NPASS Compound

Structure

NPC475332 OpenBabel07101719512D 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 4.0082 -1.0529 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 -0.5904 6.2759 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 7.5654 -0.4641 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 -0.4252 6.9117 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 -4.4355 8.8236 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 -5.3027 8.6359 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 -3.7480 8.2626 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 -2.8669 -3.9460 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 -1.3508 -2.6511 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 -8.6354 7.3753 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 -16.6733 0.5748 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 3.2831 2.4790 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 5.5715 -0.3072 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 -16.8092 -1.1519 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 -2.8669 6.9213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7074 1.4195 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 4.5746 -0.2287 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 -1.3508 5.6265 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 1 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 -8.6354 -4.4000 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 -17.2397 -0.2493 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 6.1379 0.5169 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 4.2800 2.4006 0.0000 C 0 0 3 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 -2.0579 6.3336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7105 1.4980 0.0000 C 0 0 2 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 -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 4.8464 3.2247 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 7.1349 0.4385 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 -1.4085 7.0940 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 4.1441 0.6739 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 -4.7090 7.6844 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 1 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 29 1 0 0 0 0 24 45 2 0 0 0 0 25 31 2 0 0 0 0 25 44 1 0 0 0 0 26 32 2 0 0 0 0 26 45 1 0 0 0 0 27 30 1 0 0 0 0 27 46 1 0 0 0 0 28 56 1 0 0 0 0 29 57 1 0 0 0 0 31 73 1 0 0 0 0 32 74 1 0 0 0 0 33 47 1 0 0 0 0 33 69 1 0 0 0 0 34 48 1 0 0 0 0 34 63 1 0 0 0 0 35 49 1 0 0 0 0 35 64 1 0 0 0 0 36 56 1 0 0 0 0 36 58 1 0 0 0 0 37 57 1 0 0 0 0 37 59 1 0 0 0 0 38 62 1 0 0 0 0 38 63 1 0 0 0 0 39 60 1 0 0 0 0 39 70 1 0 0 0 0 40 61 1 0 0 0 0 40 71 1 0 0 0 0 41 64 1 0 0 0 0 41 72 1 0 0 0 0 42 65 1 0 0 0 0 42 67 1 0 0 0 0 43 66 1 0 0 0 0 43 68 1 0 0 0 0 46 3 1 6 0 0 0 46 75 1 0 0 0 0 47 4 1 6 0 0 0 47 76 1 0 0 0 0 48 5 1 6 0 0 0 48 94 1 0 0 0 0 49 6 1 6 0 0 0 49 95 1 0 0 0 0 50 7 1 1 0 0 0 50 65 1 0 0 0 0 50 70 1 0 0 0 0 51 8 1 1 0 0 0 51 66 1 0 0 0 0 51 71 1 0 0 0 0 52 9 1 6 0 0 0 52 67 1 0 0 0 0 52 77 1 0 0 0 0 53 10 1 6 0 0 0 53 68 1 0 0 0 0 53 78 1 0 0 0 0 54 11 1 6 0 0 0 54 75 1 0 0 0 0 55 12 1 6 0 0 0 55 76 1 0 0 0 0 56 79 1 6 0 0 0 57 80 1 6 0 0 0 58 20 1 6 0 0 0 58 97 1 0 0 0 0 59 19 1 6 0 0 0 59 96 1 0 0 0 0 60 21 1 1 0 0 0 60 96 1 0 0 0 0 61 22 1 1 0 0 0 61 97 1 0 0 0 0 62 30 1 1 0 0 0 62 94 1 0 0 0 0 63 90 1 6 0 0 0 64 91 1 6 0 0 0 65 81 1 1 0 0 0 66 82 1 1 0 0 0 67 83 1 1 0 0 0 68 84 1 1 0 0 0 69 85 1 0 0 0 0 70 92 1 6 0 0 0 71 93 1 6 0 0 0 72 69 1 1 0 0 0 72 95 1 0 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 1 0 0 0 76 89 1 1 0 0 0 77 54 1 1 0 0 0 77 98 1 0 0 0 0 78 55 1 1 0 0 0 78 99 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1404.93
Volume:	1478.364
LogP:	6.806
LogD:	4.193
LogS:	-5.409
# 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:	8.466
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:	-5.24
MDCK Permeability:	0.00026418978814035654
Pgp-inhibitor:	1.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.988
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.783

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	67.88756561279297%
Volume Distribution (VD):	0.568
Pgp-substrate:	18.301612854003906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	3.897
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.746
Human Hepatotoxicity (H-HT):	0.996
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.991
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.637

Download Data

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

Natural Product: NPC475332

Natural Product ID:	NPC475332
*Common Name:**	Swinholide I
IUPAC Name:	n.a.
