NPASS Compound

Structure

NPC71390 OpenBabel07101718242D 45 50 0 0 1 0 0 0 0 0999 V2000 -4.3961 -0.5076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6377 -1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4026 -1.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3983 -3.0830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4133 -3.0596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7584 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8792 -0.5076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6377 -0.5076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5169 1.0152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8945 -1.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6165 -0.4730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5169 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7584 -2.0305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3868 -0.3716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7584 1.0152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7584 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8705 -2.2158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9005 -2.1688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6377 1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5400 -1.0877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8599 0.2449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7584 1.0152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3577 -1.3251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3726 -1.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8149 -0.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8792 1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5122 0.1117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8299 -0.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8792 1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8792 -0.5076 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8598 -0.4109 0.0000 C 0 0 0 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 -1.7584 -3.0457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8556 -2.2393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9154 -2.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6377 2.5381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1911 -1.8666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8792 2.5381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1267 0.9199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3170 0.4329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8792 2.5381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3320 0.4564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8748 -0.3874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8792 -1.5229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 44 1 0 0 0 0 4 5 2 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 2 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 19 2 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 33 1 0 0 0 0 13 34 2 0 0 0 0 13 45 1 0 0 0 0 14 21 1 0 0 0 0 15 6 1 1 0 0 0 15 21 1 0 0 0 0 15 27 1 0 0 0 0 16 22 2 0 0 0 0 16 31 1 0 0 0 0 17 23 2 0 0 0 0 17 35 1 0 0 0 0 18 24 2 0 0 0 0 18 36 1 0 0 0 0 19 22 1 0 0 0 0 19 37 1 0 0 0 0 20 25 2 0 0 0 0 20 38 1 0 0 0 0 21 28 2 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 32 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 26 27 1 0 0 0 0 26 30 2 0 0 0 0 26 33 1 0 0 0 0 27 39 2 0 0 0 0 28 40 1 0 0 0 0 29 41 2 0 0 0 0 30 42 1 0 0 0 0 31 33 1 1 0 0 0 31 45 1 0 0 0 0 32 43 2 0 0 0 0 32 44 1 0 0 0 0 33 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.14
Volume:	593.921
LogP:	5.512
LogD:	2.133
LogS:	-7.342
# Rotatable Bonds:	6
TPSA:	204.96
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.124
Synthetic Accessibility Score:	5.761
Fsp3:	0.242
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:	-6.341
MDCK Permeability:	8.3847207861254e-06
Pgp-inhibitor:	0.538
Pgp-substrate:	0.827
Human Intestinal Absorption (HIA):	0.854
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	99.73499298095703%
Volume Distribution (VD):	0.366
Pgp-substrate:	1.8171062469482422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.728
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.325
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.775
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.361
