NPASS Compound

Structure

CID322800 OpenBabel06191716162D 64 67 0 0 1 0 0 0 0 0999 V2000 -10.5470 4.7006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0843 -3.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5579 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7448 2.3022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3418 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9082 -2.9562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1221 1.1412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5360 0.5828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5198 -1.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5971 1.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9619 0.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1445 1.5201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1513 1.6233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7593 2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3382 2.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3309 2.8606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9535 4.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6302 -2.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5383 -2.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5971 -2.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3418 -0.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8113 1.2423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7245 0.6231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7156 1.8201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9462 3.9011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0843 -2.7815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5506 0.8239 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3528 3.2222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3491 -0.2250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5714 -2.2077 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1445 -2.5201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5383 1.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2067 0.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3601 3.3428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2175 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0240 -2.5201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9425 -0.0961 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3491 -0.7750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6302 1.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9619 -1.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2067 -1.7960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0240 1.5201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6084 -3.4459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1429 -2.6007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0843 1.7815 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5714 1.2077 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -11.7229 1.9406 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -13.1076 0.9001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9681 4.2627 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1525 0.6636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5593 -3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7848 -2.3641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0731 -4.3313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9352 -0.2166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3837 -2.3641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3573 1.2423 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 -2.1332 0.9852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6092 -3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2175 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 29 1 0 0 0 0 7 51 1 0 0 0 0 8 58 1 0 0 0 0 9 59 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 11 37 1 0 0 0 0 12 41 1 0 0 0 0 13 14 1 0 0 0 0 13 28 1 0 0 0 0 14 36 1 0 0 0 0 15 16 2 0 0 0 0 15 26 1 0 0 0 0 16 51 1 0 0 0 0 17 26 1 0 0 0 0 17 29 2 0 0 0 0 18 27 1 0 0 0 0 18 32 1 0 0 0 0 19 27 1 0 0 0 0 19 38 1 0 0 0 0 20 32 1 0 0 0 0 20 42 1 0 0 0 0 22 33 2 0 0 0 0 22 61 1 0 0 0 0 23 34 2 0 0 0 0 23 60 1 0 0 0 0 24 35 2 0 0 0 0 24 62 1 0 0 0 0 25 51 1 0 0 0 0 25 52 2 0 0 0 0 26 1 1 1 0 0 0 27 2 1 1 0 0 0 28 3 1 6 0 0 0 28 39 1 0 0 0 0 29 36 1 0 0 0 0 30 5 1 6 0 0 0 30 37 1 0 0 0 0 30 40 1 0 0 0 0 31 6 1 1 0 0 0 31 38 1 0 0 0 0 31 43 1 0 0 0 0 32 63 1 6 0 0 0 33 43 1 0 0 0 0 33 49 1 0 0 0 0 34 44 1 0 0 0 0 34 48 1 0 0 0 0 35 45 1 0 0 0 0 35 50 1 0 0 0 0 36 53 2 0 0 0 0 37 54 1 1 0 0 0 38 55 1 1 0 0 0 39 21 1 6 0 0 0 39 58 1 0 0 0 0 40 21 1 1 0 0 0 40 64 1 0 0 0 0 41 48 2 0 0 0 0 41 60 1 0 0 0 0 42 56 2 0 0 0 0 42 64 1 0 0 0 0 43 59 1 6 0 0 0 44 50 2 0 0 0 0 44 62 1 0 0 0 0 45 49 2 0 0 0 0 45 61 1 0 0 0 0 46 47 2 0 0 0 0 46 57 1 0 0 0 0 46 63 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	895.46
Volume:	904.929
LogP:	4.421
LogD:	4.653
LogS:	-4.605
# Rotatable Bonds:	15
TPSA:	253.01
# H-Bond Aceptor:	18
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.066
Synthetic Accessibility Score:	7.937
Fsp3:	0.587
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.978
MDCK Permeability:	3.074948108405806e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.244
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	73.83304595947266%
Volume Distribution (VD):	5.071
Pgp-substrate:	12.362945556640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	10.428
Half-life (T1/2):	0.152

ADMET: Toxicity

hERG Blockers:	0.869
Human Hepatotoxicity (H-HT):	0.791
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.903
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.166
Carcinogencity:	0.906
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.728

