NPASS Compound

Structure

NPC295452 OpenBabel07101719122D 23 26 0 0 1 0 0 0 0 0999 V2000 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6646 1.0751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7473 -0.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6428 0.8672 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8337 -0.5341 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 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 3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 4.3587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8025 3.6542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 9 1 0 0 0 0 2 12 1 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 5 14 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 17 2 0 0 0 0 7 18 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 11 15 2 0 0 0 0 12 20 1 0 0 0 0 13 3 1 1 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 6 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.12
Volume:	302.969
LogP:	-1.124
LogD:	-0.066
LogS:	-2.69
# Rotatable Bonds:	3
TPSA:	114.03
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.502
Synthetic Accessibility Score:	3.775
Fsp3:	0.25
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:	-5.67
MDCK Permeability:	2.9717023153352784e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.858
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.552
30% Bioavailability (F30%):	0.839

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.61
Plasma Protein Binding (PPB):	42.78969192504883%
Volume Distribution (VD):	0.724
Pgp-substrate:	67.2004165649414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.749
CYP2D6-inhibitor:	0.382
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.377
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	4.309
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.548
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.596
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC295452

Natural Product ID:	NPC295452
*Common Name:**	Hyrtioreticulin A
IUPAC Name:	(1R,3S)-6-hydroxy-1-(1H-imidazol-5-ylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
Synonyms:	Hyrtioreticulin A
Standard InCHIKey:	VXURZHPEJYLPGK-KGLIPLIRSA-N
Standard InCHI:	InChI=1S/C16H16N4O3/c21-9-1-2-12-10(4-9)11-5-14(16(22)23)19-13(15(11)20-12)3-8-6-17-7-18-8/h1-2,4,6-7,13-14,19-21H,3,5H2,(H,17,18)(H,22,23)/t13-,14+/m1/s1
SMILES:	OC(=O)[C@H]1N[C@H](Cc2cnc[nH]2)c2c(C1)c1cc(O)ccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2046768
PubChem CID:	70694527
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala 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
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[20000782]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22695182]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5282	Individual Protein	Ubiquitin-like modifier-activating enzyme 1	Homo sapiens	IC50	=	2400.0	nM	PMID[488394]

☑ 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 NPC295452 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	617
0.1-0.2	5004
0.2-0.3	12482
0.3-0.4	16713
0.4-0.5	3500
0.5-0.6	2503
0.6-0.7	1582
0.7-0.8	281
0.8-0.85	12
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC171393
0.9254	High Similarity	NPC74619
0.843	Intermediate Similarity	NPC130570
0.8364	Intermediate Similarity	NPC476098
0.8362	Intermediate Similarity	NPC39092
0.831	Intermediate Similarity	NPC315491
0.831	Intermediate Similarity	NPC45459
0.8174	Intermediate Similarity	NPC63109
0.8155	Intermediate Similarity	NPC41679
0.814	Intermediate Similarity	NPC213308
0.8095	Intermediate Similarity	NPC207686
0.8079	Intermediate Similarity	NPC323244
0.8073	Intermediate Similarity	NPC475070
0.8034	Intermediate Similarity	NPC15801
0.8027	Intermediate Similarity	NPC282247
0.8025	Intermediate Similarity	NPC178858
0.8018	Intermediate Similarity	NPC473317
0.7973	Intermediate Similarity	NPC5145
0.794	Intermediate Similarity	NPC328924
