NPASS Compound

Structure

NPC189482 OpenBabel07101718242D 33 37 0 0 0 0 0 0 0 0999 V2000 2.4969 -0.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9232 -2.5365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3933 -2.2306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6583 0.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5622 1.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8271 -0.0531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1284 -2.5365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7629 -2.2023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0516 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3744 -0.8877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6946 1.2965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9596 -0.2061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6583 -2.2306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1285 -1.3398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3292 -1.5558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2887 -3.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2093 -1.1869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6787 -0.2743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1284 0.7747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5258 -2.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2609 -0.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1742 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3933 0.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2609 -1.1869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0516 -1.7619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0516 -2.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0523 -0.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2093 -0.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7568 0.2473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8146 -3.0833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6327 -0.0794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 3 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 9 1 0 0 0 0 4 19 1 0 0 0 0 5 11 1 0 0 0 0 5 19 2 0 0 0 0 6 12 2 0 0 0 0 6 19 1 0 0 0 0 7 13 2 0 0 0 0 7 20 1 0 0 0 0 8 15 2 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 10 23 2 0 0 0 0 11 24 2 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 25 2 0 0 0 0 15 28 1 0 0 0 0 16 20 2 0 0 0 0 16 27 1 0 0 0 0 17 21 2 0 0 0 0 17 29 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 22 25 1 0 0 0 0 23 30 1 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 26 27 2 0 0 0 0 27 31 1 0 0 0 0 28 29 2 0 0 0 0 28 32 1 0 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.18
Volume:	470.881
LogP:	6.592
LogD:	4.416
LogS:	-6.075
# Rotatable Bonds:	1
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	4.576
Fsp3:	0.172
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.356
MDCK Permeability:	9.480441804043949e-06
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.902
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	100.32740020751953%
Volume Distribution (VD):	0.35
Pgp-substrate:	0.6099547743797302%

ADMET: Metabolism

CYP1A2-inhibitor:	0.85
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.686
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.554
CYP2D6-substrate:	0.953
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	9.58
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.487
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.192
AMES Toxicity:	0.254
Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.947
Carcinogencity:	0.424
Eye Corrosion:	0.003
Eye Irritation:	0.493
Respiratory Toxicity:	0.156

Download Data

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

Natural Product: NPC189482

Natural Product ID:	NPC189482
*Common Name:**	Riccardi F
IUPAC Name:	n.a.
Synonyms:	Riccardi F; Riccardin F
Standard InCHIKey:	JYKRDVGMNOVIMG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H26O4/c1-32-28-15-8-21-3-2-20-7-13-26(27(31)16-20)25-14-10-23(30)18-22(25)9-4-19-5-11-24(12-6-19)33-29(28)17-21/h5-8,10-18,30-31H,2-4,9H2,1H3
SMILES:	COc1ccc2CCc3ccc(-c4ccc(cc4CCc4ccc(cc4)Oc1c2)O)c(c3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474806
PubChem CID:	11510446
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO33046	liverworts	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16378374]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO33046	liverworts	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21652215]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30848895]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	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	3
Others	1

Activity Type	# Activity
Cell Line	3
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5000.0	nM	PMID[550561]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	15000.0	nM	PMID[550564]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	30000.0	nM	PMID[550564]
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	>	60.0	%	PMID[550563]

