NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	3.362
LogD:	2.203
LogS:	-3.922
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	2.423
Fsp3:	0.0
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:	-5.116
MDCK Permeability:	7.090899543982232e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.924
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	97.59788513183594%
Volume Distribution (VD):	0.409
Pgp-substrate:	3.8348159790039062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.419
CYP2C9-substrate:	0.382
CYP2D6-inhibitor:	0.562
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	4.298
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.647
AMES Toxicity:	0.576
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.944
Carcinogencity:	0.268
Eye Corrosion:	0.021
Eye Irritation:	0.949
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC136588

Natural Product ID:	NPC136588
*Common Name:**	Omega-Hydroxypachybasin
IUPAC Name:	1-hydroxy-3-(hydroxymethyl)anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	UZLMVCOKWZNITE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O4/c16-7-8-5-11-13(12(17)6-8)15(19)10-4-2-1-3-9(10)14(11)18/h1-6,16-17H,7H2
SMILES:	c1ccc2c(c1)C(=O)c1cc(cc(c1C2=O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229889
PubChem CID:	171106
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
NPO32651	trichoderma harzianum strain th-r16	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19650641]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	6

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	GI	=	47.3	%	PMID[552025]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	GI	=	41.5	%	PMID[552025]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	122800.0	nM	PMID[552025]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	=	11.0	mm	PMID[552025]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	20.0	mm	PMID[552025]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	<	10.0	mm	PMID[552025]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	<	10.0	mm	PMID[552025]

☑ 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 NPC136588 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	367
0.1-0.2	1635
0.2-0.3	3641
0.3-0.4	10096
0.4-0.5	9193
0.5-0.6	5710
0.6-0.7	8208
0.7-0.8	3377
0.8-0.85	304
0.85-0.9	135
0.9-0.95	26
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC199253
0.984	High Similarity	NPC70622
0.9762	High Similarity	NPC52407
0.968	High Similarity	NPC31799
0.9431	High Similarity	NPC375356
0.9365	High Similarity	NPC282923
0.936	High Similarity	NPC96915
0.9355	High Similarity	NPC142956
0.935	High Similarity	NPC300274
0.9297	High Similarity	NPC205992
0.9297	High Similarity	NPC93015
0.928	High Similarity	NPC103540
0.9231	High Similarity	NPC288089
0.9213	High Similarity	NPC48248
0.92	High Similarity	NPC152525
0.92	High Similarity	NPC68756
0.9173	High Similarity	NPC190457
0.9154	High Similarity	NPC225051
0.9154	High Similarity	NPC314048
0.9141	High Similarity	NPC99731
0.9141	High Similarity	NPC34414
0.9141	High Similarity	NPC146647
0.9091	High Similarity	NPC155211
0.907	High Similarity	NPC55949
0.9048	High Similarity	NPC173978
0.9048	High Similarity	NPC234890
0.9048	High Similarity	NPC74507
0.904	High Similarity	NPC307174
0.9023	High Similarity	NPC305060
0.9015	High Similarity	NPC80035
0.9008	High Similarity	NPC115458
0.8952	High Similarity	NPC473662
0.8952	High Similarity	NPC216297
0.8952	High Similarity	NPC7151
0.8947	High Similarity	NPC474813
0.8947	High Similarity	NPC272268
