NPASS Compound

Structure

NPC302597 OpenBabel07101718182D 82 88 0 0 1 0 0 0 0 0999 V2000 6.3138 4.6143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1915 -2.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2815 -7.5487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9757 -7.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4894 2.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0159 -0.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3010 -3.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9071 3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 -2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7492 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8831 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7492 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1970 -8.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1970 3.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0881 -8.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0171 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8831 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -7.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1480 3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 -8.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.2834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.2834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1480 -8.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6759 -7.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4404 -6.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1511 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.2834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2325 -7.2397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4948 2.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 -1.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8942 -2.9962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0171 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.7834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2851 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6973 -5.5924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1970 -6.7615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1480 2.2872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1371 -7.0706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0881 1.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6146 -1.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8997 -2.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 -3.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6918 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3309 -6.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9541 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6918 -3.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9541 -6.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 -7.1751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3309 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -5.5924 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.6973 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.2851 -4.7834 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 2.2872 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6146 -2.8917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.8997 -1.8917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1480 -7.0706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1970 1.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0881 -6.7615 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.4820 -2.1872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.2834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -4.1789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6429 -0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -7.0706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5419 2.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6429 -4.1789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5419 -7.0706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 -8.1751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 2.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 19 1 0 0 0 0 13 27 1 0 0 0 0 14 20 1 0 0 0 0 14 28 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 16 30 1 0 0 0 0 17 38 2 0 0 0 0 18 38 1 0 0 0 0 23 25 1 0 0 0 0 23 39 2 0 0 0 0 24 26 2 0 0 0 0 24 39 1 0 0 0 0 25 40 2 0 0 0 0 26 40 1 0 0 0 0 27 67 1 0 0 0 0 28 68 1 0 0 0 0 29 69 1 0 0 0 0 30 70 1 0 0 0 0 31 34 1 0 0 0 0 32 38 1 0 0 0 0 33 39 1 0 0 0 0 35 5 1 6 0 0 0 36 6 1 6 0 0 0 37 7 1 6 0 0 0 37 71 1 0 0 0 0 40 72 1 0 0 0 0 41 33 1 1 0 0 0 41 51 1 0 0 0 0 41 61 1 0 0 0 0 42 32 1 1 0 0 0 42 52 1 0 0 0 0 42 62 1 0 0 0 0 43 31 1 1 0 0 0 43 57 1 0 0 0 0 43 63 1 0 0 0 0 44 19 1 1 0 0 0 44 53 1 0 0 0 0 44 67 1 0 0 0 0 45 20 1 1 0 0 0 45 54 1 0 0 0 0 45 68 1 0 0 0 0 46 21 1 1 0 0 0 46 58 1 0 0 0 0 46 69 1 0 0 0 0 47 22 1 1 0 0 0 47 59 1 0 0 0 0 47 70 1 0 0 0 0 48 35 1 1 0 0 0 48 55 1 0 0 0 0 48 64 1 0 0 0 0 49 36 1 1 0 0 0 49 60 1 0 0 0 0 49 65 1 0 0 0 0 50 37 1 1 0 0 0 50 56 1 0 0 0 0 50 66 1 0 0 0 0 51 65 2 3 0 0 0 51 73 1 0 0 0 0 52 66 2 3 0 0 0 52 74 1 0 0 0 0 53 61 2 3 0 0 0 53 75 1 0 0 0 0 54 64 2 3 0 0 0 54 76 1 0 0 0 0 55 62 2 3 0 0 0 55 77 1 0 0 0 0 56 63 2 3 0 0 0 56 78 1 0 0 0 0 57 69 1 0 0 0 0 57 79 2 0 0 0 0 58 67 1 0 0 0 0 58 80 2 0 0 0 0 59 68 1 0 0 0 0 59 81 2 0 0 0 0 60 70 1 0 0 0 0 60 82 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1138.64
Volume:	1159.687
LogP:	3.982
LogD:	4.08
LogS:	-3.587
# Rotatable Bonds:	11
TPSA:	303.28
# H-Bond Aceptor:	22
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.161
Synthetic Accessibility Score:	6.766
Fsp3:	0.633
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:	-6.554
MDCK Permeability:	2.4521141313016415e-05
Pgp-inhibitor:	0.241
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.994
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	73.7407455444336%
Volume Distribution (VD):	0.537
Pgp-substrate:	11.819108009338379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.288
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.442
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	2.927
Half-life (T1/2):	0.608

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.062
Carcinogencity:	0.164
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.675

Download Data

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

Natural Product: NPC302597

Natural Product ID:	NPC302597
*Common Name:**	Phakellistatin 12
IUPAC Name:	n.a.
