NPASS Compound

Structure

CID115458 OpenBabel06191715472D 26 28 0 0 0 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 1.7321 -2.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -5.1962 -2.0000 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 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 1.7321 0.0000 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 -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 -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 -1.7321 -0.0000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 -1.7321 1.0000 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 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 14 2 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 23 2 0 0 0 0 16 20 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 24 2 0 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.13
Volume:	366.326
LogP:	5.733
LogD:	3.566
LogS:	-6.224
# Rotatable Bonds:	4
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	2.573
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.984
MDCK Permeability:	1.7302016203757375e-05
Pgp-inhibitor:	0.117
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	100.68803405761719%
Volume Distribution (VD):	0.437
Pgp-substrate:	0.6032158732414246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.846
CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.677
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.716
CYP2C9-substrate:	0.437
CYP2D6-inhibitor:	0.301
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.305
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	3.239
Half-life (T1/2):	0.038

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.855
Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.84
Skin Sensitization:	0.308
Carcinogencity:	0.922
Eye Corrosion:	0.003
Eye Irritation:	0.934
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC115458

Natural Product ID:	NPC115458
*Common Name:**	Galvaquinone A
IUPAC Name:	1,8-dihydroxy-3-methyl-2-(4-methylpentanoyl)anthracene-9,10-dione
Synonyms:	Galvaquinone A
Standard InCHIKey:	OAWSKJJZFQTYDQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O5/c1-10(2)7-8-15(23)16-11(3)9-13-18(20(16)25)21(26)17-12(19(13)24)5-4-6-14(17)22/h4-6,9-10,22,25H,7-8H2,1-3H3
SMILES:	CC(CCC(=O)c1c(C)cc2c(c1O)C(=O)c1c(C2=O)cccc1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152647
PubChem CID:	71458451
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO12925	Streptomyces spinoverrucosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23057874]
NPO12925	Streptomyces spinoverrucosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26489038]

☑ 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

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2311	Cell Line	Calu-3	Homo sapiens	IC50	>	50000.0	nM	PMID[558802]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[558802]

☑ 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 NPC115458 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	356
0.1-0.2	1538
0.2-0.3	3298
0.3-0.4	9503
0.4-0.5	9969
0.5-0.6	5635
0.6-0.7	8248
0.7-0.8	3624
0.8-0.85	361
0.85-0.9	118
0.9-0.95	37
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC272268
0.9603	High Similarity	NPC282923
0.9457	High Similarity	NPC58685
0.9449	High Similarity	NPC48248
0.9389	High Similarity	NPC283088
0.938	High Similarity	NPC205992
0.9375	High Similarity	NPC99731
0.9365	High Similarity	NPC103540
0.9333	High Similarity	NPC193555
0.9328	High Similarity	NPC315578
0.9323	High Similarity	NPC13715
0.9313	High Similarity	NPC288089
0.9291	High Similarity	NPC3224
0.9286	High Similarity	NPC142956
