NPASS Compound

Structure

NPC475567 OpenBabel07101718272D 86 95 0 0 1 0 0 0 0 0999 V2000 17.1401 -2.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8560 0.9896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7121 0.9896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6177 1.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5710 0.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4025 1.8936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5700 -2.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1411 -3.4635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4261 -2.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.7111 -0.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4280 5.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0297 2.6703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5710 5.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2850 5.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2943 2.0081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8239 3.6382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5710 4.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2850 4.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3531 2.3139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8828 3.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4280 2.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5710 2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7140 -1.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2850 -0.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4280 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8570 -1.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5228 0.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9411 -0.3058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4280 -1.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8560 -1.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4270 -1.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7121 -1.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7140 0.9896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1401 -1.9792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8560 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1411 -0.4948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7121 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6766 1.9575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4280 3.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1474 3.2819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5710 -1.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2850 -1.4844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7130 -1.4844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2841 -1.9792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 14.5691 -1.4844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7140 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8570 1.4844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7140 2.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9990 -1.4844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4270 -0.4948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.8551 -1.4844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.9971 -1.4844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.1401 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7130 -0.4948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1411 -1.4844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.5691 -0.4948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 17.9971 -0.4948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2062 3.5877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.2831 -0.4948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5710 -0.4948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9411 1.2954 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8570 -0.4948 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 1.7140 3.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.8541 -1.