NPASS Compound

Structure

CID160517 OpenBabel06191715532D 31 32 0 0 1 0 0 0 0 0999 V2000 -1.8096 -0.1663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1275 1.4829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5804 3.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6266 2.3022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3831 1.7923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 2.2237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6847 4.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3517 1.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2461 -1.7034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3640 -1.3006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9388 -0.9304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2461 1.7034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3203 1.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9074 0.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2120 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2059 1.5654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5403 0.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6088 -2.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4925 0.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2059 -1.5654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3640 1.3006 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8398 -0.4848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2231 1.8499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7647 2.7465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9388 0.9304 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8398 0.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0463 -3.2374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8582 2.5828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2404 3.5623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7290 2.0335 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 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 7 29 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 20 2 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 25 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 27 1 0 0 0 0 21 26 1 6 0 0 0 21 30 1 0 0 0 0 22 26 1 6 0 0 0 22 31 1 0 0 0 0 23 28 2 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 25 5 1 6 0 0 0 26 6 1 6 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.29
Volume:	471.908
LogP:	4.049
LogD:	3.623
LogS:	-4.481
# Rotatable Bonds:	8
TPSA:	68.29
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.264
Synthetic Accessibility Score:	5.435
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.682
MDCK Permeability:	1.8021075447904877e-05
Pgp-inhibitor:	0.821
Pgp-substrate:	0.255
Human Intestinal Absorption (HIA):	0.785
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.853

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.808
Plasma Protein Binding (PPB):	79.8126220703125%
Volume Distribution (VD):	0.745
Pgp-substrate:	8.05915355682373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.245
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.522
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.383
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	3.101
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.938
Carcinogencity:	0.074
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.823

Download Data

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

Natural Product: NPC160517

Natural Product ID:	NPC160517
*Common Name:**	Vibsanin Q
IUPAC Name:	[(1S,4E,7S,8E,10R,11R)-4-(hydroxymethyl)-7-[(E)-4-methoxy-4-methylpent-2-enyl]-7,11-dimethyl-12-oxabicyclo[9.1.0]dodeca-4,8-dien-10-yl] 3-methylbut-2-enoate
Synonyms:	Vibsanin Q
Standard InCHIKey:	TVVRWBNLBVCRPH-XYBUGXQZSA-N
Standard InCHI:	InChI=1S/C26H40O5/c1-19(2)17-23(28)30-21-12-16-25(5,14-8-13-24(3,4)29-7)15-11-20(18-27)9-10-22-26(21,6)31-22/h8,11-13,16-17,21-22,27H,9-10,14-15,18H2,1-7H3/b13-8+,16-12+,20-11+/t21-,22+,25+,26+/m1/s1
SMILES:	COC(/C=C/C[C@]1(C)/C=C/[C@@H](OC(=O)C=C(C)C)[C@]2(C)O[C@H]2CC/C(=CC1)/CO)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470762
PubChem CID:	11154724
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)83457-3]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843567]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125219]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665952]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27592135]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33325237]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8103	Lecanora melanophthalma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1355	Urechis caupo	Species	Urechidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9903	Engelhardia spicata	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2304	Byssovorax cruenta	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25481	Lonchocarpus oaxacensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7060	Ficus ruficaulis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO276	Miscanthus sacchariflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15610	Citrus trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10806	Achillea roseoalba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24370	Crassocephalum crepidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5319	Ulmus thomasii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3830	Euplotes rariseta	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6310	Ruta bracteosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7766	Pericopsis schliebenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4516	Fasciospongia rimosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	<	10.0	ug ml-1	PMID[514804]

