NPASS Compound

Structure

NPC473693 OpenBabel07101719122D 70 71 0 0 1 0 0 0 0 0999 V2000 -5.9505 9.0268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9541 -0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 9.2578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0471 9.9622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0606 7.4307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6862 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1639 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 3.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8309 0.6121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3309 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 7.7397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 9.5268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8202 6.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6611 3.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9016 8.7178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8202 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0140 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9290 6.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0630 5.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7950 6.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9290 4.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1970 6.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8061 8.5487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5688 4.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 9.1532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1095 7.7397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8202 0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7572 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9456 3.3698 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0630 6.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7950 5.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8061 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3309 6.2615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8116 8.6532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3609 5.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 8.2397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3664 7.0706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9541 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7377 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7377 5.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6232 7.7397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3609 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 7.7397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6232 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 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 -4.7572 8.2397 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.5688 3.3698 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 4.3698 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 -2.8116 -0.9135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 7.0706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 8.5487 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9541 6.2615 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8116 9.6532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3119 5.6570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 2.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -1.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 5.6570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2110 8.5487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3119 2.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 8.5487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2110 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6611 4.7615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3664 0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 11 50 1 0 0 0 0 12 50 1 0 0 0 0 13 56 1 0 0 0 0 14 57 1 0 0 0 0 15 58 1 0 0 0 0 16 69 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 20 22 1 0 0 0 0 20 33 2 0 0 0 0 21 23 2 0 0 0 0 21 33 1 0 0 0 0 22 34 2 0 0 0 0 23 34 1 0 0 0 0 24 33 1 0 0 0 0 25 37 1 0 0 0 0 25 51 1 0 0 0 0 26 38 1 0 0 0 0 26 52 1 0 0 0 0 28 6 1 1 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 30 35 1 0 0 0 0 30 48 1 0 0 0 0 31 9 1 1 0 0 0 31 42 1 0 0 0 0 31 53 1 0 0 0 0 32 10 1 1 0 0 0 32 43 1 0 0 0 0 32 54 1 0 0 0 0 34 69 1 0 0 0 0 35 19 1 6 0 0 0 35 55 1 0 0 0 0 36 24 1 1 0 0 0 36 44 1 0 0 0 0 36 56 1 0 0 0 0 37 57 1 0 0 0 0 37 59 2 0 0 0 0 38 58 1 0 0 0 0 38 60 2 0 0 0 0 39 27 1 1 0 0 0 39 47 1 0 0 0 0 39 57 1 0 0 0 0 40 28 1 1 0 0 0 40 45 1 0 0 0 0 40 58 1 0 0 0 0 41 29 1 1 0 0 0 41 46 1 0 0 0 0 41 70 1 0 0 0 0 42 50 1 0 0 0 0 42 61 2 0 0 0 0 43 55 2 3 0 0 0 43 62 1 0 0 0 0 44 53 2 3 0 0 0 44 63 1 0 0 0 0 45 51 2 3 0 0 0 45 64 1 0 0 0 0 46 52 2 3 0 0 0 46 65 1 0 0 0 0 47 56 1 0 0 0 0 47 66 2 0 0 0 0 48 67 2 0 0 0 0 48 70 1 0 0 0 0 49 50 1 0 0 0 0 49 54 2 3 0 0 0 49 68 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	984.59
