NPASS Compound

Structure

CID54066 OpenBabel06191715392D 22 23 0 0 0 0 0 0 0 0999 V2000 0.8660 -2.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 -1.8364 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 -4.4347 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -1.7321 -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 -5.2437 -1.0933 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 -0.8660 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 -5.4516 -0.1151 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 -4.7084 0.5540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4026 0.1939 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 -0.8660 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 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 4 7 2 0 0 0 0 5 12 2 0 0 0 0 6 8 1 0 0 0 0 6 11 1 0 0 0 0 7 17 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	305.13
Volume:	307.308
LogP:	2.233
LogD:	3.251
LogS:	-3.086
# Rotatable Bonds:	7
TPSA:	69.92
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.851
Synthetic Accessibility Score:	2.155
Fsp3:	0.312
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:	-4.73
MDCK Permeability:	1.1499058018671349e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	63.12321853637695%
Volume Distribution (VD):	0.464
Pgp-substrate:	19.845428466796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.104
CYP1A2-substrate:	0.632
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.178
CYP2C9-inhibitor:	0.286
CYP2C9-substrate:	0.568
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	8.758
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.451
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.11
Skin Sensitization:	0.078
Carcinogencity:	0.28
Eye Corrosion:	0.003
Eye Irritation:	0.053
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC54066

Natural Product ID:	NPC54066
*Common Name:**	Peyonine
IUPAC Name:	1-[2-(3,4,5-trimethoxyphenyl)ethyl]pyrrole-2-carboxylic acid
Synonyms:	Peyonine
Standard InCHIKey:	DDYNENGLSGKEPO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H19NO5/c1-20-13-9-11(10-14(21-2)15(13)22-3)6-8-17-7-4-5-12(17)16(18)19/h4-5,7,9-10H,6,8H2,1-3H3,(H,18,19)
SMILES:	COc1cc(CCn2cccc2C(=O)O)cc(c1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455359
PubChem CID:	602258
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT355	Organism	Phaseolus vulgaris	Phaseolus vulgaris	Inhibition	=	0.0	%	PMID[519475]

☑ 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 NPC54066 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	377
0.1-0.2	2875
0.2-0.3	11697
0.3-0.4	4871
0.4-0.5	10092
0.5-0.6	10799
0.6-0.7	1720
0.7-0.8	260
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8431	Intermediate Similarity	NPC210256
0.8408	Intermediate Similarity	NPC127085
0.8043	Intermediate Similarity	NPC183537
0.8038	Intermediate Similarity	NPC472287
0.8038	Intermediate Similarity	NPC472286
0.8028	Intermediate Similarity	NPC236668
0.8018	Intermediate Similarity	NPC15406
0.7991	Intermediate Similarity	NPC146976
0.7991	Intermediate Similarity	NPC129897
0.7965	Intermediate Similarity	NPC77878
0.7946	Intermediate Similarity	NPC90875
0.7937	Intermediate Similarity	NPC233334
0.7904	Intermediate Similarity	NPC124313
0.7895	Intermediate Similarity	NPC207283
0.7895	Intermediate Similarity	NPC84164
0.7851	Intermediate Similarity	NPC210296
0.783	Intermediate Similarity	NPC318068
0.7792	Intermediate Similarity	NPC107123
0.7788	Intermediate Similarity	NPC472284
0.7773	Intermediate Similarity	NPC119134
0.7772	Intermediate Similarity	NPC295158
0.7768	Intermediate Similarity	NPC24019
0.7753	Intermediate Similarity	NPC108342
0.7746	Intermediate Similarity	NPC193238
0.7719	Intermediate Similarity	NPC189903
0.7719	Intermediate Similarity	NPC182907
0.7685	Intermediate Similarity	NPC241025
