NPASS Compound

Structure

CID8196 OpenBabel06191715332D 34 36 0 0 1 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3267 1.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9246 -3.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6900 0.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9246 2.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0230 -1.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4057 -0.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6088 -0.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0364 -1.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6035 0.1377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9332 -3.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0812 1.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9332 2.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -1.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9903 -0.4102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4142 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7071 -1.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7071 0.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4142 -1.0000 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 0.5505 -4.3482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4639 2.6854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5505 3.3482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0665 -0.0275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3244 -2.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0898 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3244 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 26 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 20 2 0 0 0 0 14 27 2 0 0 0 0 14 32 1 0 0 0 0 15 28 2 0 0 0 0 15 33 1 0 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 17 11 1 1 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 30 1 1 0 0 0 19 31 2 0 0 0 0 20 23 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 6 0 0 0 22 32 1 1 0 0 0 23 24 1 0 0 0 0 23 33 1 6 0 0 0 24 26 1 1 0 0 0 24 34 1 0 0 0 0 26 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.24
Volume:	487.086
LogP:	2.635
LogD:	2.676
LogS:	-3.953
# Rotatable Bonds:	6
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.421
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.947
MDCK Permeability:	7.234163786051795e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.437
Human Intestinal Absorption (HIA):	0.196
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.162

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.456
Plasma Protein Binding (PPB):	62.8690185546875%
Volume Distribution (VD):	1.164
Pgp-substrate:	34.19466018676758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.118
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.682
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	3.187
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.829
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.125
Carcinogencity:	0.126
Eye Corrosion:	0.01
Eye Irritation:	0.018
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC8196

Natural Product ID:	NPC8196
*Common Name:**	Taxinine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OQXJKHGIAZCMBX-SOIIJPRYSA-N
Standard InCHI:	InChI=1S/C26H36O8/c1-12-18(30)9-10-26(8)21(12)22(32-14(3)27)17-11-19(31)13(2)20(25(17,6)7)23(33-15(4)28)24(26)34-16(5)29/h17-18,21-24,30H,1,9-11H2,2-8H3/t17-,18-,21-,22+,23+,24-,26+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H]2C(=C)[C@@H](O)CC[C@@]2(C)[C@@H](OC(=O)C)[C@@H](C2=C(C(=O)C[C@@H]1C2(C)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL113940
PubChem CID:	11081282
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
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[11473432]
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.	Japan	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23265441]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561894]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7908950]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[8991951]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644081]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO5067	Taxus baccata	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]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27746	Taxus mairei	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	5

