1257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0079 -4.6901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1432 -3.9693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6970 -3.3183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6297 -0.7948 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.7998 -0.5395 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.9595 -0.1008 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 0 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 1 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 23 1 0 0 0 0 22 24 1 0 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	423.91
Volume:	323.892
LogP:	2.19
LogD:	2.024
LogS:	-4.539
# Rotatable Bonds:	1
TPSA:	88.1
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	6.64
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.359
MDCK Permeability:	1.3316237527760677e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.116
Human Intestinal Absorption (HIA):	0.354
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872
Plasma Protein Binding (PPB):	72.79145050048828%
Volume Distribution (VD):	0.796
Pgp-substrate:	20.335718154907227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.746
CYP1A2-substrate:	0.418
CYP2C19-inhibitor:	0.989
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.944
CYP2C9-substrate:	0.535
CYP2D6-inhibitor:	0.653
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.49
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	9.468
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.253
Rat Oral Acute Toxicity:	0.427
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.674
Carcinogencity:	0.692
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.847

Download Data

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

Natural Product: NPC475702

Natural Product ID:	NPC475702
*Common Name:**	Tetrathioaspirochlorine
IUPAC Name:	n.a.
Synonyms:	Tetrathioaspirochlorine
Standard InCHIKey:	BYQXYZWYGWKZOQ-PFCYTDGNSA-N
Standard InCHI:	InChI=1S/C12H9ClN2O5S4/c1-19-15-10(17)9-14-11(18)12(15)8(21-23-24-22-9)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)C2SSSS[C@@H]3[C@@]1(Oc1c3cc(c(c1)O)Cl)C(=N2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512142
PubChem CID:	11510122
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]
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]
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	=	4200.0	nM	PMID[529780]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	83.0	nM	PMID[529780]
NPT27	Others	Unspecified		Ratio IC50	=	50.0	n.a.	PMID[529780]

☑ 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 NPC475702 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	3299
0.2-0.3	14053
0.3-0.4	6012
0.4-0.5	12474
0.5-0.6	6434
0.6-0.7	71
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	NPC322424
0.6683	Remote Similarity	NPC474498
0.656	Remote Similarity	NPC477665
0.6507	Remote Similarity	NPC471563
0.6473	Remote Similarity	NPC29531
0.6465	Remote Similarity	NPC151030
0.6465	Remote Similarity	NPC269383
0.6406	Remote Similarity	NPC219350
0.6406	Remote Similarity	NPC194699
0.638	Remote Similarity	NPC25539
0.6364	Remote Similarity	NPC469442
0.6364	Remote Similarity	NPC277306
0.6324	Remote Similarity	NPC134413
0.6324	Remote Similarity	NPC263507
0.6324	Remote Similarity	NPC45112
0.6324	Remote Similarity	NPC271958
0.6321	Remote Similarity	NPC473371
0.6318	Remote Similarity	NPC49315
0.6313	Remote Similarity	NPC477666
0.629	Remote Similarity	NPC92235
0.6263	Remote Similarity	NPC313414
0.625	Remote Similarity	NPC208280
0.6238	Remote Similarity	NPC51047
