NPASS Compound

Structure

NPC299583 OpenBabel07101719512D 25 26 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 3.4641 -0.0000 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 -1.0000 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 6.9282 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 9 2 0 0 0 0 3 13 1 0 0 0 0 4 10 2 0 0 0 0 4 13 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 12 1 1 0 0 0 18 25 1 0 0 0 0 19 20 2 3 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	343.14
Volume:	353.923
LogP:	2.175
LogD:	2.615
LogS:	-2.84
# Rotatable Bonds:	8
TPSA:	88.02
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	2.735
Fsp3:	0.211
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:	-4.749
MDCK Permeability:	1.2375226106087212e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.67
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	96.01249694824219%
Volume Distribution (VD):	0.524
Pgp-substrate:	2.908926248550415%

ADMET: Metabolism

CYP1A2-inhibitor:	0.259
CYP1A2-substrate:	0.325
CYP2C19-inhibitor:	0.19
CYP2C19-substrate:	0.297
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.513
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	12.499
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.416
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.527
Skin Sensitization:	0.94
Carcinogencity:	0.592
Eye Corrosion:	0.005
Eye Irritation:	0.142
Respiratory Toxicity:	0.785

Download Data

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

Natural Product: NPC299583

Natural Product ID:	NPC299583
*Common Name:**	3-(4-Hydroxy-3-Methoxyphenyl)-N-[2-(4-Hydroxyphenyl)-2-Methoxyethyl]Acrylamide
IUPAC Name:	(E)-3-(4-hydroxy-3-methoxyphenyl)-N-[(2S)-2-(4-hydroxyphenyl)-2-methoxyethyl]prop-2-enamide
Synonyms:
Standard InCHIKey:	RPYOBVFUJCZQDA-YDMXYTAQSA-N
Standard InCHI:	InChI=1S/C19H21NO5/c1-24-17-11-13(3-9-16(17)22)4-10-19(23)20-12-18(25-2)14-5-7-15(21)8-6-14/h3-11,18,21-22H,12H2,1-2H3,(H,20,23)/b10-4+/t18-/m1/s1
SMILES:	CO[C@@H](c1ccc(cc1)O)CN=C(/C=C/c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477695
PubChem CID:	643362
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
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10896056]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374970]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17338565]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21273070]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22066578]
NPO26913	Isodon excisus	Species	Lamiaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	10.2	ug.mL-1	PMID[462909]

