NPASS Compound

Structure

NPC266365 OpenBabel07101718302D 47 52 0 0 1 0 0 0 0 0999 V2000 4.5024 -0.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0268 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5302 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 1.0774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5113 1.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 -0.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0208 1.0774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 0.4906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5491 1.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0208 2.7767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6994 -2.9434 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0396 2.7767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 -0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5491 -2.4528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5113 0.2277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -1.4717 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5491 -1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8497 0.4906 0.0000 C 0 0 1 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 2.5491 1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5679 1.9270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5113 3.6264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 -3.9245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 3.6264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3987 -2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4925 0.2277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0208 -0.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 32 1 0 0 0 0 5 35 1 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 8 26 1 0 0 0 0 9 11 1 0 0 0 0 9 32 1 0 0 0 0 10 12 1 0 0 0 0 10 35 1 0 0 0 0 11 37 1 0 0 0 0 12 37 1 0 0 0 0 13 19 2 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 23 2 0 0 0 0 15 21 1 0 0 0 0 15 32 1 0 0 0 0 16 25 1 0 0 0 0 16 33 1 0 0 0 0 17 24 1 0 0 0 0 17 36 1 0 0 0 0 18 34 1 0 0 0 0 18 47 1 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 35 1 0 0 0 0 21 37 1 1 0 0 0 22 27 2 0 0 0 0 22 38 1 0 0 0 0 23 27 1 0 0 0 0 23 39 1 0 0 0 0 24 28 1 0 0 0 0 24 40 1 6 0 0 0 25 29 1 0 0 0 0 25 41 1 1 0 0 0 26 33 1 6 0 0 0 26 36 1 0 0 0 0 27 42 1 0 0 0 0 28 33 1 6 0 0 0 28 34 1 0 0 0 0 29 34 1 6 0 0 0 29 43 1 0 0 0 0 30 44 2 0 0 0 0 30 47 1 0 0 0 0 31 45 2 0 0 0 0 31 46 1 0 0 0 0 33 3 1 6 0 0 0 34 4 1 6 0 0 0 35 36 1 6 0 0 0 36 6 1 6 0 0 0 37 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.36
Volume:	669.253
LogP:	4.387
LogD:	2.441
LogS:	-3.108
# Rotatable Bonds:	5
TPSA:	184.98
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.13
Synthetic Accessibility Score:	5.343
Fsp3:	0.73
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.897
MDCK Permeability:	4.8565348151896615e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.703

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	98.3858413696289%
Volume Distribution (VD):	0.904
Pgp-substrate:	8.56443977355957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.256
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.293
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.262
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	1.874
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.12
Carcinogencity:	0.061
Eye Corrosion:	0.004
Eye Irritation:	0.542
Respiratory Toxicity:	0.827

Download Data

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

Natural Product: NPC266365

Natural Product ID:	NPC266365
*Common Name:**	23-Galloylterminolic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(3,4,5-trihydroxybenzoyl)oxymethyl]-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	23-Galloylterminolic Acid
Standard InCHIKey:	KDASALSDFBNLFU-LZFIOKTDSA-N
Standard InCHI:	InChI=1S/C37H52O10/c1-32(2)9-11-37(31(45)46)12-10-35(5)20(21(37)15-32)7-8-26-33(3)16-25(41)29(43)34(4,28(33)24(40)17-36(26,35)6)18-47-30(44)19-13-22(38)27(42)23(39)14-19/h7,13-14,21,24-26,28-29,38-43H,8-12,15-18H2,1-6H3,(H,45,46)/t21-,24+,25+,26+,28+,29-,33+,34-,35+,36+,37-/m0/s1
SMILES:	O=C(c1cc(O)c(c(c1)O)O)OC[C@]1(C)[C@@H](O)[C@H](O)C[C@]2([C@H]1[C@H](O)C[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448899
PubChem CID:	21603542
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32828	buchenavia parviflora	Species	Combretaceae	Eukaryota	roots	n.a.	n.a.	PMID[12502337]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	50.0	ug.mL-1	PMID[485026]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50.0	ug.mL-1	PMID[485026]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	50.0	ug.mL-1	PMID[485026]

