NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.07
Volume:	206.365
LogP:	-0.16
LogD:	0.054
LogS:	-1.471
# Rotatable Bonds:	4
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	2.598
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.911
MDCK Permeability:	5.9481593780219555e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.108
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.88
Plasma Protein Binding (PPB):	55.48407745361328%
Volume Distribution (VD):	0.701
Pgp-substrate:	42.37657928466797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.289
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.2
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.561
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.33
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	4.857
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.441
AMES Toxicity:	0.269
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.086
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.169
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC325625

Natural Product ID:	NPC325625
*Common Name:**	2,3-Dihydroxy-1-(4-Hydroxy-3-Methoxyphenyl)Propan-1-One
IUPAC Name:	2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	UTXNRISXYKZJTH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O5/c1-15-9-4-6(2-3-7(9)12)10(14)8(13)5-11/h2-4,8,11-13H,5H2,1H3
SMILES:	OCC(C(=O)c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL590536
PubChem CID:	15765124
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12643908]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974602]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20189399]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17691	Santalum album	Species	Santalaceae	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
Others	7

Activity Type	# Activity
Individual Protein	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	10.4	%	PMID[521178]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	Activity	=	63.0	%	PMID[521179]
NPT2	Others	Unspecified		Inhibition	=	16.5	%	PMID[521178]
NPT2	Others	Unspecified		Inhibition	=	18.1	%	PMID[521178]
NPT2	Others	Unspecified		Inhibition	=	24.0	%	PMID[521178]
NPT2	Others	Unspecified		Inhibition	=	25.8	%	PMID[521178]
NPT27	Others	Unspecified		Inhibition	<	8.8	%	PMID[521178]

☑ 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 NPC325625 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	358
0.1-0.2	1502
0.2-0.3	4268
0.3-0.4	10009
0.4-0.5	7996
0.5-0.6	3780
0.6-0.7	6768
0.7-0.8	6821
0.8-0.85	1029
0.85-0.9	153
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC139519
0.9542	High Similarity	NPC50763
0.9338	High Similarity	NPC4796
0.9209	High Similarity	NPC46161
0.9209	High Similarity	NPC239608
0.916	High Similarity	NPC16651
0.916	High Similarity	NPC32163
0.9044	High Similarity	NPC208760
0.9037	High Similarity	NPC283823
0.9037	High Similarity	NPC307006
0.9037	High Similarity	NPC129889
0.9037	High Similarity	NPC159418
0.8993	High Similarity	NPC50823
0.8963	High Similarity	NPC111888
0.8921	High Similarity	NPC474784
0.8921	High Similarity	NPC322021
0.8889	High Similarity	NPC474903
0.8873	High Similarity	NPC469683
0.8872	High Similarity	NPC203719
0.8872	High Similarity	NPC117237
0.8865	High Similarity	NPC299154
0.8815	High Similarity	NPC195292
0.8815	High Similarity	NPC66905
0.8815	High Similarity	NPC285776
0.8815	High Similarity	NPC142985
0.8811	High Similarity	NPC287495
0.8811	High Similarity	NPC9370
0.8803	High Similarity	NPC469615
0.8768	High Similarity	NPC274613
0.875	High Similarity	NPC226987
0.875	High Similarity	NPC143903
0.875	High Similarity	NPC469480
0.8741	High Similarity	NPC142165
0.8732	High Similarity	NPC312256
0.8731	High Similarity	NPC20404
0.8731	High Similarity	NPC281020
0.8731	High Similarity	NPC293641
0.8731	High Similarity	NPC12022
0.8731	High Similarity	NPC20287
0.8716	High Similarity	NPC25127
0.8699	High Similarity	NPC264550
0.8699	High Similarity	NPC40290
0.8699	High Similarity	NPC200060
0.8699	High Similarity	NPC139293
0.8699	High Similarity	NPC69430
0.8699	High Similarity	NPC195763
0.8699	High Similarity	NPC205054
0.8699	High Similarity	NPC142876
0.8699	High Similarity	NPC264289
0.8699	High Similarity	NPC333691
0.8696	High Similarity	NPC237330
0.869	High Similarity	NPC125449
0.869	High Similarity	NPC98009
0.869	High Similarity	NPC188074
0.869	High Similarity	NPC472969
