NPASS Compound

Structure

NPC2395 OpenBabel07101719132D 42 46 0 0 1 0 0 0 0 0999 V2000 -5.6071 -0.6584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1051 -3.0336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5183 3.0171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1768 3.9958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1547 -3.0496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2839 2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2839 3.3096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8866 1.1688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4746 0.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4363 1.8415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0024 1.5884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4363 3.7989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9586 -1.6435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5750 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3216 -1.5080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3554 1.0976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0826 2.8202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6316 -0.5796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6158 -2.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3293 2.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1768 3.0171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8879 -3.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6579 2.0284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5887 2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0244 1.5490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5887 3.3096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3981 0.8941 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7168 -2.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6538 0.2324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3293 1.5490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0244 2.5277 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6757 -2.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9734 0.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1768 1.0596 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6579 3.6120 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9273 -4.9372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2972 -3.1467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2746 0.5424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8720 3.0171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6283 -0.6250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7151 -3.4362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 18 1 0 0 0 0 10 24 2 0 0 0 0 11 25 1 0 0 0 0 12 26 2 0 0 0 0 13 14 2 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 16 23 1 0 0 0 0 17 23 2 0 0 0 0 17 35 1 0 0 0 0 18 1 1 1 0 0 0 19 32 1 0 0 0 0 20 21 2 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 37 2 0 0 0 0 22 42 1 0 0 0 0 23 24 1 0 0 0 0 24 26 1 0 0 0 0 25 31 1 0 0 0 0 25 34 1 1 0 0 0 26 35 1 0 0 0 0 27 16 1 6 0 0 0 27 30 1 0 0 0 0 27 36 1 0 0 0 0 28 32 1 0 0 0 0 28 38 2 0 0 0 0 29 39 2 0 0 0 0 30 34 1 1 0 0 0 31 40 1 6 0 0 0 32 42 1 6 0 0 0 33 34 1 0 0 0 0 33 36 2 0 0 0 0 33 41 1 0 0 0 0 34 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.27
Volume:	596.935
LogP:	4.232
LogD:	3.722
LogS:	-4.671
# Rotatable Bonds:	4
TPSA:	125.56
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	5.792
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	1.4562619071512017e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.072
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	90.2864761352539%
Volume Distribution (VD):	0.528
Pgp-substrate:	9.421734809875488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.192
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.935
CYP2C19-substrate:	0.389
CYP2C9-inhibitor:	0.933
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.846
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	3.268
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.087
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.937
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.72

Download Data

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

Natural Product: NPC2395

Natural Product ID:	NPC2395
*Common Name:**	19-O-Acetylchaetoglobosin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AAALKTDFGJLPNH-QGEDVQPGSA-N
Standard InCHI:	InChI=1S/C34H38N2O6/c1-18-9-8-11-25-31(40)21(4)20(3)30-27(16-23-17-35-26-12-7-6-10-24(23)26)36-33(41)34(25,30)29(39)14-13-28(38)32(19(2)15-18)42-22(5)37/h6-8,10-15,17-18,25,27,30-32,35,40H,9,16H2,1-5H3,(H,36,41)/b11-8+,14-13+,19-15-/t18-,25-,27-,30-,31+,32+,34+/m0/s1
SMILES:	CC(=O)O[C@H]1C(=O)/C=C/C(=O)[C@@]23C(=N[C@H]([C@@H]2C(=C([C@H]([C@@H]3/C=C/C[C@@H](/C=C1/C)C)O)C)C)Cc1c[nH]c2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404017
PubChem CID:	44448147
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

*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	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]

☑ 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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LD99	=	1.6	ug ml-1	PMID[455868]

