NPASS Compound

Structure

NPC474681 OpenBabel07101718192D 28 31 0 0 1 0 0 0 0 0999 V2000 3.1566 2.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7083 4.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7934 0.3912 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 1.2247 2.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 3.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 1.9659 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4495 3.4495 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 -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 -1.7321 -2.0000 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 -2.5981 -1.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 23 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 13 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 23 1 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.15
Volume:	392.361
LogP:	5.482
LogD:	3.893
LogS:	-3.395
# Rotatable Bonds:	3
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	3.611
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.863
MDCK Permeability:	1.574983798491303e-05
Pgp-inhibitor:	0.616
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	88.23002624511719%
Volume Distribution (VD):	0.698
Pgp-substrate:	10.475132942199707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.209
CYP2C19-inhibitor:	0.87
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.756
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.56
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	6.592
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.601
Rat Oral Acute Toxicity:	0.441
Maximum Recommended Daily Dose:	0.617
Skin Sensitization:	0.65
Carcinogencity:	0.891
Eye Corrosion:	0.004
Eye Irritation:	0.254
Respiratory Toxicity:	0.733

Download Data

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

Natural Product: NPC474681

Natural Product ID:	NPC474681
*Common Name:**	6,11-Dihydroxy-3-Methyl-3-(4-Methylpent-3-Enyl)Pyrano[2,3-C]Xanthen-7-One
IUPAC Name:	6,11-dihydroxy-3-methyl-3-(4-methylpent-3-enyl)pyrano[2,3-c]xanthen-7-one
Synonyms:
Standard InCHIKey:	LVANTWLBTIEHSX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H22O5/c1-13(2)6-5-10-23(3)11-9-14-18(28-23)12-17(25)19-20(26)15-7-4-8-16(24)21(15)27-22(14)19/h4,6-9,11-12,24-25H,5,10H2,1-3H3
SMILES:	CC(=CCCC1(C)C=Cc2c(O1)cc(c1c2oc2c(O)cccc2c1=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479289
PubChem CID:	5465516
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4020(01)89039-6]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[16562837]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21028890]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	64000.0	nM	PMID[475254]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	5000.0	nM	PMID[475254]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	8000.0	nM	PMID[475254]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	>	64000.0	nM	PMID[475254]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	52000.0	nM	PMID[475254]

☑ 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 NPC474681 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	449
0.1-0.2	1887
0.2-0.3	4766
0.3-0.4	11166
0.4-0.5	6429
0.5-0.6	3767
0.6-0.7	5180
0.7-0.8	4674
0.8-0.85	2320
0.85-0.9	1359
0.9-0.95	614
0.95-1	86

