NPASS Compound

Structure

NPC109406 OpenBabel07101718282D 99103 0 0 1 0 0 0 0 0999 V2000 -10.9849 -7.0940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4085 4.1186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5405 -2.2231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1472 -0.7523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.8000 0.9165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4066 -3.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5904 -6.2759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8029 3.3005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5467 -0.9092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1534 -2.0661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9772 -2.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5839 -0.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.5115 3.7027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1182 -6.6781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4252 -6.9117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9681 3.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4355 -8.8236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9579 5.8482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3027 -8.6359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0906 5.6605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7480 -8.2626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6454 5.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5264 -6.9213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0425 -5.6265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.6764 -0.4964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2831 -2.4790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3508 2.6511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6354 -7.3753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.6733 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2800 -2.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6303 -4.8174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7630 1.8421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.3726 1.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9792 -4.8729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6967 -7.8408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6967 4.8654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7579 4.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.8092 1.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4159 -4.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8669 -6.9213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5264 3.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0843 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -3.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3354 -6.3336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0579 3.3582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.1100 -1.3205 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7167 -1.6549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -18.8031 0.9950 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4097 -3.9704 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3508 -5.6265 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0425 2.6511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.5498 -0.9877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1564 -1.9877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.5467 -2.0661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1534 -0.9092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6844 -7.6844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7090 4.7090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6967 -7.8408 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6967 4.8654 