NPASS Compound

Structure

CID248265 OpenBabel06191716052D 39 43 0 0 1 0 0 0 0 0999 V2000 -2.9930 0.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8970 1.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3983 3.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5117 3.1430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2067 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 2.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6633 2.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4611 3.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7767 2.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5745 3.5469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7745 -1.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0588 1.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8943 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3726 1.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0332 2.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2323 2.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6740 0.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5489 -0.8943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.8943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6284 1.8697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8598 1.0059 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7745 0.4471 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4127 0.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5430 1.3109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3457 2.6040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8539 2.3168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5489 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 -0.9901 2.0854 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5703 3.8561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5573 0.0638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3234 -1.3414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7465 0.8892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9571 -0.4780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8013 3.3135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6720 2.9212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8943 -0.8943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0035 1.7778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2315 0.8638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 29 1 0 0 0 0 13 28 1 0 0 0 0 13 37 1 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 30 2 0 0 0 0 15 39 1 0 0 0 0 16 25 1 0 0 0 0 17 31 2 0 0 0 0 18 27 1 6 0 0 0 18 32 1 0 0 0 0 19 28 1 6 0 0 0 19 37 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 33 1 6 0 0 0 22 24 1 0 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 34 2 0 0 0 0 24 29 1 1 0 0 0 24 38 1 0 0 0 0 25 35 2 0 0 0 0 25 38 1 0 0 0 0 26 29 1 0 0 0 0 27 5 1 6 0 0 0 28 39 1 1 0 0 0 29 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.22
Volume:	534.168
LogP:	2.194
LogD:	1.333
LogS:	-4.482
# Rotatable Bonds:	5
TPSA:	153.5
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	5.569
Fsp3:	0.621
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:	-5.355
MDCK Permeability:	5.267150481813587e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.958
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.682
Plasma Protein Binding (PPB):	68.78846740722656%
Volume Distribution (VD):	0.49
Pgp-substrate:	26.65427589416504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	7.903
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.19
Human Hepatotoxicity (H-HT):	0.786
Drug-inuced Liver Injury (DILI):	0.543
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.521
Maximum Recommended Daily Dose:	0.605
Skin Sensitization:	0.132
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC248265

Natural Product ID:	NPC248265
