NPASS Compound

Structure

NPC473018 OpenBabel07101719512D 51 59 0 0 1 0 0 0 0 0999 V2000 -5.7929 -1.8080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9268 -0.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1674 -1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6986 -3.2377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0032 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6589 -1.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7929 0.1920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0335 -2.2377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1674 -3.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9543 0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6691 -3.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3164 -4.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9563 0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9268 -1.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6986 -2.2377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6589 -0.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0335 -3.2377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1622 1.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3383 -4.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9781 -3.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6254 -3.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0608 -1.8080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5646 -1.7377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.9563 -2.8025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4781 -2.1444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1473 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5249 0.1920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8995 -3.7377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1132 2.1871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0292 -5.6557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6036 -3.3378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5962 2.1100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 19 2 0 0 0 0 2 8 2 0 0 0 0 2 19 1 0 0 0 0 3 9 1 0 0 0 0 3 20 2 0 0 0 0 4 10 2 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 5 21 2 0 0 0 0 6 12 2 0 0 0 0 6 21 1 0 0 0 0 7 23 2 0 0 0 0 8 23 1 0 0 0 0 9 24 2 0 0 0 0 10 24 1 0 0 0 0 11 25 2 0 0 0 0 12 25 1 0 0 0 0 13 22 2 0 0 0 0 13 26 1 0 0 0 0 14 22 1 0 0 0 0 14 27 2 0 0 0 0 15 26 2 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 16 29 1 0 0 0 0 17 28 1 0 0 0 0 17 31 2 0 0 0 0 18 30 2 0 0 0 0 18 32 1 0 0 0 0 21 41 1 0 0 0 0 22 35 1 0 0 0 0 23 43 1 0 0 0 0 24 44 1 0 0 0 0 25 45 1 0 0 0 0 26 46 1 0 0 0 0 27 47 1 0 0 0 0 28 48 1 0 0 0 0 29 36 2 0 0 0 0 30 39 1 0 0 0 0 31 36 1 0 0 0 0 31 49 1 0 0 0 0 32 40 2 0 0 0 0 32 50 1 0 0 0 0 33 19 1 1 0 0 0 33 36 1 0 0 0 0 33 38 1 0 0 0 0 34 20 1 1 0 0 0 34 37 1 0 0 0 0 34 39 1 0 0 0 0 35 40 1 0 0 0 0 35 41 1 0 0 0 0 37 29 1 6 0 0 0 37 38 1 0 0 0 0 38 30 1 6 0 0 0 39 42 2 0 0 0 0 40 42 1 0 0 0 0 41 51 1 0 0 0 0 42 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	680.2
Volume:	689.635
LogP:	6.417
LogD:	4.012
LogS:	-3.957
# Rotatable Bonds:	4
TPSA:	171.07
# H-Bond Aceptor:	9
# H-Bond Donor:	8
# Rings:	9
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.093
Synthetic Accessibility Score:	4.63
Fsp3:	0.143
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.177
MDCK Permeability:	5.477737431647256e-06
Pgp-inhibitor:	0.643
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.984
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	97.55152130126953%
Volume Distribution (VD):	0.368
Pgp-substrate:	5.141195297241211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.724
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	0.188
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.265
CYP3A4-substrate:	0.666

ADMET: Excretion

Clearance (CL):	6.636
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.139
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.928
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.888
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC473018

