NPASS Compound

Structure

NPC312498 OpenBabel07101719142D 79 93 0 0 1 0 0 0 0 0999 V2000 -5.2181 -0.9943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5153 -3.8902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5243 -3.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8248 1.1791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8798 -0.7793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8707 0.7627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2460 -2.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8227 0.6689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7975 -2.7596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2766 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4020 -0.7609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3231 -0.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8864 -2.2397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8784 -2.1456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4364 -2.7235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1896 0.8772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5141 -1.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3596 -1.0349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9265 -1.3495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6680 -2.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6810 -0.3265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9152 -0.3557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4738 0.8246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0105 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9420 -1.8672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6467 -1.8150 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2524 -2.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5308 -2.8320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8183 0.1792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1652 -1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8772 -0.2373 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4364 -2.7300 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7038 -2.6919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6789 1.1349 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3303 -1.3092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9421 -1.8542 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3173 -2.5710 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6989 0.7345 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8046 -2.0658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9421 -1.8477 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4458 -1.0761 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3615 -1.0637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4037 -1.0699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4066 -1.3377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4422 -0.5231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2910 1.4492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9425 -1.3152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7879 0.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4000 -2.3377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9490 -0.3152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4001 -0.5169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3579 -0.5107 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7716 1.2167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5567 1.7134 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7362 1.4000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1204 1.3784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2939 1.0349 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0995 0.2923 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6745 -1.3264 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5930 -0.8052 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9420 -1.8737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9308 -3.5992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4477 -0.9915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0081 1.1232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3654 -1.5721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2112 -2.4407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2196 1.2509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8844 -1.3433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5255 1.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3491 -2.6529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9193 -0.2435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6887 1.6957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5036 0.0228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9210 -1.2505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5438 -0.8321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8053 -1.8208 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 -7.2384 1.1595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7477 0.7190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 27 2 0 0 0 0 5 30 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 11 12 1 0 0 0 0 13 26 1 0 0 0 0 13 33 1 0 0 0 0 14 27 1 0 0 0 0 14 35 1 0 0 0 0 15 32 1 0 0 0 0 15 36 1 0 0 0 0 16 34 1 0 0 0 0 16 48 1 0 0 0 0 18 40 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 21 59 1 0 0 0 0 23 46 1 0 0 0 0 23 58 1 0 0 0 0 24 60 1 0 0 0 0 25 32 1 0 0 0 0 25 61 1 0 0 0 0 26 1 1 1 0 0 0 26 30 1 0 0 0 0 27 37 1 0 0 0 0 28 3 1 1 0 0 0 28 49 1 0 0 0 0 29 4 1 1 0 0 0 29 50 1 0 0 0 0 30 39 1 0 0 0 0 31 6 1 1 0 0 0 31 51 1 0 0 0 0 31 52 1 0 0 0 0 32 62 1 6 0 0 0 33 7 1 1 0 0 0 33 66 1 0 0 0 0 34 8 1 6 0 0 0 34 67 1 0 0 0 0 35 11 1 6 0 0 0 35 65 1 0 0 0 0 36 63 1 1 0 0 0 37 9 1 1 0 0 0 37 65 1 0 0 0 0 38 10 1 1 0 0 0 38 53 1 0 0 0 0 38 69 1 0 0 0 0 39 17 1 1 0 0 0 39 66 1 0 0 0 0 40 36 1 1 0 0 0 40 70 1 0 0 0 0 41 19 1 6 0 0 0 41 45 1 0 0 0 0 41 74 1 0 0 0 0 42 17 1 1 0 0 0 42 52 1 0 0 0 0 42 68 1 0 0 0 0 43 19 1 6 0 0 0 43 51 1 0 0 0 0 43 68 1 0 0 0 0 44 18 1 1 0 0 0 44 49 1 0 0 0 0 44 75 1 0 0 0 0 45 22 1 6 0 0 0 45 71 1 0 0 0 0 46 54 1 0 0 0 0 46 72 1 1 0 0 0 47 24 1 1 0 0 0 47 50 1 0 0 0 0 47 76 1 0 0 0 0 48 64 2 0 0 0 0 48 73 1 0 0 0 0 49 70 1 1 0 0 0 50 77 1 1 0 0 0 51 71 1 6 0 0 0 52 73 1 6 0 0 0 53 57 1 0 0 0 0 53 67 1 1 0 0 0 54 55 1 0 0 0 0 54 78 1 6 0 0 0 55 56 1 0 0 0 0 55 69 1 6 0 0 0 56 57 1 0 0 0 0 56 72 1 6 0 0 0 57 79 1 6 0 0 0 58 12 1 6 0 0 0 58 78 1 0 0 0 0 58 79 1 0 0 0 0 59 20 1 1 0 0 0 59 75 1 0 0 0 0 59 76 1 0 0 0 0 60 22 1 6 0 0 0 60 74 1 0 0 0 0 60 77 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1110.58
Volume:	1077.074
LogP:	5.987
LogD:	4.092
LogS:	-6.159
# Rotatable Bonds:	4
TPSA:	216.21
# H-Bond Aceptor:	19
# H-Bond Donor:	3
# Rings:	16
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	8.916
Fsp3:	0.917
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:	-5.349
MDCK Permeability:	0.000296047335723415
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	69.50324249267578%
Volume Distribution (VD):	-0.1
Pgp-substrate:	18.03412628173828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.814
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	12.21
Half-life (T1/2):	0.011

