NPASS Compound

Structure

CID80035 OpenBabel06191715422D 24 27 0 0 1 0 0 0 0 0999 V2000 3.7229 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2575 0.3912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 10 1 0 0 0 0 4 12 2 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 2 0 0 0 0 19 1 1 1 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.08
Volume:	323.177
LogP:	3.335
LogD:	2.535
LogS:	-6.374
# Rotatable Bonds:	0
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	3.143
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	1.7344564184895717e-05
Pgp-inhibitor:	0.577
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.185
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	95.50629425048828%
Volume Distribution (VD):	0.537
Pgp-substrate:	1.4936232566833496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.48
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.656
CYP2C9-substrate:	0.425
CYP2D6-inhibitor:	0.394
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.648
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	4.556
Half-life (T1/2):	0.024

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.854
Rat Oral Acute Toxicity:	0.388
Maximum Recommended Daily Dose:	0.482
Skin Sensitization:	0.22
Carcinogencity:	0.94
Eye Corrosion:	0.003
Eye Irritation:	0.913
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC80035

Natural Product ID:	NPC80035
*Common Name:**	Tetrangomycin
IUPAC Name:	(3R)-3,8-dihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
Synonyms:	Tetrangomycin
Standard InCHIKey:	UGEKKXLEYACFTD-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C19H14O5/c1-19(24)7-9-5-6-11-16(14(9)13(21)8-19)18(23)10-3-2-4-12(20)15(10)17(11)22/h2-6,20,24H,7-8H2,1H3/t19-/m1/s1
SMILES:	C[C@]1(Cc2ccc3c(c2C(=O)C1)C(=O)c1cccc(c1C3=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668772
PubChem CID:	11738774
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003415] Angucyclines

*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
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21188999]
NPO33103	amycolatopsis sp. hca1	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23131338]
NPO33526	Streptomyces sp. CB01913	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26335269]
NPO9279	Thalictrum dasycarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9279	Thalictrum dasycarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21021	Hemisteptia lyrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29017	Acer barbinerve	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2630	Phytophthora infestans	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21021	Hemisteptia lyrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11939	Pseudocyphellaria mougeotiana	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9279	Thalictrum dasycarpum	Species	Ranunculaceae	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	9
MIC	3

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	23700.0	nM	PMID[465146]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	36070.0	nM	PMID[465146]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	=	12000.0	nM	PMID[465147]
NPT405	Cell Line	NCI-H226	Homo sapiens	IC50	=	7200.0	nM	PMID[465147]
NPT374	Cell Line	SF-539	Homo sapiens	IC50	=	3200.0	nM	PMID[465147]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	2400.0	nM	PMID[465147]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	16000.0	nM	PMID[465147]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1550.0	nM	PMID[465145]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17740.0	nM	PMID[465146]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	11.0	ug.mL-1	PMID[465147]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.1	ug.mL-1	PMID[465147]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	9.7	ug.mL-1	PMID[465147]

