NPASS Compound

Structure

CID14224 OpenBabel06191715342D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 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 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 -4.3301 -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 -0.8660 -0.5000 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 -2.5981 1.5000 0.0000 C 0 0 1 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 -4.3301 -1.5000 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 -6.0622 -0.5000 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 0.8660 1.5000 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 26 1 0 0 0 0 6 11 1 0 0 0 0 6 13 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 19 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 1 1 6 0 0 0 11 12 1 0 0 0 0 12 2 1 6 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 14 1 1 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	374.235
LogP:	3.926
LogD:	3.652
LogS:	-4.815
# Rotatable Bonds:	4
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.862
Synthetic Accessibility Score:	3.439
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.813
MDCK Permeability:	1.8015396562987007e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.281
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.562

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	93.39501953125%
Volume Distribution (VD):	1.874
Pgp-substrate:	6.177465438842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.153
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.393
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.588
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.169
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.898

ADMET: Excretion

Clearance (CL):	14.227
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.799
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.458
Maximum Recommended Daily Dose:	0.809
Skin Sensitization:	0.886
Carcinogencity:	0.054
Eye Corrosion:	0.006
Eye Irritation:	0.757
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC14224

Natural Product ID:	NPC14224
*Common Name:**	(+)-(7's,8S,8's)-4,4'-Dihydroxy-3',5,5'-Trimethoxy-2,7'-Cyclolignan
IUPAC Name:	(6S,7S,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
Synonyms:
Standard InCHIKey:	QHLOLFAIJRCECK-PVUDRZGPSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-11-6-13-7-17(24-3)16(22)10-15(13)20(12(11)2)14-8-18(25-4)21(23)19(9-14)26-5/h7-12,20,22-23H,6H2,1-5H3/t11-,12-,20-/m0/s1
SMILES:	C[C@H]1Cc2cc(c(cc2[C@@H]([C@H]1C)c1cc(c(c(c1)OC)O)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812786
PubChem CID:	53344598
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
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	64.0	%	PMID[512890]

