NPASS Compound

Structure

NPC475288 OpenBabel07101719252D 42 48 0 0 1 0 0 0 0 0999 V2000 -2.6552 -2.3007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4743 0.7447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9369 -1.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9850 0.3965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8995 -2.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1370 0.8368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6552 -0.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2941 -0.1389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1962 -0.9676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7895 -0.0541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9096 -3.0979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7277 0.6546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8995 0.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3403 -0.7553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6084 -1.7767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7950 0.0504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8708 -3.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0382 -1.4580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.6825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1808 0.2342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9096 0.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1145 -1.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1178 -1.1954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0047 -3.8413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2727 -0.8413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0706 -1.9334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6139 -1.6721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8708 -2.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2727 -1.8413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4067 -2.3413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2072 -0.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0047 -1.8413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1387 -2.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5406 -0.8413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5406 -1.8413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4067 -0.3413 0.0000 C 0 0 2 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 4.2127 -0.8631 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6613 -1.7512 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 3.1387 -3.3413 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8763 0.5416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2727 -3.8413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 5 2 0 0 0 0 2 4 1 0 0 0 0 2 6 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 27 2 0 0 0 0 16 31 2 0 0 0 0 17 24 2 0 0 0 0 17 28 1 0 0 0 0 18 23 1 0 0 0 0 18 30 1 0 0 0 0 20 36 1 0 0 0 0 21 37 1 0 0 0 0 22 39 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 0 0 0 0 25 29 2 0 0 0 0 25 36 1 0 0 0 0 26 35 1 0 0 0 0 26 39 1 0 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 28 32 2 0 0 0 0 29 30 1 0 0 0 0 29 33 1 0 0 0 0 30 35 1 1 0 0 0 31 38 1 0 0 0 0 32 33 1 0 0 0 0 32 38 1 0 0 0 0 33 40 2 0 0 0 0 34 35 1 1 0 0 0 34 36 1 0 0 0 0 34 37 1 0 0 0 0 35 19 1 1 0 0 0 36 41 1 1 0 0 0 40 42 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.36
Volume:	609.156
LogP:	3.076
LogD:	3.195
LogS:	-2.52
# Rotatable Bonds:	1
TPSA:	78.23
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	6.717
Fsp3:	0.528
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.432
MDCK Permeability:	3.543525963323191e-05
Pgp-inhibitor:	0.126
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.641
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	94.70243072509766%
Volume Distribution (VD):	2.405
Pgp-substrate:	3.1081790924072266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.9
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.905
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.538
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	4.579
Half-life (T1/2):	0.718

ADMET: Toxicity

hERG Blockers:	0.8
Human Hepatotoxicity (H-HT):	0.855
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.571
Rat Oral Acute Toxicity:	0.421
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.949
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC475288

Natural Product ID:	NPC475288
*Common Name:**	WLAKKZBRRAGCTQ-GSXVTLMESA-N
IUPAC Name:	n.a.
Synonyms:	Manzamine J N-Oxide
Standard InCHIKey:	WLAKKZBRRAGCTQ-GSXVTLMESA-N
Standard InCHI:	InChI=1S/C36H46N4O2/c41-36-20-12-6-2-4-8-14-22-39-23-18-30(35(26-39)19-11-5-1-3-7-13-21-37-34(35)36)29(25-36)33-32-28(17-24-40(33)42)27-15-9-10-16-31(27)38-32/h1-2,5-6,9-10,15-17,24-25,30,34,37-38,41H,3-4,7-8,11-14,18-23,26H2/b5-1-,6-2-/t30-,34+,35-,36-/m0/s1
SMILES:	O=n1ccc2c(c1C1=C[C@@]3(O)CC/C=CCCCCN4CC[C@@H]1[C@@]1([C@H]3NCCCC/C=CCC1)C4)[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502894
PubChem CID:	n.a.
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
NPO33515	xestospongia ashmorica	Species	Petrosiidae	Eukaryota	n.a.	Philippine	n.a.	PMID[8946747]

☑ 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
ED50	1
Others	5

Activity Type	# Activity
Cell Line	1
CELL-LINE	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	=	3.2	ug ml-1	PMID[505497]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Inhibition	=	16.2	%	PMID[505497]
NPT26591	CELL-LINE	Dendritic cells	n.a.	FC	=	2.0	n.a.	PMID[505498]
NPT20972	CELL-LINE	SU.86.86	Homo sapiens	Activity	>	20.0	%	PMID[505499]