☑ 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 NPC80035 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	368
0.1-0.2	1700
0.2-0.3	3816
0.3-0.4	10481
0.4-0.5	8714
0.5-0.6	5992
0.6-0.7	7435
0.7-0.8	3678
0.8-0.85	335
0.85-0.9	131
0.9-0.95	40
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC13715
0.9538	High Similarity	NPC225051
0.9389	High Similarity	NPC53896
0.9343	High Similarity	NPC79627
0.9328	High Similarity	NPC4214
0.9323	High Similarity	NPC155211
0.9318	High Similarity	NPC50924
0.9242	High Similarity	NPC115458
0.9231	High Similarity	NPC146647
0.9231	High Similarity	NPC34414
0.9191	High Similarity	NPC96421
0.9154	High Similarity	NPC48248
0.9154	High Similarity	NPC282923
0.9141	High Similarity	NPC142956
0.913	High Similarity	NPC53016
0.9118	High Similarity	NPC26924
0.9104	High Similarity	NPC283088
0.9098	High Similarity	NPC52407
0.9091	High Similarity	NPC244699
0.9084	High Similarity	NPC99731
0.9062	High Similarity	NPC375356
0.9058	High Similarity	NPC193555
0.9058	High Similarity	NPC19631
0.9058	High Similarity	NPC239136
0.9051	High Similarity	NPC315578
0.9037	High Similarity	NPC474813
0.9037	High Similarity	NPC272268
0.903	High Similarity	NPC288089
0.9015	High Similarity	NPC136588
0.9015	High Similarity	NPC199253
0.9015	High Similarity	NPC55949
0.8993	High Similarity	NPC471682
0.8993	High Similarity	NPC66593
0.8986	High Similarity	NPC246638
0.8984	High Similarity	NPC300274
0.8978	High Similarity	NPC242994
0.8978	High Similarity	NPC138099
0.8971	High Similarity	NPC53414
0.8971	High Similarity	NPC53206
0.8971	High Similarity	NPC245923
0.8971	High Similarity	NPC471905
0.8963	High Similarity	NPC258502
0.8951	High Similarity	NPC315520
0.8947	High Similarity	NPC474517
0.8947	High Similarity	NPC72669
0.8947	High Similarity	NPC205992
0.8936	High Similarity	NPC314437
0.8923	High Similarity	NPC103540
0.8921	High Similarity	NPC69755
0.8921	High Similarity	NPC257644
0.8913	High Similarity	NPC181560
0.8913	High Similarity	NPC169452
0.8905	High Similarity	NPC61398
0.8905	High Similarity	NPC416
0.8897	High Similarity	NPC474311
0.8897	High Similarity	NPC254847
0.8897	High Similarity	NPC193358
0.8881	High Similarity	NPC70622
0.8881	High Similarity	NPC58685
0.8873	High Similarity	NPC478018
0.8872	High Similarity	NPC31799
0.8865	High Similarity	NPC471683
0.8855	High Similarity	NPC96915
0.8846	High Similarity	NPC173978
0.8837	High Similarity	NPC307174
0.8837	High Similarity	NPC91478
0.8815	High Similarity	NPC294226
0.8806	High Similarity	NPC93015
0.8786	High Similarity	NPC73061
0.876	High Similarity	NPC120545
0.875	High Similarity	NPC287604
0.875	High Similarity	NPC161964
0.875	High Similarity	NPC44437
0.875	High Similarity	NPC472262
0.8731	High Similarity	NPC108129
0.8723	High Similarity	NPC296752
0.8722	High Similarity	NPC96024
0.8714	High Similarity	NPC477275
0.8714	High Similarity	NPC305845
0.8714	High Similarity	NPC204045
0.8714	High Similarity	NPC290550
0.8712	High Similarity	NPC3224
0.8712	High Similarity	NPC160499
0.8707	High Similarity	NPC318270
0.8705	High Similarity	NPC143438
0.8676	High Similarity	NPC267205
0.8671	High Similarity	NPC143685
0.8667	High Similarity	NPC17083
0.8662	High Similarity	NPC193703
0.8662	High Similarity	NPC21599
0.8657	High Similarity	NPC276238
0.8652	High Similarity	NPC135524
0.8652	High Similarity	NPC469520
0.8649	High Similarity	NPC474861
0.8647	High Similarity	NPC176130
0.8647	High Similarity	NPC78364
0.8647	High Similarity	NPC84672
0.8647	High Similarity	NPC69424
0.8623	High Similarity	NPC191976
0.8623	High Similarity	NPC472308
0.8613	High Similarity	NPC166480
0.8613	High Similarity	NPC202225
0.8613	High Similarity	NPC282780
0.8611	High Similarity	NPC37709
0.8611	High Similarity	NPC119767
0.8605	High Similarity	NPC285829
0.8605	High Similarity	NPC206778
0.8601	High Similarity	NPC12402
