NPASS Compound

Structure

CID129569 OpenBabel06191715482D 46 48 0 0 1 0 0 0 0 0999 V2000 -0.4986 2.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6324 -2.5832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6857 1.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4310 0.3668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2900 2.5541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7986 2.5396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3123 3.4289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3483 -0.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6756 0.7813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4503 0.5367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1993 1.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8993 0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6324 -0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3324 1.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4612 -2.1047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6857 0.1366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5972 1.3093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4612 3.0326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0655 3.1547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6447 3.4289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6324 0.2878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1993 0.6152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0655 1.2698 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6324 1.5971 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5669 1.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0655 0.6152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.8849 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6447 0.1137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6447 1.7713 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7331 0.6152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0655 1.2698 0.0000 C 0 0 1 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 -3.2900 -2.5832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5145 -0.3419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4965 1.6366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4612 3.9896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2317 4.0972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1232 4.2577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1232 -0.7151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5828 -0.7591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4612 -1.1477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8569 -0.3419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8641 1.9244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6324 2.5541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1662 2.8274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1232 2.6001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 30 1 0 0 0 0 9 30 1 0 0 0 0 11 22 1 0 0 0 0 11 24 1 0 0 0 0 12 23 1 0 0 0 0 12 32 1 0 0 0 0 13 41 1 0 0 0 0 14 23 1 0 0 0 0 14 25 2 0 0 0 0 15 33 2 0 0 0 0 15 41 1 0 0 0 0 16 34 2 0 0 0 0 16 42 1 0 0 0 0 17 35 2 0 0 0 0 17 43 1 0 0 0 0 18 36 2 0 0 0 0 18 44 1 0 0 0 0 19 37 2 0 0 0 0 19 45 1 0 0 0 0 20 38 2 0 0 0 0 20 46 1 0 0 0 0 21 13 1 6 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 42 1 1 0 0 0 23 43 1 6 0 0 0 24 31 1 6 0 0 0 24 44 1 0 0 0 0 25 27 1 0 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 31 1 6 0 0 0 27 29 1 0 0 0 0 27 45 1 6 0 0 0 28 32 1 1 0 0 0 28 39 1 0 0 0 0 29 31 1 1 0 0 0 29 46 1 0 0 0 0 30 32 1 0 0 0 0 31 10 1 6 0 0 0 32 40 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.29
Volume:	640.967
LogP:	2.061
LogD:	1.636
LogS:	-4.015
# Rotatable Bonds:	13
TPSA:	198.26
# H-Bond Aceptor:	14
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	5.881
Fsp3:	0.75
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:	0.00023377151228487492
Pgp-inhibitor:	0.997
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.957
20% Bioavailability (F20%):	0.229
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	43.183563232421875%
Volume Distribution (VD):	1.514
Pgp-substrate:	22.083316802978516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.499