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7579 -7.3753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6354 4.4000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -17.2397 0.2493 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8464 -3.2247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -17.3756 1.9760 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9823 -4.9514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8669 3.9460 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.6303 1.8421 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7630 -4.8174 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.3933 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.9754 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0579 -6.3336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3354 3.3582 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.0843 -3.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.1131 -1.2420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7198 -1.7334 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.5498 -1.9877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1564 -0.9877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9178 -8.6567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4755 5.6813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3444 4.7986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4830 2.3646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0896 -5.3399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.3657 0.2334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9724 -3.2088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.0082 -4.3091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6149 1.3337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.6826 -0.3394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2892 -2.6359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.9451 2.8786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5518 -5.8540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4085 -7.0940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9849 4.1186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.2367 0.1709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8433 -3.1462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7090 -7.6844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6844 4.7090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3933 -2.9754 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 44 1 0 0 0 0 2 45 2 0 0 0 0 13 90 1 0 0 0 0 14 91 1 0 0 0 0 15 92 1 0 0 0 0 16 93 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 23 28 1 0 0 0 0 23 44 2 0 0 0 0 24 31 2 0 0 0 0 24 44 1 0 0 0 0 25 29 1 0 0 0 0 25 46 1 0 0 0 0 26 30 1 0 0 0 0 26 47 1 0 0 0 0 27 32 2 0 0 0 0 27 45 1 0 0 0 0 28 56 1 0 0 0 0 31 73 1 0 0 0 0 32 74 1 0 0 0 0 33 48 1 0 0 0 0 33 64 1 0 0 0 0 34 49 1 0 0 0 0 34 65 1 0 0 0 0 35 56 1 0 0 0 0 35 58 1 0 0 0 0 36 57 1 0 0 0 0 36 59 1 0 0 0 0 37 57 1 0 0 0 0 37 66 1 0 0 0 0 38 62 1 0 0 0 0 38 64 1 0 0 0 0 39 63 1 0 0 0 0 39 65 1 0 0 0 0 40 60 1 0 0 0 0 40 71 1 0 0 0 0 41 61 1 0 0 0 0 41 72 1 0 0 0 0 42 67 1 0 0 0 0 42 69 1 0 0 0 0 43 68 1 0 0 0 0 43 70 1 0 0 0 0 45 66 1 0 0 0 0 46 3 1 1 0 0 0 46 75 1 0 0 0 0 47 4 1 1 0 0 0 47 76 1 0 0 0 0 48 5 1 1 0 0 0 48 94 1 0 0 0 0 49 6 1 1 0 0 0 49 95 1 0 0 0 0 50 7 1 6 0 0 0 50 68 1 0 0 0 0 50 71 1 0 0 0 0 51 8 1 6 0 0 0 51 67 1 0 0 0 0 51 72 1 0 0 0 0 52 9 1 1 0 0 0 52 69 1 0 0 0 0 52 77 1 0 0 0 0 53 10 1 1 0 0 0 53 70 1 0 0 0 0 53 78 1 0 0 0 0 54 11 1 1 0 0 0 54 75 1 0 0 0 0 55 12 1 1 0 0 0 55 76 1 0 0 0 0 56 79 1 1 0 0 0 57 80 1 1 0 0 0 58 19 1 1 0 0 0 58 96 1 0 0 0 0 59 20 1 1 0 0 0 59 97 1 0 0 0 0 60 21 1 6 0 0 0 60 96 1 0 0 0 0 61 22 1 6 0 0 0 61 97 1 0 0 0 0 62 29 1 6 0 0 0 62 94 1 0 0 0 0 63 30 1 6 0 0 0 63 95 1 0 0 0 0 64 90 1 1 0 0 0 65 91 1 1 0 0 0 66 81 1 1 0 0 0 67 82 1 6 0 0 0 68 83 1 6 0 0 0 69 84 1 6 0 0 0 70 85 1 6 0 0 0 71 92 1 1 0 0 0 72 93 1 1 0 0 0 73 86 2 0 0 0 0 73 98 1 0 0 0 0 74 87 2 0 0 0 0 74 99 1 0 0 0 0 75 88 1 6 0 0 0 76 89 1 6 0 0 0 77 54 1 6 0 0 0 77 98 1 0 0 0 0 78 55 1 6 0 0 0 78 99 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1404.93
