NPASS Compound

Structure

NPC33064 OpenBabel07101718292D 48 51 0 0 1 0 0 0 0 0999 V2000 6.1545 -2.0662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3717 -4.5687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2350 0.3895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2169 -6.0628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6740 1.8358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6973 0.7168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6053 0.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2325 -0.2380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6172 0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8715 -1.1706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2446 -3.6963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1106 -4.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0175 -3.0842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9631 -1.1123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8492 -4.6738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3786 -5.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4845 -0.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1232 -4.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1548 -2.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5660 -3.9765 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4631 -0.2462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9448 -5.1006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7840 0.8419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3786 -4.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 -0.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3217 -0.9012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2446 -5.6963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8834 -1.3243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5126 -3.6963 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5922 -0.8058 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1106 -5.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9751 -4.9919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3712 -1.8999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7090 0.4105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8908 -1.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8218 0.5698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2446 -6.6963 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.5924 -2.5271 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.7825 0.7868 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3364 -2.1614 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8632 -2.7598 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 -3.9767 -5.6963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5988 -5.9184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2327 1.2624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8813 -1.6228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3950 1.4742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9509 -5.2106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 6 42 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 25 2 0 0 0 0 10 28 2 0 0 0 0 11 12 2 0 0 0 0 11 24 1 0 0 0 0 12 31 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 0 0 0 0 18 32 1 0 0 0 0 20 2 1 6 0 0 0 21 3 1 1 0 0 0 21 34 1 0 0 0 0 22 4 1 6 0 0 0 22 48 1 0 0 0 0 23 5 1 6 0 0 0 23 36 1 0 0 0 0 23 39 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 26 33 2 0 0 0 0 27 31 2 0 0 0 0 27 37 1 0 0 0 0 28 40 1 0 0 0 0 29 24 1 6 0 0 0 29 41 1 0 0 0 0 30 17 1 1 0 0 0 30 35 1 0 0 0 0 30 42 1 0 0 0 0 31 43 1 0 0 0 0 32 44 2 0 0 0 0 32 48 1 0 0 0 0 33 38 1 0 0 0 0 33 40 1 0 0 0 0 34 39 2 3 0 0 0 34 45 1 0 0 0 0 35 41 2 3 0 0 0 35 46 1 0 0 0 0 36 42 1 0 0 0 0 36 47 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	786.16
Volume:	700.644
LogP:	6.15
LogD:	4.704
LogS:	-4.7
# Rotatable Bonds:	3
TPSA:	140.83
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	5.322
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.835
MDCK Permeability:	1.2612660611921456e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.194
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.778

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	99.10918426513672%
Volume Distribution (VD):	0.404
Pgp-substrate:	1.8017059564590454%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.915
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.93
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.322
CYP2D6-substrate:	0.345
CYP3A4-inhibitor:	0.975
CYP3A4-substrate:	0.574

ADMET: Excretion

Clearance (CL):	1.729
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.847
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.149
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.172

Download Data

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

Natural Product: NPC33064

Natural Product ID:	NPC33064
*Common Name:**	Pipestelide A
IUPAC Name:	(4R,7R,10S,13S,15E,17R,19S)-4-(3-bromo-4-hydroxyphenyl)-7-[(2-bromo-1H-indol-3-yl)methyl]-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone
Synonyms:	Pipestelide A
Standard InCHIKey:	LAIMZLKDQQEQSN-XHAFUQONSA-N
Standard InCHI:	InChI=1S/C36H44Br2N4O6/c1-19-13-20(2)15-22(4)48-32(44)18-29(24-11-12-31(43)27(37)16-24)41-35(46)30(17-26-25-9-7-8-10-28(25)40-33(26)38)42(6)36(47)23(5)39-34(45)21(3)14-19/h7-13,16,20-23,29-30,40,43H,14-15,17-18H2,1-6H3,(H,39,45)(H,41,46)/b19-13+/t20-,21-,22-,23-,29+,30+/m0/s1
SMILES:	C[C@@H]1OC(=O)C[C@@H](N=C(O)[C@@H](Cc2c(Br)[nH]c3c2cccc3)N(C)C(=O)[C@@H](N=C([C@H](C/C(=C/[C@@H](C1)C)/C)C)O)C)c1ccc(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2041198
PubChem CID:	57409351
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2007.03.162]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2008.05.037]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2008.10.076]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075778]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	Fiji (S 1822.28', E 17758.87')	2000-FEB	PMID[21241058]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21241058]
NPO33106	pipestela candelabra	Species	n.a.	n.a.	n.a.	Pacific	n.a.	PMID[22364566]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26883470]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	100.0	%	PMID[496150]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	100.0	nM	PMID[496150]

