NPASS Compound

Structure

NPC265576 OpenBabel07101718272D 41 47 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 4.0047 -3.8413 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 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 3.1387 -2.3413 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 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 3.1387 -3.3413 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 4.2127 -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 1.8763 0.5416 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 23 1 0 0 0 0 15 27 2 0 0 0 0 16 31 2 0 0 0 0 17 22 2 0 0 0 0 17 28 1 0 0 0 0 18 24 1 0 0 0 0 18 30 1 0 0 0 0 20 36 1 0 0 0 0 21 38 1 0 0 0 0 22 37 1 0 0 0 0 23 40 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 40 1 0 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 28 33 2 0 0 0 0 29 30 1 0 0 0 0 29 32 1 0 0 0 0 30 35 1 1 0 0 0 31 39 1 0 0 0 0 32 33 1 0 0 0 0 32 37 2 0 0 0 0 33 39 1 0 0 0 0 34 35 1 1 0 0 0 34 36 1 0 0 0 0 34 38 1 0 0 0 0 35 19 1 1 0 0 0 36 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.37
Volume:	600.366
LogP:	4.438
LogD:	3.704
LogS:	-2.549
# Rotatable Bonds:	1
TPSA:	64.18
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	6.482
Fsp3:	0.528
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.29
MDCK Permeability:	2.86576814687578e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.265
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.728
Plasma Protein Binding (PPB):	95.53986358642578%
Volume Distribution (VD):	2.6
Pgp-substrate:	3.502208709716797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.23
CYP1A2-substrate:	0.769
CYP2C19-inhibitor:	0.169
CYP2C19-substrate:	0.212
CYP2C9-inhibitor:	0.131
CYP2C9-substrate:	0.202
CYP2D6-inhibitor:	0.986
CYP2D6-substrate:	0.954
CYP3A4-inhibitor:	0.971
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	4.433
Half-life (T1/2):	0.531

ADMET: Toxicity

hERG Blockers:	0.822
Human Hepatotoxicity (H-HT):	0.904
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.36
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.96
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC265576

Natural Product ID:	NPC265576
*Common Name:**	Manzamine J
IUPAC Name:	n.a.
Synonyms:	Manzamine J
Standard InCHIKey:	FDTXAASVSUUWOT-GSXVTLMESA-N
Standard InCHI:	InChI=1S/C36H46N4O/c41-36-20-12-6-2-4-8-14-23-40-24-18-30(35(26-40)19-11-5-1-3-7-13-21-38-34(35)36)29(25-36)32-33-28(17-22-37-32)27-15-9-10-16-31(27)39-33/h1-2,5-6,9-10,15-17,22,25,30,34,38-39,41H,3-4,7-8,11-14,18-21,23-24,26H2/b5-1-,6-2-/t30-,34+,35-,36-/m0/s1
SMILES:	O[C@@]12CC/C=CCCCCN3C[C@]4([C@H]2NCCCC/C=CCC4)[C@H](C(=C1)c1nccc2c1[nH]c1c2cccc1)CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448704
PubChem CID:	5276609
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
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332848]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2004-Mar	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2002-May	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28452477]
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
IC50	4
MIC	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	=	25.0	ug ml-1	PMID[461264]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Inhibition	=	2.0	%	PMID[461264]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.3	ug.mL-1	PMID[461265]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.75	ug.mL-1	PMID[461265]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	25.0	ug.mL-1	PMID[461265]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	15.0	ug.mL-1	PMID[461265]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	45.0	ug.mL-1	PMID[461265]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1.7	ug.mL-1	PMID[461265]

☑ 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 NPC265576 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	515
0.1-0.2	2618
0.2-0.3	17548
0.3-0.4	14606
0.4-0.5	3170
0.5-0.6	2048
0.6-0.7	1531
0.7-0.8	600
0.8-0.85	46
0.85-0.9	6
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC475288