Natural Product ID:	NPC473018
*Common Name:**	MKGFQHBCSSPJRH-SPPRLHLUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MKGFQHBCSSPJRH-SPPRLHLUSA-N
Standard InCHI:	InChI=1S/C42H32O9/c43-23-7-1-19(2-8-23)33-36-29(16-28(48)17-31(36)49)37-34(20-3-9-24(44)10-4-20)39-30(38(33)37)18-32(50)40-35(22-13-26(46)15-27(47)14-22)41(51-42(39)40)21-5-11-25(45)12-6-21/h1-18,33-35,37-38,41,43-50H/t33-,34+,35?,37+,38+,41?/m1/s1
SMILES:	C1=CC(=CC=C1C2C3C(C(C4=C5C(=C(C=C34)O)C(C(O5)C6=CC=C(C=C6)O)C7=CC(=CC(=C7)O)O)C8=CC=C(C=C8)O)C9=C2C(=CC(=C9)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3600414
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	root bark	Mongolian	n.a.	PMID[26073007]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[31747283]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20471	Sophora alopecuroides	Species	Fabaceae	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	47700.0	nM	PMID[497477]

☑ 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 NPC473018 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	557
0.1-0.2	1832
0.2-0.3	4473
0.3-0.4	11775
0.4-0.5	6706
0.5-0.6	4781
0.6-0.7	8818
0.7-0.8	3221
0.8-0.85	367
0.85-0.9	125
0.9-0.95	26
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120633
0.9724	High Similarity	NPC218801
0.9658	High Similarity	NPC157081
0.9524	High Similarity	NPC105073
0.9524	High Similarity	NPC233886
0.9524	High Similarity	NPC224528
0.9521	High Similarity	NPC122980
0.9521	High Similarity	NPC148516
0.9521	High Similarity	NPC180605
0.9521	High Similarity	NPC177172
0.9521	High Similarity	NPC107862
0.9448	High Similarity	NPC14468
0.9384	High Similarity	NPC6702
0.9384	High Similarity	NPC112819
0.9384	High Similarity	NPC133209
0.9252	High Similarity	NPC111134
0.9247	High Similarity	NPC149633
0.9054	High Similarity	NPC176804
0.9054	High Similarity	NPC71686
0.8993	High Similarity	NPC242774
0.8993	High Similarity	NPC224921
0.8993	High Similarity	NPC231712
0.8993	High Similarity	NPC237546
0.8958	High Similarity	NPC141717
0.8954	High Similarity	NPC157333
0.8947	High Similarity	NPC476391
0.8904	High Similarity	NPC273623
0.8896	High Similarity	NPC202104
0.8889	High Similarity	NPC15109
0.8889	High Similarity	NPC125579
0.8889	High Similarity	NPC11727
0.8776	High Similarity	NPC182509
0.8776	High Similarity	NPC174787
0.8776	High Similarity	NPC213607
0.8767	High Similarity	NPC71465
0.8767	High Similarity	NPC470308
0.8767	High Similarity	NPC472646
0.8767	High Similarity	NPC470307
0.8699	High Similarity	NPC206525
0.8699	High Similarity	NPC472647
0.8699	High Similarity	NPC471522
0.8699	High Similarity	NPC191462
0.8699	High Similarity	NPC472648
0.8699	High Similarity	NPC133463
0.8699	High Similarity	NPC472649
0.8699	High Similarity	NPC170328
0.8667	High Similarity	NPC15659
0.8667	High Similarity	NPC304894
0.863	High Similarity	NPC258780
0.863	High Similarity	NPC37410
0.8618	High Similarity	NPC153182
0.8618	High Similarity	NPC174251
0.86	High Similarity	NPC163508
0.86	High Similarity	NPC173203
0.8581	High Similarity	NPC59692
0.8581	High Similarity	NPC233467
0.8562	High Similarity	NPC227516
0.8562	High Similarity	NPC20757
0.8553	High Similarity	NPC274454
0.8553	High Similarity	NPC215678
0.8493	Intermediate Similarity	NPC469610
0.8483	Intermediate Similarity	NPC471517
0.8483	Intermediate Similarity	NPC238168
0.8483	Intermediate Similarity	NPC8899
0.8483	Intermediate Similarity	NPC237424
0.8483	Intermediate Similarity	NPC473309
0.8467	Intermediate Similarity	NPC100482
0.8467	Intermediate Similarity	NPC277331
0.8462	Intermediate Similarity	NPC279406
0.8462	Intermediate Similarity	NPC226809
0.8452	Intermediate Similarity	NPC162976
0.8452	Intermediate Similarity	NPC205501
0.8452	Intermediate Similarity	NPC118000
0.8452	Intermediate Similarity	NPC477612
0.8435	Intermediate Similarity	NPC476616
0.8435	Intermediate Similarity	NPC476615
0.8435	Intermediate Similarity	NPC473107
0.8435	Intermediate Similarity	NPC476617
0.8425	Intermediate Similarity	NPC469611
0.8421	Intermediate Similarity	NPC475492
0.8414	Intermediate Similarity	NPC254000
0.8408	Intermediate Similarity	NPC224161
