NPASS Compound

Structure

CID287395 OpenBabel06191716092D 21 22 0 0 0 0 0 0 0 0999 V2000 -6.9282 -0.0000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 -0.0000 1.0000 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 -1.7321 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 -5.1962 1.0000 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 -5.1962 -0.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.08
Volume:	285.169
LogP:	2.376
LogD:	2.722
LogS:	-3.318
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	2.108
Fsp3:	0.133
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:	-4.867
MDCK Permeability:	1.1406671546865255e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	98.61917877197266%
Volume Distribution (VD):	0.457
Pgp-substrate:	3.615941047668457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.897
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.563
CYP2C9-substrate:	0.786
CYP2D6-inhibitor:	0.245
CYP2D6-substrate:	0.424
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.332

ADMET: Excretion

Clearance (CL):	11.705
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.783
AMES Toxicity:	0.674
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.316
Skin Sensitization:	0.314
Carcinogencity:	0.077
Eye Corrosion:	0.004
Eye Irritation:	0.926
Respiratory Toxicity:	0.356

Download Data

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

Natural Product: NPC287395

Natural Product ID:	NPC287395
*Common Name:**	Melanoxoin
IUPAC Name:	(2,5-dihydroxy-4-methoxyphenyl)-(3-hydroxy-4-methoxyphenyl)methanone
Synonyms:	Melanoxoin
Standard InCHIKey:	JCGYLYGMIXXHOU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O6/c1-20-13-4-3-8(5-11(13)17)15(19)9-6-12(18)14(21-2)7-10(9)16/h3-7,16-18H,1-2H3
SMILES:	COc1ccc(cc1O)C(=O)c1cc(O)c(cc1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801608
PubChem CID:	53262825
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	Heartwood	India	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[21784631]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1087	Pterocarpus santalinus	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
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	0.46	ug.mL-1	PMID[542973]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.62	ug.mL-1	PMID[542973]

