NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.11
Volume:	208.717
LogP:	1.387
LogD:	1.443
LogS:	-1.954
# Rotatable Bonds:	5
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	1.564
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.244
MDCK Permeability:	2.707750172703527e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.599
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.964
Plasma Protein Binding (PPB):	48.177085876464844%
Volume Distribution (VD):	1.171
Pgp-substrate:	23.45760726928711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.857
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.431
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.778
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.486

ADMET: Excretion

Clearance (CL):	9.48
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.778
Carcinogencity:	0.297
Eye Corrosion:	0.606
Eye Irritation:	0.938
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC137685

Natural Product ID:	NPC137685
*Common Name:**	3-(3,4-Dimethoxyphenyl)Propan-1-Ol
IUPAC Name:	3-(3,4-dimethoxyphenyl)propan-1-ol
Synonyms:
Standard InCHIKey:	ZISWRXJZUKDIOO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O3/c1-13-10-6-5-9(4-3-7-12)8-11(10)14-2/h5-6,8,12H,3-4,7H2,1-2H3
SMILES:	COc1ccc(CCCO)cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088633
PubChem CID:	77528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

*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
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22951040]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	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	5
Others	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	11750.0	nM	PMID[532469]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	21860.0	nM	PMID[532469]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	23100.0	nM	PMID[532469]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	26640.0	nM	PMID[532469]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	103.3	%	PMID[532469]
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	500000.0	nM	PMID[532469]

☑ 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 NPC137685 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	269
0.1-0.2	1641
0.2-0.3	5459
0.3-0.4	13696
0.4-0.5	4213
0.5-0.6	7414
0.6-0.7	7127
0.7-0.8	2313
0.8-0.85	439
0.85-0.9	95
0.9-0.95	29
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9515	High Similarity	NPC227894
0.9412	High Similarity	NPC292792
0.9358	High Similarity	NPC164386
0.934	High Similarity	NPC173746
0.934	High Similarity	NPC139617
0.934	High Similarity	NPC55300
0.934	High Similarity	NPC8547
0.934	High Similarity	NPC257124
0.934	High Similarity	NPC156840
0.934	High Similarity	NPC78918
0.9273	High Similarity	NPC474214
0.9273	High Similarity	NPC474040
0.9266	High Similarity	NPC221049
0.9252	High Similarity	NPC165646
0.9216	High Similarity	NPC12714
0.9216	High Similarity	NPC310905
0.9189	High Similarity	NPC474320
0.9189	High Similarity	NPC311595
0.9189	High Similarity	NPC24474
0.9189	High Similarity	NPC135961
0.9151	High Similarity	NPC7097
0.9151	High Similarity	NPC36108
0.9151	High Similarity	NPC246358
0.9151	High Similarity	NPC233731
0.9143	High Similarity	NPC258171
0.9099	High Similarity	NPC255675
0.9099	High Similarity	NPC63083
0.9027	High Similarity	NPC207613
0.902	High Similarity	NPC100870
0.9018	High Similarity	NPC320987
0.9018	High Similarity	NPC181969
0.9009	High Similarity	NPC293619
0.8981	High Similarity	NPC195873
0.8947	High Similarity	NPC54872
0.8947	High Similarity	NPC470212
0.8947	High Similarity	NPC324571
0.8947	High Similarity	NPC262156
0.8947	High Similarity	NPC343720