Download Data

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

Natural Product: NPC322800

Natural Product ID:	NPC322800
*Common Name:**	Kabiramide J
IUPAC Name:	n.a.
Synonyms:	Kabiramide J
Standard InCHIKey:	YGIPHYWFBPFNFA-AWOSXSGWSA-N
Standard InCHI:	InChI=1S/C46H65N5O13/c1-26(15-16-51(7)25-52)17-29(4)36(53)14-13-28(3)39(58-8)21-40-30(5)37(54)11-10-12-41-48-34(23-60-41)44-50-35(24-62-44)45-49-33(22-61-45)43(59-9)31(6)38(55)19-27(2)18-32(63-46(47)57)20-42(56)64-40/h10,12,15-17,22-28,30-32,37-40,43,54-55H,11,13-14,18-21H2,1-9H3,(H2,47,57)/b12-10+,16-15+,29-17+/t26-,27+,28+,30-,31+,32+,37+,38+,39+,40+,43-/m1/s1
SMILES:	CO[C@H]([C@H](CCC(=O)/C(=C/[C@@H](/C=C/N(C=O)C)C)/C)C)C[C@@H]1OC(=O)C[C@H](C[C@H](C)C[C@H](O)[C@H](C)[C@@H](OC)c2coc(c3nc(c4nc(/C=C/C[C@@H]([C@H]1C)O)oc4)oc3)n2)OC(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802297
PubChem CID:	53262840
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO29155	Pachastrissa nux	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21410162]
NPO29155	Pachastrissa nux	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	20.0	nM	PMID[516809]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	310.0	nM	PMID[516809]

