NPASS Compound

Structure

NPC475300 OpenBabel07101718322D 89 98 0 0 1 0 0 0 0 0999 V2000 -7.7155 -3.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4301 -4.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4301 -6.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.5737 -7.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7402 1.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8573 -2.4747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4391 -1.2958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8582 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0019 -1.9798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7164 -5.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7164 -10.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4291 -5.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4291 -4.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5718 -6.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5718 -4.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7146 -5.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8573 -4.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8573 -3.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5718 -0.4949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5718 -3.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7146 -2.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7146 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1903 1.0717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2058 0.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4291 -1.9798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1437 -1.9798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4301 -1.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0019 -4.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.2883 -6.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8582 -2.9697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4301 -3.4646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2873 -5.9394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.7164 -7.9192 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5344 0.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7146 -4.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5718 -1.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4291 -2.9697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0009 -1.4848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2873 -1.9798 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.0019 -5.9394 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -16.2883 -7.4242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8573 -1.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8573 -1.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7146 -2.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1437 -2.9697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5728 -1.9798 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1446 -4.4545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -17.1456 -7.9192 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -17.1456 -8.9091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -16.2883 -9.4040 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.0019 -8.9091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8582 -1.9798 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2873 -2.9697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.1446 -6.4343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.7164 -8.9091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.8592 -9.4040 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -15.4310 -8.9091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.0019 -7.9192 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7146 -1.9798 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8573 -0.4949 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5929 0.1674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8573 -0.4949 0.0000 C 0 0 2 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 -17.1456 -5.