☑ 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 NPC2395 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	266
0.1-0.2	1328
0.2-0.3	5901
0.3-0.4	20227
0.4-0.5	9891
0.5-0.6	2649
0.6-0.7	1950
0.7-0.8	446
0.8-0.85	13
0.85-0.9	10
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC235885
0.9592	High Similarity	NPC87856
0.9447	High Similarity	NPC132211
0.9394	High Similarity	NPC151976
0.935	High Similarity	NPC203614
0.9347	High Similarity	NPC267965
0.9337	High Similarity	NPC225821
0.9289	High Similarity	NPC258062
0.9184	High Similarity	NPC98715
0.9158	High Similarity	NPC204491
0.9141	High Similarity	NPC46225
0.9095	High Similarity	NPC127677
0.9087	High Similarity	NPC57690
0.905	High Similarity	NPC271862
0.899	High Similarity	NPC141428
0.8857	High Similarity	NPC267926
0.8852	High Similarity	NPC147446
0.8776	High Similarity	NPC195239
0.8776	High Similarity	NPC157828
0.8731	High Similarity	NPC11445
0.8673	High Similarity	NPC266192
0.8607	High Similarity	NPC300183
0.8519	High Similarity	NPC290529
0.809	Intermediate Similarity	NPC280290
0.8037	Intermediate Similarity	NPC474412
0.8027	Intermediate Similarity	NPC70155
0.799	Intermediate Similarity	NPC267343
0.7943	Intermediate Similarity	NPC476874
0.7941	Intermediate Similarity	NPC47190
0.7929	Intermediate Similarity	NPC213468
0.7871	Intermediate Similarity	NPC315555
0.7857	Intermediate Similarity	NPC260900
0.7847	Intermediate Similarity	NPC252338
0.7843	Intermediate Similarity	NPC154339
0.7838	Intermediate Similarity	NPC472762
0.7837	Intermediate Similarity	NPC67288
0.7824	Intermediate Similarity	NPC229348
0.7811	Intermediate Similarity	NPC469358
0.7767	Intermediate Similarity	NPC234999
0.7761	Intermediate Similarity	NPC71037
0.7714	Intermediate Similarity	NPC74413
0.7713	Intermediate Similarity	NPC476818
0.7706	Intermediate Similarity	NPC471284
0.7703	Intermediate Similarity	NPC227582
0.77	Intermediate Similarity	NPC151939
0.7696	Intermediate Similarity	NPC235684
0.7696	Intermediate Similarity	NPC475778
0.7678	Intermediate Similarity	NPC214428
0.7667	Intermediate Similarity	NPC131887
0.7662	Intermediate Similarity	NPC55772
0.766	Intermediate Similarity	NPC476516
0.7644	Intermediate Similarity	NPC476491
0.7639	Intermediate Similarity	NPC478158
0.7633	Intermediate Similarity	NPC138370
0.7624	Intermediate Similarity	NPC300688
0.7617	Intermediate Similarity	NPC477043
0.7615	Intermediate Similarity	NPC235900
0.7612	Intermediate Similarity	NPC111275
0.7606	Intermediate Similarity	NPC193761
0.7606	Intermediate Similarity	NPC123019
0.7602	Intermediate Similarity	NPC311276
0.7585	Intermediate Similarity	NPC206967
0.7583	Intermediate Similarity	NPC477041
0.7583	Intermediate Similarity	NPC477044
0.7576	Intermediate Similarity	NPC201700
0.7573	Intermediate Similarity	NPC278434
0.7562	Intermediate Similarity	NPC267885
0.7558	Intermediate Similarity	NPC284102
0.7557	Intermediate Similarity	NPC96131
0.7555	Intermediate Similarity	NPC323752
0.7546	Intermediate Similarity	NPC88008
0.7545	Intermediate Similarity	NPC478157
0.7545	Intermediate Similarity	NPC313640
0.7524	Intermediate Similarity	NPC202812
0.7523	Intermediate Similarity	NPC281049
0.7523	Intermediate Similarity	NPC155143
0.7523	Intermediate Similarity	NPC473310
0.7522	Intermediate Similarity	NPC24370
0.7522	Intermediate Similarity	NPC319232
0.7512	Intermediate Similarity	NPC79129
0.7512	Intermediate Similarity	NPC110500
0.7512	Intermediate Similarity	NPC195461
0.7512	Intermediate Similarity	NPC81654
0.7512	Intermediate Similarity	NPC149155
0.7512	Intermediate Similarity	NPC249150
0.7512	Intermediate Similarity	NPC49196
0.7512	Intermediate Similarity	NPC313985
0.7512	Intermediate Similarity	NPC203468
0.7512	Intermediate Similarity	NPC55493
0.75	Intermediate Similarity	NPC277350
0.75	Intermediate Similarity	NPC317752
0.75	Intermediate Similarity	NPC83111
0.7489	Intermediate Similarity	NPC250129
0.7489	Intermediate Similarity	NPC475258
0.7488	Intermediate Similarity	NPC283219
0.7488	Intermediate Similarity	NPC126709
0.7488	Intermediate Similarity	NPC248041
0.7487	Intermediate Similarity	NPC78020
0.7477	Intermediate Similarity	NPC475506
