NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	273.1
Volume:	278.586
LogP:	1.618
LogD:	1.883
LogS:	-2.971
# Rotatable Bonds:	5
TPSA:	89.79
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	1.789
Fsp3:	0.133
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:	-4.903
MDCK Permeability:	7.12139080860652e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.593
Human Intestinal Absorption (HIA):	0.234
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	90.65213775634766%
Volume Distribution (VD):	0.559
Pgp-substrate:	12.121193885803223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.736
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.504
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.726
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.775
CYP2D6-substrate:	0.757
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	15.344
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.135
AMES Toxicity:	0.456
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.916
Carcinogencity:	0.15
Eye Corrosion:	0.003
Eye Irritation:	0.267
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC284078

Natural Product ID:	NPC284078
*Common Name:**	N-Protocatechuoyltyramine
IUPAC Name:	3,4-dihydroxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide
Synonyms:	N-Protocatechuoyltyramine
Standard InCHIKey:	VGIFBSQQOUBLSS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H15NO4/c17-12-4-1-10(2-5-12)7-8-16-15(20)11-3-6-13(18)14(19)9-11/h1-6,9,17-19H,7-8H2,(H,16,20)
SMILES:	Oc1ccc(cc1)CCN=C(c1ccc(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564134
PubChem CID:	44521377
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004121] Norbelladine-type amaryllidaceae alkaloids

*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
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	Activity	=	88.0	%	PMID[531572]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	Activity	=	6.0	%	PMID[531572]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	9.0	%	PMID[531572]

☑ 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 NPC284078 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	272
0.1-0.2	1578
0.2-0.3	9395
0.3-0.4	9056
0.4-0.5	7785
0.5-0.6	10023
0.6-0.7	3994
0.7-0.8	531
0.8-0.85	50
0.85-0.9	7
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC268572
0.9224	High Similarity	NPC122009
0.9138	High Similarity	NPC283468
0.8879	High Similarity	NPC142599
0.885	High Similarity	NPC153690
0.8609	High Similarity	NPC71266
0.8492	Intermediate Similarity	NPC251571
0.8492	Intermediate Similarity	NPC477839
0.8438	Intermediate Similarity	NPC114102
0.8397	Intermediate Similarity	NPC126637
0.839	Intermediate Similarity	NPC146422
0.8372	Intermediate Similarity	NPC214869
0.8362	Intermediate Similarity	NPC96224
0.8362	Intermediate Similarity	NPC24101
0.8359	Intermediate Similarity	NPC35961
0.8359	Intermediate Similarity	NPC52029
0.8359	Intermediate Similarity	NPC195749
0.8333	Intermediate Similarity	NPC14600
0.8333	Intermediate Similarity	NPC160607
0.8333	Intermediate Similarity	NPC41473
0.8333	Intermediate Similarity	NPC471511
0.8333	Intermediate Similarity	NPC312770
0.8333	Intermediate Similarity	NPC204848
0.8293	Intermediate Similarity	NPC115627
0.8293	Intermediate Similarity	NPC118522
0.8293	Intermediate Similarity	NPC169207
0.8281	Intermediate Similarity	NPC271808
0.8281	Intermediate Similarity	NPC155838
0.8271	Intermediate Similarity	NPC299583
0.823	Intermediate Similarity	NPC223393
0.8195	Intermediate Similarity	NPC254610
0.8182	Intermediate Similarity	NPC6913
0.8167	Intermediate Similarity	NPC471485
0.8151	Intermediate Similarity	NPC268032
0.8134	Intermediate Similarity	NPC296898
0.813	Intermediate Similarity	NPC85276
0.8103	Intermediate Similarity	NPC239291
0.8087	Intermediate Similarity	NPC178902
0.8062	Intermediate Similarity	NPC186898
0.8062	Intermediate Similarity	NPC153990
