NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.11
Volume:	290.754
LogP:	3.979
LogD:	3.311
LogS:	-4.295
# Rotatable Bonds:	5
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	2.268
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.608
MDCK Permeability:	1.877341856015846e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.729
30% Bioavailability (F30%):	0.736

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.252
Plasma Protein Binding (PPB):	99.2137222290039%
Volume Distribution (VD):	0.638
Pgp-substrate:	0.7158113121986389%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.58
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.823
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.807
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	6.837
Half-life (T1/2):	0.475

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.217
AMES Toxicity:	0.331
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.329
Skin Sensitization:	0.602
Carcinogencity:	0.708
Eye Corrosion:	0.029
Eye Irritation:	0.919
Respiratory Toxicity:	0.693

Download Data

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

Natural Product: NPC245395

Natural Product ID:	NPC245395
*Common Name:**	4'-Methoxymagnaledehyde E
IUPAC Name:	4-hydroxy-3-(4-methoxy-3-prop-2-enylphenyl)benzaldehyde
Synonyms:	4'-Methoxymagnaledehyde E
Standard InCHIKey:	UNUXJXJQNIRFQB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O3/c1-3-4-14-10-13(6-8-17(14)20-2)15-9-12(11-18)5-7-16(15)19/h3,5-11,19H,1,4H2,2H3
SMILES:	C=CCc1cc(ccc1OC)c1cc(C=O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253759
PubChem CID:	23657447
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*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
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[555698]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[555698]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[555698]

☑ 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 NPC245395 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	300
0.1-0.2	1606
0.2-0.3	3706
0.3-0.4	10478
0.4-0.5	7797
0.5-0.6	3874
0.6-0.7	8038
0.7-0.8	6042
0.8-0.85	792
0.85-0.9	59
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9187	High Similarity	NPC216216
0.9187	High Similarity	NPC131868
0.9113	High Similarity	NPC251259
0.9113	High Similarity	NPC295034
0.8881	High Similarity	NPC24394
0.8815	High Similarity	NPC23870
0.8815	High Similarity	NPC62735
0.8797	High Similarity	NPC274876
0.8797	High Similarity	NPC27643
0.875	High Similarity	NPC471620
0.871	High Similarity	NPC469954
0.8705	High Similarity	NPC275278
0.8667	High Similarity	NPC163029
0.8667	High Similarity	NPC131039
0.8647	High Similarity	NPC112192
0.8647	High Similarity	NPC189106
0.8647	High Similarity	NPC183103
0.8647	High Similarity	NPC164236
0.8647	High Similarity	NPC128348
0.8647	High Similarity	NPC309717
0.8647	High Similarity	NPC66384
0.8629	High Similarity	NPC19290
0.8626	High Similarity	NPC2596
0.8623	High Similarity	NPC204985
0.8623	High Similarity	NPC259166
0.8623	High Similarity	NPC172250
0.8623	High Similarity	NPC213659
0.8623	High Similarity	NPC144118
0.8623	High Similarity	NPC80962
0.8623	High Similarity	NPC11056
0.8623	High Similarity	NPC326109
0.8623	High Similarity	NPC48624
0.8623	High Similarity	NPC219917
0.8623	High Similarity	NPC215311
0.8613	High Similarity	NPC21350
0.8603	High Similarity	NPC98115
0.8603	High Similarity	NPC274109
0.8603	High Similarity	NPC477244
0.8603	High Similarity	NPC12165
0.8603	High Similarity	NPC477242
0.8603	High Similarity	NPC66349
0.8603	High Similarity	NPC1486
