NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.05
Volume:	250.527
LogP:	2.356
LogD:	1.513
LogS:	-3.517
# Rotatable Bonds:	0
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	3.171
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.961
MDCK Permeability:	6.2941326177679e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.144
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	0.272
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	93.0460433959961%
Volume Distribution (VD):	0.46
Pgp-substrate:	10.584381103515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.819
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.415
CYP2C9-substrate:	0.454
CYP2D6-inhibitor:	0.594
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.121
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	9.006
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.084
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.324
Rat Oral Acute Toxicity:	0.282
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.948
Carcinogencity:	0.624
Eye Corrosion:	0.004
Eye Irritation:	0.916
Respiratory Toxicity:	0.255

Download Data

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

Natural Product: NPC156872

Natural Product ID:	NPC156872
*Common Name:**	6-Deoxy-7-O-Demethyl-3,4-Anhydrofusarubin
IUPAC Name:	7,9-dihydroxy-3-methyl-1H-benzo[g]isochromene-5,10-dione
Synonyms:
Standard InCHIKey:	ATLURBSTOUCQEI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O5/c1-6-2-8-10(5-19-6)14(18)12-9(13(8)17)3-7(15)4-11(12)16/h2-4,15-16H,5H2,1H3
SMILES:	CC1=CC2=C(CO1)C(=O)c1c(C2=O)cc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479229
PubChem CID:	125571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001649] Isochromanequinones [CHEMONTID:0002355] Benzoisochromanequinones

*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
NPO40045	Biatriospora sp.	Species	Biatriosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27556953]
NPO32584	trichopezizella nidulus	Species	Hyaloscyphaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548866]

☑ 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
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6284	Organism	Lachnellula	Lachnellula	IZ	=	14.0	mm	PMID[536625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC80	=	32.0	ug.mL-1	PMID[536626]

