NPASS Compound

Structure

NPC175275 OpenBabel07101718272D 58 64 0 0 1 0 0 0 0 0999 V2000 -4.0532 1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 -2.6037 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 1.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 0.4483 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 2.1554 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 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 -2.1213 2.1213 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 -6.1745 -4.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1745 3.7250 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 1.7071 0.7071 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 3.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 1.1554 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 -0.7071 0.7071 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 -5.4674 -4.0179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4674 3.0179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1554 2.3801 0.0000 C 0 0 0 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 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 -5.7262 -3.0520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7262 2.0520 0.0000 C 0 0 2 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 6.0191 1.3449 0.0000 C 0 0 1 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 5.0532 1.6037 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 4.7944 2.5696 0.0000 C 0 0 2 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 8.1404 3.4662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8966 3.3461 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 -6.6921 -2.7932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6921 1.7932 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 6.2779 0.3789 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 0.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 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 -2.8284 -3.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8284 2.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 1.6730 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 -4.5015 -4.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5015 3.2767 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 17 2 0 0 0 0 4 8 2 0 0 0 0 4 17 1 0 0 0 0 5 9 1 0 0 0 0 5 18 2 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 11 23 2 0 0 0 0 12 22 1 0 0 0 0 12 24 2 0 0 0 0 13 21 2 0 0 0 0 13 27 1 0 0 0 0 14 22 2 0 0 0 0 14 28 1 0 0 0 0 15 41 1 0 0 0 0 16 42 1 0 0 0 0 19 53 1 0 0 0 0 20 54 1 0 0 0 0 21 51 1 0 0 0 0 22 52 1 0 0 0 0 23 55 1 0 0 0 0 24 56 1 0 0 0 0 25 15 1 6 0 0 0 25 33 1 0 0 0 0 25 57 1 0 0 0 0 26 16 1 6 0 0 0 26 34 1 0 0 0 0 26 58 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 56 1 0 0 0 0 29 17 1 6 0 0 0 29 31 1 0 0 0 0 29 32 1 0 0 0 0 30 18 1 1 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 31 23 1 1 0 0 0 32 24 1 6 0 0 0 33 35 1 0 0 0 0 33 45 1 1 0 0 0 34 36 1 0 0 0 0 34 46 1 1 0 0 0 35 37 1 0 0 0 0 35 47 1 6 0 0 0 36 38 1 0 0 0 0 36 48 1 6 0 0 0 37 39 1 0 0 0 0 37 49 1 1 0 0 0 38 40 1 0 0 0 0 38 50 1 1 0 0 0 39 53 1 6 0 0 0 39 57 1 0 0 0 0 40 54 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:	0.578
LogD:	0.333
LogS:	-3.855
# Rotatable Bonds:	12
TPSA:	277.64
# H-Bond Aceptor:	18
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	5.151
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:	-6.062
MDCK Permeability:	3.2673735404387116e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.837
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	91.0251693725586%
Volume Distribution (VD):	1.074
Pgp-substrate:	3.029398202896118%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.168
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.346
CYP2D6-substrate:	0.64
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	2.028
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.446
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.043
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC175275

Natural Product ID:	NPC175275
*Common Name:**	Achyrodimer C
IUPAC Name:	n.a.