0.8397	Intermediate Similarity	NPC329343
0.8397	Intermediate Similarity	NPC324517
0.8397	Intermediate Similarity	NPC321972
0.8387	Intermediate Similarity	NPC295573
0.8387	Intermediate Similarity	NPC470208
0.8385	Intermediate Similarity	NPC48880
0.8377	Intermediate Similarity	NPC108811
0.8377	Intermediate Similarity	NPC202742
0.8377	Intermediate Similarity	NPC170103
0.8377	Intermediate Similarity	NPC262911
0.8377	Intermediate Similarity	NPC294558
0.8377	Intermediate Similarity	NPC236202
0.8377	Intermediate Similarity	NPC58190
0.8377	Intermediate Similarity	NPC82917
0.8377	Intermediate Similarity	NPC18185
0.8377	Intermediate Similarity	NPC204770
0.8377	Intermediate Similarity	NPC263940
0.8377	Intermediate Similarity	NPC70409
0.8377	Intermediate Similarity	NPC262297
0.8366	Intermediate Similarity	NPC181615
0.8356	Intermediate Similarity	NPC196765
0.8356	Intermediate Similarity	NPC181497
0.8356	Intermediate Similarity	NPC472590
0.8356	Intermediate Similarity	NPC12875
0.8356	Intermediate Similarity	NPC271945
0.8356	Intermediate Similarity	NPC150011
0.8356	Intermediate Similarity	NPC206224
0.8356	Intermediate Similarity	NPC129106
0.8356	Intermediate Similarity	NPC280653
0.8356	Intermediate Similarity	NPC236014
0.8356	Intermediate Similarity	NPC268917
0.8356	Intermediate Similarity	NPC17343
0.8356	Intermediate Similarity	NPC164574
0.8356	Intermediate Similarity	NPC129784
0.8356	Intermediate Similarity	NPC228369
0.8356	Intermediate Similarity	NPC207892
0.8356	Intermediate Similarity	NPC118114
0.8356	Intermediate Similarity	NPC476166
0.8356	Intermediate Similarity	NPC300875
0.8356	Intermediate Similarity	NPC282508
0.8354	Intermediate Similarity	NPC46335
0.8345	Intermediate Similarity	NPC471518
0.8345	Intermediate Similarity	NPC471519
0.8323	Intermediate Similarity	NPC329836
0.8312	Intermediate Similarity	NPC126291
0.8312	Intermediate Similarity	NPC96576
0.8312	Intermediate Similarity	NPC260397
0.8311	Intermediate Similarity	NPC225696
0.8311	Intermediate Similarity	NPC296915
0.8311	Intermediate Similarity	NPC198154
0.8311	Intermediate Similarity	NPC223008
0.8311	Intermediate Similarity	NPC97834
0.8311	Intermediate Similarity	NPC115335
0.8299	Intermediate Similarity	NPC13005
0.8289	Intermediate Similarity	NPC186033
0.8288	Intermediate Similarity	NPC470225
0.8288	Intermediate Similarity	NPC27187
0.828	Intermediate Similarity	NPC471403
0.8278	Intermediate Similarity	NPC221134
0.8272	Intermediate Similarity	NPC90822
0.8269	Intermediate Similarity	NPC476969
0.8269	Intermediate Similarity	NPC318373
0.8269	Intermediate Similarity	NPC470098
0.8269	Intermediate Similarity	NPC470826
0.8269	Intermediate Similarity	NPC473266
0.8269	Intermediate Similarity	NPC321657
0.8269	Intermediate Similarity	NPC211561
0.8264	Intermediate Similarity	NPC9292
0.8264	Intermediate Similarity	NPC145659
0.8258	Intermediate Similarity	NPC327412
0.8258	Intermediate Similarity	NPC320970
0.8258	Intermediate Similarity	NPC320671
0.8258	Intermediate Similarity	NPC328567
0.8247	Intermediate Similarity	NPC469557
0.8243	Intermediate Similarity	NPC473665
0.8239	Intermediate Similarity	NPC188578
0.8239	Intermediate Similarity	NPC80918
0.8228	Intermediate Similarity	NPC160196
0.8224	Intermediate Similarity	NPC265075
0.8221	Intermediate Similarity	NPC261896
0.8219	Intermediate Similarity	NPC93962
0.82	Intermediate Similarity	NPC126101
0.8199	Intermediate Similarity	NPC125495
0.8199	Intermediate Similarity	NPC4809
0.8199	Intermediate Similarity	NPC73517
0.8199	Intermediate Similarity	NPC470827
0.8199	Intermediate Similarity	NPC147743
0.8194	Intermediate Similarity	NPC248053
0.8194	Intermediate Similarity	NPC155564
0.8194	Intermediate Similarity	NPC324492
0.8194	Intermediate Similarity	NPC102280
0.8194	Intermediate Similarity	NPC317053
0.8194	Intermediate Similarity	NPC471608
0.8182	Intermediate Similarity	NPC473845
0.817	Intermediate Similarity	NPC277784
0.817	Intermediate Similarity	NPC472088
0.817	Intermediate Similarity	NPC472087
0.8165	Intermediate Similarity	NPC302915
0.8165	Intermediate Similarity	NPC259707
0.8151	Intermediate Similarity	NPC39064
0.8151	Intermediate Similarity	NPC38664