☑ 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 NPC287395 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	442
0.1-0.2	1911
0.2-0.3	4997
0.3-0.4	11395
0.4-0.5	5843
0.5-0.6	3644
0.6-0.7	4978
0.7-0.8	5773
0.8-0.85	2196
0.85-0.9	1069
0.9-0.95	425
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC183655
0.979	High Similarity	NPC102003
0.979	High Similarity	NPC92722
0.9724	High Similarity	NPC291802
0.9724	High Similarity	NPC131266
0.9724	High Similarity	NPC100971
0.9724	High Similarity	NPC35763
0.9724	High Similarity	NPC100263
0.9724	High Similarity	NPC121522
0.9724	High Similarity	NPC181209
0.9724	High Similarity	NPC209487
0.9724	High Similarity	NPC269451
0.9724	High Similarity	NPC245382
0.9724	High Similarity	NPC216769
0.972	High Similarity	NPC15329
0.972	High Similarity	NPC131451
0.9658	High Similarity	NPC88645
0.9658	High Similarity	NPC124714
0.9658	High Similarity	NPC206238
0.9658	High Similarity	NPC167091
0.9658	High Similarity	NPC292214
0.9658	High Similarity	NPC271779
0.9655	High Similarity	NPC45291
0.9655	High Similarity	NPC19980
0.965	High Similarity	NPC93034
0.965	High Similarity	NPC119660
0.9645	High Similarity	NPC287722
0.9592	High Similarity	NPC39184
0.9589	High Similarity	NPC161277
0.9589	High Similarity	NPC101996
0.9589	High Similarity	NPC199100
0.9589	High Similarity	NPC120537
0.9589	High Similarity	NPC39007
0.9589	High Similarity	NPC180234
0.9586	High Similarity	NPC156953
0.9586	High Similarity	NPC10467
0.9583	High Similarity	NPC218490
0.958	High Similarity	NPC143903
0.958	High Similarity	NPC165389
0.958	High Similarity	NPC226987
0.9577	High Similarity	NPC142165
0.9524	High Similarity	NPC250557
0.9521	High Similarity	NPC171010
0.9521	High Similarity	NPC149614
0.9521	High Similarity	NPC251110
0.9521	High Similarity	NPC262623
0.9517	High Similarity	NPC142876
0.9517	High Similarity	NPC333691
0.9517	High Similarity	NPC69430
0.9517	High Similarity	NPC139293
0.9517	High Similarity	NPC200060
0.9517	High Similarity	NPC264550
0.9517	High Similarity	NPC40290
0.9517	High Similarity	NPC195763
0.9517	High Similarity	NPC264289
0.9514	High Similarity	NPC125449
0.9514	High Similarity	NPC188074
0.9507	High Similarity	NPC254659
0.9463	High Similarity	NPC99597
0.9463	High Similarity	NPC210084
0.9459	High Similarity	NPC256612
0.9459	High Similarity	NPC2928
0.9459	High Similarity	NPC134287
0.9459	High Similarity	NPC130589
0.9459	High Similarity	NPC20830
0.9456	High Similarity	NPC120163
0.9456	High Similarity	NPC198826
0.9456	High Similarity	NPC275836
0.9456	High Similarity	NPC212678
0.9456	High Similarity	NPC301323
0.9456	High Similarity	NPC293183
0.9456	High Similarity	NPC162313
0.9456	High Similarity	NPC156222
0.9456	High Similarity	NPC222830
0.9456	High Similarity	NPC239128
0.9456	High Similarity	NPC71334
0.9456	High Similarity	NPC83508
0.9456	High Similarity	NPC188203
0.9456	High Similarity	NPC57030
0.9456	High Similarity	NPC241498
0.9456	High Similarity	NPC131624
0.9456	High Similarity	NPC275722
0.9456	High Similarity	NPC256283
0.9456	High Similarity	NPC187498
0.9456	High Similarity	NPC100887
0.9456	High Similarity	NPC25270
0.9452	High Similarity	NPC179183
0.9452	High Similarity	NPC239363
0.9452	High Similarity	NPC29231
0.9452	High Similarity	NPC61620
0.9452	High Similarity	NPC62042
0.9452	High Similarity	NPC472279
0.9452	High Similarity	NPC248102
0.9452	High Similarity	NPC45873
0.9448	High Similarity	NPC139364
0.9448	High Similarity	NPC254702