☑ 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 NPC189482 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	459
0.1-0.2	2060
0.2-0.3	5921
0.3-0.4	13064
0.4-0.5	3861
0.5-0.6	5071
0.6-0.7	9240
0.7-0.8	2719
0.8-0.85	283
0.85-0.9	14
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC141023
0.9685	High Similarity	NPC73656
0.9213	High Similarity	NPC156854
0.9213	High Similarity	NPC17837
0.9213	High Similarity	NPC134431
0.9213	High Similarity	NPC304630
0.9	High Similarity	NPC210655
0.8963	High Similarity	NPC55947
0.8939	High Similarity	NPC228843
0.8905	High Similarity	NPC183709
0.8837	High Similarity	NPC228771
0.8837	High Similarity	NPC29008
0.8837	High Similarity	NPC266705
0.8832	High Similarity	NPC472089
0.8797	High Similarity	NPC303144
0.8768	High Similarity	NPC472088
0.8768	High Similarity	NPC472087
0.875	High Similarity	NPC266006
0.875	High Similarity	NPC30462
0.8692	High Similarity	NPC28476
0.8692	High Similarity	NPC9067
0.8692	High Similarity	NPC133407
0.8686	High Similarity	NPC275061
0.8686	High Similarity	NPC220344
0.8686	High Similarity	NPC243996
0.8686	High Similarity	NPC132804
0.8667	High Similarity	NPC66840
0.8667	High Similarity	NPC256307
0.8661	High Similarity	NPC103916
0.8636	High Similarity	NPC307050
0.8636	High Similarity	NPC277458
0.8633	High Similarity	NPC186033
0.8623	High Similarity	NPC472092
0.8623	High Similarity	NPC308768
0.8623	High Similarity	NPC12668
0.8623	High Similarity	NPC22317
0.8623	High Similarity	NPC472090
0.8623	High Similarity	NPC472091
0.8613	High Similarity	NPC242715
0.8613	High Similarity	NPC56329
0.8613	High Similarity	NPC200935
0.8613	High Similarity	NPC266453
0.8613	High Similarity	NPC230919
0.8613	High Similarity	NPC22902
0.8603	High Similarity	NPC158142
0.8603	High Similarity	NPC111655
0.8603	High Similarity	NPC200557
0.8603	High Similarity	NPC10314
0.8603	High Similarity	NPC69029
0.8603	High Similarity	NPC108198
0.8603	High Similarity	NPC294884
0.8571	High Similarity	NPC474227
0.8551	High Similarity	NPC105847
0.8551	High Similarity	NPC243759
0.8551	High Similarity	NPC218131
0.854	High Similarity	NPC114155
0.854	High Similarity	NPC202846
0.854	High Similarity	NPC143139
0.854	High Similarity	NPC300846
0.854	High Similarity	NPC205442
0.854	High Similarity	NPC476639
0.854	High Similarity	NPC30632
0.8529	High Similarity	NPC125649
0.8521	High Similarity	NPC126291
0.8519	High Similarity	NPC131128
0.8519	High Similarity	NPC474134
0.8516	High Similarity	NPC232316
0.8516	High Similarity	NPC227217
0.8516	High Similarity	NPC165133
0.8516	High Similarity	NPC56214
0.8516	High Similarity	NPC242885
0.8516	High Similarity	NPC117780
0.8516	High Similarity	NPC95614
0.8504	High Similarity	NPC470626
0.85	High Similarity	NPC175838
0.85	High Similarity	NPC277784
0.8496	Intermediate Similarity	NPC201069
0.8496	Intermediate Similarity	NPC23012
0.8478	Intermediate Similarity	NPC272157
0.8478	Intermediate Similarity	NPC90615
0.8478	Intermediate Similarity	NPC35550
0.8478	Intermediate Similarity	NPC25111
0.8478	Intermediate Similarity	NPC6262
0.8478	Intermediate Similarity	NPC73535
0.8478	Intermediate Similarity	NPC151656
0.8478	Intermediate Similarity	NPC201145
0.8472	Intermediate Similarity	NPC321657
0.8472	Intermediate Similarity	NPC318373
0.8472	Intermediate Similarity	NPC476969
0.8467	Intermediate Similarity	NPC37410
0.8467	Intermediate Similarity	NPC313081
0.8467	Intermediate Similarity	NPC241241
0.8462	Intermediate Similarity	NPC262297
0.8456	Intermediate Similarity	NPC469610
0.8444	Intermediate Similarity	NPC282508
0.8444	Intermediate Similarity	NPC149337
0.8444	Intermediate Similarity	NPC8899
0.8444	Intermediate Similarity	NPC471983
0.8444	Intermediate Similarity	NPC474238
0.844	Intermediate Similarity	NPC173203
0.844	Intermediate Similarity	NPC163508
0.8438	Intermediate Similarity	NPC281298
0.8438	Intermediate Similarity	NPC310338
0.8433	Intermediate Similarity	NPC471518
