NPASS Compound

Structure

CID209199 OpenBabel06191716002D 28 30 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 0.0000 3.0000 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 -0.8660 -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 -4.3301 -0.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 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 -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 -4.3301 1.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 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 0.0000 1.0000 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 -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 -4.3301 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 2.5000 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 11 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 12 2 1 1 0 0 0 12 19 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 22 2 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 21 2 0 0 0 0 18 27 1 0 0 0 0 19 13 1 6 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.11
Volume:	284.522
LogP:	1.039
LogD:	1.221
LogS:	-2.566
# Rotatable Bonds:	4
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.786
Synthetic Accessibility Score:	3.507
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.742
MDCK Permeability:	4.550829908112064e-05
Pgp-inhibitor:	0.924
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	38.05131912231445%
Volume Distribution (VD):	1.072
Pgp-substrate:	45.92876052856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.897
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.463
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.732

ADMET: Excretion

Clearance (CL):	5.27
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.277
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.7
AMES Toxicity:	0.198
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.264
Skin Sensitization:	0.805
Carcinogencity:	0.112
Eye Corrosion:	0.007
Eye Irritation:	0.296
Respiratory Toxicity:	0.477

Download Data

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

Natural Product: NPC209199

Natural Product ID:	NPC209199
*Common Name:**	Sacidumlignan B
IUPAC Name:	(5R,6S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-1,3-dimethoxy-6,7-dimethyl-5,6-dihydronaphthalen-2-ol
Synonyms:	sacidumlignan B
Standard InCHIKey:	FTMPPAUMNSIYCL-CWTRNNRKSA-N
Standard InCHI:	InChI=1S/C22H26O6/c1-11-7-15-14(10-18(27-5)21(24)22(15)28-6)19(12(11)2)13-8-16(25-3)20(23)17(9-13)26-4/h7-10,12,19,23-24H,1-6H3/t12-,19-/m1/s1
SMILES:	CC1=Cc2c(cc(c(c2OC)O)OC)[C@H]([C@@H]1C)c1cc(c(c(c1)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523253
PubChem CID:	11315171
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin 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
NPO33067	sarcostemma acidum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730247]
NPO11787	Orthosiphon wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11787	Orthosiphon wulfenioides	Species	Lamiaceae	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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	130000.0	nM	PMID[476896]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	130000.0	nM	PMID[476896]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	130000.0	nM	PMID[476896]

☑ 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 NPC209199 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	435
0.1-0.2	1660
0.2-0.3	4557
0.3-0.4	12839
0.4-0.5	5368
0.5-0.6	3969
0.6-0.7	7156
0.7-0.8	5064
0.8-0.85	896
0.85-0.9	499
0.9-0.95	211
0.95-1	43