Synonyms:	Swinholide I
Standard InCHIKey:	XUQRQRKUGBIVEH-WOCFJWJXSA-N
Standard InCHI:	InChI=1S/C78H132O21/c1-44-23-28-56(79)36-58-20-18-22-61(97-58)40-71(93-16)51(8)66(82)43-68(84)53(10)78(55(12)76(89)47(4)33-69(85)72-41-64(91-14)35-49(6)95-72)99-74(87)32-26-45(2)24-29-57(80)37-59-19-17-21-60(96-59)39-70(92-15)50(7)65(81)42-67(83)52(9)77(98-73(86)31-25-44)54(11)75(88)46(3)27-30-62-38-63(90-13)34-48(5)94-62/h17-20,23-26,31-32,46-72,75-85,88-89H,21-22,27-30,33-43H2,1-16H3/b31-25+,32-26+,44-23+,45-24+/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:	CC1CC(CC(O1)CCC(C)C(C(C)C2C(C(CC(C(C(CC3CC=CC(O3)CC(CC=C(C=CC(=O)OC(C(C(CC(C(C(CC4CC=CC(O4)CC(CC=C(C=CC(=O)O2)C)O)OC)C)O)O)C)C(C)C(C(C)CC(C5CC(CC(O5)C)OC)O)O)C)O)OC)C)O)O)C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503618
PubChem CID:	44566238
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.	palau	n.a.	PMID[20078073]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	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	2
MIC	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	5.6	nM	PMID[549739]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	0.008	ug.mL-1	PMID[549739]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	62.2	ug.mL-1	PMID[549739]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	500.0	ug.mL-1	PMID[549739]

☑ 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 NPC475332 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	207
0.1-0.2	1099
0.2-0.3	3788
0.3-0.4	7207
0.4-0.5	15629
0.5-0.6	9054
0.6-0.7	5113
0.7-0.8	533
0.8-0.85	42
0.85-0.9	17
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC471324
0.9444	High Similarity	NPC206679
0.9444	High Similarity	NPC114172
0.9341	High Similarity	NPC159092
0.9341	High Similarity	NPC109406
0.9231	High Similarity	NPC476084
0.9231	High Similarity	NPC476075
0.8913	High Similarity	NPC177668
0.8878	High Similarity	NPC197736
0.8866	High Similarity	NPC57586
0.8866	High Similarity	NPC471637
0.8866	High Similarity	NPC2313
0.8866	High Similarity	NPC154132
0.8866	High Similarity	NPC475655
0.8866	High Similarity	NPC475157
0.8804	High Similarity	NPC133450
0.875	High Similarity	NPC120299
0.871	High Similarity	NPC3952
0.87	High Similarity	NPC315070
0.866	High Similarity	NPC475653
0.8646	High Similarity	NPC255410
0.8632	High Similarity	NPC256368
0.8587	High Similarity	NPC199382
0.8542	High Similarity	NPC300710
0.8454	Intermediate Similarity	NPC173329
0.8454	Intermediate Similarity	NPC288350
0.84	Intermediate Similarity	NPC473596
0.8333	Intermediate Similarity	NPC8538
0.8333	Intermediate Similarity	NPC184208
0.8247	Intermediate Similarity	NPC159698
0.8242	Intermediate Similarity	NPC477385
0.8242	Intermediate Similarity	NPC477390
0.8191	Intermediate Similarity	NPC316138
0.8191	Intermediate Similarity	NPC313658
0.8173	Intermediate Similarity	NPC193765
0.8144	Intermediate Similarity	NPC238090
0.8144	Intermediate Similarity	NPC472195
0.8144	Intermediate Similarity	NPC472196
0.8132	Intermediate Similarity	NPC315731
0.8111	Intermediate Similarity	NPC139712
0.81	Intermediate Similarity	NPC65700
0.8095	Intermediate Similarity	NPC133625
0.8085	Intermediate Similarity	NPC311163
0.8022	Intermediate Similarity	NPC133226
0.8022	Intermediate Similarity	NPC470147
0.8	Intermediate Similarity	NPC473807
0.7981	Intermediate Similarity	NPC476740
0.7981	Intermediate Similarity	NPC476738