0.8947	High Similarity	NPC312675
0.8947	High Similarity	NPC470804
0.8947	High Similarity	NPC476343
0.8947	High Similarity	NPC473853
0.8947	High Similarity	NPC113865
0.8947	High Similarity	NPC184651
0.8938	High Similarity	NPC148615
0.8938	High Similarity	NPC177475
0.8938	High Similarity	NPC35071
0.8929	High Similarity	NPC470626
0.887	High Similarity	NPC71090
0.887	High Similarity	NPC85488
0.8857	High Similarity	NPC38079
0.8857	High Similarity	NPC108875
0.885	High Similarity	NPC281298
0.885	High Similarity	NPC310338
0.8818	High Similarity	NPC165106
0.8818	High Similarity	NPC204120
0.8793	High Similarity	NPC471693
0.8793	High Similarity	NPC244876
0.8793	High Similarity	NPC280704
0.8783	High Similarity	NPC290451
0.8783	High Similarity	NPC127389
0.8783	High Similarity	NPC49341
0.8774	High Similarity	NPC470393
0.8772	High Similarity	NPC232316
0.8772	High Similarity	NPC117780
0.8772	High Similarity	NPC165133
0.8772	High Similarity	NPC56214
0.8772	High Similarity	NPC242885
0.8772	High Similarity	NPC227217
0.8772	High Similarity	NPC95614
0.8761	High Similarity	NPC205502
0.875	High Similarity	NPC81067
0.875	High Similarity	NPC9341
0.8718	High Similarity	NPC109822
0.8718	High Similarity	NPC114901
0.8718	High Similarity	NPC94276
0.8718	High Similarity	NPC48990
0.8718	High Similarity	NPC293701
0.8716	High Similarity	NPC179309
0.8716	High Similarity	NPC31279
0.8707	High Similarity	NPC209567
0.8704	High Similarity	NPC75440
0.8684	High Similarity	NPC299406
0.8684	High Similarity	NPC20674
0.8673	High Similarity	NPC86947
0.8673	High Similarity	NPC39793
0.8661	High Similarity	NPC473264
0.8661	High Similarity	NPC47194
0.8661	High Similarity	NPC475815
0.8649	High Similarity	NPC303522
0.8644	High Similarity	NPC194519
0.8644	High Similarity	NPC148627
0.8636	High Similarity	NPC203924
0.8632	High Similarity	NPC317769
0.8632	High Similarity	NPC220598
0.8632	High Similarity	NPC31344
0.8632	High Similarity	NPC165375
0.8624	High Similarity	NPC127326
0.8621	High Similarity	NPC201777
0.8621	High Similarity	NPC160380
0.8621	High Similarity	NPC38996
0.8611	High Similarity	NPC251306
0.8609	High Similarity	NPC229401
0.8585	High Similarity	NPC305205
0.8571	High Similarity	NPC58607
0.8571	High Similarity	NPC294941
0.8571	High Similarity	NPC178284
0.8571	High Similarity	NPC191037
0.8571	High Similarity	NPC206882
0.8559	High Similarity	NPC146886
0.8559	High Similarity	NPC60517
0.8559	High Similarity	NPC20443
0.8547	High Similarity	NPC41562
0.8547	High Similarity	NPC270326
0.8547	High Similarity	NPC114298
0.8547	High Similarity	NPC30462
0.8534	High Similarity	NPC204466
0.8534	High Similarity	NPC199023
0.8522	High Similarity	NPC37858
0.8509	High Similarity	NPC280001
0.8509	High Similarity	NPC259638
0.8505	High Similarity	NPC12987
0.8505	High Similarity	NPC474603
0.85	High Similarity	NPC5428
0.85	High Similarity	NPC292056
0.85	High Similarity	NPC111247
0.85	High Similarity	NPC474119
0.85	High Similarity	NPC165045
0.85	High Similarity	NPC20287
0.85	High Similarity	NPC242032
0.85	High Similarity	NPC293641
0.85	High Similarity	NPC319625
0.85	High Similarity	NPC118787
0.85	High Similarity	NPC163332
0.85	High Similarity	NPC41706
0.85	High Similarity	NPC118533
0.85	High Similarity	NPC12022
0.85	High Similarity	NPC20404
0.85	High Similarity	NPC147821
0.85	High Similarity	NPC183181
0.8491	Intermediate Similarity	NPC110764
0.8491	Intermediate Similarity	NPC51633
0.8487	Intermediate Similarity	NPC280767
0.8475	Intermediate Similarity	NPC4181
0.8475	Intermediate Similarity	NPC228922
0.8475	Intermediate Similarity	NPC197757
0.8475	Intermediate Similarity	NPC282496
0.8475	Intermediate Similarity	NPC233526
0.8475	Intermediate Similarity	NPC249788
