NPASS Compound

Structure

NPC470392 OpenBabel07101718312D 21 21 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 -0.8660 1.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 6 1 0 0 0 0 4 13 2 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 12 17 2 3 0 0 0 12 18 1 0 0 0 0 14 21 1 0 0 0 0 15 10 1 6 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	291.15
Volume:	307.075
LogP:	2.391
LogD:	1.628
LogS:	-2.973
# Rotatable Bonds:	8
TPSA:	75.63
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	2.451
Fsp3:	0.375
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:	-5.357
MDCK Permeability:	3.20682956953533e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.064
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.143
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	80.7972412109375%
Volume Distribution (VD):	0.276
Pgp-substrate:	21.9657039642334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.306
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	3.31
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.816
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.153
Carcinogencity:	0.379
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC470392

Natural Product ID:	NPC470392
*Common Name:**	N-Acetyl-O-Isopentenyl-L-Tyrosine
IUPAC Name:	(2S)-2-acetamido-3-[4-(3-methylbut-2-enoxy)phenyl]propanoic acid
Synonyms:
Standard InCHIKey:	YHKFAYFIUKFOFG-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C16H21NO4/c1-11(2)8-9-21-14-6-4-13(5-7-14)10-15(16(19)20)17-12(3)18/h4-8,15H,9-10H2,1-3H3,(H,17,18)(H,19,20)/t15-/m0/s1
SMILES:	CC(=CCOC1=CC=C(C=C1)CC(C(=O)O)NC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022663
PubChem CID:	11652223
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004321] Phenylalanine 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
NPO32943	pithomyces ellis	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]

☑ 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	7

Activity Type	# Activity
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.002	n.a.	PMID[487493]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.194	n.a.	PMID[487493]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.237	n.a.	PMID[487493]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.19	n.a.	PMID[487493]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.125	n.a.	PMID[487493]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.248	n.a.	PMID[487493]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.123	n.a.	PMID[487493]

☑ 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 NPC470392 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	147
0.1-0.2	850
0.2-0.3	4230
0.3-0.4	11846
0.4-0.5	6125
0.5-0.6	11922
0.6-0.7	7025
0.7-0.8	502
0.8-0.85	42
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8651	High Similarity	NPC319950
0.8626	High Similarity	NPC296712
0.8611	High Similarity	NPC56635
0.845	Intermediate Similarity	NPC142577
0.845	Intermediate Similarity	NPC474862
0.8433	Intermediate Similarity	NPC45191
0.8409	Intermediate Similarity	NPC476353
0.838	Intermediate Similarity	NPC132771
0.8308	Intermediate Similarity	NPC27581
0.8295	Intermediate Similarity	NPC263835
0.8284	Intermediate Similarity	NPC478147
0.8195	Intermediate Similarity	NPC124776
0.8189	Intermediate Similarity	NPC51345
0.8188	Intermediate Similarity	NPC6570
0.8175	Intermediate Similarity	NPC169766
0.8148	Intermediate Similarity	NPC325651
0.8143	Intermediate Similarity	NPC282087
0.8143	Intermediate Similarity	NPC318028
0.8143	Intermediate Similarity	NPC318984
0.8143	Intermediate Similarity	NPC241086
0.8143	Intermediate Similarity	NPC317741
0.8143	Intermediate Similarity	NPC259800
0.8143	Intermediate Similarity	NPC328137
0.8102	Intermediate Similarity	NPC244866
0.8014	Intermediate Similarity	NPC326860
0.8014	Intermediate Similarity	NPC197239
0.8	Intermediate Similarity	NPC293424
0.8	Intermediate Similarity	NPC234639
0.7987	Intermediate Similarity	NPC212699
0.7987	Intermediate Similarity	NPC207675
