NPASS Compound

Structure

NPC232275 OpenBabel07101719242D 25 26 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 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 9.5263 1.5000 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 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 7.7942 1.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 8.6603 2.0000 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 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 19 1 0 0 0 0 7 12 1 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 13 2 1 1 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	365.496
LogP:	3.55
LogD:	3.806
LogS:	-3.516
# Rotatable Bonds:	7
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	3.128
Fsp3:	0.4
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:	-4.835
MDCK Permeability:	1.5038486708363052e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.699
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	97.77642059326172%
Volume Distribution (VD):	0.988
Pgp-substrate:	2.470179796218872%

ADMET: Metabolism

CYP1A2-inhibitor:	0.892
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.781
CYP2C19-substrate:	0.368
CYP2C9-inhibitor:	0.792
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.765
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.513

ADMET: Excretion

Clearance (CL):	14.815
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.347
AMES Toxicity:	0.144
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.55
Skin Sensitization:	0.949
Carcinogencity:	0.165
Eye Corrosion:	0.056
Eye Irritation:	0.935
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC232275

Natural Product ID:	NPC232275
*Common Name:**	4-[(2S,3S)-4-(3-Hydroxy-4-Methoxyphenyl)-2,3-Dimethylbutyl]-6-Methoxybenzene-1,3-Diol
IUPAC Name:	4-[(2S,3S)-4-(3-hydroxy-4-methoxyphenyl)-2,3-dimethylbutyl]-6-methoxybenzene-1,3-diol
Synonyms:
Standard InCHIKey:	ZOOFDRPDTGLOSE-STQMWFEESA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-12(7-14-5-6-19(24-3)17(22)9-14)13(2)8-15-10-20(25-4)18(23)11-16(15)21/h5-6,9-13,21-23H,7-8H2,1-4H3/t12-,13-/m0/s1
SMILES:	C[C@@H](Cc1ccc(c(c1)O)OC)[C@@H](C)Cc1cc(c(cc1O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL363230
PubChem CID:	11290949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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	1
Others	3

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3118	Cell Line	Cell line	Homo sapiens	IC50	=	3300.0	nM	PMID[468377]
NPT3118	Cell Line	Cell line	Homo sapiens	Activity	=	7.66	AU/mm	PMID[468377]
NPT3118	Cell Line	Cell line	Homo sapiens	Activity	=	6.45	AU/mm	PMID[468377]
NPT3118	Cell Line	Cell line	Homo sapiens	Activity	=	358.9	nmol/mg LDL	PMID[468377]