0.7477	Intermediate Similarity	NPC469743
0.7465	Intermediate Similarity	NPC241024
0.7465	Intermediate Similarity	NPC477045
0.7455	Intermediate Similarity	NPC318299
0.7452	Intermediate Similarity	NPC321708
0.7452	Intermediate Similarity	NPC175474
0.7446	Intermediate Similarity	NPC35208
0.7444	Intermediate Similarity	NPC82070
0.7443	Intermediate Similarity	NPC475165
0.7442	Intermediate Similarity	NPC474116
0.743	Intermediate Similarity	NPC475151
0.7421	Intermediate Similarity	NPC54744
0.7418	Intermediate Similarity	NPC50503
0.7416	Intermediate Similarity	NPC95783
0.7399	Intermediate Similarity	NPC472285
0.7398	Intermediate Similarity	NPC469762
0.7397	Intermediate Similarity	NPC162860
0.7393	Intermediate Similarity	NPC253482
0.7391	Intermediate Similarity	NPC163421
0.7391	Intermediate Similarity	NPC188387
0.7385	Intermediate Similarity	NPC474905
0.7383	Intermediate Similarity	NPC293917
0.7378	Intermediate Similarity	NPC61813
0.7376	Intermediate Similarity	NPC219087
0.7376	Intermediate Similarity	NPC292517
0.7376	Intermediate Similarity	NPC75634
0.7376	Intermediate Similarity	NPC314603
0.7371	Intermediate Similarity	NPC156704
0.7368	Intermediate Similarity	NPC63199
0.7368	Intermediate Similarity	NPC111602
0.7368	Intermediate Similarity	NPC102338
0.7368	Intermediate Similarity	NPC475338
0.7368	Intermediate Similarity	NPC196251
0.7368	Intermediate Similarity	NPC909
0.7361	Intermediate Similarity	NPC476073
0.7361	Intermediate Similarity	NPC162730
0.7359	Intermediate Similarity	NPC89987
0.7358	Intermediate Similarity	NPC220151
0.7358	Intermediate Similarity	NPC19692
0.7357	Intermediate Similarity	NPC64216
0.7356	Intermediate Similarity	NPC62749
0.7354	Intermediate Similarity	NPC476114
0.7353	Intermediate Similarity	NPC145885
0.7353	Intermediate Similarity	NPC14113
0.7353	Intermediate Similarity	NPC84827
0.735	Intermediate Similarity	NPC160105
0.7349	Intermediate Similarity	NPC470279
0.7347	Intermediate Similarity	NPC469785
0.7342	Intermediate Similarity	NPC476517
0.7337	Intermediate Similarity	NPC40779
0.7336	Intermediate Similarity	NPC473640
0.7336	Intermediate Similarity	NPC52557
0.7336	Intermediate Similarity	NPC473747
0.7333	Intermediate Similarity	NPC52254
0.7328	Intermediate Similarity	NPC237702
0.7325	Intermediate Similarity	NPC125597
0.7324	Intermediate Similarity	NPC245916
0.7318	Intermediate Similarity	NPC223791
0.7318	Intermediate Similarity	NPC107077
0.7311	Intermediate Similarity	NPC474177
0.7309	Intermediate Similarity	NPC97388
0.7306	Intermediate Similarity	NPC323927
0.7306	Intermediate Similarity	NPC54420
0.7304	Intermediate Similarity	NPC475362
0.73	Intermediate Similarity	NPC475648
0.7297	Intermediate Similarity	NPC207020
0.7296	Intermediate Similarity	NPC211572
0.7296	Intermediate Similarity	NPC70922
0.7296	Intermediate Similarity	NPC80597
0.7296	Intermediate Similarity	NPC75540
0.7296	Intermediate Similarity	NPC212376
0.7295	Intermediate Similarity	NPC472444
0.7293	Intermediate Similarity	NPC475424
0.7293	Intermediate Similarity	NPC79107
0.7291	Intermediate Similarity	NPC313791
0.7284	Intermediate Similarity	NPC244839
0.7284	Intermediate Similarity	NPC319880
0.7284	Intermediate Similarity	NPC320324
0.7281	Intermediate Similarity	NPC475271
0.7277	Intermediate Similarity	NPC30570
0.7277	Intermediate Similarity	NPC181502
0.7277	Intermediate Similarity	NPC85066
0.7277	Intermediate Similarity	NPC36405
0.7277	Intermediate Similarity	NPC133366
0.7277	Intermediate Similarity	NPC474121
0.7273	Intermediate Similarity	NPC230869
0.7269	Intermediate Similarity	NPC45459
0.7269	Intermediate Similarity	NPC315491
0.7269	Intermediate Similarity	NPC213308
0.7269	Intermediate Similarity	NPC470497
0.7269	Intermediate Similarity	NPC473317
0.7265	Intermediate Similarity	NPC473547
0.7265	Intermediate Similarity	NPC234078
0.7265	Intermediate Similarity	NPC221100
0.7264	Intermediate Similarity	NPC49954
0.7264	Intermediate Similarity	NPC474561
0.7261	Intermediate Similarity	NPC146824
0.726	Intermediate Similarity	NPC187456
0.726	Intermediate Similarity	NPC18661
0.7257	Intermediate Similarity	NPC74360
0.7256	Intermediate Similarity	NPC149708

