NPASS Compound

Structure

NPC476479 OpenBabel07101718292D 38 40 0 0 1 0 0 0 0 0999 V2000 1.0530 -0.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2257 0.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5587 -0.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3635 -2.8241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3860 -0.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1131 -2.9156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0596 -2.9156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3351 0.8852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5730 -0.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4061 -0.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5864 -0.7353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5864 0.1722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2333 -0.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4061 1.2168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4176 -1.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9485 -2.0802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2449 -1.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1727 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4061 -1.6227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5864 -0.2029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0566 -0.5088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6599 -1.0668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1161 -0.5088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2333 -1.6227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4872 -1.0668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4002 -0.4619 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5864 -2.0959 0.0000 C 0 0 0 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 -1.4061 2.1633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1576 -1.9334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8854 -2.2148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9849 -1.9334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4240 -1.2015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2612 -0.0687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5864 0.7435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5366 -1.6891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5968 -1.2015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3638 -1.6891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 27 1 0 0 0 0 7 27 1 0 0 0 0 9 18 2 0 0 0 0 9 22 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 12 28 1 0 0 0 0 13 20 1 0 0 0 0 13 24 2 0 0 0 0 14 29 2 0 0 0 0 14 35 1 0 0 0 0 15 30 2 0 0 0 0 15 36 1 0 0 0 0 16 31 2 0 0 0 0 16 37 1 0 0 0 0 17 32 2 0 0 0 0 17 38 1 0 0 0 0 18 21 1 0 0 0 0 19 10 1 1 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 35 1 6 0 0 0 21 36 1 6 0 0 0 22 37 1 1 0 0 0 23 28 1 1 0 0 0 23 38 1 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 25 33 2 0 0 0 0 26 28 1 1 0 0 0 26 34 1 0 0 0 0 28 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.25
Volume:	536.622
LogP:	2.875
LogD:	2.242
LogS:	-4.388
# Rotatable Bonds:	8
TPSA:	139.34
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	6.509
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.921
MDCK Permeability:	0.00013222405686974525
Pgp-inhibitor:	0.999
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.272
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.365
Plasma Protein Binding (PPB):	75.66841888427734%
Volume Distribution (VD):	0.949
Pgp-substrate:	18.62394142150879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	2.827