Synonyms:	Phakellistatin 12
Standard InCHIKey:	AVIDVWPKZDUQCE-HVZWLOKRSA-N
Standard InCHI:	InChI=1S/C60H86N10O12/c1-8-35(5)48-55(77)62-42(32-38-17-11-10-12-18-38)52(74)66-50(37(7)71)56(78)63-43(31-34(3)4)57(79)69-29-15-21-46(69)58(80)67-27-13-19-44(67)53(75)61-41(33-39-23-25-40(72)26-24-39)51(73)65-49(36(6)9-2)60(82)70-30-16-22-47(70)59(81)68-28-14-20-45(68)54(76)64-48/h10-12,17-18,23-26,34-37,41-50,71-72H,8-9,13-16,19-22,27-33H2,1-7H3,(H,61,75)(H,62,77)(H,63,78)(H,64,76)(H,65,73)(H,66,74)/t35-,36-,37+,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-/m0/s1
SMILES:	CC[C@@H]([C@@H]1N=C(O)[C@H](Cc2ccc(cc2)O)N=C(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)N=C(O)[C@@H](N=C([C@@H](N=C([C@@H](N=C([C@H]2N(C(=O)[C@H]3N(C1=O)CCC3)CCC2)O)[C@H](CC)C)O)Cc1ccccc1)O)[C@H](O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2369700
PubChem CID:	21578711
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO32996	chuuk archipelago	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12639558]
NPO33037	phakellia sp.	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18489164]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.8	ug ml-1	PMID[461233]
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.8	ug ml-1	PMID[461234]

☑ 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 NPC302597 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	206
0.1-0.2	1187
0.2-0.3	5648
0.3-0.4	12002
0.4-0.5	17674
0.5-0.6	5041
0.6-0.7	616
0.7-0.8	267
0.8-0.85	37
0.85-0.9	8
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC141957
0.9308	High Similarity	NPC136797
0.9272	High Similarity	NPC5194
0.9272	High Similarity	NPC262166
0.9272	High Similarity	NPC261934
0.902	High Similarity	NPC202198
0.8981	High Similarity	NPC241794
0.8766	High Similarity	NPC473491
0.8693	High Similarity	NPC16188
0.8659	High Similarity	NPC137627
0.8654	High Similarity	NPC56685
0.8609	High Similarity	NPC476989
0.8606	High Similarity	NPC26108
0.859	High Similarity	NPC233702
0.8537	High Similarity	NPC475123
0.8537	High Similarity	NPC475204
0.85	High Similarity	NPC244336
0.8415	Intermediate Similarity	NPC107938
0.8415	Intermediate Similarity	NPC294516
0.8405	Intermediate Similarity	NPC63931
0.8383	Intermediate Similarity	NPC471165
0.8373	Intermediate Similarity	NPC328494
0.8373	Intermediate Similarity	NPC230611
0.8323	Intermediate Similarity	NPC306804
0.8313	Intermediate Similarity	NPC476268
0.8313	Intermediate Similarity	NPC40234
0.8313	Intermediate Similarity	NPC244509
0.8293	Intermediate Similarity	NPC472923
0.8274	Intermediate Similarity	NPC473402
0.8274	Intermediate Similarity	NPC279871
0.8225	Intermediate Similarity	NPC50016
0.8214	Intermediate Similarity	NPC273755
0.8204	Intermediate Similarity	NPC46009
0.8166	Intermediate Similarity	NPC476227
0.8166	Intermediate Similarity	NPC473354
0.8166	Intermediate Similarity	NPC155506
0.8166	Intermediate Similarity	NPC159767
0.8133	Intermediate Similarity	NPC61004
0.8129	Intermediate Similarity	NPC194671
0.8129	Intermediate Similarity	NPC45037
0.8129	Intermediate Similarity	NPC269750
0.8107	Intermediate Similarity	NPC475532
0.8084	Intermediate Similarity	NPC328649
0.8079	Intermediate Similarity	NPC130309
0.8059	Intermediate Similarity	NPC165285
0.8059	Intermediate Similarity	NPC17698
0.8047	Intermediate Similarity	NPC89831
0.8036	Intermediate Similarity	NPC280022
0.8024	Intermediate Similarity	NPC254700
0.8	Intermediate Similarity	NPC242159
0.8	Intermediate Similarity	NPC248670