0.8433	Intermediate Similarity	NPC471519
0.8429	Intermediate Similarity	NPC470372
0.8425	Intermediate Similarity	NPC86947
0.8425	Intermediate Similarity	NPC293619
0.8421	Intermediate Similarity	NPC21563
0.8421	Intermediate Similarity	NPC106511
0.8417	Intermediate Similarity	NPC212942
0.8417	Intermediate Similarity	NPC29868
0.8417	Intermediate Similarity	NPC79622
0.8417	Intermediate Similarity	NPC260842
0.8406	Intermediate Similarity	NPC170328
0.8406	Intermediate Similarity	NPC472648
0.8406	Intermediate Similarity	NPC472649
0.8406	Intermediate Similarity	NPC191462
0.8406	Intermediate Similarity	NPC206525
0.8406	Intermediate Similarity	NPC133463
0.8406	Intermediate Similarity	NPC472647
0.8403	Intermediate Similarity	NPC329836
0.8397	Intermediate Similarity	NPC31344
0.8397	Intermediate Similarity	NPC317769
0.8394	Intermediate Similarity	NPC71372
0.8394	Intermediate Similarity	NPC311256
0.8394	Intermediate Similarity	NPC160697
0.8394	Intermediate Similarity	NPC478085
0.8394	Intermediate Similarity	NPC471942
0.8392	Intermediate Similarity	NPC233980
0.8385	Intermediate Similarity	NPC38996
0.8385	Intermediate Similarity	NPC127389
0.8385	Intermediate Similarity	NPC160380
0.8385	Intermediate Similarity	NPC290451
0.8382	Intermediate Similarity	NPC227002
0.8382	Intermediate Similarity	NPC469611
0.838	Intermediate Similarity	NPC469795
0.838	Intermediate Similarity	NPC304894
0.838	Intermediate Similarity	NPC15659
0.837	Intermediate Similarity	NPC254000
0.837	Intermediate Similarity	NPC126836
0.8359	Intermediate Similarity	NPC474040
0.8357	Intermediate Similarity	NPC295719
0.8357	Intermediate Similarity	NPC165026
0.8357	Intermediate Similarity	NPC61783
0.8357	Intermediate Similarity	NPC20520
0.8357	Intermediate Similarity	NPC73505
0.8357	Intermediate Similarity	NPC34431
0.8346	Intermediate Similarity	NPC223953
0.8345	Intermediate Similarity	NPC71465
0.8345	Intermediate Similarity	NPC48956
0.8345	Intermediate Similarity	NPC474390
0.8345	Intermediate Similarity	NPC472646
0.8333	Intermediate Similarity	NPC258780
0.8333	Intermediate Similarity	NPC15109
0.8333	Intermediate Similarity	NPC48990
0.8333	Intermediate Similarity	NPC114901
0.8333	Intermediate Similarity	NPC293701
0.8333	Intermediate Similarity	NPC261873
0.8333	Intermediate Similarity	NPC283009
0.8333	Intermediate Similarity	NPC11727
0.8333	Intermediate Similarity	NPC61685
0.8333	Intermediate Similarity	NPC474397
0.8322	Intermediate Similarity	NPC125617
0.8321	Intermediate Similarity	NPC36661
0.8321	Intermediate Similarity	NPC85488
0.8321	Intermediate Similarity	NPC32778
0.831	Intermediate Similarity	NPC469630
0.8309	Intermediate Similarity	NPC473309
0.8309	Intermediate Similarity	NPC471517
0.8308	Intermediate Similarity	NPC207613
0.8308	Intermediate Similarity	NPC129176
0.8299	Intermediate Similarity	NPC476391
0.8299	Intermediate Similarity	NPC474442
0.8298	Intermediate Similarity	NPC265075
0.8286	Intermediate Similarity	NPC184613
0.8286	Intermediate Similarity	NPC22517
0.8284	Intermediate Similarity	NPC471986
0.8284	Intermediate Similarity	NPC100129
0.8281	Intermediate Similarity	NPC25648
0.8281	Intermediate Similarity	NPC299180
0.8276	Intermediate Similarity	NPC212142
0.8273	Intermediate Similarity	NPC77861
0.8273	Intermediate Similarity	NPC270456
0.8273	Intermediate Similarity	NPC141717
0.8273	Intermediate Similarity	NPC248727
0.8273	Intermediate Similarity	NPC234952
0.8273	Intermediate Similarity	NPC173660
0.8273	Intermediate Similarity	NPC162659
0.8273	Intermediate Similarity	NPC265433
0.8271	Intermediate Similarity	NPC105925
0.8271	Intermediate Similarity	NPC194519
0.8271	Intermediate Similarity	NPC113495
0.8268	Intermediate Similarity	NPC47194
0.8261	Intermediate Similarity	NPC209199
0.8261	Intermediate Similarity	NPC317380
0.8261	Intermediate Similarity	NPC193026
0.8261	Intermediate Similarity	NPC187616
0.8261	Intermediate Similarity	NPC49603
0.8261	Intermediate Similarity	NPC103967

