NPASS Compound

Structure

CID144644 OpenBabel06191715502D 84 93 0 0 1 0 0 0 0 0999 V2000 9.1924 0.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1851 -3.7846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2061 -3.7846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5434 -0.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8806 2.8057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8478 -1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 -0.9789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 1.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8478 1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5434 -2.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5434 -1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -2.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3912 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 0.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7823 4.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1567 2.4822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5137 -3.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9017 2.8057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1800 -6.1932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2676 -6.2934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5002 -0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -1.4684 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2390 0.4895 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1023 2.2288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.4593 -4.2049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9346 4.4053 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5434 1.4684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6956 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6956 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3556 1.2832 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0868 4.8947 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2390 4.4053 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0614 -1.8069 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2390 3.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1158 -1.5536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8981 -2.5671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7536 -1.1147 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1515 -3.5126 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6634 0.5910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.2644 -5.0624 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2390 1.4684 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9525 -2.3137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8624 -0.6080 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0868 2.9368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7178 0.8443 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.3505 -4.7116 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0800 0.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6956 -2.9368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5434 0.4895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3912 1.9579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8478 0.4895 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.2131 -6.0400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6956 -0.9789 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7823 5.8737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3912 3.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5309 -7.1071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0868 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7945 2.9210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7126 -5.1505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5434 0.