0.9448	High Similarity	NPC194653
0.9448	High Similarity	NPC203747
0.9448	High Similarity	NPC80710
0.9441	High Similarity	NPC207732
0.9437	High Similarity	NPC284556
0.9437	High Similarity	NPC312256
0.9437	High Similarity	NPC301178
0.9433	High Similarity	NPC50823
0.94	High Similarity	NPC16935
0.9396	High Similarity	NPC235165
0.9396	High Similarity	NPC255106
0.9396	High Similarity	NPC472916
0.9392	High Similarity	NPC274327
0.9392	High Similarity	NPC183878
0.9392	High Similarity	NPC231018
0.9392	High Similarity	NPC176775
0.9392	High Similarity	NPC47781
0.9392	High Similarity	NPC255350
0.9392	High Similarity	NPC69394
0.9392	High Similarity	NPC22519
0.9392	High Similarity	NPC145379
0.9392	High Similarity	NPC160951
0.9388	High Similarity	NPC117579
0.9384	High Similarity	NPC296197
0.9384	High Similarity	NPC216318
0.9384	High Similarity	NPC259713
0.9384	High Similarity	NPC17286
0.9384	High Similarity	NPC294502
0.9384	High Similarity	NPC200221
0.9379	High Similarity	NPC61871
0.9379	High Similarity	NPC55557
0.9379	High Similarity	NPC30647
0.9371	High Similarity	NPC471417
0.9371	High Similarity	NPC119663
0.9366	High Similarity	NPC110419
0.9338	High Similarity	NPC476980
0.9333	High Similarity	NPC78103
0.9333	High Similarity	NPC474208
0.9333	High Similarity	NPC78225
0.9333	High Similarity	NPC36852
0.9333	High Similarity	NPC222814
0.9333	High Similarity	NPC474836
0.9333	High Similarity	NPC262286
0.9333	High Similarity	NPC96167
0.9333	High Similarity	NPC472910
0.9333	High Similarity	NPC472914
0.9333	High Similarity	NPC245758
0.9333	High Similarity	NPC162869
0.9333	High Similarity	NPC48208
0.9333	High Similarity	NPC472911
0.9333	High Similarity	NPC156057
0.9333	High Similarity	NPC472913
0.9333	High Similarity	NPC475267
0.9329	High Similarity	NPC201136
0.9329	High Similarity	NPC196439
0.9329	High Similarity	NPC4455
0.9329	High Similarity	NPC138360
0.9329	High Similarity	NPC280339
0.9329	High Similarity	NPC201451
0.9329	High Similarity	NPC213622
0.9329	High Similarity	NPC92659
0.9329	High Similarity	NPC227325
0.9329	High Similarity	NPC44079
0.9329	High Similarity	NPC167815
0.9329	High Similarity	NPC26227
0.9329	High Similarity	NPC183597
0.9329	High Similarity	NPC146165
0.9329	High Similarity	NPC163780
0.9329	High Similarity	NPC50715
0.9329	High Similarity	NPC128863
0.9329	High Similarity	NPC2476
0.9329	High Similarity	NPC208197
0.9324	High Similarity	NPC39732
0.9324	High Similarity	NPC142540
0.9324	High Similarity	NPC60972
0.932	High Similarity	NPC184136
0.932	High Similarity	NPC306821
0.9315	High Similarity	NPC196277
0.9315	High Similarity	NPC118726
0.9315	High Similarity	NPC12367
0.9315	High Similarity	NPC276930
0.9315	High Similarity	NPC43669
0.9315	High Similarity	NPC272721
0.9315	High Similarity	NPC194856
0.931	High Similarity	NPC12377
0.9306	High Similarity	NPC242893
0.9306	High Similarity	NPC38065
0.9276	High Similarity	NPC258331
0.9276	High Similarity	NPC188486
0.9276	High Similarity	NPC308992
0.9276	High Similarity	NPC295009
0.9276	High Similarity	NPC260640
0.9276	High Similarity	NPC311740
0.9272	High Similarity	NPC195832
0.9272	High Similarity	NPC196879
0.9267	High Similarity	NPC68093
0.9267	High Similarity	NPC266960
0.9267	High Similarity	NPC49824
0.9267	High Similarity	NPC470762
0.9267	High Similarity	NPC247017
0.9267	High Similarity	NPC191146
0.9267	High Similarity	NPC98661
0.9267	High Similarity	NPC245546
0.9267	High Similarity	NPC43243

