NPASS Compound

Structure

NPC45291 OpenBabel07101718222D 23 25 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -1.7321 -0.0000 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 -2.5981 1.5000 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 -3.4641 1.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 7 2 0 0 0 0 2 12 1 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 9 2 0 0 0 0 6 23 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.06
Volume:	300.063
LogP:	2.158
LogD:	2.456
LogS:	-3.492
# Rotatable Bonds:	2
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	2.629
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:	-5.034
MDCK Permeability:	5.647457783197751e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.706
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.42
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	94.79930877685547%
Volume Distribution (VD):	0.545
Pgp-substrate:	5.80264949798584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.137
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.638
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.704
CYP2D6-substrate:	0.588
CYP3A4-inhibitor:	0.466
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	9.43
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.723
AMES Toxicity:	0.276
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.829
Skin Sensitization:	0.923
Carcinogencity:	0.034
Eye Corrosion:	0.019
Eye Irritation:	0.939
Respiratory Toxicity:	0.104

Download Data

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

Natural Product: NPC45291

Natural Product ID:	NPC45291
*Common Name:**	Khrinone B
IUPAC Name:	3-(2,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	HSMWTKNHVZRTCO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O7/c1-22-13-5-10(18)8(4-11(13)19)9-6-23-14-3-7(17)2-12(20)15(14)16(9)21/h2-6,17-20H,1H3
SMILES:	COc1cc(c(cc1O)c1coc2cc(cc(c2c1=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080371
PubChem CID:	44613667
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	>	100.0	uM	PMID[463399]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[463399]

☑ 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 NPC45291 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	508
0.1-0.2	2093
0.2-0.3	5101
0.3-0.4	11598
0.4-0.5	5738
0.5-0.6	3965
0.6-0.7	5167
0.7-0.8	4917
0.8-0.85	1875
0.85-0.9	1051
0.9-0.95	585
0.95-1	99