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3012 1.0298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0868 5.8737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3912 4.8947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3147 -2.7525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3912 2.9368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4235 -2.2458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5903 -1.8748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.0854 -4.5293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8267 1.3511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5640 -6.9540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2603 -3.0059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4645 1.7899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7344 -5.4724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5546 0.0842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9346 3.4263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6992 -1.3681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0971 -3.7660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9168 -0.3546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0868 1.9579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0256 0.1521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 51 1 0 0 0 0 3 51 1 0 0 0 0 6 54 1 0 0 0 0 8 9 1 0 0 0 0 8 24 2 0 0 0 0 9 31 1 0 0 0 0 10 11 1 0 0 0 0 10 30 1 0 0 0 0 11 54 1 0 0 0 0 12 13 1 0 0 0 0 12 51 1 0 0 0 0 13 57 1 0 0 0 0 14 25 1 0 0 0 0 14 51 1 0 0 0 0 15 26 1 0 0 0 0 15 52 1 0 0 0 0 16 32 1 0 0 0 0 16 55 1 0 0 0 0 17 58 1 0 0 0 0 18 27 1 0 0 0 0 18 76 1 0 0 0 0 19 28 1 0 0 0 0 19 75 1 0 0 0 0 20 53 1 0 0 0 0 20 59 1 0 0 0 0 21 56 1 0 0 0 0 21 60 1 0 0 0 0 22 56 1 0 0 0 0 22 77 1 0 0 0 0 23 1 1 1 0 0 0 23 40 1 0 0 0 0 23 78 1 0 0 0 0 24 25 1 0 0 0 0 24 55 1 0 0 0 0 25 57 1 1 0 0 0 26 44 1 0 0 0 0 26 61 1 6 0 0 0 27 33 1 0 0 0 0 27 62 1 6 0 0 0 28 41 1 0 0 0 0 28 63 1 6 0 0 0 29 17 1 6 0 0 0 29 34 1 0 0 0 0 29 79 1 0 0 0 0 30 52 1 6 0 0 0 30 53 1 0 0 0 0 31 52 1 6 0 0 0 31 54 1 0 0 0 0 32 57 1 1 0 0 0 32 64 1 0 0 0 0 33 42 1 0 0 0 0 33 65 1 6 0 0 0 34 35 1 0 0 0 0 34 66 1 1 0 0 0 35 37 1 0 0 0 0 35 67 1 6 0 0 0 36 38 1 0 0 0 0 36 40 1 0 0 0 0 36 68 1 1 0 0 0 37 47 1 0 0 0 0 37 69 1 1 0 0 0 38 46 1 0 0 0 0 38 70 1 1 0 0 0 39 41 1 0 0 0 0 39 45 1 0 0 0 0 39 71 1 6 0 0 0 40 80 1 6 0 0 0 41 81 1 1 0 0 0 42 48 1 0 0 0 0 42 82 1 1 0 0 0 43 49 1 0 0 0 0 43 56 1 6 0 0 0 43 72 1 0 0 0 0 44 53 1 6 0 0 0 44 83 1 0 0 0 0 45 75 1 0 0 0 0 45 80 1 1 0 0 0 46 78 1 0 0 0 0 46 82 1 6 0 0 0 47 79 1 0 0 0 0 47 83 1 6 0 0 0 48 76 1 0 0 0 0 48 84 1 6 0 0 0 49 77 1 0 0 0 0 49 81 1 1 0 0 0 50 73 2 0 0 0 0 50 84 1 0 0 0 0 52 4 1 6 0 0 0 53 5 1 6 0 0 0 54 55 1 1 0 0 0 55 7 1 1 0 0 0 56 74 1 6 0 0 0 57 50 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1208.58
Volume:	1140.926
LogP:	1.028
LogD:	0.627
LogS:	-2.855
# Rotatable Bonds:	14
TPSA:	433.05
# H-Bond Aceptor:	27
# H-Bond Donor:	16
# Rings:	10
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.047
Synthetic Accessibility Score:	7.406
Fsp3:	0.947
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:	-6.335
MDCK Permeability:	0.00016378852888010442
Pgp-inhibitor:	0.014
Pgp-substrate:	0.93
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.752
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	48.70056915283203%
Volume Distribution (VD):	-0.09
Pgp-substrate:	21.709041595458984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	-0.115
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.087
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.501

Download Data

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

Natural Product: NPC144644

Natural Product ID:	NPC144644
*Common Name:**	Polygalacin D
IUPAC Name:	[(2S,3R,4S,5S)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-5,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:	Polygalacin D
Standard InCHIKey:	BDCUGHMNUOTFKX-YJGMJMKZSA-N
Standard InCHI:	InChI=1S/C57H92O27/c1-23-40(80-45-39(71)41(28(63)19-75-45)81-49-43(72)56(74,21-60)22-77-49)36(68)38(70)46(78-23)82-42-33(65)27(62)18-76-48(42)84-50(73)57-13-12-51(2,3)14-25(57)24-8-9-31-52(4)15-26(61)44(83-47-37(69)35(67)34(66)29(17-58)79-47)53(5,20-59)30(52)10-11-54(31,6)55(24,7)16-32(57)64/h8,23,25-49,58-72,74H,9-22H2,1-7H3/t23-,25-,26-,27-,28+,29+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39+,40-,41-,42+,43-,44-,45-,46-,47-,48-,49-,52-,53-,54+,55+,56+,57+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)C[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2OC[C@@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O[C@@H]2OC[C@]([C@H]2O)(O)CO)O)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641863