☑ 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 NPC156872 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	347
0.1-0.2	1500
0.2-0.3	3681
0.3-0.4	9060
0.4-0.5	9771
0.5-0.6	3804
0.6-0.7	6603
0.7-0.8	6000
0.8-0.85	1645
0.85-0.9	262
0.9-0.95	21
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC475201
0.9275	High Similarity	NPC109007
0.9149	High Similarity	NPC19896
0.9078	High Similarity	NPC277369
0.9078	High Similarity	NPC215451
0.9065	High Similarity	NPC92655
0.9065	High Similarity	NPC268052
0.9021	High Similarity	NPC470570
0.9014	High Similarity	NPC48762
0.9014	High Similarity	NPC21599
0.9014	High Similarity	NPC193703
0.8978	High Similarity	NPC175943
0.8973	High Similarity	NPC46882
0.8973	High Similarity	NPC132990
0.8966	High Similarity	NPC84142
0.8958	High Similarity	NPC312929
0.8958	High Similarity	NPC190648
0.8958	High Similarity	NPC126767
0.8958	High Similarity	NPC289042
0.8958	High Similarity	NPC118027
0.8958	High Similarity	NPC245584
0.8958	High Similarity	NPC56433
0.8951	High Similarity	NPC28632
0.8951	High Similarity	NPC34482
0.8929	High Similarity	NPC32360
0.8912	High Similarity	NPC154683
0.8912	High Similarity	NPC40356
0.8905	High Similarity	NPC153783
0.8904	High Similarity	NPC290954
0.8904	High Similarity	NPC470568
0.8904	High Similarity	NPC164762
0.8904	High Similarity	NPC255641
0.8904	High Similarity	NPC147735
0.8859	High Similarity	NPC472050
0.8857	High Similarity	NPC61590
0.8851	High Similarity	NPC155686
0.8849	High Similarity	NPC242712
0.8849	High Similarity	NPC235115
0.8849	High Similarity	NPC254847
0.8849	High Similarity	NPC50455
0.8844	High Similarity	NPC91809
0.8844	High Similarity	NPC470569
0.8841	High Similarity	NPC44437
0.8828	High Similarity	NPC22005
0.8828	High Similarity	NPC7943
0.8828	High Similarity	NPC123202
0.8815	High Similarity	NPC179898
0.8803	High Similarity	NPC158634
0.8803	High Similarity	NPC204045
0.8803	High Similarity	NPC305845
0.8794	High Similarity	NPC295339
0.8794	High Similarity	NPC190457
0.8794	High Similarity	NPC247409
0.8794	High Similarity	NPC52358
0.8794	High Similarity	NPC57380
0.8786	High Similarity	NPC53414
0.8786	High Similarity	NPC471905
0.8786	High Similarity	NPC135837
0.8786	High Similarity	NPC53206
0.8786	High Similarity	NPC193792
0.8784	High Similarity	NPC115249
0.8784	High Similarity	NPC470340
0.8776	High Similarity	NPC202595
0.8776	High Similarity	NPC294646
0.8776	High Similarity	NPC472891
0.8776	High Similarity	NPC295036
0.8767	High Similarity	NPC153417
0.8767	High Similarity	NPC27221
0.8767	High Similarity	NPC256672
0.8767	High Similarity	NPC7025
0.8759	High Similarity	NPC189823
0.8759	High Similarity	NPC219892
0.8741	High Similarity	NPC49108
0.8741	High Similarity	NPC94076
0.8741	High Similarity	NPC135524
0.8741	High Similarity	NPC82913
0.8741	High Similarity	NPC182255
0.8732	High Similarity	NPC469523
0.8725	High Similarity	NPC214632
0.8725	High Similarity	NPC137301
0.8725	High Similarity	NPC478231
0.8725	High Similarity	NPC208806
0.8723	High Similarity	NPC191835
0.8723	High Similarity	NPC33144
0.8723	High Similarity	NPC478200
0.8723	High Similarity	NPC212767
0.8716	High Similarity	NPC230848
0.8714	High Similarity	NPC158481
0.8707	High Similarity	NPC97029
0.8707	High Similarity	NPC97028
0.8707	High Similarity	NPC158338
0.8707	High Similarity	NPC288036
0.8707	High Similarity	NPC10027
0.8707	High Similarity	NPC65589
0.8707	High Similarity	NPC134293
0.8707	High Similarity	NPC100985