0.7664	Intermediate Similarity	NPC321428
0.7647	Intermediate Similarity	NPC174049
0.7636	Intermediate Similarity	NPC473822
0.7617	Intermediate Similarity	NPC134637
0.7609	Intermediate Similarity	NPC166722
0.7588	Intermediate Similarity	NPC22481
0.7588	Intermediate Similarity	NPC172222
0.7578	Intermediate Similarity	NPC210434
0.7578	Intermediate Similarity	NPC122463
0.7548	Intermediate Similarity	NPC195268
0.7548	Intermediate Similarity	NPC133140
0.7547	Intermediate Similarity	NPC477019
0.7533	Intermediate Similarity	NPC278525
0.7523	Intermediate Similarity	NPC146418
0.7489	Intermediate Similarity	NPC476995
0.7488	Intermediate Similarity	NPC224928
0.7478	Intermediate Similarity	NPC253675
0.7455	Intermediate Similarity	NPC266931
0.7444	Intermediate Similarity	NPC74360
0.7424	Intermediate Similarity	NPC201508
0.7424	Intermediate Similarity	NPC476999
0.7419	Intermediate Similarity	NPC313189
0.7418	Intermediate Similarity	NPC4071
0.7418	Intermediate Similarity	NPC476578
0.7418	Intermediate Similarity	NPC476582
0.7414	Intermediate Similarity	NPC15801
0.7412	Intermediate Similarity	NPC246381
0.7412	Intermediate Similarity	NPC476997
0.7409	Intermediate Similarity	NPC112206
0.7409	Intermediate Similarity	NPC202605
0.7406	Intermediate Similarity	NPC473814
0.7406	Intermediate Similarity	NPC78767
0.7393	Intermediate Similarity	NPC93390
0.7387	Intermediate Similarity	NPC41717
0.738	Intermediate Similarity	NPC476996
0.738	Intermediate Similarity	NPC476998
0.7379	Intermediate Similarity	NPC207851
0.7361	Intermediate Similarity	NPC475774
0.7359	Intermediate Similarity	NPC255800
0.7359	Intermediate Similarity	NPC96584
0.7339	Intermediate Similarity	NPC473639
0.7336	Intermediate Similarity	NPC215837
0.7336	Intermediate Similarity	NPC476994
0.7331	Intermediate Similarity	NPC316224
0.733	Intermediate Similarity	NPC296482
0.733	Intermediate Similarity	NPC202768
0.733	Intermediate Similarity	NPC53069
0.7327	Intermediate Similarity	NPC36229
0.7327	Intermediate Similarity	NPC476581
0.7327	Intermediate Similarity	NPC16452
0.73	Intermediate Similarity	NPC471013
0.73	Intermediate Similarity	NPC148896
0.73	Intermediate Similarity	NPC180668
0.7273	Intermediate Similarity	NPC48042
0.7273	Intermediate Similarity	NPC304179
0.7273	Intermediate Similarity	NPC475301
0.7273	Intermediate Similarity	NPC85879
0.7273	Intermediate Similarity	NPC260434
0.7273	Intermediate Similarity	NPC326930
0.7273	Intermediate Similarity	NPC472550
0.7273	Intermediate Similarity	NPC53255
0.7264	Intermediate Similarity	NPC230403
0.726	Intermediate Similarity	NPC135549
0.7252	Intermediate Similarity	NPC316981
0.7249	Intermediate Similarity	NPC473506
0.7246	Intermediate Similarity	NPC49672
0.7246	Intermediate Similarity	NPC148889
0.7243	Intermediate Similarity	NPC13603
0.724	Intermediate Similarity	NPC470020
0.7237	Intermediate Similarity	NPC76565
0.7237	Intermediate Similarity	NPC250807
0.7237	Intermediate Similarity	NPC57797
0.7235	Intermediate Similarity	NPC66815
0.7235	Intermediate Similarity	NPC57398
0.723	Intermediate Similarity	NPC146724
0.7227	Intermediate Similarity	NPC63041
0.7224	Intermediate Similarity	NPC191489
0.7222	Intermediate Similarity	NPC234197
0.7217	Intermediate Similarity	NPC87152
0.7217	Intermediate Similarity	NPC475600
0.7217	Intermediate Similarity	NPC228377
0.7217	Intermediate Similarity	NPC477787
0.7217	Intermediate Similarity	NPC328186
0.7217	Intermediate Similarity	NPC122968
0.7217	Intermediate Similarity	NPC475631
0.7217	Intermediate Similarity	NPC476110
0.7212	Intermediate Similarity	NPC168209
0.7205	Intermediate Similarity	NPC473850
0.7205	Intermediate Similarity	NPC475137
0.7205	Intermediate Similarity	NPC475498
0.72	Intermediate Similarity	NPC6981
0.72	Intermediate Similarity	NPC246658
0.7197	Intermediate Similarity	NPC475533
0.7195	Intermediate Similarity	NPC325297