Activity Type	# Activity
Cell Line	1
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	8.9	ug.mL-1	PMID[473771]
NPT2	Others	Unspecified		Control	=	153.0	%	PMID[473771]
NPT2	Others	Unspecified		Control	=	461.0	%	PMID[473771]
NPT27	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[473771]
NPT2	Others	Unspecified		Control	=	153.0	%	PMID[473772]
NPT2	Others	Unspecified		Control	=	461.0	%	PMID[473772]
NPT2	Others	Unspecified		Relative activity	=	64.0	n.a.	PMID[473773]

☑ 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 NPC8196 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	224
0.1-0.2	1309
0.2-0.3	3961
0.3-0.4	7034
0.4-0.5	14397
0.5-0.6	7618
0.6-0.7	6595
0.7-0.8	1499
0.8-0.85	32
0.85-0.9	15
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC137430
0.9792	High Similarity	NPC99266
0.9694	High Similarity	NPC143609
0.9596	High Similarity	NPC151393
0.9592	High Similarity	NPC111952
0.9583	High Similarity	NPC97435
0.902	High Similarity	NPC469916
0.902	High Similarity	NPC472439
0.8958	High Similarity	NPC472360
0.8958	High Similarity	NPC472416
0.8854	High Similarity	NPC99653
0.8824	High Similarity	NPC472389
0.8776	High Similarity	NPC211810
0.8776	High Similarity	NPC284194
0.8776	High Similarity	NPC471765
0.8776	High Similarity	NPC221801
0.875	High Similarity	NPC124374
0.8738	High Similarity	NPC112780
0.8679	High Similarity	NPC317687
0.8673	High Similarity	NPC37603
0.8673	High Similarity	NPC471786
0.8646	High Similarity	NPC48732
0.8646	High Similarity	NPC220216
0.8627	High Similarity	NPC159533
0.8585	High Similarity	NPC317107
0.8558	High Similarity	NPC187435
0.8558	High Similarity	NPC67321
0.8542	High Similarity	NPC261320
0.8529	High Similarity	NPC469606
0.8529	High Similarity	NPC273005
0.8529	High Similarity	NPC295791
0.8529	High Similarity	NPC31058
0.8476	Intermediate Similarity	NPC476479
0.8476	Intermediate Similarity	NPC322903
0.8454	Intermediate Similarity	NPC232202
0.8438	Intermediate Similarity	NPC69713
0.8426	Intermediate Similarity	NPC471204
0.84	Intermediate Similarity	NPC202833
0.8396	Intermediate Similarity	NPC475586
0.8396	Intermediate Similarity	NPC273433
0.8384	Intermediate Similarity	NPC105375
0.8384	Intermediate Similarity	NPC182826
0.8365	Intermediate Similarity	NPC118911
0.8351	Intermediate Similarity	NPC246028
0.835	Intermediate Similarity	NPC165250
0.835	Intermediate Similarity	NPC476081
0.8333	Intermediate Similarity	NPC236217
0.8333	Intermediate Similarity	NPC471779
0.8333	Intermediate Similarity	NPC102640
0.8317	Intermediate Similarity	NPC473244
0.8302	Intermediate Similarity	NPC189075
0.8302	Intermediate Similarity	NPC275539
0.8302	Intermediate Similarity	NPC306265
0.8286	Intermediate Similarity	NPC469607
0.8269	Intermediate Similarity	NPC471208
0.8269	Intermediate Similarity	NPC95899
0.8269	Intermediate Similarity	NPC478057
0.8257	Intermediate Similarity	NPC25909
0.8252	Intermediate Similarity	NPC303559
0.8241	Intermediate Similarity	NPC324683
0.8241	Intermediate Similarity	NPC188738
0.8235	Intermediate Similarity	NPC478056
0.8235	Intermediate Similarity	NPC222303
0.8235	Intermediate Similarity	NPC23364
0.8235	Intermediate Similarity	NPC216478
0.8229	Intermediate Similarity	NPC102996
0.8218	Intermediate Similarity	NPC129569
0.8214	Intermediate Similarity	NPC475041
0.8208	Intermediate Similarity	NPC110496
0.8208	Intermediate Similarity	NPC230541
0.82	Intermediate Similarity	NPC250075
0.8198	Intermediate Similarity	NPC473968
0.819	Intermediate Similarity	NPC146731
0.819	Intermediate Similarity	NPC296950
0.8173	Intermediate Similarity	NPC472552
0.8165	Intermediate Similarity	NPC476801
0.8165	Intermediate Similarity	NPC269530
0.8158	Intermediate Similarity	NPC470265
0.8158	Intermediate Similarity	NPC23786
0.8158	Intermediate Similarity	NPC269642
0.8155	Intermediate Similarity	NPC47024
0.8155	Intermediate Similarity	NPC476274
0.8148	Intermediate Similarity	NPC469917
0.8148	Intermediate Similarity	NPC5103