0.8	Intermediate Similarity	NPC329295
0.8	Intermediate Similarity	NPC313694
0.7944	Intermediate Similarity	NPC477638
0.7944	Intermediate Similarity	NPC477632
0.7943	Intermediate Similarity	NPC294951
0.7931	Intermediate Similarity	NPC476321
0.7929	Intermediate Similarity	NPC129486
0.7886	Intermediate Similarity	NPC471526
0.7882	Intermediate Similarity	NPC198254
0.7882	Intermediate Similarity	NPC274198
0.7879	Intermediate Similarity	NPC323336
0.7879	Intermediate Similarity	NPC326349
0.7857	Intermediate Similarity	NPC287401
0.7831	Intermediate Similarity	NPC469898
0.7829	Intermediate Similarity	NPC473404
0.7816	Intermediate Similarity	NPC119652
0.7816	Intermediate Similarity	NPC97526
0.7812	Intermediate Similarity	NPC81026
0.7784	Intermediate Similarity	NPC470112
0.7784	Intermediate Similarity	NPC470903
0.7784	Intermediate Similarity	NPC167763
0.7784	Intermediate Similarity	NPC469243
0.7778	Intermediate Similarity	NPC200589
0.7778	Intermediate Similarity	NPC276506
0.775	Intermediate Similarity	NPC266741
0.7746	Intermediate Similarity	NPC158277
0.774	Intermediate Similarity	NPC471048
0.774	Intermediate Similarity	NPC471049
0.774	Intermediate Similarity	NPC471050
0.7727	Intermediate Similarity	NPC477637
0.7722	Intermediate Similarity	NPC240130
0.7722	Intermediate Similarity	NPC473305
0.7722	Intermediate Similarity	NPC163961
0.7722	Intermediate Similarity	NPC61332
0.7702	Intermediate Similarity	NPC314358
0.7701	Intermediate Similarity	NPC196243
0.7688	Intermediate Similarity	NPC476978
0.7679	Intermediate Similarity	NPC475544
0.7647	Intermediate Similarity	NPC223207
0.764	Intermediate Similarity	NPC316008
0.764	Intermediate Similarity	NPC313867
0.7637	Intermediate Similarity	NPC477631
0.7624	Intermediate Similarity	NPC477636
0.7619	Intermediate Similarity	NPC319320
0.7619	Intermediate Similarity	NPC287757
0.7616	Intermediate Similarity	NPC6975
0.7616	Intermediate Similarity	NPC46427
0.7614	Intermediate Similarity	NPC475421
0.7611	Intermediate Similarity	NPC94862
0.7602	Intermediate Similarity	NPC471771
0.7602	Intermediate Similarity	NPC290755
0.7602	Intermediate Similarity	NPC304074
0.7596	Intermediate Similarity	NPC65714
0.7596	Intermediate Similarity	NPC302715
0.759	Intermediate Similarity	NPC473002
0.759	Intermediate Similarity	NPC39431
0.7582	Intermediate Similarity	NPC473378
0.7582	Intermediate Similarity	NPC473407
0.7578	Intermediate Similarity	NPC315283
0.7578	Intermediate Similarity	NPC314388
0.7574	Intermediate Similarity	NPC469902
0.7574	Intermediate Similarity	NPC473003
0.7569	Intermediate Similarity	NPC102959
0.7564	Intermediate Similarity	NPC257390
0.755	Intermediate Similarity	NPC252878
0.7545	Intermediate Similarity	NPC473580
0.753	Intermediate Similarity	NPC122590
0.7527	Intermediate Similarity	NPC60516
0.7514	Intermediate Similarity	NPC473371
0.7514	Intermediate Similarity	NPC473000
0.75	Intermediate Similarity	NPC255447
0.7485	Intermediate Similarity	NPC133470
0.7485	Intermediate Similarity	NPC262077
0.7485	Intermediate Similarity	NPC191863
0.7485	Intermediate Similarity	NPC289776
0.7483	Intermediate Similarity	NPC202521
0.7473	Intermediate Similarity	NPC471592
0.7472	Intermediate Similarity	NPC153554
0.7456	Intermediate Similarity	NPC324850
0.7423	Intermediate Similarity	NPC315266
0.7419	Intermediate Similarity	NPC477639
0.7419	Intermediate Similarity	NPC319766
0.7417	Intermediate Similarity	NPC476990
0.7414	Intermediate Similarity	NPC186617
0.7407	Intermediate Similarity	NPC91953
