NPASS Compound

Structure

NPC97240 OpenBabel07101718222D 47 52 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 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 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 1 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 1 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 6.0191 1.3449 0.0000 C 0 0 1 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 4.7944 2.5696 0.0000 C 0 0 2 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 -2.8284 -3.8284 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 7.6921 1.7932 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 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 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 5.5015 3.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 42 1 0 0 0 0 2 43 1 0 0 0 0 3 7 1 0 0 0 0 3 16 2 0 0 0 0 4 8 2 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 17 2 0 0 0 0 6 10 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 11 22 2 0 0 0 0 12 21 1 0 0 0 0 12 23 2 0 0 0 0 13 20 2 0 0 0 0 13 25 1 0 0 0 0 14 21 2 0 0 0 0 14 26 1 0 0 0 0 15 35 1 0 0 0 0 18 36 1 0 0 0 0 19 44 1 0 0 0 0 20 42 1 0 0 0 0 21 43 1 0 0 0 0 22 45 1 0 0 0 0 23 46 1 0 0 0 0 24 15 1 6 0 0 0 24 31 1 0 0 0 0 24 47 1 0 0 0 0 25 37 2 0 0 0 0 25 45 1 0 0 0 0 26 38 2 0 0 0 0 26 46 1 0 0 0 0 27 16 1 6 0 0 0 27 29 1 0 0 0 0 27 30 1 0 0 0 0 28 17 1 1 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 29 22 1 6 0 0 0 30 23 1 1 0 0 0 31 32 1 0 0 0 0 31 39 1 1 0 0 0 32 33 1 0 0 0 0 32 40 1 6 0 0 0 33 34 1 0 0 0 0 33 41 1 1 0 0 0 34 44 1 6 0 0 0 34 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	650.2
Volume:	627.917
LogP:	0.996
LogD:	1.476
LogS:	-3.629
# Rotatable Bonds:	9
TPSA:	198.49
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	4.825
Fsp3:	0.353
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.679
MDCK Permeability:	1.503241128375521e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.706
20% Bioavailability (F20%):	0.057
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	86.78223419189453%
Volume Distribution (VD):	0.782
Pgp-substrate:	9.837908744812012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.759
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.389
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.814
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	6.069
Half-life (T1/2):	0.5

ADMET: Toxicity

hERG Blockers:	0.527
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.085
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC97240

Natural Product ID:	NPC97240
*Common Name:**	Achyrodimer B
IUPAC Name:	n.a.
Synonyms:	achyrodimer B
Standard InCHIKey:	VIGTUGDPCRCLDT-KDCVTONUSA-N
Standard InCHI:	InChI=1S/C34H34O13/c1-42-20-11-22(45-25(37)13-20)29-27(16-3-7-18(36)8-4-16)30(23-12-21(43-2)14-26(38)46-23)28(29)17-5-9-19(10-6-17)44-34-33(41)32(40)31(39)24(15-35)47-34/h3-14,24,27-36,39-41H,15H2,1-2H3/t24-,27-,28-,29+,30+,31-,32+,33-,34-/m1/s1
SMILES:	COc1cc([C@H]2[C@@H](c3ccc(cc3)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:	CHEMBL452463
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
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	=	0.08	%	PMID[514250]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	3.33	%	PMID[514250]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	1.63	%	PMID[514250]

☑ 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 NPC97240 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	381
0.1-0.2	1545
0.2-0.3	3427
0.3-0.4	8190
0.4-0.5	10351
0.5-0.6	5191
0.6-0.7	6396
0.7-0.8	6118
0.8-0.85	952
0.85-0.9	142
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC175275
0.9648	High Similarity	NPC220282
0.8904	High Similarity	NPC226722
0.8777	High Similarity	NPC295970
0.8758	High Similarity	NPC11411
0.8742	High Similarity	NPC478268
