NPASS Compound

Structure

CID13715 OpenBabel06191715342D 25 28 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 -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 1.7321 2.0000 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 -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 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 0.0000 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 -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 -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 -1.0000 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 -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 9 1 0 0 0 0 4 10 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 19 1 0 0 0 0 7 12 1 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 22 2 0 0 0 0 13 16 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 17 23 2 0 0 0 0 18 24 2 0 0 0 0 19 1 1 1 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.08
Volume:	331.968
LogP:	3.543
LogD:	2.463
LogS:	-7.179
# Rotatable Bonds:	0
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	3.255
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:	-5.42
MDCK Permeability:	1.231751866725972e-05
Pgp-inhibitor:	0.426
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.76
20% Bioavailability (F20%):	0.796
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	97.03992462158203%
Volume Distribution (VD):	0.596
Pgp-substrate:	1.6188597679138184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.653
CYP2C9-substrate:	0.35
CYP2D6-inhibitor:	0.238
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	6.237
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.81
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.537
Skin Sensitization:	0.471
Carcinogencity:	0.868
Eye Corrosion:	0.003
Eye Irritation:	0.92
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC13715

Natural Product ID:	NPC13715
*Common Name:**	Rabelomycin
IUPAC Name:	(3R)-3,6,8-trihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
Synonyms:	Rabelomycin
Standard InCHIKey:	JJOLHRYZQSDLSA-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C19H14O6/c1-19(25)6-8-5-11(21)15-16(13(8)12(22)7-19)17(23)9-3-2-4-10(20)14(9)18(15)24/h2-5,20-21,25H,6-7H2,1H3/t19-/m1/s1
SMILES:	C[C@]1(Cc2cc(c3c(c2C(=O)C1)C(=O)c1cccc(c1C3=O)O)O)O
Synthetic Gene Cluster:	BGC0000223;
ChEMBL Identifier:	CHEMBL2164969
PubChem CID:	443810
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
NPO40557	Micromonospora rosaria SCSIO N160	Strain	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23136829]

☑ 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	3
MIC	5

Activity Type	# Activity
Cell Line	3
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	9910.0	nM	PMID[450539]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4280.0	nM	PMID[450539]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	5540.0	nM	PMID[450539]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[450539]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	=	8.0	ug.mL-1	PMID[450539]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[450539]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16.0	ug.mL-1	PMID[450539]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	64.0	ug.mL-1	PMID[450539]

☑ 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 NPC13715 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	381
0.1-0.2	1717
0.2-0.3	3777
0.3-0.4	10333
0.4-0.5	8726
0.5-0.6	5525
0.6-0.7	7079
0.7-0.8	4505
0.8-0.85	437
0.85-0.9	166
0.9-0.95	43
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC80035
0.9328	High Similarity	NPC283088
0.9323	High Similarity	NPC225051
0.9323	High Similarity	NPC53896
0.9323	High Similarity	NPC115458
0.9313	High Similarity	NPC99731
