NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.07
Volume:	238.504
LogP:	1.809
LogD:	2.07
LogS:	-3.161
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	3.587
Fsp3:	0.308
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:	-4.702
MDCK Permeability:	1.7485446733189747e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	94.93631744384766%
Volume Distribution (VD):	0.855
Pgp-substrate:	5.713264465332031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.345
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.603
CYP2C9-substrate:	0.614
CYP2D6-inhibitor:	0.876
CYP2D6-substrate:	0.293
CYP3A4-inhibitor:	0.343
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	16.286
Half-life (T1/2):	0.637

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.506
Rat Oral Acute Toxicity:	0.829
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.453
Carcinogencity:	0.937
Eye Corrosion:	0.009
Eye Irritation:	0.632
Respiratory Toxicity:	0.607

Download Data

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

Natural Product: NPC276328

Natural Product ID:	NPC276328
*Common Name:**	(-)-Dihydrocitromycin
IUPAC Name:	(2R)-8,9-dihydroxy-2-methyl-3,5-dihydro-2H-pyrano[3,2-c]chromen-4-one
Synonyms:	(-)-Dihydrocitromycin
Standard InCHIKey:	SGTSJAOFFFAYJH-ZCFIWIBFSA-N
Standard InCHI:	InChI=1S/C13H12O5/c1-6-2-9(14)8-5-17-12-4-11(16)10(15)3-7(12)13(8)18-6/h3-4,6,15-16H,2,5H2,1H3/t6-/m1/s1
SMILES:	C[C@@H]1CC(=O)C2=C(c3cc(c(cc3OC2)O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253330
PubChem CID:	10514677
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO33373	penicillium spp.	Species	Aspergillaceae	Eukaryota	n.a.	Australian	n.a.	PMID[17958395]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LD99	=	0.05	uM	PMID[529465]