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2700 -0.1891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5718 -3.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.0028 -7.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.0028 -9.4040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.2883 -10.3939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1446 -9.4040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3286 -0.4949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8573 1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9845 0.1035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0009 -0.4949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1446 -1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8592 -6.4343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8592 -10.3939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0009 -3.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5728 -2.9697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2873 -4.9495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8592 -7.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2864 -3.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.4310 -7.9192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7146 -1.9798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7155 -1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1446 -3.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1446 -7.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.5737 -9.4040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 35 1 0 0 0 0 7 61 1 0 0 0 0 8 75 1 0 0 0 0 9 76 1 0 0 0 0 10 77 1 0 0 0 0 11 78 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 36 2 0 0 0 0 16 36 1 0 0 0 0 17 18 2 0 0 0 0 17 36 1 0 0 0 0 18 45 1 0 0 0 0 19 22 1 0 0 0 0 19 37 2 0 0 0 0 20 21 1 0 0 0 0 20 38 1 0 0 0 0 21 60 1 0 0 0 0 22 63 1 0 0 0 0 23 24 1 0 0 0 0 23 62 1 0 0 0 0 24 64 1 0 0 0 0 25 37 1 0 0 0 0 25 38 1 0 0 0 0 26 39 1 0 0 0 0 26 46 1 0 0 0 0 27 40 1 0 0 0 0 27 47 1 0 0 0 0 28 41 1 0 0 0 0 28 48 1 0 0 0 0 29 43 1 0 0 0 0 29 44 1 0 0 0 0 30 65 1 0 0 0 0 31 1 1 6 0 0 0 31 53 1 0 0 0 0 31 79 1 0 0 0 0 32 2 1 6 0 0 0 32 54 1 0 0 0 0 32 80 1 0 0 0 0 33 3 1 6 0 0 0 33 55 1 0 0 0 0 33 81 1 0 0 0 0 34 4 1 1 0 0 0 34 56 1 0 0 0 0 34 82 1 0 0 0 0 35 62 1 0 0 0 0 35 66 2 0 0 0 0 37 60 1 0 0 0 0 38 83 1 6 0 0 0 39 53 1 0 0 0 0 39 75 1 1 0 0 0 40 54 1 0 0 0 0 40 76 1 1 0 0 0 41 55 1 0 0 0 0 41 77 1 1 0 0 0 42 30 1 1 0 0 0 42 49 1 0 0 0 0 42 84 1 0 0 0 0 43 60 1 6 0 0 0 43 63 1 0 0 0 0 44 61 1 6 0 0 0 44 85 1 0 0 0 0 45 67 2 0 0 0 0 45 85 1 0 0 0 0 46 79 1 0 0 0 0 46 83 1 6 0 0 0 47 80 1 0 0 0 0 47 86 1 6 0 0 0 48 81 1 0 0 0 0 48 87 1 6 0 0 0 49 50 1 0 0 0 0 49 68 1 6 0 0 0 50 51 1 0 0 0 0 50 69 1 1 0 0 0 51 58 1 0 0 0 0 51 70 1 6 0 0 0 52 57 1 0 0 0 0 52 59 1 0 0 0 0 52 71 1 6 0 0 0 53 86 1 1 0 0 0 54 87 1 1 0 0 0 55 88 1 1 0 0 0 56 57 1 0 0 0 0 56 89 1 6 0 0 0 57 78 1 1 0 0 0 58 84 1 0 0 0 0 58 89 1 1 0 0 0 59 82 1 0 0 0 0 59 88 1 1 0 0 0 60 6 1 6 0 0 0 61 62 1 1 0 0 0 62 72 1 1 0 0 0 63 64 1 1 0 0 0 63 73 1 0 0 0 0 64 61 1 6 0 0 0 64 74 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1264.62
Volume:	1231.235
LogP:	3.315
LogD:	2.639
LogS:	-4.047
# Rotatable Bonds:	20
TPSA:	334.43
# H-Bond Aceptor:	25
# H-Bond Donor:	8
# Rings:	10
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.056