☑ 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 NPC160517 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	203
0.1-0.2	1440
0.2-0.3	4850
0.3-0.4	12393
0.4-0.5	13066
0.5-0.6	6824
0.6-0.7	3349
0.7-0.8	539
0.8-0.85	26
0.85-0.9	3
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC78673
1.0	High Similarity	NPC186155
0.975	High Similarity	NPC61527
0.8861	High Similarity	NPC84360
0.869	High Similarity	NPC471494
0.8642	High Similarity	NPC471537
0.8625	High Similarity	NPC477203
0.8621	High Similarity	NPC3952
0.85	High Similarity	NPC477202
0.8471	Intermediate Similarity	NPC11804
0.8452	Intermediate Similarity	NPC161045
0.8452	Intermediate Similarity	NPC474809
0.8415	Intermediate Similarity	NPC139712
0.8372	Intermediate Similarity	NPC311163
0.8354	Intermediate Similarity	NPC477085
0.8295	Intermediate Similarity	NPC83423
0.8276	Intermediate Similarity	NPC199382
0.8272	Intermediate Similarity	NPC469880
0.8272	Intermediate Similarity	NPC188860
0.8261	Intermediate Similarity	NPC205143
0.8235	Intermediate Similarity	NPC231601
0.8228	Intermediate Similarity	NPC477087
0.8228	Intermediate Similarity	NPC477086
0.8228	Intermediate Similarity	NPC477084
0.8214	Intermediate Similarity	NPC8538
0.8214	Intermediate Similarity	NPC315731
0.8214	Intermediate Similarity	NPC184208
0.8214	Intermediate Similarity	NPC474894
0.8214	Intermediate Similarity	NPC475944
0.8171	Intermediate Similarity	NPC233071
0.8111	Intermediate Similarity	NPC158061
0.8101	Intermediate Similarity	NPC4299
0.8095	Intermediate Similarity	NPC474739
0.809	Intermediate Similarity	NPC133450
0.8072	Intermediate Similarity	NPC209135
0.8072	Intermediate Similarity	NPC474816
0.8072	Intermediate Similarity	NPC248775
0.8025	Intermediate Similarity	NPC477204
0.8	Intermediate Similarity	NPC177668
0.8	Intermediate Similarity	NPC112868
0.7979	Intermediate Similarity	NPC475653
0.7976	Intermediate Similarity	NPC86971
0.7976	Intermediate Similarity	NPC180725
0.7976	Intermediate Similarity	NPC470149
0.7976	Intermediate Similarity	NPC470148
0.7975	Intermediate Similarity	NPC101622
0.7975	Intermediate Similarity	NPC269841
0.7959	Intermediate Similarity	NPC469957
0.7959	Intermediate Similarity	NPC108682
0.7959	Intermediate Similarity	NPC472263
0.7959	Intermediate Similarity	NPC469959
0.7957	Intermediate Similarity	NPC279621
0.7957	Intermediate Similarity	NPC476315
0.7957	Intermediate Similarity	NPC255410
0.7957	Intermediate Similarity	NPC57664
0.7952	Intermediate Similarity	NPC262747
0.7935	Intermediate Similarity	NPC469491
0.7935	Intermediate Similarity	NPC472467
0.7901	Intermediate Similarity	NPC329914
0.7901	Intermediate Similarity	NPC327383
0.7901	Intermediate Similarity	NPC329890
0.7901	Intermediate Similarity	NPC185186
0.7895	Intermediate Similarity	NPC79631
0.7895	Intermediate Similarity	NPC475053
0.7882	Intermediate Similarity	NPC470147
0.7882	Intermediate Similarity	NPC133226
0.7875	Intermediate Similarity	NPC469660
0.7872	Intermediate Similarity	NPC120299
0.7865	Intermediate Similarity	NPC316138
0.7865	Intermediate Similarity	NPC313658
0.7857	Intermediate Similarity	NPC279532
0.7857	Intermediate Similarity	NPC29389
0.7857	Intermediate Similarity	NPC93026
0.7857	Intermediate Similarity	NPC469960
0.7857	Intermediate Similarity	NPC265502
0.7849	Intermediate Similarity	NPC270013
0.7849	Intermediate Similarity	NPC14961
0.7849	Intermediate Similarity	NPC300710
0.7849	Intermediate Similarity	NPC220221
0.7848	Intermediate Similarity	NPC305698
0.7831	Intermediate Similarity	NPC301525
0.7826	Intermediate Similarity	NPC472196
0.7826	Intermediate Similarity	NPC472195
0.7826	Intermediate Similarity	NPC125674
0.7826	Intermediate Similarity	NPC475838
0.7826	Intermediate Similarity	NPC238090
0.7826	Intermediate Similarity	NPC228451
0.7816	Intermediate Similarity	NPC44261
0.7816	Intermediate Similarity	NPC49208
0.7816	Intermediate Similarity	NPC23748
0.7805	Intermediate Similarity	NPC227814
0.7805	Intermediate Similarity	NPC144995
0.7802	Intermediate Similarity	NPC473448
0.7802	Intermediate Similarity	NPC474761
0.7802	Intermediate Similarity	NPC476004
0.7789	Intermediate Similarity	NPC65700
0.7789	Intermediate Similarity	NPC222303
0.7778	Intermediate Similarity	NPC227379