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.916
Drug-inuced Liver Injury (DILI):	0.827
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.65
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.132
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC476479

Natural Product ID:	NPC476479
*Common Name:**	OABRJXXTRSPEKZ-JBHCYJFQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OABRJXXTRSPEKZ-JBHCYJFQSA-N
Standard InCHI:	InChI=1S/C28H38O10/c1-13-20(35-14(2)29)10-19-22(37-16(4)31)9-18-12-28(8,26(34)25(33)24(13)27(19,6)7)23(38-17(5)32)11-21(18)36-15(3)30/h9,19-23,26,34H,10-12H2,1-8H3/b18-9+/t19-,20-,21-,22-,23-,26-,28-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H](OC(=O)C)[C@@]2(C/C/1=C[C@H](OC(=O)C)[C@@H]1C[C@@H](C(=C(C(=O)[C@@H]2O)C1(C)C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL96337
PubChem CID:	44326764
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
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
ED50	3
Others	3

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	>	21.0	ug ml-1	PMID[506661]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	21.0	%	PMID[506661]
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	>	28.0	ug ml-1	PMID[506661]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	28.0	%	PMID[506661]
NPT27	Others	Unspecified		ED50	>	20.0	ug ml-1	PMID[506661]
NPT27	Others	Unspecified		Inhibition	=	10.0	%	PMID[506661]

☑ 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 NPC476479 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	220
0.1-0.2	1260
0.2-0.3	4002
0.3-0.4	6854
0.4-0.5	13648
0.5-0.6	8403
0.6-0.7	6385
0.7-0.8	1870
0.8-0.85	47
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9216	High Similarity	NPC123726
0.9216	High Similarity	NPC284365
0.8824	High Similarity	NPC476478
0.8762	High Similarity	NPC143609
0.8667	High Similarity	NPC111952
0.8624	High Similarity	NPC471204
0.8558	High Similarity	NPC476081
0.8519	High Similarity	NPC5103
0.8505	High Similarity	NPC322903
0.8505	High Similarity	NPC275539
0.8505	High Similarity	NPC189075
0.8491	Intermediate Similarity	NPC469607
0.8476	Intermediate Similarity	NPC8196
0.8455	Intermediate Similarity	NPC469454
0.8455	Intermediate Similarity	NPC25909
0.8455	Intermediate Similarity	NPC469463
0.8455	Intermediate Similarity	NPC469496
0.8447	Intermediate Similarity	NPC216478
0.8431	Intermediate Similarity	NPC202833
0.8426	Intermediate Similarity	NPC42662
0.8411	Intermediate Similarity	NPC110496
0.8407	Intermediate Similarity	NPC475775
0.8407	Intermediate Similarity	NPC476529
0.8396	Intermediate Similarity	NPC258532
0.8396	Intermediate Similarity	NPC118911
0.8393	Intermediate Similarity	NPC473590
0.8381	Intermediate Similarity	NPC137430
0.8378	Intermediate Similarity	NPC473798
0.8365	Intermediate Similarity	NPC47024
0.8365	Intermediate Similarity	NPC472972
0.8364	Intermediate Similarity	NPC317687
0.835	Intermediate Similarity	NPC285513
0.8333	Intermediate Similarity	NPC476802
0.8333	Intermediate Similarity	NPC477437
0.8333	Intermediate Similarity	NPC109607
0.8333	Intermediate Similarity	NPC107338
0.8333	Intermediate Similarity	NPC293850
0.8333	Intermediate Similarity	NPC89171
0.8333	Intermediate Similarity	NPC477438
0.8319	Intermediate Similarity	NPC251310
0.8317	Intermediate Similarity	NPC477436
0.8317	Intermediate Similarity	NPC477435
0.8304	Intermediate Similarity	NPC40632
0.8304	Intermediate Similarity	NPC96312
0.8304	Intermediate Similarity	NPC328374
0.8304	Intermediate Similarity	NPC251236
0.8302	Intermediate Similarity	NPC275583
0.8302	Intermediate Similarity	NPC99266
0.8302	Intermediate Similarity	NPC120321
0.8288	Intermediate Similarity	NPC159333
