NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	574.29
Volume:	618.141
LogP:	8.518
LogD:	4.086
LogS:	-1.843
# Rotatable Bonds:	10
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.094
Synthetic Accessibility Score:	3.663
Fsp3:	0.343
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.171
MDCK Permeability:	1.2413834156177472e-05
Pgp-inhibitor:	0.226
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.149
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	93.52794647216797%
Volume Distribution (VD):	1.606
Pgp-substrate:	9.579667091369629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.246
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.815
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.8
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	6.771
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.982
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.927
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.781
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC476631

Natural Product ID:	NPC476631
*Common Name:**	2-(2,4,5-Trihydroxyphenyl)-3,6-bis(3-methyl-2-butenyl)-5,7-dihydroxy-8-(3,7-dimethyl-2,6-octadiene-1-yl)-4H-1-benzopyran-4-one
IUPAC Name:	8-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-3,6-bis(3-methylbut-2-enyl)-2-(2,4,5-trihydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	UYSRUJGUWGNLEQ-LPYMAVHISA-N
Standard InCHI:	InChI=1S/C35H42O7/c1-19(2)9-8-10-22(7)13-16-24-31(39)23(14-11-20(3)4)32(40)30-33(41)25(15-12-21(5)6)34(42-35(24)30)26-17-28(37)29(38)18-27(26)36/h9,11-13,17-18,36-40H,8,10,14-16H2,1-7H3/b22-13+
SMILES:	CC(=CCC/C(=C/CC1=C2C(=C(C(=C1O)CC=C(C)C)O)C(=O)C(=C(O2)C3=CC(=C(C=C3O)O)O)CC=C(C)C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	102196501
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	heartwood	n.a.	n.a.	PMID[16643064]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	roots	Khon Kaen, Thailand	2009-DEC	PMID[25537111]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	30	%	PMID[25537111]

☑ 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 NPC476631 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	446
0.1-0.2	1811
0.2-0.3	4558
0.3-0.4	11095
0.4-0.5	6876
0.5-0.6	3789
0.6-0.7	5072
0.7-0.8	4788
0.8-0.85	2417
0.85-0.9	1190
0.9-0.95	611
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC249570
0.9667	High Similarity	NPC476630
0.9667	High Similarity	NPC218871
0.966	High Similarity	NPC3825
0.966	High Similarity	NPC88804
0.9603	High Similarity	NPC469658
0.96	High Similarity	NPC276444
0.9595	High Similarity	NPC205046
0.9595	High Similarity	NPC59162
0.9595	High Similarity	NPC304295
0.9536	High Similarity	NPC236796
0.9533	High Similarity	NPC113906
0.953	High Similarity	NPC63187
0.953	High Similarity	NPC37684
0.953	High Similarity	NPC157784
0.953	High Similarity	NPC471982
0.9477	High Similarity	NPC278427
0.947	High Similarity	NPC138243
0.947	High Similarity	NPC142339
0.947	High Similarity	NPC13779
0.947	High Similarity	NPC475799
0.947	High Similarity	NPC68093
0.947	High Similarity	NPC191146
0.9467	High Similarity	NPC170492
0.9467	High Similarity	NPC298692
0.9463	High Similarity	NPC154345
0.9412	High Similarity	NPC119224
0.9412	High Similarity	NPC246478
0.9412	High Similarity	NPC476980
0.9412	High Similarity	NPC320359
0.9412	High Similarity	NPC204290
0.9408	High Similarity	NPC78225
0.9408	High Similarity	NPC36852
0.9408	High Similarity	NPC237418
0.9408	High Similarity	NPC223787
0.9408	High Similarity	NPC273843
0.9408	High Similarity	NPC262286
0.9404	High Similarity	NPC133392
0.94	High Similarity	NPC106976
0.9396	High Similarity	NPC184136
0.9351	High Similarity	NPC167678
0.9351	High Similarity	NPC198829
0.9351	High Similarity	NPC258331
0.9351	High Similarity	NPC259456
0.9351	High Similarity	NPC40491
0.9351	High Similarity	NPC29876
0.9351	High Similarity	NPC278052
0.9346	High Similarity	NPC172770
0.9346	High Similarity	NPC100123