0.8151	Intermediate Similarity	NPC47283
0.8151	Intermediate Similarity	NPC53986
0.8151	Intermediate Similarity	NPC38017
0.8151	Intermediate Similarity	NPC215300
0.8148	Intermediate Similarity	NPC86630
0.8148	Intermediate Similarity	NPC159526
0.8148	Intermediate Similarity	NPC471404
0.8148	Intermediate Similarity	NPC470828
0.8148	Intermediate Similarity	NPC212614
0.8148	Intermediate Similarity	NPC106601
0.8148	Intermediate Similarity	NPC205613
0.8148	Intermediate Similarity	NPC151474
0.8146	Intermediate Similarity	NPC474687
0.8146	Intermediate Similarity	NPC94994
0.8138	Intermediate Similarity	NPC471215
0.8138	Intermediate Similarity	NPC262573
0.8133	Intermediate Similarity	NPC472370

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 NPC473018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	448
0.1-0.2	973
0.2-0.3	1771
0.3-0.4	2833
0.4-0.5	1635
0.5-0.6	929
0.6-0.7	486
0.7-0.8	70
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8288	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD4908	Phase 1
0.7973	Intermediate Similarity	NPD4625	Phase 3
0.7959	Intermediate Similarity	NPD2861	Phase 2
0.7831	Intermediate Similarity	NPD6959	Discontinued
0.7793	Intermediate Similarity	NPD1610	Phase 2
0.7682	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5735	Approved
0.7597	Intermediate Similarity	NPD6353	Approved
0.7582	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1613	Approved
0.7568	Intermediate Similarity	NPD4749	Approved
0.7532	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD3892	Phase 2
0.745	Intermediate Similarity	NPD5327	Phase 3
0.7434	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6696	Suspended
0.7399	Intermediate Similarity	NPD7228	Approved
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD7768	Phase 2
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7229	Phase 3
0.7358	Intermediate Similarity	NPD7037	Approved
0.7345	Intermediate Similarity	NPD8313	Approved
0.7345	Intermediate Similarity	NPD8312	Approved
0.7312	Intermediate Similarity	NPD6674	Discontinued
0.7305	Intermediate Similarity	NPD37	Approved
0.7301	Intermediate Similarity	NPD7447	Phase 1
0.7296	Intermediate Similarity	NPD5762	Approved
0.7296	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7262	Intermediate Similarity	NPD7819	Suspended
0.7262	Intermediate Similarity	NPD8455	Phase 2
0.7257	Intermediate Similarity	NPD5844	Phase 1
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.7244	Intermediate Similarity	NPD4140	Approved
0.7239	Intermediate Similarity	NPD7212	Phase 2
0.7239	Intermediate Similarity	NPD7213	Phase 3
0.7233	Intermediate Similarity	NPD6099	Approved
0.7233	Intermediate Similarity	NPD6100	Approved
0.7219	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7466	Approved
0.7152	Intermediate Similarity	NPD4097	Suspended
0.7152	Intermediate Similarity	NPD2157	Approved
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7134	Intermediate Similarity	NPD7390	Discontinued
0.7134	Intermediate Similarity	NPD7041	Phase 2
0.7134	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD8127	Discontinued
0.7089	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD4624	Approved
0.7076	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6232	Discontinued
0.7059	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3750	Approved
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7741	Discontinued
0.7039	Intermediate Similarity	NPD6559	Discontinued
0.7039	Intermediate Similarity	NPD7240	Approved
0.7025	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3620	Phase 2
0.7013	Intermediate Similarity	NPD3094	Phase 2
0.7006	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6166	Phase 2
0.6989	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2532	Approved
0.6988	Remote Similarity	NPD2533	Approved
0.6988	Remote Similarity	NPD2534	Approved
0.6988	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4380	Phase 2
0.6975	Remote Similarity	NPD6004	Phase 3
0.6975	Remote Similarity	NPD6002	Phase 3
0.6975	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6005	Phase 3
0.6957	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7003	Approved