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	1.128
Half-life (T1/2):	0.03

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.72
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.168
Carcinogencity:	0.192
Eye Corrosion:	0.003
Eye Irritation:	0.489
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC71390

Natural Product ID:	NPC71390
*Common Name:**	OFAIMNXQEZOWPU-RXKIPKFJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OFAIMNXQEZOWPU-RXKIPKFJSA-N
Standard InCHI:	InChI=1S/C33H26O12/c1-12-8-16-22(19(37)9-12)30(42)26-27(39)15-6-7-33(26,31(16)45-13(2)34)11-14-10-20(38)25(28(40)21(14)15)29(41)23-17(35)4-5-18(36)24(23)32(43)44-3/h4-10,15,31,35-38,40,42H,11H2,1-3H3/t15-,31-,33-/m0/s1
SMILES:	Cc1cc2c(c(c1)O)C(=C1C(=O)[C@H]3C=C[C@@]1(Cc1cc(c(c(c31)O)C(=O)c1c(ccc(c1C(=O)OC)O)O)O)[C@H]2OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408939
PubChem CID:	9895201
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO22864	Purpureocillium lilacinum	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23876004]
NPO22864	Purpureocillium lilacinum	Species	Ophiocordycipitaceae	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
Kd	1
Others	2

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1621	Individual Protein	Calmodulin	Homo sapiens	Activity	=	48.0	%	PMID[548159]
NPT1621	Individual Protein	Calmodulin	Homo sapiens	Ratio	=	70.0	n.a.	PMID[548159]
NPT1621	Individual Protein	Calmodulin	Homo sapiens	Kd	=	19.4	nM	PMID[548159]

☑ 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 NPC71390 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	379
0.1-0.2	1528
0.2-0.3	2966
0.3-0.4	7492
0.4-0.5	11157
0.5-0.6	4868
0.6-0.7	6861
0.7-0.8	6923
0.8-0.85	475
0.85-0.9	47
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.878	High Similarity	NPC315772
0.8758	High Similarity	NPC66029
0.875	High Similarity	NPC477836
0.8728	High Similarity	NPC197972
0.8608	High Similarity	NPC470570
0.8608	High Similarity	NPC147250
0.858	High Similarity	NPC474824
0.858	High Similarity	NPC470408
0.858	High Similarity	NPC182921
0.858	High Similarity	NPC218870
0.8571	High Similarity	NPC76647
0.8544	High Similarity	NPC34482
0.8537	High Similarity	NPC317580
0.8537	High Similarity	NPC67197
0.8535	High Similarity	NPC476473
0.8519	High Similarity	NPC474534
0.8519	High Similarity	NPC474533
0.8512	High Similarity	NPC30027
0.8512	High Similarity	NPC477835
0.8509	High Similarity	NPC205766
0.8485	Intermediate Similarity	NPC186113
0.8485	Intermediate Similarity	NPC326084
0.8481	Intermediate Similarity	NPC193703
0.8481	Intermediate Similarity	NPC48762
0.8481	Intermediate Similarity	NPC21599
0.8481	Intermediate Similarity	NPC10764
0.848	Intermediate Similarity	NPC131862
0.8476	Intermediate Similarity	NPC474861
0.8471	Intermediate Similarity	NPC474300
0.8466	Intermediate Similarity	NPC474621
0.8466	Intermediate Similarity	NPC474622
0.8462	Intermediate Similarity	NPC324522
0.8462	Intermediate Similarity	NPC105414
0.8462	Intermediate Similarity	NPC472058
0.8462	Intermediate Similarity	NPC234497
0.8462	Intermediate Similarity	NPC107009
0.8462	Intermediate Similarity	NPC470341
0.8447	Intermediate Similarity	NPC477221
0.8439	Intermediate Similarity	NPC477683
0.8439	Intermediate Similarity	NPC477682
0.8438	Intermediate Similarity	NPC119767
0.8434	Intermediate Similarity	NPC475449
0.8415	Intermediate Similarity	NPC318270
0.8415	Intermediate Similarity	NPC3898
0.8412	Intermediate Similarity	NPC291795
0.8412	Intermediate Similarity	NPC207574
0.8412	Intermediate Similarity	NPC297195
0.8408	Intermediate Similarity	NPC187843
0.8402	Intermediate Similarity	NPC251336
0.8395	Intermediate Similarity	NPC477914
0.8385	Intermediate Similarity	NPC221352
0.8383	Intermediate Similarity	NPC472261
0.8373	Intermediate Similarity	NPC228654
0.8373	Intermediate Similarity	NPC324736
0.8372	Intermediate Similarity	NPC229051
0.8365	Intermediate Similarity	NPC42540
0.8365	Intermediate Similarity	NPC151607
0.8365	Intermediate Similarity	NPC477913
0.8364	Intermediate Similarity	NPC146211
0.8363	Intermediate Similarity	NPC241874
0.8363	Intermediate Similarity	NPC251144
0.8363	Intermediate Similarity	NPC241387
0.8363	Intermediate Similarity	NPC193698
0.8354	Intermediate Similarity	NPC135522
0.8344	Intermediate Similarity	NPC32749
0.8344	Intermediate Similarity	NPC147542
0.8344	Intermediate Similarity	NPC327916