0.8288	Intermediate Similarity	NPC49451
0.8286	Intermediate Similarity	NPC471412
0.8276	Intermediate Similarity	NPC67251
0.8276	Intermediate Similarity	NPC265557
0.8276	Intermediate Similarity	NPC91693
0.8276	Intermediate Similarity	NPC18945
0.8276	Intermediate Similarity	NPC105926
0.8273	Intermediate Similarity	NPC304180
0.8273	Intermediate Similarity	NPC317107
0.8273	Intermediate Similarity	NPC179798
0.8269	Intermediate Similarity	NPC23364
0.8257	Intermediate Similarity	NPC474243
0.8257	Intermediate Similarity	NPC273433
0.8241	Intermediate Similarity	NPC187435
0.8241	Intermediate Similarity	NPC144854
0.8241	Intermediate Similarity	NPC3316
0.8241	Intermediate Similarity	NPC67321
0.8235	Intermediate Similarity	NPC477439
0.8235	Intermediate Similarity	NPC250075
0.8218	Intermediate Similarity	NPC473944
0.8214	Intermediate Similarity	NPC474872
0.8208	Intermediate Similarity	NPC165250
0.8208	Intermediate Similarity	NPC469606
0.8208	Intermediate Similarity	NPC273005
0.8208	Intermediate Similarity	NPC31058
0.8208	Intermediate Similarity	NPC295791
0.8208	Intermediate Similarity	NPC162973
0.8205	Intermediate Similarity	NPC476729
0.8205	Intermediate Similarity	NPC24651
0.8198	Intermediate Similarity	NPC475391
0.8198	Intermediate Similarity	NPC474516
0.8198	Intermediate Similarity	NPC277769
0.8198	Intermediate Similarity	NPC194951
0.8198	Intermediate Similarity	NPC473877
0.8198	Intermediate Similarity	NPC12046
0.819	Intermediate Similarity	NPC471413
0.819	Intermediate Similarity	NPC472644
0.819	Intermediate Similarity	NPC476933
0.819	Intermediate Similarity	NPC312833
0.819	Intermediate Similarity	NPC222688
0.8182	Intermediate Similarity	NPC206595
0.8174	Intermediate Similarity	NPC471126
0.8174	Intermediate Similarity	NPC157252
0.8174	Intermediate Similarity	NPC145182
0.8174	Intermediate Similarity	NPC471128
0.8173	Intermediate Similarity	NPC91695
0.8173	Intermediate Similarity	NPC254496
0.8173	Intermediate Similarity	NPC70145
0.8173	Intermediate Similarity	NPC69385
0.8165	Intermediate Similarity	NPC469916
0.8165	Intermediate Similarity	NPC154608
0.8165	Intermediate Similarity	NPC192813
0.8165	Intermediate Similarity	NPC151393
0.8165	Intermediate Similarity	NPC277017
0.8165	Intermediate Similarity	NPC472439
0.8158	Intermediate Similarity	NPC21326
0.8148	Intermediate Similarity	NPC28791
0.8148	Intermediate Similarity	NPC1679
0.8148	Intermediate Similarity	NPC34768
0.8148	Intermediate Similarity	NPC472645
0.8142	Intermediate Similarity	NPC148458
0.8142	Intermediate Similarity	NPC474734
0.8137	Intermediate Similarity	NPC476597
0.8137	Intermediate Similarity	NPC476598
0.8131	Intermediate Similarity	NPC254202
0.8131	Intermediate Similarity	NPC478057
0.8131	Intermediate Similarity	NPC69171
0.8131	Intermediate Similarity	NPC474165
0.8125	Intermediate Similarity	NPC71889
0.8125	Intermediate Similarity	NPC7921
0.8125	Intermediate Similarity	NPC56448
0.8125	Intermediate Similarity	NPC208998
0.8125	Intermediate Similarity	NPC472926
0.8125	Intermediate Similarity	NPC157441
0.8125	Intermediate Similarity	NPC474937
0.8125	Intermediate Similarity	NPC474271
0.812	Intermediate Similarity	NPC472399
0.8113	Intermediate Similarity	NPC111292
0.8113	Intermediate Similarity	NPC97435
0.8113	Intermediate Similarity	NPC472643
0.8108	Intermediate Similarity	NPC34315
0.8108	Intermediate Similarity	NPC171888
0.8108	Intermediate Similarity	NPC260786
0.8108	Intermediate Similarity	NPC96739
0.8108	Intermediate Similarity	NPC474871
0.8108	Intermediate Similarity	NPC469655
0.8108	Intermediate Similarity	NPC469656
0.8108	Intermediate Similarity	NPC474846
0.8108	Intermediate Similarity	NPC174471
