NPASS Compound

Structure

CID138219 OpenBabel06191715492D 74 83 0 0 1 0 0 0 0 0999 V2000 2.5074 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5074 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2188 -4.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3838 -0.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2705 -2.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0504 -0.7523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -3.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6310 -1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0074 -1.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1365 -2.6587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1365 -0.4984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 -2.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8647 -1.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0256 -2.6044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0501 -2.0275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 1.8413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4252 -1.1587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8271 -5.6587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0951 -2.6587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2260 -4.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -6.1587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3630 1.3413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5592 -1.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0951 -1.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3838 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7601 -1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1450 -1.6115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7521 -1.8673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6310 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0951 -5.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4970 1.8413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5592 -2.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2291 -1.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6310 1.3413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6932 -3.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0951 -4.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6310 0.3413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3630 -1.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8271 -2.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9611 -4.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4970 -0.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3630 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8271 -1.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0074 -3.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8258 -3.2042 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3838 -1.9386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1365 -1.9386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 -1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0646 -1.2185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 -0.8584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2291 2.8413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2912 -1.6587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6190 -4.9239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -7.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3756 -2.6491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -6.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 2.8413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4252 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -0.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7650 1.8413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6932 -4.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -4.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7650 -0.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8271 -4.6587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3630 0.3413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6932 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 46 1 0 0 0 0 2 46 1 0 0 0 0 5 49 1 0 0 0 0 6 50 1 0 0 0 0 7 11 1 0 0 0 0 7 27 1 0 0 0 0 8 12 1 0 0 0 0 8 28 1 0 0 0 0 9 10 1 0 0 0 0 9 31 1 0 0 0 0 10 48 1 0 0 0 0 11 49 1 0 0 0 0 13 14 1 0 0 0 0 13 47 1 0 0 0 0 15 29 1 0 0 0 0 15 47 1 0 0 0 0 16 30 1 0 0 0 0 16 50 1 0 0 0 0 17 53 1 0 0 0 0 18 54 1 0 0 0 0 19 23 1 0 0 0 0 19 66 1 0 0 0 0 20 26 1 0 0 0 0 20 67 1 0 0 0 0 21 47 1 0 0 0 0 21 55 2 0 0 0 0 22 51 1 0 0 0 0 22 68 1 0 0 0 0 23 32 1 0 0 0 0 23 56 1 1 0 0 0 24 17 1 1 0 0 0 24 33 1 0 0 0 0 24 69 1 0 0 0 0 25 18 1 6 0 0 0 25 34 1 0 0 0 0 25 70 1 0 0 0 0 26 35 1 0 0 0 0 26 71 1 1 0 0 0 27 46 1 0 0 0 0 27 48 1 6 0 0 0 28 48 1 6 0 0 0 28 49 1 0 0 0 0 29 51 1 6 0 0 0 29 52 1 0 0 0 0 30 51 1 1 0 0 0 30 57 1 0 0 0 0 31 46 1 0 0 0 0 31 72 1 6 0 0 0 32 38 1 0 0 0 0 32 58 1 6 0 0 0 33 36 1 0 0 0 0 33 59 1 6 0 0 0 34 37 1 0 0 0 0 34 60 1 1 0 0 0 35 40 1 0 0 0 0 35 61 1 1 0 0 0 36 39 1 0 0 0 0 36 62 1 1 0 0 0 37 41 1 0 0 0 0 37 63 1 6 0 0 0 38 42 1 0 0 0 0 38 64 1 1 0 0 0 39 43 1 0 0 0 0 39 65 1 6 0 0 0 40 44 1 0 0 0 0 40 74 1 6 0 0 0 41 45 1 0 0 0 0 41 73 1 1 0 0 0 42 66 1 0 0 0 0 42 73 1 6 0 0 0 43 69 1 0 0 0 0 43 74 1 1 0 0 0 44 67 1 0 0 0 0 44 72 1 1 0 0 0 45 70 1 0 0 0 0 45 71 1 6 0 0 0 47 3 1 6 0 0 0 48 4 1 6 0 0 0 49 50 1 1 0 0 0 50 52 1 6 0 0 0 51 14 1 1 0 0 0 52 12 1 1 0 0 0 52 68 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1060.55
Volume:	1013.132
LogP:	0.462
LogD:	1.329
LogS:	-3.546
# Rotatable Bonds:	11
TPSA:	342.9
# H-Bond Aceptor:	22
# H-Bond Donor:	12
# Rings:	10
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.079
Synthetic Accessibility Score:	5.286
Fsp3:	0.981
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.306
MDCK Permeability:	4.674035881180316e-05
Pgp-inhibitor:	0.079
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	48.105918884277344%
Volume Distribution (VD):	0.313
Pgp-substrate:	21.66269874572754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.133
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	0.209
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.399
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.005
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.901
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC138219

Natural Product ID:	NPC138219
*Common Name:**	Ardisiacrispin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JXTOWLUQSHIIDP-VKKSEJOZSA-N
Standard InCHI:	InChI=1S/C52H84O22/c1-46(2)27-7-11-49(5)28(8-12-52-29-15-47(3,21-55)13-14-51(29,22-68-52)30(57)16-50(49,52)6)48(27,4)10-9-31(46)72-44-40(74-43-39(65)36(62)33(59)24(17-53)69-43)35(61)26(20-67-44)71-45-41(37(63)34(60)25(18-54)70-45)73-42-38(64)32(58)23(56)19-66-42/h21,23-45,53-54,56-65H,7-20,22H2,1-6H3/t23-,24-,25-,26+,27+,28-,29-,30-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,47+,48+,49-,50+,51-,52+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@]34[C@@]2(C)C[C@H]([C@@]2([C@H]4C[C@@](C)(C=O)CC2)CO3)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500261
PubChem CID:	10328746
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
NPO26639	Ardisia crenata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11230	Herba glechomae longitubae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO26639	Ardisia crenata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26639	Ardisia crenata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26639	Ardisia crenata	Species	Primulaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ID50	=	7.0	ug ml-1	PMID[470859]

☑ 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 NPC138219 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	514
0.1-0.2	3919
0.2-0.3	9501
0.3-0.4	13093
0.4-0.5	6956
0.5-0.6	4375
0.6-0.7	2380
0.7-0.8	1673
0.8-0.85	202
0.85-0.9	57
0.9-0.95	11
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475630
1.0	High Similarity	NPC475234
1.0	High Similarity	NPC40716
0.9899	High Similarity	NPC231566
0.9899	High Similarity	NPC471626
0.9899	High Similarity	NPC473688
0.9899	High Similarity	NPC262567
0.9898	High Similarity	NPC119628
0.9898	High Similarity	NPC158367
0.9898	High Similarity	NPC158051
0.9703	High Similarity	NPC471431
0.96	High Similarity	NPC126753
0.9515	High Similarity	NPC157571
0.951	High Similarity	NPC66513
0.9412	High Similarity	NPC87393