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 17.1401 0.9896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0005 4.5556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7354 2.2633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8570 -1.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4025 -0.9040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5700 -1.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2841 -2.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.4261 -1.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.8541 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9990 -0.4948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2841 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8551 -0.4948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.2831 -1.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4708 2.9255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1420 -1.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8570 2.4740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5700 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9981 -1.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.4261 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7 62 1 0 0 0 0 8 73 1 0 0 0 0 9 74 1 0 0 0 0 10 75 1 0 0 0 0 11 76 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 40 2 0 0 0 0 19 40 1 0 0 0 0 20 41 2 0 0 0 0 21 41 1 0 0 0 0 22 23 2 0 0 0 0 22 40 1 0 0 0 0 23 49 1 0 0 0 0 24 27 1 0 0 0 0 24 42 2 0 0 0 0 25 26 1 0 0 0 0 25 43 1 0 0 0 0 26 61 1 0 0 0 0 27 64 1 0 0 0 0 28 29 1 0 0 0 0 28 63 1 0 0 0 0 29 65 1 0 0 0 0 30 42 1 0 0 0 0 30 43 1 0 0 0 0 31 44 1 0 0 0 0 31 50 1 0 0 0 0 32 45 1 0 0 0 0 32 51 1 0 0 0 0 33 46 1 0 0 0 0 33 52 1 0 0 0 0 34 47 1 0 0 0 0 34 48 1 0 0 0 0 35 1 1 1 0 0 0 35 53 1 0 0 0 0 35 80 1 0 0 0 0 36 2 1 6 0 0 0 36 55 1 0 0 0 0 36 77 1 0 0 0 0 37 3 1 6 0 0 0 37 56 1 0 0 0 0 37 78 1 0 0 0 0 38 4 1 6 0 0 0 38 57 1 0 0 0 0 38 79 1 0 0 0 0 39 5 1 6 0 0 0 39 63 1 0 0 0 0 39 81 1 0 0 0 0 41 59 1 0 0 0 0 42 61 1 0 0 0 0 43 82 1 6 0 0 0 44 55 1 0 0 0 0 44 73 1 1 0 0 0 45 56 1 0 0 0 0 45 74 1 1 0 0 0 46 57 1 0 0 0 0 46 75 1 6 0 0 0 47 61 1 6 0 0 0 47 64 1 0 0 0 0 48 62 1 6 0 0 0 48 83 1 0 0 0 0 49 66 2 0 0 0 0 49 83 1 0 0 0 0 50 77 1 0 0 0 0 50 82 1 6 0 0 0 51 78 1 0 0 0 0 51 84 1 6 0 0 0 52 79 1 0 0 0 0 52 85 1 6 0 0 0 53 58 1 0 0 0 0 53 67 1 1 0 0 0 54 58 1 0 0 0 0 54 60 1 0 0 0 0 54 68 1 6 0 0 0 55 84 1 1 0 0 0 56 85 1 1 0 0 0 57 86 1 1 0 0 0 58 76 1 1 0 0 0 59 69 2 0 0 0 0 59 81 1 0 0 0 0 60 80 1 0 0 0 0 60 86 1 1 0 0 0 61 6 1 6 0 0 0 62 63 1 1 0 0 0 63 70 1 1 0 0 0 64 65 1 1 0 0 0 64 71 1 0 0 0 0 65 62 1 6 0 0 0 65 72 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1208.61
Volume:	1205.461
LogP:	5.245
LogD:	3.693
LogS:	-4.975
# Rotatable Bonds:	20
TPSA:	264.51
# H-Bond Aceptor:	21
# H-Bond Donor:	5
# Rings:	10
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.066
Synthetic Accessibility Score:	7.125
Fsp3:	0.723
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.428
MDCK Permeability:	0.0001324803160969168
Pgp-inhibitor:	0.131
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	86.1124496459961%
Volume Distribution (VD):	0.16
Pgp-substrate:	6.731500625610352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.347
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	1.974
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.901
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.732
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.926
Carcinogencity:	0.242
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC475567

Natural Product ID:	NPC475567
*Common Name:**	[(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17R)-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5S,6R)-3,5-Dihydroxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-8,14,17-Trihydroxy-10,13-Dimethyl-12-[(E)-3-Phenylprop-2-Enoyl]Oxy-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-17-Yl]Ethyl] Benzoate
IUPAC Name:	[(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17R)-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-8,14,17-trihydroxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] benzoate