0.8148	Intermediate Similarity	NPC472417
0.8142	Intermediate Similarity	NPC48692
0.8137	Intermediate Similarity	NPC151681
0.8137	Intermediate Similarity	NPC121402
0.8137	Intermediate Similarity	NPC175351
0.8137	Intermediate Similarity	NPC224356
0.8137	Intermediate Similarity	NPC254496
0.8137	Intermediate Similarity	NPC132753
0.8137	Intermediate Similarity	NPC285513
0.8137	Intermediate Similarity	NPC320306
0.8137	Intermediate Similarity	NPC474343
0.8137	Intermediate Similarity	NPC474395
0.8131	Intermediate Similarity	NPC476802
0.8131	Intermediate Similarity	NPC325054
0.8131	Intermediate Similarity	NPC89171
0.8131	Intermediate Similarity	NPC88701
0.8119	Intermediate Similarity	NPC183012
0.8113	Intermediate Similarity	NPC127609
0.8113	Intermediate Similarity	NPC102352
0.8108	Intermediate Similarity	NPC471127
0.8108	Intermediate Similarity	NPC234858
0.8108	Intermediate Similarity	NPC154363
0.81	Intermediate Similarity	NPC199543
0.8095	Intermediate Similarity	NPC120321
0.8095	Intermediate Similarity	NPC69171
0.8095	Intermediate Similarity	NPC474165
0.8091	Intermediate Similarity	NPC469496
0.8091	Intermediate Similarity	NPC962
0.8091	Intermediate Similarity	NPC469454
0.8091	Intermediate Similarity	NPC250109
0.8091	Intermediate Similarity	NPC469463
0.8081	Intermediate Similarity	NPC158488
0.8077	Intermediate Similarity	NPC476240
0.8077	Intermediate Similarity	NPC476223
0.8077	Intermediate Similarity	NPC115862
0.8077	Intermediate Similarity	NPC472554
0.8077	Intermediate Similarity	NPC471412
0.8077	Intermediate Similarity	NPC224720
0.8073	Intermediate Similarity	NPC475480
0.8073	Intermediate Similarity	NPC475668
0.8073	Intermediate Similarity	NPC473921
0.807	Intermediate Similarity	NPC67569
0.8058	Intermediate Similarity	NPC316598
0.8056	Intermediate Similarity	NPC141350
0.8053	Intermediate Similarity	NPC476529
0.8053	Intermediate Similarity	NPC475775
0.8041	Intermediate Similarity	NPC473226
0.8039	Intermediate Similarity	NPC7124
0.8039	Intermediate Similarity	NPC134072
0.8039	Intermediate Similarity	NPC234993
0.8039	Intermediate Similarity	NPC472363
0.8039	Intermediate Similarity	NPC472362
0.8039	Intermediate Similarity	NPC154526
0.8037	Intermediate Similarity	NPC144854
0.8037	Intermediate Similarity	NPC3316
0.8037	Intermediate Similarity	NPC473586
0.8037	Intermediate Similarity	NPC472390
0.8036	Intermediate Similarity	NPC469684
0.8036	Intermediate Similarity	NPC10721
0.802	Intermediate Similarity	NPC196227
0.802	Intermediate Similarity	NPC57117
0.8019	Intermediate Similarity	NPC65523
0.8019	Intermediate Similarity	NPC258532
0.8019	Intermediate Similarity	NPC470104
0.8018	Intermediate Similarity	NPC474181
0.8018	Intermediate Similarity	NPC181145
0.8	Intermediate Similarity	NPC472002
0.8	Intermediate Similarity	NPC473944
0.8	Intermediate Similarity	NPC186363
0.8	Intermediate Similarity	NPC194951
0.8	Intermediate Similarity	NPC162973
0.8	Intermediate Similarity	NPC116726
0.8	Intermediate Similarity	NPC136289
0.8	Intermediate Similarity	NPC476126
0.8	Intermediate Similarity	NPC12046
0.8	Intermediate Similarity	NPC477574
0.8	Intermediate Similarity	NPC183571
0.8	Intermediate Similarity	NPC80781
0.8	Intermediate Similarity	NPC233345
0.8	Intermediate Similarity	NPC476235
0.7982	Intermediate Similarity	NPC145182
0.7982	Intermediate Similarity	NPC475134
0.7982	Intermediate Similarity	NPC471128
0.7982	Intermediate Similarity	NPC83005
0.7982	Intermediate Similarity	NPC478211
0.7982	Intermediate Similarity	NPC235014
0.7982	Intermediate Similarity	NPC475563
0.7982	Intermediate Similarity	NPC109607
0.7982	Intermediate Similarity	NPC471126
0.7982	Intermediate Similarity	NPC157252
0.7982	Intermediate Similarity	NPC107338
0.7981	Intermediate Similarity	NPC251680
0.7981	Intermediate Similarity	NPC472644
0.7981	Intermediate Similarity	NPC307954
0.7981	Intermediate Similarity	NPC471413
0.7981	Intermediate Similarity	NPC38855
0.7981	Intermediate Similarity	NPC327431
0.7981	Intermediate Similarity	NPC54705
0.7981	Intermediate Similarity	NPC476933
0.7981	Intermediate Similarity	NPC188968
0.7981	Intermediate Similarity	NPC79303
0.7981	Intermediate Similarity	NPC476767
0.798	Intermediate Similarity	NPC5509
