NPASS Compound

Structure

NPC225791 OpenBabel07101718192D 86 94 0 0 1 0 0 0 0 0999 V2000 6.7839 -3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5677 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2064 -3.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1855 -3.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9023 2.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8815 2.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7839 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9359 -2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1758 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7197 3.4271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2399 3.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1758 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5439 1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6960 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2399 1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5439 -1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2399 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7197 4.4062 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2399 4.4062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0238 0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.8718 4.8958 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0879 4.8958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0238 1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0238 4.4062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9359 4.4062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6318 0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6318 1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7839 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1758 1.9583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7839 1.9583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8480 0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6960 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7839 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0238 3.4271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9359 3.4271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3278 1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9359 1.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6960 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 0.4896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8480 0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6960 -0.9792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5439 3.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0238 -1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.5677 4.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 4.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8718 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8718 5.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 5.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8718 1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1758 4.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7839 4.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4798 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6318 -1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 -1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8718 2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3278 0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4798 1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1758 2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7839 2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 3 55 1 0 0 0 0 4 55 1 0 0 0 0 5 56 1 0 0 0 0 6 56 1 0 0 0 0 8 58 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 13 34 1 0 0 0 0 14 15 1 0 0 0 0 14 26 2 0 0 0 0 15 31 1 0 0 0 0 16 19 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 32 1 0 0 0 0 18 57 1 0 0 0 0 19 58 1 0 0 0 0 20 27 1 0 0 0 0 20 55 1 0 0 0 0 21 33 1 0 0 0 0 21 55 1 0 0 0 0 22 61 1 0 0 0 0 23 62 1 0 0 0 0 24 63 1 0 0 0 0 25 2 1 1 0 0 0 25 35 1 0 0 0 0 25 78 1 0 0 0 0 26 27 1 0 0 0 0 26 59 1 0 0 0 0 27 60 1 1 0 0 0 28 22 1 1 0 0 0 28 36 1 0 0 0 0 28 79 1 0 0 0 0 29 23 1 6 0 0 0 29 37 1 0 0 0 0 29 80 1 0 0 0 0 30 56 1 0 0 0 0 30 57 1 6 0 0 0 31 57 1 6 0 0 0 31 58 1 0 0 0 0 32 56 1 0 0 0 0 32 82 1 6 0 0 0 33 60 1 1 0 0 0 33 81 1 0 0 0 0 34 64 2 0 0 0 0 34 81 1 0 0 0 0 35 38 1 0 0 0 0 35 65 1 6 0 0 0 36 39 1 0 0 0 0 36 66 1 6 0 0 0 37 40 1 0 0 0 0 37 67 1 6 0 0 0 38 41 1 0 0 0 0 38 68 1 1 0 0 0 39 42 1 0 0 0 0 39 69 1 1 0 0 0 40 46 1 0 0 0 0 40 70 1 6 0 0 0 41 51 1 0 0 0 0 41 71 1 1 0 0 0 42 52 1 0 0 0 0 42 72 1 6 0 0 0 43 44 1 0 0 0 0 43 45 1 0 0 0 0 43 73 1 1 0 0 0 44 47 1 0 0 0 0 44 83 1 6 0 0 0 45 50 1 6 0 0 0 45 84 1 0 0 0 0 46 53 1 0 0 0 0 46 85 1 1 0 0 0 47 54 1 0 0 0 0 47 86 1 1 0 0 0 48 49 1 0 0 0 0 48 59 1 1 0 0 0 48 74 1 0 0 0 0 49 60 1 1 0 0 0 49 75 1 0 0 0 0 50 76 2 0 0 0 0 50 77 1 0 0 0 0 51 78 1 0 0 0 0 51 85 1 6 0 0 0 52 79 1 0 0 0 0 52 86 1 1 0 0 0 53 80 1 0 0 0 0 53 83 1 6 0 0 0 54 82 1 6 0 0 0 54 84 1 0 0 0 0 57 7 1 6 0 0 0 58 59 1 1 0 0 0 59 9 1 1 0 0 0 60 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1232.62
Volume:	1187.308
LogP:	2.386
LogD:	1.338
LogS:	-2.83
# Rotatable Bonds:	17
TPSA:	420.66
# H-Bond Aceptor:	26
# H-Bond Donor:	15
# Rings:	9
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.047
Synthetic Accessibility Score:	7.357
Fsp3:	0.9
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:	-6.401
MDCK Permeability:	0.0003646484692580998
Pgp-inhibitor:	0.257
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	56.196502685546875%
Volume Distribution (VD):	0.043
Pgp-substrate:	13.94763469696045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	-0.0
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.723
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.072
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC225791

Natural Product ID:	NPC225791
*Common Name:**	Sasanquasaponin I
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9S,12aS,14aR,14bR)-9-[(Z)-hex-2-enoyl]oxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:	Sasanquasaponin I
Standard InCHIKey:	IUCFFRZHJQBJND-QBFBLQJXSA-N
Standard InCHI:	InChI=1S/C60H96O26/c1-10-11-12-13-34(64)81-33-21-55(3,4)20-27-26-14-15-31-57(7)18-17-32(56(5,6)30(57)16-19-58(31,8)59(26,9)48(74)49(75)60(27,33)24-63)82-54-47(86-52-42(72)39(69)36(66)28(22-61)79-52)44(43(73)45(84-54)50(76)77)83-53-46(40(70)37(67)29(23-62)80-53)85-51-41(71)38(68)35(65)25(2)78-51/h12-14,25,27-33,35-49,51-54,61-63,65-75H,10-11,15-24H2,1-9H3,(H,76,77)/b13-12-/t25-,27-,28+,29+,30-,31+,32-,33-,35-,36+,37-,38+,39-,40-,41+,42+,43-,44-,45-,46+,47+,48-,49+,51-,52-,53-,54+,57-,58+,59-,60+/m0/s1
SMILES:	CCC/C=CC(=O)O[C@H]1CC(C)(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)[C@H]([C@H]([C@@]12CO)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087225
PubChem CID:	49871628
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
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16926516]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[22834923]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30395460]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32569471]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23380	Camellia japonica	Species	Theaceae	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	4

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	16.4	%	PMID[493403]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	44.8	%	PMID[493403]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	34.9	%	PMID[493403]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	71.5	%	PMID[493403]