0.8053	Intermediate Similarity	NPC109955
0.8051	Intermediate Similarity	NPC114392
0.8051	Intermediate Similarity	NPC105727
0.8051	Intermediate Similarity	NPC58427
0.8051	Intermediate Similarity	NPC34864
0.8049	Intermediate Similarity	NPC311737
0.8049	Intermediate Similarity	NPC38458
0.8043	Intermediate Similarity	NPC5462
0.8034	Intermediate Similarity	NPC231705
0.8017	Intermediate Similarity	NPC12278
0.8	Intermediate Similarity	NPC163674
0.8	Intermediate Similarity	NPC252817
0.7984	Intermediate Similarity	NPC301713
0.7984	Intermediate Similarity	NPC323775
0.7984	Intermediate Similarity	NPC236347
0.7983	Intermediate Similarity	NPC258056
0.7983	Intermediate Similarity	NPC254833
0.7983	Intermediate Similarity	NPC228343
0.7967	Intermediate Similarity	NPC82963
0.7966	Intermediate Similarity	NPC142297
0.7966	Intermediate Similarity	NPC176527
0.7956	Intermediate Similarity	NPC222039
0.7956	Intermediate Similarity	NPC100478
0.7951	Intermediate Similarity	NPC120280
0.792	Intermediate Similarity	NPC43275
0.7917	Intermediate Similarity	NPC474149
0.7917	Intermediate Similarity	NPC226401
0.7917	Intermediate Similarity	NPC79793
0.7917	Intermediate Similarity	NPC120982
0.7917	Intermediate Similarity	NPC174096
0.7917	Intermediate Similarity	NPC147634
0.7907	Intermediate Similarity	NPC318965
0.7899	Intermediate Similarity	NPC233835
0.7891	Intermediate Similarity	NPC318777
0.7872	Intermediate Similarity	NPC471032
0.7872	Intermediate Similarity	NPC470935
0.7851	Intermediate Similarity	NPC297657
0.7851	Intermediate Similarity	NPC179002
0.7851	Intermediate Similarity	NPC257430
0.7851	Intermediate Similarity	NPC187583
0.7845	Intermediate Similarity	NPC110764
0.7833	Intermediate Similarity	NPC55617
0.7833	Intermediate Similarity	NPC62258
0.782	Intermediate Similarity	NPC130595
0.782	Intermediate Similarity	NPC93882
0.781	Intermediate Similarity	NPC477837
0.781	Intermediate Similarity	NPC477838
0.7805	Intermediate Similarity	NPC118202
0.7801	Intermediate Similarity	NPC277857
0.7801	Intermediate Similarity	NPC115144
0.7778	Intermediate Similarity	NPC196479
0.7769	Intermediate Similarity	NPC29477
0.7761	Intermediate Similarity	NPC285078
0.7761	Intermediate Similarity	NPC313737
0.7761	Intermediate Similarity	NPC6854
0.7742	Intermediate Similarity	NPC317254
0.7742	Intermediate Similarity	NPC472893
0.7742	Intermediate Similarity	NPC37302
0.7719	Intermediate Similarity	NPC274678
0.7719	Intermediate Similarity	NPC107522
0.7717	Intermediate Similarity	NPC475245
0.7717	Intermediate Similarity	NPC472071
0.7712	Intermediate Similarity	NPC120719
0.7708	Intermediate Similarity	NPC127402
0.7705	Intermediate Similarity	NPC280382
0.7704	Intermediate Similarity	NPC218530
0.7698	Intermediate Similarity	NPC144343
0.7681	Intermediate Similarity	NPC77572
0.7672	Intermediate Similarity	NPC131587
0.7656	Intermediate Similarity	NPC470414
0.7656	Intermediate Similarity	NPC183262
0.7655	Intermediate Similarity	NPC275027
0.7638	Intermediate Similarity	NPC217174
0.7627	Intermediate Similarity	NPC68055
0.7619	Intermediate Similarity	NPC277588
0.7615	Intermediate Similarity	NPC13020
0.7615	Intermediate Similarity	NPC140359
0.7612	Intermediate Similarity	NPC329595
0.7612	Intermediate Similarity	NPC308885
0.7612	Intermediate Similarity	NPC255550
0.7612	Intermediate Similarity	NPC326599
0.7607	Intermediate Similarity	NPC155847
0.7607	Intermediate Similarity	NPC289381
0.7586	Intermediate Similarity	NPC107619
0.7583	Intermediate Similarity	NPC477814
0.7581	Intermediate Similarity	NPC264558
0.7563	Intermediate Similarity	NPC52087
0.7563	Intermediate Similarity	NPC30506
0.7557	Intermediate Similarity	NPC62101
0.7557	Intermediate Similarity	NPC95733
0.7551	Intermediate Similarity	NPC107602
0.7541	Intermediate Similarity	NPC290566
0.7541	Intermediate Similarity	NPC145638
0.754	Intermediate Similarity	NPC299252
