NPASS Compound

Structure

NPC473546 OpenBabel07101718182D 50 52 0 0 1 0 0 0 0 0999 V2000 -2.5334 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6500 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5160 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5306 2.7338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8907 1.0396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5160 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3820 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5088 2.9417 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 5.7839 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2435 1.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5279 -0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 -2.3090 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 -0.3601 -3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6500 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2216 1.7827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3820 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1779 2.1985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1859 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -1.3090 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 -4.9291 -1.7271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 -4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3359 -2.6407 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5169 -0.9181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 -3.7281 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2361 -5.4223 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 -2.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9346 -1.6226 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -4.2633 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -2.3090 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 9.2480 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1561 2.4064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 2.1100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -2.2226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 1 14 1 0 0 0 0 2 6 1 0 0 0 0 2 20 2 0 0 0 0 3 7 2 0 0 0 0 3 20 1 0 0 0 0 4 8 1 0 0 0 0 4 21 2 0 0 0 0 5 9 2 0 0 0 0 5 21 1 0 0 0 0 6 22 2 0 0 0 0 7 22 1 0 0 0 0 8 23 2 0 0 0 0 9 23 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 16 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 24 1 0 0 0 0 13 31 1 0 0 0 0 14 39 1 0 0 0 0 15 37 1 0 0 0 0 16 38 1 0 0 0 0 17 40 1 0 0 0 0 18 25 1 0 0 0 0 18 41 1 0 0 0 0 19 26 1 0 0 0 0 19 42 1 0 0 0 0 22 43 1 0 0 0 0 23 44 1 0 0 0 0 24 31 1 6 0 0 0 24 32 1 0 0 0 0 25 37 2 3 0 0 0 25 45 1 0 0 0 0 26 38 2 3 0 0 0 26 46 1 0 0 0 0 27 32 1 0 0 0 0 27 41 2 3 0 0 0 27 47 1 0 0 0 0 28 31 1 0 0 0 0 28 42 1 0 0 0 0 28 48 2 0 0 0 0 29 33 2 0 0 0 0 29 34 1 0 0 0 0 29 39 1 0 0 0 0 30 35 2 0 0 0 0 30 36 1 0 0 0 0 30 40 1 0 0 0 0 31 49 1 6 0 0 0 32 42 1 0 0 0 0 32 50 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	694.32
Volume:	679.738
LogP:	-0.615
LogD:	-0.653
LogS:	-2.591
# Rotatable Bonds:	20
TPSA:	315.49
# H-Bond Aceptor:	18
# H-Bond Donor:	13
# Rings:	3
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.052
Synthetic Accessibility Score:	4.955
Fsp3:	0.375
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:	-6.002
MDCK Permeability:	5.242342012934387e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.971
