NPASS Compound

Structure

NPC220282 OpenBabel07101719162D 58 64 0 0 1 0 0 0 0 0999 V2000 5.0532 -2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4495 2.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8978 0.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 -2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4154 2.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8637 1.0353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 -3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 -2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1213 -3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4345 1.3634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1745 -4.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1907 1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1225 2.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 -3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 -2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4686 1.1046 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4674 -4.0179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1554 -3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2098 0.1387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7262 -3.0520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2438 -0.1201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0191 -2.3449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5367 0.5870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0532 -2.6037 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7956 1.5529 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7944 -3.5696 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1416 0.6563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1404 -4.4662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8966 -4.3461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9169 -0.5684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6921 -2.7932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9850 -1.0860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2779 -1.3789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5708 0.3282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 -1.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3461 -1.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0884 2.2600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8284 -3.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 -2.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7615 1.8117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5015 -4.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 51 1 0 0 0 0 2 52 1 0 0 0 0 3 7 1 0 0 0 0 3 18 2 0 0 0 0 4 8 2 0 0 0 0 4 18 1 0 0 0 0 5 9 1 0 0 0 0 5 19 2 0 0 0 0 6 10 2 0 0 0 0 6 19 1 0 0 0 0 7 20 2 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 13 22 1 0 0 0 0 13 24 2 0 0 0 0 14 22 2 0 0 0 0 14 27 1 0 0 0 0 15 23 2 0 0 0 0 15 28 1 0 0 0 0 16 41 1 0 0 0 0 17 42 1 0 0 0 0 20 53 1 0 0 0 0 21 54 1 0 0 0 0 22 51 1 0 0 0 0 23 30 1 0 0 0 0 23 52 1 0 0 0 0 24 31 1 0 0 0 0 24 55 1 0 0 0 0 25 16 1 6 0 0 0 25 32 1 0 0 0 0 25 56 1 0 0 0 0 26 17 1 6 0 0 0 26 33 1 0 0 0 0 26 57 1 0 0 0 0 27 43 2 0 0 0 0 27 55 1 0 0 0 0 28 44 2 0 0 0 0 28 58 1 0 0 0 0 29 19 1 1 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 30 40 1 1 0 0 0 31 40 1 6 0 0 0 32 34 1 0 0 0 0 32 45 1 1 0 0 0 33 35 1 0 0 0 0 33 46 1 1 0 0 0 34 36 1 0 0 0 0 34 47 1 6 0 0 0 35 37 1 0 0 0 0 35 48 1 6 0 0 0 36 38 1 0 0 0 0 36 49 1 1 0 0 0 37 39 1 0 0 0 0 37 50 1 1 0 0 0 38 53 1 6 0 0 0 38 56 1 0 0 0 0 39 54 1 6 0 0 0 39 57 1 0 0 0 0 40 12 1 6 0 0 0 40 58 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	812.25
