NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.12
Volume:	275.732
LogP:	2.342
LogD:	1.502
LogS:	-2.824
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	4.074
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.997
MDCK Permeability:	1.4452139112108853e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.186
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	86.7702865600586%
Volume Distribution (VD):	1.588
Pgp-substrate:	8.888489723205566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.791
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.457
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.722
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	2.436
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.467
AMES Toxicity:	0.394
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.712
Skin Sensitization:	0.839
Carcinogencity:	0.728
Eye Corrosion:	0.004
Eye Irritation:	0.107
Respiratory Toxicity:	0.667

Download Data

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

Natural Product: NPC475907

Natural Product ID:	NPC475907
*Common Name:**	Radulifolin A/ Epi-Radulifolin A
IUPAC Name:	(10S)-4,5,6-trihydroxy-4,10-dimethyl-7,8,9,10-tetrahydro-1H-benzo[h]isochromen-3-one
Synonyms:	Radulifolin A/ Epi-Radulifolin A
Standard InCHIKey:	JJAZJHQERFKZAF-CIFJEQONSA-N
Standard InCHI:	InChI=1S/C15H18O5/c1-7-4-3-5-8-10(7)9-6-20-14(18)15(2,19)11(9)13(17)12(8)16/h7,16-17,19H,3-6H2,1-2H3/t7-,15?/m0/s1
SMILES:	Oc1c2CCC[C@@H](c2c2c(c1O)C(C)(O)C(=O)OC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518267
PubChem CID:	44584739
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO6737	Psacalium radulifolium	Species	Asteraceae	Eukaryota	roots	n.a.	n.a.	PMID[11325222]
NPO6737	Psacalium radulifolium	Species	Asteraceae	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
LD50	1
MIC	4

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	200.0	ug.mL-1	PMID[487790]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	400.0	ug.mL-1	PMID[487790]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	400.0	ug.mL-1	PMID[487790]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	400.0	ug.mL-1	PMID[487790]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	230.0	ppm	PMID[487790]

☑ 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 NPC475907 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	331
0.1-0.2	1452
0.2-0.3	3470
0.3-0.4	7804
0.4-0.5	11101
0.5-0.6	5219
0.6-0.7	10080
0.7-0.8	3164
0.8-0.85	63
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC169682
0.8828	High Similarity	NPC127046
0.8819	High Similarity	NPC84786
0.8759	High Similarity	NPC191899
0.8759	High Similarity	NPC474991
0.8759	High Similarity	NPC246229
0.8707	High Similarity	NPC303989
0.8503	High Similarity	NPC58752
0.8493	Intermediate Similarity	NPC126707
0.8446	Intermediate Similarity	NPC470757
0.8345	Intermediate Similarity	NPC187690
0.831	Intermediate Similarity	NPC293454
0.8235	Intermediate Similarity	NPC281703
0.8235	Intermediate Similarity	NPC125487
0.8231	Intermediate Similarity	NPC314271
0.8194	Intermediate Similarity	NPC156967
0.8188	Intermediate Similarity	NPC75295
0.8188	Intermediate Similarity	NPC258856
0.8182	Intermediate Similarity	NPC471456
0.8165	Intermediate Similarity	NPC29055
0.8163	Intermediate Similarity	NPC272907
0.8163	Intermediate Similarity	NPC2681
0.8158	Intermediate Similarity	NPC50269
0.8138	Intermediate Similarity	NPC245058
0.8133	Intermediate Similarity	NPC268366
0.8105	Intermediate Similarity	NPC221249
0.8095	Intermediate Similarity	NPC327187
0.8095	Intermediate Similarity	NPC3218