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 NPC2395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	492
0.2-0.3	672
0.3-0.4	1807
0.4-0.5	2955
0.5-0.6	2210
0.6-0.7	739
0.7-0.8	103
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
0.7925	Intermediate Similarity	NPD2510	Approved
0.7925	Intermediate Similarity	NPD2509	Approved
0.784	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7957	Phase 1
0.7746	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD7470	Discontinued
0.7723	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD2091	Phase 2
0.7685	Intermediate Similarity	NPD2096	Phase 2
0.7671	Intermediate Similarity	NPD3389	Approved
0.7671	Intermediate Similarity	NPD3394	Approved
0.7671	Intermediate Similarity	NPD3393	Approved
0.7664	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2095	Phase 2
0.7635	Intermediate Similarity	NPD2094	Phase 2
0.7635	Intermediate Similarity	NPD2092	Phase 2
0.7593	Intermediate Similarity	NPD8399	Phase 1
0.7593	Intermediate Similarity	NPD8423	Phase 2
0.7545	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD8283	Approved
0.7535	Intermediate Similarity	NPD5901	Discontinued
0.7535	Intermediate Similarity	NPD8282	Approved
0.7535	Intermediate Similarity	NPD56	Approved
0.7512	Intermediate Similarity	NPD482	Approved
0.7512	Intermediate Similarity	NPD4601	Approved
0.7512	Intermediate Similarity	NPD4600	Approved
0.75	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD8072	Approved
0.7475	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5003	Discontinued
0.7443	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7001	Phase 3
0.7399	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8326	Phase 3
0.7399	Intermediate Similarity	NPD8325	Phase 3
0.7383	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6987	Phase 1
0.7373	Intermediate Similarity	NPD5426	Phase 3
0.7361	Intermediate Similarity	NPD8073	Approved
0.7353	Intermediate Similarity	NPD2144	Approved
0.7333	Intermediate Similarity	NPD2565	Phase 2
0.7333	Intermediate Similarity	NPD2564	Approved
0.733	Intermediate Similarity	NPD3038	Discontinued
0.7313	Intermediate Similarity	NPD2844	Phase 3
0.7309	Intermediate Similarity	NPD7707	Approved
0.7302	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3947	Discontinued
0.7291	Intermediate Similarity	NPD750	Phase 2
0.7286	Intermediate Similarity	NPD7233	Approved
0.7286	Intermediate Similarity	NPD7234	Approved
0.7285	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7824	Approved
0.7269	Intermediate Similarity	NPD484	Approved
0.7265	Intermediate Similarity	NPD8094	Discontinued
0.7252	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5088	Discontinued
0.7248	Intermediate Similarity	NPD6176	Phase 1
0.7222	Intermediate Similarity	NPD6999	Discontinued
0.7222	Intermediate Similarity	NPD6248	Phase 2
0.7222	Intermediate Similarity	NPD6249	Phase 2
0.7222	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD8093	Discontinued
0.7189	Intermediate Similarity	NPD4500	Approved
0.7189	Intermediate Similarity	NPD4501	Approved
0.7188	Intermediate Similarity	NPD3794	Approved
0.7188	Intermediate Similarity	NPD3795	Approved
0.7186	Intermediate Similarity	NPD7730	Approved
0.7186	Intermediate Similarity	NPD7731	Approved
0.7179	Intermediate Similarity	NPD7790	Approved
0.7179	Intermediate Similarity	NPD7952	Approved
0.7179	Intermediate Similarity	NPD7953	Approved
0.7179	Intermediate Similarity	NPD7950	Approved
0.7179	Intermediate Similarity	NPD7789	Approved
0.7179	Intermediate Similarity	NPD7951	Approved
0.7179	Intermediate Similarity	NPD7791	Approved
0.7177	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2920	Discontinued
0.7156	Intermediate Similarity	NPD8431	Approved
0.7156	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4076	Approved
0.715	Intermediate Similarity	NPD4079	Approved
0.7116	Intermediate Similarity	NPD4427	Phase 2
0.7115	Intermediate Similarity	NPD5897	Approved
0.7115	Intermediate Similarity	NPD5899	Approved
0.7115	Intermediate Similarity	NPD5898	Approved
0.7115	Intermediate Similarity	NPD6595	Phase 3
0.711	Intermediate Similarity	NPD6479	Discontinued
0.7101	Intermediate Similarity	NPD3505	Approved