Volume:	767.087
LogP:	0.856
LogD:	0.395
LogS:	-3.186
# Rotatable Bonds:	12
TPSA:	273.73
# H-Bond Aceptor:	18
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	5.668
Fsp3:	0.45
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:	-6.407
MDCK Permeability:	7.319387805182487e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.686
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17
Plasma Protein Binding (PPB):	67.37861633300781%
Volume Distribution (VD):	0.601
Pgp-substrate:	16.6307373046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.276
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.46
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	1.309
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.365
Human Hepatotoxicity (H-HT):	0.441
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.31
Skin Sensitization:	0.094
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC220282

Natural Product ID:	NPC220282
*Common Name:**	Achyrodimer E
IUPAC Name:	(1S,6R,7S,8S)-2-methoxy-7-(4-methoxy-6-oxopyran-2-yl)-8-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-6-[(E)-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethenyl]-5-oxabicyclo[4.2.0]oct-2-en-4-one
Synonyms:	achyrodimer E
Standard InCHIKey:	QSUGKMAXQFCARZ-SCOSRVKCSA-N
Standard InCHI:	InChI=1S/C40H44O18/c1-51-22-13-24(55-27(43)14-22)31-29(19-5-9-21(10-6-19)54-39-37(50)35(48)33(46)26(17-42)57-39)30-23(52-2)15-28(44)58-40(30,31)12-11-18-3-7-20(8-4-18)53-38-36(49)34(47)32(45)25(16-41)56-38/h3-15,25-26,29-39,41-42,45-50H,16-17H2,1-2H3/b12-11+/t25-,26-,29+,30-,31-,32-,33-,34+,35+,36-,37-,38-,39-,40-/m1/s1
SMILES:	COc1cc([C@@H]2[C@@H](c3ccc(cc3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[C@H]3C(=CC(=O)O[C@@]23/C=C/c2ccc(cc2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)OC)oc(=O)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526382
PubChem CID:	11400179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001761] Kavalactones

*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
NPO18606	Achyrocline bogotensis	Species	Asteraceae	Eukaryota	n.a.	Colombian	n.a.	PMID[15844937]
NPO18606	Achyrocline bogotensis	Species	Asteraceae	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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	1.67	%	PMID[494994]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	2.28	%	PMID[494994]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	1.45	%	PMID[494994]

☑ 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 NPC220282 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	400
0.1-0.2	1547
0.2-0.3	3319
0.3-0.4	7962
0.4-0.5	10244
0.5-0.6	6471
0.6-0.7	6895
0.7-0.8	5283
0.8-0.85	534
0.85-0.9	39
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC175275
0.9648	High Similarity	NPC97240
0.8714	High Similarity	NPC295970
0.8707	High Similarity	NPC469367
0.8649	High Similarity	NPC471063
0.8611	High Similarity	NPC263829
0.8609	High Similarity	NPC259347
0.8609	High Similarity	NPC476386
0.8609	High Similarity	NPC476398
0.8609	High Similarity	NPC470933
0.8609	High Similarity	NPC94871
0.8609	High Similarity	NPC473427
0.8609	High Similarity	NPC306890
0.8609	High Similarity	NPC471062
0.86	High Similarity	NPC87950
0.86	High Similarity	NPC471764
0.8591	High Similarity	NPC226722
0.8553	High Similarity	NPC470934
0.8553	High Similarity	NPC476871
0.8553	High Similarity	NPC188393
0.8553	High Similarity	NPC470927
0.8553	High Similarity	NPC257970
0.8533	High Similarity	NPC276753
0.8533	High Similarity	NPC476865
0.8533	High Similarity	NPC37838
0.8533	High Similarity	NPC205796
0.8523	High Similarity	NPC471028
0.8523	High Similarity	NPC476867