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC19980
0.9931	High Similarity	NPC35763
0.9931	High Similarity	NPC181209
0.9931	High Similarity	NPC100971
0.9931	High Similarity	NPC100263
0.9931	High Similarity	NPC291802
0.9931	High Similarity	NPC121522
0.9931	High Similarity	NPC245382
0.9931	High Similarity	NPC209487
0.9931	High Similarity	NPC269451
0.9931	High Similarity	NPC216769
0.9931	High Similarity	NPC131266
0.9863	High Similarity	NPC124714
0.9863	High Similarity	NPC250557
0.9796	High Similarity	NPC39184
0.9796	High Similarity	NPC130589
0.9796	High Similarity	NPC134287
0.9793	High Similarity	NPC10467
0.9793	High Similarity	NPC156953
0.9793	High Similarity	NPC239363
0.9726	High Similarity	NPC262623
0.9724	High Similarity	NPC264289
0.9724	High Similarity	NPC142876
0.9724	High Similarity	NPC40290
0.9724	High Similarity	NPC333691
0.9724	High Similarity	NPC200060
0.9724	High Similarity	NPC139293
0.9724	High Similarity	NPC264550
0.9724	High Similarity	NPC69430
0.9724	High Similarity	NPC195763
0.9664	High Similarity	NPC78103
0.9655	High Similarity	NPC139364
0.9655	High Similarity	NPC194653
0.9655	High Similarity	NPC254702
0.9655	High Similarity	NPC80710
0.9655	High Similarity	NPC203747
0.9655	High Similarity	NPC218490
0.9655	High Similarity	NPC287395
0.9655	High Similarity	NPC183655
0.9595	High Similarity	NPC280937
0.9589	High Similarity	NPC102003
0.9589	High Similarity	NPC92722
0.9586	High Similarity	NPC188074
0.9586	High Similarity	NPC125449
0.9533	High Similarity	NPC210084
0.9533	High Similarity	NPC99597
0.953	High Similarity	NPC256612
0.953	High Similarity	NPC213622
0.953	High Similarity	NPC2928
0.953	High Similarity	NPC208197
0.953	High Similarity	NPC20830
0.9527	High Similarity	NPC256283
0.9527	High Similarity	NPC71334
0.9527	High Similarity	NPC293183
0.9527	High Similarity	NPC120163
0.9527	High Similarity	NPC101996
0.9527	High Similarity	NPC241498
0.9527	High Similarity	NPC188203
0.9527	High Similarity	NPC275836
0.9527	High Similarity	NPC275722
0.9527	High Similarity	NPC100887
0.9527	High Similarity	NPC222830
0.9527	High Similarity	NPC131624
0.9527	High Similarity	NPC239128
0.9527	High Similarity	NPC198826
0.9527	High Similarity	NPC187498
0.9527	High Similarity	NPC83508
0.9527	High Similarity	NPC212678
0.9527	High Similarity	NPC57030
0.9527	High Similarity	NPC301323
0.9527	High Similarity	NPC162313
0.9527	High Similarity	NPC25270
0.9527	High Similarity	NPC156222
0.9521	High Similarity	NPC131451
0.9521	High Similarity	NPC15329
0.9517	High Similarity	NPC226987
0.9517	High Similarity	NPC12377
0.9517	High Similarity	NPC143903
0.9474	High Similarity	NPC295009
0.9474	High Similarity	NPC260640
0.9467	High Similarity	NPC255106
0.9467	High Similarity	NPC235165
0.9467	High Similarity	NPC472916
0.9463	High Similarity	NPC47781
0.9463	High Similarity	NPC22519
0.9463	High Similarity	NPC176775
0.9463	High Similarity	NPC250822
0.9463	High Similarity	NPC75279
0.9463	High Similarity	NPC160951
0.9463	High Similarity	NPC274327
0.9463	High Similarity	NPC292214
0.9463	High Similarity	NPC167091
0.9463	High Similarity	NPC255350
0.9463	High Similarity	NPC145379
0.9463	High Similarity	NPC69394
0.9463	High Similarity	NPC183878
0.9463	High Similarity	NPC276409
0.9463	High Similarity	NPC88645
0.9463	High Similarity	NPC231018