0.9286	High Similarity	NPC173978
0.9254	High Similarity	NPC26924
0.9248	High Similarity	NPC245923
0.9242	High Similarity	NPC80035
0.9237	High Similarity	NPC53896
0.9225	High Similarity	NPC146647
0.9225	High Similarity	NPC34414
0.9206	High Similarity	NPC375356
0.9185	High Similarity	NPC181560
0.9185	High Similarity	NPC169452
0.9173	High Similarity	NPC474813
0.9167	High Similarity	NPC472262
0.9167	High Similarity	NPC287604
0.9167	High Similarity	NPC161964
0.916	High Similarity	NPC70622
0.9127	High Similarity	NPC300274
0.9111	High Similarity	NPC138099
0.9111	High Similarity	NPC242994
0.9091	High Similarity	NPC225051
0.9084	High Similarity	NPC17083
0.9044	High Similarity	NPC96421
0.9037	High Similarity	NPC4214
0.903	High Similarity	NPC193358
0.9008	High Similarity	NPC55949
0.9008	High Similarity	NPC136588
0.9008	High Similarity	NPC199253
0.8992	High Similarity	NPC96915
0.8976	High Similarity	NPC307174
0.8971	High Similarity	NPC1268
0.8963	High Similarity	NPC471905
0.8963	High Similarity	NPC53414
0.8963	High Similarity	NPC53206
0.8939	High Similarity	NPC244699
0.8939	High Similarity	NPC72669
0.8939	High Similarity	NPC474517
0.8913	High Similarity	NPC239136
0.8913	High Similarity	NPC19631
0.8905	High Similarity	NPC225243
0.8897	High Similarity	NPC416
0.8897	High Similarity	NPC61398
0.8889	High Similarity	NPC472308
0.8889	High Similarity	NPC155211
0.8889	High Similarity	NPC254847
0.8881	High Similarity	NPC50924
0.8864	High Similarity	NPC31799
0.8849	High Similarity	NPC471682
0.8846	High Similarity	NPC306765
0.8846	High Similarity	NPC231774
0.8841	High Similarity	NPC124365
0.8824	High Similarity	NPC305060
0.8815	High Similarity	NPC161632
0.8811	High Similarity	NPC315520
0.8806	High Similarity	NPC52407
0.8806	High Similarity	NPC314048
0.8777	High Similarity	NPC73061
0.8777	High Similarity	NPC135524
0.8777	High Similarity	NPC257644
0.875	High Similarity	NPC141934
0.875	High Similarity	NPC191976
0.8741	High Similarity	NPC166480
0.8741	High Similarity	NPC44437
0.8741	High Similarity	NPC12070
0.8741	High Similarity	NPC282780
0.874	High Similarity	NPC206778
0.874	High Similarity	NPC285829
0.8731	High Similarity	NPC246693
0.8731	High Similarity	NPC242358
0.8731	High Similarity	NPC110609
0.8723	High Similarity	NPC471683
0.8714	High Similarity	NPC66593
0.8712	High Similarity	NPC96024
0.8705	High Similarity	NPC305845
0.8705	High Similarity	NPC290550
0.8705	High Similarity	NPC246638
0.8705	High Similarity	NPC204045
0.8696	High Similarity	NPC143438
0.8676	High Similarity	NPC258502
0.8676	High Similarity	NPC249272
0.8667	High Similarity	NPC267205
0.8667	High Similarity	NPC114183
0.8667	High Similarity	NPC254603
0.8652	High Similarity	NPC21599
0.8652	High Similarity	NPC79627
0.8652	High Similarity	NPC193703
0.8647	High Similarity	NPC276238
0.8647	High Similarity	NPC25736
0.8647	High Similarity	NPC109123
0.8647	High Similarity	NPC278928
0.8636	High Similarity	NPC69424
0.8636	High Similarity	NPC176130
0.8636	High Similarity	NPC78364
0.8636	High Similarity	NPC84672
0.8636	High Similarity	NPC471530
0.8615	High Similarity	NPC275145
0.8613	High Similarity	NPC86524
0.8613	High Similarity	NPC474311
0.8603	High Similarity	NPC270899
0.8603	High Similarity	NPC1249
0.8593	High Similarity	NPC309430
0.8592	High Similarity	NPC34482
0.8582	High Similarity	NPC108129
0.8582	High Similarity	NPC475741
0.8582	High Similarity	NPC313047
0.8582	High Similarity	NPC474203
0.8582	High Similarity	NPC53016
0.8582	High Similarity	NPC295712
0.8582	High Similarity	NPC451542
0.8571	High Similarity	NPC477453
0.8571	High Similarity	NPC187843
0.8571	High Similarity	NPC477275
0.8561	High Similarity	NPC190457
