NPASS Compound

Structure

NPC471506 OpenBabel07101718282D 42 50 0 0 1 0 0 0 0 0999 V2000 3.8724 -0.0576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8414 -0.4708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7210 0.3280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6343 -0.8295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1157 0.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7090 1.4521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4173 0.6098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2920 -1.0629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7469 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0849 1.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5279 -0.2705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7145 1.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7903 -1.8351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3925 -0.6600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0214 0.7320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9242 -2.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8823 -1.1247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2891 1.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3150 -0.8654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1922 0.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3939 -0.5422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1827 -0.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5334 -0.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7903 -0.8351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1922 -0.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6118 -0.6702 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.1267 0.7476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0582 -0.8351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9242 -0.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0313 0.3351 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0313 -0.3351 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6118 0.6702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0582 -1.8351 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1322 0.6430 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4864 -1.0026 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.3939 0.5422 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.0533 1.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 11 26 2 0 0 0 0 12 30 2 0 0 0 0 13 17 1 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 27 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 16 35 1 0 0 0 0 17 36 1 0 0 0 0 18 37 1 0 0 0 0 19 39 1 0 0 0 0 20 40 1 0 0 0 0 21 39 1 0 0 0 0 22 28 2 0 0 0 0 22 35 1 0 0 0 0 23 36 1 0 0 0 0 24 34 1 0 0 0 0 24 39 1 0 0 0 0 25 10 1 1 0 0 0 25 42 1 0 0 0 0 26 27 1 0 0 0 0 26 30 1 0 0 0 0 27 32 2 0 0 0 0 28 29 1 0 0 0 0 28 31 1 0 0 0 0 29 34 1 0 0 0 0 30 38 1 0 0 0 0 31 32 1 0 0 0 0 31 37 2 0 0 0 0 32 38 1 0 0 0 0 33 34 1 1 0 0 0 33 35 1 0 0 0 0 33 40 1 0 0 0 0 34 23 1 1 0 0 0 35 41 1 1 0 0 0 36 40 1 1 0 0 0 36 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.35
Volume:	594.68
LogP:	4.82
LogD:	3.743
LogS:	-3.595
# Rotatable Bonds:	1
TPSA:	64.62
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	9
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	7.258
Fsp3:	0.583
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:	-5.086
MDCK Permeability:	2.3492835680372082e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.855
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.948
Plasma Protein Binding (PPB):	90.61609649658203%
Volume Distribution (VD):	3.642
Pgp-substrate:	7.565485000610352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.166
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.975
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.973