Synonyms:	achyrodimer C
Standard InCHIKey:	GDLOSEKDTGZMKZ-YLRYDLBXSA-N
Standard InCHI:	InChI=1S/C40H44O18/c1-51-21-11-23(55-27(43)13-21)31-29(17-3-7-19(8-4-17)53-39-37(49)35(47)33(45)25(15-41)57-39)32(24-12-22(52-2)14-28(44)56-24)30(31)18-5-9-20(10-6-18)54-40-38(50)36(48)34(46)26(16-42)58-40/h3-14,25-26,29-42,45-50H,15-16H2,1-2H3/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](c3cc(cc(=O)o3)OC)[C@@H]2c2ccc(cc2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)oc(=O)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447638
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678669]
NPO18606	Achyrocline bogotensis	Species	Asteraceae	Eukaryota	n.a.	Colombian	n.a.	PMID[15844937]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094434]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18606	Achyrocline bogotensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25148	Helichrysum italicum	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	=	0.01	%	PMID[466199]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	5.74	%	PMID[466199]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	1.48	%	PMID[466199]

☑ 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 NPC175275 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	408
0.1-0.2	1656
0.2-0.3	3520
0.3-0.4	8805
0.4-0.5	10106
0.5-0.6	6104
0.6-0.7	7607
0.7-0.8	3963
0.8-0.85	481
0.85-0.9	44
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC220282
0.9716	High Similarity	NPC97240
0.8777	High Similarity	NPC295970
0.8767	High Similarity	NPC469367
0.8707	High Similarity	NPC471063
0.8671	High Similarity	NPC263829
0.8667	High Similarity	NPC259347
0.8667	High Similarity	NPC476386
0.8667	High Similarity	NPC476398
0.8667	High Similarity	NPC94871
0.8667	High Similarity	NPC470933
0.8667	High Similarity	NPC471062
0.8667	High Similarity	NPC473427
0.8667	High Similarity	NPC306890
0.8649	High Similarity	NPC226722
0.8609	High Similarity	NPC257970
0.8609	High Similarity	NPC476871
0.8609	High Similarity	NPC470927
0.8591	High Similarity	NPC476865
0.8591	High Similarity	NPC276753
0.8591	High Similarity	NPC205796
0.8581	High Similarity	NPC471028
0.8581	High Similarity	NPC476867
0.8571	High Similarity	NPC473792
0.8571	High Similarity	NPC473873
0.8535	High Similarity	NPC149873
0.8535	High Similarity	NPC7191
0.8533	High Similarity	NPC471764
0.8533	High Similarity	NPC232992
0.8533	High Similarity	NPC87950
0.8523	High Similarity	NPC476866
0.8523	High Similarity	NPC34587
0.8523	High Similarity	NPC100998
0.8523	High Similarity	NPC476868
0.8523	High Similarity	NPC476869
0.8523	High Similarity	NPC34927
0.8523	High Similarity	NPC476382
0.8523	High Similarity	NPC252292
0.8523	High Similarity	NPC476864
0.8521	High Similarity	NPC138777
0.8521	High Similarity	NPC46137
0.8521	High Similarity	NPC235294
0.8521	High Similarity	NPC225384
0.8521	High Similarity	NPC246869
0.8516	High Similarity	NPC11411
0.8514	High Similarity	NPC278961
0.8514	High Similarity	NPC113680
0.8503	High Similarity	NPC108674
0.8497	Intermediate Similarity	NPC215060
0.8497	Intermediate Similarity	NPC476352
0.8497	Intermediate Similarity	NPC478268
0.8487	Intermediate Similarity	NPC188393
0.8487	Intermediate Similarity	NPC470934
0.8483	Intermediate Similarity	NPC166180
0.8477	Intermediate Similarity	NPC472339
0.8467	Intermediate Similarity	NPC37838
0.8462	Intermediate Similarity	NPC471878
0.8408	Intermediate Similarity	NPC478269
0.84	Intermediate Similarity	NPC138915
0.84	Intermediate Similarity	NPC85624
0.8389	Intermediate Similarity	NPC476384
0.8389	Intermediate Similarity	NPC476381
0.8389	Intermediate Similarity	NPC269141
0.8389	Intermediate Similarity	NPC96795
0.8389	Intermediate Similarity	NPC476397
0.8389	Intermediate Similarity	NPC478239
0.8389	Intermediate Similarity	NPC476375
0.8389	Intermediate Similarity	NPC298257
0.8389	Intermediate Similarity	NPC247032
0.8389	Intermediate Similarity	NPC264632
0.8389	Intermediate Similarity	NPC476378
0.8389	Intermediate Similarity	NPC175214
0.8389	Intermediate Similarity	NPC205864
0.8389	Intermediate Similarity	NPC119537
0.8389	Intermediate Similarity	NPC76406
0.8389	Intermediate Similarity	NPC476380
0.8389	Intermediate Similarity	NPC112
0.8389	Intermediate Similarity	NPC116922
0.8387	Intermediate Similarity	NPC160882
0.8378	Intermediate Similarity	NPC273932
0.8378	Intermediate Similarity	NPC134405