Volume:	1478.364
LogP:	6.798
LogD:	4.207
LogS:	-5.411
# Rotatable Bonds:	16
TPSA:	308.51
# H-Bond Aceptor:	21
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	8.475
Fsp3:	0.821
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.249
MDCK Permeability:	0.00024176837177947164
Pgp-inhibitor:	1.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.934
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.593

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	62.23345947265625%
Volume Distribution (VD):	0.757
Pgp-substrate:	19.496109008789062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.866
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	3.442
Half-life (T1/2):	0.014

ADMET: Toxicity

hERG Blockers:	0.694
Human Hepatotoxicity (H-HT):	0.996
Drug-inuced Liver Injury (DILI):	0.242
AMES Toxicity:	0.179
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.991
Carcinogencity:	0.11
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.735

Download Data

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

Natural Product: NPC109406

Natural Product ID:	NPC109406
*Common Name:**	BCFBSWSNZGXBSC-ZLIWSSSSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BCFBSWSNZGXBSC-ZLIWSSSSSA-N
Standard InCHI:	InChI=1S/C78H132O21/c1-44-23-28-56(79)35-58-19-17-21-60(96-58)40-71(92-15)50(7)68(83)43-70(85)53(10)78(55(12)76(89)47(4)26-30-63-39-65(91-14)34-49(6)95-63)99-74(87)32-27-45(2)66(81)37-57(80)36-59-20-18-22-61(97-59)41-72(93-16)51(8)67(82)42-69(84)52(9)77(98-73(86)31-24-44)54(11)75(88)46(3)25-29-62-38-64(90-13)33-48(5)94-62/h17-20,23-24,27,31-32,46-72,75-85,88-89H,2,21-22,25-26,28-30,33-43H2,1,3-16H3/b31-24+,32-27+,44-23+/t46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57+,58-,59-,60-,61-,62-,63-,64+,65+,66+,67-,68-,69+,70+,71-,72-,75-,76-,77-,78-/m0/s1
SMILES:	CO[C@H]1C[C@H](CC[C@@H]([C@@H]([C@@H]([C@H]2OC(=O)/C=C/C(=C/C[C@H](O)C[C@@H]3C=CC[C@H](O3)C[C@H](OC)[C@@H](C)[C@@H](O)C[C@@H](O)[C@H](C)[C@H](OC(=O)/C=C/C(=C)[C@@H](C[C@@H](C[C@H]3O[C@H](C[C@@H]([C@H]([C@H](C[C@H]([C@@H]2C)O)O)C)OC)CC=C3)O)O)[C@H]([C@H]([C@H](CC[C@H]2C[C@H](OC)C[C@@H](O2)C)C)O)C)/C)C)O)C)O[C@H](C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413484
PubChem CID:	71769924
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421754]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193024]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[15679329]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16441091]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125225]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318032]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[19961178]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078073]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	palau	n.a.	PMID[20078073]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428459]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23830699]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27213234]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27548648]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29989811]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30346758]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32191460]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Efficacy	=	42.67	%	PMID[451934]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	15.0	nM	PMID[451934]

☑ 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 NPC109406 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	190