0.8344	Intermediate Similarity	NPC220496
0.8344	Intermediate Similarity	NPC42262
0.8344	Intermediate Similarity	NPC37992
0.8344	Intermediate Similarity	NPC241349
0.8333	Intermediate Similarity	NPC473022
0.8333	Intermediate Similarity	NPC473961
0.8324	Intermediate Similarity	NPC86809
0.8324	Intermediate Similarity	NPC98667
0.8324	Intermediate Similarity	NPC232412
0.8323	Intermediate Similarity	NPC470342
0.8323	Intermediate Similarity	NPC472052
0.8323	Intermediate Similarity	NPC472060
0.8323	Intermediate Similarity	NPC476506
0.8313	Intermediate Similarity	NPC263483
0.8313	Intermediate Similarity	NPC44199
0.8303	Intermediate Similarity	NPC66508
0.8303	Intermediate Similarity	NPC226656
0.8302	Intermediate Similarity	NPC159721
0.8302	Intermediate Similarity	NPC471731
0.8294	Intermediate Similarity	NPC125465
0.8294	Intermediate Similarity	NPC178173
0.8293	Intermediate Similarity	NPC175978
0.8293	Intermediate Similarity	NPC281272
0.8291	Intermediate Similarity	NPC257003
0.8291	Intermediate Similarity	NPC471444
0.8286	Intermediate Similarity	NPC473785
0.8282	Intermediate Similarity	NPC315520
0.8282	Intermediate Similarity	NPC294646
0.8282	Intermediate Similarity	NPC470568
0.828	Intermediate Similarity	NPC29771
0.828	Intermediate Similarity	NPC111422
0.828	Intermediate Similarity	NPC256463
0.828	Intermediate Similarity	NPC216312
0.828	Intermediate Similarity	NPC471602
0.828	Intermediate Similarity	NPC306835
0.828	Intermediate Similarity	NPC476477
0.828	Intermediate Similarity	NPC299405
0.8276	Intermediate Similarity	NPC469345
0.8274	Intermediate Similarity	NPC219686
0.8274	Intermediate Similarity	NPC18380
0.8272	Intermediate Similarity	NPC290695
0.8272	Intermediate Similarity	NPC106524
0.8269	Intermediate Similarity	NPC305060
0.8261	Intermediate Similarity	NPC271944
0.8261	Intermediate Similarity	NPC110882
0.8261	Intermediate Similarity	NPC85393
0.8253	Intermediate Similarity	NPC478027
0.8253	Intermediate Similarity	NPC469507
0.8239	Intermediate Similarity	NPC474961
0.8239	Intermediate Similarity	NPC471733
0.8239	Intermediate Similarity	NPC135524
0.8235	Intermediate Similarity	NPC472057
0.8235	Intermediate Similarity	NPC472051
0.8235	Intermediate Similarity	NPC469664
0.8232	Intermediate Similarity	NPC470569
0.8229	Intermediate Similarity	NPC478000
0.8229	Intermediate Similarity	NPC207467
0.8228	Intermediate Similarity	NPC275903
0.8228	Intermediate Similarity	NPC169452
0.8228	Intermediate Similarity	NPC181560
0.8225	Intermediate Similarity	NPC472059
0.8225	Intermediate Similarity	NPC15374
0.8218	Intermediate Similarity	NPC294149
0.8218	Intermediate Similarity	NPC477992
0.8218	Intermediate Similarity	NPC477991
0.8214	Intermediate Similarity	NPC284495
0.8214	Intermediate Similarity	NPC184326
0.8214	Intermediate Similarity	NPC472618
0.8214	Intermediate Similarity	NPC292863
0.8214	Intermediate Similarity	NPC472055
0.8214	Intermediate Similarity	NPC143050
0.821	Intermediate Similarity	NPC162751
0.821	Intermediate Similarity	NPC37709
0.821	Intermediate Similarity	NPC290194
0.821	Intermediate Similarity	NPC52161
0.8208	Intermediate Similarity	NPC472620
0.8204	Intermediate Similarity	NPC158542
0.8198	Intermediate Similarity	NPC54903
0.8198	Intermediate Similarity	NPC49487
0.8198	Intermediate Similarity	NPC264063
0.8198	Intermediate Similarity	NPC286074
0.8198	Intermediate Similarity	NPC99613
0.8198	Intermediate Similarity	NPC469486
0.8187	Intermediate Similarity	NPC295712
0.8187	Intermediate Similarity	NPC469394
0.8187	Intermediate Similarity	NPC174905
0.8187	Intermediate Similarity	NPC474203
0.8187	Intermediate Similarity	NPC120857
0.8187	Intermediate Similarity	NPC17274
0.8187	Intermediate Similarity	NPC451542
0.8187	Intermediate Similarity	NPC66593
0.8187	Intermediate Similarity	NPC293545
0.8187	Intermediate Similarity	NPC85047
0.8187	Intermediate Similarity	NPC313047
0.8182	Intermediate Similarity	NPC478220
0.8182	Intermediate Similarity	NPC154683
0.8182	Intermediate Similarity	NPC40356
0.8176	Intermediate Similarity	NPC469395
0.8176	Intermediate Similarity	NPC472053
0.8176	Intermediate Similarity	NPC305845
0.8176	Intermediate Similarity	NPC204045
0.8176	Intermediate Similarity	NPC472603
0.8171	Intermediate Similarity	NPC290954
0.8171	Intermediate Similarity	NPC255641
0.8171	Intermediate Similarity	NPC147735
0.8171	Intermediate Similarity	NPC280295
0.8166	Intermediate Similarity	NPC137232
0.8166	Intermediate Similarity	NPC266365