0.9457	High Similarity	NPC473362
0.9457	High Similarity	NPC166492
0.911	High Similarity	NPC250835
0.8969	High Similarity	NPC473310
0.8832	High Similarity	NPC471506
0.8769	High Similarity	NPC472027
0.8763	High Similarity	NPC473757
0.8614	High Similarity	NPC6215
0.8614	High Similarity	NPC476492
0.8614	High Similarity	NPC476491
0.8485	Intermediate Similarity	NPC251936
0.8398	Intermediate Similarity	NPC476451
0.8293	Intermediate Similarity	NPC909
0.8293	Intermediate Similarity	NPC475338
0.8272	Intermediate Similarity	NPC232130
0.8252	Intermediate Similarity	NPC475258
0.8246	Intermediate Similarity	NPC41679
0.8216	Intermediate Similarity	NPC48938
0.8169	Intermediate Similarity	NPC81175
0.8128	Intermediate Similarity	NPC15102
0.8075	Intermediate Similarity	NPC472294
0.8073	Intermediate Similarity	NPC133366
0.8068	Intermediate Similarity	NPC211572
0.8068	Intermediate Similarity	NPC70922
0.8068	Intermediate Similarity	NPC75540
0.8068	Intermediate Similarity	NPC80597
0.8068	Intermediate Similarity	NPC212376
0.8066	Intermediate Similarity	NPC201700
0.8065	Intermediate Similarity	NPC471891
0.8063	Intermediate Similarity	NPC324149
0.8047	Intermediate Similarity	NPC473312
0.8011	Intermediate Similarity	NPC469760
0.8011	Intermediate Similarity	NPC25008
0.8011	Intermediate Similarity	NPC160105
0.8011	Intermediate Similarity	NPC469763
0.8011	Intermediate Similarity	NPC259644
0.8011	Intermediate Similarity	NPC469786
0.8011	Intermediate Similarity	NPC469765
0.8011	Intermediate Similarity	NPC73952
0.8	Intermediate Similarity	NPC151939
0.7989	Intermediate Similarity	NPC94752
0.798	Intermediate Similarity	NPC475070
0.7967	Intermediate Similarity	NPC63751
0.7946	Intermediate Similarity	NPC280852
0.7945	Intermediate Similarity	NPC471564
0.7935	Intermediate Similarity	NPC314603
0.7927	Intermediate Similarity	NPC474177
0.7921	Intermediate Similarity	NPC469785
0.7914	Intermediate Similarity	NPC300688
0.7912	Intermediate Similarity	NPC474561
0.7912	Intermediate Similarity	NPC49954
0.791	Intermediate Similarity	NPC325903
0.7903	Intermediate Similarity	NPC59269
0.7902	Intermediate Similarity	NPC476041
0.7902	Intermediate Similarity	NPC304926
0.7898	Intermediate Similarity	NPC105818
0.7898	Intermediate Similarity	NPC24678
0.7889	Intermediate Similarity	NPC131718
0.7886	Intermediate Similarity	NPC469811
0.7877	Intermediate Similarity	NPC469762
0.7871	Intermediate Similarity	NPC475422
0.7869	Intermediate Similarity	NPC317430
0.7865	Intermediate Similarity	NPC95783
0.7861	Intermediate Similarity	NPC215795
0.7861	Intermediate Similarity	NPC87755
0.7861	Intermediate Similarity	NPC176199
0.7849	Intermediate Similarity	NPC203754
0.7849	Intermediate Similarity	NPC150048
0.7841	Intermediate Similarity	NPC321911
0.7838	Intermediate Similarity	NPC476493
0.7833	Intermediate Similarity	NPC135141
0.7833	Intermediate Similarity	NPC92796
0.7829	Intermediate Similarity	NPC63545
0.7826	Intermediate Similarity	NPC194411
0.7812	Intermediate Similarity	NPC173028
0.7812	Intermediate Similarity	NPC65215
0.7802	Intermediate Similarity	NPC311276
0.7795	Intermediate Similarity	NPC195239
0.7795	Intermediate Similarity	NPC157828
0.779	Intermediate Similarity	NPC279918
0.7789	Intermediate Similarity	NPC284678
0.7784	Intermediate Similarity	NPC201380
0.7784	Intermediate Similarity	NPC179787
0.7771	Intermediate Similarity	NPC159856
0.776	Intermediate Similarity	NPC204565
0.776	Intermediate Similarity	NPC317030
0.7755	Intermediate Similarity	NPC11445
0.775	Intermediate Similarity	NPC98715
0.7747	Intermediate Similarity	NPC470203
0.7747	Intermediate Similarity	NPC282231
0.7742	Intermediate Similarity	NPC472123
0.7739	Intermediate Similarity	NPC300183
0.7735	Intermediate Similarity	NPC56765
0.772	Intermediate Similarity	NPC213629
0.7713	Intermediate Similarity	NPC68354
0.7711	Intermediate Similarity	NPC470505
0.7711	Intermediate Similarity	NPC470500
0.7708	Intermediate Similarity	NPC62749
0.7708	Intermediate Similarity	NPC474707
0.7705	Intermediate Similarity	NPC317105
0.7705	Intermediate Similarity	NPC40779
