NPASS Compound

Structure

NPC473378 OpenBabel07101718222D 82 86 0 0 1 0 0 0 0 0999 V2000 -6.9562 1.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8587 -1.8081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7959 -0.3248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3501 -0.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6220 -3.6694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5604 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.2337 3.3490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 -2.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0090 0.8553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9436 -2.1507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1693 -8.8038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8592 -8.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3849 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5387 -1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4360 2.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9412 0.8586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0950 -7.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2312 -1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1155 -9.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8054 -9.8727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5387 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 -0.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3686 2.7656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8738 1.1503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2769 -6.8525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2312 -2.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1448 -4.2391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0203 -3.3903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3571 0.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8462 -1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7431 -0.0849 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.1893 -1.5295 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5810 -3.4820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0411 -8.3626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3849 -0.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2223 1.5204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9335 -10.3139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0875 2.1038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3308 -5.8768 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3849 -2.9314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.8861 -4.6709 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1434 -0.0165 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8462 -2.4429 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6063 -2.7637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4245 -0.7853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9236 -4.3972 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.2742 -1.8722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3020 -5.7693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3849 -3.9086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1677 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 -2.9314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5448 -5.1514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3273 -3.7991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7856 -1.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8458 -1.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5387 -2.4429 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.3773 -5.6631 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.1857 -5.3523 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.2275 -0.2285 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0774 -4.8857 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.0487 -0.3842 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -11.4615 -2.8312 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.8797 -11.2896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8462 0.