0.8378	Intermediate Similarity	NPC257095
0.8378	Intermediate Similarity	NPC89686
0.8378	Intermediate Similarity	NPC47471
0.8378	Intermediate Similarity	NPC476377
0.8378	Intermediate Similarity	NPC186406
0.8378	Intermediate Similarity	NPC476385
0.8377	Intermediate Similarity	NPC53587
0.8377	Intermediate Similarity	NPC169404
0.8377	Intermediate Similarity	NPC176186
0.8366	Intermediate Similarity	NPC158635
0.8366	Intermediate Similarity	NPC229882
0.8366	Intermediate Similarity	NPC475224
0.8356	Intermediate Similarity	NPC469383
0.8355	Intermediate Similarity	NPC95990
0.8345	Intermediate Similarity	NPC187194
0.8345	Intermediate Similarity	NPC476411
0.8344	Intermediate Similarity	NPC107120
0.8344	Intermediate Similarity	NPC74320
0.8333	Intermediate Similarity	NPC64195
0.8333	Intermediate Similarity	NPC225445
0.8323	Intermediate Similarity	NPC150442
0.8323	Intermediate Similarity	NPC59516
0.8322	Intermediate Similarity	NPC140502
0.8322	Intermediate Similarity	NPC265648
0.8322	Intermediate Similarity	NPC222433
0.8322	Intermediate Similarity	NPC157816
0.8322	Intermediate Similarity	NPC246947
0.8322	Intermediate Similarity	NPC145319
0.8311	Intermediate Similarity	NPC475530
0.8311	Intermediate Similarity	NPC473799
0.8311	Intermediate Similarity	NPC106944
0.8302	Intermediate Similarity	NPC478267
0.8301	Intermediate Similarity	NPC95392
0.8301	Intermediate Similarity	NPC106138
0.8301	Intermediate Similarity	NPC55715
0.8301	Intermediate Similarity	NPC35877
0.8299	Intermediate Similarity	NPC87777
0.8299	Intermediate Similarity	NPC101686
0.8299	Intermediate Similarity	NPC65262
0.8299	Intermediate Similarity	NPC124149
0.8299	Intermediate Similarity	NPC469364
0.8299	Intermediate Similarity	NPC262328
0.8289	Intermediate Similarity	NPC296377
0.8288	Intermediate Similarity	NPC79957
0.8278	Intermediate Similarity	NPC287615
0.8278	Intermediate Similarity	NPC83743
0.8278	Intermediate Similarity	NPC469701
0.8278	Intermediate Similarity	NPC262182
0.8278	Intermediate Similarity	NPC216819
0.8273	Intermediate Similarity	NPC476142
0.8267	Intermediate Similarity	NPC263397
0.8267	Intermediate Similarity	NPC116104
0.8267	Intermediate Similarity	NPC470950
0.8267	Intermediate Similarity	NPC237872
0.8267	Intermediate Similarity	NPC88754
0.8267	Intermediate Similarity	NPC302286
0.8267	Intermediate Similarity	NPC185307
0.8258	Intermediate Similarity	NPC197741
0.8258	Intermediate Similarity	NPC302610
0.8258	Intermediate Similarity	NPC140915
0.8258	Intermediate Similarity	NPC187028
0.8258	Intermediate Similarity	NPC305700
0.8258	Intermediate Similarity	NPC10221
0.8258	Intermediate Similarity	NPC18249
0.8247	Intermediate Similarity	NPC182350
0.8243	Intermediate Similarity	NPC64141
0.8243	Intermediate Similarity	NPC68092
0.8243	Intermediate Similarity	NPC472350
0.8243	Intermediate Similarity	NPC197316
0.8243	Intermediate Similarity	NPC476383
0.8243	Intermediate Similarity	NPC205195
0.8243	Intermediate Similarity	NPC89105
0.8243	Intermediate Similarity	NPC81515
0.8239	Intermediate Similarity	NPC288416
0.8235	Intermediate Similarity	NPC28651
0.8235	Intermediate Similarity	NPC3460
0.8235	Intermediate Similarity	NPC80732
0.8235	Intermediate Similarity	NPC300262
0.8235	Intermediate Similarity	NPC201148
0.8235	Intermediate Similarity	NPC210611
0.8235	Intermediate Similarity	NPC199311
0.8235	Intermediate Similarity	NPC169510
0.8235	Intermediate Similarity	NPC23677
0.8235	Intermediate Similarity	NPC192763
0.8235	Intermediate Similarity	NPC93924
0.8235	Intermediate Similarity	NPC215095
0.8235	Intermediate Similarity	NPC261122
0.8231	Intermediate Similarity	NPC40664
0.8231	Intermediate Similarity	NPC103409
0.8231	Intermediate Similarity	NPC197723
0.8231	Intermediate Similarity	NPC165482
0.8231	Intermediate Similarity	NPC3293
0.8231	Intermediate Similarity	NPC138350
0.8231	Intermediate Similarity	NPC37468
0.8224	Intermediate Similarity	NPC199928
0.8224	Intermediate Similarity	NPC229505
0.8212	Intermediate Similarity	NPC300894
0.8212	Intermediate Similarity	NPC141455
0.8212	Intermediate Similarity	NPC296954
0.8212	Intermediate Similarity	NPC471667
0.8212	Intermediate Similarity	NPC79429
0.8212	Intermediate Similarity	NPC177597
0.8212	Intermediate Similarity	NPC478240
0.8212	Intermediate Similarity	NPC129417
0.8212	Intermediate Similarity	NPC292443
0.8212	Intermediate Similarity	NPC196063
