NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.09
Volume:	258.849
LogP:	2.985
LogD:	2.239
LogS:	-3.663
# Rotatable Bonds:	5
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	2.758
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.667
MDCK Permeability:	1.857847564679105e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.576
Plasma Protein Binding (PPB):	94.2546157836914%
Volume Distribution (VD):	0.869
Pgp-substrate:	3.462568998336792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.733
CYP2C19-inhibitor:	0.198
CYP2C19-substrate:	0.245
CYP2C9-inhibitor:	0.156
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.795
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	4.958
Half-life (T1/2):	0.728

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.377
AMES Toxicity:	0.92
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.929
Carcinogencity:	0.794
Eye Corrosion:	0.291
Eye Irritation:	0.963
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC222633

Natural Product ID:	NPC222633
*Common Name:**	5-(2E,4E)-Hexa-2,4-Dienoyl-4-Hydroxy-2-Methoxybenzaldehyde
IUPAC Name:	5-[(2E,4E)-hexa-2,4-dienoyl]-4-hydroxy-2-methoxybenzaldehyde
Synonyms:
Standard InCHIKey:	AOBDFCXCMVIAHU-VNKDHWASSA-N
Standard InCHI:	InChI=1S/C14H14O4/c1-3-4-5-6-12(16)11-7-10(9-15)14(18-2)8-13(11)17/h3-9,17H,1-2H3/b4-3+,6-5+
SMILES:	C/C=C/C=C/C(=O)c1cc(C=O)c(cc1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490516
PubChem CID:	44566277
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO33304	Phaeoacremonium sp. NRRL 32148	Species	Togniniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441079]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	IZ	=	40.0	mm	PMID[553152]

☑ 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 NPC222633 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	344
0.1-0.2	1559
0.2-0.3	4420
0.3-0.4	10864
0.4-0.5	7393
0.5-0.6	4133
0.6-0.7	6411
0.7-0.8	5131
0.8-0.85	1521
0.85-0.9	744
0.9-0.95	174
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC164136
0.9542	High Similarity	NPC103105
0.9407	High Similarity	NPC471620
0.9385	High Similarity	NPC8005
0.9385	High Similarity	NPC230818
0.9385	High Similarity	NPC78662
0.9313	High Similarity	NPC84772
0.9308	High Similarity	NPC186098
0.9308	High Similarity	NPC80694
0.9259	High Similarity	NPC150399
0.9259	High Similarity	NPC168105
0.9259	High Similarity	NPC274109
0.9259	High Similarity	NPC186838
0.9259	High Similarity	NPC66349
0.9259	High Similarity	NPC98115
0.9259	High Similarity	NPC477244
0.9259	High Similarity	NPC249606
0.9259	High Similarity	NPC12165
0.9259	High Similarity	NPC477242
0.9259	High Similarity	NPC41461
0.9259	High Similarity	NPC25287
0.9259	High Similarity	NPC477243
0.9259	High Similarity	NPC1486
0.9242	High Similarity	NPC324482
0.9242	High Similarity	NPC250057
0.9237	High Similarity	NPC69235
0.9237	High Similarity	NPC212379
0.9231	High Similarity	NPC128428
0.9231	High Similarity	NPC305518
0.9197	High Similarity	NPC470211
0.9197	High Similarity	NPC295384
0.9191	High Similarity	NPC317119
0.9191	High Similarity	NPC153979
0.9191	High Similarity	NPC472419
0.9185	High Similarity	NPC156092
0.9185	High Similarity	NPC60667
0.9185	High Similarity	NPC131039
0.9185	High Similarity	NPC13575
0.9185	High Similarity	NPC84699
0.9173	High Similarity	NPC27490
0.9173	High Similarity	NPC313618
0.9167	High Similarity	NPC185497
0.9143	High Similarity	NPC110776
0.9143	High Similarity	NPC271590
0.913	High Similarity	NPC259166
0.913	High Similarity	NPC144118
0.913	High Similarity	NPC16455
0.913	High Similarity	NPC213659
0.913	High Similarity	NPC215311
0.913	High Similarity	NPC204985
0.913	High Similarity	NPC326109
0.913	High Similarity	NPC219917
0.913	High Similarity	NPC48624
0.913	High Similarity	NPC307990
0.913	High Similarity	NPC101366
0.913	High Similarity	NPC80962
0.913	High Similarity	NPC172250
0.9124	High Similarity	NPC21350
0.9118	High Similarity	NPC156910
0.9111	High Similarity	NPC103842
0.9111	High Similarity	NPC286336
0.9111	High Similarity	NPC125920
0.9104	High Similarity	NPC87231
0.9104	High Similarity	NPC129132
0.9104	High Similarity	NPC212631