0.6231	Remote Similarity	NPC254700
0.6227	Remote Similarity	NPC469444
0.6216	Remote Similarity	NPC469445
0.6207	Remote Similarity	NPC227778
0.6204	Remote Similarity	NPC469443
0.6195	Remote Similarity	NPC107283
0.6184	Remote Similarity	NPC86678
0.6182	Remote Similarity	NPC220060
0.6161	Remote Similarity	NPC223384
0.6158	Remote Similarity	NPC182257
0.6132	Remote Similarity	NPC470728
0.6121	Remote Similarity	NPC264938
0.6117	Remote Similarity	NPC296898
0.6114	Remote Similarity	NPC475919
0.6114	Remote Similarity	NPC474661
0.6099	Remote Similarity	NPC14390
0.6094	Remote Similarity	NPC9373
0.6094	Remote Similarity	NPC189908
0.6091	Remote Similarity	NPC326349
0.6091	Remote Similarity	NPC323336
0.6087	Remote Similarity	NPC32064
0.6078	Remote Similarity	NPC474881
0.6078	Remote Similarity	NPC68850
0.607	Remote Similarity	NPC179250
0.607	Remote Similarity	NPC50380
0.6068	Remote Similarity	NPC474051
0.6068	Remote Similarity	NPC289743
0.6068	Remote Similarity	NPC110374
0.6059	Remote Similarity	NPC471568
0.6059	Remote Similarity	NPC473693
0.6059	Remote Similarity	NPC196091
0.6056	Remote Similarity	NPC477526
0.6048	Remote Similarity	NPC138083
0.6038	Remote Similarity	NPC295287
0.6034	Remote Similarity	NPC187868
0.6031	Remote Similarity	NPC115144
0.6031	Remote Similarity	NPC277857
0.6028	Remote Similarity	NPC318805
0.6028	Remote Similarity	NPC41122
0.602	Remote Similarity	NPC472923
0.6018	Remote Similarity	NPC326027
0.6011	Remote Similarity	NPC313694
0.6011	Remote Similarity	NPC242159
0.601	Remote Similarity	NPC186617
0.601	Remote Similarity	NPC56635
0.601	Remote Similarity	NPC469505
0.601	Remote Similarity	NPC115343
0.601	Remote Similarity	NPC475557
0.601	Remote Similarity	NPC1291
0.6	Remote Similarity	NPC326333
0.5991	Remote Similarity	NPC232872
0.599	Remote Similarity	NPC469479
0.599	Remote Similarity	NPC474902
0.599	Remote Similarity	NPC127402
0.599	Remote Similarity	NPC123011
0.599	Remote Similarity	NPC256689
0.5989	Remote Similarity	NPC2363
0.5981	Remote Similarity	NPC473407
0.5981	Remote Similarity	NPC473378
0.598	Remote Similarity	NPC87363
0.5973	Remote Similarity	NPC119291
0.5973	Remote Similarity	NPC471848
0.5973	Remote Similarity	NPC161144
0.5973	Remote Similarity	NPC471849
0.5972	Remote Similarity	NPC85381
0.5972	Remote Similarity	NPC59827
0.5972	Remote Similarity	NPC184933
0.5971	Remote Similarity	NPC164608
0.5971	Remote Similarity	NPC471165
0.597	Remote Similarity	NPC329837
0.5968	Remote Similarity	NPC193334
0.5963	Remote Similarity	NPC323662
0.5963	Remote Similarity	NPC50548
0.5957	Remote Similarity	NPC253574
0.5957	Remote Similarity	NPC98179
0.5955	Remote Similarity	NPC476662
0.5952	Remote Similarity	NPC477568
0.5952	Remote Similarity	NPC314213
0.5949	Remote Similarity	NPC324081
0.5947	Remote Similarity	NPC476989
0.5944	Remote Similarity	NPC52247
0.5944	Remote Similarity	NPC97432
0.5944	Remote Similarity	NPC190454
0.5943	Remote Similarity	NPC276120
0.5935	Remote Similarity	NPC64140
0.5935	Remote Similarity	NPC174122
0.5935	Remote Similarity	NPC314743
0.5931	Remote Similarity	NPC470936
0.5926	Remote Similarity	NPC33986
0.5924	Remote Similarity	NPC315913
0.5922	Remote Similarity	NPC204908
0.5922	Remote Similarity	NPC234053
0.5922	Remote Similarity	NPC83198
0.592	Remote Similarity	NPC206736
0.592	Remote Similarity	NPC306366
0.592	Remote Similarity	NPC195766
0.5917	Remote Similarity	NPC144314
0.5917	Remote Similarity	NPC234318
0.5916	Remote Similarity	NPC83289
0.5916	Remote Similarity	NPC86087
0.5916	Remote Similarity	NPC189724
0.5916	Remote Similarity	NPC212850
0.5915	Remote Similarity	NPC4910
