NPASS Compound

Structure

NPC291802 OpenBabel07101718282D 22 24 0 0 0 0 0 0 0 0999 V2000 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 22 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	2.509
LogD:	2.548
LogS:	-3.529
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	2.433
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.791
MDCK Permeability:	9.001604666991625e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.955
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.771

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	96.09049224853516%
Volume Distribution (VD):	0.427
Pgp-substrate:	4.043088912963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.395
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.576
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.795
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.78
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	9.124
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.764
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.763
Skin Sensitization:	0.902
Carcinogencity:	0.18
Eye Corrosion:	0.009
Eye Irritation:	0.941
Respiratory Toxicity:	0.143

Download Data

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

Natural Product: NPC291802

Natural Product ID:	NPC291802
*Common Name:**	Khrinone A
IUPAC Name:	3-(2,5-dihydroxy-4-methoxyphenyl)-7-hydroxychromen-4-one
Synonyms:
Standard InCHIKey:	MPBPGCHGTKVWMR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-21-15-6-12(18)10(5-13(15)19)11-7-22-14-4-8(17)2-3-9(14)16(11)20/h2-7,17-19H,1H3
SMILES:	COc1cc(c(cc1O)c1coc2cc(ccc2c1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080370
PubChem CID:	44613666
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO14114	Dalbergia parviflora	Species	Fabaceae	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	8.4	uM	PMID[533990]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	5.6	uM	PMID[533990]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[533990]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[533990]

☑ 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 NPC291802 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	505
0.1-0.2	2060
0.2-0.3	5013
0.3-0.4	11594
0.4-0.5	5719
0.5-0.6	3921
0.6-0.7	5204
0.7-0.8	4967
0.8-0.85	1896
0.85-0.9	1067
0.9-0.95	626
0.95-1	125

