NPASS Compound

Structure

NPC471850 OpenBabel07101719132D 57 66 0 0 1 0 0 0 0 0999 V2000 -3.3468 -0.7337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8514 -1.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4495 -2.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8514 -4.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7796 0.8006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7796 -0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9136 1.3006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9136 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0475 0.8006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5169 -2.2472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9182 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1047 -3.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5060 -2.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5834 -0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3218 -2.1168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9854 -1.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7174 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1193 -2.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7285 -3.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3155 -0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3414 -0.6292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5834 -3.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 -1.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1193 -4.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1444 0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3155 -2.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9237 -1.3337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0475 -0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4495 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0992 -2.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 -2.2213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3359 -0.5247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1815 -0.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8514 -2.1994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5834 -2.1994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7174 -3.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9346 -1.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 -0.8383 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7174 -1.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4495 -1.6994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8514 -3.1994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1193 -3.1994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9854 -3.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6870 -3.7607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7426 0.3889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7174 -4.6994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5224 -2.3518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1815 -1.6994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1499 0.2444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 -1.6473 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 4 44 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 28 2 0 0 0 0 9 28 1 0 0 0 0 10 12 1 0 0 0 0 10 27 2 0 0 0 0 11 13 2 0 0 0 0 11 27 1 0 0 0 0 12 30 2 0 0 0 0 13 30 1 0 0 0 0 14 17 1 0 0 0 0 14 29 2 0 0 0 0 15 19 1 0 0 0 0 15 31 1 0 0 0 0 16 18 2 0 0 0 0 16 34 1 0 0 0 0 17 42 1 0 0 0 0 18 45 1 0 0 0 0 20 29 1 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 21 37 1 0 0 0 0 22 35 1 0 0 0 0 22 36 1 0 0 0 0 23 41 1 0 0 0 0 24 45 1 0 0 0 0 24 46 1 0 0 0 0 25 41 1 0 0 0 0 25 55 1 0 0 0 0 26 43 1 0 0 0 0 26 54 1 0 0 0 0 27 32 1 0 0 0 0 29 43 1 0 0 0 0 30 48 1 0 0 0 0 31 38 1 0 0 0 0 31 45 1 6 0 0 0 32 49 1 6 0 0 0 33 28 1 1 0 0 0 33 54 1 0 0 0 0 34 42 1 6 0 0 0 34 44 1 0 0 0 0 35 42 1 6 0 0 0 35 43 1 0 0 0 0 36 44 1 0 0 0 0 36 50 2 0 0 0 0 37 51 2 0 0 0 0 37 56 1 0 0 0 0 38 39 1 0 0 0 0 38 40 1 6 0 0 0 39 47 1 1 0 0 0 39 52 1 0 0 0 0 40 53 2 0 0 0 0 40 57 1 0 0 0 0 41 1 1 6 0 0 0 41 56 1 0 0 0 0 42 2 1 6 0 0 0 43 3 1 1 0 0 0 44 46 1 1 0 0 0 45 46 1 1 0 0 0 46 19 1 6 0 0 0 47 23 1 6 0 0 0 47 55 1 0 0 0 0 47 57 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	778.37
Volume:	794.804
LogP:	4.154
LogD:	2.84
LogS:	-4.936
# Rotatable Bonds:	7
TPSA:	148.82
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	10
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	6.664
Fsp3:	0.596
Lipinski Rule-of-5:	Accepted
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:	-5.418
MDCK Permeability:	1.6370491721318103e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.186

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	86.5174789428711%
Volume Distribution (VD):	0.668
Pgp-substrate:	7.799468994140625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.544
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.617
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.958
CYP3A4-substrate:	0.844

ADMET: Excretion

Clearance (CL):	9.478
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.648
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.124
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.159
Carcinogencity:	0.216
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.844

