NPASS Compound

Structure

NPC471176 OpenBabel07101718322D 48 53 0 0 1 0 0 0 0 0999 V2000 0.9706 0.6567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4294 3.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5607 3.3137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8667 4.0077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8425 3.5928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1563 1.9415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5446 6.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1293 5.5641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9793 5.0734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2793 5.0734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9793 4.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2793 4.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1727 1.4176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2246 1.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1293 2.6197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6280 1.7955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9095 -0.4059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4106 4.2618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1206 1.1475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 4.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1293 3.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2288 0.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3088 0.4907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6646 3.3137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8667 2.1117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9334 -0.3033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1046 4.9558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2793 2.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6041 1.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1206 2.1290 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7294 2.6197 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5794 2.1290 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9582 0.2421 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6126 3.0597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.6197 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5794 1.1475 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7294 0.6567 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5794 5.0734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8147 1.8576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0526 4.7017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2793 1.1475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2609 2.4223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8556 -0.7340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8506 5.9038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7294 3.6012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4294 2.6197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8082 0.7329 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 1 19 2 0 0 0 0 2 20 1 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 6 36 1 0 0 0 0 7 44 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 25 1 0 0 0 0 14 35 1 0 0 0 0 15 21 1 0 0 0 0 15 28 1 0 0 0 0 16 22 2 0 0 0 0 16 29 1 0 0 0 0 17 23 1 0 0 0 0 17 26 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 20 38 2 0 0 0 0 20 45 1 0 0 0 0 22 23 1 0 0 0 0 22 33 1 0 0 0 0 23 36 1 1 0 0 0 24 34 1 0 0 0 0 24 35 1 1 0 0 0 25 34 1 0 0 0 0 25 39 2 0 0 0 0 26 37 1 1 0 0 0 26 48 1 0 0 0 0 27 40 2 0 0 0 0 27 44 1 0 0 0 0 28 41 2 0 0 0 0 28 46 1 0 0 0 0 29 42 2 0 0 0 0 29 47 1 0 0 0 0 30 19 1 6 0 0 0 30 31 1 0 0 0 0 30 35 1 0 0 0 0 31 32 1 0 0 0 0 31 45 1 6 0 0 0 32 36 1 1 0 0 0 32 46 1 0 0 0 0 33 43 1 0 0 0 0 33 47 1 0 0 0 0 35 5 1 1 0 0 0 36 37 1 1 0 0 0 37 19 1 1 0 0 0 37 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	662.27