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100263
1.0	High Similarity	NPC35763
1.0	High Similarity	NPC245382
1.0	High Similarity	NPC100971
1.0	High Similarity	NPC131266
1.0	High Similarity	NPC269451
1.0	High Similarity	NPC181209
1.0	High Similarity	NPC209487
1.0	High Similarity	NPC216769
1.0	High Similarity	NPC121522
0.9932	High Similarity	NPC124714
0.9931	High Similarity	NPC19980
0.9931	High Similarity	NPC45291
0.9864	High Similarity	NPC39184
0.9862	High Similarity	NPC10467
0.9862	High Similarity	NPC156953
0.9796	High Similarity	NPC250557
0.9795	High Similarity	NPC262623
0.9793	High Similarity	NPC40290
0.9793	High Similarity	NPC69430
0.9793	High Similarity	NPC200060
0.9793	High Similarity	NPC142876
0.9793	High Similarity	NPC195763
0.9793	High Similarity	NPC264289
0.9793	High Similarity	NPC139293
0.9793	High Similarity	NPC333691
0.9793	High Similarity	NPC264550
0.973	High Similarity	NPC134287
0.973	High Similarity	NPC130589
0.9726	High Similarity	NPC239363
0.9724	High Similarity	NPC194653
0.9724	High Similarity	NPC218490
0.9724	High Similarity	NPC139364
0.9724	High Similarity	NPC254702
0.9724	High Similarity	NPC80710
0.9724	High Similarity	NPC287395
0.9724	High Similarity	NPC183655
0.9724	High Similarity	NPC203747
0.9658	High Similarity	NPC92722
0.9658	High Similarity	NPC102003
0.9655	High Similarity	NPC125449
0.9655	High Similarity	NPC188074
0.96	High Similarity	NPC210084
0.96	High Similarity	NPC99597
0.96	High Similarity	NPC78103
0.9597	High Similarity	NPC20830
0.9597	High Similarity	NPC2928
0.9597	High Similarity	NPC213622
0.9597	High Similarity	NPC256612
0.9595	High Similarity	NPC198826
0.9595	High Similarity	NPC301323
0.9595	High Similarity	NPC100887
0.9595	High Similarity	NPC212678
0.9595	High Similarity	NPC222830
0.9595	High Similarity	NPC239128
0.9595	High Similarity	NPC131624
0.9595	High Similarity	NPC293183
0.9595	High Similarity	NPC25270
0.9595	High Similarity	NPC187498
0.9595	High Similarity	NPC256283
0.9595	High Similarity	NPC83508
0.9595	High Similarity	NPC241498
0.9595	High Similarity	NPC275722
0.9595	High Similarity	NPC162313
0.9595	High Similarity	NPC71334
0.9595	High Similarity	NPC156222
0.9595	High Similarity	NPC275836
0.9595	High Similarity	NPC188203
0.9595	High Similarity	NPC57030
0.9595	High Similarity	NPC120163
0.9589	High Similarity	NPC131451
0.9589	High Similarity	NPC15329
0.9586	High Similarity	NPC143903
0.9586	High Similarity	NPC12377
0.9586	High Similarity	NPC226987
0.9539	High Similarity	NPC260640
0.9539	High Similarity	NPC295009
0.9533	High Similarity	NPC472916
0.9533	High Similarity	NPC255106
0.9533	High Similarity	NPC235165
0.953	High Similarity	NPC271779
0.953	High Similarity	NPC255350
0.953	High Similarity	NPC167091
0.953	High Similarity	NPC274327
0.953	High Similarity	NPC145379
0.953	High Similarity	NPC69394
0.953	High Similarity	NPC160951
0.953	High Similarity	NPC176775
0.953	High Similarity	NPC183878
0.953	High Similarity	NPC47781
0.953	High Similarity	NPC280937
0.953	High Similarity	NPC88645
0.953	High Similarity	NPC22519
0.953	High Similarity	NPC231018
0.953	High Similarity	NPC206238
0.953	High Similarity	NPC292214
0.9527	High Similarity	NPC256406
0.9521	High Similarity	NPC119660
0.9521	High Similarity	NPC93034
0.9474	High Similarity	NPC225624