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC218313
0.9933	High Similarity	NPC133970
0.9933	High Similarity	NPC5322
0.9933	High Similarity	NPC204879
0.9933	High Similarity	NPC6633
0.9866	High Similarity	NPC472280
0.9866	High Similarity	NPC200246
0.9803	High Similarity	NPC167678
0.9803	High Similarity	NPC29876
0.9803	High Similarity	NPC234644
0.98	High Similarity	NPC470600
0.98	High Similarity	NPC472455
0.9799	High Similarity	NPC273462
0.9799	High Similarity	NPC33051
0.9799	High Similarity	NPC227337
0.9799	High Similarity	NPC49402
0.9799	High Similarity	NPC70433
0.9739	High Similarity	NPC472448
0.9739	High Similarity	NPC83922
0.9737	High Similarity	NPC188433
0.9737	High Similarity	NPC204290
0.9737	High Similarity	NPC471973
0.9735	High Similarity	NPC52889
0.9733	High Similarity	NPC117992
0.9733	High Similarity	NPC256925
0.9733	High Similarity	NPC234255
0.9733	High Similarity	NPC168247
0.9733	High Similarity	NPC152951
0.9733	High Similarity	NPC230149
0.9733	High Similarity	NPC57674
0.9732	High Similarity	NPC237994
0.9673	High Similarity	NPC57715
0.9673	High Similarity	NPC259456
0.9671	High Similarity	NPC74178
0.9671	High Similarity	NPC184755
0.9669	High Similarity	NPC471985
0.9664	High Similarity	NPC154345
0.961	High Similarity	NPC474162
0.961	High Similarity	NPC474150
0.9608	High Similarity	NPC476980
0.9608	High Similarity	NPC118256
0.9608	High Similarity	NPC192686
0.9608	High Similarity	NPC119209
0.9605	High Similarity	NPC136674
0.9605	High Similarity	NPC304008
0.9605	High Similarity	NPC187745
0.9605	High Similarity	NPC161960
0.9548	High Similarity	NPC303460
0.9548	High Similarity	NPC23298
0.9548	High Similarity	NPC306321
0.9548	High Similarity	NPC189473
0.9545	High Similarity	NPC134783
0.9545	High Similarity	NPC474038
0.9539	High Similarity	NPC138243
0.9539	High Similarity	NPC282307
0.9539	High Similarity	NPC191146
0.9539	High Similarity	NPC115853
0.9539	High Similarity	NPC170026
0.9539	High Similarity	NPC68093
0.9536	High Similarity	NPC170492
0.9487	High Similarity	NPC275780
0.9487	High Similarity	NPC239752
0.9487	High Similarity	NPC472450
0.9484	High Similarity	NPC474034
0.9484	High Similarity	NPC474033
0.9484	High Similarity	NPC329760
0.9484	High Similarity	NPC261470
0.9481	High Similarity	NPC475784
0.9481	High Similarity	NPC474960
0.9477	High Similarity	NPC36852
0.9477	High Similarity	NPC78225
0.9477	High Similarity	NPC219867
0.9477	High Similarity	NPC473272
0.9477	High Similarity	NPC291508
0.9477	High Similarity	NPC262286
0.9477	High Similarity	NPC476981
0.9477	High Similarity	NPC284820
0.9477	High Similarity	NPC27337
0.9477	High Similarity	NPC180011
0.947	High Similarity	NPC477231
0.947	High Similarity	NPC39732
0.947	High Similarity	NPC471982
0.947	High Similarity	NPC60972
0.947	High Similarity	NPC257648
0.9467	High Similarity	NPC88804
0.9467	High Similarity	NPC29231
0.9467	High Similarity	NPC3825
0.9463	High Similarity	NPC272721
0.9463	High Similarity	NPC196277
0.9463	High Similarity	NPC43669
0.943	High Similarity	NPC288813
0.9427	High Similarity	NPC39091
0.9427	High Similarity	NPC472449
0.9427	High Similarity	NPC37870
0.9423	High Similarity	NPC124038
0.9423	High Similarity	NPC186686
0.9423	High Similarity	NPC472625
0.9419	High Similarity	NPC472632
0.9419	High Similarity	NPC471210
0.9419	High Similarity	NPC26326