PubChem CID:	53325780
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	root	n.a.	PMID[17851435]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20939516]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	root	n.a.	PMID[20939516]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO214	Platycodon grandiflorus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO214	Platycodon grandiflorus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO214	Platycodon grandiflorus	Species	Campanulaceae	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	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	8500.0	nM	PMID[468396]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5000.0	nM	PMID[468396]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7700.0	nM	PMID[468396]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[468396]

☑ 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 NPC144644 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	263
0.1-0.2	1708
0.2-0.3	5265
0.3-0.4	11476
0.4-0.5	9960
0.5-0.6	6215
0.6-0.7	4291
0.7-0.8	2014
0.8-0.85	743
0.85-0.9	377
0.9-0.95	356
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC153673
1.0	High Similarity	NPC142151
1.0	High Similarity	NPC110385
1.0	High Similarity	NPC37860
1.0	High Similarity	NPC267694
0.991	High Similarity	NPC275225
0.991	High Similarity	NPC68767
0.991	High Similarity	NPC293031
0.991	High Similarity	NPC51099
0.982	High Similarity	NPC473645
0.9818	High Similarity	NPC475899
0.973	High Similarity	NPC471577
0.973	High Similarity	NPC477464
0.973	High Similarity	NPC207738
0.964	High Similarity	NPC105800
0.964	High Similarity	NPC237191
0.964	High Similarity	NPC232237
0.9636	High Similarity	NPC288205
0.9636	High Similarity	NPC476992
0.9636	High Similarity	NPC26626
0.9636	High Similarity	NPC305267
0.9636	High Similarity	NPC51465
0.9636	High Similarity	NPC75287
0.9558	High Similarity	NPC477463
0.9554	High Similarity	NPC51564
0.9554	High Similarity	NPC135849
0.9554	High Similarity	NPC25663
0.955	High Similarity	NPC475514
0.955	High Similarity	NPC33012
0.955	High Similarity	NPC220160
0.955	High Similarity	NPC475209
0.955	High Similarity	NPC102505
0.955	High Similarity	NPC300419
0.955	High Similarity	NPC475119
0.955	High Similarity	NPC191827
0.955	High Similarity	NPC85154
0.955	High Similarity	NPC309223
0.955	High Similarity	NPC470876
0.955	High Similarity	NPC473824
0.955	High Similarity	NPC473452
0.955	High Similarity	NPC8524
0.955	High Similarity	NPC123522
0.955	High Similarity	NPC286457
0.955	High Similarity	NPC104137
0.955	High Similarity	NPC69811
0.9545	High Similarity	NPC164389
0.9545	High Similarity	NPC475486
0.9469	High Similarity	NPC476991
0.9464	High Similarity	NPC473459
0.9459	High Similarity	NPC291903
0.9459	High Similarity	NPC37134
0.9455	High Similarity	NPC473343
0.9455	High Similarity	NPC238935
0.9455	High Similarity	NPC151543
0.9455	High Similarity	NPC323341
0.9455	High Similarity	NPC475208
0.9455	High Similarity	NPC192600
0.9455	High Similarity	NPC134835
0.9455	High Similarity	NPC155410
0.9455	High Similarity	NPC251263
0.9455	High Similarity	NPC114304
0.9455	High Similarity	NPC219180
0.9455	High Similarity	NPC150400
0.9455	High Similarity	NPC96641
0.9455	High Similarity	NPC163183
0.9455	High Similarity	NPC114287
0.9455	High Similarity	NPC475287
0.9455	High Similarity	NPC475467
0.9455	High Similarity	NPC473826
0.9455	High Similarity	NPC73318
0.9455	High Similarity	NPC133818
0.9455	High Similarity	NPC174720
0.9455	High Similarity	NPC241909
0.9455	High Similarity	NPC295823
0.9455	High Similarity	NPC46665
0.9455	High Similarity	NPC309714
0.9455	High Similarity	NPC166422
0.9381	High Similarity	NPC473386
0.9375	High Similarity	NPC471580
0.9375	High Similarity	NPC68175
0.9375	High Similarity	NPC323359
0.9369	High Similarity	NPC76972
