NPASS Compound

Structure

NPC181066 OpenBabel07101718222D 80 88 0 0 1 0 0 0 0 0999 V2000 1.7126 -7.9101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4139 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9196 -0.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4139 -1.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9196 -1.1212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8563 -2.4719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8563 1.4831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8563 0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8563 -1.4831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 -0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 -3.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7126 -2.9663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7126 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4252 0.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5689 1.4831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5689 -0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8444 -4.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4192 -0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 -4.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 -7.4157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8563 -0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7126 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9881 -4.9438 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4192 -1.4831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4252 -4.9438 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5689 -1.4831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8563 -1.4831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8563 1.4831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4252 -2.9663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9881 -5.9326 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2755 -1.9775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1318 -6.4270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2755 -2.9663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2815 -6.4270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2755 -5.9326 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1378 -5.9326 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8504 -1.9775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4252 -5.9326 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8504 -2.9663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9941 -1.4831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4192 -3.4607 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9941 -3.4607 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9941 -0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2755 -4.9438 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1378 -4.9438 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5629 -2.9663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1378 -2.9663 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4252 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4252 -1.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7126 -1.9775 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8563 -0.4944 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 -1.7126 0.9888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.7007 -4.9438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5629 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7126 -4.9438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4252 -7.9101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8563 2.4719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8444 -6.4270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1318 -1.4831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1318 -7.4157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1318 -3.4607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2815 -7.4157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4192 -6.4270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9941 -6.4270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7067 -1.4831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8504 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1378 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7126 1.9775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 -6.4270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1318 -4.4494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5629 -1.9775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2815 -4.4494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2815 -3.4607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7067 -3.4607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1378 -1.9775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4192 -4.4494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9941 -4.4494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 50 1 0 0 0 0 3 50 1 0 0 0 0 4 51 1 0 0 0 0 5 51 1 0 0 0 0 7 53 1 0 0 0 0 9 10 1 0 0 0 0 9 23 2 0 0 0 0 10 29 1 0 0 0 0 11 14 1 0 0 0 0 11 28 1 0 0 0 0 12 13 1 0 0 0 0 12 31 1 0 0 0 0 13 52 1 0 0 0 0 14 53 1 0 0 0 0 15 16 1 0 0 0 0 15 50 1 0 0 0 0 16 55 1 0 0 0 0 17 24 1 0 0 0 0 17 50 1 0 0 0 0 18 30 1 0 0 0 0 18 54 1 0 0 0 0 19 56 1 0 0 0 0 20 57 1 0 0 0 0 21 58 1 0 0 0 0 22 59 2 0 0 0 0 22 72 1 0 0 0 0 23 24 1 0 0 0 0 23 54 1 0 0 0 0 24 55 1 6 0 0 0 25 19 1 6 0 0 0 25 32 1 0 0 0 0 25 73 1 0 0 0 0 26 20 1 6 0 0 0 26 33 1 0 0 0 0 26 74 1 0 0 0 0 27 21 1 1 0 0 0 27 40 1 0 0 0 0 27 75 1 0 0 0 0 28 51 1 0 0 0 0 28 52 1 1 0 0 0 29 52 1 1 0 0 0 29 53 1 0 0 0 0 30 55 1 0 0 0 0 30 60 2 0 0 0 0 31 51 1 0 0 0 0 31 76 1 1 0 0 0 32 34 1 0 0 0 0 32 61 1 1 0 0 0 33 35 1 0 0 0 0 33 62 1 6 0 0 0 34 37 1 0 0 0 0 34 63 1 6 0 0 0 35 43 1 0 0 0 0 35 64 1 6 0 0 0 36 38 1 0 0 0 0 36 40 1 0 0 0 0 36 65 1 1 0 0 0 37 46 1 0 0 0 0 37 66 1 1 0 0 0 38 47 1 0 0 0 0 38 67 1 6 0 0 0 39 41 1 0 0 0 0 39 42 1 0 0 0 0 39 68 1 1 0 0 0 40 72 1 1 0 0 0 41 44 1 0 0 0 0 41 77 1 6 0 0 0 42 45 1 6 0 0 0 42 78 1 0 0 0 0 43 48 1 0 0 0 0 43 79 1 1 0 0 0 44 49 1 0 0 0 0 44 80 1 1 0 0 0 45 69 2 0 0 0 0 45 70 1 0 0 0 0 46 73 1 0 0 0 0 46 79 1 6 0 0 0 47 75 1 0 0 0 0 47 80 1 1 0 0 0 48 74 1 0 0 0 0 48 77 1 6 0 0 0 49 76 1 6 0 0 0 49 78 1 0 0 0 0 52 6 1 1 0 0 0 53 54 1 6 0 0 0 54 8 1 6 0 0 0 55 71 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1146.55
Volume:	1092.037
LogP:	1.288
LogD:	1.079
LogS:	-2.623
# Rotatable Bonds:	14
TPSA:	397.27
# H-Bond Aceptor:	25
# H-Bond Donor:	13
# Rings:	9
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.054
Synthetic Accessibility Score:	6.99
Fsp3:	0.909
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:	-6.376
MDCK Permeability:	0.0002551692887209356
Pgp-inhibitor:	0.527
Pgp-substrate:	0.125
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.851
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	57.60138702392578%
Volume Distribution (VD):	0.05
Pgp-substrate:	22.452062606811523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	0.151
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.024
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.562

Download Data

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

Natural Product: NPC181066

Natural Product ID:	NPC181066
*Common Name:**	Camellioside B
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aR,12aS,14aR,14bR)-8a-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8-oxo-2,3,4a,5,6,7,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-yl]oxy]-5-[(2S,3R,4R,5R,6R)-5-acetyloxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxyoxane-2-carboxylic acid
Synonyms:	Camellioside B
Standard InCHIKey:	LMZLCIKMDCPHLL-QWSKOPIRSA-N
Standard InCHI:	InChI=1S/C55H86O25/c1-22(59)72-40-27(21-58)75-47(38(67)36(40)65)80-44-41(77-48-43(35(64)33(62)26(20-57)74-48)79-46-37(66)34(63)32(61)25(19-56)73-46)39(68)42(45(69)70)78-49(44)76-31-12-13-52(6)28(51(31,4)5)11-14-53(7)29(52)10-9-23-24-17-50(2,3)15-16-55(24,71)30(60)18-54(23,53)8/h9,24-29,31-44,46-49,56-58,61-68,71H,10-21H2,1-8H3,(H,69,70)/t24-,25+,26+,27+,28-,29+,31-,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42-,43+,44+,46-,47-,48-,49+,52-,53+,54+,55+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1[C@H]([C@@H]([C@@H](C(=O)O)O[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(C(=O)C[C@@]32C)O)C1(C)C)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](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087221