0.8092	Intermediate Similarity	NPC142654
0.8077	Intermediate Similarity	NPC143328
0.8077	Intermediate Similarity	NPC302258
0.8069	Intermediate Similarity	NPC471690
0.8069	Intermediate Similarity	NPC326847
0.8069	Intermediate Similarity	NPC472599
0.8067	Intermediate Similarity	NPC471689
0.8052	Intermediate Similarity	NPC218628
0.8039	Intermediate Similarity	NPC31132
0.8026	Intermediate Similarity	NPC471852
0.8026	Intermediate Similarity	NPC94781
0.8	Intermediate Similarity	NPC291510
0.8	Intermediate Similarity	NPC43872
0.8	Intermediate Similarity	NPC273248
0.8	Intermediate Similarity	NPC471695
0.8	Intermediate Similarity	NPC238672
0.8	Intermediate Similarity	NPC62051
0.8	Intermediate Similarity	NPC312482
0.8	Intermediate Similarity	NPC197188
0.8	Intermediate Similarity	NPC116850
0.8	Intermediate Similarity	NPC144801
0.7987	Intermediate Similarity	NPC124842
0.7987	Intermediate Similarity	NPC322112
0.7987	Intermediate Similarity	NPC144843
0.7986	Intermediate Similarity	NPC239855
0.7986	Intermediate Similarity	NPC49742
0.7974	Intermediate Similarity	NPC44378
0.7974	Intermediate Similarity	NPC280753
0.7962	Intermediate Similarity	NPC167098
0.7962	Intermediate Similarity	NPC296044
0.7961	Intermediate Similarity	NPC476463
0.7961	Intermediate Similarity	NPC81835
0.7949	Intermediate Similarity	NPC16286
0.7949	Intermediate Similarity	NPC472835
0.7945	Intermediate Similarity	NPC475111
0.7937	Intermediate Similarity	NPC249181
0.7937	Intermediate Similarity	NPC208120
0.7937	Intermediate Similarity	NPC173587
0.7935	Intermediate Similarity	NPC161159
0.7935	Intermediate Similarity	NPC295646
0.7935	Intermediate Similarity	NPC180388
0.7935	Intermediate Similarity	NPC178574
0.7935	Intermediate Similarity	NPC65591
0.7935	Intermediate Similarity	NPC161778
0.7931	Intermediate Similarity	NPC475645
0.7925	Intermediate Similarity	NPC117985
0.7919	Intermediate Similarity	NPC253722
0.7919	Intermediate Similarity	NPC31751
0.7919	Intermediate Similarity	NPC253481
0.7917	Intermediate Similarity	NPC476389
0.7911	Intermediate Similarity	NPC471750
0.7911	Intermediate Similarity	NPC45846
0.7911	Intermediate Similarity	NPC470339
0.7911	Intermediate Similarity	NPC315157
0.7908	Intermediate Similarity	NPC470359
0.7908	Intermediate Similarity	NPC470479
0.7905	Intermediate Similarity	NPC147379
0.7902	Intermediate Similarity	NPC296158
0.7901	Intermediate Similarity	NPC232936
0.7901	Intermediate Similarity	NPC107009
0.7901	Intermediate Similarity	NPC473094
0.7898	Intermediate Similarity	NPC197751
0.7898	Intermediate Similarity	NPC478027
0.7898	Intermediate Similarity	NPC165483
0.7895	Intermediate Similarity	NPC260946
0.7888	Intermediate Similarity	NPC21016
0.7888	Intermediate Similarity	NPC146584
0.7888	Intermediate Similarity	NPC191930
0.7885	Intermediate Similarity	NPC192189
0.7885	Intermediate Similarity	NPC281477
0.7885	Intermediate Similarity	NPC478231
0.7875	Intermediate Similarity	NPC215612
0.7871	Intermediate Similarity	NPC477672
0.7871	Intermediate Similarity	NPC265862
0.7871	Intermediate Similarity	NPC477673
0.7871	Intermediate Similarity	NPC92747
0.7871	Intermediate Similarity	NPC205918
0.7867	Intermediate Similarity	NPC248068
0.7862	Intermediate Similarity	NPC24627
0.7862	Intermediate Similarity	NPC472055
0.7862	Intermediate Similarity	NPC47623
0.7853	Intermediate Similarity	NPC473096
0.7853	Intermediate Similarity	NPC473095
0.7853	Intermediate Similarity	NPC213416
0.7852	Intermediate Similarity	NPC471853
0.7852	Intermediate Similarity	NPC168471
0.7848	Intermediate Similarity	NPC474010
0.7848	Intermediate Similarity	NPC135222
