NPASS Compound

Structure

NPC18487 OpenBabel07101719152D 32 35 0 0 0 0 0 0 0 0999 V2000 -6.2399 4.3489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3197 2.6342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3264 3.9422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2218 2.9477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3083 2.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2038 1.5464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7989 1.6448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2989 2.5108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7111 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2989 2.5108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7989 3.3768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 1.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2989 0.7788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0823 0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 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 -2.4242 1.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7989 1.6448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2902 1.1397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 0.7788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7989 3.3768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 0.2788 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 -0.5878 -0.8090 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 -1.6810 0.9706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7111 -0.0302 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 6.2989 4.2429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 18 1 0 0 0 0 3 32 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 8 19 2 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 21 2 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 22 2 0 0 0 0 16 26 1 0 0 0 0 17 25 2 0 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 18 28 2 0 0 0 0 21 29 1 0 0 0 0 22 28 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 27 2 0 0 0 0 26 30 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	429.24
Volume:	465.528
LogP:	6.415
LogD:	4.913
LogS:	-3.13
# Rotatable Bonds:	7
TPSA:	76.83
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	3.447
Fsp3:	0.259
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.827
MDCK Permeability:	7.052636192383943e-06
Pgp-inhibitor:	0.996
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.776

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	99.07572937011719%
Volume Distribution (VD):	2.099
Pgp-substrate:	0.7170132398605347%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.979
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.707

ADMET: Excretion

Clearance (CL):	4.804
Half-life (T1/2):	0.525

ADMET: Toxicity

hERG Blockers:	0.887
Human Hepatotoxicity (H-HT):	0.444
Drug-inuced Liver Injury (DILI):	0.386
AMES Toxicity:	0.397
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.934
Carcinogencity:	0.714
Eye Corrosion:	0.003
Eye Irritation:	0.137
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC18487

Natural Product ID:	NPC18487
*Common Name:**	OXHNVYWPYWEZOW-JWGURIENSA-N
IUPAC Name:	n.a.
Synonyms:	2-(P-Hydroxybenzyl)Prodigiosin
Standard InCHIKey:	OXHNVYWPYWEZOW-JWGURIENSA-N
Standard InCHI:	InChI=1S/C27H31N3O2/c1-4-5-6-7-20-15-22(28-18(20)2)16-26-27(32-3)17-25(30-26)24-13-10-21(29-24)14-19-8-11-23(31)12-9-19/h8-13,15-17,29-31H,4-7,14H2,1-3H3/b22-16-
SMILES:	CCCCCC1=C/C(=C/c2[nH]c(cc2OC)c2ccc([nH]2)Cc2ccc(cc2)O)/N=C1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL578220
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002028] Dipyrrins

*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
NPO2937	Pseudoalteromonas rubra	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18922034]
NPO2937	Pseudoalteromonas rubra	Species	Pseudoalteromonadaceae	Bacteria	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	1300.0	nM	PMID[463373]

