NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	3.523
LogD:	2.588
LogS:	-4.046
# Rotatable Bonds:	0
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	2.657
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.956
MDCK Permeability:	1.5325253116316162e-05
Pgp-inhibitor:	0.159
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	100.33358001708984%
Volume Distribution (VD):	0.339
Pgp-substrate:	1.1978358030319214%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.275
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.607
CYP2C9-substrate:	0.447
CYP2D6-inhibitor:	0.681
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.388
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	4.927
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.31
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.842
Rat Oral Acute Toxicity:	0.721
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.915
Carcinogencity:	0.886
Eye Corrosion:	0.009
Eye Irritation:	0.951
Respiratory Toxicity:	0.191

Download Data

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

Natural Product: NPC258502

Natural Product ID:	NPC258502
*Common Name:**	1,2-Dihydroxy-3-Methyl-Anthraquinone
IUPAC Name:	1,2-dihydroxy-3-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	QPAGCTACMMYJIO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O4/c1-7-6-10-11(15(19)12(7)16)14(18)9-5-3-2-4-8(9)13(10)17/h2-6,16,19H,1H3
SMILES:	Cc1cc2c(C(=O)c3ccccc3C2=O)c(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL190512
PubChem CID:	429241
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
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
Others	8

Activity Type	# Activity
NON-MOLECULAR	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT138	Organism	Brugia malayi	Brugia malayi	Mortality	=	5.0	%	PMID[559575]
NPT138	Organism	Brugia malayi	Brugia malayi	Mortality	=	6.0	%	PMID[559575]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Mortality	=	3.0	%	PMID[559575]
NPT138	Organism	Brugia malayi	Brugia malayi	Mortality	=	1.0	day	PMID[559575]
NPT138	Organism	Brugia malayi	Brugia malayi	Mortality	=	3.0	day	PMID[559575]
NPT138	Organism	Brugia malayi	Brugia malayi	Mortality	=	4.0	day	PMID[559575]
NPT138	Organism	Brugia malayi	Brugia malayi	Mortality	=	5.0	day	PMID[559575]
NPT138	Organism	Brugia malayi	Brugia malayi	Mortality	=	6.0	day	PMID[559575]

☑ 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 NPC258502 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	404
0.1-0.2	1777
0.2-0.3	4162
0.3-0.4	11263
0.4-0.5	7463
0.5-0.6	5584
0.6-0.7	7508
0.7-0.8	4105
0.8-0.85	303
0.85-0.9	114
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC416
0.9771	High Similarity	NPC61398
0.969	High Similarity	NPC294226
0.9308	High Similarity	NPC117609
0.9302	High Similarity	NPC234175
0.9254	High Similarity	NPC147418
0.9191	High Similarity	NPC203063
0.9141	High Similarity	NPC142956
0.9104	High Similarity	NPC153088
0.9098	High Similarity	NPC111845
0.9098	High Similarity	NPC52407
0.9084	High Similarity	NPC99731
0.903	High Similarity	NPC50924
0.9008	High Similarity	NPC282923
0.9	High Similarity	NPC160777
0.9	High Similarity	NPC73416
0.8993	High Similarity	NPC238629
0.8971	High Similarity	NPC53414
0.8971	High Similarity	NPC53206
0.8963	High Similarity	NPC80035
0.8955	High Similarity	NPC225051
0.8955	High Similarity	NPC138472
0.8915	High Similarity	NPC375356
0.8905	High Similarity	NPC13715
0.8905	High Similarity	NPC4214
0.8897	High Similarity	NPC254847
0.8889	High Similarity	NPC473201