0.8601	High Similarity	NPC478019
0.8592	High Similarity	NPC313047
0.8592	High Similarity	NPC474203
0.8592	High Similarity	NPC295712
0.8592	High Similarity	NPC451542
0.8591	High Similarity	NPC317580
0.8582	High Similarity	NPC95537
0.8571	High Similarity	NPC306765
0.8571	High Similarity	NPC231774
0.8571	High Similarity	NPC254492
0.8571	High Similarity	NPC1268
0.8571	High Similarity	NPC190457
0.8562	High Similarity	NPC205766
0.8561	High Similarity	NPC310540
0.8561	High Similarity	NPC199273
0.8561	High Similarity	NPC475957
0.8561	High Similarity	NPC305060
0.8542	High Similarity	NPC147250
0.854	High Similarity	NPC477139
0.854	High Similarity	NPC171968
0.854	High Similarity	NPC314048
0.8533	High Similarity	NPC326084
0.8531	High Similarity	NPC244691
0.8531	High Similarity	NPC471906
0.8531	High Similarity	NPC48762
0.8521	High Similarity	NPC85310
0.8519	High Similarity	NPC303910
0.8514	High Similarity	NPC182921
0.8514	High Similarity	NPC218870
0.8514	High Similarity	NPC474824
0.8514	High Similarity	NPC470408
0.8511	High Similarity	NPC225243
0.8507	High Similarity	NPC72667
0.8489	Intermediate Similarity	NPC86524
0.8489	Intermediate Similarity	NPC315275
0.8478	Intermediate Similarity	NPC12070
0.8477	Intermediate Similarity	NPC475449
0.8472	Intermediate Similarity	NPC34482
0.8462	Intermediate Similarity	NPC293545
0.8462	Intermediate Similarity	NPC174905
0.8456	Intermediate Similarity	NPC117609
0.8456	Intermediate Similarity	NPC198305
0.8451	Intermediate Similarity	NPC124365
0.8444	Intermediate Similarity	NPC234175
0.844	Intermediate Similarity	NPC470407
0.8429	Intermediate Similarity	NPC471452
0.8429	Intermediate Similarity	NPC36868
0.8429	Intermediate Similarity	NPC53001
0.8429	Intermediate Similarity	NPC62272
0.8429	Intermediate Similarity	NPC147418
0.8421	Intermediate Similarity	NPC68756
0.8421	Intermediate Similarity	NPC152525
0.8417	Intermediate Similarity	NPC161632
0.8417	Intermediate Similarity	NPC249272
0.8414	Intermediate Similarity	NPC85393
0.8414	Intermediate Similarity	NPC110882
0.8414	Intermediate Similarity	NPC271944
0.8414	Intermediate Similarity	NPC285122
0.8414	Intermediate Similarity	NPC470570
0.8409	Intermediate Similarity	NPC282577
0.8406	Intermediate Similarity	NPC114183
0.8406	Intermediate Similarity	NPC254603
0.8403	Intermediate Similarity	NPC10764
0.8403	Intermediate Similarity	NPC227841
0.8397	Intermediate Similarity	NPC472046
0.8394	Intermediate Similarity	NPC85342
0.8394	Intermediate Similarity	NPC471851
0.8392	Intermediate Similarity	NPC474961
0.8389	Intermediate Similarity	NPC214632
0.8389	Intermediate Similarity	NPC208806
0.8382	Intermediate Similarity	NPC25736
0.8382	Intermediate Similarity	NPC171460
0.8382	Intermediate Similarity	NPC278928
0.838	Intermediate Similarity	NPC203063
0.837	Intermediate Similarity	NPC471530
0.8369	Intermediate Similarity	NPC87723
0.8359	Intermediate Similarity	NPC161304
0.8358	Intermediate Similarity	NPC123506
0.8357	Intermediate Similarity	NPC141934
0.8357	Intermediate Similarity	NPC118919
0.8356	Intermediate Similarity	NPC126767
0.8356	Intermediate Similarity	NPC118027
0.8356	Intermediate Similarity	NPC190648
0.8356	Intermediate Similarity	NPC289042
0.8356	Intermediate Similarity	NPC312929
0.8356	Intermediate Similarity	NPC245584
0.8356	Intermediate Similarity	NPC56433
0.8345	Intermediate Similarity	NPC270899
0.8333	Intermediate Similarity	NPC309430
0.8333	Intermediate Similarity	NPC66029
0.8333	Intermediate Similarity	NPC226656
0.8333	Intermediate Similarity	NPC66508

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 NPC80035 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	975
0.2-0.3	1354
0.3-0.4	2749
0.4-0.5	2173
0.5-0.6	1071
0.6-0.7	395
0.7-0.8	74
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8923	High Similarity	NPD1470	Approved
0.8897	High Similarity	NPD1509	Clinical (unspecified phase)
