NPASS Compound

Structure

CID124828 OpenBabel06191715482D 90 99 0 0 1 0 0 0 0 0999 V2000 9.2042 -0.5238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9096 -3.4321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1879 3.7895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2077 3.7895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5466 0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8856 -2.8093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 -1.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7081 -8.0302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4283 -7.1513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6288 -5.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9889 -5.5114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1214 -7.8444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3219 -6.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8489 1.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6978 0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2426 -4.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6978 -1.9604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2444 -0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3955 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8489 -1.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5466 2.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5466 1.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 2.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 -0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4888 -5.8812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9054 -2.8093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5111 0.1694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1633 -2.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6820 -6.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0682 -7.5908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4888 -4.9010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5466 -1.4703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6978 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6978 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2444 -1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5495 -3.8715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 1.1162 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3376 -4.4109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0716 1.8093 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3376 -3.4307 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0933 -4.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9421 -4.4109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1249 1.5556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4888 -2.9406 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3638 -1.2848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1101 -2.2316 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2444 -4.4109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9421 -3.4307 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6707 -0.5917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3955 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8712 0.6088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6399 -3.4307 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7239 -0.8454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0933 -2.9406 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0840 -0.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 2.9406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5466 -0.4901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3955 -1.9604 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8489 -0.4901 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 1.6978 0.9802 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3376 -6.3713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3955 -3.6581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5466 -0.4901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6027 -4.1252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7116 1.3698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1865 -4.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3253 2.7561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1865 -2.