NPASS Compound

Structure

CID251571 OpenBabel06191716052D 23 24 0 0 0 0 0 0 0 0999 V2000 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 6 1 0 0 0 0 2 13 2 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 2 3 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.13
Volume:	327.837
LogP:	2.65
LogD:	3.02
LogS:	-3.139
# Rotatable Bonds:	7
TPSA:	78.79
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	1.965
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.919
MDCK Permeability:	1.3178945664549246e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.209

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	97.28772735595703%
Volume Distribution (VD):	0.547
Pgp-substrate:	1.6460455656051636%

ADMET: Metabolism

CYP1A2-inhibitor:	0.822
CYP1A2-substrate:	0.874
CYP2C19-inhibitor:	0.705
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.763
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.799
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.679
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	12.619
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.336
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.658
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.865
Skin Sensitization:	0.949
Carcinogencity:	0.415
Eye Corrosion:	0.003
Eye Irritation:	0.085
Respiratory Toxicity:	0.596

Download Data

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

Natural Product: NPC251571

Natural Product ID:	NPC251571
*Common Name:**	3-(3,4-Dihydroxyphenyl)-N-(4-Methoxyphenethyl)Acrylamide
IUPAC Name:	(E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]prop-2-enamide
Synonyms:
Standard InCHIKey:	JRKPLTBLTYEYJJ-WEVVVXLNSA-N
Standard InCHI:	InChI=1S/C18H19NO4/c1-23-15-6-2-13(3-7-15)10-11-19-18(22)9-5-14-4-8-16(20)17(21)12-14/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+
SMILES:	COc1ccc(cc1)CCN=C(/C=C/c1ccc(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334872
PubChem CID:	10403282
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids 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
NPO8884	Cuscuta reflexa	Species	Convolvulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[11824569]
NPO2350	Microcos paniculata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327794]
NPO8884	Cuscuta reflexa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8884	Cuscuta reflexa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2350	Microcos paniculata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2350	Microcos paniculata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8884	Cuscuta reflexa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2350	Microcos paniculata	Species	Malvaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[477098]
NPT411	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Homo sapiens	Inhibition	=	14.0	%	PMID[477098]
NPT409	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Homo sapiens	Inhibition	=	21.8	%	PMID[477098]