☑ 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 NPC232275 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	424
0.1-0.2	1617
0.2-0.3	4818
0.3-0.4	13205
0.4-0.5	4771
0.5-0.6	4166
0.6-0.7	7358
0.7-0.8	4732
0.8-0.85	865
0.85-0.9	464
0.9-0.95	260
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.992	High Similarity	NPC6451
0.984	High Similarity	NPC474356
0.984	High Similarity	NPC12275
0.984	High Similarity	NPC45715
0.976	High Similarity	NPC299221
0.976	High Similarity	NPC234488
0.976	High Similarity	NPC224157
0.976	High Similarity	NPC311680
0.976	High Similarity	NPC192687
0.976	High Similarity	NPC51840
0.968	High Similarity	NPC58164
0.968	High Similarity	NPC10225
0.968	High Similarity	NPC190144
0.96	High Similarity	NPC266691
0.952	High Similarity	NPC159968
0.952	High Similarity	NPC82679
0.952	High Similarity	NPC74817
0.952	High Similarity	NPC127587
0.952	High Similarity	NPC236791
0.952	High Similarity	NPC124452
0.952	High Similarity	NPC324112
0.952	High Similarity	NPC169474
0.952	High Similarity	NPC246620
0.952	High Similarity	NPC282000
0.952	High Similarity	NPC293054
0.9466	High Similarity	NPC25966
0.9466	High Similarity	NPC127218
0.9466	High Similarity	NPC319647
0.9466	High Similarity	NPC245207
0.9462	High Similarity	NPC300846
0.9462	High Similarity	NPC476639
0.9462	High Similarity	NPC114155
0.9449	High Similarity	NPC126836
0.9444	High Similarity	NPC154866
0.944	High Similarity	NPC44748
0.944	High Similarity	NPC76451
0.944	High Similarity	NPC223136
0.944	High Similarity	NPC103823
0.944	High Similarity	NPC18924
0.944	High Similarity	NPC28730
0.944	High Similarity	NPC78974
0.944	High Similarity	NPC214406
0.9394	High Similarity	NPC284464
0.9394	High Similarity	NPC160283
0.9394	High Similarity	NPC254759
0.9389	High Similarity	NPC90615
0.9389	High Similarity	NPC6262
0.9389	High Similarity	NPC276490
0.9389	High Similarity	NPC201145
0.9389	High Similarity	NPC73535
0.9389	High Similarity	NPC272157
0.9389	High Similarity	NPC25111
0.9375	High Similarity	NPC474017
0.937	High Similarity	NPC212015
0.9365	High Similarity	NPC266555
0.9365	High Similarity	NPC252131
0.936	High Similarity	NPC265483
0.936	High Similarity	NPC203133
0.936	High Similarity	NPC193544
0.936	High Similarity	NPC233410
0.936	High Similarity	NPC208950
0.936	High Similarity	NPC298757
0.936	High Similarity	NPC234400
0.936	High Similarity	NPC82483
0.936	High Similarity	NPC221077
0.936	High Similarity	NPC116907
0.936	High Similarity	NPC117214
0.936	High Similarity	NPC60885
0.936	High Similarity	NPC251855
0.936	High Similarity	NPC17943
0.936	High Similarity	NPC472093
0.936	High Similarity	NPC105925
0.936	High Similarity	NPC299584
0.936	High Similarity	NPC475169
0.936	High Similarity	NPC57490
0.9355	High Similarity	NPC121115
0.9355	High Similarity	NPC197757
0.9355	High Similarity	NPC228922
0.9323	High Similarity	NPC471389
0.9318	High Similarity	NPC79622
0.9318	High Similarity	NPC30951
0.9318	High Similarity	NPC292882
0.9318	High Similarity	NPC212942
0.9318	High Similarity	NPC29868
0.9318	High Similarity	NPC6369
0.9313	High Similarity	NPC265433
0.9313	High Similarity	NPC248727
0.9313	High Similarity	NPC173660
0.9313	High Similarity	NPC270456
0.9313	High Similarity	NPC472336
0.9313	High Similarity	NPC472334
0.9313	High Similarity	NPC162659
0.9308	High Similarity	NPC276026
0.9308	High Similarity	NPC206737
0.9308	High Similarity	NPC469659
0.9308	High Similarity	NPC56764
