NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.09
Volume:	282.198
LogP:	3.478
LogD:	3.236
LogS:	-3.465
# Rotatable Bonds:	3
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	2.023
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.803
MDCK Permeability:	1.432002773071872e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.193
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	97.94617462158203%
Volume Distribution (VD):	0.669
Pgp-substrate:	1.2898690700531006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.779
CYP2C19-inhibitor:	0.971
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.759
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	5.834
Half-life (T1/2):	0.614

ADMET: Toxicity

hERG Blockers:	0.181
Human Hepatotoxicity (H-HT):	0.3
Drug-inuced Liver Injury (DILI):	0.556
AMES Toxicity:	0.625
Rat Oral Acute Toxicity:	0.629
Maximum Recommended Daily Dose:	0.653
Skin Sensitization:	0.893
Carcinogencity:	0.572
Eye Corrosion:	0.01
Eye Irritation:	0.959
Respiratory Toxicity:	0.077

Download Data

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

Natural Product: NPC7569

Natural Product ID:	NPC7569
*Common Name:**	6-Hydroxy-2-Phenethyl-Chromen-4-One
IUPAC Name:	6-hydroxy-2-(2-phenylethyl)chromen-4-one
Synonyms:
Standard InCHIKey:	QIYUDFMVCDXKBQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O3/c18-13-7-9-17-15(10-13)16(19)11-14(20-17)8-6-12-4-2-1-3-5-12/h1-5,7,9-11,18H,6,8H2
SMILES:	Oc1ccc2c(c1)c(=O)cc(o2)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL358544
PubChem CID:	5318315
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6956	Citrus limonia	Species	Rutaceae	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
ED50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	ED50	=	26.0	uM	PMID[559608]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	ED50	>	100.0	uM	PMID[559608]

☑ 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 NPC7569 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	428
0.1-0.2	1961
0.2-0.3	5216
0.3-0.4	12288
0.4-0.5	4980
0.5-0.6	5077
0.6-0.7	6707
0.7-0.8	5174
0.8-0.85	802
0.85-0.9	54
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.968	High Similarity	NPC278787
0.9603	High Similarity	NPC141549
0.944	High Similarity	NPC298884
0.92	High Similarity	NPC193805
0.912	High Similarity	NPC93730
0.9077	High Similarity	NPC118253
0.903	High Similarity	NPC18457
0.9024	High Similarity	NPC54243
0.8984	High Similarity	NPC22783
0.8947	High Similarity	NPC472881
0.8943	High Similarity	NPC32298
0.8897	High Similarity	NPC145673
0.8828	High Similarity	NPC224657
0.8779	High Similarity	NPC39753
0.8779	High Similarity	NPC115998
0.8777	High Similarity	NPC473951
0.8768	High Similarity	NPC159855
0.8768	High Similarity	NPC169479
0.875	High Similarity	NPC4012
0.872	High Similarity	NPC35744
0.8712	High Similarity	NPC137264
0.8702	High Similarity	NPC197425
0.8647	High Similarity	NPC474340
0.8623	High Similarity	NPC124365
0.8601	High Similarity	NPC101957
0.8601	High Similarity	NPC120105
0.8593	High Similarity	NPC22222
0.8593	High Similarity	NPC281513
0.8592	High Similarity	NPC118726
0.8592	High Similarity	NPC12367
0.8592	High Similarity	NPC186397
0.8592	High Similarity	NPC37135
0.8582	High Similarity	NPC301949
0.8582	High Similarity	NPC128216
0.8571	High Similarity	NPC201284
0.8571	High Similarity	NPC301717
0.856	High Similarity	NPC269414
0.855	High Similarity	NPC470841
0.855	High Similarity	NPC71525
0.8548	High Similarity	NPC240163
0.854	High Similarity	NPC228661
0.8538	High Similarity	NPC2771
0.8531	High Similarity	NPC223988
0.8531	High Similarity	NPC266499
0.8521	High Similarity	NPC46941
0.8521	High Similarity	NPC239312
0.8521	High Similarity	NPC130230
