NPASS Compound

Structure

NPC471493 OpenBabel07101719522D 51 56 0 0 1 0 0 0 0 0999 V2000 -3.0693 -0.5499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3095 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9454 -1.9454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4595 -3.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5503 -3.2232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2375 -0.8473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1586 -3.0295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8077 -2.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6004 -3.7571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8985 -2.0626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6911 -3.6374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7942 1.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0858 -1.3877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1768 3.6683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9171 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4331 -1.2103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4003 -1.6394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0596 -2.1827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3402 -2.7901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7167 -0.9746 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3826 4.1268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5884 0.9171 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9171 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6954 -1.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5884 3.6683 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5884 2.7512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9328 -1.0316 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7942 -0.4585 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4742 -0.2374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5568 -1.3444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4310 -2.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3826 2.2927 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9012 -2.3759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5884 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 -1.0154 -2.1386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0493 -2.4867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5849 -3.9544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5970 -0.0654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3826 5.0439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7942 4.1268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7942 2.2927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0325 0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8727 -3.3980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6892 -2.9956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1768 2.7512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9171 0.9171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8420 -0.9119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3826 1.3756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0800 -1.8232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2374 -0.8858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 33 1 0 0 0 0 5 33 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 36 1 0 0 0 0 14 21 1 0 0 0 0 14 46 1 0 0 0 0 15 35 1 0 0 0 0 15 47 1 0 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 37 2 0 0 0 0 17 48 1 0 0 0 0 18 38 2 0 0 0 0 18 51 1 0 0 0 0 19 31 1 0 0 0 0 20 39 1 1 0 0 0 21 25 1 0 0 0 0 21 40 1 1 0 0 0 22 34 1 1 0 0 0 22 49 1 0 0 0 0 23 35 1 1 0 0 0 23 47 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 41 1 6 0 0 0 26 32 1 0 0 0 0 26 42 1 1 0 0 0 27 29 1 0 0 0 0 27 48 1 1 0 0 0 28 30 1 0 0 0 0 28 34 1 1 0 0 0 28 35 1 0 0 0 0 29 34 1 0 0 0 0 29 43 2 0 0 0 0 30 36 1 6 0 0 0 30 50 1 0 0 0 0 31 44 2 0 0 0 0 31 50 1 0 0 0 0 32 46 1 0 0 0 0 32 49 1 1 0 0 0 33 36 1 0 0 0 0 34 6 1 1 0 0 0 35 51 1 6 0 0 0 36 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	718.28
Volume:	690.635
LogP:	1.704
LogD:	1.213
LogS:	-4.215
# Rotatable Bonds:	9
TPSA:	224.81
# H-Bond Aceptor:	15
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	6.178
Fsp3:	0.667
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:	-5.631
MDCK Permeability:	0.00010613949416438118
Pgp-inhibitor:	0.993
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.897
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	44.58564376831055%
Volume Distribution (VD):	0.622
Pgp-substrate:	20.35983657836914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.197
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	1.445
Half-life (T1/2):	0.242

ADMET: Toxicity

hERG Blockers:	0.265
Human Hepatotoxicity (H-HT):	0.602
Drug-inuced Liver Injury (DILI):	0.363
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.293
Skin Sensitization:	0.261
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC471493

Natural Product ID:	NPC471493
*Common Name:**	CFXLQLVVACEBGI-VHMPTJLLSA-N
IUPAC Name:	n.a.