0.8889	High Similarity	NPC302783
0.8889	High Similarity	NPC118427
0.8872	High Similarity	NPC136588
0.8872	High Similarity	NPC31799
0.8872	High Similarity	NPC199253
0.8864	High Similarity	NPC48248
0.8841	High Similarity	NPC138099
0.8841	High Similarity	NPC242994
0.8837	High Similarity	NPC300274
0.8837	High Similarity	NPC91478
0.8832	High Similarity	NPC471905
0.8832	High Similarity	NPC264022
0.8828	High Similarity	NPC164912
0.8824	High Similarity	NPC283088
0.8824	High Similarity	NPC72918
0.8815	High Similarity	NPC53896
0.8811	High Similarity	NPC471907
0.8806	High Similarity	NPC93015
0.8806	High Similarity	NPC205992
0.8806	High Similarity	NPC244699
0.8797	High Similarity	NPC34414
0.8797	High Similarity	NPC146647
0.8794	High Similarity	NPC79627
0.8779	High Similarity	NPC103540
0.8777	High Similarity	NPC471853
0.8777	High Similarity	NPC169452
0.8777	High Similarity	NPC181560
0.8768	High Similarity	NPC230811
0.8768	High Similarity	NPC206207
0.876	High Similarity	NPC120545
0.8759	High Similarity	NPC155211
0.8759	High Similarity	NPC144283
0.875	High Similarity	NPC44437
0.8741	High Similarity	NPC70622
0.8731	High Similarity	NPC55949
0.8712	High Similarity	NPC96915
0.8705	High Similarity	NPC143438
0.8702	High Similarity	NPC173978
0.8696	High Similarity	NPC290030
0.8692	High Similarity	NPC307174
0.869	High Similarity	NPC280295
0.8676	High Similarity	NPC115458
0.8676	High Similarity	NPC267205
0.8662	High Similarity	NPC244691
0.8652	High Similarity	NPC239136
0.8652	High Similarity	NPC193555
0.8652	High Similarity	NPC19631
0.8652	High Similarity	NPC248068
0.8647	High Similarity	NPC473787
0.8639	High Similarity	NPC107109
0.8633	High Similarity	NPC141368
0.8633	High Similarity	NPC123714
0.863	High Similarity	NPC35
0.8623	High Similarity	NPC315275
0.8623	High Similarity	NPC7464
0.8623	High Similarity	NPC264112
0.8623	High Similarity	NPC194764
0.8623	High Similarity	NPC65005
0.8613	High Similarity	NPC288089
0.8603	High Similarity	NPC58685
0.8603	High Similarity	NPC135801
0.8592	High Similarity	NPC66593
0.8591	High Similarity	NPC178976
0.8582	High Similarity	NPC246638
0.8582	High Similarity	NPC305845
0.8582	High Similarity	NPC96024
0.8582	High Similarity	NPC204045
0.8582	High Similarity	NPC84273
0.8571	High Similarity	NPC3224
0.8571	High Similarity	NPC26924
0.8571	High Similarity	NPC472903
0.8571	High Similarity	NPC160499
0.8571	High Similarity	NPC149889
0.8571	High Similarity	NPC312338
0.8571	High Similarity	NPC190457
0.8561	High Similarity	NPC49911
0.8561	High Similarity	NPC277559
0.854	High Similarity	NPC314048
0.8531	High Similarity	NPC21599
0.8531	High Similarity	NPC193703
0.8529	High Similarity	NPC474517
0.8529	High Similarity	NPC34070
0.8529	High Similarity	NPC469526
0.8529	High Similarity	NPC72669
0.8523	High Similarity	NPC5379
0.8523	High Similarity	NPC14561
0.8523	High Similarity	NPC77807
0.8521	High Similarity	NPC73061
0.8521	High Similarity	NPC135524
0.8521	High Similarity	NPC11314
0.8519	High Similarity	NPC276238
0.8511	High Similarity	NPC315578
0.8507	High Similarity	NPC69424
0.8507	High Similarity	NPC78364
0.8507	High Similarity	NPC84672
0.8507	High Similarity	NPC176130
0.8507	High Similarity	NPC324209
0.85	High Similarity	NPC42384
0.85	High Similarity	NPC46242
0.85	High Similarity	NPC5014
0.85	High Similarity	NPC165191
0.85	High Similarity	NPC473479
0.85	High Similarity	NPC91887
0.85	High Similarity	NPC157284
0.85	High Similarity	NPC28592
0.85	High Similarity	NPC50615
0.85	High Similarity	NPC473779
0.85	High Similarity	NPC469857
0.85	High Similarity	NPC477849