0.7705	Intermediate Similarity	NPC194640
0.7705	Intermediate Similarity	NPC102423
0.7701	Intermediate Similarity	NPC37423
0.7701	Intermediate Similarity	NPC275305
0.7696	Intermediate Similarity	NPC5145
0.7692	Intermediate Similarity	NPC122141
0.7692	Intermediate Similarity	NPC470204
0.7684	Intermediate Similarity	NPC233936
0.7677	Intermediate Similarity	NPC192315
0.7672	Intermediate Similarity	NPC213468
0.767	Intermediate Similarity	NPC314372
0.7654	Intermediate Similarity	NPC470233
0.7638	Intermediate Similarity	NPC476167
0.7635	Intermediate Similarity	NPC225821
0.7635	Intermediate Similarity	NPC46225
0.7626	Intermediate Similarity	NPC229332
0.7626	Intermediate Similarity	NPC477861
0.7622	Intermediate Similarity	NPC54988
0.7609	Intermediate Similarity	NPC78375
0.7609	Intermediate Similarity	NPC469813
0.7609	Intermediate Similarity	NPC476446
0.7608	Intermediate Similarity	NPC477714
0.7606	Intermediate Similarity	NPC329688
0.7606	Intermediate Similarity	NPC189812
0.7604	Intermediate Similarity	NPC228835
0.76	Intermediate Similarity	NPC23420
0.76	Intermediate Similarity	NPC303820
0.76	Intermediate Similarity	NPC106771
0.76	Intermediate Similarity	NPC205254
0.7598	Intermediate Similarity	NPC258062
0.7598	Intermediate Similarity	NPC127677
0.7598	Intermediate Similarity	NPC314957
0.7585	Intermediate Similarity	NPC475602
0.7582	Intermediate Similarity	NPC236711
0.7582	Intermediate Similarity	NPC286427
0.7569	Intermediate Similarity	NPC38736
0.7566	Intermediate Similarity	NPC474958
0.7566	Intermediate Similarity	NPC288785
0.7562	Intermediate Similarity	NPC475935
0.7562	Intermediate Similarity	NPC94211
0.7562	Intermediate Similarity	NPC52909
0.7561	Intermediate Similarity	NPC271862
0.756	Intermediate Similarity	NPC477715
0.7557	Intermediate Similarity	NPC190296
0.7553	Intermediate Similarity	NPC313791
0.7553	Intermediate Similarity	NPC34508
0.7552	Intermediate Similarity	NPC19679
0.7552	Intermediate Similarity	NPC139291
0.7552	Intermediate Similarity	NPC472108
0.755	Intermediate Similarity	NPC100321
0.7542	Intermediate Similarity	NPC37548
0.7541	Intermediate Similarity	NPC230869
0.7541	Intermediate Similarity	NPC206819
0.7541	Intermediate Similarity	NPC474880
0.7541	Intermediate Similarity	NPC475990
0.7541	Intermediate Similarity	NPC318065
0.7541	Intermediate Similarity	NPC41257
0.7541	Intermediate Similarity	NPC221786
0.7527	Intermediate Similarity	NPC49217
0.7524	Intermediate Similarity	NPC126066
0.75	Intermediate Similarity	NPC473640
0.75	Intermediate Similarity	NPC229173
0.75	Intermediate Similarity	NPC469766
0.75	Intermediate Similarity	NPC171317
0.75	Intermediate Similarity	NPC40070
0.75	Intermediate Similarity	NPC314394
0.7487	Intermediate Similarity	NPC270009
0.7487	Intermediate Similarity	NPC154293
0.7487	Intermediate Similarity	NPC133261
0.7486	Intermediate Similarity	NPC88097
0.7486	Intermediate Similarity	NPC21605
0.7486	Intermediate Similarity	NPC470111
0.7486	Intermediate Similarity	NPC129721
0.7476	Intermediate Similarity	NPC476116
0.7475	Intermediate Similarity	NPC475506
0.7474	Intermediate Similarity	NPC280290
0.7473	Intermediate Similarity	NPC476219
0.7463	Intermediate Similarity	NPC293917
0.7461	Intermediate Similarity	NPC472110
0.7461	Intermediate Similarity	NPC472109
0.7459	Intermediate Similarity	NPC16667
0.7459	Intermediate Similarity	NPC225018
0.7452	Intermediate Similarity	NPC151976
0.7452	Intermediate Similarity	NPC87856
0.7449	Intermediate Similarity	NPC321708
0.7447	Intermediate Similarity	NPC280548
0.7444	Intermediate Similarity	NPC187951
0.7443	Intermediate Similarity	NPC469780
0.7443	Intermediate Similarity	NPC469783
0.7443	Intermediate Similarity	NPC469768
0.7443	Intermediate Similarity	NPC469779
0.7443	Intermediate Similarity	NPC115611
0.7443	Intermediate Similarity	NPC469767
0.7443	Intermediate Similarity	NPC469761
0.7443	Intermediate Similarity	NPC469784
0.7441	Intermediate Similarity	NPC281049
0.7438	Intermediate Similarity	NPC155143
0.7436	Intermediate Similarity	NPC171171

