NPASS Compound

Structure

NPC475328 OpenBabel07101718242D 52 54 0 0 1 0 0 0 0 0999 V2000 0.3677 0.4044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3988 -1.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0118 -4.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6974 -0.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0880 1.2159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6032 -2.6271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4364 2.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4341 -0.6685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4729 -1.6294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5493 -3.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7164 -4.2720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5493 -2.8294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8835 -3.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7164 -2.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0506 -2.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2178 -2.8294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1004 -2.4916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2134 -2.0728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0535 -1.2903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9838 -3.1141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1464 -0.4084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5531 -0.2356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0509 -4.7785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7365 -0.5246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8795 0.6696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0255 -3.3959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5907 1.5575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8835 -2.8294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4698 -2.3013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1744 -2.0341 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3006 -1.2600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9333 -0.7013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8862 -1.8677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6938 -2.3952 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3849 -2.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1073 -0.3697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5992 -0.0484 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6213 -1.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6040 -5.6301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2895 0.3270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7484 1.0819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4024 -4.2807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4899 1.2165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3849 -1.3869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9038 0.8639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5369 -3.9657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2225 -1.3374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8021 -0.2890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0707 -3.2800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1543 0.9493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5520 -2.8294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 39 1 0 0 0 0 9 39 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 28 2 0 0 0 0 14 28 1 0 0 0 0 15 16 2 0 0 0 0 15 28 1 0 0 0 0 16 35 1 0 0 0 0 17 29 2 0 0 0 0 17 34 1 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 19 33 1 0 0 0 0 20 29 1 0 0 0 0 20 47 1 0 0 0 0 21 31 1 0 0 0 0 21 36 2 0 0 0 0 22 32 1 0 0 0 0 22 38 2 0 0 0 0 23 40 2 0 0 0 0 23 47 1 0 0 0 0 24 41 2 0 0 0 0 24 48 1 0 0 0 0 25 42 2 0 0 0 0 25 49 1 0 0 0 0 26 43 2 0 0 0 0 26 50 1 0 0 0 0 27 44 2 0 0 0 0 27 51 1 0 0 0 0 29 33 1 0 0 0 0 30 18 1 6 0 0 0 30 34 1 0 0 0 0 30 39 1 0 0 0 0 31 48 1 1 0 0 0 32 49 1 1 0 0 0 33 52 1 6 0 0 0 34 50 1 6 0 0 0 35 45 2 0 0 0 0 35 52 1 0 0 0 0 36 37 1 0 0 0 0 36 39 1 0 0 0 0 37 38 1 0 0 0 0 37 46 1 1 0 0 0 38 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	724.31
Volume:	737.429
LogP:	3.949
LogD:	2.605
LogS:	-4.609
# Rotatable Bonds:	15
TPSA:	178.03
# H-Bond Aceptor:	13
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	6.178
Fsp3:	0.487
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:	-5.022
MDCK Permeability:	0.00022099346097093076