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	45.172332763671875%
Volume Distribution (VD):	0.969
Pgp-substrate:	51.50835418701172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.269
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	2.052
Half-life (T1/2):	0.451

ADMET: Toxicity

hERG Blockers:	0.217
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.485
Maximum Recommended Daily Dose:	0.207
Skin Sensitization:	0.236
Carcinogencity:	0.654
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.288

Download Data

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

Natural Product: NPC473546

Natural Product ID:	NPC473546
*Common Name:**	Anchinopeptolide D
IUPAC Name:	(2S,3R,4S)-3-[2-(diaminomethylideneamino)ethyl]-4-[3-(diaminomethylideneamino)propyl]-2,4-dihydroxy-N,1-bis[2-[[(E)-2-(4-hydroxyphenyl)ethenyl]amino]-2-oxoethyl]-5-oxopyrrolidine-2-carboxamide
Synonyms:	Anchinopeptolide D
Standard InCHIKey:	BBMGZUODZUGTGP-YKYMCWODSA-N
Standard InCHI:	InChI=1S/C32H42N10O8/c33-29(34)39-14-1-13-31(49)24(12-17-40-30(35)36)32(50,27(47)41-18-25(45)37-15-10-20-2-6-22(43)7-3-20)42(28(31)48)19-26(46)38-16-11-21-4-8-23(44)9-5-21/h2-11,15-16,24,43-44,49-50H,1,12-14,17-19H2,(H,37,45)(H,38,46)(H,41,47)(H4,33,34,39)(H4,35,36,40)/b15-10+,16-11+/t24-,31+,32+/m1/s1
SMILES:	C1=CC(=CC=C1C=CNC(=O)CNC(=O)C2(C(C(C(=O)N2CC(=O)NC=CC3=CC=C(C=C3)O)(CCCN=C(N)N)O)CCN=C(N)N)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445234
PubChem CID:	10484815
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
NPO32717	anchinoe tenacior	Species	Hymedesmiidae	Eukaryota	n.a.	Mediterranean	n.a.	PMID[7798957]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	77.0	%	PMID[536317]

☑ 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 NPC473546 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	270
0.1-0.2	1377
0.2-0.3	9483
0.3-0.4	8531
0.4-0.5	18507
0.5-0.6	3864
0.6-0.7	495
0.7-0.8	158
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC475409
0.9875	High Similarity	NPC170302
0.9875	High Similarity	NPC475564
0.8235	Intermediate Similarity	NPC280022
0.8198	Intermediate Similarity	NPC475532
0.815	Intermediate Similarity	NPC165285
0.8114	Intermediate Similarity	NPC119652
0.8114	Intermediate Similarity	NPC97526
0.8046	Intermediate Similarity	NPC17698
0.8023	Intermediate Similarity	NPC129486
0.8012	Intermediate Similarity	NPC61004
0.7977	Intermediate Similarity	NPC198254
0.7977	Intermediate Similarity	NPC276506
0.7977	Intermediate Similarity	NPC274198
0.7935	Intermediate Similarity	NPC477632
0.7935	Intermediate Similarity	NPC477638
0.7912	Intermediate Similarity	NPC240130
0.7912	Intermediate Similarity	NPC61332
0.7821	Intermediate Similarity	NPC473404
0.7802	Intermediate Similarity	NPC94862
0.7797	Intermediate Similarity	NPC196243
0.7784	Intermediate Similarity	NPC302715
0.776	Intermediate Similarity	NPC102959
0.7759	Intermediate Similarity	NPC328649
0.774	Intermediate Similarity	NPC471165
0.7738	Intermediate Similarity	NPC56685
0.7717	Intermediate Similarity	NPC60516
0.7644	Intermediate Similarity	NPC63931
0.7634	Intermediate Similarity	NPC477631
0.7632	Intermediate Similarity	NPC477551
0.763	Intermediate Similarity	NPC241794
0.7622	Intermediate Similarity	NPC477636
0.7609	Intermediate Similarity	NPC96275
0.7606	Intermediate Similarity	NPC329295
0.7598	Intermediate Similarity	NPC50016
0.7578	Intermediate Similarity	NPC267237
0.7572	Intermediate Similarity	NPC475544
0.7572	Intermediate Similarity	NPC469243