0.9308	High Similarity	NPC7515
0.9308	High Similarity	NPC188378
0.9308	High Similarity	NPC555
0.9308	High Similarity	NPC289258
0.9297	High Similarity	NPC214860
0.9291	High Similarity	NPC28765
0.9286	High Similarity	NPC223953
0.9286	High Similarity	NPC112596
0.928	High Similarity	NPC183446
0.9274	High Similarity	NPC135414
0.9274	High Similarity	NPC41562
0.9254	High Similarity	NPC107161
0.9248	High Similarity	NPC73505
0.9248	High Similarity	NPC165026
0.9248	High Similarity	NPC259519
0.9248	High Similarity	NPC34431
0.9248	High Similarity	NPC295719
0.9242	High Similarity	NPC326797
0.9242	High Similarity	NPC103976
0.9242	High Similarity	NPC107551
0.9242	High Similarity	NPC102904
0.9242	High Similarity	NPC176051
0.9242	High Similarity	NPC474282
0.9237	High Similarity	NPC283009
0.9237	High Similarity	NPC55239
0.9237	High Similarity	NPC240279
0.9237	High Similarity	NPC195022
0.9237	High Similarity	NPC472337
0.9237	High Similarity	NPC313081
0.9237	High Similarity	NPC261873
0.9237	High Similarity	NPC256262
0.9237	High Similarity	NPC180602
0.9237	High Similarity	NPC111655
0.9237	High Similarity	NPC214853
0.9231	High Similarity	NPC158331
0.9231	High Similarity	NPC32778
0.9219	High Similarity	NPC170844
0.9219	High Similarity	NPC476968
0.9219	High Similarity	NPC45824
0.9213	High Similarity	NPC236760
0.92	High Similarity	NPC95168
0.92	High Similarity	NPC282496
0.92	High Similarity	NPC136319
0.92	High Similarity	NPC233526
0.9185	High Similarity	NPC477616
0.9179	High Similarity	NPC247291
0.9179	High Similarity	NPC311530
0.9173	High Similarity	NPC260741
0.9173	High Similarity	NPC471388
0.9173	High Similarity	NPC184613
0.9173	High Similarity	NPC70682
0.9167	High Similarity	NPC143139
0.9167	High Similarity	NPC202846
0.9167	High Similarity	NPC205442
0.9167	High Similarity	NPC197166
0.9167	High Similarity	NPC133025
0.916	High Similarity	NPC209199
0.916	High Similarity	NPC317380
0.916	High Similarity	NPC106215
0.916	High Similarity	NPC103967
0.916	High Similarity	NPC287745
0.9154	High Similarity	NPC202762
0.9154	High Similarity	NPC127624
0.9154	High Similarity	NPC175067
0.9154	High Similarity	NPC86655
0.9154	High Similarity	NPC204215
0.9141	High Similarity	NPC186843
0.9141	High Similarity	NPC206615
0.9141	High Similarity	NPC470213
0.9141	High Similarity	NPC98631
0.9134	High Similarity	NPC245060
0.9127	High Similarity	NPC5796
0.9127	High Similarity	NPC206487
0.912	High Similarity	NPC262253
0.912	High Similarity	NPC71579
0.912	High Similarity	NPC473411
0.912	High Similarity	NPC246967
0.9118	High Similarity	NPC12641
0.9118	High Similarity	NPC93323
0.9118	High Similarity	NPC280092
0.9118	High Similarity	NPC45257
0.9111	High Similarity	NPC175838
0.9104	High Similarity	NPC184797
0.9104	High Similarity	NPC27495
0.9104	High Similarity	NPC309124
0.9098	High Similarity	NPC156948
0.9098	High Similarity	NPC46277
0.9098	High Similarity	NPC86605
0.9098	High Similarity	NPC3072
0.9098	High Similarity	NPC301765
0.9091	High Similarity	NPC200557
0.9091	High Similarity	NPC255147
0.9091	High Similarity	NPC294884
0.9091	High Similarity	NPC158142
0.9091	High Similarity	NPC69029
0.9091	High Similarity	NPC10314
0.9091	High Similarity	NPC94750
0.9091	High Similarity	NPC99572
0.9091	High Similarity	NPC112939
0.9091	High Similarity	NPC126409
0.9091	High Similarity	NPC470356
0.9091	High Similarity	NPC201357
0.9091	High Similarity	NPC121812
0.9091	High Similarity	NPC134968