0.8561	High Similarity	NPC162939
0.8561	High Similarity	NPC160499
0.8551	High Similarity	NPC475957
0.8551	High Similarity	NPC62272
0.8551	High Similarity	NPC53001
0.8551	High Similarity	NPC471452
0.855	High Similarity	NPC234890
0.855	High Similarity	NPC199273
0.855	High Similarity	NPC310540
0.855	High Similarity	NPC74507
0.855	High Similarity	NPC68756
0.855	High Similarity	NPC152525
0.8538	High Similarity	NPC91478
0.8531	High Similarity	NPC147250
0.8531	High Similarity	NPC314437
0.8531	High Similarity	NPC300540
0.8531	High Similarity	NPC470570
0.8529	High Similarity	NPC294226
0.8529	High Similarity	NPC477139
0.8521	High Similarity	NPC10764
0.8521	High Similarity	NPC471906
0.8521	High Similarity	NPC48762
0.8521	High Similarity	NPC244691
0.8519	High Similarity	NPC41847
0.8519	High Similarity	NPC93015
0.8519	High Similarity	NPC85342
0.8514	High Similarity	NPC474861
0.8511	High Similarity	NPC474300
0.8511	High Similarity	NPC69755
0.8511	High Similarity	NPC474961
0.85	High Similarity	NPC183345
0.8496	Intermediate Similarity	NPC72667
0.8492	Intermediate Similarity	NPC161304
0.8489	Intermediate Similarity	NPC87723
0.8478	Intermediate Similarity	NPC315275
0.8478	Intermediate Similarity	NPC118919
0.8472	Intermediate Similarity	NPC37709
0.8467	Intermediate Similarity	NPC202225
0.8462	Intermediate Similarity	NPC170055
0.8462	Intermediate Similarity	NPC12402
0.8462	Intermediate Similarity	NPC120545
0.8456	Intermediate Similarity	NPC175738
0.8451	Intermediate Similarity	NPC476473
0.8451	Intermediate Similarity	NPC293545
0.8451	Intermediate Similarity	NPC296752
0.8451	Intermediate Similarity	NPC174905
0.8444	Intermediate Similarity	NPC198305
0.8444	Intermediate Similarity	NPC31539
0.844	Intermediate Similarity	NPC91019
0.844	Intermediate Similarity	NPC106519
0.8429	Intermediate Similarity	NPC295339
0.8425	Intermediate Similarity	NPC205766
0.8425	Intermediate Similarity	NPC108288
0.8421	Intermediate Similarity	NPC1991
0.8421	Intermediate Similarity	NPC49647
0.8421	Intermediate Similarity	NPC295202
0.8421	Intermediate Similarity	NPC227741
0.8421	Intermediate Similarity	NPC254492
0.8421	Intermediate Similarity	NPC136342
0.8417	Intermediate Similarity	NPC147418
0.8409	Intermediate Similarity	NPC236189
0.8403	Intermediate Similarity	NPC143685
0.8403	Intermediate Similarity	NPC85393
0.8403	Intermediate Similarity	NPC285122
0.8403	Intermediate Similarity	NPC271944
0.8403	Intermediate Similarity	NPC110882
0.8397	Intermediate Similarity	NPC176208
0.8397	Intermediate Similarity	NPC282577
0.8392	Intermediate Similarity	NPC84568
0.8392	Intermediate Similarity	NPC218866
0.8392	Intermediate Similarity	NPC300684
0.8392	Intermediate Similarity	NPC48130
0.8382	Intermediate Similarity	NPC471851
0.838	Intermediate Similarity	NPC85310
0.838	Intermediate Similarity	NPC469520

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 NPC115458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	948
0.2-0.3	1291
0.3-0.4	2634
0.4-0.5	2257
0.5-0.6	1167
0.6-0.7	431
0.7-0.8	86
0.8-0.85	4
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9365	High Similarity	NPD1470	Approved
0.9048	High Similarity	NPD1201	Approved
0.8889	High Similarity	NPD1509	Clinical (unspecified phase)
0.8551	High Similarity	NPD5405	Approved
0.8551	High Similarity	NPD5404	Approved
0.8551	High Similarity	NPD5406	Approved
0.8551	High Similarity	NPD5408	Approved
0.8483	Intermediate Similarity	NPD3226	Approved
0.8425	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD7390	Discontinued
0.8207	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2346	Discontinued
0.7895	Intermediate Similarity	NPD3019	Approved
