NPASS Compound

Structure

NPC329731 OpenBabel07101718222D 58 61 0 0 1 0 0 0 0 0999 V2000 -0.1767 -4.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 3.3274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2815 -5.8847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3641 4.3891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8041 0.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3887 -5.3592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6451 1.2253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0405 0.4288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7783 2.3428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5312 -4.8505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9092 -5.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7316 -0.0775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7301 -5.1146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9247 -3.1294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7786 -2.1401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3239 3.0617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2813 3.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1335 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9995 -3.0775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9995 -1.0775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8656 -2.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0290 -3.5740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7689 1.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4820 1.2655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2675 -3.0775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0226 1.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4686 2.5437 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7281 -5.0518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2804 3.3926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8305 0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0996 -4.4019 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1335 -2.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9112 2.0866 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.8656 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4015 -2.5775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2074 -1.9734 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2689 0.9632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1728 -4.1561 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9351 -0.6663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2585 3.1847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1136 -4.5686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7969 -3.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3398 -3.6027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0209 -0.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6529 1.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1542 2.7400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.7890 -1.6556 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0132 -3.9951 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1171 -4.4850 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6707 -2.8596 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.9348 -0.6873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1555 -5.5678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5113 -4.0737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6864 -4.3597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0155 -1.1043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7316 -1.0775 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 -5.1962 2.1945 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 7 45 1 0 0 0 0 8 45 1 0 0 0 0 9 45 1 0 0 0 0 10 48 1 0 0 0 0 11 49 1 0 0 0 0 12 56 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 