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 NPC232275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	928
0.2-0.3	1784
0.3-0.4	2808
0.4-0.5	1602
0.5-0.6	893
0.6-0.7	645
0.7-0.8	116
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9219	High Similarity	NPD3027	Phase 3
0.8846	High Similarity	NPD1529	Clinical (unspecified phase)
0.8769	High Similarity	NPD1530	Clinical (unspecified phase)
0.8722	High Similarity	NPD1612	Clinical (unspecified phase)
0.8722	High Similarity	NPD1613	Approved
0.8468	Intermediate Similarity	NPD5283	Phase 1
0.8346	Intermediate Similarity	NPD3018	Phase 2
0.8306	Intermediate Similarity	NPD228	Approved
0.8284	Intermediate Similarity	NPD4908	Phase 1
0.8182	Intermediate Similarity	NPD2982	Phase 2
0.8182	Intermediate Similarity	NPD2983	Phase 2
0.8168	Intermediate Similarity	NPD1610	Phase 2
0.8162	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8145	Intermediate Similarity	NPD3021	Approved
0.8145	Intermediate Similarity	NPD3022	Approved
0.8121	Intermediate Similarity	NPD2801	Approved
0.8106	Intermediate Similarity	NPD2981	Phase 2
0.8074	Intermediate Similarity	NPD2861	Phase 2
0.8045	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1934	Approved
0.791	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD4749	Approved
0.7863	Intermediate Similarity	NPD1548	Phase 1
0.7826	Intermediate Similarity	NPD4625	Phase 3
0.7792	Intermediate Similarity	NPD6234	Discontinued
0.7786	Intermediate Similarity	NPD3620	Phase 2
0.7786	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4060	Phase 1
0.7785	Intermediate Similarity	NPD1653	Approved
0.7769	Intermediate Similarity	NPD6671	Approved
0.7763	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4750	Phase 3
0.7708	Intermediate Similarity	NPD3540	Phase 1
0.7697	Intermediate Similarity	NPD37	Approved
0.7662	Intermediate Similarity	NPD3882	Suspended
0.7643	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3539	Phase 1
0.7635	Intermediate Similarity	NPD1511	Approved
0.7619	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD846	Approved
0.7581	Intermediate Similarity	NPD940	Approved
0.7568	Intermediate Similarity	NPD7124	Phase 2
0.7548	Intermediate Similarity	NPD4966	Approved
0.7548	Intermediate Similarity	NPD4967	Phase 2
0.7548	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4965	Approved
0.7547	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6166	Phase 2
0.7547	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1558	Phase 1
0.7533	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1512	Approved
0.7532	Intermediate Similarity	NPD6232	Discontinued
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.7517	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1242	Phase 1
0.75	Intermediate Similarity	NPD7473	Discontinued
0.7483	Intermediate Similarity	NPD5177	Phase 3
0.7468	Intermediate Similarity	NPD7199	Phase 2
0.7453	Intermediate Similarity	NPD7228	Approved
0.7419	Intermediate Similarity	NPD3020	Approved
0.7413	Intermediate Similarity	NPD2238	Phase 2
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD5494	Approved
0.74	Intermediate Similarity	NPD4357	Discontinued
0.7394	Intermediate Similarity	NPD5109	Approved
0.7394	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5111	Phase 2
0.7394	Intermediate Similarity	NPD5110	Phase 2
0.7386	Intermediate Similarity	NPD4005	Discontinued
0.7379	Intermediate Similarity	NPD6111	Discontinued
0.7375	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3817	Phase 2
0.7372	Intermediate Similarity	NPD422	Phase 1
0.7368	Intermediate Similarity	NPD7157	Approved
0.7365	Intermediate Similarity	NPD6674	Discontinued
0.7365	Intermediate Similarity	NPD3060	Approved
0.7365	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD2684	Approved
0.7362	Intermediate Similarity	NPD7074	Phase 3
0.7347	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3818	Discontinued
0.7344	Intermediate Similarity	NPD968	Approved
0.7343	Intermediate Similarity	NPD2674	Phase 3
0.7338	Intermediate Similarity	NPD4675	Approved
0.7338	Intermediate Similarity	NPD4678	Approved
0.7333	Intermediate Similarity	NPD7549	Discontinued
0.7319	Intermediate Similarity	NPD2233	Approved
0.7319	Intermediate Similarity	NPD2230	Approved
0.7319	Intermediate Similarity	NPD2232	Approved
0.7308	Intermediate Similarity	NPD1465	Phase 2