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 NPC265576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	540
0.2-0.3	916
0.3-0.4	1660
0.4-0.5	2542
0.5-0.6	1962
0.6-0.7	1087
0.7-0.8	200
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8389	Intermediate Similarity	NPD5065	Approved
0.8226	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD8431	Approved
0.7903	Intermediate Similarity	NPD4181	Approved
0.79	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3961	Discontinued
0.7831	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD2837	Discontinued
0.7802	Intermediate Similarity	NPD3323	Discontinued
0.7772	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD4076	Approved
0.7766	Intermediate Similarity	NPD4079	Approved
0.776	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD5255	Approved
0.7729	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6595	Phase 3
0.772	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7948	Phase 1
0.7713	Intermediate Similarity	NPD3506	Approved
0.7713	Intermediate Similarity	NPD3505	Approved
0.7707	Intermediate Similarity	NPD8093	Discontinued
0.7707	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD3330	Phase 1
0.7704	Intermediate Similarity	NPD7619	Phase 3
0.7704	Intermediate Similarity	NPD7618	Phase 3
0.7701	Intermediate Similarity	NPD4128	Approved
0.7692	Intermediate Similarity	NPD3404	Approved
0.7685	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4886	Phase 2
0.766	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7469	Discontinued
0.7619	Intermediate Similarity	NPD2144	Approved
0.76	Intermediate Similarity	NPD1722	Approved
0.7592	Intermediate Similarity	NPD3038	Discontinued
0.7581	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7824	Approved
0.7563	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD706	Phase 1
0.7513	Intermediate Similarity	NPD6178	Phase 3
0.75	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8094	Discontinued
0.75	Intermediate Similarity	NPD7867	Phase 1
0.75	Intermediate Similarity	NPD7957	Phase 1
0.75	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7731	Approved
0.7488	Intermediate Similarity	NPD7730	Approved
0.7486	Intermediate Similarity	NPD4702	Approved
0.7486	Intermediate Similarity	NPD4547	Phase 3
0.7486	Intermediate Similarity	NPD4703	Approved
0.7477	Intermediate Similarity	NPD7271	Approved
0.7474	Intermediate Similarity	NPD2381	Approved
0.7474	Intermediate Similarity	NPD4075	Phase 2
0.7474	Intermediate Similarity	NPD2380	Approved
0.7474	Intermediate Similarity	NPD2382	Approved
0.7463	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3100	Discontinued
0.7444	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6352	Phase 2
0.7441	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4615	Phase 2
0.7411	Intermediate Similarity	NPD6281	Approved
0.7407	Intermediate Similarity	NPD3610	Approved
0.7407	Intermediate Similarity	NPD3609	Approved
0.7403	Intermediate Similarity	NPD2172	Phase 1
0.7397	Intermediate Similarity	NPD7791	Approved
0.7397	Intermediate Similarity	NPD7953	Approved
0.7397	Intermediate Similarity	NPD7790	Approved
0.7397	Intermediate Similarity	NPD7789	Approved
0.7397	Intermediate Similarity	NPD7952	Approved
0.7397	Intermediate Similarity	NPD7951	Approved
0.7397	Intermediate Similarity	NPD7950	Approved
0.7396	Intermediate Similarity	NPD8386	Phase 2
0.7393	Intermediate Similarity	NPD7423	Phase 2
0.7386	Intermediate Similarity	NPD786	Approved
0.7374	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2095	Phase 2
0.7371	Intermediate Similarity	NPD2094	Phase 2
0.7371	Intermediate Similarity	NPD2092	Phase 2
0.7366	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6664	Approved
0.7363	Intermediate Similarity	NPD3830	Phase 1
0.736	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD1325	Approved
0.7354	Intermediate Similarity	NPD1326	Approved
0.735	Intermediate Similarity	NPD4998	Phase 3
0.735	Intermediate Similarity	NPD4999	Phase 3
0.7344	Intermediate Similarity	NPD8122	Approved
0.7344	Intermediate Similarity	NPD8123	Approved
0.7343	Intermediate Similarity	NPD7666	Phase 3
