NPASS Compound

Structure

NPC471626 OpenBabel07101718292D 95106 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 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 -0.2260 4.0043 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 7.9611 9.1587 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 -1.2188 4.1237 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 7.9611 6.1587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0951 8.6587 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 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 12.2912 5.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2291 9.1587 0.0000 C 0 0 2 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 5.3630 8.6587 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 10.5592 5.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3630 7.6587 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 7.0951 4.6587 0.0000 C 0 0 2 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 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 6.2291 7.1587 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 7.9611 10.1587 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 12.2912 1.6587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2117 4.2431 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 10.1587 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 4.4970 9.1587 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 6.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 7.1587 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 4.1587 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 11.4252 4.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0951 7.6587 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 6.2291 6.1587 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 58 1 0 0 0 0 3 58 1 0 0 0 0 6 61 1 0 0 0 0 7 62 1 0 0 0 0 8 12 1 0 0 0 0 8 31 1 0 0 0 0 9 13 1 0 0 0 0 9 32 1 0 0 0 0 10 11 1 0 0 0 0 10 35 1 0 0 0 0 11 60 1 0 0 0 0 12 61 1 0 0 0 0 14 15 1 0 0 0 0 14 59 1 0 0 0 0 16 33 1 0 0 0 0 16 59 1 0 0 0 0 17 34 1 0 0 0 0 17 62 1 0 0 0 0 18 65 1 0 0 0 0 19 66 1 0 0 0 0 20 67 1 0 0 0 0 21 26 1 0 0 0 0 21 83 1 0 0 0 0 22 30 1 0 0 0 0 22 84 1 0 0 0 0 23 59 1 0 0 0 0 23 68 2 0 0 0 0 24 63 1 0 0 0 0 24 85 1 0 0 0 0 25 1 1 6 0 0 0 25 36 1 0 0 0 0 25 86 1 0 0 0 0 26 48 1 0 0 0 0 26 69 1 6 0 0 0 27 18 1 1 0 0 0 27 37 1 0 0 0 0 27 87 1 0 0 0 0 28 19 1 6 0 0 0 28 38 1 0 0 0 0 28 88 1 0 0 0 0 29 20 1 1 0 0 0 29 39 1 0 0 0 0 29 89 1 0 0 0 0 30 40 1 0 0 0 0 30 90 1 6 0 0 0 31 58 1 0 0 0 0 31 60 1 1 0 0 0 32 60 1 1 0 0 0 32 61 1 0 0 0 0 33 63 1 1 0 0 0 33 64 1 0 0 0 0 34 63 1 6 0 0 0 34 70 1 0 0 0 0 35 58 1 0 0 0 0 35 91 1 1 0 0 0 36 41 1 0 0 0 0 36 71 1 1 0 0 0 37 42 1 0 0 0 0 37 72 1 6 0 0 0 38 43 1 0 0 0 0 38 73 1 1 0 0 0 39 49 1 0 0 0 0 39 74 1 6 0 0 0 40 50 1 0 0 0 0 40 75 1 6 0 0 0 41 44 1 0 0 0 0 41 76 1 6 0 0 0 42 45 1 0 0 0 0 42 77 1 1 0 0 0 43 46 1 0 0 0 0 43 78 1 6 0 0 0 44 53 1 0 0 0 0 44 79 1 6 0 0 0 45 54 1 0 0 0 0 45 80 1 6 0 0 0 46 55 1 0 0 0 0 46 81 1 1 0 0 0 47 48 1 0 0 0 0 47 52 1 0 0 0 0 47 82 1 6 0 0 0 48 92 1 1 0 0 0 49 51 1 0 0 0 0 49 93 1 1 0 0 0 50 56 1 0 0 0 0 50 94 1 1 0 0 0 51 57 1 0 0 0 0 51 95 1 6 0 0 0 52 83 1 0 0 0 0 52 95 1 1 0 0 0 53 86 1 0 0 0 0 53 93 1 1 0 0 0 54 87 1 0 0 0 0 54 92 1 1 0 0 0 55 88 1 0 0 0 0 55 94 1 6 0 0 0 56 84 1 0 0 0 0 56 91 1 6 0 0 0 57 89 1 0 0 0 0 57 90 1 1 0 0 0 59 4 1 1 0 0 0 60 5 1 1 0 0 0 61 62 1 6 0 0 0 62 64 1 1 0 0 0 63 15 1 6 0 0 0 64 13 1 6 0 0 0 64 85 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1368.66
Volume:	1282.683
LogP:	-0.434
LogD:	0.545