☑ 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 NPC299583 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	209
0.1-0.2	1307
0.2-0.3	6234
0.3-0.4	12246
0.4-0.5	4884
0.5-0.6	8950
0.6-0.7	6674
0.7-0.8	1972
0.8-0.85	181
0.85-0.9	21
0.9-0.95	13
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC160607
0.9771	High Similarity	NPC312770
0.9771	High Similarity	NPC14600
0.9771	High Similarity	NPC204848
0.9771	High Similarity	NPC41473
0.9389	High Similarity	NPC214869
0.9385	High Similarity	NPC52029
0.9385	High Similarity	NPC35961
0.9385	High Similarity	NPC195749
0.9313	High Similarity	NPC114102
0.9308	High Similarity	NPC155838
0.9281	High Similarity	NPC115144
0.9281	High Similarity	NPC277857
0.9259	High Similarity	NPC296898
0.9231	High Similarity	NPC251571
0.9084	High Similarity	NPC186898
0.9084	High Similarity	NPC153990
0.9078	High Similarity	NPC471032
0.9078	High Similarity	NPC470935
0.9008	High Similarity	NPC301713
0.8923	High Similarity	NPC211218
0.8865	High Similarity	NPC5462
0.8855	High Similarity	NPC95733
0.8855	High Similarity	NPC62101
0.875	High Similarity	NPC182119
0.8676	High Similarity	NPC130595
0.8676	High Similarity	NPC93882
0.8647	High Similarity	NPC29477
0.8636	High Similarity	NPC471693
0.863	High Similarity	NPC127402
0.8613	High Similarity	NPC285078
0.8613	High Similarity	NPC313737
0.8613	High Similarity	NPC6854
0.8551	High Similarity	NPC218530
0.8521	High Similarity	NPC100478
0.8521	High Similarity	NPC222039
0.8511	High Similarity	NPC477837
0.8511	High Similarity	NPC477838
0.8507	High Similarity	NPC148627
0.8507	High Similarity	NPC194519
0.85	High Similarity	NPC254610
0.8467	Intermediate Similarity	NPC308885
0.8467	Intermediate Similarity	NPC255550
0.8467	Intermediate Similarity	NPC329595
0.8467	Intermediate Similarity	NPC326599
0.8462	Intermediate Similarity	NPC178466
0.8462	Intermediate Similarity	NPC122009
0.8462	Intermediate Similarity	NPC63628
0.8456	Intermediate Similarity	NPC107602
0.8446	Intermediate Similarity	NPC275027
0.8444	Intermediate Similarity	NPC191037
0.8444	Intermediate Similarity	NPC178284
0.8444	Intermediate Similarity	NPC58607
0.8409	Intermediate Similarity	NPC207613
0.8397	Intermediate Similarity	NPC268572
0.8385	Intermediate Similarity	NPC283468
0.8382	Intermediate Similarity	NPC147821
0.8382	Intermediate Similarity	NPC183181
0.8382	Intermediate Similarity	NPC118787
0.8382	Intermediate Similarity	NPC118533
0.8382	Intermediate Similarity	NPC292056
0.8382	Intermediate Similarity	NPC319625
0.8382	Intermediate Similarity	NPC111247
0.8382	Intermediate Similarity	NPC163332
0.8382	Intermediate Similarity	NPC41706
0.8382	Intermediate Similarity	NPC165045
0.8346	Intermediate Similarity	NPC184651
0.8346	Intermediate Similarity	NPC343720
0.8346	Intermediate Similarity	NPC113865
0.8346	Intermediate Similarity	NPC473853
0.8346	Intermediate Similarity	NPC262156
0.8346	Intermediate Similarity	NPC312675
0.8346	Intermediate Similarity	NPC470212
0.8346	Intermediate Similarity	NPC324571
0.8346	Intermediate Similarity	NPC54872
0.8321	Intermediate Similarity	NPC474178
0.8321	Intermediate Similarity	NPC252307
0.8321	Intermediate Similarity	NPC45774
0.8321	Intermediate Similarity	NPC245826
0.8321	Intermediate Similarity	NPC184733
0.8321	Intermediate Similarity	NPC98631
0.8321	Intermediate Similarity	NPC11258
0.8321	Intermediate Similarity	NPC128208
0.8321	Intermediate Similarity	NPC470626
0.8321	Intermediate Similarity	NPC21867
0.8321	Intermediate Similarity	NPC186843
0.8321	Intermediate Similarity	NPC282703
0.8321	Intermediate Similarity	NPC255675
0.8321	Intermediate Similarity	NPC129570
0.8321	Intermediate Similarity	NPC206615
0.8321	Intermediate Similarity	NPC470213
0.8301	Intermediate Similarity	NPC179250
0.8301	Intermediate Similarity	NPC50380
0.8299	Intermediate Similarity	NPC153644
0.8296	Intermediate Similarity	NPC94276
0.8296	Intermediate Similarity	NPC48990
0.8296	Intermediate Similarity	NPC109822
0.8296	Intermediate Similarity	NPC114901
0.8296	Intermediate Similarity	NPC293701
0.8284	Intermediate Similarity	NPC71090