*Common Name:**	WMZBAMYUOYXRSF-RIFKXWPOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WMZBAMYUOYXRSF-RIFKXWPOSA-N
Standard InCHI:	InChI=1S/C29H34O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,18-19,21-22,24,32-33,36H,11-13H2,1-5H3/t18-,19+,21+,22-,24-,27+,28-,29+/m0/s1
SMILES:	CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)CC(=O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510651
PubChem CID:	15227070
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
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[12502326]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679325]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220355]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23720	Taxus wallichiana	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	4

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT376	Cell Line	A498	Homo sapiens	Inhibition	=	29.7	%	PMID[540449]
NPT405	Cell Line	NCI-H226	Homo sapiens	Inhibition	=	49.2	%	PMID[540449]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	43.9	%	PMID[540449]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	=	65.3	%	PMID[540449]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[540450]
NPT2	Others	Unspecified		IC50	>	250000.0	nM	PMID[540450]

☑ 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 NPC248265 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	347
0.1-0.2	1192
0.2-0.3	2642
0.3-0.4	5845
0.4-0.5	10093
0.5-0.6	10340
0.6-0.7	10237
0.7-0.8	1717
0.8-0.85	207
0.85-0.9	59
0.9-0.95	7
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC229545
1.0	High Similarity	NPC11588
1.0	High Similarity	NPC134685
0.9931	High Similarity	NPC155329
0.9931	High Similarity	NPC259144
0.9931	High Similarity	NPC114357
0.9861	High Similarity	NPC219419
0.986	High Similarity	NPC197037
0.979	High Similarity	NPC91730
0.965	High Similarity	NPC217918
0.9441	High Similarity	NPC38696
0.9408	High Similarity	NPC471493
0.9392	High Similarity	NPC21410
0.9392	High Similarity	NPC473670
0.9375	High Similarity	NPC127857
0.932	High Similarity	NPC471103
0.9315	High Similarity	NPC81698
0.9315	High Similarity	NPC60509
0.9315	High Similarity	NPC250046
0.9252	High Similarity	NPC161239
0.9252	High Similarity	NPC165260
0.9252	High Similarity	NPC7095
0.9252	High Similarity	NPC198455
0.9189	High Similarity	NPC306799
0.9189	High Similarity	NPC101043
0.9189	High Similarity	NPC51602
0.9167	High Similarity	NPC34012
0.9139	High Similarity	NPC472393
0.9133	High Similarity	NPC473632
0.9133	High Similarity	NPC26033
0.9133	High Similarity	NPC132599
0.9133	High Similarity	NPC469730
0.9133	High Similarity	NPC228204
0.9122	High Similarity	NPC112216
0.9073	High Similarity	NPC106895
0.9073	High Similarity	NPC217091
0.9067	High Similarity	NPC472030
0.9067	High Similarity	NPC472005
0.9067	High Similarity	NPC265395
0.9067	High Similarity	NPC249471
0.9067	High Similarity	NPC257213
0.9067	High Similarity	NPC237549
0.9067	High Similarity	NPC472022
0.9067	High Similarity	NPC242262
0.9067	High Similarity	NPC304876
0.9067	High Similarity	NPC158333
0.9067	High Similarity	NPC1173
0.9067	High Similarity	NPC473414
0.9067	High Similarity	NPC256142
0.9034	High Similarity	NPC182869
0.9007	High Similarity	NPC114410
0.9007	High Similarity	NPC112523
0.9007	High Similarity	NPC282239
0.9007	High Similarity	NPC472549
0.9007	High Similarity	NPC473611
0.898	High Similarity	NPC471107
0.898	High Similarity	NPC471100
0.8973	High Similarity	NPC477894
0.8947	High Similarity	NPC11410
0.894	High Similarity	NPC77719
0.8933	High Similarity	NPC470153
0.8897	High Similarity	NPC472547
0.8889	High Similarity	NPC469771
0.8882	High Similarity	NPC251139
0.8874	High Similarity	NPC472548
0.8851	High Similarity	NPC277053
0.8851	High Similarity	NPC301946
0.8836	High Similarity	NPC118080
0.8836	High Similarity	NPC87448
0.8836	High Similarity	NPC27377
0.8836	High Similarity	NPC291599
0.8836	High Similarity	NPC41481
0.8836	High Similarity	NPC97947