0.8108	Intermediate Similarity	NPC146945
0.8103	Intermediate Similarity	NPC52839
0.8103	Intermediate Similarity	NPC470779
0.8095	Intermediate Similarity	NPC222011
0.8091	Intermediate Similarity	NPC286174
0.8091	Intermediate Similarity	NPC77947
0.8091	Intermediate Similarity	NPC141350
0.8091	Intermediate Similarity	NPC475922
0.8087	Intermediate Similarity	NPC472933
0.8081	Intermediate Similarity	NPC220478
0.8073	Intermediate Similarity	NPC86852
0.8073	Intermediate Similarity	NPC112780
0.8073	Intermediate Similarity	NPC251824
0.807	Intermediate Similarity	NPC23046
0.807	Intermediate Similarity	NPC474654
0.807	Intermediate Similarity	NPC134430
0.807	Intermediate Similarity	NPC470854
0.807	Intermediate Similarity	NPC473968
0.807	Intermediate Similarity	NPC469684
0.807	Intermediate Similarity	NPC97908
0.807	Intermediate Similarity	NPC287343
0.807	Intermediate Similarity	NPC53396
0.807	Intermediate Similarity	NPC122033
0.807	Intermediate Similarity	NPC98249
0.807	Intermediate Similarity	NPC239273
0.807	Intermediate Similarity	NPC472927
0.8058	Intermediate Similarity	NPC476596
0.8056	Intermediate Similarity	NPC65523
0.8053	Intermediate Similarity	NPC238667
0.8053	Intermediate Similarity	NPC178289
0.8053	Intermediate Similarity	NPC474906
0.8053	Intermediate Similarity	NPC18547
0.8051	Intermediate Similarity	NPC470922
0.8037	Intermediate Similarity	NPC136289
0.8037	Intermediate Similarity	NPC472552
0.8037	Intermediate Similarity	NPC183571
0.8037	Intermediate Similarity	NPC80781
0.8036	Intermediate Similarity	NPC289312
0.8036	Intermediate Similarity	NPC476801
0.8036	Intermediate Similarity	NPC151216
0.8036	Intermediate Similarity	NPC100267
0.8036	Intermediate Similarity	NPC101825
0.8036	Intermediate Similarity	NPC472002
0.8036	Intermediate Similarity	NPC4573
0.8036	Intermediate Similarity	NPC90952
0.8036	Intermediate Similarity	NPC475524
0.8036	Intermediate Similarity	NPC221511
0.8036	Intermediate Similarity	NPC269530
0.8036	Intermediate Similarity	NPC170212
0.8036	Intermediate Similarity	NPC17138
0.8036	Intermediate Similarity	NPC11252
0.8036	Intermediate Similarity	NPC265499
0.8036	Intermediate Similarity	NPC221144
0.8036	Intermediate Similarity	NPC215643
0.8036	Intermediate Similarity	NPC89227
0.8034	Intermediate Similarity	NPC162009
0.8034	Intermediate Similarity	NPC257017
0.8019	Intermediate Similarity	NPC476274
0.8019	Intermediate Similarity	NPC293890
0.8019	Intermediate Similarity	NPC306856
0.8018	Intermediate Similarity	NPC478209

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 NPC476479 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	1642
0.2-0.3	3566
0.3-0.4	2317
0.4-0.5	925
0.5-0.6	290
0.6-0.7	192
0.7-0.8	26
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
0.7928	Intermediate Similarity	NPD6372	Approved
0.7928	Intermediate Similarity	NPD6373	Approved
0.7818	Intermediate Similarity	NPD6402	Approved
0.7818	Intermediate Similarity	NPD7128	Approved
0.7818	Intermediate Similarity	NPD5739	Approved
0.7818	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6650	Approved
0.7788	Intermediate Similarity	NPD6649	Approved
0.7757	Intermediate Similarity	NPD7638	Approved
0.7685	Intermediate Similarity	NPD7640	Approved
0.7685	Intermediate Similarity	NPD7639	Approved
0.7679	Intermediate Similarity	NPD6881	Approved
0.7679	Intermediate Similarity	NPD7320	Approved
0.7679	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6899	Approved
0.7589	Intermediate Similarity	NPD5697	Approved
0.7589	Intermediate Similarity	NPD5701	Approved
0.7565	Intermediate Similarity	NPD6882	Approved
0.7565	Intermediate Similarity	NPD8297	Approved