☑ 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 NPC251571 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	182
0.1-0.2	1540
0.2-0.3	8534
0.3-0.4	9921
0.4-0.5	5460
0.5-0.6	9764
0.6-0.7	5636
0.7-0.8	1496
0.8-0.85	118
0.85-0.9	25
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9836	High Similarity	NPC35961
0.9836	High Similarity	NPC52029
0.9836	High Similarity	NPC195749
0.9754	High Similarity	NPC155838
0.9677	High Similarity	NPC214869
0.9597	High Similarity	NPC114102
0.9512	High Similarity	NPC186898
0.9355	High Similarity	NPC153990
0.9302	High Similarity	NPC204848
0.9302	High Similarity	NPC312770
0.9302	High Similarity	NPC160607
0.9302	High Similarity	NPC14600
0.9302	High Similarity	NPC41473
0.9274	High Similarity	NPC301713
0.9231	High Similarity	NPC296898
0.9231	High Similarity	NPC299583
0.9167	High Similarity	NPC122009
0.9083	High Similarity	NPC283468
0.8934	High Similarity	NPC268572
0.8915	High Similarity	NPC130595
0.8915	High Similarity	NPC93882
0.8881	High Similarity	NPC222039
0.8881	High Similarity	NPC100478
0.8846	High Similarity	NPC313737
0.8846	High Similarity	NPC285078
0.8846	High Similarity	NPC6854
0.8837	High Similarity	NPC255550
0.8837	High Similarity	NPC308885
0.8824	High Similarity	NPC5462
0.878	High Similarity	NPC43275
0.8779	High Similarity	NPC218530
0.871	High Similarity	NPC263835
0.864	High Similarity	NPC83279
0.8633	High Similarity	NPC470935
0.8633	High Similarity	NPC471032
0.8633	High Similarity	NPC153644
0.8561	High Similarity	NPC115144
0.8561	High Similarity	NPC277857
0.8548	High Similarity	NPC470626
0.8525	High Similarity	NPC142599
0.8516	High Similarity	NPC62101
0.8516	High Similarity	NPC95733
0.8504	High Similarity	NPC471314
0.8504	High Similarity	NPC471315
0.8492	Intermediate Similarity	NPC284078
0.8473	Intermediate Similarity	NPC470706
0.8468	Intermediate Similarity	NPC293619
0.8456	Intermediate Similarity	NPC477837
0.8456	Intermediate Similarity	NPC477838
0.8455	Intermediate Similarity	NPC303370
0.8451	Intermediate Similarity	NPC127402
0.8438	Intermediate Similarity	NPC211218
0.8438	Intermediate Similarity	NPC140359
0.8438	Intermediate Similarity	NPC13020
0.843	Intermediate Similarity	NPC166837
0.8413	Intermediate Similarity	NPC117780
0.8413	Intermediate Similarity	NPC227217
0.8413	Intermediate Similarity	NPC165133
0.8413	Intermediate Similarity	NPC232316
0.8413	Intermediate Similarity	NPC56214
0.8413	Intermediate Similarity	NPC242885
0.8413	Intermediate Similarity	NPC95614
0.8385	Intermediate Similarity	NPC251466
0.8385	Intermediate Similarity	NPC156944
0.8346	Intermediate Similarity	NPC207613
0.8333	Intermediate Similarity	NPC24101
0.8333	Intermediate Similarity	NPC96224
0.8333	Intermediate Similarity	NPC310338
0.8333	Intermediate Similarity	NPC281298
0.8322	Intermediate Similarity	NPC52475
0.8321	Intermediate Similarity	NPC157740
0.8321	Intermediate Similarity	NPC41331
0.8321	Intermediate Similarity	NPC291449
0.8321	Intermediate Similarity	NPC99798
0.8309	Intermediate Similarity	NPC254610
0.8308	Intermediate Similarity	NPC29477
0.8308	Intermediate Similarity	NPC71105
0.8308	Intermediate Similarity	NPC152186
0.8308	Intermediate Similarity	NPC182147
0.8308	Intermediate Similarity	NPC170583
0.8308	Intermediate Similarity	NPC246133
0.8308	Intermediate Similarity	NPC207541
0.8281	Intermediate Similarity	NPC54872
0.8281	Intermediate Similarity	NPC184651
0.8281	Intermediate Similarity	NPC113865
0.8281	Intermediate Similarity	NPC262156
0.8281	Intermediate Similarity	NPC312675
0.8281	Intermediate Similarity	NPC324571
0.8281	Intermediate Similarity	NPC473853
0.8281	Intermediate Similarity	NPC470212
0.8281	Intermediate Similarity	NPC38996
0.8281	Intermediate Similarity	NPC160380
0.8281	Intermediate Similarity	NPC343720
0.8276	Intermediate Similarity	NPC107602
0.8268	Intermediate Similarity	NPC289330
0.8268	Intermediate Similarity	NPC17388
0.8268	Intermediate Similarity	NPC53596
0.8268	Intermediate Similarity	NPC160120
0.8268	Intermediate Similarity	NPC471308
0.8264	Intermediate Similarity	NPC18614
