NPASS Compound

Structure

NPC130570 OpenBabel07101718312D 26 30 0 0 0 0 0 0 0 0999 V2000 5.1006 1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7624 -0.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1006 0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7624 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3686 1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 -0.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0322 -0.5862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6939 2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2346 2.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 -1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3686 0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2346 0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0267 -0.4817 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6884 1.9680 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2346 3.4965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 -2.0102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 12 1 0 0 0 0 2 4 2 0 0 0 0 2 13 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 23 1 0 0 0 0 8 11 1 0 0 0 0 8 24 2 0 0 0 0 9 16 2 0 0 0 0 9 21 1 0 0 0 0 10 17 2 0 0 0 0 10 22 1 0 0 0 0 11 16 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	344.26
LogP:	3.073
LogD:	2.954
LogS:	-4.679
# Rotatable Bonds:	2
TPSA:	97.82
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	2.581
Fsp3:	0.0
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:	-5.063
MDCK Permeability:	5.519993919733679e-06
Pgp-inhibitor:	0.122
Pgp-substrate:	0.25
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.581
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	96.27384185791016%
Volume Distribution (VD):	1.752
Pgp-substrate:	2.235457420349121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.369
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.962
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.991
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	7.25
Half-life (T1/2):	0.697

ADMET: Toxicity

hERG Blockers:	0.575
Human Hepatotoxicity (H-HT):	0.821
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.916
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.25
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.08
Respiratory Toxicity:	0.668

Download Data

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

Natural Product: NPC130570

Natural Product ID:	NPC130570
*Common Name:**	Hyrtinadine A
IUPAC Name:	3-[2-(5-hydroxy-1H-indol-3-yl)pyrimidin-5-yl]-1H-indol-5-ol
Synonyms:
Standard InCHIKey:	BCHVDGBLKXHBKK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14N4O2/c25-12-1-3-18-14(5-12)16(9-21-18)11-7-23-20(24-8-11)17-10-22-19-4-2-13(26)6-15(17)19/h1-10,21-22,25-26H
SMILES:	Oc1ccc2c(c1)c(c[nH]2)c1ncc(cn1)c1c[nH]c2c1cc(O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426727
PubChem CID:	16115665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*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
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514320]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497952]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17378531]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19167886]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19783432]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	Australian	n.a.	PMID[24973030]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28834433]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	1.0	ug.mL-1	PMID[559353]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[559353]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	>	100000.0	nM	PMID[559354]