0.9463	High Similarity	NPC271779
0.9463	High Similarity	NPC206238
0.9459	High Similarity	NPC256406
0.9459	High Similarity	NPC171010
0.9452	High Similarity	NPC119660
0.9452	High Similarity	NPC93034
0.9412	High Similarity	NPC81679
0.9408	High Similarity	NPC225624
0.9408	High Similarity	NPC285973
0.9408	High Similarity	NPC476980
0.9404	High Similarity	NPC162869
0.9404	High Similarity	NPC472911
0.9404	High Similarity	NPC245758
0.9404	High Similarity	NPC470402
0.9404	High Similarity	NPC167595
0.9404	High Similarity	NPC156057
0.9404	High Similarity	NPC474208
0.9404	High Similarity	NPC475267
0.9404	High Similarity	NPC474836
0.9404	High Similarity	NPC472910
0.9404	High Similarity	NPC469584
0.9404	High Similarity	NPC48208
0.9404	High Similarity	NPC36852
0.9404	High Similarity	NPC222814
0.9404	High Similarity	NPC262286
0.9404	High Similarity	NPC472913
0.9404	High Similarity	NPC472914
0.9404	High Similarity	NPC96167
0.94	High Similarity	NPC196439
0.94	High Similarity	NPC50715
0.94	High Similarity	NPC4455
0.94	High Similarity	NPC2476
0.94	High Similarity	NPC44079
0.94	High Similarity	NPC280339
0.94	High Similarity	NPC167815
0.94	High Similarity	NPC201136
0.94	High Similarity	NPC138360
0.94	High Similarity	NPC163780
0.94	High Similarity	NPC26227
0.94	High Similarity	NPC128863
0.94	High Similarity	NPC201451
0.94	High Similarity	NPC183597
0.94	High Similarity	NPC146165
0.94	High Similarity	NPC227325
0.94	High Similarity	NPC92659
0.9396	High Similarity	NPC199100
0.9396	High Similarity	NPC180234
0.9396	High Similarity	NPC120537
0.9396	High Similarity	NPC161277
0.9396	High Similarity	NPC39007
0.9396	High Similarity	NPC142540
0.9396	High Similarity	NPC60972
0.9396	High Similarity	NPC39732
0.9392	High Similarity	NPC45873
0.9392	High Similarity	NPC184136
0.9392	High Similarity	NPC179183
0.9392	High Similarity	NPC306821
0.9388	High Similarity	NPC166036
0.9388	High Similarity	NPC238279
0.9388	High Similarity	NPC203077
0.9388	High Similarity	NPC120464
0.9384	High Similarity	NPC216314
0.9384	High Similarity	NPC120924
0.9384	High Similarity	NPC195919
0.9384	High Similarity	NPC165389
0.9379	High Similarity	NPC142165
0.9379	High Similarity	NPC38065
0.9379	High Similarity	NPC182842
0.9379	High Similarity	NPC242893
0.9346	High Similarity	NPC308992
0.9346	High Similarity	NPC258331
0.9342	High Similarity	NPC62518
0.9342	High Similarity	NPC215375
0.9338	High Similarity	NPC98661
0.9338	High Similarity	NPC245546
0.9338	High Similarity	NPC247017
0.9338	High Similarity	NPC49824
0.9338	High Similarity	NPC474520
0.9338	High Similarity	NPC43243
0.9338	High Similarity	NPC138243
0.9338	High Similarity	NPC266960
0.9333	High Similarity	NPC472915
0.9329	High Similarity	NPC226973
0.9329	High Similarity	NPC117579
0.9329	High Similarity	NPC149614
0.9329	High Similarity	NPC251110
0.9329	High Similarity	NPC208043
0.9329	High Similarity	NPC31363
0.9329	High Similarity	NPC308451
0.9324	High Similarity	NPC296197
0.9324	High Similarity	NPC52005
0.9324	High Similarity	NPC216318
0.9324	High Similarity	NPC48479
0.9324	High Similarity	NPC38545
0.9324	High Similarity	NPC223579
0.9324	High Similarity	NPC171916
0.9324	High Similarity	NPC328119
0.9324	High Similarity	NPC177298
0.9324	High Similarity	NPC17286
0.9324	High Similarity	NPC259713
0.9324	High Similarity	NPC137062