0.8475	Intermediate Similarity	NPC257976
0.8475	Intermediate Similarity	NPC163083
0.8475	Intermediate Similarity	NPC242372
0.8475	Intermediate Similarity	NPC164778
0.8468	Intermediate Similarity	NPC245552
0.8462	Intermediate Similarity	NPC285289
0.8462	Intermediate Similarity	NPC194416
0.8462	Intermediate Similarity	NPC70752
0.8462	Intermediate Similarity	NPC177291
0.8455	Intermediate Similarity	NPC165386
0.8455	Intermediate Similarity	NPC474272
0.8448	Intermediate Similarity	NPC202474
0.8448	Intermediate Similarity	NPC474565
0.844	Intermediate Similarity	NPC233320
0.8435	Intermediate Similarity	NPC272471
0.8435	Intermediate Similarity	NPC107588
0.8435	Intermediate Similarity	NPC164706
0.8435	Intermediate Similarity	NPC70744
0.8435	Intermediate Similarity	NPC137537
0.8435	Intermediate Similarity	NPC212743
0.8431	Intermediate Similarity	NPC321956
0.843	Intermediate Similarity	NPC470084
0.843	Intermediate Similarity	NPC186843
0.843	Intermediate Similarity	NPC245826
0.843	Intermediate Similarity	NPC278308
0.843	Intermediate Similarity	NPC252307
0.843	Intermediate Similarity	NPC470213
0.843	Intermediate Similarity	NPC206615
0.843	Intermediate Similarity	NPC98631
0.843	Intermediate Similarity	NPC474178
0.843	Intermediate Similarity	NPC277458
0.843	Intermediate Similarity	NPC307050
0.8421	Intermediate Similarity	NPC193067
0.8417	Intermediate Similarity	NPC40352
0.8417	Intermediate Similarity	NPC213552
0.8417	Intermediate Similarity	NPC213711
0.8417	Intermediate Similarity	NPC120225
0.8411	Intermediate Similarity	NPC192596
0.8403	Intermediate Similarity	NPC273686
0.8403	Intermediate Similarity	NPC312404
0.8381	Intermediate Similarity	NPC470161
0.8378	Intermediate Similarity	NPC46844
0.8376	Intermediate Similarity	NPC60962
0.8376	Intermediate Similarity	NPC267064
0.8376	Intermediate Similarity	NPC14007
0.8376	Intermediate Similarity	NPC158949
0.8376	Intermediate Similarity	NPC183262
0.8376	Intermediate Similarity	NPC166759
0.8376	Intermediate Similarity	NPC189844
0.8376	Intermediate Similarity	NPC109083
0.8376	Intermediate Similarity	NPC269843

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 NPC137685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	1033
0.2-0.3	1694
0.3-0.4	2688
0.4-0.5	1701
0.5-0.6	991
0.6-0.7	601
0.7-0.8	160
0.8-0.85	9
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.934	High Similarity	NPD228	Approved
0.885	High Similarity	NPD1357	Approved
0.8818	High Similarity	NPD5283	Phase 1
0.8704	High Similarity	NPD2684	Approved
0.8393	Intermediate Similarity	NPD7843	Approved
0.8361	Intermediate Similarity	NPD3027	Phase 3
0.8333	Intermediate Similarity	NPD7157	Approved
0.8273	Intermediate Similarity	NPD290	Approved
0.819	Intermediate Similarity	NPD5536	Phase 2
0.8167	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD3705	Approved
0.807	Intermediate Similarity	NPD821	Approved
0.8016	Intermediate Similarity	NPD3620	Phase 2
0.8016	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD291	Approved
0.7946	Intermediate Similarity	NPD1358	Approved
0.7937	Intermediate Similarity	NPD2674	Phase 3
0.7937	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD9296	Approved
0.7903	Intermediate Similarity	NPD9494	Approved
0.7869	Intermediate Similarity	NPD2983	Phase 2
0.7869	Intermediate Similarity	NPD2982	Phase 2
0.784	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD3022	Approved
0.7807	Intermediate Similarity	NPD3021	Approved
0.7787	Intermediate Similarity	NPD2981	Phase 2
0.776	Intermediate Similarity	NPD3018	Phase 2
0.7734	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1613	Approved
0.7717	Intermediate Similarity	NPD3145	Approved
0.7717	Intermediate Similarity	NPD3144	Approved