0.8521	High Similarity	NPC275772
0.8519	High Similarity	NPC57601
0.8516	High Similarity	NPC314329
0.8511	High Similarity	NPC47152
0.8507	High Similarity	NPC113006
0.8507	High Similarity	NPC472882
0.85	High Similarity	NPC1534
0.8473	Intermediate Similarity	NPC474264
0.8472	Intermediate Similarity	NPC184136
0.8472	Intermediate Similarity	NPC306821
0.8472	Intermediate Similarity	NPC45873
0.8467	Intermediate Similarity	NPC130976
0.8456	Intermediate Similarity	NPC172262
0.8456	Intermediate Similarity	NPC248872
0.8451	Intermediate Similarity	NPC60389
0.844	Intermediate Similarity	NPC306816
0.8421	Intermediate Similarity	NPC187907
0.8414	Intermediate Similarity	NPC226973
0.8414	Intermediate Similarity	NPC308451
0.8414	Intermediate Similarity	NPC208043
0.8406	Intermediate Similarity	NPC98395
0.8406	Intermediate Similarity	NPC299379
0.8406	Intermediate Similarity	NPC250266
0.8406	Intermediate Similarity	NPC266597
0.8403	Intermediate Similarity	NPC200221
0.8403	Intermediate Similarity	NPC259713
0.8403	Intermediate Similarity	NPC195351
0.8403	Intermediate Similarity	NPC294502
0.8403	Intermediate Similarity	NPC216318
0.8403	Intermediate Similarity	NPC296197
0.8403	Intermediate Similarity	NPC17286
0.8394	Intermediate Similarity	NPC77955
0.8394	Intermediate Similarity	NPC141934
0.8394	Intermediate Similarity	NPC324929
0.8382	Intermediate Similarity	NPC265793
0.8382	Intermediate Similarity	NPC78540
0.8382	Intermediate Similarity	NPC50898
0.8382	Intermediate Similarity	NPC213216
0.8382	Intermediate Similarity	NPC274121
0.838	Intermediate Similarity	NPC469764
0.838	Intermediate Similarity	NPC70136
0.8367	Intermediate Similarity	NPC256612
0.8367	Intermediate Similarity	NPC20830
0.8359	Intermediate Similarity	NPC470092
0.8357	Intermediate Similarity	NPC281207
0.8357	Intermediate Similarity	NPC269652
0.8356	Intermediate Similarity	NPC239128
0.8356	Intermediate Similarity	NPC187498
0.8356	Intermediate Similarity	NPC293183
0.8356	Intermediate Similarity	NPC71334
0.8356	Intermediate Similarity	NPC57030
0.8356	Intermediate Similarity	NPC301123
0.8356	Intermediate Similarity	NPC131624
0.8356	Intermediate Similarity	NPC222830
0.8356	Intermediate Similarity	NPC100887
0.8356	Intermediate Similarity	NPC83508
0.8356	Intermediate Similarity	NPC75069
0.8356	Intermediate Similarity	NPC198826
0.8356	Intermediate Similarity	NPC188203
0.8356	Intermediate Similarity	NPC301323
0.8356	Intermediate Similarity	NPC156222
0.8356	Intermediate Similarity	NPC212678
0.8356	Intermediate Similarity	NPC120163
0.8356	Intermediate Similarity	NPC162313
0.8356	Intermediate Similarity	NPC275836
0.8356	Intermediate Similarity	NPC241498
0.8356	Intermediate Similarity	NPC275722
0.8356	Intermediate Similarity	NPC256283
0.8356	Intermediate Similarity	NPC25270
0.8346	Intermediate Similarity	NPC125887
0.8346	Intermediate Similarity	NPC201419
0.8345	Intermediate Similarity	NPC37348
0.8345	Intermediate Similarity	NPC227122
0.8345	Intermediate Similarity	NPC77858
0.8345	Intermediate Similarity	NPC1268
0.8345	Intermediate Similarity	NPC295036
0.8333	Intermediate Similarity	NPC194281
0.8333	Intermediate Similarity	NPC194856
0.8333	Intermediate Similarity	NPC116775
0.8333	Intermediate Similarity	NPC281917
0.8333	Intermediate Similarity	NPC231772
0.8333	Intermediate Similarity	NPC13408
0.8333	Intermediate Similarity	NPC234133
0.8333	Intermediate Similarity	NPC187432
0.8333	Intermediate Similarity	NPC127447
0.8333	Intermediate Similarity	NPC29353
0.8333	Intermediate Similarity	NPC276930
0.8333	Intermediate Similarity	NPC47815
0.8333	Intermediate Similarity	NPC124784
0.8333	Intermediate Similarity	NPC96915
0.8333	Intermediate Similarity	NPC473887
0.8333	Intermediate Similarity	NPC256042