0.8681	High Similarity	NPC30890
0.8676	High Similarity	NPC298268
0.8675	High Similarity	NPC472962
0.8675	High Similarity	NPC472961
0.8671	High Similarity	NPC287722
0.8671	High Similarity	NPC254659
0.8671	High Similarity	NPC473090
0.8667	High Similarity	NPC278308
0.8667	High Similarity	NPC52530
0.8662	High Similarity	NPC84273
0.8662	High Similarity	NPC110419
0.8649	High Similarity	NPC327225
0.8643	High Similarity	NPC112068
0.8643	High Similarity	NPC110899
0.8643	High Similarity	NPC25305
0.8643	High Similarity	NPC95679
0.8643	High Similarity	NPC125417
0.8636	High Similarity	NPC114298
0.863	High Similarity	NPC183655
0.863	High Similarity	NPC139364
0.863	High Similarity	NPC98809
0.863	High Similarity	NPC80710
0.863	High Similarity	NPC203747
0.863	High Similarity	NPC254702
0.863	High Similarity	NPC287395
0.863	High Similarity	NPC194653
0.863	High Similarity	NPC476394
0.8626	High Similarity	NPC225245
0.8618	High Similarity	NPC308992
0.8611	High Similarity	NPC207732
0.8609	High Similarity	NPC477410
0.8603	High Similarity	NPC261759
0.8603	High Similarity	NPC226855
0.8601	High Similarity	NPC301178
0.8601	High Similarity	NPC284556
0.86	High Similarity	NPC326037
0.86	High Similarity	NPC13858
0.86	High Similarity	NPC320825
0.8593	High Similarity	NPC158654
0.8592	High Similarity	NPC326065
0.8591	High Similarity	NPC287504
0.8591	High Similarity	NPC246328
0.8591	High Similarity	NPC325028
0.8591	High Similarity	NPC27532
0.8591	High Similarity	NPC256346
0.8582	High Similarity	NPC284409
0.8581	High Similarity	NPC151425
0.8581	High Similarity	NPC31363
0.8571	High Similarity	NPC242372
0.8571	High Similarity	NPC4181
0.8571	High Similarity	NPC164778
0.8571	High Similarity	NPC324929
0.8571	High Similarity	NPC92722
0.8571	High Similarity	NPC257976
0.8571	High Similarity	NPC102003
0.8562	High Similarity	NPC294972
0.8553	High Similarity	NPC263449
0.8552	High Similarity	NPC98356
0.8542	High Similarity	NPC50954
0.8542	High Similarity	NPC119663
0.8542	High Similarity	NPC471417
0.854	High Similarity	NPC137427
0.854	High Similarity	NPC311419
0.854	High Similarity	NPC123196
0.854	High Similarity	NPC65935
0.854	High Similarity	NPC215941
0.854	High Similarity	NPC172673
0.854	High Similarity	NPC244246
0.854	High Similarity	NPC275724
0.854	High Similarity	NPC319282
0.8523	High Similarity	NPC269451
0.8523	High Similarity	NPC216769
0.8523	High Similarity	NPC246162
0.8523	High Similarity	NPC100971
0.8523	High Similarity	NPC209487
0.8523	High Similarity	NPC477231
0.8523	High Similarity	NPC131266
0.8523	High Similarity	NPC35763
0.8523	High Similarity	NPC245382
0.8523	High Similarity	NPC61506
0.8523	High Similarity	NPC240476
0.8523	High Similarity	NPC55205
0.8523	High Similarity	NPC181209
0.8523	High Similarity	NPC9743
0.8523	High Similarity	NPC121522
0.8523	High Similarity	NPC100263
0.8523	High Similarity	NPC291802
0.8523	High Similarity	NPC257648
0.8523	High Similarity	NPC36835
0.8523	High Similarity	NPC260491
0.8523	High Similarity	NPC304954
0.8521	High Similarity	NPC288452
0.8521	High Similarity	NPC289690
0.8519	High Similarity	NPC154275
0.8514	High Similarity	NPC260582
0.8514	High Similarity	NPC29231
0.8514	High Similarity	NPC472279
0.8507	High Similarity	NPC312404
0.8507	High Similarity	NPC273686
0.8503	High Similarity	NPC131451
0.8503	High Similarity	NPC15329
0.85	High Similarity	NPC470990
0.8493	Intermediate Similarity	NPC32058
0.8493	Intermediate Similarity	NPC165389
0.8493	Intermediate Similarity	NPC12377
0.8493	Intermediate Similarity	NPC85734
0.8489	Intermediate Similarity	NPC327410
0.8487	Intermediate Similarity	NPC55738
0.8483	Intermediate Similarity	NPC242893
0.8483	Intermediate Similarity	NPC275278
0.8483	Intermediate Similarity	NPC38065
0.8477	Intermediate Similarity	NPC265511
0.8477	Intermediate Similarity	NPC250922
0.8477	Intermediate Similarity	NPC474638
0.8477	Intermediate Similarity	NPC201837
0.8473	Intermediate Similarity	NPC299406
0.8467	Intermediate Similarity	NPC124714
0.8456	Intermediate Similarity	NPC45291
0.8456	Intermediate Similarity	NPC473201
0.8456	Intermediate Similarity	NPC19980
0.8456	Intermediate Similarity	NPC200740
0.8456	Intermediate Similarity	NPC54394
0.8456	Intermediate Similarity	NPC302783
0.8456	Intermediate Similarity	NPC276466
0.8456	Intermediate Similarity	NPC252933
0.8456	Intermediate Similarity	NPC256406
0.8456	Intermediate Similarity	NPC5018
0.8456	Intermediate Similarity	NPC75695
