NPASS Compound

Structure

NPC267592 OpenBabel07101718272D 86 91 0 0 1 0 0 0 0 0999 V2000 -4.1775 11.0947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1789 2.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0130 -6.7533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 -6.7533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1775 -1.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9956 0.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6710 -3.8590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3420 1.9295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8355 -1.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1775 10.1300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3192 1.8180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 9.6476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5101 2.3434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 8.6828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5065 8.2005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5065 7.2357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6710 6.7533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5065 2.7972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0541 2.9751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6710 5.7886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0407 2.4587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6299 2.9751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8355 5.3062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7023 1.9929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6505 1.9054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1775 2.7972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5243 1.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8355 4.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8414 2.4309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6434 2.4587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5243 0.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6710 3.8590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1775 -6.2709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1775 -0.4824 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1082 0.5613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5065 -3.3767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3420 0.9648 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8355 -0.4824 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9818 1.9929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7023 0.3219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6710 2.8943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0130 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9303 0.0137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0130 0.9648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3671 -0.1060 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1775 -3.3767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1775 1.4471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1775 -2.4119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3420 -0.9648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3420 -3.8590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5065 0.4824 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6710 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5065 -0.4824 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9818 0.3219 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6710 0.9648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8355 1.4471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1775 -5.3062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 0.9648 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3420 -1.9295 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1775 -0.4824 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1597 0.8695 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9648 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -0.1161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5065 2.4119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8485 -0.4824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5758 -0.7033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8485 1.4471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0690 -1.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0130 -3.8590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1775 2.4119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0130 -1.9295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3420 -1.9295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0130 -4.8238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7229 0.9892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5065 -2.4119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1775 0.4824 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 5.1597 1.4453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0407 -0.1439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8355 2.4119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 -4.8238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 -0.9648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8355 1.4471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6434 -0.1439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5065 1.4471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 28 1 0 0 0 0 24 27 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 30 39 1 0 0 0 0 31 40 1 0 0 0 0 32 41 1 0 0 0 0 33 57 1 0 0 0 0 34 5 1 1 0 0 0 34 42 1 0 0 0 0 34 74 1 0 0 0 0 35 6 1 6 0 0 0 35 43 1 0 0 0 0 35 75 1 0 0 0 0 36 7 1 1 0 0 0 36 50 1 0 0 0 0 36 76 1 0 0 0 0 37 8 1 6 0 0 0 37 51 1 0 0 0 0 37 77 1 0 0 0 0 38 9 1 1 0 0 0 38 52 1 0 0 0 0 38 78 1 0 0 0 0 39 29 1 6 0 0 0 39 79 1 0 0 0 0 40 63 2 0 0 0 0 40 80 1 0 0 0 0 41 64 2 0 0 0 0 41 81 1 0 0 0 0 42 44 1 0 0 0 0 42 65 1 6 0 0 0 43 45 1 0 0 0 0 43 66 1 6 0 0 0 44 47 1 0 0 0 0 44 67 1 1 0 0 0 45 54 1 0 0 0 0 45 68 1 6 0 0 0 46 48 1 0 0 0 0 46 50 1 0 0 0 0 46 69 1 1 0 0 0 47 58 1 0 0 0 0 47 70 1 1 0 0 0 48 59 1 0 0 0 0 48 71 1 1 0 0 0 49 53 1 0 0 0 0 49 60 1 0 0 0 0 49 72 1 6 0 0 0 50 82 1 6 0 0 0 51 53 1 0 0 0 0 51 84 1 1 0 0 0 52 55 1 0 0 0 0 52 83 1 6 0 0 0 53 80 1 6 0 0 0 54 61 1 0 0 0 0 54 85 1 1 0 0 0 55 56 1 0 0 0 0 55 86 1 1 0 0 0 56 62 1 0 0 0 0 56 81 1 1 0 0 0 57 73 2 0 0 0 0 57 82 1 0 0 0 0 58 74 1 0 0 0 0 58 86 1 6 0 0 0 59 76 1 0 0 0 0 59 83 1 6 0 0 0 60 77 1 6 0 0 0 60 85 1 0 0 0 0 61 75 1 6 0 0 0 61 79 1 0 0 0 0 62 78 1 0 0 0 0 62 84 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1236.72
Volume:	1232.625
LogP:	8.386
LogD:	4.451
LogS:	-4.976
# Rotatable Bonds:	25
TPSA:	333.04
# H-Bond Aceptor:	24
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.038
Synthetic Accessibility Score:	7.957
Fsp3:	0.952
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.244
MDCK Permeability:	9.648745617596433e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.769
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	95.40328216552734%
Volume Distribution (VD):	0.626
Pgp-substrate:	5.140904903411865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.232
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	1.189
Half-life (T1/2):	0.189