ADMET: Toxicity

hERG Blockers:	0.903
Human Hepatotoxicity (H-HT):	0.783
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.325
Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.974
Carcinogencity:	0.107
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC312498

Natural Product ID:	NPC312498
*Common Name:**	Halichondrin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FXNFULJVOQMBCW-VZBLNRDYSA-N
Standard InCHI:	InChI=1S/C60H86O19/c1-26-13-33-7-9-37-27(2)14-35(65-37)11-12-58-23-46-54(78-58)55-56(72-46)57(79-58)53-38(69-55)10-8-34(67-53)16-48(64)73-52-31(6)51-43(68-42(52)17-39(66-33)30(26)5)19-41-45(71-51)22-60(74-41)24-47-50(77-60)29(4)21-59(76-47)20-28(3)49-44(75-59)18-40(70-49)36(63)15-32(62)25-61/h26,28-29,31-47,49-57,61-63H,2,5,7-25H2,1,3-4,6H3/t26-,28+,29+,31+,32-,33+,34-,35+,36+,37+,38+,39-,40+,41-,42+,43+,44+,45-,46-,47+,49+,50+,51+,52-,53+,54+,55+,56-,57+,58+,59-,60+/m1/s1
SMILES:	C[C@@H]1C[C@@H]2CC[C@H]3C(=C)C[C@H](CC[C@]45C[C@@H]6[C@@H]([C@H]7[C@H]([C@H]([C@@H]8[C@H](CC[C@H](CC(=O)O[C@@H]9[C@@H](C)[C@H]%10[C@H](C[C@@H]%11[C@@H](C[C@]%12(C[C@H]%13[C@H]([C@@H](C)C[C@@]%14(C[C@H](C)[C@H]%15[C@H](C[C@@H]([C@H](C[C@H](CO)O)O)O%15)O%14)O%13)O%12)O%11)O%10)O[C@H]9C[C@H](C1=C)O2)O8)O7)O5)O6)O4)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387466
PubChem CID:	5488895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0001542] Disaccharides

*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
NPO32553	lissodendoryx sp.	Species	Coelosphaeridae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19081259]

☑ 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
Others	1

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	T/C	=	238.0	n.a.	PMID[488214]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.00078	ug.mL-1	PMID[488215]