0.754	Intermediate Similarity	NPC61062
0.754	Intermediate Similarity	NPC277394
0.7534	Intermediate Similarity	NPC18614
0.7521	Intermediate Similarity	NPC125732
0.7519	Intermediate Similarity	NPC161593
0.7519	Intermediate Similarity	NPC24125
0.7519	Intermediate Similarity	NPC16031
0.7519	Intermediate Similarity	NPC145888
0.75	Intermediate Similarity	NPC292452
0.75	Intermediate Similarity	NPC51698
0.75	Intermediate Similarity	NPC283760
0.75	Intermediate Similarity	NPC176893
0.75	Intermediate Similarity	NPC191866
0.7481	Intermediate Similarity	NPC45191
0.7481	Intermediate Similarity	NPC473724
0.7481	Intermediate Similarity	NPC211218
0.7481	Intermediate Similarity	NPC473451
0.748	Intermediate Similarity	NPC278652
0.748	Intermediate Similarity	NPC200988
0.748	Intermediate Similarity	NPC610
0.748	Intermediate Similarity	NPC145023
0.748	Intermediate Similarity	NPC222084
0.748	Intermediate Similarity	NPC293619
0.748	Intermediate Similarity	NPC175799
0.7479	Intermediate Similarity	NPC477802
0.7479	Intermediate Similarity	NPC477801
0.7466	Intermediate Similarity	NPC52475
0.7462	Intermediate Similarity	NPC472271
0.7462	Intermediate Similarity	NPC147654
0.7462	Intermediate Similarity	NPC237667
0.746	Intermediate Similarity	NPC4665
0.7459	Intermediate Similarity	NPC95344
0.7458	Intermediate Similarity	NPC161571
0.7458	Intermediate Similarity	NPC275053
0.7458	Intermediate Similarity	NPC248573
0.7456	Intermediate Similarity	NPC45040
0.7447	Intermediate Similarity	NPC106183
0.7438	Intermediate Similarity	NPC1786
0.7438	Intermediate Similarity	NPC294902
0.7438	Intermediate Similarity	NPC1075
0.7436	Intermediate Similarity	NPC32674
0.7429	Intermediate Similarity	NPC323123
0.7424	Intermediate Similarity	NPC131747
0.7424	Intermediate Similarity	NPC257682
0.7424	Intermediate Similarity	NPC146355
0.7422	Intermediate Similarity	NPC86198
0.7422	Intermediate Similarity	NPC470626
0.7419	Intermediate Similarity	NPC227553
0.7417	Intermediate Similarity	NPC79672
0.741	Intermediate Similarity	NPC471283
0.7405	Intermediate Similarity	NPC471314
0.7405	Intermediate Similarity	NPC471315
0.7398	Intermediate Similarity	NPC316052
0.7395	Intermediate Similarity	NPC143659
0.7395	Intermediate Similarity	NPC100340
0.7385	Intermediate Similarity	NPC83279
0.7379	Intermediate Similarity	NPC153644
0.7364	Intermediate Similarity	NPC181969
0.7364	Intermediate Similarity	NPC109371
0.7364	Intermediate Similarity	NPC70084
0.7364	Intermediate Similarity	NPC320987
0.7364	Intermediate Similarity	NPC226629
0.7364	Intermediate Similarity	NPC141791
0.7364	Intermediate Similarity	NPC477803
0.7364	Intermediate Similarity	NPC470214
0.7364	Intermediate Similarity	NPC470215

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 NPC284078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	757
0.2-0.3	1109
0.3-0.4	2245
0.4-0.5	2859
0.5-0.6	1477
0.6-0.7	428
0.7-0.8	92
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD9280	Clinical (unspecified phase)
0.8689	High Similarity	NPD2337	Clinical (unspecified phase)
0.839	Intermediate Similarity	NPD9377	Approved
0.839	Intermediate Similarity	NPD9379	Approved
0.8293	Intermediate Similarity	NPD9381	Approved
0.8293	Intermediate Similarity	NPD9384	Approved
0.8168	Intermediate Similarity	NPD3059	Approved
0.8168	Intermediate Similarity	NPD3062	Approved
0.8168	Intermediate Similarity	NPD3061	Approved
0.811	Intermediate Similarity	NPD5310	Approved
0.811	Intermediate Similarity	NPD5311	Approved
0.8047	Intermediate Similarity	NPD3053	Approved
0.8047	Intermediate Similarity	NPD3055	Approved
0.8045	Intermediate Similarity	NPD5314	Approved
0.8031	Intermediate Similarity	NPD9622	Approved
0.7984	Intermediate Similarity	NPD9621	Approved
0.7984	Intermediate Similarity	NPD9620	Approved
0.7984	Intermediate Similarity	NPD9619	Approved
0.7983	Intermediate Similarity	NPD3021	Approved
0.7983	Intermediate Similarity	NPD3022	Approved