0.8707	High Similarity	NPC4423
0.8707	High Similarity	NPC77325
0.8707	High Similarity	NPC65775
0.869	High Similarity	NPC474630
0.8686	High Similarity	NPC147757
0.8681	High Similarity	NPC472006
0.8681	High Similarity	NPC310340
0.8681	High Similarity	NPC84266
0.8681	High Similarity	NPC159721
0.8681	High Similarity	NPC478202
0.8675	High Similarity	NPC263483
0.8675	High Similarity	NPC472889
0.8671	High Similarity	NPC90411
0.8671	High Similarity	NPC472603
0.8671	High Similarity	NPC53649
0.8671	High Similarity	NPC275734
0.8671	High Similarity	NPC101366
0.8671	High Similarity	NPC472035
0.8671	High Similarity	NPC478201
0.8671	High Similarity	NPC110810
0.8671	High Similarity	NPC253822
0.8671	High Similarity	NPC283292
0.8671	High Similarity	NPC37530
0.8667	High Similarity	NPC472890
0.8667	High Similarity	NPC478221
0.8667	High Similarity	NPC317585
0.8662	High Similarity	NPC242994
0.8662	High Similarity	NPC278323
0.8662	High Similarity	NPC90665
0.8662	High Similarity	NPC309154
0.8662	High Similarity	NPC279668
0.8662	High Similarity	NPC25427
0.8662	High Similarity	NPC55162
0.8662	High Similarity	NPC275356
0.8662	High Similarity	NPC143438
0.8662	High Similarity	NPC88269
0.8662	High Similarity	NPC138099
0.8662	High Similarity	NPC12175
0.8658	High Similarity	NPC478224
0.8658	High Similarity	NPC184284
0.8658	High Similarity	NPC76041
0.8652	High Similarity	NPC235428
0.8652	High Similarity	NPC87545
0.8652	High Similarity	NPC70380
0.8649	High Similarity	NPC470107
0.8643	High Similarity	NPC180905
0.8643	High Similarity	NPC182496
0.8639	High Similarity	NPC2569
0.8639	High Similarity	NPC172329
0.8633	High Similarity	NPC267205
0.863	High Similarity	NPC472033
0.8621	High Similarity	NPC151607
0.8621	High Similarity	NPC244691
0.8621	High Similarity	NPC471906
0.8621	High Similarity	NPC42540
0.8611	High Similarity	NPC73061
0.8611	High Similarity	NPC26051
0.8611	High Similarity	NPC268204
0.8611	High Similarity	NPC55832
0.8611	High Similarity	NPC40118
0.8611	High Similarity	NPC126534
0.8611	High Similarity	NPC232021
0.8611	High Similarity	NPC52789
0.8601	High Similarity	NPC99441
0.8601	High Similarity	NPC49242
0.8601	High Similarity	NPC181560
0.8601	High Similarity	NPC169452
0.8601	High Similarity	NPC472600
0.8601	High Similarity	NPC165172
0.8601	High Similarity	NPC155205
0.8601	High Similarity	NPC472601
0.8601	High Similarity	NPC295384
0.86	High Similarity	NPC210942
0.86	High Similarity	NPC169990
0.86	High Similarity	NPC107109
0.86	High Similarity	NPC93552
0.8592	High Similarity	NPC472602
0.8592	High Similarity	NPC116632
0.8592	High Similarity	NPC173980
0.8592	High Similarity	NPC9121
0.8592	High Similarity	NPC94248
0.8592	High Similarity	NPC177307
0.8592	High Similarity	NPC209560
0.8592	High Similarity	NPC181124
0.8592	High Similarity	NPC162680
0.8592	High Similarity	NPC212693
0.8592	High Similarity	NPC7013
0.8592	High Similarity	NPC472403
0.8592	High Similarity	NPC294409
0.8592	High Similarity	NPC303644
0.8591	High Similarity	NPC149526
0.8591	High Similarity	NPC258249
0.8591	High Similarity	NPC232645
0.8591	High Similarity	NPC72958
0.8591	High Similarity	NPC474417
0.8591	High Similarity	NPC478148
0.8582	High Similarity	NPC60667
0.8582	High Similarity	NPC234560
0.8582	High Similarity	NPC315275
0.8582	High Similarity	NPC39426
0.8581	High Similarity	NPC80370
0.8571	High Similarity	NPC166480
0.8571	High Similarity	NPC34802
0.8571	High Similarity	NPC259632