0.8456	Intermediate Similarity	NPC151167
0.8456	Intermediate Similarity	NPC123228
0.8456	Intermediate Similarity	NPC123722
0.8456	Intermediate Similarity	NPC125062
0.844	Intermediate Similarity	NPC475111
0.8435	Intermediate Similarity	NPC61871
0.8435	Intermediate Similarity	NPC30647
0.8435	Intermediate Similarity	NPC168803
0.8435	Intermediate Similarity	NPC119660
0.8435	Intermediate Similarity	NPC55557
0.8435	Intermediate Similarity	NPC93034
0.8433	Intermediate Similarity	NPC244876
0.8433	Intermediate Similarity	NPC474691
0.8431	Intermediate Similarity	NPC287328
0.8431	Intermediate Similarity	NPC282009
0.8429	Intermediate Similarity	NPC155098
0.8429	Intermediate Similarity	NPC471110

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 NPC325625 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	943
0.2-0.3	1813
0.3-0.4	2621
0.4-0.5	1793
0.5-0.6	1047
0.6-0.7	501
0.7-0.8	107
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8872	High Similarity	NPD9494	Approved
0.86	High Similarity	NPD3882	Suspended
0.84	Intermediate Similarity	NPD1934	Approved
0.8243	Intermediate Similarity	NPD1512	Approved
0.8227	Intermediate Similarity	NPD230	Phase 1
0.8224	Intermediate Similarity	NPD2801	Approved
0.8217	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6166	Phase 2
0.8217	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1511	Approved
0.8105	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7935	Intermediate Similarity	NPD3817	Phase 2
0.7931	Intermediate Similarity	NPD1510	Phase 2
0.7931	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7902	Intermediate Similarity	NPD1240	Approved
0.7902	Intermediate Similarity	NPD943	Approved
0.7866	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD228	Approved
0.7853	Intermediate Similarity	NPD6797	Phase 2
0.7852	Intermediate Similarity	NPD6190	Approved
0.7852	Intermediate Similarity	NPD9545	Approved
0.7847	Intermediate Similarity	NPD447	Suspended
0.784	Intermediate Similarity	NPD7054	Approved
0.7805	Intermediate Similarity	NPD7251	Discontinued
0.7793	Intermediate Similarity	NPD1607	Approved
0.7792	Intermediate Similarity	NPD4380	Phase 2
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7791	Intermediate Similarity	NPD7472	Approved
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1549	Phase 2
0.7758	Intermediate Similarity	NPD7808	Phase 3
0.7748	Intermediate Similarity	NPD6799	Approved
0.7722	Intermediate Similarity	NPD7075	Discontinued
0.7703	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7651	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6801	Discontinued
0.7578	Intermediate Similarity	NPD1247	Approved
0.7571	Intermediate Similarity	NPD9269	Phase 2
0.7562	Intermediate Similarity	NPD919	Approved
0.755	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6232	Discontinued
0.7518	Intermediate Similarity	NPD5536	Phase 2
0.7516	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD824	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7685	Pre-registration
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5402	Approved
0.7452	Intermediate Similarity	NPD6599	Discontinued
0.7421	Intermediate Similarity	NPD1465	Phase 2
0.7412	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6386	Approved
0.7405	Intermediate Similarity	NPD6385	Approved
0.74	Intermediate Similarity	NPD2796	Approved
0.74	Intermediate Similarity	NPD2935	Discontinued
0.7384	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3926	Phase 2
0.7372	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5401	Approved
0.7353	Intermediate Similarity	NPD1241	Discontinued
0.7351	Intermediate Similarity	NPD2344	Approved
0.7349	Intermediate Similarity	NPD2163	Approved
0.7305	Intermediate Similarity	NPD5844	Phase 1
0.7305	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1613	Approved
0.7297	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD9268	Approved
0.7246	Intermediate Similarity	NPD3751	Discontinued
0.7244	Intermediate Similarity	NPD3146	Approved
0.7244	Intermediate Similarity	NPD2532	Approved
0.7244	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2533	Approved
0.7244	Intermediate Similarity	NPD2534	Approved
0.7205	Intermediate Similarity	NPD7819	Suspended
0.7203	Intermediate Similarity	NPD3972	Approved
0.7203	Intermediate Similarity	NPD9717	Approved
0.7203	Intermediate Similarity	NPD1608	Approved
0.7194	Intermediate Similarity	NPD9493	Approved