0.8939	High Similarity	NPC50924
0.8923	High Similarity	NPC198305
0.8906	High Similarity	NPC3224
0.8898	High Similarity	NPC310540
0.8897	High Similarity	NPC204045
0.8897	High Similarity	NPC305845
0.8889	High Similarity	NPC26924
0.8889	High Similarity	NPC91478
0.8881	High Similarity	NPC245923
0.8881	High Similarity	NPC53414
0.8881	High Similarity	NPC53206
0.8872	High Similarity	NPC258502
0.8872	High Similarity	NPC283088
0.8864	High Similarity	NPC53896
0.8864	High Similarity	NPC294226
0.8855	High Similarity	NPC244699
0.8849	High Similarity	NPC300540
0.8841	High Similarity	NPC471906
0.8841	High Similarity	NPC244691
0.8841	High Similarity	NPC79627
0.8832	High Similarity	NPC135524
0.8832	High Similarity	NPC73061
0.8824	High Similarity	NPC183345
0.8824	High Similarity	NPC315578
0.8815	High Similarity	NPC13715
0.8815	High Similarity	NPC4214
0.8815	High Similarity	NPC61398
0.8815	High Similarity	NPC416
0.881	High Similarity	NPC120545
0.8806	High Similarity	NPC254847
0.8806	High Similarity	NPC315275
0.88	High Similarity	NPC285829
0.88	High Similarity	NPC206778
0.8797	High Similarity	NPC202225
0.8797	High Similarity	NPC44437
0.879	High Similarity	NPC41567
0.8788	High Similarity	NPC110609
0.8788	High Similarity	NPC242358
0.8788	High Similarity	NPC58685
0.8788	High Similarity	NPC246693
0.8779	High Similarity	NPC31539
0.8769	High Similarity	NPC237225
0.876	High Similarity	NPC160499
0.876	High Similarity	NPC306765
0.876	High Similarity	NPC231774
0.8759	High Similarity	NPC124365
0.875	High Similarity	NPC138099
0.875	High Similarity	NPC143438
0.875	High Similarity	NPC1268
0.875	High Similarity	NPC242994
0.8741	High Similarity	NPC471905
0.8731	High Similarity	NPC161632
0.8714	High Similarity	NPC314437
0.8714	High Similarity	NPC147250
0.8712	High Similarity	NPC85342
0.8712	High Similarity	NPC471851
0.8705	High Similarity	NPC21599
0.8705	High Similarity	NPC193703
0.8702	High Similarity	NPC278928
0.8696	High Similarity	NPC69755
0.8696	High Similarity	NPC474961
0.8696	High Similarity	NPC469520
0.8696	High Similarity	NPC257644
0.8686	High Similarity	NPC169452
0.8686	High Similarity	NPC96421
0.8686	High Similarity	NPC181560
0.8676	High Similarity	NPC173980
0.8667	High Similarity	NPC141934
0.8652	High Similarity	NPC119767
0.8647	High Similarity	NPC309430
0.8643	High Similarity	NPC478019
0.8633	High Similarity	NPC471682
0.8633	High Similarity	NPC66593
0.8629	High Similarity	NPC108288
0.8626	High Similarity	NPC767
0.8626	High Similarity	NPC247250
0.8623	High Similarity	NPC290550
0.8615	High Similarity	NPC295202
0.8615	High Similarity	NPC51037
0.8615	High Similarity	NPC49647
0.8615	High Similarity	NPC136342
0.8615	High Similarity	NPC227741
0.8605	High Similarity	NPC236189
0.8603	High Similarity	NPC147418
0.8583	High Similarity	NPC472046
0.8582	High Similarity	NPC285122
0.8582	High Similarity	NPC171968
0.8582	High Similarity	NPC267205
0.8571	High Similarity	NPC48762
0.8571	High Similarity	NPC72669
0.8571	High Similarity	NPC218866
0.8571	High Similarity	NPC84568
0.8571	High Similarity	NPC474517
0.8571	High Similarity	NPC300684
0.8571	High Similarity	NPC48130
0.8571	High Similarity	NPC232178
0.8561	High Similarity	NPC19631
0.8561	High Similarity	NPC239136
0.8561	High Similarity	NPC193555
0.8561	High Similarity	NPC85310
0.8551	High Similarity	NPC225243
0.855	High Similarity	NPC471530
0.8548	High Similarity	NPC161304
0.8538	High Similarity	NPC131799
0.8537	High Similarity	NPC196673
0.8529	High Similarity	NPC472308
0.8529	High Similarity	NPC193358
0.8521	High Similarity	NPC478018
0.8519	High Similarity	NPC472262
