NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.05
Volume:	230.31
LogP:	3.586
LogD:	2.94
LogS:	-5.205
# Rotatable Bonds:	0
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.636
Synthetic Accessibility Score:	1.793
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.748
MDCK Permeability:	1.6158772268681787e-05
Pgp-inhibitor:	0.292
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	99.1343002319336%
Volume Distribution (VD):	0.662
Pgp-substrate:	1.382219672203064%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.489
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.619
CYP2C9-substrate:	0.541
CYP2D6-inhibitor:	0.466
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.516
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	4.304
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.871
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.118
Skin Sensitization:	0.315
Carcinogencity:	0.929
Eye Corrosion:	0.005
Eye Irritation:	0.987
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC300274

Natural Product ID:	NPC300274
*Common Name:**	1-Hydroxyanthraquinone
IUPAC Name:	1-hydroxyanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	BTLXPCBPYBNQNR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H8O3/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7,15H
SMILES:	c1ccc2c(c1)C(=O)c1cccc(c1C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501834
PubChem CID:	8512
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
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19674905]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[22784551]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[25068578]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32044231]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21919	Polysaccharidum versicolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21919	Polysaccharidum versicolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	>	800.0	ug.mL-1	PMID[489017]
NPT2	Others	Unspecified		logIC50	=	2.77	n.a.	PMID[489018]
NPT1365	Organism	Trichoplusia ni	Trichoplusia ni	mortality	=	10.0	%	PMID[489019]
NPT1365	Organism	Trichoplusia ni	Trichoplusia ni	FDI	=	-41.5	%	PMID[489019]

☑ 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 NPC300274 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	398
0.1-0.2	1783
0.2-0.3	4115
0.3-0.4	11288
0.4-0.5	7563
0.5-0.6	6709
0.6-0.7	7994
0.7-0.8	2440
0.8-0.85	274
0.85-0.9	94
0.9-0.95	34
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC375356
0.9746	High Similarity	NPC103540
0.9664	High Similarity	NPC96915
0.9661	High Similarity	NPC142956
0.9504	High Similarity	NPC282923
0.9426	High Similarity	NPC99731
0.9402	High Similarity	NPC285829
0.9402	High Similarity	NPC206778
0.935	High Similarity	NPC136588
0.935	High Similarity	NPC199253
0.9344	High Similarity	NPC48248
0.9339	High Similarity	NPC3224
0.9333	High Similarity	NPC173978
0.9328	High Similarity	NPC307174
0.9274	High Similarity	NPC205992
0.9268	High Similarity	NPC146647
0.9268	High Similarity	NPC34414
0.9244	High Similarity	NPC120545
0.9224	High Similarity	NPC108288
0.92	High Similarity	NPC70622
0.9194	High Similarity	NPC31799
0.9167	High Similarity	NPC91478
0.9127	High Similarity	NPC52407
0.9127	High Similarity	NPC225051
0.9127	High Similarity	NPC294226
0.9127	High Similarity	NPC115458
0.912	High Similarity	NPC244699
0.9055	High Similarity	NPC44437
0.9055	High Similarity	NPC288089
0.904	High Similarity	NPC55949
0.9024	High Similarity	NPC306765
0.9024	High Similarity	NPC231774
0.9016	High Similarity	NPC310540