0.8603	High Similarity	NPC213603
0.8603	High Similarity	NPC168105
0.8603	High Similarity	NPC150399
0.8603	High Similarity	NPC477243
0.8603	High Similarity	NPC186838
0.8603	High Similarity	NPC41461
0.8603	High Similarity	NPC25287
0.8603	High Similarity	NPC249606
0.8582	High Similarity	NPC39361
0.8561	High Similarity	NPC470087
0.8561	High Similarity	NPC26051
0.8561	High Similarity	NPC55832
0.8561	High Similarity	NPC321980
0.8561	High Similarity	NPC268204
0.8561	High Similarity	NPC470089
0.8561	High Similarity	NPC939
0.8561	High Similarity	NPC469404
0.8561	High Similarity	NPC52789
0.856	High Similarity	NPC174087
0.8551	High Similarity	NPC477956
0.8551	High Similarity	NPC470211
0.8551	High Similarity	NPC295384
0.8551	High Similarity	NPC283429
0.8551	High Similarity	NPC472366
0.855	High Similarity	NPC121104
0.854	High Similarity	NPC472419
0.854	High Similarity	NPC317119
0.854	High Similarity	NPC153979
0.8537	High Similarity	NPC35344
0.8537	High Similarity	NPC141003
0.8529	High Similarity	NPC156092
0.8529	High Similarity	NPC13575
0.8511	High Similarity	NPC476055
0.8511	High Similarity	NPC478019
0.85	High Similarity	NPC50954
0.85	High Similarity	NPC148545
0.8496	Intermediate Similarity	NPC247779
0.8496	Intermediate Similarity	NPC469929
0.8492	Intermediate Similarity	NPC184527
0.8489	Intermediate Similarity	NPC253822
0.8489	Intermediate Similarity	NPC101366
0.8485	Intermediate Similarity	NPC3009
0.8478	Intermediate Similarity	NPC470407
0.8473	Intermediate Similarity	NPC474737
0.8462	Intermediate Similarity	NPC184219
0.8456	Intermediate Similarity	NPC103842
0.8456	Intermediate Similarity	NPC286336
0.8455	Intermediate Similarity	NPC228988
0.845	Intermediate Similarity	NPC67300
0.844	Intermediate Similarity	NPC300603
0.844	Intermediate Similarity	NPC51887
0.844	Intermediate Similarity	NPC245482
0.844	Intermediate Similarity	NPC117836
0.844	Intermediate Similarity	NPC91694
0.844	Intermediate Similarity	NPC301751
0.844	Intermediate Similarity	NPC475705
0.844	Intermediate Similarity	NPC476178
0.8425	Intermediate Similarity	NPC473767
0.8406	Intermediate Similarity	NPC181124
0.8406	Intermediate Similarity	NPC294409
0.8406	Intermediate Similarity	NPC162680
0.8406	Intermediate Similarity	NPC116632
0.8406	Intermediate Similarity	NPC209560
0.8406	Intermediate Similarity	NPC303644
0.8406	Intermediate Similarity	NPC7013
0.84	Intermediate Similarity	NPC322197
0.8397	Intermediate Similarity	NPC470858
0.8394	Intermediate Similarity	NPC471670
0.8387	Intermediate Similarity	NPC242136
0.8385	Intermediate Similarity	NPC11799
0.8385	Intermediate Similarity	NPC141252
0.8382	Intermediate Similarity	NPC175098
0.8382	Intermediate Similarity	NPC294593
0.8382	Intermediate Similarity	NPC204960
0.8382	Intermediate Similarity	NPC472365
0.8382	Intermediate Similarity	NPC312318
0.8382	Intermediate Similarity	NPC139813
0.8382	Intermediate Similarity	NPC28753
0.8382	Intermediate Similarity	NPC82225
0.8382	Intermediate Similarity	NPC18877
0.8382	Intermediate Similarity	NPC20560
0.8382	Intermediate Similarity	NPC337373
0.8382	Intermediate Similarity	NPC56031
0.8382	Intermediate Similarity	NPC192304
0.8382	Intermediate Similarity	NPC188646
0.8382	Intermediate Similarity	NPC144051
0.8382	Intermediate Similarity	NPC242294
0.8382	Intermediate Similarity	NPC159623
0.8382	Intermediate Similarity	NPC263670
0.838	Intermediate Similarity	NPC271288
0.838	Intermediate Similarity	NPC471523
0.838	Intermediate Similarity	NPC471473
0.838	Intermediate Similarity	NPC471524
0.8374	Intermediate Similarity	NPC57879
0.837	Intermediate Similarity	NPC64359
0.837	Intermediate Similarity	NPC308037