0.7832	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD3300	Phase 2
0.7801	Intermediate Similarity	NPD943	Approved
0.7761	Intermediate Similarity	NPD2932	Approved
0.7754	Intermediate Similarity	NPD2798	Approved
0.7736	Intermediate Similarity	NPD7473	Discontinued
0.771	Intermediate Similarity	NPD5951	Approved
0.7708	Intermediate Similarity	NPD2799	Discontinued
0.7681	Intermediate Similarity	NPD1164	Approved
0.766	Intermediate Similarity	NPD3764	Approved
0.7658	Intermediate Similarity	NPD6232	Discontinued
0.7655	Intermediate Similarity	NPD2935	Discontinued
0.7578	Intermediate Similarity	NPD2342	Discontinued
0.7568	Intermediate Similarity	NPD7003	Approved
0.7557	Intermediate Similarity	NPD7635	Approved
0.7535	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1607	Approved
0.7445	Intermediate Similarity	NPD3023	Approved
0.7445	Intermediate Similarity	NPD3026	Approved
0.7436	Intermediate Similarity	NPD7819	Suspended
0.7426	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3025	Approved
0.7426	Intermediate Similarity	NPD3024	Approved
0.7403	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6959	Discontinued
0.7372	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2344	Approved
0.7365	Intermediate Similarity	NPD1471	Phase 3
0.7347	Intermediate Similarity	NPD1510	Phase 2
0.731	Intermediate Similarity	NPD1240	Approved
0.7308	Intermediate Similarity	NPD7411	Suspended
0.7305	Intermediate Similarity	NPD8312	Approved
0.7305	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD8150	Discontinued
0.7255	Intermediate Similarity	NPD2533	Approved
0.7255	Intermediate Similarity	NPD2532	Approved
0.7255	Intermediate Similarity	NPD2534	Approved
0.7252	Intermediate Similarity	NPD9266	Approved
0.7252	Intermediate Similarity	NPD74	Approved
0.7234	Intermediate Similarity	NPD1283	Approved
0.7219	Intermediate Similarity	NPD3750	Approved
0.7215	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4878	Approved
0.7206	Intermediate Similarity	NPD9493	Approved
0.72	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4750	Phase 3
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7176	Intermediate Similarity	NPD9263	Approved
0.7176	Intermediate Similarity	NPD9267	Approved
0.7176	Intermediate Similarity	NPD9264	Approved
0.7174	Intermediate Similarity	NPD1651	Approved
0.7172	Intermediate Similarity	NPD3268	Approved
0.7171	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD288	Approved
0.7134	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7132	Intermediate Similarity	NPD1930	Approved
0.7132	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1929	Approved
0.7125	Intermediate Similarity	NPD7768	Phase 2
0.7123	Intermediate Similarity	NPD6663	Approved
0.7113	Intermediate Similarity	NPD1876	Approved
0.711	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8166	Discontinued
0.7103	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1549	Phase 2
0.7083	Intermediate Similarity	NPD5736	Approved
0.7081	Intermediate Similarity	NPD3749	Approved
0.7067	Intermediate Similarity	NPD6100	Approved
0.7067	Intermediate Similarity	NPD1551	Phase 2
0.7067	Intermediate Similarity	NPD6099	Approved
0.7063	Intermediate Similarity	NPD844	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7031	Intermediate Similarity	NPD3020	Approved
0.7021	Intermediate Similarity	NPD1281	Approved
0.7021	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6020	Phase 2
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2801	Approved
0.6992	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6273	Approved
0.6986	Remote Similarity	NPD4625	Phase 3
0.6986	Remote Similarity	NPD7008	Discontinued
0.6982	Remote Similarity	NPD5031	Approved