0.9346	High Similarity	NPC185258
0.9342	High Similarity	NPC470328
0.9342	High Similarity	NPC472626
0.9342	High Similarity	NPC209614
0.9342	High Similarity	NPC3980
0.9342	High Similarity	NPC471985
0.9338	High Similarity	NPC276409
0.9338	High Similarity	NPC89474
0.9338	High Similarity	NPC274327
0.9338	High Similarity	NPC192083
0.9338	High Similarity	NPC250822
0.9338	High Similarity	NPC183878
0.9338	High Similarity	NPC231018
0.9338	High Similarity	NPC176775
0.9338	High Similarity	NPC74924
0.9338	High Similarity	NPC69394
0.9338	High Similarity	NPC75279
0.9338	High Similarity	NPC47781
0.9338	High Similarity	NPC145379
0.9338	High Similarity	NPC22519
0.9338	High Similarity	NPC160951
0.9338	High Similarity	NPC213896
0.9338	High Similarity	NPC255350
0.9329	High Similarity	NPC328119
0.9329	High Similarity	NPC48479
0.9329	High Similarity	NPC177298
0.9324	High Similarity	NPC275772
0.9324	High Similarity	NPC108406
0.9324	High Similarity	NPC130230
0.9324	High Similarity	NPC239312
0.9315	High Similarity	NPC175013
0.929	High Similarity	NPC83922
0.929	High Similarity	NPC194427
0.929	High Similarity	NPC81679
0.929	High Similarity	NPC329760
0.929	High Similarity	NPC472448
0.9286	High Similarity	NPC235018
0.9286	High Similarity	NPC228785
0.9286	High Similarity	NPC45146
0.9286	High Similarity	NPC56085
0.9286	High Similarity	NPC14353
0.9281	High Similarity	NPC79053
0.9281	High Similarity	NPC476981
0.9276	High Similarity	NPC146165
0.9276	High Similarity	NPC45849
0.9276	High Similarity	NPC200761
0.9276	High Similarity	NPC256612
0.9276	High Similarity	NPC20830
0.9276	High Similarity	NPC50715
0.9276	High Similarity	NPC208197
0.9276	High Similarity	NPC128863
0.9276	High Similarity	NPC227325
0.9276	High Similarity	NPC167815
0.9276	High Similarity	NPC234255
0.9276	High Similarity	NPC163780
0.9276	High Similarity	NPC138360
0.9276	High Similarity	NPC470327
0.9276	High Similarity	NPC2476
0.9276	High Similarity	NPC196439
0.9276	High Similarity	NPC4455
0.9276	High Similarity	NPC280339
0.9276	High Similarity	NPC213622
0.9276	High Similarity	NPC201136
0.9276	High Similarity	NPC92659
0.9276	High Similarity	NPC472280
0.9276	High Similarity	NPC183597
0.9276	High Similarity	NPC130589
0.9276	High Similarity	NPC321779
0.9276	High Similarity	NPC134287
0.9276	High Similarity	NPC477503
0.9272	High Similarity	NPC71334
0.9272	High Similarity	NPC83508
0.9272	High Similarity	NPC100887
0.9272	High Similarity	NPC275836
0.9272	High Similarity	NPC25270
0.9272	High Similarity	NPC156222
0.9272	High Similarity	NPC237994
0.9272	High Similarity	NPC57030
0.9272	High Similarity	NPC275722
0.9272	High Similarity	NPC293183
0.9272	High Similarity	NPC256283
0.9272	High Similarity	NPC187498
0.9272	High Similarity	NPC162313
0.9272	High Similarity	NPC188203
0.9272	High Similarity	NPC131624
0.9272	High Similarity	NPC222830
0.9272	High Similarity	NPC301323
0.9272	High Similarity	NPC241498
0.9272	High Similarity	NPC120163
0.9272	High Similarity	NPC239128
0.9272	High Similarity	NPC212678
0.9272	High Similarity	NPC198826
0.9267	High Similarity	NPC62042
0.9262	High Similarity	NPC203077
0.9262	High Similarity	NPC238279
0.9262	High Similarity	NPC276930
0.9262	High Similarity	NPC166036
0.9262	High Similarity	NPC12367
0.9262	High Similarity	NPC194856
0.9262	High Similarity	NPC118726
0.9262	High Similarity	NPC120464
0.9252	High Similarity	NPC279121
0.9236	High Similarity	NPC39091
0.9236	High Similarity	NPC470462
0.9231	High Similarity	NPC270837
0.9231	High Similarity	NPC7483
0.9231	High Similarity	NPC470459
0.9231	High Similarity	NPC236132
0.9231	High Similarity	NPC23298
0.9231	High Similarity	NPC189473
0.9231	High Similarity	NPC207690
0.9226	High Similarity	NPC266314
0.9226	High Similarity	NPC475883
0.9226	High Similarity	NPC472275
0.9226	High Similarity	NPC32694
0.9226	High Similarity	NPC61010
0.9226	High Similarity	NPC474351
0.9221	High Similarity	NPC210459
0.9221	High Similarity	NPC46736
0.9221	High Similarity	NPC197856