Volume:	1015.426
LogP:	3.004
LogD:	2.49
LogS:	-3.371
# Rotatable Bonds:	9
TPSA:	262.52
# H-Bond Aceptor:	20
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	6.52
Fsp3:	0.68
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:	-5.825
MDCK Permeability:	1.5834904843359254e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.838
20% Bioavailability (F20%):	0.247
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	75.74906158447266%
Volume Distribution (VD):	0.524
Pgp-substrate:	36.69618225097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	6.989
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.064
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.721

Download Data

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

Natural Product: NPC473693

Natural Product ID:	NPC473693
*Common Name:**	Majusculamide
IUPAC Name:	(2S,8S,14S,17S,20S,25S,28R,29S)-2,8-bis[(2S)-butan-2-yl]-28-ethyl-17-[(4-methoxyphenyl)methyl]-7,13,16,20,22,22,25,29-octamethyl-14-propan-2-yl-1-oxa-4,7,10,13,16,19,24,27-octazacyclotriacontane-3,6,9,12,15,18,21,23,26,30-decone
Synonyms:	Majusculamide
Standard InCHIKey:	KDZUJZSBNBCYEK-URQIXXPJSA-N
Standard InCHI:	InChI=1S/C50H80N8O12/c1-17-28(6)40-45(64)51-25-37(59)57(14)39(27(4)5)47(66)56(13)36(24-33-20-22-34(69-16)23-21-33)44(63)53-31(9)42(61)50(11,12)49(68)54-32(10)43(62)55-35(19-3)30(8)48(67)70-41(29(7)18-2)46(65)52-26-38(60)58(40)15/h20-23,27-32,35-36,39-41H,17-19,24-26H2,1-16H3,(H,51,64)(H,52,65)(H,53,63)(H,54,68)(H,55,62)/t28-,29-,30-,31-,32-,35+,36-,39-,40-,41-/m0/s1
SMILES:	CC[C@@H]([C@H]1C(=NCC(=O)N(C)[C@@H](C(C)C)C(=O)N(C)[C@@H](Cc2ccc(cc2)OC)C(=N[C@@H](C)C(=O)C(C)(C)C(=N[C@H](C(=N[C@@H]([C@@H](C(=O)O[C@H](C(=NCC(=O)N1C)O)[C@H](CC)C)C)CC)O)C)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449331
PubChem CID:	44584099
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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10514329]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10654420]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10691708]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	palauan	n.a.	PMID[10691729]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10843570]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10924172]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10978206]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076571]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076573]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076574]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11277744]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11389621]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430000]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473443]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11922791]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762816]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[12828459]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575437]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1517734]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[16643028]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125217]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17441769]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Singapore	n.a.	PMID[19093843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19489598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	eastern Caribbean	n.a.	PMID[19739598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19839606]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20030365]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	panamanian	n.a.	