0.9419	High Similarity	NPC258331
0.9416	High Similarity	NPC235448
0.9412	High Similarity	NPC276444
0.9412	High Similarity	NPC195796
0.9412	High Similarity	NPC291878
0.9412	High Similarity	NPC472907
0.9412	High Similarity	NPC35038
0.9412	High Similarity	NPC278778
0.9408	High Similarity	NPC472905
0.9404	High Similarity	NPC256406
0.9404	High Similarity	NPC31363
0.9396	High Similarity	NPC168803
0.9396	High Similarity	NPC77378
0.9363	High Similarity	NPC303174
0.9363	High Similarity	NPC300053
0.9363	High Similarity	NPC108433
0.9363	High Similarity	NPC50960
0.9363	High Similarity	NPC62261
0.9359	High Similarity	NPC476247
0.9359	High Similarity	NPC25152
0.9359	High Similarity	NPC229632
0.9359	High Similarity	NPC78332
0.9355	High Similarity	NPC174953
0.9355	High Similarity	NPC328102
0.9355	High Similarity	NPC28241
0.9355	High Similarity	NPC139036
0.9355	High Similarity	NPC472624
0.9351	High Similarity	NPC78071
0.9351	High Similarity	NPC237418
0.9351	High Similarity	NPC299520
0.9351	High Similarity	NPC474055
0.9351	High Similarity	NPC471209
0.9351	High Similarity	NPC67876
0.9351	High Similarity	NPC129684
0.9351	High Similarity	NPC472598
0.9351	High Similarity	NPC476630
0.9351	High Similarity	NPC218871
0.9351	High Similarity	NPC472963
0.9346	High Similarity	NPC470327
0.9346	High Similarity	NPC113906
0.9346	High Similarity	NPC477503
0.9346	High Similarity	NPC256612
0.9346	High Similarity	NPC45849
0.9346	High Similarity	NPC200761
0.9346	High Similarity	NPC20830
0.9342	High Similarity	NPC157784
0.9342	High Similarity	NPC63187
0.9342	High Similarity	NPC37684
0.9342	High Similarity	NPC472912
0.9338	High Similarity	NPC472279
0.9304	High Similarity	NPC235610
0.9304	High Similarity	NPC43319
0.9299	High Similarity	NPC187491
0.9299	High Similarity	NPC236521
0.9299	High Similarity	NPC319200
0.9299	High Similarity	NPC248638
0.9299	High Similarity	NPC152659
0.9299	High Similarity	NPC207690
0.9295	High Similarity	NPC472634
0.9295	High Similarity	NPC61010
0.9295	High Similarity	NPC471212
0.9295	High Similarity	NPC472906
0.9295	High Similarity	NPC471211
0.9295	High Similarity	NPC266314
0.929	High Similarity	NPC474290
0.929	High Similarity	NPC55738
0.929	High Similarity	NPC473990
0.929	High Similarity	NPC100123
0.929	High Similarity	NPC250214
0.929	High Similarity	NPC172770
0.929	High Similarity	NPC187792
0.929	High Similarity	NPC95936
0.929	High Similarity	NPC185258
0.929	High Similarity	NPC117418
0.929	High Similarity	NPC53545
0.9286	High Similarity	NPC472626
0.9286	High Similarity	NPC474638
0.9286	High Similarity	NPC209614
0.9286	High Similarity	NPC472916
0.9286	High Similarity	NPC470328
0.9286	High Similarity	NPC265511
0.9281	High Similarity	NPC255350
0.9281	High Similarity	NPC176775
0.9281	High Similarity	NPC88645
0.9281	High Similarity	NPC160951
0.9281	High Similarity	NPC271779
0.9281	High Similarity	NPC206238
0.9281	High Similarity	NPC231018
0.9281	High Similarity	NPC47781
0.9281	High Similarity	NPC18727
0.9281	High Similarity	NPC213896
0.9281	High Similarity	NPC69394
0.9281	High Similarity	NPC274327
0.9281	High Similarity	NPC145379
0.9281	High Similarity	NPC22519
0.9281	High Similarity	NPC167091
0.9281	High Similarity	NPC469550
0.9281	High Similarity	NPC192083
0.9281	High Similarity	NPC292214
0.9281	High Similarity	NPC74924