Download Data

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

Natural Product: NPC471850

Natural Product ID:	NPC471850
*Common Name:**	RFQHTJUTEVSXAZ-CXADFGQHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RFQHTJUTEVSXAZ-CXADFGQHSA-N
Standard InCHI:	InChI=1S/C47H54O10/c1-41(56-37(51)21-32(49)27-10-12-30(48)13-11-27)23-47(55-25-41)39(52)38(40(53)57-47)31-15-19-46-24-45(31,46)18-16-34-42(2)17-14-29-20-33(28-8-6-5-7-9-28)54-26-43(29,3)35(42)22-36(50)44(34,46)4/h5-14,16,18,31-35,38-39,48-49,52H,15,17,19-26H2,1-4H3/t31-,32+,33-,34+,35+,38+,39+,41+,42+,43-,44-,45+,46+,47-/m0/s1
SMILES:	O=C(O[C@@]1(C)CO[C@@]2(C1)OC(=O)[C@@H]([C@H]2O)[C@@H]1CC[C@@]23[C@]1(C=C[C@H]1[C@@]3(C)C(=O)C[C@@H]3[C@]1(C)CC=C1[C@]3(C)CO[C@@H](C1)c1ccccc1)C2)C[C@H](c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3259841
PubChem CID:	90676172
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
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5100.0	nM	PMID[547090]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	18700.0	nM	PMID[547090]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3000.0	nM	PMID[547090]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3500.0	nM	PMID[547090]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	21000.0	nM	PMID[547090]