0.7569	Intermediate Similarity	NPC153554
0.7558	Intermediate Similarity	NPC326349
0.7558	Intermediate Similarity	NPC323336
0.7545	Intermediate Similarity	NPC16188
0.7544	Intermediate Similarity	NPC476268
0.7529	Intermediate Similarity	NPC202198
0.7528	Intermediate Similarity	NPC328494
0.7527	Intermediate Similarity	NPC51047
0.7526	Intermediate Similarity	NPC477550
0.7526	Intermediate Similarity	NPC477552
0.7514	Intermediate Similarity	NPC244336
0.7513	Intermediate Similarity	NPC477639
0.75	Intermediate Similarity	NPC214988
0.7486	Intermediate Similarity	NPC248670
0.7472	Intermediate Similarity	NPC475204
0.7472	Intermediate Similarity	NPC475123
0.7471	Intermediate Similarity	NPC114806
0.7455	Intermediate Similarity	NPC476989
0.7444	Intermediate Similarity	NPC26108
0.7443	Intermediate Similarity	NPC223207
0.7442	Intermediate Similarity	NPC473580
0.7414	Intermediate Similarity	NPC24617
0.7412	Intermediate Similarity	NPC473491
0.741	Intermediate Similarity	NPC168861
0.7401	Intermediate Similarity	NPC304074
0.7401	Intermediate Similarity	NPC290755
0.7401	Intermediate Similarity	NPC471771
0.7394	Intermediate Similarity	NPC48202
0.7389	Intermediate Similarity	NPC273755
0.738	Intermediate Similarity	NPC246591
0.7374	Intermediate Similarity	NPC46009
0.7368	Intermediate Similarity	NPC233702
0.7358	Intermediate Similarity	NPC469443
0.7341	Intermediate Similarity	NPC244509
0.7326	Intermediate Similarity	NPC261934
0.7326	Intermediate Similarity	NPC262166
0.7326	Intermediate Similarity	NPC5194
0.7322	Intermediate Similarity	NPC45037
0.7318	Intermediate Similarity	NPC66490
0.7302	Intermediate Similarity	NPC470728
0.7293	Intermediate Similarity	NPC137627
0.7278	Intermediate Similarity	NPC40234
0.7277	Intermediate Similarity	NPC80514
0.7273	Intermediate Similarity	NPC478005
0.7263	Intermediate Similarity	NPC302597
0.7262	Intermediate Similarity	NPC326241
0.7243	Intermediate Similarity	NPC477637
0.7238	Intermediate Similarity	NPC89831
0.7235	Intermediate Similarity	NPC311658
0.7228	Intermediate Similarity	NPC194671
0.7228	Intermediate Similarity	NPC269750
0.7198	Intermediate Similarity	NPC306804
0.7167	Intermediate Similarity	NPC107938
0.7167	Intermediate Similarity	NPC294516
0.7167	Intermediate Similarity	NPC141957
0.7166	Intermediate Similarity	NPC294951
0.7158	Intermediate Similarity	NPC279871
0.7158	Intermediate Similarity	NPC473354
0.7136	Intermediate Similarity	NPC220060
0.7111	Intermediate Similarity	NPC254700
0.71	Intermediate Similarity	NPC469444
0.7069	Intermediate Similarity	NPC300443
0.7065	Intermediate Similarity	NPC473402
0.7065	Intermediate Similarity	NPC158277
0.7053	Intermediate Similarity	NPC478007
0.7049	Intermediate Similarity	NPC230611
0.7024	Intermediate Similarity	NPC242159
0.7024	Intermediate Similarity	NPC313694
0.7022	Intermediate Similarity	NPC1390
0.7022	Intermediate Similarity	NPC62104
0.6995	Remote Similarity	NPC469445
0.6986	Remote Similarity	NPC478008
0.6984	Remote Similarity	NPC471048
0.6984	Remote Similarity	NPC471049
0.6984	Remote Similarity	NPC471050
0.6979	Remote Similarity	NPC163961
0.6979	Remote Similarity	NPC473305
0.6973	Remote Similarity	NPC136797
0.6973	Remote Similarity	NPC159767
0.6973	Remote Similarity	NPC476227
0.6973	Remote Similarity	NPC155506
0.6968	Remote Similarity	NPC476321
0.6965	Remote Similarity	NPC194699
0.6965	Remote Similarity	NPC219350
0.6947	Remote Similarity	NPC299806
0.6931	Remote Similarity	NPC471526
