NPASS Compound

Structure

NPC475586 OpenBabel07101719252D 49 52 0 0 1 0 0 0 0 0999 V2000 -6.8552 2.1521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7258 0.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1047 0.5562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6067 -2.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3422 0.4823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9059 3.4372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8317 3.1040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4879 3.1393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5682 3.2604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0221 3.6161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1698 2.7003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2517 0.8570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9355 2.2732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8034 -1.3915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0983 1.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9277 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3708 1.5373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4612 1.2243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4101 -2.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9872 -0.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4706 2.7012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0718 2.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7365 0.9859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6067 -0.9277 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9277 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7265 1.9395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9666 1.0435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8034 0.4638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5028 0.2401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5633 1.3599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4511 1.6583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9231 2.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6971 3.0302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6067 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0271 2.1632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2135 -2.7830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5519 -1.1107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3903 2.8223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9678 1.9678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6155 0.0662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0961 2.5154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2830 3.7495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9277 -0.9277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4101 -1.3915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0675 -0.4959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1156 1.8442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8863 0.9224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2401 0.8960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 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 21 1 0 0 0 0 7 22 1 0 0 0 0 8 32 1 0 0 0 0 9 32 1 0 0 0 0 10 33 1 0 0 0 0 11 33 1 0 0 0 0 13 17 2 0 0 0 0 14 24 1 0 0 0 0 14 25 1 0 0 0 0 15 23 1 0 0 0 0 15 36 1 0 0 0 0 16 35 1 0 0 0 0 16 44 1 0 0 0 0 17 31 1 0 0 0 0 18 23 1 0 0 0 0 18 26 2 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 39 2 0 0 0 0 21 47 1 0 0 0 0 22 40 2 0 0 0 0 22 49 1 0 0 0 0 23 41 1 6 0 0 0 24 34 1 6 0 0 0 24 45 1 0 0 0 0 25 35 1 6 0 0 0 25 44 1 0 0 0 0 26 27 1 0 0 0 0 26 32 1 0 0 0 0 27 29 1 0 0 0 0 27 48 1 6 0 0 0 28 30 1 0 0 0 0 28 34 1 6 0 0 0 28 35 1 0 0 0 0 29 34 1 1 0 0 0 29 46 1 0 0 0 0 30 36 1 1 0 0 0 30 47 1 0 0 0 0 31 42 2 0 0 0 0 31 48 1 0 0 0 0 32 36 1 0 0 0 0 33 43 1 0 0 0 0 34 12 1 6 0 0 0 35 49 1 1 0 0 0 36 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	692.34
Volume:	692.804
LogP:	2.758
LogD:	2.144
LogS:	-4.72
# Rotatable Bonds:	12
TPSA:	181.19
# H-Bond Aceptor:	13
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.172
Synthetic Accessibility Score:	6.285
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:	-5.416
MDCK Permeability:	0.00016161947860382497
Pgp-inhibitor:	1.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.953
20% Bioavailability (F20%):	0.812
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	52.40321731567383%
Volume Distribution (VD):	1.756
Pgp-substrate:	17.793386459350586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.213
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.395
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.449
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	2.996
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.285
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.31
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC475586

Natural Product ID:	NPC475586
*Common Name:**	Taxuspine Q
IUPAC Name:	n.a.