☑ 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 NPC225791 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	312
0.1-0.2	1812
0.2-0.3	4658
0.3-0.4	7841
0.4-0.5	12333
0.5-0.6	8602
0.6-0.7	4420
0.7-0.8	1930
0.8-0.85	378
0.85-0.9	207
0.9-0.95	113
0.95-1	91

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC473918
0.9917	High Similarity	NPC71391
0.9917	High Similarity	NPC277212
0.9917	High Similarity	NPC312650
0.9917	High Similarity	NPC192765
0.9917	High Similarity	NPC178264
0.9917	High Similarity	NPC46823
0.9917	High Similarity	NPC30279
0.9835	High Similarity	NPC476774
0.9835	High Similarity	NPC271610
0.9835	High Similarity	NPC476780
0.9835	High Similarity	NPC476775
0.9754	High Similarity	NPC476776
0.9752	High Similarity	NPC477077
0.9752	High Similarity	NPC1314
0.9752	High Similarity	NPC141600
0.9752	High Similarity	NPC107536
0.9752	High Similarity	NPC477076
0.9752	High Similarity	NPC252657
0.9752	High Similarity	NPC305793
0.9752	High Similarity	NPC472267
0.9752	High Similarity	NPC244296
0.9752	High Similarity	NPC9470
0.9752	High Similarity	NPC97918
0.9752	High Similarity	NPC82380
0.9752	High Similarity	NPC252289
0.9752	High Similarity	NPC280029
0.9752	High Similarity	NPC265841
0.9752	High Similarity	NPC470518
0.9752	High Similarity	NPC269484
0.9752	High Similarity	NPC477079
0.9752	High Similarity	NPC470912
0.9752	High Similarity	NPC88311
0.9752	High Similarity	NPC115656
0.9752	High Similarity	NPC273878
0.9752	High Similarity	NPC470913
0.9752	High Similarity	NPC47995
0.9752	High Similarity	NPC11577
0.9677	High Similarity	NPC279915
0.9677	High Similarity	NPC110700
0.9672	High Similarity	NPC477197
0.9669	High Similarity	NPC477193
0.9669	High Similarity	NPC475281
0.9669	High Similarity	NPC477078
0.9669	High Similarity	NPC477075
0.9669	High Similarity	NPC477194
0.9669	High Similarity	NPC477192
0.9669	High Similarity	NPC477191
0.9669	High Similarity	NPC329923
0.9597	High Similarity	NPC476777
0.9597	High Similarity	NPC476778
0.9593	High Similarity	NPC478153
0.9593	High Similarity	NPC478152
0.9593	High Similarity	NPC478150
0.959	High Similarity	NPC477196
0.9516	High Similarity	NPC476779
0.9516	High Similarity	NPC478151
0.9512	High Similarity	NPC264566
0.9512	High Similarity	NPC475167
0.9512	High Similarity	NPC478065
0.9512	High Similarity	NPC329993
0.9512	High Similarity	NPC478064
0.9512	High Similarity	NPC172374
0.9512	High Similarity	NPC301639
0.9512	High Similarity	NPC478155
0.9512	High Similarity	NPC173435
0.9512	High Similarity	NPC475377
0.9512	High Similarity	NPC262796
0.9512	High Similarity	NPC25998
0.9512	High Similarity	NPC476074
0.9512	High Similarity	NPC45346
0.9512	High Similarity	NPC134914
0.9435	High Similarity	NPC478154
0.9435	High Similarity	NPC477195
0.935	High Similarity	NPC470475
0.9268	High Similarity	NPC470516
0.9262	High Similarity	NPC23275
0.9194	High Similarity	NPC470476
0.918	High Similarity	NPC257211
0.9174	High Similarity	NPC302887
0.9174	High Similarity	NPC187618
0.9106	High Similarity	NPC471962
0.9106	High Similarity	NPC471963
0.9106	High Similarity	NPC33068
0.9106	High Similarity	NPC247315
0.9098	High Similarity	NPC236870
0.9098	High Similarity	NPC475591
0.9098	High Similarity	NPC313110
0.9098	High Similarity	NPC10607
0.9098	High Similarity	NPC131469
0.9098	High Similarity	NPC213952
0.9098	High Similarity	NPC4749
0.9098	High Similarity	NPC80986
0.9098	High Similarity	NPC21691
0.9098	High Similarity	NPC187290
0.9091	High Similarity	NPC118440
0.9091	High Similarity	NPC236657
0.9048	High Similarity	NPC222951
0.9048	High Similarity	NPC311178
0.9048	High Similarity	NPC43589
0.9048	High Similarity	NPC300655
0.904	High Similarity	NPC472268
0.904	High Similarity	NPC112492
0.904	High Similarity	NPC23020
0.904	High Similarity	NPC472270
0.904	High Similarity	NPC472269
0.9032	High Similarity	NPC284449