CYP3A4-substrate:	0.925

ADMET: Excretion

Clearance (CL):	8.216
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.939
Human Hepatotoxicity (H-HT):	0.988
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.408
Rat Oral Acute Toxicity:	0.251
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.946
Carcinogencity:	0.729
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC471506

Natural Product ID:	NPC471506
*Common Name:**	6-Deoxymanzamine X
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CLKZPQNKNPCQGL-NZGBLPSWSA-N
Standard InCHI:	InChI=1S/C36H44N4O2/c41-35-16-7-3-1-2-4-8-19-39-21-15-29(34(24-39)23-36-17-13-25(42-36)10-9-20-40(36)33(34)35)28(22-35)31-32-27(14-18-37-31)26-11-5-6-12-30(26)38-32/h1,3,5-6,11-12,14,18,22,25,29,33,38,41H,2,4,7-10,13,15-17,19-21,23-24H2/b3-1-/t25-,29?,33+,34-,35-,36+/m0/s1
SMILES:	C1=CCC[C@@]2(C=C(C3CCN(CCCC1)C[C@]13C[C@]34CC[C@H](CCCN3[C@@H]21)O4)c1c2c(ccn1)c1ccccc1[nH]2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253548
PubChem CID:	44445400
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
NPO32531	sponge sp.	Species	n.a.	n.a.	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape, Manado Bay, Indonesia	2011-MAR	PMID[12828469]
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
EC50	2
ED50	1
IC50	14
MIC	2
Others	6

Activity Type	# Activity
Cell Line	4
Individual Protein	1
NON-MOLECULAR	2
Organism	17
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	Inhibition	=	88.4	%	PMID[549057]
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	=	1.8	ug ml-1	PMID[549058]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Activity	=	4760.0	ng/ml	PMID[549059]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.5	ug.mL-1	PMID[549059]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Activity	=	4.7	ug ml-1	PMID[549060]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Inhibition	=	18.5	%	PMID[549058]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1.77	ug.mL-1	PMID[549059]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.3	ug.mL-1	PMID[549059]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.4	ug.mL-1	PMID[549059]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	3.2	ug.mL-1	PMID[549059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.0	ug.mL-1	PMID[549059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.5	ug.mL-1	PMID[549059]
NPT27	Others	Unspecified		IC50	=	1.0	ug.mL-1	PMID[549059]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1600.0	nM	PMID[549059]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	7.5	ug.mL-1	PMID[549059]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.3	ug.mL-1	PMID[549060]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.4	ug.mL-1	PMID[549060]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	3.2	ug.mL-1	PMID[549060]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	1.5	ug.mL-1	PMID[549060]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	2.0	ug.mL-1	PMID[549060]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	6.25	ug.mL-1	PMID[549060]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1600.0	nM	PMID[549060]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	7.5	ug.mL-1	PMID[549060]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1.8	ug.mL-1	PMID[549060]

☑ 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 NPC471506 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	494
0.1-0.2	2055
0.2-0.3	13028
0.3-0.4	19373
0.4-0.5	3612
0.5-0.6	2255
0.6-0.7	1588
0.7-0.8	264
0.8-0.85	11
0.85-0.9	12
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9272	High Similarity	NPC476492
0.9245	High Similarity	NPC81175
0.9045	High Similarity	NPC473362
0.9045	High Similarity	NPC166492
0.8971	High Similarity	NPC472027
0.8966	High Similarity	NPC473757
0.8832	High Similarity	NPC265576
0.8829	High Similarity	NPC250835