0.9275	High Similarity	NPC19631
0.9275	High Similarity	NPC239136
0.9275	High Similarity	NPC193555
0.927	High Similarity	NPC96421
0.9265	High Similarity	NPC4214
0.9254	High Similarity	NPC50924
0.9237	High Similarity	NPC282923
0.9203	High Similarity	NPC246638
0.9197	High Similarity	NPC242994
0.9197	High Similarity	NPC26924
0.9197	High Similarity	NPC138099
0.9191	High Similarity	NPC471905
0.9191	High Similarity	NPC53414
0.9191	High Similarity	NPC53206
0.9173	High Similarity	NPC72669
0.9173	High Similarity	NPC474517
0.9143	High Similarity	NPC79627
0.913	High Similarity	NPC181560
0.913	High Similarity	NPC169452
0.913	High Similarity	NPC315578
0.9124	High Similarity	NPC416
0.9124	High Similarity	NPC61398
0.9118	High Similarity	NPC474813
0.9118	High Similarity	NPC254847
0.9118	High Similarity	NPC155211
0.9118	High Similarity	NPC272268
0.9111	High Similarity	NPC288089
0.9071	High Similarity	NPC471682
0.9051	High Similarity	NPC245923
0.9037	High Similarity	NPC52407
0.903	High Similarity	NPC244699
0.903	High Similarity	NPC205992
0.9028	High Similarity	NPC315520
0.9023	High Similarity	NPC146647
0.9023	High Similarity	NPC34414
0.9008	High Similarity	NPC103540
0.9	High Similarity	NPC73061
0.9	High Similarity	NPC257644
0.8971	High Similarity	NPC44437
0.8963	High Similarity	NPC58685
0.8963	High Similarity	NPC70622
0.8947	High Similarity	NPC48248
0.8944	High Similarity	NPC471683
0.8936	High Similarity	NPC66593
0.8936	High Similarity	NPC296752
0.8936	High Similarity	NPC53016
0.8931	High Similarity	NPC173978
0.8931	High Similarity	NPC142956
0.8929	High Similarity	NPC204045
0.8929	High Similarity	NPC477275
0.8929	High Similarity	NPC290550
0.8929	High Similarity	NPC305845
0.8921	High Similarity	NPC143438
0.8905	High Similarity	NPC258502
0.8897	High Similarity	NPC267205
0.8881	High Similarity	NPC314437
0.8873	High Similarity	NPC193703
0.8873	High Similarity	NPC21599
0.8865	High Similarity	NPC469520
0.8865	High Similarity	NPC135524
0.8855	High Similarity	NPC375356
0.8841	High Similarity	NPC191976
0.8832	High Similarity	NPC472262
0.8832	High Similarity	NPC287604
0.8832	High Similarity	NPC161964
0.8832	High Similarity	NPC282780
0.8832	High Similarity	NPC166480
0.8819	High Similarity	NPC37709
0.8819	High Similarity	NPC119767
0.8815	High Similarity	NPC136588
0.8815	High Similarity	NPC55949
0.8815	High Similarity	NPC199253
0.8811	High Similarity	NPC12402
0.8803	High Similarity	NPC451542
0.8803	High Similarity	NPC295712
0.8803	High Similarity	NPC474203
0.8803	High Similarity	NPC313047
0.8797	High Similarity	NPC3224
0.8786	High Similarity	NPC190457
0.8779	High Similarity	NPC300274
0.8779	High Similarity	NPC91478
0.8767	High Similarity	NPC205766
0.8759	High Similarity	NPC294226
0.8759	High Similarity	NPC314048
0.875	High Similarity	NPC93015
0.875	High Similarity	NPC17083
0.875	High Similarity	NPC147250
0.8741	High Similarity	NPC244691
0.8741	High Similarity	NPC471906
0.8741	High Similarity	NPC48762
0.8732	High Similarity	NPC85310
0.8732	High Similarity	NPC69755
0.8725	High Similarity	NPC474861
0.8705	High Similarity	NPC474311
0.8705	High Similarity	NPC193358
0.8705	High Similarity	NPC86524
0.8702	High Similarity	NPC120545
0.869	High Similarity	NPC478018
0.8681	High Similarity	NPC34482
0.8676	High Similarity	NPC108129
0.8676	High Similarity	NPC31799
0.8671	High Similarity	NPC174905
0.8671	High Similarity	NPC293545
0.8667	High Similarity	NPC96024
0.8658	High Similarity	NPC318270
0.8657	High Similarity	NPC96915
0.8657	High Similarity	NPC231774
0.8652	High Similarity	NPC1268
0.8643	High Similarity	NPC471452
0.8643	High Similarity	NPC62272
0.8643	High Similarity	NPC53001
0.8643	High Similarity	NPC147418
0.8643	High Similarity	NPC305060
0.8636	High Similarity	NPC307174
