NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.09
Volume:	214.871
LogP:	1.253
LogD:	4.011
LogS:	-2.103
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	1.505
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.684
MDCK Permeability:	2.052147829090245e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.223
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	73.66160583496094%
Volume Distribution (VD):	0.225
Pgp-substrate:	8.43809700012207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.459
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.812
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	9.502
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.19
Carcinogencity:	0.287
Eye Corrosion:	0.083
Eye Irritation:	0.718
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC205502

Natural Product ID:	NPC205502
*Common Name:**	Sid26659733
IUPAC Name:	3-(3,4-dimethoxyphenyl)propanoic acid
Synonyms:	3,4-Dimethoxy-Hydrocinnamic Acid; 3,4-Dimethoxyhydrocinnamic Acid
Standard InCHIKey:	LHHKQWQTBCTDQM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3,5,7H,4,6H2,1-2H3,(H,12,13)
SMILES:	COc1ccc(CCC(=O)O)cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458049
PubChem CID:	75019
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002551] Phenylpropanoic acids

*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
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387643]
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309326]
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	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	2
Others	3
Potency	3

Activity Type	# Activity
Cell Line	3
Individual Protein	2
Others	1
PROTEIN COMPLEX	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	2.3	%	PMID[525302]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[525303]
NPT466	Cell Line	U-937	Homo sapiens	CC50	>	2000000.0	nM	PMID[525304]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	2000000.0	nM	PMID[525304]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[525303]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[525303]
NPT2	Others	Unspecified		IC50	>	12000000.0	nM	PMID[525305]
NPT22587	SINGLE PROTEIN	Taste receptor type 2 member 39	Homo sapiens	Inhibition	=	35.0	%	PMID[525306]

☑ 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 NPC205502 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	249
0.1-0.2	1355
0.2-0.3	4104
0.3-0.4	10623
0.4-0.5	7785
0.5-0.6	4779
0.6-0.7	10421
0.7-0.8	3005
0.8-0.85	253
0.85-0.9	112
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9649	High Similarity	NPC177291
0.9649	High Similarity	NPC194416
0.9322	High Similarity	NPC280767
0.9217	High Similarity	NPC299406
0.9167	High Similarity	NPC281020
0.916	High Similarity	NPC173608
0.9009	High Similarity	NPC234639
0.8992	High Similarity	NPC163083
0.8992	High Similarity	NPC244876
0.8983	High Similarity	NPC201777
0.8947	High Similarity	NPC294941
0.8908	High Similarity	NPC114298
0.8862	High Similarity	NPC241354
0.886	High Similarity	NPC109241
0.886	High Similarity	NPC148969
0.886	High Similarity	NPC303522
0.8843	High Similarity	NPC53305
0.8843	High Similarity	NPC257589
0.8833	High Similarity	NPC257976
0.8833	High Similarity	NPC164778
0.8833	High Similarity	NPC4181
0.8833	High Similarity	NPC242372
0.8803	High Similarity	NPC272471
0.8803	High Similarity	NPC107588
0.8803	High Similarity	NPC70744
0.8803	High Similarity	NPC137537
0.8803	High Similarity	NPC164706
0.879	High Similarity	NPC285776
0.877	High Similarity	NPC303680
0.877	High Similarity	NPC92207
0.877	High Similarity	NPC84076
0.877	High Similarity	NPC90128
0.877	High Similarity	NPC127937
0.8761	High Similarity	NPC137685
0.876	High Similarity	NPC312404
0.876	High Similarity	NPC273686
0.8739	High Similarity	NPC1065