0.8271	Intermediate Similarity	NPC284078
0.8261	Intermediate Similarity	NPC5851
0.8261	Intermediate Similarity	NPC86030
0.8261	Intermediate Similarity	NPC476968
0.8261	Intermediate Similarity	NPC170844
0.8258	Intermediate Similarity	NPC181969
0.8258	Intermediate Similarity	NPC43275
0.8258	Intermediate Similarity	NPC320987
0.8258	Intermediate Similarity	NPC90984
0.8248	Intermediate Similarity	NPC106511
0.8248	Intermediate Similarity	NPC5428
0.8244	Intermediate Similarity	NPC293619
0.8235	Intermediate Similarity	NPC193544
0.8235	Intermediate Similarity	NPC17943
0.8235	Intermediate Similarity	NPC298757
0.8235	Intermediate Similarity	NPC203133
0.8235	Intermediate Similarity	NPC472093
0.8235	Intermediate Similarity	NPC475169
0.8235	Intermediate Similarity	NPC116907
0.8235	Intermediate Similarity	NPC208950
0.8235	Intermediate Similarity	NPC233410
0.8235	Intermediate Similarity	NPC251855
0.8235	Intermediate Similarity	NPC117214
0.8235	Intermediate Similarity	NPC221077
0.8235	Intermediate Similarity	NPC57490
0.8222	Intermediate Similarity	NPC13020
0.8222	Intermediate Similarity	NPC140359
0.8209	Intermediate Similarity	NPC470804
0.8201	Intermediate Similarity	NPC64201
0.8201	Intermediate Similarity	NPC143483
0.8201	Intermediate Similarity	NPC472338
0.8201	Intermediate Similarity	NPC42300
0.8201	Intermediate Similarity	NPC242807
0.8201	Intermediate Similarity	NPC153739
0.8201	Intermediate Similarity	NPC257582
0.8201	Intermediate Similarity	NPC174495
0.8201	Intermediate Similarity	NPC77040
0.8201	Intermediate Similarity	NPC145305
0.8201	Intermediate Similarity	NPC92164
0.8201	Intermediate Similarity	NPC187998
0.8201	Intermediate Similarity	NPC241522
0.8195	Intermediate Similarity	NPC227217
0.8195	Intermediate Similarity	NPC56214
0.8195	Intermediate Similarity	NPC263835
0.8195	Intermediate Similarity	NPC242885
0.8195	Intermediate Similarity	NPC232316
0.8195	Intermediate Similarity	NPC177475
0.8195	Intermediate Similarity	NPC117780
0.8195	Intermediate Similarity	NPC95614
0.8195	Intermediate Similarity	NPC165133
0.8195	Intermediate Similarity	NPC148615
0.8195	Intermediate Similarity	NPC35071
0.8188	Intermediate Similarity	NPC72529
0.8175	Intermediate Similarity	NPC28730
0.8175	Intermediate Similarity	NPC78974
0.8175	Intermediate Similarity	NPC223136
0.8175	Intermediate Similarity	NPC103823
0.8175	Intermediate Similarity	NPC18924
0.8175	Intermediate Similarity	NPC214406
0.8175	Intermediate Similarity	NPC44748
0.817	Intermediate Similarity	NPC329837
0.8168	Intermediate Similarity	NPC221049
0.8148	Intermediate Similarity	NPC262253
0.8148	Intermediate Similarity	NPC71579
0.8148	Intermediate Similarity	NPC85488
0.8148	Intermediate Similarity	NPC473411
0.8143	Intermediate Similarity	NPC161557
0.8143	Intermediate Similarity	NPC158079
0.8143	Intermediate Similarity	NPC228346
0.8143	Intermediate Similarity	NPC27843
0.8143	Intermediate Similarity	NPC7171
0.8143	Intermediate Similarity	NPC470096
0.8143	Intermediate Similarity	NPC115207
0.8143	Intermediate Similarity	NPC474017
0.8143	Intermediate Similarity	NPC472597
0.8143	Intermediate Similarity	NPC470095
0.8143	Intermediate Similarity	NPC40432
0.8143	Intermediate Similarity	NPC277804
0.8134	Intermediate Similarity	NPC83279
0.8133	Intermediate Similarity	NPC52475
0.8129	Intermediate Similarity	NPC475875
0.8129	Intermediate Similarity	NPC212015
0.8129	Intermediate Similarity	NPC470706
0.812	Intermediate Similarity	NPC310338
0.812	Intermediate Similarity	NPC281298
0.812	Intermediate Similarity	NPC135961
0.812	Intermediate Similarity	NPC311595
0.812	Intermediate Similarity	NPC24474
0.8116	Intermediate Similarity	NPC246620
0.8116	Intermediate Similarity	NPC236791
0.8116	Intermediate Similarity	NPC21563
0.8116	Intermediate Similarity	NPC157740
0.8116	Intermediate Similarity	NPC210355
0.8116	Intermediate Similarity	NPC127587
0.8116	Intermediate Similarity	NPC82679
0.8116	Intermediate Similarity	NPC324112
0.8116	Intermediate Similarity	NPC169474
0.8116	Intermediate Similarity	NPC282000
0.8116	Intermediate Similarity	NPC74817
0.8116	Intermediate Similarity	NPC99798