Volume:	664.861
LogP:	3.789
LogD:	2.728
LogS:	-4.89
# Rotatable Bonds:	11
TPSA:	162.1
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.17
Synthetic Accessibility Score:	5.945
Fsp3:	0.514
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:	-5.623
MDCK Permeability:	2.032596239587292e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.517
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	85.48055267333984%
Volume Distribution (VD):	0.466
Pgp-substrate:	12.632009506225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.76

ADMET: Excretion

Clearance (CL):	7.796
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.291
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.827
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.599
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.22
Carcinogencity:	0.08
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC471176

Natural Product ID:	NPC471176
*Common Name:**	Turrapubesin E
IUPAC Name:	methyl 2-[(1R,2S)-2-[(1aR,3R,3aR,4R,5R,6R,7aS)-5-acetyloxy-3-(2-hydroxy-5-oxo-2H-furan-3-yl)-3a-methyl-7-methylidene-4-(2-phenylacetyl)oxy-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate
Synonyms:
Standard InCHIKey:	OHQWQSGCWXQCSF-AAUQHIRQSA-N
Standard InCHI:	InChI=1S/C37H42O11/c1-19-30(35(5)14-13-25(39)34(3,4)24(35)18-27(40)44-7)31(45-20(2)38)32(46-28(41)15-21-11-9-8-10-12-21)36(6)23(17-26-37(19,36)48-26)22-16-29(42)47-33(22)43/h8-14,16,23-24,26,30-33,43H,1,15,17-18H2,2-7H3/t23-,24-,26+,30+,31+,32-,33?,35-,36+,37+/m0/s1
SMILES:	CC(=O)OC1C(C(=C)C23C(O2)CC(C3(C1OC(=O)CC4=CC=CC=C4)C)C5=CC(=O)OC5O)C6(C=CC(=O)C(C6CC(=O)OC)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386310
PubChem CID:	24180655
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	Species	Meliaceae	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	2
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[486587]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[486587]
NPT176	Organism	Artemia salina	Artemia salina	mortality	<	50.0	%	PMID[486587]

☑ 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 NPC471176 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	330
0.1-0.2	1123
0.2-0.3	2473
0.3-0.4	4919
0.4-0.5	9066
0.5-0.6	16150
0.6-0.7	7428
0.7-0.8	1103
0.8-0.85	102
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8679	High Similarity	NPC477491
0.8671	High Similarity	NPC478073
0.8591	High Similarity	NPC140021
0.8526	High Similarity	NPC475548
0.8526	High Similarity	NPC290683
0.8526	High Similarity	NPC475638
0.8519	High Similarity	NPC477488
0.8491	Intermediate Similarity	NPC475536
0.8491	Intermediate Similarity	NPC165234
0.8442	Intermediate Similarity	NPC476173
0.8438	Intermediate Similarity	NPC473797
0.8438	Intermediate Similarity	NPC475300
0.8438	Intermediate Similarity	NPC475464
0.8438	Intermediate Similarity	NPC473641
0.8438	Intermediate Similarity	NPC475505
0.8438	Intermediate Similarity	NPC475437
0.8418	Intermediate Similarity	NPC476784
0.8397	Intermediate Similarity	NPC472658
0.8397	Intermediate Similarity	NPC471135
0.8397	Intermediate Similarity	NPC472657
0.8366	Intermediate Similarity	NPC312393
0.8366	Intermediate Similarity	NPC478263
0.8365	Intermediate Similarity	NPC471138
0.8365	Intermediate Similarity	NPC326328
0.8365	Intermediate Similarity	NPC309991
0.8365	Intermediate Similarity	NPC323356
0.8344	Intermediate Similarity	NPC63737
0.8344	Intermediate Similarity	NPC469456
0.8333	Intermediate Similarity	NPC469647
0.8333	Intermediate Similarity	NPC469648
0.8333	Intermediate Similarity	NPC473468
0.8333	Intermediate Similarity	NPC475567
0.8333	Intermediate Similarity	NPC22571