29 2 0 0 0 0 18 20 1 0 0 0 0 18 32 2 0 0 0 0 19 21 2 0 0 0 0 19 32 1 0 0 0 0 20 34 2 0 0 0 0 21 34 1 0 0 0 0 22 50 1 0 0 0 0 23 27 1 0 0 0 0 23 37 1 0 0 0 0 24 30 2 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 26 58 1 0 0 0 0 27 2 1 6 0 0 0 28 3 1 6 0 0 0 29 40 1 0 0 0 0 30 39 1 0 0 0 0 31 6 1 6 0 0 0 31 41 1 0 0 0 0 31 48 1 0 0 0 0 33 24 1 6 0 0 0 33 46 1 0 0 0 0 34 56 1 0 0 0 0 35 25 1 6 0 0 0 35 42 1 0 0 0 0 35 47 1 0 0 0 0 36 15 1 6 0 0 0 36 44 1 0 0 0 0 36 50 1 0 0 0 0 37 45 1 1 0 0 0 37 57 1 0 0 0 0 38 28 1 6 0 0 0 38 43 1 0 0 0 0 38 49 1 0 0 0 0 39 47 2 3 0 0 0 39 51 1 0 0 0 0 40 46 2 0 0 0 0 40 58 1 0 0 0 0 41 49 1 0 0 0 0 41 52 2 0 0 0 0 42 48 1 0 0 0 0 42 53 2 0 0 0 0 43 50 1 0 0 0 0 43 54 2 0 0 0 0 44 55 2 0 0 0 0 44 57 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	821.48
Volume:	858.673
LogP:	5.823
LogD:	4.688
LogS:	-6.084
# Rotatable Bonds:	6
TPSA:	138.25
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	6.709
Fsp3:	0.667
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:	-5.016
MDCK Permeability:	2.056932498817332e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.706

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	94.45537567138672%
Volume Distribution (VD):	0.762
Pgp-substrate:	7.753857135772705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.621
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.333
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.517
CYP3A4-inhibitor:	0.98
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	8.383
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.105
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.549

Download Data

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

Natural Product: NPC329731

Natural Product ID:	NPC329731
*Common Name:**	E-Dehydroapratoxin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RDTKVQUPKFRZEV-SNTCAYBKSA-N
Standard InCHI:	InChI=1S/C45H67N5O7S/c1-13-28(3)38-43(54)50-22-14-15-36(50)44(55)57-37(45(7,8)9)23-27(2)16-17-29(4)40-46-33(26-58-40)24-30(5)39(51)47-35(25-32-18-20-34(56-12)21-19-32)42(53)48(10)31(6)41(52)49(38)11/h17-21,24,27-28,31,33,35-38H,13-16,22-23,25-26H2,1-12H3,(H,47,51)/b29-17+,30-24+/t27-,28-,31-,33-,35-,36-,37-,38-/m0/s1
SMILES:	CCC(C)C1C(=O)N2CCCC2C(=O)OC(CC(CC=C(C3=NC(CS3)C=C(C(=O)NC(C(=O)N(C(C(=O)N1C)C)C)CC4=CC=C(C=C4)OC)C)C)C)C(C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525420
PubChem CID:	44585957
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO30186	Lyngbya bouillonii	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18461997]
NPO30186	Lyngbya bouillonii	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[20131814]
NPO30186	Lyngbya bouillonii	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20704304]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	41.0	nM	PMID[527162]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	121.0	nM	PMID[527162]
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	160.0	nM	PMID[527162]

☑ 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 NPC329731 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	203
0.1-0.2	1135
0.2-0.3	5009
0.3-0.4	12395
0.4-0.5	14828
0.5-0.6	7968
0.6-0.7	951
0.7-0.8	198
0.8-0.85	4
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC4910
0.9651	High Similarity	NPC59827
0.9651	High Similarity	NPC184933
0.9486	High Similarity	NPC477527
0.9143	High Similarity	NPC477526
0.8421	Intermediate Similarity	NPC472923
0.8056	Intermediate Similarity	NPC475421
0.8022	Intermediate Similarity	NPC167763
0.8022	Intermediate Similarity	NPC470903
0.8022	Intermediate Similarity	NPC470112
0.8011	Intermediate Similarity	NPC473502
0.7929	Intermediate Similarity	NPC283783
0.7889	Intermediate Similarity	NPC26108
0.7865	Intermediate Similarity	NPC186617
0.7853	Intermediate Similarity	NPC254700
0.7838	Intermediate Similarity	NPC299806