Synthetic Accessibility Score:	7.405
Fsp3:	0.812
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:	-6.018
MDCK Permeability:	0.0002516314561944455
Pgp-inhibitor:	0.002
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.376
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	60.910579681396484%
Volume Distribution (VD):	0.121
Pgp-substrate:	13.7286958694458%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.989
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.399
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	0.689
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.743
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.818
AMES Toxicity:	0.415
Rat Oral Acute Toxicity:	0.742
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.805
Carcinogencity:	0.176
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC475300

Natural Product ID:	NPC475300
*Common Name:**	12-O-Cinnamoyldeacetylmetaplexigenin Beta-D-Glucopyranosyl-(1->4)-Beta-D-Thevetopyranosyl-(1->4)-Beta-D-Cymaropyranosyl-(1->4)-Beta-D-Cymaropyranosyl-(1->4)-Beta-D-Cymaropyranoside
IUPAC Name:	[(3S,8S,9R,10R,12R,13S,14R,17R)-17-acetyl-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	KVMSBPUIMUZEIE-FLRJXKCASA-N
Standard InCHI:	InChI=1S/C64H96O25/c1-31-53(86-47-27-40(76-9)54(32(2)80-47)87-48-28-41(77-10)55(33(3)81-48)88-59-52(71)57(78-11)56(34(4)82-59)89-58-51(70)50(69)49(68)42(30-65)84-58)39(75-8)26-46(79-31)83-38-20-21-60(6)37(25-38)19-22-63(73)43(60)29-44(85-45(67)18-17-36-15-13-12-14-16-36)61(7)62(72,35(5)66)23-24-64(61,63)74/h12-19,31-34,38-44,46-59,65,68-74H,20-30H2,1-11H3/b18-17+/t31-,32-,33-,34-,38+,39+,40+,41+,42-,43-,44-,46+,47+,48+,49-,50+,51-,52-,53-,54-,55-,56-,57-,58+,59+,60+,61-,62+,63+,64-/m1/s1
SMILES:	CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C(=CC[C@@]4([C@@H]3C[C@@H](OC(=O)/C=C/c3ccccc3)[C@]3([C@]4(O)CC[C@]3(O)C(=O)C)C)O)C2)C)O[C@@H]([C@H]1O[C@H]1C[C@H](OC)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](OC)[C@@H]([C@H](O1)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503165
PubChem CID:	44575255
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal 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
NPO32487	leptadenia pyrotechnica	Species	Apocynaceae	Eukaryota	whole plant	Dogon region, Mali	2002-Apr	PMID[16643040]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	380.0	nM	PMID[573741]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	850.0	nM	PMID[573741]
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	=	50.0	nM	PMID[573741]

☑ 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 NPC475300 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	370
0.1-0.2	1233
0.2-0.3	2860
0.3-0.4	5687
0.4-0.5	10336
0.5-0.6	14191
0.6-0.7	6111
0.7-0.8	1736
0.8-0.85	108
0.85-0.9	26
0.9-0.95	27
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473641
1.0	High Similarity	NPC475464
1.0	High Similarity	NPC475437
1.0	High Similarity	NPC473797
1.0	High Similarity	NPC475505
0.9934	High Similarity	NPC475536
0.9934	High Similarity	NPC165234
0.9272	High Similarity	NPC475447
0.9272	High Similarity	NPC70236
0.9272	High Similarity	NPC475218
0.9272	High Similarity	NPC476092
0.9205	High Similarity	NPC474564
0.9146	High Similarity	NPC475613
0.9068	High Similarity	NPC477488
0.9062	High Similarity	NPC475198
0.9062	High Similarity	NPC475531
0.9062	High Similarity	NPC475175
0.9	High Similarity	NPC473468
0.9	High Similarity	NPC475567
0.9	High Similarity	NPC473557
0.8981	High Similarity	NPC477467
0.8917	High Similarity	NPC477470
0.8917	High Similarity	NPC477474
0.8917	High Similarity	NPC477472
0.8882	High Similarity	NPC477491
0.8861	High Similarity	NPC476784
0.8758	High Similarity	NPC264270