0.7829	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD2674	Phase 3
0.7761	Intermediate Similarity	NPD1558	Phase 1
0.7744	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD597	Approved
0.7744	Intermediate Similarity	NPD598	Approved
0.7744	Intermediate Similarity	NPD601	Approved
0.7687	Intermediate Similarity	NPD1136	Approved
0.7687	Intermediate Similarity	NPD1132	Approved
0.7687	Intermediate Similarity	NPD1130	Approved
0.7676	Intermediate Similarity	NPD4123	Phase 3
0.7647	Intermediate Similarity	NPD817	Approved
0.7647	Intermediate Similarity	NPD823	Approved
0.7612	Intermediate Similarity	NPD3145	Approved
0.7612	Intermediate Similarity	NPD3144	Approved
0.7581	Intermediate Similarity	NPD2228	Approved
0.7581	Intermediate Similarity	NPD2229	Approved
0.7581	Intermediate Similarity	NPD2234	Approved
0.7554	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD1792	Phase 2
0.7519	Intermediate Similarity	NPD9569	Approved
0.75	Intermediate Similarity	NPD4093	Discontinued
0.7482	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1242	Phase 1
0.7444	Intermediate Similarity	NPD7451	Discontinued
0.7438	Intermediate Similarity	NPD1445	Approved
0.7438	Intermediate Similarity	NPD1444	Approved
0.7422	Intermediate Similarity	NPD1759	Phase 1
0.7417	Intermediate Similarity	NPD9610	Approved
0.7417	Intermediate Similarity	NPD9608	Approved
0.7415	Intermediate Similarity	NPD4675	Approved
0.7415	Intermediate Similarity	NPD4678	Approved
0.7357	Intermediate Similarity	NPD9570	Approved
0.7348	Intermediate Similarity	NPD1669	Approved
0.7344	Intermediate Similarity	NPD1758	Phase 1
0.7328	Intermediate Similarity	NPD2934	Approved
0.7328	Intermediate Similarity	NPD2933	Approved
0.7324	Intermediate Similarity	NPD3060	Approved
0.7313	Intermediate Similarity	NPD257	Approved
0.7313	Intermediate Similarity	NPD258	Approved
0.7308	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD259	Phase 1
0.7293	Intermediate Similarity	NPD2922	Phase 1
0.728	Intermediate Similarity	NPD228	Approved
0.7279	Intermediate Similarity	NPD9537	Phase 1
0.7279	Intermediate Similarity	NPD9536	Phase 1
0.7273	Intermediate Similarity	NPD2561	Approved
0.7273	Intermediate Similarity	NPD2562	Approved
0.7266	Intermediate Similarity	NPD2568	Approved
0.7265	Intermediate Similarity	NPD2860	Approved
0.7265	Intermediate Similarity	NPD2859	Approved
0.7252	Intermediate Similarity	NPD1983	Approved
0.7252	Intermediate Similarity	NPD3421	Phase 3
0.7252	Intermediate Similarity	NPD1980	Approved
0.7252	Intermediate Similarity	NPD1981	Approved
0.7244	Intermediate Similarity	NPD9618	Approved
0.7244	Intermediate Similarity	NPD9614	Approved
0.723	Intermediate Similarity	NPD4005	Discontinued
0.7227	Intermediate Similarity	NPD3020	Approved
0.7222	Intermediate Similarity	NPD302	Approved
0.7218	Intermediate Similarity	NPD4659	Approved
0.7218	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3553	Approved
0.7214	Intermediate Similarity	NPD3554	Approved
0.7214	Intermediate Similarity	NPD3555	Approved
0.7214	Intermediate Similarity	NPD3552	Approved
0.7209	Intermediate Similarity	NPD317	Approved
0.7209	Intermediate Similarity	NPD9616	Approved
0.7209	Intermediate Similarity	NPD856	Approved
0.7209	Intermediate Similarity	NPD9613	Approved
0.7209	Intermediate Similarity	NPD318	Approved
0.7209	Intermediate Similarity	NPD16	Approved
0.7209	Intermediate Similarity	NPD9615	Approved
0.7206	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD555	Phase 2
0.7176	Intermediate Similarity	NPD1751	Approved
0.7154	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD316	Approved
0.7153	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6331	Phase 2
0.7153	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD9273	Approved
0.7132	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6346	Approved
0.7111	Intermediate Similarity	NPD4103	Phase 2