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.217
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	2.529
Half-life (T1/2):	0.529

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.699
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.094
Carcinogencity:	0.066
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC129569

Natural Product ID:	NPC129569
*Common Name:**	MJFISQBJCXASCG-KUBLUVNXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MJFISQBJCXASCG-KUBLUVNXSA-N
Standard InCHI:	InChI=1S/C32H46O14/c1-14-23(43-17(4)35)12-32(40)28(39)26-21(13-41-15(2)33)22(42-16(3)34)11-24(44-18(5)36)31(26,10)29(46-20(7)38)27(45-19(6)37)25(14)30(32,8)9/h21-24,26-29,39-40H,11-13H2,1-10H3/t21-,22+,23+,24+,26+,27-,28+,29+,31-,32-/m1/s1
SMILES:	CC(=O)OC[C@@H]1[C@@H](OC(=O)C)C[C@@H]([C@@]2([C@@H]1[C@H](O)[C@]1(O)C[C@H](OC(=O)C)C(=C(C1(C)C)[C@H]([C@@H]2OC(=O)C)OC(=O)C)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL414246
PubChem CID:	5321759
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]
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	2
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	4.6	ug.mL-1	PMID[547089]
NPT2	Others	Unspecified		Control	=	147.0	%	PMID[547089]
NPT2	Others	Unspecified		Control	=	208.0	%	PMID[547089]
NPT27	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[547089]

☑ 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 NPC129569 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	251
0.1-0.2	1797
0.2-0.3	4861
0.3-0.4	10521
0.4-0.5	12373
0.5-0.6	7372
0.6-0.7	4862
0.7-0.8	607
0.8-0.85	29
0.85-0.9	13
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC182826
0.9775	High Similarity	NPC105375
0.9462	High Similarity	NPC188968
0.9462	High Similarity	NPC79303
0.9462	High Similarity	NPC271295
0.9348	High Similarity	NPC211810
0.9348	High Similarity	NPC284194
0.9348	High Similarity	NPC221801
0.9348	High Similarity	NPC471765
0.913	High Similarity	NPC472360
0.913	High Similarity	NPC472416
0.9101	High Similarity	NPC471779
0.9043	High Similarity	NPC473244
0.8901	High Similarity	NPC261320
0.8889	High Similarity	NPC472390
0.8804	High Similarity	NPC220216
0.8763	High Similarity	NPC472554
0.8737	High Similarity	NPC475304
0.8713	High Similarity	NPC475586
0.871	High Similarity	NPC124374
0.8673	High Similarity	NPC472552
0.8646	High Similarity	NPC254121
0.8632	High Similarity	NPC37603
0.8632	High Similarity	NPC471786
0.8617	High Similarity	NPC99653
0.8614	High Similarity	NPC472439
0.8614	High Similarity	NPC469916
0.86	High Similarity	NPC111952
0.8586	High Similarity	NPC474124
0.8571	High Similarity	NPC102996
0.8515	High Similarity	NPC112780
0.8515	High Similarity	NPC143609
0.85	High Similarity	NPC473543
0.8495	Intermediate Similarity	NPC246028
0.8485	Intermediate Similarity	NPC475344
0.8485	Intermediate Similarity	NPC476471
0.8478	Intermediate Similarity	NPC102640
0.8469	Intermediate Similarity	NPC38855
0.8438	Intermediate Similarity	NPC292178
0.8438	Intermediate Similarity	NPC86893
0.8404	Intermediate Similarity	NPC48732
0.84	Intermediate Similarity	NPC473523
0.8387	Intermediate Similarity	NPC69713
0.8384	Intermediate Similarity	NPC475617
0.8333	Intermediate Similarity	NPC473586
0.83	Intermediate Similarity	NPC165578
0.83	Intermediate Similarity	NPC11956
0.8298	Intermediate Similarity	NPC20946
0.8283	Intermediate Similarity	NPC274643
0.8283	Intermediate Similarity	NPC473510
0.8283	Intermediate Similarity	NPC230546
0.8252	Intermediate Similarity	NPC50124
0.8252	Intermediate Similarity	NPC475263
0.8252	Intermediate Similarity	NPC151393
0.8247	Intermediate Similarity	NPC276110
0.8229	Intermediate Similarity	NPC110022
0.8218	Intermediate Similarity	NPC99266
0.8218	Intermediate Similarity	NPC8196
0.8218	Intermediate Similarity	NPC23584
0.82	Intermediate Similarity	NPC280991
0.82	Intermediate Similarity	NPC96784
0.82	Intermediate Similarity	NPC235920
0.82	Intermediate Similarity	NPC11974
0.8182	Intermediate Similarity	NPC477875
0.8182	Intermediate Similarity	NPC477876
0.8173	Intermediate Similarity	NPC472216
0.8173	Intermediate Similarity	NPC284828
0.8173	Intermediate Similarity	NPC173905
0.8173	Intermediate Similarity	NPC5475
0.8173	Intermediate Similarity	NPC40728
0.8137	Intermediate Similarity	NPC473577
