NPASS Compound

Structure

CID302057 OpenBabel06191716112D 89 97 0 0 1 0 0 0 0 0999 V2000 0.3758 2.7068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7805 -4.8403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0895 -3.8892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5971 4.1036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5916 4.2081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0229 -0.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6659 0.0199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0013 -2.5010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3939 1.3055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6466 -2.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2092 -3.4791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4387 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2029 1.8933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4172 -4.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2797 1.4335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8675 0.6245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4145 -0.5447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2622 10.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3164 6.6402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9558 7.0916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4804 1.7122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3287 1.1245 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9034 -3.1190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9524 -2.8100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4532 10.2562 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5074 6.0524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8513 6.0971 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4876 -1.1627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2066 -1.5228 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3682 -4.7663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0984 2.8878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4604 10.6629 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5938 6.4592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6603 5.5093 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2694 10.0751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5558 4.5148 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7848 5.8714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1649 9.0806 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6422 4.1080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8893 4.8769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2513 8.6739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1668 4.6958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8029 4.4701 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1114 -4.0972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1849 3.2945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2797 -0.1846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3287 0.1245 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7445 -1.8318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1576 11.8385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2119 7.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9497 -2.1920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5649 11.6575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4893 7.4537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5739 5.9160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1830 10.4819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3648 3.9270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8713 6.2781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9739 8.4928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5377 3.1135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3758 2.7068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1468 7.6794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5577 9.