NPASS Compound

Structure

NPC471426 OpenBabel07101718292D 86 96 0 0 1 0 0 0 0 0999 V2000 13.1573 4.1587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0951 -4.3413 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 -1.2188 4.1237 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 2.5074 3.8848 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 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 6.2291 -1.8413 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 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2912 4.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0951 -3.3413 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 10.5592 1.6587 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 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 12.2912 5.6587 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 11.4252 6.1587 0.0000 C 0 0 2 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 7.0951 4.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5592 5.6587 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 9.6932 3.1587 0.0000 C 0 0 1 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 10.5592 4.6587 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 -0.8258 3.2042 0.0000 C 0 0 0 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 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 12.2912 1.6587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -2.8413 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 13.1573 6.1587 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 11.4252 7.1587 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 6.2291 4.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6932 6.1587 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 6.2291 -2.8413 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 11.4252 4.1587 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 5.3630 -0.3413 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 9.6932 4.1587 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 7.9611 3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 54 1 0 0 0 0 4 54 1 0 0 0 0 5 55 1 0 0 0 0 6 55 1 0 0 0 0 8 57 1 0 0 0 0 9 58 1 0 0 0 0 10 14 1 0 0 0 0 10 31 1 0 0 0 0 11 15 1 0 0 0 0 11 32 1 0 0 0 0 12 13 1 0 0 0 0 12 35 1 0 0 0 0 13 56 1 0 0 0 0 14 57 1 0 0 0 0 16 17 1 0 0 0 0 16 54 1 0 0 0 0 18 33 1 0 0 0 0 18 54 1 0 0 0 0 19 34 1 0 0 0 0 19 58 1 0 0 0 0 20 61 1 0 0 0 0 21 27 1 0 0 0 0 21 76 1 0 0 0 0 22 75 1 0 0 0 0 23 30 1 0 0 0 0 23 77 1 0 0 0 0 24 59 1 0 0 0 0 24 78 1 0 0 0 0 25 1 1 6 0 0 0 25 36 1 0 0 0 0 25 79 1 0 0 0 0 26 62 2 0 0 0 0 26 75 1 0 0 0 0 27 37 1 0 0 0 0 27 63 1 6 0 0 0 28 20 1 1 0 0 0 28 39 1 0 0 0 0 28 80 1 0 0 0 0 29 22 1 6 0 0 0 29 38 1 0 0 0 0 29 81 1 0 0 0 0 30 40 1 0 0 0 0 30 82 1 6 0 0 0 31 55 1 0 0 0 0 31 56 1 1 0 0 0 32 56 1 1 0 0 0 32 57 1 0 0 0 0 33 59 1 1 0 0 0 33 60 1 0 0 0 0 34 59 1 6 0 0 0 34 64 1 0 0 0 0 35 55 1 0 0 0 0 35 83 1 1 0 0 0 36 41 1 0 0 0 0 36 65 1 1 0 0 0 37 43 1 0 0 0 0 37 66 1 1 0 0 0 38 42 1 0 0 0 0 38 67 1 1 0 0 0 39 46 1 0 0 0 0 39 68 1 6 0 0 0 40 47 1 0 0 0 0 40 69 1 6 0 0 0 41 44 1 0 0 0 0 41 70 1 6 0 0 0 42 45 1 0 0 0 0 42 71 1 6 0 0 0 43 49 1 0 0 0 0 43 72 1 6 0 0 0 44 50 1 0 0 0 0 44 73 1 6 0 0 0 45 51 1 0 0 0 0 45 74 1 1 0 0 0 46 48 1 0 0 0 0 46 84 1 1 0 0 0 47 52 1 0 0 0 0 47 85 1 1 0 0 0 48 53 1 0 0 0 0 48 86 1 6 0 0 0 49 76 1 0 0 0 0 49 86 1 1 0 0 0 50 79 1 0 0 0 0 50 84 1 1 0 0 0 51 81 1 0 0 0 0 51 85 1 6 0 0 0 52 77 1 0 0 0 0 52 83 1 6 0 0 0 53 80 1 0 0 0 0 53 82 1 1 0 0 0 56 7 1 1 0 0 0 57 58 1 6 0 0 0 58 60 1 1 0 0 0 59 17 1 6 0 0 0 60 15 1 6 0 0 0 60 78 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1234.63
Volume:	1178.104
LogP:	2.061
LogD:	1.774
LogS:	-3.818
# Rotatable Bonds:	14
TPSA:	390.82
# H-Bond Aceptor:	26
# H-Bond Donor:	13
# Rings:	11
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.073
Synthetic Accessibility Score:	7.238
Fsp3:	0.983
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:	-5.931
MDCK Permeability:	0.00017152722284663469
Pgp-inhibitor:	0.079
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.993
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	64.39391326904297%
Volume Distribution (VD):	-0.151
Pgp-substrate:	15.00982666015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.549
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	-0.307
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.36
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.734
Skin Sensitization:	0.895
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.6