☑ 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 NPC14224 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	434
0.1-0.2	1637
0.2-0.3	4235
0.3-0.4	12403
0.4-0.5	6088
0.5-0.6	4080
0.6-0.7	7836
0.7-0.8	4528
0.8-0.85	821
0.85-0.9	476
0.9-0.95	138
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC161958
0.9766	High Similarity	NPC313081
0.9688	High Similarity	NPC209199
0.9688	High Similarity	NPC125649
0.9612	High Similarity	NPC200557
0.9612	High Similarity	NPC108198
0.9612	High Similarity	NPC294884
0.9612	High Similarity	NPC10314
0.9612	High Similarity	NPC158142
0.9612	High Similarity	NPC69029
0.9542	High Similarity	NPC230124
0.9542	High Similarity	NPC6300
0.9542	High Similarity	NPC114171
0.9542	High Similarity	NPC184613
0.9538	High Similarity	NPC202846
0.9538	High Similarity	NPC143139
0.952	High Similarity	NPC76451
0.9466	High Similarity	NPC22902
0.9466	High Similarity	NPC56329
0.9466	High Similarity	NPC242715
0.9462	High Similarity	NPC241241
0.9444	High Similarity	NPC127587
0.9394	High Similarity	NPC79622
0.9394	High Similarity	NPC275061
0.9394	High Similarity	NPC220344
0.9394	High Similarity	NPC132804
0.9394	High Similarity	NPC243996
0.9394	High Similarity	NPC29868
0.9394	High Similarity	NPC212942
0.9389	High Similarity	NPC30632
0.9385	High Similarity	NPC160697
0.9375	High Similarity	NPC126836
0.9328	High Similarity	NPC191231
0.9323	High Similarity	NPC12668
0.9323	High Similarity	NPC308768
0.9318	High Similarity	NPC230919
0.9318	High Similarity	NPC200935
0.9318	High Similarity	NPC266453
0.9286	High Similarity	NPC208950
0.9286	High Similarity	NPC472093
0.9286	High Similarity	NPC266705
0.9286	High Similarity	NPC203133
0.9286	High Similarity	NPC193544
0.9286	High Similarity	NPC475169
0.9286	High Similarity	NPC17943
0.9286	High Similarity	NPC251855
0.9286	High Similarity	NPC233410
0.9286	High Similarity	NPC298757
0.9286	High Similarity	NPC29008
0.9286	High Similarity	NPC221077
0.9286	High Similarity	NPC116907
0.9286	High Similarity	NPC57490
0.9286	High Similarity	NPC228771
0.9286	High Similarity	NPC117214
0.9248	High Similarity	NPC105847
0.9248	High Similarity	NPC243759
0.9248	High Similarity	NPC218131
0.9242	High Similarity	NPC205442
0.9237	High Similarity	NPC289258
0.9237	High Similarity	NPC7515
0.9237	High Similarity	NPC311256
0.9237	High Similarity	NPC56764
0.9237	High Similarity	NPC276026
0.9237	High Similarity	NPC555
0.9237	High Similarity	NPC188378
0.9237	High Similarity	NPC206737
0.9237	High Similarity	NPC469659
0.9219	High Similarity	NPC28765
0.9185	High Similarity	NPC183709
0.9185	High Similarity	NPC175838
0.9173	High Similarity	NPC266006
0.9173	High Similarity	NPC151656
0.9167	High Similarity	NPC240279
0.9167	High Similarity	NPC180602
0.9167	High Similarity	NPC55239
0.9167	High Similarity	NPC214853
0.916	High Similarity	NPC32778
0.9154	High Similarity	NPC15543
0.9154	High Similarity	NPC474017
0.9141	High Similarity	NPC236791
0.9141	High Similarity	NPC471986
0.9141	High Similarity	NPC293054
0.9141	High Similarity	NPC82679
0.9141	High Similarity	NPC159968
0.9141	High Similarity	NPC324112
0.9141	High Similarity	NPC246620
0.9141	High Similarity	NPC282000
0.9141	High Similarity	NPC169474
0.9141	High Similarity	NPC124452
0.9141	High Similarity	NPC252131
0.9141	High Similarity	NPC74817
0.9134	High Similarity	NPC9067
0.9127	High Similarity	NPC228922
0.9127	High Similarity	NPC233526
0.9127	High Similarity	NPC282496