0.1-0.2	1032
0.2-0.3	3898
0.3-0.4	7802
0.4-0.5	16168
0.5-0.6	9479
0.6-0.7	3720
0.7-0.8	363
0.8-0.85	24
0.85-0.9	13
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC206679
0.9884	High Similarity	NPC471324
0.9884	High Similarity	NPC114172
0.977	High Similarity	NPC159092
0.9655	High Similarity	NPC476084
0.9655	High Similarity	NPC476075
0.9341	High Similarity	NPC475332
0.8977	High Similarity	NPC199382
0.8764	High Similarity	NPC313658
0.8764	High Similarity	NPC316138
0.8721	High Similarity	NPC8538
0.8721	High Similarity	NPC315731
0.8721	High Similarity	NPC184208
0.8511	High Similarity	NPC300710
0.8488	Intermediate Similarity	NPC139712
0.8469	Intermediate Similarity	NPC197736
0.8454	Intermediate Similarity	NPC471637
0.8454	Intermediate Similarity	NPC57586
0.8454	Intermediate Similarity	NPC2313
0.8454	Intermediate Similarity	NPC475655
0.8454	Intermediate Similarity	NPC475157
0.8454	Intermediate Similarity	NPC154132
0.8438	Intermediate Similarity	NPC475653
0.8421	Intermediate Similarity	NPC255410
0.8333	Intermediate Similarity	NPC120299
0.83	Intermediate Similarity	NPC315070
0.828	Intermediate Similarity	NPC3952
0.828	Intermediate Similarity	NPC177668
0.8242	Intermediate Similarity	NPC47220
0.8242	Intermediate Similarity	NPC186332
0.8182	Intermediate Similarity	NPC473596
0.8172	Intermediate Similarity	NPC133450
0.814	Intermediate Similarity	NPC469880
0.8132	Intermediate Similarity	NPC242233
0.8041	Intermediate Similarity	NPC288350
0.8041	Intermediate Similarity	NPC173329
0.8023	Intermediate Similarity	NPC285840
0.8023	Intermediate Similarity	NPC327041
0.8021	Intermediate Similarity	NPC159698
0.8021	Intermediate Similarity	NPC256368
0.7935	Intermediate Similarity	NPC471494
0.7917	Intermediate Similarity	NPC238090
0.7917	Intermediate Similarity	NPC472196
0.7917	Intermediate Similarity	NPC472195
0.7879	Intermediate Similarity	NPC203627
0.7849	Intermediate Similarity	NPC61527
0.7841	Intermediate Similarity	NPC477203
0.7802	Intermediate Similarity	NPC10080
0.7802	Intermediate Similarity	NPC123908
0.7802	Intermediate Similarity	NPC477390
0.7802	Intermediate Similarity	NPC477385
0.7791	Intermediate Similarity	NPC329914
0.7791	Intermediate Similarity	NPC185186
0.7791	Intermediate Similarity	NPC327383
0.7791	Intermediate Similarity	NPC477085
0.7791	Intermediate Similarity	NPC329890
0.7788	Intermediate Similarity	NPC193765
0.7778	Intermediate Similarity	NPC470147
0.7778	Intermediate Similarity	NPC133226
0.7732	Intermediate Similarity	NPC476049
0.7727	Intermediate Similarity	NPC188860
0.7727	Intermediate Similarity	NPC477202
0.7717	Intermediate Similarity	NPC44261
0.7674	Intermediate Similarity	NPC316185
0.7674	Intermediate Similarity	NPC477087
0.7674	Intermediate Similarity	NPC477086
0.7667	Intermediate Similarity	NPC180725
0.7667	Intermediate Similarity	NPC470148
0.7667	Intermediate Similarity	NPC470149
0.766	Intermediate Similarity	NPC311163
0.766	Intermediate Similarity	NPC316426
0.766	Intermediate Similarity	NPC315395
0.7653	Intermediate Similarity	NPC469491
0.7647	Intermediate Similarity	NPC201191
0.764	Intermediate Similarity	NPC233071
0.764	Intermediate Similarity	NPC315394
0.764	Intermediate Similarity	NPC84360
0.7634	Intermediate Similarity	NPC186155
0.7634	Intermediate Similarity	NPC78673
0.7634	Intermediate Similarity	NPC160517
0.7619	Intermediate Similarity	NPC473807
0.7596	Intermediate Similarity	NPC476740
0.7596	Intermediate Similarity	NPC476738
0.7579	Intermediate Similarity	NPC86005
0.7579	Intermediate Similarity	NPC477959
0.7579	Intermediate Similarity	NPC471055
0.7579	Intermediate Similarity	NPC471056
0.7576	Intermediate Similarity	NPC272050
0.7573	Intermediate Similarity	NPC474581
0.7573	Intermediate Similarity	NPC473816
0.7573	Intermediate Similarity	NPC475367
0.7558	Intermediate Similarity	NPC476037