Synonyms:
Standard InCHIKey:	HPZZWLOXDVNZIY-KTZIEJBZSA-N
Standard InCHI:	InChI=1S/C65H92O21/c1-35-53(67)58(76-11)54(68)60(80-35)86-57-38(4)79-52(33-46(57)75-10)85-56-37(3)78-51(32-45(56)74-9)84-55-36(2)77-50(31-44(55)73-8)82-43-25-26-61(6)42(30-43)24-27-64(71)47(61)34-48(83-49(66)23-22-40-18-14-12-15-19-40)62(7)63(70,28-29-65(62,64)72)39(5)81-59(69)41-20-16-13-17-21-41/h12-24,35-39,43-48,50-58,60,67-68,70-72H,25-34H2,1-11H3/b23-22+/t35-,36-,37-,38-,39+,43+,44+,45+,46-,47-,48-,50+,51+,52+,53+,54-,55-,56-,57-,58+,60+,61+,62-,63+,64+,65-/m1/s1
SMILES:	CC1C(C(C(C(O1)OC2C(OC(CC2OC)OC3C(OC(CC3OC)OC4C(OC(CC4OC)OC5CCC6(C7CC(C8(C(CCC8(C7(CC=C6C5)O)O)(C(C)OC(=O)C9=CC=CC=C9)O)C)OC(=O)C=CC1=CC=CC=C1)C)C)C)C)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508391
PubChem CID:	44575256
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	=	1220.0	nM	PMID[458269]

☑ 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 NPC475567 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	366
0.1-0.2	1321
0.2-0.3	2713
0.3-0.4	5624
0.4-0.5	9959
0.5-0.6	14103
0.6-0.7	6827
0.7-0.8	1399
0.8-0.85	231
0.85-0.9	116
0.9-0.95	31
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473557
1.0	High Similarity	NPC473468
0.9935	High Similarity	NPC475531
0.9935	High Similarity	NPC475175
0.9935	High Similarity	NPC475198
0.9608	High Similarity	NPC476784
0.9434	High Similarity	NPC477488
0.9245	High Similarity	NPC477491
0.9108	High Similarity	NPC319404
0.9085	High Similarity	NPC474564
0.9057	High Similarity	NPC165234
0.9057	High Similarity	NPC475536
0.9051	High Similarity	NPC477623
0.9026	High Similarity	NPC475447
0.9026	High Similarity	NPC476092
0.9026	High Similarity	NPC70236
0.9026	High Similarity	NPC475218
0.9	High Similarity	NPC473641
0.9	High Similarity	NPC475505
0.9	High Similarity	NPC475300
0.9	High Similarity	NPC475464
0.9	High Similarity	NPC475437
0.9	High Similarity	NPC478125
0.9	High Similarity	NPC473797
0.8938	High Similarity	NPC478124
0.8924	High Similarity	NPC318447
0.8924	High Similarity	NPC322048
0.8903	High Similarity	NPC476173
0.8861	High Similarity	NPC323001
0.8861	High Similarity	NPC326235
0.8854	High Similarity	NPC472658
0.8854	High Similarity	NPC472657
0.8841	High Similarity	NPC477471
0.8841	High Similarity	NPC477473
0.8841	High Similarity	NPC477469
0.8841	High Similarity	NPC477466
0.8812	High Similarity	NPC326328
0.8812	High Similarity	NPC471138
0.8812	High Similarity	NPC309991
0.8812	High Similarity	NPC323356
0.8797	High Similarity	NPC469398
0.8797	High Similarity	NPC469422
0.8797	High Similarity	NPC34066
0.8782	High Similarity	NPC469448
0.8766	High Similarity	NPC29704
0.8766	High Similarity	NPC174982
0.8766	High Similarity	NPC472572
0.8766	High Similarity	NPC472571
0.8766	High Similarity	NPC470157
0.8766	High Similarity	NPC472568
0.8766	High Similarity	NPC200471
0.8766	High Similarity	NPC177940
0.8766	High Similarity	NPC476973
0.8766	High Similarity	NPC184817
0.8766	High Similarity	NPC473088
0.8766	High Similarity	NPC96903
0.8766	High Similarity	NPC472575
0.8766	High Similarity	NPC469349
0.8766	High Similarity	NPC158663
0.8766	High Similarity	NPC470159
0.8766	High Similarity	NPC171525
0.8766	High Similarity	NPC471104
0.8766	High Similarity	NPC70403
0.8734	High Similarity	NPC471135
0.8718	High Similarity	NPC471101
0.8718	High Similarity	NPC266265
0.8718	High Similarity	NPC92293
0.8718	High Similarity	NPC301556
0.8718	High Similarity	NPC270590
0.8701	High Similarity	NPC476974
0.8701	High Similarity	NPC163719
0.8701	High Similarity	NPC472569
0.8701	High Similarity	NPC472570
0.8701	High Similarity	NPC475122
0.8701	High Similarity	NPC25768
0.8701	High Similarity	NPC475759
0.8701	High Similarity	NPC57628
0.8701	High Similarity	NPC470152
0.8701	High Similarity	NPC11685
0.8701	High Similarity	NPC241951
0.8701	High Similarity	NPC95265
0.8701	High Similarity	NPC70716
0.8701	High Similarity	NPC125106
0.8701	High Similarity	NPC472573
0.8701	High Similarity	NPC95810
0.8701	High Similarity	NPC188865
0.8698	High Similarity	NPC475613
0.8679	High Similarity	NPC469456
0.8654	High Similarity	NPC281717
0.865	High Similarity	NPC150893
0.865	High Similarity	NPC329960
