NPASS Compound

Structure

NPC244691 OpenBabel07101718232D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 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 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 -3.4641 -3.0000 0.0000 C 0 0 2 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 -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 1.7321 0.0000 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 -3.4641 -2.0000 0.0000 C 0 0 2 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 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 2 7 2 0 0 0 0 2 9 1 0 0 0 0 3 7 1 0 0 0 0 3 11 2 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 1 1 1 0 0 0 6 15 1 0 0 0 0 6 18 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 15 22 1 1 0 0 0 16 23 2 0 0 0 0 17 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	317.359
LogP:	1.631
LogD:	0.992
LogS:	-3.747
# Rotatable Bonds:	2
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	3.42
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.802
MDCK Permeability:	3.6056967473996338e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.078
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.855
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	94.67478942871094%
Volume Distribution (VD):	0.5
Pgp-substrate:	8.962239265441895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.817
CYP1A2-substrate:	0.563
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.333
CYP2C9-substrate:	0.535
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	9.182
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.565
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.834
Skin Sensitization:	0.938
Carcinogencity:	0.025
Eye Corrosion:	0.004
Eye Irritation:	0.906
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC244691

Natural Product ID:	NPC244691
*Common Name:**	3-(1S,2R-Dihydroxypropyl)-1,6,8-Trihydroxyanthracene-9,10-Dione
IUPAC Name:	3-[(1S,2R)-1,2-dihydroxypropyl]-1,6,8-trihydroxyanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	BMKQPAJRQUUYGC-NPMWZIQKSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-6(18)15(22)7-2-9-13(11(20)3-7)17(24)14-10(16(9)23)4-8(19)5-12(14)21/h2-6,15,18-22H,1H3/t6-,15-/m1/s1
SMILES:	Oc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)[C@@H]([C@H](O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289788
PubChem CID:	38357209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO472	Penicillium restrictum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24911880]
NPO472	Penicillium restrictum	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4782	Individual Protein	Accessory gene regulator protein A	Staphylococcus aureus	IC50	=	26500.0	nM	PMID[511329]

☑ 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 NPC244691 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	1440
0.2-0.3	3449
0.3-0.4	8891
0.4-0.5	10353
0.5-0.6	4381
0.6-0.7	6339
0.7-0.8	6048
0.8-0.85	1121
0.85-0.9	255
0.9-0.95	44
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9781	High Similarity	NPC204045
0.9781	High Similarity	NPC305845
0.9712	High Similarity	NPC471906
0.971	High Similarity	NPC135524
0.9635	High Similarity	NPC190457
0.9568	High Similarity	NPC474961
0.9489	High Similarity	NPC471905
0.9433	High Similarity	NPC48762
0.9416	High Similarity	NPC254847
0.9366	High Similarity	NPC34482
0.9353	High Similarity	NPC242994
0.9353	High Similarity	NPC143438
0.9353	High Similarity	NPC138099
0.9348	High Similarity	NPC53206
0.9348	High Similarity	NPC53414
0.9301	High Similarity	NPC470570
0.9296	High Similarity	NPC21599