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 NPC189482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	1072
0.2-0.3	1516
0.3-0.4	2765
0.4-0.5	1696
0.5-0.6	993
0.6-0.7	621
0.7-0.8	95
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8254	Intermediate Similarity	NPD5283	Phase 1
0.8116	Intermediate Similarity	NPD4060	Phase 1
0.8088	Intermediate Similarity	NPD4908	Phase 1
0.8029	Intermediate Similarity	NPD4625	Phase 3
0.7986	Intermediate Similarity	NPD3620	Phase 2
0.7986	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD228	Approved
0.7917	Intermediate Similarity	NPD6674	Discontinued
0.7883	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1613	Approved
0.7857	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6584	Phase 3
0.777	Intermediate Similarity	NPD3027	Phase 3
0.7754	Intermediate Similarity	NPD2861	Phase 2
0.7724	Intermediate Similarity	NPD7037	Approved
0.7721	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD6671	Approved
0.7687	Intermediate Similarity	NPD4626	Approved
0.7671	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3022	Approved
0.7656	Intermediate Similarity	NPD3021	Approved
0.7643	Intermediate Similarity	NPD7095	Approved
0.7639	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2342	Discontinued
0.7591	Intermediate Similarity	NPD4749	Approved
0.7591	Intermediate Similarity	NPD6582	Phase 2
0.7591	Intermediate Similarity	NPD6583	Phase 3
0.7591	Intermediate Similarity	NPD5327	Phase 3
0.7589	Intermediate Similarity	NPD6798	Discontinued
0.7578	Intermediate Similarity	NPD2684	Approved
0.7578	Intermediate Similarity	NPD5844	Phase 1
0.7576	Intermediate Similarity	NPD7157	Approved
0.7574	Intermediate Similarity	NPD1611	Approved
0.7574	Intermediate Similarity	NPD1610	Phase 2
0.7564	Intermediate Similarity	NPD7833	Phase 2
0.7564	Intermediate Similarity	NPD7831	Phase 2
0.7564	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6516	Phase 2
0.7556	Intermediate Similarity	NPD5846	Approved
0.7552	Intermediate Similarity	NPD5735	Approved
0.7533	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD4097	Suspended
0.7484	Intermediate Similarity	NPD6232	Discontinued
0.7483	Intermediate Similarity	NPD4140	Approved
0.7483	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD7843	Approved
0.7481	Intermediate Similarity	NPD5691	Approved
0.7481	Intermediate Similarity	NPD1651	Approved
0.7481	Intermediate Similarity	NPD5535	Approved
0.7465	Intermediate Similarity	NPD5110	Phase 2
0.7465	Intermediate Similarity	NPD5109	Approved
0.7465	Intermediate Similarity	NPD5111	Phase 2
0.7463	Intermediate Similarity	NPD5536	Phase 2
0.7445	Intermediate Similarity	NPD3705	Approved
0.7431	Intermediate Similarity	NPD3657	Discovery
0.7429	Intermediate Similarity	NPD4624	Approved
0.7424	Intermediate Similarity	NPD1398	Phase 1
0.741	Intermediate Similarity	NPD6696	Suspended
0.741	Intermediate Similarity	NPD1283	Approved
0.7407	Intermediate Similarity	NPD1548	Phase 1
0.7388	Intermediate Similarity	NPD7340	Approved
0.7385	Intermediate Similarity	NPD5451	Approved
0.7383	Intermediate Similarity	NPD4110	Phase 3
0.7383	Intermediate Similarity	NPD6331	Phase 2
0.7383	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6353	Approved
0.7376	Intermediate Similarity	NPD3018	Phase 2
0.7372	Intermediate Similarity	NPD5929	Approved
0.7361	Intermediate Similarity	NPD1558	Phase 1
0.7351	Intermediate Similarity	NPD7041	Phase 2
0.7351	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7635	Approved
0.7346	Intermediate Similarity	NPD7473	Discontinued
0.7343	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5241	Discontinued
0.7324	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD709	Approved
0.7312	Intermediate Similarity	NPD7199	Phase 2
0.7312	Intermediate Similarity	NPD6959	Discontinued
0.731	Intermediate Similarity	NPD6355	Discontinued
0.7305	Intermediate Similarity	NPD8053	Approved
0.7305	Intermediate Similarity	NPD8054	Approved
0.7303	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5762	Approved
0.7297	Intermediate Similarity	NPD5763	Approved
0.7293	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD968	Approved
0.7286	Intermediate Similarity	NPD8651	Approved
0.7278	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD290	Approved
0.7226	Intermediate Similarity	NPD1357	Approved