0.7833	Intermediate Similarity	NPC137627
0.7821	Intermediate Similarity	NPC196091
0.7821	Intermediate Similarity	NPC471568
0.7821	Intermediate Similarity	NPC473693
0.7742	Intermediate Similarity	NPC315542
0.7722	Intermediate Similarity	NPC475204
0.7722	Intermediate Similarity	NPC475123
0.7688	Intermediate Similarity	NPC262166
0.7674	Intermediate Similarity	NPC324081
0.767	Intermediate Similarity	NPC319320
0.767	Intermediate Similarity	NPC287757
0.7602	Intermediate Similarity	NPC16188
0.7596	Intermediate Similarity	NPC279871
0.7544	Intermediate Similarity	NPC81026
0.7541	Intermediate Similarity	NPC306804
0.7539	Intermediate Similarity	NPC473378
0.7539	Intermediate Similarity	NPC473407
0.7514	Intermediate Similarity	NPC107938
0.7514	Intermediate Similarity	NPC294516
0.75	Intermediate Similarity	NPC155506
0.75	Intermediate Similarity	NPC159767
0.75	Intermediate Similarity	NPC326407
0.75	Intermediate Similarity	NPC317725
0.75	Intermediate Similarity	NPC317362
0.75	Intermediate Similarity	NPC318930
0.75	Intermediate Similarity	NPC63931
0.75	Intermediate Similarity	NPC476227
0.7486	Intermediate Similarity	NPC261934
0.7486	Intermediate Similarity	NPC202198
0.7486	Intermediate Similarity	NPC5194
0.7485	Intermediate Similarity	NPC266741
0.7473	Intermediate Similarity	NPC269750
0.7473	Intermediate Similarity	NPC194671
0.7457	Intermediate Similarity	NPC189908
0.7443	Intermediate Similarity	NPC39431
0.7433	Intermediate Similarity	NPC153554
0.7432	Intermediate Similarity	NPC40234
0.7432	Intermediate Similarity	NPC46009
0.7429	Intermediate Similarity	NPC233702
0.7407	Intermediate Similarity	NPC471048
0.7407	Intermediate Similarity	NPC471050
0.7407	Intermediate Similarity	NPC471049
0.7405	Intermediate Similarity	NPC471165
0.7399	Intermediate Similarity	NPC83790
0.7399	Intermediate Similarity	NPC128237
0.7391	Intermediate Similarity	NPC89831
0.7391	Intermediate Similarity	NPC230611
0.7384	Intermediate Similarity	NPC5620
0.7376	Intermediate Similarity	NPC14877
0.7376	Intermediate Similarity	NPC145178
0.7376	Intermediate Similarity	NPC475350
0.7368	Intermediate Similarity	NPC161069
0.7358	Intermediate Similarity	NPC248822
0.7351	Intermediate Similarity	NPC273755
0.7322	Intermediate Similarity	NPC302597
0.7318	Intermediate Similarity	NPC326349
0.7318	Intermediate Similarity	NPC323336
0.7316	Intermediate Similarity	NPC294951
0.7313	Intermediate Similarity	NPC246303
0.7312	Intermediate Similarity	NPC164608
0.7312	Intermediate Similarity	NPC473402
0.7312	Intermediate Similarity	NPC473354
0.731	Intermediate Similarity	NPC476989
0.7306	Intermediate Similarity	NPC64140
0.7306	Intermediate Similarity	NPC174122
0.7294	Intermediate Similarity	NPC89489
0.7288	Intermediate Similarity	NPC56685
0.7283	Intermediate Similarity	NPC313867
0.7283	Intermediate Similarity	NPC316008
0.7273	Intermediate Similarity	NPC473491
0.7273	Intermediate Similarity	NPC50016
0.7268	Intermediate Similarity	NPC251036
0.7257	Intermediate Similarity	NPC9373
0.7254	Intermediate Similarity	NPC234069
0.7249	Intermediate Similarity	NPC32064
0.7241	Intermediate Similarity	NPC314358
0.7231	Intermediate Similarity	NPC204970
0.7228	Intermediate Similarity	NPC141957
0.7225	Intermediate Similarity	NPC314388
0.7225	Intermediate Similarity	NPC476978
0.7225	Intermediate Similarity	NPC315283
0.7216	Intermediate Similarity	NPC473305
0.7216	Intermediate Similarity	NPC163961
0.7216	Intermediate Similarity	NPC129666
0.7211	Intermediate Similarity	NPC477637
0.7211	Intermediate Similarity	NPC476321
0.7209	Intermediate Similarity	NPC269398
0.7209	Intermediate Similarity	NPC263493
0.72	Intermediate Similarity	NPC138775
0.7198	Intermediate Similarity	NPC241794
0.7196	Intermediate Similarity	NPC45037
0.7193	Intermediate Similarity	NPC242159
0.7193	Intermediate Similarity	NPC313694
0.7189	Intermediate Similarity	NPC129486
0.7173	Intermediate Similarity	NPC471526
