NPASS Compound

Structure

NPC472027 OpenBabel07101718222D 41 49 0 0 1 0 0 0 0 0999 V2000 2.8120 -1.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9108 -2.1238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4385 -0.9203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7154 -2.7574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7355 -0.7291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6989 -1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2925 -0.1442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8568 -0.3984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2710 0.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8642 -0.5888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2644 -3.2434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1999 -1.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4730 -1.2965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3013 0.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5772 0.0190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1584 -3.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4057 -2.8471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2031 -0.5393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4424 -3.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6472 -3.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4819 -3.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8860 -2.8724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3019 -1.1949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4118 -3.1046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4719 -2.0909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5032 -1.4131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9410 -2.2118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4251 -2.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8627 -2.6186 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9174 -0.6316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9243 -0.3157 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2917 -2.5882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0077 -1.9239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0236 -1.5802 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0383 -2.5568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5858 -0.7815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5091 -3.5405 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9931 -0.9473 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9860 -3.4361 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.9097 -1.2923 0.0000 N 0 0 3 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 10 1 0 0 0 0 4 11 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 19 2 0 0 0 0 16 27 1 0 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 19 37 1 0 0 0 0 20 39 1 0 0 0 0 21 39 1 0 0 0 0 22 25 1 0 0 0 0 23 28 2 0 0 0 0 23 36 1 0 0 0 0 24 35 1 0 0 0 0 24 39 1 0 0 0 0 25 40 1 6 0 0 0 26 27 2 0 0 0 0 26 30 1 0 0 0 0 27 33 1 0 0 0 0 28 29 1 0 0 0 0 28 32 1 0 0 0 0 29 35 1 1 0 0 0 30 38 2 0 0 0 0 31 40 1 1 0 0 0 31 41 1 0 0 0 0 32 33 2 0 0 0 0 32 37 1 0 0 0 0 33 38 1 0 0 0 0 34 35 1 1 0 0 0 34 36 1 0 0 0 0 34 40 1 0 0 0 0 35 22 1 1 0 0 0 36 18 1 6 0 0 0 36 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.34
Volume:	583.253
LogP:	5.481
LogD:	4.308
LogS:	-3.695
# Rotatable Bonds:	1
TPSA:	44.39
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	6.832
Fsp3:	0.528
Lipinski Rule-of-5:	Rejected
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:	-5.16
MDCK Permeability:	2.343577034480404e-05
Pgp-inhibitor:	0.936
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.689

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.538
Plasma Protein Binding (PPB):	96.5344467163086%
Volume Distribution (VD):	2.069
Pgp-substrate:	2.086322784423828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.147
CYP1A2-substrate:	0.9
CYP2C19-inhibitor:	0.422
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.4
CYP2D6-inhibitor:	0.988
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	4.444
Half-life (T1/2):	0.107

ADMET: Toxicity

hERG Blockers:	0.941
Human Hepatotoxicity (H-HT):	0.989
Drug-inuced Liver Injury (DILI):	0.349
AMES Toxicity:	0.797
Rat Oral Acute Toxicity:	0.708
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.952
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC472027

Natural Product ID:	NPC472027
*Common Name:**	12,28-Oxamanzamine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	URHUZIUZTFPQSX-UGZVZIBKSA-N
Standard InCHI:	InChI=1S/C36H42N4O/c1-2-4-11-20-39-21-17-29-28(32-33-27(16-19-37-32)26-13-8-9-14-30(26)38-33)23-36(18-10-3-1)34-35(29,24-39)22-25-12-6-5-7-15-31(41-36)40(25)34/h1,3,6,8-9,12-14,16,19,23,25,29,31,34,37H,2,4-5,7,10-11,15,17-18,20-22,24H2/b3-1-,12-6-/t25-,29-,31+,34+,35-,36-/m0/s1
SMILES:	C1/C=CCC[C@]23O[C@H]4N5[C@@H]3[C@]3(CN(CCC1)CC[C@H]3C(=C2)c1[nH]ccc2c1nc1c2cccc1)C[C@@H]5C=CCCC4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL332889
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
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]

☑ 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	1
IC50	2
Others	1

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	22200.0	nM	PMID[551388]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	7.8	ug.mL-1	PMID[551389]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	22.2	ug.mL-1	PMID[551389]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	50.0	ug.mL-1	PMID[551389]