0.9221	High Similarity	NPC250214
0.9221	High Similarity	NPC95936
0.9216	High Similarity	NPC472455
0.9216	High Similarity	NPC291878
0.9216	High Similarity	NPC474520
0.9216	High Similarity	NPC282307
0.9216	High Similarity	NPC200388
0.9216	High Similarity	NPC35038
0.9216	High Similarity	NPC100916
0.9216	High Similarity	NPC55619
0.9216	High Similarity	NPC170026
0.9216	High Similarity	NPC278778
0.9216	High Similarity	NPC49824
0.9216	High Similarity	NPC274730
0.9216	High Similarity	NPC195796
0.9211	High Similarity	NPC227337
0.9211	High Similarity	NPC280937
0.9211	High Similarity	NPC70433
0.9211	High Similarity	NPC49402
0.9211	High Similarity	NPC33051
0.9211	High Similarity	NPC273462
0.9205	High Similarity	NPC208043
0.9205	High Similarity	NPC308451
0.9205	High Similarity	NPC202157
0.9205	High Similarity	NPC226973
0.92	High Similarity	NPC195351
0.92	High Similarity	NPC296197
0.92	High Similarity	NPC17286
0.92	High Similarity	NPC137062
0.92	High Similarity	NPC270465
0.92	High Similarity	NPC171916

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 NPC476631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	985
0.2-0.3	1814
0.3-0.4	2732
0.4-0.5	1742
0.5-0.6	985
0.6-0.7	331
0.7-0.8	110
0.8-0.85	41
0.85-0.9	4
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9338	High Similarity	NPD2801	Approved
0.9338	High Similarity	NPD2393	Clinical (unspecified phase)
0.9252	High Similarity	NPD1511	Approved
0.9128	High Similarity	NPD1512	Approved
0.902	High Similarity	NPD1934	Approved
0.8933	High Similarity	NPD4378	Clinical (unspecified phase)
0.8608	High Similarity	NPD3882	Suspended
0.858	High Similarity	NPD6166	Phase 2
0.858	High Similarity	NPD6168	Clinical (unspecified phase)
0.858	High Similarity	NPD6167	Clinical (unspecified phase)
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8544	High Similarity	NPD3817	Phase 2
0.8537	High Similarity	NPD7054	Approved
0.8526	High Similarity	NPD4380	Phase 2
0.8485	Intermediate Similarity	NPD7472	Approved
0.8485	Intermediate Similarity	NPD7074	Phase 3
0.8481	Intermediate Similarity	NPD7819	Suspended
0.8476	Intermediate Similarity	NPD3818	Discontinued
0.8447	Intermediate Similarity	NPD5494	Approved
0.8438	Intermediate Similarity	NPD7075	Discontinued
0.8428	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7251	Discontinued
0.8375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7808	Phase 3
0.8333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8323	Intermediate Similarity	NPD6797	Phase 2
0.8313	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8289	Intermediate Similarity	NPD1549	Phase 2
0.8278	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD943	Approved
0.8188	Intermediate Similarity	NPD1240	Approved
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8171	Intermediate Similarity	NPD6959	Discontinued
0.8158	Intermediate Similarity	NPD2935	Discontinued
0.8125	Intermediate Similarity	NPD7411	Suspended
0.8117	Intermediate Similarity	NPD2800	Approved
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8079	Intermediate Similarity	NPD1607	Approved
0.8061	Intermediate Similarity	NPD1247	Approved
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7768	Phase 2
0.8025	Intermediate Similarity	NPD1465	Phase 2
0.8025	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5402	Approved
0.7973	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3750	Approved
0.7919	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1243	Approved
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7843	Intermediate Similarity	NPD6651	Approved
0.784	Intermediate Similarity	NPD6599	Discontinued
0.7831	Intermediate Similarity	NPD919	Approved
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD6099	Approved
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1613	Approved
0.7697	Intermediate Similarity	NPD2313	Discontinued
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7390	Discontinued