PubChem CID:	21633817
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
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	12

Activity Type	# Activity
NON-MOLECULAR	9
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	33.1	%	PMID[482662]
NPT2	Others	Unspecified		Activity	=	64.6	%	PMID[482662]
NPT2	Others	Unspecified		Activity	=	95.0	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	11.9	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	26.0	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	49.0	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	111.5	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	121.5	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	132.1	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	122.3	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	130.0	%	PMID[482662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	130.1	%	PMID[482662]

☑ 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 NPC181066 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	296
0.1-0.2	1988
0.2-0.3	5296
0.3-0.4	9670
0.4-0.5	11416
0.5-0.6	7246
0.6-0.7	3857
0.7-0.8	1957
0.8-0.85	365
0.85-0.9	224
0.9-0.95	270
0.95-1	112

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469947
0.9741	High Similarity	NPC23275
0.9739	High Similarity	NPC4749
0.9739	High Similarity	NPC187290
0.9739	High Similarity	NPC475591
0.9739	High Similarity	NPC21691
0.9739	High Similarity	NPC162574
0.9739	High Similarity	NPC10607
0.9739	High Similarity	NPC80986
0.9739	High Similarity	NPC236870
0.9655	High Similarity	NPC257211
0.9655	High Similarity	NPC200049
0.9655	High Similarity	NPC283417
0.9655	High Similarity	NPC258617
0.9655	High Similarity	NPC302543
0.9652	High Similarity	NPC31838
0.9652	High Similarity	NPC297263
0.9652	High Similarity	NPC187618
0.9652	High Similarity	NPC223301
0.9652	High Similarity	NPC62725
0.9652	High Similarity	NPC75417
0.9652	High Similarity	NPC22956
0.9652	High Similarity	NPC104372
0.9652	High Similarity	NPC301449
0.9652	High Similarity	NPC159309
0.9652	High Similarity	NPC64715
0.9652	High Similarity	NPC114484
0.9652	High Similarity	NPC86222
0.9652	High Similarity	NPC222580
0.9652	High Similarity	NPC302887
0.9652	High Similarity	NPC11242
0.9652	High Similarity	NPC171544
0.9573	High Similarity	NPC33068
0.9573	High Similarity	NPC470477
0.9573	High Similarity	NPC471962
0.9573	High Similarity	NPC471963
0.9573	High Similarity	NPC247315
0.9573	High Similarity	NPC160452
0.9569	High Similarity	NPC313110
0.9569	High Similarity	NPC131469
0.9569	High Similarity	NPC213952
0.9565	High Similarity	NPC118440
0.9565	High Similarity	NPC236657
0.9496	High Similarity	NPC470475
0.9492	High Similarity	NPC470218
0.9492	High Similarity	NPC475368
0.9492	High Similarity	NPC284449
0.9487	High Similarity	NPC471961
0.9487	High Similarity	NPC262199
0.9487	High Similarity	NPC281148
0.9487	High Similarity	NPC30735
0.9487	High Similarity	NPC14617
0.9487	High Similarity	NPC2370
0.9487	High Similarity	NPC44716
0.9487	High Similarity	NPC471964
0.9487	High Similarity	NPC202666
0.9487	High Similarity	NPC235405
0.9478	High Similarity	NPC180550
0.9478	High Similarity	NPC472949
0.9478	High Similarity	NPC309780
0.9478	High Similarity	NPC473884
0.9478	High Similarity	NPC469945
0.9478	High Similarity	NPC475171
0.9478	High Similarity	NPC114441
0.9478	High Similarity	NPC157868
0.9478	High Similarity	NPC35405
0.9478	High Similarity	NPC6377
0.9478	High Similarity	NPC214484
0.9478	High Similarity	NPC11551
0.9478	High Similarity	NPC39211
0.9478	High Similarity	NPC208381
0.9478	High Similarity	NPC192791
0.9402	High Similarity	NPC40775
0.9402	High Similarity	NPC107966
0.9402	High Similarity	NPC249848
0.9402	High Similarity	NPC471965
0.9402	High Similarity	NPC235438
0.9391	High Similarity	NPC286347
0.9391	High Similarity	NPC109588
0.9333	High Similarity	NPC470476
0.9328	High Similarity	NPC285091