☑ 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 NPC18487 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	457
0.1-0.2	3968
0.2-0.3	13207
0.3-0.4	7184
0.4-0.5	12493
0.5-0.6	3839
0.6-0.7	1322
0.7-0.8	221
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8556	High Similarity	NPC84853
0.8351	Intermediate Similarity	NPC223427
0.8333	Intermediate Similarity	NPC187558
0.829	Intermediate Similarity	NPC19872
0.8227	Intermediate Similarity	NPC473179
0.8069	Intermediate Similarity	NPC469592
0.8069	Intermediate Similarity	NPC471080
0.8041	Intermediate Similarity	NPC243834
0.8041	Intermediate Similarity	NPC70956
0.8038	Intermediate Similarity	NPC473185
0.799	Intermediate Similarity	NPC470799
0.799	Intermediate Similarity	NPC8022
0.7921	Intermediate Similarity	NPC199667
0.7913	Intermediate Similarity	NPC469594
0.7874	Intermediate Similarity	NPC213530
0.7874	Intermediate Similarity	NPC193267
0.7871	Intermediate Similarity	NPC473181
0.7868	Intermediate Similarity	NPC128823
0.7857	Intermediate Similarity	NPC267928
0.7843	Intermediate Similarity	NPC26679
0.7837	Intermediate Similarity	NPC132642
0.783	Intermediate Similarity	NPC314954
0.78	Intermediate Similarity	NPC245816
0.78	Intermediate Similarity	NPC476138
0.7789	Intermediate Similarity	NPC232727
0.7783	Intermediate Similarity	NPC185782
0.7772	Intermediate Similarity	NPC242928
0.7772	Intermediate Similarity	NPC193777
0.7767	Intermediate Similarity	NPC473182
0.7756	Intermediate Similarity	NPC94157
0.7756	Intermediate Similarity	NPC294620
0.775	Intermediate Similarity	NPC199277
0.775	Intermediate Similarity	NPC135887
0.775	Intermediate Similarity	NPC475112
0.775	Intermediate Similarity	NPC475085
0.775	Intermediate Similarity	NPC291535
0.7749	Intermediate Similarity	NPC84478
0.7742	Intermediate Similarity	NPC473183
0.774	Intermediate Similarity	NPC303658
0.7721	Intermediate Similarity	NPC101543
0.7721	Intermediate Similarity	NPC469554
0.7714	Intermediate Similarity	NPC477532
0.7673	Intermediate Similarity	NPC470500
0.767	Intermediate Similarity	NPC473180
0.765	Intermediate Similarity	NPC473184
0.7644	Intermediate Similarity	NPC474798
0.763	Intermediate Similarity	NPC310118
0.7624	Intermediate Similarity	NPC475774
0.761	Intermediate Similarity	NPC209769
0.761	Intermediate Similarity	NPC469589
0.759	Intermediate Similarity	NPC110741
0.7576	Intermediate Similarity	NPC131017
0.7573	Intermediate Similarity	NPC167860
0.7573	Intermediate Similarity	NPC123976
0.757	Intermediate Similarity	NPC202503
0.7563	Intermediate Similarity	NPC324149
0.7562	Intermediate Similarity	NPC176538
0.7552	Intermediate Similarity	NPC161887
0.7552	Intermediate Similarity	NPC314394
0.755	Intermediate Similarity	NPC72211
0.7549	Intermediate Similarity	NPC476106
0.7547	Intermediate Similarity	NPC60621
0.7539	Intermediate Similarity	NPC72980
0.7526	Intermediate Similarity	NPC94943
0.7526	Intermediate Similarity	NPC42591
0.7525	Intermediate Similarity	NPC307963
0.7513	Intermediate Similarity	NPC474409
0.7513	Intermediate Similarity	NPC176127
0.7512	Intermediate Similarity	NPC475253
0.7512	Intermediate Similarity	NPC476167
0.75	Intermediate Similarity	NPC470930
0.75	Intermediate Similarity	NPC252251
0.75	Intermediate Similarity	NPC48353
0.7488	Intermediate Similarity	NPC5145
0.7487	Intermediate Similarity	NPC314573
0.7476	Intermediate Similarity	NPC170114
0.7476	Intermediate Similarity	NPC475910
0.7476	Intermediate Similarity	NPC287208
0.7474	Intermediate Similarity	NPC190007
0.7473	Intermediate Similarity	NPC26872
0.7464	Intermediate Similarity	NPC476287
0.7464	Intermediate Similarity	NPC266931
0.7463	Intermediate Similarity	NPC192315
0.7454	Intermediate Similarity	NPC110151
0.7451	Intermediate Similarity	NPC162484
0.745	Intermediate Similarity	NPC70259
0.7446	Intermediate Similarity	NPC26850
0.7431	Intermediate Similarity	NPC477531
0.7429	Intermediate Similarity	NPC470549
0.7423	Intermediate Similarity	NPC212535
0.7419	Intermediate Similarity	NPC194740
0.7419	Intermediate Similarity	NPC177404
0.7416	Intermediate Similarity	NPC316981
0.7415	Intermediate Similarity	NPC285558
0.7404	Intermediate Similarity	NPC11464
0.74	Intermediate Similarity	NPC205934
0.74	Intermediate Similarity	NPC43787