0.8758	High Similarity	NPC40085
0.8726	High Similarity	NPC69425
0.8718	High Similarity	NPC329657
0.8693	High Similarity	NPC111466
0.8606	High Similarity	NPC477469
0.8606	High Similarity	NPC477466
0.8606	High Similarity	NPC477471
0.8606	High Similarity	NPC477473
0.8545	High Similarity	NPC102465
0.8442	Intermediate Similarity	NPC473755
0.8442	Intermediate Similarity	NPC475513
0.8438	Intermediate Similarity	NPC471176
0.8438	Intermediate Similarity	NPC469456
0.8415	Intermediate Similarity	NPC295408
0.8415	Intermediate Similarity	NPC329960
0.8415	Intermediate Similarity	NPC150893
0.8395	Intermediate Similarity	NPC477736
0.8344	Intermediate Similarity	NPC290746
0.8344	Intermediate Similarity	NPC79250
0.8333	Intermediate Similarity	NPC477735
0.8323	Intermediate Similarity	NPC40138
0.8312	Intermediate Similarity	NPC473440
0.8282	Intermediate Similarity	NPC319404
0.828	Intermediate Similarity	NPC301946
0.828	Intermediate Similarity	NPC277053
0.8269	Intermediate Similarity	NPC284957
0.8253	Intermediate Similarity	NPC471493
0.825	Intermediate Similarity	NPC478123
0.8242	Intermediate Similarity	NPC275477
0.8232	Intermediate Similarity	NPC477623
0.8217	Intermediate Similarity	NPC80895
0.8217	Intermediate Similarity	NPC471912
0.821	Intermediate Similarity	NPC473611
0.821	Intermediate Similarity	NPC472549
0.821	Intermediate Similarity	NPC132599
0.821	Intermediate Similarity	NPC473632
0.821	Intermediate Similarity	NPC469730
0.8205	Intermediate Similarity	NPC63737
0.8204	Intermediate Similarity	NPC325732
0.8204	Intermediate Similarity	NPC324769
0.8193	Intermediate Similarity	NPC66193
0.8193	Intermediate Similarity	NPC478125
0.8192	Intermediate Similarity	NPC475121
0.8192	Intermediate Similarity	NPC476067
0.8187	Intermediate Similarity	NPC476173
0.8171	Intermediate Similarity	NPC469399
0.8171	Intermediate Similarity	NPC49297
0.816	Intermediate Similarity	NPC70344
0.816	Intermediate Similarity	NPC154675
0.8155	Intermediate Similarity	NPC161151
0.8144	Intermediate Similarity	NPC471134
0.8141	Intermediate Similarity	NPC325078
0.8136	Intermediate Similarity	NPC189704
0.8133	Intermediate Similarity	NPC478124
0.8129	Intermediate Similarity	NPC469421
0.811	Intermediate Similarity	NPC469417
0.811	Intermediate Similarity	NPC181924
0.811	Intermediate Similarity	NPC318447
0.811	Intermediate Similarity	NPC322048
0.8107	Intermediate Similarity	NPC469420
0.8098	Intermediate Similarity	NPC228204
0.8098	Intermediate Similarity	NPC26033
0.8098	Intermediate Similarity	NPC5115
0.8098	Intermediate Similarity	NPC469398
0.8095	Intermediate Similarity	NPC61891
0.8086	Intermediate Similarity	NPC472548
0.8079	Intermediate Similarity	NPC96194
0.8079	Intermediate Similarity	NPC299855
0.8075	Intermediate Similarity	NPC7095
0.8075	Intermediate Similarity	NPC475417
0.8075	Intermediate Similarity	NPC475561
0.8072	Intermediate Similarity	NPC476077
0.8056	Intermediate Similarity	NPC475299
0.8056	Intermediate Similarity	NPC473711
0.805	Intermediate Similarity	NPC471162
0.8049	Intermediate Similarity	NPC323001
0.8049	Intermediate Similarity	NPC326235
0.8049	Intermediate Similarity	NPC106895
0.8037	Intermediate Similarity	NPC472022
0.8037	Intermediate Similarity	NPC257213
0.8037	Intermediate Similarity	NPC256142
0.8037	Intermediate Similarity	NPC304876
0.8037	Intermediate Similarity	NPC471135
0.8037	Intermediate Similarity	NPC472658
0.8037	Intermediate Similarity	NPC249471
0.8037	Intermediate Similarity	NPC133430
0.8037	Intermediate Similarity	NPC242262
0.8037	Intermediate Similarity	NPC1173
0.8037	Intermediate Similarity	NPC158333
0.8037	Intermediate Similarity	NPC469477
0.8037	Intermediate Similarity	NPC237549
0.8037	Intermediate Similarity	NPC472005
0.8037	Intermediate Similarity	NPC472030