0.8739	High Similarity	NPC158949
0.873	High Similarity	NPC475468
0.873	High Similarity	NPC307006
0.873	High Similarity	NPC129889
0.8727	High Similarity	NPC292792
0.8707	High Similarity	NPC322358
0.8699	High Similarity	NPC293641
0.8699	High Similarity	NPC123722
0.8699	High Similarity	NPC276466
0.8699	High Similarity	NPC151167
0.8699	High Similarity	NPC223807
0.8699	High Similarity	NPC12022
0.8699	High Similarity	NPC20404
0.8699	High Similarity	NPC123228
0.8699	High Similarity	NPC20287
0.8699	High Similarity	NPC5018
0.8684	High Similarity	NPC173746
0.8684	High Similarity	NPC257124
0.8684	High Similarity	NPC245552
0.8684	High Similarity	NPC156840
0.8684	High Similarity	NPC8547
0.8661	High Similarity	NPC5310
0.8661	High Similarity	NPC471110
0.8661	High Similarity	NPC176814
0.8661	High Similarity	NPC300776
0.8661	High Similarity	NPC4982
0.8661	High Similarity	NPC68779
0.8655	High Similarity	NPC202474
0.8655	High Similarity	NPC2058
0.8651	High Similarity	NPC111888
0.8644	High Similarity	NPC124916
0.8644	High Similarity	NPC159916
0.8629	High Similarity	NPC226661
0.8629	High Similarity	NPC278308
0.8618	High Similarity	NPC179777
0.8618	High Similarity	NPC154275
0.8607	High Similarity	NPC60517
0.8607	High Similarity	NPC20443
0.8607	High Similarity	NPC146886
0.8596	High Similarity	NPC222084
0.8594	High Similarity	NPC470990
0.8594	High Similarity	NPC113295
0.8583	High Similarity	NPC225245
0.8583	High Similarity	NPC283823
0.8583	High Similarity	NPC159418
0.8583	High Similarity	NPC204466
0.8571	High Similarity	NPC37858
0.856	High Similarity	NPC304622
0.8548	High Similarity	NPC32163
0.8548	High Similarity	NPC16651
0.8545	High Similarity	NPC12714
0.8545	High Similarity	NPC310905
0.8527	High Similarity	NPC90431
0.8512	High Similarity	NPC70752
0.8509	High Similarity	NPC246358
0.8509	High Similarity	NPC233731
0.8509	High Similarity	NPC36108
0.8509	High Similarity	NPC7097
0.8496	Intermediate Similarity	NPC227894
0.8492	Intermediate Similarity	NPC477694
0.8492	Intermediate Similarity	NPC195292
0.8492	Intermediate Similarity	NPC275724
0.8492	Intermediate Similarity	NPC311419
0.8492	Intermediate Similarity	NPC477705
0.8492	Intermediate Similarity	NPC65935
0.8492	Intermediate Similarity	NPC123196
0.8492	Intermediate Similarity	NPC142985
0.8492	Intermediate Similarity	NPC244246
0.8492	Intermediate Similarity	NPC215941
0.8492	Intermediate Similarity	NPC137427
0.8492	Intermediate Similarity	NPC172673
0.8492	Intermediate Similarity	NPC319282
0.8468	Intermediate Similarity	NPC213552
0.8468	Intermediate Similarity	NPC120225
0.8468	Intermediate Similarity	NPC298224
0.843	Intermediate Similarity	NPC471877
0.843	Intermediate Similarity	NPC267064
0.8425	Intermediate Similarity	NPC469480
0.8425	Intermediate Similarity	NPC477706
0.8417	Intermediate Similarity	NPC57501
0.8413	Intermediate Similarity	NPC153547
0.8403	Intermediate Similarity	NPC293619
0.8403	Intermediate Similarity	NPC212643
0.8403	Intermediate Similarity	NPC199209
0.8403	Intermediate Similarity	NPC240664
0.8397	Intermediate Similarity	NPC284409
0.8393	Intermediate Similarity	NPC38209
0.839	Intermediate Similarity	NPC51345
0.8387	Intermediate Similarity	NPC3221
0.8387	Intermediate Similarity	NPC289459
0.8374	Intermediate Similarity	NPC474691
0.8372	Intermediate Similarity	NPC155098
0.8362	Intermediate Similarity	NPC139617
0.8362	Intermediate Similarity	NPC195873
0.8362	Intermediate Similarity	NPC78918
0.8361	Intermediate Similarity	NPC310373
0.8359	Intermediate Similarity	NPC239302
0.8359	Intermediate Similarity	NPC50763
0.8348	Intermediate Similarity	NPC259554
0.8346	Intermediate Similarity	NPC66905
0.8333	Intermediate Similarity	NPC147379
0.8333	Intermediate Similarity	NPC277460
0.8333	Intermediate Similarity	NPC255675
0.8333	Intermediate Similarity	NPC289690
0.8333	Intermediate Similarity	NPC66518