Synonyms:	7Beta-D-Xylosylbaccatin Iii
Standard InCHIKey:	CFXLQLVVACEBGI-VHMPTJLLSA-N
Standard InCHI:	InChI=1S/C36H46O15/c1-16-20(39)13-36(45)30(50-31(44)19-10-8-7-9-11-19)28-34(6,29(43)27(48-17(2)37)24(16)33(36,4)5)22(12-23-35(28,15-47-23)51-18(3)38)49-32-26(42)25(41)21(40)14-46-32/h7-11,20-23,25-28,30,32,39-42,45H,12-15H2,1-6H3/t20-,21+,22-,23+,25-,26+,27+,28-,30-,32+,34+,35-,36+/m0/s1
SMILES:	CC(=O)O[C@@H]1C2=C(C)[C@@H](O)C[C@@](C2(C)C)(O)[C@H]([C@H]2[C@@](C1=O)(C)[C@@H](O[C@H]1OC[C@H]([C@@H]([C@H]1O)O)O)C[C@@H]1[C@]2(CO1)OC(=O)C)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252932
PubChem CID:	44445497
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
NPO32766	luteibacter sp.	Species	Rhodanobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[18001087]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	<	10000.0	nM	PMID[523521]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	<	10000.0	nM	PMID[523521]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	<	10000.0	nM	PMID[523521]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[523521]
NPT179	Cell Line	A2780	Homo sapiens	IC50	<	10000.0	nM	PMID[523521]

☑ 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 NPC471493 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	384
0.1-0.2	1314
0.2-0.3	2872
0.3-0.4	5828
0.4-0.5	10262
0.5-0.6	10693
0.6-0.7	9048
0.7-0.8	2011
0.8-0.85	216
0.85-0.9	57
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC155329
0.9474	High Similarity	NPC114357
0.9474	High Similarity	NPC259144
0.9408	High Similarity	NPC134685
0.9408	High Similarity	NPC11588
0.9408	High Similarity	NPC229545
0.9408	High Similarity	NPC219419
0.9408	High Similarity	NPC248265
0.9276	High Similarity	NPC197037
0.9211	High Similarity	NPC91730
0.9097	High Similarity	NPC21410
0.9097	High Similarity	NPC473670
0.9079	High Similarity	NPC217918
0.9068	High Similarity	NPC102465
0.9045	High Similarity	NPC469399
0.9032	High Similarity	NPC469477
0.9032	High Similarity	NPC133430
0.8981	High Similarity	NPC469417
0.8981	High Similarity	NPC472393
0.8974	High Similarity	NPC5115
0.8961	High Similarity	NPC7095
0.8938	High Similarity	NPC150893
0.8938	High Similarity	NPC329960
0.8938	High Similarity	NPC295408
0.8917	High Similarity	NPC106895
0.8917	High Similarity	NPC217091
0.8903	High Similarity	NPC101043
0.8903	High Similarity	NPC471103
0.8903	High Similarity	NPC51602
0.8903	High Similarity	NPC306799
0.8896	High Similarity	NPC250046
0.8896	High Similarity	NPC60509
0.8896	High Similarity	NPC81698
0.8882	High Similarity	NPC38696
0.8861	High Similarity	NPC477735
0.8854	High Similarity	NPC473632
0.8854	High Similarity	NPC469730
0.8854	High Similarity	NPC472549
0.8854	High Similarity	NPC228204
0.8854	High Similarity	NPC26033
0.8854	High Similarity	NPC132599
0.8854	High Similarity	NPC282239
0.8854	High Similarity	NPC473611
0.8839	High Similarity	NPC165260
0.8839	High Similarity	NPC161239
0.8839	High Similarity	NPC198455
0.8839	High Similarity	NPC112216
0.8824	High Similarity	NPC127857
0.8805	High Similarity	NPC477736
0.879	High Similarity	NPC472022
0.879	High Similarity	NPC472005
0.879	High Similarity	NPC256142
0.879	High Similarity	NPC304876
0.879	High Similarity	NPC237549
0.879	High Similarity	NPC265395
0.879	High Similarity	NPC257213
0.879	High Similarity	NPC473414
0.879	High Similarity	NPC472030
0.879	High Similarity	NPC242262
0.879	High Similarity	NPC1173
0.879	High Similarity	NPC158333
0.879	High Similarity	NPC249471
0.878	High Similarity	NPC477469
0.878	High Similarity	NPC477466
0.878	High Similarity	NPC477473
0.878	High Similarity	NPC477471
0.8766	High Similarity	NPC477737
0.8765	High Similarity	NPC471134
0.875	High Similarity	NPC34012
0.8734	High Similarity	NPC112523
0.8734	High Similarity	NPC114410
0.8726	High Similarity	NPC472548
0.8704	High Similarity	NPC66193
0.8688	High Similarity	NPC471102
0.8671	High Similarity	NPC77719
0.8662	High Similarity	NPC470153
0.8645	High Similarity	NPC469513
0.8642	High Similarity	NPC43304
0.8642	High Similarity	NPC477188
0.8642	High Similarity	NPC477190
0.8627	High Similarity	NPC182869
0.8625	High Similarity	NPC469771