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0933 -5.8812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7910 -4.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4317 2.2487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4888 -1.9604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3106 -1.0311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3955 -5.8812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5466 -4.4109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8303 -1.3528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7613 -8.2839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5643 -0.0843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4702 -1.7922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6399 -4.4109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0933 -1.9604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8032 -2.9247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2444 -3.4307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7910 -2.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9244 0.3551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0308 -0.1523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 59 1 0 0 0 0 4 59 1 0 0 0 0 7 62 1 0 0 0 0 9 81 1 0 0 0 0 10 13 1 0 0 0 0 10 30 2 0 0 0 0 11 14 2 0 0 0 0 11 30 1 0 0 0 0 12 17 2 0 0 0 0 12 30 1 0 0 0 0 13 31 2 0 0 0 0 14 31 1 0 0 0 0 15 16 1 0 0 0 0 15 32 2 0 0 0 0 16 36 1 0 0 0 0 17 39 1 0 0 0 0 18 21 1 0 0 0 0 18 35 1 0 0 0 0 19 20 1 0 0 0 0 19 38 1 0 0 0 0 20 60 1 0 0 0 0 21 62 1 0 0 0 0 22 23 1 0 0 0 0 22 59 1 0 0 0 0 23 64 1 0 0 0 0 24 33 1 0 0 0 0 24 59 1 0 0 0 0 25 37 1 0 0 0 0 25 63 1 0 0 0 0 26 65 1 0 0 0 0 27 61 1 0 0 0 0 27 66 2 0 0 0 0 28 1 1 6 0 0 0 28 40 1 0 0 0 0 28 82 1 0 0 0 0 29 2 1 1 0 0 0 29 49 1 0 0 0 0 29 83 1 0 0 0 0 31 81 1 0 0 0 0 32 33 1 0 0 0 0 32 63 1 0 0 0 0 33 64 1 6 0 0 0 34 26 1 6 0 0 0 34 41 1 0 0 0 0 34 84 1 0 0 0 0 35 60 1 1 0 0 0 35 61 1 0 0 0 0 36 60 1 1 0 0 0 36 62 1 0 0 0 0 37 64 1 6 0 0 0 37 67 1 0 0 0 0 38 61 1 1 0 0 0 38 85 1 0 0 0 0 39 68 2 0 0 0 0 39 86 1 0 0 0 0 40 42 1 0 0 0 0 40 69 1 1 0 0 0 41 43 1 0 0 0 0 41 70 1 6 0 0 0 42 46 1 0 0 0 0 42 71 1 6 0 0 0 43 47 1 0 0 0 0 43 72 1 6 0 0 0 44 45 1 0 0 0 0 44 50 1 0 0 0 0 44 73 1 1 0 0 0 45 51 1 0 0 0 0 45 74 1 6 0 0 0 46 54 1 0 0 0 0 46 75 1 6 0 0 0 47 55 1 0 0 0 0 47 76 1 1 0 0 0 48 49 1 0 0 0 0 48 52 1 0 0 0 0 48 77 1 1 0 0 0 49 86 1 1 0 0 0 50 53 1 6 0 0 0 50 87 1 0 0 0 0 51 57 1 0 0 0 0 51 88 1 1 0 0 0 52 56 1 0 0 0 0 52 89 1 6 0 0 0 53 78 2 0 0 0 0 53 79 1 0 0 0 0 54 82 1 0 0 0 0 54 89 1 1 0 0 0 55 84 1 0 0 0 0 55 88 1 6 0 0 0 56 83 1 0 0 0 0 56 90 1 1 0 0 0 57 85 1 6 0 0 0 57 87 1 0 0 0 0 58 80 2 0 0 0 0 58 90 1 0 0 0 0 60 5 1 1 0 0 0 61 6 1 1 0 0 0 62 63 1 6 0 0 0 63 8 1 6 0 0 0 64 58 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1276.59
Volume:	1234.753
LogP:	2.642
LogD:	1.533
LogS:	-3.532
# Rotatable Bonds:	17
TPSA:	403.34
# H-Bond Aceptor:	26
# H-Bond Donor:	12
# Rings:	10
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.037
Synthetic Accessibility Score:	7.315
Fsp3:	0.781
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:	-6.299
MDCK Permeability:	0.00023527606390416622
Pgp-inhibitor:	0.061
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	70.52872467041016%
Volume Distribution (VD):	0.298
Pgp-substrate:	14.966919898986816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.251
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	0.232
Half-life (T1/2):	0.533

ADMET: Toxicity

hERG Blockers:	0.211
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.393
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.703
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.797

Download Data

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

Natural Product: NPC124828

Natural Product ID:	NPC124828
*Common Name:**	Jenisseensoside C/D
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-4-formyl-8-hydroxy-8a-[(2S,3R,4S,5R,6R)-4-hydroxy-5-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxycarbonyl-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:	Jenisseensoside C/D
Standard InCHIKey:	OZOKLZWUTXESGO-BBHDCDGUSA-N