0.8333	Intermediate Similarity	NPC288452
0.8333	Intermediate Similarity	NPC474040
0.8333	Intermediate Similarity	NPC470626
0.8333	Intermediate Similarity	NPC474214
0.8321	Intermediate Similarity	NPC231719
0.8321	Intermediate Similarity	NPC52968
0.832	Intermediate Similarity	NPC276014
0.8319	Intermediate Similarity	NPC221049
0.8319	Intermediate Similarity	NPC268317
0.8306	Intermediate Similarity	NPC111088
0.8306	Intermediate Similarity	NPC246704
0.8295	Intermediate Similarity	NPC327410
0.8295	Intermediate Similarity	NPC205915
0.8293	Intermediate Similarity	NPC286573
0.8279	Intermediate Similarity	NPC295317
0.8276	Intermediate Similarity	NPC179309
0.8276	Intermediate Similarity	NPC31279
0.8271	Intermediate Similarity	NPC166137
0.8271	Intermediate Similarity	NPC29599
0.8271	Intermediate Similarity	NPC100675
0.8271	Intermediate Similarity	NPC282291
0.8268	Intermediate Similarity	NPC83062
0.8264	Intermediate Similarity	NPC135961
0.8264	Intermediate Similarity	NPC24474
0.8264	Intermediate Similarity	NPC69670
0.8264	Intermediate Similarity	NPC181969
0.8264	Intermediate Similarity	NPC311595
0.8264	Intermediate Similarity	NPC474320
0.8264	Intermediate Similarity	NPC320987
0.8254	Intermediate Similarity	NPC286683
0.8254	Intermediate Similarity	NPC203719
0.8254	Intermediate Similarity	NPC117237
0.825	Intermediate Similarity	NPC39793
0.825	Intermediate Similarity	NPC164386
0.825	Intermediate Similarity	NPC185738
0.825	Intermediate Similarity	NPC280001
0.824	Intermediate Similarity	NPC300326
0.824	Intermediate Similarity	NPC58279
0.8235	Intermediate Similarity	NPC4665
0.8231	Intermediate Similarity	NPC45404
0.8231	Intermediate Similarity	NPC37065
0.8226	Intermediate Similarity	NPC279379
0.8226	Intermediate Similarity	NPC160900
0.8226	Intermediate Similarity	NPC470887
0.8226	Intermediate Similarity	NPC18984
0.8226	Intermediate Similarity	NPC229084
0.8226	Intermediate Similarity	NPC21238
0.8226	Intermediate Similarity	NPC106659
0.822	Intermediate Similarity	NPC165106
0.8209	Intermediate Similarity	NPC253722
0.8209	Intermediate Similarity	NPC52664
0.8209	Intermediate Similarity	NPC31751
0.8209	Intermediate Similarity	NPC253481
0.8205	Intermediate Similarity	NPC55300
0.8205	Intermediate Similarity	NPC226250
0.8203	Intermediate Similarity	NPC299010
0.8197	Intermediate Similarity	NPC232316
0.8197	Intermediate Similarity	NPC227217

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 NPC205502 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	908
0.2-0.3	1583
0.3-0.4	2594
0.4-0.5	1831
0.5-0.6	1144
0.6-0.7	699
0.7-0.8	149
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD228	Approved
0.8306	Intermediate Similarity	NPD1283	Approved
0.8254	Intermediate Similarity	NPD9494	Approved
0.825	Intermediate Similarity	NPD5536	Phase 2
0.8226	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD5283	Phase 1
0.8209	Intermediate Similarity	NPD4110	Phase 3
0.8209	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD447	Suspended
0.8065	Intermediate Similarity	NPD1281	Approved
0.8033	Intermediate Similarity	NPD1894	Discontinued
0.8029	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD1358	Approved
0.8	Intermediate Similarity	NPD1608	Approved
0.7984	Intermediate Similarity	NPD3847	Discontinued
0.7967	Intermediate Similarity	NPD1357	Approved
0.7923	Intermediate Similarity	NPD6798	Discontinued
0.792	Intermediate Similarity	NPD1535	Discovery
0.7903	Intermediate Similarity	NPD1778	Approved
0.7879	Intermediate Similarity	NPD6355	Discontinued
0.7863	Intermediate Similarity	NPD4062	Phase 3
0.7863	Intermediate Similarity	NPD6233	Phase 2
0.7857	Intermediate Similarity	NPD1481	Phase 2
0.7846	Intermediate Similarity	NPD7095	Approved
0.7823	Intermediate Similarity	NPD1651	Approved
0.7769	Intermediate Similarity	NPD1241	Discontinued