0.7189	Intermediate Similarity	NPC31930
0.7186	Intermediate Similarity	NPC470486
0.7186	Intermediate Similarity	NPC471977
0.7186	Intermediate Similarity	NPC475644
0.7186	Intermediate Similarity	NPC471190
0.7178	Intermediate Similarity	NPC10904
0.7176	Intermediate Similarity	NPC123395
0.7175	Intermediate Similarity	NPC171409
0.7175	Intermediate Similarity	NPC472553
0.7175	Intermediate Similarity	NPC96405
0.7173	Intermediate Similarity	NPC217554
0.7168	Intermediate Similarity	NPC294579
0.7168	Intermediate Similarity	NPC314270
0.7168	Intermediate Similarity	NPC144779
0.7167	Intermediate Similarity	NPC324619
0.7167	Intermediate Similarity	NPC161801
0.7167	Intermediate Similarity	NPC475315
0.7166	Intermediate Similarity	NPC471978
0.7163	Intermediate Similarity	NPC74153
0.7162	Intermediate Similarity	NPC290689
0.7156	Intermediate Similarity	NPC470306
0.7156	Intermediate Similarity	NPC42678
0.7156	Intermediate Similarity	NPC477907
0.7156	Intermediate Similarity	NPC477909
0.7156	Intermediate Similarity	NPC477910
0.7155	Intermediate Similarity	NPC469792
0.7155	Intermediate Similarity	NPC284141
0.7154	Intermediate Similarity	NPC473833
0.7149	Intermediate Similarity	NPC67401
0.7149	Intermediate Similarity	NPC470042
0.7143	Intermediate Similarity	NPC146824
0.7137	Intermediate Similarity	NPC301368
0.7137	Intermediate Similarity	NPC216428
0.7137	Intermediate Similarity	NPC84815
0.7137	Intermediate Similarity	NPC308906
0.7137	Intermediate Similarity	NPC315804
0.7137	Intermediate Similarity	NPC313804
0.7126	Intermediate Similarity	NPC282346
0.7124	Intermediate Similarity	NPC292416
0.7124	Intermediate Similarity	NPC316841
0.7124	Intermediate Similarity	NPC473689
0.7124	Intermediate Similarity	NPC475303
0.7124	Intermediate Similarity	NPC475596
0.7124	Intermediate Similarity	NPC206343
0.7124	Intermediate Similarity	NPC477908
0.7124	Intermediate Similarity	NPC471014
0.7124	Intermediate Similarity	NPC471016
0.7124	Intermediate Similarity	NPC475408
0.7123	Intermediate Similarity	NPC317572
0.7118	Intermediate Similarity	NPC243633
0.7118	Intermediate Similarity	NPC175150
0.7118	Intermediate Similarity	NPC477788
0.7112	Intermediate Similarity	NPC475362
0.7112	Intermediate Similarity	NPC194740
0.7112	Intermediate Similarity	NPC274640
0.7111	Intermediate Similarity	NPC228331
0.7111	Intermediate Similarity	NPC319128
0.7108	Intermediate Similarity	NPC88923
0.7108	Intermediate Similarity	NPC100734
0.7108	Intermediate Similarity	NPC315634
0.7106	Intermediate Similarity	NPC182222
0.7103	Intermediate Similarity	NPC307963
0.7103	Intermediate Similarity	NPC473821
0.7098	Intermediate Similarity	NPC251160
0.7097	Intermediate Similarity	NPC328928
0.7094	Intermediate Similarity	NPC244839
0.7094	Intermediate Similarity	NPC320324
0.7094	Intermediate Similarity	NPC30456
0.7094	Intermediate Similarity	NPC319880
0.7093	Intermediate Similarity	NPC62367
0.7093	Intermediate Similarity	NPC184408
0.7093	Intermediate Similarity	NPC173080
0.7091	Intermediate Similarity	NPC329708
0.7091	Intermediate Similarity	NPC118832
0.7091	Intermediate Similarity	NPC47059
0.7091	Intermediate Similarity	NPC165349
0.7091	Intermediate Similarity	NPC274291
0.7091	Intermediate Similarity	NPC264166
0.709	Intermediate Similarity	NPC471015

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 NPC54066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	647
0.2-0.3	959
0.3-0.4	1364
0.4-0.5	2688
0.5-0.6	2455
0.6-0.7	757
0.7-0.8	55
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8066	Intermediate Similarity	NPD5866	Approved
0.8044	Intermediate Similarity	NPD7885	Phase 2
0.8044	Intermediate Similarity	NPD7886	Phase 2
0.7662	Intermediate Similarity	NPD1483	Discontinued
0.7548	Intermediate Similarity	NPD3924	Approved
0.7548	Intermediate Similarity	NPD3922	Approved
0.7548	Intermediate Similarity	NPD3921	Approved