0.8514	High Similarity	NPC473792
0.8514	High Similarity	NPC473873
0.8481	Intermediate Similarity	NPC149873
0.8481	Intermediate Similarity	NPC7191
0.8477	Intermediate Similarity	NPC232992
0.8467	Intermediate Similarity	NPC476868
0.8467	Intermediate Similarity	NPC34927
0.8467	Intermediate Similarity	NPC85624
0.8467	Intermediate Similarity	NPC252292
0.8467	Intermediate Similarity	NPC476866
0.8467	Intermediate Similarity	NPC476869
0.8467	Intermediate Similarity	NPC476864
0.8467	Intermediate Similarity	NPC34587
0.8467	Intermediate Similarity	NPC100998
0.8467	Intermediate Similarity	NPC476382
0.8462	Intermediate Similarity	NPC138777
0.8462	Intermediate Similarity	NPC225384
0.8462	Intermediate Similarity	NPC235294
0.8462	Intermediate Similarity	NPC246869
0.8462	Intermediate Similarity	NPC46137
0.8462	Intermediate Similarity	NPC11411
0.8456	Intermediate Similarity	NPC113680
0.8456	Intermediate Similarity	NPC278961
0.8452	Intermediate Similarity	NPC160882
0.8446	Intermediate Similarity	NPC108674
0.8442	Intermediate Similarity	NPC476352
0.8442	Intermediate Similarity	NPC478268
0.8442	Intermediate Similarity	NPC215060
0.8431	Intermediate Similarity	NPC475224
0.8425	Intermediate Similarity	NPC469383
0.8425	Intermediate Similarity	NPC166180
0.8421	Intermediate Similarity	NPC472339
0.8408	Intermediate Similarity	NPC471878
0.8355	Intermediate Similarity	NPC296377
0.8354	Intermediate Similarity	NPC478269
0.8344	Intermediate Similarity	NPC469701
0.8344	Intermediate Similarity	NPC138915
0.8333	Intermediate Similarity	NPC247032
0.8333	Intermediate Similarity	NPC476397
0.8333	Intermediate Similarity	NPC476375
0.8333	Intermediate Similarity	NPC116104
0.8333	Intermediate Similarity	NPC205864
0.8333	Intermediate Similarity	NPC476384
0.8333	Intermediate Similarity	NPC264632
0.8333	Intermediate Similarity	NPC116922
0.8333	Intermediate Similarity	NPC476378
0.8333	Intermediate Similarity	NPC476380
0.8333	Intermediate Similarity	NPC175214
0.8333	Intermediate Similarity	NPC263397
0.8333	Intermediate Similarity	NPC237872
0.8333	Intermediate Similarity	NPC119537
0.8333	Intermediate Similarity	NPC76406
0.8333	Intermediate Similarity	NPC476381
0.8333	Intermediate Similarity	NPC269141
0.8333	Intermediate Similarity	NPC88754
0.8333	Intermediate Similarity	NPC96795
0.8333	Intermediate Similarity	NPC302286
0.8333	Intermediate Similarity	NPC478239
0.8333	Intermediate Similarity	NPC112
0.8333	Intermediate Similarity	NPC298257
0.8323	Intermediate Similarity	NPC169404
0.8323	Intermediate Similarity	NPC176186
0.8323	Intermediate Similarity	NPC53587
0.8322	Intermediate Similarity	NPC89686
0.8322	Intermediate Similarity	NPC257095
0.8322	Intermediate Similarity	NPC476377
0.8322	Intermediate Similarity	NPC476385
0.8322	Intermediate Similarity	NPC186406
0.8322	Intermediate Similarity	NPC273932
0.8322	Intermediate Similarity	NPC134405
0.8322	Intermediate Similarity	NPC47471
0.8312	Intermediate Similarity	NPC229882
0.8312	Intermediate Similarity	NPC158635
0.8301	Intermediate Similarity	NPC169510
0.8301	Intermediate Similarity	NPC95990
0.8289	Intermediate Similarity	NPC107120
0.8289	Intermediate Similarity	NPC74320
0.8289	Intermediate Similarity	NPC229505
0.8288	Intermediate Similarity	NPC476411
0.8288	Intermediate Similarity	NPC187194
0.8278	Intermediate Similarity	NPC141455
0.8278	Intermediate Similarity	NPC196063
0.8278	Intermediate Similarity	NPC296954
0.8278	Intermediate Similarity	NPC64195
0.8278	Intermediate Similarity	NPC478240
0.8278	Intermediate Similarity	NPC129417
0.8278	Intermediate Similarity	NPC470235
0.8278	Intermediate Similarity	NPC283995
0.8278	Intermediate Similarity	NPC225445
0.8278	Intermediate Similarity	NPC300894