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6119 5.0579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0622 5.6903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 3.4756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0803 4.2891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 56 1 0 0 0 0 3 56 1 0 0 0 0 4 57 1 0 0 0 0 5 57 1 0 0 0 0 6 58 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 25 2 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 14 34 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 58 1 0 0 0 0 17 33 1 0 0 0 0 17 59 1 0 0 0 0 18 61 1 0 0 0 0 19 62 1 0 0 0 0 20 63 1 0 0 0 0 21 80 1 0 0 0 0 22 81 1 0 0 0 0 23 1 1 6 0 0 0 23 24 1 0 0 0 0 24 59 1 6 0 0 0 25 26 1 0 0 0 0 25 56 1 0 0 0 0 26 60 1 6 0 0 0 27 18 1 6 0 0 0 27 36 1 0 0 0 0 27 82 1 0 0 0 0 28 19 1 6 0 0 0 28 37 1 0 0 0 0 28 83 1 0 0 0 0 29 20 1 1 0 0 0 29 38 1 0 0 0 0 29 84 1 0 0 0 0 30 21 1 6 0 0 0 30 39 1 0 0 0 0 30 85 1 0 0 0 0 31 22 1 1 0 0 0 31 40 1 0 0 0 0 31 86 1 0 0 0 0 32 58 1 1 0 0 0 32 60 1 0 0 0 0 33 60 1 1 0 0 0 33 64 1 0 0 0 0 34 56 1 0 0 0 0 34 87 1 6 0 0 0 35 13 1 6 0 0 0 35 57 1 0 0 0 0 35 88 1 0 0 0 0 36 41 1 0 0 0 0 36 65 1 1 0 0 0 37 42 1 0 0 0 0 37 66 1 1 0 0 0 38 45 1 0 0 0 0 38 67 1 6 0 0 0 39 43 1 0 0 0 0 39 68 1 1 0 0 0 40 44 1 0 0 0 0 40 69 1 6 0 0 0 41 46 1 0 0 0 0 41 70 1 6 0 0 0 42 47 1 0 0 0 0 42 71 1 6 0 0 0 43 48 1 0 0 0 0 43 72 1 6 0 0 0 44 49 1 0 0 0 0 44 73 1 1 0 0 0 45 50 1 0 0 0 0 45 74 1 1 0 0 0 46 51 1 0 0 0 0 46 75 1 1 0 0 0 47 52 1 0 0 0 0 47 76 1 1 0 0 0 48 53 1 0 0 0 0 48 77 1 1 0 0 0 49 54 1 0 0 0 0 49 78 1 6 0 0 0 50 55 1 0 0 0 0 50 89 1 6 0 0 0 51 80 1 6 0 0 0 51 82 1 0 0 0 0 52 81 1 6 0 0 0 52 83 1 0 0 0 0 53 85 1 0 0 0 0 53 87 1 6 0 0 0 54 86 1 0 0 0 0 54 89 1 1 0 0 0 55 84 1 0 0 0 0 55 88 1 1 0 0 0 57 79 1 0 0 0 0 58 59 1 1 0 0 0 59 7 1 6 0 0 0 60 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1286.65
Volume:	1221.588
LogP:	0.246
LogD:	0.942
LogS:	-2.382
# Rotatable Bonds:	20
TPSA:	476.67
# H-Bond Aceptor:	29
# H-Bond Donor:	19
# Rings:	9
# Heavy Atoms:	29

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	7.498
Fsp3:	0.967
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:	-6.455
MDCK Permeability:	0.0005045691505074501
Pgp-inhibitor:	0.425
Pgp-substrate:	0.22
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	55.41867446899414%
Volume Distribution (VD):	-0.378
Pgp-substrate:	14.729375839233398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-0.526
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.68
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC302057

Natural Product ID:	NPC302057
*Common Name:**	7-Oxomogroside V
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(3S,8S,9R,10R,11R,13R,14S,17R)-17-[(2R,5R)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-6-hydroxy-6-methylheptan-2-yl]-11-hydroxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	7-oxomogroside V
Standard InCHIKey:	GRWRKEKBKNZMOA-SJJZSDDKSA-N
Standard InCHI:	InChI=1S/C60H102O29/c1-23(9-13-35(57(4,5)79)88-55-50(45(74)38(67)29(20-63)84-55)89-54-49(78)44(73)40(69)31(86-54)22-81-52-47(76)42(71)37(66)28(19-62)83-52)24-15-16-58(6)32-12-10-25-26(60(32,8)33(64)17-59(24,58)7)11-14-34(56(25,2)3)87-53-48(77)43(72)39(68)30(85-53)21-80-51-46(75)41(70)36(65)27(18-61)82-51/h10,23-24,26-55,61-79H,9,11-22H2,1-8H3/t23-,24-,26-,27-,28+,29-,30-,31-,32+,33-,34+,35-,36-,37+,38-,39-,40-,41+,42-,43+,44+,45+,46-,47+,48-,49-,50-,51-,52+,53+,54+,55+,58+,59-,60+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H](C(O)(C)C)CC[C@H]([C@H]2CC[C@@]3([C@]2(C)C[C@@H](O)[C@@]2([C@H]3CC=C3[C@H]2CC[C@@H](C3(C)C)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO[C@H]2O[C@@H](CO)[C@@H]([C@H]([C@@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227760
PubChem CID:	44423070
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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