Standard InCHI:	InChI=1S/C64H92O26/c1-28-40(69)42(71)46(75)54(82-28)89-52-48(77)49(86-39(68)17-12-30-10-13-31(81-9)14-11-30)29(2)83-56(52)90-58(80)64-23-22-59(3,4)24-33(64)32-15-16-36-60(5)20-19-38(61(6,27-66)35(60)18-21-62(36,7)63(32,8)25-37(64)67)85-57-51(45(74)44(73)50(87-57)53(78)79)88-55-47(76)43(72)41(70)34(26-65)84-55/h10-15,17,27-29,33-38,40-52,54-57,65,67,69-77H,16,18-26H2,1-9H3,(H,78,79)/b17-12+/t28-,29+,33-,34+,35+,36+,37+,38-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49-,50-,51+,52+,54-,55-,56-,57+,60-,61-,62+,63+,64+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)C(=O)O)O[C@H]2CC[C@]3([C@H]([C@]2(C)C=O)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]2O[C@H](C)[C@@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)OC(=O)/C=C/c2ccc(cc2)OC)O)C)C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509232
PubChem CID:	44576216
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
NPO11017	Silene fortunei	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444678]
NPO11017	Silene fortunei	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917300]
NPO11017	Silene fortunei	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11017	Silene fortunei	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11017	Silene fortunei	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10820	Galium spurium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10187	Protoblastenia incrustans	Species	Psoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	FC	=	9.0	n.a.	PMID[543705]
NPT15	Cell Line	Jurkat	Homo sapiens	Activity	=	1.36	n.a.	PMID[543705]

☑ 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 NPC124828 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	413
0.1-0.2	1481
0.2-0.3	3190
0.3-0.4	6030
0.4-0.5	9142
0.5-0.6	9020
0.6-0.7	9897
0.7-0.8	3299
0.8-0.85	178
0.85-0.9	45
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8882	High Similarity	NPC469772
0.8882	High Similarity	NPC100925
0.8882	High Similarity	NPC135334
0.8882	High Similarity	NPC469777
0.8882	High Similarity	NPC469776
0.8882	High Similarity	NPC469778
0.8882	High Similarity	NPC295941
0.8882	High Similarity	NPC469773
0.8882	High Similarity	NPC469775
0.8882	High Similarity	NPC32723
0.8882	High Similarity	NPC469774
0.8721	High Similarity	NPC471871
0.8683	High Similarity	NPC329960
0.8683	High Similarity	NPC150893
0.8683	High Similarity	NPC295408
0.8663	High Similarity	NPC13989
0.8655	High Similarity	NPC471870
0.8642	High Similarity	NPC329657
0.8613	High Similarity	NPC195972
0.8596	High Similarity	NPC189704
0.858	High Similarity	NPC326278
0.8547	High Similarity	NPC476067
0.8547	High Similarity	NPC475121
0.8539	High Similarity	NPC299855
0.8539	High Similarity	NPC96194
0.8538	High Similarity	NPC477466
0.8538	High Similarity	NPC477473
0.8538	High Similarity	NPC477469
0.8538	High Similarity	NPC477471
0.8537	High Similarity	NPC69425
0.8529	High Similarity	NPC327694
0.8514	High Similarity	NPC475613
0.848	Intermediate Similarity	NPC102465
0.848	Intermediate Similarity	NPC318472
0.8471	Intermediate Similarity	NPC471873
0.8452	Intermediate Similarity	NPC471878
0.8443	Intermediate Similarity	NPC477467
0.8412	Intermediate Similarity	NPC471869
0.8407	Intermediate Similarity	NPC475299
0.8385	Intermediate Similarity	NPC111466
0.8383	Intermediate Similarity	NPC477472
0.8383	Intermediate Similarity	NPC477470
0.8383	Intermediate Similarity	NPC477474
0.8352	Intermediate Similarity	NPC112708
0.8352	Intermediate Similarity	NPC473630
0.8343	Intermediate Similarity	NPC472639
0.8343	Intermediate Similarity	NPC472638
0.8333	Intermediate Similarity	NPC40085
0.8333	Intermediate Similarity	NPC264270
0.8324	Intermediate Similarity	NPC473776
0.8324	Intermediate Similarity	NPC473205
0.8306	Intermediate Similarity	NPC473711
0.8297	Intermediate Similarity	NPC230670
0.8297	Intermediate Similarity	NPC71385
0.8286	Intermediate Similarity	NPC472803
0.828	Intermediate Similarity	NPC131405
0.8266	Intermediate Similarity	NPC100333
0.8249	Intermediate Similarity	NPC186800
0.8249	Intermediate Similarity	NPC470667
0.8246	Intermediate Similarity	NPC211777
0.8229	Intermediate Similarity	NPC160818
0.8229	Intermediate Similarity	NPC169299
0.8218	Intermediate Similarity	NPC469419
0.8216	Intermediate Similarity	NPC470197
0.8216	Intermediate Similarity	NPC282474
0.8216	Intermediate Similarity	NPC470200
0.8216	Intermediate Similarity	NPC470195
0.8216	Intermediate Similarity	NPC470193
0.8216	Intermediate Similarity	NPC470198
0.8216	Intermediate Similarity	NPC470194
0.8216	Intermediate Similarity	NPC316274
0.8216	Intermediate Similarity	NPC470196
0.8208	Intermediate Similarity	NPC475779