☑ 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 NPC266365 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	385
0.1-0.2	1442
0.2-0.3	3010
0.3-0.4	5700
0.4-0.5	9435
0.5-0.6	8290
0.6-0.7	7933
0.7-0.8	6067
0.8-0.85	378
0.85-0.9	51
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9085	High Similarity	NPC325032
0.9085	High Similarity	NPC477483
0.8974	High Similarity	NPC221249
0.8968	High Similarity	NPC327962
0.8963	High Similarity	NPC472803
0.8924	High Similarity	NPC472807
0.8902	High Similarity	NPC202428
0.8902	High Similarity	NPC266545
0.8896	High Similarity	NPC200726
0.8841	High Similarity	NPC217781
0.8841	High Similarity	NPC177362
0.8831	High Similarity	NPC75295
0.8831	High Similarity	NPC258856
0.878	High Similarity	NPC26536
0.878	High Similarity	NPC49983
0.878	High Similarity	NPC317671
0.878	High Similarity	NPC142707
0.8766	High Similarity	NPC53520
0.8758	High Similarity	NPC469447
0.8758	High Similarity	NPC477873
0.872	High Similarity	NPC162169
0.872	High Similarity	NPC166851
0.8698	High Similarity	NPC469418
0.8698	High Similarity	NPC260300
0.8688	High Similarity	NPC203757
0.8688	High Similarity	NPC156624
0.8688	High Similarity	NPC172920
0.8683	High Similarity	NPC100251
0.8683	High Similarity	NPC65333
0.8667	High Similarity	NPC175793
0.8662	High Similarity	NPC279442
0.8631	High Similarity	NPC98583
0.8625	High Similarity	NPC62051
0.8623	High Similarity	NPC470272
0.8616	High Similarity	NPC475579
0.8616	High Similarity	NPC473773
0.8614	High Similarity	NPC190204
0.8614	High Similarity	NPC43918
0.8614	High Similarity	NPC261411
0.8614	High Similarity	NPC470271
0.8614	High Similarity	NPC311389
0.8599	High Similarity	NPC142528
0.8598	High Similarity	NPC315772
0.8589	High Similarity	NPC24627
0.8588	High Similarity	NPC80360
0.8581	High Similarity	NPC25491
0.8581	High Similarity	NPC226738
0.8581	High Similarity	NPC22176
0.8581	High Similarity	NPC190587
0.8581	High Similarity	NPC121573
0.858	High Similarity	NPC104275
0.858	High Similarity	NPC4747
0.8562	High Similarity	NPC271494
0.8562	High Similarity	NPC473591
0.8562	High Similarity	NPC155192
0.8554	High Similarity	NPC469394
0.8553	High Similarity	NPC118033
0.8547	High Similarity	NPC473205
0.8547	High Similarity	NPC473776
0.8545	High Similarity	NPC161151
0.8538	High Similarity	NPC195114
0.8535	High Similarity	NPC474991
0.8535	High Similarity	NPC268366
0.8528	High Similarity	NPC318826
0.8528	High Similarity	NPC114791
0.8528	High Similarity	NPC210501
0.8528	High Similarity	NPC141331
0.8528	High Similarity	NPC104222
0.8521	High Similarity	NPC471969
0.8519	High Similarity	NPC247629
0.8519	High Similarity	NPC134925
0.8519	High Similarity	NPC239019
0.8512	High Similarity	NPC47521
0.8512	High Similarity	NPC180768
0.8509	High Similarity	NPC281703
0.8509	High Similarity	NPC125487
0.8506	High Similarity	NPC172311
0.8506	High Similarity	NPC27518
0.8506	High Similarity	NPC304110
0.8506	High Similarity	NPC470035
0.8503	High Similarity	NPC31034
0.85	High Similarity	NPC124842
0.8497	Intermediate Similarity	NPC182249
0.8497	Intermediate Similarity	NPC239943
0.8491	Intermediate Similarity	NPC142654
0.8491	Intermediate Similarity	NPC306343
0.8488	Intermediate Similarity	NPC102367
0.8487	Intermediate Similarity	NPC156892
0.8485	Intermediate Similarity	NPC291957
0.8485	Intermediate Similarity	NPC476372
0.8485	Intermediate Similarity	NPC476371
0.8485	Intermediate Similarity	NPC14030
0.8481	Intermediate Similarity	NPC43123
0.8481	Intermediate Similarity	NPC81835
0.8476	Intermediate Similarity	NPC476373
0.8476	Intermediate Similarity	NPC472055
0.8475	Intermediate Similarity	NPC476358
0.8471	Intermediate Similarity	NPC469354
0.8471	Intermediate Similarity	NPC66894
0.8471	Intermediate Similarity	NPC8102
0.8471	Intermediate Similarity	NPC294149
0.8466	Intermediate Similarity	NPC238419
0.8466	Intermediate Similarity	NPC172419
0.8452	Intermediate Similarity	NPC476017
0.8442	Intermediate Similarity	NPC75763