0.5915	Remote Similarity	NPC329731
0.5913	Remote Similarity	NPC228040
0.5909	Remote Similarity	NPC476661
0.5909	Remote Similarity	NPC474560
0.5909	Remote Similarity	NPC475654
0.5905	Remote Similarity	NPC314025
0.5904	Remote Similarity	NPC163557
0.5902	Remote Similarity	NPC167571
0.5902	Remote Similarity	NPC29477
0.5902	Remote Similarity	NPC278552
0.5902	Remote Similarity	NPC207179
0.5902	Remote Similarity	NPC90984
0.59	Remote Similarity	NPC319320
0.59	Remote Similarity	NPC287757
0.59	Remote Similarity	NPC107602
0.59	Remote Similarity	NPC150670
0.5899	Remote Similarity	NPC74821
0.5896	Remote Similarity	NPC315542
0.5895	Remote Similarity	NPC262585
0.5895	Remote Similarity	NPC18189
0.5895	Remote Similarity	NPC20829
0.5894	Remote Similarity	NPC26108
0.5892	Remote Similarity	NPC87224
0.5892	Remote Similarity	NPC222572
0.589	Remote Similarity	NPC477527
0.5888	Remote Similarity	NPC234069
0.5887	Remote Similarity	NPC319774
0.5885	Remote Similarity	NPC123761
0.5885	Remote Similarity	NPC197125
0.5882	Remote Similarity	NPC162801
0.5882	Remote Similarity	NPC247018
0.5882	Remote Similarity	NPC307123
0.5882	Remote Similarity	NPC470392
0.5882	Remote Similarity	NPC97870
0.5879	Remote Similarity	NPC473778
0.5876	Remote Similarity	NPC136951
0.5876	Remote Similarity	NPC97004
0.5876	Remote Similarity	NPC161155
0.5873	Remote Similarity	NPC124085
0.5873	Remote Similarity	NPC117048
0.5873	Remote Similarity	NPC92830
0.5872	Remote Similarity	NPC149962
0.5869	Remote Similarity	NPC471801
0.5868	Remote Similarity	NPC49583
0.5866	Remote Similarity	NPC295259
0.5865	Remote Similarity	NPC129578
0.5865	Remote Similarity	NPC231371
0.5864	Remote Similarity	NPC299583
0.5864	Remote Similarity	NPC36434
0.5862	Remote Similarity	NPC274268
0.5862	Remote Similarity	NPC66678
0.5862	Remote Similarity	NPC202839
0.586	Remote Similarity	NPC246991
0.5857	Remote Similarity	NPC188618
0.5855	Remote Similarity	NPC266741
0.5853	Remote Similarity	NPC328763
0.5851	Remote Similarity	NPC105541
0.5849	Remote Similarity	NPC45072
0.5849	Remote Similarity	NPC474607
0.5847	Remote Similarity	NPC95733
0.5847	Remote Similarity	NPC62101
0.5846	Remote Similarity	NPC110337
0.5846	Remote Similarity	NPC200207
0.5846	Remote Similarity	NPC97282
0.5845	Remote Similarity	NPC281629
0.5842	Remote Similarity	NPC235628
0.5838	Remote Similarity	NPC471032
0.5838	Remote Similarity	NPC470935
0.5837	Remote Similarity	NPC232386
0.5837	Remote Similarity	NPC190783
0.5837	Remote Similarity	NPC242728
0.5837	Remote Similarity	NPC152680
0.5833	Remote Similarity	NPC298821
0.5833	Remote Similarity	NPC477837

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 NPC475702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	788
0.2-0.3	1596
0.3-0.4	2901
0.4-0.5	2659
0.5-0.6	976
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
0.7268	Intermediate Similarity	NPD1715	Phase 1
0.7268	Intermediate Similarity	NPD1714	Approved
0.725	Intermediate Similarity	NPD6312	Discontinued
0.6548	Remote Similarity	NPD2517	Approved
0.6545	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4064	Discontinued
0.6497	Remote Similarity	NPD2516	Approved
0.6443	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4361	Phase 2
0.6393	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD2219	Phase 1
0.6364	Remote Similarity	NPD3365	Discontinued
0.6355	Remote Similarity	NPD5542	Phase 2
0.634	Remote Similarity	NPD6072	Discontinued
0.6324	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD7131	Phase 3
0.6296	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5623	Approved
0.623	Remote Similarity	NPD7212	Phase 2