☑ 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 NPC33064 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	334
0.1-0.2	2028
0.2-0.3	12840
0.3-0.4	11782
0.4-0.5	9872
0.5-0.6	3613
0.6-0.7	1906
0.7-0.8	296
0.8-0.85	2
0.85-0.9	6
0.9-0.95	3
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.971	High Similarity	NPC34580
0.971	High Similarity	NPC124920
0.971	High Similarity	NPC304307
0.971	High Similarity	NPC118559
0.9663	High Similarity	NPC100547
0.9621	High Similarity	NPC245055
0.9617	High Similarity	NPC95240
0.9617	High Similarity	NPC322135
0.9617	High Similarity	NPC223409
0.9615	High Similarity	NPC261251
0.9571	High Similarity	NPC14288
0.9567	High Similarity	NPC214142
0.9526	High Similarity	NPC54803
0.9526	High Similarity	NPC321592
0.9481	High Similarity	NPC284888
0.9306	High Similarity	NPC82472
0.9227	High Similarity	NPC74969
0.893	High Similarity	NPC24370
0.893	High Similarity	NPC319232
0.8778	High Similarity	NPC272549
0.8688	High Similarity	NPC323198
0.8688	High Similarity	NPC323752
0.8646	High Similarity	NPC181081
0.8077	Intermediate Similarity	NPC243716
0.7982	Intermediate Similarity	NPC326363
0.7875	Intermediate Similarity	NPC314882
0.7857	Intermediate Similarity	NPC303658
0.785	Intermediate Similarity	NPC306376
0.7848	Intermediate Similarity	NPC330009
0.7845	Intermediate Similarity	NPC325976
0.7807	Intermediate Similarity	NPC125597
0.7753	Intermediate Similarity	NPC473317
0.7752	Intermediate Similarity	NPC476098
0.7738	Intermediate Similarity	NPC478158
0.7725	Intermediate Similarity	NPC220852
0.7723	Intermediate Similarity	NPC478157
0.7719	Intermediate Similarity	NPC470501
0.7702	Intermediate Similarity	NPC28945
0.7702	Intermediate Similarity	NPC315467
0.7689	Intermediate Similarity	NPC469928
0.7675	Intermediate Similarity	NPC470502
0.7673	Intermediate Similarity	NPC478006
0.7629	Intermediate Similarity	NPC194740
0.7627	Intermediate Similarity	NPC285343
0.7611	Intermediate Similarity	NPC67658
0.7609	Intermediate Similarity	NPC470503
0.76	Intermediate Similarity	NPC478009
0.7595	Intermediate Similarity	NPC470784
0.7556	Intermediate Similarity	NPC207020
0.7554	Intermediate Similarity	NPC33949
0.7553	Intermediate Similarity	NPC184680
0.7546	Intermediate Similarity	NPC276517
0.7544	Intermediate Similarity	NPC281049
0.7541	Intermediate Similarity	NPC153400
0.7532	Intermediate Similarity	NPC200553
0.7521	Intermediate Similarity	NPC470785
0.752	Intermediate Similarity	NPC314056
0.7511	Intermediate Similarity	NPC162002
0.75	Intermediate Similarity	NPC305984
0.7468	Intermediate Similarity	NPC174489
0.746	Intermediate Similarity	NPC216369
0.746	Intermediate Similarity	NPC478010
0.7451	Intermediate Similarity	NPC321939
0.7451	Intermediate Similarity	NPC478011
0.7431	Intermediate Similarity	NPC478013