☑ 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 NPC475288 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	498
0.1-0.2	2498
0.2-0.3	17577
0.3-0.4	14745
0.4-0.5	3188
0.5-0.6	2089
0.6-0.7	1504
0.7-0.8	564
0.8-0.85	20
0.85-0.9	6
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC265576
0.9476	High Similarity	NPC250835
0.911	High Similarity	NPC473362
0.911	High Similarity	NPC166492
0.875	High Similarity	NPC473310
0.8621	High Similarity	NPC471506
0.8465	Intermediate Similarity	NPC472027
0.8458	Intermediate Similarity	NPC473757
0.8446	Intermediate Similarity	NPC232130
0.8413	Intermediate Similarity	NPC476491
0.8413	Intermediate Similarity	NPC476492
0.8413	Intermediate Similarity	NPC6215
0.8208	Intermediate Similarity	NPC476451
0.8195	Intermediate Similarity	NPC251936
0.8104	Intermediate Similarity	NPC909
0.8104	Intermediate Similarity	NPC475338
0.8066	Intermediate Similarity	NPC475258
0.8065	Intermediate Similarity	NPC41679
0.7991	Intermediate Similarity	NPC81175
0.7917	Intermediate Similarity	NPC48938
0.7892	Intermediate Similarity	NPC471891
0.7879	Intermediate Similarity	NPC133366
0.7873	Intermediate Similarity	NPC473312
0.7869	Intermediate Similarity	NPC236711
0.7835	Intermediate Similarity	NPC15102
0.7807	Intermediate Similarity	NPC160105
0.7795	Intermediate Similarity	NPC94752
0.7784	Intermediate Similarity	NPC472294
0.7778	Intermediate Similarity	NPC324149
0.7778	Intermediate Similarity	NPC471564
0.7766	Intermediate Similarity	NPC63751
0.7766	Intermediate Similarity	NPC201700
0.776	Intermediate Similarity	NPC70922
0.776	Intermediate Similarity	NPC211572
0.776	Intermediate Similarity	NPC75540
0.776	Intermediate Similarity	NPC80597
0.776	Intermediate Similarity	NPC212376
0.7739	Intermediate Similarity	NPC474177
0.7737	Intermediate Similarity	NPC314603
0.7713	Intermediate Similarity	NPC474561
0.7713	Intermediate Similarity	NPC49954
0.7708	Intermediate Similarity	NPC59269
0.7708	Intermediate Similarity	NPC151939
0.7707	Intermediate Similarity	NPC475070
0.7705	Intermediate Similarity	NPC73952
0.7705	Intermediate Similarity	NPC469760
0.7705	Intermediate Similarity	NPC469765
0.7705	Intermediate Similarity	NPC259644
0.7705	Intermediate Similarity	NPC25008
0.7705	Intermediate Similarity	NPC469786
0.7705	Intermediate Similarity	NPC469763
0.7692	Intermediate Similarity	NPC475422
0.7676	Intermediate Similarity	NPC469762
0.7675	Intermediate Similarity	NPC476493
0.7656	Intermediate Similarity	NPC280852
0.7642	Intermediate Similarity	NPC476041
0.7642	Intermediate Similarity	NPC304926
0.7629	Intermediate Similarity	NPC300688
0.7626	Intermediate Similarity	NPC65215
0.7626	Intermediate Similarity	NPC173028
0.7622	Intermediate Similarity	NPC469785
0.7612	Intermediate Similarity	NPC157828
0.7612	Intermediate Similarity	NPC195239
0.7609	Intermediate Similarity	NPC325903
0.7606	Intermediate Similarity	NPC311276
0.7596	Intermediate Similarity	NPC87755
0.7596	Intermediate Similarity	NPC24678
0.7596	Intermediate Similarity	NPC105818
0.7594	Intermediate Similarity	NPC131718
0.7594	Intermediate Similarity	NPC279918
0.7588	Intermediate Similarity	NPC95783
0.7582	Intermediate Similarity	NPC469811
0.7579	Intermediate Similarity	NPC317430
0.7577	Intermediate Similarity	NPC215795
0.7577	Intermediate Similarity	NPC176199
0.7576	Intermediate Similarity	NPC204565
0.7576	Intermediate Similarity	NPC317030
0.7574	Intermediate Similarity	NPC11445
0.7573	Intermediate Similarity	NPC98715
0.7565	Intermediate Similarity	NPC150048
0.7565	Intermediate Similarity	NPC203754
0.7561	Intermediate Similarity	NPC300183
0.7553	Intermediate Similarity	NPC282231
0.7541	Intermediate Similarity	NPC321911
0.754	Intermediate Similarity	NPC135141
0.754	Intermediate Similarity	NPC92796
0.7539	Intermediate Similarity	NPC194411
0.7538	Intermediate Similarity	NPC213629
0.7536	Intermediate Similarity	NPC470500
0.7527	Intermediate Similarity	NPC63545
0.7526	Intermediate Similarity	NPC68354
0.7525	Intermediate Similarity	NPC474707
0.7525	Intermediate Similarity	NPC62749
0.7524	Intermediate Similarity	NPC5145
0.7513	Intermediate Similarity	NPC194640
0.7513	Intermediate Similarity	NPC40779
0.7513	Intermediate Similarity	NPC284678