0.7965	Intermediate Similarity	NPC291564
0.7965	Intermediate Similarity	NPC251310
0.7965	Intermediate Similarity	NPC475913
0.7965	Intermediate Similarity	NPC234522
0.7963	Intermediate Similarity	NPC475263
0.7963	Intermediate Similarity	NPC293850
0.7963	Intermediate Similarity	NPC154608
0.7963	Intermediate Similarity	NPC277017
0.7963	Intermediate Similarity	NPC192813
0.7961	Intermediate Similarity	NPC170131
0.7961	Intermediate Similarity	NPC70145
0.7961	Intermediate Similarity	NPC253826
0.7961	Intermediate Similarity	NPC91695

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 NPC8196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1702
0.2-0.3	3527
0.3-0.4	2339
0.4-0.5	904
0.5-0.6	316
0.6-0.7	153
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
0.7981	Intermediate Similarity	NPD7640	Approved
0.7981	Intermediate Similarity	NPD7639	Approved
0.7885	Intermediate Similarity	NPD7638	Approved
0.7818	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6686	Approved
0.7727	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD6698	Approved
0.7723	Intermediate Similarity	NPD46	Approved
0.7719	Intermediate Similarity	NPD7115	Discovery
0.7714	Intermediate Similarity	NPD4225	Approved
0.7619	Intermediate Similarity	NPD7902	Approved
0.7573	Intermediate Similarity	NPD6399	Phase 3
0.7545	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD7632	Discontinued
0.7476	Intermediate Similarity	NPD7515	Phase 2
0.7411	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6371	Approved
0.7333	Intermediate Similarity	NPD7900	Approved
0.7333	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6372	Approved
0.7257	Intermediate Similarity	NPD6373	Approved
0.7248	Intermediate Similarity	NPD5344	Discontinued
0.7238	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD5779	Approved
0.7232	Intermediate Similarity	NPD6412	Phase 2
0.7228	Intermediate Similarity	NPD1694	Approved
0.7222	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8297	Approved
0.7213	Intermediate Similarity	NPD7507	Approved
0.719	Intermediate Similarity	NPD8328	Phase 3
0.7168	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3618	Phase 1
0.7155	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.71	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6319	Approved
0.7069	Intermediate Similarity	NPD6053	Discontinued
0.7048	Intermediate Similarity	NPD5785	Approved
0.7048	Intermediate Similarity	NPD7838	Discovery
0.704	Intermediate Similarity	NPD7319	Approved
0.7018	Intermediate Similarity	NPD6899	Approved
0.7018	Intermediate Similarity	NPD6881	Approved
0.7018	Intermediate Similarity	NPD7320	Approved
0.7009	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD6648	Approved
0.699	Remote Similarity	NPD6409	Approved
0.699	Remote Similarity	NPD5330	Approved
0.699	Remote Similarity	NPD7146	Approved
0.699	Remote Similarity	NPD6684	Approved
0.699	Remote Similarity	NPD7521	Approved
0.699	Remote Similarity	NPD7334	Approved
0.6981	Remote Similarity	NPD7983	Approved
0.6975	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6009	Approved
0.6972	Remote Similarity	NPD6084	Phase 2
0.6972	Remote Similarity	NPD6083	Phase 2
0.6961	Remote Similarity	NPD4786	Approved
0.6952	Remote Similarity	NPD5328	Approved
0.6931	Remote Similarity	NPD3667	Approved
0.693	Remote Similarity	NPD5701	Approved
0.693	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5697	Approved
0.6929	Remote Similarity	NPD7260	Phase 2
0.6923	Remote Similarity	NPD6882	Approved
0.6917	Remote Similarity	NPD7327	Approved
0.6917	Remote Similarity	NPD7328	Approved
0.6911	Remote Similarity	NPD7604	Phase 2
0.6897	Remote Similarity	NPD6883	Approved
0.6897	Remote Similarity	NPD7102	Approved
0.6897	Remote Similarity	NPD7290	Approved
0.6885	Remote Similarity	NPD8033	Approved
0.6885	Remote Similarity	NPD8516	Approved
0.6885	Remote Similarity	NPD5983	Phase 2
0.6885	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD8515	Approved
0.6885	Remote Similarity	NPD8517	Approved
0.687	Remote Similarity	NPD6011	Approved
0.686	Remote Similarity	NPD7516	Approved
0.6857	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6672	Approved
0.6857	Remote Similarity	NPD5737	Approved
0.6857	Remote Similarity	NPD6903	Approved