0.7985	Intermediate Similarity	NPC95733
0.7985	Intermediate Similarity	NPC62101
0.7974	Intermediate Similarity	NPC473502
0.7958	Intermediate Similarity	NPC212850
0.7958	Intermediate Similarity	NPC83289
0.7958	Intermediate Similarity	NPC91953
0.7958	Intermediate Similarity	NPC189724
0.7945	Intermediate Similarity	NPC324081
0.7939	Intermediate Similarity	NPC43275
0.7931	Intermediate Similarity	NPC17760
0.791	Intermediate Similarity	NPC211218
0.7902	Intermediate Similarity	NPC66518
0.7899	Intermediate Similarity	NPC326966
0.7891	Intermediate Similarity	NPC26524
0.7887	Intermediate Similarity	NPC197921
0.7874	Intermediate Similarity	NPC166837
0.7871	Intermediate Similarity	NPC196091
0.7868	Intermediate Similarity	NPC474476
0.7857	Intermediate Similarity	NPC259554
0.7846	Intermediate Similarity	NPC106551
0.7846	Intermediate Similarity	NPC188867
0.7846	Intermediate Similarity	NPC281686
0.7843	Intermediate Similarity	NPC472923
0.7842	Intermediate Similarity	NPC274732
0.7842	Intermediate Similarity	NPC471953
0.7832	Intermediate Similarity	NPC469360
0.7823	Intermediate Similarity	NPC473855
0.7808	Intermediate Similarity	NPC313414
0.7803	Intermediate Similarity	NPC264976
0.7803	Intermediate Similarity	NPC256369
0.7801	Intermediate Similarity	NPC6913
0.7801	Intermediate Similarity	NPC196708
0.7794	Intermediate Similarity	NPC29477
0.7761	Intermediate Similarity	NPC160493
0.776	Intermediate Similarity	NPC1065
0.7752	Intermediate Similarity	NPC109241
0.7744	Intermediate Similarity	NPC471308
0.7744	Intermediate Similarity	NPC160120
0.7744	Intermediate Similarity	NPC289330
0.7744	Intermediate Similarity	NPC17388
0.7744	Intermediate Similarity	NPC53596
0.774	Intermediate Similarity	NPC247298
0.7721	Intermediate Similarity	NPC221798
0.7721	Intermediate Similarity	NPC4974
0.7714	Intermediate Similarity	NPC328070
0.7697	Intermediate Similarity	NPC319320
0.7697	Intermediate Similarity	NPC287757
0.7692	Intermediate Similarity	NPC471316
0.7692	Intermediate Similarity	NPC186617
0.7687	Intermediate Similarity	NPC326079
0.7687	Intermediate Similarity	NPC9373
0.768	Intermediate Similarity	NPC470393
0.7671	Intermediate Similarity	NPC81026
0.7669	Intermediate Similarity	NPC239697
0.7664	Intermediate Similarity	NPC280767
0.766	Intermediate Similarity	NPC132308
0.7655	Intermediate Similarity	NPC204546
0.7643	Intermediate Similarity	NPC473693
0.7643	Intermediate Similarity	NPC471568
0.7638	Intermediate Similarity	NPC31274
0.7635	Intermediate Similarity	NPC245974
0.7634	Intermediate Similarity	NPC317254
0.7622	Intermediate Similarity	NPC106606
0.7622	Intermediate Similarity	NPC473055
0.7622	Intermediate Similarity	NPC473052
0.7612	Intermediate Similarity	NPC474874
0.7612	Intermediate Similarity	NPC80150
0.7612	Intermediate Similarity	NPC190663
0.7612	Intermediate Similarity	NPC476183
0.7603	Intermediate Similarity	NPC266741
0.76	Intermediate Similarity	NPC38079
0.76	Intermediate Similarity	NPC283546
0.76	Intermediate Similarity	NPC108875
0.7594	Intermediate Similarity	NPC205502
0.7591	Intermediate Similarity	NPC89630
0.7589	Intermediate Similarity	NPC247018
0.7589	Intermediate Similarity	NPC307123
0.7589	Intermediate Similarity	NPC97870
0.7586	Intermediate Similarity	NPC470709
0.7578	Intermediate Similarity	NPC475421
0.7574	Intermediate Similarity	NPC471315
0.7574	Intermediate Similarity	NPC69403
0.7574	Intermediate Similarity	NPC471314
0.7574	Intermediate Similarity	NPC291189
0.7571	Intermediate Similarity	NPC241354
0.7569	Intermediate Similarity	NPC322526
0.7564	Intermediate Similarity	NPC254700
0.7561	Intermediate Similarity	NPC315542
0.7559	Intermediate Similarity	NPC157473
0.7559	Intermediate Similarity	NPC151530
0.7557	Intermediate Similarity	NPC235250
0.7556	Intermediate Similarity	NPC56634
0.7556	Intermediate Similarity	NPC476184
0.7556	Intermediate Similarity	NPC476281
0.7554	Intermediate Similarity	NPC251571
0.7554	Intermediate Similarity	NPC153990
0.7535	Intermediate Similarity	NPC105541
0.7533	Intermediate Similarity	NPC153644
0.7532	Intermediate Similarity	NPC151030