0.7847	Intermediate Similarity	NPC291001
0.7847	Intermediate Similarity	NPC78575
0.7843	Intermediate Similarity	NPC166583
0.7843	Intermediate Similarity	NPC53362
0.784	Intermediate Similarity	NPC20237
0.784	Intermediate Similarity	NPC472452
0.7838	Intermediate Similarity	NPC230811
0.7834	Intermediate Similarity	NPC16082
0.7834	Intermediate Similarity	NPC82592
0.7834	Intermediate Similarity	NPC199926
0.7826	Intermediate Similarity	NPC477689
0.7826	Intermediate Similarity	NPC223006
0.7826	Intermediate Similarity	NPC272750
0.7826	Intermediate Similarity	NPC173729
0.7826	Intermediate Similarity	NPC134047
0.7821	Intermediate Similarity	NPC76041
0.7821	Intermediate Similarity	NPC115249
0.7821	Intermediate Similarity	NPC184284
0.7821	Intermediate Similarity	NPC167903
0.7815	Intermediate Similarity	NPC114242
0.7815	Intermediate Similarity	NPC50221
0.7815	Intermediate Similarity	NPC159721
0.7812	Intermediate Similarity	NPC139540
0.7812	Intermediate Similarity	NPC318081
0.7812	Intermediate Similarity	NPC177100
0.78	Intermediate Similarity	NPC92079
0.7799	Intermediate Similarity	NPC85121
0.7793	Intermediate Similarity	NPC59239
0.7792	Intermediate Similarity	NPC220006
0.7792	Intermediate Similarity	NPC181452
0.7791	Intermediate Similarity	NPC283041
0.7785	Intermediate Similarity	NPC295492
0.7785	Intermediate Similarity	NPC26241
0.7785	Intermediate Similarity	NPC150227
0.7785	Intermediate Similarity	NPC474875
0.7785	Intermediate Similarity	NPC276815
0.7785	Intermediate Similarity	NPC476820
0.7785	Intermediate Similarity	NPC48105
0.7785	Intermediate Similarity	NPC205751
0.7785	Intermediate Similarity	NPC227062
0.7785	Intermediate Similarity	NPC471819
0.7785	Intermediate Similarity	NPC25850
0.7785	Intermediate Similarity	NPC274891
0.7785	Intermediate Similarity	NPC303683
0.7785	Intermediate Similarity	NPC471968
0.7785	Intermediate Similarity	NPC88269
0.7785	Intermediate Similarity	NPC476819
0.7778	Intermediate Similarity	NPC51513
0.7778	Intermediate Similarity	NPC473023
0.7778	Intermediate Similarity	NPC202112
0.7778	Intermediate Similarity	NPC229264
0.7778	Intermediate Similarity	NPC162169
0.7778	Intermediate Similarity	NPC99795
0.7778	Intermediate Similarity	NPC30720
0.7778	Intermediate Similarity	NPC166851
0.7778	Intermediate Similarity	NPC102372
0.7771	Intermediate Similarity	NPC477669
0.7771	Intermediate Similarity	NPC137301
0.777	Intermediate Similarity	NPC470721
0.777	Intermediate Similarity	NPC6100
0.777	Intermediate Similarity	NPC156888
0.777	Intermediate Similarity	NPC470722
0.7764	Intermediate Similarity	NPC144557
0.7764	Intermediate Similarity	NPC211107
0.7764	Intermediate Similarity	NPC474763
0.7763	Intermediate Similarity	NPC151607
0.7763	Intermediate Similarity	NPC475813
0.7763	Intermediate Similarity	NPC42540
0.7756	Intermediate Similarity	NPC228662
0.7756	Intermediate Similarity	NPC115869
0.7756	Intermediate Similarity	NPC75377
0.775	Intermediate Similarity	NPC161947
0.775	Intermediate Similarity	NPC155302
0.775	Intermediate Similarity	NPC21046
0.775	Intermediate Similarity	NPC155101
0.7748	Intermediate Similarity	NPC258469
0.7748	Intermediate Similarity	NPC192831
0.7748	Intermediate Similarity	NPC472016
0.7748	Intermediate Similarity	NPC43158
0.7748	Intermediate Similarity	NPC277315
0.7748	Intermediate Similarity	NPC82913
0.7742	Intermediate Similarity	NPC247219
0.7742	Intermediate Similarity	NPC306343
0.7742	Intermediate Similarity	NPC120171

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 NPC475907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	1017
0.2-0.3	2112
0.3-0.4	2743
0.4-0.5	1711
0.5-0.6	905
0.6-0.7	340
