NPASS Compound

Structure

NPC51047 OpenBabel07101719512D 42 44 0 0 1 0 0 0 0 0999 V2000 -0.2579 3.5963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9052 3.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9067 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9067 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8689 1.2475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8470 1.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4067 -2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2290 -0.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5817 0.0885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 2.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5599 0.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2071 -0.2388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5162 0.7122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9126 0.8316 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9344 0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9067 -0.0475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8763 -0.9820 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.4067 0.8185 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9067 -0.0475 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.6456 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4067 -0.9135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2653 1.3669 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 1.6092 3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4943 0.9201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2216 1.7827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 -0.3273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 8 2 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 7 19 1 0 0 0 0 8 24 1 0 0 0 0 9 33 1 0 0 0 0 10 34 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 18 6 1 1 0 0 0 18 22 1 0 0 0 0 19 37 1 6 0 0 0 20 24 2 0 0 0 0 20 30 1 0 0 0 0 21 11 1 6 0 0 0 21 28 1 0 0 0 0 21 35 1 0 0 0 0 22 15 1 1 0 0 0 22 36 1 0 0 0 0 23 26 1 1 0 0 0 23 36 1 0 0 0 0 24 38 1 0 0 0 0 25 27 1 0 0 0 0 25 39 1 1 0 0 0 26 33 2 3 0 0 0 26 40 1 0 0 0 0 27 35 2 3 0 0 0 27 41 1 0 0 0 0 28 36 1 0 0 0 0 28 42 2 0 0 0 0 29 31 2 0 0 0 0 29 32 1 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.31
Volume:	599.948
LogP:	1.883
LogD:	1.272
LogS:	-3.545
# Rotatable Bonds:	16
TPSA:	203.6
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.097
Synthetic Accessibility Score:	4.368
Fsp3:	0.655
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:	-5.955
MDCK Permeability:	3.889453364536166e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	60.149986267089844%
Volume Distribution (VD):	0.789
Pgp-substrate:	39.51262664794922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	6.238
Half-life (T1/2):	0.229

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.963
Drug-inuced Liver Injury (DILI):	0.806
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.223
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC51047

Natural Product ID:	NPC51047
*Common Name:**	(2S,3As,6R,7As)-1-((R)-2-((R)-3-(3-Chloro-4-Hydroxyphenyl)-2-Hydroxypropanamido)-4-Methylpentanoyl)-N-(4-Guanidinobutyl)-6-Hydroxyoctahydro-1H-Indole-2-Carboxamide
IUPAC Name:	(2S,3aS,6R,7aS)-1-[(2R)-2-[[(2R)-3-(3-chloro-4-hydroxyphenyl)-2-hydroxypropanoyl]amino]-4-methylpentanoyl]-N-[4-(diaminomethylideneamino)butyl]-6-hydroxy-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxamide
Synonyms:
Standard InCHIKey:	ZJNOSDFPXZTAGG-JDAMQYKPSA-N
Standard InCHI:	InChI=1S/C29H45ClN6O6/c1-16(2)11-21(35-27(41)25(39)13-17-5-8-24(38)20(30)12-17)28(42)36-22-15-19(37)7-6-18(22)14-23(36)26(40)33-9-3-4-10-34-29(31)32/h5,8,12,16,18-19,21-23,25,37-39H,3-4,6-7,9-11,13-15H2,1-2H3,(H,33,40)(H,35,41)(H4,31,32,34)/t18-,19+,21+,22-,23-,25+/m0/s1
SMILES:	CC(C[C@H](C(=O)N1[C@H]2C[C@H](O)CC[C@H]2C[C@H]1C(=NCCCCNC(=N)N)O)N=C([C@@H](Cc1ccc(c(c1)Cl)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386694
PubChem CID:	71726249
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004830] Dipeptides

*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
NPO32761	microcystis sp.	Species	Microcystaceae	Bacteria	n.a.	Germany	n.a.	PMID[18163584]
NPO32761	microcystis sp.	Species	Microcystaceae	Bacteria	Israeli fishpond water bloom	n.a.	n.a.	PMID[20028081]
NPO32761	microcystis sp.	Species	Microcystaceae	Bacteria	n.a.	Varanasi, India	n.a.	PMID[23777401]
NPO32761	microcystis sp.	Species	Microcystaceae	Bacteria	n.a.	Tel Aviv Safari in Israel	n.a.	Database[Title]