0.9127	High Similarity	NPC136319
0.9127	High Similarity	NPC197757
0.9111	High Similarity	NPC472089
0.9104	High Similarity	NPC55947
0.9098	High Similarity	NPC133025
0.9091	High Similarity	NPC471942
0.9084	High Similarity	NPC204215
0.9084	High Similarity	NPC6451
0.9084	High Similarity	NPC228843
0.9084	High Similarity	NPC175067
0.907	High Similarity	NPC98631
0.907	High Similarity	NPC154866
0.907	High Similarity	NPC307050
0.907	High Similarity	NPC277458
0.907	High Similarity	NPC186843
0.907	High Similarity	NPC206615
0.907	High Similarity	NPC470213
0.9062	High Similarity	NPC214406
0.9062	High Similarity	NPC103823
0.9062	High Similarity	NPC44748
0.9062	High Similarity	NPC28730
0.9062	High Similarity	NPC78974
0.9062	High Similarity	NPC18924
0.9062	High Similarity	NPC223136
0.9058	High Similarity	NPC112251
0.9055	High Similarity	NPC5796
0.9055	High Similarity	NPC206487
0.9051	High Similarity	NPC469795
0.9048	High Similarity	NPC71579
0.9048	High Similarity	NPC41562
0.9048	High Similarity	NPC473411
0.9048	High Similarity	NPC262253
0.9044	High Similarity	NPC472088
0.9044	High Similarity	NPC472087
0.9044	High Similarity	NPC470917
0.9037	High Similarity	NPC73505
0.9037	High Similarity	NPC472091
0.9037	High Similarity	NPC472092
0.9037	High Similarity	NPC34431
0.9037	High Similarity	NPC295719
0.9037	High Similarity	NPC165026
0.9037	High Similarity	NPC472090
0.903	High Similarity	NPC6262
0.903	High Similarity	NPC272157
0.903	High Similarity	NPC25111
0.903	High Similarity	NPC73535
0.903	High Similarity	NPC301765
0.903	High Similarity	NPC201145
0.903	High Similarity	NPC90615
0.903	High Similarity	NPC3072
0.903	High Similarity	NPC156948
0.903	High Similarity	NPC86605
0.903	High Similarity	NPC46277
0.9015	High Similarity	NPC158331
0.9008	High Similarity	NPC45715
0.9008	High Similarity	NPC12275
0.9008	High Similarity	NPC232275
0.9008	High Similarity	NPC474356
0.9	High Similarity	NPC476968
0.9	High Similarity	NPC170844
0.8992	High Similarity	NPC210355
0.8992	High Similarity	NPC266555
0.8992	High Similarity	NPC236760
0.8984	High Similarity	NPC105925
0.8984	High Similarity	NPC234400
0.8984	High Similarity	NPC82483
0.8984	High Similarity	NPC265483
0.8984	High Similarity	NPC60885
0.8984	High Similarity	NPC299584
0.8978	High Similarity	NPC469630
0.8976	High Similarity	NPC84086
0.8963	High Similarity	NPC260741
0.8963	High Similarity	NPC471183
0.8963	High Similarity	NPC70682
0.8955	High Similarity	NPC248727
0.8955	High Similarity	NPC162659
0.8955	High Similarity	NPC300846
0.8955	High Similarity	NPC265433
0.8955	High Similarity	NPC476639
0.8955	High Similarity	NPC270456
0.8955	High Similarity	NPC114155
0.8947	High Similarity	NPC326095
0.8947	High Similarity	NPC287745
0.8947	High Similarity	NPC317380
0.8947	High Similarity	NPC244983
0.8939	High Similarity	NPC253105
0.8939	High Similarity	NPC127624
0.8939	High Similarity	NPC201587
0.8931	High Similarity	NPC299221
0.8931	High Similarity	NPC234488
0.8931	High Similarity	NPC192687
0.8931	High Similarity	NPC311680
0.8931	High Similarity	NPC51840
0.8931	High Similarity	NPC224157
0.8915	High Similarity	NPC181361
0.8915	High Similarity	NPC223953
0.8915	High Similarity	NPC170485
0.8913	High Similarity	NPC473108
0.8905	High Similarity	NPC277784
0.8898	High Similarity	NPC30462
0.8897	High Similarity	NPC291101
0.8897	High Similarity	NPC259519
0.8897	High Similarity	NPC266197
0.8889	High Similarity	NPC166759
0.8881	High Similarity	NPC126409