0.9016	High Similarity	NPC234890
0.9016	High Similarity	NPC74507
0.8984	High Similarity	NPC283088
0.8984	High Similarity	NPC80035
0.8976	High Similarity	NPC53896
0.8974	High Similarity	NPC161304
0.8917	High Similarity	NPC473662
0.8917	High Similarity	NPC7151
0.8917	High Similarity	NPC216297
0.8915	High Similarity	NPC193358
0.8915	High Similarity	NPC474813
0.8915	High Similarity	NPC272268
0.8915	High Similarity	NPC141934
0.8915	High Similarity	NPC155211
0.8906	High Similarity	NPC50924
0.8898	High Similarity	NPC477453
0.8898	High Similarity	NPC58685
0.8871	High Similarity	NPC160499
0.8862	High Similarity	NPC152525
0.8862	High Similarity	NPC68756
0.8862	High Similarity	NPC236189
0.8846	High Similarity	NPC245923
0.8846	High Similarity	NPC53414
0.8846	High Similarity	NPC53206
0.8837	High Similarity	NPC258502
0.8833	High Similarity	NPC232178
0.8819	High Similarity	NPC72669
0.8819	High Similarity	NPC474517
0.8819	High Similarity	NPC93015
0.88	High Similarity	NPC471530
0.8779	High Similarity	NPC4214
0.8779	High Similarity	NPC61398
0.8779	High Similarity	NPC13715
0.8779	High Similarity	NPC416
0.8769	High Similarity	NPC254847
0.874	High Similarity	NPC31539
0.874	High Similarity	NPC475741
0.873	High Similarity	NPC237225
0.873	High Similarity	NPC234175
0.8712	High Similarity	NPC138099
0.8712	High Similarity	NPC1268
0.8712	High Similarity	NPC26924
0.8712	High Similarity	NPC242994
0.8702	High Similarity	NPC471905
0.8702	High Similarity	NPC147418
0.8699	High Similarity	NPC283514
0.8699	High Similarity	NPC244351
0.8692	High Similarity	NPC161632
0.8682	High Similarity	NPC171968
0.8682	High Similarity	NPC314048
0.8655	High Similarity	NPC240163
0.8647	High Similarity	NPC203063
0.8647	High Similarity	NPC169452
0.8647	High Similarity	NPC315578
0.8647	High Similarity	NPC181560
0.8647	High Similarity	NPC96421
0.8618	High Similarity	NPC198336
0.8615	High Similarity	NPC287604
0.8615	High Similarity	NPC161964
0.8615	High Similarity	NPC472262
0.8609	High Similarity	NPC141523
0.8605	High Similarity	NPC246693
0.8605	High Similarity	NPC110609
0.8605	High Similarity	NPC242358
0.8595	High Similarity	NPC41567
0.8594	High Similarity	NPC198305
0.8594	High Similarity	NPC117609
0.8583	High Similarity	NPC95537
0.8583	High Similarity	NPC96024
0.8582	High Similarity	NPC124365
0.8571	High Similarity	NPC51037
0.8571	High Similarity	NPC1991
0.8571	High Similarity	NPC190457
0.8571	High Similarity	NPC143438
0.8561	High Similarity	NPC305060
0.8538	High Similarity	NPC267205
0.8534	High Similarity	NPC224584
0.8525	High Similarity	NPC233165
0.8525	High Similarity	NPC184579
0.8519	High Similarity	NPC193555
0.8519	High Similarity	NPC257644
0.8519	High Similarity	NPC69755
0.8519	High Similarity	NPC73061
0.8519	High Similarity	NPC239136
0.8519	High Similarity	NPC19631
0.8516	High Similarity	NPC276238
0.8516	High Similarity	NPC278928
0.8516	High Similarity	NPC57552
0.8512	High Similarity	NPC125252
0.8512	High Similarity	NPC269414
0.8507	High Similarity	NPC225243
0.8504	High Similarity	NPC69424
0.8504	High Similarity	NPC84672
0.8504	High Similarity	NPC176130
0.8504	High Similarity	NPC78364
0.848	Intermediate Similarity	NPC135062
0.848	Intermediate Similarity	NPC275145
0.8473	Intermediate Similarity	NPC166480
0.8473	Intermediate Similarity	NPC282780
0.8462	Intermediate Similarity	NPC309430
0.8456	Intermediate Similarity	NPC66593
0.8456	Intermediate Similarity	NPC238629
0.8456	Intermediate Similarity	NPC471682
0.845	Intermediate Similarity	NPC108129
0.8448	Intermediate Similarity	NPC34715
0.8444	Intermediate Similarity	NPC305845
0.8444	Intermediate Similarity	NPC204045