☑ 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 NPC472027 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	574
0.1-0.2	2812
0.2-0.3	21416
0.3-0.4	10737
0.4-0.5	3104
0.5-0.6	2239
0.6-0.7	1521
0.7-0.8	270
0.8-0.85	11
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC473757
0.9216	High Similarity	NPC475258
0.9179	High Similarity	NPC166492
0.9179	High Similarity	NPC473362
0.9073	High Similarity	NPC909
0.9073	High Similarity	NPC475338
0.8971	High Similarity	NPC471506
0.8861	High Similarity	NPC250835
0.8802	High Similarity	NPC471891
0.8769	High Similarity	NPC265576
0.8578	High Similarity	NPC476492
0.8551	High Similarity	NPC473310
0.8544	High Similarity	NPC251936
0.8465	Intermediate Similarity	NPC475288
0.8404	Intermediate Similarity	NPC6215
0.8318	Intermediate Similarity	NPC81175
0.8259	Intermediate Similarity	NPC471564
0.8213	Intermediate Similarity	NPC126066
0.8203	Intermediate Similarity	NPC476451
0.815	Intermediate Similarity	NPC476493
0.8069	Intermediate Similarity	NPC232130
0.8065	Intermediate Similarity	NPC476491
0.7902	Intermediate Similarity	NPC41679
0.7867	Intermediate Similarity	NPC475422
0.7857	Intermediate Similarity	NPC87755
0.784	Intermediate Similarity	NPC475602
0.775	Intermediate Similarity	NPC15102
0.7719	Intermediate Similarity	NPC473312
0.7703	Intermediate Similarity	NPC314954
0.77	Intermediate Similarity	NPC284678
0.7576	Intermediate Similarity	NPC280852
0.7534	Intermediate Similarity	NPC477714
0.7525	Intermediate Similarity	NPC472294
0.7489	Intermediate Similarity	NPC304926
0.7489	Intermediate Similarity	NPC477715
0.7489	Intermediate Similarity	NPC476041
0.7478	Intermediate Similarity	NPC477861
0.7477	Intermediate Similarity	NPC155444
0.7452	Intermediate Similarity	NPC133366
0.745	Intermediate Similarity	NPC59269
0.7445	Intermediate Similarity	NPC469554
0.7442	Intermediate Similarity	NPC314957
0.7431	Intermediate Similarity	NPC234078
0.7431	Intermediate Similarity	NPC221100
0.7427	Intermediate Similarity	NPC95783
0.7413	Intermediate Similarity	NPC141377
0.7411	Intermediate Similarity	NPC317430
0.7407	Intermediate Similarity	NPC162860
0.7395	Intermediate Similarity	NPC54420
0.7389	Intermediate Similarity	NPC56109
0.7389	Intermediate Similarity	NPC191382
0.7389	Intermediate Similarity	NPC48938
0.7371	Intermediate Similarity	NPC193761
0.7368	Intermediate Similarity	NPC101543
0.7347	Intermediate Similarity	NPC317105
0.7346	Intermediate Similarity	NPC171317
0.7333	Intermediate Similarity	NPC255229
0.7333	Intermediate Similarity	NPC98371
0.7333	Intermediate Similarity	NPC81229
0.7333	Intermediate Similarity	NPC313884
0.7327	Intermediate Similarity	NPC478158
0.7323	Intermediate Similarity	NPC201700
0.7321	Intermediate Similarity	NPC474177
0.7311	Intermediate Similarity	NPC100321
0.7304	Intermediate Similarity	NPC472108
0.7304	Intermediate Similarity	NPC139291
0.7302	Intermediate Similarity	NPC475070
0.73	Intermediate Similarity	NPC472123
0.7295	Intermediate Similarity	NPC213629
0.7295	Intermediate Similarity	NPC65215
0.7295	Intermediate Similarity	NPC173028
0.7294	Intermediate Similarity	NPC167860
0.7294	Intermediate Similarity	NPC123976
0.7281	Intermediate Similarity	NPC470730
0.7281	Intermediate Similarity	NPC477175
0.7277	Intermediate Similarity	NPC151939
0.7277	Intermediate Similarity	NPC19872
0.7277	Intermediate Similarity	NPC176538
0.7277	Intermediate Similarity	NPC303820
0.7277	Intermediate Similarity	NPC106771
0.7277	Intermediate Similarity	NPC205254
0.7277	Intermediate Similarity	NPC23420
0.7273	Intermediate Similarity	NPC160105
0.7264	Intermediate Similarity	NPC473640
0.7254	Intermediate Similarity	NPC325903
0.7249	Intermediate Similarity	NPC475969
0.7249	Intermediate Similarity	NPC475859
0.7248	Intermediate Similarity	NPC223791
0.7248	Intermediate Similarity	NPC107077
0.7246	Intermediate Similarity	NPC317030
0.7246	Intermediate Similarity	NPC204565
0.7243	Intermediate Similarity	NPC52909
0.7243	Intermediate Similarity	NPC475506
0.7243	Intermediate Similarity	NPC94211
0.7243	Intermediate Similarity	NPC475935
0.724	Intermediate Similarity	NPC478157
0.7236	Intermediate Similarity	NPC63751
0.7231	Intermediate Similarity	NPC216643