☑ 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 NPC312498 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	364
0.1-0.2	2689
0.2-0.3	8345
0.3-0.4	15342
0.4-0.5	9230
0.5-0.6	4974
0.6-0.7	1720
0.7-0.8	26
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473849
0.981	High Similarity	NPC475537
0.981	High Similarity	NPC308858
0.9423	High Similarity	NPC473771
0.9423	High Similarity	NPC475275
0.9279	High Similarity	NPC475298
0.8091	Intermediate Similarity	NPC470519
0.8091	Intermediate Similarity	NPC231271
0.7826	Intermediate Similarity	NPC126897
0.7826	Intermediate Similarity	NPC297945
0.7692	Intermediate Similarity	NPC51662
0.7652	Intermediate Similarity	NPC313668
0.7652	Intermediate Similarity	NPC315836
0.7583	Intermediate Similarity	NPC109603
0.7583	Intermediate Similarity	NPC93688
0.7391	Intermediate Similarity	NPC476740
0.7391	Intermediate Similarity	NPC476738
0.7387	Intermediate Similarity	NPC236580
0.7387	Intermediate Similarity	NPC304445
0.7358	Intermediate Similarity	NPC314364
0.7333	Intermediate Similarity	NPC54395
0.7297	Intermediate Similarity	NPC475164
0.7297	Intermediate Similarity	NPC475375
0.7297	Intermediate Similarity	NPC475525
0.7297	Intermediate Similarity	NPC475593
0.7297	Intermediate Similarity	NPC475540
0.7297	Intermediate Similarity	NPC475241
0.7297	Intermediate Similarity	NPC473765
0.7297	Intermediate Similarity	NPC473605
0.7297	Intermediate Similarity	NPC476066
0.7258	Intermediate Similarity	NPC183353
0.7258	Intermediate Similarity	NPC469812
0.7217	Intermediate Similarity	NPC473148
0.7217	Intermediate Similarity	NPC474581
0.7217	Intermediate Similarity	NPC473816
0.7217	Intermediate Similarity	NPC309398
0.7217	Intermediate Similarity	NPC475367
0.7213	Intermediate Similarity	NPC156651
0.7193	Intermediate Similarity	NPC67296
0.7179	Intermediate Similarity	NPC287269
0.7177	Intermediate Similarity	NPC317635
0.7177	Intermediate Similarity	NPC329008
0.7168	Intermediate Similarity	NPC49833
0.7168	Intermediate Similarity	NPC249171
0.7167	Intermediate Similarity	NPC470543
0.7156	Intermediate Similarity	NPC474323
0.7156	Intermediate Similarity	NPC206614
0.7143	Intermediate Similarity	NPC60849
0.7143	Intermediate Similarity	NPC477332
0.7143	Intermediate Similarity	NPC472352
0.7143	Intermediate Similarity	NPC474297
0.7131	Intermediate Similarity	NPC469820
0.7131	Intermediate Similarity	NPC469823
0.712	Intermediate Similarity	NPC275225
0.712	Intermediate Similarity	NPC68767
0.712	Intermediate Similarity	NPC51099
0.712	Intermediate Similarity	NPC170880
0.712	Intermediate Similarity	NPC293031
0.712	Intermediate Similarity	NPC477463
0.7119	Intermediate Similarity	NPC193765
0.7119	Intermediate Similarity	NPC224414
0.7117	Intermediate Similarity	NPC472198
0.7117	Intermediate Similarity	NPC477345
0.7117	Intermediate Similarity	NPC477348
0.7117	Intermediate Similarity	NPC44682
0.7117	Intermediate Similarity	NPC163409
0.7117	Intermediate Similarity	NPC238264
0.7107	Intermediate Similarity	NPC146563
0.7097	Intermediate Similarity	NPC207738
0.7094	Intermediate Similarity	NPC478038
0.7094	Intermediate Similarity	NPC315070
0.708	Intermediate Similarity	NPC261372
0.708	Intermediate Similarity	NPC263674
0.708	Intermediate Similarity	NPC58267
0.7077	Intermediate Similarity	NPC311178
0.7077	Intermediate Similarity	NPC300655
0.7077	Intermediate Similarity	NPC43589
0.7077	Intermediate Similarity	NPC222951
0.7073	Intermediate Similarity	NPC473452
0.7073	Intermediate Similarity	NPC475514
0.7073	Intermediate Similarity	NPC185466
0.7073	Intermediate Similarity	NPC85154
0.7073	Intermediate Similarity	NPC286457
0.7073	Intermediate Similarity	NPC8524
0.7073	Intermediate Similarity	NPC470876
0.7073	Intermediate Similarity	NPC123522
0.7073	Intermediate Similarity	NPC191827
0.7073	Intermediate Similarity	NPC102505
0.7073	Intermediate Similarity	NPC104137
0.7073	Intermediate Similarity	NPC220160
0.7073	Intermediate Similarity	NPC475209
0.7073	Intermediate Similarity	NPC69811
