NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.09
Volume:	273.458
LogP:	3.885
LogD:	3.148
LogS:	-3.634
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.433
Fsp3:	0.062
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:	-4.652
MDCK Permeability:	1.533011527499184e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	99.43207550048828%
Volume Distribution (VD):	0.507
Pgp-substrate:	0.7179482579231262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.731
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.549
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.834
CYP3A4-inhibitor:	0.621
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	6.893
Half-life (T1/2):	0.592

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.324
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.448
Skin Sensitization:	0.688
Carcinogencity:	0.466
Eye Corrosion:	0.055
Eye Irritation:	0.959
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC295034

Natural Product ID:	NPC295034
*Common Name:**	Magnaldehyde
IUPAC Name:	4-hydroxy-3-(2-hydroxy-5-prop-2-enylphenyl)benzaldehyde
Synonyms:	Magnaldehyde; Magnaldehyde D
Standard InCHIKey:	KDWYPRNOEMXUNA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O3/c1-2-3-11-4-6-15(18)13(8-11)14-9-12(10-17)5-7-16(14)19/h2,4-10,18-19H,1,3H2
SMILES:	C=CCc1ccc(c(c1)c1cc(C=O)ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550166
PubChem CID:	5319189
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]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[23434030]
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]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4093781]
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]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	4
Others	3

Activity Type	# Activity
Cell Line	1
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	9.2	ug.mL-1	PMID[455646]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	1000000.0	nM	PMID[455647]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	4.83	n.a.	PMID[455647]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	41380.0	nM	PMID[455647]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.84	n.a.	PMID[455647]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	108570.0	nM	PMID[455647]
NPT27	Others	Unspecified		CC50	=	200000.0	nM	PMID[455647]

☑ 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 NPC295034 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	289
0.1-0.2	1585
0.2-0.3	3541
0.3-0.4	10741
0.4-0.5	8462
0.5-0.6	5518
0.6-0.7	8961
0.7-0.8	3342
0.8-0.85	227
0.85-0.9	23
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC216216
0.9145	High Similarity	NPC184527
0.9113	High Similarity	NPC245395
0.8957	High Similarity	NPC228988
0.8908	High Similarity	NPC473767
0.8898	High Similarity	NPC174087
0.8889	High Similarity	NPC322197
0.88	High Similarity	NPC3009
0.8793	High Similarity	NPC286222
0.8718	High Similarity	NPC242136
0.8667	High Similarity	NPC249435
0.8651	High Similarity	NPC96024
0.8621	High Similarity	NPC116842
0.8609	High Similarity	NPC17525
0.8595	High Similarity	NPC182240
0.8594	High Similarity	NPC41847
0.8594	High Similarity	NPC85342
0.8583	High Similarity	NPC476119
0.8525	High Similarity	NPC473136
0.8522	High Similarity	NPC141523
0.8512	High Similarity	NPC273282
0.8512	High Similarity	NPC474890
0.8512	High Similarity	NPC161943
0.8509	High Similarity	NPC219913
0.8468	Intermediate Similarity	NPC475192
0.8462	Intermediate Similarity	NPC477139
0.8462	Intermediate Similarity	NPC213485
0.8462	Intermediate Similarity	NPC139074
0.8462	Intermediate Similarity	NPC40524
0.8462	Intermediate Similarity	NPC52407
0.845	Intermediate Similarity	NPC93015
0.845	Intermediate Similarity	NPC471851
0.8438	Intermediate Similarity	NPC276238
