NPASS Compound

Structure

NPC471891 OpenBabel07101718192D 42 50 0 0 1 0 0 0 0 0999 V2000 2.8135 -1.4690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9124 -2.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4398 -0.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7168 -2.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7370 -0.7295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7004 -1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2937 -0.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8653 -0.5891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2656 -3.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8605 -0.3986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2011 -2.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4765 -1.2972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2744 0.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5780 0.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1612 -3.1657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4059 -2.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2037 -0.5396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4448 -3.8304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6481 -3.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4821 -3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8865 -2.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3026 -1.1955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4120 -3.1063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4727 -2.0921 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5062 -1.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9437 -2.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4259 -2.0136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8632 -2.6200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3041 0.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9248 -0.3159 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9201 -0.6320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2935 -2.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0099 -1.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0237 -1.5810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0383 -2.5582 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5862 -0.7819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5110 -3.5424 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9953 -0.9478 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9865 -3.4380 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.9102 -1.2930 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.7180 1.0485 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 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 29 2 0 0 0 0 14 30 1 0 0 0 0 15 18 2 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 18 37 1 0 0 0 0 19 39 1 0 0 0 0 20 39 1 0 0 0 0 21 24 1 0 0 0 0 22 27 2 0 0 0 0 22 36 1 0 0 0 0 23 35 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 6 0 0 0 25 26 2 0 0 0 0 25 31 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 32 1 0 0 0 0 28 35 1 1 0 0 0 29 31 1 0 0 0 0 29 41 1 0 0 0 0 30 40 1 1 0 0 0 30 42 1 0 0 0 0 31 38 2 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 21 1 1 0 0 0 36 17 1 6 0 0 0 36 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.33
Volume:	592.043
LogP:	5.347
LogD:	4.159
LogS:	-3.31
# 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:	0.315
Synthetic Accessibility Score:	6.95
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:	-5.248
MDCK Permeability:	1.7859809304354712e-05
Pgp-inhibitor:	0.508
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.797