0.6928	Remote Similarity	NPC326966
0.6885	Remote Similarity	NPC209463
0.6884	Remote Similarity	NPC328924
0.6872	Remote Similarity	NPC324850
0.6868	Remote Similarity	NPC210377
0.6868	Remote Similarity	NPC217804
0.6868	Remote Similarity	NPC5719
0.6868	Remote Similarity	NPC22883
0.6866	Remote Similarity	NPC81845
0.6831	Remote Similarity	NPC15068
0.6829	Remote Similarity	NPC469442
0.6829	Remote Similarity	NPC277306
0.6818	Remote Similarity	NPC323662
0.6813	Remote Similarity	NPC289776
0.6813	Remote Similarity	NPC191863
0.6813	Remote Similarity	NPC133470
0.6802	Remote Similarity	NPC251439
0.6793	Remote Similarity	NPC63040
0.6786	Remote Similarity	NPC65714
0.678	Remote Similarity	NPC295795
0.6776	Remote Similarity	NPC323244
0.6765	Remote Similarity	NPC64205
0.6763	Remote Similarity	NPC25539
0.675	Remote Similarity	NPC473450
0.6721	Remote Similarity	NPC22014
0.6718	Remote Similarity	NPC283207
0.6717	Remote Similarity	NPC473371
0.6707	Remote Similarity	NPC271808
0.6707	Remote Similarity	NPC325651
0.6684	Remote Similarity	NPC473378
0.6684	Remote Similarity	NPC475421
0.6684	Remote Similarity	NPC138083
0.6684	Remote Similarity	NPC473407
0.6684	Remote Similarity	NPC235194
0.6683	Remote Similarity	NPC471592
0.6667	Remote Similarity	NPC73655
0.6667	Remote Similarity	NPC109580
0.6648	Remote Similarity	NPC287757
0.6648	Remote Similarity	NPC122590
0.6648	Remote Similarity	NPC319320
0.6616	Remote Similarity	NPC328763
0.6614	Remote Similarity	NPC477462
0.6608	Remote Similarity	NPC273907
0.6608	Remote Similarity	NPC474811
0.6608	Remote Similarity	NPC79465
0.6608	Remote Similarity	NPC293377
0.6608	Remote Similarity	NPC476102
0.6608	Remote Similarity	NPC118099
0.6608	Remote Similarity	NPC474855
0.6608	Remote Similarity	NPC260045
0.6608	Remote Similarity	NPC151706
0.6608	Remote Similarity	NPC475598
0.6608	Remote Similarity	NPC474787
0.6608	Remote Similarity	NPC76785
0.6608	Remote Similarity	NPC90194
0.6608	Remote Similarity	NPC9687
0.6608	Remote Similarity	NPC475318
0.6608	Remote Similarity	NPC49577
0.6605	Remote Similarity	NPC283760
0.6595	Remote Similarity	NPC472923
0.6593	Remote Similarity	NPC197743
0.6593	Remote Similarity	NPC297145
0.6582	Remote Similarity	NPC234069
0.658	Remote Similarity	NPC470112
0.658	Remote Similarity	NPC167763
0.658	Remote Similarity	NPC470903
0.6578	Remote Similarity	NPC186617
0.6562	Remote Similarity	NPC39822
0.6548	Remote Similarity	NPC174122
0.6548	Remote Similarity	NPC64140
0.6543	Remote Similarity	NPC196091
0.6543	Remote Similarity	NPC471568
0.6543	Remote Similarity	NPC473693
0.6542	Remote Similarity	NPC473317
0.6538	Remote Similarity	NPC14390
0.6538	Remote Similarity	NPC197125

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 NPC473546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	433
0.2-0.3	756
0.3-0.4	1824
0.4-0.5	3963
0.5-0.6	1883
0.6-0.7	134
0.7-0.8	9
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
0.8118	Intermediate Similarity	NPD8303	Discontinued
0.7633	Intermediate Similarity	NPD7523	Phase 3
0.7542	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7617	Discontinued
0.7414	Intermediate Similarity	NPD8019	Approved
0.7314	Intermediate Similarity	NPD7495	Discontinued
0.7257	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8076	Discontinued
0.6989	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8292	Phase 2
0.6804	Remote Similarity	NPD6836	Approved
0.68	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7303	Discontinued