0.8272	Intermediate Similarity	NPC59516
0.8269	Intermediate Similarity	NPC150442
0.8269	Intermediate Similarity	NPC469699
0.8267	Intermediate Similarity	NPC246947
0.8267	Intermediate Similarity	NPC140502
0.8267	Intermediate Similarity	NPC145319
0.8267	Intermediate Similarity	NPC157816
0.8267	Intermediate Similarity	NPC472353
0.8267	Intermediate Similarity	NPC222433
0.8267	Intermediate Similarity	NPC265648
0.8255	Intermediate Similarity	NPC473799
0.8255	Intermediate Similarity	NPC475530
0.8255	Intermediate Similarity	NPC106944
0.825	Intermediate Similarity	NPC478267
0.8247	Intermediate Similarity	NPC35877
0.8247	Intermediate Similarity	NPC106138
0.8247	Intermediate Similarity	NPC95392
0.8247	Intermediate Similarity	NPC55715
0.8243	Intermediate Similarity	NPC469364
0.8243	Intermediate Similarity	NPC262328
0.8243	Intermediate Similarity	NPC65262
0.8243	Intermediate Similarity	NPC124149
0.8243	Intermediate Similarity	NPC101686
0.8243	Intermediate Similarity	NPC87777
0.8231	Intermediate Similarity	NPC79957
0.8224	Intermediate Similarity	NPC262182
0.8224	Intermediate Similarity	NPC287615
0.8224	Intermediate Similarity	NPC83743
0.8224	Intermediate Similarity	NPC216819
0.8221	Intermediate Similarity	NPC208818
0.8214	Intermediate Similarity	NPC476142
0.8212	Intermediate Similarity	NPC105005
0.8212	Intermediate Similarity	NPC185307
0.8212	Intermediate Similarity	NPC46092
0.8212	Intermediate Similarity	NPC470950
0.8207	Intermediate Similarity	NPC478255
0.8205	Intermediate Similarity	NPC187028
0.8205	Intermediate Similarity	NPC305700
0.8205	Intermediate Similarity	NPC10221
0.8205	Intermediate Similarity	NPC18249
0.8205	Intermediate Similarity	NPC197741
0.8205	Intermediate Similarity	NPC302610
0.8205	Intermediate Similarity	NPC140915
0.82	Intermediate Similarity	NPC476442
0.82	Intermediate Similarity	NPC215512
0.8194	Intermediate Similarity	NPC107197
0.8194	Intermediate Similarity	NPC182350
0.8188	Intermediate Similarity	NPC205195
0.8188	Intermediate Similarity	NPC68092
0.8188	Intermediate Similarity	NPC197316
0.8188	Intermediate Similarity	NPC64141
0.8188	Intermediate Similarity	NPC476383
0.8188	Intermediate Similarity	NPC81515
0.8188	Intermediate Similarity	NPC472350
0.8188	Intermediate Similarity	NPC89105
0.8187	Intermediate Similarity	NPC478265
0.8182	Intermediate Similarity	NPC199311
0.8182	Intermediate Similarity	NPC80732
0.8182	Intermediate Similarity	NPC23677
0.8182	Intermediate Similarity	NPC288416
0.8182	Intermediate Similarity	NPC93924
0.8182	Intermediate Similarity	NPC210611
0.8182	Intermediate Similarity	NPC308178
0.8182	Intermediate Similarity	NPC201148
0.8182	Intermediate Similarity	NPC3460
0.8182	Intermediate Similarity	NPC192763
0.8182	Intermediate Similarity	NPC28651
0.8182	Intermediate Similarity	NPC106677
0.8182	Intermediate Similarity	NPC261122
0.8182	Intermediate Similarity	NPC215095
0.8182	Intermediate Similarity	NPC300262
0.8176	Intermediate Similarity	NPC138350
0.8176	Intermediate Similarity	NPC40664
0.8176	Intermediate Similarity	NPC103409
0.8176	Intermediate Similarity	NPC37468
0.8176	Intermediate Similarity	NPC3293
0.8176	Intermediate Similarity	NPC165482
0.8176	Intermediate Similarity	NPC197723
0.817	Intermediate Similarity	NPC199928
0.817	Intermediate Similarity	NPC112861
0.8163	Intermediate Similarity	NPC471029
0.8158	Intermediate Similarity	NPC217635

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 NPC220282 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	885
0.2-0.3	1811
0.3-0.4	2724
0.4-0.5	2025
0.5-0.6	975
0.6-0.7	270
0.7-0.8	99
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD8455	Phase 2
0.8188	Intermediate Similarity	NPD7266	Discontinued