0.9296	High Similarity	NPC193703
0.9286	High Similarity	NPC169452
0.9286	High Similarity	NPC181560
0.922	High Similarity	NPC246638
0.9197	High Similarity	NPC267205
0.9178	High Similarity	NPC147735
0.9178	High Similarity	NPC280295
0.9155	High Similarity	NPC193555
0.9155	High Similarity	NPC73061
0.9137	High Similarity	NPC315275
0.9137	High Similarity	NPC191976
0.913	High Similarity	NPC44437
0.9116	High Similarity	NPC470569
0.9085	High Similarity	NPC290550
0.9058	High Similarity	NPC314048
0.9058	High Similarity	NPC52407
0.9048	High Similarity	NPC290954
0.9048	High Similarity	NPC470568
0.9048	High Similarity	NPC255641
0.9021	High Similarity	NPC137649
0.9014	High Similarity	NPC203063
0.8993	High Similarity	NPC472211
0.8993	High Similarity	NPC282780
0.8993	High Similarity	NPC166480
0.8986	High Similarity	NPC70622
0.898	High Similarity	NPC477221
0.8978	High Similarity	NPC147757
0.8973	High Similarity	NPC190648
0.8973	High Similarity	NPC290194
0.8973	High Similarity	NPC37709
0.8973	High Similarity	NPC126767
0.8973	High Similarity	NPC312929
0.8973	High Similarity	NPC289042
0.8973	High Similarity	NPC245584
0.8973	High Similarity	NPC118027
0.8973	High Similarity	NPC56433
0.8958	High Similarity	NPC238629
0.8951	High Similarity	NPC187843
0.8921	High Similarity	NPC40524
0.8921	High Similarity	NPC139074
0.8921	High Similarity	NPC213485
0.8919	High Similarity	NPC294646
0.8913	High Similarity	NPC93015
0.8912	High Similarity	NPC471907
0.8904	High Similarity	NPC136878
0.8873	High Similarity	NPC61398
0.8873	High Similarity	NPC416
0.8867	High Similarity	NPC107109
0.8849	High Similarity	NPC478190
0.8841	High Similarity	NPC199253
0.8841	High Similarity	NPC31799
0.8841	High Similarity	NPC136588
0.8819	High Similarity	NPC110810
0.88	High Similarity	NPC470340
0.88	High Similarity	NPC268992
0.88	High Similarity	NPC51824
0.88	High Similarity	NPC40356
0.88	High Similarity	NPC470337
0.88	High Similarity	NPC154683
0.88	High Similarity	NPC180944
0.88	High Similarity	NPC470338
0.88	High Similarity	NPC113608
0.8794	High Similarity	NPC61153
0.8794	High Similarity	NPC130899
0.8794	High Similarity	NPC283590
0.8794	High Similarity	NPC161632
0.8794	High Similarity	NPC70859
0.8777	High Similarity	NPC475042
0.8776	High Similarity	NPC285122
0.8768	High Similarity	NPC99731
0.8767	High Similarity	NPC79627
0.8767	High Similarity	NPC19896
0.8767	High Similarity	NPC227841
0.8759	High Similarity	NPC469520
0.8758	High Similarity	NPC324736
0.875	High Similarity	NPC183345
0.875	High Similarity	NPC14561
0.875	High Similarity	NPC5379
0.875	High Similarity	NPC77807
0.8742	High Similarity	NPC155686
0.8742	High Similarity	NPC470408
0.8742	High Similarity	NPC182921
0.8742	High Similarity	NPC474824
0.8742	High Similarity	NPC218870
0.8742	High Similarity	NPC208806
0.8741	High Similarity	NPC4214
0.8741	High Similarity	NPC13715
0.8733	High Similarity	NPC46882
0.8733	High Similarity	NPC132990
0.8732	High Similarity	NPC118919
0.8726	High Similarity	NPC105414
0.8726	High Similarity	NPC234497
0.8726	High Similarity	NPC324522
0.8726	High Similarity	NPC470341
0.8726	High Similarity	NPC472058
0.8723	High Similarity	NPC474519
0.8707	High Similarity	NPC170055
0.8705	High Similarity	NPC62219
0.8701	High Similarity	NPC84571
0.8701	High Similarity	NPC470810
0.8699	High Similarity	NPC451542
0.8699	High Similarity	NPC474203
0.8699	High Similarity	NPC295712
0.8699	High Similarity	NPC174905
0.8699	High Similarity	NPC293545
0.8699	High Similarity	NPC313047
0.8696	High Similarity	NPC282923
0.8693	High Similarity	NPC37543
0.8693	High Similarity	NPC199463
0.8693	High Similarity	NPC178976