0.8037	Intermediate Similarity	NPC472657
0.8037	Intermediate Similarity	NPC265395
0.8037	Intermediate Similarity	NPC473414
0.8035	Intermediate Similarity	NPC195972
0.8025	Intermediate Similarity	NPC471103
0.8025	Intermediate Similarity	NPC62792
0.8025	Intermediate Similarity	NPC51602
0.8025	Intermediate Similarity	NPC298072
0.8024	Intermediate Similarity	NPC477190
0.8024	Intermediate Similarity	NPC43304
0.8024	Intermediate Similarity	NPC477188
0.8013	Intermediate Similarity	NPC102015
0.8012	Intermediate Similarity	NPC471138
0.8012	Intermediate Similarity	NPC323356
0.8012	Intermediate Similarity	NPC81698
0.8012	Intermediate Similarity	NPC250046
0.8012	Intermediate Similarity	NPC60509
0.8012	Intermediate Similarity	NPC326328
0.8012	Intermediate Similarity	NPC309991
0.8	Intermediate Similarity	NPC112708
0.7988	Intermediate Similarity	NPC112523
0.7988	Intermediate Similarity	NPC469422
0.7988	Intermediate Similarity	NPC282239
0.7988	Intermediate Similarity	NPC114410
0.7988	Intermediate Similarity	NPC34066
0.7987	Intermediate Similarity	NPC4242
0.7987	Intermediate Similarity	NPC471911
0.7976	Intermediate Similarity	NPC322420
0.7975	Intermediate Similarity	NPC477905
0.7974	Intermediate Similarity	NPC80599
0.7974	Intermediate Similarity	NPC476976
0.7963	Intermediate Similarity	NPC161239
0.7963	Intermediate Similarity	NPC165260
0.7963	Intermediate Similarity	NPC198455
0.7963	Intermediate Similarity	NPC470245
0.7963	Intermediate Similarity	NPC473214
0.7963	Intermediate Similarity	NPC469448
0.7963	Intermediate Similarity	NPC112216
0.7952	Intermediate Similarity	NPC471102
0.7947	Intermediate Similarity	NPC473519
0.7947	Intermediate Similarity	NPC473805
0.7947	Intermediate Similarity	NPC471855
0.7944	Intermediate Similarity	NPC71385
0.7944	Intermediate Similarity	NPC230670
0.7939	Intermediate Similarity	NPC290683
0.7939	Intermediate Similarity	NPC475638
0.7939	Intermediate Similarity	NPC475548
0.7937	Intermediate Similarity	NPC127857
0.7931	Intermediate Similarity	NPC124828
0.7927	Intermediate Similarity	NPC146310
0.7927	Intermediate Similarity	NPC77719
0.7922	Intermediate Similarity	NPC159811
0.7917	Intermediate Similarity	NPC55744
0.7914	Intermediate Similarity	NPC306799
0.7914	Intermediate Similarity	NPC101043
0.7914	Intermediate Similarity	NPC469415
0.7908	Intermediate Similarity	NPC476977
0.7901	Intermediate Similarity	NPC476975
0.7901	Intermediate Similarity	NPC473215
0.7895	Intermediate Similarity	NPC471024
0.7892	Intermediate Similarity	NPC472393
0.7892	Intermediate Similarity	NPC469771
0.7888	Intermediate Similarity	NPC474241
0.7881	Intermediate Similarity	NPC198918
0.7881	Intermediate Similarity	NPC231888
0.7881	Intermediate Similarity	NPC290276
0.7881	Intermediate Similarity	NPC124878
0.7881	Intermediate Similarity	NPC92283
0.7881	Intermediate Similarity	NPC63404
0.7881	Intermediate Similarity	NPC10121
0.7881	Intermediate Similarity	NPC35338
0.7881	Intermediate Similarity	NPC10883
0.7881	Intermediate Similarity	NPC204214
0.7881	Intermediate Similarity	NPC471026
0.7879	Intermediate Similarity	NPC473670
0.7879	Intermediate Similarity	NPC21410
0.7875	Intermediate Similarity	NPC471139
0.7874	Intermediate Similarity	NPC477617
0.7871	Intermediate Similarity	NPC470143
0.7871	Intermediate Similarity	NPC322503

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 NPC475300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	814
0.2-0.3	2058
0.3-0.4	3311
0.4-0.5	1838
0.5-0.6	617
0.6-0.7	179
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8118	Intermediate Similarity	NPD7799	Discontinued
0.7826	Intermediate Similarity	NPD7236	Approved
0.7697	Intermediate Similarity	NPD7239	Suspended
0.758	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8368	Discontinued