0.8444	Intermediate Similarity	NPC290550
0.8444	Intermediate Similarity	NPC246638
0.8443	Intermediate Similarity	NPC184527
0.8438	Intermediate Similarity	NPC165257
0.8425	Intermediate Similarity	NPC8745
0.8425	Intermediate Similarity	NPC295202
0.8425	Intermediate Similarity	NPC227741
0.8425	Intermediate Similarity	NPC254492
0.8425	Intermediate Similarity	NPC49647
0.8425	Intermediate Similarity	NPC136342
0.8413	Intermediate Similarity	NPC164014
0.8413	Intermediate Similarity	NPC199273
0.8409	Intermediate Similarity	NPC22222
0.8409	Intermediate Similarity	NPC281513
0.84	Intermediate Similarity	NPC176208
0.84	Intermediate Similarity	NPC217756
0.84	Intermediate Similarity	NPC282577
0.8394	Intermediate Similarity	NPC21599
0.8394	Intermediate Similarity	NPC193703
0.8394	Intermediate Similarity	NPC79627
0.8387	Intermediate Similarity	NPC222876
0.8387	Intermediate Similarity	NPC179092
0.8387	Intermediate Similarity	NPC472046
0.8387	Intermediate Similarity	NPC272454
0.8387	Intermediate Similarity	NPC178395
0.8387	Intermediate Similarity	NPC115188
0.8387	Intermediate Similarity	NPC190971
0.8387	Intermediate Similarity	NPC159760
0.8387	Intermediate Similarity	NPC301987
0.8387	Intermediate Similarity	NPC35856
0.8387	Intermediate Similarity	NPC26433
0.8387	Intermediate Similarity	NPC292665
0.8387	Intermediate Similarity	NPC244994
0.8385	Intermediate Similarity	NPC85342
0.8385	Intermediate Similarity	NPC17083
0.8382	Intermediate Similarity	NPC474300
0.8382	Intermediate Similarity	NPC135524
0.8372	Intermediate Similarity	NPC25736
0.8372	Intermediate Similarity	NPC92624
0.837	Intermediate Similarity	NPC183345
0.8359	Intermediate Similarity	NPC72667
0.8358	Intermediate Similarity	NPC173980
0.8358	Intermediate Similarity	NPC61590
0.8346	Intermediate Similarity	NPC131799
0.8346	Intermediate Similarity	NPC472308
0.8346	Intermediate Similarity	NPC191976
0.8346	Intermediate Similarity	NPC10926
0.8346	Intermediate Similarity	NPC315275
0.8333	Intermediate Similarity	NPC1249
0.8333	Intermediate Similarity	NPC477153
0.8333	Intermediate Similarity	NPC471683
0.8333	Intermediate Similarity	NPC478019
0.8333	Intermediate Similarity	NPC12070
0.8333	Intermediate Similarity	NPC160777
0.8333	Intermediate Similarity	NPC182646
0.8333	Intermediate Similarity	NPC73416
0.8321	Intermediate Similarity	NPC476473
0.8309	Intermediate Similarity	NPC477275
0.8308	Intermediate Similarity	NPC27659
0.8308	Intermediate Similarity	NPC278787

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 NPC300274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	958
0.2-0.3	1270
0.3-0.4	2713
0.4-0.5	2179
0.5-0.6	1123
0.6-0.7	422
0.7-0.8	76
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9746	High Similarity	NPD1470	Approved
0.9573	High Similarity	NPD1201	Approved
0.9224	High Similarity	NPD405	Clinical (unspecified phase)
0.8769	High Similarity	NPD1509	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD5406	Approved
0.8284	Intermediate Similarity	NPD5405	Approved
0.8284	Intermediate Similarity	NPD5404	Approved
0.8284	Intermediate Similarity	NPD5408	Approved
0.8203	Intermediate Similarity	NPD1164	Approved
0.8088	Intermediate Similarity	NPD2346	Discontinued
0.8045	Intermediate Similarity	NPD943	Approved
0.8016	Intermediate Similarity	NPD3019	Approved
0.7972	Intermediate Similarity	NPD3226	Approved
0.7917	Intermediate Similarity	NPD74	Approved
0.7917	Intermediate Similarity	NPD9266	Approved
0.7874	Intermediate Similarity	NPD2932	Approved
0.7872	Intermediate Similarity	NPD7390	Discontinued
0.7863	Intermediate Similarity	NPD2798	Approved