0.7226	Intermediate Similarity	NPD3444	Approved
0.7226	Intermediate Similarity	NPD3443	Approved
0.7226	Intermediate Similarity	NPD3445	Approved
0.7222	Intermediate Similarity	NPD3020	Approved
0.7222	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2983	Phase 2
0.7214	Intermediate Similarity	NPD1669	Approved
0.7214	Intermediate Similarity	NPD2982	Phase 2
0.7211	Intermediate Similarity	NPD7097	Phase 1
0.7205	Intermediate Similarity	NPD8127	Discontinued
0.7197	Intermediate Similarity	NPD37	Approved
0.7197	Intermediate Similarity	NPD1934	Approved
0.7194	Intermediate Similarity	NPD1281	Approved
0.719	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4584	Approved
0.7188	Intermediate Similarity	NPD6234	Discontinued
0.7181	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6166	Phase 2
0.7178	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2489	Approved
0.7178	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD27	Approved
0.7174	Intermediate Similarity	NPD2286	Discontinued
0.7172	Intermediate Similarity	NPD7265	Discontinued
0.7172	Intermediate Similarity	NPD4475	Approved
0.7172	Intermediate Similarity	NPD4474	Approved
0.7172	Intermediate Similarity	NPD6233	Phase 2
0.717	Intermediate Similarity	NPD4966	Approved
0.717	Intermediate Similarity	NPD4965	Approved
0.717	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4967	Phase 2
0.7163	Intermediate Similarity	NPD2922	Phase 1
0.7162	Intermediate Similarity	NPD2154	Approved
0.7162	Intermediate Similarity	NPD2155	Approved
0.7162	Intermediate Similarity	NPD2156	Approved
0.716	Intermediate Similarity	NPD3051	Approved
0.7153	Intermediate Similarity	NPD6581	Approved
0.7153	Intermediate Similarity	NPD6580	Approved
0.7153	Intermediate Similarity	NPD3091	Approved
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD2801	Approved
0.7143	Intermediate Similarity	NPD2232	Approved
0.7143	Intermediate Similarity	NPD2230	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD2233	Approved
0.7143	Intermediate Similarity	NPD4319	Phase 2
0.7143	Intermediate Similarity	NPD2981	Phase 2
0.7133	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2979	Phase 3
0.7122	Intermediate Similarity	NPD3496	Discontinued
0.712	Intermediate Similarity	NPD2859	Approved
0.712	Intermediate Similarity	NPD844	Approved
0.712	Intermediate Similarity	NPD2860	Approved
0.7117	Intermediate Similarity	NPD2970	Approved
0.7117	Intermediate Similarity	NPD2969	Approved
0.7114	Intermediate Similarity	NPD6100	Approved
0.7114	Intermediate Similarity	NPD6099	Approved
0.7114	Intermediate Similarity	NPD2161	Phase 2
0.7114	Intermediate Similarity	NPD2438	Suspended
0.7113	Intermediate Similarity	NPD2797	Approved
0.7105	Intermediate Similarity	NPD2677	Approved
0.7105	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7294	Phase 1
0.7101	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8252	Approved
0.7091	Intermediate Similarity	NPD8251	Approved
0.7091	Intermediate Similarity	NPD8099	Discontinued
0.7086	Intermediate Similarity	NPD3060	Approved
0.7086	Intermediate Similarity	NPD5177	Phase 3
0.7086	Intermediate Similarity	NPD4162	Approved
0.7081	Intermediate Similarity	NPD5709	Phase 3
0.7078	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7447	Phase 1
0.7078	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3092	Approved
0.7067	Intermediate Similarity	NPD2346	Discontinued
0.7063	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7768	Phase 2
0.7063	Intermediate Similarity	NPD288	Approved
0.7055	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8032	Phase 2
0.7055	Intermediate Similarity	NPD2674	Phase 3
0.705	Intermediate Similarity	NPD1778	Approved
0.7048	Intermediate Similarity	NPD8156	Discontinued
0.7047	Intermediate Similarity	NPD4108	Discontinued
0.7044	Intermediate Similarity	NPD8455	Phase 2
0.7044	Intermediate Similarity	NPD1465	Phase 2
0.7044	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD2933	Approved
0.704	Intermediate Similarity	NPD2934	Approved
0.7039	Intermediate Similarity	NPD3750	Approved
0.7039	Intermediate Similarity	NPD4628	Phase 3
0.7037	Intermediate Similarity	NPD4666	Phase 3
0.7037	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6090	Discontinued
0.7027	Intermediate Similarity	NPD2157	Approved
0.7027	Intermediate Similarity	NPD4579	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