0.8333	Intermediate Similarity	NPC283875
0.8333	Intermediate Similarity	NPC473440
0.8333	Intermediate Similarity	NPC473557
0.8333	Intermediate Similarity	NPC472547
0.8333	Intermediate Similarity	NPC138641
0.8323	Intermediate Similarity	NPC475417
0.8323	Intermediate Similarity	NPC475561
0.8301	Intermediate Similarity	NPC478264
0.8291	Intermediate Similarity	NPC70344
0.8289	Intermediate Similarity	NPC477894
0.8282	Intermediate Similarity	NPC475175
0.8282	Intermediate Similarity	NPC475198
0.8282	Intermediate Similarity	NPC475531
0.8278	Intermediate Similarity	NPC325078
0.8269	Intermediate Similarity	NPC62792
0.8269	Intermediate Similarity	NPC472398
0.8261	Intermediate Similarity	NPC478124
0.8258	Intermediate Similarity	NPC474564
0.8247	Intermediate Similarity	NPC240115
0.8239	Intermediate Similarity	NPC322048
0.8239	Intermediate Similarity	NPC318447
0.8235	Intermediate Similarity	NPC34943
0.8232	Intermediate Similarity	NPC40138
0.8224	Intermediate Similarity	NPC34012
0.8221	Intermediate Similarity	NPC325732
0.8221	Intermediate Similarity	NPC324769
0.8217	Intermediate Similarity	NPC145649
0.8217	Intermediate Similarity	NPC233581
0.8212	Intermediate Similarity	NPC90614
0.8205	Intermediate Similarity	NPC475218
0.8205	Intermediate Similarity	NPC70236
0.8205	Intermediate Similarity	NPC475447
0.8205	Intermediate Similarity	NPC476092
0.82	Intermediate Similarity	NPC39549
0.8194	Intermediate Similarity	NPC104382
0.8194	Intermediate Similarity	NPC327031
0.8187	Intermediate Similarity	NPC319404
0.8187	Intermediate Similarity	NPC49297
0.8182	Intermediate Similarity	NPC125882
0.8182	Intermediate Similarity	NPC472556
0.8176	Intermediate Similarity	NPC11410
0.8176	Intermediate Similarity	NPC323001
0.8176	Intermediate Similarity	NPC154675
0.8176	Intermediate Similarity	NPC326235
0.817	Intermediate Similarity	NPC91703
0.8163	Intermediate Similarity	NPC472418
0.8158	Intermediate Similarity	NPC118080
0.8158	Intermediate Similarity	NPC472576
0.8158	Intermediate Similarity	NPC291599
0.8158	Intermediate Similarity	NPC16912
0.8158	Intermediate Similarity	NPC27377
0.8158	Intermediate Similarity	NPC87448
0.8158	Intermediate Similarity	NPC97947
0.8158	Intermediate Similarity	NPC41481
0.8153	Intermediate Similarity	NPC469415
0.8153	Intermediate Similarity	NPC478123
0.8153	Intermediate Similarity	NPC298072
0.8148	Intermediate Similarity	NPC477190
0.8148	Intermediate Similarity	NPC43304
0.8148	Intermediate Similarity	NPC477188
0.8141	Intermediate Similarity	NPC76103
0.8138	Intermediate Similarity	NPC471170
0.8133	Intermediate Similarity	NPC472545
0.8133	Intermediate Similarity	NPC472551
0.8129	Intermediate Similarity	NPC20255
0.8125	Intermediate Similarity	NPC181924
0.8121	Intermediate Similarity	NPC4242
0.8121	Intermediate Similarity	NPC471911
0.8117	Intermediate Similarity	NPC38696
0.8117	Intermediate Similarity	NPC471139
0.8113	Intermediate Similarity	NPC34066
0.8113	Intermediate Similarity	NPC251139
0.8113	Intermediate Similarity	NPC469422
0.8108	Intermediate Similarity	NPC80599
0.8105	Intermediate Similarity	NPC192658
0.8105	Intermediate Similarity	NPC472546
0.8105	Intermediate Similarity	NPC472235
0.8105	Intermediate Similarity	NPC472236
0.8098	Intermediate Similarity	NPC478125
0.8095	Intermediate Similarity	NPC472388
0.8092	Intermediate Similarity	NPC97667
0.8092	Intermediate Similarity	NPC275592
0.8092	Intermediate Similarity	NPC171207
0.8092	Intermediate Similarity	NPC162613
0.8092	Intermediate Similarity	NPC87934
0.8092	Intermediate Similarity	NPC100913
0.8089	Intermediate Similarity	NPC303429
0.8089	Intermediate Similarity	NPC222102
0.8082	Intermediate Similarity	NPC230331
0.8077	Intermediate Similarity	NPC132652
0.8077	Intermediate Similarity	NPC473760
0.8069	Intermediate Similarity	NPC175186