0.9104	High Similarity	NPC285054
0.9104	High Similarity	NPC257756
0.9104	High Similarity	NPC205468
0.9091	High Similarity	NPC60558
0.9078	High Similarity	NPC476153
0.9078	High Similarity	NPC215885
0.9078	High Similarity	NPC2416
0.9065	High Similarity	NPC52789
0.9065	High Similarity	NPC470087
0.9065	High Similarity	NPC321980
0.9065	High Similarity	NPC55832
0.9065	High Similarity	NPC268204
0.9065	High Similarity	NPC469404
0.9065	High Similarity	NPC470089
0.9065	High Similarity	NPC3188
0.9065	High Similarity	NPC26051
0.9058	High Similarity	NPC472366
0.9058	High Similarity	NPC473076
0.9058	High Similarity	NPC477956
0.9058	High Similarity	NPC137009
0.9058	High Similarity	NPC37206
0.9058	High Similarity	NPC23257
0.9058	High Similarity	NPC283429
0.9051	High Similarity	NPC7013
0.9051	High Similarity	NPC116632
0.9051	High Similarity	NPC303644
0.9051	High Similarity	NPC209560
0.9051	High Similarity	NPC294409
0.9051	High Similarity	NPC162680
0.9051	High Similarity	NPC181124
0.9044	High Similarity	NPC39426
0.9044	High Similarity	NPC234560
0.9044	High Similarity	NPC151113
0.9037	High Similarity	NPC263670
0.9037	High Similarity	NPC144051
0.9037	High Similarity	NPC472365
0.9037	High Similarity	NPC159623
0.9037	High Similarity	NPC192304
0.9037	High Similarity	NPC28753
0.9037	High Similarity	NPC139813
0.9037	High Similarity	NPC294593
0.9037	High Similarity	NPC93756
0.9037	High Similarity	NPC175098
0.9037	High Similarity	NPC108113
0.9037	High Similarity	NPC188646
0.9037	High Similarity	NPC242294
0.9037	High Similarity	NPC312318
0.9037	High Similarity	NPC82225
0.9037	High Similarity	NPC18877
0.9037	High Similarity	NPC204960
0.9037	High Similarity	NPC56031
0.9037	High Similarity	NPC27643
0.9037	High Similarity	NPC20560
0.9037	High Similarity	NPC337373
0.903	High Similarity	NPC64359
0.903	High Similarity	NPC308037
0.903	High Similarity	NPC262359
0.9023	High Similarity	NPC42292
0.9023	High Similarity	NPC307732
0.9021	High Similarity	NPC214493
0.9	High Similarity	NPC255073
0.8993	High Similarity	NPC253822
0.8993	High Similarity	NPC471587
0.8993	High Similarity	NPC11056
0.8986	High Similarity	NPC243528
0.8986	High Similarity	NPC55162
0.8986	High Similarity	NPC309154
0.8986	High Similarity	NPC90665
0.8986	High Similarity	NPC124269
0.8986	High Similarity	NPC12175
0.8986	High Similarity	NPC251681
0.8986	High Similarity	NPC279668
0.8986	High Similarity	NPC278323
0.8978	High Similarity	NPC174999
0.8978	High Similarity	NPC187826
0.8978	High Similarity	NPC235428
0.8978	High Similarity	NPC87545
0.8971	High Similarity	NPC236974
0.8971	High Similarity	NPC144027
0.8963	High Similarity	NPC203817
0.8936	High Similarity	NPC257097
0.8936	High Similarity	NPC51887
0.8936	High Similarity	NPC68104
0.8936	High Similarity	NPC117836
0.8936	High Similarity	NPC169591
0.8936	High Similarity	NPC39329
0.8936	High Similarity	NPC221432
0.8936	High Similarity	NPC476178
0.8936	High Similarity	NPC149026
0.8936	High Similarity	NPC91560
0.8936	High Similarity	NPC475705
0.8936	High Similarity	NPC175504
0.8936	High Similarity	NPC75049
0.8936	High Similarity	NPC143896
0.8936	High Similarity	NPC245482
0.8936	High Similarity	NPC310130
0.8936	High Similarity	NPC301751
0.8936	High Similarity	NPC150408
0.8936	High Similarity	NPC164980
0.8931	High Similarity	NPC65041
0.8929	High Similarity	NPC171870
0.8929	High Similarity	NPC312391
0.8929	High Similarity	NPC324386
0.8929	High Similarity	NPC4743
0.8929	High Similarity	NPC213322
0.8929	High Similarity	NPC110969
0.8921	High Similarity	NPC78913
0.8921	High Similarity	NPC49242
0.8921	High Similarity	NPC471697
0.8921	High Similarity	NPC18260
0.8921	High Similarity	NPC139554
0.8913	High Similarity	NPC212767
0.8913	High Similarity	NPC188879
0.8904	High Similarity	NPC208806
0.8897	High Similarity	NPC223457
0.8889	High Similarity	NPC309717
0.8889	High Similarity	NPC164236
0.8889	High Similarity	NPC66384
0.8889	High Similarity	NPC128348
0.8889	High Similarity	NPC475589
0.8889	High Similarity	NPC189106
0.8889	High Similarity	NPC65060
0.8889	High Similarity	NPC186097
0.8889	High Similarity	NPC475009
0.8889	High Similarity	NPC473584
0.8889	High Similarity	NPC112192
0.8889	High Similarity	NPC31872