0.8684	High Similarity	NPC68727
0.8681	High Similarity	NPC162939
0.8671	High Similarity	NPC305060
0.8671	High Similarity	NPC290030
0.8671	High Similarity	NPC53001
0.8667	High Similarity	NPC202595
0.8667	High Similarity	NPC225854
0.8662	High Similarity	NPC283088
0.8662	High Similarity	NPC258502
0.8649	High Similarity	NPC314437
0.8649	High Similarity	NPC300540
0.8649	High Similarity	NPC143685
0.8645	High Similarity	NPC311740
0.8643	High Similarity	NPC205992
0.8639	High Similarity	NPC300684
0.8639	High Similarity	NPC218866
0.8639	High Similarity	NPC29932
0.8639	High Similarity	NPC84568
0.8639	High Similarity	NPC48130
0.8639	High Similarity	NPC10764
0.8636	High Similarity	NPC470559
0.8633	High Similarity	NPC92624
0.863	High Similarity	NPC85310
0.8627	High Similarity	NPC474861
0.8621	High Similarity	NPC156872
0.8621	High Similarity	NPC471853
0.8618	High Similarity	NPC93552
0.8613	High Similarity	NPC10926
0.8611	High Similarity	NPC175552
0.8611	High Similarity	NPC87723
0.8609	High Similarity	NPC35
0.8608	High Similarity	NPC107009
0.8601	High Similarity	NPC65005
0.8601	High Similarity	NPC264112
0.8601	High Similarity	NPC194764
0.8599	High Similarity	NPC472057
0.8599	High Similarity	NPC472051
0.8592	High Similarity	NPC12070
0.8592	High Similarity	NPC474394
0.8592	High Similarity	NPC50924
0.8592	High Similarity	NPC202225
0.8591	High Similarity	NPC34802
0.8591	High Similarity	NPC166583
0.8591	High Similarity	NPC53362
0.8582	High Similarity	NPC175738
0.8582	High Similarity	NPC17843
0.8581	High Similarity	NPC49282
0.8581	High Similarity	NPC12402
0.8581	High Similarity	NPC478019
0.8571	High Similarity	NPC66593
0.8571	High Similarity	NPC259942
0.8571	High Similarity	NPC471682
0.8571	High Similarity	NPC167663
0.8562	High Similarity	NPC226656
0.8562	High Similarity	NPC111536
0.8562	High Similarity	NPC472904
0.8562	High Similarity	NPC106519
0.8562	High Similarity	NPC76128
0.8562	High Similarity	NPC66508
0.8562	High Similarity	NPC91019
0.8562	High Similarity	NPC30432
0.8562	High Similarity	NPC5029
0.8562	High Similarity	NPC271385
0.8561	High Similarity	NPC247250
0.8561	High Similarity	NPC767
0.8553	High Similarity	NPC149889
0.8553	High Similarity	NPC312338
0.8552	High Similarity	NPC26924
0.8552	High Similarity	NPC472903
0.8551	High Similarity	NPC8745
0.8543	High Similarity	NPC205766
0.8542	High Similarity	NPC170742
0.8542	High Similarity	NPC147418

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 NPC244691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	913
0.2-0.3	1643
0.3-0.4	2832
0.4-0.5	1967
0.5-0.6	999
0.6-0.7	338
0.7-0.8	110
0.8-0.85	12
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9416	High Similarity	NPD1509	Clinical (unspecified phase)
0.8767	High Similarity	NPD7390	Discontinued
0.8478	Intermediate Similarity	NPD1470	Approved
0.8451	Intermediate Similarity	NPD943	Approved
0.8239	Intermediate Similarity	NPD6232	Discontinued
0.8219	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7473	Discontinued
0.8188	Intermediate Similarity	NPD1201	Approved
0.8182	Intermediate Similarity	NPD4380	Phase 2
0.8176	Intermediate Similarity	NPD6959	Discontinued
0.8163	Intermediate Similarity	NPD5405	Approved
0.8163	Intermediate Similarity	NPD5404	Approved
0.8163	Intermediate Similarity	NPD5408	Approved
0.8163	Intermediate Similarity	NPD5406	Approved
0.8141	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2532	Approved
0.7974	Intermediate Similarity	NPD2534	Approved
0.7974	Intermediate Similarity	NPD2533	Approved
0.7973	Intermediate Similarity	NPD1510	Phase 2
0.7962	Intermediate Similarity	NPD1934	Approved