0.85	High Similarity	NPC149773
0.85	High Similarity	NPC23667
0.85	High Similarity	NPC297797
0.85	High Similarity	NPC51531
0.85	High Similarity	NPC245760
0.85	High Similarity	NPC289358
0.85	High Similarity	NPC114333
0.8489	Intermediate Similarity	NPC272268
0.8489	Intermediate Similarity	NPC191976
0.8489	Intermediate Similarity	NPC474813
0.8483	Intermediate Similarity	NPC10842
0.8478	Intermediate Similarity	NPC166480
0.8478	Intermediate Similarity	NPC282780
0.8472	Intermediate Similarity	NPC68441
0.8467	Intermediate Similarity	NPC199463
0.8467	Intermediate Similarity	NPC37543
0.8462	Intermediate Similarity	NPC285829
0.8462	Intermediate Similarity	NPC206778
0.8462	Intermediate Similarity	NPC199936
0.8456	Intermediate Similarity	NPC108129
0.8456	Intermediate Similarity	NPC233056
0.8456	Intermediate Similarity	NPC26697
0.8451	Intermediate Similarity	NPC290550
0.8451	Intermediate Similarity	NPC472904
0.844	Intermediate Similarity	NPC223336
0.844	Intermediate Similarity	NPC294330
0.8433	Intermediate Similarity	NPC231774
0.8433	Intermediate Similarity	NPC254492
0.8429	Intermediate Similarity	NPC245923
0.8421	Intermediate Similarity	NPC311740
0.8421	Intermediate Similarity	NPC199273
0.8421	Intermediate Similarity	NPC310540
0.8409	Intermediate Similarity	NPC282577
0.8406	Intermediate Similarity	NPC4170
0.8403	Intermediate Similarity	NPC309169
0.8403	Intermediate Similarity	NPC196941
0.8403	Intermediate Similarity	NPC471906
0.8403	Intermediate Similarity	NPC48762
0.84	Intermediate Similarity	NPC279605
0.8397	Intermediate Similarity	NPC472046
0.8394	Intermediate Similarity	NPC291001
0.8392	Intermediate Similarity	NPC192597
0.8392	Intermediate Similarity	NPC69755
0.8392	Intermediate Similarity	NPC141817
0.8392	Intermediate Similarity	NPC229218
0.8392	Intermediate Similarity	NPC176030
0.8392	Intermediate Similarity	NPC314271
0.8392	Intermediate Similarity	NPC291078
0.8392	Intermediate Similarity	NPC169214
0.838	Intermediate Similarity	NPC476534
0.838	Intermediate Similarity	NPC473527
0.838	Intermediate Similarity	NPC96421
0.8372	Intermediate Similarity	NPC150919
0.837	Intermediate Similarity	NPC72667
0.8369	Intermediate Similarity	NPC471974
0.8369	Intermediate Similarity	NPC469680
0.8369	Intermediate Similarity	NPC469681
0.8367	Intermediate Similarity	NPC37220
0.8357	Intermediate Similarity	NPC223836
0.8357	Intermediate Similarity	NPC324929
0.8357	Intermediate Similarity	NPC474311
0.8356	Intermediate Similarity	NPC52692
0.8356	Intermediate Similarity	NPC58373
0.8355	Intermediate Similarity	NPC84571

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 NPC258502 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	972
0.2-0.3	1478
0.3-0.4	2864
0.4-0.5	2000
0.5-0.6	1020
0.6-0.7	359
0.7-0.8	60
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8897	High Similarity	NPD1509	Clinical (unspecified phase)
0.8779	High Similarity	NPD1470	Approved
0.8603	High Similarity	NPD943	Approved
0.8473	Intermediate Similarity	NPD1201	Approved
0.8472	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD5405	Approved
0.8169	Intermediate Similarity	NPD5404	Approved
0.8169	Intermediate Similarity	NPD5408	Approved
0.8169	Intermediate Similarity	NPD5406	Approved
0.8154	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD7390	Discontinued
0.7898	Intermediate Similarity	NPD6232	Discontinued
0.7862	Intermediate Similarity	NPD2346	Discontinued
0.7862	Intermediate Similarity	NPD7473	Discontinued
0.7763	Intermediate Similarity	NPD3226	Approved