NPO32612	siraitia gros venorii	Species	Cucurbitaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17477572]

☑ 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	6

Activity Type	# Activity
Cell Line	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[575545]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	13.7	%	PMID[575545]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	31.0	%	PMID[575545]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	84.7	%	PMID[575545]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	100.0	%	PMID[575545]
NPT2	Others	Unspecified		Ratio	=	1.4	n.a.	PMID[575545]

☑ 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 NPC302057 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	285
0.1-0.2	2056
0.2-0.3	6393
0.3-0.4	13411
0.4-0.5	9099
0.5-0.6	5307
0.6-0.7	3384
0.7-0.8	1545
0.8-0.85	625
0.85-0.9	356
0.9-0.95	183
0.95-1	53

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC190395
0.9703	High Similarity	NPC159005
0.9703	High Similarity	NPC6931
0.97	High Similarity	NPC309448
0.9604	High Similarity	NPC14946
0.9604	High Similarity	NPC63368
0.9604	High Similarity	NPC208650
0.96	High Similarity	NPC221562
0.96	High Similarity	NPC470885
0.96	High Similarity	NPC187400
0.9524	High Similarity	NPC477810
0.951	High Similarity	NPC246124
0.951	High Similarity	NPC180183
0.9505	High Similarity	NPC269627
0.9505	High Similarity	NPC152584
0.9505	High Similarity	NPC160816
0.9505	High Similarity	NPC208477
0.9505	High Similarity	NPC194842
0.9505	High Similarity	NPC127801
0.9505	High Similarity	NPC69737
0.9505	High Similarity	NPC208594
0.9429	High Similarity	NPC476671
0.9412	High Similarity	NPC94272
0.9412	High Similarity	NPC181467
0.934	High Similarity	NPC167183
0.934	High Similarity	NPC32707
0.9333	High Similarity	NPC31896
0.9333	High Similarity	NPC263359
0.9333	High Similarity	NPC32361
0.9333	High Similarity	NPC210569
0.9333	High Similarity	NPC244431
0.9327	High Similarity	NPC222202
0.9327	High Similarity	NPC269297
0.9327	High Similarity	NPC23808
0.9327	High Similarity	NPC477811
0.9327	High Similarity	NPC224314
0.9327	High Similarity	NPC87998
0.932	High Similarity	NPC220427
0.9314	High Similarity	NPC242748
0.9307	High Similarity	NPC31907
0.9307	High Similarity	NPC472252
0.9307	High Similarity	NPC16520
0.9307	High Similarity	NPC155010
0.9307	High Similarity	NPC157659
0.9307	High Similarity	NPC189852
0.9307	High Similarity	NPC473020
0.9307	High Similarity	NPC131479
0.9307	High Similarity	NPC8039
0.9307	High Similarity	NPC245280
0.9307	High Similarity	NPC211879
0.9307	High Similarity	NPC114874
0.9307	High Similarity	NPC120123
0.9307	High Similarity	NPC286969
0.9252	High Similarity	NPC146652
0.9245	High Similarity	NPC79900
0.9238	High Similarity	NPC477028
0.9238	High Similarity	NPC124677
0.9238	High Similarity	NPC13193
0.9238	High Similarity	NPC475247
0.9238	High Similarity	NPC294129
0.9238	High Similarity	NPC197231
0.9238	High Similarity	NPC477032
0.9238	High Similarity	NPC476547
0.9231	High Similarity	NPC475550
0.9231	High Similarity	NPC224098
0.9231	High Similarity	NPC84956
0.9231	High Similarity	NPC244086
0.9231	High Similarity	NPC194207
0.9231	High Similarity	NPC477809
0.9231	High Similarity	NPC73243
0.9231	High Similarity	NPC475333
0.9231	High Similarity	NPC102016
0.9231	High Similarity	NPC46190
0.9231	High Similarity	NPC232054
0.9231	High Similarity	NPC6806
0.9231	High Similarity	NPC150372
0.9231	High Similarity	NPC171073
0.9231	High Similarity	NPC95051
0.9231	High Similarity	NPC470433
0.9231	High Similarity	NPC309278
0.9231	High Similarity	NPC218571
0.9231	High Similarity	NPC249265
0.9231	High Similarity	NPC248746
0.9231	High Similarity	NPC208383
0.9231	High Similarity	NPC22779
0.9231	High Similarity	NPC300557
0.9216	High Similarity	NPC165033
0.9216	High Similarity	NPC273879
0.9208	High Similarity	NPC272015
0.9208	High Similarity	NPC136816
0.9208	High Similarity	NPC312553
0.9208	High Similarity	NPC159036
0.9208	High Similarity	NPC288694