0.9135	High Similarity	NPC470622
0.9126	High Similarity	NPC207693
0.9118	High Similarity	NPC184805
0.9118	High Similarity	NPC273189
0.9038	High Similarity	NPC22709
0.9029	High Similarity	NPC471430
0.902	High Similarity	NPC267637
0.89	High Similarity	NPC209798
0.89	High Similarity	NPC471374
0.89	High Similarity	NPC471375
0.8878	High Similarity	NPC148593
0.8878	High Similarity	NPC267238
0.8878	High Similarity	NPC77717
0.8878	High Similarity	NPC253611
0.8878	High Similarity	NPC471373
0.8824	High Similarity	NPC80640
0.8812	High Similarity	NPC471427
0.8812	High Similarity	NPC51579
0.8812	High Similarity	NPC471426
0.8812	High Similarity	NPC471428
0.8796	High Similarity	NPC477465
0.8788	High Similarity	NPC205129
0.8788	High Similarity	NPC189575
0.8788	High Similarity	NPC471425
0.8788	High Similarity	NPC106701
0.8788	High Similarity	NPC471424
0.8788	High Similarity	NPC471429
0.8776	High Similarity	NPC323231
0.8776	High Similarity	NPC171741
0.8776	High Similarity	NPC470623
0.8776	High Similarity	NPC18724
0.8776	High Similarity	NPC224003
0.8762	High Similarity	NPC469826
0.8627	High Similarity	NPC80417
0.8585	High Similarity	NPC92890
0.8585	High Similarity	NPC202898
0.8585	High Similarity	NPC475319
0.8519	High Similarity	NPC469824
0.8505	High Similarity	NPC92297
0.8505	High Similarity	NPC233433
0.8505	High Similarity	NPC228190
0.8505	High Similarity	NPC220836
0.8505	High Similarity	NPC236753
0.8505	High Similarity	NPC273002
0.8505	High Similarity	NPC473817
0.8505	High Similarity	NPC94086
0.8476	Intermediate Similarity	NPC469827
0.844	Intermediate Similarity	NPC477492
0.8396	Intermediate Similarity	NPC215408
0.8365	Intermediate Similarity	NPC477172
0.8333	Intermediate Similarity	NPC469825
0.8318	Intermediate Similarity	NPC203974
0.8304	Intermediate Similarity	NPC179429
0.8286	Intermediate Similarity	NPC80191
0.8286	Intermediate Similarity	NPC310031
0.8252	Intermediate Similarity	NPC472273
0.8208	Intermediate Similarity	NPC34562
0.8137	Intermediate Similarity	NPC305418
0.8125	Intermediate Similarity	NPC79193
0.8108	Intermediate Similarity	NPC477489
0.8095	Intermediate Similarity	NPC20028
0.807	Intermediate Similarity	NPC475899
0.8058	Intermediate Similarity	NPC477494
0.8053	Intermediate Similarity	NPC137414
0.802	Intermediate Similarity	NPC50443
0.802	Intermediate Similarity	NPC18536
0.8018	Intermediate Similarity	NPC1876
0.8018	Intermediate Similarity	NPC91838
0.8018	Intermediate Similarity	NPC275668
0.8018	Intermediate Similarity	NPC240734
0.8018	Intermediate Similarity	NPC204392
0.8	Intermediate Similarity	NPC477464
0.8	Intermediate Similarity	NPC472144
0.7981	Intermediate Similarity	NPC237071
0.7981	Intermediate Similarity	NPC139271
0.7981	Intermediate Similarity	NPC203434
0.7981	Intermediate Similarity	NPC304011
0.7981	Intermediate Similarity	NPC475765
0.7981	Intermediate Similarity	NPC475785
0.7981	Intermediate Similarity	NPC238796
0.7965	Intermediate Similarity	NPC469821
0.7963	Intermediate Similarity	NPC470167
0.7941	Intermediate Similarity	NPC210759
0.7941	Intermediate Similarity	NPC307167
0.7941	Intermediate Similarity	NPC229801
0.7931	Intermediate Similarity	NPC110385
0.7931	Intermediate Similarity	NPC153673
0.7931	Intermediate Similarity	NPC267694
0.7931	Intermediate Similarity	NPC144644
0.7931	Intermediate Similarity	NPC142151
0.7931	Intermediate Similarity	NPC37860
0.7925	Intermediate Similarity	NPC41843
0.7921	Intermediate Similarity	NPC131466
0.7913	Intermediate Similarity	NPC469822
0.7913	Intermediate Similarity	NPC473459
0.7905	Intermediate Similarity	NPC476112
0.7905	Intermediate Similarity	NPC307534
0.7905	Intermediate Similarity	NPC274200
0.7905	Intermediate Similarity	NPC470591
0.7905	Intermediate Similarity	NPC472145
0.7895	Intermediate Similarity	NPC472718
0.7885	Intermediate Similarity	NPC473727
0.7885	Intermediate Similarity	NPC473610
0.7885	Intermediate Similarity	NPC19400
0.7885	Intermediate Similarity	NPC107962
0.7885	Intermediate Similarity	NPC94582
0.7885	Intermediate Similarity	NPC107188
0.7885	Intermediate Similarity	NPC475351
0.7885	Intermediate Similarity	NPC57964
0.7885	Intermediate Similarity	NPC206003
0.7885	Intermediate Similarity	NPC211354
0.7885	Intermediate Similarity	NPC6295
0.7876	Intermediate Similarity	NPC146563