0.8065	Intermediate Similarity	NPC96903
0.8065	Intermediate Similarity	NPC158663
0.8065	Intermediate Similarity	NPC171525
0.8065	Intermediate Similarity	NPC472568
0.8065	Intermediate Similarity	NPC200471
0.8065	Intermediate Similarity	NPC92867
0.8065	Intermediate Similarity	NPC184817
0.8065	Intermediate Similarity	NPC70403
0.8065	Intermediate Similarity	NPC470159
0.8065	Intermediate Similarity	NPC473088
0.8065	Intermediate Similarity	NPC476973
0.8065	Intermediate Similarity	NPC469349
0.8065	Intermediate Similarity	NPC472571
0.8065	Intermediate Similarity	NPC29704
0.8065	Intermediate Similarity	NPC311825
0.8065	Intermediate Similarity	NPC177940
0.8065	Intermediate Similarity	NPC471104
0.8065	Intermediate Similarity	NPC470157
0.8065	Intermediate Similarity	NPC174982
0.8065	Intermediate Similarity	NPC472575
0.8065	Intermediate Similarity	NPC472572
0.8059	Intermediate Similarity	NPC475613
0.8052	Intermediate Similarity	NPC95449
0.8052	Intermediate Similarity	NPC163087
0.8052	Intermediate Similarity	NPC131966
0.8052	Intermediate Similarity	NPC191387
0.805	Intermediate Similarity	NPC469477
0.805	Intermediate Similarity	NPC133430
0.8049	Intermediate Similarity	NPC471493
0.8039	Intermediate Similarity	NPC242355
0.8039	Intermediate Similarity	NPC224491
0.8038	Intermediate Similarity	NPC96308
0.8038	Intermediate Similarity	NPC197037
0.8037	Intermediate Similarity	NPC275477
0.8027	Intermediate Similarity	NPC225103
0.8026	Intermediate Similarity	NPC9905
0.8025	Intermediate Similarity	NPC477623
0.8013	Intermediate Similarity	NPC48599
0.8013	Intermediate Similarity	NPC474935
0.8013	Intermediate Similarity	NPC209592
0.8013	Intermediate Similarity	NPC472374
0.8013	Intermediate Similarity	NPC473602
0.8013	Intermediate Similarity	NPC472372
0.8	Intermediate Similarity	NPC475122
0.8	Intermediate Similarity	NPC163719
0.8	Intermediate Similarity	NPC470152
0.8	Intermediate Similarity	NPC95810
0.8	Intermediate Similarity	NPC57628
0.8	Intermediate Similarity	NPC469730
0.8	Intermediate Similarity	NPC472569
0.8	Intermediate Similarity	NPC473611
0.8	Intermediate Similarity	NPC472570
0.8	Intermediate Similarity	NPC475759
0.8	Intermediate Similarity	NPC241951
0.8	Intermediate Similarity	NPC132599
0.8	Intermediate Similarity	NPC70716
0.8	Intermediate Similarity	NPC469398
0.8	Intermediate Similarity	NPC125106
0.8	Intermediate Similarity	NPC476974
0.8	Intermediate Similarity	NPC11685
0.8	Intermediate Similarity	NPC473632
0.8	Intermediate Similarity	NPC61891
0.8	Intermediate Similarity	NPC472573
0.8	Intermediate Similarity	NPC95265
0.8	Intermediate Similarity	NPC25768
0.8	Intermediate Similarity	NPC188865
0.7988	Intermediate Similarity	NPC322420
0.7987	Intermediate Similarity	NPC475135
0.7975	Intermediate Similarity	NPC470245
0.7975	Intermediate Similarity	NPC473214
0.7975	Intermediate Similarity	NPC469448
0.7975	Intermediate Similarity	NPC91730
0.7975	Intermediate Similarity	NPC125033
0.7973	Intermediate Similarity	NPC473443
0.7963	Intermediate Similarity	NPC469399

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 NPC471176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	762
0.2-0.3	1738
0.3-0.4	3170
0.4-0.5	2066
0.5-0.6	889
0.6-0.7	249
0.7-0.8	11
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
0.8133	Intermediate Similarity	NPD7799	Discontinued
0.7834	Intermediate Similarity	NPD7236	Approved
0.7702	Intermediate Similarity	NPD7239	Suspended
0.7457	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8368	Discontinued
0.7303	Intermediate Similarity	NPD8407	Phase 2
0.7278	Intermediate Similarity	NPD7058	Phase 2
0.7278	Intermediate Similarity	NPD7057	Phase 3
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7685	Pre-registration
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.719	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8360	Approved