0.75	Intermediate Similarity	NPD8407	Phase 2
0.7459	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7058	Phase 2
0.7283	Intermediate Similarity	NPD7057	Phase 3
0.7243	Intermediate Similarity	NPD8361	Approved
0.7243	Intermediate Similarity	NPD8435	Approved
0.7243	Intermediate Similarity	NPD8360	Approved
0.7166	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7319	Approved
0.7124	Intermediate Similarity	NPD8378	Approved
0.7124	Intermediate Similarity	NPD8296	Approved
0.7124	Intermediate Similarity	NPD8033	Approved
0.7124	Intermediate Similarity	NPD8380	Approved
0.7124	Intermediate Similarity	NPD8335	Approved
0.7124	Intermediate Similarity	NPD8379	Approved
0.7083	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7961	Discontinued
0.707	Intermediate Similarity	NPD7736	Approved
0.7059	Intermediate Similarity	NPD8294	Approved
0.7059	Intermediate Similarity	NPD8377	Approved
0.7032	Intermediate Similarity	NPD8328	Phase 3
0.7013	Intermediate Similarity	NPD7503	Approved
0.6993	Remote Similarity	NPD7516	Approved
0.6952	Remote Similarity	NPD8150	Discontinued
0.6939	Remote Similarity	NPD8320	Phase 1
0.6939	Remote Similarity	NPD8319	Approved
0.6928	Remote Similarity	NPD7327	Approved
0.6928	Remote Similarity	NPD7328	Approved
0.6927	Remote Similarity	NPD8485	Approved
0.6923	Remote Similarity	NPD7228	Approved
0.6903	Remote Similarity	NPD8516	Approved
0.6903	Remote Similarity	NPD8515	Approved
0.6903	Remote Similarity	NPD8517	Approved
0.6891	Remote Similarity	NPD7699	Phase 2
0.6891	Remote Similarity	NPD7700	Phase 2
0.6887	Remote Similarity	NPD8133	Approved
0.6887	Remote Similarity	NPD6858	Approved
0.6887	Remote Similarity	NPD7094	Approved
0.6882	Remote Similarity	NPD8312	Approved
0.6882	Remote Similarity	NPD8313	Approved
0.6865	Remote Similarity	NPD7240	Approved
0.6833	Remote Similarity	NPD8127	Discontinued
0.6824	Remote Similarity	NPD6190	Approved
0.6795	Remote Similarity	NPD8513	Phase 3
0.678	Remote Similarity	NPD8455	Phase 2
0.6765	Remote Similarity	NPD8166	Discontinued
0.6752	Remote Similarity	NPD6370	Approved
0.6739	Remote Similarity	NPD3751	Discontinued
0.6736	Remote Similarity	NPD6535	Approved
0.6736	Remote Similarity	NPD6534	Approved
0.6717	Remote Similarity	NPD7435	Discontinued
0.6711	Remote Similarity	NPD6882	Approved
0.6711	Remote Similarity	NPD8297	Approved
0.6709	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD8293	Discontinued
0.6686	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7808	Phase 3
0.6648	Remote Similarity	NPD7199	Phase 2
0.6646	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6009	Approved
0.6645	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7698	Approved
0.6633	Remote Similarity	NPD7697	Approved
0.6633	Remote Similarity	NPD7497	Discontinued
0.6633	Remote Similarity	NPD7696	Phase 3
0.6629	Remote Similarity	NPD37	Approved
0.6625	Remote Similarity	NPD6616	Approved
0.6624	Remote Similarity	NPD6319	Approved
0.6624	Remote Similarity	NPD6054	Approved
0.6624	Remote Similarity	NPD7741	Discontinued
0.6612	Remote Similarity	NPD3787	Discontinued
0.6611	Remote Similarity	NPD4966	Approved
0.6611	Remote Similarity	NPD4965	Approved
0.6611	Remote Similarity	NPD4967	Phase 2
0.661	Remote Similarity	NPD7028	Phase 2
0.6601	Remote Similarity	NPD7874	Approved
0.6601	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7251	Discontinued
0.6596	Remote Similarity	NPD6765	Approved
0.6596	Remote Similarity	NPD6764	Approved
0.6584	Remote Similarity	NPD7701	Phase 2
0.6584	Remote Similarity	NPD7078	Approved
0.6578	Remote Similarity	NPD7074	Phase 3
0.6566	Remote Similarity	NPD6781	Approved
0.6566	Remote Similarity	NPD6777	Approved
0.6566	Remote Similarity	NPD6779	Approved
0.6566	Remote Similarity	NPD6776	Approved
