NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.15
Volume:	286.874
LogP:	3.469
LogD:	2.848
LogS:	-3.771
# Rotatable Bonds:	1
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	4.601
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.591
MDCK Permeability:	2.1341576939448714e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.788
Plasma Protein Binding (PPB):	95.01808166503906%
Volume Distribution (VD):	1.755
Pgp-substrate:	3.3663218021392822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.361
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.413
CYP2C9-substrate:	0.611
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.337
CYP3A4-inhibitor:	0.441
CYP3A4-substrate:	0.767

ADMET: Excretion

Clearance (CL):	10.19
Half-life (T1/2):	0.595

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.635
Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.32
Carcinogencity:	0.759
Eye Corrosion:	0.01
Eye Irritation:	0.828
Respiratory Toxicity:	0.782

Download Data

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

Natural Product: NPC24913

Natural Product ID:	NPC24913
*Common Name:**	DIFREUFYEBCDCG-YZTUOPDFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DIFREUFYEBCDCG-YZTUOPDFSA-N
Standard InCHI:	InChI=1S/C16H22O4/c1-8-10(3)19-13-7-16(4,18-5)20-12-6-11(17)9(2)14(8)15(12)13/h6,8,10,13,17H,7H2,1-5H3/t8-,10-,13-,16-/m1/s1
SMILES:	C[C@@H]1[C@@H](C)O[C@@H]2C[C@](C)(OC)Oc3cc(c(C)c1c23)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3422276
PubChem CID:	52952877
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-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
NPO32511	Penicillium chrysogenum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25611519]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[527341]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	42500.0	nM	PMID[527341]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	35500.0	nM	PMID[527341]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[527341]