0.7143	Intermediate Similarity	NPD8361	Approved
0.7133	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8435	Approved
0.7047	Intermediate Similarity	NPD7741	Discontinued
0.7039	Intermediate Similarity	NPD7507	Approved
0.7033	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7319	Approved
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.6986	Remote Similarity	NPD6858	Approved
0.6986	Remote Similarity	NPD7094	Approved
0.698	Remote Similarity	NPD7516	Approved
0.6962	Remote Similarity	NPD7961	Discontinued
0.6944	Remote Similarity	NPD6764	Approved
0.6944	Remote Similarity	NPD6765	Approved
0.6913	Remote Similarity	NPD7328	Approved
0.6913	Remote Similarity	NPD7327	Approved
0.6882	Remote Similarity	NPD7028	Phase 2
0.6879	Remote Similarity	NPD4967	Phase 2
0.6879	Remote Similarity	NPD4966	Approved
0.6879	Remote Similarity	NPD4965	Approved
0.6855	Remote Similarity	NPD6663	Approved
0.6848	Remote Similarity	NPD8166	Discontinued
0.6839	Remote Similarity	NPD7736	Approved
0.6807	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD37	Approved
0.6793	Remote Similarity	NPD6785	Approved
0.6793	Remote Similarity	NPD6784	Approved
0.6791	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2629	Approved
0.6776	Remote Similarity	NPD8380	Approved
0.6776	Remote Similarity	NPD8335	Approved
0.6776	Remote Similarity	NPD7503	Approved
0.6776	Remote Similarity	NPD8033	Approved
0.6776	Remote Similarity	NPD8379	Approved
0.6776	Remote Similarity	NPD8378	Approved
0.6776	Remote Similarity	NPD8296	Approved
0.6763	Remote Similarity	NPD5761	Phase 2
0.6763	Remote Similarity	NPD5760	Phase 2
0.6737	Remote Similarity	NPD8485	Approved
0.6733	Remote Similarity	NPD7115	Discovery
0.6732	Remote Similarity	NPD6370	Approved
0.6723	Remote Similarity	NPD7199	Phase 2
0.6722	Remote Similarity	NPD7228	Approved
0.6711	Remote Similarity	NPD8377	Approved
0.6711	Remote Similarity	NPD8294	Approved
0.6709	Remote Similarity	NPD5736	Approved
0.6707	Remote Similarity	NPD6190	Approved
0.6705	Remote Similarity	NPD6234	Discontinued
0.669	Remote Similarity	NPD6685	Approved
0.6689	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7055	Discontinued
0.6667	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD8150	Discontinued
0.6647	Remote Similarity	NPD6273	Approved
0.6647	Remote Similarity	NPD4628	Phase 3
0.6645	Remote Similarity	NPD7492	Approved
0.6628	Remote Similarity	NPD7458	Discontinued
0.6627	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7497	Discontinued
0.6603	Remote Similarity	NPD6616	Approved
0.6601	Remote Similarity	NPD6054	Approved
0.66	Remote Similarity	NPD8462	Phase 1
0.6599	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD8312	Approved
0.6595	Remote Similarity	NPD8313	Approved
0.6588	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6882	Approved
0.6566	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6002	Phase 3
0.6566	Remote Similarity	NPD6005	Phase 3
0.6566	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6004	Phase 3
0.6561	Remote Similarity	NPD7078	Approved
0.6556	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7305	Phase 1
0.6536	Remote Similarity	NPD7610	Discontinued
0.6531	Remote Similarity	NPD6686	Approved
0.6517	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD5125	Phase 3
0.6516	Remote Similarity	NPD5126	Approved
0.6516	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6009	Approved
0.6508	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5844	Phase 1
0.6494	Remote Similarity	NPD7009	Phase 2
0.6494	Remote Similarity	NPD6319	Approved
0.6491	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7240	Approved
0.6486	Remote Similarity	NPD6559	Discontinued
0.6483	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5765	Approved