Download Data

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

Natural Product: NPC471426

Natural Product ID:	NPC471426
*Common Name:**	DCQSTROBYCAYEV-NEDZPZAFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DCQSTROBYCAYEV-NEDZPZAFSA-N
Standard InCHI:	InChI=1S/C60H98O26/c1-25-36(65)41(70)44(73)50(79-25)84-46-39(68)28(20-61)80-53(48(46)86-49-43(72)37(66)27(63)21-76-49)82-30-23-77-52(47(40(30)69)85-51-45(74)42(71)38(67)29(81-51)22-75-26(2)62)83-35-12-13-56(7)31(55(35,5)6)10-14-57(8)32(56)11-15-60-33-18-54(3,4)16-17-59(33,24-78-60)34(64)19-58(57,60)9/h25,27-53,61,63-74H,10-24H2,1-9H3/t25-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39+,40-,41+,42-,43+,44+,45+,46-,47+,48+,49-,50-,51-,52-,53-,56-,57+,58-,59+,60-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CO[C@H]([C@@H]([C@H]2O)O[C@@H]2O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]2O)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]4CC(C)(C)CC2)CO3)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2442980
PubChem CID:	46930488
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
NPO32586	ardisia gigantifolia stapf.	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24095094]

☑ 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
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	9280.0	nM	PMID[537294]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	8400.0	nM	PMID[537294]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8060.0	nM	PMID[537294]