0.8204	Intermediate Similarity	NPC119252
0.8202	Intermediate Similarity	NPC66820
0.8202	Intermediate Similarity	NPC176246
0.8202	Intermediate Similarity	NPC76112
0.8202	Intermediate Similarity	NPC170018
0.8202	Intermediate Similarity	NPC92403
0.8198	Intermediate Similarity	NPC198047
0.8193	Intermediate Similarity	NPC473719
0.8192	Intermediate Similarity	NPC262386
0.8182	Intermediate Similarity	NPC470330
0.8171	Intermediate Similarity	NPC82602
0.8167	Intermediate Similarity	NPC85316
0.8167	Intermediate Similarity	NPC197357
0.8166	Intermediate Similarity	NPC160882
0.8161	Intermediate Similarity	NPC99216
0.815	Intermediate Similarity	NPC146991
0.814	Intermediate Similarity	NPC207978
0.8136	Intermediate Similarity	NPC148185
0.8136	Intermediate Similarity	NPC477617
0.8136	Intermediate Similarity	NPC183441
0.8132	Intermediate Similarity	NPC241847
0.8132	Intermediate Similarity	NPC473686
0.8132	Intermediate Similarity	NPC221140
0.8132	Intermediate Similarity	NPC229817
0.8132	Intermediate Similarity	NPC475220
0.8132	Intermediate Similarity	NPC475352
0.8118	Intermediate Similarity	NPC472807
0.8118	Intermediate Similarity	NPC477736
0.8111	Intermediate Similarity	NPC72783
0.8108	Intermediate Similarity	NPC470199
0.8108	Intermediate Similarity	NPC314459
0.8103	Intermediate Similarity	NPC97574
0.8103	Intermediate Similarity	NPC93172
0.8103	Intermediate Similarity	NPC120012
0.8103	Intermediate Similarity	NPC100420
0.8101	Intermediate Similarity	NPC289876
0.8101	Intermediate Similarity	NPC231787
0.8098	Intermediate Similarity	NPC314672
0.8095	Intermediate Similarity	NPC231668
0.8092	Intermediate Similarity	NPC477627
0.809	Intermediate Similarity	NPC65118
0.8087	Intermediate Similarity	NPC294863
0.8087	Intermediate Similarity	NPC282636
0.8077	Intermediate Similarity	NPC224557
0.8077	Intermediate Similarity	NPC75574
0.8077	Intermediate Similarity	NPC292706
0.807	Intermediate Similarity	NPC10945
0.8068	Intermediate Similarity	NPC128403
0.8068	Intermediate Similarity	NPC302392
0.8066	Intermediate Similarity	NPC477860
0.8066	Intermediate Similarity	NPC475161
0.8059	Intermediate Similarity	NPC469771
0.8059	Intermediate Similarity	NPC477735
0.8054	Intermediate Similarity	NPC48474
0.8049	Intermediate Similarity	NPC204644
0.8047	Intermediate Similarity	NPC48671
0.8047	Intermediate Similarity	NPC473773
0.8047	Intermediate Similarity	NPC475579
0.8045	Intermediate Similarity	NPC475244
0.8045	Intermediate Similarity	NPC223735
0.8045	Intermediate Similarity	NPC307754
0.8043	Intermediate Similarity	NPC205721
0.8036	Intermediate Similarity	NPC327962
0.8036	Intermediate Similarity	NPC162569
0.8036	Intermediate Similarity	NPC116292
0.8036	Intermediate Similarity	NPC267469
0.8036	Intermediate Similarity	NPC12006
0.8036	Intermediate Similarity	NPC179128
0.8036	Intermediate Similarity	NPC35160
0.8036	Intermediate Similarity	NPC87630
0.8034	Intermediate Similarity	NPC474522
0.8034	Intermediate Similarity	NPC470714
0.8034	Intermediate Similarity	NPC470715
0.8034	Intermediate Similarity	NPC470716
0.8033	Intermediate Similarity	NPC87583
0.8033	Intermediate Similarity	NPC33083
0.8024	Intermediate Similarity	NPC477483
0.8024	Intermediate Similarity	NPC325032
0.8023	Intermediate Similarity	NPC268602
0.8023	Intermediate Similarity	NPC266545
0.8023	Intermediate Similarity	NPC202428
0.8023	Intermediate Similarity	NPC262872
0.8022	Intermediate Similarity	NPC475662
0.8022	Intermediate Similarity	NPC473717
0.8022	Intermediate Similarity	NPC293227
0.8022	Intermediate Similarity	NPC473631
0.8012	Intermediate Similarity	NPC320734
0.8011	Intermediate Similarity	NPC58538
0.8011	Intermediate Similarity	NPC187441
0.8011	Intermediate Similarity	NPC200726
0.8011	Intermediate Similarity	NPC306475
0.8011	Intermediate Similarity	NPC283980
0.8	Intermediate Similarity	NPC201814
0.8	Intermediate Similarity	NPC227297
0.8	Intermediate Similarity	NPC471874
0.8	Intermediate Similarity	NPC25889
0.8	Intermediate Similarity	NPC25491
0.7989	Intermediate Similarity	NPC72554
0.7989	Intermediate Similarity	NPC471493
0.7989	Intermediate Similarity	NPC473467
0.7989	Intermediate Similarity	NPC30011
0.7989	Intermediate Similarity	NPC203751
0.7989	Intermediate Similarity	NPC475197
0.7989	Intermediate Similarity	NPC97817
0.7989	Intermediate Similarity	NPC168789
0.7988	Intermediate Similarity	NPC472022
0.7988	Intermediate Similarity	NPC472005