0.7425	Intermediate Similarity	NPC21638
0.7422	Intermediate Similarity	NPC314176
0.7417	Intermediate Similarity	NPC475816
0.7411	Intermediate Similarity	NPC270918
0.7406	Intermediate Similarity	NPC26641
0.7406	Intermediate Similarity	NPC184225
0.7401	Intermediate Similarity	NPC75634
0.7397	Intermediate Similarity	NPC262898
0.7391	Intermediate Similarity	NPC473041
0.7387	Intermediate Similarity	NPC476874
0.7384	Intermediate Similarity	NPC279189
0.738	Intermediate Similarity	NPC322064
0.738	Intermediate Similarity	NPC152768
0.738	Intermediate Similarity	NPC148183
0.7378	Intermediate Similarity	NPC39679
0.7376	Intermediate Similarity	NPC315491
0.7376	Intermediate Similarity	NPC249040
0.7376	Intermediate Similarity	NPC45459
0.7368	Intermediate Similarity	NPC54744
0.7359	Intermediate Similarity	NPC313804
0.7359	Intermediate Similarity	NPC315804
0.7353	Intermediate Similarity	NPC473105
0.7352	Intermediate Similarity	NPC179701
0.7345	Intermediate Similarity	NPC162860
0.7344	Intermediate Similarity	NPC37152
0.7339	Intermediate Similarity	NPC243633
0.7339	Intermediate Similarity	NPC220851
0.7339	Intermediate Similarity	NPC175150
0.7336	Intermediate Similarity	NPC50562
0.7322	Intermediate Similarity	NPC97902
0.7315	Intermediate Similarity	NPC478012
0.7311	Intermediate Similarity	NPC474192
0.7311	Intermediate Similarity	NPC475720
0.7295	Intermediate Similarity	NPC470504
0.7293	Intermediate Similarity	NPC471080
0.7293	Intermediate Similarity	NPC469592
0.7265	Intermediate Similarity	NPC471944
0.7265	Intermediate Similarity	NPC475506
0.7264	Intermediate Similarity	NPC72980
0.7257	Intermediate Similarity	NPC88008
0.7257	Intermediate Similarity	NPC54420
0.7257	Intermediate Similarity	NPC311906
0.7252	Intermediate Similarity	NPC293917
0.7247	Intermediate Similarity	NPC477635
0.7247	Intermediate Similarity	NPC477630
0.7241	Intermediate Similarity	NPC96321
0.7241	Intermediate Similarity	NPC469594
0.7238	Intermediate Similarity	NPC89987
0.7234	Intermediate Similarity	NPC64216
0.7232	Intermediate Similarity	NPC155143
0.7232	Intermediate Similarity	NPC193761
0.7229	Intermediate Similarity	NPC183407
0.7222	Intermediate Similarity	NPC60621
0.7222	Intermediate Similarity	NPC94752
0.722	Intermediate Similarity	NPC79129
0.722	Intermediate Similarity	NPC313985
0.722	Intermediate Similarity	NPC49196
0.722	Intermediate Similarity	NPC81654
0.722	Intermediate Similarity	NPC249150
0.722	Intermediate Similarity	NPC195461
0.722	Intermediate Similarity	NPC477549
0.7217	Intermediate Similarity	NPC477610
0.7215	Intermediate Similarity	NPC186351
0.7212	Intermediate Similarity	NPC277350
0.7211	Intermediate Similarity	NPC475746
0.7205	Intermediate Similarity	NPC87413
0.7205	Intermediate Similarity	NPC23294