0.7225	Intermediate Similarity	NPC469811
0.7225	Intermediate Similarity	NPC472762
0.722	Intermediate Similarity	NPC281049
0.722	Intermediate Similarity	NPC472109
0.722	Intermediate Similarity	NPC472110
0.7217	Intermediate Similarity	NPC165743
0.7215	Intermediate Similarity	NPC5145
0.7214	Intermediate Similarity	NPC314603
0.7209	Intermediate Similarity	NPC155143
0.7207	Intermediate Similarity	NPC183407
0.7206	Intermediate Similarity	NPC300688
0.7198	Intermediate Similarity	NPC474707
0.7194	Intermediate Similarity	NPC221786
0.7194	Intermediate Similarity	NPC135141
0.7194	Intermediate Similarity	NPC92796
0.7194	Intermediate Similarity	NPC475990
0.7194	Intermediate Similarity	NPC474880
0.7188	Intermediate Similarity	NPC321911
0.7186	Intermediate Similarity	NPC180504
0.7186	Intermediate Similarity	NPC474561
0.7186	Intermediate Similarity	NPC49954
0.7183	Intermediate Similarity	NPC67288
0.7179	Intermediate Similarity	NPC469785
0.7178	Intermediate Similarity	NPC189812
0.7178	Intermediate Similarity	NPC329688
0.7176	Intermediate Similarity	NPC476138
0.7176	Intermediate Similarity	NPC245816
0.7173	Intermediate Similarity	NPC63545
0.7172	Intermediate Similarity	NPC311276
0.7171	Intermediate Similarity	NPC233936
0.7163	Intermediate Similarity	NPC232727
0.7157	Intermediate Similarity	NPC229173
0.7149	Intermediate Similarity	NPC118940
0.7143	Intermediate Similarity	NPC469762
0.7136	Intermediate Similarity	NPC19679
0.7136	Intermediate Similarity	NPC229332
0.7135	Intermediate Similarity	NPC179787
0.7135	Intermediate Similarity	NPC201380
0.713	Intermediate Similarity	NPC473761
0.7129	Intermediate Similarity	NPC196251
0.7129	Intermediate Similarity	NPC111602
0.7129	Intermediate Similarity	NPC63199
0.7129	Intermediate Similarity	NPC102338
0.7128	Intermediate Similarity	NPC80597
0.7128	Intermediate Similarity	NPC75540
0.7128	Intermediate Similarity	NPC212376
0.7128	Intermediate Similarity	NPC70922
0.7128	Intermediate Similarity	NPC211572
0.7124	Intermediate Similarity	NPC295228
0.7121	Intermediate Similarity	NPC470203
0.7116	Intermediate Similarity	NPC214428
0.7115	Intermediate Similarity	NPC62749
0.7115	Intermediate Similarity	NPC94752
0.7114	Intermediate Similarity	NPC474897
0.7111	Intermediate Similarity	NPC213530
0.7111	Intermediate Similarity	NPC193267
0.711	Intermediate Similarity	NPC238457
0.7109	Intermediate Similarity	NPC324149
0.7107	Intermediate Similarity	NPC56765
0.7107	Intermediate Similarity	NPC230869
0.71	Intermediate Similarity	NPC54988
0.71	Intermediate Similarity	NPC477177
0.7097	Intermediate Similarity	NPC98715
0.7095	Intermediate Similarity	NPC231536
0.7093	Intermediate Similarity	NPC162748
0.7091	Intermediate Similarity	NPC476116
0.7091	Intermediate Similarity	NPC271862
0.7089	Intermediate Similarity	NPC245916
0.7083	Intermediate Similarity	NPC300183
0.7078	Intermediate Similarity	NPC477065
0.7077	Intermediate Similarity	NPC469786
0.7077	Intermediate Similarity	NPC25008
0.7077	Intermediate Similarity	NPC259644
0.7077	Intermediate Similarity	NPC73952
0.7077	Intermediate Similarity	NPC469760
0.7077	Intermediate Similarity	NPC469765
0.7077	Intermediate Similarity	NPC469763
0.7075	Intermediate Similarity	NPC473178
0.7073	Intermediate Similarity	NPC133261
0.7073	Intermediate Similarity	NPC215795
0.7073	Intermediate Similarity	NPC176199
0.7073	Intermediate Similarity	NPC6093
0.7072	Intermediate Similarity	NPC26679
0.7072	Intermediate Similarity	NPC75634
0.7071	Intermediate Similarity	NPC122141
0.7071	Intermediate Similarity	NPC470204
0.7071	Intermediate Similarity	NPC279918
0.707	Intermediate Similarity	NPC293917
0.7067	Intermediate Similarity	NPC280290
0.7067	Intermediate Similarity	NPC473189
0.7062	Intermediate Similarity	NPC53947
0.7059	Intermediate Similarity	NPC150048
0.7059	Intermediate Similarity	NPC203754
0.7056	Intermediate Similarity	NPC470729
0.7056	Intermediate Similarity	NPC477176
0.7054	Intermediate Similarity	NPC36405
0.7051	Intermediate Similarity	NPC476874
0.7051	Intermediate Similarity	NPC260900
0.7048	Intermediate Similarity	NPC2395
0.7048	Intermediate Similarity	NPC321708
0.7048	Intermediate Similarity	NPC474896
0.7048	Intermediate Similarity	NPC310118