0.8264	Intermediate Similarity	NPC275027
0.8258	Intermediate Similarity	NPC246974
0.8258	Intermediate Similarity	NPC147247
0.8231	Intermediate Similarity	NPC300955
0.8217	Intermediate Similarity	NPC85488
0.8203	Intermediate Similarity	NPC60962
0.8203	Intermediate Similarity	NPC224814
0.8203	Intermediate Similarity	NPC189844
0.8203	Intermediate Similarity	NPC269843
0.8203	Intermediate Similarity	NPC109083
0.8203	Intermediate Similarity	NPC14007
0.8189	Intermediate Similarity	NPC256369
0.8182	Intermediate Similarity	NPC191302
0.8175	Intermediate Similarity	NPC86947
0.8175	Intermediate Similarity	NPC193528
0.816	Intermediate Similarity	NPC37302
0.8154	Intermediate Similarity	NPC136319
0.8154	Intermediate Similarity	NPC31344
0.8154	Intermediate Similarity	NPC317769
0.8154	Intermediate Similarity	NPC471693
0.8154	Intermediate Similarity	NPC280704
0.813	Intermediate Similarity	NPC156840
0.813	Intermediate Similarity	NPC173746
0.813	Intermediate Similarity	NPC8547
0.813	Intermediate Similarity	NPC257124
0.812	Intermediate Similarity	NPC469977
0.8115	Intermediate Similarity	NPC36108
0.8115	Intermediate Similarity	NPC246358
0.8115	Intermediate Similarity	NPC233731
0.8115	Intermediate Similarity	NPC7097
0.8099	Intermediate Similarity	NPC142297
0.8088	Intermediate Similarity	NPC473463
0.8077	Intermediate Similarity	NPC473411
0.8077	Intermediate Similarity	NPC71579
0.8077	Intermediate Similarity	NPC262253
0.8056	Intermediate Similarity	NPC182119
0.8047	Intermediate Similarity	NPC311595
0.8047	Intermediate Similarity	NPC226629
0.8047	Intermediate Similarity	NPC24474
0.8045	Intermediate Similarity	NPC172403
0.8033	Intermediate Similarity	NPC75440
0.8031	Intermediate Similarity	NPC164386
0.803	Intermediate Similarity	NPC298757
0.803	Intermediate Similarity	NPC148627
0.803	Intermediate Similarity	NPC193544
0.803	Intermediate Similarity	NPC221077
0.803	Intermediate Similarity	NPC116907
0.803	Intermediate Similarity	NPC117214
0.803	Intermediate Similarity	NPC9067
0.803	Intermediate Similarity	NPC194519
0.803	Intermediate Similarity	NPC57490
0.803	Intermediate Similarity	NPC251855
0.803	Intermediate Similarity	NPC17943
0.803	Intermediate Similarity	NPC228771
0.803	Intermediate Similarity	NPC233410
0.803	Intermediate Similarity	NPC475169
0.803	Intermediate Similarity	NPC53305
0.803	Intermediate Similarity	NPC266705
0.803	Intermediate Similarity	NPC203133
0.803	Intermediate Similarity	NPC472093
0.803	Intermediate Similarity	NPC29008
0.803	Intermediate Similarity	NPC257589
0.803	Intermediate Similarity	NPC208950
0.8029	Intermediate Similarity	NPC6913
0.8017	Intermediate Similarity	NPC231705
0.8015	Intermediate Similarity	NPC197757
0.8015	Intermediate Similarity	NPC229084
0.8015	Intermediate Similarity	NPC160900
0.8015	Intermediate Similarity	NPC228922
0.8015	Intermediate Similarity	NPC106659
0.8015	Intermediate Similarity	NPC18984
0.8	Intermediate Similarity	NPC12987
0.8	Intermediate Similarity	NPC290451
0.8	Intermediate Similarity	NPC478189
0.8	Intermediate Similarity	NPC127389
0.8	Intermediate Similarity	NPC474603
0.8	Intermediate Similarity	NPC326599
0.8	Intermediate Similarity	NPC329595
0.7987	Intermediate Similarity	NPC329837
0.7986	Intermediate Similarity	NPC135538
0.7986	Intermediate Similarity	NPC428
0.7986	Intermediate Similarity	NPC24233
0.7986	Intermediate Similarity	NPC246587
0.7986	Intermediate Similarity	NPC476571
0.7986	Intermediate Similarity	NPC231572
0.7986	Intermediate Similarity	NPC147390
0.7985	Intermediate Similarity	NPC271808
0.7984	Intermediate Similarity	NPC41801
0.7984	Intermediate Similarity	NPC247364
0.7984	Intermediate Similarity	NPC10932
0.7984	Intermediate Similarity	NPC61516
0.7984	Intermediate Similarity	NPC474565
0.7984	Intermediate Similarity	NPC252817
0.7984	Intermediate Similarity	NPC139617
0.7984	Intermediate Similarity	NPC78918
0.7984	Intermediate Similarity	NPC321133
0.7984	Intermediate Similarity	NPC232084
0.797	Intermediate Similarity	NPC17837
0.797	Intermediate Similarity	NPC28730
0.797	Intermediate Similarity	NPC304630