☑ 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 NPC130570 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	906
0.1-0.2	7782
0.2-0.3	10397
0.3-0.4	16129
0.4-0.5	3646
0.5-0.6	2119
0.6-0.7	1443
0.7-0.8	253
0.8-0.85	20
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8514	High Similarity	NPC39092
0.8469	Intermediate Similarity	NPC471603
0.843	Intermediate Similarity	NPC295452
0.843	Intermediate Similarity	NPC171393
0.8325	Intermediate Similarity	NPC77555
0.8308	Intermediate Similarity	NPC99666
0.8221	Intermediate Similarity	NPC475070
0.8191	Intermediate Similarity	NPC314002
0.8182	Intermediate Similarity	NPC220765
0.8141	Intermediate Similarity	NPC204717
0.814	Intermediate Similarity	NPC304926
0.814	Intermediate Similarity	NPC476041
0.812	Intermediate Similarity	NPC74619
0.8091	Intermediate Similarity	NPC103687
0.8091	Intermediate Similarity	NPC132631
0.8084	Intermediate Similarity	NPC477610
0.806	Intermediate Similarity	NPC171171
0.8028	Intermediate Similarity	NPC5145
0.8	Intermediate Similarity	NPC63109
0.798	Intermediate Similarity	NPC184964
0.7951	Intermediate Similarity	NPC324149
0.7854	Intermediate Similarity	NPC477609
0.7837	Intermediate Similarity	NPC242209
0.7805	Intermediate Similarity	NPC472289
0.7799	Intermediate Similarity	NPC156704
0.7783	Intermediate Similarity	NPC276657
0.7778	Intermediate Similarity	NPC477607
0.7778	Intermediate Similarity	NPC477608
0.7756	Intermediate Similarity	NPC46580
0.7753	Intermediate Similarity	NPC207686
0.7733	Intermediate Similarity	NPC6215
0.7731	Intermediate Similarity	NPC476116
0.7689	Intermediate Similarity	NPC45459
0.7689	Intermediate Similarity	NPC315491
0.7685	Intermediate Similarity	NPC144114
0.7685	Intermediate Similarity	NPC477891
0.7674	Intermediate Similarity	NPC477113
0.7671	Intermediate Similarity	NPC282247
0.7656	Intermediate Similarity	NPC307963
0.7628	Intermediate Similarity	NPC470500
0.7617	Intermediate Similarity	NPC178858
0.7606	Intermediate Similarity	NPC213308
0.7604	Intermediate Similarity	NPC477111
0.7604	Intermediate Similarity	NPC476465
0.7594	Intermediate Similarity	NPC192315
0.7591	Intermediate Similarity	NPC266931
0.7583	Intermediate Similarity	NPC251090
0.7581	Intermediate Similarity	NPC77101
0.7562	Intermediate Similarity	NPC208060
0.7559	Intermediate Similarity	NPC476167
0.7548	Intermediate Similarity	NPC296527
0.7548	Intermediate Similarity	NPC32771
0.7537	Intermediate Similarity	NPC59269
0.7536	Intermediate Similarity	NPC326634
0.7534	Intermediate Similarity	NPC264285
0.7523	Intermediate Similarity	NPC477110
0.7523	Intermediate Similarity	NPC176538
0.7512	Intermediate Similarity	NPC76748
0.7511	Intermediate Similarity	NPC473317
0.75	Intermediate Similarity	NPC208284
0.75	Intermediate Similarity	NPC193267
0.75	Intermediate Similarity	NPC88363
0.75	Intermediate Similarity	NPC213530
0.7488	Intermediate Similarity	NPC329541
0.7488	Intermediate Similarity	NPC15102
0.7476	Intermediate Similarity	NPC92111
0.7463	Intermediate Similarity	NPC164664
0.7454	Intermediate Similarity	NPC211813
0.7442	Intermediate Similarity	NPC249040
0.7436	Intermediate Similarity	NPC41679
0.7422	Intermediate Similarity	NPC48317
0.7422	Intermediate Similarity	NPC250178
0.7419	Intermediate Similarity	NPC223427
0.7418	Intermediate Similarity	NPC222018
0.7416	Intermediate Similarity	NPC254762
0.7412	Intermediate Similarity	NPC125597
0.7411	Intermediate Similarity	NPC469727
0.7403	Intermediate Similarity	NPC476451
0.7397	Intermediate Similarity	NPC88008
0.7393	Intermediate Similarity	NPC15801
0.7373	Intermediate Similarity	NPC81175
0.7366	Intermediate Similarity	NPC96890
0.7337	Intermediate Similarity	NPC131718
0.7331	Intermediate Similarity	NPC477861
0.7327	Intermediate Similarity	NPC278874
0.7325	Intermediate Similarity	NPC16352
0.7316	Intermediate Similarity	NPC253580
0.7309	Intermediate Similarity	NPC128084
0.7306	Intermediate Similarity	NPC285558
0.7299	Intermediate Similarity	NPC128751
0.7299	Intermediate Similarity	NPC246700
0.7299	Intermediate Similarity	NPC230805
0.7289	Intermediate Similarity	NPC170114
0.7286	Intermediate Similarity	NPC92796
0.7286	Intermediate Similarity	NPC135141
0.7285	Intermediate Similarity	NPC171787
0.7284	Intermediate Similarity	NPC326363