0.9032	High Similarity	NPC469947
0.9032	High Similarity	NPC181066
0.9024	High Similarity	NPC258617
0.9024	High Similarity	NPC14617
0.9024	High Similarity	NPC471964
0.9024	High Similarity	NPC302543
0.9024	High Similarity	NPC262199
0.9024	High Similarity	NPC202666
0.9024	High Similarity	NPC200049
0.9024	High Similarity	NPC283417
0.9024	High Similarity	NPC471961
0.9024	High Similarity	NPC478066
0.9016	High Similarity	NPC62725
0.9016	High Similarity	NPC104372
0.9016	High Similarity	NPC22956
0.9016	High Similarity	NPC159309
0.9016	High Similarity	NPC297263
0.9016	High Similarity	NPC31838
0.9016	High Similarity	NPC64715
0.9016	High Similarity	NPC11242
0.9016	High Similarity	NPC301449
0.9016	High Similarity	NPC86222
0.9016	High Similarity	NPC222580
0.9016	High Similarity	NPC114484
0.9016	High Similarity	NPC171544
0.9016	High Similarity	NPC223301
0.8976	High Similarity	NPC475444
0.8976	High Similarity	NPC473679
0.8976	High Similarity	NPC196874
0.8976	High Similarity	NPC322904
0.8976	High Similarity	NPC475177
0.8976	High Similarity	NPC183816
0.8976	High Similarity	NPC319719
0.8976	High Similarity	NPC233223
0.8976	High Similarity	NPC324933
0.8952	High Similarity	NPC160452
0.8952	High Similarity	NPC470477
0.8943	High Similarity	NPC162574
0.8943	High Similarity	NPC471965
0.8926	High Similarity	NPC470515
0.8923	High Similarity	NPC596
0.8889	High Similarity	NPC45606
0.8889	High Similarity	NPC220838
0.888	High Similarity	NPC285091
0.888	High Similarity	NPC297950
0.888	High Similarity	NPC475368
0.888	High Similarity	NPC470218
0.8871	High Similarity	NPC281148
0.8871	High Similarity	NPC2370
0.8871	High Similarity	NPC44716
0.8871	High Similarity	NPC235405
0.8871	High Similarity	NPC30735
0.8862	High Similarity	NPC75417
0.8852	High Similarity	NPC180550
0.8852	High Similarity	NPC192791
0.8852	High Similarity	NPC114441
0.8852	High Similarity	NPC472949
0.8852	High Similarity	NPC473884
0.8852	High Similarity	NPC208381
0.8852	High Similarity	NPC39211
0.8852	High Similarity	NPC469945
0.8852	High Similarity	NPC470915
0.8852	High Similarity	NPC309780
0.8852	High Similarity	NPC214484
0.8852	High Similarity	NPC35405
0.8852	High Similarity	NPC11551
0.8852	High Similarity	NPC470517
0.8852	High Similarity	NPC6377
0.8852	High Similarity	NPC475171
0.8852	High Similarity	NPC157868
0.8852	High Similarity	NPC470911
0.8846	High Similarity	NPC141215
0.8846	High Similarity	NPC471089
0.8846	High Similarity	NPC190065
0.8843	High Similarity	NPC224121
0.879	High Similarity	NPC40775
0.879	High Similarity	NPC235438
0.879	High Similarity	NPC249848
0.879	High Similarity	NPC107966
0.8779	High Similarity	NPC295885
0.8779	High Similarity	NPC140045
0.877	High Similarity	NPC471548
0.877	High Similarity	NPC286347
0.8769	High Similarity	NPC262813
0.871	High Similarity	NPC31193
0.871	High Similarity	NPC242840
0.8702	High Similarity	NPC251998
0.8699	High Similarity	NPC473401
0.8699	High Similarity	NPC470914
0.8689	High Similarity	NPC475119
0.8689	High Similarity	NPC473405
0.8689	High Similarity	NPC300419
0.8689	High Similarity	NPC473824

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 NPC225791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	1979
0.2-0.3	3716
0.3-0.4	2032
0.4-0.5	695
0.5-0.6	281
0.6-0.7	127
0.7-0.8	30
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9024	High Similarity	NPD8328	Phase 3
0.8689	High Similarity	NPD8295	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8517	Approved
0.8125	Intermediate Similarity	NPD8515	Approved
0.8125	Intermediate Similarity	NPD8516	Approved
0.7984	Intermediate Similarity	NPD8513	Phase 3
0.7895	Intermediate Similarity	NPD7736	Approved
0.7836	Intermediate Similarity	NPD7319	Approved
0.7769	Intermediate Similarity	NPD8294	Approved
0.7769	Intermediate Similarity	NPD8377	Approved
0.7744	Intermediate Similarity	NPD7507	Approved