0.7544	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7290	Approved
0.7544	Intermediate Similarity	NPD6883	Approved
0.7544	Intermediate Similarity	NPD7102	Approved
0.7522	Intermediate Similarity	NPD6686	Approved
0.7521	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD7902	Approved
0.7478	Intermediate Similarity	NPD6617	Approved
0.7478	Intermediate Similarity	NPD6869	Approved
0.7478	Intermediate Similarity	NPD6847	Approved
0.7478	Intermediate Similarity	NPD8130	Phase 1
0.7456	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6014	Approved
0.7456	Intermediate Similarity	NPD6012	Approved
0.7456	Intermediate Similarity	NPD6013	Approved
0.7453	Intermediate Similarity	NPD6399	Phase 3
0.7429	Intermediate Similarity	NPD46	Approved
0.7429	Intermediate Similarity	NPD6698	Approved
0.7417	Intermediate Similarity	NPD6319	Approved
0.7414	Intermediate Similarity	NPD6053	Discontinued
0.7383	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD6011	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.735	Intermediate Similarity	NPD4632	Approved
0.7345	Intermediate Similarity	NPD6008	Approved
0.7339	Intermediate Similarity	NPD6083	Phase 2
0.7339	Intermediate Similarity	NPD6084	Phase 2
0.7339	Intermediate Similarity	NPD4755	Approved
0.7328	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7115	Discovery
0.729	Intermediate Similarity	NPD5778	Approved
0.729	Intermediate Similarity	NPD5779	Approved
0.7281	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4225	Approved
0.7258	Intermediate Similarity	NPD7507	Approved
0.7248	Intermediate Similarity	NPD4697	Phase 3
0.7244	Intermediate Similarity	NPD7260	Phase 2
0.7232	Intermediate Similarity	NPD5211	Phase 2
0.7222	Intermediate Similarity	NPD7319	Approved
0.7222	Intermediate Similarity	NPD7900	Approved
0.7222	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5285	Approved
0.7207	Intermediate Similarity	NPD4700	Approved
0.7207	Intermediate Similarity	NPD5286	Approved
0.7207	Intermediate Similarity	NPD4696	Approved
0.7177	Intermediate Similarity	NPD7492	Approved
0.717	Intermediate Similarity	NPD5328	Approved
0.7167	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6009	Approved
0.7156	Intermediate Similarity	NPD5695	Phase 3
0.7156	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6059	Approved
0.7131	Intermediate Similarity	NPD6054	Approved
0.712	Intermediate Similarity	NPD6616	Approved
0.7117	Intermediate Similarity	NPD5696	Approved
0.7115	Intermediate Similarity	NPD1694	Approved
0.7105	Intermediate Similarity	NPD5141	Approved
0.7097	Intermediate Similarity	NPD7604	Phase 2
0.7091	Intermediate Similarity	NPD5222	Approved
0.7091	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6274	Approved
0.708	Intermediate Similarity	NPD5224	Approved
0.708	Intermediate Similarity	NPD5226	Approved
0.708	Intermediate Similarity	NPD4633	Approved
0.708	Intermediate Similarity	NPD5225	Approved
0.708	Intermediate Similarity	NPD7632	Discontinued
0.7075	Intermediate Similarity	NPD6672	Approved
0.7075	Intermediate Similarity	NPD5737	Approved
0.7073	Intermediate Similarity	NPD6921	Approved
0.7073	Intermediate Similarity	NPD5983	Phase 2
0.7063	Intermediate Similarity	NPD7078	Approved
0.7063	Intermediate Similarity	NPD8293	Discontinued
0.7049	Intermediate Similarity	NPD7101	Approved
0.7049	Intermediate Similarity	NPD7100	Approved
0.7048	Intermediate Similarity	NPD3618	Phase 1
0.7043	Intermediate Similarity	NPD4768	Approved
0.7043	Intermediate Similarity	NPD4767	Approved
0.7037	Intermediate Similarity	NPD6411	Approved
0.7037	Intermediate Similarity	NPD6079	Approved
0.7027	Intermediate Similarity	NPD5173	Approved
0.7018	Intermediate Similarity	NPD5175	Approved