LogS:	-2.984
# Rotatable Bonds:	16
TPSA:	480.97
# H-Bond Aceptor:	31
# H-Bond Donor:	17
# Rings:	12
# Heavy Atoms:	31

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	7.978
Fsp3:	0.984
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:	-6.541
MDCK Permeability:	0.0003256530617363751
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.295
Plasma Protein Binding (PPB):	38.86166000366211%
Volume Distribution (VD):	-0.183
Pgp-substrate:	26.891950607299805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-0.881
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.464
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.005
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.92
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC471626

Natural Product ID:	NPC471626
*Common Name:**	LKDANUVPWBCRLE-OMAMTLKUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LKDANUVPWBCRLE-OMAMTLKUSA-N
Standard InCHI:	InChI=1S/C64H104O31/c1-25-36(71)41(76)44(79)53(86-25)93-49-39(74)29(20-67)89-57(51(49)95-52-47(82)48(26(69)21-83-52)92-54-45(80)42(77)37(72)27(18-65)87-54)90-30-22-84-56(50(40(30)75)94-55-46(81)43(78)38(73)28(19-66)88-55)91-35-10-11-60(5)31(58(35,2)3)8-12-61(6)32(60)9-13-64-33-16-59(4,23-68)14-15-63(33,24-85-64)34(70)17-62(61,64)7/h23,25-57,65-67,69-82H,8-22,24H2,1-7H3/t25-,26+,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-,54-,55-,56-,57-,59-,60-,61+,62-,63+,64-/m0/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[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)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:	CHEMBL3037935
PubChem CID:	25147101
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	=	2000.0	nM	PMID[456263]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	3200.0	nM	PMID[456263]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3200.0	nM	PMID[456263]

☑ 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 NPC471626 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	NPC231566
1.0	High Similarity	NPC473688
1.0	High Similarity	NPC262567
0.9899	High Similarity	NPC138219
0.9899	High Similarity	NPC40716
0.9899	High Similarity	NPC475630
0.9899	High Similarity	NPC475234
0.9802	High Similarity	NPC471431
0.9798	High Similarity	NPC158367
0.9798	High Similarity	NPC158051
0.9798	High Similarity	NPC119628
0.9505	High Similarity	NPC126753
0.9423	High Similarity	NPC157571
0.9417	High Similarity	NPC66513
0.932	High Similarity	NPC87393
0.9135	High Similarity	NPC22709
0.9126	High Similarity	NPC471430
0.9048	High Similarity	NPC470622
0.9038	High Similarity	NPC207693
0.9029	High Similarity	NPC273189
0.9029	High Similarity	NPC184805
0.8932	High Similarity	NPC267637
0.8911	High Similarity	NPC471428
0.8911	High Similarity	NPC471426
0.8911	High Similarity	NPC471427
0.8889	High Similarity	NPC471424
0.8889	High Similarity	NPC471425
0.8889	High Similarity	NPC106701
0.8889	High Similarity	NPC189575
0.8889	High Similarity	NPC471429
0.8889	High Similarity	NPC477465
0.8889	High Similarity	NPC205129
0.8812	High Similarity	NPC471375
0.8812	High Similarity	NPC471374
0.8812	High Similarity	NPC209798
0.8788	High Similarity	NPC253611
0.8788	High Similarity	NPC471373
0.8788	High Similarity	NPC77717
0.8788	High Similarity	NPC148593
0.8788	High Similarity	NPC267238
0.8738	High Similarity	NPC80640
0.8725	High Similarity	NPC51579
0.8687	High Similarity	NPC323231
0.8687	High Similarity	NPC224003
0.8687	High Similarity	NPC171741
0.8687	High Similarity	NPC470623
0.8687	High Similarity	NPC18724
0.8679	High Similarity	NPC469826
0.8598	High Similarity	NPC273002
0.8598	High Similarity	NPC92297
0.8598	High Similarity	NPC94086