0.9369	High Similarity	NPC123199
0.9369	High Similarity	NPC71065
0.9369	High Similarity	NPC67857
0.9369	High Similarity	NPC70809
0.9369	High Similarity	NPC4328
0.9369	High Similarity	NPC471385
0.9369	High Similarity	NPC309907
0.9369	High Similarity	NPC119592
0.9369	High Similarity	NPC475160
0.9369	High Similarity	NPC294453
0.9369	High Similarity	NPC54636
0.9369	High Similarity	NPC298034
0.9369	High Similarity	NPC293330
0.9369	High Similarity	NPC100639
0.9369	High Similarity	NPC57484
0.9369	High Similarity	NPC224381
0.9369	High Similarity	NPC161717
0.9369	High Similarity	NPC227551
0.9369	High Similarity	NPC79643
0.9369	High Similarity	NPC471550
0.9369	High Similarity	NPC204414
0.9369	High Similarity	NPC469782
0.9369	High Similarity	NPC236638
0.9369	High Similarity	NPC250247
0.9369	High Similarity	NPC202828
0.9369	High Similarity	NPC305981
0.9369	High Similarity	NPC65105
0.9369	High Similarity	NPC41061
0.9369	High Similarity	NPC476068
0.9369	High Similarity	NPC475140
0.9369	High Similarity	NPC43550
0.9369	High Similarity	NPC60557
0.9369	High Similarity	NPC473714
0.9369	High Similarity	NPC261506
0.9364	High Similarity	NPC109079
0.9364	High Similarity	NPC471383
0.9364	High Similarity	NPC101744
0.9364	High Similarity	NPC324875
0.9364	High Similarity	NPC102439
0.9364	High Similarity	NPC104071
0.9364	High Similarity	NPC139894
0.9364	High Similarity	NPC80843
0.9364	High Similarity	NPC79718
0.9364	High Similarity	NPC469946
0.9364	High Similarity	NPC10320
0.9364	High Similarity	NPC139044
0.9364	High Similarity	NPC1046
0.9364	High Similarity	NPC475516
0.9364	High Similarity	NPC292677
0.9364	High Similarity	NPC104400
0.9364	High Similarity	NPC475504
0.9364	High Similarity	NPC473383
0.9364	High Similarity	NPC257468
0.9364	High Similarity	NPC276093
0.9364	High Similarity	NPC48249
0.9364	High Similarity	NPC473373
0.9292	High Similarity	NPC36831
0.9292	High Similarity	NPC470514
0.9292	High Similarity	NPC470513
0.9286	High Similarity	NPC471384
0.9286	High Similarity	NPC160415
0.9286	High Similarity	NPC161674
0.9286	High Similarity	NPC58448
0.9279	High Similarity	NPC258885
0.9279	High Similarity	NPC124296
0.9273	High Similarity	NPC164419
0.9273	High Similarity	NPC179434
0.9273	High Similarity	NPC31839
0.9231	High Similarity	NPC470218
0.9224	High Similarity	NPC235405
0.9224	High Similarity	NPC257211
0.9224	High Similarity	NPC281148
0.9224	High Similarity	NPC30735
0.9204	High Similarity	NPC148417
0.9204	High Similarity	NPC136768
0.9204	High Similarity	NPC185466
0.9204	High Similarity	NPC110633
0.9204	High Similarity	NPC471547
0.9182	High Similarity	NPC75747
0.9182	High Similarity	NPC474589
0.9182	High Similarity	NPC475296
0.9182	High Similarity	NPC59804
0.9182	High Similarity	NPC68419
0.9182	High Similarity	NPC174679
0.9182	High Similarity	NPC90856
0.9182	High Similarity	NPC199457
0.9182	High Similarity	NPC7870
0.9182	High Similarity	NPC127056
0.9182	High Similarity	NPC242611
0.9182	High Similarity	NPC164194
0.9182	High Similarity	NPC279554
0.9182	High Similarity	NPC102914
0.9182	High Similarity	NPC270667
0.9182	High Similarity	NPC136877
0.9182	High Similarity	NPC110139
0.9182	High Similarity	NPC29069
0.9182	High Similarity	NPC56713
0.9182	High Similarity	NPC108709
0.9145	High Similarity	NPC23275
0.9145	High Similarity	NPC33068
0.9145	High Similarity	NPC470477
0.9138	High Similarity	NPC475591
0.9138	High Similarity	NPC235438
0.9138	High Similarity	NPC107966
0.9138	High Similarity	NPC236870
0.9138	High Similarity	NPC21691
0.9138	High Similarity	NPC10607
0.9138	High Similarity	NPC80986
0.9138	High Similarity	NPC213952
0.9138	High Similarity	NPC40775
0.9138	High Similarity	NPC187290
0.9138	High Similarity	NPC4749
0.9138	High Similarity	NPC249848
0.913	High Similarity	NPC268184
0.9123	High Similarity	NPC471548
0.9107	High Similarity	NPC138334
0.9107	High Similarity	NPC269315
0.9107	High Similarity	NPC47063

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 NPC144644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1986
0.2-0.3	4017
0.3-0.4	1904
0.4-0.5	525
0.5-0.6	294
0.6-0.7	151
0.7-0.8	34
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8739	High Similarity	NPD8328	Phase 3