0.7698	Intermediate Similarity	NPD1164	Approved
0.7677	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1511	Approved
0.76	Intermediate Similarity	NPD3300	Phase 2
0.7574	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1512	Approved
0.7518	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD1934	Approved
0.7467	Intermediate Similarity	NPD8166	Discontinued
0.7466	Intermediate Similarity	NPD1607	Approved
0.7452	Intermediate Similarity	NPD2801	Approved
0.7432	Intermediate Similarity	NPD2935	Discontinued
0.7412	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2932	Approved
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7365	Intermediate Similarity	NPD2799	Discontinued
0.7358	Intermediate Similarity	NPD3882	Suspended
0.7357	Intermediate Similarity	NPD9269	Phase 2
0.7348	Intermediate Similarity	NPD3021	Approved
0.7348	Intermediate Similarity	NPD3022	Approved
0.7343	Intermediate Similarity	NPD9494	Approved
0.7333	Intermediate Similarity	NPD5951	Approved
0.7329	Intermediate Similarity	NPD1240	Approved
0.7328	Intermediate Similarity	NPD2342	Discontinued
0.731	Intermediate Similarity	NPD2313	Discontinued
0.731	Intermediate Similarity	NPD3764	Approved
0.7303	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7237	Intermediate Similarity	NPD7003	Approved
0.7233	Intermediate Similarity	NPD7819	Suspended
0.7197	Intermediate Similarity	NPD7458	Discontinued
0.7178	Intermediate Similarity	NPD6959	Discontinued
0.7162	Intermediate Similarity	NPD230	Phase 1
0.7161	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD2534	Approved
0.7161	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2533	Approved
0.7153	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD4380	Phase 2
0.7152	Intermediate Similarity	NPD6166	Phase 2
0.7152	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1283	Approved
0.7133	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7125	Intermediate Similarity	NPD1465	Phase 2
0.7105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1549	Phase 2
0.7093	Intermediate Similarity	NPD8150	Discontinued
0.7092	Intermediate Similarity	NPD3026	Approved
0.7092	Intermediate Similarity	NPD3023	Approved
0.7071	Intermediate Similarity	NPD3025	Approved
0.7071	Intermediate Similarity	NPD9268	Approved
0.7071	Intermediate Similarity	NPD1651	Approved
0.7071	Intermediate Similarity	NPD3024	Approved
0.7066	Intermediate Similarity	NPD3818	Discontinued
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7635	Approved
0.7047	Intermediate Similarity	NPD447	Suspended
0.7039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9266	Approved
0.7015	Intermediate Similarity	NPD74	Approved
0.7012	Intermediate Similarity	NPD5494	Approved
0.6994	Remote Similarity	NPD3749	Approved
0.6994	Remote Similarity	NPD7075	Discontinued
0.6993	Remote Similarity	NPD3972	Approved
0.6978	Remote Similarity	NPD9493	Approved
0.6975	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6190	Approved
0.6949	Remote Similarity	NPD6534	Approved
0.6949	Remote Similarity	NPD6535	Approved
0.694	Remote Similarity	NPD9264	Approved
0.694	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.694	Remote Similarity	NPD9263	Approved
0.694	Remote Similarity	NPD9267	Approved
0.6923	Remote Similarity	NPD1281	Approved
0.6914	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4628	Phase 3
0.6903	Remote Similarity	NPD3750	Approved
0.6897	Remote Similarity	NPD1876	Approved
0.6894	Remote Similarity	NPD7411	Suspended
0.6893	Remote Similarity	NPD6212	Phase 3
0.6893	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6213	Phase 3