0.7301	Intermediate Similarity	NPD7054	Approved
0.7292	Intermediate Similarity	NPD1240	Approved
0.7292	Intermediate Similarity	NPD943	Approved
0.7279	Intermediate Similarity	NPD6099	Approved
0.7279	Intermediate Similarity	NPD6100	Approved
0.7279	Intermediate Similarity	NPD1357	Approved
0.7278	Intermediate Similarity	NPD4055	Discovery
0.7273	Intermediate Similarity	NPD7843	Approved
0.7273	Intermediate Similarity	NPD3145	Approved
0.7273	Intermediate Similarity	NPD7635	Approved
0.7273	Intermediate Similarity	NPD3144	Approved
0.7267	Intermediate Similarity	NPD2219	Phase 1
0.7256	Intermediate Similarity	NPD7472	Approved
0.7246	Intermediate Similarity	NPD1091	Approved
0.7241	Intermediate Similarity	NPD6355	Discontinued
0.7237	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7266	Discontinued
0.7229	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4626	Approved
0.7226	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2922	Phase 1
0.7214	Intermediate Similarity	NPD8651	Approved
0.7214	Intermediate Similarity	NPD6696	Suspended
0.7211	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1510	Phase 2
0.7203	Intermediate Similarity	NPD7095	Approved
0.72	Intermediate Similarity	NPD3892	Phase 2
0.7192	Intermediate Similarity	NPD4097	Suspended
0.7192	Intermediate Similarity	NPD1607	Approved
0.7181	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2860	Approved
0.7177	Intermediate Similarity	NPD2859	Approved
0.7174	Intermediate Similarity	NPD3496	Discontinued
0.7171	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD8054	Approved
0.7143	Intermediate Similarity	NPD6895	Approved
0.7143	Intermediate Similarity	NPD6896	Approved
0.7143	Intermediate Similarity	NPD4538	Approved
0.7143	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8053	Approved
0.7143	Intermediate Similarity	NPD4536	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7447	Phase 1
0.7123	Intermediate Similarity	NPD230	Phase 1
0.7114	Intermediate Similarity	NPD5762	Approved
0.7114	Intermediate Similarity	NPD5763	Approved
0.7113	Intermediate Similarity	NPD6584	Phase 3
0.7108	Intermediate Similarity	NPD6797	Phase 2
0.7103	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD2668	Approved
0.7101	Intermediate Similarity	NPD2667	Approved
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD9296	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7089	Intermediate Similarity	NPD2978	Approved
0.7089	Intermediate Similarity	NPD2977	Approved
0.7086	Intermediate Similarity	NPD6331	Phase 2
0.7086	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4110	Phase 3
0.7086	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3750	Approved
0.707	Intermediate Similarity	NPD5090	Approved
0.707	Intermediate Similarity	NPD5089	Approved
0.7066	Intermediate Similarity	NPD7251	Discontinued
0.7063	Intermediate Similarity	NPD9494	Approved
0.7059	Intermediate Similarity	NPD7212	Phase 2
0.7059	Intermediate Similarity	NPD7340	Approved
0.7059	Intermediate Similarity	NPD7213	Phase 3
0.7051	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5451	Approved
0.7044	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3094	Phase 2
0.7042	Intermediate Similarity	NPD2797	Approved
0.7039	Intermediate Similarity	NPD2677	Approved
0.7039	Intermediate Similarity	NPD6190	Approved
0.7034	Intermediate Similarity	NPD6798	Discontinued
0.7024	Intermediate Similarity	NPD7808	Phase 3
0.702	Intermediate Similarity	NPD4237	Approved
0.702	Intermediate Similarity	NPD1652	Phase 2
0.702	Intermediate Similarity	NPD4236	Phase 3
0.7014	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4123	Phase 3
0.7013	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5735	Approved
0.7007	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5124	Phase 1
0.7007	Intermediate Similarity	NPD3657	Discovery
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1611	Approved
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1375	Discontinued
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4624	Approved
0.6985	Remote Similarity	NPD709	Approved
0.6984	Remote Similarity	NPD288	Approved
0.698	Remote Similarity	NPD5588	Approved
0.698	Remote Similarity	NPD5960	Phase 3
0.6978	Remote Similarity	NPD6516	Phase 2
0.6978	Remote Similarity	NPD5846	Approved
0.6972	Remote Similarity	NPD1283	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