0.8519	High Similarity	NPC161964
0.8519	High Similarity	NPC287604
0.8511	High Similarity	NPC170055
0.8511	High Similarity	NPC471683
0.8511	High Similarity	NPC34482
0.8496	Intermediate Similarity	NPC27659
0.8496	Intermediate Similarity	NPC108129
0.8496	Intermediate Similarity	NPC475741
0.8489	Intermediate Similarity	NPC246638
0.8489	Intermediate Similarity	NPC187843
0.8485	Intermediate Similarity	NPC96024
0.8485	Intermediate Similarity	NPC234175
0.8478	Intermediate Similarity	NPC103337
0.8478	Intermediate Similarity	NPC114620
0.8473	Intermediate Similarity	NPC472047
0.8473	Intermediate Similarity	NPC1991
0.8472	Intermediate Similarity	NPC290954
0.8472	Intermediate Similarity	NPC255641
0.8472	Intermediate Similarity	NPC147735
0.8467	Intermediate Similarity	NPC475957
0.8451	Intermediate Similarity	NPC470570
0.8444	Intermediate Similarity	NPC254603
0.8444	Intermediate Similarity	NPC78307
0.844	Intermediate Similarity	NPC29932
0.8433	Intermediate Similarity	NPC17083
0.8433	Intermediate Similarity	NPC41847
0.8429	Intermediate Similarity	NPC137649
0.8429	Intermediate Similarity	NPC474300
0.8425	Intermediate Similarity	NPC218870
0.8425	Intermediate Similarity	NPC470408
0.8425	Intermediate Similarity	NPC474824
0.8425	Intermediate Similarity	NPC182921
0.8421	Intermediate Similarity	NPC57552
0.8421	Intermediate Similarity	NPC276238
0.8417	Intermediate Similarity	NPC203063
0.8409	Intermediate Similarity	NPC176130
0.8409	Intermediate Similarity	NPC78364
0.8409	Intermediate Similarity	NPC69424
0.8409	Intermediate Similarity	NPC84672
0.8406	Intermediate Similarity	NPC206207
0.8394	Intermediate Similarity	NPC191976
0.8394	Intermediate Similarity	NPC474311
0.8394	Intermediate Similarity	NPC86524
0.8385	Intermediate Similarity	NPC275145
0.8382	Intermediate Similarity	NPC282780
0.8382	Intermediate Similarity	NPC1249
0.8382	Intermediate Similarity	NPC166480
0.8382	Intermediate Similarity	NPC12070
0.837	Intermediate Similarity	NPC17843
0.837	Intermediate Similarity	NPC477406
0.8369	Intermediate Similarity	NPC53016
0.8369	Intermediate Similarity	NPC238629
0.8369	Intermediate Similarity	NPC476473
0.8367	Intermediate Similarity	NPC266469
0.8358	Intermediate Similarity	NPC117609

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 NPC136588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	948
0.2-0.3	1360
0.3-0.4	2712
0.4-0.5	2134
0.5-0.6	1142
0.6-0.7	417
0.7-0.8	71
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.928	High Similarity	NPD1470	Approved
0.896	High Similarity	NPD1201	Approved
0.8806	High Similarity	NPD1509	Clinical (unspecified phase)
0.8629	High Similarity	NPD405	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD5405	Approved
0.8201	Intermediate Similarity	NPD5406	Approved
0.8201	Intermediate Similarity	NPD5404	Approved
0.8201	Intermediate Similarity	NPD5408	Approved
0.8151	Intermediate Similarity	NPD3226	Approved
0.8143	Intermediate Similarity	NPD2346	Discontinued
0.8056	Intermediate Similarity	NPD7390	Discontinued
0.8	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1164	Approved
0.7842	Intermediate Similarity	NPD943	Approved
0.774	Intermediate Similarity	NPD3300	Phase 2
0.7698	Intermediate Similarity	NPD2313	Discontinued
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7622	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1510	Phase 2
0.7619	Intermediate Similarity	NPD2342	Discontinued
0.758	Intermediate Similarity	NPD6232	Discontinued
0.755	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7473	Discontinued