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.249
Plasma Protein Binding (PPB):	96.27507019042969%
Volume Distribution (VD):	1.419
Pgp-substrate:	3.5195071697235107%

ADMET: Metabolism

CYP1A2-inhibitor:	0.191
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.388
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.316
CYP2C9-substrate:	0.465
CYP2D6-inhibitor:	0.968
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.901

ADMET: Excretion

Clearance (CL):	4.868
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.931
Human Hepatotoxicity (H-HT):	0.989
Drug-inuced Liver Injury (DILI):	0.366
AMES Toxicity:	0.763
Rat Oral Acute Toxicity:	0.523
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.945
Carcinogencity:	0.134
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC471891

Natural Product ID:	NPC471891
*Common Name:**	12,28-Oxa-8-Hydroxy-Manzamine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DDRSBWWAQLWQBR-YGSMERMXSA-N
Standard InCHI:	InChI=1S/C36H42N4O2/c41-29-13-10-12-25-26-15-18-37-32(33(26)38-31(25)29)27-22-36-17-8-3-1-2-4-9-19-39-20-16-28(27)35(23-39)21-24-11-6-5-7-14-30(42-36)40(24)34(35)36/h1,3,6,10-13,15,18,22,24,28,30,34,37,41H,2,4-5,7-9,14,16-17,19-21,23H2/b3-1-,11-6-/t24-,28-,30+,34+,35-,36-/m0/s1
SMILES:	Oc1cccc2c1nc1c2cc[nH]c1C1=C[C@]23CC/C=CCCCCN4CC[C@@H]1[C@@]1([C@H]3N3[C@H](O2)CCCC=C[C@H]3C1)C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL326530
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
IC50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	24.0	ug.mL-1	PMID[564904]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	4.0	ug.mL-1	PMID[564904]

☑ 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 NPC471891 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	581
0.1-0.2	2774
0.2-0.3	13866
0.3-0.4	16383
0.4-0.5	4438
0.5-0.6	2739
0.6-0.7	1681
0.7-0.8	215
0.8-0.85	11
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9401	High Similarity	NPC476451
0.9087	High Similarity	NPC6215
0.8982	High Similarity	NPC81175
0.886	High Similarity	NPC473312
0.8802	High Similarity	NPC472027
0.871	High Similarity	NPC473757
0.8565	High Similarity	NPC41679
0.8438	Intermediate Similarity	NPC471506
0.8433	Intermediate Similarity	NPC166492
0.8433	Intermediate Similarity	NPC473362
0.8291	Intermediate Similarity	NPC477861
0.8253	Intermediate Similarity	NPC475258
0.8251	Intermediate Similarity	NPC250835
0.821	Intermediate Similarity	NPC475338
0.821	Intermediate Similarity	NPC909
0.8112	Intermediate Similarity	NPC469554
0.8097	Intermediate Similarity	NPC476041
0.8097	Intermediate Similarity	NPC304926
0.8095	Intermediate Similarity	NPC476492
0.8065	Intermediate Similarity	NPC265576
0.8065	Intermediate Similarity	NPC192315
0.8034	Intermediate Similarity	NPC101543
0.8028	Intermediate Similarity	NPC476167
0.7991	Intermediate Similarity	NPC5145
0.7983	Intermediate Similarity	NPC314954
0.7982	Intermediate Similarity	NPC473310
0.7974	Intermediate Similarity	NPC251936
0.7928	Intermediate Similarity	NPC475070
0.7895	Intermediate Similarity	NPC8022
0.7895	Intermediate Similarity	NPC470799
0.7892	Intermediate Similarity	NPC475288
0.7828	Intermediate Similarity	NPC471564
0.7803	Intermediate Similarity	NPC476138
0.7803	Intermediate Similarity	NPC245816
0.7782	Intermediate Similarity	NPC295228
0.7763	Intermediate Similarity	NPC26679
0.7759	Intermediate Similarity	NPC132642
0.7739	Intermediate Similarity	NPC477110
0.7733	Intermediate Similarity	NPC476493
0.7709	Intermediate Similarity	NPC476116
0.7679	Intermediate Similarity	NPC253580
0.7665	Intermediate Similarity	NPC477111
0.7662	Intermediate Similarity	NPC183407
0.7655	Intermediate Similarity	NPC477113
