NPASS Compound

Structure

NPC120335 OpenBabel07101718292D 75 77 0 0 1 0 0 0 0 0999 V2000 -12.5727 -5.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2645 2.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8846 -8.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3846 -7.9654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5855 -4.7605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7876 -6.2978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8558 -6.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0412 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1822 0.2258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6041 4.2908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0381 3.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1733 -8.7578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3205 -4.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1079 -6.2926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3489 -7.2866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1089 -10.3328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1990 -1.6443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6993 -4.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3392 1.4367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8849 2.2924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9223 -8.6137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9954 -2.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1221 1.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4617 -7.7261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4321 -1.6547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7510 2.7924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1846 1.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7963 0.7341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9088 -8.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3837 -3.2720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6711 -2.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9973 -8.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3846 -7.9654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7428 -5.2988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8409 -5.4721 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4414 2.1943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2569 -0.1535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6788 3.2936 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5907 2.7200 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4870 0.8734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1635 -7.0138 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4723 -1.9352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0122 -7.8460 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6923 3.1298 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.5517 -1.1090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6113 -3.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8846 -7.0994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1448 -4.8382 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9675 -4.9851 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3633 -6.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0177 -7.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9773 -7.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4041 -5.8114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2344 -3.9129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6787 3.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3232 -0.9463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0094 -7.7713 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.3742 -4.0716 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6832 -5.6809 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.7023 -6.5237 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0578 -7.4611 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4423 -2.9347 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4408 4.0976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6001 -3.2491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6942 -7.1571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8245 -8.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3146 -8.4611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1766 -6.4465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1900 -4.2076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7833 4.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2947 -0.7092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1239 -9.3329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5298 -0.9011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6599 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 9 37 1 0 0 0 0 12 57 1 0 0 0 0 13 58 1 0 0 0 0 14 59 1 0 0 0 0 15 60 1 0 0 0 0 16 72 1 0 0 0 0 17 73 1 0 0 0 0 18 35 1 0 0 0 0 20 23 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 29 1 0 0 0 0 22 25 1 0 0 0 0 22 30 1 0 0 0 0 23 40 1 0 0 0 0 26 44 1 0 0 0 0 27 28 1 0 0 0 0 27 36 1 0 0 0 0 28 37 2 0 0 0 0 29 61 1 0 0 0 0 30 62 1 0 0 0 0 31 45 2 0 0 0 0 31 46 1 0 0 0 0 32 72 1 0 0 0 0 35 7 1 1 0 0 0 36 8 1 6 0 0 0 36 39 1 0 0 0 0 37 45 1 0 0 0 0 38 10 1 6 0 0 0 38 44 1 0 0 0 0 38 55 1 0 0 0 0 39 11 1 1 0 0 0 39 74 1 0 0 0 0 40 19 1 1 0 0 0 40 75 1 0 0 0 0 41 24 1 6 0 0 0 41 50 1 0 0 0 0 41 61 1 0 0 0 0 42 25 1 6 0 0 0 42 56 1 0 0 0 0 42 62 1 0 0 0 0 43 32 1 6 0 0 0 43 51 1 0 0 0 0 43 57 1 0 0 0 0 44 63 1 6 0 0 0 45 73 1 0 0 0 0 46 58 1 0 0 0 0 46 64 2 0 0 0 0 47 33 1 6 0 0 0 47 52 1 0 0 0 0 47 60 1 0 0 0 0 48 34 1 6 0 0 0 48 54 1 0 0 0 0 48 59 1 0 0 0 0 49 35 1 6 0 0 0 49 53 1 0 0 0 0 49 58 1 0 0 0 0 50 59 1 0 0 0 0 50 65 2 0 0 0 0 51 61 1 0 0 0 0 51 66 2 0 0 0 0 52 57 1 0 0 0 0 52 67 2 0 0 0 0 53 60 1 0 0 0 0 53 68 2 0 0 0 0 54 62 1 0 0 0 0 54 69 2 0 0 0 0 55 70 2 0 0 0 0 55 74 1 0 0 0 0 56 71 2 0 0 0 0 56 75 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1058.69
Volume:	1105.351
LogP:	4.651
LogD:	3.209
LogS:	-4.597
# Rotatable Bonds:	8
TPSA:	213.15
# H-Bond Aceptor:	19
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	6.698
Fsp3:	0.786
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:	-5.003
MDCK Permeability:	3.1035619031172246e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.706
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.889
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	85.36014556884766%
Volume Distribution (VD):	1.024
Pgp-substrate:	3.2095539569854736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	7.457
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.996
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.316
Skin Sensitization:	0.364
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC120335

Natural Product ID:	NPC120335
*Common Name:**	Lyngbyastatin 2
IUPAC Name:	n.a.