0.8836	High Similarity	NPC472576
0.8831	High Similarity	NPC471102
0.8819	High Similarity	NPC472374
0.8819	High Similarity	NPC472372
0.8816	High Similarity	NPC469477
0.8816	High Similarity	NPC133430
0.8792	High Similarity	NPC474935
0.8784	High Similarity	NPC471912
0.8784	High Similarity	NPC80895
0.8776	High Similarity	NPC472546
0.8767	High Similarity	NPC171207
0.8767	High Similarity	NPC97667
0.8767	High Similarity	NPC100913
0.8767	High Similarity	NPC90614
0.8767	High Similarity	NPC275592
0.8759	High Similarity	NPC39549
0.875	High Similarity	NPC138641
0.875	High Similarity	NPC469648
0.875	High Similarity	NPC477896
0.875	High Similarity	NPC477905
0.875	High Similarity	NPC283875
0.875	High Similarity	NPC22571
0.875	High Similarity	NPC477893
0.875	High Similarity	NPC469647
0.8742	High Similarity	NPC473214
0.8742	High Similarity	NPC470245
0.8742	High Similarity	NPC254558
0.8733	High Similarity	NPC132652
0.8725	High Similarity	NPC311825
0.8725	High Similarity	NPC92867
0.8718	High Similarity	NPC476077
0.871	High Similarity	NPC469399
0.8707	High Similarity	NPC16912
0.869	High Similarity	NPC472551
0.869	High Similarity	NPC472545
0.8684	High Similarity	NPC472398
0.8675	High Similarity	NPC473215
0.8675	High Similarity	NPC476975
0.8671	High Similarity	NPC80599
0.8667	High Similarity	NPC477737
0.8667	High Similarity	NPC20255
0.8658	High Similarity	NPC241951
0.8658	High Similarity	NPC475759
0.8658	High Similarity	NPC470152
0.8645	High Similarity	NPC469417
0.8639	High Similarity	NPC477904
0.8639	High Similarity	NPC183270
0.8636	High Similarity	NPC5115
0.8627	High Similarity	NPC233581
0.8627	High Similarity	NPC145649
0.86	High Similarity	NPC472568
0.86	High Similarity	NPC469349
0.86	High Similarity	NPC171525
0.86	High Similarity	NPC472572
0.86	High Similarity	NPC177940
0.86	High Similarity	NPC158663
0.86	High Similarity	NPC174982
0.86	High Similarity	NPC470159
0.86	High Similarity	NPC472556
0.86	High Similarity	NPC29704
0.86	High Similarity	NPC472575
0.86	High Similarity	NPC200471
0.86	High Similarity	NPC184817
0.86	High Similarity	NPC70403
0.86	High Similarity	NPC470157
0.86	High Similarity	NPC96903
0.86	High Similarity	NPC471104
0.86	High Similarity	NPC473088
0.86	High Similarity	NPC472571
0.86	High Similarity	NPC125882
0.86	High Similarity	NPC476973
0.8591	High Similarity	NPC163087
0.8591	High Similarity	NPC95449
0.8581	High Similarity	NPC213567
0.8553	High Similarity	NPC471134
0.8544	High Similarity	NPC477188
0.8544	High Similarity	NPC477190
0.8544	High Similarity	NPC43304
0.8543	High Similarity	NPC469513
0.8542	High Similarity	NPC209851
0.8542	High Similarity	NPC472394
0.8533	High Similarity	NPC475122
0.8533	High Similarity	NPC472569
0.8533	High Similarity	NPC70716
0.8533	High Similarity	NPC125106
0.8533	High Similarity	NPC25768
0.8533	High Similarity	NPC476974
0.8533	High Similarity	NPC163719
0.8533	High Similarity	NPC95265
0.8533	High Similarity	NPC57628
0.8533	High Similarity	NPC188865
0.8533	High Similarity	NPC472570
0.8533	High Similarity	NPC34943
0.8533	High Similarity	NPC472573
0.8533	High Similarity	NPC11685
0.8533	High Similarity	NPC95810
0.8509	High Similarity	NPC102465
0.8493	Intermediate Similarity	NPC195647
0.8493	Intermediate Similarity	NPC66761
0.8493	Intermediate Similarity	NPC472577
0.8493	Intermediate Similarity	NPC291638
0.8493	Intermediate Similarity	NPC17877
0.8491	Intermediate Similarity	NPC66193
0.8487	Intermediate Similarity	NPC473760
0.8467	Intermediate Similarity	NPC91703
0.8462	Intermediate Similarity	NPC317882
0.8462	Intermediate Similarity	NPC471754
0.8462	Intermediate Similarity	NPC70344
0.8462	Intermediate Similarity	NPC475336
0.8462	Intermediate Similarity	NPC473300
0.8462	Intermediate Similarity	NPC453583
0.8456	Intermediate Similarity	NPC224491
0.8447	Intermediate Similarity	NPC161151
0.8431	Intermediate Similarity	NPC266265
0.8431	Intermediate Similarity	NPC301556
0.8431	Intermediate Similarity	NPC471101