0.7396	Intermediate Similarity	NPC283152
0.7389	Intermediate Similarity	NPC121772
0.7389	Intermediate Similarity	NPC329747
0.7385	Intermediate Similarity	NPC284678
0.7385	Intermediate Similarity	NPC209174
0.738	Intermediate Similarity	NPC118511
0.738	Intermediate Similarity	NPC476118
0.7374	Intermediate Similarity	NPC76748
0.7371	Intermediate Similarity	NPC219963
0.7371	Intermediate Similarity	NPC118776
0.7371	Intermediate Similarity	NPC266551
0.7363	Intermediate Similarity	NPC251090
0.7361	Intermediate Similarity	NPC179287
0.736	Intermediate Similarity	NPC46580
0.7358	Intermediate Similarity	NPC305984
0.7354	Intermediate Similarity	NPC477861
0.7353	Intermediate Similarity	NPC470586
0.735	Intermediate Similarity	NPC475190
0.7349	Intermediate Similarity	NPC280272
0.7342	Intermediate Similarity	NPC184680
0.7337	Intermediate Similarity	NPC92111
0.7336	Intermediate Similarity	NPC86078
0.733	Intermediate Similarity	NPC182222
0.7327	Intermediate Similarity	NPC153042
0.7323	Intermediate Similarity	NPC296527
0.7309	Intermediate Similarity	NPC470784
0.7309	Intermediate Similarity	NPC470785
0.73	Intermediate Similarity	NPC99666
0.7299	Intermediate Similarity	NPC478074
0.7297	Intermediate Similarity	NPC295228
0.7297	Intermediate Similarity	NPC473187
0.7296	Intermediate Similarity	NPC62069
0.7286	Intermediate Similarity	NPC87413
0.7281	Intermediate Similarity	NPC63971
0.7281	Intermediate Similarity	NPC91868
0.7277	Intermediate Similarity	NPC13880
0.7273	Intermediate Similarity	NPC260434
0.7268	Intermediate Similarity	NPC476044
0.7268	Intermediate Similarity	NPC88363
0.7264	Intermediate Similarity	NPC226202
0.7263	Intermediate Similarity	NPC1527
0.726	Intermediate Similarity	NPC321428
0.7259	Intermediate Similarity	NPC20249
0.7256	Intermediate Similarity	NPC150239
0.7256	Intermediate Similarity	NPC477533
0.7249	Intermediate Similarity	NPC165964
0.7246	Intermediate Similarity	NPC475070
0.7245	Intermediate Similarity	NPC48938
0.7243	Intermediate Similarity	NPC184408
0.7241	Intermediate Similarity	NPC77555
0.723	Intermediate Similarity	NPC288349
0.7225	Intermediate Similarity	NPC477888
0.7222	Intermediate Similarity	NPC204385
0.722	Intermediate Similarity	NPC249040
0.7209	Intermediate Similarity	NPC208084
0.7209	Intermediate Similarity	NPC292958
0.7202	Intermediate Similarity	NPC312872
0.719	Intermediate Similarity	NPC201697
0.7184	Intermediate Similarity	NPC267423
0.7182	Intermediate Similarity	NPC274640
0.7179	Intermediate Similarity	NPC42979
0.7176	Intermediate Similarity	NPC225279
0.7176	Intermediate Similarity	NPC323969
0.7174	Intermediate Similarity	NPC26543
0.7173	Intermediate Similarity	NPC44161
0.7172	Intermediate Similarity	NPC314002
0.7169	Intermediate Similarity	NPC227908
0.7165	Intermediate Similarity	NPC224764
0.7165	Intermediate Similarity	NPC288943
0.7163	Intermediate Similarity	NPC264285
0.7163	Intermediate Similarity	NPC247803
0.7162	Intermediate Similarity	NPC471891
0.7162	Intermediate Similarity	NPC473186
0.7162	Intermediate Similarity	NPC132329
0.7162	Intermediate Similarity	NPC196718
0.7156	Intermediate Similarity	NPC101350
0.7156	Intermediate Similarity	NPC122436
0.715	Intermediate Similarity	NPC128751
0.715	Intermediate Similarity	NPC246700
0.715	Intermediate Similarity	NPC66815
0.715	Intermediate Similarity	NPC183407
0.7143	Intermediate Similarity	NPC39679
0.7143	Intermediate Similarity	NPC195314
0.7136	Intermediate Similarity	NPC329793
0.7136	Intermediate Similarity	NPC171171
0.713	Intermediate Similarity	NPC141053
0.7128	Intermediate Similarity	NPC96890
0.7123	Intermediate Similarity	NPC187501
0.7122	Intermediate Similarity	NPC306376
0.7121	Intermediate Similarity	NPC204717
0.7116	Intermediate Similarity	NPC304926
0.7116	Intermediate Similarity	NPC314552
0.7116	Intermediate Similarity	NPC476041
0.7116	Intermediate Similarity	NPC312645
0.7114	Intermediate Similarity	NPC106833
0.7114	Intermediate Similarity	NPC469497
0.7112	Intermediate Similarity	NPC141353
0.7111	Intermediate Similarity	NPC235685
0.711	Intermediate Similarity	NPC144452
0.711	Intermediate Similarity	NPC470501
0.71	Intermediate Similarity	NPC66083
0.7098	Intermediate Similarity	NPC121658
0.7098	Intermediate Similarity	NPC39370