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2529 -1.8527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5679 -6.7096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5387 -4.3972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0603 1.0086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 -3.9086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9031 -5.8883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2599 -4.0908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5399 -0.4047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9739 -1.1315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9771 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9771 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.0201 2.3955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5541 -2.5053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 6 62 1 0 0 0 0 7 78 1 0 0 0 0 8 79 1 0 0 0 0 9 31 1 0 0 0 0 10 32 1 0 0 0 0 11 19 1 0 0 0 0 11 34 2 0 0 0 0 12 20 2 0 0 0 0 12 34 1 0 0 0 0 13 21 1 0 0 0 0 13 35 2 0 0 0 0 14 22 2 0 0 0 0 14 35 1 0 0 0 0 15 23 1 0 0 0 0 15 36 2 0 0 0 0 16 24 2 0 0 0 0 16 36 1 0 0 0 0 17 25 1 0 0 0 0 17 34 1 0 0 0 0 18 26 1 0 0 0 0 18 35 1 0 0 0 0 19 37 2 0 0 0 0 20 37 1 0 0 0 0 21 38 2 0 0 0 0 22 38 1 0 0 0 0 23 39 2 0 0 0 0 24 39 1 0 0 0 0 27 28 1 0 0 0 0 28 45 1 0 0 0 0 29 36 1 0 0 0 0 30 80 1 0 0 0 0 31 3 1 1 0 0 0 32 4 1 6 0 0 0 33 5 1 6 0 0 0 33 47 1 0 0 0 0 33 81 1 0 0 0 0 37 64 1 0 0 0 0 38 65 1 0 0 0 0 39 78 1 0 0 0 0 40 25 1 1 0 0 0 40 49 1 0 0 0 0 40 58 1 0 0 0 0 41 26 1 6 0 0 0 41 50 1 0 0 0 0 41 57 1 0 0 0 0 42 27 1 1 0 0 0 42 54 1 0 0 0 0 42 59 1 0 0 0 0 43 29 1 1 0 0 0 43 51 1 0 0 0 0 43 62 1 0 0 0 0 44 30 1 1 0 0 0 44 52 1 0 0 0 0 44 79 1 0 0 0 0 45 63 1 0 0 0 0 45 66 1 6 0 0 0 46 31 1 1 0 0 0 46 56 1 0 0 0 0 46 60 1 0 0 0 0 47 53 1 0 0 0 0 47 61 1 6 0 0 0 48 32 1 1 0 0 0 48 55 1 0 0 0 0 48 63 1 0 0 0 0 49 59 2 3 0 0 0 49 67 1 0 0 0 0 50 61 2 3 0 0 0 50 68 1 0 0 0 0 51 60 2 3 0 0 0 51 69 1 0 0 0 0 52 57 2 3 0 0 0 52 70 1 0 0 0 0 53 58 2 3 0 0 0 53 71 1 0 0 0 0 54 63 1 0 0 0 0 54 72 2 0 0 0 0 55 62 1 0 0 0 0 55 73 2 0 0 0 0 56 74 2 0 0 0 0 56 81 1 0 0 0 0 75 82 1 0 0 0 0 76 82 2 0 0 0 0 77 82 2 0 0 0 0 80 82 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1167.5
Volume:	1143.24
LogP:	1.253
LogD:	1.649
LogS:	-1.287
# Rotatable Bonds:	22
TPSA:	358.66
# H-Bond Aceptor:	25
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.032
Synthetic Accessibility Score:	7.478
Fsp3:	0.536
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:	-6.546
MDCK Permeability:	1.0414483767817728e-05
Pgp-inhibitor:	0.566
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.993
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	84.58870697021484%
Volume Distribution (VD):	0.482
Pgp-substrate:	2.4517507553100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.12
CYP2C9-substrate:	0.348
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	2.125
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.181
Human Hepatotoxicity (H-HT):	0.982
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.509
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.23
Carcinogencity:	0.197
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.73

Download Data

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

Natural Product: NPC473378

Natural Product ID:	NPC473378
*Common Name:**	Oscillapeptin A
IUPAC Name:	[(2R)-3-[[(2S)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-8-[(2R)-butan-2-yl]-2-[(2S)-butan-2-yl]-21-hydroxy-15-[2-(4-hydroxyphenyl)ethyl]-5-[(4-methoxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-4-(4-hydroxyphenyl)-1-oxobutan-2-yl]amino]-2-methoxy-3-oxopropyl] hydrogen sulfate
Synonyms:
Standard InCHIKey:	MPCIPLGLKBYIIR-UCRHDSKUSA-N
Standard InCHI:	InChI=1S/C56H77N7O18S/c1-9-31(3)46-56(74)81-33(5)47(61-50(68)41(26-18-35-13-21-38(65)22-14-35)57-52(70)44(79-8)30-80-82(75,76)77)53(71)58-40(25-17-34-11-19-37(64)20-12-34)49(67)59-42-27-28-45(66)63(54(42)72)48(32(4)10-2)55(73)62(6)43(51(69)60-46)29-36-15-23-39(78-7)24-16-36/h11-16,19-24,31-33,40-48,64-66H,9-10,17-18,25-30H2,1-8H3,(H,57,70)(H,58,71)(H,59,67)(H,60,69)(H,61,68)(H,75,76,77)/t31-,32+,33-,40+,41+,42+,43+,44-,45-,46+,47+,48+/m1/s1