0.6483	Remote Similarity	NPD6647	Phase 2
0.6477	Remote Similarity	NPD8455	Phase 2
0.6477	Remote Similarity	NPD7819	Suspended
0.6467	Remote Similarity	NPD5763	Approved
0.6467	Remote Similarity	NPD5762	Approved
0.6467	Remote Similarity	NPD6912	Phase 3
0.6461	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6016	Approved
0.6452	Remote Similarity	NPD6015	Approved
0.6448	Remote Similarity	NPD3818	Discontinued
0.6448	Remote Similarity	NPD3751	Discontinued
0.6443	Remote Similarity	NPD7699	Phase 2
0.6443	Remote Similarity	NPD7700	Phase 2
0.6438	Remote Similarity	NPD6085	Phase 2
0.6438	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4632	Approved
0.642	Remote Similarity	NPD7008	Discontinued
0.6419	Remote Similarity	NPD6899	Approved
0.6419	Remote Similarity	NPD6881	Approved
0.6414	Remote Similarity	NPD8319	Approved
0.6414	Remote Similarity	NPD8320	Phase 1
0.6413	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5988	Approved
0.6405	Remote Similarity	NPD4198	Discontinued
0.64	Remote Similarity	NPD6650	Approved
0.64	Remote Similarity	NPD8130	Phase 1
0.64	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6649	Approved
0.6398	Remote Similarity	NPD7084	Phase 3
0.6395	Remote Similarity	NPD6008	Approved
0.6393	Remote Similarity	NPD7473	Discontinued
0.6391	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.639	Remote Similarity	NPD8404	Phase 2
0.6387	Remote Similarity	NPD6059	Approved
0.6382	Remote Similarity	NPD6010	Discontinued
0.6378	Remote Similarity	NPD7074	Phase 3
0.6376	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6535	Approved
0.6373	Remote Similarity	NPD6534	Approved
0.6369	Remote Similarity	NPD7604	Phase 2
0.6369	Remote Similarity	NPD7075	Discontinued
0.6364	Remote Similarity	NPD7435	Discontinued
0.6351	Remote Similarity	NPD5697	Approved
0.6351	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6412	Phase 2
0.6348	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD3226	Approved
0.634	Remote Similarity	NPD690	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5951	Approved
0.6333	Remote Similarity	NPD2067	Discontinued
0.6333	Remote Similarity	NPD7102	Approved
0.6333	Remote Similarity	NPD7290	Approved
0.6333	Remote Similarity	NPD6883	Approved
0.6324	Remote Similarity	NPD7054	Approved
0.6322	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7137	Phase 2
0.6309	Remote Similarity	NPD7320	Approved
0.6307	Remote Similarity	NPD4380	Phase 2
0.6306	Remote Similarity	NPD2932	Approved
0.6303	Remote Similarity	NPD4140	Approved
0.63	Remote Similarity	NPD7999	Approved
0.6293	Remote Similarity	NPD7930	Approved
0.6292	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6869	Approved
0.6291	Remote Similarity	NPD6617	Approved
0.6291	Remote Similarity	NPD6847	Approved
0.629	Remote Similarity	NPD7472	Approved
0.6284	Remote Similarity	NPD6675	Approved
0.6284	Remote Similarity	NPD5048	Discontinued
0.6284	Remote Similarity	NPD6402	Approved
0.6284	Remote Similarity	NPD7128	Approved
0.6284	Remote Similarity	NPD5739	Approved
0.6281	Remote Similarity	NPD7696	Phase 3
0.6281	Remote Similarity	NPD7697	Approved
0.6281	Remote Similarity	NPD7698	Approved
0.628	Remote Similarity	NPD3764	Approved
0.6277	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7808	Phase 3
0.6276	Remote Similarity	NPD7640	Approved
0.6276	Remote Similarity	NPD7639	Approved
0.6276	Remote Similarity	NPD2066	Phase 3
0.6273	Remote Similarity	NPD3094	Phase 2
0.6271	Remote Similarity	NPD7411	Suspended
0.6267	Remote Similarity	NPD6013	Approved
0.6267	Remote Similarity	NPD6373	Approved
0.6267	Remote Similarity	NPD6372	Approved
0.6267	Remote Similarity	NPD6012	Approved
0.6267	Remote Similarity	NPD6014	Approved
0.6264	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7874	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