0.8137	Intermediate Similarity	NPC475585
0.8137	Intermediate Similarity	NPC474550
0.8137	Intermediate Similarity	NPC470768
0.8125	Intermediate Similarity	NPC477574
0.8125	Intermediate Similarity	NPC41239
0.8119	Intermediate Similarity	NPC137430
0.8119	Intermediate Similarity	NPC295791
0.81	Intermediate Similarity	NPC272223
0.81	Intermediate Similarity	NPC475877
0.8095	Intermediate Similarity	NPC177047
0.8085	Intermediate Similarity	NPC131329
0.8085	Intermediate Similarity	NPC245004
0.8081	Intermediate Similarity	NPC199099
0.8081	Intermediate Similarity	NPC210337
0.8077	Intermediate Similarity	NPC128795
0.8077	Intermediate Similarity	NPC217921
0.8077	Intermediate Similarity	NPC135015
0.8077	Intermediate Similarity	NPC48548
0.8077	Intermediate Similarity	NPC38948
0.8065	Intermediate Similarity	NPC35933
0.8058	Intermediate Similarity	NPC470763
0.8058	Intermediate Similarity	NPC88349
0.8058	Intermediate Similarity	NPC470767
0.8058	Intermediate Similarity	NPC475290
0.8039	Intermediate Similarity	NPC474822
0.8039	Intermediate Similarity	NPC159533
0.802	Intermediate Similarity	NPC97435
0.802	Intermediate Similarity	NPC476132
0.8	Intermediate Similarity	NPC470067
0.8	Intermediate Similarity	NPC247233
0.8	Intermediate Similarity	NPC470068
0.8	Intermediate Similarity	NPC316974
0.8	Intermediate Similarity	NPC470066
0.8	Intermediate Similarity	NPC206618
0.7981	Intermediate Similarity	NPC475781
0.7981	Intermediate Similarity	NPC187435
0.7981	Intermediate Similarity	NPC125423
0.7981	Intermediate Similarity	NPC471205
0.7981	Intermediate Similarity	NPC469318
0.7981	Intermediate Similarity	NPC122816
0.7981	Intermediate Similarity	NPC473173
0.7981	Intermediate Similarity	NPC67321
0.7981	Intermediate Similarity	NPC88013
0.798	Intermediate Similarity	NPC57664
0.798	Intermediate Similarity	NPC227583
0.798	Intermediate Similarity	NPC472995
0.798	Intermediate Similarity	NPC98457
0.798	Intermediate Similarity	NPC12103
0.798	Intermediate Similarity	NPC88009
0.7959	Intermediate Similarity	NPC105490
0.7957	Intermediate Similarity	NPC83702
0.7944	Intermediate Similarity	NPC470025
0.7944	Intermediate Similarity	NPC328074
0.7944	Intermediate Similarity	NPC317460
0.7944	Intermediate Similarity	NPC321272
0.7941	Intermediate Similarity	NPC470053
0.7925	Intermediate Similarity	NPC475563
0.7925	Intermediate Similarity	NPC475134
0.7925	Intermediate Similarity	NPC472214
0.7925	Intermediate Similarity	NPC472215
0.7925	Intermediate Similarity	NPC316708
0.7921	Intermediate Similarity	NPC474571
0.7921	Intermediate Similarity	NPC474190
0.7921	Intermediate Similarity	NPC254567
0.7921	Intermediate Similarity	NPC476195
0.7905	Intermediate Similarity	NPC311223
0.7905	Intermediate Similarity	NPC472218
0.7905	Intermediate Similarity	NPC472217
0.7905	Intermediate Similarity	NPC472219
0.79	Intermediate Similarity	NPC125551
0.79	Intermediate Similarity	NPC96597
0.79	Intermediate Similarity	NPC274793
0.79	Intermediate Similarity	NPC239547
0.79	Intermediate Similarity	NPC91197
0.79	Intermediate Similarity	NPC309503
0.79	Intermediate Similarity	NPC155319
0.7895	Intermediate Similarity	NPC233744
0.7885	Intermediate Similarity	NPC477877
0.7885	Intermediate Similarity	NPC51719
0.7885	Intermediate Similarity	NPC471206
0.7879	Intermediate Similarity	NPC476720
0.7879	Intermediate Similarity	NPC8774
0.787	Intermediate Similarity	NPC471204
0.787	Intermediate Similarity	NPC470027
0.787	Intermediate Similarity	NPC311592
0.787	Intermediate Similarity	NPC75167
0.7864	Intermediate Similarity	NPC475334
0.7864	Intermediate Similarity	NPC475623
0.7864	Intermediate Similarity	NPC475889
0.7864	Intermediate Similarity	NPC7644
0.7864	Intermediate Similarity	NPC7613
0.7864	Intermediate Similarity	NPC281378
0.7864	Intermediate Similarity	NPC127933
0.7864	Intermediate Similarity	NPC473694
0.7864	Intermediate Similarity	NPC218513
0.7864	Intermediate Similarity	NPC55954
0.7857	Intermediate Similarity	NPC472640
0.7857	Intermediate Similarity	NPC27918
0.7857	Intermediate Similarity	NPC53555
0.7857	Intermediate Similarity	NPC472641
0.7857	Intermediate Similarity	NPC137461
0.7857	Intermediate Similarity	NPC7349
0.785	Intermediate Similarity	NPC475668
0.785	Intermediate Similarity	NPC475480
0.785	Intermediate Similarity	NPC17791
0.785	Intermediate Similarity	NPC473921