0.9322	High Similarity	NPC478066
0.9316	High Similarity	NPC242840
0.9316	High Similarity	NPC31193
0.931	High Similarity	NPC135849
0.931	High Similarity	NPC25663
0.931	High Similarity	NPC51564
0.9304	High Similarity	NPC473824
0.9304	High Similarity	NPC224121
0.9304	High Similarity	NPC68175
0.9304	High Similarity	NPC475119
0.9231	High Similarity	NPC476991
0.9231	High Similarity	NPC294112
0.9224	High Similarity	NPC36831
0.9217	High Similarity	NPC75287
0.9217	High Similarity	NPC161674
0.9217	High Similarity	NPC305267
0.9217	High Similarity	NPC26626
0.9217	High Similarity	NPC160415
0.9217	High Similarity	NPC288205
0.9217	High Similarity	NPC58448
0.9217	High Similarity	NPC37134
0.9217	High Similarity	NPC476992
0.9217	High Similarity	NPC51465
0.9217	High Similarity	NPC471384
0.9217	High Similarity	NPC291903
0.9145	High Similarity	NPC471577
0.9145	High Similarity	NPC207738
0.9138	High Similarity	NPC136768
0.9138	High Similarity	NPC220160
0.9138	High Similarity	NPC309223
0.9138	High Similarity	NPC102505
0.9138	High Similarity	NPC104137
0.9138	High Similarity	NPC33012
0.9138	High Similarity	NPC69811
0.9138	High Similarity	NPC475514
0.9138	High Similarity	NPC123522
0.9138	High Similarity	NPC85154
0.9138	High Similarity	NPC148417
0.9138	High Similarity	NPC191827
0.9138	High Similarity	NPC473452
0.9138	High Similarity	NPC470876
0.9138	High Similarity	NPC110633
0.9138	High Similarity	NPC8524
0.9138	High Similarity	NPC475209
0.9138	High Similarity	NPC471580
0.9138	High Similarity	NPC300419
0.9138	High Similarity	NPC286457
0.913	High Similarity	NPC164389
0.913	High Similarity	NPC475486
0.9106	High Similarity	NPC46823
0.9106	High Similarity	NPC192765
0.9106	High Similarity	NPC30279
0.9106	High Similarity	NPC71391
0.9106	High Similarity	NPC473918
0.9106	High Similarity	NPC277212
0.9106	High Similarity	NPC476776
0.9106	High Similarity	NPC178264
0.9098	High Similarity	NPC470912
0.9098	High Similarity	NPC47995
0.9098	High Similarity	NPC265841
0.9083	High Similarity	NPC130229
0.9076	High Similarity	NPC275343
0.9068	High Similarity	NPC37860
0.9068	High Similarity	NPC144644
0.9068	High Similarity	NPC110385
0.9068	High Similarity	NPC267694
0.9068	High Similarity	NPC142151
0.9068	High Similarity	NPC268184
0.9068	High Similarity	NPC153673
0.9068	High Similarity	NPC473645
0.906	High Similarity	NPC470514
0.906	High Similarity	NPC470513
0.906	High Similarity	NPC237191
0.906	High Similarity	NPC105800
0.906	High Similarity	NPC473459
0.906	High Similarity	NPC232237
0.9043	High Similarity	NPC241909
0.9043	High Similarity	NPC192600
0.9043	High Similarity	NPC295823
0.9043	High Similarity	NPC475467
0.9043	High Similarity	NPC47063
0.9043	High Similarity	NPC251263
0.9043	High Similarity	NPC46665
0.9043	High Similarity	NPC124296
0.9043	High Similarity	NPC473826
0.9043	High Similarity	NPC323341
0.9043	High Similarity	NPC475287
0.9043	High Similarity	NPC174720
0.9043	High Similarity	NPC151543
0.9043	High Similarity	NPC114287
0.9043	High Similarity	NPC309714
0.9043	High Similarity	NPC189884
0.9043	High Similarity	NPC155410
0.9043	High Similarity	NPC166422
0.9043	High Similarity	NPC114304
0.9043	High Similarity	NPC219180
0.9043	High Similarity	NPC258885
0.9043	High Similarity	NPC133818
0.9043	High Similarity	NPC204458
0.9043	High Similarity	NPC138334
0.9032	High Similarity	NPC225791
0.9032	High Similarity	NPC476779
0.9024	High Similarity	NPC476780
0.9024	High Similarity	NPC476775
0.9024	High Similarity	NPC271610
0.9024	High Similarity	NPC476774
0.9024	High Similarity	NPC477197
0.9016	High Similarity	NPC329923
0.9016	High Similarity	NPC477078
0.9016	High Similarity	NPC475281
0.9016	High Similarity	NPC477075
0.8992	High Similarity	NPC470478
0.8992	High Similarity	NPC51099
0.8992	High Similarity	NPC293031
0.8992	High Similarity	NPC275225
0.8992	High Similarity	NPC68767
0.8983	High Similarity	NPC473401
0.8983	High Similarity	NPC473386
0.8974	High Similarity	NPC323359

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 NPC181066 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	2255
0.2-0.3	3816
0.3-0.4	1764
0.4-0.5	587
0.5-0.6	263
0.6-0.7	129
0.7-0.8	44