0.7876	Intermediate Similarity	NPC114304
0.7876	Intermediate Similarity	NPC174720
0.7876	Intermediate Similarity	NPC192600
0.7876	Intermediate Similarity	NPC151543
0.7876	Intermediate Similarity	NPC133818
0.7876	Intermediate Similarity	NPC323341
0.7876	Intermediate Similarity	NPC219180
0.7876	Intermediate Similarity	NPC241909
0.7876	Intermediate Similarity	NPC473826
0.7876	Intermediate Similarity	NPC166422
0.7876	Intermediate Similarity	NPC475287
0.7876	Intermediate Similarity	NPC155410
0.7876	Intermediate Similarity	NPC251263
0.7876	Intermediate Similarity	NPC309714
0.7876	Intermediate Similarity	NPC295823
0.7876	Intermediate Similarity	NPC46665
0.7876	Intermediate Similarity	NPC114287
0.7876	Intermediate Similarity	NPC475467
0.787	Intermediate Similarity	NPC107385
0.7864	Intermediate Similarity	NPC172838
0.7864	Intermediate Similarity	NPC137004
0.7863	Intermediate Similarity	NPC477463
0.7863	Intermediate Similarity	NPC293031
0.7863	Intermediate Similarity	NPC470478
0.7863	Intermediate Similarity	NPC68767
0.7863	Intermediate Similarity	NPC275225
0.7863	Intermediate Similarity	NPC51099
0.7857	Intermediate Similarity	NPC473062
0.785	Intermediate Similarity	NPC475574
0.7845	Intermediate Similarity	NPC473386
0.7845	Intermediate Similarity	NPC207738
0.7845	Intermediate Similarity	NPC25663
0.7845	Intermediate Similarity	NPC51564
0.7845	Intermediate Similarity	NPC135849
0.7843	Intermediate Similarity	NPC185529
0.7843	Intermediate Similarity	NPC472146
0.7838	Intermediate Similarity	NPC473844
0.7838	Intermediate Similarity	NPC51947
0.783	Intermediate Similarity	NPC473518
0.7826	Intermediate Similarity	NPC323359
0.7826	Intermediate Similarity	NPC68175
0.7815	Intermediate Similarity	NPC160452
0.781	Intermediate Similarity	NPC116756
0.781	Intermediate Similarity	NPC160426
0.781	Intermediate Similarity	NPC30856
0.781	Intermediate Similarity	NPC473601
0.781	Intermediate Similarity	NPC103616
0.781	Intermediate Similarity	NPC475625
0.781	Intermediate Similarity	NPC470865
0.781	Intermediate Similarity	NPC235109
0.781	Intermediate Similarity	NPC284104
0.781	Intermediate Similarity	NPC470866
0.781	Intermediate Similarity	NPC475643
0.781	Intermediate Similarity	NPC195297
0.781	Intermediate Similarity	NPC128572
0.781	Intermediate Similarity	NPC232037
0.781	Intermediate Similarity	NPC470864
0.781	Intermediate Similarity	NPC287483
0.781	Intermediate Similarity	NPC470863
0.781	Intermediate Similarity	NPC97700
0.781	Intermediate Similarity	NPC98018
0.781	Intermediate Similarity	NPC132080
0.781	Intermediate Similarity	NPC184617
0.781	Intermediate Similarity	NPC121453
0.781	Intermediate Similarity	NPC84111
0.7807	Intermediate Similarity	NPC475140
0.7807	Intermediate Similarity	NPC298034
0.7807	Intermediate Similarity	NPC65105
0.7807	Intermediate Similarity	NPC305981
0.7807	Intermediate Similarity	NPC70809
0.7807	Intermediate Similarity	NPC294453
0.7807	Intermediate Similarity	NPC204414

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 NPC138219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	557
0.1-0.2	3987
0.2-0.3	3154
0.3-0.4	788
0.4-0.5	371
0.5-0.6	217
0.6-0.7	60
0.7-0.8	14
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8476	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8133	Approved
0.7692	Intermediate Similarity	NPD8171	Discontinued
0.7521	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD8328	Phase 3
0.7217	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7507	Approved
0.6875	Remote Similarity	NPD7319	Approved
0.672	Remote Similarity	NPD8517	Approved
0.672	Remote Similarity	NPD8516	Approved
0.672	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3669	Approved
0.664	Remote Similarity	NPD8294	Approved
0.664	Remote Similarity	NPD8377	Approved
0.6635	Remote Similarity	NPD1779	Approved
0.6635	Remote Similarity	NPD1780	Approved
0.661	Remote Similarity	NPD6412	Phase 2
0.6587	Remote Similarity	NPD8513	Phase 3
0.6587	Remote Similarity	NPD8296	Approved
0.6587	Remote Similarity	NPD8380	Approved
0.6587	Remote Similarity	NPD8379	Approved
0.6587	Remote Similarity	NPD8378	Approved
0.6587	Remote Similarity	NPD8335	Approved
0.6585	Remote Similarity	NPD6940	Discontinued
0.6555	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6928	Phase 2