Synonyms:	taxuspine Q
Standard InCHIKey:	OZIMPKBLWPXMGY-UPIPKAODSA-N
Standard InCHI:	InChI=1S/C36H52O13/c1-13-17(2)31(42)48-27-26-18(3)23(41)15-36(32(26,8)9,33(10,11)43)30(47-21(6)39)28-34(12,29(27)46-20(5)38)24(45-19(4)37)14-25-35(28,16-44-25)49-22(7)40/h13,23-25,27-30,41,43H,14-16H2,1-12H3/b17-13+/t23-,24-,25+,27+,28-,29-,30-,34+,35-,36+/m0/s1
SMILES:	C/C=C(/C(=O)O[C@H]1[C@H](OC(=O)C)[C@]2(C)[C@@H](OC(=O)C)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](O)C2)(C)C)C(O)(C)C)OC(=O)C)(CO3)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508695
PubChem CID:	44566210
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.08	ug.mL-1	PMID[483122]

☑ 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 NPC475586 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	235
0.1-0.2	1600
0.2-0.3	4584
0.3-0.4	7438
0.4-0.5	15319
0.5-0.6	8049
0.6-0.7	4716
0.7-0.8	722
0.8-0.85	26
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.89	High Similarity	NPC211810
0.89	High Similarity	NPC284194
0.89	High Similarity	NPC471765
0.89	High Similarity	NPC221801
0.8835	High Similarity	NPC472552
0.8762	High Similarity	NPC111952
0.8738	High Similarity	NPC472554
0.8713	High Similarity	NPC472995
0.8713	High Similarity	NPC129569
0.87	High Similarity	NPC472416
0.87	High Similarity	NPC105375
0.87	High Similarity	NPC182826
0.87	High Similarity	NPC472360
0.8679	High Similarity	NPC143609
0.8641	High Similarity	NPC188968
0.8641	High Similarity	NPC271295
0.8641	High Similarity	NPC79303
0.8627	High Similarity	NPC473244
0.8598	High Similarity	NPC475263
0.8505	High Similarity	NPC473586
0.8505	High Similarity	NPC471205
0.85	High Similarity	NPC124374
0.8491	Intermediate Similarity	NPC473543
0.8476	Intermediate Similarity	NPC109195
0.8476	Intermediate Similarity	NPC475038
0.8462	Intermediate Similarity	NPC38855
0.8426	Intermediate Similarity	NPC181994
0.8416	Intermediate Similarity	NPC99653
0.8411	Intermediate Similarity	NPC88349
0.84	Intermediate Similarity	NPC220216
0.8396	Intermediate Similarity	NPC473523
0.8396	Intermediate Similarity	NPC8196
0.8396	Intermediate Similarity	NPC23584
0.8364	Intermediate Similarity	NPC17791
0.835	Intermediate Similarity	NPC472996
0.835	Intermediate Similarity	NPC472997
0.8333	Intermediate Similarity	NPC472390
0.8302	Intermediate Similarity	NPC137430
0.8302	Intermediate Similarity	NPC11956
0.8302	Intermediate Similarity	NPC476471
0.8302	Intermediate Similarity	NPC475344
0.83	Intermediate Similarity	NPC314727
0.83	Intermediate Similarity	NPC246028
0.83	Intermediate Similarity	NPC261320
0.8288	Intermediate Similarity	NPC321272
0.8288	Intermediate Similarity	NPC317460
0.8288	Intermediate Similarity	NPC328074
0.8288	Intermediate Similarity	NPC470025
0.8257	Intermediate Similarity	NPC472439
0.8257	Intermediate Similarity	NPC50124
0.8257	Intermediate Similarity	NPC151393
0.8257	Intermediate Similarity	NPC469916
0.8252	Intermediate Similarity	NPC469583
0.8252	Intermediate Similarity	NPC37603
0.8252	Intermediate Similarity	NPC276110
0.8252	Intermediate Similarity	NPC471786
0.8241	Intermediate Similarity	NPC51719
0.8241	Intermediate Similarity	NPC471206
0.8224	Intermediate Similarity	NPC474124
0.8224	Intermediate Similarity	NPC99266
0.8218	Intermediate Similarity	NPC48732
0.8214	Intermediate Similarity	NPC470027
0.8208	Intermediate Similarity	NPC473160
0.8208	Intermediate Similarity	NPC11974
0.8173	Intermediate Similarity	NPC165632
0.8165	Intermediate Similarity	NPC187435