PMID[20158242]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[20166701]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20936843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21138309]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2128518]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21341718]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21539315]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806011]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22035372]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792428]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3924698]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[7623050]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[8699186]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9584405]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599278]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599279]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO28999	Schizothrix calcicola	Species	Schizotrichaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28999	Schizothrix calcicola	Species	Schizotrichaceae	Bacteria	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
Others	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	Activity	=	500.0	Zone units	PMID[515791]
NPT730	Cell Line	MC-38	Mus musculus	Activity	=	730.0	Zone units	PMID[515791]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	710.0	Zone units	PMID[515791]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	450.0	Zone units	PMID[515791]

☑ 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 NPC473693 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	188
0.1-0.2	1029
0.2-0.3	4682
0.3-0.4	12591
0.4-0.5	8787
0.5-0.6	13804
0.6-0.7	1275
0.7-0.8	295
0.8-0.85	30
0.85-0.9	12
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471568
0.9677	High Similarity	NPC186617
0.9006	High Similarity	NPC196091
0.8642	High Similarity	NPC472923
0.8571	High Similarity	NPC475421
0.8562	High Similarity	NPC176226
0.8537	High Similarity	NPC473502
0.8421	Intermediate Similarity	NPC470112
0.8421	Intermediate Similarity	NPC470903
0.8421	Intermediate Similarity	NPC167763
0.8324	Intermediate Similarity	NPC299806
0.8312	Intermediate Similarity	NPC476259
0.8302	Intermediate Similarity	NPC324081
0.8258	Intermediate Similarity	NPC168113
0.8218	Intermediate Similarity	NPC315542
0.8205	Intermediate Similarity	NPC197682
0.8192	Intermediate Similarity	NPC473378
0.8192	Intermediate Similarity	NPC473407
0.8176	Intermediate Similarity	NPC26108
0.8129	Intermediate Similarity	NPC50016
0.8118	Intermediate Similarity	NPC248670
0.807	Intermediate Similarity	NPC471165
0.807	Intermediate Similarity	NPC473354
0.8061	Intermediate Similarity	NPC319320
0.8061	Intermediate Similarity	NPC287757
0.805	Intermediate Similarity	NPC81026
0.8036	Intermediate Similarity	NPC254700
0.8023	Intermediate Similarity	NPC4910
0.8012	Intermediate Similarity	NPC273755
0.8012	Intermediate Similarity	NPC132771
0.8	Intermediate Similarity	NPC40234
0.8	Intermediate Similarity	NPC475123
0.8	Intermediate Similarity	NPC475204
0.7987	Intermediate Similarity	NPC266741
0.7966	Intermediate Similarity	NPC276120
0.7949	Intermediate Similarity	NPC6570
0.7931	Intermediate Similarity	NPC45037
0.7927	Intermediate Similarity	NPC39431
0.7895	Intermediate Similarity	NPC46009
0.7892	Intermediate Similarity	NPC56635
0.7889	Intermediate Similarity	NPC248822
0.7889	Intermediate Similarity	NPC477526
0.7882	Intermediate Similarity	NPC209463
0.7882	Intermediate Similarity	NPC294516
0.7882	Intermediate Similarity	NPC107938
0.787	Intermediate Similarity	NPC63931
0.7861	Intermediate Similarity	NPC476227
0.7861	Intermediate Similarity	NPC164608
0.7849	Intermediate Similarity	NPC230611
0.7841	Intermediate Similarity	NPC476321
0.7834	Intermediate Similarity	NPC127741
0.7833	Intermediate Similarity	NPC174122
0.7833	Intermediate Similarity	NPC64140
0.7826	Intermediate Similarity	NPC323662
0.7826	Intermediate Similarity	NPC477550
0.7826	Intermediate Similarity	NPC477552
0.7821	Intermediate Similarity	NPC329731
0.7803	Intermediate Similarity	NPC137627
0.7803	Intermediate Similarity	NPC306804
0.7797	Intermediate Similarity	NPC471526
0.7784	Intermediate Similarity	NPC212699
0.7784	Intermediate Similarity	NPC207675
0.7784	Intermediate Similarity	NPC32064
0.7778	Intermediate Similarity	NPC135121
0.7778	Intermediate Similarity	NPC234069
0.7771	Intermediate Similarity	NPC244509
0.7764	Intermediate Similarity	NPC201244
0.7764	Intermediate Similarity	NPC477217
0.776	Intermediate Similarity	NPC59827
0.776	Intermediate Similarity	NPC184933
0.7759	Intermediate Similarity	NPC158277