0.839	Intermediate Similarity	NPC212718
0.839	Intermediate Similarity	NPC114682
0.839	Intermediate Similarity	NPC268388
0.8387	Intermediate Similarity	NPC120545
0.8387	Intermediate Similarity	NPC31936
0.8376	Intermediate Similarity	NPC95172
0.8374	Intermediate Similarity	NPC159525
0.8362	Intermediate Similarity	NPC226699
0.8359	Intermediate Similarity	NPC229894
0.8347	Intermediate Similarity	NPC83718
0.8346	Intermediate Similarity	NPC62952
0.8346	Intermediate Similarity	NPC254492
0.8333	Intermediate Similarity	NPC130899
0.8333	Intermediate Similarity	NPC199273
0.8333	Intermediate Similarity	NPC164014
0.8333	Intermediate Similarity	NPC61153
0.8333	Intermediate Similarity	NPC283590
0.8333	Intermediate Similarity	NPC70859
0.832	Intermediate Similarity	NPC68167
0.832	Intermediate Similarity	NPC282577
0.832	Intermediate Similarity	NPC91478
0.8308	Intermediate Similarity	NPC475042
0.8308	Intermediate Similarity	NPC275504
0.8306	Intermediate Similarity	NPC131868
0.8306	Intermediate Similarity	NPC190971
0.8295	Intermediate Similarity	NPC474998
0.8295	Intermediate Similarity	NPC117899
0.8293	Intermediate Similarity	NPC158222
0.8291	Intermediate Similarity	NPC262365
0.8284	Intermediate Similarity	NPC477593
0.8281	Intermediate Similarity	NPC23126
0.8281	Intermediate Similarity	NPC30501
0.8281	Intermediate Similarity	NPC105157
0.8281	Intermediate Similarity	NPC266689
0.8281	Intermediate Similarity	NPC72158
0.8281	Intermediate Similarity	NPC190043
0.8281	Intermediate Similarity	NPC72667
0.8281	Intermediate Similarity	NPC169250
0.8281	Intermediate Similarity	NPC162612
0.8281	Intermediate Similarity	NPC100067
0.8281	Intermediate Similarity	NPC176130
0.8281	Intermediate Similarity	NPC103356
0.8281	Intermediate Similarity	NPC78364
0.8281	Intermediate Similarity	NPC84672
0.8281	Intermediate Similarity	NPC98254
0.8281	Intermediate Similarity	NPC69424
0.8276	Intermediate Similarity	NPC95178
0.8276	Intermediate Similarity	NPC69332
0.8276	Intermediate Similarity	NPC29989
0.8276	Intermediate Similarity	NPC6984
0.8268	Intermediate Similarity	NPC137750
0.8261	Intermediate Similarity	NPC288411
0.8258	Intermediate Similarity	NPC50924
0.8258	Intermediate Similarity	NPC202225
0.8254	Intermediate Similarity	NPC174991
0.825	Intermediate Similarity	NPC11824
0.824	Intermediate Similarity	NPC251259
0.824	Intermediate Similarity	NPC156139
0.8231	Intermediate Similarity	NPC136588
0.8231	Intermediate Similarity	NPC199253
0.8231	Intermediate Similarity	NPC108129
0.822	Intermediate Similarity	NPC88141
0.8217	Intermediate Similarity	NPC473744
0.8217	Intermediate Similarity	NPC221777
0.8217	Intermediate Similarity	NPC193203
0.8217	Intermediate Similarity	NPC473017
0.8217	Intermediate Similarity	NPC21305
0.8209	Intermediate Similarity	NPC44960
0.8209	Intermediate Similarity	NPC474110
0.8205	Intermediate Similarity	NPC303264
0.8203	Intermediate Similarity	NPC227741
0.8203	Intermediate Similarity	NPC295202
0.8203	Intermediate Similarity	NPC49647
0.8203	Intermediate Similarity	NPC160499
0.8203	Intermediate Similarity	NPC267846
0.8203	Intermediate Similarity	NPC136342
0.819	Intermediate Similarity	NPC138942
0.8189	Intermediate Similarity	NPC184219
0.8189	Intermediate Similarity	NPC231767
0.8188	Intermediate Similarity	NPC275278
0.8182	Intermediate Similarity	NPC285350
0.8182	Intermediate Similarity	NPC78307
0.8175	Intermediate Similarity	NPC133909
0.8175	Intermediate Similarity	NPC32032
0.8175	Intermediate Similarity	NPC67300
0.8174	Intermediate Similarity	NPC168829
0.8168	Intermediate Similarity	NPC244699
0.8168	Intermediate Similarity	NPC18798
0.8167	Intermediate Similarity	NPC231717
0.816	Intermediate Similarity	NPC297186
0.816	Intermediate Similarity	NPC248363
0.8154	Intermediate Similarity	NPC171460