☑ 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 NPC471850 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	376
0.1-0.2	1291
0.2-0.3	2838
0.3-0.4	5181
0.4-0.5	10363
0.5-0.6	13511
0.6-0.7	8100
0.7-0.8	1019
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC471858
0.962	High Similarity	NPC471859
0.9554	High Similarity	NPC471861
0.9497	High Similarity	NPC471860
0.875	High Similarity	NPC475244
0.8693	High Similarity	NPC471856
0.8627	High Similarity	NPC471862
0.8393	Intermediate Similarity	NPC469419
0.8385	Intermediate Similarity	NPC261659
0.8375	Intermediate Similarity	NPC253591
0.8363	Intermediate Similarity	NPC475197
0.8363	Intermediate Similarity	NPC195972
0.8363	Intermediate Similarity	NPC473467
0.8313	Intermediate Similarity	NPC475561
0.8313	Intermediate Similarity	NPC475417
0.821	Intermediate Similarity	NPC35097
0.8204	Intermediate Similarity	NPC130489
0.8204	Intermediate Similarity	NPC208676
0.8204	Intermediate Similarity	NPC269668
0.8198	Intermediate Similarity	NPC477617
0.8176	Intermediate Similarity	NPC149002
0.8176	Intermediate Similarity	NPC469458
0.8176	Intermediate Similarity	NPC88176
0.8176	Intermediate Similarity	NPC469396
0.8176	Intermediate Similarity	NPC96447
0.8161	Intermediate Similarity	NPC475613
0.8155	Intermediate Similarity	NPC477627
0.8133	Intermediate Similarity	NPC10945
0.8107	Intermediate Similarity	NPC326278
0.8089	Intermediate Similarity	NPC62800
0.8089	Intermediate Similarity	NPC79921
0.8089	Intermediate Similarity	NPC324262
0.8086	Intermediate Similarity	NPC120728
0.8077	Intermediate Similarity	NPC262324
0.8077	Intermediate Similarity	NPC243893
0.807	Intermediate Similarity	NPC469459
0.8061	Intermediate Similarity	NPC257847
0.8049	Intermediate Similarity	NPC77310
0.8025	Intermediate Similarity	NPC470330
0.8025	Intermediate Similarity	NPC469696
0.8025	Intermediate Similarity	NPC472936
0.8025	Intermediate Similarity	NPC472938
0.8025	Intermediate Similarity	NPC472937
0.8011	Intermediate Similarity	NPC469418
0.7989	Intermediate Similarity	NPC13989
0.7989	Intermediate Similarity	NPC149502
0.7989	Intermediate Similarity	NPC299855
0.7989	Intermediate Similarity	NPC222665
0.7989	Intermediate Similarity	NPC271755
0.7989	Intermediate Similarity	NPC96194
0.7989	Intermediate Similarity	NPC254071
0.7989	Intermediate Similarity	NPC148185
0.7988	Intermediate Similarity	NPC472939
0.7967	Intermediate Similarity	NPC475299
0.7963	Intermediate Similarity	NPC320734
0.7953	Intermediate Similarity	NPC327694
0.7953	Intermediate Similarity	NPC161151
0.795	Intermediate Similarity	NPC296659
0.795	Intermediate Similarity	NPC202391
0.795	Intermediate Similarity	NPC25491
0.7944	Intermediate Similarity	NPC189704
0.7939	Intermediate Similarity	NPC472657
0.7939	Intermediate Similarity	NPC472658
0.7937	Intermediate Similarity	NPC469623
0.7937	Intermediate Similarity	NPC148080
0.7925	Intermediate Similarity	NPC164743
0.7917	Intermediate Similarity	NPC475378
0.791	Intermediate Similarity	NPC260300
0.7907	Intermediate Similarity	NPC318472
0.7901	Intermediate Similarity	NPC476067
0.7901	Intermediate Similarity	NPC475121
0.7885	Intermediate Similarity	NPC164172
0.7879	Intermediate Similarity	NPC240592
0.7879	Intermediate Similarity	NPC267469
0.7879	Intermediate Similarity	NPC117346
0.7879	Intermediate Similarity	NPC472548
0.7879	Intermediate Similarity	NPC162569
0.7879	Intermediate Similarity	NPC116292
0.7879	Intermediate Similarity	NPC179128
0.7879	Intermediate Similarity	NPC35160
0.7879	Intermediate Similarity	NPC87630
0.7874	Intermediate Similarity	NPC471870
0.7857	Intermediate Similarity	NPC472807
0.7853	Intermediate Similarity	NPC473147
0.7853	Intermediate Similarity	NPC208293
0.7844	Intermediate Similarity	NPC87403
0.7844	Intermediate Similarity	NPC154675
0.7841	Intermediate Similarity	NPC471871
0.784	Intermediate Similarity	NPC194938
0.7836	Intermediate Similarity	NPC117943
0.7836	Intermediate Similarity	NPC293568
0.7834	Intermediate Similarity	NPC471864
0.7829	Intermediate Similarity	NPC179240
0.7824	Intermediate Similarity	NPC275477
0.7821	Intermediate Similarity	NPC471066
0.7821	Intermediate Similarity	NPC471095
0.7818	Intermediate Similarity	NPC96599
0.7818	Intermediate Similarity	NPC161955