0.7759	Intermediate Similarity	NPC279871
0.7759	Intermediate Similarity	NPC473402
0.7753	Intermediate Similarity	NPC294951
0.7753	Intermediate Similarity	NPC471049
0.7753	Intermediate Similarity	NPC471050
0.7753	Intermediate Similarity	NPC471048
0.7746	Intermediate Similarity	NPC89831
0.7744	Intermediate Similarity	NPC473491
0.7742	Intermediate Similarity	NPC477551
0.772	Intermediate Similarity	NPC326027
0.7709	Intermediate Similarity	NPC138083
0.7708	Intermediate Similarity	NPC326333
0.7705	Intermediate Similarity	NPC65714
0.7705	Intermediate Similarity	NPC328763
0.7688	Intermediate Similarity	NPC123859
0.7657	Intermediate Similarity	NPC155506
0.7657	Intermediate Similarity	NPC159767
0.7651	Intermediate Similarity	NPC56685
0.7651	Intermediate Similarity	NPC262166
0.7644	Intermediate Similarity	NPC328494
0.7643	Intermediate Similarity	NPC470392
0.7634	Intermediate Similarity	NPC477527
0.7633	Intermediate Similarity	NPC244336
0.7627	Intermediate Similarity	NPC269750
0.7627	Intermediate Similarity	NPC194671
0.7622	Intermediate Similarity	NPC473371
0.7616	Intermediate Similarity	NPC61004
0.761	Intermediate Similarity	NPC68865
0.7592	Intermediate Similarity	NPC194699
0.7592	Intermediate Similarity	NPC219350
0.7582	Intermediate Similarity	NPC102959
0.7581	Intermediate Similarity	NPC471592
0.7561	Intermediate Similarity	NPC145113
0.756	Intermediate Similarity	NPC473580
0.756	Intermediate Similarity	NPC476268
0.7553	Intermediate Similarity	NPC473450
0.7545	Intermediate Similarity	NPC261934
0.7545	Intermediate Similarity	NPC5194
0.7542	Intermediate Similarity	NPC473404
0.7541	Intermediate Similarity	NPC473305
0.7541	Intermediate Similarity	NPC60516
0.7541	Intermediate Similarity	NPC163961
0.7531	Intermediate Similarity	NPC91953
0.7527	Intermediate Similarity	NPC149962
0.7516	Intermediate Similarity	NPC46098
0.7516	Intermediate Similarity	NPC268841
0.7516	Intermediate Similarity	NPC307357
0.7487	Intermediate Similarity	NPC144314
0.7485	Intermediate Similarity	NPC469243
0.7485	Intermediate Similarity	NPC162104
0.7485	Intermediate Similarity	NPC233702
0.7469	Intermediate Similarity	NPC197921
0.7468	Intermediate Similarity	NPC246079
0.746	Intermediate Similarity	NPC242728
0.7455	Intermediate Similarity	NPC16188
0.7447	Intermediate Similarity	NPC50548
0.7446	Intermediate Similarity	NPC29531
0.7446	Intermediate Similarity	NPC240130
0.7446	Intermediate Similarity	NPC61332
0.744	Intermediate Similarity	NPC202198
0.7436	Intermediate Similarity	NPC277306
0.7436	Intermediate Similarity	NPC319766
0.7436	Intermediate Similarity	NPC469442
0.7432	Intermediate Similarity	NPC94862
0.7429	Intermediate Similarity	NPC469505
0.7423	Intermediate Similarity	NPC212850
0.7423	Intermediate Similarity	NPC469360
0.7423	Intermediate Similarity	NPC83289
0.7423	Intermediate Similarity	NPC189724
0.7419	Intermediate Similarity	NPC302715
0.741	Intermediate Similarity	NPC9373
0.7384	Intermediate Similarity	NPC475544
0.7382	Intermediate Similarity	NPC311357
0.7371	Intermediate Similarity	NPC302597
0.7362	Intermediate Similarity	NPC476989
0.7362	Intermediate Similarity	NPC469427
0.7362	Intermediate Similarity	NPC469426
0.736	Intermediate Similarity	NPC136797
0.736	Intermediate Similarity	NPC25539
0.7356	Intermediate Similarity	NPC223207
0.7355	Intermediate Similarity	NPC476241
0.7355	Intermediate Similarity	NPC476260
0.7349	Intermediate Similarity	NPC247298
0.7333	Intermediate Similarity	NPC313867
0.7333	Intermediate Similarity	NPC316008
0.7317	Intermediate Similarity	NPC139326
0.7314	Intermediate Similarity	NPC471771
0.7314	Intermediate Similarity	NPC304074
0.7314	Intermediate Similarity	NPC290755
0.7314	Intermediate Similarity	NPC469479
0.7312	Intermediate Similarity	NPC274732
0.7308	Intermediate Similarity	NPC476179
0.7308	Intermediate Similarity	NPC476125
0.7301	Intermediate Similarity	NPC239762
0.7301	Intermediate Similarity	NPC163392
0.7289	Intermediate Similarity	NPC314358
0.7288	Intermediate Similarity	NPC274198
0.7288	Intermediate Similarity	NPC151030
0.7288	Intermediate Similarity	NPC269383
0.7288	Intermediate Similarity	NPC198254
0.7287	Intermediate Similarity	NPC471563
0.7284	Intermediate Similarity	NPC471264
0.7284	Intermediate Similarity	NPC471265
0.7273	Intermediate Similarity	NPC315283
0.7273	Intermediate Similarity	NPC204546
0.7273	Intermediate Similarity	NPC314388
0.7267	Intermediate Similarity	NPC197743
0.7267	Intermediate Similarity	NPC326349
0.7267	Intermediate Similarity	NPC323336