0.8333	Intermediate Similarity	NPC216361
0.8322	Intermediate Similarity	NPC300540
0.8322	Intermediate Similarity	NPC469758
0.8322	Intermediate Similarity	NPC308799
0.8322	Intermediate Similarity	NPC211565
0.8321	Intermediate Similarity	NPC298900
0.8321	Intermediate Similarity	NPC56332
0.831	Intermediate Similarity	NPC279121
0.831	Intermediate Similarity	NPC59551
0.8309	Intermediate Similarity	NPC287533
0.8308	Intermediate Similarity	NPC46634
0.8299	Intermediate Similarity	NPC255350
0.8299	Intermediate Similarity	NPC145379
0.8299	Intermediate Similarity	NPC178964
0.8299	Intermediate Similarity	NPC160951
0.8299	Intermediate Similarity	NPC472915
0.8299	Intermediate Similarity	NPC477691
0.8299	Intermediate Similarity	NPC47781
0.8299	Intermediate Similarity	NPC86485
0.8299	Intermediate Similarity	NPC69394
0.8299	Intermediate Similarity	NPC95842
0.8299	Intermediate Similarity	NPC280530
0.8299	Intermediate Similarity	NPC22519
0.8299	Intermediate Similarity	NPC280937
0.8299	Intermediate Similarity	NPC274327
0.8299	Intermediate Similarity	NPC176775
0.8299	Intermediate Similarity	NPC231018
0.8299	Intermediate Similarity	NPC183878
0.8298	Intermediate Similarity	NPC214919
0.8298	Intermediate Similarity	NPC136840
0.8298	Intermediate Similarity	NPC329493
0.8298	Intermediate Similarity	NPC124467
0.8296	Intermediate Similarity	NPC324488
0.8288	Intermediate Similarity	NPC225731
0.8288	Intermediate Similarity	NPC117579
0.8288	Intermediate Similarity	NPC251110
0.8288	Intermediate Similarity	NPC149614
0.8286	Intermediate Similarity	NPC143799
0.8286	Intermediate Similarity	NPC152042
0.8286	Intermediate Similarity	NPC241838
0.8286	Intermediate Similarity	NPC473499
0.8276	Intermediate Similarity	NPC328119
0.8276	Intermediate Similarity	NPC65775
0.8276	Intermediate Similarity	NPC10027
0.8273	Intermediate Similarity	NPC275055
0.8273	Intermediate Similarity	NPC212767
0.8273	Intermediate Similarity	NPC290291
0.8271	Intermediate Similarity	NPC45537
0.8271	Intermediate Similarity	NPC41721
0.8264	Intermediate Similarity	NPC168803
0.8264	Intermediate Similarity	NPC61284
0.8264	Intermediate Similarity	NPC207729
0.8264	Intermediate Similarity	NPC113428
0.8264	Intermediate Similarity	NPC12200
0.8264	Intermediate Similarity	NPC108406
0.8264	Intermediate Similarity	NPC74881
0.8264	Intermediate Similarity	NPC51443
0.8261	Intermediate Similarity	NPC64157
0.8261	Intermediate Similarity	NPC9985
0.8261	Intermediate Similarity	NPC278832
0.8261	Intermediate Similarity	NPC239495

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 NPC7569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	1011
0.2-0.3	1370
0.3-0.4	2685
0.4-0.5	1906
0.5-0.6	1207
0.6-0.7	398
0.7-0.8	126
0.8-0.85	16
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8923	High Similarity	NPD2313	Discontinued
0.854	High Similarity	NPD2346	Discontinued
0.8538	High Similarity	NPD1203	Approved
0.8516	High Similarity	NPD1547	Clinical (unspecified phase)
0.8473	Intermediate Similarity	NPD2798	Approved
0.8467	Intermediate Similarity	NPD2935	Discontinued
0.8406	Intermediate Similarity	NPD2344	Approved
0.831	Intermediate Similarity	NPD1511	Approved
0.8299	Intermediate Similarity	NPD2801	Approved
0.8261	Intermediate Similarity	NPD2799	Discontinued
0.8231	Intermediate Similarity	NPD6844	Discontinued
0.8194	Intermediate Similarity	NPD1512	Approved
0.8175	Intermediate Similarity	NPD447	Suspended
0.8169	Intermediate Similarity	NPD2309	Approved
0.8168	Intermediate Similarity	NPD9717	Approved
0.8151	Intermediate Similarity	NPD3226	Approved
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5402	Approved
0.8085	Intermediate Similarity	NPD1549	Phase 2