☑ 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

Activity Type	# Activity
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1644	Protein Family	Trypsin	Homo sapiens	IC50	=	4300.0	nM	PMID[553268]

☑ 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 NPC51047 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	238
0.1-0.2	1294
0.2-0.3	9718
0.3-0.4	10551
0.4-0.5	17846
0.5-0.6	2471
0.6-0.7	433
0.7-0.8	118
0.8-0.85	15
0.85-0.9	6
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9708	High Similarity	NPC470728
0.9071	High Similarity	NPC81845
0.883	High Similarity	NPC295795
0.8713	High Similarity	NPC280022
0.8686	High Similarity	NPC97526
0.8686	High Similarity	NPC119652
0.8649	High Similarity	NPC469443
0.8453	Intermediate Similarity	NPC94862
0.8453	Intermediate Similarity	NPC96275
0.8452	Intermediate Similarity	NPC476268
0.8377	Intermediate Similarity	NPC220060
0.8333	Intermediate Similarity	NPC469444
0.8207	Intermediate Similarity	NPC246591
0.8205	Intermediate Similarity	NPC469445
0.8187	Intermediate Similarity	NPC194699
0.8187	Intermediate Similarity	NPC219350
0.802	Intermediate Similarity	NPC277306
0.802	Intermediate Similarity	NPC469442
0.7989	Intermediate Similarity	NPC80514
0.794	Intermediate Similarity	NPC25539
0.7889	Intermediate Similarity	NPC89831
0.7853	Intermediate Similarity	NPC473371
0.7845	Intermediate Similarity	NPC475532
0.7821	Intermediate Similarity	NPC209463
0.7809	Intermediate Similarity	NPC63931
0.7802	Intermediate Similarity	NPC17698
0.7802	Intermediate Similarity	NPC165285
0.7778	Intermediate Similarity	NPC129486
0.7637	Intermediate Similarity	NPC274198
0.7637	Intermediate Similarity	NPC276506
0.7637	Intermediate Similarity	NPC198254
0.7634	Intermediate Similarity	NPC475409
0.7634	Intermediate Similarity	NPC170302
0.7634	Intermediate Similarity	NPC475564
0.7632	Intermediate Similarity	NPC102959
0.7617	Intermediate Similarity	NPC477638
0.7617	Intermediate Similarity	NPC477632
0.7609	Intermediate Similarity	NPC471165
0.7594	Intermediate Similarity	NPC473404
0.7592	Intermediate Similarity	NPC60516
0.7588	Intermediate Similarity	NPC168861
0.7586	Intermediate Similarity	NPC473491
0.7565	Intermediate Similarity	NPC302715
0.7527	Intermediate Similarity	NPC473546
0.7514	Intermediate Similarity	NPC16188
0.75	Intermediate Similarity	NPC240130
0.75	Intermediate Similarity	NPC61332
0.7486	Intermediate Similarity	NPC244336
0.7473	Intermediate Similarity	NPC196243
0.7444	Intermediate Similarity	NPC475544
0.7444	Intermediate Similarity	NPC469243
0.7427	Intermediate Similarity	NPC476989
0.7423	Intermediate Similarity	NPC477631
0.7416	Intermediate Similarity	NPC244509
0.7416	Intermediate Similarity	NPC473580
0.7411	Intermediate Similarity	NPC477550
0.7411	Intermediate Similarity	NPC477552
0.7409	Intermediate Similarity	NPC477636
0.7405	Intermediate Similarity	NPC328494
0.7401	Intermediate Similarity	NPC56685
0.7401	Intermediate Similarity	NPC262166
0.7398	Intermediate Similarity	NPC329295
0.7351	Intermediate Similarity	NPC475123
0.7351	Intermediate Similarity	NPC475204
0.7337	Intermediate Similarity	NPC328649
0.7337	Intermediate Similarity	NPC477551
0.7326	Intermediate Similarity	NPC26108
0.7322	Intermediate Similarity	NPC223207
0.7314	Intermediate Similarity	NPC311658
0.7308	Intermediate Similarity	NPC241794
0.7303	Intermediate Similarity	NPC202198
0.7287	Intermediate Similarity	NPC50016
0.7283	Intermediate Similarity	NPC471771
0.7283	Intermediate Similarity	NPC61004
0.7283	Intermediate Similarity	NPC304074
0.7283	Intermediate Similarity	NPC290755
0.7273	Intermediate Similarity	NPC273755
0.7267	Intermediate Similarity	NPC214988
0.7263	Intermediate Similarity	NPC153554
0.7243	Intermediate Similarity	NPC302597
0.7238	Intermediate Similarity	NPC323336
0.7238	Intermediate Similarity	NPC326349
0.7222	Intermediate Similarity	NPC477639
0.7204	Intermediate Similarity	NPC66490
0.7181	Intermediate Similarity	NPC248670
0.7168	Intermediate Similarity	NPC48202
0.7166	Intermediate Similarity	NPC46009