Synonyms:	Lyngbyastatin 2
Standard InCHIKey:	VXNKUFHPWIHJDR-CCOKTPOLSA-N
Standard InCHI:	InChI=1S/C56H94N6O13/c1-18-35(7)49-53(68)60(15)47(33(3)4)52(67)57(12)43(32-72-16)51(66)61-29-21-24-41(61)50(65)59(14)48(34(5)6)54(69)62-30-22-25-42(62)56(71)75-40(19-2)23-20-26-44(63)38(10)55(70)74-39(11)36(8)27-28-37(9)45(73-17)31-46(64)58(49)13/h28,31,33-36,38-44,47-49,63H,18-27,29-30,32H2,1-17H3/b37-28+,45-31+/t35-,36-,38+,39+,40+,41-,42-,43-,44+,47-,48-,49-/m0/s1
SMILES:	COC[C@H]1C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](C(C)C)C(=O)N2CCC[C@H]2C(=O)O[C@H](CC)CCC[C@@H](O)[C@H](C(=O)O[C@@H]([C@H](C/C=C(/C(=CC(=O)N([C@H](C(=O)N([C@H](C(=O)N1C)C(C)C)C)[C@H](CC)C)C)/OC)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507890
PubChem CID:	10102613
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]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	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
IC50	2
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.02	ug.mL-1	PMID[528922]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.014	ug.mL-1	PMID[528922]
NPT32	Organism	Mus musculus	Mus musculus	LD100	=	3.0	mg kg-1	PMID[528922]

☑ 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 NPC120335 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	124
0.1-0.2	755
0.2-0.3	3988
0.3-0.4	21064
0.4-0.5	13161
0.5-0.6	3211
0.6-0.7	367
0.7-0.8	25
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8952	High Similarity	NPC309525
0.7755	Intermediate Similarity	NPC475342
0.7603	Intermediate Similarity	NPC188785
0.7302	Intermediate Similarity	NPC271562
0.7293	Intermediate Similarity	NPC11379
0.7209	Intermediate Similarity	NPC476875
0.7176	Intermediate Similarity	NPC103391
0.7176	Intermediate Similarity	NPC472536
0.7143	Intermediate Similarity	NPC235625
0.7132	Intermediate Similarity	NPC469603
0.7008	Intermediate Similarity	NPC205176
0.6977	Remote Similarity	NPC474099
0.6977	Remote Similarity	NPC171734
0.6957	Remote Similarity	NPC469999
0.695	Remote Similarity	NPC477988
0.6933	Remote Similarity	NPC314358
0.6929	Remote Similarity	NPC476877
0.6928	Remote Similarity	NPC314050
0.6928	Remote Similarity	NPC315809
0.6923	Remote Similarity	NPC120420
0.6913	Remote Similarity	NPC476978
0.6912	Remote Similarity	NPC230849
0.6889	Remote Similarity	NPC106791
0.6889	Remote Similarity	NPC201889
0.6884	Remote Similarity	NPC477990
0.6884	Remote Similarity	NPC293550
0.6884	Remote Similarity	NPC477989
0.6884	Remote Similarity	NPC111162
0.6884	Remote Similarity	NPC323168
0.6875	Remote Similarity	NPC469604
0.6875	Remote Similarity	NPC99864
0.6867	Remote Similarity	NPC313867
0.6867	Remote Similarity	NPC316008
0.6861	Remote Similarity	NPC315188
0.6861	Remote Similarity	NPC23963
0.6846	Remote Similarity	NPC207820
0.6833	Remote Similarity	NPC322966
0.6822	Remote Similarity	NPC476876
0.6818	Remote Similarity	NPC21713
0.6818	Remote Similarity	NPC475608
0.6809	Remote Similarity	NPC471086
0.6809	Remote Similarity	NPC173173
0.68	Remote Similarity	NPC315283
0.68	Remote Similarity	NPC314388
0.6786	Remote Similarity	NPC477987
0.6786	Remote Similarity	NPC474371
0.6786	Remote Similarity	NPC329401
0.6767	Remote Similarity	NPC314550
0.6719	Remote Similarity	NPC474244
0.6716	Remote Similarity	NPC469597
0.6714	Remote Similarity	NPC477985
0.6714	Remote Similarity	NPC470654
0.6714	Remote Similarity	NPC470650
0.6714	Remote Similarity	NPC471087
0.6714	Remote Similarity	NPC326386
0.6714	Remote Similarity	NPC470653
0.6692	Remote Similarity	NPC58281
0.6691	Remote Similarity	NPC273185
0.6691	Remote Similarity	NPC65045
0.6667	Remote Similarity	NPC474827
0.6667	Remote Similarity	NPC199831
0.6667	Remote Similarity	NPC474828