0.8212	Intermediate Similarity	NPC470235
0.8212	Intermediate Similarity	NPC283995
0.8212	Intermediate Similarity	NPC217635
0.8212	Intermediate Similarity	NPC232228
0.8205	Intermediate Similarity	NPC246893
0.8205	Intermediate Similarity	NPC299706
0.8205	Intermediate Similarity	NPC115466
0.8205	Intermediate Similarity	NPC61604
0.8205	Intermediate Similarity	NPC469699
0.8205	Intermediate Similarity	NPC245615
0.82	Intermediate Similarity	NPC476356
0.82	Intermediate Similarity	NPC472353
0.8194	Intermediate Similarity	NPC475379

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 NPC175275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	900
0.2-0.3	1838
0.3-0.4	2790
0.4-0.5	2006
0.5-0.6	911
0.6-0.7	265
0.7-0.8	69
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8506	High Similarity	NPD8455	Phase 2
0.8243	Intermediate Similarity	NPD7266	Discontinued
0.7919	Intermediate Similarity	NPD7097	Phase 1
0.7892	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8312	Approved
0.7765	Intermediate Similarity	NPD8313	Approved
0.7738	Intermediate Similarity	NPD7472	Approved
0.7722	Intermediate Similarity	NPD1653	Approved
0.7706	Intermediate Similarity	NPD7808	Phase 3
0.7692	Intermediate Similarity	NPD1091	Approved
0.7679	Intermediate Similarity	NPD7054	Approved
0.7667	Intermediate Similarity	NPD5124	Phase 1
0.7667	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6674	Discontinued
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.7633	Intermediate Similarity	NPD7074	Phase 3
0.7619	Intermediate Similarity	NPD7228	Approved
0.7613	Intermediate Similarity	NPD4628	Phase 3
0.7588	Intermediate Similarity	NPD6797	Phase 2
0.755	Intermediate Similarity	NPD6355	Discontinued
0.7548	Intermediate Similarity	NPD1652	Phase 2
0.7544	Intermediate Similarity	NPD7685	Pre-registration
0.7544	Intermediate Similarity	NPD7240	Approved
0.7516	Intermediate Similarity	NPD5058	Phase 3
0.7482	Intermediate Similarity	NPD7843	Approved
0.745	Intermediate Similarity	NPD4908	Phase 1
0.7447	Intermediate Similarity	NPD7157	Approved
0.7434	Intermediate Similarity	NPD4340	Discontinued
0.7417	Intermediate Similarity	NPD6233	Phase 2
0.74	Intermediate Similarity	NPD7095	Approved
0.7368	Intermediate Similarity	NPD4060	Phase 1
0.7351	Intermediate Similarity	NPD6798	Discontinued
0.7351	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4536	Approved
0.7338	Intermediate Similarity	NPD4538	Approved
0.7338	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.7317	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD5763	Approved
0.7308	Intermediate Similarity	NPD5762	Approved
0.7299	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8651	Approved
0.7289	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD4966	Approved
0.7289	Intermediate Similarity	NPD4967	Phase 2
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2861	Phase 2
0.7255	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1613	Approved
0.725	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2797	Approved
0.7246	Intermediate Similarity	NPD7075	Discontinued
0.7241	Intermediate Similarity	NPD6559	Discontinued
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5535	Approved
0.7222	Intermediate Similarity	NPD5403	Approved
0.7219	Intermediate Similarity	NPD8127	Discontinued
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1610	Phase 2
0.7209	Intermediate Similarity	NPD3818	Discontinued
0.7205	Intermediate Similarity	NPD5401	Approved
0.7202	Intermediate Similarity	NPD6234	Discontinued
0.7195	Intermediate Similarity	NPD4380	Phase 2
0.7194	Intermediate Similarity	NPD2684	Approved
0.7186	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3225	Approved
0.7179	Intermediate Similarity	NPD5588	Approved
0.7179	Intermediate Similarity	NPD5960	Phase 3
0.7179	Intermediate Similarity	NPD7033	Discontinued
0.7175	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3027	Phase 3
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6653	Approved
0.716	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4140	Approved
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5402	Approved
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3268	Approved
0.7108	Intermediate Similarity	NPD6801	Discontinued
0.7099	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD422	Phase 1
0.7093	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6166	Phase 2