0.7833	Intermediate Similarity	NPD9264	Approved
0.7833	Intermediate Similarity	NPD9267	Approved
0.7833	Intermediate Similarity	NPD9263	Approved
0.7833	Intermediate Similarity	NPD2342	Discontinued
0.7801	Intermediate Similarity	NPD3300	Phase 2
0.7761	Intermediate Similarity	NPD3764	Approved
0.7761	Intermediate Similarity	NPD2313	Discontinued
0.7698	Intermediate Similarity	NPD2344	Approved
0.7698	Intermediate Similarity	NPD9493	Approved
0.7692	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5951	Approved
0.7626	Intermediate Similarity	NPD2935	Discontinued
0.7615	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1510	Phase 2
0.7554	Intermediate Similarity	NPD2799	Discontinued
0.7536	Intermediate Similarity	NPD1607	Approved
0.7519	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1203	Approved
0.7518	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD9261	Approved
0.7483	Intermediate Similarity	NPD2309	Approved
0.7447	Intermediate Similarity	NPD1471	Phase 3
0.7438	Intermediate Similarity	NPD1237	Approved
0.7424	Intermediate Similarity	NPD4878	Approved
0.7413	Intermediate Similarity	NPD7003	Approved
0.7405	Intermediate Similarity	NPD3026	Approved
0.7405	Intermediate Similarity	NPD3023	Approved
0.7402	Intermediate Similarity	NPD9281	Approved
0.7385	Intermediate Similarity	NPD3024	Approved
0.7385	Intermediate Similarity	NPD3025	Approved
0.7381	Intermediate Similarity	NPD7635	Approved
0.7373	Intermediate Similarity	NPD288	Approved
0.7328	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1876	Approved
0.7313	Intermediate Similarity	NPD1283	Approved
0.7292	Intermediate Similarity	NPD3750	Approved
0.729	Intermediate Similarity	NPD6232	Discontinued
0.7288	Intermediate Similarity	NPD844	Approved
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7273	Intermediate Similarity	NPD1932	Approved
0.7261	Intermediate Similarity	NPD7473	Discontinued
0.7258	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1651	Approved
0.7248	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1930	Approved
0.7213	Intermediate Similarity	NPD1929	Approved
0.7213	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6663	Approved
0.719	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7819	Suspended
0.7165	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9717	Approved
0.7153	Intermediate Similarity	NPD5736	Approved
0.7153	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7122	Intermediate Similarity	NPD411	Approved
0.7107	Intermediate Similarity	NPD3020	Approved
0.7095	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD447	Suspended
0.709	Intermediate Similarity	NPD1281	Approved
0.7083	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2286	Discontinued
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7055	Intermediate Similarity	NPD8166	Discontinued
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1512	Approved
0.7047	Intermediate Similarity	NPD6273	Approved
0.7045	Intermediate Similarity	NPD3091	Approved
0.7037	Intermediate Similarity	NPD3972	Approved
0.7015	Intermediate Similarity	NPD4879	Approved
0.7007	Intermediate Similarity	NPD2797	Approved
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.7	Intermediate Similarity	NPD2860	Approved
0.7	Intermediate Similarity	NPD2859	Approved
0.6986	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1755	Approved
0.6975	Remote Similarity	NPD845	Approved
0.6974	Remote Similarity	NPD4380	Phase 2
0.6951	Remote Similarity	NPD8312	Approved
0.6951	Remote Similarity	NPD8313	Approved
0.695	Remote Similarity	NPD520	Approved