ADMET: Toxicity

hERG Blockers:	0.936
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.627
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.947
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC267592

Natural Product ID:	NPC267592
*Common Name:**	Pescaprein Ii
IUPAC Name:	n.a.
Synonyms:	pescaprein II
Standard InCHIKey:	PNRJNPJRTTWEBB-JYPGLRBKSA-N
Standard InCHI:	InChI=1S/C62H108O24/c1-10-12-14-15-16-17-20-23-28-32-41(64)81-56-55(86-58-47(70)44(67)42(65)34(5)74-58)52(83-59-48(71)46(69)50(36(7)76-59)82-57(73)33(3)4)38(9)78-62(56)84-51-37(8)77-60-49(72)53(51)80-40(63)31-27-24-21-18-19-22-26-30-39(29-25-13-11-2)79-61-54(85-60)45(68)43(66)35(6)75-61/h33-39,42-56,58-62,65-72H,10-32H2,1-9H3/t34-,35+,36-,37-,38-,39-,42-,43-,44+,45-,46-,47+,48+,49+,50-,51-,52-,53-,54+,55+,56+,58-,59-,60-,61-,62-/m0/s1
SMILES:	CCCCCCCCCCCC(=O)O[C@@H]1[C@@H]([C@H]([C@H](C)O[C@H]1O[C@H]1[C@H](C)O[C@@H]2[C@@H]([C@@H]1OC(=O)CCCCCCCCC[C@H](CCCCC)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](C)O1)O)O)O2)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)OC(=O)C(C)C)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509568
PubChem CID:	44575414
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730248]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	Leaves	Khon Kaen, Thailand	2002-APR	PMID[15921434]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	ground entire plants	Hainan Province, China	2004-APR	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21338052]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31017778]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	4

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	5.0	ug ml-1	PMID[495832]