0.9159	High Similarity	NPC208832
0.9151	High Similarity	NPC308140
0.9151	High Similarity	NPC472716
0.9151	High Similarity	NPC19888
0.9135	High Similarity	NPC98696
0.9126	High Similarity	NPC470512
0.9126	High Similarity	NPC474569
0.9126	High Similarity	NPC473923
0.9126	High Similarity	NPC473476
0.9126	High Similarity	NPC173859
0.9118	High Similarity	NPC16573
0.9118	High Similarity	NPC123796
0.9109	High Similarity	NPC309425
0.9109	High Similarity	NPC160734
0.9109	High Similarity	NPC88000
0.9109	High Similarity	NPC129372
0.9109	High Similarity	NPC472023
0.9109	High Similarity	NPC4831
0.9109	High Similarity	NPC47566
0.9091	High Similarity	NPC475358
0.9091	High Similarity	NPC473566
0.9074	High Similarity	NPC279638
0.9074	High Similarity	NPC477030
0.9074	High Similarity	NPC477029
0.9065	High Similarity	NPC476546
0.9065	High Similarity	NPC476693
0.9065	High Similarity	NPC307642
0.9057	High Similarity	NPC472715
0.9057	High Similarity	NPC65167
0.9048	High Similarity	NPC475670
0.9048	High Similarity	NPC42482
0.9048	High Similarity	NPC477026
0.9048	High Similarity	NPC40440
0.9048	High Similarity	NPC306131
0.9048	High Similarity	NPC477027
0.9048	High Similarity	NPC70204
0.9038	High Similarity	NPC14704
0.9038	High Similarity	NPC230507
0.9038	High Similarity	NPC283829
0.9038	High Similarity	NPC113044
0.9038	High Similarity	NPC161676
0.9038	High Similarity	NPC470432
0.9038	High Similarity	NPC78034
0.9038	High Similarity	NPC231340
0.9038	High Similarity	NPC305423
0.9038	High Similarity	NPC473469
0.9029	High Similarity	NPC148603
0.9029	High Similarity	NPC476360
0.9029	High Similarity	NPC75608
0.9029	High Similarity	NPC476361
0.902	High Similarity	NPC30289
0.902	High Similarity	NPC213674
0.902	High Similarity	NPC76497
0.902	High Similarity	NPC256133
0.901	High Similarity	NPC7341
0.901	High Similarity	NPC282669
0.901	High Similarity	NPC473200
0.9	High Similarity	NPC473890
0.9	High Similarity	NPC243728
0.8991	High Similarity	NPC20979
0.8991	High Similarity	NPC477807
0.8981	High Similarity	NPC477808
0.8981	High Similarity	NPC11548
0.8972	High Similarity	NPC254255
0.8972	High Similarity	NPC42171
0.8962	High Similarity	NPC247037
0.8962	High Similarity	NPC472717
0.8952	High Similarity	NPC476541
0.8952	High Similarity	NPC472897
0.8952	High Similarity	NPC7213
0.8952	High Similarity	NPC472896
0.8952	High Similarity	NPC476539
0.8952	High Similarity	NPC476540
0.8952	High Similarity	NPC38217
0.8952	High Similarity	NPC472988
0.8952	High Similarity	NPC476538
0.8952	High Similarity	NPC126147
0.8942	High Similarity	NPC181845
0.8942	High Similarity	NPC472899
0.8942	High Similarity	NPC472898
0.8942	High Similarity	NPC138057
0.8942	High Similarity	NPC472900
0.8932	High Similarity	NPC213190
0.8932	High Similarity	NPC473198
0.8922	High Similarity	NPC117714
0.8922	High Similarity	NPC263756
0.8911	High Similarity	NPC234287
0.8911	High Similarity	NPC158088
0.8911	High Similarity	NPC280825
0.8899	High Similarity	NPC63609
0.8899	High Similarity	NPC477031
0.8879	High Similarity	NPC470748
0.8879	High Similarity	NPC114188
0.8879	High Similarity	NPC473021
0.8879	High Similarity	NPC472987
0.8868	High Similarity	NPC476835
0.8868	High Similarity	NPC154085
0.8868	High Similarity	NPC125361
0.8868	High Similarity	NPC43976
0.8868	High Similarity	NPC14630
0.8868	High Similarity	NPC296761
0.8868	High Similarity	NPC250089
0.8868	High Similarity	NPC51925
0.8868	High Similarity	NPC157530
0.8857	High Similarity	NPC234160
0.8857	High Similarity	NPC226642
0.8857	High Similarity	NPC257964

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 NPC302057 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	2208
0.2-0.3	4276
0.3-0.4	1609
0.4-0.5	437
0.5-0.6	242
0.6-0.7	122
0.7-0.8	19
0.8-0.85	3
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD8377	Approved
0.8261	Intermediate Similarity	NPD8294	Approved
0.819	Intermediate Similarity	NPD8379	Approved
0.819	Intermediate Similarity	NPD8378	Approved
0.819	Intermediate Similarity	NPD8296	Approved