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 NPC18487 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	742
0.2-0.3	830
0.3-0.4	1299
0.4-0.5	2913
0.5-0.6	2416
0.6-0.7	668
0.7-0.8	48
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
0.79	Intermediate Similarity	NPD8403	Phase 1
0.7654	Intermediate Similarity	NPD3835	Phase 3
0.7654	Intermediate Similarity	NPD3833	Phase 3
0.7635	Intermediate Similarity	NPD3003	Approved
0.76	Intermediate Similarity	NPD1768	Approved
0.7561	Intermediate Similarity	NPD5658	Approved
0.7525	Intermediate Similarity	NPD1038	Approved
0.7476	Intermediate Similarity	NPD5612	Discontinued
0.7474	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD8512	Phase 3
0.7453	Intermediate Similarity	NPD3875	Discontinued
0.7429	Intermediate Similarity	NPD5903	Approved
0.7429	Intermediate Similarity	NPD5902	Approved
0.7426	Intermediate Similarity	NPD8396	Approved
0.7426	Intermediate Similarity	NPD8395	Approved
0.74	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5256	Discontinued
0.738	Intermediate Similarity	NPD5138	Approved
0.738	Intermediate Similarity	NPD5140	Approved
0.7368	Intermediate Similarity	NPD4502	Phase 2
0.736	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD1592	Phase 3
0.7349	Intermediate Similarity	NPD7221	Approved
0.7349	Intermediate Similarity	NPD7219	Approved
0.7343	Intermediate Similarity	NPD7453	Approved
0.7343	Intermediate Similarity	NPD7452	Approved
0.7343	Intermediate Similarity	NPD7222	Phase 2
0.7343	Intermediate Similarity	NPD1392	Approved
0.7313	Intermediate Similarity	NPD6590	Discontinued
0.729	Intermediate Similarity	NPD7194	Discontinued
0.7286	Intermediate Similarity	NPD5066	Phase 2
0.7286	Intermediate Similarity	NPD5067	Phase 2
0.7282	Intermediate Similarity	NPD4203	Approved
0.7282	Intermediate Similarity	NPD4204	Approved
0.7277	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4548	Discontinued
0.7255	Intermediate Similarity	NPD2151	Approved
0.7251	Intermediate Similarity	NPD6202	Discontinued
0.7248	Intermediate Similarity	NPD1273	Discontinued
0.7245	Intermediate Similarity	NPD5596	Phase 2
0.7243	Intermediate Similarity	NPD6985	Discontinued
0.7228	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7558	Phase 2
0.7204	Intermediate Similarity	NPD4131	Phase 3
0.7192	Intermediate Similarity	NPD5512	Phase 3
0.7189	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7948	Phase 1
0.7129	Intermediate Similarity	NPD6569	Phase 2
0.7128	Intermediate Similarity	NPD6159	Phase 2
0.7124	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD949	Phase 1
0.7116	Intermediate Similarity	NPD5164	Discontinued
0.7098	Intermediate Similarity	NPD3838	Phase 3
0.7089	Intermediate Similarity	NPD2794	Discontinued
0.7087	Intermediate Similarity	NPD2175	Phase 3
0.7087	Intermediate Similarity	NPD2176	Approved
0.7087	Intermediate Similarity	NPD3825	Phase 3
0.7087	Intermediate Similarity	NPD2177	Approved
0.7083	Intermediate Similarity	NPD5632	Approved
0.7078	Intermediate Similarity	NPD983	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3396	Approved
0.7059	Intermediate Similarity	NPD3395	Approved
0.7048	Intermediate Similarity	NPD5530	Phase 1
0.7044	Intermediate Similarity	NPD4372	Phase 1
0.7042	Intermediate Similarity	NPD5416	Discontinued
0.7032	Intermediate Similarity	NPD1856	Discontinued
0.7032	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6550	Discontinued
0.701	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4927	Discontinued
0.7005	Intermediate Similarity	NPD3920	Phase 2
0.7005	Intermediate Similarity	NPD3814	Phase 1
0.7	Intermediate Similarity	NPD4795	Phase 2
0.6995	Remote Similarity	NPD5913	Phase 3
0.6995	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6643	Discontinued
0.699	Remote Similarity	NPD6988	Phase 1
0.699	Remote Similarity	NPD5003	Discontinued
0.6986	Remote Similarity	NPD7726	Phase 1
0.6978	Remote Similarity	NPD4080	Discontinued
0.6976	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD1739	Approved
0.6971	Remote Similarity	NPD1740	Approved
0.6963	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD3343	Phase 3