0.7922	Intermediate Similarity	NPC6215
0.792	Intermediate Similarity	NPC304926
0.792	Intermediate Similarity	NPC476041
0.7918	Intermediate Similarity	NPC478006
0.7917	Intermediate Similarity	NPC156704
0.7913	Intermediate Similarity	NPC125597
0.7871	Intermediate Similarity	NPC315467
0.787	Intermediate Similarity	NPC229893
0.7854	Intermediate Similarity	NPC69843
0.784	Intermediate Similarity	NPC478009
0.784	Intermediate Similarity	NPC478010
0.7838	Intermediate Similarity	NPC88008
0.7828	Intermediate Similarity	NPC314882
0.7824	Intermediate Similarity	NPC473312
0.7822	Intermediate Similarity	NPC471603
0.7817	Intermediate Similarity	NPC276657
0.7783	Intermediate Similarity	NPC60621
0.7761	Intermediate Similarity	NPC477633
0.776	Intermediate Similarity	NPC314056
0.7758	Intermediate Similarity	NPC270918
0.7756	Intermediate Similarity	NPC77101
0.7748	Intermediate Similarity	NPC473376
0.7731	Intermediate Similarity	NPC99666
0.7731	Intermediate Similarity	NPC184225
0.7725	Intermediate Similarity	NPC319232
0.7725	Intermediate Similarity	NPC24370
0.7717	Intermediate Similarity	NPC192315
0.7686	Intermediate Similarity	NPC478012
0.7686	Intermediate Similarity	NPC478011
0.7682	Intermediate Similarity	NPC476167
0.7674	Intermediate Similarity	NPC321708
0.7671	Intermediate Similarity	NPC77555
0.7668	Intermediate Similarity	NPC478013
0.7664	Intermediate Similarity	NPC62749
0.7656	Intermediate Similarity	NPC314176
0.7652	Intermediate Similarity	NPC264285
0.7627	Intermediate Similarity	NPC326363
0.7621	Intermediate Similarity	NPC82370
0.7617	Intermediate Similarity	NPC314002
0.7606	Intermediate Similarity	NPC220765
0.7595	Intermediate Similarity	NPC476451
0.7588	Intermediate Similarity	NPC477634
0.7585	Intermediate Similarity	NPC156003
0.7583	Intermediate Similarity	NPC28945
0.7581	Intermediate Similarity	NPC171171
0.758	Intermediate Similarity	NPC276517
0.7573	Intermediate Similarity	NPC97902
0.7573	Intermediate Similarity	NPC325976
0.757	Intermediate Similarity	NPC204717
0.7569	Intermediate Similarity	NPC324149
0.7566	Intermediate Similarity	NPC116555
0.7565	Intermediate Similarity	NPC469928
0.7562	Intermediate Similarity	NPC81175
0.7555	Intermediate Similarity	NPC477610
0.7555	Intermediate Similarity	NPC54744
0.7532	Intermediate Similarity	NPC27041
0.7531	Intermediate Similarity	NPC220852
0.7531	Intermediate Similarity	NPC323752
0.75	Intermediate Similarity	NPC211813
0.75	Intermediate Similarity	NPC57398
0.75	Intermediate Similarity	NPC182222
0.7489	Intermediate Similarity	NPC176538
0.7477	Intermediate Similarity	NPC306376
0.7469	Intermediate Similarity	NPC477549
0.7466	Intermediate Similarity	NPC242209
0.7461	Intermediate Similarity	NPC117980
0.7456	Intermediate Similarity	NPC476116
0.7447	Intermediate Similarity	NPC16352
0.7438	Intermediate Similarity	NPC285343
0.7435	Intermediate Similarity	NPC118940
0.7434	Intermediate Similarity	NPC470500
0.7432	Intermediate Similarity	NPC141454
0.7425	Intermediate Similarity	NPC473310
0.7424	Intermediate Similarity	NPC309845
0.7418	Intermediate Similarity	NPC183662
0.7418	Intermediate Similarity	NPC217372
0.7418	Intermediate Similarity	NPC15573
0.7418	Intermediate Similarity	NPC184964
0.7417	Intermediate Similarity	NPC89987
0.7391	Intermediate Similarity	NPC54981
0.7384	Intermediate Similarity	NPC245348
0.7383	Intermediate Similarity	NPC248041
0.7383	Intermediate Similarity	NPC219336
0.7383	Intermediate Similarity	NPC283219
0.7383	Intermediate Similarity	NPC126709
0.7382	Intermediate Similarity	NPC469727
0.7375	Intermediate Similarity	NPC260434
0.7359	Intermediate Similarity	NPC219087
0.7353	Intermediate Similarity	NPC60006
0.735	Intermediate Similarity	NPC475736
0.7349	Intermediate Similarity	NPC477630
0.7349	Intermediate Similarity	NPC477635
0.7339	Intermediate Similarity	NPC471891
0.7336	Intermediate Similarity	NPC171787
0.7328	Intermediate Similarity	NPC476287
0.7324	Intermediate Similarity	NPC203468
0.7324	Intermediate Similarity	NPC110500