0.7407	Intermediate Similarity	NPC161069
0.7403	Intermediate Similarity	NPC299806
0.7403	Intermediate Similarity	NPC315542
0.7394	Intermediate Similarity	NPC240848
0.7391	Intermediate Similarity	NPC163392
0.7391	Intermediate Similarity	NPC239762
0.7374	Intermediate Similarity	NPC170302
0.7374	Intermediate Similarity	NPC472999
0.7374	Intermediate Similarity	NPC32064
0.7374	Intermediate Similarity	NPC475564
0.7374	Intermediate Similarity	NPC475409
0.7372	Intermediate Similarity	NPC473322
0.7372	Intermediate Similarity	NPC469666
0.7371	Intermediate Similarity	NPC471568
0.7371	Intermediate Similarity	NPC473693
0.7371	Intermediate Similarity	NPC196091
0.7366	Intermediate Similarity	NPC59827
0.7366	Intermediate Similarity	NPC184933
0.7363	Intermediate Similarity	NPC276120
0.7356	Intermediate Similarity	NPC209463
0.7349	Intermediate Similarity	NPC2501
0.7346	Intermediate Similarity	NPC197921
0.7345	Intermediate Similarity	NPC164608
0.7345	Intermediate Similarity	NPC477462
0.7342	Intermediate Similarity	NPC326966
0.7337	Intermediate Similarity	NPC469903
0.7322	Intermediate Similarity	NPC4910
0.7322	Intermediate Similarity	NPC329731
0.7322	Intermediate Similarity	NPC96275
0.7317	Intermediate Similarity	NPC209509
0.7314	Intermediate Similarity	NPC469904
0.7305	Intermediate Similarity	NPC475168
0.7305	Intermediate Similarity	NPC7817
0.7305	Intermediate Similarity	NPC324081
0.7303	Intermediate Similarity	NPC469900
0.7301	Intermediate Similarity	NPC469360
0.7297	Intermediate Similarity	NPC248822
0.7285	Intermediate Similarity	NPC470546
0.7267	Intermediate Similarity	NPC127741
0.7267	Intermediate Similarity	NPC469901
0.7267	Intermediate Similarity	NPC6570
0.7263	Intermediate Similarity	NPC473546
0.725	Intermediate Similarity	NPC141050
0.7249	Intermediate Similarity	NPC477527
0.7243	Intermediate Similarity	NPC51047
0.7229	Intermediate Similarity	NPC138775
0.7219	Intermediate Similarity	NPC473341
0.7219	Intermediate Similarity	NPC470545
0.7213	Intermediate Similarity	NPC138083
0.7212	Intermediate Similarity	NPC5620
0.7195	Intermediate Similarity	NPC251439
0.719	Intermediate Similarity	NPC200964
0.7188	Intermediate Similarity	NPC244866
0.7178	Intermediate Similarity	NPC214988
0.7176	Intermediate Similarity	NPC470902
0.7173	Intermediate Similarity	NPC469443
0.716	Intermediate Similarity	NPC471265
0.716	Intermediate Similarity	NPC471264
0.7159	Intermediate Similarity	NPC473502
0.7158	Intermediate Similarity	NPC477552
0.7158	Intermediate Similarity	NPC50548
0.7158	Intermediate Similarity	NPC477550
0.7152	Intermediate Similarity	NPC52748
0.7152	Intermediate Similarity	NPC470544

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 NPC302597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	491
0.2-0.3	822
0.3-0.4	2010
0.4-0.5	3651
0.5-0.6	1796
0.6-0.7	229
0.7-0.8	9
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.879	High Similarity	NPD7118	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD8303	Discontinued
0.7425	Intermediate Similarity	NPD7131	Phase 3
0.7365	Intermediate Similarity	NPD7303	Discontinued
0.7317	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7485	Phase 3
0.7314	Intermediate Similarity	NPD7484	Phase 3
0.7301	Intermediate Similarity	NPD7978	Discontinued
0.7278	Intermediate Similarity	NPD3136	Phase 2
0.7267	Intermediate Similarity	NPD8173	Phase 2
0.7267	Intermediate Similarity	NPD8172	Phase 2
0.7239	Intermediate Similarity	NPD7450	Phase 2
0.7232	Intermediate Similarity	NPD5137	Approved