0.6948	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3748	Approved
0.694	Remote Similarity	NPD4626	Approved
0.694	Remote Similarity	NPD4059	Approved
0.6929	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7008	Discontinued
0.6929	Remote Similarity	NPD2329	Discontinued
0.6917	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9545	Approved
0.6917	Remote Similarity	NPD2933	Approved
0.6917	Remote Similarity	NPD2934	Approved
0.6912	Remote Similarity	NPD1608	Approved
0.6908	Remote Similarity	NPD7458	Discontinued
0.6903	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2296	Approved
0.6897	Remote Similarity	NPD2796	Approved
0.6883	Remote Similarity	NPD1934	Approved
0.6879	Remote Similarity	NPD3268	Approved
0.6875	Remote Similarity	NPD4750	Phase 3
0.6875	Remote Similarity	NPD3021	Approved
0.6875	Remote Similarity	NPD3022	Approved
0.687	Remote Similarity	NPD497	Approved
0.6867	Remote Similarity	NPD2533	Approved
0.6867	Remote Similarity	NPD2534	Approved
0.6867	Remote Similarity	NPD2532	Approved
0.6866	Remote Similarity	NPD4093	Discontinued
0.6864	Remote Similarity	NPD9258	Approved
0.6864	Remote Similarity	NPD9256	Approved
0.6859	Remote Similarity	NPD7768	Phase 2
0.6857	Remote Similarity	NPD6832	Phase 2
0.6853	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2801	Approved
0.6838	Remote Similarity	NPD3092	Approved
0.6833	Remote Similarity	NPD1202	Approved
0.6829	Remote Similarity	NPD2066	Phase 3
0.6826	Remote Similarity	NPD8150	Discontinued
0.6818	Remote Similarity	NPD7411	Suspended
0.6815	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD496	Approved
0.6794	Remote Similarity	NPD498	Approved
0.6794	Remote Similarity	NPD495	Approved
0.6788	Remote Similarity	NPD9269	Phase 2
0.6786	Remote Similarity	NPD9494	Approved
0.6783	Remote Similarity	NPD4307	Phase 2
0.6781	Remote Similarity	NPD6099	Approved
0.6781	Remote Similarity	NPD6100	Approved
0.6777	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1242	Phase 1
0.6774	Remote Similarity	NPD6844	Discontinued
0.6765	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3882	Suspended
0.6752	Remote Similarity	NPD650	Approved
0.6746	Remote Similarity	NPD164	Approved
0.6746	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1792	Phase 2
0.6741	Remote Similarity	NPD9268	Approved
0.6739	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5027	Approved
0.6727	Remote Similarity	NPD5031	Approved
0.6727	Remote Similarity	NPD5029	Approved
0.6721	Remote Similarity	NPD1809	Phase 2
0.6716	Remote Similarity	NPD7610	Discontinued
0.6713	Remote Similarity	NPD8032	Phase 2
0.6711	Remote Similarity	NPD1196	Approved
0.6711	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7075	Discontinued
0.6692	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD17	Approved
0.6691	Remote Similarity	NPD3095	Discontinued
0.669	Remote Similarity	NPD4625	Phase 3
0.6689	Remote Similarity	NPD1543	Discontinued
0.6688	Remote Similarity	NPD5402	Approved
0.6688	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD36	Approved
0.6687	Remote Similarity	NPD4954	Approved
0.6687	Remote Similarity	NPD5026	Approved
0.6687	Remote Similarity	NPD5034	Approved
0.6687	Remote Similarity	NPD5028	Approved
0.6687	Remote Similarity	NPD4955	Approved
0.6667	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7609	Phase 3
0.6667	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD1239	Approved
0.6646	Remote Similarity	NPD6020	Phase 2
0.6644	Remote Similarity	NPD2800	Approved
0.6644	Remote Similarity	NPD1195	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3094	Phase 2

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