0.8741	High Similarity	NPC166180
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
0.8658	High Similarity	NPC232992
0.8654	High Similarity	NPC149873
0.8654	High Similarity	NPC7191
0.8652	High Similarity	NPC225384
0.8652	High Similarity	NPC246869
0.8652	High Similarity	NPC138777
0.8652	High Similarity	NPC235294
0.8652	High Similarity	NPC46137
0.8649	High Similarity	NPC34927
0.8649	High Similarity	NPC34587
0.8649	High Similarity	NPC100998
0.8649	High Similarity	NPC252292
0.8649	High Similarity	NPC138915
0.8649	High Similarity	NPC476382
0.8645	High Similarity	NPC478269
0.8639	High Similarity	NPC478239
0.863	High Similarity	NPC186406
0.8618	High Similarity	NPC169404
0.8618	High Similarity	NPC53587
0.8618	High Similarity	NPC176186
0.8609	High Similarity	NPC257970
0.8609	High Similarity	NPC476871
0.8609	High Similarity	NPC470927
0.8591	High Similarity	NPC476865
0.8581	High Similarity	NPC476867
0.8571	High Similarity	NPC140502
0.8571	High Similarity	NPC157816
0.8571	High Similarity	NPC145319
0.8562	High Similarity	NPC150442
0.8552	High Similarity	NPC124149
0.8543	High Similarity	NPC106138
0.8542	High Similarity	NPC79957
0.8535	High Similarity	NPC478267
0.8523	High Similarity	NPC476866
0.8523	High Similarity	NPC476869
0.8523	High Similarity	NPC476868
0.8523	High Similarity	NPC476864
0.8514	High Similarity	NPC278961
0.8514	High Similarity	NPC470950
0.8514	High Similarity	NPC469367
0.8514	High Similarity	NPC113680
0.8514	High Similarity	NPC185307
0.85	High Similarity	NPC288416
0.8487	Intermediate Similarity	NPC188393
0.8487	Intermediate Similarity	NPC470934
0.8467	Intermediate Similarity	NPC74320
0.8467	Intermediate Similarity	NPC199928
0.8467	Intermediate Similarity	NPC107120
0.8456	Intermediate Similarity	NPC283995
0.8456	Intermediate Similarity	NPC471063
0.8456	Intermediate Similarity	NPC129417
0.8456	Intermediate Similarity	NPC470235
0.8456	Intermediate Similarity	NPC292443
0.8456	Intermediate Similarity	NPC471028
0.8456	Intermediate Similarity	NPC232228
0.8446	Intermediate Similarity	NPC222433
0.8446	Intermediate Similarity	NPC265648
0.8446	Intermediate Similarity	NPC476356
0.8442	Intermediate Similarity	NPC245615
0.8442	Intermediate Similarity	NPC115466
0.8442	Intermediate Similarity	NPC61604
0.8442	Intermediate Similarity	NPC299706
0.8438	Intermediate Similarity	NPC59516
0.8435	Intermediate Similarity	NPC106944
0.8425	Intermediate Similarity	NPC262328
0.8425	Intermediate Similarity	NPC138738
0.8425	Intermediate Similarity	NPC87777
0.8425	Intermediate Similarity	NPC470413
0.8411	Intermediate Similarity	NPC87950
0.8411	Intermediate Similarity	NPC471764
0.84	Intermediate Similarity	NPC85624
0.84	Intermediate Similarity	NPC262182
0.84	Intermediate Similarity	NPC287615
0.84	Intermediate Similarity	NPC22150
0.84	Intermediate Similarity	NPC216819
0.84	Intermediate Similarity	NPC38041
0.84	Intermediate Similarity	NPC279298
0.84	Intermediate Similarity	NPC83743
0.8397	Intermediate Similarity	NPC228357
0.8392	Intermediate Similarity	NPC478255
0.8389	Intermediate Similarity	NPC476384
0.8389	Intermediate Similarity	NPC302286
0.8389	Intermediate Similarity	NPC476378
0.8389	Intermediate Similarity	NPC112
0.8389	Intermediate Similarity	NPC476381
0.8389	Intermediate Similarity	NPC269141
0.8389	Intermediate Similarity	NPC298257
0.8389	Intermediate Similarity	NPC96795
0.8389	Intermediate Similarity	NPC476397
0.8389	Intermediate Similarity	NPC476375
0.8389	Intermediate Similarity	NPC247032
0.8389	Intermediate Similarity	NPC237872
0.8389	Intermediate Similarity	NPC88754
0.8389	Intermediate Similarity	NPC263397
0.8389	Intermediate Similarity	NPC264632
0.8389	Intermediate Similarity	NPC175214
0.8389	Intermediate Similarity	NPC204644
0.8389	Intermediate Similarity	NPC205864
0.8389	Intermediate Similarity	NPC119537
0.8389	Intermediate Similarity	NPC76406
0.8389	Intermediate Similarity	NPC476380