0.7987	Intermediate Similarity	NPD7097	Phase 1
0.7844	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5124	Phase 1
0.7733	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8313	Approved
0.7719	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD7472	Approved
0.7673	Intermediate Similarity	NPD1653	Approved
0.7661	Intermediate Similarity	NPD7808	Phase 3
0.7639	Intermediate Similarity	NPD1091	Approved
0.7633	Intermediate Similarity	NPD7054	Approved
0.7613	Intermediate Similarity	NPD6674	Discontinued
0.7602	Intermediate Similarity	NPD7251	Discontinued
0.7602	Intermediate Similarity	NPD7685	Pre-registration
0.7588	Intermediate Similarity	NPD7074	Phase 3
0.758	Intermediate Similarity	NPD5058	Phase 3
0.7574	Intermediate Similarity	NPD7228	Approved
0.7564	Intermediate Similarity	NPD4628	Phase 3
0.7544	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7467	Intermediate Similarity	NPD7095	Approved
0.7429	Intermediate Similarity	NPD7843	Approved
0.74	Intermediate Similarity	NPD4908	Phase 1
0.7394	Intermediate Similarity	NPD7157	Approved
0.7386	Intermediate Similarity	NPD4340	Discontinued
0.7368	Intermediate Similarity	NPD6233	Phase 2
0.732	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.729	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4536	Approved
0.729	Intermediate Similarity	NPD4538	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD5763	Approved
0.7261	Intermediate Similarity	NPD5762	Approved
0.7257	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8651	Approved
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4965	Approved
0.7246	Intermediate Similarity	NPD4966	Approved
0.7244	Intermediate Similarity	NPD7033	Discontinued
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7208	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1613	Approved
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7075	Discontinued
0.72	Intermediate Similarity	NPD6559	Discontinued
0.72	Intermediate Similarity	NPD2797	Approved
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.719	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5535	Approved
0.7178	Intermediate Similarity	NPD5403	Approved
0.7176	Intermediate Similarity	NPD8127	Discontinued
0.717	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3818	Discontinued
0.7162	Intermediate Similarity	NPD1610	Phase 2
0.716	Intermediate Similarity	NPD5401	Approved
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5588	Approved
0.7134	Intermediate Similarity	NPD5960	Phase 3
0.7133	Intermediate Similarity	NPD3225	Approved
0.7126	Intermediate Similarity	NPD7819	Suspended
0.7124	Intermediate Similarity	NPD3027	Phase 3
0.7115	Intermediate Similarity	NPD6653	Approved
0.7107	Intermediate Similarity	NPD2424	Discontinued
0.7097	Intermediate Similarity	NPD4140	Approved
0.7093	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5402	Approved
0.7083	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3268	Approved
0.7066	Intermediate Similarity	NPD6801	Discontinued
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6166	Phase 2
0.7052	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD422	Phase 1
0.7035	Intermediate Similarity	NPD3787	Discontinued
0.7032	Intermediate Similarity	NPD4062	Phase 3
0.7027	Intermediate Similarity	NPD5126	Approved
0.7027	Intermediate Similarity	NPD5125	Phase 3
0.7019	Intermediate Similarity	NPD3750	Approved
0.7	Intermediate Similarity	NPD8434	Phase 2
0.7	Intermediate Similarity	NPD1608	Approved
0.6982	Remote Similarity	NPD3817	Phase 2
0.6971	Remote Similarity	NPD3751	Discontinued
0.6966	Remote Similarity	NPD7549	Discontinued
0.6962	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1358	Approved