0.72	Intermediate Similarity	NPC165599
0.7198	Intermediate Similarity	NPC312645
0.7191	Intermediate Similarity	NPC478141
0.7186	Intermediate Similarity	NPC477979
0.7185	Intermediate Similarity	NPC471762
0.7183	Intermediate Similarity	NPC219336
0.7181	Intermediate Similarity	NPC53344
0.7176	Intermediate Similarity	NPC242872
0.7176	Intermediate Similarity	NPC94943
0.7176	Intermediate Similarity	NPC125181
0.7176	Intermediate Similarity	NPC263117
0.7168	Intermediate Similarity	NPC470500
0.7168	Intermediate Similarity	NPC473376
0.7168	Intermediate Similarity	NPC470505
0.7167	Intermediate Similarity	NPC264285
0.7167	Intermediate Similarity	NPC63031
0.7162	Intermediate Similarity	NPC471304
0.7162	Intermediate Similarity	NPC156704
0.7162	Intermediate Similarity	NPC303951
0.7162	Intermediate Similarity	NPC5145
0.7161	Intermediate Similarity	NPC51388
0.716	Intermediate Similarity	NPC474183
0.7156	Intermediate Similarity	NPC175474
0.7156	Intermediate Similarity	NPC213629
0.7155	Intermediate Similarity	NPC3207
0.715	Intermediate Similarity	NPC469896
0.715	Intermediate Similarity	NPC91179
0.7143	Intermediate Similarity	NPC213308
0.7137	Intermediate Similarity	NPC255110
0.7136	Intermediate Similarity	NPC99666
0.7136	Intermediate Similarity	NPC15573
0.7136	Intermediate Similarity	NPC183662
0.7136	Intermediate Similarity	NPC217372
0.7136	Intermediate Similarity	NPC55493
0.713	Intermediate Similarity	NPC190007
0.713	Intermediate Similarity	NPC52557
0.713	Intermediate Similarity	NPC50503
0.713	Intermediate Similarity	NPC473640
0.7126	Intermediate Similarity	NPC469734
0.7125	Intermediate Similarity	NPC474701
0.7119	Intermediate Similarity	NPC15801
0.7118	Intermediate Similarity	NPC107077
0.7118	Intermediate Similarity	NPC476116
0.7118	Intermediate Similarity	NPC223791
0.7112	Intermediate Similarity	NPC118228
0.7106	Intermediate Similarity	NPC472099
0.7105	Intermediate Similarity	NPC244741
0.7101	Intermediate Similarity	NPC60006
0.7098	Intermediate Similarity	NPC241024
0.7093	Intermediate Similarity	NPC117980
0.7091	Intermediate Similarity	NPC117244
0.7091	Intermediate Similarity	NPC473763
0.7085	Intermediate Similarity	NPC81939
0.7085	Intermediate Similarity	NPC70956
0.7085	Intermediate Similarity	NPC243834
0.7083	Intermediate Similarity	NPC212535
0.7078	Intermediate Similarity	NPC196251
0.7078	Intermediate Similarity	NPC63199
0.7078	Intermediate Similarity	NPC111602
0.7078	Intermediate Similarity	NPC102338
0.7076	Intermediate Similarity	NPC474896
0.7074	Intermediate Similarity	NPC86834
0.7074	Intermediate Similarity	NPC475910
0.7074	Intermediate Similarity	NPC210828
0.7069	Intermediate Similarity	NPC74562
0.7069	Intermediate Similarity	NPC316181
0.7069	Intermediate Similarity	NPC151781
0.7069	Intermediate Similarity	NPC89508