0.7669	Intermediate Similarity	NPD3226	Approved
0.7665	Intermediate Similarity	NPD3749	Approved
0.7654	Intermediate Similarity	NPD5403	Approved
0.7654	Intermediate Similarity	NPD920	Approved
0.7647	Intermediate Similarity	NPD3926	Phase 2
0.7628	Intermediate Similarity	NPD2799	Discontinued
0.7628	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1551	Phase 2
0.7572	Intermediate Similarity	NPD7286	Phase 2
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD447	Suspended
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7532	Intermediate Similarity	NPD2344	Approved
0.7531	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7394	Intermediate Similarity	NPD1653	Approved
0.7391	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1203	Approved
0.7362	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3268	Approved
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2309	Approved
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD2798	Approved
0.7317	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4625	Phase 3
0.7285	Intermediate Similarity	NPD9269	Phase 2
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7283	Intermediate Similarity	NPD5711	Approved
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7255	Intermediate Similarity	NPD2797	Approved
0.7241	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6190	Approved
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7237	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD37	Approved
0.7219	Intermediate Similarity	NPD6844	Discontinued
0.7216	Intermediate Similarity	NPD3751	Discontinued
0.7216	Intermediate Similarity	NPD7228	Approved
0.7215	Intermediate Similarity	NPD1933	Approved
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4965	Approved
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7181	Intermediate Similarity	NPD1548	Phase 1
0.7171	Intermediate Similarity	NPD9717	Approved
0.7171	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD9494	Approved
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD7584	Approved
0.7124	Intermediate Similarity	NPD4749	Approved
0.7117	Intermediate Similarity	NPD2654	Approved
0.7107	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1201	Approved
0.7105	Intermediate Similarity	NPD1610	Phase 2
0.709	Intermediate Similarity	NPD6779	Approved
0.709	Intermediate Similarity	NPD6780	Approved
0.709	Intermediate Similarity	NPD6782	Approved
0.709	Intermediate Similarity	NPD6781	Approved
0.709	Intermediate Similarity	NPD6777	Approved
0.709	Intermediate Similarity	NPD6778	Approved
0.709	Intermediate Similarity	NPD6776	Approved
0.7078	Intermediate Similarity	NPD3225	Approved
0.7077	Intermediate Similarity	NPD7783	Phase 2
0.7077	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7698	Approved
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7037	Intermediate Similarity	NPD5408	Approved
0.7037	Intermediate Similarity	NPD5405	Approved
0.7037	Intermediate Similarity	NPD5404	Approved
0.7037	Intermediate Similarity	NPD5406	Approved
0.7035	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD1470	Approved
0.7032	Intermediate Similarity	NPD3267	Approved
0.7032	Intermediate Similarity	NPD3266	Approved
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.7025	Intermediate Similarity	NPD411	Approved
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD9268	Approved
0.701	Intermediate Similarity	NPD7701	Phase 2
0.7006	Intermediate Similarity	NPD2403	Approved
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6233	Phase 2
0.698	Remote Similarity	NPD6671	Approved
0.6977	Remote Similarity	NPD8455	Phase 2
0.6974	Remote Similarity	NPD17	Approved
0.697	Remote Similarity	NPD8166	Discontinued
0.6949	Remote Similarity	NPD5242	Approved
0.6948	Remote Similarity	NPD1481	Phase 2
0.6944	Remote Similarity	NPD1729	Discontinued
0.6941	Remote Similarity	NPD5808	Clinical (unspecified phase)

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