0.7324	Intermediate Similarity	NPC149155
0.7322	Intermediate Similarity	NPC476491
0.7321	Intermediate Similarity	NPC131887
0.7319	Intermediate Similarity	NPC74360
0.7313	Intermediate Similarity	NPC165599
0.7312	Intermediate Similarity	NPC475746
0.7309	Intermediate Similarity	NPC91868
0.7309	Intermediate Similarity	NPC63971
0.7308	Intermediate Similarity	NPC472285
0.7306	Intermediate Similarity	NPC477861
0.7306	Intermediate Similarity	NPC46580
0.7304	Intermediate Similarity	NPC478158
0.7296	Intermediate Similarity	NPC478157
0.7294	Intermediate Similarity	NPC15102
0.7293	Intermediate Similarity	NPC244741
0.7293	Intermediate Similarity	NPC53344
0.729	Intermediate Similarity	NPC267885
0.7288	Intermediate Similarity	NPC272174
0.7284	Intermediate Similarity	NPC110182
0.7277	Intermediate Similarity	NPC477609
0.7273	Intermediate Similarity	NPC53534
0.7269	Intermediate Similarity	NPC64216
0.7265	Intermediate Similarity	NPC322064
0.7265	Intermediate Similarity	NPC101350
0.7265	Intermediate Similarity	NPC36405
0.7261	Intermediate Similarity	NPC71238
0.7261	Intermediate Similarity	NPC476465
0.7261	Intermediate Similarity	NPC470730
0.7261	Intermediate Similarity	NPC470729
0.7261	Intermediate Similarity	NPC477175
0.7261	Intermediate Similarity	NPC477176
0.726	Intermediate Similarity	NPC235684
0.7257	Intermediate Similarity	NPC249040
0.7256	Intermediate Similarity	NPC84827
0.7256	Intermediate Similarity	NPC145885
0.7256	Intermediate Similarity	NPC111275
0.7256	Intermediate Similarity	NPC14113
0.7249	Intermediate Similarity	NPC175602
0.7244	Intermediate Similarity	NPC67288
0.7241	Intermediate Similarity	NPC320968
0.7237	Intermediate Similarity	NPC223427
0.7234	Intermediate Similarity	NPC267811
0.7231	Intermediate Similarity	NPC477177
0.7231	Intermediate Similarity	NPC474877
0.7231	Intermediate Similarity	NPC475969
0.7231	Intermediate Similarity	NPC475859
0.7227	Intermediate Similarity	NPC17059
0.7224	Intermediate Similarity	NPC235685
0.7222	Intermediate Similarity	NPC153400
0.722	Intermediate Similarity	NPC307963
0.7208	Intermediate Similarity	NPC132631
0.7208	Intermediate Similarity	NPC103687
0.7203	Intermediate Similarity	NPC303658
0.7202	Intermediate Similarity	NPC165743
0.7202	Intermediate Similarity	NPC48938
0.72	Intermediate Similarity	NPC227582
0.7197	Intermediate Similarity	NPC122436
0.7191	Intermediate Similarity	NPC330009
0.7191	Intermediate Similarity	NPC470799
0.7191	Intermediate Similarity	NPC8022
0.7189	Intermediate Similarity	NPC469896
0.7188	Intermediate Similarity	NPC41982
0.7186	Intermediate Similarity	NPC266249
0.7185	Intermediate Similarity	NPC474896
0.7184	Intermediate Similarity	NPC295228
0.7183	Intermediate Similarity	NPC473800
0.7176	Intermediate Similarity	NPC258048
0.7173	Intermediate Similarity	NPC193267
0.7173	Intermediate Similarity	NPC213530
0.7172	Intermediate Similarity	NPC63279
0.7171	Intermediate Similarity	NPC152620
0.7162	Intermediate Similarity	NPC245816
0.7162	Intermediate Similarity	NPC476138
0.7161	Intermediate Similarity	NPC312645
0.7161	Intermediate Similarity	NPC238945
0.7156	Intermediate Similarity	NPC251090
0.7155	Intermediate Similarity	NPC61038
0.7155	Intermediate Similarity	NPC31097
0.7149	Intermediate Similarity	NPC314954
0.7149	Intermediate Similarity	NPC477607
0.7149	Intermediate Similarity	NPC477608
0.7149	Intermediate Similarity	NPC54537
0.7143	Intermediate Similarity	NPC472099
0.7143	Intermediate Similarity	NPC321428

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 NPC295452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	639
0.2-0.3	861
0.3-0.4	1821
0.4-0.5	2488
0.5-0.6	1831
0.6-0.7	1118
0.7-0.8	102
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.831	Intermediate Similarity	NPD484	Approved
0.7958	Intermediate Similarity	NPD4558	Phase 2
0.7922	Intermediate Similarity	NPD6165	Phase 2
0.7922	Intermediate Similarity	NPD6164	Phase 2
0.7845	Intermediate Similarity	NPD8292	Phase 2
0.78	Intermediate Similarity	NPD4442	Phase 2