0.8615	High Similarity	NPD1201	Approved
0.8429	Intermediate Similarity	NPD5408	Approved
0.8429	Intermediate Similarity	NPD5404	Approved
0.8429	Intermediate Similarity	NPD5406	Approved
0.8429	Intermediate Similarity	NPD5405	Approved
0.8403	Intermediate Similarity	NPD7390	Discontinued
0.8295	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD3226	Approved
0.7986	Intermediate Similarity	NPD2346	Discontinued
0.7973	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD943	Approved
0.7718	Intermediate Similarity	NPD3300	Phase 2
0.7698	Intermediate Similarity	NPD1164	Approved
0.7647	Intermediate Similarity	NPD3019	Approved
0.7619	Intermediate Similarity	NPD2344	Approved
0.7619	Intermediate Similarity	NPD1471	Phase 3
0.7584	Intermediate Similarity	NPD7003	Approved
0.7574	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6232	Discontinued
0.7552	Intermediate Similarity	NPD3764	Approved
0.7551	Intermediate Similarity	NPD2935	Discontinued
0.7531	Intermediate Similarity	NPD7473	Discontinued
0.7518	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.7466	Intermediate Similarity	NPD1607	Approved
0.7463	Intermediate Similarity	NPD5951	Approved
0.7462	Intermediate Similarity	NPD2342	Discontinued
0.7431	Intermediate Similarity	NPD2313	Discontinued
0.7419	Intermediate Similarity	NPD7458	Discontinued
0.7417	Intermediate Similarity	NPD2309	Approved
0.7405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2798	Approved
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7342	Intermediate Similarity	NPD7819	Suspended
0.7329	Intermediate Similarity	NPD1240	Approved
0.7326	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7411	Suspended
0.7312	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3026	Approved
0.7214	Intermediate Similarity	NPD3023	Approved
0.7197	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3025	Approved
0.7194	Intermediate Similarity	NPD3024	Approved
0.7193	Intermediate Similarity	NPD8150	Discontinued
0.7185	Intermediate Similarity	NPD7635	Approved
0.7161	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD2534	Approved
0.7161	Intermediate Similarity	NPD2533	Approved
0.7152	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7143	Intermediate Similarity	NPD6535	Approved
0.7133	Intermediate Similarity	NPD1283	Approved
0.7125	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3750	Approved
0.7124	Intermediate Similarity	NPD8166	Discontinued
0.7113	Intermediate Similarity	NPD4878	Approved
0.7113	Intermediate Similarity	NPD3972	Approved
0.711	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1549	Phase 2
0.7101	Intermediate Similarity	NPD9493	Approved
0.7071	Intermediate Similarity	NPD1651	Approved
0.7068	Intermediate Similarity	NPD9264	Approved
0.7068	Intermediate Similarity	NPD9267	Approved
0.7068	Intermediate Similarity	NPD9263	Approved
0.7039	Intermediate Similarity	NPD6780	Approved
0.7039	Intermediate Similarity	NPD6776	Approved
0.7039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6777	Approved
0.7039	Intermediate Similarity	NPD6779	Approved
0.7039	Intermediate Similarity	NPD6781	Approved
0.7039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6778	Approved
0.7039	Intermediate Similarity	NPD6782	Approved
0.7037	Intermediate Similarity	NPD7768	Phase 2
0.7022	Intermediate Similarity	NPD7699	Phase 2
0.7022	Intermediate Similarity	NPD7700	Phase 2
0.702	Intermediate Similarity	NPD4308	Phase 3
0.7018	Intermediate Similarity	NPD8313	Approved
0.7018	Intermediate Similarity	NPD8312	Approved
0.7014	Intermediate Similarity	NPD1876	Approved
0.7007	Intermediate Similarity	NPD7008	Discontinued
0.7006	Intermediate Similarity	NPD6273	Approved
0.6989	Remote Similarity	NPD6212	Phase 3
0.6989	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6213	Phase 3
0.6987	Remote Similarity	NPD1511	Approved