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC313081
0.969	High Similarity	NPC125649
0.9688	High Similarity	NPC161958
0.9688	High Similarity	NPC14224
0.9615	High Similarity	NPC108198
0.9615	High Similarity	NPC10314
0.9615	High Similarity	NPC200557
0.9615	High Similarity	NPC294884
0.9615	High Similarity	NPC158142
0.9615	High Similarity	NPC69029
0.9545	High Similarity	NPC230124
0.9545	High Similarity	NPC6300
0.9545	High Similarity	NPC114171
0.9545	High Similarity	NPC184613
0.9542	High Similarity	NPC143139
0.9542	High Similarity	NPC202846
0.9531	High Similarity	NPC126836
0.947	High Similarity	NPC22902
0.947	High Similarity	NPC56329
0.947	High Similarity	NPC242715
0.9466	High Similarity	NPC241241
0.9398	High Similarity	NPC79622
0.9398	High Similarity	NPC212942
0.9398	High Similarity	NPC275061
0.9398	High Similarity	NPC220344
0.9398	High Similarity	NPC243996
0.9398	High Similarity	NPC132804
0.9398	High Similarity	NPC29868
0.9394	High Similarity	NPC30632
0.9389	High Similarity	NPC206737
0.9389	High Similarity	NPC56764
0.9389	High Similarity	NPC7515
0.9389	High Similarity	NPC188378
0.9389	High Similarity	NPC555
0.9389	High Similarity	NPC469659
0.9389	High Similarity	NPC160697
0.9389	High Similarity	NPC289258
0.9389	High Similarity	NPC276026
0.9375	High Similarity	NPC28765
0.937	High Similarity	NPC76451
0.9333	High Similarity	NPC191231
0.9328	High Similarity	NPC12668
0.9328	High Similarity	NPC308768
0.9323	High Similarity	NPC200935
0.9323	High Similarity	NPC230919
0.9323	High Similarity	NPC266453
0.9318	High Similarity	NPC55239
0.9318	High Similarity	NPC180602
0.9318	High Similarity	NPC214853
0.9318	High Similarity	NPC240279
0.9313	High Similarity	NPC32778
0.9308	High Similarity	NPC15543
0.9297	High Similarity	NPC82679
0.9297	High Similarity	NPC159968
0.9297	High Similarity	NPC282000
0.9297	High Similarity	NPC74817
0.9297	High Similarity	NPC236791
0.9297	High Similarity	NPC169474
0.9297	High Similarity	NPC246620
0.9297	High Similarity	NPC293054
0.9297	High Similarity	NPC252131
0.9297	High Similarity	NPC324112
0.9297	High Similarity	NPC124452
0.9297	High Similarity	NPC127587
0.9254	High Similarity	NPC105847
0.9254	High Similarity	NPC243759
0.9254	High Similarity	NPC218131
0.9248	High Similarity	NPC133025
0.9248	High Similarity	NPC205442
0.9237	High Similarity	NPC6451
0.9225	High Similarity	NPC154866
0.9219	High Similarity	NPC103823
0.9219	High Similarity	NPC44748
0.9219	High Similarity	NPC18924
0.9219	High Similarity	NPC78974
0.9219	High Similarity	NPC214406
0.9219	High Similarity	NPC223136
0.9219	High Similarity	NPC28730
0.9197	High Similarity	NPC469795
0.9191	High Similarity	NPC175838
0.9191	High Similarity	NPC470917
0.9191	High Similarity	NPC183709
0.9179	High Similarity	NPC156948
0.9179	High Similarity	NPC266006
0.9179	High Similarity	NPC86605
0.9179	High Similarity	NPC46277
0.9179	High Similarity	NPC151656
0.9179	High Similarity	NPC301765
0.9179	High Similarity	NPC3072
0.916	High Similarity	NPC12275
0.916	High Similarity	NPC232275
0.916	High Similarity	NPC474356
0.916	High Similarity	NPC45715
0.9147	High Similarity	NPC266555
0.9147	High Similarity	NPC236760
0.9147	High Similarity	NPC471986
0.9141	High Similarity	NPC221077
0.9141	High Similarity	NPC17943
0.9141	High Similarity	NPC208950
0.9141	High Similarity	NPC60885