0.8621	High Similarity	NPC143685
0.8621	High Similarity	NPC470570
0.8621	High Similarity	NPC110882
0.8621	High Similarity	NPC271944
0.8621	High Similarity	NPC85393
0.8611	High Similarity	NPC227841
0.8611	High Similarity	NPC10764
0.8603	High Similarity	NPC276238
0.8601	High Similarity	NPC474961
0.8593	High Similarity	NPC69424
0.8593	High Similarity	NPC84672
0.8593	High Similarity	NPC176130
0.8593	High Similarity	NPC78364
0.8592	High Similarity	NPC203063
0.8592	High Similarity	NPC225243
0.8591	High Similarity	NPC182921
0.8591	High Similarity	NPC214632
0.8591	High Similarity	NPC474824
0.8591	High Similarity	NPC218870
0.8591	High Similarity	NPC208806
0.8591	High Similarity	NPC470408
0.8582	High Similarity	NPC87723
0.8571	High Similarity	NPC315275
0.8571	High Similarity	NPC118919
0.8562	High Similarity	NPC312929
0.8562	High Similarity	NPC245584
0.8562	High Similarity	NPC190648
0.8562	High Similarity	NPC126767
0.8562	High Similarity	NPC289042
0.8562	High Similarity	NPC118027
0.8562	High Similarity	NPC56433
0.8561	High Similarity	NPC202225
0.8561	High Similarity	NPC12070
0.8552	High Similarity	NPC478019
0.8543	High Similarity	NPC317580
0.8533	High Similarity	NPC66508
0.8533	High Similarity	NPC226656
0.8533	High Similarity	NPC66029
0.8531	High Similarity	NPC124365
0.8529	High Similarity	NPC95537
0.8521	High Similarity	NPC162939
0.8519	High Similarity	NPC160499
0.8519	High Similarity	NPC473751
0.8519	High Similarity	NPC254492
0.8514	High Similarity	NPC255641
0.8514	High Similarity	NPC290954
0.8511	High Similarity	NPC475957
0.8507	High Similarity	NPC199273
0.8503	High Similarity	NPC471907
0.85	High Similarity	NPC161632
0.85	High Similarity	NPC249272
0.8493	Intermediate Similarity	NPC285122
0.8489	Intermediate Similarity	NPC48036
0.8489	Intermediate Similarity	NPC254603
0.8489	Intermediate Similarity	NPC114183
0.8489	Intermediate Similarity	NPC477139
0.8487	Intermediate Similarity	NPC326084
0.8478	Intermediate Similarity	NPC41847
0.8467	Intermediate Similarity	NPC303910
0.8467	Intermediate Similarity	NPC474998
0.8467	Intermediate Similarity	NPC92624
0.8467	Intermediate Similarity	NPC278928
0.8456	Intermediate Similarity	NPC72667
0.8456	Intermediate Similarity	NPC35
0.8456	Intermediate Similarity	NPC473201
0.8456	Intermediate Similarity	NPC302783
0.844	Intermediate Similarity	NPC141934
0.844	Intermediate Similarity	NPC472308
0.8435	Intermediate Similarity	NPC472135
0.8435	Intermediate Similarity	NPC290194
0.8431	Intermediate Similarity	NPC475449
0.8429	Intermediate Similarity	NPC270899
0.8429	Intermediate Similarity	NPC474519
0.8417	Intermediate Similarity	NPC309430
0.8417	Intermediate Similarity	NPC175738
0.8414	Intermediate Similarity	NPC238629
0.8409	Intermediate Similarity	NPC285829
0.8409	Intermediate Similarity	NPC206778
0.8406	Intermediate Similarity	NPC117609
0.8406	Intermediate Similarity	NPC259942

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 NPC13715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	972
0.2-0.3	1414
0.3-0.4	2791
0.4-0.5	2096
0.5-0.6	1043
0.6-0.7	382
0.7-0.8	80
0.8-0.85	5
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD1509	Clinical (unspecified phase)
0.9008	High Similarity	NPD1470	Approved
0.8702	High Similarity	NPD1201	Approved
0.8643	High Similarity	NPD5406	Approved
0.8643	High Similarity	NPD5405	Approved
0.8643	High Similarity	NPD5404	Approved
0.8643	High Similarity	NPD5408	Approved
0.8611	High Similarity	NPD7390	Discontinued
0.8322	Intermediate Similarity	NPD3226	Approved
0.8176	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD943	Approved
0.7823	Intermediate Similarity	NPD2346	Discontinued
0.7762	Intermediate Similarity	NPD3764	Approved
0.775	Intermediate Similarity	NPD6232	Discontinued