0.7742	Intermediate Similarity	NPD6686	Approved
0.7717	Intermediate Similarity	NPD8133	Approved
0.771	Intermediate Similarity	NPD8296	Approved
0.771	Intermediate Similarity	NPD8380	Approved
0.771	Intermediate Similarity	NPD8379	Approved
0.771	Intermediate Similarity	NPD8378	Approved
0.771	Intermediate Similarity	NPD8335	Approved
0.771	Intermediate Similarity	NPD8033	Approved
0.768	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6370	Approved
0.746	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7503	Approved
0.7426	Intermediate Similarity	NPD8293	Discontinued
0.7424	Intermediate Similarity	NPD7516	Approved
0.7422	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7492	Approved
0.7368	Intermediate Similarity	NPD6319	Approved
0.7368	Intermediate Similarity	NPD6054	Approved
0.7353	Intermediate Similarity	NPD6616	Approved
0.7348	Intermediate Similarity	NPD7328	Approved
0.7348	Intermediate Similarity	NPD7327	Approved
0.7299	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7231	Intermediate Similarity	NPD6882	Approved
0.7231	Intermediate Similarity	NPD8297	Approved
0.7185	Intermediate Similarity	NPD6015	Approved
0.7185	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7132	Intermediate Similarity	NPD5988	Approved
0.7111	Intermediate Similarity	NPD6059	Approved
0.7109	Intermediate Similarity	NPD6412	Phase 2
0.7097	Intermediate Similarity	NPD4225	Approved
0.705	Intermediate Similarity	NPD8074	Phase 3
0.7023	Intermediate Similarity	NPD6650	Approved
0.7023	Intermediate Similarity	NPD6649	Approved
0.7016	Intermediate Similarity	NPD7902	Approved
0.696	Remote Similarity	NPD7638	Approved
0.6934	Remote Similarity	NPD6921	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6917	Remote Similarity	NPD4632	Approved
0.6911	Remote Similarity	NPD7748	Approved
0.6905	Remote Similarity	NPD7640	Approved
0.6905	Remote Similarity	NPD7639	Approved
0.6894	Remote Similarity	NPD8130	Phase 1
0.687	Remote Similarity	NPD6373	Approved
0.687	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6372	Approved
0.6846	Remote Similarity	NPD5697	Approved
0.6825	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD6883	Approved
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7290	Approved
0.6774	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7900	Approved
0.6769	Remote Similarity	NPD5739	Approved
0.6769	Remote Similarity	NPD6675	Approved
0.6769	Remote Similarity	NPD6402	Approved
0.6769	Remote Similarity	NPD7128	Approved
0.6767	Remote Similarity	NPD6869	Approved
0.6767	Remote Similarity	NPD6617	Approved
0.6767	Remote Similarity	NPD6847	Approved
0.6748	Remote Similarity	NPD7515	Phase 2
0.6742	Remote Similarity	NPD6012	Approved
0.6742	Remote Similarity	NPD6013	Approved
0.6742	Remote Similarity	NPD6014	Approved
0.6714	Remote Similarity	NPD7830	Approved
0.6714	Remote Similarity	NPD7604	Phase 2
0.6714	Remote Similarity	NPD7829	Approved
0.6692	Remote Similarity	NPD4634	Approved
0.6691	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6647	Remote Similarity	NPD7799	Discontinued
0.6643	Remote Similarity	NPD6033	Approved
0.6622	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7260	Phase 2
0.662	Remote Similarity	NPD6336	Discontinued
0.6591	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5701	Approved
0.6591	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5344	Discontinued
0.6573	Remote Similarity	NPD8448	Approved
0.6565	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8392	Approved
0.6552	Remote Similarity	NPD8391	Approved
0.6552	Remote Similarity	NPD8390	Approved
0.6532	Remote Similarity	NPD6698	Approved
0.6532	Remote Similarity	NPD46	Approved
0.6503	Remote Similarity	NPD8451	Approved
0.6491	Remote Similarity	NPD8368	Discontinued
0.6486	Remote Similarity	NPD8415	Approved
0.648	Remote Similarity	NPD6411	Approved
0.648	Remote Similarity	NPD7983	Approved