0.8165	Intermediate Similarity	NPC67321
0.8165	Intermediate Similarity	NPC122816
0.8158	Intermediate Similarity	NPC10721
0.8155	Intermediate Similarity	NPC105490
0.8131	Intermediate Similarity	NPC258547
0.8131	Intermediate Similarity	NPC165578
0.8131	Intermediate Similarity	NPC273668
0.8131	Intermediate Similarity	NPC283343
0.8113	Intermediate Similarity	NPC274643
0.8113	Intermediate Similarity	NPC272223
0.8108	Intermediate Similarity	NPC316708
0.8108	Intermediate Similarity	NPC177047
0.81	Intermediate Similarity	NPC102640
0.81	Intermediate Similarity	NPC471779
0.8095	Intermediate Similarity	NPC472998
0.8095	Intermediate Similarity	NPC475446
0.8095	Intermediate Similarity	NPC311241
0.8095	Intermediate Similarity	NPC287668
0.8091	Intermediate Similarity	NPC88701
0.8091	Intermediate Similarity	NPC470024
0.8091	Intermediate Similarity	NPC38948
0.807	Intermediate Similarity	NPC471127
0.807	Intermediate Similarity	NPC234858
0.807	Intermediate Similarity	NPC154363
0.8058	Intermediate Similarity	NPC7349
0.8056	Intermediate Similarity	NPC474822
0.8037	Intermediate Similarity	NPC235920
0.8037	Intermediate Similarity	NPC475617
0.8037	Intermediate Similarity	NPC96784
0.8037	Intermediate Similarity	NPC97435
0.8036	Intermediate Similarity	NPC470026
0.8034	Intermediate Similarity	NPC52839
0.802	Intermediate Similarity	NPC69713
0.8019	Intermediate Similarity	NPC107806
0.8019	Intermediate Similarity	NPC72647
0.8018	Intermediate Similarity	NPC322912
0.8018	Intermediate Similarity	NPC40728
0.8018	Intermediate Similarity	NPC206618
0.8017	Intermediate Similarity	NPC473636
0.8017	Intermediate Similarity	NPC77689
0.8	Intermediate Similarity	NPC209297
0.8	Intermediate Similarity	NPC202833
0.8	Intermediate Similarity	NPC475380
0.8	Intermediate Similarity	NPC473968
0.8	Intermediate Similarity	NPC102996
0.8	Intermediate Similarity	NPC109376
0.7982	Intermediate Similarity	NPC118911
0.7981	Intermediate Similarity	NPC469491
0.7963	Intermediate Similarity	NPC476081
0.7961	Intermediate Similarity	NPC473675
0.7949	Intermediate Similarity	NPC329080
0.7949	Intermediate Similarity	NPC471128
0.7949	Intermediate Similarity	NPC145182
0.7949	Intermediate Similarity	NPC472759
0.7949	Intermediate Similarity	NPC157252
0.7949	Intermediate Similarity	NPC471126
0.7949	Intermediate Similarity	NPC48692
0.7946	Intermediate Similarity	NPC472214
0.7946	Intermediate Similarity	NPC472215
0.7944	Intermediate Similarity	NPC473510
0.7944	Intermediate Similarity	NPC16601
0.7944	Intermediate Similarity	NPC474190
0.7944	Intermediate Similarity	NPC475877
0.7944	Intermediate Similarity	NPC230546
0.7944	Intermediate Similarity	NPC324841
0.7931	Intermediate Similarity	NPC124676
0.7931	Intermediate Similarity	NPC146280
0.7928	Intermediate Similarity	NPC128795
0.7928	Intermediate Similarity	NPC217921
0.7928	Intermediate Similarity	NPC48548
0.7928	Intermediate Similarity	NPC135015
0.7928	Intermediate Similarity	NPC306265
0.7928	Intermediate Similarity	NPC224660
0.7925	Intermediate Similarity	NPC120446
0.7925	Intermediate Similarity	NPC205143
0.7925	Intermediate Similarity	NPC199099
0.7925	Intermediate Similarity	NPC100912
0.7913	Intermediate Similarity	NPC470075
0.7913	Intermediate Similarity	NPC471816
0.7909	Intermediate Similarity	NPC172867
0.79	Intermediate Similarity	NPC35933
0.7895	Intermediate Similarity	NPC473159
0.7895	Intermediate Similarity	NPC472757
0.7895	Intermediate Similarity	NPC471204