0.7073	Intermediate Similarity	NPC33012
0.7073	Intermediate Similarity	NPC309223
0.7073	Intermediate Similarity	NPC471580
0.7064	Intermediate Similarity	NPC92974
0.7049	Intermediate Similarity	NPC469821
0.704	Intermediate Similarity	NPC108072
0.704	Intermediate Similarity	NPC144644
0.704	Intermediate Similarity	NPC37860
0.704	Intermediate Similarity	NPC110385
0.704	Intermediate Similarity	NPC153673
0.704	Intermediate Similarity	NPC142151
0.704	Intermediate Similarity	NPC476150
0.704	Intermediate Similarity	NPC267694
0.704	Intermediate Similarity	NPC476127
0.7027	Intermediate Similarity	NPC471483
0.7027	Intermediate Similarity	NPC320089
0.7023	Intermediate Similarity	NPC196874
0.7023	Intermediate Similarity	NPC473679
0.7023	Intermediate Similarity	NPC233223
0.7023	Intermediate Similarity	NPC475444
0.7023	Intermediate Similarity	NPC324933
0.7023	Intermediate Similarity	NPC183816
0.7023	Intermediate Similarity	NPC475177
0.7023	Intermediate Similarity	NPC322904
0.7023	Intermediate Similarity	NPC319719
0.7016	Intermediate Similarity	NPC105800
0.7016	Intermediate Similarity	NPC232237
0.7016	Intermediate Similarity	NPC469822
0.7016	Intermediate Similarity	NPC237191
0.7008	Intermediate Similarity	NPC202261
0.7008	Intermediate Similarity	NPC106589
0.7008	Intermediate Similarity	NPC256983
0.7008	Intermediate Similarity	NPC186339
0.7	Intermediate Similarity	NPC106760
0.6992	Remote Similarity	NPC305267
0.6992	Remote Similarity	NPC189126
0.6992	Remote Similarity	NPC75287
0.6992	Remote Similarity	NPC476992
0.6992	Remote Similarity	NPC26626
0.6992	Remote Similarity	NPC137414
0.6992	Remote Similarity	NPC288205
0.6992	Remote Similarity	NPC51465
0.6984	Remote Similarity	NPC476204
0.6984	Remote Similarity	NPC170084
0.6984	Remote Similarity	NPC475182
0.6983	Remote Similarity	NPC313569
0.6983	Remote Similarity	NPC80144
0.6977	Remote Similarity	NPC11732
0.6972	Remote Similarity	NPC177629
0.6972	Remote Similarity	NPC58219
0.6967	Remote Similarity	NPC293658
0.6967	Remote Similarity	NPC474410
0.696	Remote Similarity	NPC471577
0.696	Remote Similarity	NPC477464
0.696	Remote Similarity	NPC473386
0.6953	Remote Similarity	NPC248202
0.6953	Remote Similarity	NPC473474
0.6952	Remote Similarity	NPC477331
0.6952	Remote Similarity	NPC119583
0.6952	Remote Similarity	NPC307400
0.6952	Remote Similarity	NPC297768
0.6952	Remote Similarity	NPC472202
0.6952	Remote Similarity	NPC123204
0.6952	Remote Similarity	NPC290012
0.6952	Remote Similarity	NPC259294
0.6952	Remote Similarity	NPC472201
0.6952	Remote Similarity	NPC44782
0.6952	Remote Similarity	NPC89843
0.6952	Remote Similarity	NPC475270
0.6952	Remote Similarity	NPC472205
0.6952	Remote Similarity	NPC477317
0.6952	Remote Similarity	NPC475327
0.6952	Remote Similarity	NPC169345
0.6952	Remote Similarity	NPC477319
0.6952	Remote Similarity	NPC173328
0.6952	Remote Similarity	NPC186992
0.6952	Remote Similarity	NPC184915
0.6952	Remote Similarity	NPC475667
0.6952	Remote Similarity	NPC27289
0.6952	Remote Similarity	NPC477347
0.6952	Remote Similarity	NPC224953
0.6952	Remote Similarity	NPC472200
0.6952	Remote Similarity	NPC183888
0.6952	Remote Similarity	NPC143421
0.6952	Remote Similarity	NPC115013
0.6952	Remote Similarity	NPC269318
0.6952	Remote Similarity	NPC472204
0.6952	Remote Similarity	NPC238056
0.6952	Remote Similarity	NPC476087
0.6952	Remote Similarity	NPC477318
0.6952	Remote Similarity	NPC472203
0.6952	Remote Similarity	NPC126685
0.6944	Remote Similarity	NPC474949
0.6944	Remote Similarity	NPC474762
0.6944	Remote Similarity	NPC475019
0.6944	Remote Similarity	NPC476015
0.6942	Remote Similarity	NPC204392
0.6942	Remote Similarity	NPC91838
0.6942	Remote Similarity	NPC11035
0.6942	Remote Similarity	NPC272242
0.6942	Remote Similarity	NPC1876
0.6942	Remote Similarity	NPC240734
0.6942	Remote Similarity	NPC275668
0.6937	Remote Similarity	NPC472199
0.6937	Remote Similarity	NPC477349
0.6935	Remote Similarity	NPC148417
0.6935	Remote Similarity	NPC473824
0.6935	Remote Similarity	NPC136768