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 NPC33064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	543
0.2-0.3	874
0.3-0.4	1438
0.4-0.5	2764
0.5-0.6	2586
0.6-0.7	717
0.7-0.8	35
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
0.8265	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7470	Discontinued
0.7619	Intermediate Similarity	NPD7603	Discontinued
0.7477	Intermediate Similarity	NPD7948	Phase 1
0.7382	Intermediate Similarity	NPD7716	Approved
0.7382	Intermediate Similarity	NPD7717	Approved
0.7376	Intermediate Similarity	NPD484	Approved
0.7349	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD8106	Phase 2
0.7318	Intermediate Similarity	NPD5003	Discontinued
0.7311	Intermediate Similarity	NPD4885	Approved
0.7273	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8356	Approved
0.7252	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2916	Discontinued
0.722	Intermediate Similarity	NPD4600	Approved
0.722	Intermediate Similarity	NPD4601	Approved
0.7217	Intermediate Similarity	NPD3243	Approved
0.7215	Intermediate Similarity	NPD8430	Approved
0.7185	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8255	Phase 2
0.7167	Intermediate Similarity	NPD5632	Approved
0.716	Intermediate Similarity	NPD8463	Approved
0.7149	Intermediate Similarity	NPD7944	Discontinued
0.7149	Intermediate Similarity	NPD7853	Phase 2
0.7149	Intermediate Similarity	NPD6376	Discontinued
0.7137	Intermediate Similarity	NPD3003	Approved
0.7137	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD8016	Phase 3
0.7131	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6176	Phase 1
0.7112	Intermediate Similarity	NPD4897	Phase 2
0.7112	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8322	Phase 2
0.7105	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8093	Discontinued
0.7097	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7878	Phase 2
0.7082	Intermediate Similarity	NPD5612	Discontinued
0.7074	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7957	Phase 1
0.7056	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7777	Approved
0.7054	Intermediate Similarity	NPD7778	Approved
0.7054	Intermediate Similarity	NPD53	Approved
0.704	Intermediate Similarity	NPD5512	Phase 3
0.704	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8364	Approved
0.7027	Intermediate Similarity	NPD8363	Approved
0.7026	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8459	Approved
0.7019	Intermediate Similarity	NPD8460	Approved
0.7018	Intermediate Similarity	NPD8272	Phase 2
0.7013	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5050	Approved
0.7005	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD6517	Phase 3
0.7	Intermediate Similarity	NPD7994	Phase 2
0.6996	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4501	Approved
0.6991	Remote Similarity	NPD4500	Approved
0.698	Remote Similarity	NPD7955	Approved
0.698	Remote Similarity	NPD7956	Approved
0.6974	Remote Similarity	NPD6991	Approved
0.6974	Remote Similarity	NPD8072	Approved
0.6973	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2564	Approved
0.6968	Remote Similarity	NPD4499	Approved
0.6968	Remote Similarity	NPD2565	Phase 2
0.6957	Remote Similarity	NPD7452	Approved
0.6957	Remote Similarity	NPD7222	Phase 2
0.6957	Remote Similarity	NPD7453	Approved
0.6955	Remote Similarity	NPD2383	Phase 1
0.6951	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8115	Approved
0.6943	Remote Similarity	NPD8114	Approved
0.694	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6716	Phase 1
0.6933	Remote Similarity	NPD5506	Approved
0.6933	Remote Similarity	NPD5507	Approved
0.6932	Remote Similarity	NPD8466	Approved
0.6932	Remote Similarity	NPD8429	Approved
0.6932	Remote Similarity	NPD8465	Approved
0.6932	Remote Similarity	NPD8467	Approved
0.6932	Remote Similarity	NPD8428	Approved
0.6932	Remote Similarity	NPD8427	Approved
0.6929	Remote Similarity	NPD3259	Approved
0.6926	Remote Similarity	NPD4373	Phase 2
0.6926	Remote Similarity	NPD7952	Approved
0.6926	Remote Similarity	NPD7953	Approved