0.789	Intermediate Similarity	NPC471938
0.789	Intermediate Similarity	NPC281378
0.789	Intermediate Similarity	NPC61442
0.789	Intermediate Similarity	NPC474575
0.7885	Intermediate Similarity	NPC110022
0.7885	Intermediate Similarity	NPC53555
0.7876	Intermediate Similarity	NPC470076
0.787	Intermediate Similarity	NPC476132
0.7864	Intermediate Similarity	NPC78973
0.7863	Intermediate Similarity	NPC236918
0.7863	Intermediate Similarity	NPC211093
0.7863	Intermediate Similarity	NPC22628
0.7863	Intermediate Similarity	NPC5989
0.7863	Intermediate Similarity	NPC255081
0.7863	Intermediate Similarity	NPC473839
0.7863	Intermediate Similarity	NPC470914
0.7863	Intermediate Similarity	NPC471108
0.7863	Intermediate Similarity	NPC275696
0.7863	Intermediate Similarity	NPC156745
0.7863	Intermediate Similarity	NPC469380
0.7863	Intermediate Similarity	NPC5991
0.7857	Intermediate Similarity	NPC173905
0.7857	Intermediate Similarity	NPC472216
0.7857	Intermediate Similarity	NPC5475
0.7857	Intermediate Similarity	NPC316974
0.7857	Intermediate Similarity	NPC284828
0.785	Intermediate Similarity	NPC278673
0.785	Intermediate Similarity	NPC477875
0.785	Intermediate Similarity	NPC216478
0.785	Intermediate Similarity	NPC275086
0.785	Intermediate Similarity	NPC247233
0.785	Intermediate Similarity	NPC218107
0.785	Intermediate Similarity	NPC325229
0.785	Intermediate Similarity	NPC477876
0.7845	Intermediate Similarity	NPC469684
0.7845	Intermediate Similarity	NPC134430
0.7838	Intermediate Similarity	NPC475781
0.7838	Intermediate Similarity	NPC112780
0.7838	Intermediate Similarity	NPC88013
0.7838	Intermediate Similarity	NPC125423
0.7838	Intermediate Similarity	NPC319438
0.7833	Intermediate Similarity	NPC145238
0.783	Intermediate Similarity	NPC475304
0.7826	Intermediate Similarity	NPC472400
0.7826	Intermediate Similarity	NPC43213
0.7826	Intermediate Similarity	NPC216665
0.7826	Intermediate Similarity	NPC181145
0.7818	Intermediate Similarity	NPC474550
0.7818	Intermediate Similarity	NPC471937
0.7818	Intermediate Similarity	NPC146731

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 NPC475586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1877
0.2-0.3	3790
0.3-0.4	2217
0.4-0.5	711
0.5-0.6	269
0.6-0.7	74
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
0.8208	Intermediate Similarity	NPD5344	Discontinued
0.7944	Intermediate Similarity	NPD6648	Approved
0.7699	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD4225	Approved
0.7632	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD7639	Approved
0.7615	Intermediate Similarity	NPD7640	Approved
0.7563	Intermediate Similarity	NPD7516	Approved
0.7523	Intermediate Similarity	NPD7638	Approved
0.7479	Intermediate Similarity	NPD7328	Approved
0.7479	Intermediate Similarity	NPD7327	Approved
0.7368	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7838	Discovery
0.7304	Intermediate Similarity	NPD6686	Approved
0.7295	Intermediate Similarity	NPD8378	Approved
0.7295	Intermediate Similarity	NPD8379	Approved
0.7295	Intermediate Similarity	NPD8033	Approved
0.7295	Intermediate Similarity	NPD8296	Approved
0.7295	Intermediate Similarity	NPD8335	Approved
0.7295	Intermediate Similarity	NPD8380	Approved
0.725	Intermediate Similarity	NPD7115	Discovery
0.7213	Intermediate Similarity	NPD8377	Approved
0.7213	Intermediate Similarity	NPD8294	Approved
0.7207	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7503	Approved
0.7059	Intermediate Similarity	NPD8297	Approved