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 NPC472027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	556
0.2-0.3	1072
0.3-0.4	1833
0.4-0.5	2653
0.5-0.6	2005
0.6-0.7	699
0.7-0.8	49
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
0.7828	Intermediate Similarity	NPD7824	Approved
0.775	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7730	Approved
0.7738	Intermediate Similarity	NPD7731	Approved
0.7727	Intermediate Similarity	NPD7271	Approved
0.7644	Intermediate Similarity	NPD7953	Approved
0.7644	Intermediate Similarity	NPD7951	Approved
0.7644	Intermediate Similarity	NPD7791	Approved
0.7644	Intermediate Similarity	NPD7952	Approved
0.7644	Intermediate Similarity	NPD7950	Approved
0.7644	Intermediate Similarity	NPD7789	Approved
0.7644	Intermediate Similarity	NPD7790	Approved
0.7538	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3402	Phase 1
0.7389	Intermediate Similarity	NPD7781	Approved
0.7389	Intermediate Similarity	NPD7780	Approved
0.7385	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6595	Phase 3
0.735	Intermediate Similarity	NPD5065	Approved
0.7333	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5913	Phase 3
0.7291	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2144	Approved
0.7269	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6978	Phase 2
0.726	Intermediate Similarity	NPD7470	Discontinued
0.7256	Intermediate Similarity	NPD4886	Phase 2
0.7255	Intermediate Similarity	NPD3038	Discontinued
0.7246	Intermediate Similarity	NPD8431	Approved
0.7233	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD3330	Phase 1
0.7202	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3323	Discontinued
0.7165	Intermediate Similarity	NPD2837	Discontinued
0.7149	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7957	Phase 1
0.7108	Intermediate Similarity	NPD4181	Approved
0.7095	Intermediate Similarity	NPD6281	Approved
0.7089	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3961	Discontinued
0.7081	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4079	Approved
0.7073	Intermediate Similarity	NPD4076	Approved
0.707	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5426	Phase 3
0.7062	Intermediate Similarity	NPD2172	Phase 1
0.7059	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2510	Approved
0.7045	Intermediate Similarity	NPD2509	Approved
0.7045	Intermediate Similarity	NPD7666	Phase 3
0.7045	Intermediate Similarity	NPD7665	Phase 2
0.7024	Intermediate Similarity	NPD3506	Approved
0.7024	Intermediate Similarity	NPD3505	Approved
0.7018	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5559	Phase 2
0.7009	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8322	Phase 2
0.698	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3393	Approved
0.6978	Remote Similarity	NPD3389	Approved
0.6978	Remote Similarity	NPD3394	Approved
0.6977	Remote Similarity	NPD7948	Phase 1
0.6974	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2581	Approved
0.697	Remote Similarity	NPD2582	Approved
0.6963	Remote Similarity	NPD1722	Approved
0.696	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4500	Approved
0.6959	Remote Similarity	NPD4501	Approved
0.6955	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3404	Approved
0.6936	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8063	Discontinued
0.6927	Remote Similarity	NPD4128	Approved
0.6912	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5862	Discovery
0.6894	Remote Similarity	NPD7558	Phase 2
0.6893	Remote Similarity	NPD5104	Approved
0.6893	Remote Similarity	NPD4075	Phase 2
0.6891	Remote Similarity	NPD6992	Phase 2
0.6888	Remote Similarity	NPD3835	Phase 3
0.6888	Remote Similarity	NPD3833	Phase 3
0.6884	Remote Similarity	NPD7618	Phase 3
0.6884	Remote Similarity	NPD7619	Phase 3