0.8431	Intermediate Similarity	NPC92293
0.8431	Intermediate Similarity	NPC270590
0.8428	Intermediate Similarity	NPC55744
0.8425	Intermediate Similarity	NPC474608
0.8421	Intermediate Similarity	NPC478263
0.8421	Intermediate Similarity	NPC209592
0.8421	Intermediate Similarity	NPC240115
0.8421	Intermediate Similarity	NPC48599
0.8412	Intermediate Similarity	NPC33372
0.8412	Intermediate Similarity	NPC67246
0.8411	Intermediate Similarity	NPC470231

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 NPC248265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	793
0.2-0.3	1757
0.3-0.4	2897
0.4-0.5	2167
0.5-0.6	952
0.6-0.7	270
0.7-0.8	17
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD8368	Discontinued
0.8614	High Similarity	NPD8434	Phase 2
0.8606	High Similarity	NPD8407	Phase 2
0.8512	High Similarity	NPD8361	Approved
0.8512	High Similarity	NPD8360	Approved
0.8402	Intermediate Similarity	NPD8435	Approved
0.8242	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD8485	Approved
0.8117	Intermediate Similarity	NPD7236	Approved
0.8079	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7239	Suspended
0.7964	Intermediate Similarity	NPD7799	Discontinued
0.7759	Intermediate Similarity	NPD8150	Discontinued
0.753	Intermediate Similarity	NPD7057	Phase 3
0.753	Intermediate Similarity	NPD7058	Phase 2
0.7516	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8462	Phase 1
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7484	Intermediate Similarity	NPD6190	Approved
0.7448	Intermediate Similarity	NPD8404	Phase 2
0.7421	Intermediate Similarity	NPD4628	Phase 3
0.7413	Intermediate Similarity	NPD2629	Approved
0.741	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6801	Discontinued
0.7333	Intermediate Similarity	NPD6599	Discontinued
0.732	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7473	Discontinued
0.7262	Intermediate Similarity	NPD5402	Approved
0.7229	Intermediate Similarity	NPD4380	Phase 2
0.7202	Intermediate Similarity	NPD7819	Suspended
0.716	Intermediate Similarity	NPD3817	Phase 2
0.7123	Intermediate Similarity	NPD4198	Discontinued
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.711	Intermediate Similarity	NPD6232	Discontinued
0.7102	Intermediate Similarity	NPD5844	Phase 1
0.7099	Intermediate Similarity	NPD8166	Discontinued
0.7097	Intermediate Similarity	NPD7699	Phase 2
0.7097	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7435	Discontinued
0.7088	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6799	Approved
0.7053	Intermediate Similarity	NPD8320	Phase 1
0.7053	Intermediate Similarity	NPD8319	Approved
0.7048	Intermediate Similarity	NPD5403	Approved
0.7045	Intermediate Similarity	NPD3751	Discontinued
0.7039	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6166	Phase 2
0.7029	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7961	Discontinued
0.7006	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5760	Phase 2
0.6987	Remote Similarity	NPD7008	Discontinued
0.6983	Remote Similarity	NPD6765	Approved
0.6983	Remote Similarity	NPD6764	Approved
0.6977	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7458	Discontinued
0.6964	Remote Similarity	NPD3226	Approved
0.6949	Remote Similarity	NPD3818	Discontinued
0.6941	Remote Similarity	NPD1934	Approved
0.6931	Remote Similarity	NPD6777	Approved
0.6931	Remote Similarity	NPD6780	Approved
0.6931	Remote Similarity	NPD6782	Approved
0.6931	Remote Similarity	NPD6781	Approved
0.6931	Remote Similarity	NPD6779	Approved
0.6931	Remote Similarity	NPD6778	Approved
0.6931	Remote Similarity	NPD6776	Approved
0.6928	Remote Similarity	NPD2534	Approved
0.6928	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2533	Approved
0.6928	Remote Similarity	NPD5401	Approved
0.6928	Remote Similarity	NPD2532	Approved
0.6927	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3882	Suspended
0.6918	Remote Similarity	NPD230	Phase 1
0.6901	Remote Similarity	NPD2801	Approved
0.6897	Remote Similarity	NPD5494	Approved