0.8598	High Similarity	NPC473817
0.8598	High Similarity	NPC220836
0.8598	High Similarity	NPC233433
0.8544	High Similarity	NPC80417
0.8505	High Similarity	NPC92890
0.8505	High Similarity	NPC202898
0.8505	High Similarity	NPC475319
0.844	Intermediate Similarity	NPC469824
0.8426	Intermediate Similarity	NPC228190
0.8426	Intermediate Similarity	NPC236753
0.8396	Intermediate Similarity	NPC469827
0.8364	Intermediate Similarity	NPC477492
0.8318	Intermediate Similarity	NPC215408
0.8286	Intermediate Similarity	NPC477172
0.8257	Intermediate Similarity	NPC469825
0.8241	Intermediate Similarity	NPC203974
0.823	Intermediate Similarity	NPC179429
0.8208	Intermediate Similarity	NPC310031
0.8208	Intermediate Similarity	NPC80191
0.8173	Intermediate Similarity	NPC472273
0.8131	Intermediate Similarity	NPC34562
0.8087	Intermediate Similarity	NPC477464
0.8058	Intermediate Similarity	NPC305418
0.8053	Intermediate Similarity	NPC79193
0.8036	Intermediate Similarity	NPC477489
0.8019	Intermediate Similarity	NPC20028
0.8	Intermediate Similarity	NPC307534
0.8	Intermediate Similarity	NPC476112
0.8	Intermediate Similarity	NPC475899
0.7982	Intermediate Similarity	NPC137414
0.7981	Intermediate Similarity	NPC477494
0.7949	Intermediate Similarity	NPC275225
0.7949	Intermediate Similarity	NPC477463
0.7949	Intermediate Similarity	NPC68767
0.7949	Intermediate Similarity	NPC293031
0.7949	Intermediate Similarity	NPC51099
0.7946	Intermediate Similarity	NPC1876
0.7946	Intermediate Similarity	NPC204392
0.7946	Intermediate Similarity	NPC240734
0.7946	Intermediate Similarity	NPC275668
0.7946	Intermediate Similarity	NPC91838
0.7941	Intermediate Similarity	NPC18536
0.7941	Intermediate Similarity	NPC50443
0.7931	Intermediate Similarity	NPC473386
0.7925	Intermediate Similarity	NPC472144
0.7925	Intermediate Similarity	NPC473518
0.7905	Intermediate Similarity	NPC287483
0.7905	Intermediate Similarity	NPC475643
0.7905	Intermediate Similarity	NPC238796
0.7905	Intermediate Similarity	NPC132080
0.7905	Intermediate Similarity	NPC284104
0.7905	Intermediate Similarity	NPC30856
0.7905	Intermediate Similarity	NPC184617
0.7905	Intermediate Similarity	NPC103616
0.7905	Intermediate Similarity	NPC128572
0.7905	Intermediate Similarity	NPC84111
0.7905	Intermediate Similarity	NPC116756
0.7905	Intermediate Similarity	NPC203434
0.7905	Intermediate Similarity	NPC475625
0.7905	Intermediate Similarity	NPC237071
0.7905	Intermediate Similarity	NPC470866
0.7905	Intermediate Similarity	NPC160426
0.7905	Intermediate Similarity	NPC470864
0.7905	Intermediate Similarity	NPC139271
0.7905	Intermediate Similarity	NPC98018
0.7905	Intermediate Similarity	NPC470863
0.7905	Intermediate Similarity	NPC232037
0.7905	Intermediate Similarity	NPC475765
0.7905	Intermediate Similarity	NPC470865
0.7905	Intermediate Similarity	NPC97700
0.7905	Intermediate Similarity	NPC304011
0.7905	Intermediate Similarity	NPC475785
0.7895	Intermediate Similarity	NPC123199
0.7895	Intermediate Similarity	NPC54636
0.7895	Intermediate Similarity	NPC161717
0.7895	Intermediate Similarity	NPC43550
0.7895	Intermediate Similarity	NPC60557
0.7895	Intermediate Similarity	NPC309907
0.7895	Intermediate Similarity	NPC202828
0.7895	Intermediate Similarity	NPC261506
0.7895	Intermediate Similarity	NPC250247
0.7895	Intermediate Similarity	NPC224381
0.7895	Intermediate Similarity	NPC298034
0.7895	Intermediate Similarity	NPC305981
0.7895	Intermediate Similarity	NPC100639
0.7895	Intermediate Similarity	NPC57484
0.7895	Intermediate Similarity	NPC475140
0.7895	Intermediate Similarity	NPC471550
0.7895	Intermediate Similarity	NPC119592
0.7895	Intermediate Similarity	NPC227551