SMILES:	CCC(C)C1C(=O)OC(C(C(=O)NC(C(=O)NC2CCC(N(C2=O)C(C(=O)N(C(C(=O)N1)CC3=CC=C(C=C3)OC)C)C(C)CC)O)CCC4=CC=C(C=C4)O)NC(=O)C(CCC5=CC=C(C=C5)O)NC(=O)C(COS(=O)(=O)O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404109
PubChem CID:	44448170
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO32547.1	oscillatoria agardhii	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[Title]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1890.0	nM	PMID[557157]

☑ 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 NPC473378 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	221
0.1-0.2	1142
0.2-0.3	4629
0.3-0.4	12728
0.4-0.5	7357
0.5-0.6	14711
0.6-0.7	1606
0.7-0.8	234
0.8-0.85	45
0.85-0.9	18
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473407
0.9586	High Similarity	NPC471526
0.9412	High Similarity	NPC476321
0.9148	High Similarity	NPC163961
0.9148	High Similarity	NPC473305
0.9118	High Similarity	NPC473354
0.8971	High Similarity	NPC471049
0.8971	High Similarity	NPC471050
0.8971	High Similarity	NPC471048
0.896	High Similarity	NPC45037
0.8889	High Similarity	NPC230611
0.8864	High Similarity	NPC294951
0.8837	High Similarity	NPC273755
0.8786	High Similarity	NPC473402
0.8786	High Similarity	NPC155506
0.8786	High Similarity	NPC159767
0.8736	High Similarity	NPC50016
0.8713	High Similarity	NPC107938
0.8713	High Similarity	NPC294516
0.8613	High Similarity	NPC40234
0.8571	High Similarity	NPC476227
0.8514	High Similarity	NPC137627
0.8514	High Similarity	NPC306804
0.8478	Intermediate Similarity	NPC302715
0.8466	Intermediate Similarity	NPC26108
0.8466	Intermediate Similarity	NPC279871
0.8462	Intermediate Similarity	NPC102959
0.8415	Intermediate Similarity	NPC64140
0.8415	Intermediate Similarity	NPC174122
0.8415	Intermediate Similarity	NPC60516
0.8361	Intermediate Similarity	NPC234069
0.8342	Intermediate Similarity	NPC471592
0.8324	Intermediate Similarity	NPC269750
0.8324	Intermediate Similarity	NPC194671
0.8295	Intermediate Similarity	NPC46009
0.8295	Intermediate Similarity	NPC475204
0.8295	Intermediate Similarity	NPC196091
0.8295	Intermediate Similarity	NPC475123
0.8201	Intermediate Similarity	NPC50548
0.8197	Intermediate Similarity	NPC138083
0.8192	Intermediate Similarity	NPC473693
0.8192	Intermediate Similarity	NPC471568
0.8182	Intermediate Similarity	NPC65714
0.8177	Intermediate Similarity	NPC32064
0.8171	Intermediate Similarity	NPC472923
0.8156	Intermediate Similarity	NPC471165
0.8152	Intermediate Similarity	NPC276120
0.8148	Intermediate Similarity	NPC144314
0.8136	Intermediate Similarity	NPC186617
0.8115	Intermediate Similarity	NPC242728
0.8114	Intermediate Similarity	NPC471051
0.8114	Intermediate Similarity	NPC471053
0.8114	Intermediate Similarity	NPC471052
0.8103	Intermediate Similarity	NPC471527
0.8101	Intermediate Similarity	NPC248670
0.8098	Intermediate Similarity	NPC315542
0.8095	Intermediate Similarity	NPC149962
0.8095	Intermediate Similarity	NPC473371
0.8092	Intermediate Similarity	NPC56635
0.8075	Intermediate Similarity	NPC248822
0.8056	Intermediate Similarity	NPC164608
0.8022	Intermediate Similarity	NPC475421
0.799	Intermediate Similarity	NPC25539
0.798	Intermediate Similarity	NPC469442
0.798	Intermediate Similarity	NPC277306
0.7969	Intermediate Similarity	NPC123859
0.7944	Intermediate Similarity	NPC89831
0.7935	Intermediate Similarity	NPC473404
0.7926	Intermediate Similarity	NPC61332
0.7926	Intermediate Similarity	NPC240130
0.7926	Intermediate Similarity	NPC29531
0.7921	Intermediate Similarity	NPC254700
0.7892	Intermediate Similarity	NPC470112
0.7892	Intermediate Similarity	NPC470903
0.7892	Intermediate Similarity	NPC167763
0.7865	Intermediate Similarity	NPC63931
0.7835	Intermediate Similarity	NPC477551
0.7824	Intermediate Similarity	NPC477552
0.7824	Intermediate Similarity	NPC477550
0.7807	Intermediate Similarity	NPC299806
0.7778	Intermediate Similarity	NPC219350
0.7778	Intermediate Similarity	NPC194699
0.7778	Intermediate Similarity	NPC220060
0.776	Intermediate Similarity	NPC471563