0.7537	Intermediate Similarity	NPD3019	Approved
0.7483	Intermediate Similarity	NPD1607	Approved
0.7481	Intermediate Similarity	NPD5951	Approved
0.7447	Intermediate Similarity	NPD3764	Approved
0.7426	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD74	Approved
0.7422	Intermediate Similarity	NPD9266	Approved
0.741	Intermediate Similarity	NPD2798	Approved
0.7407	Intermediate Similarity	NPD2932	Approved
0.7405	Intermediate Similarity	NPD6959	Discontinued
0.7397	Intermediate Similarity	NPD2344	Approved
0.7386	Intermediate Similarity	NPD4380	Phase 2
0.7381	Intermediate Similarity	NPD1237	Approved
0.7379	Intermediate Similarity	NPD2799	Discontinued
0.7379	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9493	Approved
0.7365	Intermediate Similarity	NPD7003	Approved
0.7355	Intermediate Similarity	NPD7819	Suspended
0.7347	Intermediate Similarity	NPD1549	Phase 2
0.7344	Intermediate Similarity	NPD9267	Approved
0.7344	Intermediate Similarity	NPD9263	Approved
0.7344	Intermediate Similarity	NPD9264	Approved
0.7343	Intermediate Similarity	NPD1240	Approved
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8312	Approved
0.7328	Intermediate Similarity	NPD7635	Approved
0.7305	Intermediate Similarity	NPD8150	Discontinued
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2534	Approved
0.7285	Intermediate Similarity	NPD2532	Approved
0.7285	Intermediate Similarity	NPD2533	Approved
0.7279	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1471	Phase 3
0.7266	Intermediate Similarity	NPD1283	Approved
0.7244	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1203	Approved
0.7211	Intermediate Similarity	NPD1551	Phase 2
0.7208	Intermediate Similarity	NPD7458	Discontinued
0.7206	Intermediate Similarity	NPD1651	Approved
0.72	Intermediate Similarity	NPD2309	Approved
0.7181	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4878	Approved
0.7118	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1511	Approved
0.7101	Intermediate Similarity	NPD3026	Approved
0.7101	Intermediate Similarity	NPD3023	Approved
0.7093	Intermediate Similarity	NPD6213	Phase 3
0.7093	Intermediate Similarity	NPD6212	Phase 3
0.7093	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9281	Approved
0.7089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3024	Approved
0.708	Intermediate Similarity	NPD3025	Approved
0.707	Intermediate Similarity	NPD1934	Approved
0.7059	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6535	Approved
0.7052	Intermediate Similarity	NPD6534	Approved
0.705	Intermediate Similarity	NPD1281	Approved
0.7045	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD288	Approved
0.7034	Intermediate Similarity	NPD6663	Approved
0.7031	Intermediate Similarity	NPD9261	Approved
0.703	Intermediate Similarity	NPD5844	Phase 1
0.7029	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1876	Approved
0.702	Intermediate Similarity	NPD8166	Discontinued
0.702	Intermediate Similarity	NPD3750	Approved
0.7014	Intermediate Similarity	NPD7008	Discontinued
0.7013	Intermediate Similarity	NPD1512	Approved
0.7013	Intermediate Similarity	NPD6273	Approved
0.7007	Intermediate Similarity	NPD3091	Approved
0.7006	Intermediate Similarity	NPD7411	Suspended
0.7	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD3749	Approved
0.6993	Remote Similarity	NPD5736	Approved
0.6966	Remote Similarity	NPD411	Approved
0.6964	Remote Similarity	NPD5026	Approved
0.6964	Remote Similarity	NPD4955	Approved
0.6964	Remote Similarity	NPD36	Approved
0.6964	Remote Similarity	NPD4954	Approved
0.6964	Remote Similarity	NPD5034	Approved