0.8154	Intermediate Similarity	NPC120488
0.8154	Intermediate Similarity	NPC102829
0.8154	Intermediate Similarity	NPC474546
0.8148	Intermediate Similarity	NPC206207
0.814	Intermediate Similarity	NPC116513
0.8125	Intermediate Similarity	NPC123506
0.8125	Intermediate Similarity	NPC127975
0.8125	Intermediate Similarity	NPC131799
0.812	Intermediate Similarity	NPC282780
0.812	Intermediate Similarity	NPC70843
0.812	Intermediate Similarity	NPC274876
0.812	Intermediate Similarity	NPC166480
0.8115	Intermediate Similarity	NPC23402
0.811	Intermediate Similarity	NPC275145
0.8106	Intermediate Similarity	NPC70622
0.8103	Intermediate Similarity	NPC261573
0.8103	Intermediate Similarity	NPC8931
0.8103	Intermediate Similarity	NPC120693
0.8095	Intermediate Similarity	NPC242895
0.8095	Intermediate Similarity	NPC224273
0.8095	Intermediate Similarity	NPC115159
0.8095	Intermediate Similarity	NPC45438
0.8095	Intermediate Similarity	NPC267552
0.8095	Intermediate Similarity	NPC19174
0.8095	Intermediate Similarity	NPC143427
0.8095	Intermediate Similarity	NPC73532
0.8095	Intermediate Similarity	NPC253627
0.8092	Intermediate Similarity	NPC27659
0.8092	Intermediate Similarity	NPC62219
0.8083	Intermediate Similarity	NPC308689
0.808	Intermediate Similarity	NPC473662
0.808	Intermediate Similarity	NPC216297
0.808	Intermediate Similarity	NPC7151
0.8077	Intermediate Similarity	NPC95537
0.8077	Intermediate Similarity	NPC48248
0.8074	Intermediate Similarity	NPC477592
0.8074	Intermediate Similarity	NPC24394
0.8065	Intermediate Similarity	NPC283844
0.8065	Intermediate Similarity	NPC41567
0.8062	Intermediate Similarity	NPC8745
0.8062	Intermediate Similarity	NPC473751
0.806	Intermediate Similarity	NPC470210
0.8051	Intermediate Similarity	NPC228737
0.8047	Intermediate Similarity	NPC13238
0.8047	Intermediate Similarity	NPC236189
0.8047	Intermediate Similarity	NPC74507
0.8047	Intermediate Similarity	NPC234890
0.8047	Intermediate Similarity	NPC152525
0.8047	Intermediate Similarity	NPC68756
0.8045	Intermediate Similarity	NPC314048
0.8045	Intermediate Similarity	NPC225051
0.8043	Intermediate Similarity	NPC73061
0.8043	Intermediate Similarity	NPC469520
0.8043	Intermediate Similarity	NPC477209
0.8034	Intermediate Similarity	NPC163734
0.8033	Intermediate Similarity	NPC163154
0.8031	Intermediate Similarity	NPC300274
0.8031	Intermediate Similarity	NPC11250
0.8031	Intermediate Similarity	NPC176208
0.8031	Intermediate Similarity	NPC283514
0.8031	Intermediate Similarity	NPC309765
0.8031	Intermediate Similarity	NPC139171
0.803	Intermediate Similarity	NPC72669
0.803	Intermediate Similarity	NPC474517
0.803	Intermediate Similarity	NPC473777
0.8029	Intermediate Similarity	NPC476534
0.8015	Intermediate Similarity	NPC62735
0.8015	Intermediate Similarity	NPC99731
0.8015	Intermediate Similarity	NPC303910
0.8015	Intermediate Similarity	NPC92624
0.8015	Intermediate Similarity	NPC141368
0.8015	Intermediate Similarity	NPC23870
0.8	Intermediate Similarity	NPC21162
0.8	Intermediate Similarity	NPC163029
0.8	Intermediate Similarity	NPC252544

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 NPC295034 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	982
0.2-0.3	1218
0.3-0.4	2636
0.4-0.5	2189
0.5-0.6	1264
0.6-0.7	470
0.7-0.8	96
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8413	Intermediate Similarity	NPD1164	Approved
0.8293	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD1201	Approved
0.7899	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD1470	Approved
0.781	Intermediate Similarity	NPD2935	Discontinued
0.7778	Intermediate Similarity	NPD9545	Approved
0.776	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD2344	Approved
0.7754	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1510	Phase 2