☑ 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 NPC276328 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	350
0.1-0.2	1677
0.2-0.3	5375
0.3-0.4	12204
0.4-0.5	5317
0.5-0.6	4362
0.6-0.7	5483
0.7-0.8	7084
0.8-0.85	758
0.85-0.9	86
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC309031
0.8824	High Similarity	NPC277021
0.8777	High Similarity	NPC13067
0.8768	High Similarity	NPC82271
0.8768	High Similarity	NPC126682
0.875	High Similarity	NPC61871
0.875	High Similarity	NPC55557
0.875	High Similarity	NPC30647
0.8705	High Similarity	NPC76336
0.8705	High Similarity	NPC139548
0.8705	High Similarity	NPC52086
0.8705	High Similarity	NPC148835
0.8705	High Similarity	NPC20511
0.8705	High Similarity	NPC95162
0.8699	High Similarity	NPC184136
0.8681	High Similarity	NPC208507
0.8681	High Similarity	NPC472333
0.8667	High Similarity	NPC469658
0.8639	High Similarity	NPC204515
0.8621	High Similarity	NPC275772
0.8621	High Similarity	NPC130230
0.8621	High Similarity	NPC108406
0.8621	High Similarity	NPC239312
0.8621	High Similarity	NPC48366
0.8613	High Similarity	NPC137949
0.8611	High Similarity	NPC472917
0.8601	High Similarity	NPC175013
0.86	High Similarity	NPC470402
0.8591	High Similarity	NPC213622
0.8581	High Similarity	NPC100887
0.8581	High Similarity	NPC120163
0.8581	High Similarity	NPC256283
0.8581	High Similarity	NPC275836
0.8581	High Similarity	NPC198826
0.8581	High Similarity	NPC57030
0.8581	High Similarity	NPC212678
0.8581	High Similarity	NPC187498
0.8581	High Similarity	NPC162313
0.8581	High Similarity	NPC239128
0.8581	High Similarity	NPC25270
0.8581	High Similarity	NPC71334
0.8581	High Similarity	NPC131624
0.8581	High Similarity	NPC222830
0.8581	High Similarity	NPC142540
0.8581	High Similarity	NPC83508
0.8581	High Similarity	NPC301323
0.8581	High Similarity	NPC156222
0.8581	High Similarity	NPC275722
0.8581	High Similarity	NPC188203
0.8581	High Similarity	NPC293183
0.8581	High Similarity	NPC241498
0.8571	High Similarity	NPC62042
0.8571	High Similarity	NPC38874
0.8562	High Similarity	NPC294852
0.8562	High Similarity	NPC188679
0.8562	High Similarity	NPC321011
0.8562	High Similarity	NPC120464
0.8562	High Similarity	NPC12367
0.8562	High Similarity	NPC119059
0.8562	High Similarity	NPC118726
0.8552	High Similarity	NPC226987
0.8552	High Similarity	NPC143903
0.8551	High Similarity	NPC26673
0.8542	High Similarity	NPC279121
0.8533	High Similarity	NPC317383
0.8533	High Similarity	NPC255106
0.8533	High Similarity	NPC235165
0.8531	High Similarity	NPC7439
0.8531	High Similarity	NPC230157
0.8531	High Similarity	NPC236419
0.8531	High Similarity	NPC110067
0.8531	High Similarity	NPC34245
0.8531	High Similarity	NPC91492
0.8531	High Similarity	NPC256555
0.8529	High Similarity	NPC45824
0.8523	High Similarity	NPC69394
0.8523	High Similarity	NPC145379
0.8523	High Similarity	NPC75279
0.8523	High Similarity	NPC183878
0.8523	High Similarity	NPC160951
0.8523	High Similarity	NPC47781
0.8523	High Similarity	NPC276409
0.8523	High Similarity	NPC231018
0.8523	High Similarity	NPC255350
0.8523	High Similarity	NPC250822
0.8523	High Similarity	NPC22519
0.8523	High Similarity	NPC274327
0.8523	High Similarity	NPC176775
0.8514	High Similarity	NPC171010
0.8514	High Similarity	NPC475076
0.8503	High Similarity	NPC195351
0.8503	High Similarity	NPC177298
0.8503	High Similarity	NPC1612
0.8503	High Similarity	NPC87125
0.8503	High Similarity	NPC296197
0.8503	High Similarity	NPC48479
0.8503	High Similarity	NPC259713
0.8503	High Similarity	NPC17286
0.8503	High Similarity	NPC137062
0.8503	High Similarity	NPC183950
0.8503	High Similarity	NPC287101
0.8503	High Similarity	NPC328119
0.8503	High Similarity	NPC52005
0.8503	High Similarity	NPC270465
0.8503	High Similarity	NPC216318
0.8503	High Similarity	NPC183959
0.8503	High Similarity	NPC223579