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 NPC251571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	760
0.2-0.3	1109
0.3-0.4	2080
0.4-0.5	2543
0.5-0.6	1567
0.6-0.7	781
0.7-0.8	164
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8915	High Similarity	NPD2674	Phase 3
0.8837	High Similarity	NPD3144	Approved
0.8837	High Similarity	NPD3145	Approved
0.8438	Intermediate Similarity	NPD1669	Approved
0.8217	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD6331	Phase 2
0.813	Intermediate Similarity	NPD228	Approved
0.8092	Intermediate Similarity	NPD2922	Phase 1
0.8071	Intermediate Similarity	NPD3060	Approved
0.8042	Intermediate Similarity	NPD4123	Phase 3
0.8015	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2161	Phase 2
0.7985	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD2667	Approved
0.7984	Intermediate Similarity	NPD2668	Approved
0.7895	Intermediate Similarity	NPD3053	Approved
0.7895	Intermediate Similarity	NPD3055	Approved
0.7883	Intermediate Similarity	NPD1558	Phase 1
0.7872	Intermediate Similarity	NPD7153	Discontinued
0.7868	Intermediate Similarity	NPD5718	Phase 2
0.7857	Intermediate Similarity	NPD5283	Phase 1
0.7836	Intermediate Similarity	NPD6584	Phase 3
0.7823	Intermediate Similarity	NPD3021	Approved
0.7823	Intermediate Similarity	NPD3022	Approved
0.782	Intermediate Similarity	NPD5310	Approved
0.782	Intermediate Similarity	NPD5311	Approved
0.7817	Intermediate Similarity	NPD4162	Approved
0.7803	Intermediate Similarity	NPD2232	Approved
0.7803	Intermediate Similarity	NPD2230	Approved
0.7803	Intermediate Similarity	NPD2233	Approved
0.7794	Intermediate Similarity	NPD3027	Phase 3
0.7778	Intermediate Similarity	NPD9377	Approved
0.7778	Intermediate Similarity	NPD9379	Approved
0.777	Intermediate Similarity	NPD4675	Approved
0.777	Intermediate Similarity	NPD4678	Approved
0.774	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD5111	Phase 2
0.7737	Intermediate Similarity	NPD5109	Approved
0.7737	Intermediate Similarity	NPD5110	Phase 2
0.7714	Intermediate Similarity	NPD6895	Approved
0.7714	Intermediate Similarity	NPD6896	Approved
0.7708	Intermediate Similarity	NPD5241	Discontinued
0.7703	Intermediate Similarity	NPD4005	Discontinued
0.7681	Intermediate Similarity	NPD839	Approved
0.7681	Intermediate Similarity	NPD840	Approved
0.7671	Intermediate Similarity	NPD4739	Approved
0.7667	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1024	Discontinued
0.766	Intermediate Similarity	NPD4108	Discontinued
0.7626	Intermediate Similarity	NPD3059	Approved
0.7626	Intermediate Similarity	NPD3062	Approved
0.7626	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD3061	Approved
0.7616	Intermediate Similarity	NPD2978	Approved
0.7616	Intermediate Similarity	NPD2977	Approved
0.7612	Intermediate Similarity	NPD6583	Phase 3
0.7612	Intermediate Similarity	NPD6582	Phase 2
0.7603	Intermediate Similarity	NPD4357	Discontinued
0.7569	Intermediate Similarity	NPD4236	Phase 3
0.7569	Intermediate Similarity	NPD4237	Approved
0.7569	Intermediate Similarity	NPD5177	Phase 3
0.7554	Intermediate Similarity	NPD7477	Discontinued
0.7552	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1375	Discontinued
0.7537	Intermediate Similarity	NPD2231	Phase 2
0.7537	Intermediate Similarity	NPD2235	Phase 2
0.7518	Intermediate Similarity	NPD2157	Approved
0.7518	Intermediate Similarity	NPD4993	Discontinued
0.7518	Intermediate Similarity	NPD1712	Approved
0.7518	Intermediate Similarity	NPD5314	Approved
0.75	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5773	Approved
0.75	Intermediate Similarity	NPD821	Approved
0.75	Intermediate Similarity	NPD7526	Approved
0.75	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD52	Approved
0.75	Intermediate Similarity	NPD5772	Approved
0.7482	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD5536	Phase 2
0.7468	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD709	Approved
0.7452	Intermediate Similarity	NPD4083	Discontinued
0.7444	Intermediate Similarity	NPD9381	Approved
0.7444	Intermediate Similarity	NPD9384	Approved
0.7442	Intermediate Similarity	NPD2228	Approved
0.7442	Intermediate Similarity	NPD2234	Approved
0.7442	Intermediate Similarity	NPD2229	Approved
0.7431	Intermediate Similarity	NPD3656	Approved
0.7429	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3054	Approved