0.6566	Remote Similarity	NPD6778	Approved
0.6566	Remote Similarity	NPD6780	Approved
0.6566	Remote Similarity	NPD6782	Approved
0.6564	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4632	Approved
0.6554	Remote Similarity	NPD7458	Discontinued
0.6543	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6797	Phase 2
0.6538	Remote Similarity	NPD6234	Discontinued
0.6537	Remote Similarity	NPD8462	Phase 1
0.6536	Remote Similarity	NPD6650	Approved
0.6536	Remote Similarity	NPD6649	Approved
0.6528	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7871	Phase 2
0.6517	Remote Similarity	NPD7870	Phase 2
0.65	Remote Similarity	NPD5760	Phase 2
0.65	Remote Similarity	NPD5761	Phase 2
0.649	Remote Similarity	NPD6412	Phase 2
0.649	Remote Similarity	NPD6685	Approved
0.6489	Remote Similarity	NPD7472	Approved
0.6488	Remote Similarity	NPD7801	Approved
0.6478	Remote Similarity	NPD6016	Approved
0.6478	Remote Similarity	NPD6015	Approved
0.6474	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2629	Approved
0.6471	Remote Similarity	NPD8151	Discontinued
0.6458	Remote Similarity	NPD6785	Approved
0.6458	Remote Similarity	NPD6784	Approved
0.6447	Remote Similarity	NPD6881	Approved
0.6447	Remote Similarity	NPD6686	Approved
0.6447	Remote Similarity	NPD6899	Approved
0.6438	Remote Similarity	NPD5988	Approved
0.6438	Remote Similarity	NPD5126	Approved
0.6438	Remote Similarity	NPD5125	Phase 3
0.6437	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7054	Approved
0.6433	Remote Similarity	NPD7115	Discovery
0.6433	Remote Similarity	NPD4198	Discontinued
0.6429	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6059	Approved
0.6411	Remote Similarity	NPD8404	Phase 2
0.6408	Remote Similarity	NPD7783	Phase 2
0.6408	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6372	Approved
0.6405	Remote Similarity	NPD6373	Approved
0.6395	Remote Similarity	NPD5763	Approved
0.6395	Remote Similarity	NPD5762	Approved
0.6393	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7962	Phase 2
0.6384	Remote Similarity	NPD6273	Approved
0.6382	Remote Similarity	NPD5697	Approved
0.6369	Remote Similarity	NPD6663	Approved
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6352	Remote Similarity	NPD7610	Discontinued
0.6349	Remote Similarity	NPD5844	Phase 1
0.634	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5736	Approved
0.6323	Remote Similarity	NPD6617	Approved
0.6323	Remote Similarity	NPD6869	Approved
0.6323	Remote Similarity	NPD6847	Approved
0.6319	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD7128	Approved
0.6316	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6675	Approved
0.6306	Remote Similarity	NPD6010	Discontinued
0.6305	Remote Similarity	NPD7680	Approved
0.6304	Remote Similarity	NPD7075	Discontinued
0.6299	Remote Similarity	NPD6012	Approved
0.6299	Remote Similarity	NPD6013	Approved
0.6299	Remote Similarity	NPD6014	Approved
0.6296	Remote Similarity	NPD3818	Discontinued
0.6296	Remote Similarity	NPD7604	Phase 2
0.6291	Remote Similarity	NPD5765	Approved
0.6291	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7055	Discontinued
0.6286	Remote Similarity	NPD4628	Phase 3
0.6282	Remote Similarity	NPD6912	Phase 3
0.6279	Remote Similarity	NPD7305	Phase 1
0.6277	Remote Similarity	NPD6166	Phase 2
0.6277	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5983	Phase 2
0.627	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6212	Phase 3
0.6263	Remote Similarity	NPD6213	Phase 3
0.6263	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6823	Phase 2
0.625	Remote Similarity	NPD6559	Discontinued
0.625	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6011	Approved
0.6234	Remote Similarity	NPD7320	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