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 NPC299583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	683
0.2-0.3	1186
0.3-0.4	2292
0.4-0.5	2373
0.5-0.6	1506
0.6-0.7	772
0.7-0.8	173
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8676	High Similarity	NPD2674	Phase 3
0.8611	High Similarity	NPD4123	Phase 3
0.8521	High Similarity	NPD3060	Approved
0.8467	Intermediate Similarity	NPD3145	Approved
0.8467	Intermediate Similarity	NPD3144	Approved
0.8322	Intermediate Similarity	NPD4678	Approved
0.8322	Intermediate Similarity	NPD4675	Approved
0.8299	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD4237	Approved
0.8264	Intermediate Similarity	NPD4236	Phase 3
0.8261	Intermediate Similarity	NPD3027	Phase 3
0.8207	Intermediate Similarity	NPD6331	Phase 2
0.8133	Intermediate Similarity	NPD4005	Discontinued
0.8125	Intermediate Similarity	NPD1375	Discontinued
0.8117	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1558	Phase 1
0.8082	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD7153	Discontinued
0.8056	Intermediate Similarity	NPD2161	Phase 2
0.8039	Intermediate Similarity	NPD2977	Approved
0.8039	Intermediate Similarity	NPD2978	Approved
0.8039	Intermediate Similarity	NPD5773	Approved
0.8039	Intermediate Similarity	NPD5772	Approved
0.8014	Intermediate Similarity	NPD4162	Approved
0.8	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1669	Approved
0.7929	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD228	Approved
0.7905	Intermediate Similarity	NPD5241	Discontinued
0.7899	Intermediate Similarity	NPD2922	Phase 1
0.7832	Intermediate Similarity	NPD3062	Approved
0.7832	Intermediate Similarity	NPD3061	Approved
0.7832	Intermediate Similarity	NPD3059	Approved
0.7826	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6584	Phase 3
0.7785	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD4739	Approved
0.7742	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3054	Approved
0.7724	Intermediate Similarity	NPD5314	Approved
0.7724	Intermediate Similarity	NPD3052	Approved
0.7712	Intermediate Similarity	NPD3687	Approved
0.7712	Intermediate Similarity	NPD3686	Approved
0.7698	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD52	Approved
0.7697	Intermediate Similarity	NPD7526	Approved
0.7692	Intermediate Similarity	NPD5718	Phase 2
0.7692	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4357	Discontinued
0.7669	Intermediate Similarity	NPD5283	Phase 1
0.7664	Intermediate Similarity	NPD9384	Approved
0.7664	Intermediate Similarity	NPD9381	Approved
0.7651	Intermediate Similarity	NPD5177	Phase 3
0.7647	Intermediate Similarity	NPD2122	Discontinued
0.7639	Intermediate Similarity	NPD839	Approved
0.7639	Intermediate Similarity	NPD840	Approved
0.7626	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1613	Approved
0.7586	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD9622	Approved
0.7571	Intermediate Similarity	NPD6582	Phase 2
0.7571	Intermediate Similarity	NPD6583	Phase 3
0.7569	Intermediate Similarity	NPD5110	Phase 2
0.7569	Intermediate Similarity	NPD5111	Phase 2
0.7569	Intermediate Similarity	NPD5109	Approved
0.7564	Intermediate Similarity	NPD6072	Discontinued
0.7551	Intermediate Similarity	NPD6896	Approved
0.7551	Intermediate Similarity	NPD6895	Approved
0.755	Intermediate Similarity	NPD2219	Phase 1
0.7547	Intermediate Similarity	NPD4055	Discovery
0.7536	Intermediate Similarity	NPD2667	Approved
0.7536	Intermediate Similarity	NPD2668	Approved
0.7535	Intermediate Similarity	NPD9619	Approved
0.7535	Intermediate Similarity	NPD9620	Approved
0.7535	Intermediate Similarity	NPD9621	Approved
0.7517	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3536	Discontinued
0.75	Intermediate Similarity	NPD7124	Phase 2
0.7468	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2238	Phase 2
0.7465	Intermediate Similarity	NPD3053	Approved
0.7465	Intermediate Similarity	NPD3055	Approved
0.7448	Intermediate Similarity	NPD597	Approved
0.7448	Intermediate Similarity	NPD601	Approved
0.7448	Intermediate Similarity	NPD598	Approved
0.7447	Intermediate Similarity	NPD3685	Discontinued
0.7438	Intermediate Similarity	NPD5604	Discontinued
0.7436	Intermediate Similarity	NPD3455	Phase 2
0.7434	Intermediate Similarity	NPD2677	Approved
0.7431	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4083	Discontinued
0.7397	Intermediate Similarity	NPD3532	Approved