☑ 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 NPC267592 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	728
0.1-0.2	4725
0.2-0.3	14199
0.3-0.4	11305
0.4-0.5	6863
0.5-0.6	2889
0.6-0.7	1444
0.7-0.8	444
0.8-0.85	15
0.85-0.9	8
0.9-0.95	29
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC44782
0.9867	High Similarity	NPC123204
0.9867	High Similarity	NPC477331
0.9867	High Similarity	NPC89843
0.9867	High Similarity	NPC126685
0.9867	High Similarity	NPC115013
0.9867	High Similarity	NPC143421
0.9867	High Similarity	NPC224953
0.9867	High Similarity	NPC169345
0.9867	High Similarity	NPC119583
0.9867	High Similarity	NPC183888
0.9867	High Similarity	NPC184915
0.9867	High Similarity	NPC477318
0.9867	High Similarity	NPC472204
0.9867	High Similarity	NPC472205
0.9867	High Similarity	NPC477319
0.9867	High Similarity	NPC27289
0.9867	High Similarity	NPC477317
0.9867	High Similarity	NPC259294
0.9867	High Similarity	NPC472203
0.9867	High Similarity	NPC472202
0.9867	High Similarity	NPC472200
0.9867	High Similarity	NPC307400
0.9867	High Similarity	NPC290012
0.9867	High Similarity	NPC472201
0.973	High Similarity	NPC113745
0.973	High Similarity	NPC475425
0.973	High Similarity	NPC477329
0.973	High Similarity	NPC281563
0.973	High Similarity	NPC477330
0.973	High Similarity	NPC109887
0.973	High Similarity	NPC477320
0.973	High Similarity	NPC477325
0.973	High Similarity	NPC477323
0.973	High Similarity	NPC477328
0.973	High Similarity	NPC477326
0.973	High Similarity	NPC146380
0.961	High Similarity	NPC477332
0.961	High Similarity	NPC60849
0.961	High Similarity	NPC472352
0.96	High Similarity	NPC294748
0.96	High Similarity	NPC85759
0.96	High Similarity	NPC146992
0.96	High Similarity	NPC158302
0.96	High Similarity	NPC22742
0.96	High Similarity	NPC477344
0.96	High Similarity	NPC477346
0.9459	High Similarity	NPC477350
0.9351	High Similarity	NPC475667
0.9351	High Similarity	NPC476087
0.9351	High Similarity	NPC269318
0.9351	High Similarity	NPC297768
0.9351	High Similarity	NPC475327
0.9351	High Similarity	NPC186992
0.9351	High Similarity	NPC475270
0.9351	High Similarity	NPC173328
0.9351	High Similarity	NPC238056
0.9351	High Similarity	NPC477347
0.9333	High Similarity	NPC476783
0.9333	High Similarity	NPC216883
0.9333	High Similarity	NPC476781
0.9333	High Similarity	NPC476782
0.9054	High Similarity	NPC206823
0.9054	High Similarity	NPC9763
0.9054	High Similarity	NPC169085
0.9054	High Similarity	NPC39266
0.9054	High Similarity	NPC163812
0.9054	High Similarity	NPC225748
0.8784	High Similarity	NPC52268
0.8784	High Similarity	NPC53760
0.8649	High Similarity	NPC211428
0.8649	High Similarity	NPC285003
0.8649	High Similarity	NPC241265
0.8553	High Similarity	NPC291228
0.8553	High Similarity	NPC308096
0.8514	High Similarity	NPC250619
0.8514	High Similarity	NPC67099
0.8514	High Similarity	NPC50228
0.8514	High Similarity	NPC97736
0.8421	Intermediate Similarity	NPC184550
0.8421	Intermediate Similarity	NPC185419
0.8378	Intermediate Similarity	NPC206601
0.8295	Intermediate Similarity	NPC44682
0.8295	Intermediate Similarity	NPC163409
0.8108	Intermediate Similarity	NPC76881
0.8108	Intermediate Similarity	NPC471761
0.8108	Intermediate Similarity	NPC190418
0.8108	Intermediate Similarity	NPC471760
0.8108	Intermediate Similarity	NPC12040
0.809	Intermediate Similarity	NPC477345
0.809	Intermediate Similarity	NPC477348
0.809	Intermediate Similarity	NPC238264
0.8068	Intermediate Similarity	NPC477349
0.7973	Intermediate Similarity	NPC6848
0.7912	Intermediate Similarity	NPC475164
0.7912	Intermediate Similarity	NPC476066
0.7912	Intermediate Similarity	NPC475375
0.7912	Intermediate Similarity	NPC473605
0.7912	Intermediate Similarity	NPC475241
0.7912	Intermediate Similarity	NPC475525
0.7912	Intermediate Similarity	NPC475540
0.7912	Intermediate Similarity	NPC475593
0.7912	Intermediate Similarity	NPC473765
0.7857	Intermediate Similarity	NPC248415
0.7838	Intermediate Similarity	NPC325773