0.7-0.8	37
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
0.7712	Intermediate Similarity	NPD2534	Approved
0.7712	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7654	Intermediate Similarity	NPD6232	Discontinued
0.7632	Intermediate Similarity	NPD6190	Approved
0.7622	Intermediate Similarity	NPD7473	Discontinued
0.7619	Intermediate Similarity	NPD230	Phase 1
0.7562	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1465	Phase 2
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8150	Discontinued
0.7484	Intermediate Similarity	NPD37	Approved
0.747	Intermediate Similarity	NPD7228	Approved
0.7453	Intermediate Similarity	NPD4967	Phase 2
0.7453	Intermediate Similarity	NPD4966	Approved
0.7453	Intermediate Similarity	NPD4965	Approved
0.7438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7985	Registered
0.7415	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4060	Phase 1
0.7289	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6674	Discontinued
0.7267	Intermediate Similarity	NPD1934	Approved
0.7235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5710	Approved
0.7229	Intermediate Similarity	NPD5711	Approved
0.7226	Intermediate Similarity	NPD8166	Discontinued
0.7216	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7075	Discontinued
0.719	Intermediate Similarity	NPD6099	Approved
0.719	Intermediate Similarity	NPD6100	Approved
0.7178	Intermediate Similarity	NPD3817	Phase 2
0.7169	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3882	Suspended
0.7123	Intermediate Similarity	NPD1283	Approved
0.7117	Intermediate Similarity	NPD7819	Suspended
0.7117	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2801	Approved
0.7115	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1512	Approved
0.7102	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6959	Discontinued
0.7052	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7240	Approved
0.6981	Remote Similarity	NPD1511	Approved
0.6981	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2979	Phase 3
0.6974	Remote Similarity	NPD1613	Approved
0.6968	Remote Similarity	NPD5408	Approved
0.6968	Remote Similarity	NPD5406	Approved
0.6968	Remote Similarity	NPD5404	Approved
0.6968	Remote Similarity	NPD5405	Approved
0.6968	Remote Similarity	NPD2438	Suspended
0.6954	Remote Similarity	NPD3764	Approved
0.6951	Remote Similarity	NPD6801	Discontinued
0.6944	Remote Similarity	NPD6535	Approved
0.6944	Remote Similarity	NPD6534	Approved
0.6937	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6797	Phase 2
0.6933	Remote Similarity	NPD4380	Phase 2
0.6933	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6599	Discontinued
0.6928	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD3787	Discontinued
0.6923	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD7266	Discontinued
0.6918	Remote Similarity	NPD1281	Approved
0.6905	Remote Similarity	NPD5494	Approved
0.6897	Remote Similarity	NPD7685	Pre-registration
0.6897	Remote Similarity	NPD7251	Discontinued
0.6882	Remote Similarity	NPD8320	Phase 1
0.6882	Remote Similarity	NPD8319	Approved
0.6879	Remote Similarity	NPD7074	Phase 3
0.6879	Remote Similarity	NPD1398	Phase 1
0.6875	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3226	Approved
0.6871	Remote Similarity	NPD1608	Approved
0.6871	Remote Similarity	NPD9269	Phase 2
0.6863	Remote Similarity	NPD943	Approved
0.686	Remote Similarity	NPD3818	Discontinued
0.6859	Remote Similarity	NPD2935	Discontinued
0.6853	Remote Similarity	NPD7340	Approved
0.6842	Remote Similarity	NPD6798	Discontinued
0.6842	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7700	Phase 2
