NPASS Compound

Structure

CID95449 OpenBabel06191715432D 44 47 0 0 1 0 0 0 0 0999 V2000 -1.6493 1.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 1.2780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7941 -2.2498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9615 3.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7023 -0.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8782 -0.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6226 0.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2134 0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6931 -1.6608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8625 -2.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6931 -0.7016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0318 -1.6608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8625 -0.2220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5465 -0.6070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4808 2.7368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2989 1.0358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6185 1.6812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 -2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0050 3.3803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9524 -1.5816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0318 -0.7016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8969 0.2859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4332 2.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5980 -0.7499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7808 1.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3504 0.8929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7091 0.2576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1292 1.7236 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9166 -0.2827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2011 -0.2220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2112 1.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0776 1.8665 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4952 -3.2856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5353 4.1728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0954 -2.5301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8454 0.4289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0856 3.3254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2011 0.7372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5784 1.9998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2476 -1.6428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4112 2.5161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0595 -1.2312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3704 -0.7016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 31 1 0 0 0 0 7 31 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 21 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 24 1 0 0 0 0 15 23 1 0 0 0 0 15 33 1 0 0 0 0 16 22 1 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 17 25 2 0 0 0 0 18 34 2 0 0 0 0 18 41 1 0 0 0 0 19 35 2 0 0 0 0 19 42 1 0 0 0 0 20 36 2 0 0 0 0 20 43 1 0 0 0 0 21 30 1 0 0 0 0 22 37 1 6 0 0 0 23 38 2 0 0 0 0 24 32 1 1 0 0 0 24 41 1 0 0 0 0 25 27 1 0 0 0 0 25 33 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 1 0 0 0 27 29 1 0 0 0 0 27 44 1 1 0 0 0 28 33 1 6 0 0 0 28 42 1 0 0 0 0 29 32 1 6 0 0 0 29 43 1 0 0 0 0 30 39 2 0 0 0 0 30 44 1 0 0 0 0 31 40 1 0 0 0 0 32 8 1 1 0 0 0 33 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.26
Volume:	615.426
LogP:	2.411
LogD:	1.882
LogS:	-4.267
# Rotatable Bonds:	10
TPSA:	162.73
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	5.18
Fsp3:	0.545
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:	-5.307
MDCK Permeability:	9.304494597017765e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.878
30% Bioavailability (F30%):	0.914

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.793
Plasma Protein Binding (PPB):	62.333770751953125%
Volume Distribution (VD):	1.011
Pgp-substrate:	29.659822463989258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	3.342
Half-life (T1/2):	0.625

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.294
Carcinogencity:	0.126
Eye Corrosion:	0.007
Eye Irritation:	0.051
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC95449

Natural Product ID:	NPC95449
*Common Name:**	13-Oxo-Taxchinin A
IUPAC Name:	[(4R,5R,5aS,6S,8S,9aR,10S,10aS)-5,6,10-triacetyloxy-8-hydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-9-methylidene-2-oxo-1,4,5,6,7,8,9a,10-octahydrobenzo[g]azulen-4-yl] benzoate
Synonyms:
Standard InCHIKey:	CXSZDWCQWKJJEB-AGSJQTBMSA-N
Standard InCHI:	InChI=1S/C33H40O11/c1-16-22(37)14-24(41-18(3)34)32(8)26(16)28(42-19(4)35)33(31(6,7)40)15-23(38)17(2)25(33)27(29(32)43-20(5)36)44-30(39)21-12-10-9-11-13-21/h9-13,22,24,26-29,37,40H,1,14-15H2,2-8H3/t22-,24-,26-,27+,28-,29-,32+,33-/m0/s1
SMILES:	C=C1[C@H](C[C@@H]([C@]2(C)[C@@H]1[C@@H]([C@@]1(CC(=O)C(=C1[C@H]([C@@H]2OC(=O)C)OC(=O)c1ccccc1)C)C(C)(C)O)OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508581
PubChem CID:	5321734
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO40371	Taxus cuspidata var. nana	Strain	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134747]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	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	6
Others	4