☑ 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 NPC24913 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	377
0.1-0.2	1598
0.2-0.3	4081
0.3-0.4	11413
0.4-0.5	7347
0.5-0.6	4030
0.6-0.7	8135
0.7-0.8	4901
0.8-0.85	661
0.85-0.9	143
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177712
0.9375	High Similarity	NPC474494
0.9375	High Similarity	NPC25729
0.9313	High Similarity	NPC473107
0.9127	High Similarity	NPC57199
0.9051	High Similarity	NPC472451
0.8936	High Similarity	NPC470208
0.8936	High Similarity	NPC295573
0.8923	High Similarity	NPC473134
0.8915	High Similarity	NPC293801
0.8889	High Similarity	NPC3239
0.8889	High Similarity	NPC282255
0.8864	High Similarity	NPC470225
0.8864	High Similarity	NPC27187
0.8855	High Similarity	NPC53986
0.8855	High Similarity	NPC38664
0.8815	High Similarity	NPC137580
0.8797	High Similarity	NPC129784
0.8797	High Similarity	NPC280653
0.8797	High Similarity	NPC164574
0.8797	High Similarity	NPC300875
0.8797	High Similarity	NPC228369
0.8797	High Similarity	NPC181497
0.8797	High Similarity	NPC206224
0.8797	High Similarity	NPC476166
0.8797	High Similarity	NPC12875
0.8797	High Similarity	NPC271945
0.8797	High Similarity	NPC207892
0.8797	High Similarity	NPC17343
0.8797	High Similarity	NPC196765
0.8797	High Similarity	NPC118114
0.8797	High Similarity	NPC129106
0.8797	High Similarity	NPC236014
0.8797	High Similarity	NPC150011
0.8797	High Similarity	NPC268917
0.8788	High Similarity	NPC93962
0.8769	High Similarity	NPC188022
0.8769	High Similarity	NPC17809
0.8769	High Similarity	NPC285040
0.8769	High Similarity	NPC103420
0.8769	High Similarity	NPC102540
0.8759	High Similarity	NPC32630
0.8731	High Similarity	NPC13005
0.8731	High Similarity	NPC472798
0.8714	High Similarity	NPC473108
0.8712	High Similarity	NPC274717
0.8702	High Similarity	NPC276212
0.8702	High Similarity	NPC283049
0.8702	High Similarity	NPC26879
0.8702	High Similarity	NPC50315
0.8702	High Similarity	NPC230479
0.8692	High Similarity	NPC86502
0.8692	High Similarity	NPC134195
0.8692	High Similarity	NPC197351
0.8692	High Similarity	NPC246648
0.8692	High Similarity	NPC106914
0.8657	High Similarity	NPC160623
0.8657	High Similarity	NPC68205
0.8657	High Similarity	NPC211413
0.8657	High Similarity	NPC244888
0.8657	High Similarity	NPC118683
0.8657	High Similarity	NPC164804
0.8657	High Similarity	NPC293203
0.8647	High Similarity	NPC472795
0.8647	High Similarity	NPC472797
0.8647	High Similarity	NPC472796
0.8633	High Similarity	NPC265075
0.8633	High Similarity	NPC5155
0.8621	High Similarity	NPC476452
0.8615	High Similarity	NPC76465
0.8615	High Similarity	NPC38761
0.8613	High Similarity	NPC472800
0.8613	High Similarity	NPC234952
0.8603	High Similarity	NPC115335
0.8603	High Similarity	NPC97834
0.8603	High Similarity	NPC223008
0.8603	High Similarity	NPC198154
0.8603	High Similarity	NPC296915
0.8603	High Similarity	NPC225696
0.8601	High Similarity	NPC71726
0.8592	High Similarity	NPC471608
0.8571	High Similarity	NPC47283
0.8571	High Similarity	NPC38604
0.8571	High Similarity	NPC211179
0.8571	High Similarity	NPC223912
0.8571	High Similarity	NPC39064
0.854	High Similarity	NPC15109
0.854	High Similarity	NPC11727
0.854	High Similarity	NPC125579
0.854	High Similarity	NPC473413
0.8538	High Similarity	NPC100099
0.8538	High Similarity	NPC36016
0.8538	High Similarity	NPC74137
0.8529	High Similarity	NPC469610
0.8529	High Similarity	NPC215037
0.8529	High Similarity	NPC77196
0.8529	High Similarity	NPC85435
0.8521	High Similarity	NPC180953
0.8519	High Similarity	NPC8899
0.8519	High Similarity	NPC103799
0.8507	High Similarity	NPC16577
0.85	High Similarity	NPC210192
0.8496	Intermediate Similarity	NPC149796
0.8489	Intermediate Similarity	NPC70682
0.8489	Intermediate Similarity	NPC470209
0.8489	Intermediate Similarity	NPC260741
0.8489	Intermediate Similarity	NPC475836