0.819	Intermediate Similarity	NPD8033	Approved
0.819	Intermediate Similarity	NPD8335	Approved
0.819	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD8133	Approved
0.7778	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD7327	Approved
0.7731	Intermediate Similarity	NPD7503	Approved
0.7714	Intermediate Similarity	NPD8171	Discontinued
0.7712	Intermediate Similarity	NPD7516	Approved
0.7679	Intermediate Similarity	NPD6412	Phase 2
0.7619	Intermediate Similarity	NPD8450	Suspended
0.7544	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD8449	Approved
0.7459	Intermediate Similarity	NPD8328	Phase 3
0.7395	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7507	Approved
0.7228	Intermediate Similarity	NPD7525	Registered
0.7165	Intermediate Similarity	NPD7319	Approved
0.7154	Intermediate Similarity	NPD8517	Approved
0.7154	Intermediate Similarity	NPD8515	Approved
0.7154	Intermediate Similarity	NPD8516	Approved
0.7097	Intermediate Similarity	NPD6370	Approved
0.7087	Intermediate Similarity	NPD7736	Approved
0.7075	Intermediate Similarity	NPD7524	Approved
0.7043	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8513	Phase 3
0.7009	Intermediate Similarity	NPD6686	Approved
0.7008	Intermediate Similarity	NPD8293	Discontinued
0.6961	Remote Similarity	NPD7645	Phase 2
0.6952	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6054	Approved
0.6935	Remote Similarity	NPD6059	Approved
0.69	Remote Similarity	NPD6942	Approved
0.69	Remote Similarity	NPD7339	Approved
0.6857	Remote Similarity	NPD6695	Phase 3
0.6833	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8297	Approved
0.6777	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD7750	Discontinued
0.6746	Remote Similarity	NPD6015	Approved
0.6746	Remote Similarity	NPD6016	Approved
0.6719	Remote Similarity	NPD7492	Approved
0.6694	Remote Similarity	NPD6009	Approved
0.6693	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6319	Approved
0.6641	Remote Similarity	NPD6067	Discontinued
0.6615	Remote Similarity	NPD7078	Approved
0.6609	Remote Similarity	NPD7638	Approved
0.6607	Remote Similarity	NPD6399	Phase 3
0.6606	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD6930	Phase 2
0.6571	Remote Similarity	NPD6928	Phase 2
0.6571	Remote Similarity	NPD6931	Approved
0.656	Remote Similarity	NPD7115	Discovery
0.6555	Remote Similarity	NPD5739	Approved
0.6555	Remote Similarity	NPD6675	Approved
0.6555	Remote Similarity	NPD6402	Approved
0.6555	Remote Similarity	NPD7128	Approved
0.6552	Remote Similarity	NPD7640	Approved
0.6552	Remote Similarity	NPD7639	Approved
0.6529	Remote Similarity	NPD6373	Approved
0.6529	Remote Similarity	NPD6372	Approved
0.6481	Remote Similarity	NPD4786	Approved
0.6479	Remote Similarity	NPD7625	Phase 1
0.6476	Remote Similarity	NPD6929	Approved
0.6471	Remote Similarity	NPD6924	Approved
0.6471	Remote Similarity	NPD6926	Approved
0.6446	Remote Similarity	NPD6881	Approved
0.6446	Remote Similarity	NPD7320	Approved
0.6446	Remote Similarity	NPD6899	Approved
0.6442	Remote Similarity	NPD6932	Approved
0.6439	Remote Similarity	NPD6033	Approved
0.6423	Remote Similarity	NPD8130	Phase 1
0.6423	Remote Similarity	NPD6650	Approved
0.6423	Remote Similarity	NPD6649	Approved
0.6404	Remote Similarity	NPD7748	Approved
0.6379	Remote Similarity	NPD4755	Approved
0.6379	Remote Similarity	NPD7902	Approved
0.6372	Remote Similarity	NPD8034	Phase 2
0.6372	Remote Similarity	NPD8035	Phase 2
0.6372	Remote Similarity	NPD7087	Discontinued
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6341	Remote Similarity	NPD7290	Approved
0.6341	Remote Similarity	NPD7102	Approved
0.6341	Remote Similarity	NPD6883	Approved
0.6341	Remote Similarity	NPD4634	Approved
0.6339	Remote Similarity	NPD5328	Approved
0.6321	Remote Similarity	NPD6683	Phase 2
0.6316	Remote Similarity	NPD4202	Approved
0.6311	Remote Similarity	NPD4785	Approved
0.6311	Remote Similarity	NPD4784	Approved
0.6311	Remote Similarity	NPD1810	Approved
0.6311	Remote Similarity	NPD1811	Approved
0.6296	Remote Similarity	NPD3667	Approved