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7697	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7687	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3300	Phase 2
0.7671	Intermediate Similarity	NPD1607	Approved
0.766	Intermediate Similarity	NPD1164	Approved
0.7609	Intermediate Similarity	NPD3019	Approved
0.76	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2344	Approved
0.7568	Intermediate Similarity	NPD1510	Phase 2
0.755	Intermediate Similarity	NPD7003	Approved
0.7536	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1240	Approved
0.7532	Intermediate Similarity	NPD7819	Suspended
0.7517	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD3749	Approved
0.7482	Intermediate Similarity	NPD2932	Approved
0.7468	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1471	Phase 3
0.745	Intermediate Similarity	NPD2799	Discontinued
0.7439	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7458	Discontinued
0.7386	Intermediate Similarity	NPD2309	Approved
0.7355	Intermediate Similarity	NPD2533	Approved
0.7355	Intermediate Similarity	NPD2534	Approved
0.7355	Intermediate Similarity	NPD2532	Approved
0.7342	Intermediate Similarity	NPD4380	Phase 2
0.732	Intermediate Similarity	NPD3750	Approved
0.7312	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1549	Phase 2
0.7299	Intermediate Similarity	NPD5951	Approved
0.7293	Intermediate Similarity	NPD2342	Discontinued
0.7283	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2313	Discontinued
0.7267	Intermediate Similarity	NPD8150	Discontinued
0.7241	Intermediate Similarity	NPD2798	Approved
0.7237	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7768	Phase 2
0.7216	Intermediate Similarity	NPD6535	Approved
0.7216	Intermediate Similarity	NPD6534	Approved
0.7183	Intermediate Similarity	NPD3026	Approved
0.7183	Intermediate Similarity	NPD3023	Approved
0.7179	Intermediate Similarity	NPD1511	Approved
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3025	Approved
0.7163	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD1934	Approved
0.7113	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6781	Approved
0.7111	Intermediate Similarity	NPD6778	Approved
0.7111	Intermediate Similarity	NPD6782	Approved
0.7111	Intermediate Similarity	NPD6780	Approved
0.7111	Intermediate Similarity	NPD6777	Approved
0.7111	Intermediate Similarity	NPD6776	Approved
0.7111	Intermediate Similarity	NPD6779	Approved
0.7103	Intermediate Similarity	NPD1283	Approved
0.7101	Intermediate Similarity	NPD5844	Phase 1
0.7099	Intermediate Similarity	NPD2801	Approved
0.7097	Intermediate Similarity	NPD8166	Discontinued
0.7095	Intermediate Similarity	NPD7699	Phase 2
0.7095	Intermediate Similarity	NPD7700	Phase 2
0.7093	Intermediate Similarity	NPD8312	Approved
0.7093	Intermediate Similarity	NPD8313	Approved
0.7089	Intermediate Similarity	NPD1512	Approved
0.7083	Intermediate Similarity	NPD3972	Approved
0.7073	Intermediate Similarity	NPD7075	Discontinued
0.7063	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2796	Approved
0.7042	Intermediate Similarity	NPD1651	Approved
0.7041	Intermediate Similarity	NPD7177	Discontinued
0.7032	Intermediate Similarity	NPD2800	Approved
0.7029	Intermediate Similarity	NPD7635	Approved
0.7012	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD6020	Phase 2
0.6995	Remote Similarity	NPD7698	Approved
0.6995	Remote Similarity	NPD7435	Discontinued
0.6995	Remote Similarity	NPD7696	Phase 3
0.6995	Remote Similarity	NPD7697	Approved
0.6994	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3748	Approved
0.6988	Remote Similarity	NPD5494	Approved
0.6987	Remote Similarity	NPD4628	Phase 3
0.6986	Remote Similarity	NPD1876	Approved
0.6985	Remote Similarity	NPD9266	Approved
0.6985	Remote Similarity	NPD74	Approved