0.865	High Similarity	NPC295408
0.8645	High Similarity	NPC472556
0.8636	High Similarity	NPC163087
0.8634	High Similarity	NPC469399
0.8625	High Similarity	NPC475638
0.8625	High Similarity	NPC290683
0.8625	High Similarity	NPC475548
0.8608	High Similarity	NPC469415
0.8608	High Similarity	NPC478123
0.8608	High Similarity	NPC96308
0.8599	High Similarity	NPC476975
0.859	High Similarity	NPC473602
0.859	High Similarity	NPC474935
0.8581	High Similarity	NPC111466
0.8571	High Similarity	NPC469421
0.8554	High Similarity	NPC102465
0.8554	High Similarity	NPC469420
0.8553	High Similarity	NPC472548
0.8553	High Similarity	NPC477905
0.8544	High Similarity	NPC222102
0.8544	High Similarity	NPC473214
0.8544	High Similarity	NPC303429
0.8544	High Similarity	NPC470245
0.8526	High Similarity	NPC264270
0.8526	High Similarity	NPC40085
0.8516	High Similarity	NPC91703
0.8506	High Similarity	NPC224491
0.8506	High Similarity	NPC87448
0.8506	High Similarity	NPC118080
0.8506	High Similarity	NPC16912
0.8506	High Similarity	NPC97947
0.8506	High Similarity	NPC27377
0.8506	High Similarity	NPC41481
0.8506	High Similarity	NPC291599
0.8506	High Similarity	NPC472576
0.8491	Intermediate Similarity	NPC470153
0.8481	Intermediate Similarity	NPC76103
0.8481	Intermediate Similarity	NPC473215
0.8471	Intermediate Similarity	NPC312393
0.8471	Intermediate Similarity	NPC478263
0.8457	Intermediate Similarity	NPC469417
0.8452	Intermediate Similarity	NPC34012
0.8452	Intermediate Similarity	NPC473755
0.8452	Intermediate Similarity	NPC475513
0.8447	Intermediate Similarity	NPC5115
0.8447	Intermediate Similarity	NPC472549
0.8443	Intermediate Similarity	NPC40138
0.8442	Intermediate Similarity	NPC97667
0.8442	Intermediate Similarity	NPC473081
0.8442	Intermediate Similarity	NPC211137
0.8442	Intermediate Similarity	NPC100913
0.8442	Intermediate Similarity	NPC476094
0.8442	Intermediate Similarity	NPC4341
0.8442	Intermediate Similarity	NPC472547
0.8442	Intermediate Similarity	NPC200592
0.8442	Intermediate Similarity	NPC275592
0.8442	Intermediate Similarity	NPC90614
0.8442	Intermediate Similarity	NPC473613
0.8442	Intermediate Similarity	NPC43241
0.8442	Intermediate Similarity	NPC473112
0.8442	Intermediate Similarity	NPC473758
0.8442	Intermediate Similarity	NPC473085
0.8442	Intermediate Similarity	NPC48017
0.8442	Intermediate Similarity	NPC184747
0.8442	Intermediate Similarity	NPC147880
0.8442	Intermediate Similarity	NPC171207
0.8442	Intermediate Similarity	NPC473060
0.8442	Intermediate Similarity	NPC473109
0.8428	Intermediate Similarity	NPC475417
0.8428	Intermediate Similarity	NPC475561
0.8428	Intermediate Similarity	NPC31829
0.8418	Intermediate Similarity	NPC327031
0.8418	Intermediate Similarity	NPC473760
0.8415	Intermediate Similarity	NPC476077
0.8412	Intermediate Similarity	NPC477617
0.8408	Intermediate Similarity	NPC478264
0.8405	Intermediate Similarity	NPC477736
0.8397	Intermediate Similarity	NPC139067
0.8397	Intermediate Similarity	NPC246480
0.8397	Intermediate Similarity	NPC473673
0.8397	Intermediate Similarity	NPC147217
0.8397	Intermediate Similarity	NPC270498
0.8397	Intermediate Similarity	NPC177340
0.8397	Intermediate Similarity	NPC475429
0.8397	Intermediate Similarity	NPC191082
0.8385	Intermediate Similarity	NPC133430
0.8385	Intermediate Similarity	NPC469477
0.8377	Intermediate Similarity	NPC214550
0.8377	Intermediate Similarity	NPC210591
0.8377	Intermediate Similarity	NPC475652
0.8375	Intermediate Similarity	NPC298072
0.8375	Intermediate Similarity	NPC62792
0.8354	Intermediate Similarity	NPC209592
0.8354	Intermediate Similarity	NPC48599
0.8352	Intermediate Similarity	NPC189704
0.8344	Intermediate Similarity	NPC34943
0.8344	Intermediate Similarity	NPC477735
0.8344	Intermediate Similarity	NPC67777
0.8344	Intermediate Similarity	NPC51314
0.8333	Intermediate Similarity	NPC132599
0.8333	Intermediate Similarity	NPC228204
0.8333	Intermediate Similarity	NPC26033
0.8333	Intermediate Similarity	NPC473632
0.8333	Intermediate Similarity	NPC473611
0.8333	Intermediate Similarity	NPC469730
0.8333	Intermediate Similarity	NPC471176
0.8313	Intermediate Similarity	NPC66193