0.8889	High Similarity	NPC475008
0.8881	High Similarity	NPC247779
0.8873	High Similarity	NPC476055
0.8873	High Similarity	NPC236766
0.8873	High Similarity	NPC209040
0.8873	High Similarity	NPC473013
0.8873	High Similarity	NPC473015
0.8873	High Similarity	NPC197252

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 NPC222633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	1004
0.2-0.3	1697
0.3-0.4	2689
0.4-0.5	1814
0.5-0.6	1126
0.6-0.7	359
0.7-0.8	112
0.8-0.85	29
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9173	High Similarity	NPD1240	Approved
0.9044	High Similarity	NPD1510	Phase 2
0.9037	High Similarity	NPD1607	Approved
0.8849	High Similarity	NPD1549	Phase 2
0.8777	High Similarity	NPD1550	Clinical (unspecified phase)
0.8777	High Similarity	NPD1552	Clinical (unspecified phase)
0.8639	High Similarity	NPD7411	Suspended
0.8611	High Similarity	NPD4378	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD4380	Phase 2
0.8357	Intermediate Similarity	NPD6651	Approved
0.8322	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD2796	Approved
0.831	Intermediate Similarity	NPD1551	Phase 2
0.8278	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD920	Approved
0.8235	Intermediate Similarity	NPD7075	Discontinued
0.8219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD6799	Approved
0.8158	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7819	Suspended
0.8153	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2800	Approved
0.8108	Intermediate Similarity	NPD2534	Approved
0.8108	Intermediate Similarity	NPD2533	Approved
0.8108	Intermediate Similarity	NPD2532	Approved
0.8108	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1934	Approved
0.8092	Intermediate Similarity	NPD6801	Discontinued
0.8056	Intermediate Similarity	NPD2935	Discontinued
0.8041	Intermediate Similarity	NPD1511	Approved
0.8014	Intermediate Similarity	NPD1243	Approved
0.7962	Intermediate Similarity	NPD1247	Approved
0.7961	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD7768	Phase 2
0.7935	Intermediate Similarity	NPD3882	Suspended
0.7933	Intermediate Similarity	NPD1512	Approved
0.791	Intermediate Similarity	NPD9545	Approved
0.7895	Intermediate Similarity	NPD9493	Approved
0.7885	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD9717	Approved
0.7862	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD3750	Approved
0.7834	Intermediate Similarity	NPD919	Approved
0.7832	Intermediate Similarity	NPD943	Approved
0.7817	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2801	Approved
0.777	Intermediate Similarity	NPD2654	Approved
0.7736	Intermediate Similarity	NPD6959	Discontinued
0.7714	Intermediate Similarity	NPD1203	Approved
0.7688	Intermediate Similarity	NPD6232	Discontinued
0.7683	Intermediate Similarity	NPD5953	Discontinued
0.7669	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7286	Phase 2
0.7658	Intermediate Similarity	NPD3749	Approved
0.7655	Intermediate Similarity	NPD230	Phase 1
0.7654	Intermediate Similarity	NPD7473	Discontinued
0.7636	Intermediate Similarity	NPD6559	Discontinued
0.7635	Intermediate Similarity	NPD2344	Approved
0.7619	Intermediate Similarity	NPD2799	Discontinued
0.7606	Intermediate Similarity	NPD9494	Approved
0.7593	Intermediate Similarity	NPD6166	Phase 2
0.7593	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD5494	Approved
0.7554	Intermediate Similarity	NPD422	Phase 1
0.7554	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD5403	Approved
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.7516	Intermediate Similarity	NPD5401	Approved
0.7515	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2313	Discontinued
0.7434	Intermediate Similarity	NPD2309	Approved
0.7431	Intermediate Similarity	NPD6832	Phase 2
0.7413	Intermediate Similarity	NPD1019	Discontinued
0.7413	Intermediate Similarity	NPD2798	Approved
0.741	Intermediate Similarity	NPD7074	Phase 3
0.7407	Intermediate Similarity	NPD1241	Discontinued
0.7391	Intermediate Similarity	NPD1548	Phase 1
0.7376	Intermediate Similarity	NPD3972	Approved
0.7375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7362	Intermediate Similarity	NPD5711	Approved