0.7171	Intermediate Similarity	NPD1551	Phase 2
0.717	Intermediate Similarity	NPD3455	Phase 2
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1357	Approved
0.7161	Intermediate Similarity	NPD2354	Approved
0.7161	Intermediate Similarity	NPD2309	Approved
0.716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7266	Discontinued
0.7123	Intermediate Similarity	NPD5647	Approved
0.7107	Intermediate Similarity	NPD1653	Approved
0.7105	Intermediate Similarity	NPD2799	Discontinued
0.7102	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7411	Suspended
0.7076	Intermediate Similarity	NPD6559	Discontinued
0.7071	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8434	Phase 2
0.7063	Intermediate Similarity	NPD3226	Approved
0.7055	Intermediate Similarity	NPD1470	Approved
0.7055	Intermediate Similarity	NPD1203	Approved
0.7051	Intermediate Similarity	NPD3887	Approved
0.7047	Intermediate Similarity	NPD6798	Discontinued
0.7047	Intermediate Similarity	NPD411	Approved
0.7047	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD37	Approved
0.7032	Intermediate Similarity	NPD2800	Approved
0.703	Intermediate Similarity	NPD6234	Discontinued
0.7027	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1933	Approved
0.702	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD1471	Phase 3
0.7007	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD3787	Discontinued
0.7	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6994	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD17	Approved
0.6993	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4110	Phase 3
0.6987	Remote Similarity	NPD3750	Approved
0.6987	Remote Similarity	NPD8166	Discontinued
0.6986	Remote Similarity	NPD1876	Approved
0.6978	Remote Similarity	NPD5283	Phase 1
0.6977	Remote Similarity	NPD7038	Approved
0.6977	Remote Similarity	NPD7039	Approved
0.6974	Remote Similarity	NPD6651	Approved
0.6964	Remote Similarity	NPD5242	Approved
0.6962	Remote Similarity	NPD4357	Discontinued
0.6959	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7458	Discontinued
0.6954	Remote Similarity	NPD1558	Phase 1
0.6954	Remote Similarity	NPD3620	Phase 2
0.6954	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD9570	Approved
0.6946	Remote Similarity	NPD6959	Discontinued
0.6937	Remote Similarity	NPD920	Approved
0.6933	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2313	Discontinued
0.6918	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1358	Approved
0.6909	Remote Similarity	NPD4967	Phase 2
0.6909	Remote Similarity	NPD4966	Approved
0.6909	Remote Similarity	NPD4965	Approved
0.6903	Remote Similarity	NPD2346	Discontinued
0.6903	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2353	Approved
0.6897	Remote Similarity	NPD3705	Approved
0.6897	Remote Similarity	NPD1201	Approved
0.6883	Remote Similarity	NPD7033	Discontinued
0.6875	Remote Similarity	NPD1778	Approved
0.6875	Remote Similarity	NPD8150	Discontinued
0.6871	Remote Similarity	NPD1283	Approved
0.6871	Remote Similarity	NPD958	Approved
0.6867	Remote Similarity	NPD3749	Approved
0.6864	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2684	Approved
0.6852	Remote Similarity	NPD2651	Approved
0.6852	Remote Similarity	NPD2649	Approved
0.6848	Remote Similarity	NPD5978	Approved
0.6848	Remote Similarity	NPD5977	Approved
0.6845	Remote Similarity	NPD7199	Phase 2
0.6845	Remote Similarity	NPD8127	Discontinued
0.6842	Remote Similarity	NPD3140	Approved
0.6842	Remote Similarity	NPD7228	Approved
0.6842	Remote Similarity	NPD4060	Phase 1
0.6842	Remote Similarity	NPD3142	Approved
0.6831	Remote Similarity	NPD6777	Approved
0.6831	Remote Similarity	NPD6781	Approved
0.6831	Remote Similarity	NPD6778	Approved
0.6831	Remote Similarity	NPD6782	Approved
0.6831	Remote Similarity	NPD6776	Approved
0.6831	Remote Similarity	NPD6780	Approved
0.6831	Remote Similarity	NPD6779	Approved
0.6829	Remote Similarity	NPD6844	Discontinued
0.6824	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1237	Approved
0.6815	Remote Similarity	NPD3060	Approved
0.6815	Remote Similarity	NPD2654	Approved
0.6815	Remote Similarity	NPD1243	Approved
0.6813	Remote Similarity	NPD4662	Approved
0.6813	Remote Similarity	NPD4661	Approved
0.6813	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7768	Phase 2
0.6806	Remote Similarity	NPD1651	Approved
0.68	Remote Similarity	NPD8312	Approved
0.68	Remote Similarity	NPD3534	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