0.6667	Remote Similarity	NPC68001
0.6642	Remote Similarity	NPC174463
0.6627	Remote Similarity	NPC477462
0.6623	Remote Similarity	NPC240848
0.6599	Remote Similarity	NPC82129
0.6596	Remote Similarity	NPC97580
0.6594	Remote Similarity	NPC477986
0.6594	Remote Similarity	NPC138534
0.6593	Remote Similarity	NPC193471
0.6593	Remote Similarity	NPC130124
0.6585	Remote Similarity	NPC47230
0.6585	Remote Similarity	NPC17143
0.6581	Remote Similarity	NPC2501
0.6569	Remote Similarity	NPC475642
0.6567	Remote Similarity	NPC30911
0.6567	Remote Similarity	NPC474411
0.6567	Remote Similarity	NPC316984
0.6567	Remote Similarity	NPC474431
0.6562	Remote Similarity	NPC26597
0.6558	Remote Similarity	NPC135121
0.6547	Remote Similarity	NPC470652
0.6544	Remote Similarity	NPC474984
0.6536	Remote Similarity	NPC5620
0.6519	Remote Similarity	NPC474995
0.6508	Remote Similarity	NPC150041
0.6507	Remote Similarity	NPC133089
0.6503	Remote Similarity	NPC314282
0.65	Remote Similarity	NPC470000
0.6497	Remote Similarity	NPC162104
0.6489	Remote Similarity	NPC133420
0.6489	Remote Similarity	NPC64168
0.6484	Remote Similarity	NPC220234
0.6475	Remote Similarity	NPC241050
0.6467	Remote Similarity	NPC25025
0.6462	Remote Similarity	NPC473289
0.6456	Remote Similarity	NPC122590
0.6447	Remote Similarity	NPC247776
0.6447	Remote Similarity	NPC475278
0.6447	Remote Similarity	NPC263493
0.6447	Remote Similarity	NPC309450
0.6447	Remote Similarity	NPC71866
0.6447	Remote Similarity	NPC304299
0.6447	Remote Similarity	NPC475266
0.6447	Remote Similarity	NPC269398
0.6444	Remote Similarity	NPC181510
0.6444	Remote Similarity	NPC168758
0.6444	Remote Similarity	NPC47857
0.6429	Remote Similarity	NPC477217
0.6429	Remote Similarity	NPC201244
0.6424	Remote Similarity	NPC315848
0.6424	Remote Similarity	NPC315210
0.6423	Remote Similarity	NPC272166
0.6412	Remote Similarity	NPC279833
0.6412	Remote Similarity	NPC265094
0.6412	Remote Similarity	NPC6271
0.6412	Remote Similarity	NPC80439
0.6412	Remote Similarity	NPC173690
0.6408	Remote Similarity	NPC314629
0.6406	Remote Similarity	NPC476344
0.6406	Remote Similarity	NPC52820
0.6405	Remote Similarity	NPC161069
0.6403	Remote Similarity	NPC17581
0.6403	Remote Similarity	NPC476155
0.6403	Remote Similarity	NPC284656
0.6402	Remote Similarity	NPC472923
0.6398	Remote Similarity	NPC319334
0.6398	Remote Similarity	NPC197743
0.6398	Remote Similarity	NPC327517
0.6398	Remote Similarity	NPC322372
0.6398	Remote Similarity	NPC297145
0.6397	Remote Similarity	NPC43648
0.6395	Remote Similarity	NPC470112
0.6395	Remote Similarity	NPC167763
0.6395	Remote Similarity	NPC470903
0.6387	Remote Similarity	NPC262077
0.6383	Remote Similarity	NPC156379
0.6383	Remote Similarity	NPC160688
0.6383	Remote Similarity	NPC475383
0.6377	Remote Similarity	NPC66007
0.6376	Remote Similarity	NPC287401
0.637	Remote Similarity	NPC215507
0.6369	Remote Similarity	NPC129666
0.6364	Remote Similarity	NPC313333
0.6364	Remote Similarity	NPC313342
0.6364	Remote Similarity	NPC52748
0.6364	Remote Similarity	NPC314451
0.6364	Remote Similarity	NPC321197
0.6364	Remote Similarity	NPC314512
0.6357	Remote Similarity	NPC470788
0.6351	Remote Similarity	NPC475987
0.6351	Remote Similarity	NPC130309
0.6351	Remote Similarity	NPC313348
0.6346	Remote Similarity	NPC225648
0.6346	Remote Similarity	NPC145113
0.6346	Remote Similarity	NPC329761
0.6343	Remote Similarity	NPC67009
0.6336	Remote Similarity	NPC471097
0.6336	Remote Similarity	NPC475149
0.6331	Remote Similarity	NPC6531
0.6327	Remote Similarity	NPC316401
0.6323	Remote Similarity	NPC209509
0.6316	Remote Similarity	NPC178662
0.6316	Remote Similarity	NPC470884
0.6316	Remote Similarity	NPC98424
0.6316	Remote Similarity	NPC476133