0.785	Intermediate Similarity	NPC470026
0.7849	Intermediate Similarity	NPC23748
0.7849	Intermediate Similarity	NPC49208
0.7843	Intermediate Similarity	NPC470054
0.7843	Intermediate Similarity	NPC49532
0.7835	Intermediate Similarity	NPC473269
0.7835	Intermediate Similarity	NPC209816
0.783	Intermediate Similarity	NPC299590
0.783	Intermediate Similarity	NPC42662
0.7826	Intermediate Similarity	NPC25554
0.7822	Intermediate Similarity	NPC278673
0.7822	Intermediate Similarity	NPC477928
0.7818	Intermediate Similarity	NPC473590
0.781	Intermediate Similarity	NPC109376
0.78	Intermediate Similarity	NPC165632
0.78	Intermediate Similarity	NPC472997
0.78	Intermediate Similarity	NPC472996
0.78	Intermediate Similarity	NPC288970
0.7798	Intermediate Similarity	NPC181145
0.7789	Intermediate Similarity	NPC255143
0.7789	Intermediate Similarity	NPC476217
0.7788	Intermediate Similarity	NPC288502
0.7788	Intermediate Similarity	NPC121518

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 NPC129569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	2264
0.2-0.3	3649
0.3-0.4	2006
0.4-0.5	667
0.5-0.6	288
0.6-0.7	49
0.7-0.8	4
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
0.783	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5344	Discontinued
0.7593	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7327	Approved
0.7434	Intermediate Similarity	NPD7328	Approved
0.7391	Intermediate Similarity	NPD8380	Approved
0.7391	Intermediate Similarity	NPD8379	Approved
0.7391	Intermediate Similarity	NPD8378	Approved
0.7391	Intermediate Similarity	NPD8033	Approved
0.7391	Intermediate Similarity	NPD8296	Approved
0.7391	Intermediate Similarity	NPD8335	Approved
0.7368	Intermediate Similarity	NPD7516	Approved
0.7339	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4225	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7304	Intermediate Similarity	NPD8294	Approved
0.7304	Intermediate Similarity	NPD8377	Approved
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD6648	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7129	Intermediate Similarity	NPD7838	Discovery
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7094	Intermediate Similarity	NPD7503	Approved
0.7091	Intermediate Similarity	NPD6686	Approved
0.7091	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6698	Approved
0.6961	Remote Similarity	NPD46	Approved
0.693	Remote Similarity	NPD8133	Approved
0.6897	Remote Similarity	NPD7115	Discovery
0.686	Remote Similarity	NPD7507	Approved
0.6852	Remote Similarity	NPD4159	Approved
0.6832	Remote Similarity	NPD7524	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.67	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6604	Remote Similarity	NPD7748	Approved
0.66	Remote Similarity	NPD6695	Phase 3
0.6583	Remote Similarity	NPD6319	Approved
0.6574	Remote Similarity	NPD7902	Approved
0.6571	Remote Similarity	NPD7983	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6557	Remote Similarity	NPD8328	Phase 3
0.6538	Remote Similarity	NPD6051	Approved
0.6531	Remote Similarity	NPD7645	Phase 2
0.6529	Remote Similarity	NPD6921	Approved
0.6509	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD5778	Approved
0.6509	Remote Similarity	NPD6399	Phase 3
0.6505	Remote Similarity	NPD7750	Discontinued
0.6496	Remote Similarity	NPD4632	Approved
0.6466	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7525	Registered
0.646	Remote Similarity	NPD6675	Approved
0.646	Remote Similarity	NPD6402	Approved
0.646	Remote Similarity	NPD7128	Approved
0.646	Remote Similarity	NPD5739	Approved
0.6435	Remote Similarity	NPD6372	Approved
0.6435	Remote Similarity	NPD6373	Approved
0.6415	Remote Similarity	NPD7515	Phase 2
0.641	Remote Similarity	NPD6053	Discontinued
0.6404	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6412	Phase 2
0.64	Remote Similarity	NPD8074	Phase 3
0.6383	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6371	Approved
0.6373	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6881	Approved
0.6348	Remote Similarity	NPD6899	Approved
0.6348	Remote Similarity	NPD7320	Approved
0.6325	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD8130	Phase 1
0.6325	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD3168	Discontinued
0.63	Remote Similarity	NPD6930	Phase 2
0.63	Remote Similarity	NPD6931	Approved