0.7548	Intermediate Similarity	NPD3923	Approved
0.7543	Intermediate Similarity	NPD7417	Discontinued
0.7468	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6974	Phase 3
0.7426	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5640	Discontinued
0.7368	Intermediate Similarity	NPD3259	Approved
0.7366	Intermediate Similarity	NPD3386	Phase 2
0.7354	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3816	Phase 1
0.733	Intermediate Similarity	NPD3815	Phase 1
0.7321	Intermediate Similarity	NPD3354	Phase 2
0.7311	Intermediate Similarity	NPD3328	Phase 2
0.7282	Intermediate Similarity	NPD3178	Discontinued
0.7265	Intermediate Similarity	NPD5805	Approved
0.726	Intermediate Similarity	NPD4889	Approved
0.7257	Intermediate Similarity	NPD7180	Phase 3
0.7257	Intermediate Similarity	NPD6856	Discontinued
0.7257	Intermediate Similarity	NPD8479	Phase 2
0.7252	Intermediate Similarity	NPD7069	Discontinued
0.723	Intermediate Similarity	NPD4418	Discontinued
0.7227	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD7708	Approved
0.722	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4551	Phase 2
0.7183	Intermediate Similarity	NPD6361	Phase 2
0.7181	Intermediate Similarity	NPD6242	Discontinued
0.7178	Intermediate Similarity	NPD5482	Discontinued
0.7178	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3263	Phase 3
0.7162	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5612	Discontinued
0.7156	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD3006	Discontinued
0.7143	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD3258	Approved
0.7131	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4131	Phase 3
0.7124	Intermediate Similarity	NPD4989	Phase 2
0.7111	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7803	Approved
0.7103	Intermediate Similarity	NPD1038	Approved
0.7101	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7395	Discontinued
0.7091	Intermediate Similarity	NPD4035	Approved
0.7091	Intermediate Similarity	NPD4037	Approved
0.7091	Intermediate Similarity	NPD4034	Approved
0.7091	Intermediate Similarity	NPD4038	Approved
0.7091	Intermediate Similarity	NPD32	Approved
0.7091	Intermediate Similarity	NPD4036	Approved
0.7091	Intermediate Similarity	NPD31	Approved
0.7091	Intermediate Similarity	NPD4039	Approved
0.7091	Intermediate Similarity	NPD4033	Approved
0.7091	Intermediate Similarity	NPD4122	Approved
0.7071	Intermediate Similarity	NPD6716	Phase 1
0.7064	Intermediate Similarity	NPD484	Approved
0.7062	Intermediate Similarity	NPD4375	Approved
0.7056	Intermediate Similarity	NPD6569	Phase 2
0.7045	Intermediate Similarity	NPD7956	Approved
0.7045	Intermediate Similarity	NPD7955	Approved
0.7043	Intermediate Similarity	NPD8356	Approved
0.7029	Intermediate Similarity	NPD6790	Phase 1
0.7019	Intermediate Similarity	NPD3920	Phase 2
0.7019	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4429	Discontinued
0.7014	Intermediate Similarity	NPD2831	Approved
0.7014	Intermediate Similarity	NPD3947	Discontinued
0.7009	Intermediate Similarity	NPD5022	Discontinued
0.7004	Intermediate Similarity	NPD8091	Phase 3
0.7	Intermediate Similarity	NPD6517	Phase 3
0.6996	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD4328	Approved
0.6996	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6494	Phase 2
0.6992	Remote Similarity	NPD4080	Discontinued
0.6978	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5513	Phase 2
0.696	Remote Similarity	NPD3257	Approved
0.696	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5512	Phase 3
0.6952	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7452	Approved
0.6951	Remote Similarity	NPD7222	Phase 2
0.6951	Remote Similarity	NPD7453	Approved
0.6951	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6727	Phase 2
0.6946	Remote Similarity	NPD6825	Phase 1
0.6946	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6568	Discontinued