0.7979	Intermediate Similarity	NPC471494
0.7957	Intermediate Similarity	NPC44261
0.7921	Intermediate Similarity	NPC203627
0.7912	Intermediate Similarity	NPC180725
0.7912	Intermediate Similarity	NPC470149
0.7912	Intermediate Similarity	NPC470148
0.7895	Intermediate Similarity	NPC477389
0.7895	Intermediate Similarity	NPC477387
0.7895	Intermediate Similarity	NPC186332
0.7895	Intermediate Similarity	NPC47220
0.7889	Intermediate Similarity	NPC474026
0.7879	Intermediate Similarity	NPC469491
0.7864	Intermediate Similarity	NPC201191
0.7857	Intermediate Similarity	NPC110072
0.7835	Intermediate Similarity	NPC285588
0.7812	Intermediate Similarity	NPC477386
0.7812	Intermediate Similarity	NPC477388
0.781	Intermediate Similarity	NPC29389
0.781	Intermediate Similarity	NPC265502
0.781	Intermediate Similarity	NPC469960
0.781	Intermediate Similarity	NPC93026
0.7802	Intermediate Similarity	NPC248775
0.7788	Intermediate Similarity	NPC474581
0.7788	Intermediate Similarity	NPC475367
0.7788	Intermediate Similarity	NPC473816
0.7788	Intermediate Similarity	NPC309398
0.7778	Intermediate Similarity	NPC469880
0.7767	Intermediate Similarity	NPC169365
0.7767	Intermediate Similarity	NPC197447
0.7745	Intermediate Similarity	NPC161855
0.7745	Intermediate Similarity	NPC308567
0.7745	Intermediate Similarity	NPC83895
0.7745	Intermediate Similarity	NPC187761
0.7745	Intermediate Similarity	NPC255592
0.7745	Intermediate Similarity	NPC261377
0.7742	Intermediate Similarity	NPC474894
0.7736	Intermediate Similarity	NPC472263
0.7736	Intermediate Similarity	NPC469959
0.7736	Intermediate Similarity	NPC108682
0.7736	Intermediate Similarity	NPC469957
0.7723	Intermediate Similarity	NPC472995
0.7708	Intermediate Similarity	NPC208473
0.7708	Intermediate Similarity	NPC61527
0.7692	Intermediate Similarity	NPC475711
0.7684	Intermediate Similarity	NPC266718
0.767	Intermediate Similarity	NPC475053
0.7667	Intermediate Similarity	NPC327041
0.7667	Intermediate Similarity	NPC285840
0.7664	Intermediate Similarity	NPC475263
0.7652	Intermediate Similarity	NPC219804
0.7647	Intermediate Similarity	NPC40812
0.7642	Intermediate Similarity	NPC82251
0.7629	Intermediate Similarity	NPC118077
0.7629	Intermediate Similarity	NPC475186
0.7624	Intermediate Similarity	NPC170204
0.7624	Intermediate Similarity	NPC272050
0.7615	Intermediate Similarity	NPC126897
0.7615	Intermediate Similarity	NPC297945
0.7604	Intermediate Similarity	NPC242233
0.76	Intermediate Similarity	NPC320552
0.7593	Intermediate Similarity	NPC313668
0.7593	Intermediate Similarity	NPC315836
0.7576	Intermediate Similarity	NPC202886
0.7576	Intermediate Similarity	NPC327253
0.757	Intermediate Similarity	NPC473586
0.7556	Intermediate Similarity	NPC107654
0.7549	Intermediate Similarity	NPC472997
0.7549	Intermediate Similarity	NPC472996
0.7549	Intermediate Similarity	NPC473291
0.7545	Intermediate Similarity	NPC470025
0.7545	Intermediate Similarity	NPC328074
0.7545	Intermediate Similarity	NPC321272
0.7545	Intermediate Similarity	NPC317460
0.7545	Intermediate Similarity	NPC241477
0.7527	Intermediate Similarity	NPC1180
0.7525	Intermediate Similarity	NPC294293
0.7525	Intermediate Similarity	NPC71589
0.7525	Intermediate Similarity	NPC472198
0.7523	Intermediate Similarity	NPC316708
0.7521	Intermediate Similarity	NPC179261
0.75	Intermediate Similarity	NPC78673
0.75	Intermediate Similarity	NPC477203
0.75	Intermediate Similarity	NPC473308