0.8623	High Similarity	NPC469421
0.8616	High Similarity	NPC469422
0.8616	High Similarity	NPC34066
0.8608	High Similarity	NPC477905
0.8606	High Similarity	NPC469420
0.8599	High Similarity	NPC469448
0.8599	High Similarity	NPC470245
0.8599	High Similarity	NPC473214
0.8599	High Similarity	NPC254558
0.8598	High Similarity	NPC61891
0.8598	High Similarity	NPC477491
0.8589	High Similarity	NPC322420
0.8589	High Similarity	NPC478073
0.8581	High Similarity	NPC471107
0.8581	High Similarity	NPC277053
0.8581	High Similarity	NPC301946
0.8581	High Similarity	NPC471100
0.858	High Similarity	NPC476077
0.8562	High Similarity	NPC11410
0.8554	High Similarity	NPC469419
0.8544	High Similarity	NPC329657
0.8544	High Similarity	NPC469415
0.8539	High Similarity	NPC472391
0.8537	High Similarity	NPC477627
0.8535	High Similarity	NPC476975
0.8535	High Similarity	NPC473215
0.8526	High Similarity	NPC474935
0.8519	High Similarity	NPC477623
0.8516	High Similarity	NPC80895
0.8516	High Similarity	NPC471912
0.8506	High Similarity	NPC472546
0.85	High Similarity	NPC469456
0.85	High Similarity	NPC469398
0.85	High Similarity	NPC251139
0.8497	Intermediate Similarity	NPC471623
0.8494	Intermediate Similarity	NPC40138
0.8485	Intermediate Similarity	NPC324769
0.8485	Intermediate Similarity	NPC325732
0.8483	Intermediate Similarity	NPC472392
0.8483	Intermediate Similarity	NPC472375
0.8481	Intermediate Similarity	NPC303429
0.8481	Intermediate Similarity	NPC222102
0.8457	Intermediate Similarity	NPC49297
0.8452	Intermediate Similarity	NPC477894
0.8443	Intermediate Similarity	NPC477488
0.8442	Intermediate Similarity	NPC77493
0.8438	Intermediate Similarity	NPC69425
0.8421	Intermediate Similarity	NPC472372
0.8421	Intermediate Similarity	NPC472374
0.8415	Intermediate Similarity	NPC275477
0.8398	Intermediate Similarity	NPC116862
0.8395	Intermediate Similarity	NPC181924
0.8383	Intermediate Similarity	NPC470735
0.8383	Intermediate Similarity	NPC329647
0.8377	Intermediate Similarity	NPC183270
0.8377	Intermediate Similarity	NPC477904
0.8377	Intermediate Similarity	NPC472547
0.8375	Intermediate Similarity	NPC469647
0.8375	Intermediate Similarity	NPC469648
0.8375	Intermediate Similarity	NPC22571
0.8375	Intermediate Similarity	NPC283875
0.8375	Intermediate Similarity	NPC138641
0.8363	Intermediate Similarity	NPC19056
0.8363	Intermediate Similarity	NPC470583
0.8344	Intermediate Similarity	NPC174982
0.8344	Intermediate Similarity	NPC476973
0.8344	Intermediate Similarity	NPC29704
0.8344	Intermediate Similarity	NPC473088
0.8344	Intermediate Similarity	NPC472572
0.8344	Intermediate Similarity	NPC472575
0.8344	Intermediate Similarity	NPC184817
0.8344	Intermediate Similarity	NPC471104
0.8344	Intermediate Similarity	NPC472568
0.8344	Intermediate Similarity	NPC158663
0.8344	Intermediate Similarity	NPC70403
0.8344	Intermediate Similarity	NPC470159
0.8344	Intermediate Similarity	NPC200471
0.8344	Intermediate Similarity	NPC477467
0.8344	Intermediate Similarity	NPC470157
0.8344	Intermediate Similarity	NPC177940
0.8344	Intermediate Similarity	NPC171525
0.8344	Intermediate Similarity	NPC472571
0.8344	Intermediate Similarity	NPC472556
0.8344	Intermediate Similarity	NPC96903
0.8344	Intermediate Similarity	NPC469349
0.8344	Intermediate Similarity	NPC476784
0.8343	Intermediate Similarity	NPC289383
0.8333	Intermediate Similarity	NPC149002
0.8333	Intermediate Similarity	NPC91703
0.8333	Intermediate Similarity	NPC469458
0.8333	Intermediate Similarity	NPC88176
0.8333	Intermediate Similarity	NPC469459
0.8333	Intermediate Similarity	NPC469396
0.8323	Intermediate Similarity	NPC472576
0.8323	Intermediate Similarity	NPC118080
0.8323	Intermediate Similarity	NPC291599
0.8323	Intermediate Similarity	NPC27377
0.8323	Intermediate Similarity	NPC97947
0.8323	Intermediate Similarity	NPC87448
0.8323	Intermediate Similarity	NPC41481
0.8323	Intermediate Similarity	NPC16912
0.8313	Intermediate Similarity	NPC472398
0.8303	Intermediate Similarity	NPC165234
0.8303	Intermediate Similarity	NPC475536
0.8295	Intermediate Similarity	NPC33372
0.8295	Intermediate Similarity	NPC67246
0.8294	Intermediate Similarity	NPC470580
0.8291	Intermediate Similarity	NPC20255