0.8166	Intermediate Similarity	NPC301256
0.8166	Intermediate Similarity	NPC189552
0.8166	Intermediate Similarity	NPC312273
0.8166	Intermediate Similarity	NPC273467
0.8165	Intermediate Similarity	NPC19622
0.8165	Intermediate Similarity	NPC143438
0.8165	Intermediate Similarity	NPC242994
0.8165	Intermediate Similarity	NPC138099
0.8165	Intermediate Similarity	NPC295339
0.8165	Intermediate Similarity	NPC112789
0.8161	Intermediate Similarity	NPC154986
0.8161	Intermediate Similarity	NPC470333
0.8161	Intermediate Similarity	NPC472054
0.816	Intermediate Similarity	NPC2569
0.816	Intermediate Similarity	NPC5537
0.816	Intermediate Similarity	NPC172329
0.8155	Intermediate Similarity	NPC470339
0.8155	Intermediate Similarity	NPC195167
0.8155	Intermediate Similarity	NPC105584
0.8155	Intermediate Similarity	NPC239118
0.8155	Intermediate Similarity	NPC474373
0.8155	Intermediate Similarity	NPC90497
0.8155	Intermediate Similarity	NPC4950
0.8148	Intermediate Similarity	NPC314437
0.8148	Intermediate Similarity	NPC202112

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 NPC71390 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	959
0.2-0.3	1593
0.3-0.4	2664
0.4-0.5	2053
0.5-0.6	1051
0.6-0.7	369
0.7-0.8	128
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8294	Intermediate Similarity	NPD7473	Discontinued
0.8225	Intermediate Similarity	NPD6232	Discontinued
0.8166	Intermediate Similarity	NPD6959	Discontinued
0.8137	Intermediate Similarity	NPD7390	Discontinued
0.8045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD8150	Discontinued
0.8024	Intermediate Similarity	NPD7819	Suspended
0.7976	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5408	Approved
0.7925	Intermediate Similarity	NPD5405	Approved
0.7925	Intermediate Similarity	NPD5404	Approved
0.7925	Intermediate Similarity	NPD5406	Approved
0.7886	Intermediate Similarity	NPD5844	Phase 1
0.7866	Intermediate Similarity	NPD2532	Approved
0.7866	Intermediate Similarity	NPD2534	Approved
0.7866	Intermediate Similarity	NPD2533	Approved
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7798	Intermediate Similarity	NPD7411	Suspended
0.7784	Intermediate Similarity	NPD3226	Approved
0.7765	Intermediate Similarity	NPD8312	Approved
0.7765	Intermediate Similarity	NPD8313	Approved
0.773	Intermediate Similarity	NPD7003	Approved
0.7651	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4380	Phase 2
0.7622	Intermediate Similarity	NPD3750	Approved
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7075	Discontinued
0.7558	Intermediate Similarity	NPD5402	Approved
0.7556	Intermediate Similarity	NPD6559	Discontinued
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7545	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8166	Discontinued
0.7514	Intermediate Similarity	NPD6166	Phase 2
0.7514	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7486	Intermediate Similarity	NPD5494	Approved
0.7471	Intermediate Similarity	NPD3749	Approved
0.746	Intermediate Similarity	NPD7700	Phase 2
0.746	Intermediate Similarity	NPD7699	Phase 2
0.7448	Intermediate Similarity	NPD7435	Discontinued
0.7436	Intermediate Similarity	NPD8151	Discontinued
0.7427	Intermediate Similarity	NPD6599	Discontinued
0.7423	Intermediate Similarity	NPD2799	Discontinued
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD8319	Approved
0.7409	Intermediate Similarity	NPD8320	Phase 1
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7399	Intermediate Similarity	NPD2801	Approved
0.7399	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6781	Approved
0.7382	Intermediate Similarity	NPD6778	Approved
0.7382	Intermediate Similarity	NPD6779	Approved
0.7382	Intermediate Similarity	NPD6776	Approved
0.7382	Intermediate Similarity	NPD6777	Approved
0.7382	Intermediate Similarity	NPD6782	Approved
0.7382	Intermediate Similarity	NPD6780	Approved
0.7375	Intermediate Similarity	NPD3764	Approved
0.7368	Intermediate Similarity	NPD7458	Discontinued
0.7358	Intermediate Similarity	NPD7698	Approved
0.7358	Intermediate Similarity	NPD7696	Phase 3
0.7358	Intermediate Similarity	NPD7697	Approved
0.7355	Intermediate Similarity	NPD1201	Approved
0.7341	Intermediate Similarity	NPD6801	Discontinued
0.7341	Intermediate Similarity	NPD37	Approved
0.7341	Intermediate Similarity	NPD1934	Approved
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6234	Discontinued
0.7322	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3748	Approved