0.6881	Remote Similarity	NPD4601	Approved
0.6881	Remote Similarity	NPD4600	Approved
0.6878	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7001	Phase 3
0.6872	Remote Similarity	NPD4547	Phase 3
0.6856	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD8289	Discontinued
0.6853	Remote Similarity	NPD6352	Phase 2
0.6844	Remote Similarity	NPD8093	Discontinued
0.684	Remote Similarity	NPD7716	Approved
0.684	Remote Similarity	NPD7717	Approved
0.6837	Remote Similarity	NPD3100	Discontinued
0.6837	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8272	Phase 2
0.6833	Remote Similarity	NPD4795	Phase 2
0.6829	Remote Similarity	NPD3610	Approved
0.6829	Remote Similarity	NPD3609	Approved
0.6827	Remote Similarity	NPD8386	Phase 2
0.6812	Remote Similarity	NPD6455	Phase 3
0.681	Remote Similarity	NPD5596	Phase 2
0.68	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD8072	Approved
0.6784	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD8123	Approved
0.6779	Remote Similarity	NPD8122	Approved
0.6777	Remote Similarity	NPD4957	Phase 2
0.6774	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD786	Approved
0.6769	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5255	Approved
0.6766	Remote Similarity	NPD6969	Phase 2
0.6766	Remote Similarity	NPD6968	Phase 2
0.6765	Remote Similarity	NPD5891	Approved
0.6761	Remote Similarity	NPD7394	Phase 2
0.6761	Remote Similarity	NPD8020	Approved
0.6761	Remote Similarity	NPD8021	Approved
0.6759	Remote Similarity	NPD1038	Approved
0.6758	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3825	Phase 3
0.6758	Remote Similarity	NPD6999	Discontinued
0.6757	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5612	Discontinued
0.6753	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6164	Phase 2
0.6752	Remote Similarity	NPD6165	Phase 2
0.675	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5003	Discontinued
0.6742	Remote Similarity	NPD8073	Approved
0.6735	Remote Similarity	NPD7469	Discontinued
0.6732	Remote Similarity	NPD2641	Approved
0.6732	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2640	Approved
0.6731	Remote Similarity	NPD2381	Approved
0.6731	Remote Similarity	NPD2380	Approved
0.6731	Remote Similarity	NPD2382	Approved
0.673	Remote Similarity	NPD2095	Phase 2
0.673	Remote Similarity	NPD2092	Phase 2
0.673	Remote Similarity	NPD2094	Phase 2
0.6721	Remote Similarity	NPD8358	Approved
0.6714	Remote Similarity	NPD706	Phase 1
0.6711	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7711	Discontinued
0.6708	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD198	Clinical (unspecified phase)
0.67	Remote Similarity	NPD977	Approved
0.67	Remote Similarity	NPD975	Approved
0.67	Remote Similarity	NPD976	Approved
0.6699	Remote Similarity	NPD1325	Approved
0.6699	Remote Similarity	NPD1326	Approved
0.6698	Remote Similarity	NPD2091	Phase 2
0.6698	Remote Similarity	NPD6178	Phase 3
0.6698	Remote Similarity	NPD4499	Approved
0.6698	Remote Similarity	NPD2096	Phase 2
0.6697	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1392	Approved
0.6694	Remote Similarity	NPD8442	Discontinued
0.6694	Remote Similarity	NPD8246	Approved
0.6694	Remote Similarity	NPD8247	Approved
0.6683	Remote Similarity	NPD2639	Approved
0.6683	Remote Similarity	NPD2642	Approved
0.6683	Remote Similarity	NPD482	Approved
0.6682	Remote Similarity	NPD8408	Discontinued
0.6682	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7726	Phase 1
0.6681	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6664	Approved
0.6667	Remote Similarity	NPD8094	Discontinued
0.6667	Remote Similarity	NPD5075	Discontinued
0.6667	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4612	Discontinued
0.6667	Remote Similarity	NPD5270	Discontinued
0.6667	Remote Similarity	NPD3082	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