0.7712	Intermediate Similarity	NPD6671	Approved
0.771	Intermediate Similarity	NPD2161	Phase 2
0.7699	Intermediate Similarity	NPD968	Approved
0.7699	Intermediate Similarity	NPD3134	Approved
0.7686	Intermediate Similarity	NPD5846	Approved
0.7686	Intermediate Similarity	NPD6516	Phase 2
0.7686	Intermediate Similarity	NPD4626	Approved
0.7669	Intermediate Similarity	NPD3060	Approved
0.7669	Intermediate Similarity	NPD4237	Approved
0.7669	Intermediate Similarity	NPD4236	Phase 3
0.7652	Intermediate Similarity	NPD5451	Approved
0.7642	Intermediate Similarity	NPD9365	Approved
0.7603	Intermediate Similarity	NPD5691	Approved
0.7597	Intermediate Similarity	NPD1558	Phase 1
0.7594	Intermediate Similarity	NPD7153	Discontinued
0.7593	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2933	Approved
0.7593	Intermediate Similarity	NPD2934	Approved
0.7581	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5110	Phase 2
0.7578	Intermediate Similarity	NPD5718	Phase 2
0.7578	Intermediate Similarity	NPD5111	Phase 2
0.7578	Intermediate Similarity	NPD5109	Approved
0.7559	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5241	Discontinued
0.7541	Intermediate Similarity	NPD2667	Approved
0.7541	Intermediate Similarity	NPD1778	Approved
0.7541	Intermediate Similarity	NPD2668	Approved
0.754	Intermediate Similarity	NPD6584	Phase 3
0.7537	Intermediate Similarity	NPD4162	Approved
0.7523	Intermediate Similarity	NPD2860	Approved
0.7523	Intermediate Similarity	NPD2859	Approved
0.7523	Intermediate Similarity	NPD844	Approved
0.752	Intermediate Similarity	NPD2922	Phase 1
0.7519	Intermediate Similarity	NPD1375	Discontinued
0.75	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2235	Phase 2
0.75	Intermediate Similarity	NPD2231	Phase 2
0.7481	Intermediate Similarity	NPD6331	Phase 2
0.7481	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD4110	Phase 3
0.748	Intermediate Similarity	NPD3496	Discontinued
0.748	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD3020	Approved
0.7462	Intermediate Similarity	NPD4060	Phase 1
0.746	Intermediate Similarity	NPD1819	Approved
0.746	Intermediate Similarity	NPD1818	Approved
0.746	Intermediate Similarity	NPD1817	Approved
0.746	Intermediate Similarity	NPD1820	Approved
0.7459	Intermediate Similarity	NPD1651	Approved
0.744	Intermediate Similarity	NPD3685	Discontinued
0.744	Intermediate Similarity	NPD1669	Approved
0.7417	Intermediate Similarity	NPD709	Approved
0.7407	Intermediate Similarity	NPD5177	Phase 3
0.7405	Intermediate Similarity	NPD3657	Discovery
0.7405	Intermediate Similarity	NPD5735	Approved
0.7404	Intermediate Similarity	NPD111	Approved
0.7402	Intermediate Similarity	NPD4624	Approved
0.7402	Intermediate Similarity	NPD3690	Phase 2
0.7402	Intermediate Similarity	NPD3691	Phase 2
0.7395	Intermediate Similarity	NPD1241	Discontinued
0.7385	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1283	Approved
0.7381	Intermediate Similarity	NPD8651	Approved
0.7377	Intermediate Similarity	NPD1548	Phase 1
0.7377	Intermediate Similarity	NPD1182	Approved
0.7368	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7095	Approved
0.736	Intermediate Similarity	NPD2233	Approved
0.736	Intermediate Similarity	NPD2230	Approved
0.736	Intermediate Similarity	NPD2232	Approved
0.735	Intermediate Similarity	NPD556	Approved
0.7344	Intermediate Similarity	NPD2861	Phase 2
0.7339	Intermediate Similarity	NPD3847	Discontinued
0.7338	Intermediate Similarity	NPD7526	Approved
0.7338	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD52	Approved
0.7328	Intermediate Similarity	NPD4140	Approved
0.7311	Intermediate Similarity	NPD9379	Approved
0.7311	Intermediate Similarity	NPD9377	Approved