0.837	Intermediate Similarity	NPC313618
0.837	Intermediate Similarity	NPC262359
0.8369	Intermediate Similarity	NPC297600
0.8358	Intermediate Similarity	NPC86774
0.8358	Intermediate Similarity	NPC109778
0.8358	Intermediate Similarity	NPC327457
0.8357	Intermediate Similarity	NPC265178
0.8356	Intermediate Similarity	NPC131121
0.8346	Intermediate Similarity	NPC96024
0.8346	Intermediate Similarity	NPC50583
0.8346	Intermediate Similarity	NPC473744
0.8345	Intermediate Similarity	NPC90665
0.8345	Intermediate Similarity	NPC251681
0.8345	Intermediate Similarity	NPC12175
0.8345	Intermediate Similarity	NPC278323
0.8345	Intermediate Similarity	NPC279668
0.8345	Intermediate Similarity	NPC309154
0.8345	Intermediate Similarity	NPC55162
0.8345	Intermediate Similarity	NPC243528
0.8345	Intermediate Similarity	NPC124269
0.8345	Intermediate Similarity	NPC472368
0.8333	Intermediate Similarity	NPC186647
0.8333	Intermediate Similarity	NPC240593
0.8333	Intermediate Similarity	NPC473391
0.8333	Intermediate Similarity	NPC476333
0.8333	Intermediate Similarity	NPC135325
0.8333	Intermediate Similarity	NPC472367
0.8333	Intermediate Similarity	NPC472364
0.8333	Intermediate Similarity	NPC39195
0.8333	Intermediate Similarity	NPC222633
0.8322	Intermediate Similarity	NPC316769
0.8322	Intermediate Similarity	NPC51641
0.8322	Intermediate Similarity	NPC300267
0.8322	Intermediate Similarity	NPC477955
0.8322	Intermediate Similarity	NPC25844
0.8321	Intermediate Similarity	NPC89630
0.8321	Intermediate Similarity	NPC164136
0.8321	Intermediate Similarity	NPC22644
0.8311	Intermediate Similarity	NPC213401
0.8311	Intermediate Similarity	NPC160015
0.8311	Intermediate Similarity	NPC247677
0.831	Intermediate Similarity	NPC39329
0.831	Intermediate Similarity	NPC310130
0.831	Intermediate Similarity	NPC257097
0.831	Intermediate Similarity	NPC471621
0.831	Intermediate Similarity	NPC18585
0.831	Intermediate Similarity	NPC150408
0.831	Intermediate Similarity	NPC75049
0.831	Intermediate Similarity	NPC91560
0.831	Intermediate Similarity	NPC166138
0.831	Intermediate Similarity	NPC149026
0.831	Intermediate Similarity	NPC143896
0.831	Intermediate Similarity	NPC169591
0.831	Intermediate Similarity	NPC164980
0.831	Intermediate Similarity	NPC106985
0.831	Intermediate Similarity	NPC221432
0.831	Intermediate Similarity	NPC105213
0.831	Intermediate Similarity	NPC175504
0.831	Intermediate Similarity	NPC260152
0.831	Intermediate Similarity	NPC68104
0.8309	Intermediate Similarity	NPC129132
0.8309	Intermediate Similarity	NPC212631

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 NPC245395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	1018
0.2-0.3	1231
0.3-0.4	2395
0.4-0.5	2083
0.5-0.6	1330
0.6-0.7	613
0.7-0.8	175
0.8-0.85	17
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8467	Intermediate Similarity	NPD2935	Discontinued
0.845	Intermediate Similarity	NPD3972	Approved
0.8417	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD2344	Approved
0.837	Intermediate Similarity	NPD1240	Approved
0.8357	Intermediate Similarity	NPD7003	Approved
0.8273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1510	Phase 2
0.8261	Intermediate Similarity	NPD2799	Discontinued
0.8248	Intermediate Similarity	NPD1607	Approved
0.8195	Intermediate Similarity	NPD2798	Approved
0.8169	Intermediate Similarity	NPD2309	Approved
0.8151	Intermediate Similarity	NPD7458	Discontinued
0.8134	Intermediate Similarity	NPD9494	Approved
0.8125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD4628	Phase 3
0.8045	Intermediate Similarity	NPD1283	Approved
0.8045	Intermediate Similarity	NPD1876	Approved