0.776	Intermediate Similarity	NPC158277
0.7744	Intermediate Similarity	NPC473450
0.7701	Intermediate Similarity	NPC233702
0.7696	Intermediate Similarity	NPC477526
0.768	Intermediate Similarity	NPC473502
0.7665	Intermediate Similarity	NPC311357
0.7657	Intermediate Similarity	NPC262166
0.7641	Intermediate Similarity	NPC323662
0.764	Intermediate Similarity	NPC319320
0.764	Intermediate Similarity	NPC287757
0.7633	Intermediate Similarity	NPC163392
0.7633	Intermediate Similarity	NPC239762
0.7632	Intermediate Similarity	NPC94862
0.7632	Intermediate Similarity	NPC4910
0.7624	Intermediate Similarity	NPC469445
0.7616	Intermediate Similarity	NPC81026
0.7586	Intermediate Similarity	NPC245974
0.7582	Intermediate Similarity	NPC302597
0.7577	Intermediate Similarity	NPC59827
0.7577	Intermediate Similarity	NPC184933
0.7563	Intermediate Similarity	NPC469443
0.7562	Intermediate Similarity	NPC469444
0.7558	Intermediate Similarity	NPC266741
0.7557	Intermediate Similarity	NPC473341
0.7549	Intermediate Similarity	NPC326027
0.7543	Intermediate Similarity	NPC473491
0.7539	Intermediate Similarity	NPC329731
0.7537	Intermediate Similarity	NPC326333
0.7527	Intermediate Similarity	NPC304074
0.7527	Intermediate Similarity	NPC61004
0.7527	Intermediate Similarity	NPC290755
0.7527	Intermediate Similarity	NPC471771
0.7527	Intermediate Similarity	NPC196243
0.7526	Intermediate Similarity	NPC328763
0.7515	Intermediate Similarity	NPC127741
0.7515	Intermediate Similarity	NPC6570
0.7514	Intermediate Similarity	NPC39431
0.7486	Intermediate Similarity	NPC207675
0.7486	Intermediate Similarity	NPC63040
0.7486	Intermediate Similarity	NPC212699
0.7486	Intermediate Similarity	NPC132771
0.7473	Intermediate Similarity	NPC22883
0.7473	Intermediate Similarity	NPC210377
0.7473	Intermediate Similarity	NPC217804
0.7473	Intermediate Similarity	NPC5719
0.7473	Intermediate Similarity	NPC223207
0.7472	Intermediate Similarity	NPC476268
0.7471	Intermediate Similarity	NPC247298
0.7471	Intermediate Similarity	NPC16188
0.7462	Intermediate Similarity	NPC477527
0.7459	Intermediate Similarity	NPC328494
0.7436	Intermediate Similarity	NPC314083
0.7432	Intermediate Similarity	NPC15068
0.7391	Intermediate Similarity	NPC328649
0.7391	Intermediate Similarity	NPC141957
0.7384	Intermediate Similarity	NPC476989
0.738	Intermediate Similarity	NPC136797
0.7371	Intermediate Similarity	NPC135121
0.7368	Intermediate Similarity	NPC477637
0.736	Intermediate Similarity	NPC202198
0.7356	Intermediate Similarity	NPC201244
0.7356	Intermediate Similarity	NPC477217
0.7348	Intermediate Similarity	NPC244336
0.7345	Intermediate Similarity	NPC324081
0.7341	Intermediate Similarity	NPC91953
0.7312	Intermediate Similarity	NPC198254
0.7312	Intermediate Similarity	NPC274198
0.7312	Intermediate Similarity	NPC276506
0.7308	Intermediate Similarity	NPC475544
0.7308	Intermediate Similarity	NPC469243
0.7297	Intermediate Similarity	NPC209463
0.7283	Intermediate Similarity	NPC197921
0.7263	Intermediate Similarity	NPC261934
0.7263	Intermediate Similarity	NPC122590
0.7263	Intermediate Similarity	NPC97526
0.7263	Intermediate Similarity	NPC119652
0.7263	Intermediate Similarity	NPC5194
0.7258	Intermediate Similarity	NPC280022
0.7253	Intermediate Similarity	NPC62104
0.7253	Intermediate Similarity	NPC1390
0.7241	Intermediate Similarity	NPC212850
0.7241	Intermediate Similarity	NPC469360
0.7241	Intermediate Similarity	NPC83289
0.7241	Intermediate Similarity	NPC189724
0.7232	Intermediate Similarity	NPC9373
0.7222	Intermediate Similarity	NPC477638
0.7222	Intermediate Similarity	NPC477632
0.722	Intermediate Similarity	NPC478005
0.7192	Intermediate Similarity	NPC473460
0.7184	Intermediate Similarity	NPC293347
0.7182	Intermediate Similarity	NPC244509
0.717	Intermediate Similarity	NPC478007
0.7167	Intermediate Similarity	NPC56685
0.7157	Intermediate Similarity	NPC473422
0.7135	Intermediate Similarity	NPC244866
0.7119	Intermediate Similarity	NPC262077
0.711	Intermediate Similarity	NPC68865
0.7104	Intermediate Similarity	NPC197743
0.7104	Intermediate Similarity	NPC297145
0.7103	Intermediate Similarity	NPC478008
0.7095	Intermediate Similarity	NPC2501