0.7704	Intermediate Similarity	NPD943	Approved
0.7704	Intermediate Similarity	NPD1240	Approved
0.7681	Intermediate Similarity	NPD5408	Approved
0.7681	Intermediate Similarity	NPD5406	Approved
0.7681	Intermediate Similarity	NPD5404	Approved
0.7681	Intermediate Similarity	NPD5405	Approved
0.7647	Intermediate Similarity	NPD1237	Approved
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD3972	Approved
0.7607	Intermediate Similarity	NPD3020	Approved
0.7591	Intermediate Similarity	NPD1607	Approved
0.7589	Intermediate Similarity	NPD7003	Approved
0.7556	Intermediate Similarity	NPD3764	Approved
0.7552	Intermediate Similarity	NPD7390	Discontinued
0.7541	Intermediate Similarity	NPD9266	Approved
0.7541	Intermediate Similarity	NPD74	Approved
0.7535	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD2859	Approved
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2860	Approved
0.7483	Intermediate Similarity	NPD4380	Phase 2
0.7482	Intermediate Similarity	NPD2799	Discontinued
0.748	Intermediate Similarity	NPD9493	Approved
0.7463	Intermediate Similarity	NPD9494	Approved
0.7459	Intermediate Similarity	NPD9267	Approved
0.7459	Intermediate Similarity	NPD9263	Approved
0.7459	Intermediate Similarity	NPD9264	Approved
0.7447	Intermediate Similarity	NPD1549	Phase 2
0.7426	Intermediate Similarity	NPD2313	Discontinued
0.7417	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1930	Approved
0.7417	Intermediate Similarity	NPD1929	Approved
0.7415	Intermediate Similarity	NPD7458	Discontinued
0.7414	Intermediate Similarity	NPD2933	Approved
0.7414	Intermediate Similarity	NPD2934	Approved
0.7388	Intermediate Similarity	NPD2798	Approved
0.7385	Intermediate Similarity	NPD3019	Approved
0.7385	Intermediate Similarity	NPD2932	Approved
0.7376	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1876	Approved
0.7368	Intermediate Similarity	NPD1283	Approved
0.7343	Intermediate Similarity	NPD4628	Phase 3
0.7323	Intermediate Similarity	NPD5951	Approved
0.7317	Intermediate Similarity	NPD2342	Discontinued
0.7302	Intermediate Similarity	NPD7635	Approved
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3400	Discontinued
0.7222	Intermediate Similarity	NPD3750	Approved
0.7219	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1809	Phase 2
0.7185	Intermediate Similarity	NPD1203	Approved
0.7183	Intermediate Similarity	NPD1551	Phase 2
0.7183	Intermediate Similarity	NPD2796	Approved
0.7179	Intermediate Similarity	NPD845	Approved
0.7176	Intermediate Similarity	NPD1651	Approved
0.7171	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2346	Discontinued
0.7131	Intermediate Similarity	NPD9261	Approved
0.7124	Intermediate Similarity	NPD7768	Phase 2
0.7123	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1241	Discontinued
0.7107	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7819	Suspended
0.709	Intermediate Similarity	NPD9269	Phase 2
0.7086	Intermediate Similarity	NPD7411	Suspended
0.708	Intermediate Similarity	NPD4208	Discontinued
0.7078	Intermediate Similarity	NPD7075	Discontinued
0.7067	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4476	Approved
0.7063	Intermediate Similarity	NPD3022	Approved
0.7063	Intermediate Similarity	NPD3021	Approved
0.7063	Intermediate Similarity	NPD4477	Approved
0.7059	Intermediate Similarity	NPD2797	Approved
0.7054	Intermediate Similarity	NPD9281	Approved
0.7049	Intermediate Similarity	NPD1932	Approved
0.7047	Intermediate Similarity	NPD920	Approved
0.7045	Intermediate Similarity	NPD9268	Approved
0.7039	Intermediate Similarity	NPD1934	Approved
0.7025	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD3300	Phase 2
0.7007	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD6663	Approved
0.7	Intermediate Similarity	NPD288	Approved