0.8442	Intermediate Similarity	NPC225036
0.8442	Intermediate Similarity	NPC12218
0.8442	Intermediate Similarity	NPC105525
0.8438	Intermediate Similarity	NPC473680
0.8438	Intermediate Similarity	NPC225854
0.8438	Intermediate Similarity	NPC473579
0.8438	Intermediate Similarity	NPC475454
0.8438	Intermediate Similarity	NPC475311
0.8438	Intermediate Similarity	NPC252979
0.8434	Intermediate Similarity	NPC470898
0.8434	Intermediate Similarity	NPC100420
0.8431	Intermediate Similarity	NPC22676
0.8431	Intermediate Similarity	NPC198621
0.8431	Intermediate Similarity	NPC216940
0.8431	Intermediate Similarity	NPC475482
0.8428	Intermediate Similarity	NPC42464
0.8421	Intermediate Similarity	NPC478050
0.8421	Intermediate Similarity	NPC472723
0.8421	Intermediate Similarity	NPC18646
0.8415	Intermediate Similarity	NPC471750
0.8415	Intermediate Similarity	NPC470339
0.8415	Intermediate Similarity	NPC87317
0.8412	Intermediate Similarity	NPC469393
0.8405	Intermediate Similarity	NPC104983
0.8405	Intermediate Similarity	NPC318432
0.8405	Intermediate Similarity	NPC300845
0.8405	Intermediate Similarity	NPC291948
0.8405	Intermediate Similarity	NPC471968
0.8405	Intermediate Similarity	NPC88803
0.8405	Intermediate Similarity	NPC250436
0.8402	Intermediate Similarity	NPC475058
0.8402	Intermediate Similarity	NPC193698
0.8397	Intermediate Similarity	NPC235557
0.8397	Intermediate Similarity	NPC184935
0.8395	Intermediate Similarity	NPC116850
0.8395	Intermediate Similarity	NPC144801
0.8395	Intermediate Similarity	NPC238672
0.8395	Intermediate Similarity	NPC291510
0.8395	Intermediate Similarity	NPC197188
0.8395	Intermediate Similarity	NPC43872
0.8393	Intermediate Similarity	NPC107009
0.8383	Intermediate Similarity	NPC471788
0.8375	Intermediate Similarity	NPC35160
0.8375	Intermediate Similarity	NPC162569
0.8375	Intermediate Similarity	NPC267469
0.8375	Intermediate Similarity	NPC116292
0.8375	Intermediate Similarity	NPC179128
0.8375	Intermediate Similarity	NPC87630
0.8373	Intermediate Similarity	NPC149389
0.8373	Intermediate Similarity	NPC473445
0.8366	Intermediate Similarity	NPC249817
0.8365	Intermediate Similarity	NPC248257
0.8365	Intermediate Similarity	NPC127046
0.8365	Intermediate Similarity	NPC120621
0.8364	Intermediate Similarity	NPC24164
0.8364	Intermediate Similarity	NPC53889
0.8354	Intermediate Similarity	NPC114179
0.8354	Intermediate Similarity	NPC474010
0.8354	Intermediate Similarity	NPC289322
0.8354	Intermediate Similarity	NPC160512
0.8354	Intermediate Similarity	NPC135222
0.8354	Intermediate Similarity	NPC38779
0.8354	Intermediate Similarity	NPC84786
0.8354	Intermediate Similarity	NPC68324
0.8354	Intermediate Similarity	NPC156818
0.8353	Intermediate Similarity	NPC135334
0.8353	Intermediate Similarity	NPC469773
0.8353	Intermediate Similarity	NPC469776
0.8353	Intermediate Similarity	NPC469778
0.8353	Intermediate Similarity	NPC469775
0.8353	Intermediate Similarity	NPC469777
0.8353	Intermediate Similarity	NPC472620
0.8353	Intermediate Similarity	NPC469772
0.8353	Intermediate Similarity	NPC295941
0.8353	Intermediate Similarity	NPC469774
0.8353	Intermediate Similarity	NPC100925
0.8353	Intermediate Similarity	NPC32723
0.8344	Intermediate Similarity	NPC26045
0.8344	Intermediate Similarity	NPC50221
0.8344	Intermediate Similarity	NPC114242
0.8333	Intermediate Similarity	NPC44260
0.8333	Intermediate Similarity	NPC205037
0.8333	Intermediate Similarity	NPC178574
0.8333	Intermediate Similarity	NPC16024
0.8333	Intermediate Similarity	NPC65591
0.8333	Intermediate Similarity	NPC207575
0.8333	Intermediate Similarity	NPC13481
0.8333	Intermediate Similarity	NPC472621
0.8333	Intermediate Similarity	NPC61152
0.8333	Intermediate Similarity	NPC180944
0.8333	Intermediate Similarity	NPC3746
0.8323	Intermediate Similarity	NPC256142
0.8323	Intermediate Similarity	NPC304876
0.8323	Intermediate Similarity	NPC472005
0.8323	Intermediate Similarity	NPC1173