0.8047	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4308	Phase 3
0.7985	Intermediate Similarity	NPD2797	Approved
0.7985	Intermediate Similarity	NPD1470	Approved
0.7972	Intermediate Similarity	NPD3750	Approved
0.7971	Intermediate Similarity	NPD1240	Approved
0.7956	Intermediate Similarity	NPD411	Approved
0.7955	Intermediate Similarity	NPD1201	Approved
0.7943	Intermediate Similarity	NPD1551	Phase 2
0.7943	Intermediate Similarity	NPD2796	Approved
0.7941	Intermediate Similarity	NPD6832	Phase 2
0.7895	Intermediate Similarity	NPD1481	Phase 2
0.7877	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1934	Approved
0.7857	Intermediate Similarity	NPD1607	Approved
0.7829	Intermediate Similarity	NPD6671	Approved
0.7826	Intermediate Similarity	NPD3268	Approved
0.782	Intermediate Similarity	NPD1535	Discovery
0.7815	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD9493	Approved
0.7762	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4380	Phase 2
0.7724	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4307	Phase 2
0.7712	Intermediate Similarity	NPD3882	Suspended
0.768	Intermediate Similarity	NPD968	Approved
0.7674	Intermediate Similarity	NPD1241	Discontinued
0.7662	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1933	Approved
0.7655	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5403	Approved
0.7647	Intermediate Similarity	NPD3225	Approved
0.7635	Intermediate Similarity	NPD5401	Approved
0.763	Intermediate Similarity	NPD1608	Approved
0.7622	Intermediate Similarity	NPD3748	Approved
0.7612	Intermediate Similarity	NPD3496	Discontinued
0.761	Intermediate Similarity	NPD3818	Discontinued
0.7591	Intermediate Similarity	NPD3267	Approved
0.7591	Intermediate Similarity	NPD3266	Approved
0.7586	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7819	Suspended
0.7548	Intermediate Similarity	NPD3749	Approved
0.7536	Intermediate Similarity	NPD1019	Discontinued
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.7532	Intermediate Similarity	NPD2296	Approved
0.7517	Intermediate Similarity	NPD1471	Phase 3
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2861	Phase 2
0.7465	Intermediate Similarity	NPD943	Approved
0.7452	Intermediate Similarity	NPD5494	Approved
0.7451	Intermediate Similarity	NPD7411	Suspended
0.745	Intermediate Similarity	NPD6799	Approved
0.7447	Intermediate Similarity	NPD3764	Approved
0.7436	Intermediate Similarity	NPD7075	Discontinued
0.7434	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD9266	Approved
0.7422	Intermediate Similarity	NPD74	Approved
0.7419	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2800	Approved
0.7407	Intermediate Similarity	NPD17	Approved
0.74	Intermediate Similarity	NPD4662	Approved
0.74	Intermediate Similarity	NPD4661	Approved
0.7391	Intermediate Similarity	NPD1876	Approved
0.7388	Intermediate Similarity	NPD1894	Discontinued
0.7375	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6166	Phase 2
0.7375	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3972	Approved
0.7372	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7768	Phase 2
0.7357	Intermediate Similarity	NPD9494	Approved
0.7355	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7054	Approved
0.7344	Intermediate Similarity	NPD9267	Approved
0.7344	Intermediate Similarity	NPD9263	Approved
0.7344	Intermediate Similarity	NPD9264	Approved
0.7338	Intermediate Similarity	NPD1164	Approved
0.7329	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7323	Intermediate Similarity	NPD9697	Approved
0.7319	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7472	Approved
0.7297	Intermediate Similarity	NPD1243	Approved
0.7296	Intermediate Similarity	NPD6959	Discontinued
0.729	Intermediate Similarity	NPD6801	Discontinued