0.6316	Remote Similarity	NPC92784
0.6312	Remote Similarity	NPC477140
0.6312	Remote Similarity	NPC477143
0.6309	Remote Similarity	NPC239252
0.6309	Remote Similarity	NPC473703
0.6306	Remote Similarity	NPC471820
0.6306	Remote Similarity	NPC471821
0.6304	Remote Similarity	NPC471645
0.6301	Remote Similarity	NPC316205
0.6301	Remote Similarity	NPC315387
0.6294	Remote Similarity	NPC316133
0.6294	Remote Similarity	NPC318445
0.6277	Remote Similarity	NPC261750
0.6277	Remote Similarity	NPC1111
0.6276	Remote Similarity	NPC247902
0.6276	Remote Similarity	NPC262880
0.6275	Remote Similarity	NPC239762
0.6275	Remote Similarity	NPC163392
0.626	Remote Similarity	NPC130436
0.626	Remote Similarity	NPC469861
0.626	Remote Similarity	NPC469860
0.6259	Remote Similarity	NPC30196
0.6259	Remote Similarity	NPC296043
0.6259	Remote Similarity	NPC41162
0.6259	Remote Similarity	NPC307165
0.625	Remote Similarity	NPC471264
0.625	Remote Similarity	NPC36254
0.625	Remote Similarity	NPC471265
0.6242	Remote Similarity	NPC138775
0.6241	Remote Similarity	NPC471261
0.6233	Remote Similarity	NPC470655
0.6233	Remote Similarity	NPC329919
0.6233	Remote Similarity	NPC477793

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 NPC120335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	100
0.1-0.2	505
0.2-0.3	2444
0.3-0.4	4078
0.4-0.5	1700
0.5-0.6	293
0.6-0.7	30
0.7-0.8	0
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
0.7153	Intermediate Similarity	NPD8273	Phase 1
0.6944	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8415	Approved
0.6716	Remote Similarity	NPD1376	Discontinued
0.66	Remote Similarity	NPD8384	Approved
0.6582	Remote Similarity	NPD8414	Discontinued
0.6567	Remote Similarity	NPD2204	Approved
0.6549	Remote Similarity	NPD8451	Approved
0.6503	Remote Similarity	NPD8448	Approved
0.6483	Remote Similarity	NPD8391	Approved
0.6483	Remote Similarity	NPD8390	Approved
0.6483	Remote Similarity	NPD8392	Approved
0.6467	Remote Similarity	NPD8172	Phase 2
0.6467	Remote Similarity	NPD8173	Phase 2
0.6423	Remote Similarity	NPD1000	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8340	Approved
0.6364	Remote Similarity	NPD8299	Approved
0.6364	Remote Similarity	NPD8341	Approved
0.6364	Remote Similarity	NPD8342	Approved
0.6331	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7642	Approved
0.6286	Remote Similarity	NPD7641	Discontinued
0.625	Remote Similarity	NPD5725	Approved
0.6224	Remote Similarity	NPD8080	Discontinued
0.6216	Remote Similarity	NPD4175	Approved
0.6216	Remote Similarity	NPD4177	Approved
0.6214	Remote Similarity	NPD961	Discontinued
0.6207	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7830	Approved
0.6181	Remote Similarity	NPD7829	Approved
0.6164	Remote Similarity	NPD7746	Phase 1
0.6164	Remote Similarity	NPD7747	Phase 1
0.6154	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3715	Approved
0.6154	Remote Similarity	NPD3714	Approved
0.6154	Remote Similarity	NPD3713	Approved
0.6144	Remote Similarity	NPD6073	Approved
0.6107	Remote Similarity	NPD2101	Approved
0.6084	Remote Similarity	NPD2645	Approved
0.6067	Remote Similarity	NPD2613	Approved
0.6056	Remote Similarity	NPD1773	Discontinued
0.6053	Remote Similarity	NPD3615	Approved
0.6053	Remote Similarity	NPD5747	Discontinued
0.6053	Remote Similarity	NPD3088	Approved
0.6053	Remote Similarity	NPD2571	Approved
0.6053	Remote Similarity	NPD2574	Discontinued
0.6053	Remote Similarity	NPD3614	Approved
0.6053	Remote Similarity	NPD4745	Approved
0.6053	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3089	Approved
0.6053	Remote Similarity	NPD2566	Approved
0.6053	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3087	Approved
0.6053	Remote Similarity	NPD4746	Phase 3