0.7037	Intermediate Similarity	NPD46	Approved
0.7037	Intermediate Similarity	NPD6698	Approved
0.7018	Intermediate Similarity	NPD7632	Discontinued
0.7009	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7507	Approved
0.6899	Remote Similarity	NPD7319	Approved
0.6847	Remote Similarity	NPD7748	Approved
0.6814	Remote Similarity	NPD7902	Approved
0.6807	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6319	Approved
0.6759	Remote Similarity	NPD7524	Approved
0.675	Remote Similarity	NPD6371	Approved
0.6723	Remote Similarity	NPD6881	Approved
0.6723	Remote Similarity	NPD6899	Approved
0.6721	Remote Similarity	NPD4632	Approved
0.6695	Remote Similarity	NPD6675	Approved
0.6695	Remote Similarity	NPD7128	Approved
0.6695	Remote Similarity	NPD6402	Approved
0.6695	Remote Similarity	NPD5739	Approved
0.6694	Remote Similarity	NPD6649	Approved
0.6694	Remote Similarity	NPD6650	Approved
0.6694	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD7637	Suspended
0.6641	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD6053	Discontinued
0.6639	Remote Similarity	NPD6882	Approved
0.6639	Remote Similarity	NPD5697	Approved
0.6639	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8517	Approved
0.6614	Remote Similarity	NPD8515	Approved
0.6614	Remote Similarity	NPD8516	Approved
0.6614	Remote Similarity	NPD8513	Phase 3
0.6612	Remote Similarity	NPD7290	Approved
0.6612	Remote Similarity	NPD6883	Approved
0.6612	Remote Similarity	NPD7102	Approved
0.6607	Remote Similarity	NPD5778	Approved
0.6607	Remote Similarity	NPD5779	Approved
0.6589	Remote Similarity	NPD7492	Approved
0.6585	Remote Similarity	NPD8133	Approved
0.6583	Remote Similarity	NPD7320	Approved
0.6565	Remote Similarity	NPD7736	Approved
0.656	Remote Similarity	NPD6009	Approved
0.6557	Remote Similarity	NPD6847	Approved
0.6557	Remote Similarity	NPD6869	Approved
0.6557	Remote Similarity	NPD6617	Approved
0.6549	Remote Similarity	NPD7900	Approved
0.6549	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6695	Phase 3
0.6538	Remote Similarity	NPD6616	Approved
0.6535	Remote Similarity	NPD6054	Approved
0.6529	Remote Similarity	NPD6014	Approved
0.6529	Remote Similarity	NPD6012	Approved
0.6529	Remote Similarity	NPD6013	Approved
0.6518	Remote Similarity	NPD7983	Approved
0.6512	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD5701	Approved
0.65	Remote Similarity	NPD6412	Phase 2
0.6489	Remote Similarity	NPD8293	Discontinued
0.6489	Remote Similarity	NPD7078	Approved
0.6484	Remote Similarity	NPD6921	Approved
0.6484	Remote Similarity	NPD5983	Phase 2
0.646	Remote Similarity	NPD6399	Phase 3
0.6455	Remote Similarity	NPD7750	Discontinued
0.6449	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6011	Approved
0.6441	Remote Similarity	NPD5211	Phase 2
0.6434	Remote Similarity	NPD6370	Approved
0.6429	Remote Similarity	NPD3168	Discontinued
0.6429	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD1694	Approved
0.6417	Remote Similarity	NPD6008	Approved
0.6412	Remote Similarity	NPD6336	Discontinued
0.6406	Remote Similarity	NPD6059	Approved
0.6379	Remote Similarity	NPD6083	Phase 2
0.6379	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD8074	Phase 3
0.6357	Remote Similarity	NPD6015	Approved
0.6357	Remote Similarity	NPD6016	Approved
0.6339	Remote Similarity	NPD6051	Approved
0.6333	Remote Similarity	NPD5141	Approved
0.6321	Remote Similarity	NPD7645	Phase 2
0.6308	Remote Similarity	NPD5988	Approved
0.6296	Remote Similarity	NPD7260	Phase 2