☑ 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 NPC322800 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	269
0.1-0.2	1555
0.2-0.3	7571
0.3-0.4	20297
0.4-0.5	11545
0.5-0.6	1363
0.6-0.7	56
0.7-0.8	10
0.8-0.85	0
0.85-0.9	5
0.9-0.95	18
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168135
0.9951	High Similarity	NPC177432
0.9951	High Similarity	NPC299035
0.9903	High Similarity	NPC477218
0.9805	High Similarity	NPC325683
0.9756	High Similarity	NPC37924
0.9707	High Similarity	NPC477219
0.9519	High Similarity	NPC476828
0.9375	High Similarity	NPC476831
0.9375	High Similarity	NPC476827
0.9375	High Similarity	NPC476826
0.933	High Similarity	NPC476830
0.8972	High Similarity	NPC476832
0.8104	Intermediate Similarity	NPC476829
0.7311	Intermediate Similarity	NPC314523
0.7311	Intermediate Similarity	NPC58001
0.7246	Intermediate Similarity	NPC30527
0.713	Intermediate Similarity	NPC224395
0.713	Intermediate Similarity	NPC208297
0.7049	Intermediate Similarity	NPC477590
0.7049	Intermediate Similarity	NPC477586
0.7049	Intermediate Similarity	NPC477585
0.7049	Intermediate Similarity	NPC477588
0.7018	Intermediate Similarity	NPC258022
0.6967	Remote Similarity	NPC477587
0.6967	Remote Similarity	NPC477589
0.6933	Remote Similarity	NPC107458
0.6933	Remote Similarity	NPC295653
0.6906	Remote Similarity	NPC88938
0.6906	Remote Similarity	NPC58112
0.6906	Remote Similarity	NPC306300
0.6798	Remote Similarity	NPC289029
0.6798	Remote Similarity	NPC48323
0.6778	Remote Similarity	NPC315411
0.6754	Remote Similarity	NPC314222
0.6754	Remote Similarity	NPC196449
0.6723	Remote Similarity	NPC49195
0.6723	Remote Similarity	NPC309919
0.6711	Remote Similarity	NPC199461
0.6711	Remote Similarity	NPC46313
0.6711	Remote Similarity	NPC103452
0.6705	Remote Similarity	NPC472436
0.6606	Remote Similarity	NPC315061
0.6589	Remote Similarity	NPC472435
0.6562	Remote Similarity	NPC165964
0.6481	Remote Similarity	NPC315872
0.6466	Remote Similarity	NPC102593
0.6466	Remote Similarity	NPC196718
0.6412	Remote Similarity	NPC258048
0.6372	Remote Similarity	NPC211555
0.6353	Remote Similarity	NPC148889
0.6342	Remote Similarity	NPC472434
0.6326	Remote Similarity	NPC186452
0.6303	Remote Similarity	NPC207620
0.6285	Remote Similarity	NPC182222
0.6284	Remote Similarity	NPC12660
0.6281	Remote Similarity	NPC169716
0.6256	Remote Similarity	NPC54983
0.6255	Remote Similarity	NPC72715
0.625	Remote Similarity	NPC314633
0.624	Remote Similarity	NPC316224
0.6231	Remote Similarity	NPC161801
0.6189	Remote Similarity	NPC477979
0.6185	Remote Similarity	NPC471979
0.6171	Remote Similarity	NPC152620
0.6128	Remote Similarity	NPC53534
0.6089	Remote Similarity	NPC313804
0.6089	Remote Similarity	NPC315804
0.6077	Remote Similarity	NPC124300
0.6074	Remote Similarity	NPC471978
0.6069	Remote Similarity	NPC58209
0.6069	Remote Similarity	NPC310618
0.6061	Remote Similarity	NPC10904
0.6061	Remote Similarity	NPC26543
0.6059	Remote Similarity	NPC473833
0.6054	Remote Similarity	NPC291609
0.6047	Remote Similarity	NPC140296
0.6032	Remote Similarity	NPC97746
0.6024	Remote Similarity	NPC194740
0.6018	Remote Similarity	NPC475455
0.6015	Remote Similarity	NPC328928
0.6008	Remote Similarity	NPC220408
0.6008	Remote Similarity	NPC57453
0.5993	Remote Similarity	NPC471015
0.5992	Remote Similarity	NPC141053
0.5992	Remote Similarity	NPC205372
0.5992	Remote Similarity	NPC208364
0.5985	Remote Similarity	NPC476514
0.5984	Remote Similarity	NPC131885
0.5984	Remote Similarity	NPC186351
0.5977	Remote Similarity	NPC473800
0.5977	Remote Similarity	NPC67401
0.597	Remote Similarity	NPC326930
0.597	Remote Similarity	NPC475301
0.5962	Remote Similarity	NPC91868