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 NPC156872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	947
0.2-0.3	1662
0.3-0.4	2715
0.4-0.5	1916
0.5-0.6	1129
0.6-0.7	336
0.7-0.8	118
0.8-0.85	18
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8849	High Similarity	NPD1509	Clinical (unspecified phase)
0.8794	High Similarity	NPD970	Clinical (unspecified phase)
0.8582	High Similarity	NPD1510	Phase 2
0.8311	Intermediate Similarity	NPD2534	Approved
0.8311	Intermediate Similarity	NPD2533	Approved
0.8311	Intermediate Similarity	NPD2532	Approved
0.831	Intermediate Similarity	NPD1607	Approved
0.8298	Intermediate Similarity	NPD1240	Approved
0.8276	Intermediate Similarity	NPD1549	Phase 2
0.8235	Intermediate Similarity	NPD7819	Suspended
0.8207	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1470	Approved
0.8188	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1511	Approved
0.8069	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD943	Approved
0.8041	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3750	Approved
0.8039	Intermediate Similarity	NPD4380	Phase 2
0.8038	Intermediate Similarity	NPD6959	Discontinued
0.8014	Intermediate Similarity	NPD2796	Approved
0.8013	Intermediate Similarity	NPD1512	Approved
0.8	Intermediate Similarity	NPD7390	Discontinued
0.8	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2801	Approved
0.7987	Intermediate Similarity	NPD6232	Discontinued
0.7986	Intermediate Similarity	NPD230	Phase 1
0.7985	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2800	Approved
0.795	Intermediate Similarity	NPD7473	Discontinued
0.7947	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1934	Approved
0.7899	Intermediate Similarity	NPD1201	Approved
0.7898	Intermediate Similarity	NPD3882	Suspended
0.7834	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1551	Phase 2
0.7756	Intermediate Similarity	NPD7411	Suspended
0.7742	Intermediate Similarity	NPD3226	Approved
0.7736	Intermediate Similarity	NPD7075	Discontinued
0.7736	Intermediate Similarity	NPD3749	Approved
0.7703	Intermediate Similarity	NPD3748	Approved
0.7687	Intermediate Similarity	NPD6651	Approved
0.7658	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5710	Approved
0.7654	Intermediate Similarity	NPD5711	Approved
0.7647	Intermediate Similarity	NPD6799	Approved
0.7625	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1243	Approved
0.7613	Intermediate Similarity	NPD920	Approved
0.761	Intermediate Similarity	NPD3817	Phase 2
0.7609	Intermediate Similarity	NPD9545	Approved
0.7595	Intermediate Similarity	NPD6801	Discontinued
0.758	Intermediate Similarity	NPD6599	Discontinued
0.7576	Intermediate Similarity	NPD3818	Discontinued
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7768	Phase 2
0.7561	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7533	Intermediate Similarity	NPD5408	Approved
0.7533	Intermediate Similarity	NPD5404	Approved
0.7533	Intermediate Similarity	NPD2935	Discontinued
0.7533	Intermediate Similarity	NPD5405	Approved
0.7533	Intermediate Similarity	NPD5406	Approved
0.7531	Intermediate Similarity	NPD5494	Approved
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD9493	Approved
0.7455	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6166	Phase 2
0.7455	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7425	Intermediate Similarity	NPD7054	Approved
0.7425	Intermediate Similarity	NPD5844	Phase 1
0.7415	Intermediate Similarity	NPD3764	Approved
0.7391	Intermediate Similarity	NPD5402	Approved
0.7386	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7472	Approved
0.7378	Intermediate Similarity	NPD1247	Approved
0.7362	Intermediate Similarity	NPD919	Approved
0.7343	Intermediate Similarity	NPD9269	Phase 2
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7337	Intermediate Similarity	NPD6797	Phase 2
0.7321	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD9268	Approved
0.7297	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7251	Discontinued
0.7294	Intermediate Similarity	NPD6559	Discontinued
0.729	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD5403	Approved
0.7278	Intermediate Similarity	NPD7074	Phase 3
0.7262	Intermediate Similarity	NPD3751	Discontinued
0.7261	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5401	Approved
0.7255	Intermediate Similarity	NPD1471	Phase 3
0.7251	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7808	Phase 3
0.7251	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2799	Discontinued
0.7226	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9717	Approved
0.7192	Intermediate Similarity	NPD1164	Approved
0.7192	Intermediate Similarity	NPD1203	Approved
0.7186	Intermediate Similarity	NPD3926	Phase 2
0.7184	Intermediate Similarity	NPD8150	Discontinued
0.7181	Intermediate Similarity	NPD2313	Discontinued
0.7181	Intermediate Similarity	NPD411	Approved
0.7161	Intermediate Similarity	NPD2654	Approved
0.7153	Intermediate Similarity	NPD422	Phase 1
0.7152	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD2798	Approved
0.7118	Intermediate Similarity	NPD7286	Phase 2
0.7115	Intermediate Similarity	NPD4628	Phase 3
0.7113	Intermediate Similarity	NPD1548	Phase 1
0.7102	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD9494	Approved
0.7073	Intermediate Similarity	NPD4288	Approved
0.7067	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD37	Approved
0.7055	Intermediate Similarity	NPD4749	Approved
0.7048	Intermediate Similarity	NPD6234	Discontinued
0.7039	Intermediate Similarity	NPD6534	Approved
0.7039	Intermediate Similarity	NPD6535	Approved
0.7035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1610	Phase 2
0.7033	Intermediate Similarity	NPD6780	Approved
0.7033	Intermediate Similarity	NPD6777	Approved
0.7033	Intermediate Similarity	NPD6779	Approved
0.7033	Intermediate Similarity	NPD6781	Approved
0.7033	Intermediate Similarity	NPD6778	Approved
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6782	Approved
0.7033	Intermediate Similarity	NPD6776	Approved
0.703	Intermediate Similarity	NPD4965	Approved
0.703	Intermediate Similarity	NPD4966	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.7027	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3300	Phase 2
0.7014	Intermediate Similarity	NPD2932	Approved
0.7007	Intermediate Similarity	NPD74	Approved
0.7007	Intermediate Similarity	NPD9266	Approved
0.7006	Intermediate Similarity	NPD8166	Discontinued
0.7005	Intermediate Similarity	NPD8151	Discontinued
0.7	Intermediate Similarity	NPD1241	Discontinued
0.7	Intermediate Similarity	NPD4625	Phase 3
0.6975	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6190	Approved
0.6957	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4750	Phase 3
0.6954	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD9267	Approved
0.6934	Remote Similarity	NPD9263	Approved
0.6934	Remote Similarity	NPD9264	Approved
0.6933	Remote Similarity	NPD6832	Phase 2
0.6933	Remote Similarity	NPD4908	Phase 1
0.6928	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD7699	Phase 2
0.6923	Remote Similarity	NPD7700	Phase 2
0.6919	Remote Similarity	NPD7697	Approved
0.6919	Remote Similarity	NPD7435	Discontinued
0.6919	Remote Similarity	NPD7698	Approved
0.6919	Remote Similarity	NPD7696	Phase 3
0.6914	Remote Similarity	NPD8313	Approved
0.6914	Remote Similarity	NPD8312	Approved
0.6903	Remote Similarity	NPD4308	Phase 3
0.6903	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7003	Approved
0.6897	Remote Similarity	NPD3019	Approved
0.6897	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8434	Phase 2
0.6892	Remote Similarity	NPD1283	Approved
0.6892	Remote Similarity	NPD1876	Approved
0.6882	Remote Similarity	NPD7871	Phase 2
0.6882	Remote Similarity	NPD7870	Phase 2
0.6871	Remote Similarity	NPD3972	Approved
0.6871	Remote Similarity	NPD1608	Approved
0.6871	Remote Similarity	NPD7458	Discontinued
0.6851	Remote Similarity	NPD4360	Phase 2
0.6851	Remote Similarity	NPD4363	Phase 3
0.6842	Remote Similarity	NPD3268	Approved
0.6832	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1651	Approved
0.6824	Remote Similarity	NPD3787	Discontinued
0.6816	Remote Similarity	NPD4287	Approved
0.6813	Remote Similarity	NPD4361	Phase 2
0.6813	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5761	Phase 2
0.6807	Remote Similarity	NPD5760	Phase 2
0.68	Remote Similarity	NPD1019	Discontinued
0.6797	Remote Similarity	NPD520	Approved
0.6796	Remote Similarity	NPD6212	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