NPASS Compound

Structure

NPC475733 OpenBabel07101719242D 25 25 0 0 1 0 0 0 0 0999 V2000 2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -6.5000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 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 -3.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -0.0000 1.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 7 12 2 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.21
Volume:	376.689
LogP:	4.492
LogD:	2.731
LogS:	-3.71
# Rotatable Bonds:	8
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	3.514
Fsp3:	0.55
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:	-4.759
MDCK Permeability:	1.3758414752373938e-05
Pgp-inhibitor:	0.427
Pgp-substrate:	0.074
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	99.52437591552734%
Volume Distribution (VD):	2.575
Pgp-substrate:	2.1011674404144287%

ADMET: Metabolism

CYP1A2-inhibitor:	0.788
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.359
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.536
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.893
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.396
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	12.463
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.223
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.76
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.489
Respiratory Toxicity:	0.513

Download Data

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

Natural Product: NPC475733

Natural Product ID:	NPC475733
*Common Name:**	Hyperjovinol A
IUPAC Name:	2-methyl-1-[2,4,6-trihydroxy-3-(3-hydroxy-3,7-dimethyloct-6-enyl)phenyl]propan-1-one
Synonyms:
Standard InCHIKey:	DJILNHQPAHLEMJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H30O5/c1-12(2)7-6-9-20(5,25)10-8-14-15(21)11-16(22)17(19(14)24)18(23)13(3)4/h7,11,13,21-22,24-25H,6,8-10H2,1-5H3
SMILES:	CC(C)C(=O)C1=C(C=C(C(=C1O)CCC(C)(CCC=C(C)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513396
PubChem CID:	11725449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO7800	Hypericum jovis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217276]
NPO7800	Hypericum jovis	Species	Hypericaceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	76.1	%	PMID[482907]
NPT2	Others	Unspecified		Activity	=	49.2	%	PMID[482907]