0.7277	Intermediate Similarity	NPC295228
0.7273	Intermediate Similarity	NPC470126
0.7265	Intermediate Similarity	NPC180504
0.7264	Intermediate Similarity	NPC106833
0.7264	Intermediate Similarity	NPC469497
0.7261	Intermediate Similarity	NPC245348
0.726	Intermediate Similarity	NPC476098
0.726	Intermediate Similarity	NPC475774
0.7255	Intermediate Similarity	NPC105758
0.7255	Intermediate Similarity	NPC476688
0.7255	Intermediate Similarity	NPC476686
0.7246	Intermediate Similarity	NPC184225
0.7244	Intermediate Similarity	NPC470549
0.7241	Intermediate Similarity	NPC156003
0.7241	Intermediate Similarity	NPC63751
0.7234	Intermediate Similarity	NPC325976
0.7232	Intermediate Similarity	NPC316981
0.7232	Intermediate Similarity	NPC219087
0.7229	Intermediate Similarity	NPC60006
0.7229	Intermediate Similarity	NPC214980
0.7222	Intermediate Similarity	NPC469554
0.722	Intermediate Similarity	NPC167860
0.722	Intermediate Similarity	NPC474409
0.722	Intermediate Similarity	NPC123976
0.7215	Intermediate Similarity	NPC470678
0.7214	Intermediate Similarity	NPC224632
0.7209	Intermediate Similarity	NPC276517
0.7203	Intermediate Similarity	NPC477549
0.7189	Intermediate Similarity	NPC131887
0.7181	Intermediate Similarity	NPC27041
0.7178	Intermediate Similarity	NPC102423
0.7175	Intermediate Similarity	NPC80596
0.7167	Intermediate Similarity	NPC314954
0.7166	Intermediate Similarity	NPC478006
0.7163	Intermediate Similarity	NPC106937
0.7163	Intermediate Similarity	NPC72980
0.7162	Intermediate Similarity	NPC270918
0.7155	Intermediate Similarity	NPC2497
0.7149	Intermediate Similarity	NPC471891
0.7149	Intermediate Similarity	NPC101543
0.7143	Intermediate Similarity	NPC153042
0.7143	Intermediate Similarity	NPC227582
0.7143	Intermediate Similarity	NPC11408
0.7143	Intermediate Similarity	NPC167908
0.7143	Intermediate Similarity	NPC211416
0.7143	Intermediate Similarity	NPC48938
0.7137	Intermediate Similarity	NPC469928
0.7137	Intermediate Similarity	NPC183407
0.7136	Intermediate Similarity	NPC321708
0.713	Intermediate Similarity	NPC18348
0.713	Intermediate Similarity	NPC314957
0.7126	Intermediate Similarity	NPC475746
0.7125	Intermediate Similarity	NPC473312
0.7117	Intermediate Similarity	NPC175602
0.7117	Intermediate Similarity	NPC476121
0.7117	Intermediate Similarity	NPC476124
0.7115	Intermediate Similarity	NPC477633
0.7108	Intermediate Similarity	NPC49217
0.7106	Intermediate Similarity	NPC160666
0.7105	Intermediate Similarity	NPC477114
0.7105	Intermediate Similarity	NPC267811
0.7103	Intermediate Similarity	NPC478009
0.7103	Intermediate Similarity	NPC478010
0.7101	Intermediate Similarity	NPC28945
0.71	Intermediate Similarity	NPC470501
0.7097	Intermediate Similarity	NPC150447
0.7094	Intermediate Similarity	NPC97367
0.7094	Intermediate Similarity	NPC317105
0.7091	Intermediate Similarity	NPC232727
0.7087	Intermediate Similarity	NPC132642
0.7083	Intermediate Similarity	NPC217554
0.708	Intermediate Similarity	NPC294620
0.7079	Intermediate Similarity	NPC279918
0.7075	Intermediate Similarity	NPC188387
0.7075	Intermediate Similarity	NPC117980
0.7075	Intermediate Similarity	NPC163421
0.7073	Intermediate Similarity	NPC314882
0.7067	Intermediate Similarity	NPC309845
0.7067	Intermediate Similarity	NPC11464
0.7063	Intermediate Similarity	NPC315467
0.7062	Intermediate Similarity	NPC176127
0.7061	Intermediate Similarity	NPC8022
0.7061	Intermediate Similarity	NPC470799
0.7059	Intermediate Similarity	NPC193761
0.7056	Intermediate Similarity	NPC470502
0.7056	Intermediate Similarity	NPC310118
0.7054	Intermediate Similarity	NPC116555
0.7048	Intermediate Similarity	NPC478074
0.7045	Intermediate Similarity	NPC252338
0.7045	Intermediate Similarity	NPC106771
0.7045	Intermediate Similarity	NPC303820
0.7045	Intermediate Similarity	NPC205254
0.7045	Intermediate Similarity	NPC23420
0.7045	Intermediate Similarity	NPC329793
0.7044	Intermediate Similarity	NPC282231
0.7043	Intermediate Similarity	NPC74360
0.7039	Intermediate Similarity	NPC473764
0.7039	Intermediate Similarity	NPC314940
0.7035	Intermediate Similarity	NPC82370
0.703	Intermediate Similarity	NPC230869
0.7027	Intermediate Similarity	NPC476138
0.7027	Intermediate Similarity	NPC200836
0.7027	Intermediate Similarity	NPC245816