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[537918]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	100.0	ug.mL-1	PMID[537919]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	100.0	ug.mL-1	PMID[537919]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	=	100.0	ug.mL-1	PMID[537919]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	96.6	ug.mL-1	PMID[537919]
NPT91	Cell Line	KB	Homo sapiens	IC90	=	100.0	ug.mL-1	PMID[537919]
NPT83	Cell Line	MCF7	Homo sapiens	IC90	=	100.0	ug.mL-1	PMID[537919]
NPT492	Cell Line	Caco-2	Homo sapiens	IC90	=	100.0	ug.mL-1	PMID[537919]
NPT65	Cell Line	HepG2	Homo sapiens	IC90	=	100.0	ug.mL-1	PMID[537919]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	91620.0	nM	PMID[537917]

☑ 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 NPC95449 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	294
0.1-0.2	1030
0.2-0.3	2278
0.3-0.4	4861
0.4-0.5	9084
0.5-0.6	11222
0.6-0.7	11403
0.7-0.8	2168
0.8-0.85	300
0.85-0.9	43
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC87934
0.963	High Similarity	NPC162613
0.9556	High Similarity	NPC9905
0.9489	High Similarity	NPC192658
0.9353	High Similarity	NPC34943
0.9286	High Similarity	NPC125882
0.9275	High Similarity	NPC266374
0.922	High Similarity	NPC20255
0.922	High Similarity	NPC240115
0.9149	High Similarity	NPC311825
0.9149	High Similarity	NPC92867
0.9034	High Similarity	NPC22571
0.9034	High Similarity	NPC138641
0.9034	High Similarity	NPC469648
0.9034	High Similarity	NPC283875
0.9034	High Similarity	NPC469647
0.9021	High Similarity	NPC473760
0.9007	High Similarity	NPC477894
0.8951	High Similarity	NPC473602
0.8951	High Similarity	NPC48599
0.8951	High Similarity	NPC209592
0.8913	High Similarity	NPC477893
0.8912	High Similarity	NPC251139
0.8904	High Similarity	NPC145649
0.8904	High Similarity	NPC233581
0.8889	High Similarity	NPC132652
0.8851	High Similarity	NPC11410
0.8836	High Similarity	NPC472398
0.8819	High Similarity	NPC312393
0.8803	High Similarity	NPC140021
0.8803	High Similarity	NPC182869
0.8794	High Similarity	NPC472547
0.8794	High Similarity	NPC90614
0.8784	High Similarity	NPC473611
0.8784	High Similarity	NPC469730
0.8784	High Similarity	NPC473632
0.8784	High Similarity	NPC21410
0.8784	High Similarity	NPC473670
0.8784	High Similarity	NPC132599
0.8777	High Similarity	NPC477896
0.8767	High Similarity	NPC31829
0.8767	High Similarity	NPC7095
0.8767	High Similarity	NPC125033
0.875	High Similarity	NPC472556
0.875	High Similarity	NPC127857
0.8732	High Similarity	NPC97947
0.8732	High Similarity	NPC87448
0.8732	High Similarity	NPC291599
0.8732	High Similarity	NPC41481
0.8732	High Similarity	NPC118080
0.8732	High Similarity	NPC16912
0.8732	High Similarity	NPC242355
0.8732	High Similarity	NPC27377
0.8732	High Similarity	NPC472576
0.8714	High Similarity	NPC472374
0.8714	High Similarity	NPC472372
0.8707	High Similarity	NPC197037
0.8707	High Similarity	NPC471103
0.8707	High Similarity	NPC51602
0.8699	High Similarity	NPC60509
0.8699	High Similarity	NPC250046
0.8699	High Similarity	NPC81698
0.8676	High Similarity	NPC58061
0.8671	High Similarity	NPC34012
0.8662	High Similarity	NPC275592
0.8662	High Similarity	NPC171207
0.8662	High Similarity	NPC97667
0.8662	High Similarity	NPC100913
0.8652	High Similarity	NPC39549
0.8649	High Similarity	NPC477905
0.8649	High Similarity	NPC472548
0.8639	High Similarity	NPC112216
0.8639	High Similarity	NPC91730
0.8639	High Similarity	NPC165260
0.8639	High Similarity	NPC161239
0.8639	High Similarity	NPC198455
0.8621	High Similarity	NPC184817
0.8621	High Similarity	NPC25043
0.8621	High Similarity	NPC473088
0.8621	High Similarity	NPC470157
0.8621	High Similarity	NPC470159
0.8621	High Similarity	NPC70403
0.8621	High Similarity	NPC471104
0.8621	High Similarity	NPC472572
0.8621	High Similarity	NPC472571
0.8621	High Similarity	NPC200471
0.8621	High Similarity	NPC177940
0.8621	High Similarity	NPC469349
0.8621	High Similarity	NPC472568
0.8621	High Similarity	NPC29704