0.6943	Remote Similarity	NPD5632	Approved
0.6933	Remote Similarity	NPD7853	Phase 2
0.6926	Remote Similarity	NPD4923	Phase 1
0.6926	Remote Similarity	NPD6298	Discontinued
0.6923	Remote Similarity	NPD7994	Phase 2
0.6923	Remote Similarity	NPD8430	Approved
0.6923	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4373	Phase 2
0.6912	Remote Similarity	NPD3395	Approved
0.6912	Remote Similarity	NPD3396	Approved
0.6911	Remote Similarity	NPD7859	Phase 2
0.6907	Remote Similarity	NPD1867	Approved
0.6907	Remote Similarity	NPD6962	Phase 2
0.6906	Remote Similarity	NPD5601	Phase 2
0.6894	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6963	Approved
0.6891	Remote Similarity	NPD6964	Approved
0.6885	Remote Similarity	NPD6276	Discontinued
0.6878	Remote Similarity	NPD7031	Phase 1
0.6878	Remote Similarity	NPD4885	Approved
0.687	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4952	Phase 3
0.6864	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1631	Approved
0.6861	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7022	Phase 2
0.686	Remote Similarity	NPD4083	Discontinued
0.6853	Remote Similarity	NPD5147	Discontinued
0.6847	Remote Similarity	NPD2779	Approved
0.6846	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2821	Approved
0.684	Remote Similarity	NPD3763	Approved
0.6838	Remote Similarity	NPD5450	Discontinued
0.6836	Remote Similarity	NPD5922	Phase 3
0.6835	Remote Similarity	NPD1505	Phase 2
0.6833	Remote Similarity	NPD6219	Discontinued
0.6829	Remote Similarity	NPD8101	Phase 3
0.6829	Remote Similarity	NPD7588	Discontinued
0.6824	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6209	Approved
0.6815	Remote Similarity	NPD5532	Phase 2
0.6815	Remote Similarity	NPD8463	Approved
0.6813	Remote Similarity	NPD6228	Discontinued
0.6812	Remote Similarity	NPD1638	Discovery
0.6812	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6550	Discontinued
0.6803	Remote Similarity	NPD7967	Discontinued
0.68	Remote Similarity	NPD1392	Approved
0.68	Remote Similarity	NPD5429	Discontinued
0.6789	Remote Similarity	NPD4558	Phase 2
0.6786	Remote Similarity	NPD3397	Phase 2
0.678	Remote Similarity	NPD7826	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5658	Approved
0.677	Remote Similarity	NPD7467	Discontinued
0.6766	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4021	Phase 2
0.6754	Remote Similarity	NPD7470	Discontinued
0.6754	Remote Similarity	NPD5416	Discontinued
0.6749	Remote Similarity	NPD820	Phase 3
0.6748	Remote Similarity	NPD6205	Discontinued
0.6745	Remote Similarity	NPD7673	Phase 3
0.6731	Remote Similarity	NPD1573	Approved
0.6731	Remote Similarity	NPD1575	Approved
0.673	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1096	Discontinued
0.6726	Remote Similarity	NPD7263	Phase 2
0.6724	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4454	Phase 2
0.6716	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1630	Approved
0.6714	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1034	Phase 3
0.6712	Remote Similarity	NPD6874	Approved
0.6712	Remote Similarity	NPD2778	Approved
0.6711	Remote Similarity	NPD5901	Discontinued
0.6711	Remote Similarity	NPD3392	Approved
0.6711	Remote Similarity	NPD7396	Approved
0.6709	Remote Similarity	NPD4086	Phase 1
0.6709	Remote Similarity	NPD4845	Discontinued
0.6708	Remote Similarity	NPD2929	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7558	Phase 2
0.6708	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8468	Phase 2
0.6707	Remote Similarity	NPD8100	Phase 3
0.6705	Remote Similarity	NPD7689	Approved
0.6699	Remote Similarity	NPD5088	Discontinued
0.6699	Remote Similarity	NPD5242	Approved
0.6698	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD3945	Discontinued
0.6695	Remote Similarity	NPD1467	Approved
0.6695	Remote Similarity	NPD1466	Phase 3

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