0.75	Intermediate Similarity	NPC233936
0.7487	Intermediate Similarity	NPC213468
0.7486	Intermediate Similarity	NPC179787
0.7486	Intermediate Similarity	NPC201380
0.7473	Intermediate Similarity	NPC159856
0.7467	Intermediate Similarity	NPC477861
0.7464	Intermediate Similarity	NPC225821
0.7464	Intermediate Similarity	NPC46225
0.7461	Intermediate Similarity	NPC472123
0.746	Intermediate Similarity	NPC470203
0.7452	Intermediate Similarity	NPC470505
0.7451	Intermediate Similarity	NPC229332
0.7447	Intermediate Similarity	NPC56765
0.7442	Intermediate Similarity	NPC477714
0.7435	Intermediate Similarity	NPC54988
0.7429	Intermediate Similarity	NPC258062
0.7429	Intermediate Similarity	NPC314957
0.7429	Intermediate Similarity	NPC127677
0.7424	Intermediate Similarity	NPC165495
0.7424	Intermediate Similarity	NPC228835
0.7423	Intermediate Similarity	NPC275305
0.7423	Intermediate Similarity	NPC37423
0.7421	Intermediate Similarity	NPC317105
0.7421	Intermediate Similarity	NPC102423
0.7421	Intermediate Similarity	NPC469813
0.7421	Intermediate Similarity	NPC476446
0.7421	Intermediate Similarity	NPC78375
0.7418	Intermediate Similarity	NPC475602
0.7415	Intermediate Similarity	NPC192315
0.7407	Intermediate Similarity	NPC122141
0.7407	Intermediate Similarity	NPC470204
0.7395	Intermediate Similarity	NPC477715
0.7393	Intermediate Similarity	NPC271862
0.7391	Intermediate Similarity	NPC470111
0.7385	Intermediate Similarity	NPC288785
0.738	Intermediate Similarity	NPC38736
0.7379	Intermediate Similarity	NPC100321
0.7379	Intermediate Similarity	NPC476167
0.7377	Intermediate Similarity	NPC314372
0.7376	Intermediate Similarity	NPC473763
0.7376	Intermediate Similarity	NPC117244
0.7374	Intermediate Similarity	NPC472108
0.7374	Intermediate Similarity	NPC139291
0.7371	Intermediate Similarity	NPC34508
0.7368	Intermediate Similarity	NPC225018
0.7366	Intermediate Similarity	NPC470233
0.7358	Intermediate Similarity	NPC32534
0.7351	Intermediate Similarity	NPC37548
0.7343	Intermediate Similarity	NPC205254
0.7343	Intermediate Similarity	NPC303820
0.7343	Intermediate Similarity	NPC106771
0.7343	Intermediate Similarity	NPC23420
0.7333	Intermediate Similarity	NPC189812
0.7333	Intermediate Similarity	NPC329688
0.733	Intermediate Similarity	NPC473640
0.733	Intermediate Similarity	NPC171317
0.7323	Intermediate Similarity	NPC314394
0.731	Intermediate Similarity	NPC270009
0.731	Intermediate Similarity	NPC133261
0.7308	Intermediate Similarity	NPC475506
0.7308	Intermediate Similarity	NPC475935
0.7308	Intermediate Similarity	NPC94211
0.7308	Intermediate Similarity	NPC52909
0.7302	Intermediate Similarity	NPC286427
0.73	Intermediate Similarity	NPC280290
0.7296	Intermediate Similarity	NPC474958
0.7295	Intermediate Similarity	NPC293917
0.729	Intermediate Similarity	NPC151976
0.729	Intermediate Similarity	NPC87856
0.7286	Intermediate Similarity	NPC472109
0.7286	Intermediate Similarity	NPC19679
0.7286	Intermediate Similarity	NPC472110
0.7282	Intermediate Similarity	NPC313791
0.7281	Intermediate Similarity	NPC281049
0.7277	Intermediate Similarity	NPC126066
0.7277	Intermediate Similarity	NPC16667
0.7277	Intermediate Similarity	NPC321708
0.7273	Intermediate Similarity	NPC155143
0.7268	Intermediate Similarity	NPC280548
0.7268	Intermediate Similarity	NPC190296
0.7263	Intermediate Similarity	NPC475990
0.7263	Intermediate Similarity	NPC474880
0.7263	Intermediate Similarity	NPC41257
0.7263	Intermediate Similarity	NPC230869
0.7263	Intermediate Similarity	NPC221786
0.7263	Intermediate Similarity	NPC318065
0.7263	Intermediate Similarity	NPC206819
0.7259	Intermediate Similarity	NPC248454
0.7259	Intermediate Similarity	NPC326575
0.7258	Intermediate Similarity	NPC187951
0.7257	Intermediate Similarity	NPC295228
0.7256	Intermediate Similarity	NPC267965
0.7255	Intermediate Similarity	NPC99666
0.7255	Intermediate Similarity	NPC47190
0.7254	Intermediate Similarity	NPC49217
0.7249	Intermediate Similarity	NPC285469
0.7248	Intermediate Similarity	NPC213530
0.7248	Intermediate Similarity	NPC193267
0.7246	Intermediate Similarity	NPC470499
0.7245	Intermediate Similarity	NPC469938
0.724	Intermediate Similarity	NPC472587
0.7231	Intermediate Similarity	NPC470498
0.723	Intermediate Similarity	NPC476116