0.6296	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD8264	Approved
0.6271	Remote Similarity	NPD6882	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6264	Remote Similarity	NPD371	Approved
0.6262	Remote Similarity	NPD8035	Phase 2
0.6262	Remote Similarity	NPD8034	Phase 2
0.6262	Remote Similarity	NPD6411	Approved
0.6261	Remote Similarity	NPD5701	Approved
0.6261	Remote Similarity	NPD5697	Approved
0.624	Remote Similarity	NPD7492	Approved
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.622	Remote Similarity	NPD7736	Approved
0.62	Remote Similarity	NPD6929	Approved
0.6198	Remote Similarity	NPD6009	Approved
0.619	Remote Similarity	NPD6616	Approved
0.619	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD6869	Approved
0.6179	Remote Similarity	NPD6059	Approved
0.6179	Remote Similarity	NPD6054	Approved
0.6174	Remote Similarity	NPD6008	Approved
0.616	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6142	Remote Similarity	NPD7078	Approved
0.6139	Remote Similarity	NPD7332	Phase 2
0.6139	Remote Similarity	NPD7514	Phase 3
0.6139	Remote Similarity	NPD4748	Discontinued
0.6129	Remote Similarity	NPD5983	Phase 2
0.6126	Remote Similarity	NPD6084	Phase 2
0.6126	Remote Similarity	NPD6083	Phase 2
0.6122	Remote Similarity	NPD6942	Approved
0.6122	Remote Similarity	NPD7339	Approved
0.6111	Remote Similarity	NPD7087	Discontinued
0.608	Remote Similarity	NPD6370	Approved
0.6075	Remote Similarity	NPD6101	Approved
0.6075	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6011	Approved
0.6063	Remote Similarity	NPD6336	Discontinued
0.6061	Remote Similarity	NPD6933	Approved
0.6061	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4786	Approved
0.6053	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6640	Phase 3
0.6019	Remote Similarity	NPD3667	Approved
0.6019	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD6925	Approved
0.5982	Remote Similarity	NPD4755	Approved
0.5966	Remote Similarity	NPD4634	Approved
0.5962	Remote Similarity	NPD3669	Approved
0.5962	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD7260	Phase 2
0.5952	Remote Similarity	NPD5988	Approved
0.5946	Remote Similarity	NPD5695	Phase 3
0.5943	Remote Similarity	NPD3618	Phase 1
0.5941	Remote Similarity	NPD6115	Approved
0.5941	Remote Similarity	NPD6114	Approved
0.5941	Remote Similarity	NPD6118	Approved
0.5941	Remote Similarity	NPD7145	Approved
0.5941	Remote Similarity	NPD6697	Approved
0.5938	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5328	Approved
0.5922	Remote Similarity	NPD6902	Approved
0.5922	Remote Similarity	NPD6898	Phase 1
0.5913	Remote Similarity	NPD5211	Phase 2
0.5909	Remote Similarity	NPD6845	Suspended
0.5909	Remote Similarity	NPD4202	Approved
0.5909	Remote Similarity	NPD8171	Discontinued
0.5897	Remote Similarity	NPD5357	Phase 1
0.5893	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4250	Approved
0.5888	Remote Similarity	NPD4251	Approved
0.5882	Remote Similarity	NPD6683	Phase 2
0.5877	Remote Similarity	NPD4700	Approved
0.5877	Remote Similarity	NPD5286	Approved
0.5877	Remote Similarity	NPD4696	Approved
0.5877	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD6926	Approved
0.5859	Remote Similarity	NPD6924	Approved
0.5854	Remote Similarity	NPD6274	Approved
0.5849	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6116	Phase 1
0.584	Remote Similarity	NPD7100	Approved
0.584	Remote Similarity	NPD7101	Approved
0.5825	Remote Similarity	NPD4819	Approved
0.5825	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD4821	Approved
0.5825	Remote Similarity	NPD7509	Discontinued
0.5825	Remote Similarity	NPD4820	Approved
0.5825	Remote Similarity	NPD4822	Approved
0.5818	Remote Similarity	NPD6079	Approved
0.5816	Remote Similarity	NPD7625	Phase 1
0.5812	Remote Similarity	NPD5141	Approved
0.58	Remote Similarity	NPD8039	Approved
0.5794	Remote Similarity	NPD6409	Approved
0.5794	Remote Similarity	NPD7146	Approved
0.5794	Remote Similarity	NPD7334	Approved
0.5794	Remote Similarity	NPD6684	Approved
0.5794	Remote Similarity	NPD5330	Approved
0.5794	Remote Similarity	NPD7521	Approved
0.5794	Remote Similarity	NPD4249	Approved
0.5789	Remote Similarity	NPD5696	Approved
0.5781	Remote Similarity	NPD6067	Discontinued
0.5776	Remote Similarity	NPD5225	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