0.8547	High Similarity	NPD8295	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD8133	Approved
0.8421	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD8517	Approved
0.8115	Intermediate Similarity	NPD8515	Approved
0.8115	Intermediate Similarity	NPD8516	Approved
0.7967	Intermediate Similarity	NPD8513	Phase 3
0.7886	Intermediate Similarity	NPD8294	Approved
0.7886	Intermediate Similarity	NPD8377	Approved
0.7874	Intermediate Similarity	NPD7736	Approved
0.7823	Intermediate Similarity	NPD8378	Approved
0.7823	Intermediate Similarity	NPD8379	Approved
0.7823	Intermediate Similarity	NPD8335	Approved
0.7823	Intermediate Similarity	NPD8296	Approved
0.7823	Intermediate Similarity	NPD8380	Approved
0.7812	Intermediate Similarity	NPD7319	Approved
0.7778	Intermediate Similarity	NPD6412	Phase 2
0.7717	Intermediate Similarity	NPD7507	Approved
0.7712	Intermediate Similarity	NPD6686	Approved
0.768	Intermediate Similarity	NPD8033	Approved
0.7656	Intermediate Similarity	NPD8293	Discontinued
0.752	Intermediate Similarity	NPD7516	Approved
0.748	Intermediate Similarity	NPD6370	Approved
0.744	Intermediate Similarity	NPD7328	Approved
0.744	Intermediate Similarity	NPD7327	Approved
0.7434	Intermediate Similarity	NPD7748	Approved
0.7391	Intermediate Similarity	NPD7902	Approved
0.7377	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7492	Approved
0.7323	Intermediate Similarity	NPD6054	Approved
0.7323	Intermediate Similarity	NPD6059	Approved
0.7311	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6616	Approved
0.7266	Intermediate Similarity	NPD7503	Approved
0.7257	Intermediate Similarity	NPD7515	Phase 2
0.7252	Intermediate Similarity	NPD7078	Approved
0.7188	Intermediate Similarity	NPD6319	Approved
0.7132	Intermediate Similarity	NPD6016	Approved
0.7132	Intermediate Similarity	NPD6015	Approved
0.7131	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7900	Approved
0.7077	Intermediate Similarity	NPD5988	Approved
0.7073	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8297	Approved
0.704	Intermediate Similarity	NPD6882	Approved
0.6992	Remote Similarity	NPD8074	Phase 3
0.6957	Remote Similarity	NPD8034	Phase 2
0.6957	Remote Similarity	NPD8035	Phase 2
0.6953	Remote Similarity	NPD7115	Discovery
0.6953	Remote Similarity	NPD6009	Approved
0.6897	Remote Similarity	NPD8171	Discontinued
0.6894	Remote Similarity	NPD6067	Discontinued
0.6891	Remote Similarity	NPD7638	Approved
0.688	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4632	Approved
0.6833	Remote Similarity	NPD7639	Approved
0.6833	Remote Similarity	NPD7640	Approved
0.6829	Remote Similarity	NPD6675	Approved
0.6829	Remote Similarity	NPD7128	Approved
0.6829	Remote Similarity	NPD5739	Approved
0.6829	Remote Similarity	NPD6402	Approved
0.6815	Remote Similarity	NPD6033	Approved
0.68	Remote Similarity	NPD6373	Approved
0.68	Remote Similarity	NPD6372	Approved
0.6752	Remote Similarity	NPD6399	Phase 3
0.675	Remote Similarity	NPD4225	Approved
0.6726	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6881	Approved
0.672	Remote Similarity	NPD7320	Approved
0.672	Remote Similarity	NPD6899	Approved
0.6693	Remote Similarity	NPD8130	Phase 1
0.6693	Remote Similarity	NPD6649	Approved
0.6693	Remote Similarity	NPD6650	Approved
0.6691	Remote Similarity	NPD8450	Suspended
0.6667	Remote Similarity	NPD6411	Approved
0.664	Remote Similarity	NPD5701	Approved
0.664	Remote Similarity	NPD5697	Approved
0.664	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7645	Phase 2
0.6619	Remote Similarity	NPD8449	Approved
0.6617	Remote Similarity	NPD6921	Approved
0.6614	Remote Similarity	NPD6883	Approved
0.6614	Remote Similarity	NPD7290	Approved
0.6614	Remote Similarity	NPD4634	Approved
0.6614	Remote Similarity	NPD7102	Approved
0.6562	Remote Similarity	NPD6847	Approved
0.6562	Remote Similarity	NPD6869	Approved
0.6562	Remote Similarity	NPD6617	Approved
0.656	Remote Similarity	NPD6008	Approved
0.6535	Remote Similarity	NPD6012	Approved
0.6535	Remote Similarity	NPD6013	Approved
0.6535	Remote Similarity	NPD6014	Approved
0.6529	Remote Similarity	NPD6084	Phase 2
0.6529	Remote Similarity	NPD6083	Phase 2
0.6519	Remote Similarity	NPD7604	Phase 2