0.7558	Intermediate Similarity	NPC476012
0.7558	Intermediate Similarity	NPC4299
0.7556	Intermediate Similarity	NPC248775
0.7547	Intermediate Similarity	NPC133625
0.7527	Intermediate Similarity	NPC16488
0.7525	Intermediate Similarity	NPC308567
0.7525	Intermediate Similarity	NPC65700
0.7525	Intermediate Similarity	NPC261377
0.7525	Intermediate Similarity	NPC255592
0.75	Intermediate Similarity	NPC315843
0.75	Intermediate Similarity	NPC477204
0.7474	Intermediate Similarity	NPC477387
0.7474	Intermediate Similarity	NPC208473
0.7474	Intermediate Similarity	NPC477389
0.7473	Intermediate Similarity	NPC471537
0.7453	Intermediate Similarity	NPC470024
0.7451	Intermediate Similarity	NPC475053
0.7449	Intermediate Similarity	NPC110072
0.7444	Intermediate Similarity	NPC474026
0.7442	Intermediate Similarity	NPC101622
0.7442	Intermediate Similarity	NPC151481
0.7423	Intermediate Similarity	NPC212598
0.7423	Intermediate Similarity	NPC285588
0.7419	Intermediate Similarity	NPC224455
0.7404	Intermediate Similarity	NPC309398
0.7396	Intermediate Similarity	NPC118077
0.7396	Intermediate Similarity	NPC477386
0.7396	Intermediate Similarity	NPC477388
0.7396	Intermediate Similarity	NPC475186
0.7379	Intermediate Similarity	NPC477717
0.7368	Intermediate Similarity	NPC92633
0.7358	Intermediate Similarity	NPC469959
0.7358	Intermediate Similarity	NPC108682
0.7358	Intermediate Similarity	NPC472263
0.7358	Intermediate Similarity	NPC109376
0.7358	Intermediate Similarity	NPC469957
0.7353	Intermediate Similarity	NPC161855
0.7353	Intermediate Similarity	NPC83895
0.7353	Intermediate Similarity	NPC187761
0.7347	Intermediate Similarity	NPC313670
0.734	Intermediate Similarity	NPC185949
0.734	Intermediate Similarity	NPC107498
0.734	Intermediate Similarity	NPC474809
0.7327	Intermediate Similarity	NPC472995
0.7327	Intermediate Similarity	NPC473291
0.7312	Intermediate Similarity	NPC475944
0.7312	Intermediate Similarity	NPC112868
0.7304	Intermediate Similarity	NPC219804
0.7303	Intermediate Similarity	NPC107654
0.7292	Intermediate Similarity	NPC164393
0.7292	Intermediate Similarity	NPC122502
0.729	Intermediate Similarity	NPC224660
0.7283	Intermediate Similarity	NPC477088
0.7283	Intermediate Similarity	NPC1180
0.7283	Intermediate Similarity	NPC55304
0.7283	Intermediate Similarity	NPC226226
0.7283	Intermediate Similarity	NPC86971
0.7282	Intermediate Similarity	NPC477721
0.7282	Intermediate Similarity	NPC477716
0.7264	Intermediate Similarity	NPC93026
0.7264	Intermediate Similarity	NPC29389
0.7264	Intermediate Similarity	NPC265502
0.7264	Intermediate Similarity	NPC469960
0.7264	Intermediate Similarity	NPC172867
0.7263	Intermediate Similarity	NPC473308
0.7263	Intermediate Similarity	NPC266718
0.7255	Intermediate Similarity	NPC477718
0.7255	Intermediate Similarity	NPC40812
0.7255	Intermediate Similarity	NPC477719
0.7253	Intermediate Similarity	NPC475711
0.7248	Intermediate Similarity	NPC17791
0.7248	Intermediate Similarity	NPC297945
0.7248	Intermediate Similarity	NPC126897
0.7228	Intermediate Similarity	NPC170204
0.7222	Intermediate Similarity	NPC313668
0.7222	Intermediate Similarity	NPC315836
0.7212	Intermediate Similarity	NPC197447
0.7212	Intermediate Similarity	NPC169365
0.72	Intermediate Similarity	NPC162615
0.72	Intermediate Similarity	NPC205034
0.72	Intermediate Similarity	NPC152778
0.72	Intermediate Similarity	NPC320552
0.7188	Intermediate Similarity	NPC471223
0.7188	Intermediate Similarity	NPC67081
0.7184	Intermediate Similarity	NPC275086
0.7184	Intermediate Similarity	NPC325229
0.7182	Intermediate Similarity	NPC470025
0.7182	Intermediate Similarity	NPC328074
0.7182	Intermediate Similarity	NPC317460
0.7182	Intermediate Similarity	NPC321272
0.7174	Intermediate Similarity	NPC209135
0.7174	Intermediate Similarity	NPC474816
0.7172	Intermediate Similarity	NPC182136
0.7172	Intermediate Similarity	NPC327253