0.7818	Intermediate Similarity	NPC279442
0.7816	Intermediate Similarity	NPC185498
0.7812	Intermediate Similarity	NPC470616
0.7812	Intermediate Similarity	NPC470617
0.7811	Intermediate Similarity	NPC478055
0.7809	Intermediate Similarity	NPC80360
0.7803	Intermediate Similarity	NPC40138
0.7803	Intermediate Similarity	NPC469420
0.7798	Intermediate Similarity	NPC469417
0.7798	Intermediate Similarity	NPC160882
0.7791	Intermediate Similarity	NPC210330
0.7785	Intermediate Similarity	NPC472804
0.7784	Intermediate Similarity	NPC472549
0.7778	Intermediate Similarity	NPC186746
0.7778	Intermediate Similarity	NPC204644
0.7778	Intermediate Similarity	NPC478073
0.7771	Intermediate Similarity	NPC266545
0.7771	Intermediate Similarity	NPC327962
0.7771	Intermediate Similarity	NPC202428
0.7771	Intermediate Similarity	NPC477905
0.7765	Intermediate Similarity	NPC108191
0.7765	Intermediate Similarity	NPC208651
0.7765	Intermediate Similarity	NPC195114
0.7765	Intermediate Similarity	NPC206641
0.7765	Intermediate Similarity	NPC93685
0.7764	Intermediate Similarity	NPC472801
0.7764	Intermediate Similarity	NPC172311
0.7764	Intermediate Similarity	NPC27518
0.7764	Intermediate Similarity	NPC304110
0.776	Intermediate Similarity	NPC71385
0.776	Intermediate Similarity	NPC230670
0.7759	Intermediate Similarity	NPC306475
0.7758	Intermediate Similarity	NPC95990
0.7751	Intermediate Similarity	NPC474501
0.7751	Intermediate Similarity	NPC186316
0.775	Intermediate Similarity	NPC116742
0.775	Intermediate Similarity	NPC248287
0.775	Intermediate Similarity	NPC139243
0.775	Intermediate Similarity	NPC234548
0.7746	Intermediate Similarity	NPC116759
0.7746	Intermediate Similarity	NPC14294
0.7746	Intermediate Similarity	NPC109990
0.7744	Intermediate Similarity	NPC143246
0.7744	Intermediate Similarity	NPC119773
0.7744	Intermediate Similarity	NPC474268
0.7744	Intermediate Similarity	NPC475539
0.7744	Intermediate Similarity	NPC212808
0.774	Intermediate Similarity	NPC105137
0.774	Intermediate Similarity	NPC124828
0.7733	Intermediate Similarity	NPC471134
0.7733	Intermediate Similarity	NPC152424
0.7733	Intermediate Similarity	NPC100465
0.7733	Intermediate Similarity	NPC186228
0.773	Intermediate Similarity	NPC477207
0.7727	Intermediate Similarity	NPC469421
0.7725	Intermediate Similarity	NPC158546
0.7725	Intermediate Similarity	NPC289021
0.7722	Intermediate Similarity	NPC188217
0.7719	Intermediate Similarity	NPC314795
0.7719	Intermediate Similarity	NPC53139
0.7717	Intermediate Similarity	NPC112708
0.7714	Intermediate Similarity	NPC177362
0.7714	Intermediate Similarity	NPC286809
0.7711	Intermediate Similarity	NPC473719
0.7711	Intermediate Similarity	NPC477206
0.7706	Intermediate Similarity	NPC283480
0.7706	Intermediate Similarity	NPC148323
0.7701	Intermediate Similarity	NPC265600
0.7701	Intermediate Similarity	NPC102465
0.7692	Intermediate Similarity	NPC474622
0.7692	Intermediate Similarity	NPC470122
0.7692	Intermediate Similarity	NPC469705
0.7692	Intermediate Similarity	NPC17968
0.7692	Intermediate Similarity	NPC474621
0.7688	Intermediate Similarity	NPC61891
0.7688	Intermediate Similarity	NPC325732
0.7688	Intermediate Similarity	NPC22676
0.7688	Intermediate Similarity	NPC216940
0.7688	Intermediate Similarity	NPC308976
0.7688	Intermediate Similarity	NPC477491
0.7688	Intermediate Similarity	NPC475482
0.7688	Intermediate Similarity	NPC97637
0.7688	Intermediate Similarity	NPC187934
0.7688	Intermediate Similarity	NPC145847
0.7688	Intermediate Similarity	NPC471873
0.7688	Intermediate Similarity	NPC324769
0.7688	Intermediate Similarity	NPC198621
0.7683	Intermediate Similarity	NPC475528
0.768	Intermediate Similarity	NPC478001
0.7679	Intermediate Similarity	NPC106818
0.7676	Intermediate Similarity	NPC473711
0.7674	Intermediate Similarity	NPC310399
0.7674	Intermediate Similarity	NPC150943
0.7674	Intermediate Similarity	NPC66193
0.7674	Intermediate Similarity	NPC91634
0.7674	Intermediate Similarity	NPC268718
0.7674	Intermediate Similarity	NPC73422
0.7669	Intermediate Similarity	NPC478250
0.7667	Intermediate Similarity	NPC254588
0.7657	Intermediate Similarity	NPC200726
0.7654	Intermediate Similarity	NPC469397
0.7654	Intermediate Similarity	NPC23593