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 NPC14224 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	953
0.2-0.3	1691
0.3-0.4	2853
0.4-0.5	1639
0.5-0.6	913
0.6-0.7	609
0.7-0.8	113
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD3027	Phase 3
0.8561	High Similarity	NPD1530	Clinical (unspecified phase)
0.8519	High Similarity	NPD3620	Phase 2
0.8519	High Similarity	NPD3619	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8254	Intermediate Similarity	NPD5283	Phase 1
0.8243	Intermediate Similarity	NPD37	Approved
0.8235	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD4908	Phase 1
0.8162	Intermediate Similarity	NPD4625	Phase 3
0.812	Intermediate Similarity	NPD2983	Phase 2
0.812	Intermediate Similarity	NPD2982	Phase 2
0.8095	Intermediate Similarity	NPD228	Approved
0.8079	Intermediate Similarity	NPD4966	Approved
0.8079	Intermediate Similarity	NPD4965	Approved
0.8079	Intermediate Similarity	NPD4967	Phase 2
0.8045	Intermediate Similarity	NPD2981	Phase 2
0.8015	Intermediate Similarity	NPD3018	Phase 2
0.7985	Intermediate Similarity	NPD4749	Approved
0.797	Intermediate Similarity	NPD1610	Phase 2
0.7962	Intermediate Similarity	NPD7228	Approved
0.7941	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3022	Approved
0.7937	Intermediate Similarity	NPD3021	Approved
0.7852	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6232	Discontinued
0.78	Intermediate Similarity	NPD4005	Discontinued
0.7793	Intermediate Similarity	NPD6674	Discontinued
0.7785	Intermediate Similarity	NPD7473	Discontinued
0.773	Intermediate Similarity	NPD4060	Phase 1
0.7704	Intermediate Similarity	NPD3705	Approved
0.7676	Intermediate Similarity	NPD3657	Discovery
0.7669	Intermediate Similarity	NPD1548	Phase 1
0.7647	Intermediate Similarity	NPD1934	Approved
0.7643	Intermediate Similarity	NPD7199	Phase 2
0.7622	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2801	Approved
0.7597	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4624	Approved
0.7552	Intermediate Similarity	NPD5735	Approved
0.7551	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4750	Phase 3
0.7517	Intermediate Similarity	NPD7124	Phase 2
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD4097	Suspended
0.7483	Intermediate Similarity	NPD1558	Phase 1
0.7482	Intermediate Similarity	NPD3094	Phase 2
0.7469	Intermediate Similarity	NPD5844	Phase 1
0.7466	Intermediate Similarity	NPD6099	Approved
0.7466	Intermediate Similarity	NPD6100	Approved
0.7465	Intermediate Similarity	NPD5110	Phase 2
0.7465	Intermediate Similarity	NPD5109	Approved
0.7465	Intermediate Similarity	NPD5111	Phase 2
0.745	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6111	Discontinued
0.7445	Intermediate Similarity	NPD3092	Approved
0.7439	Intermediate Similarity	NPD7240	Approved
0.7415	Intermediate Similarity	NPD3540	Phase 1
0.7391	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6166	Phase 2
0.7389	Intermediate Similarity	NPD3882	Suspended
0.7372	Intermediate Similarity	NPD1465	Phase 2
0.7368	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4357	Discontinued
0.7351	Intermediate Similarity	NPD1511	Approved
0.7351	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3539	Phase 1
0.7338	Intermediate Similarity	NPD5327	Phase 3
0.7333	Intermediate Similarity	NPD5536	Phase 2
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8053	Approved
0.7305	Intermediate Similarity	NPD8054	Approved
0.7302	Intermediate Similarity	NPD1242	Phase 1
0.7299	Intermediate Similarity	NPD4626	Approved
0.7297	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1283	Approved
0.7279	Intermediate Similarity	NPD3091	Approved
0.7273	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD7095	Approved
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1512	Approved
0.7248	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4140	Approved
0.7233	Intermediate Similarity	NPD4055	Discovery
0.7226	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1651	Approved
0.7222	Intermediate Similarity	NPD3020	Approved
0.7219	Intermediate Similarity	NPD2219	Phase 1
0.7219	Intermediate Similarity	NPD5241	Discontinued
0.72	Intermediate Similarity	NPD3060	Approved
0.719	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD7157	Approved