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 NPC130570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	706
0.2-0.3	752
0.3-0.4	2023
0.4-0.5	2291
0.5-0.6	1707
0.6-0.7	1096
0.7-0.8	152
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD3013	Phase 3
0.8462	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8178	Intermediate Similarity	NPD7112	Discontinued
0.8068	Intermediate Similarity	NPD3814	Phase 1
0.7971	Intermediate Similarity	NPD7948	Phase 1
0.792	Intermediate Similarity	NPD2757	Phase 2
0.7873	Intermediate Similarity	NPD1954	Phase 1
0.787	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD2127	Suspended
0.7834	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5428	Discontinued
0.7812	Intermediate Similarity	NPD6164	Phase 2
0.7812	Intermediate Similarity	NPD6165	Phase 2
0.7803	Intermediate Similarity	NPD4403	Phase 3
0.7803	Intermediate Similarity	NPD4401	Phase 2
0.7763	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7067	Approved
0.7759	Intermediate Similarity	NPD7068	Approved
0.7745	Intermediate Similarity	NPD6243	Phase 3
0.7745	Intermediate Similarity	NPD6244	Phase 3
0.7713	Intermediate Similarity	NPD3233	Phase 2
0.7713	Intermediate Similarity	NPD3234	Phase 3
0.7706	Intermediate Similarity	NPD2794	Discontinued
0.7703	Intermediate Similarity	NPD4998	Phase 3
0.7703	Intermediate Similarity	NPD4999	Phase 3
0.7692	Intermediate Similarity	NPD4615	Phase 2
0.7689	Intermediate Similarity	NPD484	Approved
0.7685	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD5529	Phase 1
0.7682	Intermediate Similarity	NPD5802	Phase 2
0.7679	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD1038	Approved
0.7653	Intermediate Similarity	NPD4511	Phase 1
0.765	Intermediate Similarity	NPD5044	Phase 2
0.7642	Intermediate Similarity	NPD8395	Approved
0.7642	Intermediate Similarity	NPD8396	Approved
0.7639	Intermediate Similarity	NPD1197	Approved
0.7636	Intermediate Similarity	NPD6528	Phase 1
0.7617	Intermediate Similarity	NPD6132	Phase 1
0.7612	Intermediate Similarity	NPD5065	Approved
0.7611	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7051	Phase 3
0.7604	Intermediate Similarity	NPD2189	Approved
0.7604	Intermediate Similarity	NPD4612	Discontinued
0.7604	Intermediate Similarity	NPD2187	Approved
0.7602	Intermediate Similarity	NPD6772	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6958	Approved
0.7602	Intermediate Similarity	NPD6957	Approved
0.7602	Intermediate Similarity	NPD5612	Discontinued
0.76	Intermediate Similarity	NPD5045	Phase 2
0.7597	Intermediate Similarity	NPD3872	Phase 3
0.758	Intermediate Similarity	NPD949	Phase 1
0.7578	Intermediate Similarity	NPD534	Phase 2
0.7578	Intermediate Similarity	NPD537	Phase 2
0.7574	Intermediate Similarity	NPD3962	Phase 2
0.7574	Intermediate Similarity	NPD3959	Phase 2
0.7573	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7423	Phase 2
0.7551	Intermediate Similarity	NPD4442	Phase 2
0.7523	Intermediate Similarity	NPD6711	Approved
0.7522	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD6750	Phase 2
0.7489	Intermediate Similarity	NPD7415	Suspended
0.7488	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD8442	Discontinued
0.7463	Intermediate Similarity	NPD6595	Phase 3
0.7454	Intermediate Similarity	NPD5486	Discontinued
0.7431	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2410	Phase 2
0.7415	Intermediate Similarity	NPD7856	Phase 2
0.7415	Intermediate Similarity	NPD7857	Phase 3
0.7415	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4306	Phase 1
0.7406	Intermediate Similarity	NPD4558	Phase 2
0.7404	Intermediate Similarity	NPD2762	Phase 2
0.7404	Intermediate Similarity	NPD5905	Phase 1
0.7399	Intermediate Similarity	NPD4358	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7445	Phase 1
0.7387	Intermediate Similarity	NPD3330	Phase 1
0.7383	Intermediate Similarity	NPD3830	Phase 1
0.738	Intermediate Similarity	NPD1273	Discontinued
0.7376	Intermediate Similarity	NPD8321	Discontinued
0.7375	Intermediate Similarity	NPD6482	Phase 1
0.7368	Intermediate Similarity	NPD3343	Phase 3
0.7368	Intermediate Similarity	NPD706	Phase 1
0.7358	Intermediate Similarity	NPD994	Phase 2
0.7358	Intermediate Similarity	NPD996	Phase 2
0.7352	Intermediate Similarity	NPD5458	Discontinued
0.735	Intermediate Similarity	NPD7052	Phase 1
0.7345	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6473	Phase 1
0.7339	Intermediate Similarity	NPD2364	Suspended