0.9141	High Similarity	NPC105925
0.9141	High Similarity	NPC475169
0.9141	High Similarity	NPC82483
0.9141	High Similarity	NPC265483
0.9141	High Similarity	NPC233410
0.9141	High Similarity	NPC193544
0.9141	High Similarity	NPC203133
0.9141	High Similarity	NPC116907
0.9141	High Similarity	NPC234400
0.9141	High Similarity	NPC298757
0.9141	High Similarity	NPC9067
0.9141	High Similarity	NPC251855
0.9141	High Similarity	NPC117214
0.9141	High Similarity	NPC472093
0.9141	High Similarity	NPC299584
0.9141	High Similarity	NPC57490
0.9118	High Similarity	NPC472089
0.9111	High Similarity	NPC260741
0.9111	High Similarity	NPC70682
0.9111	High Similarity	NPC471183
0.9104	High Similarity	NPC265433
0.9104	High Similarity	NPC248727
0.9104	High Similarity	NPC270456
0.9104	High Similarity	NPC162659
0.9098	High Similarity	NPC311256
0.9098	High Similarity	NPC317380
0.9091	High Similarity	NPC228843
0.9091	High Similarity	NPC127624
0.9084	High Similarity	NPC234488
0.9084	High Similarity	NPC51840
0.9084	High Similarity	NPC224157
0.9084	High Similarity	NPC192687
0.9084	High Similarity	NPC299221
0.9084	High Similarity	NPC311680
0.907	High Similarity	NPC223953
0.9065	High Similarity	NPC112251
0.9058	High Similarity	NPC473108
0.9051	High Similarity	NPC472087
0.9051	High Similarity	NPC472088
0.9044	High Similarity	NPC259519
0.9044	High Similarity	NPC472091
0.9044	High Similarity	NPC472090
0.9044	High Similarity	NPC165026
0.9044	High Similarity	NPC295719
0.9044	High Similarity	NPC73505
0.9044	High Similarity	NPC472092
0.9044	High Similarity	NPC34431
0.9037	High Similarity	NPC201145
0.9037	High Similarity	NPC25111
0.9037	High Similarity	NPC90615
0.9037	High Similarity	NPC73535
0.9037	High Similarity	NPC272157
0.9037	High Similarity	NPC6262
0.903	High Similarity	NPC256262
0.9015	High Similarity	NPC474017
0.9008	High Similarity	NPC58164
0.9008	High Similarity	NPC212015
0.9008	High Similarity	NPC190144
0.9008	High Similarity	NPC10225
0.8992	High Similarity	NPC266705
0.8992	High Similarity	NPC228771
0.8992	High Similarity	NPC29008
0.8986	High Similarity	NPC469630
0.8984	High Similarity	NPC121115
0.8984	High Similarity	NPC95168
0.8984	High Similarity	NPC197757
0.8984	High Similarity	NPC136319
0.8984	High Similarity	NPC228922
0.8984	High Similarity	NPC282496
0.8984	High Similarity	NPC233526
0.8978	High Similarity	NPC265075
0.8978	High Similarity	NPC71046
0.8978	High Similarity	NPC35216
0.8971	High Similarity	NPC25966
0.8971	High Similarity	NPC245207
0.8971	High Similarity	NPC32630
0.8971	High Similarity	NPC127218
0.8971	High Similarity	NPC319647
0.8963	High Similarity	NPC476639
0.8963	High Similarity	NPC114155
0.8963	High Similarity	NPC234952
0.8963	High Similarity	NPC300846
0.8947	High Similarity	NPC204215
0.8947	High Similarity	NPC102256
0.8947	High Similarity	NPC202762
0.8947	High Similarity	NPC86655
0.8947	High Similarity	NPC175067
0.8931	High Similarity	NPC98631
0.8931	High Similarity	NPC206615
0.8931	High Similarity	NPC186843
0.8931	High Similarity	NPC266691
0.8931	High Similarity	NPC470213
0.8929	High Similarity	NPC233980
0.8923	High Similarity	NPC170485
0.8921	High Similarity	NPC50250
0.8915	High Similarity	NPC5796
0.8915	High Similarity	NPC206487
0.8913	High Similarity	NPC2613
0.8913	High Similarity	NPC204347
0.8913	High Similarity	NPC184684