0.7151	Intermediate Similarity	NPC233702
0.7143	Intermediate Similarity	NPC136797
0.7135	Intermediate Similarity	NPC267237
0.712	Intermediate Similarity	NPC45037
0.7111	Intermediate Similarity	NPC261934
0.7111	Intermediate Similarity	NPC5194
0.711	Intermediate Similarity	NPC242159
0.711	Intermediate Similarity	NPC313694
0.709	Intermediate Similarity	NPC137627
0.7087	Intermediate Similarity	NPC478005
0.7053	Intermediate Similarity	NPC473354
0.7047	Intermediate Similarity	NPC477637
0.7005	Intermediate Similarity	NPC254700
0.7	Intermediate Similarity	NPC306804
0.6984	Remote Similarity	NPC40234
0.698	Remote Similarity	NPC323662
0.6968	Remote Similarity	NPC294516
0.6968	Remote Similarity	NPC107938
0.6966	Remote Similarity	NPC81026
0.6963	Remote Similarity	NPC476227
0.6919	Remote Similarity	NPC1390
0.6919	Remote Similarity	NPC62104
0.691	Remote Similarity	NPC266741
0.691	Remote Similarity	NPC315266
0.6895	Remote Similarity	NPC269383
0.6895	Remote Similarity	NPC151030
0.6878	Remote Similarity	NPC141957
0.6875	Remote Similarity	NPC227778
0.6872	Remote Similarity	NPC476321
0.6866	Remote Similarity	NPC328763
0.6859	Remote Similarity	NPC230611
0.6856	Remote Similarity	NPC194671
0.6856	Remote Similarity	NPC269750
0.6845	Remote Similarity	NPC73655
0.6837	Remote Similarity	NPC471526
0.6821	Remote Similarity	NPC326966
0.6806	Remote Similarity	NPC478007
0.6802	Remote Similarity	NPC294951
0.6793	Remote Similarity	NPC39431
0.6791	Remote Similarity	NPC114806
0.6788	Remote Similarity	NPC159767
0.6788	Remote Similarity	NPC279871
0.6788	Remote Similarity	NPC473402
0.6788	Remote Similarity	NPC158277
0.6788	Remote Similarity	NPC155506
0.6774	Remote Similarity	NPC324850
0.6772	Remote Similarity	NPC5719
0.6772	Remote Similarity	NPC217804
0.6772	Remote Similarity	NPC210377
0.6772	Remote Similarity	NPC22883
0.676	Remote Similarity	NPC326241
0.6743	Remote Similarity	NPC478008
0.6738	Remote Similarity	NPC24617
0.6738	Remote Similarity	NPC287757
0.6738	Remote Similarity	NPC319320
0.6736	Remote Similarity	NPC49315
0.6724	Remote Similarity	NPC48909
0.672	Remote Similarity	NPC133470
0.672	Remote Similarity	NPC289776
0.672	Remote Similarity	NPC191863
0.6717	Remote Similarity	NPC471048
0.6717	Remote Similarity	NPC471049
0.6717	Remote Similarity	NPC471050
0.6704	Remote Similarity	NPC251439
0.6702	Remote Similarity	NPC63040
0.6685	Remote Similarity	NPC300443
0.6684	Remote Similarity	NPC472923
0.6683	Remote Similarity	NPC299806
0.6667	Remote Similarity	NPC6570
0.6667	Remote Similarity	NPC473450
0.6667	Remote Similarity	NPC186617
0.665	Remote Similarity	NPC45112
0.665	Remote Similarity	NPC263507
0.665	Remote Similarity	NPC134413
0.665	Remote Similarity	NPC276120
0.665	Remote Similarity	NPC271958
0.6649	Remote Similarity	NPC15068
0.6647	Remote Similarity	NPC6975
0.6634	Remote Similarity	NPC163961
0.6634	Remote Similarity	NPC473305
0.6632	Remote Similarity	NPC471568
0.6632	Remote Similarity	NPC473693
0.6632	Remote Similarity	NPC196091
0.663	Remote Similarity	NPC324081
0.6622	Remote Similarity	NPC323198
0.6618	Remote Similarity	NPC65714
0.6601	Remote Similarity	NPC473407
0.6601	Remote Similarity	NPC473378
0.66	Remote Similarity	NPC138083
0.6591	Remote Similarity	NPC208757
0.6588	Remote Similarity	NPC252878
0.6573	Remote Similarity	NPC64205
0.6566	Remote Similarity	NPC32064
0.6566	Remote Similarity	NPC39822
0.6559	Remote Similarity	NPC122590
0.6552	Remote Similarity	NPC283207
0.655	Remote Similarity	NPC46427
0.6541	Remote Similarity	NPC7817
0.6541	Remote Similarity	NPC475168
0.6534	Remote Similarity	NPC257390
0.6529	Remote Similarity	NPC202521
0.6522	Remote Similarity	NPC471592
0.6519	Remote Similarity	NPC91953
0.6517	Remote Similarity	NPC315542
0.6514	Remote Similarity	NPC325651
0.6509	Remote Similarity	NPC283760
0.65	Remote Similarity	NPC86678
0.6497	Remote Similarity	NPC287401
0.6486	Remote Similarity	NPC2501
0.6484	Remote Similarity	NPC52748
0.648	Remote Similarity	NPC127741
0.6471	Remote Similarity	NPC476990
0.6464	Remote Similarity	NPC197921