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 NPC266365 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	922
0.2-0.3	1782
0.3-0.4	2719
0.4-0.5	2015
0.5-0.6	968
0.6-0.7	323
0.7-0.8	91
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD8166	Discontinued
0.8405	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD230	Phase 1
0.8246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7228	Approved
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6234	Discontinued
0.7941	Intermediate Similarity	NPD6232	Discontinued
0.7937	Intermediate Similarity	NPD6190	Approved
0.791	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD37	Approved
0.7865	Intermediate Similarity	NPD8150	Discontinued
0.7857	Intermediate Similarity	NPD4967	Phase 2
0.7857	Intermediate Similarity	NPD4966	Approved
0.7857	Intermediate Similarity	NPD4965	Approved
0.7849	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6166	Phase 2
0.7849	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD1465	Phase 2
0.7844	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8127	Discontinued
0.7771	Intermediate Similarity	NPD7074	Phase 3
0.7738	Intermediate Similarity	NPD7819	Suspended
0.7714	Intermediate Similarity	NPD7054	Approved
0.7692	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1934	Approved
0.7674	Intermediate Similarity	NPD6959	Discontinued
0.767	Intermediate Similarity	NPD7472	Approved
0.7665	Intermediate Similarity	NPD4380	Phase 2
0.7657	Intermediate Similarity	NPD3818	Discontinued
0.7654	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7605	Intermediate Similarity	NPD7458	Discontinued
0.7602	Intermediate Similarity	NPD7075	Discontinued
0.7598	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD8313	Approved
0.7588	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7251	Discontinued
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7584	Intermediate Similarity	NPD7240	Approved
0.7576	Intermediate Similarity	NPD2533	Approved
0.7576	Intermediate Similarity	NPD2534	Approved
0.7576	Intermediate Similarity	NPD2532	Approved
0.7576	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8434	Phase 2
0.7566	Intermediate Similarity	NPD9269	Phase 2
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7544	Intermediate Similarity	NPD7768	Phase 2
0.7543	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7808	Phase 3
0.7531	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2801	Approved
0.7528	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7469	Intermediate Similarity	NPD7266	Discontinued
0.7442	Intermediate Similarity	NPD3882	Suspended
0.7439	Intermediate Similarity	NPD3750	Approved
0.7439	Intermediate Similarity	NPD7003	Approved
0.7427	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6273	Approved
0.7421	Intermediate Similarity	NPD943	Approved
0.7416	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5494	Approved
0.7412	Intermediate Similarity	NPD7411	Suspended
0.741	Intermediate Similarity	NPD1511	Approved
0.7399	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD6801	Discontinued
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6599	Discontinued
0.7349	Intermediate Similarity	NPD7236	Approved
0.7346	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8319	Approved
0.7344	Intermediate Similarity	NPD8320	Phase 1
0.7321	Intermediate Similarity	NPD1512	Approved
0.7303	Intermediate Similarity	NPD9268	Approved
0.7301	Intermediate Similarity	NPD6100	Approved
0.7301	Intermediate Similarity	NPD6099	Approved
0.7296	Intermediate Similarity	NPD3764	Approved
0.7283	Intermediate Similarity	NPD5402	Approved
0.7263	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7239	Suspended
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7202	Intermediate Similarity	NPD7680	Approved
0.7202	Intermediate Similarity	NPD7435	Discontinued
0.7198	Intermediate Similarity	NPD6559	Discontinued
0.7195	Intermediate Similarity	NPD5408	Approved
0.7195	Intermediate Similarity	NPD5404	Approved