0.7778	Intermediate Similarity	NPC474471
0.7766	Intermediate Similarity	NPC472995
0.7765	Intermediate Similarity	NPC325869
0.7765	Intermediate Similarity	NPC1180
0.7765	Intermediate Similarity	NPC477088
0.7753	Intermediate Similarity	NPC122502
0.7742	Intermediate Similarity	NPC474035
0.7742	Intermediate Similarity	NPC159698
0.7742	Intermediate Similarity	NPC81386
0.7742	Intermediate Similarity	NPC256368
0.7742	Intermediate Similarity	NPC474247
0.7742	Intermediate Similarity	NPC303942
0.7742	Intermediate Similarity	NPC57405
0.7738	Intermediate Similarity	NPC474026
0.7738	Intermediate Similarity	NPC475711
0.7732	Intermediate Similarity	NPC473596
0.7727	Intermediate Similarity	NPC471301
0.7722	Intermediate Similarity	NPC259299
0.7717	Intermediate Similarity	NPC472468
0.7711	Intermediate Similarity	NPC327041
0.7711	Intermediate Similarity	NPC285840
0.7708	Intermediate Similarity	NPC38855
0.7708	Intermediate Similarity	NPC288876
0.7701	Intermediate Similarity	NPC323251
0.7701	Intermediate Similarity	NPC471298
0.7692	Intermediate Similarity	NPC246028
0.7684	Intermediate Similarity	NPC182811
0.7667	Intermediate Similarity	NPC474765
0.766	Intermediate Similarity	NPC469583
0.766	Intermediate Similarity	NPC36954
0.766	Intermediate Similarity	NPC240838
0.7654	Intermediate Similarity	NPC329904
0.7654	Intermediate Similarity	NPC473361
0.7654	Intermediate Similarity	NPC476037
0.7654	Intermediate Similarity	NPC129630
0.7654	Intermediate Similarity	NPC476012
0.7647	Intermediate Similarity	NPC474005
0.7647	Intermediate Similarity	NPC477089
0.764	Intermediate Similarity	NPC137033
0.7634	Intermediate Similarity	NPC212486
0.7634	Intermediate Similarity	NPC109406
0.7634	Intermediate Similarity	NPC475912
0.7629	Intermediate Similarity	NPC472753
0.7619	Intermediate Similarity	NPC203277
0.7619	Intermediate Similarity	NPC256720
0.7619	Intermediate Similarity	NPC236228
0.7614	Intermediate Similarity	NPC471297
0.7609	Intermediate Similarity	NPC475855
0.7609	Intermediate Similarity	NPC472466
0.7609	Intermediate Similarity	NPC202886
0.7604	Intermediate Similarity	NPC274458
0.7604	Intermediate Similarity	NPC203627
0.7604	Intermediate Similarity	NPC475068
0.7604	Intermediate Similarity	NPC161855
0.759	Intermediate Similarity	NPC315843
0.759	Intermediate Similarity	NPC471525
0.759	Intermediate Similarity	NPC474280
0.759	Intermediate Similarity	NPC107654
0.7582	Intermediate Similarity	NPC153805
0.7582	Intermediate Similarity	NPC281516
0.7579	Intermediate Similarity	NPC173329
0.7579	Intermediate Similarity	NPC288350
0.7579	Intermediate Similarity	NPC230800
0.7579	Intermediate Similarity	NPC473291
0.7579	Intermediate Similarity	NPC473859
0.7579	Intermediate Similarity	NPC472997
0.7579	Intermediate Similarity	NPC472996
0.7561	Intermediate Similarity	NPC316185
0.7561	Intermediate Similarity	NPC472254
0.7558	Intermediate Similarity	NPC5908
0.7558	Intermediate Similarity	NPC55304
0.7558	Intermediate Similarity	NPC226226
0.7558	Intermediate Similarity	NPC110373
0.7558	Intermediate Similarity	NPC80471
0.7556	Intermediate Similarity	NPC47220
0.7556	Intermediate Similarity	NPC164393
0.7556	Intermediate Similarity	NPC261253
0.7556	Intermediate Similarity	NPC204048
0.7556	Intermediate Similarity	NPC474045
0.7556	Intermediate Similarity	NPC186332
0.7551	Intermediate Similarity	NPC470972
0.7551	Intermediate Similarity	NPC472754
0.7551	Intermediate Similarity	NPC11956
0.7551	Intermediate Similarity	NPC109195
0.7551	Intermediate Similarity	NPC475038
0.7551	Intermediate Similarity	NPC201191
0.7529	Intermediate Similarity	NPC474278
0.7529	Intermediate Similarity	NPC476703
0.7529	Intermediate Similarity	NPC40049
0.7528	Intermediate Similarity	NPC474865
0.7528	Intermediate Similarity	NPC474776
0.7528	Intermediate Similarity	NPC31086
0.7528	Intermediate Similarity	NPC471302
0.7528	Intermediate Similarity	NPC266718
0.7528	Intermediate Similarity	NPC475035
0.7528	Intermediate Similarity	NPC126518
0.7527	Intermediate Similarity	NPC30515
0.7527	Intermediate Similarity	NPC206679
0.7527	Intermediate Similarity	NPC471324
0.7527	Intermediate Similarity	NPC184463
0.7527	Intermediate Similarity	NPC114172
0.7527	Intermediate Similarity	NPC476084