0.7397	Intermediate Similarity	NPD3531	Approved
0.7397	Intermediate Similarity	NPD3530	Approved
0.7397	Intermediate Similarity	NPD1132	Approved
0.7397	Intermediate Similarity	NPD1136	Approved
0.7397	Intermediate Similarity	NPD1130	Approved
0.7394	Intermediate Similarity	NPD5311	Approved
0.7394	Intermediate Similarity	NPD5310	Approved
0.7386	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4108	Discontinued
0.7383	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2231	Phase 2
0.7376	Intermediate Similarity	NPD2230	Approved
0.7376	Intermediate Similarity	NPD2232	Approved
0.7376	Intermediate Similarity	NPD2233	Approved
0.7376	Intermediate Similarity	NPD2235	Phase 2
0.7372	Intermediate Similarity	NPD4210	Discontinued
0.7368	Intermediate Similarity	NPD3022	Approved
0.7368	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3021	Approved
0.7361	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4993	Discontinued
0.7351	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3620	Phase 2
0.7338	Intermediate Similarity	NPD7213	Phase 3
0.7338	Intermediate Similarity	NPD7212	Phase 2
0.7333	Intermediate Similarity	NPD9377	Approved
0.7333	Intermediate Similarity	NPD9379	Approved
0.7329	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2983	Phase 2
0.7324	Intermediate Similarity	NPD2982	Phase 2
0.7312	Intermediate Similarity	NPD2560	Approved
0.7312	Intermediate Similarity	NPD2563	Approved
0.7308	Intermediate Similarity	NPD5976	Discontinued
0.729	Intermediate Similarity	NPD7447	Phase 1
0.729	Intermediate Similarity	NPD3985	Discontinued
0.7279	Intermediate Similarity	NPD7477	Discontinued
0.7273	Intermediate Similarity	NPD27	Approved
0.7273	Intermediate Similarity	NPD2489	Approved
0.726	Intermediate Similarity	NPD3179	Approved
0.726	Intermediate Similarity	NPD3180	Approved
0.726	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1024	Discontinued
0.7254	Intermediate Similarity	NPD2981	Phase 2
0.7254	Intermediate Similarity	NPD2562	Approved
0.7254	Intermediate Similarity	NPD2561	Approved
0.725	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD817	Approved
0.7248	Intermediate Similarity	NPD2157	Approved
0.7248	Intermediate Similarity	NPD823	Approved
0.7246	Intermediate Similarity	NPD3596	Phase 2
0.7241	Intermediate Similarity	NPD1712	Approved
0.7241	Intermediate Similarity	NPD3018	Phase 2
0.7239	Intermediate Similarity	NPD4666	Phase 3
0.7239	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6385	Approved
0.7233	Intermediate Similarity	NPD5090	Approved
0.7233	Intermediate Similarity	NPD6386	Approved
0.7233	Intermediate Similarity	NPD5089	Approved
0.7226	Intermediate Similarity	NPD1774	Approved
0.7219	Intermediate Similarity	NPD6032	Approved
0.7214	Intermediate Similarity	NPD1357	Approved
0.7212	Intermediate Similarity	NPD2969	Approved
0.7212	Intermediate Similarity	NPD2970	Approved
0.7211	Intermediate Similarity	NPD1048	Approved
0.7208	Intermediate Similarity	NPD3692	Discontinued
0.7206	Intermediate Similarity	NPD821	Approved
0.7203	Intermediate Similarity	NPD4659	Approved
0.72	Intermediate Similarity	NPD6111	Discontinued
0.7194	Intermediate Similarity	NPD5536	Phase 2
0.7185	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3705	Approved
0.7178	Intermediate Similarity	NPD5709	Phase 3
0.7171	Intermediate Similarity	NPD3656	Approved
0.7163	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1423	Approved
0.7161	Intermediate Similarity	NPD3122	Phase 3
0.7152	Intermediate Similarity	NPD3051	Approved
0.7143	Intermediate Similarity	NPD6581	Approved
0.7143	Intermediate Similarity	NPD6580	Approved
0.7133	Intermediate Similarity	NPD2568	Approved
0.7133	Intermediate Similarity	NPD2653	Approved
0.7125	Intermediate Similarity	NPD3778	Approved
0.7124	Intermediate Similarity	NPD7037	Approved
0.7124	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2861	Phase 2
0.7118	Intermediate Similarity	NPD7039	Approved
0.7118	Intermediate Similarity	NPD7038	Approved
0.7117	Intermediate Similarity	NPD7831	Phase 2
0.7117	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7833	Phase 2
0.7111	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3111	Phase 1
0.7103	Intermediate Similarity	NPD4103	Phase 2
0.7103	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2821	Approved
0.7089	Intermediate Similarity	NPD7131	Phase 3
0.7089	Intermediate Similarity	NPD6031	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