0.8733	High Similarity	NPC471564
0.8702	High Similarity	NPC473310
0.8638	High Similarity	NPC475258
0.8621	High Similarity	NPC475288
0.8616	High Similarity	NPC476493
0.8592	High Similarity	NPC909
0.8592	High Similarity	NPC475338
0.8465	Intermediate Similarity	NPC6215
0.8438	Intermediate Similarity	NPC471891
0.8341	Intermediate Similarity	NPC251936
0.8295	Intermediate Similarity	NPC476491
0.8265	Intermediate Similarity	NPC476451
0.819	Intermediate Similarity	NPC475422
0.8125	Intermediate Similarity	NPC41679
0.8095	Intermediate Similarity	NPC87755
0.8049	Intermediate Similarity	NPC232130
0.8019	Intermediate Similarity	NPC126066
0.7991	Intermediate Similarity	NPC475602
0.7939	Intermediate Similarity	NPC473312
0.7811	Intermediate Similarity	NPC139291
0.7811	Intermediate Similarity	NPC472108
0.7793	Intermediate Similarity	NPC313884
0.7793	Intermediate Similarity	NPC98371
0.7734	Intermediate Similarity	NPC15102
0.7717	Intermediate Similarity	NPC476041
0.7717	Intermediate Similarity	NPC304926
0.7696	Intermediate Similarity	NPC477861
0.7692	Intermediate Similarity	NPC133366
0.7674	Intermediate Similarity	NPC314957
0.7644	Intermediate Similarity	NPC474177
0.7635	Intermediate Similarity	NPC472109
0.7635	Intermediate Similarity	NPC472110
0.7635	Intermediate Similarity	NPC48938
0.7612	Intermediate Similarity	NPC59269
0.7604	Intermediate Similarity	NPC5145
0.7602	Intermediate Similarity	NPC477714
0.76	Intermediate Similarity	NPC189812
0.76	Intermediate Similarity	NPC329688
0.7598	Intermediate Similarity	NPC472294
0.7585	Intermediate Similarity	NPC95783
0.7557	Intermediate Similarity	NPC477715
0.7547	Intermediate Similarity	NPC100321
0.7535	Intermediate Similarity	NPC470500
0.7535	Intermediate Similarity	NPC475070
0.7533	Intermediate Similarity	NPC33949
0.7525	Intermediate Similarity	NPC326575
0.7523	Intermediate Similarity	NPC193761
0.7511	Intermediate Similarity	NPC469554
0.75	Intermediate Similarity	NPC221100
0.75	Intermediate Similarity	NPC234078
0.7487	Intermediate Similarity	NPC317430
0.7477	Intermediate Similarity	NPC162860
0.7477	Intermediate Similarity	NPC478158
0.7477	Intermediate Similarity	NPC476116
0.7477	Intermediate Similarity	NPC475506
0.7475	Intermediate Similarity	NPC24594
0.7475	Intermediate Similarity	NPC472122
0.7463	Intermediate Similarity	NPC472123
0.7452	Intermediate Similarity	NPC65215
0.7452	Intermediate Similarity	NPC213629
0.7452	Intermediate Similarity	NPC173028
0.7444	Intermediate Similarity	NPC281049
0.7442	Intermediate Similarity	NPC155143
0.7438	Intermediate Similarity	NPC151939
0.7437	Intermediate Similarity	NPC160105
0.7418	Intermediate Similarity	NPC171317
0.7418	Intermediate Similarity	NPC473640
0.7416	Intermediate Similarity	NPC469501
0.7416	Intermediate Similarity	NPC469470
0.7415	Intermediate Similarity	NPC314394
0.7404	Intermediate Similarity	NPC317030
0.7404	Intermediate Similarity	NPC204565
0.7402	Intermediate Similarity	NPC133261
0.74	Intermediate Similarity	NPC63751
0.74	Intermediate Similarity	NPC201700
0.7397	Intermediate Similarity	NPC107077
0.7397	Intermediate Similarity	NPC223791
0.7389	Intermediate Similarity	NPC280852
0.7389	Intermediate Similarity	NPC203754
0.7389	Intermediate Similarity	NPC150048
0.7389	Intermediate Similarity	NPC155444
0.7387	Intermediate Similarity	NPC478157
0.7385	Intermediate Similarity	NPC54420
0.738	Intermediate Similarity	NPC314954
0.7379	Intermediate Similarity	NPC19679
0.7376	Intermediate Similarity	NPC314603
0.7366	Intermediate Similarity	NPC187827
0.7366	Intermediate Similarity	NPC472105
0.7366	Intermediate Similarity	NPC300688
0.7359	Intermediate Similarity	NPC101543
0.7356	Intermediate Similarity	NPC474707
0.735	Intermediate Similarity	NPC474561
0.735	Intermediate Similarity	NPC49954
0.7348	Intermediate Similarity	NPC470729
0.7348	Intermediate Similarity	NPC477176
0.7348	Intermediate Similarity	NPC470730