0.6993	Remote Similarity	NPD4308	Phase 3
0.6993	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4626	Approved
0.6978	Remote Similarity	NPD7008	Discontinued
0.6975	Remote Similarity	NPD688	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1894	Discontinued
0.6968	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1481	Phase 2
0.6963	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD5736	Approved
0.6954	Remote Similarity	NPD3226	Approved
0.6953	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2979	Phase 3
0.6948	Remote Similarity	NPD2296	Approved
0.6943	Remote Similarity	NPD6959	Discontinued
0.6929	Remote Similarity	NPD3268	Approved
0.6929	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9258	Approved
0.6923	Remote Similarity	NPD9256	Approved
0.6918	Remote Similarity	NPD2800	Approved
0.6917	Remote Similarity	NPD844	Approved
0.6913	Remote Similarity	NPD2533	Approved
0.6913	Remote Similarity	NPD2532	Approved
0.6913	Remote Similarity	NPD2534	Approved
0.6912	Remote Similarity	NPD1755	Approved
0.6912	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD940	Approved
0.6911	Remote Similarity	NPD846	Approved
0.6906	Remote Similarity	NPD6832	Phase 2
0.6903	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6355	Discontinued
0.6894	Remote Similarity	NPD5844	Phase 1
0.6891	Remote Similarity	NPD1202	Approved
0.6889	Remote Similarity	NPD1535	Discovery
0.6885	Remote Similarity	NPD1238	Approved
0.6879	Remote Similarity	NPD520	Approved
0.6875	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7473	Discontinued
0.6871	Remote Similarity	NPD8166	Discontinued
0.687	Remote Similarity	NPD255	Approved
0.687	Remote Similarity	NPD256	Approved
0.6867	Remote Similarity	NPD6273	Approved
0.6867	Remote Similarity	NPD1512	Approved
0.6866	Remote Similarity	NPD4589	Approved
0.6866	Remote Similarity	NPD2286	Discontinued
0.6859	Remote Similarity	NPD3749	Approved
0.6857	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6799	Approved
0.6842	Remote Similarity	NPD3091	Approved
0.6842	Remote Similarity	NPD5303	Approved
0.6842	Remote Similarity	NPD5304	Approved
0.6838	Remote Similarity	NPD4878	Approved
0.6838	Remote Similarity	NPD9717	Approved
0.6831	Remote Similarity	NPD4060	Phase 1
0.6829	Remote Similarity	NPD1242	Phase 1
0.6824	Remote Similarity	NPD6190	Approved
0.6818	Remote Similarity	NPD6801	Discontinued
0.6815	Remote Similarity	NPD3026	Approved
0.6815	Remote Similarity	NPD3023	Approved
0.6809	Remote Similarity	NPD6798	Discontinued
0.6803	Remote Similarity	NPD1243	Approved
0.6797	Remote Similarity	NPD6599	Discontinued
0.6795	Remote Similarity	NPD3882	Suspended
0.6791	Remote Similarity	NPD5691	Approved
0.6791	Remote Similarity	NPD3024	Approved
0.6791	Remote Similarity	NPD3025	Approved
0.6788	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4207	Discontinued
0.6783	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD111	Approved
0.6779	Remote Similarity	NPD7440	Discontinued
0.6774	Remote Similarity	NPD2801	Approved
0.6768	Remote Similarity	NPD6559	Discontinued
0.6765	Remote Similarity	NPD1610	Phase 2
0.6757	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2066	Phase 3
0.6744	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD17	Approved
0.6741	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6651	Approved
0.6723	Remote Similarity	NPD1239	Approved
0.6719	Remote Similarity	NPD2329	Discontinued
0.6718	Remote Similarity	NPD2229	Approved
0.6718	Remote Similarity	NPD2228	Approved
0.6718	Remote Similarity	NPD2234	Approved
0.6714	Remote Similarity	NPD2861	Phase 2
0.6713	Remote Similarity	NPD3142	Approved
0.6713	Remote Similarity	NPD3140	Approved
0.6713	Remote Similarity	NPD4307	Phase 2
0.6711	Remote Similarity	NPD3295	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