0.7267	Intermediate Similarity	NPC297145
0.7262	Intermediate Similarity	NPC245974
0.7262	Intermediate Similarity	NPC2501
0.7256	Intermediate Similarity	NPC263493
0.7256	Intermediate Similarity	NPC269398
0.7241	Intermediate Similarity	NPC241794
0.7232	Intermediate Similarity	NPC129486
0.7229	Intermediate Similarity	NPC5620
0.7212	Intermediate Similarity	NPC161069
0.7208	Intermediate Similarity	NPC476183
0.7205	Intermediate Similarity	NPC307123
0.7205	Intermediate Similarity	NPC97870
0.7205	Intermediate Similarity	NPC247018
0.7191	Intermediate Similarity	NPC276506
0.7188	Intermediate Similarity	NPC469443
0.7175	Intermediate Similarity	NPC328649
0.7169	Intermediate Similarity	NPC52748
0.7161	Intermediate Similarity	NPC476184
0.7161	Intermediate Similarity	NPC476281
0.7158	Intermediate Similarity	NPC477637

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 NPC473693 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	435
0.2-0.3	999
0.3-0.4	2075
0.4-0.5	2719
0.5-0.6	2187
0.6-0.7	569
0.7-0.8	43
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
0.8107	Intermediate Similarity	NPD7608	Discontinued
0.7871	Intermediate Similarity	NPD5745	Approved
0.7866	Intermediate Similarity	NPD7131	Phase 3
0.7742	Intermediate Similarity	NPD5746	Approved
0.7733	Intermediate Similarity	NPD7484	Phase 3
0.7733	Intermediate Similarity	NPD7485	Phase 3
0.7692	Intermediate Similarity	NPD7972	Discontinued
0.7514	Intermediate Similarity	NPD8303	Discontinued
0.7471	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3007	Approved
0.7427	Intermediate Similarity	NPD2515	Approved
0.7425	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7978	Discontinued
0.7421	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7811	Phase 3
0.7407	Intermediate Similarity	NPD7810	Phase 3
0.7381	Intermediate Similarity	NPD6390	Discontinued
0.7368	Intermediate Similarity	NPD2513	Approved
0.7362	Intermediate Similarity	NPD2240	Approved
0.7362	Intermediate Similarity	NPD2239	Approved
0.7337	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2053	Approved
0.731	Intermediate Similarity	NPD22	Approved
0.7308	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6681	Discovery
0.7273	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8031	Discontinued
0.7251	Intermediate Similarity	NPD2052	Approved
0.7238	Intermediate Similarity	NPD5485	Approved
0.7238	Intermediate Similarity	NPD5484	Approved
0.7228	Intermediate Similarity	NPD6851	Approved
0.7228	Intermediate Similarity	NPD6853	Approved
0.7212	Intermediate Similarity	NPD3656	Approved
0.7205	Intermediate Similarity	NPD1423	Approved
0.7174	Intermediate Similarity	NPD7280	Phase 3
0.7174	Intermediate Similarity	NPD7281	Phase 3
0.7168	Intermediate Similarity	NPD6677	Suspended
0.7158	Intermediate Similarity	NPD8014	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6297	Approved
0.7104	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5312	Approved
0.7088	Intermediate Similarity	NPD5313	Approved
0.7086	Intermediate Similarity	NPD5773	Approved
0.7086	Intermediate Similarity	NPD5772	Approved
0.7081	Intermediate Similarity	NPD3136	Phase 2
0.7073	Intermediate Similarity	NPD8172	Phase 2
0.7073	Intermediate Similarity	NPD8173	Phase 2
0.7069	Intermediate Similarity	NPD6072	Discontinued
0.7062	Intermediate Similarity	NPD8070	Approved
0.7047	Intermediate Similarity	NPD7565	Approved
0.7045	Intermediate Similarity	NPD7318	Phase 3
0.7037	Intermediate Similarity	NPD6504	Approved
0.7037	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6505	Approved
0.7024	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3536	Discontinued
0.7018	Intermediate Similarity	NPD6419	Discontinued
0.7	Intermediate Similarity	NPD5295	Discontinued
0.6983	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2904	Discontinued
0.6983	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8416	Discontinued
0.6949	Remote Similarity	NPD2097	Approved
0.6946	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1725	Approved
0.6944	Remote Similarity	NPD2516	Approved
0.6936	Remote Similarity	NPD7523	Phase 3
0.6932	Remote Similarity	NPD5355	Approved
0.6932	Remote Similarity	NPD7317	Phase 3
0.6932	Remote Similarity	NPD5356	Approved
0.6932	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4652	Approved
0.6906	Remote Similarity	NPD2517	Approved
0.6906	Remote Similarity	NPD7315	Approved
0.6905	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5481	Discontinued
0.6879	Remote Similarity	NPD7526	Approved