0.6053	Remote Similarity	NPD3616	Approved
0.6053	Remote Similarity	NPD2570	Approved
0.6053	Remote Similarity	NPD2573	Approved
0.6053	Remote Similarity	NPD3090	Approved
0.6042	Remote Similarity	NPD8444	Approved
0.6014	Remote Similarity	NPD3159	Discontinued
0.6014	Remote Similarity	NPD2132	Phase 3
0.6	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD4686	Approved
0.5974	Remote Similarity	NPD4685	Phase 3
0.5974	Remote Similarity	NPD4684	Phase 3
0.5912	Remote Similarity	NPD5265	Approved
0.5912	Remote Similarity	NPD5264	Approved
0.5891	Remote Similarity	NPD7983	Approved
0.589	Remote Similarity	NPD7623	Phase 3
0.589	Remote Similarity	NPD1806	Approved
0.589	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7896	Approved
0.5878	Remote Similarity	NPD3072	Approved
0.5878	Remote Similarity	NPD3071	Approved
0.5878	Remote Similarity	NPD3073	Approved
0.5871	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD5767	Discontinued
0.586	Remote Similarity	NPD6077	Discontinued
0.5855	Remote Similarity	NPD6845	Suspended
0.5855	Remote Similarity	NPD4676	Approved
0.5839	Remote Similarity	NPD7333	Discontinued
0.5833	Remote Similarity	NPD7839	Suspended
0.5822	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6698	Approved
0.5814	Remote Similarity	NPD46	Approved
0.5811	Remote Similarity	NPD4762	Approved
0.5811	Remote Similarity	NPD4761	Approved
0.5806	Remote Similarity	NPD4153	Approved
0.5806	Remote Similarity	NPD8416	Discontinued
0.58	Remote Similarity	NPD8336	Approved
0.58	Remote Similarity	NPD8337	Approved
0.5797	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD8140	Approved
0.5796	Remote Similarity	NPD2569	Approved
0.5796	Remote Similarity	NPD2567	Approved
0.5793	Remote Similarity	NPD2495	Phase 3
0.5789	Remote Similarity	NPD8038	Phase 2
0.5786	Remote Similarity	NPD6421	Discontinued
0.5786	Remote Similarity	NPD5193	Discontinued
0.5776	Remote Similarity	NPD2575	Approved
0.5772	Remote Similarity	NPD2584	Suspended
0.5772	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD7500	Approved
0.5758	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD1689	Approved
0.5752	Remote Similarity	NPD5263	Approved
0.5732	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD7512	Approved
0.5723	Remote Similarity	NPD7511	Approved
0.5714	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.5705	Remote Similarity	NPD2609	Approved
0.5705	Remote Similarity	NPD3132	Approved
0.5705	Remote Similarity	NPD3131	Approved
0.5705	Remote Similarity	NPD4218	Approved
0.5705	Remote Similarity	NPD2612	Approved
0.5705	Remote Similarity	NPD2608	Approved
0.5705	Remote Similarity	NPD4217	Approved
0.5705	Remote Similarity	NPD2610	Approved
0.5705	Remote Similarity	NPD2611	Approved
0.5705	Remote Similarity	NPD4216	Approved
0.5705	Remote Similarity	NPD4215	Approved
0.5693	Remote Similarity	NPD2258	Approved
0.5693	Remote Similarity	NPD2259	Approved
0.5692	Remote Similarity	NPD7838	Discovery
0.5692	Remote Similarity	NPD2682	Approved
0.5686	Remote Similarity	NPD7260	Phase 2
0.5683	Remote Similarity	NPD8307	Discontinued
0.5676	Remote Similarity	NPD2838	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD9512	Approved
0.5661	Remote Similarity	NPD7811	Phase 3
0.5661	Remote Similarity	NPD7810	Phase 3
0.5649	Remote Similarity	NPD8338	Approved
0.5644	Remote Similarity	NPD8323	Discontinued
0.5641	Remote Similarity	NPD8065	Phase 2
0.5617	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD777	Phase 3
0.5612	Remote Similarity	NPD4211	Phase 1
0.5606	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD5296	Approved
0.5602	Remote Similarity	NPD7613	Discontinued
0.56	Remote Similarity	NPD4706	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