0.6443	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7101	Approved
0.6429	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD7100	Approved
0.6429	Remote Similarity	NPD5778	Approved
0.6412	Remote Similarity	NPD7632	Discontinued
0.6412	Remote Similarity	NPD5211	Phase 2
0.64	Remote Similarity	NPD7838	Discovery
0.6397	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5285	Approved
0.6385	Remote Similarity	NPD4696	Approved
0.6385	Remote Similarity	NPD5286	Approved
0.6379	Remote Similarity	NPD8407	Phase 2
0.6364	Remote Similarity	NPD7642	Approved
0.6357	Remote Similarity	NPD6335	Approved
0.6346	Remote Similarity	NPD7625	Phase 1
0.6338	Remote Similarity	NPD8444	Approved
0.6331	Remote Similarity	NPD6868	Approved
0.6331	Remote Similarity	NPD6274	Approved
0.6324	Remote Similarity	NPD6371	Approved
0.632	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6101	Approved
0.6319	Remote Similarity	NPD8342	Approved
0.6319	Remote Similarity	NPD8340	Approved
0.6319	Remote Similarity	NPD8341	Approved
0.6319	Remote Similarity	NPD8299	Approved
0.6316	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5141	Approved
0.6294	Remote Similarity	NPD8080	Discontinued
0.629	Remote Similarity	NPD3573	Approved
0.6288	Remote Similarity	NPD5225	Approved
0.6288	Remote Similarity	NPD5226	Approved
0.6288	Remote Similarity	NPD4633	Approved
0.6288	Remote Similarity	NPD5224	Approved
0.6286	Remote Similarity	NPD6317	Approved
0.6279	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5221	Approved
0.6279	Remote Similarity	NPD5222	Approved
0.6269	Remote Similarity	NPD6008	Approved
0.626	Remote Similarity	NPD6648	Approved
0.6257	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6067	Discontinued
0.6242	Remote Similarity	NPD6845	Suspended
0.6241	Remote Similarity	NPD5175	Approved
0.6241	Remote Similarity	NPD6314	Approved
0.6241	Remote Similarity	NPD6313	Approved
0.6241	Remote Similarity	NPD5174	Approved
0.6236	Remote Similarity	NPD8435	Approved
0.6232	Remote Similarity	NPD6053	Discontinued
0.6231	Remote Similarity	NPD5173	Approved
0.6231	Remote Similarity	NPD4755	Approved
0.6231	Remote Similarity	NPD6084	Phase 2
0.6231	Remote Similarity	NPD6083	Phase 2
0.622	Remote Similarity	NPD8034	Phase 2
0.622	Remote Similarity	NPD8035	Phase 2
0.622	Remote Similarity	NPD6079	Approved
0.6216	Remote Similarity	NPD5956	Approved
0.6212	Remote Similarity	NPD5223	Approved
0.6202	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4730	Approved
0.6176	Remote Similarity	NPD4729	Approved
0.6172	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD7839	Suspended
0.6154	Remote Similarity	NPD4697	Phase 3
0.615	Remote Similarity	NPD8319	Approved
0.615	Remote Similarity	NPD8320	Phase 1
0.6145	Remote Similarity	NPD8360	Approved
0.6145	Remote Similarity	NPD8361	Approved
0.6136	Remote Similarity	NPD8313	Approved
0.6136	Remote Similarity	NPD8312	Approved
0.6136	Remote Similarity	NPD4700	Approved
0.6133	Remote Similarity	NPD8338	Approved
0.6127	Remote Similarity	NPD7641	Discontinued
0.6124	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6908	Approved
0.6111	Remote Similarity	NPD6909	Approved
0.6111	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD8450	Suspended
0.6087	Remote Similarity	NPD5250	Approved
0.6087	Remote Similarity	NPD5248	Approved
0.6087	Remote Similarity	NPD5251	Approved
0.6087	Remote Similarity	NPD5249	Phase 3
0.6087	Remote Similarity	NPD5247	Approved
0.6081	Remote Similarity	NPD8337	Approved
0.6081	Remote Similarity	NPD8336	Approved
0.6063	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD5328	Approved
0.6062	Remote Similarity	NPD7236	Approved
0.6061	Remote Similarity	NPD5696	Approved
0.6047	Remote Similarity	NPD8171	Discontinued
0.6039	Remote Similarity	NPD6333	Approved
0.6039	Remote Similarity	NPD6334	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