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9487	High Similarity	NPD8328	Phase 3
0.9304	High Similarity	NPD8295	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7736	Approved
0.808	Intermediate Similarity	NPD8517	Approved
0.808	Intermediate Similarity	NPD8515	Approved
0.808	Intermediate Similarity	NPD8516	Approved
0.7951	Intermediate Similarity	NPD8133	Approved
0.7937	Intermediate Similarity	NPD8513	Phase 3
0.7907	Intermediate Similarity	NPD8293	Discontinued
0.7734	Intermediate Similarity	NPD6370	Approved
0.7652	Intermediate Similarity	NPD7319	Approved
0.7615	Intermediate Similarity	NPD7492	Approved
0.7578	Intermediate Similarity	NPD6054	Approved
0.7578	Intermediate Similarity	NPD6059	Approved
0.7578	Intermediate Similarity	NPD6319	Approved
0.7557	Intermediate Similarity	NPD7507	Approved
0.7557	Intermediate Similarity	NPD6616	Approved
0.7541	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7078	Approved
0.7459	Intermediate Similarity	NPD6412	Phase 2
0.7442	Intermediate Similarity	NPD8377	Approved
0.7442	Intermediate Similarity	NPD8294	Approved
0.744	Intermediate Similarity	NPD6882	Approved
0.744	Intermediate Similarity	NPD8297	Approved
0.7385	Intermediate Similarity	NPD8379	Approved
0.7385	Intermediate Similarity	NPD6016	Approved
0.7385	Intermediate Similarity	NPD8335	Approved
0.7385	Intermediate Similarity	NPD6015	Approved
0.7385	Intermediate Similarity	NPD8296	Approved
0.7385	Intermediate Similarity	NPD8378	Approved
0.7385	Intermediate Similarity	NPD8380	Approved
0.7385	Intermediate Similarity	NPD8033	Approved
0.7373	Intermediate Similarity	NPD7902	Approved
0.736	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6009	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7328	Intermediate Similarity	NPD5988	Approved
0.7265	Intermediate Similarity	NPD7748	Approved
0.7258	Intermediate Similarity	NPD6686	Approved
0.7236	Intermediate Similarity	NPD5739	Approved
0.7236	Intermediate Similarity	NPD6402	Approved
0.7236	Intermediate Similarity	NPD7128	Approved
0.7236	Intermediate Similarity	NPD6675	Approved
0.7222	Intermediate Similarity	NPD6649	Approved
0.7222	Intermediate Similarity	NPD6650	Approved
0.7154	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7320	Approved
0.712	Intermediate Similarity	NPD6881	Approved
0.712	Intermediate Similarity	NPD6899	Approved
0.7119	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7900	Approved
0.7109	Intermediate Similarity	NPD4632	Approved
0.7094	Intermediate Similarity	NPD7515	Phase 2
0.7087	Intermediate Similarity	NPD8130	Phase 1
0.7059	Intermediate Similarity	NPD6033	Approved
0.704	Intermediate Similarity	NPD5697	Approved
0.704	Intermediate Similarity	NPD5701	Approved
0.7023	Intermediate Similarity	NPD7327	Approved
0.7023	Intermediate Similarity	NPD7328	Approved
0.7008	Intermediate Similarity	NPD7102	Approved
0.7008	Intermediate Similarity	NPD6883	Approved
0.7008	Intermediate Similarity	NPD7290	Approved
0.6992	Remote Similarity	NPD6921	Approved
0.6985	Remote Similarity	NPD8074	Phase 3
0.697	Remote Similarity	NPD7516	Approved
0.6953	Remote Similarity	NPD6869	Approved
0.6953	Remote Similarity	NPD6847	Approved
0.6953	Remote Similarity	NPD6617	Approved
0.6947	Remote Similarity	NPD7115	Discovery
0.6929	Remote Similarity	NPD6014	Approved
0.6929	Remote Similarity	NPD6012	Approved
0.6929	Remote Similarity	NPD6013	Approved
0.6889	Remote Similarity	NPD7604	Phase 2
0.6875	Remote Similarity	NPD4634	Approved
0.6866	Remote Similarity	NPD5983	Phase 2
0.6866	Remote Similarity	NPD7503	Approved
0.685	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6411	Approved
0.6788	Remote Similarity	NPD6336	Discontinued
0.675	Remote Similarity	NPD6399	Phase 3
0.6741	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6008	Approved
0.6691	Remote Similarity	NPD8080	Discontinued
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4755	Approved
0.6639	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6101	Approved
0.6617	Remote Similarity	NPD6274	Approved
0.6593	Remote Similarity	NPD7101	Approved
0.6593	Remote Similarity	NPD7100	Approved
0.656	Remote Similarity	NPD4696	Approved
0.656	Remote Similarity	NPD4700	Approved