0.7895	Intermediate Similarity	NPC70809
0.7895	Intermediate Similarity	NPC469821
0.7895	Intermediate Similarity	NPC65105
0.7895	Intermediate Similarity	NPC204414
0.7895	Intermediate Similarity	NPC67857
0.7895	Intermediate Similarity	NPC294453
0.7895	Intermediate Similarity	NPC471385
0.7895	Intermediate Similarity	NPC293330
0.7895	Intermediate Similarity	NPC476068
0.7895	Intermediate Similarity	NPC469782
0.7895	Intermediate Similarity	NPC41061
0.7895	Intermediate Similarity	NPC473714
0.7895	Intermediate Similarity	NPC79643
0.7895	Intermediate Similarity	NPC71065
0.7895	Intermediate Similarity	NPC475160
0.7895	Intermediate Similarity	NPC4328
0.7895	Intermediate Similarity	NPC236638
0.7895	Intermediate Similarity	NPC76972
0.789	Intermediate Similarity	NPC470167
0.7864	Intermediate Similarity	NPC229801
0.7864	Intermediate Similarity	NPC210759
0.7864	Intermediate Similarity	NPC307167
0.7863	Intermediate Similarity	NPC144644
0.7863	Intermediate Similarity	NPC476991
0.7863	Intermediate Similarity	NPC142151
0.7863	Intermediate Similarity	NPC153673
0.7863	Intermediate Similarity	NPC37860
0.7863	Intermediate Similarity	NPC110385
0.7863	Intermediate Similarity	NPC267694
0.785	Intermediate Similarity	NPC41843
0.7845	Intermediate Similarity	NPC473459
0.7845	Intermediate Similarity	NPC36831
0.7845	Intermediate Similarity	NPC469822
0.7843	Intermediate Similarity	NPC131466
0.7833	Intermediate Similarity	NPC475368
0.7833	Intermediate Similarity	NPC470218
0.783	Intermediate Similarity	NPC51520
0.783	Intermediate Similarity	NPC232611
0.783	Intermediate Similarity	NPC472145
0.783	Intermediate Similarity	NPC115165
0.783	Intermediate Similarity	NPC274200
0.783	Intermediate Similarity	NPC83137
0.783	Intermediate Similarity	NPC470591
0.783	Intermediate Similarity	NPC470861
0.783	Intermediate Similarity	NPC303069
0.783	Intermediate Similarity	NPC470862
0.7826	Intermediate Similarity	NPC472718
0.781	Intermediate Similarity	NPC107962
0.781	Intermediate Similarity	NPC475351
0.781	Intermediate Similarity	NPC57964
0.781	Intermediate Similarity	NPC94582
0.781	Intermediate Similarity	NPC473610
0.781	Intermediate Similarity	NPC6295
0.781	Intermediate Similarity	NPC206003
0.781	Intermediate Similarity	NPC19400
0.781	Intermediate Similarity	NPC211354
0.781	Intermediate Similarity	NPC107188
0.781	Intermediate Similarity	NPC473727
0.7807	Intermediate Similarity	NPC251263

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 NPC471626 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
0.8396	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD8133	Approved
0.7619	Intermediate Similarity	NPD8171	Discontinued
0.7458	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD8328	Phase 3
0.7155	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7507	Approved
0.6822	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6604	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3669	Approved
0.6587	Remote Similarity	NPD8377	Approved
0.6587	Remote Similarity	NPD8294	Approved
0.6571	Remote Similarity	NPD1779	Approved
0.6571	Remote Similarity	NPD1780	Approved
0.6555	Remote Similarity	NPD6412	Phase 2
0.6535	Remote Similarity	NPD8378	Approved
0.6535	Remote Similarity	NPD8380	Approved
0.6535	Remote Similarity	NPD8379	Approved
0.6535	Remote Similarity	NPD8513	Phase 3
0.6535	Remote Similarity	NPD8296	Approved
0.6535	Remote Similarity	NPD8335	Approved
0.6532	Remote Similarity	NPD6940	Discontinued
0.65	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7736	Approved
0.6476	Remote Similarity	NPD6928	Phase 2
0.6471	Remote Similarity	NPD3703	Phase 2
0.6442	Remote Similarity	NPD6114	Approved