0.7348	Intermediate Similarity	NPC477175
0.7343	Intermediate Similarity	NPC284678
0.7342	Intermediate Similarity	NPC229348
0.7337	Intermediate Similarity	NPC311276
0.733	Intermediate Similarity	NPC320968
0.733	Intermediate Similarity	NPC233936
0.7328	Intermediate Similarity	NPC70155
0.7327	Intermediate Similarity	NPC98715
0.7318	Intermediate Similarity	NPC271862
0.7316	Intermediate Similarity	NPC474877
0.7316	Intermediate Similarity	NPC475969
0.7316	Intermediate Similarity	NPC475859
0.7315	Intermediate Similarity	NPC300183
0.7308	Intermediate Similarity	NPC62510
0.7304	Intermediate Similarity	NPC253580
0.7304	Intermediate Similarity	NPC56109
0.7304	Intermediate Similarity	NPC191382
0.7295	Intermediate Similarity	NPC472444
0.7294	Intermediate Similarity	NPC470505
0.729	Intermediate Similarity	NPC229332
0.7289	Intermediate Similarity	NPC469594
0.7286	Intermediate Similarity	NPC46413
0.7284	Intermediate Similarity	NPC165743
0.7281	Intermediate Similarity	NPC476874
0.7277	Intermediate Similarity	NPC183407
0.7273	Intermediate Similarity	NPC62749
0.7273	Intermediate Similarity	NPC258062
0.7273	Intermediate Similarity	NPC127677
0.7269	Intermediate Similarity	NPC303820
0.7269	Intermediate Similarity	NPC205254
0.7269	Intermediate Similarity	NPC310118
0.7269	Intermediate Similarity	NPC106771
0.7269	Intermediate Similarity	NPC23420
0.7265	Intermediate Similarity	NPC295228
0.7264	Intermediate Similarity	NPC54988
0.7261	Intermediate Similarity	NPC470126
0.7261	Intermediate Similarity	NPC57690
0.7257	Intermediate Similarity	NPC213530
0.7257	Intermediate Similarity	NPC193267
0.7236	Intermediate Similarity	NPC279918
0.7235	Intermediate Similarity	NPC475935
0.7235	Intermediate Similarity	NPC94211
0.7235	Intermediate Similarity	NPC52909
0.7233	Intermediate Similarity	NPC141377
0.7233	Intermediate Similarity	NPC472443
0.7227	Intermediate Similarity	NPC477065
0.7227	Intermediate Similarity	NPC46225
0.7227	Intermediate Similarity	NPC225821
0.7225	Intermediate Similarity	NPC163421
0.7225	Intermediate Similarity	NPC188387
0.7222	Intermediate Similarity	NPC469762
0.7222	Intermediate Similarity	NPC293917
0.7222	Intermediate Similarity	NPC325976
0.722	Intermediate Similarity	NPC151976
0.722	Intermediate Similarity	NPC87856
0.722	Intermediate Similarity	NPC75634
0.7217	Intermediate Similarity	NPC472762
0.7206	Intermediate Similarity	NPC34508
0.7204	Intermediate Similarity	NPC321708
0.72	Intermediate Similarity	NPC132211
0.72	Intermediate Similarity	NPC282231
0.7196	Intermediate Similarity	NPC195314
0.719	Intermediate Similarity	NPC94752
0.7189	Intermediate Similarity	NPC81654
0.7189	Intermediate Similarity	NPC195461
0.7189	Intermediate Similarity	NPC249150
0.7189	Intermediate Similarity	NPC49196
0.7189	Intermediate Similarity	NPC313985
0.7189	Intermediate Similarity	NPC249040
0.7189	Intermediate Similarity	NPC79129
0.7188	Intermediate Similarity	NPC54744
0.7188	Intermediate Similarity	NPC469592
0.7188	Intermediate Similarity	NPC471080
0.7188	Intermediate Similarity	NPC267965
0.7186	Intermediate Similarity	NPC110151
0.7186	Intermediate Similarity	NPC135141
0.7186	Intermediate Similarity	NPC92796
0.7183	Intermediate Similarity	NPC324149
0.7182	Intermediate Similarity	NPC238457
0.7176	Intermediate Similarity	NPC192315
0.7176	Intermediate Similarity	NPC50503
0.7172	Intermediate Similarity	NPC469785
0.7164	Intermediate Similarity	NPC40779
0.7164	Intermediate Similarity	NPC194640
0.7163	Intermediate Similarity	NPC11445
0.7162	Intermediate Similarity	NPC162748
0.715	Intermediate Similarity	NPC81229
0.715	Intermediate Similarity	NPC176199
0.715	Intermediate Similarity	NPC270009
0.715	Intermediate Similarity	NPC255229
0.715	Intermediate Similarity	NPC215795
0.7143	Intermediate Similarity	NPC24370
0.7143	Intermediate Similarity	NPC319232
0.7143	Intermediate Similarity	NPC32200