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 NPC287395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	1000
0.2-0.3	1809
0.3-0.4	2734
0.4-0.5	1661
0.5-0.6	994
0.6-0.7	364
0.7-0.8	129
0.8-0.85	25
0.85-0.9	14
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9392	High Similarity	NPD2801	Approved
0.9195	High Similarity	NPD1934	Approved
0.9041	High Similarity	NPD1511	Approved
0.9013	High Similarity	NPD3882	Suspended
0.8919	High Similarity	NPD1512	Approved
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8865	High Similarity	NPD1240	Approved
0.8865	High Similarity	NPD943	Approved
0.875	High Similarity	NPD1510	Phase 2
0.8741	High Similarity	NPD1607	Approved
0.8625	High Similarity	NPD3818	Discontinued
0.8616	High Similarity	NPD6168	Clinical (unspecified phase)
0.8616	High Similarity	NPD6166	Phase 2
0.8616	High Similarity	NPD6167	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6232	Discontinued
0.8481	Intermediate Similarity	NPD5494	Approved
0.8462	Intermediate Similarity	NPD3817	Phase 2
0.8447	Intermediate Similarity	NPD7473	Discontinued
0.8446	Intermediate Similarity	NPD1549	Phase 2
0.8442	Intermediate Similarity	NPD4380	Phase 2
0.8408	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7074	Phase 3
0.8378	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7054	Approved
0.8313	Intermediate Similarity	NPD1247	Approved
0.8311	Intermediate Similarity	NPD2935	Discontinued
0.8293	Intermediate Similarity	NPD7472	Approved
0.8288	Intermediate Similarity	NPD230	Phase 1
0.828	Intermediate Similarity	NPD1465	Phase 2
0.8243	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD6797	Phase 2
0.8125	Intermediate Similarity	NPD9494	Approved
0.8125	Intermediate Similarity	NPD7075	Discontinued
0.8125	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7251	Discontinued
0.8067	Intermediate Similarity	NPD2796	Approved
0.805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD447	Suspended
0.8036	Intermediate Similarity	NPD7808	Phase 3
0.8014	Intermediate Similarity	NPD3027	Phase 3
0.8013	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5402	Approved
0.7988	Intermediate Similarity	NPD3926	Phase 2
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7963	Intermediate Similarity	NPD919	Approved
0.7945	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7819	Suspended
0.7917	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6801	Discontinued
0.7857	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1613	Approved
0.7852	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1551	Phase 2
0.7812	Intermediate Similarity	NPD7411	Suspended
0.7792	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9269	Phase 2
0.7771	Intermediate Similarity	NPD2533	Approved
0.7771	Intermediate Similarity	NPD2534	Approved
0.7771	Intermediate Similarity	NPD2532	Approved
0.7759	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3750	Approved
0.7692	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3749	Approved
0.7673	Intermediate Similarity	NPD920	Approved
0.7662	Intermediate Similarity	NPD2344	Approved
0.7661	Intermediate Similarity	NPD6559	Discontinued
0.7651	Intermediate Similarity	NPD6959	Discontinued
0.7632	Intermediate Similarity	NPD6651	Approved
0.7595	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6190	Approved
0.7564	Intermediate Similarity	NPD1243	Approved
0.7562	Intermediate Similarity	NPD5403	Approved
0.7547	Intermediate Similarity	NPD5401	Approved
0.7547	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD1653	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD7768	Phase 2
0.7515	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD9268	Approved
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3226	Approved
0.7468	Intermediate Similarity	NPD2309	Approved
0.7456	Intermediate Similarity	NPD5242	Approved
0.7452	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1933	Approved
0.7439	Intermediate Similarity	NPD37	Approved
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7421	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2799	Discontinued
0.7419	Intermediate Similarity	NPD3748	Approved
0.7399	Intermediate Similarity	NPD5953	Discontinued
0.7384	Intermediate Similarity	NPD7286	Phase 2
0.7383	Intermediate Similarity	NPD1470	Approved
0.7377	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7390	Discontinued
0.7375	Intermediate Similarity	NPD4357	Discontinued
0.7368	Intermediate Similarity	NPD2313	Discontinued
0.7361	Intermediate Similarity	NPD5536	Phase 2
0.7337	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD2798	Approved
0.7325	Intermediate Similarity	NPD2346	Discontinued
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD228	Approved
0.7305	Intermediate Similarity	NPD4966	Approved
0.7297	Intermediate Similarity	NPD9717	Approved
0.7292	Intermediate Similarity	NPD9493	Approved
0.7285	Intermediate Similarity	NPD3018	Phase 2
0.7273	Intermediate Similarity	NPD6386	Approved
0.7273	Intermediate Similarity	NPD6385	Approved
0.7261	Intermediate Similarity	NPD6100	Approved
0.7261	Intermediate Similarity	NPD6099	Approved
0.7257	Intermediate Similarity	NPD7685	Pre-registration
0.7251	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5353	Approved
0.7233	Intermediate Similarity	NPD2654	Approved
0.723	Intermediate Similarity	NPD1201	Approved
0.723	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5710	Approved
0.7193	Intermediate Similarity	NPD5711	Approved
0.7193	Intermediate Similarity	NPD3787	Discontinued
0.7192	Intermediate Similarity	NPD9545	Approved
0.7189	Intermediate Similarity	NPD6776	Approved
0.7189	Intermediate Similarity	NPD6777	Approved
0.7189	Intermediate Similarity	NPD6781	Approved
0.7189	Intermediate Similarity	NPD6778	Approved
0.7189	Intermediate Similarity	NPD6782	Approved
0.7189	Intermediate Similarity	NPD6780	Approved
0.7189	Intermediate Similarity	NPD6779	Approved
0.7181	Intermediate Similarity	NPD1608	Approved
0.7181	Intermediate Similarity	NPD3972	Approved
0.7179	Intermediate Similarity	NPD2899	Discontinued
0.7143	Intermediate Similarity	NPD411	Approved
0.7133	Intermediate Similarity	NPD2982	Phase 2
0.7133	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD6832	Phase 2
0.7119	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1610	Phase 2
0.7114	Intermediate Similarity	NPD422	Phase 1
0.7081	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1548	Phase 1
0.7074	Intermediate Similarity	NPD7435	Discontinued
0.7067	Intermediate Similarity	NPD2981	Phase 2
0.7056	Intermediate Similarity	NPD8434	Phase 2
0.7056	Intermediate Similarity	NPD8150	Discontinued
0.7055	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD824	Approved
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7039	Intermediate Similarity	NPD1164	Approved
0.7032	Intermediate Similarity	NPD3764	Approved
0.7024	Intermediate Similarity	NPD6844	Discontinued
0.7013	Intermediate Similarity	NPD4908	Phase 1
0.7011	Intermediate Similarity	NPD2403	Approved
0.7	Intermediate Similarity	NPD1471	Phase 3
0.6984	Remote Similarity	NPD7696	Phase 3
0.6984	Remote Similarity	NPD7697	Approved
0.6984	Remote Similarity	NPD7698	Approved
0.6983	Remote Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD8313	Approved
0.6981	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD17	Approved
0.6979	Remote Similarity	NPD8151	Discontinued
0.6974	Remote Similarity	NPD1876	Approved
0.6966	Remote Similarity	NPD5283	Phase 1
0.6954	Remote Similarity	NPD1481	Phase 2
0.6947	Remote Similarity	NPD7870	Phase 2
0.6947	Remote Similarity	NPD7871	Phase 2
0.6941	Remote Similarity	NPD2296	Approved
0.6937	Remote Similarity	NPD5408	Approved
0.6937	Remote Similarity	NPD5405	Approved
0.6937	Remote Similarity	NPD5404	Approved
0.6937	Remote Similarity	NPD5406	Approved
0.6935	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2354	Approved
0.6931	Remote Similarity	NPD6823	Phase 2
0.6927	Remote Similarity	NPD7701	Phase 2
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD6535	Approved
0.6894	Remote Similarity	NPD7266	Discontinued
0.6887	Remote Similarity	NPD1535	Discovery

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