0.629	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5286	Approved
0.6271	Remote Similarity	NPD5285	Approved
0.6271	Remote Similarity	NPD4696	Approved
0.6262	Remote Similarity	NPD6930	Phase 2
0.6262	Remote Similarity	NPD7525	Registered
0.6262	Remote Similarity	NPD6931	Approved
0.625	Remote Similarity	NPD8264	Approved
0.6239	Remote Similarity	NPD4755	Approved
0.6228	Remote Similarity	NPD6411	Approved
0.6228	Remote Similarity	NPD6079	Approved
0.6226	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6274	Approved
0.6218	Remote Similarity	NPD4159	Approved
0.6216	Remote Similarity	NPD3618	Phase 1
0.621	Remote Similarity	NPD4634	Approved
0.6207	Remote Similarity	NPD5695	Phase 3
0.6202	Remote Similarity	NPD7101	Approved
0.6202	Remote Similarity	NPD7100	Approved
0.6195	Remote Similarity	NPD5328	Approved
0.6174	Remote Similarity	NPD4202	Approved
0.6168	Remote Similarity	NPD6929	Approved
0.6167	Remote Similarity	NPD5226	Approved
0.6167	Remote Similarity	NPD5225	Approved
0.6167	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4633	Approved
0.6167	Remote Similarity	NPD5224	Approved
0.6161	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3573	Approved
0.614	Remote Similarity	NPD5785	Approved
0.6134	Remote Similarity	NPD4700	Approved
0.6124	Remote Similarity	NPD6335	Approved
0.6116	Remote Similarity	NPD5174	Approved
0.6116	Remote Similarity	NPD5175	Approved
0.6111	Remote Similarity	NPD8368	Discontinued
0.6111	Remote Similarity	NPD7514	Phase 3
0.6111	Remote Similarity	NPD7332	Phase 2
0.6087	Remote Similarity	NPD8034	Phase 2
0.6087	Remote Similarity	NPD7087	Discontinued
0.6087	Remote Similarity	NPD8035	Phase 2
0.6083	Remote Similarity	NPD5223	Approved
0.6071	Remote Similarity	NPD7521	Approved
0.6071	Remote Similarity	NPD6684	Approved
0.6071	Remote Similarity	NPD5330	Approved
0.6071	Remote Similarity	NPD6409	Approved
0.6071	Remote Similarity	NPD7146	Approved
0.6071	Remote Similarity	NPD7334	Approved
0.6068	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6101	Approved
0.605	Remote Similarity	NPD5696	Approved
0.6048	Remote Similarity	NPD4729	Approved
0.6048	Remote Similarity	NPD4730	Approved
0.6047	Remote Similarity	NPD6317	Approved
0.6036	Remote Similarity	NPD4786	Approved
0.6024	Remote Similarity	NPD8434	Phase 2
0.6018	Remote Similarity	NPD4250	Approved
0.6018	Remote Similarity	NPD4251	Approved
0.6017	Remote Similarity	NPD5222	Approved
0.6017	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5221	Approved
0.6016	Remote Similarity	NPD5357	Phase 1
0.6016	Remote Similarity	NPD4768	Approved
0.6016	Remote Similarity	NPD4767	Approved
0.6015	Remote Similarity	NPD6067	Discontinued
0.6014	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD8407	Phase 2
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD6313	Approved
0.5986	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD6909	Approved
0.5985	Remote Similarity	NPD6908	Approved
0.5982	Remote Similarity	NPD6893	Approved
0.5982	Remote Similarity	NPD1696	Phase 3
0.5981	Remote Similarity	NPD6925	Approved
0.5981	Remote Similarity	NPD5776	Phase 2
0.5969	Remote Similarity	NPD6868	Approved
0.5966	Remote Similarity	NPD5173	Approved
0.5965	Remote Similarity	NPD5737	Approved
0.5965	Remote Similarity	NPD6903	Approved
0.5965	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6672	Approved
0.5963	Remote Similarity	NPD4821	Approved
0.5963	Remote Similarity	NPD4820	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