0.8282	Intermediate Similarity	NPC477470
0.8282	Intermediate Similarity	NPC477474
0.8282	Intermediate Similarity	NPC477472
0.828	Intermediate Similarity	NPC475122
0.828	Intermediate Similarity	NPC472569
0.828	Intermediate Similarity	NPC472573
0.828	Intermediate Similarity	NPC476974
0.828	Intermediate Similarity	NPC472570
0.828	Intermediate Similarity	NPC470152
0.828	Intermediate Similarity	NPC11685

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 NPC471493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	841
0.2-0.3	1882
0.3-0.4	3009
0.4-0.5	2027
0.5-0.6	841
0.6-0.7	181
0.7-0.8	35
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8855	High Similarity	NPD8368	Discontinued
0.8698	High Similarity	NPD8407	Phase 2
0.8675	High Similarity	NPD8470	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD8360	Approved
0.8497	Intermediate Similarity	NPD8361	Approved
0.8497	Intermediate Similarity	NPD8435	Approved
0.8393	Intermediate Similarity	NPD7799	Discontinued
0.8278	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD8434	Phase 2
0.8171	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD8485	Approved
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7236	Approved
0.7758	Intermediate Similarity	NPD7239	Suspended
0.7756	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8150	Discontinued
0.7611	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8462	Phase 1
0.7526	Intermediate Similarity	NPD8320	Phase 1
0.7526	Intermediate Similarity	NPD8319	Approved
0.7514	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7444	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6534	Approved
0.7419	Intermediate Similarity	NPD6535	Approved
0.7403	Intermediate Similarity	NPD8312	Approved
0.7403	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8404	Phase 2
0.7348	Intermediate Similarity	NPD7808	Phase 3
0.7341	Intermediate Similarity	NPD7058	Phase 2
0.7341	Intermediate Similarity	NPD7057	Phase 3
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7299	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7075	Discontinued
0.7293	Intermediate Similarity	NPD7251	Discontinued
0.7263	Intermediate Similarity	NPD3751	Discontinued
0.7238	Intermediate Similarity	NPD6797	Phase 2
0.7233	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6781	Approved
0.7225	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6776	Approved
0.7225	Intermediate Similarity	NPD6778	Approved
0.7225	Intermediate Similarity	NPD6779	Approved
0.7225	Intermediate Similarity	NPD6782	Approved
0.7225	Intermediate Similarity	NPD6777	Approved
0.7225	Intermediate Similarity	NPD6780	Approved
0.7204	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7697	Approved
0.7202	Intermediate Similarity	NPD7696	Phase 3
0.7202	Intermediate Similarity	NPD7698	Approved
0.7198	Intermediate Similarity	NPD7685	Pre-registration
0.7186	Intermediate Similarity	NPD6190	Approved
0.7182	Intermediate Similarity	NPD7074	Phase 3
0.7165	Intermediate Similarity	NPD7871	Phase 2
0.7165	Intermediate Similarity	NPD7870	Phase 2
0.716	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7127	Intermediate Similarity	NPD7054	Approved
0.7121	Intermediate Similarity	NPD7801	Approved
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7088	Intermediate Similarity	NPD7472	Approved
0.7086	Intermediate Similarity	NPD5402	Approved
0.7072	Intermediate Similarity	NPD3818	Discontinued
0.7069	Intermediate Similarity	NPD6801	Discontinued
0.7052	Intermediate Similarity	NPD4380	Phase 2
0.7052	Intermediate Similarity	NPD6599	Discontinued
0.7039	Intermediate Similarity	NPD3787	Discontinued
0.7029	Intermediate Similarity	NPD7819	Suspended
0.7024	Intermediate Similarity	NPD4628	Phase 3
0.7011	Intermediate Similarity	NPD6559	Discontinued
0.6978	Remote Similarity	NPD7228	Approved
0.6976	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2629	Approved
0.6946	Remote Similarity	NPD7266	Discontinued
0.694	Remote Similarity	NPD5844	Phase 1
0.6935	Remote Similarity	NPD8151	Discontinued
0.6933	Remote Similarity	NPD7961	Discontinued
0.6923	Remote Similarity	NPD8166	Discontinued
0.6923	Remote Similarity	NPD7473	Discontinued