0.6964	Remote Similarity	NPD5028	Approved
0.6963	Remote Similarity	NPD497	Approved
0.6962	Remote Similarity	NPD6844	Discontinued
0.696	Remote Similarity	NPD844	Approved
0.6953	Remote Similarity	NPD1932	Approved
0.6949	Remote Similarity	NPD6782	Approved
0.6949	Remote Similarity	NPD6778	Approved
0.6949	Remote Similarity	NPD6780	Approved
0.6949	Remote Similarity	NPD6776	Approved
0.6949	Remote Similarity	NPD6777	Approved
0.6949	Remote Similarity	NPD6779	Approved
0.6949	Remote Similarity	NPD6781	Approved
0.6947	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD447	Suspended
0.6937	Remote Similarity	NPD7768	Phase 2
0.6932	Remote Similarity	NPD7700	Phase 2
0.6932	Remote Similarity	NPD7699	Phase 2
0.6918	Remote Similarity	NPD520	Approved
0.6918	Remote Similarity	NPD2801	Approved
0.6913	Remote Similarity	NPD4308	Phase 3
0.6908	Remote Similarity	NPD4628	Phase 3
0.6906	Remote Similarity	NPD2286	Discontinued
0.6906	Remote Similarity	NPD4626	Approved
0.6905	Remote Similarity	NPD6559	Discontinued
0.6905	Remote Similarity	NPD5030	Phase 2
0.6899	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1930	Approved
0.6899	Remote Similarity	NPD1929	Approved
0.6894	Remote Similarity	NPD7075	Discontinued
0.6894	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD495	Approved
0.6889	Remote Similarity	NPD498	Approved
0.6889	Remote Similarity	NPD496	Approved
0.6884	Remote Similarity	NPD9545	Approved
0.6879	Remote Similarity	NPD9717	Approved
0.6875	Remote Similarity	NPD5402	Approved
0.6875	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2979	Phase 3
0.6867	Remote Similarity	NPD2796	Approved
0.6867	Remote Similarity	NPD3818	Discontinued
0.6867	Remote Similarity	NPD7177	Discontinued
0.6866	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3094	Phase 2
0.6848	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6166	Phase 2
0.6839	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7696	Phase 3
0.6833	Remote Similarity	NPD7435	Discontinued
0.6833	Remote Similarity	NPD7697	Approved
0.6833	Remote Similarity	NPD7698	Approved
0.6832	Remote Similarity	NPD3882	Suspended
0.6828	Remote Similarity	NPD6832	Phase 2
0.6813	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5494	Approved
0.6809	Remote Similarity	NPD3092	Approved
0.6802	Remote Similarity	NPD5037	Approved
0.6802	Remote Similarity	NPD5038	Approved
0.6797	Remote Similarity	NPD3400	Discontinued
0.6796	Remote Similarity	NPD7870	Phase 2
0.6796	Remote Similarity	NPD8320	Phase 1
0.6796	Remote Similarity	NPD8319	Approved
0.6796	Remote Similarity	NPD7871	Phase 2
0.6788	Remote Similarity	NPD3317	Approved
0.6786	Remote Similarity	NPD3095	Discontinued
0.6767	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3751	Discontinued
0.6765	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD9269	Phase 2
0.6759	Remote Similarity	NPD9494	Approved
0.6753	Remote Similarity	NPD6190	Approved
0.675	Remote Similarity	NPD6801	Discontinued
0.6744	Remote Similarity	NPD5036	Approved
0.6738	Remote Similarity	NPD4879	Approved
0.6735	Remote Similarity	NPD3268	Approved
0.6732	Remote Similarity	NPD2800	Approved
0.673	Remote Similarity	NPD6599	Discontinued
0.6728	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5711	Approved
0.6727	Remote Similarity	NPD5710	Approved
0.6718	Remote Similarity	NPD164	Approved
0.6714	Remote Similarity	NPD9268	Approved
0.6714	Remote Similarity	NPD5691	Approved
0.6713	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1755	Approved
0.6711	Remote Similarity	NPD230	Phase 1

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