0.7639	Intermediate Similarity	NPC213530
0.7639	Intermediate Similarity	NPC193267
0.7637	Intermediate Similarity	NPC470126
0.7632	Intermediate Similarity	NPC185782
0.7611	Intermediate Similarity	NPC470500
0.7609	Intermediate Similarity	NPC94157
0.7589	Intermediate Similarity	NPC249040
0.7576	Intermediate Similarity	NPC476287
0.7566	Intermediate Similarity	NPC475774
0.7563	Intermediate Similarity	NPC476491
0.7563	Intermediate Similarity	NPC473185
0.7542	Intermediate Similarity	NPC162748
0.7534	Intermediate Similarity	NPC232130
0.7521	Intermediate Similarity	NPC325976
0.7511	Intermediate Similarity	NPC176538
0.7511	Intermediate Similarity	NPC19872
0.7511	Intermediate Similarity	NPC324149
0.75	Intermediate Similarity	NPC475602
0.7479	Intermediate Similarity	NPC180504
0.7455	Intermediate Similarity	NPC77555
0.7446	Intermediate Similarity	NPC475422
0.744	Intermediate Similarity	NPC26543
0.7432	Intermediate Similarity	NPC99666
0.7426	Intermediate Similarity	NPC310118
0.7425	Intermediate Similarity	NPC469592
0.7425	Intermediate Similarity	NPC471080
0.7397	Intermediate Similarity	NPC475253
0.7395	Intermediate Similarity	NPC280272
0.7388	Intermediate Similarity	NPC15801
0.7375	Intermediate Similarity	NPC319232
0.7375	Intermediate Similarity	NPC24370
0.7373	Intermediate Similarity	NPC469594
0.7371	Intermediate Similarity	NPC126066
0.7371	Intermediate Similarity	NPC123976
0.7371	Intermediate Similarity	NPC167860
0.7364	Intermediate Similarity	NPC171171
0.7362	Intermediate Similarity	NPC53534
0.7359	Intermediate Similarity	NPC87755
0.7355	Intermediate Similarity	NPC326363
0.735	Intermediate Similarity	NPC477610
0.7344	Intermediate Similarity	NPC110151
0.7342	Intermediate Similarity	NPC473179
0.7339	Intermediate Similarity	NPC295452
0.7339	Intermediate Similarity	NPC171393
0.7336	Intermediate Similarity	NPC223427
0.7326	Intermediate Similarity	NPC152620
0.7318	Intermediate Similarity	NPC314002
0.7317	Intermediate Similarity	NPC473183
0.7314	Intermediate Similarity	NPC477608
0.7306	Intermediate Similarity	NPC220765
0.7306	Intermediate Similarity	NPC48938
0.7303	Intermediate Similarity	NPC132631
0.7303	Intermediate Similarity	NPC103687
0.7281	Intermediate Similarity	NPC329793
0.7273	Intermediate Similarity	NPC284678
0.7273	Intermediate Similarity	NPC204717
0.7269	Intermediate Similarity	NPC292958
0.7265	Intermediate Similarity	NPC323752
0.7265	Intermediate Similarity	NPC208284
0.7261	Intermediate Similarity	NPC313884
0.7261	Intermediate Similarity	NPC98371
0.7257	Intermediate Similarity	NPC251090
0.7251	Intermediate Similarity	NPC469734
0.7249	Intermediate Similarity	NPC232727
0.7244	Intermediate Similarity	NPC307963
0.7243	Intermediate Similarity	NPC477607
0.724	Intermediate Similarity	NPC15102
0.7237	Intermediate Similarity	NPC128823
0.7236	Intermediate Similarity	NPC473184
0.7224	Intermediate Similarity	NPC207686
0.7222	Intermediate Similarity	NPC199667
0.7217	Intermediate Similarity	NPC211813
0.721	Intermediate Similarity	NPC475910
0.7206	Intermediate Similarity	NPC477549
0.7203	Intermediate Similarity	NPC315467
0.7198	Intermediate Similarity	NPC475841
0.7198	Intermediate Similarity	NPC474145
0.7179	Intermediate Similarity	NPC469589
0.7179	Intermediate Similarity	NPC473181
0.7175	Intermediate Similarity	NPC46580
0.7166	Intermediate Similarity	NPC182222
0.7162	Intermediate Similarity	NPC187558
0.7162	Intermediate Similarity	NPC18487
0.7161	Intermediate Similarity	NPC473180
0.716	Intermediate Similarity	NPC60006
0.7156	Intermediate Similarity	NPC92111
0.7155	Intermediate Similarity	NPC329708
0.7155	Intermediate Similarity	NPC118832
0.7155	Intermediate Similarity	NPC165349