0.7343	Intermediate Similarity	NPD7665	Phase 2
0.7336	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2096	Phase 2
0.7333	Intermediate Similarity	NPD2091	Phase 2
0.733	Intermediate Similarity	NPD482	Approved
0.7324	Intermediate Similarity	NPD3402	Phase 1
0.732	Intermediate Similarity	NPD8408	Discontinued
0.7316	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7394	Phase 2
0.7308	Intermediate Similarity	NPD4463	Approved
0.7308	Intermediate Similarity	NPD4462	Approved
0.7308	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2640	Approved
0.7302	Intermediate Similarity	NPD4640	Approved
0.7302	Intermediate Similarity	NPD4638	Approved
0.7302	Intermediate Similarity	NPD5862	Discovery
0.7302	Intermediate Similarity	NPD4639	Approved
0.7302	Intermediate Similarity	NPD2641	Approved
0.7287	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2720	Phase 1
0.7283	Intermediate Similarity	NPD975	Approved
0.7283	Intermediate Similarity	NPD976	Approved
0.7283	Intermediate Similarity	NPD977	Approved
0.7282	Intermediate Similarity	NPD5426	Phase 3
0.7282	Intermediate Similarity	NPD8272	Phase 2
0.7282	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7603	Discontinued
0.7273	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3013	Phase 3
0.7269	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8073	Approved
0.7268	Intermediate Similarity	NPD2882	Phase 1
0.7264	Intermediate Similarity	NPD6957	Approved
0.7264	Intermediate Similarity	NPD6958	Approved
0.7263	Intermediate Similarity	NPD3717	Discontinued
0.7258	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6164	Phase 2
0.7248	Intermediate Similarity	NPD6165	Phase 2
0.7234	Intermediate Similarity	NPD5138	Approved
0.7234	Intermediate Similarity	NPD5140	Approved
0.7228	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8020	Approved
0.7222	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8021	Approved
0.7215	Intermediate Similarity	NPD7780	Approved
0.7215	Intermediate Similarity	NPD7781	Approved
0.7214	Intermediate Similarity	NPD5428	Discontinued
0.7208	Intermediate Similarity	NPD3082	Discontinued
0.7202	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD1661	Suspended
0.7198	Intermediate Similarity	NPD5901	Discontinued
0.7194	Intermediate Similarity	NPD5596	Phase 2
0.7194	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6850	Phase 2
0.7189	Intermediate Similarity	NPD6849	Phase 2
0.7183	Intermediate Similarity	NPD6711	Approved
0.7183	Intermediate Similarity	NPD7112	Discontinued
0.7177	Intermediate Similarity	NPD4612	Discontinued
0.7174	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6158	Phase 2
0.7172	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4601	Approved
0.7171	Intermediate Similarity	NPD4600	Approved
0.7165	Intermediate Similarity	NPD7111	Discontinued
0.7163	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD424	Approved
0.7158	Intermediate Similarity	NPD425	Approved
0.7157	Intermediate Similarity	NPD6469	Phase 3
0.7157	Intermediate Similarity	NPD4957	Phase 2
0.7157	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7470	Discontinued
0.7156	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8072	Approved
0.715	Intermediate Similarity	NPD6492	Phase 2
0.715	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1683	Approved
0.7136	Intermediate Similarity	NPD4511	Phase 1
0.7136	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7188	Phase 3
0.7129	Intermediate Similarity	NPD8322	Phase 2
0.7123	Intermediate Similarity	NPD8289	Discontinued
0.7121	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5021	Discontinued
0.7109	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD8321	Discontinued
0.7103	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6132	Phase 1
0.71	Intermediate Similarity	NPD6363	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD750	Phase 2
0.7094	Intermediate Similarity	NPD7944	Discontinued
0.7091	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6978	Phase 2
0.709	Intermediate Similarity	NPD6771	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