0.7101	Intermediate Similarity	NPD3506	Approved
0.71	Intermediate Similarity	NPD7271	Approved
0.7097	Intermediate Similarity	NPD7778	Approved
0.7097	Intermediate Similarity	NPD7777	Approved
0.7097	Intermediate Similarity	NPD53	Approved
0.7097	Intermediate Similarity	NPD7946	Pre-registration
0.7095	Intermediate Similarity	NPD8468	Phase 2
0.7094	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5487	Phase 1
0.7089	Intermediate Similarity	NPD4499	Approved
0.7087	Intermediate Similarity	NPD5065	Approved
0.7083	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD7780	Approved
0.7082	Intermediate Similarity	NPD7781	Approved
0.7081	Intermediate Similarity	NPD3178	Discontinued
0.7074	Intermediate Similarity	NPD6242	Discontinued
0.7072	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8289	Discontinued
0.7067	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7878	Phase 2
0.7061	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8272	Phase 2
0.7059	Intermediate Similarity	NPD8098	Approved
0.7059	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7665	Phase 2
0.704	Intermediate Similarity	NPD7666	Phase 3
0.7037	Intermediate Similarity	NPD7944	Discontinued
0.7027	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7010	Phase 3
0.7018	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2336	Approved
0.6974	Remote Similarity	NPD8160	Phase 2
0.6972	Remote Similarity	NPD6206	Phase 1
0.6972	Remote Similarity	NPD7948	Phase 1
0.6967	Remote Similarity	NPD5596	Phase 2
0.6963	Remote Similarity	NPD4334	Discontinued
0.6947	Remote Similarity	NPD5475	Discontinued
0.6943	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6995	Phase 1
0.6933	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7970	Approved
0.692	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.692	Remote Similarity	NPD1392	Approved
0.6916	Remote Similarity	NPD8096	Phase 3
0.6916	Remote Similarity	NPD8097	Phase 3
0.6913	Remote Similarity	NPD5632	Approved
0.6912	Remote Similarity	NPD1038	Approved
0.6909	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3006	Discontinued
0.6898	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6664	Approved
0.6894	Remote Similarity	NPD6165	Phase 2
0.6894	Remote Similarity	NPD6164	Phase 2
0.6894	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7618	Phase 3
0.6881	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7619	Phase 3
0.6878	Remote Similarity	NPD7688	Phase 1
0.6867	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6665	Discontinued
0.686	Remote Similarity	NPD1325	Approved
0.686	Remote Similarity	NPD1326	Approved
0.6858	Remote Similarity	NPD4506	Discontinued
0.6858	Remote Similarity	NPD6529	Discontinued
0.6857	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3280	Approved
0.6852	Remote Similarity	NPD6281	Approved
0.6849	Remote Similarity	NPD2307	Discontinued
0.6844	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4852	Phase 2
0.6837	Remote Similarity	NPD4948	Discontinued
0.6837	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4454	Phase 2
0.683	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5072	Discontinued
0.6826	Remote Similarity	NPD5612	Discontinued
0.6822	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.682	Remote Similarity	NPD4373	Phase 2
0.682	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7956	Approved
0.6813	Remote Similarity	NPD7955	Approved
0.6804	Remote Similarity	NPD4602	Approved
0.6802	Remote Similarity	NPD5482	Discontinued
0.6798	Remote Similarity	NPD5067	Phase 2
0.6798	Remote Similarity	NPD5066	Phase 2
0.6791	Remote Similarity	NPD5444	Phase 1
0.6791	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4315	Phase 2
0.6787	Remote Similarity	NPD6261	Phase 3
0.6786	Remote Similarity	NPD6531	Approved
0.6786	Remote Similarity	NPD6530	Approved
0.6786	Remote Similarity	NPD7708	Approved
0.6784	Remote Similarity	NPD5835	Phase 3
0.6784	Remote Similarity	NPD5834	Phase 3
0.678	Remote Similarity	NPD7711	Discontinued
0.6777	Remote Similarity	NPD8123	Approved
0.6777	Remote Similarity	NPD8122	Approved
0.6776	Remote Similarity	NPD6178	Phase 3
0.6774	Remote Similarity	NPD3871	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