0.6911	Remote Similarity	NPD6213	Phase 3
0.6911	Remote Similarity	NPD6212	Phase 3
0.6911	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3817	Phase 2
0.6888	Remote Similarity	NPD6823	Phase 2
0.6879	Remote Similarity	NPD5403	Approved
0.6879	Remote Similarity	NPD8328	Phase 3
0.6875	Remote Similarity	NPD37	Approved
0.6872	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6166	Phase 2
0.6868	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4967	Phase 2
0.6854	Remote Similarity	NPD4966	Approved
0.6854	Remote Similarity	NPD4965	Approved
0.6854	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8455	Phase 2
0.6818	Remote Similarity	NPD4198	Discontinued
0.6802	Remote Similarity	NPD6799	Approved
0.6798	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7783	Phase 2
0.6778	Remote Similarity	NPD6234	Discontinued
0.6763	Remote Similarity	NPD5401	Approved
0.6758	Remote Similarity	NPD6232	Discontinued
0.6742	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5494	Approved
0.6738	Remote Similarity	NPD6765	Approved
0.6738	Remote Similarity	NPD6764	Approved
0.6738	Remote Similarity	NPD7240	Approved
0.6723	Remote Similarity	NPD7411	Suspended
0.6709	Remote Similarity	NPD5125	Phase 3
0.6709	Remote Similarity	NPD5126	Approved
0.6707	Remote Similarity	NPD7008	Discontinued
0.6703	Remote Similarity	NPD8127	Discontinued
0.6685	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5761	Phase 2
0.6648	Remote Similarity	NPD5760	Phase 2
0.6646	Remote Similarity	NPD8513	Phase 3
0.6646	Remote Similarity	NPD8515	Approved
0.6646	Remote Similarity	NPD8516	Approved
0.6646	Remote Similarity	NPD8517	Approved
0.663	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3226	Approved
0.6605	Remote Similarity	NPD7736	Approved
0.6604	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6785	Approved
0.6597	Remote Similarity	NPD6784	Approved
0.6595	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7741	Discontinued
0.6571	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2532	Approved
0.6571	Remote Similarity	NPD2534	Approved
0.6571	Remote Similarity	NPD2533	Approved
0.6571	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7319	Approved
0.6556	Remote Similarity	NPD2801	Approved
0.6552	Remote Similarity	NPD3300	Phase 2
0.655	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2346	Discontinued
0.6548	Remote Similarity	NPD230	Phase 1
0.6538	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7305	Phase 1
0.6522	Remote Similarity	NPD6959	Discontinued
0.6522	Remote Similarity	NPD7199	Phase 2
0.6517	Remote Similarity	NPD7497	Discontinued
0.6514	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7768	Phase 2
0.6477	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6010	Discontinued
0.6474	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3764	Approved
0.6465	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD1465	Phase 2
0.6448	Remote Similarity	NPD3749	Approved
0.6442	Remote Similarity	NPD7930	Approved
0.6441	Remote Similarity	NPD6273	Approved
0.6437	Remote Similarity	NPD3750	Approved
0.6433	Remote Similarity	NPD5951	Approved
0.6425	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7584	Approved
0.6419	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD8059	Phase 3
0.6416	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD1549	Phase 2
0.6415	Remote Similarity	NPD7907	Approved
0.64	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6370	Approved
0.6398	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6100	Approved
0.6395	Remote Similarity	NPD6099	Approved
0.6395	Remote Similarity	NPD2935	Discontinued
0.6389	Remote Similarity	NPD7028	Phase 2
0.6387	Remote Similarity	NPD5030	Phase 2
0.6387	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7507	Approved
0.6379	Remote Similarity	NPD6674	Discontinued
0.6374	Remote Similarity	NPD7097	Phase 1
0.6373	Remote Similarity	NPD7999	Approved
0.6369	Remote Similarity	NPD1653	Approved
0.6364	Remote Similarity	NPD2182	Approved
0.6358	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1552	Clinical (unspecified phase)

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