0.8312	Intermediate Similarity	NPC39549
0.8312	Intermediate Similarity	NPC183122

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 NPC475567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	822
0.2-0.3	1744
0.3-0.4	3122
0.4-0.5	2154
0.5-0.6	821
0.6-0.7	153
0.7-0.8	32
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD7799	Discontinued
0.7977	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7236	Approved
0.7818	Intermediate Similarity	NPD7239	Suspended
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.7542	Intermediate Similarity	NPD8368	Discontinued
0.7514	Intermediate Similarity	NPD8407	Phase 2
0.7459	Intermediate Similarity	NPD8312	Approved
0.7459	Intermediate Similarity	NPD8313	Approved
0.7405	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7058	Phase 2
0.7399	Intermediate Similarity	NPD7057	Phase 3
0.7384	Intermediate Similarity	NPD8455	Phase 2
0.7377	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD8435	Approved
0.7351	Intermediate Similarity	NPD8361	Approved
0.7351	Intermediate Similarity	NPD8360	Approved
0.7277	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7243	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8127	Discontinued
0.7222	Intermediate Similarity	NPD7228	Approved
0.7176	Intermediate Similarity	NPD6273	Approved
0.7158	Intermediate Similarity	NPD7240	Approved
0.7128	Intermediate Similarity	NPD8320	Phase 1
0.7128	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD8485	Approved
0.7107	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7700	Phase 2
0.7083	Intermediate Similarity	NPD7699	Phase 2
0.7077	Intermediate Similarity	NPD7497	Discontinued
0.7059	Intermediate Similarity	NPD8150	Discontinued
0.7052	Intermediate Similarity	NPD7458	Discontinued
0.7032	Intermediate Similarity	NPD8379	Approved
0.7032	Intermediate Similarity	NPD8296	Approved
0.7032	Intermediate Similarity	NPD8378	Approved
0.7032	Intermediate Similarity	NPD8033	Approved
0.7032	Intermediate Similarity	NPD8380	Approved
0.7032	Intermediate Similarity	NPD8335	Approved
0.7006	Intermediate Similarity	NPD7266	Discontinued
0.6994	Remote Similarity	NPD7961	Discontinued
0.6984	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8166	Discontinued
0.6968	Remote Similarity	NPD8377	Approved
0.6968	Remote Similarity	NPD7741	Discontinued
0.6968	Remote Similarity	NPD8294	Approved
0.6957	Remote Similarity	NPD7074	Phase 3
0.6951	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD37	Approved
0.6927	Remote Similarity	NPD6535	Approved
0.6927	Remote Similarity	NPD6534	Approved
0.6923	Remote Similarity	NPD7503	Approved
0.691	Remote Similarity	NPD4965	Approved
0.691	Remote Similarity	NPD4967	Phase 2
0.691	Remote Similarity	NPD4966	Approved
0.6904	Remote Similarity	NPD7435	Discontinued
0.6903	Remote Similarity	NPD7516	Approved
0.6902	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5126	Approved
0.6879	Remote Similarity	NPD5125	Phase 3
0.6871	Remote Similarity	NPD7008	Discontinued
0.6865	Remote Similarity	NPD7472	Approved
0.6855	Remote Similarity	NPD7507	Approved
0.6851	Remote Similarity	NPD7199	Phase 2
0.6845	Remote Similarity	NPD7808	Phase 3
0.6839	Remote Similarity	NPD7328	Approved
0.6839	Remote Similarity	NPD7327	Approved
0.6835	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6234	Discontinued
0.6832	Remote Similarity	NPD7319	Approved
0.6821	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD7698	Approved
0.6818	Remote Similarity	NPD7697	Approved
0.6818	Remote Similarity	NPD7028	Phase 2
0.6816	Remote Similarity	NPD8151	Discontinued
0.6811	Remote Similarity	NPD5844	Phase 1
0.6811	Remote Similarity	NPD7054	Approved
0.6798	Remote Similarity	NPD5761	Phase 2
0.6798	Remote Similarity	NPD5760	Phase 2
0.6797	Remote Similarity	NPD8133	Approved
0.6791	Remote Similarity	NPD6559	Discontinued
0.6791	Remote Similarity	NPD7251	Discontinued
0.6784	Remote Similarity	NPD4628	Phase 3
0.6782	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7874	Approved
0.6778	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6823	Phase 2
0.6766	Remote Similarity	NPD7701	Phase 2
0.6751	Remote Similarity	NPD6778	Approved
0.6751	Remote Similarity	NPD6776	Approved