0.776	Intermediate Similarity	NPD17	Approved
0.776	Intermediate Similarity	NPD4626	Approved
0.7734	Intermediate Similarity	NPD196	Phase 1
0.7652	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.7647	Intermediate Similarity	NPD2684	Approved
0.7638	Intermediate Similarity	NPD3705	Approved
0.7634	Intermediate Similarity	NPD2614	Approved
0.7627	Intermediate Similarity	NPD3134	Approved
0.7615	Intermediate Similarity	NPD257	Approved
0.7615	Intermediate Similarity	NPD258	Approved
0.7612	Intermediate Similarity	NPD230	Phase 1
0.76	Intermediate Similarity	NPD9545	Approved
0.7594	Intermediate Similarity	NPD259	Phase 1
0.7589	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3146	Approved
0.7578	Intermediate Similarity	NPD9717	Approved
0.7576	Intermediate Similarity	NPD3027	Phase 3
0.7559	Intermediate Similarity	NPD3496	Discontinued
0.7557	Intermediate Similarity	NPD454	Approved
0.7556	Intermediate Similarity	NPD2653	Approved
0.7556	Intermediate Similarity	NPD6653	Approved
0.7541	Intermediate Similarity	NPD5535	Approved
0.7541	Intermediate Similarity	NPD7843	Approved
0.754	Intermediate Similarity	NPD5691	Approved
0.754	Intermediate Similarity	NPD5585	Approved
0.7538	Intermediate Similarity	NPD987	Approved
0.7537	Intermediate Similarity	NPD826	Approved
0.7537	Intermediate Similarity	NPD2979	Phase 3
0.7537	Intermediate Similarity	NPD825	Approved
0.7537	Intermediate Similarity	NPD4060	Phase 1
0.7518	Intermediate Similarity	NPD2438	Suspended
0.75	Intermediate Similarity	NPD7157	Approved
0.7483	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD555	Phase 2
0.7481	Intermediate Similarity	NPD5647	Approved
0.7481	Intermediate Similarity	NPD1933	Approved
0.7466	Intermediate Similarity	NPD37	Approved
0.7463	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7028	Phase 2
0.744	Intermediate Similarity	NPD9493	Approved
0.7429	Intermediate Similarity	NPD4628	Phase 3
0.7424	Intermediate Similarity	NPD9569	Approved
0.7417	Intermediate Similarity	NPD290	Approved
0.7415	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4534	Discontinued
0.7405	Intermediate Similarity	NPD2797	Approved
0.7391	Intermediate Similarity	NPD2239	Approved
0.7391	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2240	Approved
0.7388	Intermediate Similarity	NPD411	Approved
0.7385	Intermediate Similarity	NPD2983	Phase 2
0.7385	Intermediate Similarity	NPD2982	Phase 2
0.7368	Intermediate Similarity	NPD9296	Approved
0.7365	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD2674	Phase 3
0.7333	Intermediate Similarity	NPD8032	Phase 2
0.7319	Intermediate Similarity	NPD2799	Discontinued
0.7315	Intermediate Similarity	NPD4966	Approved
0.7315	Intermediate Similarity	NPD4967	Phase 2
0.7315	Intermediate Similarity	NPD4965	Approved
0.731	Intermediate Similarity	NPD3687	Approved
0.731	Intermediate Similarity	NPD3686	Approved
0.7308	Intermediate Similarity	NPD2981	Phase 2
0.7305	Intermediate Similarity	NPD8166	Discontinued
0.7295	Intermediate Similarity	NPD3021	Approved
0.7295	Intermediate Similarity	NPD3022	Approved
0.7293	Intermediate Similarity	NPD3018	Phase 2
0.7288	Intermediate Similarity	NPD291	Approved
0.7286	Intermediate Similarity	NPD5958	Discontinued
0.7279	Intermediate Similarity	NPD6873	Phase 2
0.7279	Intermediate Similarity	NPD6386	Approved
0.7279	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD1203	Approved
0.7266	Intermediate Similarity	NPD2531	Phase 2
0.7266	Intermediate Similarity	NPD9268	Approved
0.7266	Intermediate Similarity	NPD4477	Approved
0.7266	Intermediate Similarity	NPD4476	Approved
0.7266	Intermediate Similarity	NPD6032	Approved
0.7259	Intermediate Similarity	NPD3268	Approved
0.7258	Intermediate Similarity	NPD821	Approved
0.7252	Intermediate Similarity	NPD4359	Approved
0.7246	Intermediate Similarity	NPD7097	Phase 1