0.7155	Intermediate Similarity	NPC264166
0.7155	Intermediate Similarity	NPC274291
0.7155	Intermediate Similarity	NPC47059
0.7155	Intermediate Similarity	NPC477609
0.7149	Intermediate Similarity	NPC267928
0.7149	Intermediate Similarity	NPC167908
0.7149	Intermediate Similarity	NPC130570
0.7143	Intermediate Similarity	NPC470678
0.7143	Intermediate Similarity	NPC170114
0.7143	Intermediate Similarity	NPC469928
0.7137	Intermediate Similarity	NPC314957
0.7131	Intermediate Similarity	NPC39092
0.7131	Intermediate Similarity	NPC266931
0.7124	Intermediate Similarity	NPC472111
0.7123	Intermediate Similarity	NPC184964
0.7121	Intermediate Similarity	NPC478080
0.7119	Intermediate Similarity	NPC245348
0.7119	Intermediate Similarity	NPC125597
0.7117	Intermediate Similarity	NPC472294
0.7111	Intermediate Similarity	NPC76748
0.711	Intermediate Similarity	NPC478010
0.711	Intermediate Similarity	NPC478009
0.7109	Intermediate Similarity	NPC153400
0.7107	Intermediate Similarity	NPC470501
0.7104	Intermediate Similarity	NPC478006
0.7101	Intermediate Similarity	NPC470549
0.7097	Intermediate Similarity	NPC39370
0.7093	Intermediate Similarity	NPC84853
0.709	Intermediate Similarity	NPC202503
0.7089	Intermediate Similarity	NPC294620
0.7085	Intermediate Similarity	NPC473186
0.7083	Intermediate Similarity	NPC477714
0.7082	Intermediate Similarity	NPC285558
0.7074	Intermediate Similarity	NPC156704
0.7069	Intermediate Similarity	NPC193761
0.7067	Intermediate Similarity	NPC296527
0.7066	Intermediate Similarity	NPC470502
0.7066	Intermediate Similarity	NPC60621
0.7063	Intermediate Similarity	NPC478081
0.7061	Intermediate Similarity	NPC133366
0.7059	Intermediate Similarity	NPC478074
0.7056	Intermediate Similarity	NPC45459
0.7056	Intermediate Similarity	NPC473182
0.7056	Intermediate Similarity	NPC315491
0.7051	Intermediate Similarity	NPC473764
0.7051	Intermediate Similarity	NPC314940
0.7045	Intermediate Similarity	NPC477112
0.7042	Intermediate Similarity	NPC477715
0.704	Intermediate Similarity	NPC184225
0.704	Intermediate Similarity	NPC28945
0.7037	Intermediate Similarity	NPC155444
0.7035	Intermediate Similarity	NPC95783
0.7035	Intermediate Similarity	NPC3715
0.7033	Intermediate Similarity	NPC33949
0.7027	Intermediate Similarity	NPC314394
0.7024	Intermediate Similarity	NPC477066
0.702	Intermediate Similarity	NPC214980
0.702	Intermediate Similarity	NPC17437
0.7019	Intermediate Similarity	NPC117980
0.7016	Intermediate Similarity	NPC329982
0.7016	Intermediate Similarity	NPC314882
0.7012	Intermediate Similarity	NPC11408
0.7008	Intermediate Similarity	NPC470503
0.7004	Intermediate Similarity	NPC11464
0.7	Intermediate Similarity	NPC475746
0.7	Intermediate Similarity	NPC258048
0.6996	Remote Similarity	NPC477067

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 NPC471891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	583
0.2-0.3	928
0.3-0.4	1757
0.4-0.5	2815
0.5-0.6	1977
0.6-0.7	761
0.7-0.8	50
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
0.7609	Intermediate Similarity	NPD3330	Phase 1
0.7595	Intermediate Similarity	NPD7603	Discontinued
0.7554	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD7948	Phase 1
0.7511	Intermediate Similarity	NPD5612	Discontinued
0.7477	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7726	Phase 1
0.7415	Intermediate Similarity	NPD3402	Phase 1
0.7373	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7824	Approved
0.7314	Intermediate Similarity	NPD5559	Phase 2
0.73	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7731	Approved
0.7273	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7730	Approved
0.7265	Intermediate Similarity	NPD7558	Phase 2
0.7261	Intermediate Similarity	NPD7271	Approved