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 NPC312498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	2860
0.2-0.3	4112
0.3-0.4	1283
0.4-0.5	441
0.5-0.6	83
0.6-0.7	15
0.7-0.8	9
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
0.7826	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD8268	Approved
0.7686	Intermediate Similarity	NPD8266	Approved
0.7686	Intermediate Similarity	NPD8267	Approved
0.7686	Intermediate Similarity	NPD8269	Approved
0.7258	Intermediate Similarity	NPD8517	Approved
0.7258	Intermediate Similarity	NPD8515	Approved
0.7258	Intermediate Similarity	NPD8516	Approved
0.725	Intermediate Similarity	NPD8133	Approved
0.712	Intermediate Similarity	NPD8513	Phase 3
0.6696	Remote Similarity	NPD6698	Approved
0.6696	Remote Similarity	NPD46	Approved
0.6694	Remote Similarity	NPD6686	Approved
0.6612	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7983	Approved
0.6466	Remote Similarity	NPD8074	Phase 3
0.6441	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8328	Phase 3
0.626	Remote Similarity	NPD8294	Approved
0.626	Remote Similarity	NPD8377	Approved
0.625	Remote Similarity	NPD7319	Approved
0.624	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8448	Approved
0.6212	Remote Similarity	NPD8033	Approved
0.6212	Remote Similarity	NPD8379	Approved
0.6212	Remote Similarity	NPD8296	Approved
0.6212	Remote Similarity	NPD8380	Approved
0.6212	Remote Similarity	NPD8335	Approved
0.6212	Remote Similarity	NPD8378	Approved
0.6204	Remote Similarity	NPD8391	Approved
0.6204	Remote Similarity	NPD8392	Approved
0.6204	Remote Similarity	NPD8390	Approved
0.6154	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8451	Approved
0.6148	Remote Similarity	NPD7507	Approved
0.6134	Remote Similarity	NPD7839	Suspended
0.6121	Remote Similarity	NPD7838	Discovery
0.6119	Remote Similarity	NPD7830	Approved
0.6119	Remote Similarity	NPD7829	Approved
0.609	Remote Similarity	NPD8444	Approved
0.608	Remote Similarity	NPD6412	Phase 2
0.6063	Remote Similarity	NPD6371	Approved
0.6048	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.597	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6053	Discontinued
0.5956	Remote Similarity	NPD8299	Approved
0.5956	Remote Similarity	NPD8340	Approved
0.5956	Remote Similarity	NPD8341	Approved
0.5956	Remote Similarity	NPD8342	Approved
0.5926	Remote Similarity	NPD8080	Discontinued
0.5917	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6101	Approved
0.5897	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5779	Approved
0.5882	Remote Similarity	NPD5778	Approved
0.5865	Remote Similarity	NPD7327	Approved
0.5865	Remote Similarity	NPD7328	Approved
0.5856	Remote Similarity	NPD7329	Approved
0.5833	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7736	Approved
0.5821	Remote Similarity	NPD7516	Approved
0.5798	Remote Similarity	NPD6411	Approved
0.5797	Remote Similarity	NPD8273	Phase 1
0.5772	Remote Similarity	NPD4225	Approved
0.5764	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.576	Remote Similarity	NPD8084	Approved
0.576	Remote Similarity	NPD8139	Approved
0.576	Remote Similarity	NPD8138	Approved
0.576	Remote Similarity	NPD8086	Approved
0.576	Remote Similarity	NPD8085	Approved
0.576	Remote Similarity	NPD8082	Approved
0.576	Remote Similarity	NPD8083	Approved
0.5755	Remote Similarity	NPD7078	Approved
0.5755	Remote Similarity	NPD8293	Discontinued
0.5748	Remote Similarity	NPD8393	Approved
0.5735	Remote Similarity	NPD7503	Approved
0.5725	Remote Similarity	NPD7492	Approved
0.5714	Remote Similarity	NPD8276	Approved
0.5714	Remote Similarity	NPD8275	Approved
0.5702	Remote Similarity	NPD5282	Discontinued
0.5694	Remote Similarity	NPD8415	Approved
0.5683	Remote Similarity	NPD6616	Approved
0.5672	Remote Similarity	NPD7115	Discovery
0.5669	Remote Similarity	NPD8081	Approved
0.5662	Remote Similarity	NPD6059	Approved
0.5662	Remote Similarity	NPD6054	Approved
0.5652	Remote Similarity	NPD7642	Approved
0.563	Remote Similarity	NPD1695	Approved
0.562	Remote Similarity	NPD8171	Discontinued
0.562	Remote Similarity	NPD6921	Approved
0.5615	Remote Similarity	NPD4061	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