0.7172	Intermediate Similarity	NPC202886
0.7172	Intermediate Similarity	NPC475855
0.7172	Intermediate Similarity	NPC473448
0.7159	Intermediate Similarity	NPC473361
0.7159	Intermediate Similarity	NPC329904
0.7158	Intermediate Similarity	NPC142111
0.7158	Intermediate Similarity	NPC263087
0.7158	Intermediate Similarity	NPC106912
0.7158	Intermediate Similarity	NPC2379
0.7158	Intermediate Similarity	NPC473315
0.7158	Intermediate Similarity	NPC31019
0.7158	Intermediate Similarity	NPC27314
0.7158	Intermediate Similarity	NPC116543
0.7157	Intermediate Similarity	NPC180722

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 NPC109406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1136
0.2-0.3	3536
0.3-0.4	2794
0.4-0.5	1130
0.5-0.6	315
0.6-0.7	70
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8247	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD7838	Discovery
0.7526	Intermediate Similarity	NPD46	Approved
0.7526	Intermediate Similarity	NPD6698	Approved
0.7273	Intermediate Similarity	NPD7983	Approved
0.7248	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7839	Suspended
0.7115	Intermediate Similarity	NPD6648	Approved
0.7083	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5344	Discontinued
0.703	Intermediate Similarity	NPD5779	Approved
0.703	Intermediate Similarity	NPD5778	Approved
0.6983	Remote Similarity	NPD8513	Phase 3
0.6931	Remote Similarity	NPD7637	Suspended
0.6838	Remote Similarity	NPD8517	Approved
0.6838	Remote Similarity	NPD8515	Approved
0.6838	Remote Similarity	NPD7503	Approved
0.6838	Remote Similarity	NPD8516	Approved
0.6818	Remote Similarity	NPD6686	Approved
0.6792	Remote Similarity	NPD7639	Approved
0.6792	Remote Similarity	NPD7640	Approved
0.6733	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6101	Approved
0.6698	Remote Similarity	NPD7638	Approved
0.6633	Remote Similarity	NPD7154	Phase 3
0.6602	Remote Similarity	NPD6411	Approved
0.6583	Remote Similarity	NPD7830	Approved
0.6583	Remote Similarity	NPD7829	Approved
0.6579	Remote Similarity	NPD6053	Discontinued
0.6555	Remote Similarity	NPD8033	Approved
0.6542	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD4250	Approved
0.6535	Remote Similarity	NPD4251	Approved
0.6505	Remote Similarity	NPD5785	Approved
0.6495	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8294	Approved
0.6471	Remote Similarity	NPD8377	Approved
0.6465	Remote Similarity	NPD6695	Phase 3
0.6436	Remote Similarity	NPD4249	Approved
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8074	Phase 3
0.6417	Remote Similarity	NPD8379	Approved
0.6417	Remote Similarity	NPD8296	Approved
0.6417	Remote Similarity	NPD8335	Approved
0.6417	Remote Similarity	NPD8378	Approved
0.6417	Remote Similarity	NPD8380	Approved
0.6404	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7750	Discontinued
0.6356	Remote Similarity	NPD7115	Discovery
0.6337	Remote Similarity	NPD5363	Approved
0.6327	Remote Similarity	NPD4820	Approved
0.6327	Remote Similarity	NPD7332	Phase 2
0.6327	Remote Similarity	NPD4819	Approved
0.6327	Remote Similarity	NPD7514	Phase 3
0.6327	Remote Similarity	NPD4821	Approved
0.6327	Remote Similarity	NPD4822	Approved
0.6316	Remote Similarity	NPD8039	Approved
0.6316	Remote Similarity	NPD8264	Approved
0.6303	Remote Similarity	NPD7328	Approved
0.6303	Remote Similarity	NPD7327	Approved
0.63	Remote Similarity	NPD5362	Discontinued
0.6289	Remote Similarity	NPD4271	Approved
0.6289	Remote Similarity	NPD4268	Approved
0.6289	Remote Similarity	NPD7145	Approved
0.6263	Remote Similarity	NPD6902	Approved
0.6261	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD7516	Approved
0.6224	Remote Similarity	NPD6929	Approved
0.6218	Remote Similarity	NPD7505	Discontinued
0.6216	Remote Similarity	NPD7632	Discontinued
0.6214	Remote Similarity	NPD7524	Approved
0.62	Remote Similarity	NPD5209	Approved
0.6186	Remote Similarity	NPD6925	Approved