Pgp-inhibitor:	1.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.085
20% Bioavailability (F20%):	0.231
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	79.01395416259766%
Volume Distribution (VD):	1.639
Pgp-substrate:	11.340849876403809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.705
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.253
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.436
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	3.298
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.38
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.691
Carcinogencity:	0.031
Eye Corrosion:	0.033
Eye Irritation:	0.1
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC475328

Natural Product ID:	NPC475328
*Common Name:**	Taxuspine X
IUPAC Name:	[(1R,2S,3E,5S,7S,8Z,10R,13S)-2,7,9,13-tetraacetyloxy-4-(acetyloxymethyl)-10-hydroxy-8,12,15,15-tetramethyl-5-bicyclo[9.3.1]pentadeca-3,8,11-trienyl] (E)-3-phenylprop-2-enoate
Synonyms:	taxuspine X
Standard InCHIKey:	VOVBOUNKNIVZDV-AXCJLGEXSA-N
Standard InCHI:	InChI=1S/C39H48O13/c1-21-31(48-24(4)41)18-30-34(50-26(6)43)17-29(20-47-23(3)40)33(52-35(45)16-15-28-13-11-10-12-14-28)19-32(49-25(5)42)22(2)38(51-27(7)44)37(46)36(21)39(30,8)9/h10-17,30-34,37,46H,18-20H2,1-9H3/b16-15+,29-17+,38-22-/t30-,31-,32-,33-,34-,37+/m0/s1
SMILES:	CC1=C2C(C(=C(C(CC(C(=CC(C(C2(C)C)CC1OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C=CC3=CC=CC=C3)OC(=O)C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503539
PubChem CID:	44566205
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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	105.0	%	PMID[534448]

☑ 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 NPC475328 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	222
0.1-0.2	862
0.2-0.3	2007
0.3-0.4	5811
0.4-0.5	9261
0.5-0.6	16321
0.6-0.7	7438
0.7-0.8	733
0.8-0.85	32
0.85-0.9	8
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9386	High Similarity	NPC476476
0.9262	High Similarity	NPC93632
0.9174	High Similarity	NPC45821
0.9167	High Similarity	NPC472373
0.9091	High Similarity	NPC471758
0.9083	High Similarity	NPC12016
0.8974	High Similarity	NPC470820
0.876	High Similarity	NPC300827
0.876	High Similarity	NPC473439
0.872	High Similarity	NPC58061
0.872	High Similarity	NPC230331
0.8667	High Similarity	NPC89324
0.864	High Similarity	NPC476972
0.864	High Similarity	NPC476971
0.8594	High Similarity	NPC80599
0.8583	High Similarity	NPC473443
0.8583	High Similarity	NPC472388
0.856	High Similarity	NPC476970
0.856	High Similarity	NPC475933
0.856	High Similarity	NPC470158
0.8548	High Similarity	NPC470815
0.8537	High Similarity	NPC473749
0.8504	High Similarity	NPC225103
0.848	Intermediate Similarity	NPC284022
0.845	Intermediate Similarity	NPC476976
0.8372	Intermediate Similarity	NPC476977
0.8333	Intermediate Similarity	NPC472374
0.8333	Intermediate Similarity	NPC472372
0.832	Intermediate Similarity	NPC473871
0.832	Intermediate Similarity	NPC473870
0.8308	Intermediate Similarity	NPC209851
0.8281	Intermediate Similarity	NPC195224
0.8276	Intermediate Similarity	NPC477251
0.824	Intermediate Similarity	NPC473889
0.824	Intermediate Similarity	NPC70973
0.8189	Intermediate Similarity	NPC473083
0.8175	Intermediate Similarity	NPC204644
0.8162	Intermediate Similarity	NPC473755
0.8162	Intermediate Similarity	NPC34012
0.8162	Intermediate Similarity	NPC475513
0.816	Intermediate Similarity	NPC311175
0.816	Intermediate Similarity	NPC37641
0.8148	Intermediate Similarity	NPC472547
0.8145	Intermediate Similarity	NPC470814
0.813	Intermediate Similarity	NPC84129
0.8129	Intermediate Similarity	NPC320734
0.8125	Intermediate Similarity	NPC473111
0.8125	Intermediate Similarity	NPC473110
0.811	Intermediate Similarity	NPC469742
0.8106	Intermediate Similarity	NPC15850
0.8092	Intermediate Similarity	NPC472418
0.8083	Intermediate Similarity	NPC477250
0.8062	Intermediate Similarity	NPC171007
0.8062	Intermediate Similarity	NPC190849
0.8047	Intermediate Similarity	NPC114927
0.8047	Intermediate Similarity	NPC474532
0.8043	Intermediate Similarity	NPC38696
0.8029	Intermediate Similarity	NPC192658
0.8	Intermediate Similarity	NPC27721
0.8	Intermediate Similarity	NPC39549
0.7986	Intermediate Similarity	NPC472556
0.7984	Intermediate Similarity	NPC473082
0.7984	Intermediate Similarity	NPC470816
0.7969	Intermediate Similarity	NPC140118
0.7969	Intermediate Similarity	NPC12881
0.7966	Intermediate Similarity	NPC136962
0.7966	Intermediate Similarity	NPC37115