0.7209	Intermediate Similarity	NPD7495	Discontinued
0.7188	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7613	Discontinued
0.7143	Intermediate Similarity	NPD2098	Approved
0.711	Intermediate Similarity	NPD8019	Approved
0.7079	Intermediate Similarity	NPD4652	Approved
0.7059	Intermediate Similarity	NPD7617	Discontinued
0.7056	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2097	Approved
0.7006	Intermediate Similarity	NPD4659	Approved
0.6994	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7523	Phase 3
0.6914	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1330	Phase 2
0.6894	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7608	Discontinued
0.6867	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2562	Approved
0.6835	Remote Similarity	NPD2561	Approved
0.6824	Remote Similarity	NPD8323	Discontinued
0.6824	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7011	Discontinued
0.6813	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4103	Phase 2
0.6813	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3552	Approved
0.6807	Remote Similarity	NPD3554	Approved
0.6807	Remote Similarity	NPD3555	Approved
0.6807	Remote Similarity	NPD3553	Approved
0.677	Remote Similarity	NPD7451	Discontinued
0.6765	Remote Similarity	NPD3400	Discontinued
0.6765	Remote Similarity	NPD6676	Phase 2
0.676	Remote Similarity	NPD8031	Discontinued
0.675	Remote Similarity	NPD3125	Approved
0.6747	Remote Similarity	NPD2568	Approved
0.674	Remote Similarity	NPD2888	Approved
0.674	Remote Similarity	NPD2890	Approved
0.674	Remote Similarity	NPD2889	Approved
0.674	Remote Similarity	NPD2017	Approved
0.6727	Remote Similarity	NPD6346	Approved
0.6727	Remote Similarity	NPD8416	Discontinued
0.6702	Remote Similarity	NPD7280	Phase 3
0.6702	Remote Similarity	NPD7281	Phase 3
0.6687	Remote Similarity	NPD8643	Discontinued
0.6686	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5773	Approved
0.6685	Remote Similarity	NPD5772	Approved
0.6684	Remote Similarity	NPD7810	Phase 3
0.6684	Remote Similarity	NPD7811	Phase 3
0.6667	Remote Similarity	NPD5745	Approved
0.6667	Remote Similarity	NPD6557	Phase 2
0.6649	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6681	Discovery
0.6646	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2584	Suspended
0.6624	Remote Similarity	NPD5303	Approved
0.6624	Remote Similarity	NPD5304	Approved
0.6604	Remote Similarity	NPD3421	Phase 3
0.6603	Remote Similarity	NPD3123	Discovery
0.6591	Remote Similarity	NPD8315	Phase 1
0.659	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8076	Discontinued
0.6578	Remote Similarity	NPD5484	Approved
0.6578	Remote Similarity	NPD5485	Approved
0.657	Remote Similarity	NPD5481	Discontinued
0.657	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3588	Discontinued
0.6556	Remote Similarity	NPD5967	Approved
0.6552	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6073	Approved
0.6548	Remote Similarity	NPD5314	Approved
0.6545	Remote Similarity	NPD5746	Approved
0.6503	Remote Similarity	NPD7133	Discontinued
0.6495	Remote Similarity	NPD6505	Approved
0.6495	Remote Similarity	NPD6504	Approved
0.6492	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD8161	Suspended
0.6485	Remote Similarity	NPD4125	Approved
0.6485	Remote Similarity	NPD5263	Approved
0.6477	Remote Similarity	NPD4435	Approved
0.6477	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6405	Approved
0.6467	Remote Similarity	NPD6407	Approved
0.6464	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD317	Approved