0.6186	Remote Similarity	NPD5776	Phase 2
0.6176	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6931	Approved
0.6162	Remote Similarity	NPD6930	Phase 2
0.616	Remote Similarity	NPD8448	Approved
0.6148	Remote Similarity	NPD8444	Approved
0.6139	Remote Similarity	NPD5331	Approved
0.6139	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4790	Discontinued
0.6087	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8273	Phase 1
0.608	Remote Similarity	NPD8451	Approved
0.6061	Remote Similarity	NPD5124	Phase 1
0.6061	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4270	Approved
0.604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4269	Approved
0.6033	Remote Similarity	NPD7641	Discontinued
0.602	Remote Similarity	NPD4756	Discovery
0.602	Remote Similarity	NPD6932	Approved
0.6019	Remote Similarity	NPD7748	Approved
0.6019	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6647	Phase 2
0.6016	Remote Similarity	NPD8392	Approved
0.6016	Remote Similarity	NPD8390	Approved
0.6016	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7087	Discontinued
0.5969	Remote Similarity	NPD7260	Phase 2
0.5966	Remote Similarity	NPD8133	Approved
0.5962	Remote Similarity	NPD5786	Approved
0.596	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7507	Approved
0.595	Remote Similarity	NPD7500	Approved
0.5941	Remote Similarity	NPD6898	Phase 1
0.5938	Remote Similarity	NPD4732	Discontinued
0.5932	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8328	Phase 3
0.5913	Remote Similarity	NPD4211	Phase 1
0.5909	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD4193	Approved
0.5889	Remote Similarity	NPD4194	Approved
0.5889	Remote Similarity	NPD4191	Approved
0.5889	Remote Similarity	NPD4192	Approved
0.5882	Remote Similarity	NPD6435	Approved
0.5872	Remote Similarity	NPD5282	Discontinued
0.5865	Remote Similarity	NPD6893	Approved
0.5865	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD1694	Approved
0.5862	Remote Similarity	NPD6412	Phase 2
0.5856	Remote Similarity	NPD7902	Approved
0.5842	Remote Similarity	NPD4252	Approved
0.5839	Remote Similarity	NPD7266	Discontinued
0.5833	Remote Similarity	NPD7515	Phase 2
0.5825	Remote Similarity	NPD6110	Phase 1
0.5814	Remote Similarity	NPD7319	Approved
0.5794	Remote Similarity	NPD7642	Approved
0.5794	Remote Similarity	NPD6051	Approved
0.5794	Remote Similarity	NPD1695	Approved
0.5784	Remote Similarity	NPD5369	Approved
0.5776	Remote Similarity	NPD6640	Phase 3
0.5776	Remote Similarity	NPD5048	Discontinued
0.5763	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.575	Remote Similarity	NPD8297	Approved
0.5743	Remote Similarity	NPD6683	Phase 2
0.5741	Remote Similarity	NPD7136	Phase 2
0.5729	Remote Similarity	NPD7144	Approved
0.5729	Remote Similarity	NPD7143	Approved
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6926	Approved
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD6924	Approved
0.5714	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.569	Remote Similarity	NPD5909	Discontinued
0.5688	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5368	Approved
0.568	Remote Similarity	NPD7741	Discontinued
0.5678	Remote Similarity	NPD6881	Approved
0.5678	Remote Similarity	NPD6899	Approved
0.567	Remote Similarity	NPD7152	Approved
0.567	Remote Similarity	NPD7151	Approved
0.567	Remote Similarity	NPD7150	Approved
0.5667	Remote Similarity	NPD8130	Phase 1
0.5667	Remote Similarity	NPD6650	Approved
0.5667	Remote Similarity	NPD6649	Approved
0.566	Remote Similarity	NPD6422	Discontinued
0.5648	Remote Similarity	NPD5370	Suspended
0.5648	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6399	Phase 3
0.563	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6922	Approved
0.5625	Remote Similarity	NPD6923	Approved
0.562	Remote Similarity	NPD6882	Approved
0.56	Remote Similarity	NPD6933	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