0.716	Intermediate Similarity	NPC470392
0.7159	Intermediate Similarity	NPC105717
0.7157	Intermediate Similarity	NPC478005
0.715	Intermediate Similarity	NPC276120
0.7128	Intermediate Similarity	NPC136797
0.7127	Intermediate Similarity	NPC56635
0.712	Intermediate Similarity	NPC473404
0.7119	Intermediate Similarity	NPC132771
0.7113	Intermediate Similarity	NPC94862
0.7111	Intermediate Similarity	NPC473580
0.7111	Intermediate Similarity	NPC244509
0.7111	Intermediate Similarity	NPC476268
0.7102	Intermediate Similarity	NPC329761
0.7102	Intermediate Similarity	NPC225648
0.7102	Intermediate Similarity	NPC145113
0.7098	Intermediate Similarity	NPC138083
0.7097	Intermediate Similarity	NPC315388
0.7094	Intermediate Similarity	NPC257511
0.7093	Intermediate Similarity	NPC178662
0.7093	Intermediate Similarity	NPC98424
0.7093	Intermediate Similarity	NPC92784
0.7093	Intermediate Similarity	NPC476133
0.7093	Intermediate Similarity	NPC470884
0.7086	Intermediate Similarity	NPC209509
0.7086	Intermediate Similarity	NPC322878
0.7086	Intermediate Similarity	NPC471680
0.7081	Intermediate Similarity	NPC61004
0.7074	Intermediate Similarity	NPC248670
0.7074	Intermediate Similarity	NPC475532
0.7071	Intermediate Similarity	NPC477632
0.7071	Intermediate Similarity	NPC477638
0.7065	Intermediate Similarity	NPC473450
0.7059	Intermediate Similarity	NPC274198
0.7059	Intermediate Similarity	NPC198254
0.705	Intermediate Similarity	NPC477552
0.705	Intermediate Similarity	NPC477550
0.7049	Intermediate Similarity	NPC469243
0.7045	Intermediate Similarity	NPC262077
0.7041	Intermediate Similarity	NPC174629
0.7041	Intermediate Similarity	NPC61332
0.7041	Intermediate Similarity	NPC240130
0.7037	Intermediate Similarity	NPC165285
0.7035	Intermediate Similarity	NPC471265
0.7035	Intermediate Similarity	NPC471264
0.7024	Intermediate Similarity	NPC296712
0.7022	Intermediate Similarity	NPC2501
0.7021	Intermediate Similarity	NPC328494
0.702	Intermediate Similarity	NPC328763
0.702	Intermediate Similarity	NPC302715
0.7018	Intermediate Similarity	NPC169766
0.7006	Intermediate Similarity	NPC135121
0.7005	Intermediate Similarity	NPC469505
0.7005	Intermediate Similarity	NPC280022
0.7	Intermediate Similarity	NPC286551
0.7	Intermediate Similarity	NPC144314
0.6995	Remote Similarity	NPC244336
0.699	Remote Similarity	NPC102959
0.6982	Remote Similarity	NPC300315
0.698	Remote Similarity	NPC477551
0.6971	Remote Similarity	NPC91953
0.697	Remote Similarity	NPC477631
0.6968	Remote Similarity	NPC276506
0.6966	Remote Similarity	NPC240848
0.6965	Remote Similarity	NPC50548
0.6961	Remote Similarity	NPC75498
0.6957	Remote Similarity	NPC475544
0.6954	Remote Similarity	NPC60516
0.6954	Remote Similarity	NPC29531
0.6954	Remote Similarity	NPC477636
0.6952	Remote Similarity	NPC328649
0.695	Remote Similarity	NPC149962
0.695	Remote Similarity	NPC477639
0.6948	Remote Similarity	NPC478007
0.6947	Remote Similarity	NPC158277
0.6947	Remote Similarity	NPC17698
0.6944	Remote Similarity	NPC162104
0.6944	Remote Similarity	NPC214239
0.6941	Remote Similarity	NPC475196
0.694	Remote Similarity	NPC212699
0.694	Remote Similarity	NPC207675
0.6936	Remote Similarity	NPC6570
0.6935	Remote Similarity	NPC223207
0.6932	Remote Similarity	NPC52748
0.6923	Remote Similarity	NPC256689
0.6923	Remote Similarity	NPC123011
0.6914	Remote Similarity	NPC197921
0.6911	Remote Similarity	NPC196243
0.6906	Remote Similarity	NPC122590
0.6901	Remote Similarity	NPC246079

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 NPC329731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	473
0.2-0.3	865
0.3-0.4	1983
0.4-0.5	3070
0.5-0.6	2158
0.6-0.7	433
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8047	Intermediate Similarity	NPD6390	Discontinued
0.7791	Intermediate Similarity	NPD7131	Phase 3
0.776	Intermediate Similarity	NPD5485	Approved
0.776	Intermediate Similarity	NPD5484	Approved