0.5962	Remote Similarity	NPC63971
0.596	Remote Similarity	NPC298436
0.5959	Remote Similarity	NPC269367
0.5949	Remote Similarity	NPC470042
0.5948	Remote Similarity	NPC13603
0.5944	Remote Similarity	NPC312645
0.593	Remote Similarity	NPC220852
0.5923	Remote Similarity	NPC184680
0.5923	Remote Similarity	NPC240384
0.5914	Remote Similarity	NPC260434
0.5911	Remote Similarity	NPC53255
0.5911	Remote Similarity	NPC85879
0.5909	Remote Similarity	NPC180668
0.5909	Remote Similarity	NPC148896
0.5909	Remote Similarity	NPC471013
0.5906	Remote Similarity	NPC289423
0.5906	Remote Similarity	NPC212766
0.5902	Remote Similarity	NPC316403
0.5902	Remote Similarity	NPC173250
0.59	Remote Similarity	NPC470785
0.59	Remote Similarity	NPC470784
0.5899	Remote Similarity	NPC314254
0.5899	Remote Similarity	NPC313966
0.5897	Remote Similarity	NPC230683
0.5897	Remote Similarity	NPC209981
0.5894	Remote Similarity	NPC166712
0.5889	Remote Similarity	NPC120513
0.5878	Remote Similarity	NPC168922
0.5874	Remote Similarity	NPC329982
0.5873	Remote Similarity	NPC323969
0.5871	Remote Similarity	NPC160100
0.5871	Remote Similarity	NPC188400
0.5871	Remote Similarity	NPC75179
0.5869	Remote Similarity	NPC284888
0.5865	Remote Similarity	NPC1608
0.5863	Remote Similarity	NPC153452
0.5863	Remote Similarity	NPC16066
0.5862	Remote Similarity	NPC285343
0.5859	Remote Similarity	NPC244536
0.5858	Remote Similarity	NPC315893
0.5858	Remote Similarity	NPC313587
0.5858	Remote Similarity	NPC181081
0.5858	Remote Similarity	NPC316110
0.5857	Remote Similarity	NPC281049
0.5856	Remote Similarity	NPC99891
0.5853	Remote Similarity	NPC14288
0.5846	Remote Similarity	NPC34770
0.584	Remote Similarity	NPC474183
0.584	Remote Similarity	NPC101350
0.584	Remote Similarity	NPC85702
0.583	Remote Similarity	NPC54803
0.583	Remote Similarity	NPC321592
0.583	Remote Similarity	NPC123839
0.5827	Remote Similarity	NPC473639
0.5827	Remote Similarity	NPC478141
0.5827	Remote Similarity	NPC101312
0.5824	Remote Similarity	NPC185197
0.5823	Remote Similarity	NPC89508
0.5821	Remote Similarity	NPC203373
0.582	Remote Similarity	NPC24370
0.582	Remote Similarity	NPC319232
0.5816	Remote Similarity	NPC172355
0.5814	Remote Similarity	NPC322135
0.5814	Remote Similarity	NPC223409
0.5812	Remote Similarity	NPC216507
0.5809	Remote Similarity	NPC18487
0.5806	Remote Similarity	NPC146418
0.5805	Remote Similarity	NPC324619
0.5805	Remote Similarity	NPC475315
0.5804	Remote Similarity	NPC475271
0.5803	Remote Similarity	NPC215837
0.5802	Remote Similarity	NPC235685
0.5802	Remote Similarity	NPC15801
0.5802	Remote Similarity	NPC28945
0.5799	Remote Similarity	NPC476515
0.5797	Remote Similarity	NPC315634
0.5797	Remote Similarity	NPC88923
0.5797	Remote Similarity	NPC100734
0.5794	Remote Similarity	NPC303658
0.5794	Remote Similarity	NPC314270
0.5789	Remote Similarity	NPC478158
0.5787	Remote Similarity	NPC90019
0.5785	Remote Similarity	NPC475619
0.5779	Remote Similarity	NPC317572
0.5776	Remote Similarity	NPC227824
0.5775	Remote Similarity	NPC33949
0.5775	Remote Similarity	NPC100547
0.5768	Remote Similarity	NPC475533
0.5766	Remote Similarity	NPC191489
0.5766	Remote Similarity	NPC314834
0.5758	Remote Similarity	NPC475816
0.5756	Remote Similarity	NPC314882
0.5754	Remote Similarity	NPC260909
0.5753	Remote Similarity	NPC95240
0.5749	Remote Similarity	NPC287208
0.5749	Remote Similarity	NPC266249
0.5747	Remote Similarity	NPC323752
0.5745	Remote Similarity	NPC282346
0.5744	Remote Similarity	NPC187558
0.5742	Remote Similarity	NPC115282
0.5741	Remote Similarity	NPC14812
0.5737	Remote Similarity	NPC478157
0.5736	Remote Similarity	NPC304307
0.5736	Remote Similarity	NPC124920
0.5736	Remote Similarity	NPC34580