0.7088	Intermediate Similarity	NPC473580
0.7081	Intermediate Similarity	NPC241794
0.7077	Intermediate Similarity	NPC229234
0.7076	Intermediate Similarity	NPC257390
0.7047	Intermediate Similarity	NPC153554
0.7043	Intermediate Similarity	NPC191863
0.7043	Intermediate Similarity	NPC289776
0.7043	Intermediate Similarity	NPC133470
0.7019	Intermediate Similarity	NPC471561
0.7016	Intermediate Similarity	NPC477462
0.7011	Intermediate Similarity	NPC197741
0.7011	Intermediate Similarity	NPC140915
0.7011	Intermediate Similarity	NPC187028
0.7011	Intermediate Similarity	NPC10221
0.7011	Intermediate Similarity	NPC305700

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 NPC473378 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	466
0.2-0.3	924
0.3-0.4	2048
0.4-0.5	2643
0.5-0.6	2294
0.6-0.7	610
0.7-0.8	24
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
0.7989	Intermediate Similarity	NPD7608	Discontinued
0.7692	Intermediate Similarity	NPD7810	Phase 3
0.7692	Intermediate Similarity	NPD7811	Phase 3
0.7657	Intermediate Similarity	NPD7131	Phase 3
0.7541	Intermediate Similarity	NPD7484	Phase 3
0.7541	Intermediate Similarity	NPD7485	Phase 3
0.7526	Intermediate Similarity	NPD6853	Approved
0.7526	Intermediate Similarity	NPD6851	Approved
0.7513	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8031	Discontinued
0.7316	Intermediate Similarity	NPD6297	Approved
0.7293	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8070	Approved
0.7175	Intermediate Similarity	NPD8323	Discontinued
0.7151	Intermediate Similarity	NPD8245	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5745	Approved
0.712	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8019	Approved
0.7059	Intermediate Similarity	NPD8303	Discontinued
0.7039	Intermediate Similarity	NPD8161	Suspended
0.7018	Intermediate Similarity	NPD5746	Approved
0.6995	Remote Similarity	NPD7565	Approved
0.6961	Remote Similarity	NPD3536	Discontinued
0.6939	Remote Similarity	NPD7281	Phase 3
0.6939	Remote Similarity	NPD7280	Phase 3
0.6935	Remote Similarity	NPD5773	Approved
0.6935	Remote Similarity	NPD7972	Discontinued
0.6935	Remote Similarity	NPD5772	Approved
0.6931	Remote Similarity	NPD2904	Discontinued
0.6923	Remote Similarity	NPD6390	Discontinued
0.6919	Remote Similarity	NPD6677	Suspended
0.6898	Remote Similarity	NPD5967	Approved
0.6882	Remote Similarity	NPD5356	Approved
0.6882	Remote Similarity	NPD5355	Approved
0.6872	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5312	Approved
0.6856	Remote Similarity	NPD5313	Approved
0.6854	Remote Similarity	NPD7978	Discontinued
0.6854	Remote Similarity	NPD3656	Approved
0.6854	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6667	Approved
0.6851	Remote Similarity	NPD6666	Approved
0.685	Remote Similarity	NPD7861	Discontinued
0.6845	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7110	Phase 1
0.6828	Remote Similarity	NPD6072	Discontinued
0.6824	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5484	Approved
0.6821	Remote Similarity	NPD5485	Approved
0.6821	Remote Similarity	NPD3136	Phase 2
0.6818	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6681	Discovery
0.6811	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7585	Approved
0.6806	Remote Similarity	NPD6107	Approved
0.68	Remote Similarity	NPD4435	Approved
0.6798	Remote Similarity	NPD7450	Phase 2
0.6796	Remote Similarity	NPD5241	Discontinued
0.6791	Remote Similarity	NPD3007	Approved
0.6791	Remote Similarity	NPD2515	Approved
0.6791	Remote Similarity	NPD7495	Discontinued
0.6786	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7447	Phase 1
0.6774	Remote Similarity	NPD8417	Discontinued
0.6769	Remote Similarity	NPD42	Phase 2
0.6769	Remote Similarity	NPD6042	Phase 2
0.6762	Remote Similarity	NPD7583	Approved
0.6758	Remote Similarity	NPD5295	Discontinued
0.6758	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4434	Approved
0.6743	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5481	Discontinued
0.6739	Remote Similarity	NPD7303	Discontinued
0.6738	Remote Similarity	NPD2513	Approved
0.6737	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6504	Approved