0.7632	Intermediate Similarity	NPD6504	Approved
0.7632	Intermediate Similarity	NPD6505	Approved
0.7624	Intermediate Similarity	NPD2517	Approved
0.7619	Intermediate Similarity	NPD4435	Approved
0.7614	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD2098	Approved
0.7584	Intermediate Similarity	NPD2097	Approved
0.7569	Intermediate Similarity	NPD2516	Approved
0.7566	Intermediate Similarity	NPD4434	Approved
0.7527	Intermediate Similarity	NPD4652	Approved
0.7514	Intermediate Similarity	NPD2513	Approved
0.7514	Intermediate Similarity	NPD7133	Discontinued
0.7474	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD2515	Approved
0.7472	Intermediate Similarity	NPD3007	Approved
0.7401	Intermediate Similarity	NPD2052	Approved
0.7363	Intermediate Similarity	NPD8303	Discontinued
0.736	Intermediate Similarity	NPD2053	Approved
0.736	Intermediate Similarity	NPD22	Approved
0.7283	Intermediate Similarity	NPD7484	Phase 3
0.7283	Intermediate Similarity	NPD7485	Phase 3
0.7186	Intermediate Similarity	NPD4125	Approved
0.716	Intermediate Similarity	NPD5745	Approved
0.7151	Intermediate Similarity	NPD7608	Discontinued
0.7135	Intermediate Similarity	NPD7280	Phase 3
0.7135	Intermediate Similarity	NPD7281	Phase 3
0.71	Intermediate Similarity	NPD7810	Phase 3
0.71	Intermediate Similarity	NPD7811	Phase 3
0.7097	Intermediate Similarity	NPD2017	Approved
0.7097	Intermediate Similarity	NPD2890	Approved
0.7097	Intermediate Similarity	NPD2889	Approved
0.7097	Intermediate Similarity	NPD2888	Approved
0.7088	Intermediate Similarity	NPD5355	Approved
0.7088	Intermediate Similarity	NPD5356	Approved
0.7086	Intermediate Similarity	NPD5264	Approved
0.7086	Intermediate Similarity	NPD5265	Approved
0.7049	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5746	Approved
0.7039	Intermediate Similarity	NPD7303	Discontinued
0.7011	Intermediate Similarity	NPD5967	Approved
0.701	Intermediate Similarity	NPD6853	Approved
0.701	Intermediate Similarity	NPD6851	Approved
0.7005	Intermediate Similarity	NPD5994	Discontinued
0.7	Intermediate Similarity	NPD1670	Discontinued
0.6995	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4557	Approved
0.6954	Remote Similarity	NPD5113	Approved
0.6954	Remote Similarity	NPD5114	Approved
0.6954	Remote Similarity	NPD5112	Approved
0.6936	Remote Similarity	NPD8173	Phase 2
0.6936	Remote Similarity	NPD8172	Phase 2
0.6927	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3988	Approved
0.6927	Remote Similarity	NPD3987	Approved
0.6905	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5852	Approved
0.6904	Remote Similarity	NPD5851	Approved
0.6875	Remote Similarity	NPD2022	Approved
0.6868	Remote Similarity	NPD4648	Approved
0.6868	Remote Similarity	NPD4647	Approved
0.6868	Remote Similarity	NPD4646	Approved
0.686	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5230	Approved
0.6851	Remote Similarity	NPD5229	Approved
0.6839	Remote Similarity	NPD5557	Phase 1
0.6836	Remote Similarity	NPD2437	Approved
0.6836	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD2436	Approved
0.6836	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3878	Approved
0.6804	Remote Similarity	NPD6297	Approved
0.68	Remote Similarity	NPD4126	Approved
0.6798	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4739	Approved
0.6793	Remote Similarity	NPD2891	Approved
0.6782	Remote Similarity	NPD3659	Discontinued
0.678	Remote Similarity	NPD2088	Approved
0.678	Remote Similarity	NPD2087	Approved
0.6777	Remote Similarity	NPD3879	Approved
0.6761	Remote Similarity	NPD3480	Approved
0.6758	Remote Similarity	NPD7613	Discontinued
0.6758	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD8031	Discontinued
0.6751	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2046	Approved
0.6744	Remote Similarity	NPD2048	Approved
0.6744	Remote Similarity	NPD21	Approved
0.6744	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2044	Approved