0.8497	Intermediate Similarity	NPC194427
0.8493	Intermediate Similarity	NPC139839
0.8493	Intermediate Similarity	NPC207729
0.8489	Intermediate Similarity	NPC92830
0.8489	Intermediate Similarity	NPC106215
0.8483	Intermediate Similarity	NPC70136
0.8477	Intermediate Similarity	NPC156057
0.8477	Intermediate Similarity	NPC475267
0.8477	Intermediate Similarity	NPC474208
0.8477	Intermediate Similarity	NPC99597
0.8477	Intermediate Similarity	NPC162869
0.8477	Intermediate Similarity	NPC223787
0.8477	Intermediate Similarity	NPC474836
0.8477	Intermediate Similarity	NPC210084
0.8477	Intermediate Similarity	NPC48208
0.8467	Intermediate Similarity	NPC44079
0.8467	Intermediate Similarity	NPC214138
0.8467	Intermediate Similarity	NPC208197
0.8467	Intermediate Similarity	NPC163780
0.8467	Intermediate Similarity	NPC201136
0.8467	Intermediate Similarity	NPC146165
0.8467	Intermediate Similarity	NPC227325
0.8467	Intermediate Similarity	NPC2476
0.8467	Intermediate Similarity	NPC214860
0.8467	Intermediate Similarity	NPC50715
0.8467	Intermediate Similarity	NPC92659
0.8467	Intermediate Similarity	NPC280339
0.8467	Intermediate Similarity	NPC128863
0.8467	Intermediate Similarity	NPC256612
0.8467	Intermediate Similarity	NPC196439
0.8467	Intermediate Similarity	NPC138360
0.8467	Intermediate Similarity	NPC201451
0.8467	Intermediate Similarity	NPC2928
0.8467	Intermediate Similarity	NPC4455
0.8467	Intermediate Similarity	NPC167815
0.8467	Intermediate Similarity	NPC20830
0.8467	Intermediate Similarity	NPC183597
0.8467	Intermediate Similarity	NPC26227
0.8462	Intermediate Similarity	NPC472335
0.8462	Intermediate Similarity	NPC472332
0.8456	Intermediate Similarity	NPC120537
0.8456	Intermediate Similarity	NPC249570
0.8456	Intermediate Similarity	NPC302950
0.8456	Intermediate Similarity	NPC219582
0.8456	Intermediate Similarity	NPC180234
0.8456	Intermediate Similarity	NPC101996
0.8456	Intermediate Similarity	NPC106976
0.8456	Intermediate Similarity	NPC199100
0.8456	Intermediate Similarity	NPC39007
0.8456	Intermediate Similarity	NPC236637
0.8456	Intermediate Similarity	NPC161277
0.8446	Intermediate Similarity	NPC45873
0.8446	Intermediate Similarity	NPC149127
0.8446	Intermediate Similarity	NPC10467
0.8446	Intermediate Similarity	NPC286342
0.8446	Intermediate Similarity	NPC77858
0.8446	Intermediate Similarity	NPC188871
0.8446	Intermediate Similarity	NPC306821
0.844	Intermediate Similarity	NPC474282
0.844	Intermediate Similarity	NPC107551
0.844	Intermediate Similarity	NPC102904
0.844	Intermediate Similarity	NPC326797
0.844	Intermediate Similarity	NPC103976
0.844	Intermediate Similarity	NPC474886
0.844	Intermediate Similarity	NPC176051
0.8435	Intermediate Similarity	NPC30688
0.8435	Intermediate Similarity	NPC194856
0.8435	Intermediate Similarity	NPC176903
0.8435	Intermediate Similarity	NPC10010
0.8435	Intermediate Similarity	NPC276930
0.8435	Intermediate Similarity	NPC218490
0.8431	Intermediate Similarity	NPC198829
0.8429	Intermediate Similarity	NPC472337
0.8425	Intermediate Similarity	NPC231149
0.8425	Intermediate Similarity	NPC179271
0.8425	Intermediate Similarity	NPC169749
0.8425	Intermediate Similarity	NPC20791
0.8421	Intermediate Similarity	NPC329091
0.8417	Intermediate Similarity	NPC11060
0.8417	Intermediate Similarity	NPC168059
0.8417	Intermediate Similarity	NPC229442
0.8411	Intermediate Similarity	NPC49824
0.8411	Intermediate Similarity	NPC43243
0.8411	Intermediate Similarity	NPC276444
0.8411	Intermediate Similarity	NPC266960
0.8411	Intermediate Similarity	NPC245546
0.8411	Intermediate Similarity	NPC201837
0.8411	Intermediate Similarity	NPC200388
0.8411	Intermediate Similarity	NPC472916
0.8411	Intermediate Similarity	NPC98661
0.8411	Intermediate Similarity	NPC268161
0.8411	Intermediate Similarity	NPC247017
0.8411	Intermediate Similarity	NPC55619