0.75	Intermediate Similarity	NPC477749
0.75	Intermediate Similarity	NPC160517
0.75	Intermediate Similarity	NPC186155
0.7477	Intermediate Similarity	NPC470027
0.7477	Intermediate Similarity	NPC473159
0.7477	Intermediate Similarity	NPC88349
0.7477	Intermediate Similarity	NPC101400
0.7477	Intermediate Similarity	NPC101965
0.7475	Intermediate Similarity	NPC477748
0.7474	Intermediate Similarity	NPC10080
0.7474	Intermediate Similarity	NPC251026
0.7474	Intermediate Similarity	NPC123908
0.7456	Intermediate Similarity	NPC470914
0.7455	Intermediate Similarity	NPC470026
0.7455	Intermediate Similarity	NPC17791
0.7455	Intermediate Similarity	NPC71680
0.7451	Intermediate Similarity	NPC36954
0.7451	Intermediate Similarity	NPC469583
0.7451	Intermediate Similarity	NPC469543
0.7444	Intermediate Similarity	NPC327383
0.7444	Intermediate Similarity	NPC185186
0.7444	Intermediate Similarity	NPC329914
0.7429	Intermediate Similarity	NPC198992
0.7429	Intermediate Similarity	NPC11974
0.7426	Intermediate Similarity	NPC320089
0.7426	Intermediate Similarity	NPC476300
0.7426	Intermediate Similarity	NPC476049
0.7411	Intermediate Similarity	NPC305044
0.7411	Intermediate Similarity	NPC265290
0.7407	Intermediate Similarity	NPC109376
0.74	Intermediate Similarity	NPC313670
0.74	Intermediate Similarity	NPC473448
0.7396	Intermediate Similarity	NPC473315
0.7396	Intermediate Similarity	NPC231601
0.7396	Intermediate Similarity	NPC142111
0.7391	Intermediate Similarity	NPC135369
0.7391	Intermediate Similarity	NPC477202
0.7387	Intermediate Similarity	NPC313921
0.7387	Intermediate Similarity	NPC98038
0.7383	Intermediate Similarity	NPC470768
0.7379	Intermediate Similarity	NPC57664
0.7374	Intermediate Similarity	NPC248312
0.7368	Intermediate Similarity	NPC469469
0.7368	Intermediate Similarity	NPC470515
0.7364	Intermediate Similarity	NPC177047
0.7364	Intermediate Similarity	NPC181298
0.7364	Intermediate Similarity	NPC15551
0.7363	Intermediate Similarity	NPC315843
0.7358	Intermediate Similarity	NPC11956
0.7353	Intermediate Similarity	NPC477348
0.7353	Intermediate Similarity	NPC238264
0.7353	Intermediate Similarity	NPC477345
0.7347	Intermediate Similarity	NPC47937
0.7347	Intermediate Similarity	NPC164393
0.7345	Intermediate Similarity	NPC207637
0.734	Intermediate Similarity	NPC86971
0.734	Intermediate Similarity	NPC471537
0.7339	Intermediate Similarity	NPC219900
0.7339	Intermediate Similarity	NPC470024
0.7339	Intermediate Similarity	NPC224660
0.7339	Intermediate Similarity	NPC392
0.7339	Intermediate Similarity	NPC177524
0.7333	Intermediate Similarity	NPC475762
0.7333	Intermediate Similarity	NPC13743
0.7333	Intermediate Similarity	NPC98813
0.7333	Intermediate Similarity	NPC79631
0.7328	Intermediate Similarity	NPC476204
0.7328	Intermediate Similarity	NPC170084
0.7327	Intermediate Similarity	NPC472197

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 NPC475332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1196
0.2-0.3	3526
0.3-0.4	2707
0.4-0.5	1126
0.5-0.6	334
0.6-0.7	78
0.7-0.8	8
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD7838	Discovery
0.8283	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD6698	Approved
0.7938	Intermediate Similarity	NPD46	Approved
0.7615	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7983	Approved
0.7429	Intermediate Similarity	NPD5344	Discontinued
0.7339	Intermediate Similarity	NPD6686	Approved