0.9474	High Similarity	NPC285973
0.9474	High Similarity	NPC476980
0.947	High Similarity	NPC472910
0.947	High Similarity	NPC472911
0.947	High Similarity	NPC156057
0.947	High Similarity	NPC475267
0.947	High Similarity	NPC472913
0.947	High Similarity	NPC472914
0.947	High Similarity	NPC474208
0.947	High Similarity	NPC470402
0.947	High Similarity	NPC474836
0.947	High Similarity	NPC162869
0.947	High Similarity	NPC96167
0.947	High Similarity	NPC245758
0.947	High Similarity	NPC222814
0.947	High Similarity	NPC48208
0.9467	High Similarity	NPC208197
0.9467	High Similarity	NPC201451
0.9467	High Similarity	NPC4455
0.9467	High Similarity	NPC2476
0.9467	High Similarity	NPC146165
0.9467	High Similarity	NPC138360
0.9467	High Similarity	NPC280339
0.9467	High Similarity	NPC92659
0.9467	High Similarity	NPC196439
0.9467	High Similarity	NPC183597
0.9467	High Similarity	NPC44079
0.9467	High Similarity	NPC26227
0.9467	High Similarity	NPC163780
0.9467	High Similarity	NPC50715
0.9467	High Similarity	NPC167815
0.9467	High Similarity	NPC227325
0.9467	High Similarity	NPC128863
0.9467	High Similarity	NPC201136
0.9463	High Similarity	NPC161277
0.9463	High Similarity	NPC142540
0.9463	High Similarity	NPC60972
0.9463	High Similarity	NPC199100
0.9463	High Similarity	NPC39732
0.9463	High Similarity	NPC180234
0.9463	High Similarity	NPC101996
0.9463	High Similarity	NPC39007
0.9463	High Similarity	NPC120537
0.9459	High Similarity	NPC45873
0.9459	High Similarity	NPC184136
0.9459	High Similarity	NPC306821
0.9452	High Similarity	NPC120924
0.9452	High Similarity	NPC216314
0.9452	High Similarity	NPC165389
0.9452	High Similarity	NPC195919
0.9448	High Similarity	NPC242893
0.9448	High Similarity	NPC142165
0.9448	High Similarity	NPC38065
0.9412	High Similarity	NPC308992
0.9412	High Similarity	NPC258331
0.9408	High Similarity	NPC215375
0.9408	High Similarity	NPC62518
0.9404	High Similarity	NPC49824
0.9404	High Similarity	NPC266960
0.9404	High Similarity	NPC247017
0.9404	High Similarity	NPC98661
0.9404	High Similarity	NPC245546
0.9404	High Similarity	NPC43243
0.94	High Similarity	NPC276409
0.94	High Similarity	NPC472915
0.94	High Similarity	NPC75279
0.94	High Similarity	NPC250822
0.9396	High Similarity	NPC308451
0.9396	High Similarity	NPC31363
0.9396	High Similarity	NPC208043
0.9396	High Similarity	NPC251110
0.9396	High Similarity	NPC226973
0.9396	High Similarity	NPC117579
0.9396	High Similarity	NPC171010
0.9396	High Similarity	NPC149614
0.9392	High Similarity	NPC183950
0.9392	High Similarity	NPC296197
0.9392	High Similarity	NPC216318
0.9392	High Similarity	NPC52005
0.9392	High Similarity	NPC287101
0.9392	High Similarity	NPC137062
0.9392	High Similarity	NPC38545
0.9392	High Similarity	NPC171916
0.9392	High Similarity	NPC259713
0.9392	High Similarity	NPC223579
0.9392	High Similarity	NPC17286
0.9379	High Similarity	NPC287722
0.9379	High Similarity	NPC254659
0.9351	High Similarity	NPC472448
0.9351	High Similarity	NPC261470
0.9351	High Similarity	NPC83922
0.9351	High Similarity	NPC81679
0.9346	High Similarity	NPC263449
0.9342	High Similarity	NPC176665
0.9342	High Similarity	NPC224137
0.9342	High Similarity	NPC469584
0.9342	High Similarity	NPC129684
0.9342	High Similarity	NPC305663
0.9342	High Similarity	NPC110070
0.9342	High Similarity	NPC78225