☑ 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 NPC475733 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	303
0.1-0.2	1498
0.2-0.3	3747
0.3-0.4	10895
0.4-0.5	8702
0.5-0.6	5347
0.6-0.7	6830
0.7-0.8	4259
0.8-0.85	861
0.85-0.9	181
0.9-0.95	62
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC65761
0.9831	High Similarity	NPC472029
0.9746	High Similarity	NPC91105
0.9661	High Similarity	NPC215392
0.9576	High Similarity	NPC146642
0.9576	High Similarity	NPC149246
0.9512	High Similarity	NPC474998
0.9492	High Similarity	NPC294037
0.9431	High Similarity	NPC21305
0.9431	High Similarity	NPC473017
0.9426	High Similarity	NPC267846
0.9417	High Similarity	NPC309765
0.935	High Similarity	NPC266689
0.935	High Similarity	NPC169250
0.935	High Similarity	NPC23126
0.935	High Similarity	NPC72158
0.935	High Similarity	NPC98254
0.935	High Similarity	NPC103356
0.935	High Similarity	NPC116513
0.935	High Similarity	NPC105157
0.935	High Similarity	NPC30501
0.935	High Similarity	NPC162612
0.935	High Similarity	NPC100067
0.935	High Similarity	NPC190043
0.9333	High Similarity	NPC226275
0.9333	High Similarity	NPC303737
0.9322	High Similarity	NPC209486
0.9322	High Similarity	NPC40649
0.9274	High Similarity	NPC221777
0.9268	High Similarity	NPC62952
0.9187	High Similarity	NPC477454
0.9134	High Similarity	NPC175738
0.9113	High Similarity	NPC473691
0.9083	High Similarity	NPC161617
0.9076	High Similarity	NPC121259
0.9062	High Similarity	NPC139074
0.9062	High Similarity	NPC213485
0.9062	High Similarity	NPC40524
0.9055	High Similarity	NPC475042
0.9016	High Similarity	NPC196976
0.9016	High Similarity	NPC242895
0.8992	High Similarity	NPC282780
0.8992	High Similarity	NPC166480
0.8992	High Similarity	NPC475088
0.8984	High Similarity	NPC27490
0.896	High Similarity	NPC473751
0.896	High Similarity	NPC328983
0.8943	High Similarity	NPC32032
0.8943	High Similarity	NPC133909
0.8939	High Similarity	NPC470671
0.8939	High Similarity	NPC470672
0.8939	High Similarity	NPC474487
0.8939	High Similarity	NPC474504
0.8934	High Similarity	NPC229649
0.8923	High Similarity	NPC283590
0.8923	High Similarity	NPC70859
0.8923	High Similarity	NPC290803
0.8923	High Similarity	NPC61153
0.8923	High Similarity	NPC130899
0.8915	High Similarity	NPC37299
0.8915	High Similarity	NPC180261
0.8906	High Similarity	NPC275504
0.8906	High Similarity	NPC324482
0.8898	High Similarity	NPC92624
0.8898	High Similarity	NPC476119
0.8898	High Similarity	NPC109123
0.8889	High Similarity	NPC329205
0.8889	High Similarity	NPC316625
0.888	High Similarity	NPC10926
0.8871	High Similarity	NPC306288
0.8862	High Similarity	NPC156139
0.8862	High Similarity	NPC224273
0.8862	High Similarity	NPC143427
0.8862	High Similarity	NPC19174
0.8862	High Similarity	NPC73532
0.8862	High Similarity	NPC115159
0.8862	High Similarity	NPC45438
0.8862	High Similarity	NPC267552
0.8855	High Similarity	NPC264112
0.8855	High Similarity	NPC65005
0.8855	High Similarity	NPC475955
0.8855	High Similarity	NPC474726
0.8855	High Similarity	NPC191976
0.8855	High Similarity	NPC194764
0.8828	High Similarity	NPC84772
0.8828	High Similarity	NPC259942
0.8828	High Similarity	NPC17840
0.8828	High Similarity	NPC247477
0.8824	High Similarity	NPC276111
0.8824	High Similarity	NPC118288
0.8819	High Similarity	NPC470981
0.881	High Similarity	NPC8745
0.8806	High Similarity	NPC477272
0.88	High Similarity	NPC13238
0.8797	High Similarity	NPC470669
0.8797	High Similarity	NPC21350