0.6456	Remote Similarity	NPD318	Approved
0.6456	Remote Similarity	NPD16	Approved
0.6456	Remote Similarity	NPD856	Approved
0.645	Remote Similarity	NPD5725	Approved
0.645	Remote Similarity	NPD6255	Approved
0.645	Remote Similarity	NPD6254	Approved
0.645	Remote Similarity	NPD6256	Approved
0.6449	Remote Similarity	NPD8292	Phase 2
0.6446	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3059	Approved
0.6429	Remote Similarity	NPD3061	Approved
0.6429	Remote Similarity	NPD3062	Approved
0.6425	Remote Similarity	NPD4434	Approved
0.6424	Remote Similarity	NPD4175	Approved
0.6424	Remote Similarity	NPD4177	Approved
0.642	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3072	Approved
0.642	Remote Similarity	NPD2874	Phase 2
0.642	Remote Similarity	NPD3071	Approved
0.642	Remote Similarity	NPD3073	Approved
0.6413	Remote Similarity	NPD5823	Approved
0.641	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2228	Approved
0.641	Remote Similarity	NPD2229	Approved
0.641	Remote Similarity	NPD2234	Approved
0.6406	Remote Similarity	NPD6851	Approved
0.6406	Remote Similarity	NPD6853	Approved
0.6404	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6253	Approved
0.6398	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4676	Approved
0.6384	Remote Similarity	NPD6390	Discontinued
0.6383	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7738	Approved
0.6374	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7737	Approved
0.6369	Remote Similarity	NPD7086	Phase 2
0.6368	Remote Similarity	NPD6297	Approved
0.6364	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8124	Phase 3
0.6358	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4761	Approved
0.6358	Remote Similarity	NPD4762	Approved
0.6358	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4227	Discontinued
0.6353	Remote Similarity	NPD3052	Approved
0.6353	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3054	Approved
0.6349	Remote Similarity	NPD6020	Phase 2
0.6344	Remote Similarity	NPD2517	Approved
0.6341	Remote Similarity	NPD6792	Phase 3
0.634	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8351	Phase 2
0.6338	Remote Similarity	NPD8356	Approved
0.6333	Remote Similarity	NPD8417	Discontinued
0.6328	Remote Similarity	NPD7020	Approved
0.6328	Remote Similarity	NPD7019	Approved
0.6325	Remote Similarity	NPD3626	Phase 3
0.6324	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2459	Approved
0.6322	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2460	Phase 3
0.6322	Remote Similarity	NPD2458	Approved
0.6319	Remote Similarity	NPD4557	Approved
0.6316	Remote Similarity	NPD6852	Discontinued
0.6312	Remote Similarity	NPD316	Approved
0.631	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4621	Approved
0.631	Remote Similarity	NPD4619	Approved
0.631	Remote Similarity	NPD601	Approved
0.631	Remote Similarity	NPD598	Approved
0.631	Remote Similarity	NPD597	Approved
0.6308	Remote Similarity	NPD8025	Phase 2
0.6307	Remote Similarity	NPD6667	Approved
0.6307	Remote Similarity	NPD6666	Approved
0.6303	Remote Similarity	NPD1134	Approved
0.6303	Remote Similarity	NPD1133	Approved
0.6303	Remote Similarity	NPD1129	Approved
0.6303	Remote Similarity	NPD1131	Approved
0.6303	Remote Similarity	NPD1135	Approved
0.6303	Remote Similarity	NPD3053	Approved
0.6303	Remote Similarity	NPD3055	Approved
0.6302	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD2022	Approved
0.6301	Remote Similarity	NPD7720	Phase 2

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