0.7018	Intermediate Similarity	NPD5174	Approved
0.7016	Intermediate Similarity	NPD6370	Approved
0.7009	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD7736	Approved
0.6991	Remote Similarity	NPD5223	Approved
0.6991	Remote Similarity	NPD5344	Discontinued
0.699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6336	Discontinued
0.6983	Remote Similarity	NPD6412	Phase 2
0.6983	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6335	Approved
0.6949	Remote Similarity	NPD6371	Approved
0.6949	Remote Similarity	NPD4634	Approved
0.6942	Remote Similarity	NPD6868	Approved
0.6935	Remote Similarity	NPD6015	Approved
0.6935	Remote Similarity	NPD6909	Approved
0.6935	Remote Similarity	NPD6016	Approved
0.6935	Remote Similarity	NPD6908	Approved
0.6923	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD6845	Suspended
0.6909	Remote Similarity	NPD5282	Discontinued
0.6887	Remote Similarity	NPD6684	Approved
0.6887	Remote Similarity	NPD7521	Approved
0.6887	Remote Similarity	NPD5330	Approved
0.6887	Remote Similarity	NPD7146	Approved
0.6887	Remote Similarity	NPD6409	Approved
0.6887	Remote Similarity	NPD7334	Approved
0.6885	Remote Similarity	NPD6317	Approved
0.6881	Remote Similarity	NPD7983	Approved
0.6881	Remote Similarity	NPD5693	Phase 1
0.688	Remote Similarity	NPD5988	Approved
0.687	Remote Similarity	NPD4754	Approved
0.6857	Remote Similarity	NPD4786	Approved
0.6852	Remote Similarity	NPD4753	Phase 2
0.6852	Remote Similarity	NPD6101	Approved
0.6852	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6313	Approved
0.6829	Remote Similarity	NPD7328	Approved
0.6829	Remote Similarity	NPD7327	Approved
0.6829	Remote Similarity	NPD6314	Approved
0.6827	Remote Similarity	NPD3667	Approved
0.6822	Remote Similarity	NPD3573	Approved
0.6807	Remote Similarity	NPD5248	Approved
0.6807	Remote Similarity	NPD5247	Approved
0.6807	Remote Similarity	NPD5251	Approved
0.6807	Remote Similarity	NPD5249	Phase 3
0.6807	Remote Similarity	NPD5250	Approved
0.68	Remote Similarity	NPD8513	Phase 3
0.68	Remote Similarity	NPD8515	Approved
0.68	Remote Similarity	NPD8517	Approved
0.68	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8516	Approved
0.6796	Remote Similarity	NPD4695	Discontinued
0.6789	Remote Similarity	NPD5785	Approved
0.6789	Remote Similarity	NPD7838	Discovery
0.678	Remote Similarity	NPD5128	Approved
0.6774	Remote Similarity	NPD7516	Approved
0.6759	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6903	Approved
0.6754	Remote Similarity	NPD6648	Approved
0.675	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5279	Phase 3
0.6727	Remote Similarity	NPD7637	Suspended
0.6698	Remote Similarity	NPD3665	Phase 1
0.6698	Remote Similarity	NPD3133	Approved
0.6698	Remote Similarity	NPD3666	Approved
0.6697	Remote Similarity	NPD6080	Approved
0.6697	Remote Similarity	NPD6673	Approved
0.6697	Remote Similarity	NPD6904	Approved
0.6696	Remote Similarity	NPD5210	Approved
0.6696	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6636	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6033	Approved
0.6612	Remote Similarity	NPD5216	Approved
0.6612	Remote Similarity	NPD5215	Approved
0.6612	Remote Similarity	NPD5217	Approved
0.6587	Remote Similarity	NPD8294	Approved
0.6587	Remote Similarity	NPD8377	Approved
0.6577	Remote Similarity	NPD5284	Approved
0.6577	Remote Similarity	NPD5281	Approved
0.6577	Remote Similarity	NPD6050	Approved
0.6577	Remote Similarity	NPD8034	Phase 2
0.6577	Remote Similarity	NPD8035	Phase 2
0.6549	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD7503	Approved
0.6529	Remote Similarity	NPD5135	Approved
0.6529	Remote Similarity	NPD5169	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