0.6982	Remote Similarity	NPD5029	Approved
0.6982	Remote Similarity	NPD5027	Approved
0.6978	Remote Similarity	NPD3091	Approved
0.6975	Remote Similarity	NPD7075	Discontinued
0.6972	Remote Similarity	NPD3972	Approved
0.6968	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2796	Approved
0.6946	Remote Similarity	NPD7177	Discontinued
0.6944	Remote Similarity	NPD2797	Approved
0.694	Remote Similarity	NPD3021	Approved
0.694	Remote Similarity	NPD3022	Approved
0.6939	Remote Similarity	NPD411	Approved
0.6937	Remote Similarity	NPD1934	Approved
0.6934	Remote Similarity	NPD9281	Approved
0.6932	Remote Similarity	NPD6535	Approved
0.6932	Remote Similarity	NPD6534	Approved
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1932	Approved
0.6917	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3882	Suspended
0.6905	Remote Similarity	NPD845	Approved
0.6905	Remote Similarity	NPD5844	Phase 1
0.6901	Remote Similarity	NPD3092	Approved
0.6899	Remote Similarity	NPD2066	Phase 3
0.6894	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5494	Approved
0.6887	Remote Similarity	NPD3748	Approved
0.6886	Remote Similarity	NPD5033	Approved
0.6883	Remote Similarity	NPD4628	Phase 3
0.6882	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD2286	Discontinued
0.6879	Remote Similarity	NPD1512	Approved
0.6879	Remote Similarity	NPD4059	Approved
0.6875	Remote Similarity	NPD6213	Phase 3
0.6875	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6212	Phase 3
0.687	Remote Similarity	NPD9261	Approved
0.6866	Remote Similarity	NPD2329	Discontinued
0.6853	Remote Similarity	NPD9717	Approved
0.6853	Remote Similarity	NPD1608	Approved
0.6846	Remote Similarity	NPD2979	Phase 3
0.6842	Remote Similarity	NPD36	Approved
0.6842	Remote Similarity	NPD4955	Approved
0.6842	Remote Similarity	NPD5026	Approved
0.6842	Remote Similarity	NPD5028	Approved
0.6842	Remote Similarity	NPD5034	Approved
0.6842	Remote Similarity	NPD4954	Approved
0.6833	Remote Similarity	NPD6781	Approved
0.6833	Remote Similarity	NPD6778	Approved
0.6833	Remote Similarity	NPD6780	Approved
0.6833	Remote Similarity	NPD6782	Approved
0.6833	Remote Similarity	NPD6777	Approved
0.6833	Remote Similarity	NPD6776	Approved
0.6833	Remote Similarity	NPD6779	Approved
0.6831	Remote Similarity	NPD4879	Approved
0.6828	Remote Similarity	NPD3267	Approved
0.6828	Remote Similarity	NPD3266	Approved
0.6828	Remote Similarity	NPD3094	Phase 2
0.6818	Remote Similarity	NPD2800	Approved
0.6818	Remote Similarity	NPD1237	Approved
0.6816	Remote Similarity	NPD7700	Phase 2
0.6816	Remote Similarity	NPD7699	Phase 2
0.6815	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6599	Discontinued
0.6812	Remote Similarity	NPD497	Approved
0.6809	Remote Similarity	NPD4093	Discontinued
0.6803	Remote Similarity	NPD6832	Phase 2
0.68	Remote Similarity	NPD447	Suspended
0.6797	Remote Similarity	NPD2860	Approved
0.6797	Remote Similarity	NPD2859	Approved
0.6795	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7610	Discontinued
0.6784	Remote Similarity	NPD5030	Phase 2
0.6782	Remote Similarity	NPD5038	Approved
0.6782	Remote Similarity	NPD5037	Approved
0.6776	Remote Similarity	NPD8320	Phase 1
0.6776	Remote Similarity	NPD8319	Approved
0.6765	Remote Similarity	NPD4956	Approved
0.6761	Remote Similarity	NPD3095	Discontinued
0.6755	Remote Similarity	NPD6651	Approved
0.6748	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5402	Approved
0.6746	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5032	Approved
0.6744	Remote Similarity	NPD3495	Discontinued
0.6739	Remote Similarity	NPD498	Approved
0.6739	Remote Similarity	NPD495	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