0.6985	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1203	Approved
0.6964	Remote Similarity	NPD7177	Discontinued
0.6959	Remote Similarity	NPD3268	Approved
0.6957	Remote Similarity	NPD1934	Approved
0.694	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7610	Discontinued
0.6923	Remote Similarity	NPD7435	Discontinued
0.6923	Remote Similarity	NPD5844	Phase 1
0.6923	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7698	Approved
0.6923	Remote Similarity	NPD7697	Approved
0.6923	Remote Similarity	NPD7696	Phase 3
0.6914	Remote Similarity	NPD2801	Approved
0.6913	Remote Similarity	NPD6663	Approved
0.6901	Remote Similarity	NPD2286	Discontinued
0.6901	Remote Similarity	NPD4626	Approved
0.6899	Remote Similarity	NPD288	Approved
0.6899	Remote Similarity	NPD1512	Approved
0.6894	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1930	Approved
0.6894	Remote Similarity	NPD1929	Approved
0.6892	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7075	Discontinued
0.6885	Remote Similarity	NPD8320	Phase 1
0.6885	Remote Similarity	NPD8319	Approved
0.6885	Remote Similarity	NPD7871	Phase 2
0.6885	Remote Similarity	NPD7870	Phase 2
0.6871	Remote Similarity	NPD5736	Approved
0.6871	Remote Similarity	NPD2296	Approved
0.6863	Remote Similarity	NPD2796	Approved
0.6863	Remote Similarity	NPD6099	Approved
0.6863	Remote Similarity	NPD6100	Approved
0.6846	Remote Similarity	NPD411	Approved
0.6839	Remote Similarity	NPD2800	Approved
0.6835	Remote Similarity	NPD9281	Approved
0.6829	Remote Similarity	NPD3882	Suspended
0.6824	Remote Similarity	NPD6020	Phase 2
0.6822	Remote Similarity	NPD844	Approved
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1932	Approved
0.681	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5494	Approved
0.6802	Remote Similarity	NPD5031	Approved
0.6802	Remote Similarity	NPD5027	Approved
0.6802	Remote Similarity	NPD5029	Approved
0.6797	Remote Similarity	NPD3748	Approved
0.6795	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4628	Phase 3
0.6794	Remote Similarity	NPD3020	Approved
0.6788	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4059	Approved
0.6783	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7701	Phase 2
0.6767	Remote Similarity	NPD9261	Approved
0.6765	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD36	Approved
0.6763	Remote Similarity	NPD5028	Approved
0.6763	Remote Similarity	NPD4954	Approved
0.6763	Remote Similarity	NPD4955	Approved
0.6763	Remote Similarity	NPD5034	Approved
0.6763	Remote Similarity	NPD5026	Approved
0.6761	Remote Similarity	NPD3091	Approved
0.6761	Remote Similarity	NPD9545	Approved
0.6759	Remote Similarity	NPD9717	Approved
0.6757	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4307	Phase 2
0.6753	Remote Similarity	NPD1551	Phase 2
0.6746	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6166	Phase 2
0.6746	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4879	Approved
0.6735	Remote Similarity	NPD3267	Approved
0.6735	Remote Similarity	NPD3266	Approved
0.6728	Remote Similarity	NPD6599	Discontinued
0.6716	Remote Similarity	NPD1237	Approved
0.6715	Remote Similarity	NPD3021	Approved
0.6715	Remote Similarity	NPD3022	Approved
0.6714	Remote Similarity	NPD497	Approved
0.6712	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1755	Approved
0.6711	Remote Similarity	NPD447	Suspended
0.6706	Remote Similarity	NPD5033	Approved
0.6705	Remote Similarity	NPD5030	Phase 2
0.6702	Remote Similarity	NPD7874	Approved
0.6702	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2860	Approved
0.6692	Remote Similarity	NPD2859	Approved
0.6688	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD3317	Approved
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD5032	Approved
0.6646	Remote Similarity	NPD6801	Discontinued
0.6646	Remote Similarity	NPD6844	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