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 NPC475288 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	537
0.2-0.3	915
0.3-0.4	1720
0.4-0.5	2548
0.5-0.6	1993
0.6-0.7	1052
0.7-0.8	156
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8075	Intermediate Similarity	NPD5065	Approved
0.7927	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD8431	Approved
0.7718	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3961	Discontinued
0.766	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD4181	Approved
0.7577	Intermediate Similarity	NPD4076	Approved
0.7577	Intermediate Similarity	NPD4079	Approved
0.7576	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6595	Phase 3
0.7538	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD7948	Phase 1
0.7536	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD3330	Phase 1
0.7536	Intermediate Similarity	NPD8093	Discontinued
0.7526	Intermediate Similarity	NPD3506	Approved
0.7526	Intermediate Similarity	NPD3505	Approved
0.7525	Intermediate Similarity	NPD7619	Phase 3
0.7525	Intermediate Similarity	NPD7618	Phase 3
0.7514	Intermediate Similarity	NPD2837	Discontinued
0.7513	Intermediate Similarity	NPD3323	Discontinued
0.7512	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5255	Approved
0.7436	Intermediate Similarity	NPD2144	Approved
0.7426	Intermediate Similarity	NPD3404	Approved
0.7426	Intermediate Similarity	NPD4615	Phase 2
0.7423	Intermediate Similarity	NPD4128	Approved
0.7421	Intermediate Similarity	NPD7824	Approved
0.7411	Intermediate Similarity	NPD3038	Discontinued
0.7404	Intermediate Similarity	NPD4886	Phase 2
0.7396	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3830	Phase 1
0.7337	Intermediate Similarity	NPD7469	Discontinued
0.7337	Intermediate Similarity	NPD6178	Phase 3
0.7336	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD8094	Discontinued
0.7333	Intermediate Similarity	NPD7957	Phase 1
0.7333	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7731	Approved
0.733	Intermediate Similarity	NPD7730	Approved
0.7323	Intermediate Similarity	NPD7867	Phase 1
0.7318	Intermediate Similarity	NPD7271	Approved
0.7312	Intermediate Similarity	NPD4462	Approved
0.7312	Intermediate Similarity	NPD4463	Approved
0.7308	Intermediate Similarity	NPD1722	Approved
0.7304	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD706	Phase 1
0.7244	Intermediate Similarity	NPD7953	Approved
0.7244	Intermediate Similarity	NPD7952	Approved
0.7244	Intermediate Similarity	NPD7951	Approved
0.7244	Intermediate Similarity	NPD7950	Approved
0.7244	Intermediate Similarity	NPD7789	Approved
0.7244	Intermediate Similarity	NPD7790	Approved
0.7244	Intermediate Similarity	NPD7791	Approved
0.7241	Intermediate Similarity	NPD6281	Approved
0.7222	Intermediate Similarity	NPD8386	Phase 2
0.7208	Intermediate Similarity	NPD2380	Approved
0.7208	Intermediate Similarity	NPD2382	Approved
0.7208	Intermediate Similarity	NPD4075	Phase 2
0.7208	Intermediate Similarity	NPD2381	Approved
0.7207	Intermediate Similarity	NPD6352	Phase 2
0.7206	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4702	Approved
0.7204	Intermediate Similarity	NPD4703	Approved
0.7204	Intermediate Similarity	NPD4547	Phase 3
0.72	Intermediate Similarity	NPD2094	Phase 2
0.72	Intermediate Similarity	NPD2095	Phase 2
0.72	Intermediate Similarity	NPD2092	Phase 2
0.7198	Intermediate Similarity	NPD6664	Approved
0.7194	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7666	Phase 3
0.7183	Intermediate Similarity	NPD7665	Phase 2
0.7182	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8122	Approved
0.7172	Intermediate Similarity	NPD8123	Approved
0.7166	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD3100	Discontinued
0.7164	Intermediate Similarity	NPD2096	Phase 2
0.7164	Intermediate Similarity	NPD2091	Phase 2
0.7157	Intermediate Similarity	NPD482	Approved
0.7156	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7423	Phase 2
0.715	Intermediate Similarity	NPD8408	Discontinued