0.656	Remote Similarity	NPD5285	Approved
0.656	Remote Similarity	NPD5286	Approved
0.6538	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD6067	Discontinued
0.6519	Remote Similarity	NPD6335	Approved
0.65	Remote Similarity	NPD8448	Approved
0.6496	Remote Similarity	NPD6909	Approved
0.6496	Remote Similarity	NPD6908	Approved
0.6489	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4225	Approved
0.648	Remote Similarity	NPD7638	Approved
0.648	Remote Similarity	NPD5696	Approved
0.6479	Remote Similarity	NPD8390	Approved
0.6479	Remote Similarity	NPD8392	Approved
0.6479	Remote Similarity	NPD8391	Approved
0.6475	Remote Similarity	NPD8342	Approved
0.6475	Remote Similarity	NPD8340	Approved
0.6475	Remote Similarity	NPD8299	Approved
0.6475	Remote Similarity	NPD5778	Approved
0.6475	Remote Similarity	NPD5779	Approved
0.6475	Remote Similarity	NPD8341	Approved
0.6471	Remote Similarity	NPD3573	Approved
0.6457	Remote Similarity	NPD5211	Phase 2
0.6457	Remote Similarity	NPD5226	Approved
0.6457	Remote Similarity	NPD4633	Approved
0.6457	Remote Similarity	NPD5224	Approved
0.6457	Remote Similarity	NPD5225	Approved
0.6452	Remote Similarity	NPD4697	Phase 3
0.6444	Remote Similarity	NPD6317	Approved
0.6444	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4768	Approved
0.6434	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD7640	Approved
0.6429	Remote Similarity	NPD7639	Approved
0.6429	Remote Similarity	NPD8451	Approved
0.6406	Remote Similarity	NPD5175	Approved
0.6406	Remote Similarity	NPD5174	Approved
0.6397	Remote Similarity	NPD6314	Approved
0.6397	Remote Similarity	NPD6313	Approved
0.6386	Remote Similarity	NPD7799	Discontinued
0.6378	Remote Similarity	NPD5223	Approved
0.6371	Remote Similarity	NPD5695	Phase 3
0.637	Remote Similarity	NPD6868	Approved
0.637	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5956	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5328	Approved
0.6357	Remote Similarity	NPD5141	Approved
0.6348	Remote Similarity	NPD7329	Approved
0.6348	Remote Similarity	NPD7645	Phase 2
0.6345	Remote Similarity	NPD8450	Suspended
0.6341	Remote Similarity	NPD8171	Discontinued
0.6336	Remote Similarity	NPD4730	Approved
0.6336	Remote Similarity	NPD4729	Approved
0.632	Remote Similarity	NPD5221	Approved
0.632	Remote Similarity	NPD5222	Approved
0.632	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD8415	Approved
0.629	Remote Similarity	NPD5282	Discontinued
0.6281	Remote Similarity	NPD5737	Approved
0.6281	Remote Similarity	NPD6672	Approved
0.6279	Remote Similarity	NPD4754	Approved
0.6276	Remote Similarity	NPD8449	Approved
0.627	Remote Similarity	NPD5173	Approved
0.626	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6079	Approved
0.626	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD8444	Approved
0.6259	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3618	Phase 1
0.6241	Remote Similarity	NPD5248	Approved
0.6241	Remote Similarity	NPD5251	Approved
0.6241	Remote Similarity	NPD5250	Approved
0.6241	Remote Similarity	NPD5247	Approved
0.6241	Remote Similarity	NPD5249	Phase 3
0.6224	Remote Similarity	NPD8337	Approved
0.6224	Remote Similarity	NPD8336	Approved
0.622	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4786	Approved
0.6216	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5128	Approved
0.6207	Remote Similarity	NPD7260	Phase 2
0.619	Remote Similarity	NPD7839	Suspended
0.6186	Remote Similarity	NPD3667	Approved
0.6179	Remote Similarity	NPD46	Approved
0.6179	Remote Similarity	NPD6698	Approved
0.617	Remote Similarity	NPD7829	Approved
0.617	Remote Similarity	NPD7830	Approved
0.6159	Remote Similarity	NPD7641	Discontinued
0.6148	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.614	Remote Similarity	NPD8368	Discontinued
0.6134	Remote Similarity	NPD3669	Approved
0.6134	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6371	Approved
0.6116	Remote Similarity	NPD6098	Approved
0.6102	Remote Similarity	NPD1779	Approved
0.6102	Remote Similarity	NPD1780	Approved
0.6098	Remote Similarity	NPD6904	Approved
0.6098	Remote Similarity	NPD6080	Approved
0.6098	Remote Similarity	NPD6673	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