0.6751	Remote Similarity	NPD6781	Approved
0.6751	Remote Similarity	NPD6780	Approved
0.6751	Remote Similarity	NPD6779	Approved
0.6751	Remote Similarity	NPD6782	Approved
0.6751	Remote Similarity	NPD6777	Approved
0.6749	Remote Similarity	NPD7783	Phase 2
0.6749	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6797	Phase 2
0.6738	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6764	Approved
0.6702	Remote Similarity	NPD6765	Approved
0.67	Remote Similarity	NPD7870	Phase 2
0.67	Remote Similarity	NPD7871	Phase 2
0.6688	Remote Similarity	NPD6858	Approved
0.6688	Remote Similarity	NPD7094	Approved
0.6685	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7801	Approved
0.6647	Remote Similarity	NPD6190	Approved
0.6634	Remote Similarity	NPD8462	Phase 1
0.663	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6213	Phase 3
0.6615	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6212	Phase 3
0.6611	Remote Similarity	NPD7819	Suspended
0.6608	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2629	Approved
0.659	Remote Similarity	NPD7003	Approved
0.6587	Remote Similarity	NPD6663	Approved
0.6582	Remote Similarity	NPD7610	Discontinued
0.6579	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3818	Discontinued
0.6578	Remote Similarity	NPD3751	Discontinued
0.6567	Remote Similarity	NPD7680	Approved
0.6562	Remote Similarity	NPD6785	Approved
0.6562	Remote Similarity	NPD6784	Approved
0.6561	Remote Similarity	NPD4198	Discontinued
0.6554	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5736	Approved
0.6541	Remote Similarity	NPD3787	Discontinued
0.6536	Remote Similarity	NPD4380	Phase 2
0.6533	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7097	Phase 1
0.6527	Remote Similarity	NPD3764	Approved
0.6519	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5762	Approved
0.6512	Remote Similarity	NPD5763	Approved
0.6507	Remote Similarity	NPD8404	Phase 2
0.6503	Remote Similarity	NPD7075	Discontinued
0.65	Remote Similarity	NPD8515	Approved
0.65	Remote Similarity	NPD8517	Approved
0.65	Remote Similarity	NPD8516	Approved
0.6497	Remote Similarity	NPD5951	Approved
0.6494	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6166	Phase 2
0.6471	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7736	Approved
0.6462	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7768	Phase 2
0.6437	Remote Similarity	NPD6674	Discontinued
0.6436	Remote Similarity	NPD7473	Discontinued
0.6432	Remote Similarity	NPD5494	Approved
0.6422	Remote Similarity	NPD7999	Approved
0.6422	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.642	Remote Similarity	NPD8328	Phase 3
0.6416	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6004	Phase 3
0.6416	Remote Similarity	NPD6005	Phase 3
0.6416	Remote Similarity	NPD6002	Phase 3
0.6416	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6685	Approved
0.6398	Remote Similarity	NPD8513	Phase 3
0.6398	Remote Similarity	NPD6959	Discontinued
0.6393	Remote Similarity	NPD5402	Approved
0.6393	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6232	Discontinued
0.6364	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6686	Approved
0.6358	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6599	Discontinued
0.6353	Remote Similarity	NPD4140	Approved
0.6346	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7009	Phase 2
0.6333	Remote Similarity	NPD7930	Approved
0.6325	Remote Similarity	NPD3094	Phase 2
0.6323	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7411	Suspended
0.6316	Remote Similarity	NPD6355	Discontinued
0.6307	Remote Similarity	NPD3750	Approved
0.6299	Remote Similarity	NPD6412	Phase 2
0.6296	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7715	Approved
0.6294	Remote Similarity	NPD7714	Approved
0.629	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6801	Discontinued
0.6279	Remote Similarity	NPD6653	Approved
0.6278	Remote Similarity	NPD5403	Approved
0.6264	Remote Similarity	NPD5404	Approved
0.6264	Remote Similarity	NPD5405	Approved
0.6264	Remote Similarity	NPD5406	Approved
0.6264	Remote Similarity	NPD5408	Approved
0.6257	Remote Similarity	NPD5401	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