☑ 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 NPC471426 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	485
0.1-0.2	4181
0.2-0.3	11995
0.3-0.4	11613
0.4-0.5	6070
0.5-0.6	4062
0.6-0.7	2289
0.7-0.8	1544
0.8-0.85	268
0.85-0.9	150
0.9-0.95	16
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471427
1.0	High Similarity	NPC471428
0.9891	High Similarity	NPC471374
0.9891	High Similarity	NPC209798
0.9891	High Similarity	NPC471375
0.9785	High Similarity	NPC51579
0.9565	High Similarity	NPC471424
0.9565	High Similarity	NPC471429
0.9565	High Similarity	NPC471425
0.9565	High Similarity	NPC205129
0.9565	High Similarity	NPC106701
0.9565	High Similarity	NPC189575
0.9457	High Similarity	NPC77717
0.9457	High Similarity	NPC267238
0.9457	High Similarity	NPC253611
0.9457	High Similarity	NPC471373
0.9457	High Similarity	NPC148593
0.9348	High Similarity	NPC171741
0.9348	High Similarity	NPC18724
0.9348	High Similarity	NPC323231
0.9348	High Similarity	NPC224003
0.9348	High Similarity	NPC470623
0.92	High Similarity	NPC22709
0.9192	High Similarity	NPC126753
0.9109	High Similarity	NPC471431
0.91	High Similarity	NPC207693
0.8911	High Similarity	NPC471626
0.8911	High Similarity	NPC473688
0.8911	High Similarity	NPC262567
0.8911	High Similarity	NPC231566
0.8854	High Similarity	NPC237071
0.8854	High Similarity	NPC238796
0.8854	High Similarity	NPC203434
0.8812	High Similarity	NPC40716
0.8812	High Similarity	NPC475630
0.8812	High Similarity	NPC475234
0.8812	High Similarity	NPC138219
0.8812	High Similarity	NPC471430
0.8763	High Similarity	NPC470591
0.8762	High Similarity	NPC477465
0.875	High Similarity	NPC157571
0.875	High Similarity	NPC57964
0.875	High Similarity	NPC94582
0.8738	High Similarity	NPC470622
0.8713	High Similarity	NPC158051
0.8713	High Similarity	NPC273189
0.8713	High Similarity	NPC184805
0.8713	High Similarity	NPC119628
0.8713	High Similarity	NPC158367
0.8696	High Similarity	NPC471410
0.8696	High Similarity	NPC471411
0.8687	High Similarity	NPC475574
0.8646	High Similarity	NPC305418
0.8614	High Similarity	NPC267637
0.8571	High Similarity	NPC307534
0.8571	High Similarity	NPC210157
0.8571	High Similarity	NPC476112
0.8557	High Similarity	NPC477494
0.85	High Similarity	NPC108227
0.85	High Similarity	NPC476839
0.85	High Similarity	NPC476512
0.85	High Similarity	NPC476838
0.85	High Similarity	NPC472081
0.8485	Intermediate Similarity	NPC473518
0.8469	Intermediate Similarity	NPC296936
0.8469	Intermediate Similarity	NPC160426
0.8469	Intermediate Similarity	NPC98018
0.8469	Intermediate Similarity	NPC304011
0.8469	Intermediate Similarity	NPC132080
0.8469	Intermediate Similarity	NPC470863
0.8469	Intermediate Similarity	NPC470866
0.8469	Intermediate Similarity	NPC287483
0.8469	Intermediate Similarity	NPC103616
0.8469	Intermediate Similarity	NPC475625
0.8469	Intermediate Similarity	NPC470864
0.8469	Intermediate Similarity	NPC475643
0.8469	Intermediate Similarity	NPC139271
0.8469	Intermediate Similarity	NPC284104
0.8469	Intermediate Similarity	NPC232037
0.8469	Intermediate Similarity	NPC470865
0.8469	Intermediate Similarity	NPC128572
0.8469	Intermediate Similarity	NPC116756
0.8469	Intermediate Similarity	NPC84111
0.8469	Intermediate Similarity	NPC184617
0.8469	Intermediate Similarity	NPC97700
0.8469	Intermediate Similarity	NPC30856
0.8454	Intermediate Similarity	NPC151214
0.8454	Intermediate Similarity	NPC191915
0.8438	Intermediate Similarity	NPC210759
0.8438	Intermediate Similarity	NPC307167
0.8438	Intermediate Similarity	NPC229801
0.8431	Intermediate Similarity	NPC469827
0.8421	Intermediate Similarity	NPC131466
0.8416	Intermediate Similarity	NPC310138
0.8416	Intermediate Similarity	NPC80640
0.8416	Intermediate Similarity	NPC470029
0.8416	Intermediate Similarity	NPC114700
0.8416	Intermediate Similarity	NPC134967
0.8384	Intermediate Similarity	NPC470862
0.8384	Intermediate Similarity	NPC470861
0.8384	Intermediate Similarity	NPC232611
0.8384	Intermediate Similarity	NPC303069
0.8384	Intermediate Similarity	NPC274200