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 NPC209199 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	960
0.2-0.3	1744
0.3-0.4	2812
0.4-0.5	1621
0.5-0.6	879
0.6-0.7	615
0.7-0.8	140
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD3027	Phase 3
0.8712	High Similarity	NPD1530	Clinical (unspecified phase)
0.8647	High Similarity	NPD1529	Clinical (unspecified phase)
0.8529	High Similarity	NPD1613	Approved
0.8529	High Similarity	NPD1612	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD4625	Phase 3
0.8271	Intermediate Similarity	NPD4749	Approved
0.8261	Intermediate Similarity	NPD3620	Phase 2
0.8261	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4908	Phase 1
0.8224	Intermediate Similarity	NPD6234	Discontinued
0.8222	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD3018	Phase 2
0.8133	Intermediate Similarity	NPD37	Approved
0.8125	Intermediate Similarity	NPD5283	Phase 1
0.812	Intermediate Similarity	NPD1610	Phase 2
0.8116	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2983	Phase 2
0.8	Intermediate Similarity	NPD2982	Phase 2
0.8	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD4965	Approved
0.7974	Intermediate Similarity	NPD4967	Phase 2
0.7974	Intermediate Similarity	NPD4966	Approved
0.7969	Intermediate Similarity	NPD228	Approved
0.7926	Intermediate Similarity	NPD2981	Phase 2
0.7872	Intermediate Similarity	NPD4060	Phase 1
0.7862	Intermediate Similarity	NPD7228	Approved
0.7834	Intermediate Similarity	NPD6232	Discontinued
0.782	Intermediate Similarity	NPD1548	Phase 1
0.7812	Intermediate Similarity	NPD3021	Approved
0.7812	Intermediate Similarity	NPD3022	Approved
0.7812	Intermediate Similarity	NPD4750	Phase 3
0.7808	Intermediate Similarity	NPD6674	Discontinued
0.7799	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD1934	Approved
0.7737	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2801	Approved
0.7697	Intermediate Similarity	NPD4005	Discontinued
0.7687	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7199	Phase 2
0.7643	Intermediate Similarity	NPD2861	Phase 2
0.7603	Intermediate Similarity	NPD6099	Approved
0.7603	Intermediate Similarity	NPD6100	Approved
0.7591	Intermediate Similarity	NPD3705	Approved
0.7562	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3540	Phase 1
0.7517	Intermediate Similarity	NPD4097	Suspended
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD3539	Phase 1
0.7448	Intermediate Similarity	NPD3657	Discovery
0.7445	Intermediate Similarity	NPD4626	Approved
0.7432	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8651	Approved
0.7425	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7124	Phase 2
0.7407	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6166	Phase 2
0.7407	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1653	Approved
0.74	Intermediate Similarity	NPD3750	Approved
0.7386	Intermediate Similarity	NPD1512	Approved
0.7383	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1558	Phase 1
0.7361	Intermediate Similarity	NPD5109	Approved
0.7361	Intermediate Similarity	NPD5111	Phase 2
0.7361	Intermediate Similarity	NPD5110	Phase 2
0.7358	Intermediate Similarity	NPD4055	Discovery
0.7351	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7240	Approved
0.7347	Intermediate Similarity	NPD6111	Discontinued
0.7329	Intermediate Similarity	NPD5735	Approved
0.7324	Intermediate Similarity	NPD4624	Approved
0.7321	Intermediate Similarity	NPD8054	Approved
0.7321	Intermediate Similarity	NPD8053	Approved
0.7315	Intermediate Similarity	NPD5762	Approved
0.7315	Intermediate Similarity	NPD5763	Approved
0.7305	Intermediate Similarity	NPD6696	Suspended
0.7301	Intermediate Similarity	NPD2489	Approved
0.7301	Intermediate Similarity	NPD27	Approved
0.7285	Intermediate Similarity	NPD3892	Phase 2
0.7273	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD940	Approved
0.7261	Intermediate Similarity	NPD5089	Approved
0.7261	Intermediate Similarity	NPD5090	Approved
0.7255	Intermediate Similarity	NPD4357	Discontinued
0.7254	Intermediate Similarity	NPD3094	Phase 2
0.725	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2969	Approved
0.7239	Intermediate Similarity	NPD2970	Approved