0.7532	Intermediate Similarity	NPC269383
0.752	Intermediate Similarity	NPC298224
0.7519	Intermediate Similarity	NPC25067
0.7519	Intermediate Similarity	NPC88868
0.7519	Intermediate Similarity	NPC231251
0.7519	Intermediate Similarity	NPC169328
0.7518	Intermediate Similarity	NPC114102
0.7517	Intermediate Similarity	NPC40321
0.75	Intermediate Similarity	NPC2596
0.75	Intermediate Similarity	NPC97811
0.75	Intermediate Similarity	NPC164608
0.75	Intermediate Similarity	NPC136951
0.75	Intermediate Similarity	NPC303370
0.75	Intermediate Similarity	NPC291837
0.75	Intermediate Similarity	NPC161155
0.75	Intermediate Similarity	NPC97004
0.7483	Intermediate Similarity	NPC282477
0.7483	Intermediate Similarity	NPC182119
0.7483	Intermediate Similarity	NPC284855
0.7482	Intermediate Similarity	NPC301713
0.7482	Intermediate Similarity	NPC475236
0.7481	Intermediate Similarity	NPC193193
0.7481	Intermediate Similarity	NPC309808
0.7481	Intermediate Similarity	NPC31314
0.7481	Intermediate Similarity	NPC321133
0.748	Intermediate Similarity	NPC231705
0.748	Intermediate Similarity	NPC176971
0.7465	Intermediate Similarity	NPC88667
0.7465	Intermediate Similarity	NPC214869
0.7463	Intermediate Similarity	NPC142638
0.7463	Intermediate Similarity	NPC310467
0.7463	Intermediate Similarity	NPC317784
0.746	Intermediate Similarity	NPC38209
0.745	Intermediate Similarity	NPC189908
0.745	Intermediate Similarity	NPC97282
0.7448	Intermediate Similarity	NPC41473
0.7448	Intermediate Similarity	NPC160607
0.7448	Intermediate Similarity	NPC312770
0.7448	Intermediate Similarity	NPC471201
0.7448	Intermediate Similarity	NPC204848
0.7448	Intermediate Similarity	NPC14600
0.7447	Intermediate Similarity	NPC52029
0.7447	Intermediate Similarity	NPC195749
0.7447	Intermediate Similarity	NPC35961
0.7445	Intermediate Similarity	NPC476278
0.7444	Intermediate Similarity	NPC19290
0.7442	Intermediate Similarity	NPC258056
0.744	Intermediate Similarity	NPC307425
0.7439	Intermediate Similarity	NPC470112
0.7439	Intermediate Similarity	NPC470903
0.7439	Intermediate Similarity	NPC167763
0.7436	Intermediate Similarity	NPC67080
0.7434	Intermediate Similarity	NPC39431
0.7432	Intermediate Similarity	NPC178466
0.7432	Intermediate Similarity	NPC63628
0.7424	Intermediate Similarity	NPC118202
0.7422	Intermediate Similarity	NPC142297
0.7419	Intermediate Similarity	NPC12730
0.741	Intermediate Similarity	NPC320242
0.7407	Intermediate Similarity	NPC283760
0.7403	Intermediate Similarity	NPC197741
0.7403	Intermediate Similarity	NPC305700
0.7403	Intermediate Similarity	NPC187028
0.7403	Intermediate Similarity	NPC140915
0.7403	Intermediate Similarity	NPC18249
0.7403	Intermediate Similarity	NPC10221
0.7402	Intermediate Similarity	NPC238115
0.7402	Intermediate Similarity	NPC128730
0.7402	Intermediate Similarity	NPC473393
0.7397	Intermediate Similarity	NPC299583
0.7391	Intermediate Similarity	NPC476260

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 NPC470392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	114
0.1-0.2	497
0.2-0.3	995
0.3-0.4	1991
0.4-0.5	2378
0.5-0.6	1909
0.6-0.7	1037
0.7-0.8	209
0.8-0.85	17
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8963	High Similarity	NPD7596	Clinical (unspecified phase)
0.8652	High Similarity	NPD6390	Discontinued
0.8538	High Similarity	NPD196	Phase 1
0.8507	High Similarity	NPD5745	Approved
0.8493	Intermediate Similarity	NPD7972	Discontinued
0.8358	Intermediate Similarity	NPD5746	Approved
0.8321	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD2614	Approved
0.8273	Intermediate Similarity	NPD2240	Approved
0.8273	Intermediate Similarity	NPD2239	Approved
0.8264	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1536	Approved
0.8227	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD3136	Phase 2
0.8207	Intermediate Similarity	NPD7131	Phase 3
0.8143	Intermediate Similarity	NPD1519	Approved
0.8143	Intermediate Similarity	NPD1537	Approved
0.8143	Intermediate Similarity	NPD1538	Phase 1
0.8129	Intermediate Similarity	NPD1521	Approved