0.6879	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD52	Approved
0.6879	Remote Similarity	NPD7613	Discontinued
0.6878	Remote Similarity	NPD4434	Approved
0.6872	Remote Similarity	NPD2098	Approved
0.6871	Remote Similarity	NPD3166	Approved
0.6871	Remote Similarity	NPD3164	Approved
0.6871	Remote Similarity	NPD3165	Approved
0.6871	Remote Similarity	NPD3167	Approved
0.6854	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6032	Approved
0.6842	Remote Similarity	NPD4435	Approved
0.6839	Remote Similarity	NPD5291	Approved
0.6839	Remote Similarity	NPD1670	Discontinued
0.6839	Remote Similarity	NPD5292	Approved
0.6837	Remote Similarity	NPD6519	Phase 2
0.6832	Remote Similarity	NPD1817	Approved
0.6832	Remote Similarity	NPD1820	Approved
0.6832	Remote Similarity	NPD1818	Approved
0.6832	Remote Similarity	NPD1819	Approved
0.6825	Remote Similarity	NPD3153	Approved
0.6825	Remote Similarity	NPD3154	Approved
0.6821	Remote Similarity	NPD3985	Discontinued
0.6821	Remote Similarity	NPD4739	Approved
0.6807	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5756	Phase 2
0.6798	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2245	Discovery
0.6782	Remote Similarity	NPD7303	Discontinued
0.6772	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.677	Remote Similarity	NPD196	Phase 1
0.6768	Remote Similarity	NPD3180	Approved
0.6768	Remote Similarity	NPD5163	Phase 2
0.6768	Remote Similarity	NPD3179	Approved
0.6768	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5967	Approved
0.6758	Remote Similarity	NPD6107	Approved
0.675	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6346	Approved
0.6744	Remote Similarity	NPD2219	Phase 1
0.6742	Remote Similarity	NPD8019	Approved
0.6742	Remote Similarity	NPD7495	Discontinued
0.674	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4237	Approved
0.6725	Remote Similarity	NPD4236	Phase 3
0.6724	Remote Similarity	NPD3146	Approved
0.6724	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8643	Discontinued
0.6706	Remote Similarity	NPD8076	Discontinued
0.6705	Remote Similarity	NPD3686	Approved
0.6705	Remote Similarity	NPD6666	Approved
0.6705	Remote Similarity	NPD4210	Discontinued
0.6705	Remote Similarity	NPD3687	Approved
0.6705	Remote Similarity	NPD6667	Approved
0.6704	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6385	Approved
0.6685	Remote Similarity	NPD6386	Approved
0.6685	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2388	Discontinued
0.6684	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6863	Phase 2
0.6667	Remote Similarity	NPD2888	Approved
0.6667	Remote Similarity	NPD2667	Approved
0.6667	Remote Similarity	NPD2017	Approved
0.6667	Remote Similarity	NPD7153	Discontinued
0.6667	Remote Similarity	NPD3125	Approved
0.6667	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2889	Approved
0.6667	Remote Similarity	NPD2668	Approved
0.6667	Remote Similarity	NPD2890	Approved
0.6648	Remote Similarity	NPD6862	Phase 2
0.6648	Remote Similarity	NPD6315	Phase 2
0.6648	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3692	Discontinued
0.6647	Remote Similarity	NPD2161	Phase 2
0.6647	Remote Similarity	NPD7450	Phase 2
0.6629	Remote Similarity	NPD8417	Discontinued
0.6629	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2460	Phase 3
0.6628	Remote Similarity	NPD2459	Approved
0.6628	Remote Similarity	NPD2458	Approved
0.6627	Remote Similarity	NPD1048	Approved
0.6626	Remote Similarity	NPD1794	Approved
0.6611	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4152	Approved
0.6605	Remote Similarity	NPD1421	Approved
0.6605	Remote Similarity	NPD3685	Discontinued
0.6605	Remote Similarity	NPD1420	Approved
0.66	Remote Similarity	NPD8162	Phase 2
0.66	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5557	Phase 1
0.6595	Remote Similarity	NPD5137	Approved
0.6593	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6873	Phase 2
0.659	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2674	Phase 3
0.658	Remote Similarity	NPD4157	Discontinued
0.6578	Remote Similarity	NPD6620	Discovery
0.6575	Remote Similarity	NPD6063	Approved
0.6568	Remote Similarity	NPD3052	Approved
0.6568	Remote Similarity	NPD3054	Approved
0.6564	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5722	Discontinued
0.6554	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2122	Discontinued
0.6552	Remote Similarity	NPD8323	Discontinued
0.6548	Remote Similarity	NPD3142	Approved
0.6548	Remote Similarity	NPD3140	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