0.8485	Intermediate Similarity	NPC105031
0.8485	Intermediate Similarity	NPC113495
0.8483	Intermediate Similarity	NPC472710
0.8483	Intermediate Similarity	NPC472709
0.8478	Intermediate Similarity	NPC470802
0.8478	Intermediate Similarity	NPC471522
0.8473	Intermediate Similarity	NPC96940
0.8467	Intermediate Similarity	NPC476615
0.8467	Intermediate Similarity	NPC124085
0.8467	Intermediate Similarity	NPC476617
0.8467	Intermediate Similarity	NPC476616
0.8467	Intermediate Similarity	NPC117048
0.8462	Intermediate Similarity	NPC102280
0.8462	Intermediate Similarity	NPC248053
0.8462	Intermediate Similarity	NPC54972
0.8462	Intermediate Similarity	NPC155564
0.8462	Intermediate Similarity	NPC476633
0.8462	Intermediate Similarity	NPC193364
0.8456	Intermediate Similarity	NPC469611
0.8451	Intermediate Similarity	NPC473845
0.8451	Intermediate Similarity	NPC50250
0.8444	Intermediate Similarity	NPC262606
0.8444	Intermediate Similarity	NPC254000
0.844	Intermediate Similarity	NPC49542
0.844	Intermediate Similarity	NPC84207
0.844	Intermediate Similarity	NPC128337
0.844	Intermediate Similarity	NPC230718
0.844	Intermediate Similarity	NPC5253
0.844	Intermediate Similarity	NPC139976
0.8429	Intermediate Similarity	NPC109240
0.8429	Intermediate Similarity	NPC259519
0.8421	Intermediate Similarity	NPC471215
0.8421	Intermediate Similarity	NPC170485
0.8421	Intermediate Similarity	NPC262573
0.8417	Intermediate Similarity	NPC474687
0.8417	Intermediate Similarity	NPC470307
0.8417	Intermediate Similarity	NPC134260
0.8417	Intermediate Similarity	NPC87777
0.8417	Intermediate Similarity	NPC470308
0.8417	Intermediate Similarity	NPC262328
0.8403	Intermediate Similarity	NPC474397
0.8394	Intermediate Similarity	NPC92805
0.8394	Intermediate Similarity	NPC11060
0.8394	Intermediate Similarity	NPC185777
0.8392	Intermediate Similarity	NPC161700
0.8392	Intermediate Similarity	NPC307466
0.8392	Intermediate Similarity	NPC277867
0.8389	Intermediate Similarity	NPC164244
0.8385	Intermediate Similarity	NPC102639
0.8382	Intermediate Similarity	NPC162801
0.8382	Intermediate Similarity	NPC282508
0.838	Intermediate Similarity	NPC81638
0.838	Intermediate Similarity	NPC47633
0.838	Intermediate Similarity	NPC85264
0.838	Intermediate Similarity	NPC102044
0.838	Intermediate Similarity	NPC37793
0.837	Intermediate Similarity	NPC96719
0.837	Intermediate Similarity	NPC471518
0.837	Intermediate Similarity	NPC222108
0.837	Intermediate Similarity	NPC134360
0.837	Intermediate Similarity	NPC471519
0.8369	Intermediate Similarity	NPC35216
0.8369	Intermediate Similarity	NPC71046
0.8369	Intermediate Similarity	NPC108674
0.8367	Intermediate Similarity	NPC469944
0.8367	Intermediate Similarity	NPC226108
0.8367	Intermediate Similarity	NPC272552
0.8367	Intermediate Similarity	NPC134911
0.8367	Intermediate Similarity	NPC21902
0.8367	Intermediate Similarity	NPC44192
0.8367	Intermediate Similarity	NPC322899
0.8367	Intermediate Similarity	NPC46283
0.8357	Intermediate Similarity	NPC471388
0.8357	Intermediate Similarity	NPC292487
0.8356	Intermediate Similarity	NPC260781
0.8356	Intermediate Similarity	NPC9933
0.8356	Intermediate Similarity	NPC218041
0.8356	Intermediate Similarity	NPC214326
0.8356	Intermediate Similarity	NPC182368
0.8356	Intermediate Similarity	NPC185955
0.8356	Intermediate Similarity	NPC225815
0.8356	Intermediate Similarity	NPC145979
0.8356	Intermediate Similarity	NPC469707
0.8356	Intermediate Similarity	NPC469706
0.8346	Intermediate Similarity	NPC476653
0.8345	Intermediate Similarity	NPC473876
0.8345	Intermediate Similarity	NPC162659
0.8345	Intermediate Similarity	NPC18189
0.8345	Intermediate Similarity	NPC270751
0.8345	Intermediate Similarity	NPC173660
0.8345	Intermediate Similarity	NPC126101
0.8345	Intermediate Similarity	NPC248727
0.8345	Intermediate Similarity	NPC265433