0.7143	Intermediate Similarity	NPC476167
0.7137	Intermediate Similarity	NPC107836

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 NPC471506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	566
0.2-0.3	885
0.3-0.4	2067
0.4-0.5	2733
0.5-0.6	1919
0.6-0.7	703
0.7-0.8	43
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7822	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7824	Approved
0.7793	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD6978	Phase 2
0.7723	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7731	Approved
0.7723	Intermediate Similarity	NPD7730	Approved
0.7713	Intermediate Similarity	NPD7271	Approved
0.7632	Intermediate Similarity	NPD7789	Approved
0.7632	Intermediate Similarity	NPD7951	Approved
0.7632	Intermediate Similarity	NPD7791	Approved
0.7632	Intermediate Similarity	NPD7952	Approved
0.7632	Intermediate Similarity	NPD7953	Approved
0.7632	Intermediate Similarity	NPD7950	Approved
0.7632	Intermediate Similarity	NPD7790	Approved
0.7537	Intermediate Similarity	NPD6595	Phase 3
0.7525	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD4886	Phase 2
0.7466	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3330	Phase 1
0.7455	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5065	Approved
0.7404	Intermediate Similarity	NPD8431	Approved
0.7366	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7957	Phase 1
0.7339	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6455	Phase 3
0.7304	Intermediate Similarity	NPD7781	Approved
0.7304	Intermediate Similarity	NPD7780	Approved
0.7301	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7666	Phase 3
0.7273	Intermediate Similarity	NPD7665	Phase 2
0.7252	Intermediate Similarity	NPD7470	Discontinued
0.7227	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5426	Phase 3
0.7209	Intermediate Similarity	NPD7948	Phase 1
0.7204	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4601	Approved
0.7189	Intermediate Similarity	NPD4600	Approved
0.7184	Intermediate Similarity	NPD2144	Approved
0.7175	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3038	Discontinued
0.7162	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4076	Approved
0.715	Intermediate Similarity	NPD4079	Approved
0.7149	Intermediate Similarity	NPD8322	Phase 2
0.7143	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD7558	Phase 2
0.7105	Intermediate Similarity	NPD3402	Phase 1
0.7104	Intermediate Similarity	NPD7001	Phase 3
0.7101	Intermediate Similarity	NPD3505	Approved
0.7101	Intermediate Similarity	NPD3506	Approved
0.7083	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7502	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD8021	Approved
0.7075	Intermediate Similarity	NPD8020	Approved
0.7075	Intermediate Similarity	NPD3961	Discontinued
0.7075	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7921	Approved
0.7048	Intermediate Similarity	NPD5596	Phase 2
0.7032	Intermediate Similarity	NPD4501	Approved
0.7032	Intermediate Similarity	NPD4500	Approved
0.7023	Intermediate Similarity	NPD3404	Approved
0.7019	Intermediate Similarity	NPD8123	Approved
0.7019	Intermediate Similarity	NPD8122	Approved
0.7019	Intermediate Similarity	NPD4181	Approved
0.7009	Intermediate Similarity	NPD6281	Approved
0.7009	Intermediate Similarity	NPD8063	Discontinued
0.7004	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8408	Discontinued
0.6996	Remote Similarity	NPD6352	Phase 2
0.6991	Remote Similarity	NPD8093	Discontinued
0.6991	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD8386	Phase 2
0.6986	Remote Similarity	NPD6999	Discontinued
0.6985	Remote Similarity	NPD2837	Discontinued
0.6982	Remote Similarity	NPD4036	Approved
0.6982	Remote Similarity	NPD4039	Approved
0.6982	Remote Similarity	NPD4038	Approved
0.6982	Remote Similarity	NPD4033	Approved
0.6982	Remote Similarity	NPD4035	Approved