0.7333	Intermediate Similarity	NPD6648	Approved
0.7328	Intermediate Similarity	NPD7503	Approved
0.7179	Intermediate Similarity	NPD8513	Phase 3
0.7034	Intermediate Similarity	NPD8515	Approved
0.7034	Intermediate Similarity	NPD8516	Approved
0.7034	Intermediate Similarity	NPD8517	Approved
0.7034	Intermediate Similarity	NPD8033	Approved
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6937	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7829	Approved
0.6917	Remote Similarity	NPD7830	Approved
0.6891	Remote Similarity	NPD8379	Approved
0.6891	Remote Similarity	NPD8335	Approved
0.6891	Remote Similarity	NPD8296	Approved
0.6891	Remote Similarity	NPD8378	Approved
0.6891	Remote Similarity	NPD8380	Approved
0.678	Remote Similarity	NPD7327	Approved
0.678	Remote Similarity	NPD7328	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6759	Remote Similarity	NPD4225	Approved
0.6729	Remote Similarity	NPD7839	Suspended
0.6723	Remote Similarity	NPD7516	Approved
0.6638	Remote Similarity	NPD6053	Discontinued
0.6635	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6101	Approved
0.6634	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD8448	Approved
0.6609	Remote Similarity	NPD6371	Approved
0.6606	Remote Similarity	NPD7638	Approved
0.6555	Remote Similarity	NPD7505	Discontinued
0.6555	Remote Similarity	NPD7115	Discovery
0.6545	Remote Similarity	NPD7639	Approved
0.6545	Remote Similarity	NPD7640	Approved
0.6532	Remote Similarity	NPD8451	Approved
0.6509	Remote Similarity	NPD6411	Approved
0.6509	Remote Similarity	NPD7637	Suspended
0.6475	Remote Similarity	NPD8444	Approved
0.6457	Remote Similarity	NPD8392	Approved
0.6457	Remote Similarity	NPD8391	Approved
0.6457	Remote Similarity	NPD8390	Approved
0.6442	Remote Similarity	NPD7524	Approved
0.6441	Remote Similarity	NPD8133	Approved
0.64	Remote Similarity	NPD8273	Phase 1
0.64	Remote Similarity	NPD7507	Approved
0.6371	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD7641	Discontinued
0.6348	Remote Similarity	NPD6412	Phase 2
0.632	Remote Similarity	NPD8340	Approved
0.632	Remote Similarity	NPD8342	Approved
0.632	Remote Similarity	NPD8341	Approved
0.632	Remote Similarity	NPD8299	Approved
0.6311	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4251	Approved
0.6286	Remote Similarity	NPD4250	Approved
0.6279	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD7319	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6695	Phase 3
0.6214	Remote Similarity	NPD7154	Phase 3
0.619	Remote Similarity	NPD4249	Approved
0.6182	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7750	Discontinued
0.6131	Remote Similarity	NPD7266	Discontinued
0.6129	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7642	Approved
0.6111	Remote Similarity	NPD5785	Approved
0.6102	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8297	Approved
0.6078	Remote Similarity	NPD4821	Approved
0.6078	Remote Similarity	NPD4819	Approved
0.6078	Remote Similarity	NPD4822	Approved
0.6078	Remote Similarity	NPD4820	Approved
0.6061	Remote Similarity	NPD8039	Approved
0.605	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4271	Approved
0.604	Remote Similarity	NPD4268	Approved
0.6017	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7500	Approved
0.6016	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.5982	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6929	Approved