0.6496	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6101	Approved
0.6493	Remote Similarity	NPD5983	Phase 2
0.6457	Remote Similarity	NPD6011	Approved
0.6439	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6336	Discontinued
0.641	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4755	Approved
0.6387	Remote Similarity	NPD7983	Approved
0.6379	Remote Similarity	NPD3618	Phase 1
0.6376	Remote Similarity	NPD7625	Phase 1
0.6357	Remote Similarity	NPD5956	Approved
0.6356	Remote Similarity	NPD5328	Approved
0.6348	Remote Similarity	NPD4786	Approved
0.6333	Remote Similarity	NPD5779	Approved
0.6333	Remote Similarity	NPD4202	Approved
0.6333	Remote Similarity	NPD5778	Approved
0.6331	Remote Similarity	NPD8337	Approved
0.6331	Remote Similarity	NPD8336	Approved
0.6325	Remote Similarity	NPD3573	Approved
0.632	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD3667	Approved
0.6303	Remote Similarity	NPD46	Approved
0.6303	Remote Similarity	NPD6698	Approved
0.629	Remote Similarity	NPD5285	Approved
0.629	Remote Similarity	NPD4696	Approved
0.629	Remote Similarity	NPD5286	Approved
0.629	Remote Similarity	NPD4700	Approved
0.6283	Remote Similarity	NPD7525	Registered
0.6268	Remote Similarity	NPD8338	Approved
0.6261	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD3669	Approved
0.6259	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6079	Approved
0.6241	Remote Similarity	NPD8392	Approved
0.6241	Remote Similarity	NPD8390	Approved
0.6241	Remote Similarity	NPD6274	Approved
0.6241	Remote Similarity	NPD6940	Discontinued
0.6241	Remote Similarity	NPD8391	Approved
0.6239	Remote Similarity	NPD6684	Approved
0.6239	Remote Similarity	NPD7334	Approved
0.6239	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD6409	Approved
0.6239	Remote Similarity	NPD5330	Approved
0.6232	Remote Similarity	NPD8341	Approved
0.6232	Remote Similarity	NPD8342	Approved
0.6232	Remote Similarity	NPD8299	Approved
0.6232	Remote Similarity	NPD8340	Approved
0.623	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5695	Phase 3
0.6222	Remote Similarity	NPD7100	Approved
0.6222	Remote Similarity	NPD7101	Approved
0.621	Remote Similarity	NPD5696	Approved
0.621	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8080	Discontinued
0.619	Remote Similarity	NPD5211	Phase 2
0.619	Remote Similarity	NPD5225	Approved
0.619	Remote Similarity	NPD5224	Approved
0.619	Remote Similarity	NPD4633	Approved
0.619	Remote Similarity	NPD5226	Approved
0.6187	Remote Similarity	NPD8451	Approved
0.6172	Remote Similarity	NPD4768	Approved
0.6172	Remote Similarity	NPD4767	Approved
0.6148	Remote Similarity	NPD6335	Approved
0.6148	Remote Similarity	NPD5282	Discontinued
0.6142	Remote Similarity	NPD5175	Approved
0.6142	Remote Similarity	NPD5174	Approved
0.6134	Remote Similarity	NPD5737	Approved
0.6134	Remote Similarity	NPD6903	Approved
0.6134	Remote Similarity	NPD6672	Approved
0.6131	Remote Similarity	NPD6909	Approved
0.6131	Remote Similarity	NPD6908	Approved
0.6116	Remote Similarity	NPD7637	Suspended
0.6111	Remote Similarity	NPD5223	Approved
0.6111	Remote Similarity	NPD5344	Discontinued
0.6107	Remote Similarity	NPD6371	Approved
0.6106	Remote Similarity	NPD6114	Approved
0.6106	Remote Similarity	NPD6697	Approved
0.6106	Remote Similarity	NPD6115	Approved
0.6106	Remote Similarity	NPD6118	Approved
0.6102	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5141	Approved
0.6087	Remote Similarity	NPD1780	Approved
0.6087	Remote Similarity	NPD1779	Approved
0.6084	Remote Similarity	NPD7799	Discontinued
0.6083	Remote Similarity	NPD4753	Phase 2
0.6083	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD4730	Approved
0.6077	Remote Similarity	NPD4729	Approved
0.6074	Remote Similarity	NPD6317	Approved
0.6068	Remote Similarity	NPD3665	Phase 1
0.6068	Remote Similarity	NPD3133	Approved
0.6068	Remote Similarity	NPD3666	Approved
0.605	Remote Similarity	NPD7524	Approved
0.6048	Remote Similarity	NPD5221	Approved
0.6048	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4697	Phase 3
0.6048	Remote Similarity	NPD5222	Approved
0.6048	Remote Similarity	NPD7839	Suspended

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