0.6982	Remote Similarity	NPD4037	Approved
0.6982	Remote Similarity	NPD8272	Phase 2
0.6982	Remote Similarity	NPD4122	Approved
0.6982	Remote Similarity	NPD32	Approved
0.6982	Remote Similarity	NPD31	Approved
0.6982	Remote Similarity	NPD4034	Approved
0.6981	Remote Similarity	NPD3082	Discontinued
0.6978	Remote Similarity	NPD8321	Discontinued
0.6977	Remote Similarity	NPD5913	Phase 3
0.6977	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5862	Discovery
0.6971	Remote Similarity	NPD2380	Approved
0.6971	Remote Similarity	NPD2381	Approved
0.6971	Remote Similarity	NPD2382	Approved
0.6968	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2095	Phase 2
0.6967	Remote Similarity	NPD2094	Phase 2
0.6967	Remote Similarity	NPD2092	Phase 2
0.6959	Remote Similarity	NPD7618	Phase 3
0.6959	Remote Similarity	NPD7619	Phase 3
0.6959	Remote Similarity	NPD7944	Discontinued
0.6957	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8072	Approved
0.6934	Remote Similarity	NPD2091	Phase 2
0.6934	Remote Similarity	NPD2096	Phase 2
0.6934	Remote Similarity	NPD4957	Phase 2
0.6931	Remote Similarity	NPD5255	Approved
0.693	Remote Similarity	NPD4499	Approved
0.6927	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3323	Discontinued
0.6909	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6165	Phase 2
0.6894	Remote Similarity	NPD6164	Phase 2
0.6892	Remote Similarity	NPD8073	Approved
0.6888	Remote Similarity	NPD6992	Phase 2
0.6875	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6970	Phase 2
0.686	Remote Similarity	NPD1325	Approved
0.686	Remote Similarity	NPD1326	Approved
0.6857	Remote Similarity	NPD8250	Phase 2
0.6854	Remote Similarity	NPD6178	Phase 3
0.6851	Remote Similarity	NPD8289	Discontinued
0.6851	Remote Similarity	NPD7711	Discontinued
0.6847	Remote Similarity	NPD8629	Discontinued
0.6842	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4128	Approved
0.6842	Remote Similarity	NPD482	Approved
0.6838	Remote Similarity	NPD7717	Approved
0.6838	Remote Similarity	NPD7716	Approved
0.6837	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.683	Remote Similarity	NPD5901	Discontinued
0.6828	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3013	Phase 3
0.6827	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7112	Discontinued
0.6826	Remote Similarity	NPD3393	Approved
0.6826	Remote Similarity	NPD3389	Approved
0.6826	Remote Similarity	NPD5612	Discontinued
0.6826	Remote Similarity	NPD3394	Approved
0.6818	Remote Similarity	NPD7469	Discontinued
0.6814	Remote Similarity	NPD2510	Approved
0.6814	Remote Similarity	NPD4612	Discontinued
0.6814	Remote Similarity	NPD2509	Approved
0.6812	Remote Similarity	NPD4638	Approved
0.6812	Remote Similarity	NPD4640	Approved
0.6812	Remote Similarity	NPD4639	Approved
0.6812	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD8094	Discontinued
0.68	Remote Similarity	NPD2172	Phase 1
0.68	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7423	Phase 2
0.6791	Remote Similarity	NPD706	Phase 1
0.6784	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6850	Phase 2
0.6766	Remote Similarity	NPD6849	Phase 2
0.6762	Remote Similarity	NPD7770	Phase 3
0.6761	Remote Similarity	NPD7867	Phase 1
0.676	Remote Similarity	NPD8247	Approved
0.676	Remote Similarity	NPD8246	Approved
0.676	Remote Similarity	NPD8442	Discontinued
0.6757	Remote Similarity	NPD8395	Approved
0.6757	Remote Similarity	NPD8396	Approved
0.6754	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7726	Phase 1
0.675	Remote Similarity	NPD7415	Suspended
0.6744	Remote Similarity	NPD6227	Discontinued
0.6743	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5003	Discontinued
0.6736	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7769	Phase 3
0.673	Remote Similarity	NPD5100	Phase 3
0.673	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4602	Approved

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