0.6774	Remote Similarity	NPD5137	Approved
0.6768	Remote Similarity	NPD7282	Approved
0.6766	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7450	Phase 2
0.6725	Remote Similarity	NPD6901	Phase 3
0.6705	Remote Similarity	NPD7978	Discontinued
0.6685	Remote Similarity	NPD7613	Discontinued
0.6647	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD4652	Approved
0.6627	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1330	Phase 2
0.6601	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD8162	Phase 2
0.6582	Remote Similarity	NPD6835	Approved
0.6579	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3136	Phase 2
0.6513	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD8031	Discontinued
0.6505	Remote Similarity	NPD5219	Approved
0.6505	Remote Similarity	NPD5218	Approved
0.6497	Remote Similarity	NPD6676	Phase 2
0.6494	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7484	Phase 3
0.6489	Remote Similarity	NPD7485	Phase 3
0.6488	Remote Similarity	NPD7451	Discontinued
0.6477	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5314	Approved
0.6467	Remote Similarity	NPD5311	Approved
0.6467	Remote Similarity	NPD5310	Approved
0.6455	Remote Similarity	NPD7608	Discontinued
0.6443	Remote Similarity	NPD5029	Approved
0.6443	Remote Similarity	NPD5031	Approved
0.6443	Remote Similarity	NPD5027	Approved
0.6432	Remote Similarity	NPD7283	Approved
0.6425	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD2098	Approved
0.6416	Remote Similarity	NPD8643	Discontinued
0.641	Remote Similarity	NPD5032	Approved
0.64	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6796	Discontinued
0.6389	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5038	Approved
0.6364	Remote Similarity	NPD5037	Approved
0.6358	Remote Similarity	NPD3061	Approved
0.6358	Remote Similarity	NPD3059	Approved
0.6358	Remote Similarity	NPD3062	Approved
0.6358	Remote Similarity	NPD6346	Approved
0.6331	Remote Similarity	NPD3053	Approved
0.6331	Remote Similarity	NPD3055	Approved
0.633	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5028	Approved
0.6327	Remote Similarity	NPD5026	Approved
0.6327	Remote Similarity	NPD4955	Approved
0.6327	Remote Similarity	NPD4954	Approved
0.6327	Remote Similarity	NPD5034	Approved
0.6327	Remote Similarity	NPD36	Approved
0.6326	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5968	Phase 3
0.6313	Remote Similarity	NPD5036	Approved
0.631	Remote Similarity	NPD2097	Approved
0.6303	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7565	Approved
0.6292	Remote Similarity	NPD6681	Discovery
0.6286	Remote Similarity	NPD2568	Approved
0.6286	Remote Similarity	NPD8173	Phase 2
0.6286	Remote Similarity	NPD8172	Phase 2
0.6284	Remote Similarity	NPD7131	Phase 3
0.6276	Remote Similarity	NPD5030	Phase 2
0.6272	Remote Similarity	NPD3125	Approved
0.6264	Remote Similarity	NPD6419	Discontinued
0.6263	Remote Similarity	NPD6557	Phase 2
0.6257	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2561	Approved
0.625	Remote Similarity	NPD3552	Approved
0.625	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3554	Approved
0.625	Remote Similarity	NPD3555	Approved
0.625	Remote Similarity	NPD3553	Approved
0.625	Remote Similarity	NPD2562	Approved
0.6243	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5035	Approved
0.6207	Remote Similarity	NPD7086	Phase 2
0.6205	Remote Similarity	NPD4603	Phase 2
0.6193	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5605	Phase 2