0.8384	Intermediate Similarity	NPC83137
0.8384	Intermediate Similarity	NPC51520
0.8384	Intermediate Similarity	NPC115165
0.8381	Intermediate Similarity	NPC66513
0.837	Intermediate Similarity	NPC213737
0.837	Intermediate Similarity	NPC474284
0.837	Intermediate Similarity	NPC474346
0.837	Intermediate Similarity	NPC475820
0.837	Intermediate Similarity	NPC474253
0.8367	Intermediate Similarity	NPC475351
0.8367	Intermediate Similarity	NPC6295
0.8367	Intermediate Similarity	NPC19400
0.8367	Intermediate Similarity	NPC107962
0.8367	Intermediate Similarity	NPC107188
0.8367	Intermediate Similarity	NPC473610
0.8367	Intermediate Similarity	NPC206003
0.8367	Intermediate Similarity	NPC211354
0.8367	Intermediate Similarity	NPC473727
0.8365	Intermediate Similarity	NPC469826
0.8351	Intermediate Similarity	NPC172838
0.8351	Intermediate Similarity	NPC137004
0.8333	Intermediate Similarity	NPC476837
0.8333	Intermediate Similarity	NPC139181
0.8333	Intermediate Similarity	NPC97260
0.83	Intermediate Similarity	NPC291548
0.8286	Intermediate Similarity	NPC87393
0.8283	Intermediate Similarity	NPC121453
0.8283	Intermediate Similarity	NPC473601
0.8283	Intermediate Similarity	NPC195297
0.8283	Intermediate Similarity	NPC252056
0.8265	Intermediate Similarity	NPC253268
0.8265	Intermediate Similarity	NPC174024
0.8265	Intermediate Similarity	NPC312678
0.8265	Intermediate Similarity	NPC252253
0.8265	Intermediate Similarity	NPC217205
0.8265	Intermediate Similarity	NPC291203
0.8265	Intermediate Similarity	NPC179859
0.8265	Intermediate Similarity	NPC291547
0.8265	Intermediate Similarity	NPC475436
0.8265	Intermediate Similarity	NPC131693
0.8265	Intermediate Similarity	NPC473851
0.8265	Intermediate Similarity	NPC264101
0.8265	Intermediate Similarity	NPC45959
0.8265	Intermediate Similarity	NPC471464
0.8261	Intermediate Similarity	NPC208912
0.8261	Intermediate Similarity	NPC2096
0.8229	Intermediate Similarity	NPC82955
0.8218	Intermediate Similarity	NPC80417
0.8211	Intermediate Similarity	NPC140446
0.8211	Intermediate Similarity	NPC43912
0.82	Intermediate Similarity	NPC477223
0.82	Intermediate Similarity	NPC477222
0.8182	Intermediate Similarity	NPC474399
0.8163	Intermediate Similarity	NPC177834
0.8163	Intermediate Similarity	NPC48339
0.8163	Intermediate Similarity	NPC477547
0.8163	Intermediate Similarity	NPC144790
0.8163	Intermediate Similarity	NPC141769
0.8163	Intermediate Similarity	NPC325828
0.8163	Intermediate Similarity	NPC297348
0.8163	Intermediate Similarity	NPC477451
0.8163	Intermediate Similarity	NPC88962
0.8163	Intermediate Similarity	NPC249204
0.8163	Intermediate Similarity	NPC149400
0.8163	Intermediate Similarity	NPC250393
0.8163	Intermediate Similarity	NPC234352
0.8144	Intermediate Similarity	NPC65550
0.8131	Intermediate Similarity	NPC469824
0.8113	Intermediate Similarity	NPC236753
0.8113	Intermediate Similarity	NPC469825
0.8113	Intermediate Similarity	NPC228190
0.8108	Intermediate Similarity	NPC477464
0.81	Intermediate Similarity	NPC142264
0.81	Intermediate Similarity	NPC476510
0.8085	Intermediate Similarity	NPC18953
0.8081	Intermediate Similarity	NPC309866
0.8081	Intermediate Similarity	NPC473774
0.8081	Intermediate Similarity	NPC24960
0.8081	Intermediate Similarity	NPC222731
0.8081	Intermediate Similarity	NPC294686
0.8061	Intermediate Similarity	NPC204881
0.8061	Intermediate Similarity	NPC473830
0.8043	Intermediate Similarity	NPC475456
0.8039	Intermediate Similarity	NPC470030
0.8021	Intermediate Similarity	NPC45833
0.8021	Intermediate Similarity	NPC110365
0.8021	Intermediate Similarity	NPC62202
0.8021	Intermediate Similarity	NPC213658
0.802	Intermediate Similarity	NPC233649
0.802	Intermediate Similarity	NPC470028
0.8018	Intermediate Similarity	NPC475899
0.8	Intermediate Similarity	NPC290612
0.8	Intermediate Similarity	NPC92196
0.7982	Intermediate Similarity	NPC473128
0.7982	Intermediate Similarity	NPC49413
0.7982	Intermediate Similarity	NPC44298
0.7982	Intermediate Similarity	NPC290608