0.7195	Intermediate Similarity	NPD5406	Approved
0.7195	Intermediate Similarity	NPD5405	Approved
0.7193	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5353	Approved
0.7169	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD6535	Approved
0.7134	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD1510	Phase 2
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.7125	Intermediate Similarity	NPD3027	Phase 3
0.7124	Intermediate Similarity	NPD9545	Approved
0.7117	Intermediate Similarity	NPD6651	Approved
0.7112	Intermediate Similarity	NPD8361	Approved
0.7112	Intermediate Similarity	NPD8360	Approved
0.7108	Intermediate Similarity	NPD1549	Phase 2
0.7107	Intermediate Similarity	NPD5736	Approved
0.7104	Intermediate Similarity	NPD8368	Discontinued
0.7102	Intermediate Similarity	NPD3749	Approved
0.7101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6799	Approved
0.7093	Intermediate Similarity	NPD3226	Approved
0.7091	Intermediate Similarity	NPD2935	Discontinued
0.7081	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7871	Phase 2
0.7077	Intermediate Similarity	NPD7870	Phase 2
0.7076	Intermediate Similarity	NPD5403	Approved
0.7072	Intermediate Similarity	NPD7799	Discontinued
0.7072	Intermediate Similarity	NPD3751	Discontinued
0.7071	Intermediate Similarity	NPD7874	Approved
0.7071	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD8485	Approved
0.7066	Intermediate Similarity	NPD2800	Approved
0.7048	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6777	Approved
0.7047	Intermediate Similarity	NPD6779	Approved
0.7047	Intermediate Similarity	NPD6776	Approved
0.7047	Intermediate Similarity	NPD6780	Approved
0.7047	Intermediate Similarity	NPD6778	Approved
0.7047	Intermediate Similarity	NPD6781	Approved
0.7047	Intermediate Similarity	NPD6782	Approved
0.7039	Intermediate Similarity	NPD5711	Approved
0.7039	Intermediate Similarity	NPD7229	Phase 3
0.7039	Intermediate Similarity	NPD5710	Approved
0.7035	Intermediate Similarity	NPD1653	Approved
0.7033	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5760	Phase 2
0.7029	Intermediate Similarity	NPD5761	Phase 2
0.7026	Intermediate Similarity	NPD7697	Approved
0.7026	Intermediate Similarity	NPD7698	Approved
0.7026	Intermediate Similarity	NPD7696	Phase 3
0.7026	Intermediate Similarity	NPD7497	Discontinued
0.7021	Intermediate Similarity	NPD8435	Approved
0.7012	Intermediate Similarity	NPD1607	Approved
0.7005	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5242	Approved
0.6994	Remote Similarity	NPD1240	Approved
0.6994	Remote Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8407	Phase 2
0.6988	Remote Similarity	NPD2796	Approved
0.6975	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7701	Phase 2
0.6959	Remote Similarity	NPD5401	Approved
0.6959	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7783	Phase 2
0.695	Remote Similarity	NPD7801	Approved
0.695	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3787	Discontinued
0.6937	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6213	Phase 3
0.6911	Remote Similarity	NPD6212	Phase 3
0.6911	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3455	Phase 2
0.6894	Remote Similarity	NPD9494	Approved
0.6891	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3620	Phase 2
0.689	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6823	Phase 2
0.6886	Remote Similarity	NPD1551	Phase 2
0.6867	Remote Similarity	NPD7097	Phase 1
0.6854	Remote Similarity	NPD7058	Phase 2
0.6854	Remote Similarity	NPD7057	Phase 3
0.6824	Remote Similarity	NPD4110	Phase 3
0.6824	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6386	Approved
0.6818	Remote Similarity	NPD6385	Approved
0.6818	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7008	Discontinued
0.681	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7177	Discontinued
0.679	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD919	Approved
0.6774	Remote Similarity	NPD5953	Discontinued
0.677	Remote Similarity	NPD3094	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