0.8129	Intermediate Similarity	NPD1520	Approved
0.8105	Intermediate Similarity	NPD7608	Discontinued
0.8054	Intermediate Similarity	NPD5355	Approved
0.8054	Intermediate Similarity	NPD5356	Approved
0.8045	Intermediate Similarity	NPD3685	Discontinued
0.8014	Intermediate Similarity	NPD1522	Approved
0.8014	Intermediate Similarity	NPD1523	Approved
0.7971	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD821	Approved
0.7945	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6502	Phase 2
0.7887	Intermediate Similarity	NPD4477	Approved
0.7887	Intermediate Similarity	NPD4476	Approved
0.7863	Intermediate Similarity	NPD1894	Discontinued
0.7846	Intermediate Similarity	NPD9568	Approved
0.7842	Intermediate Similarity	NPD7477	Discontinued
0.7836	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5163	Phase 2
0.782	Intermediate Similarity	NPD3847	Discontinued
0.777	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1048	Approved
0.7748	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5689	Approved
0.7746	Intermediate Similarity	NPD5688	Approved
0.7703	Intermediate Similarity	NPD3536	Discontinued
0.766	Intermediate Similarity	NPD3142	Approved
0.766	Intermediate Similarity	NPD3140	Approved
0.7652	Intermediate Similarity	NPD1758	Phase 1
0.7643	Intermediate Similarity	NPD6798	Discontinued
0.7643	Intermediate Similarity	NPD7315	Approved
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD256	Approved
0.7634	Intermediate Similarity	NPD255	Approved
0.7628	Intermediate Similarity	NPD6746	Phase 2
0.7625	Intermediate Similarity	NPD3965	Phase 1
0.7606	Intermediate Similarity	NPD555	Phase 2
0.7606	Intermediate Similarity	NPD4622	Approved
0.7606	Intermediate Similarity	NPD4618	Approved
0.7597	Intermediate Similarity	NPD7318	Phase 3
0.7594	Intermediate Similarity	NPD1759	Phase 1
0.7589	Intermediate Similarity	NPD1423	Approved
0.7589	Intermediate Similarity	NPD6233	Phase 2
0.7589	Intermediate Similarity	NPD4062	Phase 3
0.7586	Intermediate Similarity	NPD7978	Discontinued
0.7586	Intermediate Similarity	NPD3656	Approved
0.7586	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4739	Approved
0.7578	Intermediate Similarity	NPD5557	Phase 1
0.7568	Intermediate Similarity	NPD6667	Approved
0.7568	Intermediate Similarity	NPD6666	Approved
0.7562	Intermediate Similarity	NPD3909	Discontinued
0.7554	Intermediate Similarity	NPD1712	Approved
0.7552	Intermediate Similarity	NPD3054	Approved
0.7552	Intermediate Similarity	NPD3052	Approved
0.7552	Intermediate Similarity	NPD2157	Approved
0.7534	Intermediate Similarity	NPD7153	Discontinued
0.7534	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6583	Phase 3
0.7518	Intermediate Similarity	NPD1669	Approved
0.7518	Intermediate Similarity	NPD6582	Phase 2
0.7517	Intermediate Similarity	NPD6032	Approved
0.7517	Intermediate Similarity	NPD2161	Phase 2
0.7516	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3274	Phase 2
0.7516	Intermediate Similarity	NPD6677	Suspended
0.75	Intermediate Similarity	NPD1535	Discovery
0.7483	Intermediate Similarity	NPD2458	Approved
0.7483	Intermediate Similarity	NPD7427	Discontinued
0.7483	Intermediate Similarity	NPD2460	Phase 3
0.7483	Intermediate Similarity	NPD2459	Approved
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7481	Intermediate Similarity	NPD2668	Approved
0.7481	Intermediate Similarity	NPD2667	Approved
0.7481	Intermediate Similarity	NPD1241	Discontinued
0.7468	Intermediate Similarity	NPD7317	Phase 3
0.7465	Intermediate Similarity	NPD259	Phase 1
0.7448	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1481	Phase 2
0.7444	Intermediate Similarity	NPD3596	Phase 2
0.7434	Intermediate Similarity	NPD3686	Approved
0.7434	Intermediate Similarity	NPD4003	Phase 3
0.7434	Intermediate Similarity	NPD3687	Approved
0.7432	Intermediate Similarity	NPD4110	Phase 3
0.7432	Intermediate Similarity	NPD3400	Discontinued
0.7432	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2653	Approved
0.7429	Intermediate Similarity	NPD4993	Discontinued
0.7419	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7526	Approved