0.7285	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD7440	Discontinued
0.726	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7033	Discontinued
0.7259	Intermediate Similarity	NPD1548	Phase 1
0.7256	Intermediate Similarity	NPD6797	Phase 2
0.7255	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7003	Approved
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7237	Intermediate Similarity	NPD6273	Approved
0.7229	Intermediate Similarity	NPD8313	Approved
0.7229	Intermediate Similarity	NPD8312	Approved
0.7212	Intermediate Similarity	NPD6559	Discontinued
0.7212	Intermediate Similarity	NPD7251	Discontinued
0.7208	Intermediate Similarity	NPD2651	Approved
0.7208	Intermediate Similarity	NPD2649	Approved
0.7206	Intermediate Similarity	NPD5585	Approved
0.7203	Intermediate Similarity	NPD6798	Discontinued
0.72	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7074	Phase 3
0.719	Intermediate Similarity	NPD920	Approved
0.7188	Intermediate Similarity	NPD1247	Approved
0.7174	Intermediate Similarity	NPD1611	Approved
0.7174	Intermediate Similarity	NPD422	Phase 1
0.7172	Intermediate Similarity	NPD1184	Approved
0.7169	Intermediate Similarity	NPD7808	Phase 3
0.7161	Intermediate Similarity	NPD6599	Discontinued
0.716	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1778	Approved
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD1283	Approved
0.7134	Intermediate Similarity	NPD1465	Phase 2
0.7134	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9545	Approved
0.7117	Intermediate Similarity	NPD7473	Discontinued
0.7095	Intermediate Similarity	NPD5405	Approved
0.7095	Intermediate Similarity	NPD5404	Approved
0.7095	Intermediate Similarity	NPD5408	Approved
0.7095	Intermediate Similarity	NPD5406	Approved
0.7086	Intermediate Similarity	NPD2354	Approved
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1651	Approved
0.7073	Intermediate Similarity	NPD3751	Discontinued
0.707	Intermediate Similarity	NPD6279	Approved
0.707	Intermediate Similarity	NPD6280	Approved
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5536	Phase 2
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7059	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4622	Approved
0.7055	Intermediate Similarity	NPD4618	Approved
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD6585	Discontinued
0.705	Intermediate Similarity	NPD1610	Phase 2
0.7048	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3300	Phase 2
0.7031	Intermediate Similarity	NPD9261	Approved
0.703	Intermediate Similarity	NPD5844	Phase 1
0.7027	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7095	Approved
0.7014	Intermediate Similarity	NPD4625	Phase 3
0.7013	Intermediate Similarity	NPD5049	Phase 3
0.7006	Intermediate Similarity	NPD5890	Approved
0.7006	Intermediate Similarity	NPD5889	Approved
0.6993	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7458	Discontinued
0.6987	Remote Similarity	NPD3769	Discontinued
0.6986	Remote Similarity	NPD3140	Approved
0.6986	Remote Similarity	NPD4060	Phase 1
0.6986	Remote Similarity	NPD3142	Approved
0.6981	Remote Similarity	NPD4288	Approved
0.698	Remote Similarity	NPD6032	Approved
0.698	Remote Similarity	NPD4477	Approved
0.698	Remote Similarity	NPD1537	Approved
0.698	Remote Similarity	NPD1519	Approved
0.698	Remote Similarity	NPD4476	Approved
0.698	Remote Similarity	NPD1538	Phase 1
0.6963	Remote Similarity	NPD9281	Approved
0.6959	Remote Similarity	NPD5689	Approved
0.6959	Remote Similarity	NPD5688	Approved
0.695	Remote Similarity	NPD4359	Approved
0.695	Remote Similarity	NPD4749	Approved
0.6946	Remote Similarity	NPD5953	Discontinued
0.6946	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2614	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