0.8621	High Similarity	NPC472575
0.8621	High Similarity	NPC476973
0.8621	High Similarity	NPC96903
0.8621	High Similarity	NPC158663
0.8621	High Similarity	NPC171525
0.8621	High Similarity	NPC174982
0.8621	High Similarity	NPC134131
0.8611	High Similarity	NPC163087
0.86	High Similarity	NPC106895
0.8593	High Similarity	NPC284022
0.8592	High Similarity	NPC473301
0.8591	High Similarity	NPC158333
0.8591	High Similarity	NPC242262
0.8591	High Similarity	NPC265395
0.8591	High Similarity	NPC249471
0.8591	High Similarity	NPC134685
0.8591	High Similarity	NPC473414
0.8591	High Similarity	NPC237549
0.8591	High Similarity	NPC256142
0.8591	High Similarity	NPC304876
0.8591	High Similarity	NPC11588
0.8591	High Similarity	NPC472030
0.8591	High Similarity	NPC229545
0.8591	High Similarity	NPC248265
0.8591	High Similarity	NPC257213
0.8591	High Similarity	NPC1173
0.8591	High Similarity	NPC472022
0.8591	High Similarity	NPC472005
0.8582	High Similarity	NPC472551
0.8582	High Similarity	NPC472545
0.8571	High Similarity	NPC471134
0.8571	High Similarity	NPC28836
0.8552	High Similarity	NPC70716
0.8552	High Similarity	NPC472569
0.8552	High Similarity	NPC38696
0.8552	High Similarity	NPC163719
0.8552	High Similarity	NPC125106
0.8552	High Similarity	NPC241951
0.8552	High Similarity	NPC470152
0.8552	High Similarity	NPC25768
0.8552	High Similarity	NPC57628
0.8552	High Similarity	NPC475759
0.8552	High Similarity	NPC188865
0.8552	High Similarity	NPC476974
0.8552	High Similarity	NPC472570
0.8552	High Similarity	NPC95265
0.8552	High Similarity	NPC472573
0.8552	High Similarity	NPC475122
0.8552	High Similarity	NPC11685
0.8552	High Similarity	NPC95810
0.8542	High Similarity	NPC183540
0.8542	High Similarity	NPC472546
0.8533	High Similarity	NPC114410
0.8533	High Similarity	NPC259144
0.8533	High Similarity	NPC282239
0.8533	High Similarity	NPC472549
0.8533	High Similarity	NPC112523
0.8533	High Similarity	NPC228204
0.8533	High Similarity	NPC26033
0.8533	High Similarity	NPC114357
0.8533	High Similarity	NPC155329
0.8514	High Similarity	NPC470245
0.8514	High Similarity	NPC473214
0.8511	High Similarity	NPC291638
0.8511	High Similarity	NPC66761
0.8511	High Similarity	NPC472577
0.8511	High Similarity	NPC17877
0.8511	High Similarity	NPC195647
0.8503	High Similarity	NPC217918
0.8503	High Similarity	NPC205389
0.8503	High Similarity	NPC327031
0.85	High Similarity	NPC472248
0.8497	Intermediate Similarity	NPC476077
0.8493	Intermediate Similarity	NPC471100
0.8493	Intermediate Similarity	NPC471107
0.8483	Intermediate Similarity	NPC153214
0.8483	Intermediate Similarity	NPC131966
0.8483	Intermediate Similarity	NPC91703
0.8483	Intermediate Similarity	NPC191387
0.8477	Intermediate Similarity	NPC217091
0.8477	Intermediate Similarity	NPC70344
0.8472	Intermediate Similarity	NPC187566
0.8472	Intermediate Similarity	NPC473497
0.8472	Intermediate Similarity	NPC224491
0.8467	Intermediate Similarity	NPC219419
0.8467	Intermediate Similarity	NPC169913
0.8467	Intermediate Similarity	NPC77719
0.8456	Intermediate Similarity	NPC101043
0.8456	Intermediate Similarity	NPC306799
0.8456	Intermediate Similarity	NPC470153
0.8451	Intermediate Similarity	NPC202729
0.8446	Intermediate Similarity	NPC270590
0.8446	Intermediate Similarity	NPC473215
0.8446	Intermediate Similarity	NPC266265
0.8446	Intermediate Similarity	NPC301556
0.8446	Intermediate Similarity	NPC476975
0.8446	Intermediate Similarity	NPC471101
0.8446	Intermediate Similarity	NPC92293
0.8442	Intermediate Similarity	NPC55744
0.8442	Intermediate Similarity	NPC477190
0.8442	Intermediate Similarity	NPC43304
0.8442	Intermediate Similarity	NPC477188
0.844	Intermediate Similarity	NPC311492
0.844	Intermediate Similarity	NPC474608
0.8435	Intermediate Similarity	NPC474935
0.8435	Intermediate Similarity	NPC475552
0.8435	Intermediate Similarity	NPC478263
0.8429	Intermediate Similarity	NPC233860
0.8429	Intermediate Similarity	NPC472394
0.8429	Intermediate Similarity	NPC239358