0.8797	High Similarity	NPC131130
0.8797	High Similarity	NPC162939
0.8797	High Similarity	NPC470668
0.879	High Similarity	NPC232708
0.879	High Similarity	NPC66252
0.879	High Similarity	NPC218333
0.8788	High Similarity	NPC156910
0.878	High Similarity	NPC297186
0.8779	High Similarity	NPC470210
0.877	High Similarity	NPC188814
0.877	High Similarity	NPC195262
0.8769	High Similarity	NPC470988
0.8769	High Similarity	NPC285054
0.8769	High Similarity	NPC267205
0.8769	High Similarity	NPC48036
0.875	High Similarity	NPC69235
0.875	High Similarity	NPC230818
0.875	High Similarity	NPC212379
0.8731	High Similarity	NPC181560
0.8731	High Similarity	NPC169452
0.8731	High Similarity	NPC477956
0.873	High Similarity	NPC262671
0.873	High Similarity	NPC201728
0.8722	High Similarity	NPC153979
0.8722	High Similarity	NPC317119
0.8722	High Similarity	NPC473622
0.8712	High Similarity	NPC118919
0.8712	High Similarity	NPC13575
0.8712	High Similarity	NPC84699
0.8712	High Similarity	NPC131039
0.8702	High Similarity	NPC470984
0.8702	High Similarity	NPC474519
0.8699	High Similarity	NPC159525
0.8692	High Similarity	NPC185624
0.8682	High Similarity	NPC21378
0.8682	High Similarity	NPC470987
0.8682	High Similarity	NPC62219
0.8672	High Similarity	NPC41263
0.8657	High Similarity	NPC242994
0.8657	High Similarity	NPC138099
0.8647	High Similarity	NPC477242
0.8647	High Similarity	NPC174999
0.8647	High Similarity	NPC249606
0.8647	High Similarity	NPC274109
0.8647	High Similarity	NPC12165
0.8647	High Similarity	NPC187826
0.8647	High Similarity	NPC1486
0.8647	High Similarity	NPC477243
0.8647	High Similarity	NPC66349
0.8647	High Similarity	NPC44960
0.8647	High Similarity	NPC194579
0.8647	High Similarity	NPC471905
0.8647	High Similarity	NPC168105
0.8647	High Similarity	NPC474110
0.8647	High Similarity	NPC150399
0.8647	High Similarity	NPC477244
0.8647	High Similarity	NPC186838
0.8647	High Similarity	NPC41461
0.8647	High Similarity	NPC213603
0.8647	High Similarity	NPC25287
0.8647	High Similarity	NPC98115
0.8636	High Similarity	NPC474076
0.8636	High Similarity	NPC164136
0.8636	High Similarity	NPC144027
0.8636	High Similarity	NPC103842
0.8636	High Similarity	NPC236974
0.8618	High Similarity	NPC158222
0.8607	High Similarity	NPC230349
0.8605	High Similarity	NPC73203
0.8603	High Similarity	NPC193555
0.8594	High Similarity	NPC305518
0.8594	High Similarity	NPC128428
0.8593	High Similarity	NPC470986
0.8593	High Similarity	NPC23257
0.8583	High Similarity	NPC242136
0.8583	High Similarity	NPC290466
0.8582	High Similarity	NPC472419
0.8571	High Similarity	NPC254847
0.8571	High Similarity	NPC156092
0.8561	High Similarity	NPC108113
0.8561	High Similarity	NPC93756
0.8561	High Similarity	NPC18877
0.8561	High Similarity	NPC28753
0.8561	High Similarity	NPC204960
0.8561	High Similarity	NPC20560
0.8561	High Similarity	NPC144051
0.8561	High Similarity	NPC159623
0.8561	High Similarity	NPC294593
0.8561	High Similarity	NPC82225
0.8561	High Similarity	NPC474394
0.8551	High Similarity	NPC328623
0.854	High Similarity	NPC297600
0.854	High Similarity	NPC474203
0.854	High Similarity	NPC293545
0.854	High Similarity	NPC144499
0.854	High Similarity	NPC451542
0.854	High Similarity	NPC313047
0.854	High Similarity	NPC295712
0.854	High Similarity	NPC174905
0.8538	High Similarity	NPC244441
0.8538	High Similarity	NPC233056
0.8537	High Similarity	NPC474890
0.8537	High Similarity	NPC273282
0.8537	High Similarity	NPC161943