0.7362	Intermediate Similarity	NPD5710	Approved
0.7349	Intermediate Similarity	NPD7054	Approved
0.7343	Intermediate Similarity	NPD1164	Approved
0.7338	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD411	Approved
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3268	Approved
0.7305	Intermediate Similarity	NPD1610	Phase 2
0.7305	Intermediate Similarity	NPD7472	Approved
0.7297	Intermediate Similarity	NPD447	Suspended
0.7293	Intermediate Similarity	NPD9266	Approved
0.7293	Intermediate Similarity	NPD74	Approved
0.7262	Intermediate Similarity	NPD6797	Phase 2
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5844	Phase 1
0.7222	Intermediate Similarity	NPD1470	Approved
0.7219	Intermediate Similarity	NPD7251	Discontinued
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD6100	Approved
0.7218	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9264	Approved
0.7218	Intermediate Similarity	NPD9267	Approved
0.7218	Intermediate Similarity	NPD9263	Approved
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7211	Intermediate Similarity	NPD1296	Phase 2
0.7205	Intermediate Similarity	NPD5402	Approved
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4908	Phase 1
0.7183	Intermediate Similarity	NPD1201	Approved
0.7181	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5124	Phase 1
0.7176	Intermediate Similarity	NPD7808	Phase 3
0.7171	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1471	Phase 3
0.7171	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7118	Intermediate Similarity	NPD6104	Discontinued
0.7108	Intermediate Similarity	NPD3926	Phase 2
0.7103	Intermediate Similarity	NPD3267	Approved
0.7103	Intermediate Similarity	NPD3266	Approved
0.7099	Intermediate Similarity	NPD846	Approved
0.7099	Intermediate Similarity	NPD940	Approved
0.7079	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4363	Phase 3
0.7062	Intermediate Similarity	NPD4360	Phase 2
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4308	Phase 3
0.7037	Intermediate Similarity	NPD1465	Phase 2
0.7034	Intermediate Similarity	NPD1876	Approved
0.7034	Intermediate Similarity	NPD3225	Approved
0.7032	Intermediate Similarity	NPD7003	Approved
0.7022	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4361	Phase 2
0.7019	Intermediate Similarity	NPD5889	Approved
0.7019	Intermediate Similarity	NPD5890	Approved
0.7019	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1608	Approved
0.7014	Intermediate Similarity	NPD9269	Phase 2
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6986	Remote Similarity	NPD2797	Approved
0.6982	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3764	Approved
0.6978	Remote Similarity	NPD9281	Approved
0.6972	Remote Similarity	NPD9268	Approved
0.6964	Remote Similarity	NPD2403	Approved
0.6959	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1933	Approved
0.6949	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4626	Approved
0.6918	Remote Similarity	NPD1283	Approved
0.6917	Remote Similarity	NPD9261	Approved
0.6913	Remote Similarity	NPD3027	Phase 3
0.689	Remote Similarity	NPD4288	Approved
0.689	Remote Similarity	NPD2296	Approved
0.6887	Remote Similarity	NPD1613	Approved
0.6887	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3142	Approved
0.6887	Remote Similarity	NPD3140	Approved
0.6853	Remote Similarity	NPD1651	Approved
0.6852	Remote Similarity	NPD6585	Discontinued
0.6846	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6004	Phase 3
0.6839	Remote Similarity	NPD6005	Phase 3
0.6839	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6002	Phase 3
0.6829	Remote Similarity	NPD5760	Phase 2
0.6829	Remote Similarity	NPD5761	Phase 2
0.6824	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD520	Approved
0.6818	Remote Similarity	NPD8434	Phase 2
0.6806	Remote Similarity	NPD1778	Approved
0.6806	Remote Similarity	NPD17	Approved
0.68	Remote Similarity	NPD4625	Phase 3
0.6795	Remote Similarity	NPD2424	Discontinued
0.6792	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1481	Phase 2
0.6779	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4307	Phase 2
0.6772	Remote Similarity	NPD2354	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