0.7078	Intermediate Similarity	NPD4062	Phase 3
0.7075	Intermediate Similarity	NPD5125	Phase 3
0.7075	Intermediate Similarity	NPD5126	Approved
0.7063	Intermediate Similarity	NPD3750	Approved
0.7047	Intermediate Similarity	NPD1608	Approved
0.7044	Intermediate Similarity	NPD2424	Discontinued
0.7024	Intermediate Similarity	NPD3817	Phase 2
0.7006	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1358	Approved
0.6993	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5735	Approved
0.6982	Remote Similarity	NPD7768	Phase 2
0.698	Remote Similarity	NPD3705	Approved
0.6977	Remote Similarity	NPD3787	Discontinued
0.6975	Remote Similarity	NPD6667	Approved
0.6975	Remote Similarity	NPD6666	Approved
0.6971	Remote Similarity	NPD5844	Phase 1
0.6962	Remote Similarity	NPD3748	Approved
0.6962	Remote Similarity	NPD4108	Discontinued
0.6959	Remote Similarity	NPD6516	Phase 2
0.6959	Remote Similarity	NPD5846	Approved
0.6951	Remote Similarity	NPD6273	Approved
0.6946	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7411	Suspended
0.6944	Remote Similarity	NPD8434	Phase 2
0.6939	Remote Similarity	NPD1548	Phase 1
0.6937	Remote Similarity	NPD5958	Discontinued
0.6937	Remote Similarity	NPD4534	Discontinued
0.6933	Remote Similarity	NPD6799	Approved
0.6929	Remote Similarity	NPD3134	Approved
0.6928	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3751	Discontinued
0.6913	Remote Similarity	NPD3496	Discontinued
0.691	Remote Similarity	NPD7549	Discontinued
0.6909	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6362	Approved
0.6908	Remote Similarity	NPD3266	Approved
0.6908	Remote Similarity	NPD3267	Approved
0.6905	Remote Similarity	NPD1934	Approved
0.6897	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5585	Approved
0.6891	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7783	Phase 2
0.689	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3685	Discontinued
0.6886	Remote Similarity	NPD6599	Discontinued
0.6879	Remote Similarity	NPD290	Approved
0.6878	Remote Similarity	NPD7680	Approved
0.6875	Remote Similarity	NPD6004	Phase 3
0.6875	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6002	Phase 3
0.6875	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6005	Phase 3
0.6868	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2799	Discontinued
0.6852	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4535	Phase 3
0.6852	Remote Similarity	NPD4110	Phase 3
0.6852	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD17	Approved
0.6845	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5283	Phase 1
0.6826	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1894	Discontinued
0.6815	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6032	Approved
0.6813	Remote Similarity	NPD2438	Suspended
0.6813	Remote Similarity	NPD2796	Approved
0.681	Remote Similarity	NPD6190	Approved
0.6805	Remote Similarity	NPD4433	Discontinued
0.68	Remote Similarity	NPD3847	Discontinued
0.6797	Remote Similarity	NPD987	Approved
0.6795	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3536	Discontinued
0.6788	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8151	Discontinued
0.6788	Remote Similarity	NPD7447	Phase 1
0.6779	Remote Similarity	NPD5691	Approved
0.6774	Remote Similarity	NPD6832	Phase 2
0.6772	Remote Similarity	NPD1933	Approved
0.6771	Remote Similarity	NPD7583	Approved
0.677	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1465	Phase 2
0.6763	Remote Similarity	NPD5494	Approved
0.6753	Remote Similarity	NPD2798	Approved
0.6753	Remote Similarity	NPD5647	Approved
0.6748	Remote Similarity	NPD8166	Discontinued
0.6746	Remote Similarity	NPD6677	Suspended
0.6736	Remote Similarity	NPD7585	Approved
0.6733	Remote Similarity	NPD4626	Approved
0.6728	Remote Similarity	NPD1549	Phase 2
0.6727	Remote Similarity	NPD7212	Phase 2
0.6727	Remote Similarity	NPD7213	Phase 3
0.6724	Remote Similarity	NPD6959	Discontinued
0.6721	Remote Similarity	NPD6842	Approved
0.6721	Remote Similarity	NPD6841	Approved
0.6721	Remote Similarity	NPD6843	Phase 3
0.6709	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7435	Discontinued
0.669	Remote Similarity	NPD969	Suspended
0.6688	Remote Similarity	NPD2313	Discontinued
0.6688	Remote Similarity	NPD7985	Registered
0.6687	Remote Similarity	NPD7119	Phase 2
0.6667	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD5865	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