0.6183	Remote Similarity	NPD8417	Discontinued
0.6175	Remote Similarity	NPD2874	Phase 2
0.6173	Remote Similarity	NPD5190	Phase 2
0.6171	Remote Similarity	NPD8416	Discontinued
0.617	Remote Similarity	NPD7972	Discontinued
0.6169	Remote Similarity	NPD8025	Phase 2
0.6165	Remote Similarity	NPD5856	Discontinued
0.6154	Remote Similarity	NPD7554	Discontinued
0.615	Remote Similarity	NPD2469	Approved
0.615	Remote Similarity	NPD2468	Approved
0.615	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD4619	Approved
0.6149	Remote Similarity	NPD4621	Approved
0.6146	Remote Similarity	NPD2889	Approved
0.6146	Remote Similarity	NPD2890	Approved
0.6146	Remote Similarity	NPD2888	Approved
0.6146	Remote Similarity	NPD2017	Approved
0.6145	Remote Similarity	NPD5303	Approved
0.6145	Remote Similarity	NPD5304	Approved
0.614	Remote Similarity	NPD6188	Approved
0.614	Remote Similarity	NPD6189	Approved
0.6138	Remote Similarity	NPD5967	Approved
0.6135	Remote Similarity	NPD2228	Approved
0.6135	Remote Similarity	NPD2234	Approved
0.6135	Remote Similarity	NPD2229	Approved
0.6127	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD4466	Phase 1
0.6124	Remote Similarity	NPD6863	Phase 2
0.6122	Remote Similarity	NPD6042	Phase 2
0.6122	Remote Similarity	NPD42	Phase 2
0.6119	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6405	Approved
0.6114	Remote Similarity	NPD6407	Approved
0.6108	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD5033	Approved
0.61	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD3879	Approved
0.6093	Remote Similarity	NPD7827	Phase 1
0.6093	Remote Similarity	NPD6187	Approved
0.6089	Remote Similarity	NPD4173	Approved
0.6089	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD4172	Approved
0.6087	Remote Similarity	NPD3985	Discontinued
0.6087	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3536	Discontinued
0.6077	Remote Similarity	NPD2458	Approved
0.6077	Remote Similarity	NPD6254	Approved
0.6077	Remote Similarity	NPD2460	Phase 3
0.6077	Remote Similarity	NPD2209	Approved
0.6077	Remote Similarity	NPD6255	Approved
0.6077	Remote Similarity	NPD6256	Approved
0.6077	Remote Similarity	NPD2211	Approved
0.6077	Remote Similarity	NPD2459	Approved
0.6071	Remote Similarity	NPD3909	Discontinued
0.6064	Remote Similarity	NPD6072	Discontinued
0.6061	Remote Similarity	NPD5445	Approved
0.6061	Remote Similarity	NPD6297	Approved
0.6057	Remote Similarity	NPD598	Approved
0.6057	Remote Similarity	NPD601	Approved
0.6057	Remote Similarity	NPD597	Approved
0.6054	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4103	Phase 2
0.6047	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD3878	Approved
0.6044	Remote Similarity	NPD5481	Discontinued
0.6038	Remote Similarity	NPD6807	Phase 3
0.6034	Remote Similarity	NPD5263	Approved
0.6029	Remote Similarity	NPD6253	Approved
0.6028	Remote Similarity	NPD3592	Approved
0.6028	Remote Similarity	NPD3591	Approved
0.6027	Remote Similarity	NPD4086	Phase 1
0.6023	Remote Similarity	NPD1136	Approved
0.6023	Remote Similarity	NPD1130	Approved
0.6023	Remote Similarity	NPD1132	Approved
0.602	Remote Similarity	NPD6851	Approved
0.602	Remote Similarity	NPD6853	Approved
0.6011	Remote Similarity	NPD823	Approved
0.6011	Remote Similarity	NPD817	Approved
0.601	Remote Similarity	NPD5557	Phase 1
0.601	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4762	Approved
0.6	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3175	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