0.8389	Intermediate Similarity	NPC116104
0.8389	Intermediate Similarity	NPC46092
0.8387	Intermediate Similarity	NPC160882
0.8385	Intermediate Similarity	NPC208818
0.8378	Intermediate Similarity	NPC476377
0.8378	Intermediate Similarity	NPC273932
0.8378	Intermediate Similarity	NPC108674
0.8378	Intermediate Similarity	NPC134405
0.8378	Intermediate Similarity	NPC257095
0.8378	Intermediate Similarity	NPC89686
0.8378	Intermediate Similarity	NPC472711
0.8378	Intermediate Similarity	NPC47471
0.8378	Intermediate Similarity	NPC476385
0.8377	Intermediate Similarity	NPC215060
0.8377	Intermediate Similarity	NPC476352
0.8367	Intermediate Similarity	NPC100389
0.8367	Intermediate Similarity	NPC476383
0.8367	Intermediate Similarity	NPC68092
0.8367	Intermediate Similarity	NPC64141
0.8367	Intermediate Similarity	NPC472350
0.8367	Intermediate Similarity	NPC89105
0.8367	Intermediate Similarity	NPC81515
0.8367	Intermediate Similarity	NPC197316
0.8366	Intermediate Similarity	NPC158635
0.8366	Intermediate Similarity	NPC229882
0.8366	Intermediate Similarity	NPC100818
0.8366	Intermediate Similarity	NPC475224
0.8366	Intermediate Similarity	NPC182350
0.8356	Intermediate Similarity	NPC197723
0.8356	Intermediate Similarity	NPC52277
0.8356	Intermediate Similarity	NPC40664
0.8356	Intermediate Similarity	NPC177035
0.8356	Intermediate Similarity	NPC3293
0.8356	Intermediate Similarity	NPC138350
0.8356	Intermediate Similarity	NPC199459
0.8356	Intermediate Similarity	NPC165482
0.8356	Intermediate Similarity	NPC37468
0.8355	Intermediate Similarity	NPC80732
0.8355	Intermediate Similarity	NPC261122
0.8355	Intermediate Similarity	NPC28651
0.8355	Intermediate Similarity	NPC201148
0.8355	Intermediate Similarity	NPC215095
0.8355	Intermediate Similarity	NPC95990
0.8355	Intermediate Similarity	NPC169510
0.8355	Intermediate Similarity	NPC3460
0.8355	Intermediate Similarity	NPC300262
0.8355	Intermediate Similarity	NPC210611
0.8355	Intermediate Similarity	NPC199311
0.8355	Intermediate Similarity	NPC192763
0.8355	Intermediate Similarity	NPC472339
0.8345	Intermediate Similarity	NPC187194
0.8345	Intermediate Similarity	NPC476411
0.8345	Intermediate Similarity	NPC169398
0.8344	Intermediate Similarity	NPC112861
0.8344	Intermediate Similarity	NPC291153
0.8344	Intermediate Similarity	NPC205796
0.8344	Intermediate Similarity	NPC276753
0.8344	Intermediate Similarity	NPC37838
0.8333	Intermediate Similarity	NPC110063
0.8333	Intermediate Similarity	NPC471824
0.8333	Intermediate Similarity	NPC64195
0.8333	Intermediate Similarity	NPC184464
0.8333	Intermediate Similarity	NPC225445
0.8333	Intermediate Similarity	NPC296659
0.8333	Intermediate Similarity	NPC202391
0.8333	Intermediate Similarity	NPC251062
0.8322	Intermediate Similarity	NPC473873
0.8322	Intermediate Similarity	NPC473792
0.8322	Intermediate Similarity	NPC246947
0.8322	Intermediate Similarity	NPC472353
0.8312	Intermediate Similarity	NPC85192
0.8312	Intermediate Similarity	NPC125823
0.8312	Intermediate Similarity	NPC7145
0.8312	Intermediate Similarity	NPC143480
0.8312	Intermediate Similarity	NPC259707
0.8311	Intermediate Similarity	NPC475530
0.8311	Intermediate Similarity	NPC202700
0.8311	Intermediate Similarity	NPC473799
0.831	Intermediate Similarity	NPC225307
0.831	Intermediate Similarity	NPC146540
0.8301	Intermediate Similarity	NPC44452
0.8299	Intermediate Similarity	NPC78363
0.8299	Intermediate Similarity	NPC101686

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 NPC97240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	869
0.2-0.3	1788
0.3-0.4	2689
0.4-0.5	2017
0.5-0.6	1017
0.6-0.7	297
0.7-0.8	114
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD7266	Discontinued
0.8269	Intermediate Similarity	NPD8455	Phase 2
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1653	Approved
0.7919	Intermediate Similarity	NPD7097	Phase 1