0.7956	Intermediate Similarity	NPC472576
0.7956	Intermediate Similarity	NPC27377
0.7956	Intermediate Similarity	NPC16912
0.7956	Intermediate Similarity	NPC470617
0.7956	Intermediate Similarity	NPC87448
0.7956	Intermediate Similarity	NPC470616
0.7956	Intermediate Similarity	NPC118080
0.7956	Intermediate Similarity	NPC291599
0.7956	Intermediate Similarity	NPC41481
0.7956	Intermediate Similarity	NPC97947
0.7934	Intermediate Similarity	NPC234376
0.7926	Intermediate Similarity	NPC472545
0.7926	Intermediate Similarity	NPC202729
0.7926	Intermediate Similarity	NPC472551
0.7923	Intermediate Similarity	NPC473423
0.792	Intermediate Similarity	NPC473860
0.7914	Intermediate Similarity	NPC34943
0.7914	Intermediate Similarity	NPC111466
0.791	Intermediate Similarity	NPC38420
0.791	Intermediate Similarity	NPC28836
0.791	Intermediate Similarity	NPC136608
0.7899	Intermediate Similarity	NPC140021
0.7899	Intermediate Similarity	NPC472546
0.7886	Intermediate Similarity	NPC473869
0.7883	Intermediate Similarity	NPC97667
0.7883	Intermediate Similarity	NPC87934
0.7883	Intermediate Similarity	NPC171207
0.7883	Intermediate Similarity	NPC139243
0.7883	Intermediate Similarity	NPC100913
0.7883	Intermediate Similarity	NPC275592
0.7883	Intermediate Similarity	NPC473440
0.7883	Intermediate Similarity	NPC162613
0.7883	Intermediate Similarity	NPC116742
0.7883	Intermediate Similarity	NPC90614
0.7869	Intermediate Similarity	NPC265002
0.7857	Intermediate Similarity	NPC470159
0.7857	Intermediate Similarity	NPC29704
0.7857	Intermediate Similarity	NPC158663
0.7857	Intermediate Similarity	NPC171525
0.7857	Intermediate Similarity	NPC469349
0.7857	Intermediate Similarity	NPC277053
0.7857	Intermediate Similarity	NPC177940
0.7857	Intermediate Similarity	NPC264270
0.7857	Intermediate Similarity	NPC471104
0.7857	Intermediate Similarity	NPC96903
0.7857	Intermediate Similarity	NPC40085
0.7857	Intermediate Similarity	NPC470157
0.7857	Intermediate Similarity	NPC472575
0.7857	Intermediate Similarity	NPC200471
0.7857	Intermediate Similarity	NPC472572
0.7857	Intermediate Similarity	NPC174982
0.7857	Intermediate Similarity	NPC472568
0.7857	Intermediate Similarity	NPC473088
0.7857	Intermediate Similarity	NPC301946
0.7857	Intermediate Similarity	NPC472571
0.7857	Intermediate Similarity	NPC70403
0.7857	Intermediate Similarity	NPC184817
0.7857	Intermediate Similarity	NPC476973
0.7852	Intermediate Similarity	NPC477896
0.7852	Intermediate Similarity	NPC477893
0.7842	Intermediate Similarity	NPC477894
0.7836	Intermediate Similarity	NPC472248
0.7833	Intermediate Similarity	NPC184633
0.7826	Intermediate Similarity	NPC224491
0.782	Intermediate Similarity	NPC472361
0.7817	Intermediate Similarity	NPC474564
0.7815	Intermediate Similarity	NPC474376
0.7815	Intermediate Similarity	NPC475203
0.7815	Intermediate Similarity	NPC472315
0.7815	Intermediate Similarity	NPC472316
0.781	Intermediate Similarity	NPC475195
0.781	Intermediate Similarity	NPC9905
0.781	Intermediate Similarity	NPC473301
0.7805	Intermediate Similarity	NPC474641
0.7801	Intermediate Similarity	NPC240115
0.7801	Intermediate Similarity	NPC473602
0.7801	Intermediate Similarity	NPC20255
0.7801	Intermediate Similarity	NPC474935
0.7797	Intermediate Similarity	NPC171831
0.7797	Intermediate Similarity	NPC242913
0.7797	Intermediate Similarity	NPC280616
0.7787	Intermediate Similarity	NPC470825
0.7786	Intermediate Similarity	NPC476974
0.7786	Intermediate Similarity	NPC472573
0.7786	Intermediate Similarity	NPC276047
0.7786	Intermediate Similarity	NPC472570
0.7786	Intermediate Similarity	NPC95265
0.7786	Intermediate Similarity	NPC475122
0.7786	Intermediate Similarity	NPC470152
0.7786	Intermediate Similarity	NPC11685
0.7786	Intermediate Similarity	NPC163719
0.7786	Intermediate Similarity	NPC5486
0.7786	Intermediate Similarity	NPC57628
0.7786	Intermediate Similarity	NPC70716
0.7786	Intermediate Similarity	NPC267733
0.7786	Intermediate Similarity	NPC80895
0.7786	Intermediate Similarity	NPC241951
0.7786	Intermediate Similarity	NPC125106
0.7786	Intermediate Similarity	NPC188865
0.7786	Intermediate Similarity	NPC95810
0.7786	Intermediate Similarity	NPC475759
0.7786	Intermediate Similarity	NPC25768
0.7786	Intermediate Similarity	NPC471912
0.7786	Intermediate Similarity	NPC472569
0.7778	Intermediate Similarity	NPC311492
0.777	Intermediate Similarity	NPC63737
0.7769	Intermediate Similarity	NPC145287
0.7762	Intermediate Similarity	NPC476092
0.7762	Intermediate Similarity	NPC475447