0.7797	Intermediate Similarity	NPD7112	Discontinued
0.7788	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3962	Phase 2
0.7759	Intermediate Similarity	NPD3959	Phase 2
0.7743	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7603	Discontinued
0.7717	Intermediate Similarity	NPD5018	Phase 3
0.7686	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD534	Phase 2
0.7619	Intermediate Similarity	NPD537	Phase 2
0.7615	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7415	Suspended
0.7544	Intermediate Similarity	NPD949	Phase 1
0.7531	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD3814	Phase 1
0.7521	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD2880	Discontinued
0.751	Intermediate Similarity	NPD8442	Discontinued
0.75	Intermediate Similarity	NPD3013	Phase 3
0.75	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4414	Discontinued
0.7467	Intermediate Similarity	NPD7470	Discontinued
0.7459	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7948	Phase 1
0.7429	Intermediate Similarity	NPD7067	Approved
0.7429	Intermediate Similarity	NPD7068	Approved
0.7424	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3343	Phase 3
0.7403	Intermediate Similarity	NPD7689	Approved
0.7401	Intermediate Similarity	NPD2008	Discontinued
0.7391	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1571	Phase 2
0.7361	Intermediate Similarity	NPD2095	Phase 2
0.7361	Intermediate Similarity	NPD2094	Phase 2
0.7361	Intermediate Similarity	NPD2092	Phase 2
0.7361	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1572	Phase 2
0.7342	Intermediate Similarity	NPD8641	Approved
0.7336	Intermediate Similarity	NPD2442	Approved
0.7336	Intermediate Similarity	NPD4612	Discontinued
0.7336	Intermediate Similarity	NPD2443	Approved
0.733	Intermediate Similarity	NPD994	Phase 2
0.733	Intermediate Similarity	NPD996	Phase 2
0.7327	Intermediate Similarity	NPD2096	Phase 2
0.7327	Intermediate Similarity	NPD2091	Phase 2
0.7324	Intermediate Similarity	NPD482	Approved
0.7296	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7970	Approved
0.7293	Intermediate Similarity	NPD796	Phase 2
0.7288	Intermediate Similarity	NPD5827	Discontinued
0.7284	Intermediate Similarity	NPD2794	Discontinued
0.7284	Intermediate Similarity	NPD2411	Approved
0.7281	Intermediate Similarity	NPD5901	Discontinued
0.728	Intermediate Similarity	NPD5482	Discontinued
0.7273	Intermediate Similarity	NPD7465	Suspended
0.7269	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6753	Phase 1
0.7269	Intermediate Similarity	NPD6752	Phase 1
0.7266	Intermediate Similarity	NPD8525	Approved
0.7265	Intermediate Similarity	NPD5612	Discontinued
0.7262	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2187	Approved
0.7261	Intermediate Similarity	NPD2189	Approved
0.726	Intermediate Similarity	NPD706	Phase 1
0.7253	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD2127	Suspended
0.7247	Intermediate Similarity	NPD7860	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8524	Approved
0.724	Intermediate Similarity	NPD5644	Phase 1
0.7238	Intermediate Similarity	NPD4403	Phase 3
0.7238	Intermediate Similarity	NPD4401	Phase 2
0.7234	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2813	Phase 3
0.7232	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD1038	Approved
0.7218	Intermediate Similarity	NPD5802	Phase 2
0.7217	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1197	Approved
0.7209	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5426	Phase 3
0.72	Intermediate Similarity	NPD8421	Discontinued
0.7191	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5116	Phase 1
0.7188	Intermediate Similarity	NPD7923	Phase 2
0.7177	Intermediate Similarity	NPD6473	Phase 1
0.7174	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4080	Discontinued
0.7166	Intermediate Similarity	NPD7117	Phase 2
0.7162	Intermediate Similarity	NPD1043	Phase 3
0.7161	Intermediate Similarity	NPD8271	Discontinued
0.7155	Intermediate Similarity	NPD2408	Discontinued