0.6442	Remote Similarity	NPD6118	Approved
0.6442	Remote Similarity	NPD6115	Approved
0.6442	Remote Similarity	NPD6697	Approved
0.6406	Remote Similarity	NPD8033	Approved
0.6373	Remote Similarity	NPD1810	Approved
0.6373	Remote Similarity	NPD1811	Approved
0.6364	Remote Similarity	NPD6686	Approved
0.6357	Remote Similarity	NPD6370	Approved
0.6346	Remote Similarity	NPD6116	Phase 1
0.6299	Remote Similarity	NPD7328	Approved
0.6299	Remote Similarity	NPD7327	Approved
0.6288	Remote Similarity	NPD8293	Discontinued
0.625	Remote Similarity	NPD6117	Approved
0.625	Remote Similarity	NPD7516	Approved
0.621	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6059	Approved
0.6202	Remote Similarity	NPD6054	Approved
0.614	Remote Similarity	NPD8034	Phase 2
0.614	Remote Similarity	NPD8035	Phase 2
0.6083	Remote Similarity	NPD8086	Approved
0.6083	Remote Similarity	NPD8083	Approved
0.6083	Remote Similarity	NPD8082	Approved
0.6083	Remote Similarity	NPD8138	Approved
0.6083	Remote Similarity	NPD8085	Approved
0.6083	Remote Similarity	NPD8139	Approved
0.6083	Remote Similarity	NPD8084	Approved
0.6078	Remote Similarity	NPD2686	Approved
0.6078	Remote Similarity	NPD2687	Approved
0.6078	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD2254	Approved
0.6075	Remote Similarity	NPD7329	Approved
0.6066	Remote Similarity	NPD8393	Approved
0.6058	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8276	Approved
0.6033	Remote Similarity	NPD8275	Approved
0.6031	Remote Similarity	NPD6016	Approved
0.6031	Remote Similarity	NPD6921	Approved
0.6031	Remote Similarity	NPD6015	Approved
0.6019	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD1700	Approved
0.5985	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD8081	Approved
0.598	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.597	Remote Similarity	NPD6616	Approved
0.5962	Remote Similarity	NPD3181	Approved
0.5926	Remote Similarity	NPD7078	Approved
0.5909	Remote Similarity	NPD7503	Approved
0.5906	Remote Similarity	NPD6882	Approved
0.5906	Remote Similarity	NPD8297	Approved
0.5897	Remote Similarity	NPD7748	Approved
0.5893	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD8140	Approved
0.5887	Remote Similarity	NPD8307	Discontinued
0.5882	Remote Similarity	NPD7902	Approved
0.5873	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD3702	Approved
0.5847	Remote Similarity	NPD7991	Discontinued
0.5846	Remote Similarity	NPD6009	Approved
0.5833	Remote Similarity	NPD6319	Approved
0.5821	Remote Similarity	NPD6067	Discontinued
0.5794	Remote Similarity	NPD8306	Approved
0.5794	Remote Similarity	NPD8305	Approved
0.5769	Remote Similarity	NPD4245	Approved
0.5769	Remote Similarity	NPD4244	Approved
0.5766	Remote Similarity	NPD6033	Approved
0.5748	Remote Similarity	NPD8087	Discontinued
0.5736	Remote Similarity	NPD4632	Approved
0.5728	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5360	Phase 3
0.5726	Remote Similarity	NPD7515	Phase 2
0.5693	Remote Similarity	NPD8074	Phase 3
0.568	Remote Similarity	NPD7128	Approved
0.568	Remote Similarity	NPD6402	Approved
0.568	Remote Similarity	NPD5739	Approved
0.568	Remote Similarity	NPD6675	Approved
0.5674	Remote Similarity	NPD8450	Suspended
0.5673	Remote Similarity	NPD3698	Phase 2
0.5669	Remote Similarity	NPD6372	Approved
0.5669	Remote Similarity	NPD6373	Approved
0.5657	Remote Similarity	NPD6123	Approved
0.5644	Remote Similarity	NPD371	Approved
0.5635	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7900	Approved
0.5619	Remote Similarity	NPD4789	Approved
0.5606	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD8449	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