0.6538	Remote Similarity	NPD7736	Approved
0.6535	Remote Similarity	NPD3703	Phase 2
0.6505	Remote Similarity	NPD6697	Approved
0.6505	Remote Similarity	NPD6118	Approved
0.6505	Remote Similarity	NPD6115	Approved
0.6505	Remote Similarity	NPD6114	Approved
0.6457	Remote Similarity	NPD8033	Approved
0.6436	Remote Similarity	NPD1810	Approved
0.6436	Remote Similarity	NPD1811	Approved
0.6417	Remote Similarity	NPD6686	Approved
0.6408	Remote Similarity	NPD6116	Phase 1
0.6406	Remote Similarity	NPD6370	Approved
0.6349	Remote Similarity	NPD7327	Approved
0.6349	Remote Similarity	NPD7328	Approved
0.6336	Remote Similarity	NPD8293	Discontinued
0.6311	Remote Similarity	NPD6117	Approved
0.6299	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6059	Approved
0.6195	Remote Similarity	NPD8035	Phase 2
0.6195	Remote Similarity	NPD8034	Phase 2
0.6139	Remote Similarity	NPD2687	Approved
0.6139	Remote Similarity	NPD2686	Approved
0.6139	Remote Similarity	NPD2254	Approved
0.6139	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8083	Approved
0.6134	Remote Similarity	NPD8084	Approved
0.6134	Remote Similarity	NPD8138	Approved
0.6134	Remote Similarity	NPD8139	Approved
0.6134	Remote Similarity	NPD8085	Approved
0.6134	Remote Similarity	NPD8086	Approved
0.6134	Remote Similarity	NPD8082	Approved
0.6132	Remote Similarity	NPD7329	Approved
0.6129	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8393	Approved
0.6098	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8275	Approved
0.6083	Remote Similarity	NPD8276	Approved
0.6078	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6015	Approved
0.6077	Remote Similarity	NPD6016	Approved
0.6077	Remote Similarity	NPD6921	Approved
0.6061	Remote Similarity	NPD7492	Approved
0.605	Remote Similarity	NPD1700	Approved
0.604	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8081	Approved
0.6031	Remote Similarity	NPD5988	Approved
0.6019	Remote Similarity	NPD3181	Approved
0.6015	Remote Similarity	NPD6616	Approved
0.597	Remote Similarity	NPD7078	Approved
0.5954	Remote Similarity	NPD7503	Approved
0.5952	Remote Similarity	NPD8297	Approved
0.5952	Remote Similarity	NPD6882	Approved
0.5948	Remote Similarity	NPD7748	Approved
0.5946	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8307	Discontinued
0.5935	Remote Similarity	NPD8140	Approved
0.5932	Remote Similarity	NPD7902	Approved
0.592	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD3702	Approved
0.5902	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7991	Discontinued
0.5891	Remote Similarity	NPD6009	Approved
0.5878	Remote Similarity	NPD6319	Approved
0.5865	Remote Similarity	NPD6067	Discontinued
0.584	Remote Similarity	NPD8306	Approved
0.584	Remote Similarity	NPD8305	Approved
0.5825	Remote Similarity	NPD4244	Approved
0.5825	Remote Similarity	NPD4245	Approved
0.5809	Remote Similarity	NPD6033	Approved
0.5794	Remote Similarity	NPD8087	Discontinued
0.5784	Remote Similarity	NPD5360	Phase 3
0.5784	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD4632	Approved
0.5776	Remote Similarity	NPD7515	Phase 2
0.5735	Remote Similarity	NPD8074	Phase 3
0.5728	Remote Similarity	NPD3698	Phase 2
0.5726	Remote Similarity	NPD6675	Approved
0.5726	Remote Similarity	NPD5739	Approved
0.5726	Remote Similarity	NPD7128	Approved
0.5726	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD6123	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD8450	Suspended
0.5714	Remote Similarity	NPD6372	Approved
0.57	Remote Similarity	NPD371	Approved
0.568	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD7900	Approved
0.5673	Remote Similarity	NPD4789	Approved
0.5649	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD8449	Approved
0.5639	Remote Similarity	NPD8347	Approved
0.5639	Remote Similarity	NPD8346	Approved
0.5639	Remote Similarity	NPD8345	Approved
0.5635	Remote Similarity	NPD6899	Approved
0.5635	Remote Similarity	NPD8174	Phase 2
0.5635	Remote Similarity	NPD6881	Approved
0.5635	Remote Similarity	NPD7320	Approved
0.5625	Remote Similarity	NPD8130	Phase 1
0.5625	Remote Similarity	NPD6650	Approved
0.5625	Remote Similarity	NPD6649	Approved
0.562	Remote Similarity	NPD7638	Approved
0.5619	Remote Similarity	NPD5777	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