0.6948	Remote Similarity	NPD8651	Approved
0.6946	Remote Similarity	NPD6273	Approved
0.6941	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7411	Suspended
0.6936	Remote Similarity	NPD3749	Approved
0.6936	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7833	Phase 2
0.6936	Remote Similarity	NPD7831	Phase 2
0.6933	Remote Similarity	NPD3091	Approved
0.6923	Remote Similarity	NPD8054	Approved
0.6923	Remote Similarity	NPD8053	Approved
0.6913	Remote Similarity	NPD7340	Approved
0.6894	Remote Similarity	NPD7097	Phase 1
0.6886	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7680	Approved
0.6872	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3092	Approved
0.6859	Remote Similarity	NPD6584	Phase 3
0.6857	Remote Similarity	NPD5494	Approved
0.6855	Remote Similarity	NPD6663	Approved
0.6855	Remote Similarity	NPD8032	Phase 2
0.6852	Remote Similarity	NPD5588	Approved
0.6846	Remote Similarity	NPD6671	Approved
0.6842	Remote Similarity	NPD4626	Approved
0.6839	Remote Similarity	NPD7075	Discontinued
0.6829	Remote Similarity	NPD1549	Phase 2
0.6815	Remote Similarity	NPD5736	Approved
0.6811	Remote Similarity	NPD7906	Approved
0.6802	Remote Similarity	NPD1934	Approved
0.6791	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7119	Phase 2
0.6786	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4750	Phase 3
0.678	Remote Similarity	NPD3787	Discontinued
0.6778	Remote Similarity	NPD8156	Discontinued
0.6776	Remote Similarity	NPD5691	Approved
0.677	Remote Similarity	NPD6355	Discontinued
0.6763	Remote Similarity	NPD5929	Approved
0.6759	Remote Similarity	NPD2342	Discontinued
0.6757	Remote Similarity	NPD7635	Approved
0.6753	Remote Similarity	NPD1611	Approved
0.6753	Remote Similarity	NPD422	Phase 1
0.6748	Remote Similarity	NPD3748	Approved
0.6746	Remote Similarity	NPD6090	Discontinued
0.6743	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7074	Phase 3
0.6732	Remote Similarity	NPD3095	Discontinued
0.6725	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3226	Approved
0.6722	Remote Similarity	NPD8099	Discontinued
0.6722	Remote Similarity	NPD8252	Approved
0.6722	Remote Similarity	NPD3818	Discontinued
0.6722	Remote Similarity	NPD8251	Approved
0.6711	Remote Similarity	NPD1398	Phase 1
0.6709	Remote Similarity	NPD3018	Phase 2
0.6708	Remote Similarity	NPD2238	Phase 2
0.6707	Remote Similarity	NPD5406	Approved
0.6707	Remote Similarity	NPD5405	Approved
0.6707	Remote Similarity	NPD5408	Approved
0.6707	Remote Similarity	NPD5404	Approved
0.6687	Remote Similarity	NPD4536	Approved
0.6687	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4538	Approved
0.6685	Remote Similarity	NPD4578	Approved
0.6685	Remote Similarity	NPD7311	Approved
0.6685	Remote Similarity	NPD7054	Approved
0.6685	Remote Similarity	NPD7313	Approved
0.6685	Remote Similarity	NPD4577	Approved
0.6685	Remote Similarity	NPD7312	Approved
0.6685	Remote Similarity	NPD7310	Approved
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6583	Phase 3
0.6667	Remote Similarity	NPD1653	Approved
0.6667	Remote Similarity	NPD4663	Approved
0.6667	Remote Similarity	NPD6582	Phase 2
0.6667	Remote Similarity	NPD5760	Phase 2
0.6649	Remote Similarity	NPD7309	Approved
0.6648	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7472	Approved
0.6647	Remote Similarity	NPD4319	Phase 2
0.6646	Remote Similarity	NPD7033	Discontinued
0.6646	Remote Similarity	NPD1510	Phase 2
0.6646	Remote Similarity	NPD5960	Phase 3
0.6645	Remote Similarity	NPD1091	Approved
0.6644	Remote Similarity	NPD7843	Approved
0.663	Remote Similarity	NPD7549	Discontinued
0.663	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7808	Phase 3
0.663	Remote Similarity	NPD7177	Discontinued
0.6628	Remote Similarity	NPD7458	Discontinued
0.6627	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1511	Approved
0.6624	Remote Similarity	NPD1283	Approved
0.6623	Remote Similarity	NPD5125	Phase 3
0.6623	Remote Similarity	NPD5126	Approved
0.6623	Remote Similarity	NPD7157	Approved
0.6623	Remote Similarity	NPD4059	Approved
0.6616	Remote Similarity	NPD8151	Discontinued

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