0.6948	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5735	Approved
0.6943	Remote Similarity	NPD7783	Phase 2
0.6943	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7768	Phase 2
0.6933	Remote Similarity	NPD3705	Approved
0.6933	Remote Similarity	NPD6667	Approved
0.6933	Remote Similarity	NPD6666	Approved
0.6932	Remote Similarity	NPD5844	Phase 1
0.6918	Remote Similarity	NPD4108	Discontinued
0.6918	Remote Similarity	NPD3748	Approved
0.6914	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6516	Phase 2
0.6913	Remote Similarity	NPD5846	Approved
0.6909	Remote Similarity	NPD6273	Approved
0.6905	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7411	Suspended
0.6894	Remote Similarity	NPD5958	Discontinued
0.6894	Remote Similarity	NPD4534	Discontinued
0.6892	Remote Similarity	NPD1548	Phase 1
0.689	Remote Similarity	NPD6799	Approved
0.6886	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3134	Approved
0.6871	Remote Similarity	NPD6190	Approved
0.6867	Remote Similarity	NPD3496	Discontinued
0.6867	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1934	Approved
0.6864	Remote Similarity	NPD4433	Discontinued
0.6863	Remote Similarity	NPD987	Approved
0.6863	Remote Similarity	NPD3266	Approved
0.6863	Remote Similarity	NPD3267	Approved
0.6863	Remote Similarity	NPD6362	Approved
0.6859	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5585	Approved
0.6845	Remote Similarity	NPD6599	Discontinued
0.6842	Remote Similarity	NPD3685	Discontinued
0.6842	Remote Similarity	NPD7680	Approved
0.6832	Remote Similarity	NPD6004	Phase 3
0.6832	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6005	Phase 3
0.6832	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6002	Phase 3
0.6831	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD290	Approved
0.6824	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7583	Approved
0.6813	Remote Similarity	NPD2799	Discontinued
0.681	Remote Similarity	NPD4535	Phase 3
0.681	Remote Similarity	NPD4110	Phase 3
0.681	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.68	Remote Similarity	NPD17	Approved
0.6788	Remote Similarity	NPD7585	Approved
0.6786	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5283	Phase 1
0.6779	Remote Similarity	NPD1894	Discontinued
0.6772	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2796	Approved
0.677	Remote Similarity	NPD2438	Suspended
0.677	Remote Similarity	NPD6032	Approved
0.6755	Remote Similarity	NPD3847	Discontinued
0.6754	Remote Similarity	NPD7435	Discontinued
0.6753	Remote Similarity	NPD8151	Discontinued
0.6752	Remote Similarity	NPD7985	Registered
0.6747	Remote Similarity	NPD3536	Discontinued
0.6747	Remote Similarity	NPD7447	Phase 1
0.6747	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5691	Approved
0.6732	Remote Similarity	NPD4749	Approved
0.6731	Remote Similarity	NPD6832	Phase 2
0.673	Remote Similarity	NPD1933	Approved
0.6728	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1465	Phase 2
0.6724	Remote Similarity	NPD5494	Approved
0.671	Remote Similarity	NPD5647	Approved
0.671	Remote Similarity	NPD2798	Approved
0.6708	Remote Similarity	NPD4308	Phase 3
0.6707	Remote Similarity	NPD8166	Discontinued
0.6706	Remote Similarity	NPD6677	Suspended
0.6705	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4626	Approved
0.6689	Remote Similarity	NPD6671	Approved
0.6688	Remote Similarity	NPD4625	Phase 3
0.6687	Remote Similarity	NPD7213	Phase 3
0.6687	Remote Similarity	NPD7212	Phase 2
0.6687	Remote Similarity	NPD1549	Phase 2
0.6686	Remote Similarity	NPD2415	Discontinued
0.6686	Remote Similarity	NPD6959	Discontinued
0.6685	Remote Similarity	NPD6843	Phase 3
0.6685	Remote Similarity	NPD6842	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