0.7155	Intermediate Similarity	NPD1600	Suspended
0.7149	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6856	Discontinued
0.7143	Intermediate Similarity	NPD6970	Phase 2
0.7143	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD7051	Phase 3
0.7137	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2762	Phase 2
0.7136	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6228	Discontinued
0.7119	Intermediate Similarity	NPD6958	Approved
0.7119	Intermediate Similarity	NPD6957	Approved
0.7107	Intermediate Similarity	NPD4845	Discontinued
0.7102	Intermediate Similarity	NPD2471	Approved
0.7102	Intermediate Similarity	NPD2472	Approved
0.7097	Intermediate Similarity	NPD6992	Phase 2
0.7095	Intermediate Similarity	NPD1258	Discontinued
0.7089	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5065	Approved
0.7078	Intermediate Similarity	NPD1895	Discontinued
0.7077	Intermediate Similarity	NPD7273	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6243	Phase 3
0.7075	Intermediate Similarity	NPD6244	Phase 3
0.7071	Intermediate Similarity	NPD6242	Discontinued
0.707	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1273	Discontinued
0.7064	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD3918	Approved
0.7064	Intermediate Similarity	NPD3917	Approved
0.7056	Intermediate Similarity	NPD3500	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5045	Phase 2
0.7046	Intermediate Similarity	NPD3353	Approved
0.7046	Intermediate Similarity	NPD6711	Approved
0.7046	Intermediate Similarity	NPD6643	Discontinued
0.704	Intermediate Similarity	NPD6490	Phase 2
0.704	Intermediate Similarity	NPD7856	Phase 2
0.704	Intermediate Similarity	NPD7857	Phase 3
0.7039	Intermediate Similarity	NPD7665	Phase 2
0.7039	Intermediate Similarity	NPD7666	Phase 3
0.7037	Intermediate Similarity	NPD750	Phase 2
0.7037	Intermediate Similarity	NPD1037	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6595	Phase 3
0.7026	Intermediate Similarity	NPD6403	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3938	Phase 1
0.7022	Intermediate Similarity	NPD4615	Phase 2
0.7022	Intermediate Similarity	NPD6665	Discontinued
0.7021	Intermediate Similarity	NPD3915	Approved
0.7017	Intermediate Similarity	NPD7423	Phase 2
0.7017	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1954	Phase 1
0.7008	Intermediate Similarity	NPD5509	Phase 1
0.7008	Intermediate Similarity	NPD5559	Phase 2
0.7004	Intermediate Similarity	NPD2757	Phase 2
0.7	Intermediate Similarity	NPD4511	Phase 1
0.6996	Remote Similarity	NPD6352	Phase 2
0.6992	Remote Similarity	NPD8119	Discontinued
0.6992	Remote Similarity	NPD4885	Approved
0.6991	Remote Similarity	NPD5428	Discontinued
0.6988	Remote Similarity	NPD6531	Approved
0.6988	Remote Similarity	NPD6530	Approved
0.6987	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6999	Discontinued
0.6987	Remote Similarity	NPD3354	Phase 2
0.6983	Remote Similarity	NPD1915	Phase 1
0.6982	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8261	Discontinued
0.6974	Remote Similarity	NPD3830	Phase 1
0.6971	Remote Similarity	NPD7726	Phase 1
0.6966	Remote Similarity	NPD2916	Discontinued
0.6966	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2509	Approved
0.6966	Remote Similarity	NPD2510	Approved
0.6966	Remote Similarity	NPD5529	Phase 1
0.696	Remote Similarity	NPD4999	Phase 3
0.696	Remote Similarity	NPD4998	Phase 3
0.6955	Remote Similarity	NPD3043	Approved
0.6955	Remote Similarity	NPD3042	Approved
0.6953	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5450	Discontinued
0.6946	Remote Similarity	NPD8256	Approved
0.6946	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8257	Approved
0.6944	Remote Similarity	NPD6573	Phase 3
0.6944	Remote Similarity	NPD6572	Phase 2
0.6939	Remote Similarity	NPD7767	Approved
0.6938	Remote Similarity	NPD8049	Phase 2
0.6934	Remote Similarity	NPD8349	Phase 1
0.6933	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7898	Clinical (unspecified phase)

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