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 NPC276328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	954
0.2-0.3	2222
0.3-0.4	2700
0.4-0.5	1517
0.5-0.6	890
0.6-0.7	449
0.7-0.8	95
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8542	High Similarity	NPD1511	Approved
0.8523	High Similarity	NPD2801	Approved
0.8456	Intermediate Similarity	NPD1934	Approved
0.8425	Intermediate Similarity	NPD1512	Approved
0.84	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1613	Approved
0.8345	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1653	Approved
0.8248	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3882	Suspended
0.7925	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6166	Phase 2
0.7888	Intermediate Similarity	NPD7054	Approved
0.7877	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD3027	Phase 3
0.7871	Intermediate Similarity	NPD3817	Phase 2
0.784	Intermediate Similarity	NPD7472	Approved
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7823	Intermediate Similarity	NPD1549	Phase 2
0.7821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD422	Phase 1
0.7805	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD1548	Phase 1
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7756	Intermediate Similarity	NPD5402	Approved
0.7748	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7251	Discontinued
0.774	Intermediate Similarity	NPD1510	Phase 2
0.773	Intermediate Similarity	NPD7074	Phase 3
0.7703	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4380	Phase 2
0.759	Intermediate Similarity	NPD7808	Phase 3
0.7571	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2796	Approved
0.7562	Intermediate Similarity	NPD5494	Approved
0.7554	Intermediate Similarity	NPD1610	Phase 2
0.7547	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1652	Phase 2
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7466	Intermediate Similarity	NPD1240	Approved
0.745	Intermediate Similarity	NPD1551	Phase 2
0.7438	Intermediate Similarity	NPD7075	Discontinued
0.7431	Intermediate Similarity	NPD4908	Phase 1
0.7419	Intermediate Similarity	NPD5403	Approved
0.7415	Intermediate Similarity	NPD447	Suspended
0.7415	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5124	Phase 1
0.7407	Intermediate Similarity	NPD1247	Approved
0.7407	Intermediate Similarity	NPD6959	Discontinued
0.7405	Intermediate Similarity	NPD6801	Discontinued
0.7403	Intermediate Similarity	NPD5401	Approved
0.7368	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1607	Approved
0.7361	Intermediate Similarity	NPD2861	Phase 2
0.7358	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5844	Phase 1
0.7347	Intermediate Similarity	NPD943	Approved
0.7338	Intermediate Similarity	NPD6799	Approved
0.7329	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4749	Approved
0.7312	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2800	Approved
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD3225	Approved
0.7259	Intermediate Similarity	NPD228	Approved
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7819	Suspended
0.7246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3496	Discontinued
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD2935	Discontinued
0.7219	Intermediate Similarity	NPD6100	Approved
0.7219	Intermediate Similarity	NPD6559	Discontinued
0.7211	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6190	Approved
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7183	Intermediate Similarity	NPD1091	Approved
0.7178	Intermediate Similarity	NPD919	Approved
0.7152	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7473	Discontinued
0.7125	Intermediate Similarity	NPD7411	Suspended
0.7124	Intermediate Similarity	NPD2424	Discontinued
0.7123	Intermediate Similarity	NPD3018	Phase 2
0.7123	Intermediate Similarity	NPD9494	Approved
0.709	Intermediate Similarity	NPD290	Approved
0.7089	Intermediate Similarity	NPD920	Approved
0.7081	Intermediate Similarity	NPD37	Approved
0.7075	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5536	Phase 2
0.707	Intermediate Similarity	NPD2532	Approved
0.707	Intermediate Similarity	NPD2534	Approved
0.707	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD6599	Discontinued
0.7059	Intermediate Similarity	NPD7266	Discontinued
0.7055	Intermediate Similarity	NPD4965	Approved
0.7055	Intermediate Similarity	NPD4967	Phase 2
0.7055	Intermediate Similarity	NPD4966	Approved
0.7055	Intermediate Similarity	NPD7768	Phase 2
0.705	Intermediate Similarity	NPD6671	Approved
0.7048	Intermediate Similarity	NPD3787	Discontinued
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7042	Intermediate Similarity	NPD1778	Approved
0.7039	Intermediate Similarity	NPD7033	Discontinued
0.7039	Intermediate Similarity	NPD3748	Approved
0.7027	Intermediate Similarity	NPD4625	Phase 3
0.7015	Intermediate Similarity	NPD968	Approved
0.7014	Intermediate Similarity	NPD9717	Approved
0.7014	Intermediate Similarity	NPD9269	Phase 2
0.7006	Intermediate Similarity	NPD4357	Discontinued
0.6988	Remote Similarity	NPD7199	Phase 2
0.6986	Remote Similarity	NPD1203	Approved
0.6982	Remote Similarity	NPD7228	Approved
0.698	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1296	Phase 2
0.6977	Remote Similarity	NPD7549	Discontinued
0.6968	Remote Similarity	NPD1243	Approved
0.6966	Remote Similarity	NPD2983	Phase 2
0.6966	Remote Similarity	NPD2982	Phase 2
0.6918	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6651	Approved
0.6906	Remote Similarity	NPD1241	Discontinued
0.6905	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2981	Phase 2
0.6887	Remote Similarity	NPD4060	Phase 1
0.6887	Remote Similarity	NPD1558	Phase 1
0.6871	Remote Similarity	NPD2797	Approved
0.6867	Remote Similarity	NPD6798	Discontinued
0.6867	Remote Similarity	NPD411	Approved
0.6867	Remote Similarity	NPD3268	Approved
0.6864	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1933	Approved
0.6836	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1535	Discovery
0.6824	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4628	Phase 3
0.681	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3749	Approved
0.6805	Remote Similarity	NPD3926	Phase 2
0.6803	Remote Similarity	NPD6696	Suspended
0.6792	Remote Similarity	NPD7213	Phase 3
0.6792	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7212	Phase 2
0.6781	Remote Similarity	NPD1481	Phase 2
0.6772	Remote Similarity	NPD2219	Phase 1
0.677	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6844	Discontinued
0.6761	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2313	Discontinued
0.6752	Remote Similarity	NPD6674	Discontinued
0.675	Remote Similarity	NPD7447	Phase 1
0.6748	Remote Similarity	NPD4675	Approved
0.6748	Remote Similarity	NPD4678	Approved
0.6736	Remote Similarity	NPD9268	Approved
0.6732	Remote Similarity	NPD6355	Discontinued
0.6732	Remote Similarity	NPD4340	Discontinued
0.6712	Remote Similarity	NPD3705	Approved
0.6711	Remote Similarity	NPD1019	Discontinued
0.671	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD8651	Approved
0.6688	Remote Similarity	NPD6653	Approved
0.6687	Remote Similarity	NPD5353	Approved
0.6687	Remote Similarity	NPD3226	Approved
0.6686	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD9545	Approved
0.6647	Remote Similarity	NPD7286	Phase 2
0.6646	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1578	Phase 2
0.6644	Remote Similarity	NPD3267	Approved
0.6644	Remote Similarity	NPD3266	Approved
0.6643	Remote Similarity	NPD9493	Approved
0.6642	Remote Similarity	NPD1242	Phase 1
0.6629	Remote Similarity	NPD7685	Pre-registration
0.6626	Remote Similarity	NPD3687	Approved
0.6626	Remote Similarity	NPD3686	Approved
0.6624	Remote Similarity	NPD3540	Phase 1
0.6624	Remote Similarity	NPD2346	Discontinued
0.6624	Remote Similarity	NPD2344	Approved
0.6624	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6832	Phase 2
0.6621	Remote Similarity	NPD1357	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