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 NPC45291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	1023
0.2-0.3	2015
0.3-0.4	2635
0.4-0.5	1648
0.5-0.6	903
0.6-0.7	308
0.7-0.8	100
0.8-0.85	25
0.85-0.9	14
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9463	High Similarity	NPD2801	Approved
0.9267	High Similarity	NPD1934	Approved
0.8986	High Similarity	NPD1511	Approved
0.8961	High Similarity	NPD3882	Suspended
0.8954	High Similarity	NPD2393	Clinical (unspecified phase)
0.8867	High Similarity	NPD1512	Approved
0.8828	High Similarity	NPD1510	Phase 2
0.8812	High Similarity	NPD3818	Discontinued
0.8688	High Similarity	NPD6168	Clinical (unspecified phase)
0.8688	High Similarity	NPD6166	Phase 2
0.8688	High Similarity	NPD6167	Clinical (unspecified phase)
0.8654	High Similarity	NPD3817	Phase 2
0.8636	High Similarity	NPD4380	Phase 2
0.8599	High Similarity	NPD4868	Clinical (unspecified phase)
0.8553	High Similarity	NPD5494	Approved
0.8552	High Similarity	NPD943	Approved
0.8552	High Similarity	NPD1240	Approved
0.8545	High Similarity	NPD4338	Clinical (unspecified phase)
0.8528	High Similarity	NPD7054	Approved
0.8476	Intermediate Similarity	NPD7472	Approved
0.8476	Intermediate Similarity	NPD7074	Phase 3
0.8447	Intermediate Similarity	NPD6232	Discontinued
0.8435	Intermediate Similarity	NPD1607	Approved
0.8431	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7473	Discontinued
0.84	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6797	Phase 2
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD1247	Approved
0.8267	Intermediate Similarity	NPD2796	Approved
0.8263	Intermediate Similarity	NPD7251	Discontinued
0.8243	Intermediate Similarity	NPD230	Phase 1
0.8239	Intermediate Similarity	NPD1465	Phase 2
0.8214	Intermediate Similarity	NPD7808	Phase 3
0.8199	Intermediate Similarity	NPD7075	Discontinued
0.8187	Intermediate Similarity	NPD5402	Approved
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2935	Discontinued
0.8129	Intermediate Similarity	NPD6799	Approved
0.8125	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8077	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD7819	Suspended
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3027	Phase 3
0.7961	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD9494	Approved
0.7937	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD919	Approved
0.7888	Intermediate Similarity	NPD7411	Suspended
0.787	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2533	Approved
0.7848	Intermediate Similarity	NPD2532	Approved
0.7848	Intermediate Similarity	NPD2534	Approved
0.7844	Intermediate Similarity	NPD3926	Phase 2
0.7843	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6959	Discontinued
0.7829	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3750	Approved
0.7815	Intermediate Similarity	NPD1613	Approved
0.7815	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD447	Suspended
0.7756	Intermediate Similarity	NPD2800	Approved
0.775	Intermediate Similarity	NPD5403	Approved
0.7736	Intermediate Similarity	NPD5401	Approved
0.7733	Intermediate Similarity	NPD6559	Discontinued
0.7711	Intermediate Similarity	NPD6234	Discontinued
0.7687	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1551	Phase 2
0.7658	Intermediate Similarity	NPD6190	Approved
0.7651	Intermediate Similarity	NPD3749	Approved
0.764	Intermediate Similarity	NPD920	Approved
0.7622	Intermediate Similarity	NPD37	Approved
0.7619	Intermediate Similarity	NPD9269	Phase 2
0.7597	Intermediate Similarity	NPD6651	Approved
0.7593	Intermediate Similarity	NPD1653	Approved
0.759	Intermediate Similarity	NPD7768	Phase 2
0.7588	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1243	Approved
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4966	Approved
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD7390	Discontinued
0.7451	Intermediate Similarity	NPD2313	Discontinued
0.7451	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3226	Approved
0.7429	Intermediate Similarity	NPD7685	Pre-registration
0.7427	Intermediate Similarity	NPD5242	Approved
0.7419	Intermediate Similarity	NPD1933	Approved
0.7417	Intermediate Similarity	NPD2798	Approved
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7407	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7228	Approved
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7347	Intermediate Similarity	NPD9268	Approved
0.7342	Intermediate Similarity	NPD6099	Approved
0.7342	Intermediate Similarity	NPD6100	Approved
0.7329	Intermediate Similarity	NPD2309	Approved
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5353	Approved
0.7296	Intermediate Similarity	NPD2346	Discontinued
0.7288	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD5710	Approved
0.7267	Intermediate Similarity	NPD5711	Approved
0.7258	Intermediate Similarity	NPD6780	Approved
0.7258	Intermediate Similarity	NPD6781	Approved
0.7258	Intermediate Similarity	NPD6779	Approved
0.7258	Intermediate Similarity	NPD6776	Approved
0.7258	Intermediate Similarity	NPD6777	Approved
0.7258	Intermediate Similarity	NPD6778	Approved
0.7258	Intermediate Similarity	NPD6782	Approved
0.7246	Intermediate Similarity	NPD6385	Approved
0.7246	Intermediate Similarity	NPD6386	Approved
0.7239	Intermediate Similarity	NPD4357	Discontinued
0.7237	Intermediate Similarity	NPD1470	Approved
0.7237	Intermediate Similarity	NPD1203	Approved
0.7211	Intermediate Similarity	NPD5536	Phase 2
0.7205	Intermediate Similarity	NPD2654	Approved
0.7202	Intermediate Similarity	NPD6844	Discontinued
0.72	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1548	Phase 1
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD2899	Discontinued
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4908	Phase 1
0.7097	Intermediate Similarity	NPD6832	Phase 2
0.7086	Intermediate Similarity	NPD1201	Approved
0.7086	Intermediate Similarity	NPD1610	Phase 2
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7056	Intermediate Similarity	NPD8313	Approved
0.7056	Intermediate Similarity	NPD8312	Approved
0.7053	Intermediate Similarity	NPD7696	Phase 3
0.7053	Intermediate Similarity	NPD7698	Approved
0.7053	Intermediate Similarity	NPD7697	Approved
0.7047	Intermediate Similarity	NPD9545	Approved
0.7039	Intermediate Similarity	NPD9717	Approved
0.7039	Intermediate Similarity	NPD3972	Approved
0.7034	Intermediate Similarity	NPD228	Approved
0.7027	Intermediate Similarity	NPD9493	Approved
0.7016	Intermediate Similarity	NPD7870	Phase 2
0.7016	Intermediate Similarity	NPD7871	Phase 2
0.7006	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD6823	Phase 2
0.6995	Remote Similarity	NPD7701	Phase 2
0.6993	Remote Similarity	NPD2983	Phase 2
0.6993	Remote Similarity	NPD2982	Phase 2
0.6989	Remote Similarity	NPD4363	Phase 3
0.6989	Remote Similarity	NPD2403	Approved
0.6989	Remote Similarity	NPD4360	Phase 2
0.6989	Remote Similarity	NPD6535	Approved
0.6989	Remote Similarity	NPD6534	Approved
0.6975	Remote Similarity	NPD7266	Discontinued
0.6974	Remote Similarity	NPD422	Phase 1
0.6962	Remote Similarity	NPD6233	Phase 2
0.6944	Remote Similarity	NPD7240	Approved
0.6943	Remote Similarity	NPD7584	Approved
0.6928	Remote Similarity	NPD2981	Phase 2
0.6928	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2861	Phase 2
0.6923	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7874	Approved
0.6919	Remote Similarity	NPD4288	Approved
0.6914	Remote Similarity	NPD5406	Approved
0.6914	Remote Similarity	NPD5408	Approved
0.6914	Remote Similarity	NPD5405	Approved
0.6914	Remote Similarity	NPD5404	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