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 NPC51047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	453
0.2-0.3	759
0.3-0.4	2044
0.4-0.5	3920
0.5-0.6	1681
0.6-0.7	138
0.7-0.8	4
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
0.7865	Intermediate Similarity	NPD8303	Discontinued
0.7528	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7495	Discontinued
0.7234	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7523	Phase 3
0.7143	Intermediate Similarity	NPD7617	Discontinued
0.7128	Intermediate Similarity	NPD5137	Approved
0.7104	Intermediate Similarity	NPD8019	Approved
0.6966	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7303	Discontinued
0.6857	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7484	Phase 3
0.6842	Remote Similarity	NPD7485	Phase 3
0.6839	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4652	Approved
0.68	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3136	Phase 2
0.6742	Remote Similarity	NPD7450	Phase 2
0.6721	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD8076	Discontinued
0.6702	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2098	Approved
0.6667	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6901	Phase 3
0.6629	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7978	Discontinued
0.6603	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7613	Discontinued
0.6593	Remote Similarity	NPD6676	Phase 2
0.6591	Remote Similarity	NPD829	Discontinued
0.659	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2097	Approved
0.6559	Remote Similarity	NPD7131	Phase 3
0.6541	Remote Similarity	NPD6419	Discontinued
0.6535	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4731	Phase 3
0.65	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD3933	Discontinued
0.6465	Remote Similarity	NPD5096	Phase 3
0.6465	Remote Similarity	NPD5095	Phase 3
0.6453	Remote Similarity	NPD2561	Approved
0.6453	Remote Similarity	NPD2562	Approved
0.6448	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6058	Phase 2
0.6436	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1972	Approved
0.6436	Remote Similarity	NPD1973	Approved
0.6432	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD3364	Phase 3
0.641	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6681	Discovery
0.6389	Remote Similarity	NPD5314	Approved
0.6389	Remote Similarity	NPD8173	Phase 2
0.6389	Remote Similarity	NPD8172	Phase 2
0.6389	Remote Similarity	NPD6073	Approved
0.6378	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7608	Discontinued
0.6355	Remote Similarity	NPD6557	Phase 2
0.6354	Remote Similarity	NPD3555	Approved
0.6354	Remote Similarity	NPD3553	Approved
0.6354	Remote Similarity	NPD3552	Approved
0.6354	Remote Similarity	NPD3554	Approved
0.6348	Remote Similarity	NPD1330	Phase 2
0.6348	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6312	Discontinued
0.6344	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5263	Approved
0.6327	Remote Similarity	NPD2888	Approved
0.6327	Remote Similarity	NPD2889	Approved
0.6327	Remote Similarity	NPD2017	Approved
0.6327	Remote Similarity	NPD2890	Approved
0.6316	Remote Similarity	NPD6057	Approved
0.6316	Remote Similarity	NPD6056	Approved
0.6313	Remote Similarity	NPD1130	Approved
0.6313	Remote Similarity	NPD1136	Approved
0.6313	Remote Similarity	NPD1132	Approved
0.6307	Remote Similarity	NPD7451	Discontinued
0.6298	Remote Similarity	NPD2568	Approved
0.6284	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD3062	Approved
0.6278	Remote Similarity	NPD3061	Approved
0.6278	Remote Similarity	NPD3059	Approved
0.6277	Remote Similarity	NPD3985	Discontinued
0.6274	Remote Similarity	NPD5542	Phase 2
0.6269	Remote Similarity	NPD5773	Approved
0.6269	Remote Similarity	NPD5772	Approved
0.6262	Remote Similarity	NPD4157	Discontinued
0.6257	Remote Similarity	NPD597	Approved