0.7111	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1791	Approved
0.7109	Intermediate Similarity	NPD1793	Approved
0.7095	Intermediate Similarity	NPD2122	Discontinued
0.7075	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1375	Discontinued
0.7055	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3845	Phase 1
0.705	Intermediate Similarity	NPD6405	Approved
0.705	Intermediate Similarity	NPD6407	Approved
0.7039	Intermediate Similarity	NPD2977	Approved
0.7039	Intermediate Similarity	NPD2978	Approved
0.7027	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5303	Approved
0.7023	Intermediate Similarity	NPD5304	Approved
0.7013	Intermediate Similarity	NPD5604	Discontinued
0.7007	Intermediate Similarity	NPD2420	Approved
0.7007	Intermediate Similarity	NPD2421	Approved
0.7	Intermediate Similarity	NPD826	Approved
0.7	Intermediate Similarity	NPD825	Approved
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1613	Approved
0.6993	Remote Similarity	NPD2161	Phase 2
0.6992	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2219	Phase 1
0.6957	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.695	Remote Similarity	NPD274	Approved
0.695	Remote Similarity	NPD275	Approved
0.694	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5772	Approved
0.6928	Remote Similarity	NPD5773	Approved
0.6923	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3400	Discontinued
0.6917	Remote Similarity	NPD2668	Approved
0.6917	Remote Similarity	NPD2667	Approved
0.6906	Remote Similarity	NPD5156	Approved
0.6906	Remote Similarity	NPD2372	Approved
0.6906	Remote Similarity	NPD5155	Approved
0.6906	Remote Similarity	NPD3136	Phase 2
0.6903	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7153	Discontinued
0.6892	Remote Similarity	NPD4357	Discontinued
0.6891	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2232	Approved
0.6889	Remote Similarity	NPD2230	Approved
0.6889	Remote Similarity	NPD2233	Approved
0.6885	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3636	Approved
0.6884	Remote Similarity	NPD3635	Approved
0.6884	Remote Similarity	NPD3637	Approved
0.6879	Remote Similarity	NPD1555	Discontinued
0.6879	Remote Similarity	NPD943	Approved
0.6875	Remote Similarity	NPD7450	Phase 2
0.687	Remote Similarity	NPD9568	Approved
0.6857	Remote Similarity	NPD5718	Phase 2
0.6857	Remote Similarity	NPD5111	Phase 2
0.6857	Remote Similarity	NPD5109	Approved
0.6857	Remote Similarity	NPD5110	Phase 2
0.6849	Remote Similarity	NPD4162	Approved
0.6849	Remote Similarity	NPD4237	Approved
0.6849	Remote Similarity	NPD4236	Phase 3
0.6842	Remote Similarity	NPD111	Approved
0.6838	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3595	Approved
0.6835	Remote Similarity	NPD3594	Approved
0.6835	Remote Similarity	NPD2606	Approved
0.6835	Remote Similarity	NPD2605	Approved
0.6833	Remote Similarity	NPD844	Approved
0.6829	Remote Similarity	NPD846	Approved
0.6829	Remote Similarity	NPD940	Approved
0.6821	Remote Similarity	NPD1972	Approved
0.6821	Remote Similarity	NPD1973	Approved
0.6821	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD599	Approved
0.6812	Remote Similarity	NPD602	Approved
0.6812	Remote Similarity	NPD6584	Phase 3
0.6812	Remote Similarity	NPD858	Approved
0.6812	Remote Similarity	NPD859	Approved
0.6812	Remote Similarity	NPD2195	Approved
0.6812	Remote Similarity	NPD2194	Approved
0.6809	Remote Similarity	NPD840	Approved
0.6809	Remote Similarity	NPD839	Approved
0.6809	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD709	Approved
0.6791	Remote Similarity	NPD2286	Discontinued
0.6783	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD288	Approved
0.6776	Remote Similarity	NPD3455	Phase 2
0.6769	Remote Similarity	NPD5283	Phase 1
0.6765	Remote Similarity	NPD2231	Phase 2
0.6765	Remote Similarity	NPD2235	Phase 2
0.6761	Remote Similarity	NPD2238	Phase 2

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