0.7394	Intermediate Similarity	NPD3052	Approved
0.7379	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2238	Phase 2
0.7368	Intermediate Similarity	NPD4093	Discontinued
0.7355	Intermediate Similarity	NPD4055	Discovery
0.7353	Intermediate Similarity	NPD9622	Approved
0.7353	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3685	Discontinued
0.7347	Intermediate Similarity	NPD2219	Phase 1
0.7344	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2122	Discontinued
0.7319	Intermediate Similarity	NPD9619	Approved
0.7319	Intermediate Similarity	NPD7451	Discontinued
0.7319	Intermediate Similarity	NPD7905	Discontinued
0.7319	Intermediate Similarity	NPD9621	Approved
0.7319	Intermediate Similarity	NPD9620	Approved
0.7315	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7124	Phase 2
0.7273	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2653	Approved
0.7273	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3596	Phase 2
0.7266	Intermediate Similarity	NPD1792	Phase 2
0.7266	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3421	Phase 3
0.7259	Intermediate Similarity	NPD3847	Discontinued
0.7255	Intermediate Similarity	NPD6072	Discontinued
0.7254	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3620	Phase 2
0.7254	Intermediate Similarity	NPD1613	Approved
0.7254	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5604	Discontinued
0.7239	Intermediate Similarity	NPD1357	Approved
0.7237	Intermediate Similarity	NPD3455	Phase 2
0.7234	Intermediate Similarity	NPD601	Approved
0.7234	Intermediate Similarity	NPD598	Approved
0.7234	Intermediate Similarity	NPD1039	Discontinued
0.7234	Intermediate Similarity	NPD597	Approved
0.7234	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3692	Discontinued
0.7226	Intermediate Similarity	NPD2982	Phase 2
0.7226	Intermediate Similarity	NPD2983	Phase 2
0.7215	Intermediate Similarity	NPD2821	Approved
0.72	Intermediate Similarity	NPD3985	Discontinued
0.72	Intermediate Similarity	NPD3536	Discontinued
0.72	Intermediate Similarity	NPD4584	Approved
0.719	Intermediate Similarity	NPD2933	Approved
0.719	Intermediate Similarity	NPD2934	Approved
0.7188	Intermediate Similarity	NPD2684	Approved
0.7185	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1132	Approved
0.7183	Intermediate Similarity	NPD1136	Approved
0.7183	Intermediate Similarity	NPD259	Phase 1
0.7183	Intermediate Similarity	NPD1130	Approved
0.7183	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3687	Approved
0.7171	Intermediate Similarity	NPD3686	Approved
0.717	Intermediate Similarity	NPD4010	Discontinued
0.717	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1445	Approved
0.7165	Intermediate Similarity	NPD1444	Approved
0.7164	Intermediate Similarity	NPD6581	Approved
0.7164	Intermediate Similarity	NPD6580	Approved
0.7164	Intermediate Similarity	NPD2486	Discontinued
0.7161	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2981	Phase 2
0.7153	Intermediate Similarity	NPD4097	Suspended
0.7143	Intermediate Similarity	NPD3796	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7037	Approved
0.7143	Intermediate Similarity	NPD2808	Discontinued
0.7134	Intermediate Similarity	NPD7833	Phase 2
0.7134	Intermediate Similarity	NPD7831	Phase 2
0.7134	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4060	Phase 1
0.7131	Intermediate Similarity	NPD2859	Approved
0.7131	Intermediate Similarity	NPD2860	Approved
0.7124	Intermediate Similarity	NPD824	Approved
0.7114	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2595	Approved
0.7111	Intermediate Similarity	NPD2594	Approved
0.7105	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6031	Approved
0.7105	Intermediate Similarity	NPD7131	Phase 3
0.7105	Intermediate Similarity	NPD6030	Approved
0.7101	Intermediate Similarity	NPD4129	Approved
0.7101	Intermediate Similarity	NPD2428	Approved
0.7101	Intermediate Similarity	NPD2429	Approved
0.7099	Intermediate Similarity	NPD7843	Approved
0.7097	Intermediate Similarity	NPD3020	Approved
0.7095	Intermediate Similarity	NPD2459	Approved
0.7095	Intermediate Similarity	NPD2460	Phase 3
0.7095	Intermediate Similarity	NPD2458	Approved
0.7092	Intermediate Similarity	NPD2614	Approved
0.7092	Intermediate Similarity	NPD596	Approved
0.7092	Intermediate Similarity	NPD600	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data