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 NPC160517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1880
0.2-0.3	3803
0.3-0.4	2356
0.4-0.5	663
0.5-0.6	210
0.6-0.7	46
0.7-0.8	9
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
0.8409	Intermediate Similarity	NPD7838	Discovery
0.8202	Intermediate Similarity	NPD6698	Approved
0.8202	Intermediate Similarity	NPD46	Approved
0.8	Intermediate Similarity	NPD5344	Discontinued
0.7708	Intermediate Similarity	NPD6648	Approved
0.7692	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6371	Approved
0.734	Intermediate Similarity	NPD7983	Approved
0.7071	Intermediate Similarity	NPD4225	Approved
0.7065	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5785	Approved
0.7033	Intermediate Similarity	NPD7154	Phase 3
0.7	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.6979	Remote Similarity	NPD7637	Suspended
0.6915	Remote Similarity	NPD4251	Approved
0.6915	Remote Similarity	NPD4250	Approved
0.69	Remote Similarity	NPD7638	Approved
0.6889	Remote Similarity	NPD4819	Approved
0.6889	Remote Similarity	NPD4822	Approved
0.6889	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4821	Approved
0.6889	Remote Similarity	NPD4820	Approved
0.6857	Remote Similarity	NPD6686	Approved
0.6818	Remote Similarity	NPD7115	Discovery
0.6809	Remote Similarity	NPD4249	Approved
0.6762	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7524	Approved
0.6735	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4268	Approved
0.6636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5209	Approved
0.6535	Remote Similarity	NPD7839	Suspended
0.6526	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5363	Approved
0.6522	Remote Similarity	NPD7514	Phase 3
0.6522	Remote Similarity	NPD7332	Phase 2
0.6517	Remote Similarity	NPD8039	Approved
0.6506	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5332	Approved
0.6489	Remote Similarity	NPD5331	Approved
0.6477	Remote Similarity	NPD4732	Discontinued
0.646	Remote Similarity	NPD7328	Approved
0.646	Remote Similarity	NPD7327	Approved
0.6452	Remote Similarity	NPD6902	Approved
0.6452	Remote Similarity	NPD4790	Discontinued
0.6435	Remote Similarity	NPD7503	Approved
0.6435	Remote Similarity	NPD8033	Approved
0.6429	Remote Similarity	NPD1695	Approved
0.6422	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7516	Approved
0.6392	Remote Similarity	NPD7750	Discontinued
0.6383	Remote Similarity	NPD4270	Approved
0.6383	Remote Similarity	NPD4269	Approved
0.6381	Remote Similarity	NPD7632	Discontinued
0.6373	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8377	Approved
0.6348	Remote Similarity	NPD8294	Approved
0.6344	Remote Similarity	NPD6930	Phase 2
0.6344	Remote Similarity	NPD6931	Approved
0.6337	Remote Similarity	NPD5282	Discontinued
0.6316	Remote Similarity	NPD6110	Phase 1
0.6306	Remote Similarity	NPD6053	Discontinued
0.6304	Remote Similarity	NPD7145	Approved
0.63	Remote Similarity	NPD6411	Approved
0.6296	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8378	Approved
0.6293	Remote Similarity	NPD8380	Approved
0.6293	Remote Similarity	NPD8296	Approved
0.6293	Remote Similarity	NPD8379	Approved
0.6293	Remote Similarity	NPD8335	Approved
0.6289	Remote Similarity	NPD5786	Approved
0.6279	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5369	Approved
0.6265	Remote Similarity	NPD4194	Approved
0.6265	Remote Similarity	NPD4192	Approved
0.6265	Remote Similarity	NPD4193	Approved
0.6265	Remote Similarity	NPD4191	Approved
0.6237	Remote Similarity	NPD6929	Approved
0.6218	Remote Similarity	NPD8273	Phase 1
0.6211	Remote Similarity	NPD6435	Approved
0.6211	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6932	Approved
0.6196	Remote Similarity	NPD6925	Approved
0.6196	Remote Similarity	NPD5776	Phase 2
0.6186	Remote Similarity	NPD7642	Approved
0.6186	Remote Similarity	NPD7830	Approved
0.6186	Remote Similarity	NPD7829	Approved
0.617	Remote Similarity	NPD4252	Approved