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 NPC471850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	770
0.2-0.3	1812
0.3-0.4	2816
0.4-0.5	2240
0.5-0.6	963
0.6-0.7	223
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7816	Intermediate Similarity	NPD7228	Approved
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.7602	Intermediate Similarity	NPD4967	Phase 2
0.7602	Intermediate Similarity	NPD4965	Approved
0.7602	Intermediate Similarity	NPD4966	Approved
0.7514	Intermediate Similarity	NPD7799	Discontinued
0.75	Intermediate Similarity	NPD8166	Discontinued
0.7444	Intermediate Similarity	NPD7240	Approved
0.7444	Intermediate Similarity	NPD7685	Pre-registration
0.7432	Intermediate Similarity	NPD8150	Discontinued
0.7427	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD6663	Approved
0.7384	Intermediate Similarity	NPD8455	Phase 2
0.7366	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8312	Approved
0.7363	Intermediate Similarity	NPD8313	Approved
0.7351	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7199	Phase 2
0.733	Intermediate Similarity	NPD8127	Discontinued
0.731	Intermediate Similarity	NPD7028	Phase 2
0.7278	Intermediate Similarity	NPD5736	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7239	Intermediate Similarity	NPD7097	Phase 1
0.7182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7680	Approved
0.7151	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7266	Discontinued
0.7101	Intermediate Similarity	NPD7236	Approved
0.7095	Intermediate Similarity	NPD3787	Discontinued
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7062	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8319	Approved
0.7041	Intermediate Similarity	NPD6190	Approved
0.7041	Intermediate Similarity	NPD8320	Phase 1
0.7037	Intermediate Similarity	NPD3764	Approved
0.7033	Intermediate Similarity	NPD3751	Discontinued
0.7012	Intermediate Similarity	NPD6355	Discontinued
0.7011	Intermediate Similarity	NPD4380	Phase 2
0.6994	Remote Similarity	NPD7239	Suspended
0.6994	Remote Similarity	NPD8032	Phase 2
0.6987	Remote Similarity	NPD3019	Approved
0.6987	Remote Similarity	NPD2932	Approved
0.6977	Remote Similarity	NPD6273	Approved
0.6975	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6559	Discontinued
0.6966	Remote Similarity	NPD7075	Discontinued
0.6959	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7074	Phase 3
0.6949	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3094	Phase 2
0.6907	Remote Similarity	NPD7700	Phase 2
0.6907	Remote Similarity	NPD7699	Phase 2
0.6904	Remote Similarity	NPD7435	Discontinued
0.6902	Remote Similarity	NPD7054	Approved
0.6894	Remote Similarity	NPD5647	Approved
0.6893	Remote Similarity	NPD5760	Phase 2
0.6893	Remote Similarity	NPD5761	Phase 2
0.6886	Remote Similarity	NPD7033	Discontinued
0.6885	Remote Similarity	NPD7473	Discontinued
0.6879	Remote Similarity	NPD5126	Approved
0.6879	Remote Similarity	NPD5125	Phase 3
0.6865	Remote Similarity	NPD7472	Approved
0.6862	Remote Similarity	NPD8407	Phase 2
0.6862	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7741	Discontinued
0.6848	Remote Similarity	NPD4140	Approved
0.6848	Remote Similarity	NPD3818	Discontinued
0.6845	Remote Similarity	NPD7808	Phase 3
0.6839	Remote Similarity	NPD6535	Approved
0.6839	Remote Similarity	NPD6534	Approved
0.6807	Remote Similarity	NPD5735	Approved
0.6806	Remote Similarity	NPD8361	Approved
0.6806	Remote Similarity	NPD8360	Approved
0.6805	Remote Similarity	NPD6004	Phase 3
0.6805	Remote Similarity	NPD5763	Approved
0.6805	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6005	Phase 3
0.6805	Remote Similarity	NPD5762	Approved
0.6805	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6002	Phase 3
0.6798	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7819	Suspended
0.6792	Remote Similarity	NPD3092	Approved
0.6791	Remote Similarity	NPD8368	Discontinued
0.6791	Remote Similarity	NPD7251	Discontinued
0.6789	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6233	Phase 2