0.7239	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD8127	Discontinued
0.7237	Intermediate Similarity	NPD7199	Phase 2
0.7231	Intermediate Similarity	NPD422	Phase 1
0.723	Intermediate Similarity	NPD1934	Approved
0.7226	Intermediate Similarity	NPD275	Approved
0.7226	Intermediate Similarity	NPD274	Approved
0.7222	Intermediate Similarity	NPD256	Approved
0.7222	Intermediate Similarity	NPD255	Approved
0.7219	Intermediate Similarity	NPD6234	Discontinued
0.7197	Intermediate Similarity	NPD1876	Approved
0.719	Intermediate Similarity	NPD6232	Discontinued
0.7185	Intermediate Similarity	NPD9537	Phase 1
0.7185	Intermediate Similarity	NPD9536	Phase 1
0.7181	Intermediate Similarity	NPD2801	Approved
0.7176	Intermediate Similarity	NPD3972	Approved
0.7176	Intermediate Similarity	NPD9269	Phase 2
0.7164	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4140	Approved
0.7153	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1558	Phase 1
0.7153	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1613	Approved
0.7153	Intermediate Similarity	NPD1511	Approved
0.7153	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD3455	Phase 2
0.7143	Intermediate Similarity	NPD6362	Approved
0.7143	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD2354	Approved
0.7133	Intermediate Similarity	NPD6190	Approved
0.7132	Intermediate Similarity	NPD5110	Phase 2
0.7132	Intermediate Similarity	NPD5111	Phase 2
0.7132	Intermediate Similarity	NPD3145	Approved
0.7132	Intermediate Similarity	NPD5109	Approved
0.7132	Intermediate Similarity	NPD3144	Approved
0.7132	Intermediate Similarity	NPD2313	Discontinued
0.7131	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2821	Approved
0.7123	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1536	Approved
0.7121	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6832	Phase 2
0.7111	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD9697	Approved
0.7103	Intermediate Similarity	NPD4739	Approved
0.7101	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1611	Approved
0.7092	Intermediate Similarity	NPD1375	Discontinued
0.7092	Intermediate Similarity	NPD2346	Discontinued
0.709	Intermediate Similarity	NPD1019	Discontinued
0.709	Intermediate Similarity	NPD2798	Approved
0.7087	Intermediate Similarity	NPD6671	Approved
0.7087	Intermediate Similarity	NPD709	Approved
0.7086	Intermediate Similarity	NPD3882	Suspended
0.7086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4308	Phase 3
0.7068	Intermediate Similarity	NPD2922	Phase 1
0.7068	Intermediate Similarity	NPD3225	Approved
0.7067	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD5163	Phase 2
0.7055	Intermediate Similarity	NPD6273	Approved
0.7055	Intermediate Similarity	NPD1512	Approved
0.7051	Intermediate Similarity	NPD7473	Discontinued
0.7049	Intermediate Similarity	NPD968	Approved
0.7042	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4357	Discontinued
0.7034	Intermediate Similarity	NPD9495	Approved
0.7034	Intermediate Similarity	NPD6799	Approved
0.7031	Intermediate Similarity	NPD9568	Approved
0.7029	Intermediate Similarity	NPD1240	Approved
0.7027	Intermediate Similarity	NPD824	Approved
0.7027	Intermediate Similarity	NPD7458	Discontinued
0.7021	Intermediate Similarity	NPD1537	Approved
0.7021	Intermediate Similarity	NPD1538	Phase 1
0.7021	Intermediate Similarity	NPD9570	Approved
0.7021	Intermediate Similarity	NPD1519	Approved
0.7021	Intermediate Similarity	NPD2161	Phase 2
0.7016	Intermediate Similarity	NPD5451	Approved
0.7007	Intermediate Similarity	NPD3764	Approved
0.7007	Intermediate Similarity	NPD1296	Phase 2
0.7007	Intermediate Similarity	NPD5718	Phase 2
0.7	Intermediate Similarity	NPD1521	Approved
0.7	Intermediate Similarity	NPD1520	Approved
0.6993	Remote Similarity	NPD2976	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