0.6892	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7074	Phase 3
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4878	Approved
0.6871	Remote Similarity	NPD3817	Phase 2
0.6861	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1203	Approved
0.6839	Remote Similarity	NPD2800	Approved
0.6833	Remote Similarity	NPD7700	Phase 2
0.6833	Remote Similarity	NPD7699	Phase 2
0.6832	Remote Similarity	NPD6599	Discontinued
0.6824	Remote Similarity	NPD7054	Approved
0.6821	Remote Similarity	NPD8312	Approved
0.6821	Remote Similarity	NPD8313	Approved
0.6806	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD257	Approved
0.6803	Remote Similarity	NPD258	Approved
0.68	Remote Similarity	NPD6663	Approved
0.6788	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7472	Approved
0.6783	Remote Similarity	NPD2286	Discontinued
0.6783	Remote Similarity	NPD4626	Approved
0.6772	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD288	Approved
0.6768	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2296	Approved
0.6767	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1929	Approved
0.6767	Remote Similarity	NPD1930	Approved
0.6761	Remote Similarity	NPD9545	Approved
0.6758	Remote Similarity	NPD6778	Approved
0.6758	Remote Similarity	NPD6776	Approved
0.6758	Remote Similarity	NPD6781	Approved
0.6758	Remote Similarity	NPD6782	Approved
0.6758	Remote Similarity	NPD6780	Approved
0.6758	Remote Similarity	NPD6777	Approved
0.6758	Remote Similarity	NPD6779	Approved
0.6757	Remote Similarity	NPD5736	Approved
0.6753	Remote Similarity	NPD2796	Approved
0.6748	Remote Similarity	NPD6801	Discontinued
0.6746	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6797	Phase 2
0.6743	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD411	Approved
0.6727	Remote Similarity	NPD7768	Phase 2
0.6725	Remote Similarity	NPD1221	Approved
0.6725	Remote Similarity	NPD6020	Phase 2
0.6716	Remote Similarity	NPD1237	Approved
0.6714	Remote Similarity	NPD9281	Approved
0.671	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5027	Approved
0.6705	Remote Similarity	NPD5031	Approved
0.6705	Remote Similarity	NPD5029	Approved
0.6705	Remote Similarity	NPD7251	Discontinued
0.6705	Remote Similarity	NPD6559	Discontinued
0.6692	Remote Similarity	NPD1932	Approved
0.6692	Remote Similarity	NPD844	Approved
0.669	Remote Similarity	NPD3092	Approved
0.6688	Remote Similarity	NPD4308	Phase 3
0.6687	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6273	Approved
0.6686	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD5028	Approved
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD5026	Approved
0.6667	Remote Similarity	NPD36	Approved
0.6667	Remote Similarity	NPD5034	Approved
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD4955	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4954	Approved
0.6649	Remote Similarity	NPD7435	Discontinued
0.6647	Remote Similarity	NPD6234	Discontinued
0.6647	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD919	Approved
0.6646	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1551	Phase 2
0.6645	Remote Similarity	NPD4060	Phase 1
0.6644	Remote Similarity	NPD9717	Approved
0.6643	Remote Similarity	NPD3091	Approved
0.6643	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD9261	Approved
0.6629	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5710	Approved
0.6627	Remote Similarity	NPD5711	Approved
0.6622	Remote Similarity	NPD3094	Phase 2
0.6613	Remote Similarity	NPD8320	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