0.7762	Intermediate Similarity	NPC475218
0.7762	Intermediate Similarity	NPC70236
0.7761	Intermediate Similarity	NPC239358
0.7761	Intermediate Similarity	NPC233860
0.7761	Intermediate Similarity	NPC472394
0.7761	Intermediate Similarity	NPC233692
0.7752	Intermediate Similarity	NPC182333
0.7752	Intermediate Similarity	NPC273336
0.7752	Intermediate Similarity	NPC108286
0.7746	Intermediate Similarity	NPC217918
0.7744	Intermediate Similarity	NPC475138
0.773	Intermediate Similarity	NPC311825
0.773	Intermediate Similarity	NPC26045
0.773	Intermediate Similarity	NPC125882
0.773	Intermediate Similarity	NPC92867
0.7724	Intermediate Similarity	NPC477246
0.7724	Intermediate Similarity	NPC477245
0.7721	Intermediate Similarity	NPC200154
0.7714	Intermediate Similarity	NPC95449
0.7714	Intermediate Similarity	NPC163087
0.7714	Intermediate Similarity	NPC91703
0.771	Intermediate Similarity	NPC275576
0.7708	Intermediate Similarity	NPC197037
0.7708	Intermediate Similarity	NPC470153

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 NPC475328 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	676
0.2-0.3	1522
0.3-0.4	2969
0.4-0.5	2149
0.5-0.6	1379
0.6-0.7	251
0.7-0.8	12
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
0.7574	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7741	Discontinued
0.7417	Intermediate Similarity	NPD6647	Phase 2
0.7385	Intermediate Similarity	NPD5126	Approved
0.7385	Intermediate Similarity	NPD5125	Phase 3
0.7323	Intermediate Similarity	NPD2629	Approved
0.7266	Intermediate Similarity	NPD4198	Discontinued
0.7259	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6685	Approved
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD7266	Discontinued
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD5763	Approved
0.7109	Intermediate Similarity	NPD6010	Discontinued
0.7103	Intermediate Similarity	NPD8166	Discontinued
0.7101	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5909	Discontinued
0.7063	Intermediate Similarity	NPD2067	Discontinued
0.7016	Intermediate Similarity	NPD5048	Discontinued
0.7008	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7236	Approved
0.7007	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5765	Approved
0.6992	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8651	Approved
0.6984	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1282	Approved
0.6953	Remote Similarity	NPD6912	Phase 3
0.6943	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD7838	Discovery
0.6917	Remote Similarity	NPD7503	Approved
0.6899	Remote Similarity	NPD7094	Approved
0.6899	Remote Similarity	NPD6858	Approved
0.6894	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7239	Suspended
0.687	Remote Similarity	NPD7157	Approved
0.6867	Remote Similarity	NPD8434	Phase 2
0.6833	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6049	Phase 2
0.6832	Remote Similarity	NPD7799	Discontinued
0.6831	Remote Similarity	NPD4060	Phase 1
0.6822	Remote Similarity	NPD969	Suspended
0.6809	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5124	Phase 1
0.6781	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6002	Phase 3
0.6781	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6005	Phase 3
0.6781	Remote Similarity	NPD6004	Phase 3
0.6768	Remote Similarity	NPD8368	Discontinued
0.6757	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4626	Approved
0.6738	Remote Similarity	NPD7008	Discontinued
0.6736	Remote Similarity	NPD6653	Approved
0.6714	Remote Similarity	NPD5736	Approved
0.6713	Remote Similarity	NPD4140	Approved
0.6694	Remote Similarity	NPD5344	Discontinued
0.6691	Remote Similarity	NPD3496	Discontinued
0.6691	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD5951	Approved
0.6647	Remote Similarity	NPD8407	Phase 2
0.6645	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1091	Approved
0.6641	Remote Similarity	NPD7843	Approved
0.6618	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2066	Phase 3
0.6613	Remote Similarity	NPD6648	Approved
0.6613	Remote Similarity	NPD7798	Approved
0.6603	Remote Similarity	NPD37	Approved
0.66	Remote Similarity	NPD6190	Approved
0.6594	Remote Similarity	NPD6637	Approved
0.6591	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD2182	Approved
0.6588	Remote Similarity	NPD8361	Approved
0.6588	Remote Similarity	NPD8360	Approved
0.6587	Remote Similarity	NPD8313	Approved
0.6587	Remote Similarity	NPD8312	Approved
0.6587	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4966	Approved