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 NPC475733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	964
0.2-0.3	1633
0.3-0.4	2845
0.4-0.5	1980
0.5-0.6	1012
0.6-0.7	316
0.7-0.8	89
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD1509	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD943	Approved
0.8345	Intermediate Similarity	NPD7390	Discontinued
0.8286	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD1240	Approved
0.8175	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1510	Phase 2
0.8156	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6651	Approved
0.8148	Intermediate Similarity	NPD1607	Approved
0.8029	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2800	Approved
0.7914	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1164	Approved
0.7877	Intermediate Similarity	NPD4380	Phase 2
0.7857	Intermediate Similarity	NPD1549	Phase 2
0.7846	Intermediate Similarity	NPD1201	Approved
0.7838	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD940	Approved
0.7815	Intermediate Similarity	NPD846	Approved
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7744	Intermediate Similarity	NPD1470	Approved
0.7724	Intermediate Similarity	NPD74	Approved
0.7724	Intermediate Similarity	NPD9266	Approved
0.7714	Intermediate Similarity	NPD5406	Approved
0.7714	Intermediate Similarity	NPD5404	Approved
0.7714	Intermediate Similarity	NPD5408	Approved
0.7714	Intermediate Similarity	NPD2935	Discontinued
0.7714	Intermediate Similarity	NPD2796	Approved
0.7714	Intermediate Similarity	NPD5405	Approved
0.7703	Intermediate Similarity	NPD7411	Suspended
0.7682	Intermediate Similarity	NPD7075	Discontinued
0.7656	Intermediate Similarity	NPD9493	Approved
0.7652	Intermediate Similarity	NPD9269	Phase 2
0.7642	Intermediate Similarity	NPD9264	Approved
0.7642	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD9263	Approved
0.7642	Intermediate Similarity	NPD9267	Approved
0.7615	Intermediate Similarity	NPD9268	Approved
0.76	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7819	Suspended
0.7586	Intermediate Similarity	NPD1511	Approved
0.7552	Intermediate Similarity	NPD1243	Approved
0.7533	Intermediate Similarity	NPD1934	Approved
0.752	Intermediate Similarity	NPD4750	Phase 3
0.7519	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1512	Approved
0.7483	Intermediate Similarity	NPD2801	Approved
0.7466	Intermediate Similarity	NPD6799	Approved
0.7452	Intermediate Similarity	NPD7473	Discontinued
0.7431	Intermediate Similarity	NPD2654	Approved
0.7429	Intermediate Similarity	NPD230	Phase 1
0.7419	Intermediate Similarity	NPD6959	Discontinued
0.7417	Intermediate Similarity	NPD6801	Discontinued
0.7405	Intermediate Similarity	NPD9545	Approved
0.7389	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3882	Suspended
0.7386	Intermediate Similarity	NPD7768	Phase 2
0.7379	Intermediate Similarity	NPD3750	Approved
0.7372	Intermediate Similarity	NPD6232	Discontinued
0.7364	Intermediate Similarity	NPD9281	Approved
0.7343	Intermediate Similarity	NPD6099	Approved
0.7343	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3749	Approved
0.7317	Intermediate Similarity	NPD9261	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2798	Approved
0.7297	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2344	Approved
0.7285	Intermediate Similarity	NPD6599	Discontinued
0.7279	Intermediate Similarity	NPD3300	Phase 2
0.726	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9717	Approved
0.725	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1551	Phase 2
0.7214	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD920	Approved
0.7178	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6166	Phase 2
0.717	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3019	Approved
0.7164	Intermediate Similarity	NPD2932	Approved
0.7162	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD6020	Phase 2
0.7134	Intermediate Similarity	NPD5494	Approved
0.7107	Intermediate Similarity	NPD1809	Phase 2
0.7101	Intermediate Similarity	NPD1203	Approved
0.7097	Intermediate Similarity	NPD3817	Phase 2
0.7095	Intermediate Similarity	NPD2309	Approved
0.7092	Intermediate Similarity	NPD3764	Approved
0.7092	Intermediate Similarity	NPD2313	Discontinued
0.7083	Intermediate Similarity	NPD845	Approved
0.7073	Intermediate Similarity	NPD3020	Approved
0.7067	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5710	Approved
0.7044	Intermediate Similarity	NPD5711	Approved
0.7037	Intermediate Similarity	NPD7286	Phase 2
0.7034	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3748	Approved
0.7016	Intermediate Similarity	NPD1242	Phase 1
0.6994	Remote Similarity	NPD7074	Phase 3
0.6975	Remote Similarity	NPD3818	Discontinued
0.6972	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3268	Approved
0.6967	Remote Similarity	NPD2860	Approved
0.6967	Remote Similarity	NPD2859	Approved
0.6943	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD422	Phase 1
0.6933	Remote Similarity	NPD7054	Approved
0.6909	Remote Similarity	NPD6559	Discontinued
0.6899	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7472	Approved
0.6885	Remote Similarity	NPD2933	Approved
0.6885	Remote Similarity	NPD2934	Approved
0.6885	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3972	Approved
0.6883	Remote Similarity	NPD3226	Approved
0.6883	Remote Similarity	NPD7458	Discontinued
0.6863	Remote Similarity	NPD5403	Approved
0.6857	Remote Similarity	NPD2797	Approved
0.6855	Remote Similarity	NPD919	Approved
0.6853	Remote Similarity	NPD411	Approved
0.6848	Remote Similarity	NPD6797	Phase 2
0.6835	Remote Similarity	NPD4749	Approved
0.6831	Remote Similarity	NPD6832	Phase 2
0.6831	Remote Similarity	NPD4908	Phase 1
0.6829	Remote Similarity	NPD844	Approved
0.6828	Remote Similarity	NPD5124	Phase 1
0.6828	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD447	Suspended
0.6824	Remote Similarity	NPD2346	Discontinued
0.6807	Remote Similarity	NPD7251	Discontinued
0.6806	Remote Similarity	NPD520	Approved
0.6803	Remote Similarity	NPD4308	Phase 3
0.68	Remote Similarity	NPD7003	Approved
0.68	Remote Similarity	NPD3400	Discontinued
0.68	Remote Similarity	NPD4628	Phase 3
0.6788	Remote Similarity	NPD1729	Discontinued
0.6774	Remote Similarity	NPD288	Approved
0.6772	Remote Similarity	NPD1929	Approved
0.6772	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1930	Approved
0.6772	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1247	Approved
0.6766	Remote Similarity	NPD7808	Phase 3
0.6765	Remote Similarity	NPD1759	Phase 1
0.6763	Remote Similarity	NPD4363	Phase 3
0.6763	Remote Similarity	NPD4360	Phase 2
0.6753	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2403	Approved
0.6742	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3023	Approved
0.6739	Remote Similarity	NPD3026	Approved
0.6732	Remote Similarity	NPD5401	Approved
0.6727	Remote Similarity	NPD5844	Phase 1
0.6724	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4361	Phase 2
0.6718	Remote Similarity	NPD3021	Approved
0.6718	Remote Similarity	NPD3022	Approved
0.6715	Remote Similarity	NPD3024	Approved
0.6715	Remote Similarity	NPD3025	Approved
0.6714	Remote Similarity	NPD1755	Approved
0.6691	Remote Similarity	NPD1610	Phase 2
0.6691	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1758	Phase 1
0.6689	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD255	Approved
0.6643	Remote Similarity	NPD9494	Approved
0.6643	Remote Similarity	NPD1608	Approved
0.6642	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1296	Phase 2
0.6621	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3267	Approved
0.662	Remote Similarity	NPD3266	Approved
0.6614	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD8150	Discontinued
0.6604	Remote Similarity	NPD1465	Phase 2
0.6593	Remote Similarity	NPD5951	Approved
0.6589	Remote Similarity	NPD1237	Approved
0.6582	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1019	Discontinued

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