0.5962	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5209	Approved
0.5946	Remote Similarity	NPD5282	Discontinued
0.5946	Remote Similarity	NPD7748	Approved
0.5943	Remote Similarity	NPD5363	Approved
0.5929	Remote Similarity	NPD7902	Approved
0.5922	Remote Similarity	NPD6930	Phase 2
0.5922	Remote Similarity	NPD6931	Approved
0.5922	Remote Similarity	NPD7514	Phase 3
0.5922	Remote Similarity	NPD7332	Phase 2
0.5905	Remote Similarity	NPD5362	Discontinued
0.5905	Remote Similarity	NPD6110	Phase 1
0.5902	Remote Similarity	NPD4632	Approved
0.59	Remote Similarity	NPD8264	Approved
0.5896	Remote Similarity	NPD8415	Approved
0.5882	Remote Similarity	NPD7145	Approved
0.5872	Remote Similarity	NPD1695	Approved
0.5865	Remote Similarity	NPD6845	Suspended
0.5865	Remote Similarity	NPD6902	Approved
0.5852	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6640	Phase 3
0.5842	Remote Similarity	NPD6933	Approved
0.581	Remote Similarity	NPD6435	Approved
0.5802	Remote Similarity	NPD7736	Approved
0.5798	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD1694	Approved
0.5785	Remote Similarity	NPD6421	Discontinued
0.5784	Remote Similarity	NPD5776	Phase 2
0.5784	Remote Similarity	NPD6932	Approved
0.5784	Remote Similarity	NPD6925	Approved
0.5781	Remote Similarity	NPD5125	Phase 3
0.5781	Remote Similarity	NPD5126	Approved
0.5781	Remote Similarity	NPD8080	Discontinued
0.5769	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7087	Discontinued
0.5766	Remote Similarity	NPD7515	Phase 2
0.5766	Remote Similarity	NPD5124	Phase 1
0.576	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5332	Approved
0.5755	Remote Similarity	NPD5331	Approved
0.575	Remote Similarity	NPD6899	Approved
0.575	Remote Similarity	NPD6881	Approved
0.5738	Remote Similarity	NPD6650	Approved
0.5738	Remote Similarity	NPD6649	Approved
0.5738	Remote Similarity	NPD8130	Phase 1
0.5727	Remote Similarity	NPD6051	Approved
0.5724	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4211	Phase 1
0.5714	Remote Similarity	NPD4790	Discontinued
0.5714	Remote Similarity	NPD6399	Phase 3
0.5692	Remote Similarity	NPD7492	Approved
0.5691	Remote Similarity	NPD6882	Approved
0.5678	Remote Similarity	NPD6647	Phase 2
0.5676	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.567	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5697	Approved
0.5667	Remote Similarity	NPD6685	Approved
0.5664	Remote Similarity	NPD7900	Approved
0.5664	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4270	Approved
0.566	Remote Similarity	NPD4269	Approved
0.5656	Remote Similarity	NPD6883	Approved
0.5656	Remote Similarity	NPD7290	Approved
0.5656	Remote Similarity	NPD7102	Approved
0.5652	Remote Similarity	NPD6083	Phase 2
0.5652	Remote Similarity	NPD6084	Phase 2
0.5649	Remote Similarity	NPD6616	Approved
0.5648	Remote Similarity	NPD6893	Approved
0.5644	Remote Similarity	NPD6924	Approved
0.5644	Remote Similarity	NPD6926	Approved
0.5635	Remote Similarity	NPD6009	Approved
0.5631	Remote Similarity	NPD4756	Discovery
0.5625	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6054	Approved
0.5625	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5368	Approved
0.5615	Remote Similarity	NPD7604	Phase 2
0.561	Remote Similarity	NPD6869	Approved
0.561	Remote Similarity	NPD6847	Approved
0.561	Remote Similarity	NPD6617	Approved
0.5606	Remote Similarity	NPD7078	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