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 NPC95449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	726
0.2-0.3	1555
0.3-0.4	2730
0.4-0.5	2250
0.5-0.6	1222
0.6-0.7	397
0.7-0.8	28
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
0.8121	Intermediate Similarity	NPD7236	Approved
0.7974	Intermediate Similarity	NPD7239	Suspended
0.7853	Intermediate Similarity	NPD7799	Discontinued
0.7665	Intermediate Similarity	NPD8368	Discontinued
0.7647	Intermediate Similarity	NPD8434	Phase 2
0.7633	Intermediate Similarity	NPD8407	Phase 2
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7057	Phase 3
0.7516	Intermediate Similarity	NPD7058	Phase 2
0.7457	Intermediate Similarity	NPD8360	Approved
0.7457	Intermediate Similarity	NPD8361	Approved
0.7429	Intermediate Similarity	NPD7741	Discontinued
0.7391	Intermediate Similarity	NPD2629	Approved
0.7384	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8435	Approved
0.7353	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7819	Suspended
0.7248	Intermediate Similarity	NPD3764	Approved
0.7244	Intermediate Similarity	NPD6190	Approved
0.7207	Intermediate Similarity	NPD8485	Approved
0.7206	Intermediate Similarity	NPD2182	Approved
0.72	Intermediate Similarity	NPD7961	Discontinued
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7105	Intermediate Similarity	NPD230	Phase 1
0.7099	Intermediate Similarity	NPD4380	Phase 2
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7091	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6647	Phase 2
0.7088	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7305	Phase 1
0.7073	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5761	Phase 2
0.7073	Intermediate Similarity	NPD5760	Phase 2
0.7067	Intermediate Similarity	NPD7008	Discontinued
0.7063	Intermediate Similarity	NPD9545	Approved
0.7059	Intermediate Similarity	NPD7473	Discontinued
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.7021	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6801	Discontinued
0.7006	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2533	Approved
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD2532	Approved
0.6994	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5844	Phase 1
0.6972	Remote Similarity	NPD4198	Discontinued
0.6962	Remote Similarity	NPD8166	Discontinued
0.6957	Remote Similarity	NPD6273	Approved
0.6954	Remote Similarity	NPD6765	Approved
0.6954	Remote Similarity	NPD6764	Approved
0.6946	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6799	Approved
0.6928	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5402	Approved
0.6919	Remote Similarity	NPD3818	Discontinued
0.6918	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD164	Approved
0.6909	Remote Similarity	NPD37	Approved
0.6901	Remote Similarity	NPD5951	Approved
0.6894	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4965	Approved
0.6886	Remote Similarity	NPD4967	Phase 2
0.6886	Remote Similarity	NPD4966	Approved
0.6882	Remote Similarity	NPD6232	Discontinued
0.6879	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8313	Approved
0.6875	Remote Similarity	NPD8312	Approved
0.6871	Remote Similarity	NPD6287	Discontinued
0.6867	Remote Similarity	NPD6085	Phase 2
0.6867	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5048	Discontinued
0.6859	Remote Similarity	NPD2799	Discontinued
0.6855	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3750	Approved
0.6855	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7411	Suspended
0.6829	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3226	Approved
0.6826	Remote Similarity	NPD3817	Phase 2
0.6815	Remote Similarity	NPD6099	Approved
0.6815	Remote Similarity	NPD6100	Approved
0.6812	Remote Similarity	NPD6685	Approved
0.681	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5403	Approved