0.6782	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7874	Approved
0.6768	Remote Similarity	NPD7095	Approved
0.6755	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6778	Approved
0.6751	Remote Similarity	NPD6781	Approved
0.6751	Remote Similarity	NPD6780	Approved
0.6751	Remote Similarity	NPD6782	Approved
0.6751	Remote Similarity	NPD6777	Approved
0.6751	Remote Similarity	NPD6779	Approved
0.6751	Remote Similarity	NPD6776	Approved
0.6749	Remote Similarity	NPD7783	Phase 2
0.6749	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6166	Phase 2
0.6738	Remote Similarity	NPD6797	Phase 2
0.6734	Remote Similarity	NPD7698	Approved
0.6734	Remote Similarity	NPD7697	Approved
0.6734	Remote Similarity	NPD7696	Phase 3
0.6733	Remote Similarity	NPD8151	Discontinued
0.6732	Remote Similarity	NPD7930	Approved
0.6727	Remote Similarity	NPD6798	Discontinued
0.6724	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6232	Discontinued
0.6719	Remote Similarity	NPD8435	Approved
0.67	Remote Similarity	NPD7870	Phase 2
0.67	Remote Similarity	NPD7871	Phase 2
0.6686	Remote Similarity	NPD4110	Phase 3
0.6686	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7003	Approved
0.6686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3749	Approved
0.6685	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7411	Suspended
0.6683	Remote Similarity	NPD6823	Phase 2
0.6683	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD6653	Approved
0.665	Remote Similarity	NPD7497	Discontinued
0.6649	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6801	Discontinued
0.6648	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3620	Phase 2
0.6647	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6100	Approved
0.6647	Remote Similarity	NPD6099	Approved
0.6647	Remote Similarity	NPD2438	Suspended
0.6646	Remote Similarity	NPD3091	Approved
0.6631	Remote Similarity	NPD5844	Phase 1
0.6631	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7058	Phase 2
0.663	Remote Similarity	NPD7057	Phase 3
0.663	Remote Similarity	NPD7768	Phase 2
0.663	Remote Similarity	NPD7315	Approved
0.6629	Remote Similarity	NPD6599	Discontinued
0.6625	Remote Similarity	NPD3026	Approved
0.6625	Remote Similarity	NPD3023	Approved
0.6615	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6213	Phase 3
0.6615	Remote Similarity	NPD6212	Phase 3
0.6614	Remote Similarity	NPD6764	Approved
0.6614	Remote Similarity	NPD6765	Approved
0.6611	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5058	Phase 3
0.6604	Remote Similarity	NPD3025	Approved
0.6604	Remote Similarity	NPD3024	Approved
0.6584	Remote Similarity	NPD7999	Approved
0.6573	Remote Similarity	NPD3226	Approved
0.6568	Remote Similarity	NPD6353	Approved
0.6561	Remote Similarity	NPD4198	Discontinued
0.6556	Remote Similarity	NPD1934	Approved
0.6554	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4060	Phase 1
0.6541	Remote Similarity	NPD7229	Phase 3
0.6534	Remote Similarity	NPD2532	Approved
0.6534	Remote Similarity	NPD2533	Approved
0.6534	Remote Similarity	NPD2534	Approved
0.6534	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6674	Discontinued
0.6529	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5494	Approved
0.6515	Remote Similarity	NPD8485	Approved
0.6507	Remote Similarity	NPD8404	Phase 2
0.65	Remote Similarity	NPD6677	Suspended
0.6497	Remote Similarity	NPD2629	Approved
0.6494	Remote Similarity	NPD3400	Discontinued
0.6494	Remote Similarity	NPD3750	Approved
0.6491	Remote Similarity	NPD7305	Phase 1
0.6491	Remote Similarity	NPD2799	Discontinued
0.6485	Remote Similarity	NPD6085	Phase 2
0.6485	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5402	Approved
0.648	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7296	Approved
0.6477	Remote Similarity	NPD7390	Discontinued
0.6477	Remote Similarity	NPD6785	Approved
0.6477	Remote Similarity	NPD6784	Approved
0.6474	Remote Similarity	NPD5958	Discontinued

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