0.629	Remote Similarity	NPD6847	Approved
0.629	Remote Similarity	NPD6617	Approved
0.629	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD5776	Phase 2
0.6286	Remote Similarity	NPD6925	Approved
0.6283	Remote Similarity	NPD3168	Discontinued
0.6281	Remote Similarity	NPD6008	Approved
0.6275	Remote Similarity	NPD4243	Approved
0.6273	Remote Similarity	NPD6893	Approved
0.6271	Remote Similarity	NPD5285	Approved
0.6271	Remote Similarity	NPD5286	Approved
0.6271	Remote Similarity	NPD4700	Approved
0.6271	Remote Similarity	NPD4696	Approved
0.6262	Remote Similarity	NPD7509	Discontinued
0.6262	Remote Similarity	NPD7514	Phase 3
0.6262	Remote Similarity	NPD4748	Discontinued
0.626	Remote Similarity	NPD6012	Approved
0.626	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6014	Approved
0.626	Remote Similarity	NPD7604	Phase 2
0.626	Remote Similarity	NPD6013	Approved
0.6239	Remote Similarity	NPD6083	Phase 2
0.6239	Remote Similarity	NPD6084	Phase 2
0.6238	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5983	Phase 2
0.6228	Remote Similarity	NPD6079	Approved
0.6228	Remote Similarity	NPD7515	Phase 2
0.6226	Remote Similarity	NPD7145	Approved
0.6218	Remote Similarity	NPD4159	Approved
0.6216	Remote Similarity	NPD3618	Phase 1
0.6186	Remote Similarity	NPD4225	Approved
0.6179	Remote Similarity	NPD6011	Approved
0.6167	Remote Similarity	NPD5211	Phase 2
0.6167	Remote Similarity	NPD5226	Approved
0.6167	Remote Similarity	NPD5225	Approved
0.6167	Remote Similarity	NPD4633	Approved
0.6167	Remote Similarity	NPD5224	Approved
0.6165	Remote Similarity	NPD6336	Discontinued
0.616	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4768	Approved
0.6148	Remote Similarity	NPD4767	Approved
0.6126	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7900	Approved
0.6121	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD8074	Phase 3
0.6117	Remote Similarity	NPD7151	Approved
0.6117	Remote Similarity	NPD7152	Approved
0.6117	Remote Similarity	NPD7150	Approved
0.6116	Remote Similarity	NPD5174	Approved
0.6116	Remote Similarity	NPD5175	Approved
0.6111	Remote Similarity	NPD7332	Phase 2
0.6087	Remote Similarity	NPD7637	Suspended
0.6083	Remote Similarity	NPD5344	Discontinued
0.6083	Remote Similarity	NPD5223	Approved
0.608	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6923	Approved
0.6078	Remote Similarity	NPD6922	Approved
0.6066	Remote Similarity	NPD5141	Approved
0.6055	Remote Similarity	NPD6902	Approved
0.6055	Remote Similarity	NPD6898	Phase 1
0.6053	Remote Similarity	NPD6051	Approved
0.6053	Remote Similarity	NPD4753	Phase 2
0.605	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4729	Approved
0.6048	Remote Similarity	NPD4730	Approved
0.6033	Remote Similarity	NPD7632	Discontinued
0.6019	Remote Similarity	NPD2686	Approved
0.6019	Remote Similarity	NPD2687	Approved
0.6019	Remote Similarity	NPD2254	Approved
0.6019	Remote Similarity	NPD7143	Approved
0.6019	Remote Similarity	NPD7144	Approved
0.6017	Remote Similarity	NPD5222	Approved
0.6017	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD4697	Phase 3
0.6017	Remote Similarity	NPD5221	Approved
0.5985	Remote Similarity	NPD5956	Approved
0.5984	Remote Similarity	NPD6430	Approved
0.5984	Remote Similarity	NPD6429	Approved
0.5984	Remote Similarity	NPD4754	Approved
0.5969	Remote Similarity	NPD6274	Approved
0.5966	Remote Similarity	NPD5173	Approved
0.5954	Remote Similarity	NPD7101	Approved
0.5954	Remote Similarity	NPD7100	Approved
0.5952	Remote Similarity	NPD5250	Approved
0.5952	Remote Similarity	NPD5248	Approved
0.5952	Remote Similarity	NPD5247	Approved
0.5952	Remote Similarity	NPD5251	Approved
0.5952	Remote Similarity	NPD5249	Phase 3
0.5946	Remote Similarity	NPD3669	Approved
0.5946	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4190	Phase 3
0.5943	Remote Similarity	NPD5275	Approved
0.5932	Remote Similarity	NPD7991	Discontinued
0.5932	Remote Similarity	NPD5695	Phase 3
0.592	Remote Similarity	NPD5128	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