0.623	Remote Similarity	NPD7213	Phase 3
0.6214	Remote Similarity	NPD3303	Discontinued
0.6198	Remote Similarity	NPD7447	Phase 1
0.6196	Remote Similarity	NPD1555	Discontinued
0.6193	Remote Similarity	NPD5772	Approved
0.6193	Remote Similarity	NPD5773	Approved
0.619	Remote Similarity	NPD4435	Approved
0.6162	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD2498	Approved
0.6143	Remote Similarity	NPD4434	Approved
0.6139	Remote Similarity	NPD7608	Discontinued
0.6122	Remote Similarity	NPD4675	Approved
0.6122	Remote Similarity	NPD4678	Approved
0.6121	Remote Similarity	NPD4363	Phase 3
0.6121	Remote Similarity	NPD4360	Phase 2
0.6111	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD6447	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD2377	Approved
0.6085	Remote Similarity	NPD2378	Approved
0.6085	Remote Similarity	NPD2376	Approved
0.6071	Remote Similarity	NPD6056	Approved
0.6071	Remote Similarity	NPD6057	Approved
0.6068	Remote Similarity	NPD4873	Discontinued
0.6066	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD6034	Phase 2
0.6054	Remote Similarity	NPD5745	Approved
0.6047	Remote Similarity	NPD4771	Phase 2
0.6039	Remote Similarity	NPD3885	Approved
0.6032	Remote Similarity	NPD1725	Approved
0.6031	Remote Similarity	NPD3536	Discontinued
0.6031	Remote Similarity	NPD3985	Discontinued
0.6029	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD1652	Phase 2
0.6011	Remote Similarity	NPD2200	Suspended
0.601	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4466	Phase 1
0.6	Remote Similarity	NPD3337	Discontinued
0.5991	Remote Similarity	NPD3120	Approved
0.5991	Remote Similarity	NPD3119	Phase 1
0.599	Remote Similarity	NPD5095	Phase 3
0.599	Remote Similarity	NPD3933	Discontinued
0.599	Remote Similarity	NPD5096	Phase 3
0.599	Remote Similarity	NPD1718	Discontinued
0.599	Remote Similarity	NPD4005	Discontinued
0.598	Remote Similarity	NPD3007	Approved
0.598	Remote Similarity	NPD2515	Approved
0.5979	Remote Similarity	NPD5297	Approved
0.5967	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD1339	Discontinued
0.5961	Remote Similarity	NPD1413	Approved
0.5961	Remote Similarity	NPD1414	Approved
0.596	Remote Similarity	NPD22	Approved
0.596	Remote Similarity	NPD2053	Approved
0.5953	Remote Similarity	NPD3819	Phase 2
0.5952	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5746	Approved
0.5944	Remote Similarity	NPD422	Phase 1
0.5943	Remote Similarity	NPD5565	Discontinued
0.5938	Remote Similarity	NPD1416	Approved
0.5931	Remote Similarity	NPD7484	Phase 3
0.5931	Remote Similarity	NPD7485	Phase 3
0.593	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.593	Remote Similarity	NPD2513	Approved
0.5928	Remote Similarity	NPD6815	Approved
0.5924	Remote Similarity	NPD1285	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD2403	Approved
0.5918	Remote Similarity	NPD6390	Discontinued
0.5918	Remote Similarity	NPD2183	Approved
0.5918	Remote Similarity	NPD2184	Approved
0.5918	Remote Similarity	NPD7303	Discontinued
0.5917	Remote Similarity	NPD5650	Approved
0.5917	Remote Similarity	NPD5652	Approved
0.5917	Remote Similarity	NPD5651	Approved
0.5914	Remote Similarity	NPD1048	Approved
0.5909	Remote Similarity	NPD2052	Approved
0.5907	Remote Similarity	NPD5481	Discontinued
0.5899	Remote Similarity	NPD1548	Phase 1
0.5897	Remote Similarity	NPD1786	Approved
0.5897	Remote Similarity	NPD4357	Discontinued
0.5897	Remote Similarity	NPD1787	Approved
0.5897	Remote Similarity	NPD1785	Approved
0.5895	Remote Similarity	NPD3260	Discontinued
0.5888	Remote Similarity	NPD4113	Discontinued
0.5885	Remote Similarity	NPD5484	Approved
0.5885	Remote Similarity	NPD1716	Phase 3