0.6926	Remote Similarity	NPD7791	Approved
0.6926	Remote Similarity	NPD7671	Approved
0.6926	Remote Similarity	NPD7950	Approved
0.6926	Remote Similarity	NPD7789	Approved
0.6926	Remote Similarity	NPD7951	Approved
0.6926	Remote Similarity	NPD7672	Approved
0.6926	Remote Similarity	NPD5658	Approved
0.6926	Remote Similarity	NPD7790	Approved
0.6923	Remote Similarity	NPD8094	Discontinued
0.692	Remote Similarity	NPD4418	Discontinued
0.692	Remote Similarity	NPD7194	Discontinued
0.692	Remote Similarity	NPD8359	Phase 2
0.6914	Remote Similarity	NPD7688	Phase 1
0.6909	Remote Similarity	NPD8253	Phase 3
0.6906	Remote Similarity	NPD6665	Discontinued
0.6904	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4520	Approved
0.6894	Remote Similarity	NPD5903	Approved
0.6894	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5902	Approved
0.6892	Remote Similarity	NPD8358	Approved
0.6887	Remote Similarity	NPD7708	Approved
0.6886	Remote Similarity	NPD7727	Phase 2
0.6886	Remote Similarity	NPD7817	Phase 1
0.6886	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4511	Phase 1
0.6885	Remote Similarity	NPD7796	Approved
0.6885	Remote Similarity	NPD7797	Approved
0.6878	Remote Similarity	NPD4948	Discontinued
0.6872	Remote Similarity	NPD2176	Approved
0.6872	Remote Similarity	NPD2177	Approved
0.6872	Remote Similarity	NPD4952	Phase 3
0.6872	Remote Similarity	NPD1768	Approved
0.6872	Remote Similarity	NPD3814	Phase 1
0.6872	Remote Similarity	NPD2175	Phase 3
0.687	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5901	Discontinued
0.6863	Remote Similarity	NPD8246	Approved
0.6863	Remote Similarity	NPD8247	Approved
0.686	Remote Similarity	NPD7731	Approved
0.686	Remote Similarity	NPD7730	Approved
0.6857	Remote Similarity	NPD7558	Phase 2
0.6856	Remote Similarity	NPD8073	Approved
0.6854	Remote Similarity	NPD2844	Phase 3
0.6849	Remote Similarity	NPD6770	Approved
0.6849	Remote Similarity	NPD5596	Phase 2
0.6849	Remote Similarity	NPD2094	Phase 2
0.6849	Remote Similarity	NPD2095	Phase 2
0.6849	Remote Similarity	NPD2092	Phase 2
0.6847	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7803	Approved
0.6844	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8403	Phase 1
0.684	Remote Similarity	NPD7001	Phase 3
0.6838	Remote Similarity	NPD5482	Discontinued
0.6835	Remote Similarity	NPD6452	Discontinued
0.6831	Remote Similarity	NPD7781	Approved
0.6831	Remote Similarity	NPD5559	Phase 2
0.6831	Remote Similarity	NPD7780	Approved
0.6828	Remote Similarity	NPD8426	Approved
0.6828	Remote Similarity	NPD7946	Pre-registration
0.6828	Remote Similarity	NPD8425	Approved
0.6828	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1325	Approved
0.6822	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1326	Approved
0.6822	Remote Similarity	NPD7970	Approved
0.682	Remote Similarity	NPD1996	Discontinued
0.6818	Remote Similarity	NPD2091	Phase 2
0.6818	Remote Similarity	NPD8289	Discontinued
0.6818	Remote Similarity	NPD7426	Phase 1
0.6818	Remote Similarity	NPD2096	Phase 2
0.6818	Remote Similarity	NPD7711	Discontinued
0.6818	Remote Similarity	NPD3263	Phase 3
0.6816	Remote Similarity	NPD7181	Phase 3
0.681	Remote Similarity	NPD6290	Phase 2
0.6809	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD482	Approved
0.6803	Remote Similarity	NPD7824	Approved
0.6798	Remote Similarity	NPD8396	Approved
0.6798	Remote Similarity	NPD8395	Approved
0.6798	Remote Similarity	NPD6248	Phase 2
0.6798	Remote Similarity	NPD6249	Phase 2
0.6798	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8098	Approved
0.6792	Remote Similarity	NPD7726	Phase 1
0.679	Remote Similarity	NPD4086	Phase 1
0.6781	Remote Similarity	NPD2509	Approved
0.6781	Remote Similarity	NPD2510	Approved
0.6777	Remote Similarity	NPD7271	Approved
0.6774	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4334	Discontinued
0.677	Remote Similarity	NPD7618	Phase 3
0.677	Remote Similarity	NPD7619	Phase 3
0.6766	Remote Similarity	NPD5936	Approved
0.6766	Remote Similarity	NPD5939	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