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 NPC471426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	502
0.1-0.2	4144
0.2-0.3	3108
0.3-0.4	778
0.4-0.5	367
0.5-0.6	180
0.6-0.7	53
0.7-0.8	15
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8163	Intermediate Similarity	NPD8171	Discontinued
0.7736	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD8133	Approved
0.7265	Intermediate Similarity	NPD8294	Approved
0.7265	Intermediate Similarity	NPD8377	Approved
0.7203	Intermediate Similarity	NPD8380	Approved
0.7203	Intermediate Similarity	NPD8379	Approved
0.7203	Intermediate Similarity	NPD8296	Approved
0.7203	Intermediate Similarity	NPD8378	Approved
0.7203	Intermediate Similarity	NPD8335	Approved
0.7155	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3669	Approved
0.7071	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8033	Approved
0.6949	Remote Similarity	NPD7328	Approved
0.6949	Remote Similarity	NPD7327	Approved
0.6942	Remote Similarity	NPD8328	Phase 3
0.6939	Remote Similarity	NPD6928	Phase 2
0.6891	Remote Similarity	NPD7516	Approved
0.6842	Remote Similarity	NPD1810	Approved
0.6842	Remote Similarity	NPD1811	Approved
0.6702	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2686	Approved
0.6526	Remote Similarity	NPD2687	Approved
0.6526	Remote Similarity	NPD2254	Approved
0.6504	Remote Similarity	NPD7503	Approved
0.65	Remote Similarity	NPD6940	Discontinued
0.6429	Remote Similarity	NPD7507	Approved
0.6421	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6114	Approved
0.64	Remote Similarity	NPD6115	Approved
0.64	Remote Similarity	NPD6118	Approved
0.64	Remote Similarity	NPD6697	Approved
0.6373	Remote Similarity	NPD1780	Approved
0.6373	Remote Similarity	NPD1779	Approved
0.6371	Remote Similarity	NPD8516	Approved
0.6371	Remote Similarity	NPD8517	Approved
0.6371	Remote Similarity	NPD8515	Approved
0.6325	Remote Similarity	NPD6686	Approved
0.63	Remote Similarity	NPD6116	Phase 1
0.6279	Remote Similarity	NPD7319	Approved
0.624	Remote Similarity	NPD8513	Phase 3
0.6239	Remote Similarity	NPD6412	Phase 2
0.6216	Remote Similarity	NPD7991	Discontinued
0.6202	Remote Similarity	NPD7736	Approved
0.62	Remote Similarity	NPD6117	Approved
0.6186	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD8034	Phase 2
0.6091	Remote Similarity	NPD8035	Phase 2
0.6087	Remote Similarity	NPD6123	Approved
0.6064	Remote Similarity	NPD371	Approved
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.597	Remote Similarity	NPD8450	Suspended
0.5917	Remote Similarity	NPD8174	Phase 2
0.5896	Remote Similarity	NPD8449	Approved
0.5865	Remote Similarity	NPD7329	Approved
0.5841	Remote Similarity	NPD7748	Approved
0.5833	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7902	Approved
0.582	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6370	Approved
0.5784	Remote Similarity	NPD3703	Phase 2
0.5776	Remote Similarity	NPD7638	Approved
0.5763	Remote Similarity	NPD8084	Approved
0.5763	Remote Similarity	NPD8082	Approved
0.5763	Remote Similarity	NPD8139	Approved
0.5763	Remote Similarity	NPD8138	Approved
0.5763	Remote Similarity	NPD8086	Approved
0.5763	Remote Similarity	NPD8083	Approved
0.5763	Remote Similarity	NPD8085	Approved
0.575	Remote Similarity	NPD8393	Approved
0.5736	Remote Similarity	NPD6921	Approved
0.5726	Remote Similarity	NPD7639	Approved
0.5726	Remote Similarity	NPD7640	Approved
0.5725	Remote Similarity	NPD7492	Approved
0.5714	Remote Similarity	NPD8276	Approved
0.5714	Remote Similarity	NPD7645	Phase 2
0.5714	Remote Similarity	NPD8275	Approved
0.5694	Remote Similarity	NPD7625	Phase 1
0.5682	Remote Similarity	NPD6616	Approved
0.5678	Remote Similarity	NPD1700	Approved
0.5667	Remote Similarity	NPD8081	Approved
0.5664	Remote Similarity	NPD7515	Phase 2
0.5659	Remote Similarity	NPD6059	Approved
0.5659	Remote Similarity	NPD6054	Approved
0.5644	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD7078	Approved
0.5631	Remote Similarity	NPD3702	Approved
0.563	Remote Similarity	NPD7632	Discontinued
0.56	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.56	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6882	Approved
0.56	Remote Similarity	NPD8297	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