0.7817	Intermediate Similarity	NPD1091	Approved
0.7785	Intermediate Similarity	NPD5124	Phase 1
0.7785	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7054	Approved
0.7765	Intermediate Similarity	NPD8312	Approved
0.7765	Intermediate Similarity	NPD8313	Approved
0.7751	Intermediate Similarity	NPD7685	Pre-registration
0.7738	Intermediate Similarity	NPD7472	Approved
0.7738	Intermediate Similarity	NPD7074	Phase 3
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7725	Intermediate Similarity	NPD7228	Approved
0.7706	Intermediate Similarity	NPD7808	Phase 3
0.7687	Intermediate Similarity	NPD4908	Phase 1
0.7662	Intermediate Similarity	NPD6674	Discontinued
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.76	Intermediate Similarity	NPD4060	Phase 1
0.7588	Intermediate Similarity	NPD6797	Phase 2
0.7584	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6355	Discontinued
0.755	Intermediate Similarity	NPD4340	Discontinued
0.7548	Intermediate Similarity	NPD1652	Phase 2
0.7516	Intermediate Similarity	NPD5058	Phase 3
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2861	Phase 2
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD7843	Approved
0.7455	Intermediate Similarity	NPD7075	Discontinued
0.7448	Intermediate Similarity	NPD1610	Phase 2
0.7447	Intermediate Similarity	NPD7157	Approved
0.7442	Intermediate Similarity	NPD6559	Discontinued
0.7423	Intermediate Similarity	NPD37	Approved
0.7417	Intermediate Similarity	NPD6233	Phase 2
0.7412	Intermediate Similarity	NPD3818	Discontinued
0.741	Intermediate Similarity	NPD6234	Discontinued
0.7407	Intermediate Similarity	NPD4380	Phase 2
0.74	Intermediate Similarity	NPD3027	Phase 3
0.74	Intermediate Similarity	NPD7095	Approved
0.7394	Intermediate Similarity	NPD4966	Approved
0.7394	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4967	Phase 2
0.7394	Intermediate Similarity	NPD4965	Approved
0.7371	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2797	Approved
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6798	Discontinued
0.7346	Intermediate Similarity	NPD7458	Discontinued
0.7341	Intermediate Similarity	NPD7240	Approved
0.7338	Intermediate Similarity	NPD4536	Approved
0.7338	Intermediate Similarity	NPD4538	Approved
0.7338	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7329	Intermediate Similarity	NPD5403	Approved
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.7308	Intermediate Similarity	NPD5763	Approved
0.7308	Intermediate Similarity	NPD5762	Approved
0.7297	Intermediate Similarity	NPD8651	Approved
0.7297	Intermediate Similarity	NPD3225	Approved
0.729	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD3750	Approved
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6653	Approved
0.7237	Intermediate Similarity	NPD3268	Approved
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5535	Approved
0.7229	Intermediate Similarity	NPD5402	Approved
0.7226	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8127	Discontinued
0.7219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6801	Discontinued
0.7205	Intermediate Similarity	NPD5401	Approved
0.7205	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2684	Approved
0.7193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6166	Phase 2
0.7193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7768	Phase 2
0.7184	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5588	Approved
0.7179	Intermediate Similarity	NPD5960	Phase 3
0.7172	Intermediate Similarity	NPD1548	Phase 1
0.7169	Intermediate Similarity	NPD7819	Suspended
0.716	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4140	Approved
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1934	Approved
0.7107	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6666	Approved
0.7081	Intermediate Similarity	NPD6667	Approved
0.7078	Intermediate Similarity	NPD4062	Phase 3
0.7075	Intermediate Similarity	NPD5125	Phase 3