0.7988	Intermediate Similarity	NPC265395
0.7988	Intermediate Similarity	NPC237549
0.7988	Intermediate Similarity	NPC158333
0.7988	Intermediate Similarity	NPC473414
0.7988	Intermediate Similarity	NPC256142
0.7988	Intermediate Similarity	NPC472030
0.7988	Intermediate Similarity	NPC118033
0.7988	Intermediate Similarity	NPC257213
0.7988	Intermediate Similarity	NPC304876
0.7988	Intermediate Similarity	NPC475379
0.7988	Intermediate Similarity	NPC1173
0.7988	Intermediate Similarity	NPC249471
0.7988	Intermediate Similarity	NPC242262
0.7979	Intermediate Similarity	NPC3474
0.7978	Intermediate Similarity	NPC249560
0.7978	Intermediate Similarity	NPC106700
0.7978	Intermediate Similarity	NPC52598
0.7978	Intermediate Similarity	NPC223860
0.7978	Intermediate Similarity	NPC193698
0.7978	Intermediate Similarity	NPC164704

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 NPC124828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	912
0.2-0.3	1936
0.3-0.4	2704
0.4-0.5	1909
0.5-0.6	974
0.6-0.7	297
0.7-0.8	64
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8202	Intermediate Similarity	NPD8313	Approved
0.8202	Intermediate Similarity	NPD8312	Approved
0.8187	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD8455	Phase 2
0.7921	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD8434	Phase 2
0.7824	Intermediate Similarity	NPD7458	Discontinued
0.7814	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7228	Approved
0.7747	Intermediate Similarity	NPD7808	Phase 3
0.7692	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD7240	Approved
0.7688	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7435	Discontinued
0.7637	Intermediate Similarity	NPD6797	Phase 2
0.7629	Intermediate Similarity	NPD8320	Phase 1
0.7629	Intermediate Similarity	NPD8319	Approved
0.7584	Intermediate Similarity	NPD8127	Discontinued
0.7582	Intermediate Similarity	NPD7074	Phase 3
0.7569	Intermediate Similarity	NPD7799	Discontinued
0.7569	Intermediate Similarity	NPD3751	Discontinued
0.7563	Intermediate Similarity	NPD8151	Discontinued
0.7543	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3787	Discontinued
0.7525	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7874	Approved
0.7514	Intermediate Similarity	NPD7075	Discontinued
0.7514	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7698	Approved
0.7486	Intermediate Similarity	NPD37	Approved
0.7486	Intermediate Similarity	NPD7472	Approved
0.7459	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4967	Phase 2
0.7458	Intermediate Similarity	NPD4966	Approved
0.7458	Intermediate Similarity	NPD4965	Approved
0.7456	Intermediate Similarity	NPD4628	Phase 3
0.7456	Intermediate Similarity	NPD8166	Discontinued
0.7449	Intermediate Similarity	NPD7870	Phase 2
0.7449	Intermediate Similarity	NPD7871	Phase 2
0.7446	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7054	Approved
0.7424	Intermediate Similarity	NPD7701	Phase 2
0.7423	Intermediate Similarity	NPD6777	Approved
0.7423	Intermediate Similarity	NPD6781	Approved
0.7423	Intermediate Similarity	NPD6779	Approved
0.7423	Intermediate Similarity	NPD6776	Approved
0.7423	Intermediate Similarity	NPD6778	Approved
0.7423	Intermediate Similarity	NPD6780	Approved
0.7423	Intermediate Similarity	NPD6782	Approved
0.741	Intermediate Similarity	NPD7097	Phase 1
0.7405	Intermediate Similarity	NPD6559	Discontinued
0.7405	Intermediate Similarity	NPD7685	Pre-registration
0.74	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7783	Phase 2
0.7394	Intermediate Similarity	NPD8150	Discontinued
0.7374	Intermediate Similarity	NPD6234	Discontinued
0.7371	Intermediate Similarity	NPD6599	Discontinued
0.7345	Intermediate Similarity	NPD7819	Suspended
0.732	Intermediate Similarity	NPD7699	Phase 2
0.732	Intermediate Similarity	NPD7700	Phase 2
0.7313	Intermediate Similarity	NPD7801	Approved
0.7312	Intermediate Similarity	NPD8368	Discontinued
0.7308	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6801	Discontinued
0.7278	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD4380	Phase 2
0.7268	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6166	Phase 2
0.7246	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6190	Approved
0.7198	Intermediate Similarity	NPD7199	Phase 2
0.7196	Intermediate Similarity	NPD8407	Phase 2
0.7189	Intermediate Similarity	NPD3818	Discontinued
0.7186	Intermediate Similarity	NPD6355	Discontinued
0.7184	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6534	Approved