0.7959	Intermediate Similarity	NPD1607	Approved
0.7911	Intermediate Similarity	NPD7819	Suspended
0.7857	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1240	Approved
0.7815	Intermediate Similarity	NPD1549	Phase 2
0.7771	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.7764	Intermediate Similarity	NPD7075	Discontinued
0.775	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6166	Phase 2
0.7697	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2801	Approved
0.7688	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1511	Approved
0.7654	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6559	Discontinued
0.7628	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6801	Discontinued
0.7616	Intermediate Similarity	NPD8150	Discontinued
0.7605	Intermediate Similarity	NPD3818	Discontinued
0.7593	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3882	Suspended
0.758	Intermediate Similarity	NPD1512	Approved
0.7566	Intermediate Similarity	NPD2935	Discontinued
0.7566	Intermediate Similarity	NPD2796	Approved
0.7562	Intermediate Similarity	NPD7411	Suspended
0.7561	Intermediate Similarity	NPD5494	Approved
0.7557	Intermediate Similarity	NPD6535	Approved
0.7557	Intermediate Similarity	NPD6534	Approved
0.7533	Intermediate Similarity	NPD230	Phase 1
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD9269	Phase 2
0.7466	Intermediate Similarity	NPD1164	Approved
0.7456	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6778	Approved
0.7444	Intermediate Similarity	NPD6780	Approved
0.7444	Intermediate Similarity	NPD6776	Approved
0.7444	Intermediate Similarity	NPD6782	Approved
0.7444	Intermediate Similarity	NPD6779	Approved
0.7444	Intermediate Similarity	NPD6777	Approved
0.7444	Intermediate Similarity	NPD6781	Approved
0.7439	Intermediate Similarity	NPD3749	Approved
0.743	Intermediate Similarity	NPD7700	Phase 2
0.743	Intermediate Similarity	NPD7699	Phase 2
0.7419	Intermediate Similarity	NPD2800	Approved
0.7412	Intermediate Similarity	NPD7074	Phase 3
0.7405	Intermediate Similarity	NPD8151	Discontinued
0.7389	Intermediate Similarity	NPD3300	Phase 2
0.7381	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7768	Phase 2
0.7372	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD5710	Approved
0.7353	Intermediate Similarity	NPD7054	Approved
0.7343	Intermediate Similarity	NPD9268	Approved
0.7342	Intermediate Similarity	NPD6799	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7341	Intermediate Similarity	NPD8313	Approved
0.733	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7435	Discontinued
0.7317	Intermediate Similarity	NPD5402	Approved
0.7317	Intermediate Similarity	NPD3817	Phase 2
0.731	Intermediate Similarity	NPD7472	Approved
0.7303	Intermediate Similarity	NPD6212	Phase 3
0.7303	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6213	Phase 3
0.7301	Intermediate Similarity	NPD37	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7283	Intermediate Similarity	NPD8320	Phase 1
0.7283	Intermediate Similarity	NPD8319	Approved
0.7267	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6797	Phase 2
0.7261	Intermediate Similarity	NPD4628	Phase 3
0.7256	Intermediate Similarity	NPD1465	Phase 2
0.7228	Intermediate Similarity	NPD7696	Phase 3
0.7228	Intermediate Similarity	NPD7697	Approved
0.7228	Intermediate Similarity	NPD7698	Approved
0.7226	Intermediate Similarity	NPD1551	Phase 2
0.7225	Intermediate Similarity	NPD7251	Discontinued
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3764	Approved
0.7215	Intermediate Similarity	NPD6190	Approved