0.6744	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2043	Approved
0.6744	Remote Similarity	NPD2045	Approved
0.6744	Remote Similarity	NPD2051	Approved
0.6744	Remote Similarity	NPD2047	Approved
0.6739	Remote Similarity	NPD3111	Phase 1
0.6738	Remote Similarity	NPD8255	Phase 2
0.6736	Remote Similarity	NPD3909	Discontinued
0.6731	Remote Similarity	NPD8161	Suspended
0.6726	Remote Similarity	NPD2584	Suspended
0.6724	Remote Similarity	NPD5323	Approved
0.6715	Remote Similarity	NPD3802	Phase 3
0.6705	Remote Similarity	NPD1330	Phase 2
0.6705	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7315	Approved
0.67	Remote Similarity	NPD7861	Discontinued
0.6685	Remote Similarity	NPD4210	Discontinued
0.6684	Remote Similarity	NPD5772	Approved
0.6684	Remote Similarity	NPD7972	Discontinued
0.6684	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5773	Approved
0.6683	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5481	Discontinued
0.6667	Remote Similarity	NPD5077	Approved
0.6667	Remote Similarity	NPD5076	Approved
0.6667	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6253	Approved
0.6649	Remote Similarity	NPD7318	Phase 3
0.6649	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5725	Approved
0.6648	Remote Similarity	NPD5614	Approved
0.6648	Remote Similarity	NPD5613	Approved
0.6634	Remote Similarity	NPD3479	Discontinued
0.6632	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8124	Phase 3
0.6631	Remote Similarity	NPD7495	Discontinued
0.6629	Remote Similarity	NPD2240	Approved
0.6629	Remote Similarity	NPD2239	Approved
0.6628	Remote Similarity	NPD4175	Approved
0.6628	Remote Similarity	NPD4177	Approved
0.6618	Remote Similarity	NPD6256	Approved
0.6618	Remote Similarity	NPD6255	Approved
0.6618	Remote Similarity	NPD6254	Approved
0.6617	Remote Similarity	NPD1986	Approved
0.6615	Remote Similarity	NPD5313	Approved
0.6615	Remote Similarity	NPD5312	Approved
0.6613	Remote Similarity	NPD6502	Phase 2
0.6612	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5299	Approved
0.6602	Remote Similarity	NPD7565	Approved
0.6601	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6667	Approved
0.6593	Remote Similarity	NPD6666	Approved
0.6591	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6863	Phase 2
0.6584	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4483	Discontinued
0.6578	Remote Similarity	NPD6677	Suspended
0.6571	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6681	Discovery
0.6554	Remote Similarity	NPD6073	Approved
0.6552	Remote Similarity	NPD3136	Phase 2
0.655	Remote Similarity	NPD3125	Approved
0.6545	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8019	Approved
0.6543	Remote Similarity	NPD7317	Phase 3
0.6538	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3692	Discontinued
0.6538	Remote Similarity	NPD6238	Discontinued
0.6537	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1725	Approved
0.6534	Remote Similarity	NPD8416	Discontinued
0.6524	Remote Similarity	NPD5055	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2874	Phase 2
0.6522	Remote Similarity	NPD7020	Approved
0.6522	Remote Similarity	NPD7019	Approved
0.652	Remote Similarity	NPD3958	Approved
0.6517	Remote Similarity	NPD1987	Approved
0.6517	Remote Similarity	NPD1985	Approved
0.651	Remote Similarity	NPD4508	Discontinued
0.6505	Remote Similarity	NPD5564	Approved
0.6497	Remote Similarity	NPD6598	Approved
0.6497	Remote Similarity	NPD6597	Approved
0.6493	Remote Similarity	NPD6551	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6971	Discontinued
0.6491	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.648	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD2245	Discovery
0.6477	Remote Similarity	NPD6303	Approved
0.6477	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6304	Approved
0.6477	Remote Similarity	NPD7634	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