0.7261	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8442	Discontinued
0.7244	Intermediate Similarity	NPD1038	Approved
0.7237	Intermediate Similarity	NPD8395	Approved
0.7237	Intermediate Similarity	NPD2177	Approved
0.7237	Intermediate Similarity	NPD2175	Phase 3
0.7237	Intermediate Similarity	NPD2176	Approved
0.7237	Intermediate Similarity	NPD8396	Approved
0.7215	Intermediate Similarity	NPD7112	Discontinued
0.7202	Intermediate Similarity	NPD6978	Phase 2
0.7202	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7952	Approved
0.7195	Intermediate Similarity	NPD7791	Approved
0.7195	Intermediate Similarity	NPD7953	Approved
0.7195	Intermediate Similarity	NPD7950	Approved
0.7195	Intermediate Similarity	NPD7789	Approved
0.7195	Intermediate Similarity	NPD7951	Approved
0.7195	Intermediate Similarity	NPD7790	Approved
0.7191	Intermediate Similarity	NPD5939	Approved
0.7191	Intermediate Similarity	NPD4131	Phase 3
0.7191	Intermediate Similarity	NPD4502	Phase 2
0.7191	Intermediate Similarity	NPD5936	Approved
0.7179	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7222	Phase 2
0.7167	Intermediate Similarity	NPD6290	Phase 2
0.7162	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6961	Discontinued
0.7155	Intermediate Similarity	NPD4122	Approved
0.7155	Intermediate Similarity	NPD4035	Approved
0.7155	Intermediate Similarity	NPD4037	Approved
0.7155	Intermediate Similarity	NPD4038	Approved
0.7155	Intermediate Similarity	NPD4039	Approved
0.7155	Intermediate Similarity	NPD4033	Approved
0.7155	Intermediate Similarity	NPD31	Approved
0.7155	Intermediate Similarity	NPD4034	Approved
0.7155	Intermediate Similarity	NPD32	Approved
0.7155	Intermediate Similarity	NPD4036	Approved
0.7143	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7470	Discontinued
0.7119	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4886	Phase 2
0.711	Intermediate Similarity	NPD5065	Approved
0.7107	Intermediate Similarity	NPD1856	Discontinued
0.7093	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD4795	Phase 2
0.7075	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD6456	Discontinued
0.7056	Intermediate Similarity	NPD484	Approved
0.7043	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3343	Phase 3
0.702	Intermediate Similarity	NPD8358	Approved
0.7019	Intermediate Similarity	NPD8364	Approved
0.7019	Intermediate Similarity	NPD8363	Approved
0.7013	Intermediate Similarity	NPD3825	Phase 3
0.7009	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3006	Discontinued
0.6996	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5644	Phase 1
0.6988	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8247	Approved
0.6988	Remote Similarity	NPD8246	Approved
0.6987	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7925	Phase 2
0.6981	Remote Similarity	NPD7924	Phase 2
0.6979	Remote Similarity	NPD5530	Phase 1
0.6977	Remote Similarity	NPD7659	Discontinued
0.6974	Remote Similarity	NPD6569	Phase 2
0.6971	Remote Similarity	NPD8525	Approved
0.6971	Remote Similarity	NPD5164	Discontinued
0.697	Remote Similarity	NPD8284	Discontinued
0.6969	Remote Similarity	NPD7067	Approved
0.6969	Remote Similarity	NPD7068	Approved
0.6966	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD8101	Phase 3
0.6964	Remote Similarity	NPD7781	Approved
0.6964	Remote Similarity	NPD7780	Approved
0.6958	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3477	Phase 2
0.6957	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4511	Phase 1
0.6949	Remote Similarity	NPD7452	Approved
0.6949	Remote Similarity	NPD7453	Approved
0.6949	Remote Similarity	NPD1392	Approved
0.6949	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8512	Phase 3