0.7317	Intermediate Similarity	NPD1510	Phase 2
0.7314	Intermediate Similarity	NPD4966	Approved
0.7314	Intermediate Similarity	NPD4965	Approved
0.7314	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7874	Approved
0.7305	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5710	Approved
0.7303	Intermediate Similarity	NPD5711	Approved
0.7301	Intermediate Similarity	NPD1607	Approved
0.7297	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6273	Approved
0.7289	Intermediate Similarity	NPD1549	Phase 2
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7783	Phase 2
0.7258	Intermediate Similarity	NPD8434	Phase 2
0.7257	Intermediate Similarity	NPD3817	Phase 2
0.7253	Intermediate Similarity	NPD7074	Phase 3
0.7249	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6213	Phase 3
0.7249	Intermediate Similarity	NPD6212	Phase 3
0.7246	Intermediate Similarity	NPD2800	Approved
0.7246	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7228	Approved
0.7216	Intermediate Similarity	NPD6823	Phase 2
0.7208	Intermediate Similarity	NPD7701	Phase 2
0.7198	Intermediate Similarity	NPD7054	Approved
0.7195	Intermediate Similarity	NPD6651	Approved
0.7186	Intermediate Similarity	NPD7801	Approved
0.7178	Intermediate Similarity	NPD1240	Approved
0.7169	Intermediate Similarity	NPD2796	Approved
0.7158	Intermediate Similarity	NPD7472	Approved
0.7157	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7135	Intermediate Similarity	NPD7808	Phase 3
0.712	Intermediate Similarity	NPD6797	Phase 2
0.712	Intermediate Similarity	NPD5953	Discontinued
0.7117	Intermediate Similarity	NPD6663	Approved
0.7111	Intermediate Similarity	NPD7229	Phase 3
0.7108	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4628	Phase 3
0.7099	Intermediate Similarity	NPD7008	Discontinued
0.7081	Intermediate Similarity	NPD7251	Discontinued
0.7081	Intermediate Similarity	NPD5736	Approved
0.7076	Intermediate Similarity	NPD1511	Approved
0.7076	Intermediate Similarity	NPD6799	Approved
0.7073	Intermediate Similarity	NPD943	Approved
0.7066	Intermediate Similarity	NPD6100	Approved
0.7066	Intermediate Similarity	NPD6099	Approved
0.7055	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7049	Intermediate Similarity	NPD3751	Discontinued
0.7039	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5401	Approved
0.703	Intermediate Similarity	NPD230	Phase 1
0.7022	Intermediate Similarity	NPD3882	Suspended
0.7018	Intermediate Similarity	NPD3300	Phase 2
0.7006	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD1283	Approved
0.6994	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1512	Approved
0.697	Remote Similarity	NPD2979	Phase 3
0.6964	Remote Similarity	NPD2438	Suspended
0.6961	Remote Similarity	NPD8127	Discontinued
0.6959	Remote Similarity	NPD6190	Approved
0.6957	Remote Similarity	NPD1164	Approved
0.6954	Remote Similarity	NPD920	Approved
0.6933	Remote Similarity	NPD4908	Phase 1
0.6923	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7286	Phase 2
0.6919	Remote Similarity	NPD7236	Approved
0.6914	Remote Similarity	NPD7239	Suspended
0.691	Remote Similarity	NPD8455	Phase 2
0.6899	Remote Similarity	NPD3019	Approved
0.6899	Remote Similarity	NPD2932	Approved
0.6898	Remote Similarity	NPD7240	Approved
0.6893	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7199	Phase 2
0.6865	Remote Similarity	NPD7177	Discontinued
0.6859	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD9493	Approved
0.6857	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3787	Discontinued
0.6829	Remote Similarity	NPD6832	Phase 2
0.6824	Remote Similarity	NPD2344	Approved
0.6813	Remote Similarity	NPD1281	Approved
0.681	Remote Similarity	NPD2798	Approved
0.6807	Remote Similarity	NPD8032	Phase 2
0.6805	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8285	Discontinued
0.6793	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4626	Approved
0.6792	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4625	Phase 3
0.6778	Remote Similarity	NPD4288	Approved
0.6774	Remote Similarity	NPD7799	Discontinued
0.6774	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4060	Phase 1
0.6748	Remote Similarity	NPD1203	Approved
0.6748	Remote Similarity	NPD2797	Approved
0.6747	Remote Similarity	NPD3268	Approved
0.6747	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1243	Approved
0.6736	Remote Similarity	NPD8360	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