0.6855	Remote Similarity	NPD7492	Approved
0.6838	Remote Similarity	NPD6869	Approved
0.6838	Remote Similarity	NPD8130	Phase 1
0.6838	Remote Similarity	NPD6847	Approved
0.6838	Remote Similarity	NPD6617	Approved
0.6838	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6079	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.6822	Remote Similarity	NPD8034	Phase 2
0.6822	Remote Similarity	NPD8035	Phase 2
0.681	Remote Similarity	NPD6013	Approved
0.681	Remote Similarity	NPD6012	Approved
0.681	Remote Similarity	NPD6014	Approved
0.6803	Remote Similarity	NPD8377	Approved
0.6803	Remote Similarity	NPD6059	Approved
0.6803	Remote Similarity	NPD8294	Approved
0.6803	Remote Similarity	NPD6054	Approved
0.68	Remote Similarity	NPD6616	Approved
0.68	Remote Similarity	NPD6336	Discontinued
0.6796	Remote Similarity	NPD3665	Phase 1
0.6796	Remote Similarity	NPD3133	Approved
0.6796	Remote Similarity	NPD3666	Approved
0.6789	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5695	Phase 3
0.6759	Remote Similarity	NPD4202	Approved
0.6757	Remote Similarity	NPD5696	Approved
0.6748	Remote Similarity	NPD8335	Approved
0.6748	Remote Similarity	NPD7503	Approved
0.6748	Remote Similarity	NPD8379	Approved
0.6748	Remote Similarity	NPD8296	Approved
0.6748	Remote Similarity	NPD8378	Approved
0.6748	Remote Similarity	NPD8380	Approved
0.6746	Remote Similarity	NPD8293	Discontinued
0.6746	Remote Similarity	NPD7078	Approved
0.6744	Remote Similarity	NPD6845	Suspended
0.6727	Remote Similarity	NPD4697	Phase 3
0.6726	Remote Similarity	NPD5211	Phase 2
0.6694	Remote Similarity	NPD6370	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.664	Remote Similarity	NPD6067	Discontinued
0.6636	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD6016	Approved
0.6613	Remote Similarity	NPD6921	Approved
0.6613	Remote Similarity	NPD6015	Approved
0.6609	Remote Similarity	NPD5141	Approved
0.6604	Remote Similarity	NPD3573	Approved
0.6577	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5222	Approved
0.6577	Remote Similarity	NPD5221	Approved
0.6571	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5363	Approved
0.6569	Remote Similarity	NPD4695	Discontinued
0.656	Remote Similarity	NPD5988	Approved
0.6549	Remote Similarity	NPD4700	Approved
0.6549	Remote Similarity	NPD4696	Approved
0.6549	Remote Similarity	NPD5285	Approved
0.6549	Remote Similarity	NPD5286	Approved
0.6545	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD6110	Phase 1
0.6535	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5173	Approved
0.6509	Remote Similarity	NPD4519	Discontinued
0.6509	Remote Similarity	NPD4623	Approved
0.6509	Remote Similarity	NPD5279	Phase 3
0.6504	Remote Similarity	NPD6335	Approved
0.6491	Remote Similarity	NPD5223	Approved
0.6481	Remote Similarity	NPD6904	Approved
0.6481	Remote Similarity	NPD6080	Approved
0.6481	Remote Similarity	NPD6673	Approved
0.6481	Remote Similarity	NPD4753	Phase 2
0.6476	Remote Similarity	NPD3668	Phase 3
0.6475	Remote Similarity	NPD6274	Approved
0.6475	Remote Similarity	NPD6868	Approved
0.6471	Remote Similarity	NPD4634	Approved
0.6452	Remote Similarity	NPD7101	Approved
0.6452	Remote Similarity	NPD7100	Approved
0.6442	Remote Similarity	NPD4269	Approved
0.6442	Remote Similarity	NPD4270	Approved
0.6435	Remote Similarity	NPD5226	Approved
0.6435	Remote Similarity	NPD5225	Approved
0.6435	Remote Similarity	NPD4633	Approved
0.6435	Remote Similarity	NPD5224	Approved
0.6434	Remote Similarity	NPD6033	Approved
0.6423	Remote Similarity	NPD6317	Approved
0.641	Remote Similarity	NPD4767	Approved
0.641	Remote Similarity	NPD4768	Approved
0.6408	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8039	Approved
0.6381	Remote Similarity	NPD5362	Discontinued
0.6381	Remote Similarity	NPD7154	Phase 3
0.6379	Remote Similarity	NPD5175	Approved
0.6379	Remote Similarity	NPD4754	Approved
0.6379	Remote Similarity	NPD5174	Approved
0.6371	Remote Similarity	NPD6313	Approved
0.6371	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD6050	Approved
0.6355	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5786	Approved
0.6349	Remote Similarity	NPD6909	Approved
0.6349	Remote Similarity	NPD6908	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