0.7233	Intermediate Similarity	NPD3817	Phase 2
0.7229	Intermediate Similarity	NPD7074	Phase 3
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7219	Intermediate Similarity	NPD5177	Phase 3
0.7214	Intermediate Similarity	NPD3092	Approved
0.7214	Intermediate Similarity	NPD422	Phase 1
0.7212	Intermediate Similarity	NPD3818	Discontinued
0.7208	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4380	Phase 2
0.7188	Intermediate Similarity	NPD1242	Phase 1
0.7183	Intermediate Similarity	NPD1283	Approved
0.7181	Intermediate Similarity	NPD1510	Phase 2
0.717	Intermediate Similarity	NPD7819	Suspended
0.7169	Intermediate Similarity	NPD7054	Approved
0.7162	Intermediate Similarity	NPD1607	Approved
0.716	Intermediate Similarity	NPD7313	Approved
0.716	Intermediate Similarity	NPD5494	Approved
0.716	Intermediate Similarity	NPD7310	Approved
0.716	Intermediate Similarity	NPD7311	Approved
0.716	Intermediate Similarity	NPD7312	Approved
0.7143	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD7041	Phase 2
0.7126	Intermediate Similarity	NPD7472	Approved
0.7124	Intermediate Similarity	NPD2219	Phase 1
0.7122	Intermediate Similarity	NPD1651	Approved
0.7122	Intermediate Similarity	NPD5691	Approved
0.7118	Intermediate Similarity	NPD7309	Approved
0.7117	Intermediate Similarity	NPD6959	Discontinued
0.7115	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5327	Phase 3
0.7111	Intermediate Similarity	NPD7635	Approved
0.7109	Intermediate Similarity	NPD3020	Approved
0.7105	Intermediate Similarity	NPD3060	Approved
0.7097	Intermediate Similarity	NPD2533	Approved
0.7097	Intermediate Similarity	NPD2532	Approved
0.7097	Intermediate Similarity	NPD7447	Phase 1
0.7097	Intermediate Similarity	NPD2534	Approved
0.7095	Intermediate Similarity	NPD5124	Phase 1
0.7095	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4675	Approved
0.7089	Intermediate Similarity	NPD4678	Approved
0.7086	Intermediate Similarity	NPD7266	Discontinued
0.708	Intermediate Similarity	NPD7157	Approved
0.708	Intermediate Similarity	NPD6671	Approved
0.7076	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2674	Phase 3
0.7073	Intermediate Similarity	NPD3051	Approved
0.7068	Intermediate Similarity	NPD2684	Approved
0.7067	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD6331	Phase 2
0.7059	Intermediate Similarity	NPD4577	Approved
0.7059	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD4578	Approved
0.7055	Intermediate Similarity	NPD7095	Approved
0.705	Intermediate Similarity	NPD3091	Approved
0.7042	Intermediate Similarity	NPD2232	Approved
0.7042	Intermediate Similarity	NPD2230	Approved
0.7042	Intermediate Similarity	NPD2233	Approved
0.7037	Intermediate Similarity	NPD7075	Discontinued
0.7035	Intermediate Similarity	NPD4663	Approved
0.7032	Intermediate Similarity	NPD7212	Phase 2
0.7032	Intermediate Similarity	NPD7213	Phase 3
0.7029	Intermediate Similarity	NPD7340	Approved
0.7027	Intermediate Similarity	NPD943	Approved
0.7027	Intermediate Similarity	NPD4140	Approved
0.7025	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2935	Discontinued
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2560	Approved
0.7019	Intermediate Similarity	NPD2563	Approved
0.7013	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5241	Discontinued
0.7013	Intermediate Similarity	NPD2677	Approved
0.7007	Intermediate Similarity	NPD3145	Approved
0.7007	Intermediate Similarity	NPD3144	Approved
0.7	Intermediate Similarity	NPD1357	Approved
0.7	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4536	Approved
0.7	Intermediate Similarity	NPD4538	Approved
0.6994	Remote Similarity	NPD7906	Approved
0.6993	Remote Similarity	NPD1669	Approved
0.6992	Remote Similarity	NPD2342	Discontinued
0.6987	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7843	Approved
0.6982	Remote Similarity	NPD6797	Phase 2
0.6982	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7028	Phase 2
0.698	Remote Similarity	NPD6355	Discontinued
0.698	Remote Similarity	NPD230	Phase 1
0.6974	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1281	Approved
0.6972	Remote Similarity	NPD1091	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