0.7075	Intermediate Similarity	NPD5126	Approved
0.7069	Intermediate Similarity	NPD5844	Phase 1
0.7066	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7048	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1608	Approved
0.7044	Intermediate Similarity	NPD2424	Discontinued
0.7027	Intermediate Similarity	NPD3496	Discontinued
0.7024	Intermediate Similarity	NPD3817	Phase 2
0.7019	Intermediate Similarity	NPD6190	Approved
0.7013	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3751	Discontinued
0.7006	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD1358	Approved
0.6994	Remote Similarity	NPD7447	Phase 1
0.6994	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3536	Discontinued
0.6987	Remote Similarity	NPD5735	Approved
0.6981	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6004	Phase 3
0.6981	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6002	Phase 3
0.6981	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6005	Phase 3
0.698	Remote Similarity	NPD3705	Approved
0.6979	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7783	Phase 2
0.6977	Remote Similarity	NPD3787	Discontinued
0.6968	Remote Similarity	NPD7680	Approved
0.6962	Remote Similarity	NPD4108	Discontinued
0.6962	Remote Similarity	NPD3748	Approved
0.6959	Remote Similarity	NPD6516	Phase 2
0.6959	Remote Similarity	NPD5846	Approved
0.6957	Remote Similarity	NPD8166	Discontinued
0.6951	Remote Similarity	NPD6273	Approved
0.6944	Remote Similarity	NPD8434	Phase 2
0.6937	Remote Similarity	NPD1549	Phase 2
0.6937	Remote Similarity	NPD5958	Discontinued
0.6937	Remote Similarity	NPD4534	Discontinued
0.6935	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6799	Approved
0.6933	Remote Similarity	NPD7212	Phase 2
0.6933	Remote Similarity	NPD7213	Phase 3
0.6929	Remote Similarity	NPD3134	Approved
0.6928	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7585	Approved
0.6909	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3266	Approved
0.6908	Remote Similarity	NPD6362	Approved
0.6908	Remote Similarity	NPD3267	Approved
0.6892	Remote Similarity	NPD5585	Approved
0.689	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3685	Discontinued
0.6887	Remote Similarity	NPD4749	Approved
0.6886	Remote Similarity	NPD6599	Discontinued
0.6879	Remote Similarity	NPD290	Approved
0.6878	Remote Similarity	NPD7435	Discontinued
0.6867	Remote Similarity	NPD1535	Discovery
0.6864	Remote Similarity	NPD1465	Phase 2
0.6864	Remote Similarity	NPD2801	Approved
0.6863	Remote Similarity	NPD5647	Approved
0.6859	Remote Similarity	NPD7583	Approved
0.6855	Remote Similarity	NPD2799	Discontinued
0.6852	Remote Similarity	NPD4110	Phase 3
0.6852	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4535	Phase 3
0.6852	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6671	Approved
0.6846	Remote Similarity	NPD4626	Approved
0.6846	Remote Similarity	NPD17	Approved
0.6839	Remote Similarity	NPD4625	Phase 3
0.6828	Remote Similarity	NPD5283	Phase 1
0.6824	Remote Similarity	NPD1894	Discontinued
0.6821	Remote Similarity	NPD1481	Phase 2
0.6821	Remote Similarity	NPD6959	Discontinued
0.6815	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2796	Approved
0.6813	Remote Similarity	NPD6032	Approved
0.6813	Remote Similarity	NPD2438	Suspended
0.6813	Remote Similarity	NPD2935	Discontinued
0.6809	Remote Similarity	NPD968	Approved
0.6805	Remote Similarity	NPD4433	Discontinued
0.68	Remote Similarity	NPD3847	Discontinued
0.6797	Remote Similarity	NPD987	Approved
0.6795	Remote Similarity	NPD3764	Approved
0.6788	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8151	Discontinued
0.6779	Remote Similarity	NPD5691	Approved
0.6779	Remote Similarity	NPD1357	Approved
0.6776	Remote Similarity	NPD6583	Phase 3
0.6776	Remote Similarity	NPD6582	Phase 2
0.6774	Remote Similarity	NPD6832	Phase 2

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