0.6981	Remote Similarity	NPD6273	Approved
0.6972	Remote Similarity	NPD9545	Approved
0.6966	Remote Similarity	NPD6213	Phase 3
0.6966	Remote Similarity	NPD6212	Phase 3
0.6966	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4878	Approved
0.6957	Remote Similarity	NPD7870	Phase 2
0.6957	Remote Similarity	NPD7871	Phase 2
0.6957	Remote Similarity	NPD8320	Phase 1
0.6957	Remote Similarity	NPD8319	Approved
0.6951	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.695	Remote Similarity	NPD9493	Approved
0.6948	Remote Similarity	NPD6099	Approved
0.6948	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD6166	Phase 2
0.6923	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6599	Discontinued
0.6912	Remote Similarity	NPD9264	Approved
0.6912	Remote Similarity	NPD9263	Approved
0.6912	Remote Similarity	NPD9267	Approved
0.6897	Remote Similarity	NPD1281	Approved
0.6887	Remote Similarity	NPD6663	Approved
0.6883	Remote Similarity	NPD4308	Phase 3
0.6879	Remote Similarity	NPD5029	Approved
0.6879	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5031	Approved
0.6879	Remote Similarity	NPD5027	Approved
0.6875	Remote Similarity	NPD4626	Approved
0.6875	Remote Similarity	NPD2286	Discontinued
0.6867	Remote Similarity	NPD7008	Discontinued
0.6867	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD9269	Phase 2
0.6848	Remote Similarity	NPD2296	Approved
0.6846	Remote Similarity	NPD5736	Approved
0.6845	Remote Similarity	NPD7701	Phase 2
0.6842	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1551	Phase 2
0.6835	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6801	Discontinued
0.6828	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1203	Approved
0.6821	Remote Similarity	NPD3268	Approved
0.6807	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD9268	Approved
0.6805	Remote Similarity	NPD5710	Approved
0.6805	Remote Similarity	NPD5711	Approved
0.6788	Remote Similarity	NPD1465	Phase 2
0.6784	Remote Similarity	NPD5033	Approved
0.6783	Remote Similarity	NPD7610	Discontinued
0.6782	Remote Similarity	NPD6559	Discontinued
0.6781	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7874	Approved
0.6772	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3020	Approved
0.6759	Remote Similarity	NPD4059	Approved
0.6757	Remote Similarity	NPD6823	Phase 2
0.6755	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4625	Phase 3
0.6753	Remote Similarity	NPD6651	Approved
0.675	Remote Similarity	NPD6799	Approved
0.6744	Remote Similarity	NPD3818	Discontinued
0.6744	Remote Similarity	NPD3751	Discontinued
0.6743	Remote Similarity	NPD5026	Approved
0.6743	Remote Similarity	NPD5034	Approved
0.6743	Remote Similarity	NPD5032	Approved
0.6743	Remote Similarity	NPD4955	Approved
0.6743	Remote Similarity	NPD36	Approved
0.6743	Remote Similarity	NPD5028	Approved
0.6743	Remote Similarity	NPD4954	Approved
0.6742	Remote Similarity	NPD288	Approved
0.6741	Remote Similarity	NPD1930	Approved
0.6741	Remote Similarity	NPD1929	Approved
0.6741	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7801	Approved
0.6736	Remote Similarity	NPD3091	Approved
0.6735	Remote Similarity	NPD1608	Approved
0.673	Remote Similarity	NPD6190	Approved
0.6724	Remote Similarity	NPD5953	Discontinued
0.672	Remote Similarity	NPD8151	Discontinued
0.6711	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD411	Approved
0.6709	Remote Similarity	NPD1243	Approved
0.6708	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5035	Approved
0.6705	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4750	Phase 3
0.6691	Remote Similarity	NPD3022	Approved
0.6691	Remote Similarity	NPD3021	Approved
0.669	Remote Similarity	NPD9281	Approved
0.6689	Remote Similarity	NPD3600	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