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 NPC322800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	510
0.2-0.3	1562
0.3-0.4	3546
0.4-0.5	2915
0.5-0.6	438
0.6-0.7	13
0.7-0.8	1
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
0.6978	Remote Similarity	NPD7896	Approved
0.652	Remote Similarity	NPD7853	Phase 2
0.6507	Remote Similarity	NPD6347	Phase 2
0.6488	Remote Similarity	NPD6974	Phase 3
0.6486	Remote Similarity	NPD8370	Discontinued
0.6481	Remote Similarity	NPD6444	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7490	Discontinued
0.6382	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD4368	Phase 2
0.627	Remote Similarity	NPD7031	Phase 1
0.623	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3263	Phase 3
0.6194	Remote Similarity	NPD7180	Phase 3
0.6189	Remote Similarity	NPD8255	Phase 2
0.6177	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5532	Phase 2
0.6157	Remote Similarity	NPD2951	Discontinued
0.6148	Remote Similarity	NPD3945	Discontinued
0.6134	Remote Similarity	NPD2779	Approved
0.6084	Remote Similarity	NPD8324	Phase 2
0.6082	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD8116	Phase 3
0.6077	Remote Similarity	NPD8117	Approved
0.607	Remote Similarity	NPD3006	Discontinued
0.6063	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD5924	Discontinued
0.6063	Remote Similarity	NPD8374	Phase 3
0.6062	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5482	Discontinued
0.6047	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5922	Phase 3
0.6031	Remote Similarity	NPD8329	Phase 3
0.6023	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8356	Approved
0.6015	Remote Similarity	NPD7022	Phase 2
0.6008	Remote Similarity	NPD8375	Approved
0.6008	Remote Similarity	NPD2778	Approved
0.6	Remote Similarity	NPD8479	Phase 2
0.6	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.5993	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD4373	Phase 2
0.5992	Remote Similarity	NPD5293	Phase 2
0.5985	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8430	Approved
0.5962	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD3392	Approved
0.5947	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD5640	Discontinued
0.5944	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4952	Phase 3
0.5936	Remote Similarity	NPD5850	Phase 3
0.5935	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.5927	Remote Similarity	NPD6169	Phase 1
0.5926	Remote Similarity	NPD3507	Phase 2
0.5911	Remote Similarity	NPD5866	Approved
0.5909	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD8160	Phase 2
0.5899	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD6857	Phase 3
0.5874	Remote Similarity	NPD8463	Approved
0.587	Remote Similarity	NPD8421	Discontinued
0.5863	Remote Similarity	NPD1638	Discovery
0.5859	Remote Similarity	NPD4086	Phase 1
0.5859	Remote Similarity	NPD7994	Phase 2
0.5857	Remote Similarity	NPD7878	Phase 2
0.5856	Remote Similarity	NPD7417	Discontinued
0.5855	Remote Similarity	NPD5450	Discontinued
0.5853	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.5853	Remote Similarity	NPD1867	Approved
0.5852	Remote Similarity	NPD8247	Approved
0.5852	Remote Similarity	NPD8246	Approved
0.5837	Remote Similarity	NPD8104	Phase 3
0.5817	Remote Similarity	NPD7885	Phase 2
0.5817	Remote Similarity	NPD7886	Phase 2
0.5817	Remote Similarity	NPD8326	Phase 3
0.5817	Remote Similarity	NPD8325	Phase 3
0.5817	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD1659	Phase 1
0.5814	Remote Similarity	NPD5479	Discontinued
0.5806	Remote Similarity	NPD5416	Discontinued
0.5806	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD7803	Approved
0.5792	Remote Similarity	NPD1505	Phase 2
0.5785	Remote Similarity	NPD3074	Discontinued
0.5784	Remote Similarity	NPD1955	Discontinued
0.5776	Remote Similarity	NPD6023	Discontinued
0.5774	Remote Similarity	NPD6716	Phase 1
0.5772	Remote Similarity	NPD4392	Phase 2
0.5768	Remote Similarity	NPD772	Phase 3
0.5766	Remote Similarity	NPD7708	Approved
0.5759	Remote Similarity	NPD8289	Discontinued
0.5756	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD8459	Approved
0.5754	Remote Similarity	NPD8460	Approved
0.5752	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD7470	Discontinued
0.5737	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.5731	Remote Similarity	NPD5632	Approved
0.573	Remote Similarity	NPD7956	Approved
0.573	Remote Similarity	NPD7955	Approved
0.5725	Remote Similarity	NPD4369	Phase 2
0.572	Remote Similarity	NPD5857	Phase 3
0.572	Remote Similarity	NPD8096	Phase 3
0.572	Remote Similarity	NPD8097	Phase 3
0.5709	Remote Similarity	NPD8322	Phase 2
0.5709	Remote Similarity	NPD7797	Approved
0.5709	Remote Similarity	NPD7796	Approved
0.5703	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7777	Approved
0.5702	Remote Similarity	NPD7778	Approved
0.5702	Remote Similarity	NPD53	Approved
0.5695	Remote Similarity	NPD8253	Phase 3
0.5692	Remote Similarity	NPD5022	Discontinued
0.5687	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3259	Approved
0.5673	Remote Similarity	NPD6863	Phase 2
0.567	Remote Similarity	NPD7688	Phase 1
0.567	Remote Similarity	NPD6962	Phase 2
0.5668	Remote Similarity	NPD5461	Discontinued
0.5667	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.5662	Remote Similarity	NPD8357	Approved
0.5657	Remote Similarity	NPD7605	Discovery
0.5655	Remote Similarity	NPD4322	Discontinued
0.5651	Remote Similarity	NPD5817	Discontinued
0.5649	Remote Similarity	NPD6627	Discontinued
0.5641	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.5637	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5633	Remote Similarity	NPD7727	Phase 2
0.5629	Remote Similarity	NPD8107	Approved
0.5628	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD8098	Approved
0.5627	Remote Similarity	NPD8284	Discontinued
0.5627	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.5623	Remote Similarity	NPD8363	Approved
0.5623	Remote Similarity	NPD8364	Approved
0.5621	Remote Similarity	NPD8525	Approved
0.5618	Remote Similarity	NPD6790	Phase 1
0.5618	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8465	Approved
0.5614	Remote Similarity	NPD8467	Approved
0.5614	Remote Similarity	NPD8108	Approved
0.5614	Remote Similarity	NPD8428	Approved
0.5614	Remote Similarity	NPD8427	Approved
0.5614	Remote Similarity	NPD8429	Approved
0.5614	Remote Similarity	NPD8466	Approved
0.5613	Remote Similarity	NPD7967	Discontinued
0.5613	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.561	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.5609	Remote Similarity	NPD4887	Discontinued
0.5609	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8049	Phase 2
0.56	Remote Similarity	NPD7941	Phase 3

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