0.6733	Remote Similarity	NPD6505	Approved
0.6728	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7212	Phase 2
0.6721	Remote Similarity	NPD7213	Phase 3
0.6715	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6346	Approved
0.6704	Remote Similarity	NPD2239	Approved
0.6704	Remote Similarity	NPD2240	Approved
0.6704	Remote Similarity	NPD1725	Approved
0.6703	Remote Similarity	NPD7427	Discontinued
0.6703	Remote Similarity	NPD3692	Discontinued
0.6702	Remote Similarity	NPD6862	Phase 2
0.6686	Remote Similarity	NPD5718	Phase 2
0.6685	Remote Similarity	NPD3985	Discontinued
0.6685	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6419	Discontinued
0.6684	Remote Similarity	NPD2053	Approved
0.6684	Remote Similarity	NPD22	Approved
0.6684	Remote Similarity	NPD6502	Phase 2
0.6683	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5756	Phase 2
0.6667	Remote Similarity	NPD7039	Approved
0.6667	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5677	Discontinued
0.6667	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8315	Phase 1
0.6667	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7038	Approved
0.6651	Remote Similarity	NPD6863	Phase 2
0.665	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5557	Phase 1
0.665	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7613	Discontinued
0.6634	Remote Similarity	NPD7291	Discontinued
0.6634	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6312	Discontinued
0.6633	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD2052	Approved
0.663	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3052	Approved
0.6629	Remote Similarity	NPD3054	Approved
0.6614	Remote Similarity	NPD7577	Discontinued
0.6613	Remote Similarity	NPD2122	Discontinued
0.6613	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6032	Approved
0.6605	Remote Similarity	NPD7827	Phase 1
0.6598	Remote Similarity	NPD7315	Approved
0.6595	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3060	Approved
0.6591	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7047	Phase 3
0.659	Remote Similarity	NPD8149	Discontinued
0.6584	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.658	Remote Similarity	NPD4666	Phase 3
0.658	Remote Similarity	NPD6746	Phase 2
0.6579	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8162	Phase 2
0.657	Remote Similarity	NPD4659	Approved
0.657	Remote Similarity	NPD6583	Phase 3
0.657	Remote Similarity	NPD6582	Phase 2
0.657	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2490	Approved
0.6569	Remote Similarity	NPD2488	Approved
0.6569	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5137	Approved
0.6562	Remote Similarity	NPD2098	Approved
0.6561	Remote Similarity	NPD7438	Suspended
0.6561	Remote Similarity	NPD8356	Approved
0.6561	Remote Similarity	NPD6385	Approved
0.6561	Remote Similarity	NPD6386	Approved
0.6559	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1753	Discontinued
0.6556	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1423	Approved
0.6552	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7906	Approved
0.6552	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6584	Phase 3
0.655	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3909	Discontinued
0.6545	Remote Similarity	NPD6063	Approved
0.6543	Remote Similarity	NPD3455	Phase 2
0.6536	Remote Similarity	NPD8172	Phase 2
0.6536	Remote Similarity	NPD8173	Phase 2
0.6533	Remote Similarity	NPD3823	Discontinued
0.6532	Remote Similarity	NPD3125	Approved
0.6531	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5723	Approved
0.6528	Remote Similarity	NPD5709	Phase 3
0.6526	Remote Similarity	NPD4227	Discontinued
0.6526	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7584	Approved
0.6524	Remote Similarity	NPD2493	Approved
0.6524	Remote Similarity	NPD2494	Approved
0.6524	Remote Similarity	NPD1670	Discontinued
0.6518	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD8059	Phase 3
0.6517	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3933	Discontinued
0.6515	Remote Similarity	NPD5096	Phase 3
0.6515	Remote Similarity	NPD5095	Phase 3
0.6513	Remote Similarity	NPD4652	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data