0.6957	Remote Similarity	NPD7946	Pre-registration
0.6955	Remote Similarity	NPD6736	Discontinued
0.6947	Remote Similarity	NPD2951	Discontinued
0.6944	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD774	Phase 3
0.6942	Remote Similarity	NPD3477	Phase 2
0.6942	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD4511	Phase 1
0.6937	Remote Similarity	NPD7603	Discontinued
0.6935	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3746	Discontinued
0.6931	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.693	Remote Similarity	NPD3330	Phase 1
0.6927	Remote Similarity	NPD862	Approved
0.6927	Remote Similarity	NPD863	Approved
0.6927	Remote Similarity	NPD861	Approved
0.6926	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4083	Discontinued
0.6923	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5479	Discontinued
0.6913	Remote Similarity	NPD6473	Phase 1
0.6908	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2189	Approved
0.6901	Remote Similarity	NPD2187	Approved
0.6894	Remote Similarity	NPD6743	Phase 2
0.6894	Remote Similarity	NPD6742	Phase 2
0.6893	Remote Similarity	NPD4418	Discontinued
0.6887	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6220	Phase 3
0.6884	Remote Similarity	NPD5936	Approved
0.6884	Remote Similarity	NPD5939	Approved
0.6884	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5482	Discontinued
0.6872	Remote Similarity	NPD565	Phase 2
0.686	Remote Similarity	NPD4442	Phase 2
0.686	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD4885	Approved
0.6854	Remote Similarity	NPD6290	Phase 2
0.6854	Remote Similarity	NPD5429	Discontinued
0.6851	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3037	Phase 1
0.6849	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1034	Phase 3
0.6847	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD802	Phase 2
0.6842	Remote Similarity	NPD7853	Phase 2
0.6842	Remote Similarity	NPD5999	Phase 2
0.6834	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2762	Phase 2
0.683	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD2952	Discontinued
0.6821	Remote Similarity	NPD2844	Phase 3
0.682	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3402	Phase 1
0.6818	Remote Similarity	NPD8284	Discontinued
0.6816	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7068	Approved
0.681	Remote Similarity	NPD1838	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7067	Approved
0.6806	Remote Similarity	NPD3570	Phase 2
0.68	Remote Similarity	NPD5559	Phase 2
0.6798	Remote Similarity	NPD6760	Discontinued
0.6798	Remote Similarity	NPD4375	Approved
0.6787	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2565	Phase 2
0.678	Remote Similarity	NPD1043	Phase 3
0.678	Remote Similarity	NPD2564	Approved
0.6771	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4454	Phase 2
0.6766	Remote Similarity	NPD5644	Phase 1
0.6765	Remote Similarity	NPD2383	Phase 1
0.6761	Remote Similarity	NPD4033	Approved
0.6761	Remote Similarity	NPD4037	Approved
0.6761	Remote Similarity	NPD4039	Approved
0.6761	Remote Similarity	NPD4122	Approved
0.6761	Remote Similarity	NPD4034	Approved
0.6761	Remote Similarity	NPD31	Approved
0.6761	Remote Similarity	NPD32	Approved
0.6761	Remote Similarity	NPD3397	Phase 2
0.6761	Remote Similarity	NPD4036	Approved
0.6761	Remote Similarity	NPD4038	Approved
0.6761	Remote Similarity	NPD4035	Approved
0.6756	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6978	Phase 2
0.6745	Remote Similarity	NPD2779	Approved
0.6743	Remote Similarity	NPD4457	Phase 2
0.6743	Remote Similarity	NPD3945	Discontinued
0.6742	Remote Similarity	NPD534	Phase 2
0.6742	Remote Similarity	NPD537	Phase 2
0.6741	Remote Similarity	NPD6246	Approved
0.6739	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4021	Phase 2
0.6731	Remote Similarity	NPD6251	Discontinued
0.673	Remote Similarity	NPD484	Approved
0.6729	Remote Similarity	NPD6150	Discontinued
0.6728	Remote Similarity	NPD3939	Suspended
0.6727	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6607	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