0.5885	Remote Similarity	NPD5485	Approved
0.5885	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1423	Approved
0.5877	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3692	Discontinued
0.5873	Remote Similarity	NPD3054	Approved
0.5873	Remote Similarity	NPD3052	Approved
0.5871	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD3157	Approved
0.5867	Remote Similarity	NPD4123	Phase 3
0.5867	Remote Similarity	NPD3158	Phase 1
0.5862	Remote Similarity	NPD6971	Discontinued
0.5862	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.586	Remote Similarity	NPD7861	Discontinued
0.5857	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD468	Phase 1
0.5841	Remote Similarity	NPD3065	Discontinued
0.5838	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD454	Approved
0.5829	Remote Similarity	NPD3111	Phase 1
0.5829	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD4523	Approved
0.5826	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7466	Approved
0.5814	Remote Similarity	NPD6843	Phase 3
0.5814	Remote Similarity	NPD6842	Approved
0.5814	Remote Similarity	NPD6841	Approved
0.5813	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD2122	Discontinued
0.5806	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD3601	Discontinued
0.5805	Remote Similarity	NPD5677	Discontinued
0.5805	Remote Similarity	NPD4666	Phase 3
0.5805	Remote Similarity	NPD6746	Phase 2
0.5802	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD2388	Discontinued
0.5797	Remote Similarity	NPD2215	Approved
0.5797	Remote Similarity	NPD2216	Approved
0.5792	Remote Similarity	NPD7810	Phase 3
0.5792	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD7811	Phase 3
0.5787	Remote Similarity	NPD4739	Approved
0.5787	Remote Similarity	NPD681	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD8070	Approved
0.5782	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4590	Approved
0.578	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD3179	Approved
0.5775	Remote Similarity	NPD3180	Approved
0.5773	Remote Similarity	NPD4237	Approved
0.5773	Remote Similarity	NPD4236	Phase 3
0.5771	Remote Similarity	NPD3778	Approved
0.5771	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.576	Remote Similarity	NPD6505	Approved
0.576	Remote Similarity	NPD6504	Approved
0.5756	Remote Similarity	NPD5709	Phase 3
0.5753	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.5751	Remote Similarity	NPD3656	Approved
0.5748	Remote Similarity	NPD8054	Approved
0.5748	Remote Similarity	NPD8053	Approved
0.5744	Remote Similarity	NPD4535	Phase 3
0.5743	Remote Similarity	NPD5355	Approved
0.5743	Remote Similarity	NPD5356	Approved
0.5742	Remote Similarity	NPD3366	Approved
0.5741	Remote Similarity	NPD4157	Discontinued
0.5741	Remote Similarity	NPD779	Phase 2
0.5729	Remote Similarity	NPD5588	Approved
0.5729	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD1361	Discontinued
0.5728	Remote Similarity	NPD4012	Approved
0.5728	Remote Similarity	NPD7129	Suspended
0.5727	Remote Similarity	NPD7585	Approved
0.5722	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD4972	Discontinued
0.5714	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2674	Phase 3
0.5714	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5929	Approved
0.5714	Remote Similarity	NPD840	Approved
0.5714	Remote Similarity	NPD829	Discontinued
0.5714	Remote Similarity	NPD839	Approved
0.5714	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2677	Approved
0.5708	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD7007	Discovery
0.5708	Remote Similarity	NPD2168	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