0.7143	Intermediate Similarity	NPD3609	Approved
0.7143	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3610	Approved
0.713	Intermediate Similarity	NPD7603	Discontinued
0.7128	Intermediate Similarity	NPD2172	Phase 1
0.7128	Intermediate Similarity	NPD4639	Approved
0.7128	Intermediate Similarity	NPD2640	Approved
0.7128	Intermediate Similarity	NPD2641	Approved
0.7128	Intermediate Similarity	NPD4638	Approved
0.7128	Intermediate Similarity	NPD5862	Discovery
0.7128	Intermediate Similarity	NPD4640	Approved
0.7123	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5426	Phase 3
0.7123	Intermediate Similarity	NPD8272	Phase 2
0.7117	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD3013	Phase 3
0.7113	Intermediate Similarity	NPD2720	Phase 1
0.7113	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD8073	Approved
0.7104	Intermediate Similarity	NPD786	Approved
0.7101	Intermediate Similarity	NPD4998	Phase 3
0.7101	Intermediate Similarity	NPD4999	Phase 3
0.7098	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6164	Phase 2
0.7098	Intermediate Similarity	NPD6165	Phase 2
0.7092	Intermediate Similarity	NPD1326	Approved
0.7092	Intermediate Similarity	NPD1325	Approved
0.7091	Intermediate Similarity	NPD3402	Phase 1
0.7081	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7780	Approved
0.7067	Intermediate Similarity	NPD7781	Approved
0.7062	Intermediate Similarity	NPD5138	Approved
0.7062	Intermediate Similarity	NPD5140	Approved
0.7059	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7394	Phase 2
0.7059	Intermediate Similarity	NPD8021	Approved
0.7059	Intermediate Similarity	NPD8020	Approved
0.7056	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3082	Discontinued
0.7044	Intermediate Similarity	NPD6227	Discontinued
0.7042	Intermediate Similarity	NPD5901	Discontinued
0.704	Intermediate Similarity	NPD6849	Phase 2
0.704	Intermediate Similarity	NPD6850	Phase 2
0.7037	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6957	Approved
0.7032	Intermediate Similarity	NPD6958	Approved
0.703	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5596	Phase 2
0.7023	Intermediate Similarity	NPD4612	Discontinued
0.7021	Intermediate Similarity	NPD1661	Suspended
0.7016	Intermediate Similarity	NPD975	Approved
0.7016	Intermediate Similarity	NPD976	Approved
0.7016	Intermediate Similarity	NPD977	Approved
0.7014	Intermediate Similarity	NPD4600	Approved
0.7014	Intermediate Similarity	NPD4601	Approved
0.7009	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7470	Discontinued
0.7	Intermediate Similarity	NPD2882	Phase 1
0.6995	Remote Similarity	NPD8072	Approved
0.6995	Remote Similarity	NPD4957	Phase 2
0.6995	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3717	Discontinued
0.6986	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6492	Phase 2
0.6978	Remote Similarity	NPD8289	Discontinued
0.6977	Remote Similarity	NPD8322	Phase 2
0.6971	Remote Similarity	NPD5428	Discontinued
0.6959	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8321	Discontinued
0.6955	Remote Similarity	NPD6711	Approved
0.6955	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7112	Discontinued
0.6954	Remote Similarity	NPD5021	Discontinued
0.6947	Remote Similarity	NPD6978	Phase 2
0.6947	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7415	Suspended
0.6942	Remote Similarity	NPD6363	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7944	Discontinued
0.6937	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD750	Phase 2
0.693	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8026	Phase 1
0.6923	Remote Similarity	NPD7185	Discontinued
0.6919	Remote Similarity	NPD6469	Phase 3
0.6919	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7111	Discontinued
0.6911	Remote Similarity	NPD6158	Phase 2
0.6911	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7188	Phase 3
0.6908	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD8063	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