0.7417	Intermediate Similarity	NPD52	Approved
0.7417	Intermediate Similarity	NPD2186	Approved
0.7413	Intermediate Similarity	NPD2203	Discontinued
0.7413	Intermediate Similarity	NPD826	Approved
0.7413	Intermediate Similarity	NPD825	Approved
0.741	Intermediate Similarity	NPD1820	Approved
0.741	Intermediate Similarity	NPD1818	Approved
0.741	Intermediate Similarity	NPD1819	Approved
0.741	Intermediate Similarity	NPD1817	Approved
0.7405	Intermediate Similarity	NPD5535	Approved
0.74	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7450	Phase 2
0.7397	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3455	Phase 2
0.7368	Intermediate Similarity	NPD1670	Discontinued
0.7364	Intermediate Similarity	NPD2684	Approved
0.7358	Intermediate Similarity	NPD7485	Phase 3
0.7358	Intermediate Similarity	NPD7484	Phase 3
0.7357	Intermediate Similarity	NPD6584	Phase 3
0.7357	Intermediate Similarity	NPD3691	Phase 2
0.7357	Intermediate Similarity	NPD3690	Phase 2
0.7355	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1778	Approved
0.7351	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3146	Approved
0.7347	Intermediate Similarity	NPD1375	Discontinued
0.7344	Intermediate Similarity	NPD3134	Approved
0.7343	Intermediate Similarity	NPD2674	Phase 3
0.7343	Intermediate Similarity	NPD839	Approved
0.7343	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD840	Approved
0.7333	Intermediate Similarity	NPD6580	Approved
0.7333	Intermediate Similarity	NPD6581	Approved
0.7324	Intermediate Similarity	NPD3164	Approved
0.7324	Intermediate Similarity	NPD3167	Approved
0.7324	Intermediate Similarity	NPD3166	Approved
0.7324	Intermediate Similarity	NPD3165	Approved
0.7324	Intermediate Similarity	NPD3179	Approved
0.7324	Intermediate Similarity	NPD3180	Approved
0.7315	Intermediate Similarity	NPD6331	Phase 2
0.731	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD454	Approved
0.7305	Intermediate Similarity	NPD9569	Approved
0.7297	Intermediate Similarity	NPD2897	Discontinued
0.729	Intermediate Similarity	NPD6386	Approved
0.729	Intermediate Similarity	NPD6385	Approved
0.7287	Intermediate Similarity	NPD1358	Approved
0.7286	Intermediate Similarity	NPD2797	Approved
0.7286	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1725	Approved
0.7279	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7843	Approved
0.7267	Intermediate Similarity	NPD3692	Discontinued
0.7255	Intermediate Similarity	NPD7523	Phase 3
0.7244	Intermediate Similarity	NPD4433	Discontinued
0.7244	Intermediate Similarity	NPD8019	Approved
0.7244	Intermediate Similarity	NPD7495	Discontinued
0.7239	Intermediate Similarity	NPD2557	Approved
0.7237	Intermediate Similarity	NPD2874	Phase 2
0.7234	Intermediate Similarity	NPD558	Phase 2
0.7234	Intermediate Similarity	NPD5647	Approved
0.7233	Intermediate Similarity	NPD6315	Phase 2
0.7222	Intermediate Similarity	NPD5822	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3823	Discontinued
0.7212	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4108	Discontinued
0.7203	Intermediate Similarity	NPD1024	Discontinued
0.72	Intermediate Similarity	NPD1662	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5773	Approved
0.7197	Intermediate Similarity	NPD5772	Approved
0.7194	Intermediate Similarity	NPD9717	Approved
0.7194	Intermediate Similarity	NPD2235	Phase 2
0.7194	Intermediate Similarity	NPD2231	Phase 2
0.7194	Intermediate Similarity	NPD1608	Approved
0.7183	Intermediate Similarity	NPD2237	Approved
0.7181	Intermediate Similarity	NPD2030	Discontinued
0.7179	Intermediate Similarity	NPD2366	Approved
0.7179	Intermediate Similarity	NPD6072	Discontinued
0.7174	Intermediate Similarity	NPD3496	Discontinued
0.7172	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8031	Discontinued
0.717	Intermediate Similarity	NPD6971	Discontinued
0.7169	Intermediate Similarity	NPD8014	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD593	Approved
0.7164	Intermediate Similarity	NPD595	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