0.7311	Intermediate Similarity	NPD5535	Approved
0.7302	Intermediate Similarity	NPD6582	Phase 2
0.7302	Intermediate Similarity	NPD6583	Phase 3
0.7302	Intermediate Similarity	NPD5327	Phase 3
0.7302	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD288	Approved
0.7293	Intermediate Similarity	NPD6896	Approved
0.7293	Intermediate Similarity	NPD6895	Approved
0.729	Intermediate Similarity	NPD9295	Approved
0.7287	Intermediate Similarity	NPD600	Approved
0.7287	Intermediate Similarity	NPD596	Approved
0.728	Intermediate Similarity	NPD1091	Approved
0.728	Intermediate Similarity	NPD1610	Phase 2
0.7266	Intermediate Similarity	NPD4739	Approved
0.7266	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD558	Phase 2
0.7258	Intermediate Similarity	NPD9381	Approved
0.7258	Intermediate Similarity	NPD9384	Approved
0.7257	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1423	Approved
0.7236	Intermediate Similarity	NPD1894	Discontinued
0.7234	Intermediate Similarity	NPD3686	Approved
0.7234	Intermediate Similarity	NPD3687	Approved
0.7231	Intermediate Similarity	NPD3166	Approved
0.7231	Intermediate Similarity	NPD3167	Approved
0.7231	Intermediate Similarity	NPD3164	Approved
0.7231	Intermediate Similarity	NPD3165	Approved
0.7222	Intermediate Similarity	NPD1840	Phase 2
0.7218	Intermediate Similarity	NPD6653	Approved
0.7218	Intermediate Similarity	NPD2653	Approved
0.7214	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3596	Phase 2
0.7209	Intermediate Similarity	NPD1712	Approved
0.7206	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2238	Phase 2
0.7194	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD846	Approved
0.7193	Intermediate Similarity	NPD940	Approved
0.7188	Intermediate Similarity	NPD1794	Approved
0.7188	Intermediate Similarity	NPD987	Approved
0.7177	Intermediate Similarity	NPD5585	Approved
0.7176	Intermediate Similarity	NPD6798	Discontinued
0.7167	Intermediate Similarity	NPD1138	Approved
0.7165	Intermediate Similarity	NPD9622	Approved
0.7164	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6111	Discontinued
0.7164	Intermediate Similarity	NPD4538	Approved
0.7164	Intermediate Similarity	NPD4536	Approved
0.7154	Intermediate Similarity	NPD4908	Phase 1
0.7153	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD776	Approved
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4123	Phase 3
0.7132	Intermediate Similarity	NPD3540	Phase 1
0.7121	Intermediate Similarity	NPD840	Approved
0.7121	Intermediate Similarity	NPD4062	Phase 3
0.7121	Intermediate Similarity	NPD839	Approved
0.7121	Intermediate Similarity	NPD6233	Phase 2
0.7105	Intermediate Similarity	NPD1242	Phase 1
0.7101	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3179	Approved
0.7099	Intermediate Similarity	NPD3180	Approved
0.7097	Intermediate Similarity	NPD6581	Approved
0.7097	Intermediate Similarity	NPD6580	Approved
0.7097	Intermediate Similarity	NPD3091	Approved
0.709	Intermediate Similarity	NPD2157	Approved
0.709	Intermediate Similarity	NPD6353	Approved
0.7087	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD1137	Approved
0.7083	Intermediate Similarity	NPD1139	Approved
0.708	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2808	Discontinued
0.7071	Intermediate Similarity	NPD1774	Approved
0.7063	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4005	Discontinued
0.7059	Intermediate Similarity	NPD3539	Phase 1
0.7054	Intermediate Similarity	NPD1809	Phase 2
0.705	Intermediate Similarity	NPD2677	Approved
0.705	Intermediate Similarity	NPD2219	Phase 1
0.705	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1039	Discontinued
0.7045	Intermediate Similarity	NPD6410	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