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 NPC24913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	969
0.2-0.3	1916
0.3-0.4	2711
0.4-0.5	1605
0.5-0.6	930
0.6-0.7	584
0.7-0.8	100
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8722	High Similarity	NPD4907	Clinical (unspecified phase)
0.8571	High Similarity	NPD4908	Phase 1
0.8507	High Similarity	NPD4625	Phase 3
0.8473	Intermediate Similarity	NPD4749	Approved
0.8462	Intermediate Similarity	NPD1610	Phase 2
0.8444	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD2861	Phase 2
0.8058	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1613	Approved
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.8015	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5124	Phase 1
0.8	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6674	Discontinued
0.7956	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4060	Phase 1
0.7899	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1091	Approved
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7737	Intermediate Similarity	NPD6696	Suspended
0.7714	Intermediate Similarity	NPD3027	Phase 3
0.7712	Intermediate Similarity	NPD37	Approved
0.7707	Intermediate Similarity	NPD6959	Discontinued
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7677	Intermediate Similarity	NPD4967	Phase 2
0.7677	Intermediate Similarity	NPD4966	Approved
0.7677	Intermediate Similarity	NPD4965	Approved
0.7662	Intermediate Similarity	NPD7819	Suspended
0.7647	Intermediate Similarity	NPD422	Phase 1
0.7594	Intermediate Similarity	NPD7340	Approved
0.7586	Intermediate Similarity	NPD4108	Discontinued
0.7578	Intermediate Similarity	NPD7228	Approved
0.7566	Intermediate Similarity	NPD1653	Approved
0.7551	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6671	Approved
0.7518	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1398	Phase 1
0.7484	Intermediate Similarity	NPD7199	Phase 2
0.7482	Intermediate Similarity	NPD8651	Approved
0.7462	Intermediate Similarity	NPD4750	Phase 3
0.745	Intermediate Similarity	NPD3892	Phase 2
0.745	Intermediate Similarity	NPD3750	Approved
0.7431	Intermediate Similarity	NPD4140	Approved
0.7426	Intermediate Similarity	NPD5691	Approved
0.7419	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7212	Phase 2
0.7417	Intermediate Similarity	NPD7213	Phase 3
0.741	Intermediate Similarity	NPD5327	Phase 3
0.7391	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5735	Approved
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2533	Approved
0.7368	Intermediate Similarity	NPD2534	Approved
0.7368	Intermediate Similarity	NPD7447	Phase 1
0.7368	Intermediate Similarity	NPD2532	Approved
0.7365	Intermediate Similarity	NPD5763	Approved
0.7365	Intermediate Similarity	NPD5762	Approved
0.7365	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5058	Phase 3
0.7329	Intermediate Similarity	NPD4097	Suspended
0.7329	Intermediate Similarity	NPD7229	Phase 3
0.7317	Intermediate Similarity	NPD5844	Phase 1
0.7317	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1549	Phase 2
0.7303	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7041	Phase 2
0.7296	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7075	Discontinued
0.7289	Intermediate Similarity	NPD6559	Discontinued
0.7273	Intermediate Similarity	NPD7074	Phase 3
0.7267	Intermediate Similarity	NPD1652	Phase 2
0.7261	Intermediate Similarity	NPD1934	Approved
0.7255	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7768	Phase 2
0.7215	Intermediate Similarity	NPD8455	Phase 2
0.7215	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7054	Approved
0.7211	Intermediate Similarity	NPD6353	Approved
0.7211	Intermediate Similarity	NPD2157	Approved
0.7197	Intermediate Similarity	NPD7411	Suspended
0.7192	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2238	Phase 2
0.7192	Intermediate Similarity	NPD3620	Phase 2
0.7188	Intermediate Similarity	NPD846	Approved
0.7188	Intermediate Similarity	NPD940	Approved
0.7186	Intermediate Similarity	NPD7240	Approved
0.7179	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7472	Approved
0.7163	Intermediate Similarity	NPD3685	Discontinued