0.7614	Intermediate Similarity	NPC51662
0.7568	Intermediate Similarity	NPC477757
0.7568	Intermediate Similarity	NPC477753
0.7568	Intermediate Similarity	NPC477750
0.7568	Intermediate Similarity	NPC477755
0.7568	Intermediate Similarity	NPC477763
0.7568	Intermediate Similarity	NPC477762
0.7558	Intermediate Similarity	NPC38295
0.7558	Intermediate Similarity	NPC473500
0.7558	Intermediate Similarity	NPC156089
0.7558	Intermediate Similarity	NPC470313
0.7532	Intermediate Similarity	NPC477756
0.7532	Intermediate Similarity	NPC477751
0.7532	Intermediate Similarity	NPC477764
0.7532	Intermediate Similarity	NPC477752
0.7436	Intermediate Similarity	NPC477758
0.7436	Intermediate Similarity	NPC477754
0.7436	Intermediate Similarity	NPC477760
0.7436	Intermediate Similarity	NPC477761
0.7436	Intermediate Similarity	NPC477759
0.74	Intermediate Similarity	NPC22709
0.7374	Intermediate Similarity	NPC126753
0.7347	Intermediate Similarity	NPC231271
0.7347	Intermediate Similarity	NPC470519
0.7347	Intermediate Similarity	NPC469827
0.7327	Intermediate Similarity	NPC471431
0.7326	Intermediate Similarity	NPC236649
0.7326	Intermediate Similarity	NPC21693
0.7303	Intermediate Similarity	NPC470657
0.73	Intermediate Similarity	NPC207693
0.7297	Intermediate Similarity	NPC317023
0.7222	Intermediate Similarity	NPC314364
0.7222	Intermediate Similarity	NPC31349
0.72	Intermediate Similarity	NPC287269
0.72	Intermediate Similarity	NPC471430
0.7162	Intermediate Similarity	NPC472025
0.7157	Intermediate Similarity	NPC470622
0.7143	Intermediate Similarity	NPC80191
0.7143	Intermediate Similarity	NPC310031
0.7129	Intermediate Similarity	NPC262567
0.7129	Intermediate Similarity	NPC471626
0.7129	Intermediate Similarity	NPC473688
0.7129	Intermediate Similarity	NPC231566
0.7129	Intermediate Similarity	NPC469826
0.7113	Intermediate Similarity	NPC471428
0.7113	Intermediate Similarity	NPC471426
0.7113	Intermediate Similarity	NPC471427
0.71	Intermediate Similarity	NPC273189
0.71	Intermediate Similarity	NPC184805
0.7079	Intermediate Similarity	NPC288471
0.7059	Intermediate Similarity	NPC94086
0.7059	Intermediate Similarity	NPC473817
0.7059	Intermediate Similarity	NPC228190
0.7059	Intermediate Similarity	NPC92297
0.7059	Intermediate Similarity	NPC220836
0.7059	Intermediate Similarity	NPC273002
0.7059	Intermediate Similarity	NPC469825
0.7059	Intermediate Similarity	NPC236753
0.7059	Intermediate Similarity	NPC474003
0.7059	Intermediate Similarity	NPC233433
0.7053	Intermediate Similarity	NPC215570
0.7048	Intermediate Similarity	NPC43550
0.7048	Intermediate Similarity	NPC70809
0.7048	Intermediate Similarity	NPC305981
0.7048	Intermediate Similarity	NPC227551
0.7048	Intermediate Similarity	NPC71065
0.7048	Intermediate Similarity	NPC475140
0.7048	Intermediate Similarity	NPC4328
0.7048	Intermediate Similarity	NPC236638
0.7048	Intermediate Similarity	NPC202828
0.7048	Intermediate Similarity	NPC309907
0.7048	Intermediate Similarity	NPC60557
0.7048	Intermediate Similarity	NPC67857
0.7048	Intermediate Similarity	NPC261506
0.7048	Intermediate Similarity	NPC65105
0.7048	Intermediate Similarity	NPC294453
0.7048	Intermediate Similarity	NPC298034
0.7048	Intermediate Similarity	NPC475160
0.7048	Intermediate Similarity	NPC119592
0.7048	Intermediate Similarity	NPC100639
0.7048	Intermediate Similarity	NPC57484
0.7048	Intermediate Similarity	NPC471550
0.7048	Intermediate Similarity	NPC54636
0.7048	Intermediate Similarity	NPC161717
0.7048	Intermediate Similarity	NPC79643
0.7048	Intermediate Similarity	NPC76972
0.7048	Intermediate Similarity	NPC123199
0.7048	Intermediate Similarity	NPC471385
0.7048	Intermediate Similarity	NPC250247
0.7048	Intermediate Similarity	NPC293330
0.7048	Intermediate Similarity	NPC469782
0.7048	Intermediate Similarity	NPC224381
0.7048	Intermediate Similarity	NPC204414
0.7048	Intermediate Similarity	NPC473714
0.7048	Intermediate Similarity	NPC41061