0.7333	Intermediate Similarity	NPD5644	Phase 1
0.7321	Intermediate Similarity	NPD7188	Phase 3
0.7318	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD796	Phase 2
0.7311	Intermediate Similarity	NPD6572	Phase 2
0.7311	Intermediate Similarity	NPD6573	Phase 3
0.7311	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6760	Discontinued
0.7308	Intermediate Similarity	NPD6970	Phase 2
0.7304	Intermediate Similarity	NPD7603	Discontinued
0.7301	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD2872	Phase 2
0.7284	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4925	Approved
0.7277	Intermediate Similarity	NPD3404	Approved
0.7265	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD1043	Phase 3
0.7261	Intermediate Similarity	NPD1258	Discontinued
0.7261	Intermediate Similarity	NPD3938	Phase 1
0.726	Intermediate Similarity	NPD1895	Discontinued
0.7258	Intermediate Similarity	NPD5949	Phase 3
0.7256	Intermediate Similarity	NPD7935	Phase 2
0.7256	Intermediate Similarity	NPD6594	Discontinued
0.7253	Intermediate Similarity	NPD4995	Approved
0.7253	Intermediate Similarity	NPD4996	Approved
0.7249	Intermediate Similarity	NPD4945	Discontinued
0.7241	Intermediate Similarity	NPD1624	Phase 2
0.724	Intermediate Similarity	NPD4533	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6856	Discontinued
0.7215	Intermediate Similarity	NPD3928	Approved
0.7215	Intermediate Similarity	NPD3931	Approved
0.7209	Intermediate Similarity	NPD1912	Approved
0.7203	Intermediate Similarity	NPD1259	Discontinued
0.7189	Intermediate Similarity	NPD7419	Discontinued
0.7186	Intermediate Similarity	NPD5703	Discontinued
0.7183	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4886	Phase 2
0.7173	Intermediate Similarity	NPD5804	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5413	Phase 2
0.7163	Intermediate Similarity	NPD802	Phase 2
0.7163	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3825	Phase 3
0.7155	Intermediate Similarity	NPD6352	Phase 2
0.7154	Intermediate Similarity	NPD8525	Approved
0.7154	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD1915	Phase 1
0.7148	Intermediate Similarity	NPD7926	Phase 2
0.7136	Intermediate Similarity	NPD3224	Phase 2
0.7126	Intermediate Similarity	NPD5018	Phase 3
0.7125	Intermediate Similarity	NPD5051	Phase 1
0.7118	Intermediate Similarity	NPD5270	Discontinued
0.7115	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6992	Phase 2
0.7113	Intermediate Similarity	NPD4858	Phase 2
0.7111	Intermediate Similarity	NPD4563	Phase 2
0.7106	Intermediate Similarity	NPD8004	Discontinued
0.7106	Intermediate Similarity	NPD2062	Phase 2
0.7101	Intermediate Similarity	NPD2928	Phase 2
0.7097	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5559	Phase 2
0.7094	Intermediate Similarity	NPD5925	Phase 1
0.7091	Intermediate Similarity	NPD6151	Phase 2
0.7091	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5827	Discontinued
0.7087	Intermediate Similarity	NPD6242	Discontinued
0.7085	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2446	Approved
0.7083	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9695	Approved
0.7083	Intermediate Similarity	NPD2445	Approved
0.7082	Intermediate Similarity	NPD4295	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3976	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3255	Phase 1
0.7075	Intermediate Similarity	NPD3254	Phase 1
0.7075	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3500	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5426	Phase 3
0.7064	Intermediate Similarity	NPD3261	Phase 1
0.7056	Intermediate Similarity	NPD7726	Phase 1
0.7056	Intermediate Similarity	NPD6589	Phase 1
0.7054	Intermediate Similarity	NPD5833	Phase 1
0.7048	Intermediate Similarity	NPD4457	Phase 2
0.7046	Intermediate Similarity	NPD7558	Phase 2
0.7046	Intermediate Similarity	NPD4080	Discontinued
0.704	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5118	Phase 2
0.7037	Intermediate Similarity	NPD1234	Discontinued
0.7032	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5885	Approved
0.7032	Intermediate Similarity	NPD6469	Phase 3
0.7031	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4343	Phase 1
0.7025	Intermediate Similarity	NPD7620	Phase 2
0.7022	Intermediate Similarity	NPD7409	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5509	Phase 1
0.7016	Intermediate Similarity	NPD6458	Discontinued

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