0.6894	Remote Similarity	NPD7305	Phase 1
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7251	Discontinued
0.6882	Remote Similarity	NPD7411	Suspended
0.6875	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7074	Phase 3
0.6872	Remote Similarity	NPD7874	Approved
0.6867	Remote Similarity	NPD7741	Discontinued
0.686	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8127	Discontinued
0.6851	Remote Similarity	NPD7808	Phase 3
0.6842	Remote Similarity	NPD37	Approved
0.6835	Remote Similarity	NPD3764	Approved
0.6833	Remote Similarity	NPD6797	Phase 2
0.6831	Remote Similarity	NPD6784	Approved
0.6831	Remote Similarity	NPD6785	Approved
0.6829	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5951	Approved
0.6823	Remote Similarity	NPD7698	Approved
0.6823	Remote Similarity	NPD7697	Approved
0.6823	Remote Similarity	NPD7696	Phase 3
0.6821	Remote Similarity	NPD4965	Approved
0.6821	Remote Similarity	NPD4967	Phase 2
0.6821	Remote Similarity	NPD4966	Approved
0.6818	Remote Similarity	NPD3787	Discontinued
0.6816	Remote Similarity	NPD7054	Approved
0.681	Remote Similarity	NPD2346	Discontinued
0.6807	Remote Similarity	NPD3300	Phase 2
0.6806	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6559	Discontinued
0.6796	Remote Similarity	NPD7685	Pre-registration
0.6788	Remote Similarity	NPD7871	Phase 2
0.6788	Remote Similarity	NPD7870	Phase 2
0.6781	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7472	Approved
0.6769	Remote Similarity	NPD7701	Phase 2
0.6768	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2182	Approved
0.6757	Remote Similarity	NPD6010	Discontinued
0.6751	Remote Similarity	NPD7801	Approved
0.6748	Remote Similarity	NPD2935	Discontinued
0.6747	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6234	Discontinued
0.6735	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD3750	Approved
0.6687	Remote Similarity	NPD2799	Discontinued
0.6686	Remote Similarity	NPD6273	Approved
0.6686	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD5125	Phase 3
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD7228	Approved
0.6667	Remote Similarity	NPD6651	Approved
0.6667	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD5126	Approved
0.6649	Remote Similarity	NPD7497	Discontinued
0.6648	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6100	Approved
0.6646	Remote Similarity	NPD2796	Approved
0.6646	Remote Similarity	NPD6099	Approved
0.6645	Remote Similarity	NPD9545	Approved
0.6629	Remote Similarity	NPD7768	Phase 2
0.6627	Remote Similarity	NPD2800	Approved
0.6627	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2313	Discontinued
0.6623	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6212	Phase 3
0.6614	Remote Similarity	NPD6213	Phase 3
0.6612	Remote Similarity	NPD5030	Phase 2
0.6609	Remote Similarity	NPD1465	Phase 2
0.6606	Remote Similarity	NPD7266	Discontinued
0.6606	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6355	Discontinued
0.6598	Remote Similarity	NPD6823	Phase 2
0.6597	Remote Similarity	NPD1237	Approved
0.6591	Remote Similarity	NPD3749	Approved
0.6587	Remote Similarity	NPD7003	Approved
0.6587	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7033	Discontinued
0.6582	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6085	Phase 2
0.6581	Remote Similarity	NPD6287	Discontinued
0.6581	Remote Similarity	NPD4806	Approved
0.6581	Remote Similarity	NPD4807	Approved
0.6576	Remote Similarity	NPD36	Approved
0.6576	Remote Similarity	NPD4955	Approved
0.6576	Remote Similarity	NPD5026	Approved
0.6576	Remote Similarity	NPD5028	Approved
0.6576	Remote Similarity	NPD5034	Approved
0.6576	Remote Similarity	NPD4954	Approved
0.657	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD1511	Approved
0.6566	Remote Similarity	NPD8151	Discontinued
0.6564	Remote Similarity	NPD1607	Approved
0.6559	Remote Similarity	NPD5036	Approved
0.6558	Remote Similarity	NPD5306	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