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 NPC474681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	1009
0.2-0.3	1741
0.3-0.4	2703
0.4-0.5	1765
0.5-0.6	990
0.6-0.7	371
0.7-0.8	107
0.8-0.85	40
0.85-0.9	12
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD2393	Clinical (unspecified phase)
0.9281	High Similarity	NPD2801	Approved
0.9216	High Similarity	NPD1934	Approved
0.9067	High Similarity	NPD1511	Approved
0.9038	High Similarity	NPD3882	Suspended
0.8947	High Similarity	NPD1512	Approved
0.8882	High Similarity	NPD6166	Phase 2
0.8882	High Similarity	NPD6167	Clinical (unspecified phase)
0.8882	High Similarity	NPD6168	Clinical (unspecified phase)
0.8882	High Similarity	NPD7410	Clinical (unspecified phase)
0.8839	High Similarity	NPD4380	Phase 2
0.8773	High Similarity	NPD3818	Discontinued
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.875	High Similarity	NPD5494	Approved
0.872	High Similarity	NPD7054	Approved
0.8679	High Similarity	NPD4868	Clinical (unspecified phase)
0.8667	High Similarity	NPD7074	Phase 3
0.8667	High Similarity	NPD7472	Approved
0.8625	High Similarity	NPD7075	Discontinued
0.8616	High Similarity	NPD3817	Phase 2
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8512	High Similarity	NPD4338	Clinical (unspecified phase)
0.8509	High Similarity	NPD4381	Clinical (unspecified phase)
0.8503	High Similarity	NPD6797	Phase 2
0.8487	Intermediate Similarity	NPD1549	Phase 2
0.8452	Intermediate Similarity	NPD7251	Discontinued
0.8438	Intermediate Similarity	NPD7819	Suspended
0.8438	Intermediate Similarity	NPD1465	Phase 2
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6232	Discontinued
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8402	Intermediate Similarity	NPD7808	Phase 3
0.8389	Intermediate Similarity	NPD943	Approved
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8373	Intermediate Similarity	NPD7473	Discontinued
0.8355	Intermediate Similarity	NPD2796	Approved
0.8274	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8267	Intermediate Similarity	NPD1240	Approved
0.8217	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3749	Approved
0.8158	Intermediate Similarity	NPD1607	Approved
0.8141	Intermediate Similarity	NPD3750	Approved
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8133	Intermediate Similarity	NPD1247	Approved
0.8121	Intermediate Similarity	NPD919	Approved
0.8095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5402	Approved
0.8036	Intermediate Similarity	NPD3926	Phase 2
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8023	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2800	Approved
0.795	Intermediate Similarity	NPD5403	Approved
0.7933	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD447	Suspended
0.7848	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1243	Approved
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5401	Approved
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7821	Intermediate Similarity	NPD3748	Approved
0.7821	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7771	Intermediate Similarity	NPD6099	Approved
0.7771	Intermediate Similarity	NPD6100	Approved
0.7744	Intermediate Similarity	NPD3226	Approved
0.7742	Intermediate Similarity	NPD230	Phase 1
0.773	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD2346	Discontinued
0.7716	Intermediate Similarity	NPD2534	Approved
0.7716	Intermediate Similarity	NPD2533	Approved
0.7716	Intermediate Similarity	NPD2532	Approved
0.7709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.7657	Intermediate Similarity	NPD5953	Discontinued
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1933	Approved
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.7593	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3751	Discontinued
0.7582	Intermediate Similarity	NPD9494	Approved
0.758	Intermediate Similarity	NPD6651	Approved
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7571	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7390	Discontinued
0.7546	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7286	Phase 2
0.7531	Intermediate Similarity	NPD2309	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD4625	Phase 3
0.747	Intermediate Similarity	NPD1653	Approved
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3787	Discontinued
0.7451	Intermediate Similarity	NPD1203	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7414	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2798	Approved
0.7386	Intermediate Similarity	NPD7228	Approved
0.7382	Intermediate Similarity	NPD7584	Approved
0.7375	Intermediate Similarity	NPD4308	Phase 3
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD6777	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.7325	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5124	Phase 1
0.7296	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD37	Approved
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD7033	Discontinued
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7257	Intermediate Similarity	NPD5711	Approved
0.7257	Intermediate Similarity	NPD5710	Approved
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7255	Intermediate Similarity	NPD9717	Approved
0.7228	Intermediate Similarity	NPD4287	Approved
0.7226	Intermediate Similarity	NPD2797	Approved
0.7226	Intermediate Similarity	NPD1470	Approved
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7222	Intermediate Similarity	NPD5405	Approved
0.7222	Intermediate Similarity	NPD5404	Approved
0.7222	Intermediate Similarity	NPD5406	Approved
0.7222	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7216	Intermediate Similarity	NPD5242	Approved
0.7213	Intermediate Similarity	NPD8434	Phase 2
0.7209	Intermediate Similarity	NPD4288	Approved
0.7208	Intermediate Similarity	NPD4749	Approved
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7193	Intermediate Similarity	NPD6844	Discontinued
0.719	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD1610	Phase 2
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6585	Discontinued
0.7161	Intermediate Similarity	NPD3225	Approved
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7697	Approved
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7128	Intermediate Similarity	NPD4361	Phase 2
0.7128	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4357	Discontinued
0.7125	Intermediate Similarity	NPD4307	Phase 2
0.711	Intermediate Similarity	NPD5353	Approved
0.7108	Intermediate Similarity	NPD2354	Approved
0.7107	Intermediate Similarity	NPD411	Approved
0.7107	Intermediate Similarity	NPD3764	Approved
0.7098	Intermediate Similarity	NPD7870	Phase 2
0.7098	Intermediate Similarity	NPD7871	Phase 2
0.7088	Intermediate Similarity	NPD7549	Discontinued
0.7086	Intermediate Similarity	NPD5536	Phase 2
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2403	Approved
0.7078	Intermediate Similarity	NPD1201	Approved
0.7077	Intermediate Similarity	NPD7701	Phase 2
0.7074	Intermediate Similarity	NPD6534	Approved
0.7074	Intermediate Similarity	NPD6535	Approved
0.7073	Intermediate Similarity	NPD1471	Phase 3
0.7062	Intermediate Similarity	NPD7229	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