0.6809	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1934	Approved
0.6805	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6785	Approved
0.6798	Remote Similarity	NPD6784	Approved
0.6797	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1237	Approved
0.6786	Remote Similarity	NPD2067	Discontinued
0.6786	Remote Similarity	NPD3882	Suspended
0.6782	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6355	Discontinued
0.6772	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6004	Phase 3
0.6772	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6005	Phase 3
0.6772	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6002	Phase 3
0.6766	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5494	Approved
0.6755	Remote Similarity	NPD8320	Phase 1
0.6755	Remote Similarity	NPD8319	Approved
0.6753	Remote Similarity	NPD6663	Approved
0.6752	Remote Similarity	NPD1510	Phase 2
0.6752	Remote Similarity	NPD7033	Discontinued
0.6746	Remote Similarity	NPD3749	Approved
0.6743	Remote Similarity	NPD7074	Phase 3
0.6741	Remote Similarity	NPD1238	Approved
0.6738	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5126	Approved
0.6735	Remote Similarity	NPD5125	Phase 3
0.673	Remote Similarity	NPD1549	Phase 2
0.6728	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7199	Phase 2
0.6715	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1929	Approved
0.6715	Remote Similarity	NPD1930	Approved
0.6711	Remote Similarity	NPD5736	Approved
0.6711	Remote Similarity	NPD1608	Approved
0.671	Remote Similarity	NPD1240	Approved
0.6709	Remote Similarity	NPD2796	Approved
0.6709	Remote Similarity	NPD2935	Discontinued
0.6706	Remote Similarity	NPD6234	Discontinued
0.6705	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6166	Phase 2
0.6703	Remote Similarity	NPD7700	Phase 2
0.6703	Remote Similarity	NPD7699	Phase 2
0.6687	Remote Similarity	NPD2800	Approved
0.6687	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5401	Approved
0.6687	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7768	Phase 2
0.6686	Remote Similarity	NPD7054	Approved
0.6685	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8462	Phase 1
0.6667	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD1465	Phase 2
0.6648	Remote Similarity	NPD7472	Approved
0.6646	Remote Similarity	NPD3748	Approved
0.6646	Remote Similarity	NPD7003	Approved
0.6644	Remote Similarity	NPD4807	Approved
0.6644	Remote Similarity	NPD7610	Discontinued
0.6644	Remote Similarity	NPD4806	Approved
0.6643	Remote Similarity	NPD6858	Approved
0.6643	Remote Similarity	NPD7094	Approved
0.6633	Remote Similarity	NPD8404	Phase 2
0.663	Remote Similarity	NPD6535	Approved
0.663	Remote Similarity	NPD6534	Approved
0.6629	Remote Similarity	NPD7808	Phase 3
0.6629	Remote Similarity	NPD7228	Approved
0.6629	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1607	Approved
0.6624	Remote Similarity	NPD6651	Approved
0.6624	Remote Similarity	NPD6653	Approved
0.6622	Remote Similarity	NPD5306	Approved
0.6622	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5305	Approved
0.6618	Remote Similarity	NPD2066	Phase 3
0.6614	Remote Similarity	NPD7497	Discontinued
0.6614	Remote Similarity	NPD7435	Discontinued
0.66	Remote Similarity	NPD3972	Approved
0.6594	Remote Similarity	NPD5765	Approved
0.6594	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2313	Discontinued
0.6581	Remote Similarity	NPD3268	Approved
0.6573	Remote Similarity	NPD6912	Phase 3
0.6573	Remote Similarity	NPD7251	Discontinued
0.6568	Remote Similarity	NPD8455	Phase 2
0.6562	Remote Similarity	NPD5762	Approved
0.6562	Remote Similarity	NPD5763	Approved
0.6558	Remote Similarity	NPD6832	Phase 2
0.6552	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6385	Approved
0.6548	Remote Similarity	NPD6386	Approved
0.6547	Remote Similarity	NPD5909	Discontinued

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