0.6257	Remote Similarity	NPD598	Approved
0.6257	Remote Similarity	NPD601	Approved
0.6256	Remote Similarity	NPD5218	Approved
0.6256	Remote Similarity	NPD5219	Approved
0.6256	Remote Similarity	NPD8031	Discontinued
0.6243	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5967	Approved
0.6223	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD1423	Approved
0.6215	Remote Similarity	NPD4386	Approved
0.6215	Remote Similarity	NPD4387	Approved
0.6209	Remote Similarity	NPD817	Approved
0.6209	Remote Similarity	NPD823	Approved
0.6209	Remote Similarity	NPD4915	Approved
0.6199	Remote Similarity	NPD856	Approved
0.6199	Remote Similarity	NPD318	Approved
0.6199	Remote Similarity	NPD317	Approved
0.6199	Remote Similarity	NPD16	Approved
0.6195	Remote Similarity	NPD6851	Approved
0.6195	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6853	Approved
0.619	Remote Similarity	NPD2874	Phase 2
0.6188	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5567	Approved
0.6184	Remote Similarity	NPD8292	Phase 2
0.6173	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD3053	Approved
0.6158	Remote Similarity	NPD6297	Approved
0.6158	Remote Similarity	NPD3055	Approved
0.6154	Remote Similarity	NPD3577	Discontinued
0.615	Remote Similarity	NPD1967	Approved
0.615	Remote Similarity	NPD1968	Approved
0.6143	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD4590	Approved
0.6136	Remote Similarity	NPD4659	Approved
0.6135	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4388	Approved
0.6132	Remote Similarity	NPD5543	Approved
0.6121	Remote Similarity	NPD3602	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4914	Approved
0.612	Remote Similarity	NPD5725	Approved
0.6117	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD1714	Approved
0.6114	Remote Similarity	NPD1715	Phase 1
0.6111	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3365	Discontinued
0.6108	Remote Similarity	NPD2240	Approved
0.6108	Remote Similarity	NPD2239	Approved
0.6106	Remote Similarity	NPD6796	Discontinued
0.6105	Remote Similarity	NPD828	Approved
0.6105	Remote Similarity	NPD3536	Discontinued
0.6103	Remote Similarity	NPD2978	Approved
0.6103	Remote Similarity	NPD2977	Approved
0.6102	Remote Similarity	NPD5310	Approved
0.6102	Remote Similarity	NPD5311	Approved
0.6099	Remote Similarity	NPD4153	Approved
0.6099	Remote Similarity	NPD6346	Approved
0.6098	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD1416	Approved
0.6096	Remote Similarity	NPD3638	Discontinued
0.6095	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7342	Discontinued
0.6091	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD8070	Approved
0.6089	Remote Similarity	NPD3040	Approved
0.6089	Remote Similarity	NPD4175	Approved
0.6089	Remote Similarity	NPD4177	Approved
0.608	Remote Similarity	NPD3072	Approved
0.608	Remote Similarity	NPD3071	Approved
0.608	Remote Similarity	NPD3073	Approved
0.6077	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5544	Approved
0.6069	Remote Similarity	NPD2218	Phase 2
0.6069	Remote Similarity	NPD2217	Approved
0.6069	Remote Similarity	NPD316	Approved
0.6067	Remote Similarity	NPD4103	Phase 2
0.6067	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6086	Phase 2
0.6065	Remote Similarity	NPD6863	Phase 2
0.6059	Remote Similarity	NPD6042	Phase 2
0.6059	Remote Similarity	NPD42	Phase 2
0.6056	Remote Similarity	NPD7282	Approved
0.6056	Remote Similarity	NPD4676	Approved
0.6056	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD7011	Discontinued
0.6051	Remote Similarity	NPD4227	Discontinued
0.6048	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD6405	Approved
0.6044	Remote Similarity	NPD6407	Approved
0.6044	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD9620	Approved
0.6034	Remote Similarity	NPD9621	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data