0.6582	Remote Similarity	NPD4967	Phase 2
0.6582	Remote Similarity	NPD4965	Approved
0.6579	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1652	Phase 2
0.6575	Remote Similarity	NPD7097	Phase 1
0.6573	Remote Similarity	NPD7985	Registered
0.6569	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD8150	Discontinued
0.6568	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8455	Phase 2
0.6552	Remote Similarity	NPD5735	Approved
0.6541	Remote Similarity	NPD7075	Discontinued
0.6532	Remote Similarity	NPD5926	Approved
0.6532	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4225	Approved
0.6531	Remote Similarity	NPD7305	Phase 1
0.6528	Remote Similarity	NPD6663	Approved
0.6528	Remote Similarity	NPD7961	Discontinued
0.6522	Remote Similarity	NPD3092	Approved
0.6516	Remote Similarity	NPD7458	Discontinued
0.6512	Remote Similarity	NPD6686	Approved
0.6512	Remote Similarity	NPD1358	Approved
0.6509	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3027	Phase 3
0.6503	Remote Similarity	NPD7095	Approved
0.65	Remote Similarity	NPD6234	Discontinued
0.6496	Remote Similarity	NPD1778	Approved
0.6496	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8435	Approved
0.6478	Remote Similarity	NPD7057	Phase 3
0.6478	Remote Similarity	NPD7058	Phase 2
0.6474	Remote Similarity	NPD6599	Discontinued
0.6474	Remote Similarity	NPD4380	Phase 2
0.6467	Remote Similarity	NPD6674	Discontinued
0.6467	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD3971	Phase 1
0.6457	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1929	Approved
0.6457	Remote Similarity	NPD1930	Approved
0.6456	Remote Similarity	NPD7819	Suspended
0.6456	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD2797	Approved
0.6452	Remote Similarity	NPD1653	Approved
0.6434	Remote Similarity	NPD3134	Approved
0.6429	Remote Similarity	NPD6273	Approved
0.6424	Remote Similarity	NPD7228	Approved
0.6424	Remote Similarity	NPD7003	Approved
0.6419	Remote Similarity	NPD7033	Discontinued
0.6417	Remote Similarity	NPD689	Discontinued
0.6414	Remote Similarity	NPD4248	Discontinued
0.641	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6085	Phase 2
0.6403	Remote Similarity	NPD4807	Approved
0.6403	Remote Similarity	NPD4806	Approved
0.6403	Remote Similarity	NPD422	Phase 1
0.64	Remote Similarity	NPD9495	Approved
0.64	Remote Similarity	NPD2424	Discontinued
0.6393	Remote Similarity	NPD1088	Approved
0.6392	Remote Similarity	NPD6801	Discontinued
0.6387	Remote Similarity	NPD5403	Approved
0.6386	Remote Similarity	NPD5844	Phase 1
0.6385	Remote Similarity	NPD290	Approved
0.6383	Remote Similarity	NPD6696	Suspended
0.6377	Remote Similarity	NPD5306	Approved
0.6377	Remote Similarity	NPD5305	Approved
0.6376	Remote Similarity	NPD2438	Suspended
0.637	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.637	Remote Similarity	NPD3620	Phase 2
0.6364	Remote Similarity	NPD8485	Approved
0.6364	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5886	Approved
0.6351	Remote Similarity	NPD41	Approved
0.635	Remote Similarity	NPD9545	Approved
0.635	Remote Similarity	NPD3091	Approved
0.6349	Remote Similarity	NPD7640	Approved
0.6349	Remote Similarity	NPD7639	Approved
0.6345	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD6798	Discontinued
0.6345	Remote Similarity	NPD3764	Approved
0.6345	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3268	Approved
0.634	Remote Similarity	NPD6666	Approved
0.634	Remote Similarity	NPD6667	Approved
0.6338	Remote Similarity	NPD6362	Approved
0.6336	Remote Similarity	NPD2684	Approved
0.6333	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4340	Discontinued
0.6322	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4908	Phase 1
0.6316	Remote Similarity	NPD7835	Discontinued
0.6316	Remote Similarity	NPD4110	Phase 3
0.6316	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3750	Approved
0.6312	Remote Similarity	NPD7876	Discontinued
0.6312	Remote Similarity	NPD5402	Approved
0.6312	Remote Similarity	NPD4749	Approved
0.6306	Remote Similarity	NPD3226	Approved
0.6306	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5585	Approved
0.6304	Remote Similarity	NPD8033	Approved
0.6301	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7715	Approved
0.6301	Remote Similarity	NPD6233	Phase 2
0.6301	Remote Similarity	NPD7714	Approved
0.6294	Remote Similarity	NPD5647	Approved
0.6288	Remote Similarity	NPD4750	Phase 3
0.6286	Remote Similarity	NPD6287	Discontinued
0.6279	Remote Similarity	NPD164	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