0.7183	Intermediate Similarity	NPD6584	Phase 3
0.7181	Intermediate Similarity	NPD5762	Approved
0.7181	Intermediate Similarity	NPD7266	Discontinued
0.7181	Intermediate Similarity	NPD5763	Approved
0.7179	Intermediate Similarity	NPD4678	Approved
0.7179	Intermediate Similarity	NPD4675	Approved
0.7176	Intermediate Similarity	NPD2684	Approved
0.7172	Intermediate Similarity	NPD2674	Phase 3
0.7163	Intermediate Similarity	NPD8651	Approved
0.7163	Intermediate Similarity	NPD6696	Suspended
0.716	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD3750	Approved
0.7152	Intermediate Similarity	NPD3892	Phase 2
0.7152	Intermediate Similarity	NPD6331	Phase 2
0.7143	Intermediate Similarity	NPD6353	Approved
0.7143	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5090	Approved
0.7134	Intermediate Similarity	NPD5089	Approved
0.7133	Intermediate Similarity	NPD7037	Approved
0.7125	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7833	Phase 2
0.7125	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7831	Phase 2
0.7124	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7041	Phase 2
0.7123	Intermediate Similarity	NPD2238	Phase 2
0.7121	Intermediate Similarity	NPD5451	Approved
0.7109	Intermediate Similarity	NPD940	Approved
0.7109	Intermediate Similarity	NPD846	Approved
0.7108	Intermediate Similarity	NPD7074	Phase 3
0.7107	Intermediate Similarity	NPD3817	Phase 2
0.7103	Intermediate Similarity	NPD3145	Approved
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3144	Approved
0.7102	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1357	Approved
0.7099	Intermediate Similarity	NPD6959	Discontinued
0.7095	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4536	Approved
0.7095	Intermediate Similarity	NPD4538	Approved
0.7092	Intermediate Similarity	NPD1669	Approved
0.7091	Intermediate Similarity	NPD3818	Discontinued
0.709	Intermediate Similarity	NPD7843	Approved
0.7086	Intermediate Similarity	NPD5177	Phase 3
0.7078	Intermediate Similarity	NPD7447	Phase 1
0.7078	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD230	Phase 1
0.7073	Intermediate Similarity	NPD27	Approved
0.7073	Intermediate Similarity	NPD2489	Approved
0.7071	Intermediate Similarity	NPD1281	Approved
0.7071	Intermediate Similarity	NPD422	Phase 1
0.707	Intermediate Similarity	NPD4380	Phase 2
0.7055	Intermediate Similarity	NPD3051	Approved
0.705	Intermediate Similarity	NPD3019	Approved
0.705	Intermediate Similarity	NPD4059	Approved
0.705	Intermediate Similarity	NPD5846	Approved
0.705	Intermediate Similarity	NPD3095	Discontinued
0.705	Intermediate Similarity	NPD6516	Phase 2
0.7048	Intermediate Similarity	NPD7054	Approved
0.7047	Intermediate Similarity	NPD1510	Phase 2
0.7047	Intermediate Similarity	NPD4108	Discontinued
0.7044	Intermediate Similarity	NPD7819	Suspended
0.7041	Intermediate Similarity	NPD4578	Approved
0.7041	Intermediate Similarity	NPD4577	Approved
0.7039	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4110	Phase 3
0.7037	Intermediate Similarity	NPD5494	Approved
0.7027	Intermediate Similarity	NPD1607	Approved
0.7021	Intermediate Similarity	NPD2232	Approved
0.7021	Intermediate Similarity	NPD2233	Approved
0.7021	Intermediate Similarity	NPD2230	Approved
0.702	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4663	Approved
0.7013	Intermediate Similarity	NPD7212	Phase 2
0.7013	Intermediate Similarity	NPD7213	Phase 3
0.7012	Intermediate Similarity	NPD2970	Approved
0.7012	Intermediate Similarity	NPD2969	Approved
0.7007	Intermediate Similarity	NPD1240	Approved
0.7006	Intermediate Similarity	NPD7472	Approved
0.7006	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6190	Approved
0.6986	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2859	Approved
0.6984	Remote Similarity	NPD2860	Approved
0.6982	Remote Similarity	NPD7549	Discontinued
0.698	Remote Similarity	NPD6896	Approved
0.698	Remote Similarity	NPD6895	Approved
0.6978	Remote Similarity	NPD4093	Discontinued
0.6978	Remote Similarity	NPD5691	Approved
0.6977	Remote Similarity	NPD7906	Approved
0.6974	Remote Similarity	NPD4237	Approved
0.6974	Remote Similarity	NPD4236	Phase 3
0.6972	Remote Similarity	NPD6582	Phase 2
0.6972	Remote Similarity	NPD6583	Phase 3

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