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 NPC291802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	476
0.1-0.2	1012
0.2-0.3	1943
0.3-0.4	2630
0.4-0.5	1690
0.5-0.6	914
0.6-0.7	331
0.7-0.8	107
0.8-0.85	25
0.85-0.9	16
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.953	High Similarity	NPD2801	Approved
0.9333	High Similarity	NPD1934	Approved
0.9054	High Similarity	NPD1511	Approved
0.9026	High Similarity	NPD3882	Suspended
0.902	High Similarity	NPD2393	Clinical (unspecified phase)
0.8933	High Similarity	NPD1512	Approved
0.8897	High Similarity	NPD1510	Phase 2
0.8875	High Similarity	NPD3818	Discontinued
0.875	High Similarity	NPD6167	Clinical (unspecified phase)
0.875	High Similarity	NPD6168	Clinical (unspecified phase)
0.875	High Similarity	NPD6166	Phase 2
0.8718	High Similarity	NPD3817	Phase 2
0.8701	High Similarity	NPD4380	Phase 2
0.8621	High Similarity	NPD1240	Approved
0.8621	High Similarity	NPD943	Approved
0.8616	High Similarity	NPD5494	Approved
0.8606	High Similarity	NPD4338	Clinical (unspecified phase)
0.8589	High Similarity	NPD7054	Approved
0.8544	High Similarity	NPD4868	Clinical (unspecified phase)
0.8537	High Similarity	NPD7472	Approved
0.8537	High Similarity	NPD7074	Phase 3
0.8509	High Similarity	NPD6232	Discontinued
0.8503	High Similarity	NPD1607	Approved
0.8497	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1549	Phase 2
0.8466	Intermediate Similarity	NPD7473	Discontinued
0.84	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD1247	Approved
0.8333	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD7251	Discontinued
0.8274	Intermediate Similarity	NPD7808	Phase 3
0.8261	Intermediate Similarity	NPD7075	Discontinued
0.825	Intermediate Similarity	NPD5402	Approved
0.8212	Intermediate Similarity	NPD2935	Discontinued
0.8194	Intermediate Similarity	NPD6799	Approved
0.8188	Intermediate Similarity	NPD230	Phase 1
0.8187	Intermediate Similarity	NPD1465	Phase 2
0.8187	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.8141	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6801	Discontinued
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7819	Suspended
0.8047	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3027	Phase 3
0.8038	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD9494	Approved
0.8026	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD919	Approved
0.795	Intermediate Similarity	NPD7411	Suspended
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD3926	Phase 2
0.7886	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD3750	Approved
0.7881	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1613	Approved
0.7852	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD447	Suspended
0.7812	Intermediate Similarity	NPD5403	Approved
0.7799	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD2534	Approved
0.7799	Intermediate Similarity	NPD5401	Approved
0.7799	Intermediate Similarity	NPD2532	Approved
0.7792	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7785	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6959	Discontinued
0.7755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7722	Intermediate Similarity	NPD6190	Approved
0.7711	Intermediate Similarity	NPD3749	Approved
0.7707	Intermediate Similarity	NPD2800	Approved
0.7702	Intermediate Similarity	NPD920	Approved
0.7665	Intermediate Similarity	NPD6234	Discontinued
0.7654	Intermediate Similarity	NPD1653	Approved
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD37	Approved
0.7568	Intermediate Similarity	NPD9269	Phase 2
0.7564	Intermediate Similarity	NPD3748	Approved
0.7558	Intermediate Similarity	NPD3751	Discontinued
0.7548	Intermediate Similarity	NPD6651	Approved
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7485	Intermediate Similarity	NPD5242	Approved
0.7484	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7483	Intermediate Similarity	NPD2798	Approved
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4965	Approved
0.744	Intermediate Similarity	NPD4966	Approved
0.744	Intermediate Similarity	NPD4967	Phase 2
0.7429	Intermediate Similarity	NPD5953	Discontinued
0.7414	Intermediate Similarity	NPD7286	Phase 2
0.7407	Intermediate Similarity	NPD7390	Discontinued
0.7391	Intermediate Similarity	NPD2309	Approved
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2346	Discontinued
0.7356	Intermediate Similarity	NPD7228	Approved
0.7345	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2799	Discontinued
0.7326	Intermediate Similarity	NPD3787	Discontinued
0.7312	Intermediate Similarity	NPD6777	Approved
0.7312	Intermediate Similarity	NPD6782	Approved
0.7312	Intermediate Similarity	NPD6780	Approved
0.7312	Intermediate Similarity	NPD6779	Approved
0.7312	Intermediate Similarity	NPD6776	Approved
0.7312	Intermediate Similarity	NPD6778	Approved
0.7312	Intermediate Similarity	NPD6781	Approved
0.7305	Intermediate Similarity	NPD6386	Approved
0.7305	Intermediate Similarity	NPD6385	Approved
0.7303	Intermediate Similarity	NPD1203	Approved
0.7303	Intermediate Similarity	NPD1470	Approved
0.7301	Intermediate Similarity	NPD4357	Discontinued
0.7297	Intermediate Similarity	NPD9268	Approved
0.7296	Intermediate Similarity	NPD6099	Approved
0.7296	Intermediate Similarity	NPD6100	Approved
0.7279	Intermediate Similarity	NPD5536	Phase 2
0.7278	Intermediate Similarity	NPD5353	Approved
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7225	Intermediate Similarity	NPD5710	Approved
0.7225	Intermediate Similarity	NPD5711	Approved
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7208	Intermediate Similarity	NPD2899	Discontinued
0.7196	Intermediate Similarity	NPD7435	Discontinued
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.7161	Intermediate Similarity	NPD6832	Phase 2
0.7161	Intermediate Similarity	NPD4908	Phase 1
0.716	Intermediate Similarity	NPD2654	Approved
0.7152	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD1610	Phase 2
0.7151	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7033	Discontinued
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7117	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9545	Approved
0.7111	Intermediate Similarity	NPD8313	Approved
0.7111	Intermediate Similarity	NPD8312	Approved
0.7105	Intermediate Similarity	NPD7696	Phase 3
0.7105	Intermediate Similarity	NPD3972	Approved
0.7105	Intermediate Similarity	NPD7698	Approved
0.7105	Intermediate Similarity	NPD9717	Approved
0.7105	Intermediate Similarity	NPD7697	Approved
0.7103	Intermediate Similarity	NPD228	Approved
0.7098	Intermediate Similarity	NPD8151	Discontinued
0.7095	Intermediate Similarity	NPD9493	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD3764	Approved
0.707	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7871	Phase 2
0.7068	Intermediate Similarity	NPD7870	Phase 2
0.7059	Intermediate Similarity	NPD2982	Phase 2
0.7059	Intermediate Similarity	NPD2983	Phase 2
0.7056	Intermediate Similarity	NPD7549	Discontinued
0.7053	Intermediate Similarity	NPD6823	Phase 2
0.7047	Intermediate Similarity	NPD7701	Phase 2
0.7043	Intermediate Similarity	NPD6534	Approved
0.7043	Intermediate Similarity	NPD4360	Phase 2
0.7043	Intermediate Similarity	NPD6535	Approved
0.7043	Intermediate Similarity	NPD4363	Phase 3
0.7039	Intermediate Similarity	NPD422	Phase 1
0.7037	Intermediate Similarity	NPD7266	Discontinued
0.7025	Intermediate Similarity	NPD6233	Phase 2
0.6995	Remote Similarity	NPD7584	Approved
0.6993	Remote Similarity	NPD1608	Approved
0.6993	Remote Similarity	NPD2981	Phase 2
0.6987	Remote Similarity	NPD2861	Phase 2
0.6977	Remote Similarity	NPD4288	Approved
0.6975	Remote Similarity	NPD5408	Approved
0.6975	Remote Similarity	NPD5404	Approved
0.6975	Remote Similarity	NPD5406	Approved
0.6975	Remote Similarity	NPD5405	Approved
0.6974	Remote Similarity	NPD7874	Approved
0.6974	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2797	Approved
0.6962	Remote Similarity	NPD6798	Discontinued
0.6962	Remote Similarity	NPD411	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