0.8	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1651	Approved
0.7973	Intermediate Similarity	NPD4380	Phase 2
0.7958	Intermediate Similarity	NPD1549	Phase 2
0.7943	Intermediate Similarity	NPD2796	Approved
0.7923	Intermediate Similarity	NPD9545	Approved
0.7887	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1164	Approved
0.7852	Intermediate Similarity	NPD2797	Approved
0.7829	Intermediate Similarity	NPD7768	Phase 2
0.7826	Intermediate Similarity	NPD2313	Discontinued
0.782	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1281	Approved
0.7817	Intermediate Similarity	NPD4477	Approved
0.7817	Intermediate Similarity	NPD4476	Approved
0.7815	Intermediate Similarity	NPD7819	Suspended
0.7815	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1241	Discontinued
0.7803	Intermediate Similarity	NPD4626	Approved
0.78	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD7075	Discontinued
0.7724	Intermediate Similarity	NPD3750	Approved
0.7721	Intermediate Similarity	NPD1203	Approved
0.7707	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3268	Approved
0.7698	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1551	Phase 2
0.7681	Intermediate Similarity	NPD6832	Phase 2
0.7667	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6355	Discontinued
0.7639	Intermediate Similarity	NPD2346	Discontinued
0.7634	Intermediate Similarity	NPD9493	Approved
0.763	Intermediate Similarity	NPD1608	Approved
0.7622	Intermediate Similarity	NPD4308	Phase 3
0.7619	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5691	Approved
0.7589	Intermediate Similarity	NPD2979	Phase 3
0.7589	Intermediate Similarity	NPD4060	Phase 1
0.7586	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6273	Approved
0.758	Intermediate Similarity	NPD6232	Discontinued
0.7574	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3764	Approved
0.7571	Intermediate Similarity	NPD6798	Discontinued
0.7568	Intermediate Similarity	NPD6799	Approved
0.7533	Intermediate Similarity	NPD920	Approved
0.7532	Intermediate Similarity	NPD2296	Approved
0.7519	Intermediate Similarity	NPD1894	Discontinued
0.7517	Intermediate Similarity	NPD2532	Approved
0.7517	Intermediate Similarity	NPD2533	Approved
0.7517	Intermediate Similarity	NPD2534	Approved
0.7517	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD6959	Discontinued
0.7516	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.7484	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD6651	Approved
0.7481	Intermediate Similarity	NPD3847	Discontinued
0.7465	Intermediate Similarity	NPD3142	Approved
0.7465	Intermediate Similarity	NPD3140	Approved
0.7453	Intermediate Similarity	NPD5844	Phase 1
0.7447	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7473	Discontinued
0.7436	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3226	Approved
0.7426	Intermediate Similarity	NPD1201	Approved
0.7415	Intermediate Similarity	NPD2800	Approved
0.7415	Intermediate Similarity	NPD1243	Approved
0.7407	Intermediate Similarity	NPD17	Approved
0.7403	Intermediate Similarity	NPD7577	Discontinued
0.7403	Intermediate Similarity	NPD6279	Approved
0.7403	Intermediate Similarity	NPD6280	Approved
0.7379	Intermediate Similarity	NPD3748	Approved
0.7379	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1481	Phase 2
0.7372	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2801	Approved
0.7351	Intermediate Similarity	NPD5049	Phase 3
0.7344	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4307	Phase 2
0.7339	Intermediate Similarity	NPD3020	Approved
0.7338	Intermediate Similarity	NPD3266	Approved
0.7338	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD3267	Approved