0.7162	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2200	Suspended
0.7162	Intermediate Similarity	NPD4538	Approved
0.7162	Intermediate Similarity	NPD7097	Phase 1
0.7162	Intermediate Similarity	NPD4536	Approved
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7133	Intermediate Similarity	NPD6584	Phase 3
0.7133	Intermediate Similarity	NPD6005	Phase 3
0.7133	Intermediate Similarity	NPD6002	Phase 3
0.7133	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6004	Phase 3
0.7132	Intermediate Similarity	NPD7157	Approved
0.7126	Intermediate Similarity	NPD6797	Phase 2
0.7122	Intermediate Similarity	NPD5125	Phase 3
0.7122	Intermediate Similarity	NPD5126	Approved
0.7121	Intermediate Similarity	NPD2684	Approved
0.7117	Intermediate Similarity	NPD3787	Discontinued
0.7114	Intermediate Similarity	NPD3748	Approved
0.7107	Intermediate Similarity	NPD1465	Phase 2
0.7105	Intermediate Similarity	NPD7466	Approved
0.7099	Intermediate Similarity	NPD5494	Approved
0.7083	Intermediate Similarity	NPD7251	Discontinued
0.7083	Intermediate Similarity	NPD3018	Phase 2
0.7071	Intermediate Similarity	NPD3496	Discontinued
0.7067	Intermediate Similarity	NPD2796	Approved
0.7063	Intermediate Similarity	NPD2797	Approved
0.7048	Intermediate Similarity	NPD3818	Discontinued
0.7047	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD290	Approved
0.7044	Intermediate Similarity	NPD6801	Discontinued
0.7041	Intermediate Similarity	NPD7808	Phase 3
0.7039	Intermediate Similarity	NPD2800	Approved
0.7039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1138	Approved
0.7037	Intermediate Similarity	NPD7843	Approved
0.7032	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6166	Phase 2
0.7029	Intermediate Similarity	NPD7644	Approved
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7021	Intermediate Similarity	NPD1611	Approved
0.702	Intermediate Similarity	NPD7266	Discontinued
0.7014	Intermediate Similarity	NPD3690	Phase 2
0.7014	Intermediate Similarity	NPD3691	Phase 2
0.7014	Intermediate Similarity	NPD4624	Approved
0.7013	Intermediate Similarity	NPD6667	Approved
0.7013	Intermediate Similarity	NPD6666	Approved
0.7012	Intermediate Similarity	NPD6232	Discontinued
0.7007	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD5588	Approved
0.7	Intermediate Similarity	NPD5960	Phase 3
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD1510	Phase 2
0.6993	Remote Similarity	NPD1283	Approved
0.6993	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7473	Discontinued
0.6985	Remote Similarity	NPD5283	Phase 1
0.6978	Remote Similarity	NPD3091	Approved
0.6974	Remote Similarity	NPD7037	Approved
0.6974	Remote Similarity	NPD2424	Discontinued
0.6972	Remote Similarity	NPD1608	Approved
0.6966	Remote Similarity	NPD1712	Approved
0.6963	Remote Similarity	NPD1139	Approved
0.6963	Remote Similarity	NPD1137	Approved
0.6954	Remote Similarity	NPD4476	Approved
0.6954	Remote Similarity	NPD2935	Discontinued
0.6954	Remote Similarity	NPD4477	Approved
0.6948	Remote Similarity	NPD2677	Approved
0.6946	Remote Similarity	NPD3751	Discontinued
0.6944	Remote Similarity	NPD3094	Phase 2
0.6939	Remote Similarity	NPD3268	Approved
0.6939	Remote Similarity	NPD6798	Discontinued
0.6939	Remote Similarity	NPD7985	Registered
0.6933	Remote Similarity	NPD5709	Phase 3
0.6929	Remote Similarity	NPD1357	Approved
0.6923	Remote Similarity	NPD2983	Phase 2
0.6923	Remote Similarity	NPD6582	Phase 2
0.6923	Remote Similarity	NPD6583	Phase 3
0.6923	Remote Similarity	NPD2982	Phase 2
0.6912	Remote Similarity	NPD5535	Approved
0.6909	Remote Similarity	NPD5710	Approved
0.6909	Remote Similarity	NPD5711	Approved
0.6908	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3092	Approved
0.6894	Remote Similarity	NPD2801	Approved
0.6894	Remote Similarity	NPD5929	Approved
0.689	Remote Similarity	NPD4666	Phase 3
0.6884	Remote Similarity	NPD6387	Discontinued
0.6879	Remote Similarity	NPD6090	Discontinued
0.6871	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7095	Approved
0.6871	Remote Similarity	NPD3749	Approved
0.6867	Remote Similarity	NPD6651	Approved
0.686	Remote Similarity	NPD7090	Clinical (unspecified phase)

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