0.6154	Remote Similarity	NPD8517	Approved
0.6154	Remote Similarity	NPD8516	Approved
0.6154	Remote Similarity	NPD8515	Approved
0.6154	Remote Similarity	NPD8264	Approved
0.6154	Remote Similarity	NPD8513	Phase 3
0.6147	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7087	Discontinued
0.6129	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6898	Phase 1
0.61	Remote Similarity	NPD6051	Approved
0.61	Remote Similarity	NPD6101	Approved
0.61	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7505	Discontinued
0.6083	Remote Similarity	NPD7507	Approved
0.6055	Remote Similarity	NPD6640	Phase 3
0.604	Remote Similarity	NPD3168	Discontinued
0.602	Remote Similarity	NPD1694	Approved
0.602	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6421	Discontinued
0.5946	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5370	Suspended
0.5935	Remote Similarity	NPD7319	Approved
0.593	Remote Similarity	NPD3197	Phase 1
0.5914	Remote Similarity	NPD6933	Approved
0.5909	Remote Similarity	NPD4211	Phase 1
0.5902	Remote Similarity	NPD8074	Phase 3
0.5895	Remote Similarity	NPD6683	Phase 2
0.5882	Remote Similarity	NPD368	Approved
0.5877	Remote Similarity	NPD8297	Approved
0.587	Remote Similarity	NPD6926	Approved
0.587	Remote Similarity	NPD6924	Approved
0.5865	Remote Similarity	NPD7748	Approved
0.5859	Remote Similarity	NPD1696	Phase 3
0.5851	Remote Similarity	NPD4756	Discovery
0.5826	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD7515	Phase 2
0.5825	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7500	Approved
0.581	Remote Similarity	NPD5695	Phase 3
0.5804	Remote Similarity	NPD6881	Approved
0.5804	Remote Similarity	NPD6899	Approved
0.5798	Remote Similarity	NPD6319	Approved
0.5795	Remote Similarity	NPD7331	Phase 2
0.5789	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7604	Phase 2
0.578	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6399	Phase 3
0.5766	Remote Similarity	NPD7128	Approved
0.5766	Remote Similarity	NPD6402	Approved
0.5766	Remote Similarity	NPD5739	Approved
0.5766	Remote Similarity	NPD6008	Approved
0.5766	Remote Similarity	NPD6675	Approved
0.5763	Remote Similarity	NPD7641	Discontinued
0.575	Remote Similarity	NPD8444	Approved
0.5743	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7492	Approved
0.5728	Remote Similarity	NPD7136	Phase 2
0.5727	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD7260	Phase 2
0.5714	Remote Similarity	NPD7144	Approved
0.5714	Remote Similarity	NPD7143	Approved
0.5714	Remote Similarity	NPD6109	Phase 1
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD7102	Approved
0.5702	Remote Similarity	NPD6883	Approved
0.5701	Remote Similarity	NPD7902	Approved
0.5691	Remote Similarity	NPD8451	Approved
0.5691	Remote Similarity	NPD6616	Approved
0.569	Remote Similarity	NPD8133	Approved
0.5678	Remote Similarity	NPD6009	Approved
0.5667	Remote Similarity	NPD6054	Approved
0.5664	Remote Similarity	NPD7320	Approved
0.5663	Remote Similarity	NPD4219	Approved
0.5652	Remote Similarity	NPD6869	Approved
0.5652	Remote Similarity	NPD6847	Approved
0.5652	Remote Similarity	NPD6617	Approved
0.5652	Remote Similarity	NPD6649	Approved
0.5652	Remote Similarity	NPD7152	Approved
0.5652	Remote Similarity	NPD8130	Phase 1
0.5652	Remote Similarity	NPD7150	Approved
0.5652	Remote Similarity	NPD7151	Approved
0.5652	Remote Similarity	NPD6650	Approved
0.5648	Remote Similarity	NPD5696	Approved
0.5645	Remote Similarity	NPD8448	Approved
0.5645	Remote Similarity	NPD7078	Approved
0.5644	Remote Similarity	NPD7334	Approved
0.5644	Remote Similarity	NPD6684	Approved
0.5644	Remote Similarity	NPD6409	Approved
0.5644	Remote Similarity	NPD5330	Approved
0.5644	Remote Similarity	NPD7521	Approved
0.5644	Remote Similarity	NPD7146	Approved
0.5625	Remote Similarity	NPD5357	Phase 1
0.5625	Remote Similarity	NPD6927	Phase 3
0.5625	Remote Similarity	NPD5048	Discontinued

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