0.7333	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2531	Phase 2
0.7329	Intermediate Similarity	NPD5408	Approved
0.7329	Intermediate Similarity	NPD2438	Suspended
0.7329	Intermediate Similarity	NPD5405	Approved
0.7329	Intermediate Similarity	NPD5406	Approved
0.7329	Intermediate Similarity	NPD5404	Approved
0.7325	Intermediate Similarity	NPD3749	Approved
0.7317	Intermediate Similarity	NPD6559	Discontinued
0.7315	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3887	Approved
0.7315	Intermediate Similarity	NPD2354	Approved
0.7313	Intermediate Similarity	NPD5536	Phase 2
0.7305	Intermediate Similarity	NPD4908	Phase 1
0.7299	Intermediate Similarity	NPD1535	Discovery
0.7299	Intermediate Similarity	NPD1610	Phase 2
0.7292	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7177	Discontinued
0.7279	Intermediate Similarity	NPD1471	Phase 3
0.7267	Intermediate Similarity	NPD7440	Discontinued
0.7266	Intermediate Similarity	NPD3134	Approved
0.726	Intermediate Similarity	NPD7033	Discontinued
0.7256	Intermediate Similarity	NPD5953	Discontinued
0.7254	Intermediate Similarity	NPD7008	Discontinued
0.7239	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1512	Approved
0.7236	Intermediate Similarity	NPD2859	Approved
0.7236	Intermediate Similarity	NPD2860	Approved
0.7234	Intermediate Similarity	NPD2861	Phase 2
0.7233	Intermediate Similarity	NPD5494	Approved
0.7222	Intermediate Similarity	NPD943	Approved
0.7219	Intermediate Similarity	NPD7390	Discontinued
0.7211	Intermediate Similarity	NPD6099	Approved
0.7211	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7427	Discontinued
0.7171	Intermediate Similarity	NPD4662	Approved
0.7171	Intermediate Similarity	NPD4661	Approved
0.717	Intermediate Similarity	NPD919	Approved
0.7169	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6671	Approved
0.7162	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2353	Approved
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2934	Approved
0.7154	Intermediate Similarity	NPD2933	Approved
0.7154	Intermediate Similarity	NPD2684	Approved
0.7153	Intermediate Similarity	NPD4062	Phase 3
0.7153	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1778	Approved
0.7153	Intermediate Similarity	NPD2932	Approved
0.7153	Intermediate Similarity	NPD3019	Approved
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD3823	Discontinued
0.7143	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7134	Intermediate Similarity	NPD7286	Phase 2
0.7133	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7132	Intermediate Similarity	NPD1548	Phase 1
0.7132	Intermediate Similarity	NPD968	Approved
0.7114	Intermediate Similarity	NPD2424	Discontinued
0.7114	Intermediate Similarity	NPD4534	Discontinued
0.7109	Intermediate Similarity	NPD1237	Approved
0.7101	Intermediate Similarity	NPD3496	Discontinued
0.7099	Intermediate Similarity	NPD5451	Approved
0.709	Intermediate Similarity	NPD5951	Approved
0.7089	Intermediate Similarity	NPD3817	Phase 2
0.7083	Intermediate Similarity	NPD411	Approved
0.7081	Intermediate Similarity	NPD1247	Approved
0.708	Intermediate Similarity	NPD5585	Approved
0.7078	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1358	Approved
0.7073	Intermediate Similarity	NPD3818	Discontinued
0.7073	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6583	Phase 3
0.7071	Intermediate Similarity	NPD1669	Approved
0.7071	Intermediate Similarity	NPD6582	Phase 2
0.7068	Intermediate Similarity	NPD5535	Approved
0.7055	Intermediate Similarity	NPD230	Phase 1
0.7055	Intermediate Similarity	NPD4622	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