0.6831	Remote Similarity	NPD7699	Phase 2
0.6828	Remote Similarity	NPD7435	Discontinued
0.6821	Remote Similarity	NPD7054	Approved
0.6818	Remote Similarity	NPD8312	Approved
0.6818	Remote Similarity	NPD8313	Approved
0.6815	Remote Similarity	NPD5762	Approved
0.6815	Remote Similarity	NPD5763	Approved
0.6806	Remote Similarity	NPD7644	Approved
0.6797	Remote Similarity	NPD6663	Approved
0.6782	Remote Similarity	NPD7472	Approved
0.6776	Remote Similarity	NPD3027	Phase 3
0.6776	Remote Similarity	NPD4625	Phase 3
0.6774	Remote Similarity	NPD6651	Approved
0.677	Remote Similarity	NPD6799	Approved
0.677	Remote Similarity	NPD7390	Discontinued
0.6768	Remote Similarity	NPD7458	Discontinued
0.6763	Remote Similarity	NPD3751	Discontinued
0.6761	Remote Similarity	NPD7808	Phase 3
0.6759	Remote Similarity	NPD9545	Approved
0.6757	Remote Similarity	NPD6778	Approved
0.6757	Remote Similarity	NPD6781	Approved
0.6757	Remote Similarity	NPD6780	Approved
0.6757	Remote Similarity	NPD6779	Approved
0.6757	Remote Similarity	NPD6782	Approved
0.6757	Remote Similarity	NPD6776	Approved
0.6757	Remote Similarity	NPD6777	Approved
0.6755	Remote Similarity	NPD5736	Approved
0.673	Remote Similarity	NPD2800	Approved
0.673	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2493	Approved
0.672	Remote Similarity	NPD2494	Approved
0.671	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5124	Phase 1
0.6709	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8455	Phase 2
0.6705	Remote Similarity	NPD6559	Discontinued
0.6704	Remote Similarity	NPD8434	Phase 2
0.6703	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4582	Approved
0.6702	Remote Similarity	NPD4583	Approved
0.6688	Remote Similarity	NPD6233	Phase 2
0.6687	Remote Similarity	NPD3750	Approved
0.6687	Remote Similarity	NPD4110	Phase 3
0.6687	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7003	Approved
0.6687	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD17	Approved
0.6649	Remote Similarity	NPD4004	Approved
0.6649	Remote Similarity	NPD4002	Approved
0.6647	Remote Similarity	NPD919	Approved
0.6646	Remote Similarity	NPD2531	Phase 2
0.6645	Remote Similarity	NPD3620	Phase 2
0.6645	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD9494	Approved
0.6631	Remote Similarity	NPD3450	Approved
0.6631	Remote Similarity	NPD3452	Approved
0.6626	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7874	Approved
0.6615	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1653	Approved
0.6605	Remote Similarity	NPD3300	Phase 2
0.6604	Remote Similarity	NPD6005	Phase 3
0.6604	Remote Similarity	NPD6004	Phase 3
0.6604	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6002	Phase 3
0.6604	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD447	Suspended
0.66	Remote Similarity	NPD4749	Approved
0.6599	Remote Similarity	NPD1651	Approved
0.6599	Remote Similarity	NPD5691	Approved
0.6599	Remote Similarity	NPD9268	Approved
0.6597	Remote Similarity	NPD2629	Approved
0.6593	Remote Similarity	NPD2488	Approved
0.6593	Remote Similarity	NPD2490	Approved
0.6588	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3749	Approved
0.6582	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7033	Discontinued
0.6582	Remote Similarity	NPD1510	Phase 2
0.6568	Remote Similarity	NPD5402	Approved
0.6562	Remote Similarity	NPD1549	Phase 2
0.6562	Remote Similarity	NPD8151	Discontinued
0.6561	Remote Similarity	NPD7698	Approved
0.6561	Remote Similarity	NPD7680	Approved
0.6561	Remote Similarity	NPD7696	Phase 3
0.6561	Remote Similarity	NPD1607	Approved
0.6561	Remote Similarity	NPD7697	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data