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 NPC267592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	788
0.1-0.2	4321
0.2-0.3	2778
0.3-0.4	786
0.4-0.5	299
0.5-0.6	132
0.6-0.7	42
0.7-0.8	4
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
0.7927	Intermediate Similarity	NPD7329	Approved
0.7568	Intermediate Similarity	NPD6123	Approved
0.6988	Remote Similarity	NPD3181	Approved
0.6832	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8133	Approved
0.679	Remote Similarity	NPD898	Approved
0.679	Remote Similarity	NPD896	Approved
0.679	Remote Similarity	NPD897	Approved
0.6762	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3728	Approved
0.6757	Remote Similarity	NPD3730	Approved
0.6757	Remote Similarity	NPD7346	Approved
0.6634	Remote Similarity	NPD8139	Approved
0.6634	Remote Similarity	NPD8083	Approved
0.6634	Remote Similarity	NPD8138	Approved
0.6634	Remote Similarity	NPD8082	Approved
0.6634	Remote Similarity	NPD8085	Approved
0.6634	Remote Similarity	NPD8086	Approved
0.6634	Remote Similarity	NPD8084	Approved
0.6622	Remote Similarity	NPD892	Phase 3
0.6622	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD891	Phase 3
0.6622	Remote Similarity	NPD893	Approved
0.6622	Remote Similarity	NPD888	Phase 3
0.6602	Remote Similarity	NPD8393	Approved
0.6571	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8276	Approved
0.6569	Remote Similarity	NPD8275	Approved
0.6505	Remote Similarity	NPD8081	Approved
0.6486	Remote Similarity	NPD2269	Approved
0.642	Remote Similarity	NPD7909	Approved
0.6413	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3669	Approved
0.6381	Remote Similarity	NPD8140	Approved
0.6381	Remote Similarity	NPD8307	Discontinued
0.6372	Remote Similarity	NPD8515	Approved
0.6372	Remote Similarity	NPD8517	Approved
0.6372	Remote Similarity	NPD8516	Approved
0.6353	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD905	Approved
0.6351	Remote Similarity	NPD904	Phase 3
0.6327	Remote Similarity	NPD8171	Discontinued
0.6311	Remote Similarity	NPD7139	Approved
0.6311	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7140	Approved
0.6306	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8305	Approved
0.6262	Remote Similarity	NPD8306	Approved
0.6228	Remote Similarity	NPD8513	Phase 3
0.6204	Remote Similarity	NPD8087	Discontinued
0.6196	Remote Similarity	NPD1779	Approved
0.6196	Remote Similarity	NPD1780	Approved
0.6184	Remote Similarity	NPD887	Approved
0.6184	Remote Similarity	NPD895	Approved
0.6184	Remote Similarity	NPD889	Approved
0.6184	Remote Similarity	NPD894	Approved
0.6168	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD2267	Suspended
0.6121	Remote Similarity	NPD8328	Phase 3
0.6098	Remote Similarity	NPD8961	Approved
0.6	Remote Similarity	NPD8345	Approved
0.6	Remote Similarity	NPD8347	Approved
0.6	Remote Similarity	NPD8346	Approved
0.5963	Remote Similarity	NPD6941	Approved
0.596	Remote Similarity	NPD6698	Approved
0.596	Remote Similarity	NPD46	Approved
0.5946	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6412	Phase 2
0.5877	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD369	Approved
0.5849	Remote Similarity	NPD8300	Approved
0.5849	Remote Similarity	NPD8301	Approved
0.5789	Remote Similarity	NPD6940	Discontinued
0.5778	Remote Similarity	NPD1810	Approved
0.5778	Remote Similarity	NPD1811	Approved
0.5743	Remote Similarity	NPD7983	Approved
0.5714	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4238	Approved
0.5699	Remote Similarity	NPD4802	Phase 2
0.5696	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD1447	Phase 3
0.5686	Remote Similarity	NPD1446	Phase 3
0.5679	Remote Similarity	NPD8959	Approved
0.5678	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8998	Phase 2
0.5676	Remote Similarity	NPD9000	Phase 3
0.5676	Remote Similarity	NPD8999	Phase 3
0.5676	Remote Similarity	NPD8997	Approved
0.5676	Remote Similarity	NPD8993	Phase 1
0.5673	Remote Similarity	NPD6428	Approved
0.563	Remote Similarity	NPD8080	Discontinued
0.56	Remote Similarity	NPD618	Clinical (unspecified phase)

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