0.6932	Remote Similarity	NPD4454	Phase 2
0.693	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5913	Phase 3
0.6923	Remote Similarity	NPD8430	Approved
0.6914	Remote Similarity	NPD534	Phase 2
0.6914	Remote Similarity	NPD7194	Discontinued
0.6914	Remote Similarity	NPD537	Phase 2
0.6913	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.691	Remote Similarity	NPD1739	Approved
0.691	Remote Similarity	NPD1740	Approved
0.6906	Remote Similarity	NPD6595	Phase 3
0.6898	Remote Similarity	NPD7221	Approved
0.6898	Remote Similarity	NPD8356	Approved
0.6898	Remote Similarity	NPD7219	Approved
0.6897	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8063	Discontinued
0.6881	Remote Similarity	NPD425	Approved
0.6881	Remote Similarity	NPD424	Approved
0.688	Remote Similarity	NPD4442	Phase 2
0.688	Remote Similarity	NPD3746	Discontinued
0.6878	Remote Similarity	NPD9690	Approved
0.6877	Remote Similarity	NPD5018	Phase 3
0.6872	Remote Similarity	NPD1034	Phase 3
0.6872	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6969	Phase 2
0.6867	Remote Similarity	NPD6968	Phase 2
0.6867	Remote Similarity	NPD5999	Phase 2
0.6863	Remote Similarity	NPD8467	Approved
0.6863	Remote Similarity	NPD8466	Approved
0.6863	Remote Similarity	NPD8465	Approved
0.685	Remote Similarity	NPD8016	Phase 3
0.685	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5658	Approved
0.6848	Remote Similarity	NPD8100	Phase 3
0.6835	Remote Similarity	NPD3003	Approved
0.6835	Remote Similarity	NPD8349	Phase 1
0.6834	Remote Similarity	NPD5482	Discontinued
0.6833	Remote Similarity	NPD5066	Phase 2
0.6833	Remote Similarity	NPD5067	Phase 2
0.683	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8426	Approved
0.6825	Remote Similarity	NPD8425	Approved
0.682	Remote Similarity	NPD8370	Discontinued
0.6816	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6159	Phase 2
0.6815	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7674	Phase 3
0.6815	Remote Similarity	NPD7675	Phase 3
0.6813	Remote Similarity	NPD7181	Phase 3
0.6812	Remote Similarity	NPD6281	Approved
0.6803	Remote Similarity	NPD5948	Phase 2
0.6801	Remote Similarity	NPD8429	Approved
0.6801	Remote Similarity	NPD8428	Approved
0.6801	Remote Similarity	NPD8427	Approved
0.6798	Remote Similarity	NPD8431	Approved
0.6797	Remote Similarity	NPD9695	Approved
0.6797	Remote Similarity	NPD802	Phase 2
0.6795	Remote Similarity	NPD4548	Discontinued
0.6793	Remote Similarity	NPD5426	Phase 3
0.679	Remote Similarity	NPD6643	Discontinued
0.6786	Remote Similarity	NPD6494	Phase 2
0.6784	Remote Similarity	NPD6992	Phase 2
0.6778	Remote Similarity	NPD2189	Approved
0.6778	Remote Similarity	NPD7666	Phase 3
0.6778	Remote Similarity	NPD2187	Approved
0.6778	Remote Similarity	NPD7665	Phase 2
0.6777	Remote Similarity	NPD2616	Phase 3
0.6777	Remote Similarity	NPD2615	Phase 3
0.6776	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6455	Phase 3
0.6774	Remote Similarity	NPD9705	Discontinued
0.6774	Remote Similarity	NPD112	Approved
0.6773	Remote Similarity	NPD8524	Approved
0.6765	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8403	Phase 1
0.6764	Remote Similarity	NPD8459	Approved
0.6764	Remote Similarity	NPD8460	Approved
0.6763	Remote Similarity	NPD3939	Suspended
0.6761	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6531	Approved
0.6755	Remote Similarity	NPD6530	Approved
0.6753	Remote Similarity	NPD3404	Approved
0.6748	Remote Similarity	NPD6242	Discontinued
0.6747	Remote Similarity	NPD6352	Phase 2
0.6742	Remote Similarity	NPD7169	Suspended
0.6736	Remote Similarity	NPD796	Phase 2
0.6736	Remote Similarity	NPD8093	Discontinued
0.6736	Remote Similarity	NPD7594	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data