0.7197	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7871	Phase 2
0.7189	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD6234	Discontinued
0.7184	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7808	Phase 3
0.7179	Intermediate Similarity	NPD2344	Approved
0.7172	Intermediate Similarity	NPD3019	Approved
0.7169	Intermediate Similarity	NPD4966	Approved
0.7169	Intermediate Similarity	NPD4965	Approved
0.7169	Intermediate Similarity	NPD4967	Phase 2
0.7166	Intermediate Similarity	NPD7701	Phase 2
0.7151	Intermediate Similarity	NPD6020	Phase 2
0.7143	Intermediate Similarity	NPD6651	Approved
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD6100	Approved
0.7115	Intermediate Similarity	NPD6099	Approved
0.7114	Intermediate Similarity	NPD3094	Phase 2
0.7099	Intermediate Similarity	NPD5403	Approved
0.7099	Intermediate Similarity	NPD920	Approved
0.709	Intermediate Similarity	NPD7874	Approved
0.709	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5401	Approved
0.7081	Intermediate Similarity	NPD6823	Phase 2
0.7069	Intermediate Similarity	NPD5953	Discontinued
0.7055	Intermediate Similarity	NPD2932	Approved
0.7053	Intermediate Similarity	NPD7801	Approved
0.7051	Intermediate Similarity	NPD2799	Discontinued
0.7051	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3748	Approved
0.7044	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD4750	Phase 3
0.7	Intermediate Similarity	NPD1247	Approved
0.7	Intermediate Similarity	NPD2309	Approved
0.6994	Remote Similarity	NPD7228	Approved
0.6993	Remote Similarity	NPD2313	Discontinued
0.6989	Remote Similarity	NPD5034	Approved
0.6989	Remote Similarity	NPD5028	Approved
0.6989	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4955	Approved
0.6989	Remote Similarity	NPD4954	Approved
0.6989	Remote Similarity	NPD5026	Approved
0.6989	Remote Similarity	NPD36	Approved
0.6981	Remote Similarity	NPD1243	Approved
0.6975	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3787	Discontinued
0.6959	Remote Similarity	NPD3092	Approved
0.6954	Remote Similarity	NPD7286	Phase 2
0.6949	Remote Similarity	NPD5035	Approved
0.6937	Remote Similarity	NPD8166	Discontinued
0.6937	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5030	Phase 2
0.6931	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8434	Phase 2
0.6927	Remote Similarity	NPD5037	Approved
0.6927	Remote Similarity	NPD5038	Approved
0.6919	Remote Similarity	NPD3926	Phase 2
0.6897	Remote Similarity	NPD9493	Approved
0.689	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD919	Approved
0.6875	Remote Similarity	NPD5951	Approved
0.6875	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7783	Phase 2
0.6872	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5036	Approved
0.6871	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7229	Phase 3
0.6857	Remote Similarity	NPD2342	Discontinued
0.6855	Remote Similarity	NPD1471	Phase 3
0.6852	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2798	Approved
0.6839	Remote Similarity	NPD6663	Approved
0.6832	Remote Similarity	NPD3400	Discontinued
0.6831	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6273	Approved
0.6821	Remote Similarity	NPD1283	Approved
0.6818	Remote Similarity	NPD4625	Phase 3
0.6818	Remote Similarity	NPD3027	Phase 3
0.6811	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD9266	Approved
0.6809	Remote Similarity	NPD74	Approved
0.6803	Remote Similarity	NPD9545	Approved
0.6803	Remote Similarity	NPD3091	Approved
0.6802	Remote Similarity	NPD7199	Phase 2
0.68	Remote Similarity	NPD3972	Approved
0.6797	Remote Similarity	NPD5736	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