0.7165	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD5844	Phase 1
0.7151	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7135	Intermediate Similarity	NPD7473	Discontinued
0.7126	Intermediate Similarity	NPD6799	Approved
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5402	Approved
0.7111	Intermediate Similarity	NPD3817	Phase 2
0.7111	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6798	Discontinued
0.7104	Intermediate Similarity	NPD6959	Discontinued
0.7093	Intermediate Similarity	NPD6674	Discontinued
0.7085	Intermediate Similarity	NPD6823	Phase 2
0.7081	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7236	Approved
0.7066	Intermediate Similarity	NPD6233	Phase 2
0.7065	Intermediate Similarity	NPD6232	Discontinued
0.7056	Intermediate Similarity	NPD5761	Phase 2
0.7056	Intermediate Similarity	NPD5760	Phase 2
0.7053	Intermediate Similarity	NPD8404	Phase 2
0.7052	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7680	Approved
0.7048	Intermediate Similarity	NPD7095	Approved
0.7047	Intermediate Similarity	NPD8435	Approved
0.7039	Intermediate Similarity	NPD7411	Suspended
0.7037	Intermediate Similarity	NPD6764	Approved
0.7037	Intermediate Similarity	NPD6765	Approved
0.702	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5403	Approved
0.6989	Remote Similarity	NPD5401	Approved
0.6985	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7768	Phase 2
0.6977	Remote Similarity	NPD5762	Approved
0.6977	Remote Similarity	NPD5763	Approved
0.6966	Remote Similarity	NPD7239	Suspended
0.6959	Remote Similarity	NPD8361	Approved
0.6959	Remote Similarity	NPD8360	Approved
0.6957	Remote Similarity	NPD5494	Approved
0.6943	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3226	Approved
0.6914	Remote Similarity	NPD8328	Phase 3
0.691	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6784	Approved
0.6891	Remote Similarity	NPD6785	Approved
0.6889	Remote Similarity	NPD7028	Phase 2
0.6881	Remote Similarity	NPD7497	Discontinued
0.6868	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6212	Phase 3
0.6853	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6213	Phase 3
0.6834	Remote Similarity	NPD8485	Approved
0.6833	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4060	Phase 1
0.6813	Remote Similarity	NPD1934	Approved
0.6805	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2534	Approved
0.6798	Remote Similarity	NPD2532	Approved
0.6798	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2533	Approved
0.6798	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3882	Suspended
0.6782	Remote Similarity	NPD2346	Discontinued
0.6778	Remote Similarity	NPD1653	Approved
0.6776	Remote Similarity	NPD1465	Phase 2
0.6765	Remote Similarity	NPD8032	Phase 2
0.6763	Remote Similarity	NPD2799	Discontinued
0.6763	Remote Similarity	NPD7033	Discontinued
0.675	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4534	Discontinued
0.6732	Remote Similarity	NPD7999	Approved
0.6725	Remote Similarity	NPD4140	Approved
0.6724	Remote Similarity	NPD6100	Approved
0.6724	Remote Similarity	NPD6099	Approved
0.6724	Remote Similarity	NPD2935	Discontinued
0.6724	Remote Similarity	NPD2438	Suspended
0.6714	Remote Similarity	NPD7930	Approved
0.6704	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6677	Suspended
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4110	Phase 3
0.665	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1549	Phase 2
0.6647	Remote Similarity	NPD8651	Approved
0.6646	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD919	Approved
0.6629	Remote Similarity	NPD2796	Approved
0.6627	Remote Similarity	NPD1608	Approved
0.6613	Remote Similarity	NPD7057	Phase 3
0.6613	Remote Similarity	NPD7058	Phase 2
0.6611	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8059	Phase 3
0.6606	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD2801	Approved
0.6591	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5735	Approved
0.6582	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3748	Approved
0.6571	Remote Similarity	NPD1510	Phase 2
0.657	Remote Similarity	NPD6663	Approved
0.6568	Remote Similarity	NPD2798	Approved
0.6566	Remote Similarity	NPD1091	Approved
0.6554	Remote Similarity	NPD5958	Discontinued
0.655	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1283	Approved
0.6538	Remote Similarity	NPD7584	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