NPASS Compound

Structure

NPC159092 OpenBabel07101718312D 96100 0 0 1 0 0 0 0 0999 V2000 7.3286 10.3854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1537 7.0241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1679 -0.6782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9794 -2.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.1144 5.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3640 0.3218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9684 0.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0593 5.9551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5977 5.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9331 1.3755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4453 7.3092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4358 -0.6782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.6841 1.8728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4980 3.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2741 0.0728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4580 6.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5587 9.7840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7559 -2.6820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4348 9.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8689 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1212 9.0123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3144 -1.9928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9979 9.7574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8445 9.0074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3953 -1.7606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7610 5.4020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0339 0.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0073 9.8948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3497 -2.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6975 5.7527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8999 0.3218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6503 8.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.0133 3.8455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4980 1.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0263 9.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3399 -2.1689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.3048 4.1306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7660 1.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2049 7.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8958 -0.4908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6712 3.0175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3787 3.6823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9523 9.4589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9891 6.0378 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1679 0.3218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5031 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1779 4.8319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4980 0.8218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0762 1.1152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1049 5.6566 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.6163 5.0099 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9966 1.7261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2807 6.3228 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4358 0.3218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0077 9.8672 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3402 -2.1964 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0897 9.3249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3213 -1.9772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4518 8.1891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1239 -1.1265 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 15.4694 5.1169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7660 0.8218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 16.0768 3.4949 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6320 2.3218 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4525 2.0417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3236 4.6808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7263 4.0160 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2687 2.6884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5525 0.2633 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7286 6.5831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3476 7.6983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0526 5.6871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3019 0.8218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3442 5.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5698 0.8218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6973 -0.7168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8977 10.8611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2852 -3.1949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4069 1.7432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3141 4.8182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7259 4.0436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2501 2.4967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1195 8.3341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8880 4.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3019 1.8218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0405 -1.4709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.9122 2.5085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6320 3.3218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3583 -0.3289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6209 7.0346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.4060 5.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6320 0.3218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2237 8.8249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2578 -1.6265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9174 6.8766 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 43 1 0 0 0 0 4 46 1 0 0 0 0 13 87 1 0 0 0 0 14 88 1 0 0 0 0 15 89 1 0 0 0 0 16 90 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 43 2 0 0 0 0 24 32 2 0 0 0 0 24 43 1 0 0 0 0 25 29 1 0 0 0 0 25 46 2 0 0 0 0 26 30 1 0 0 0 0 26 44 1 0 0 0 0 27 31 1 0 0 0 0 27 45 1 0 0 0 0 28 55 1 0 0 0 0 29 56 1 0 0 0 0 32 71 1 0 0 0 0 33 47 1 0 0 0 0 33 63 1 0 0 0 0 34 48 1 0 0 0 0 34 64 1 0 0 0 0 35 55 1 0 0 0 0 35 57 1 0 0 0 0 36 56 1 0 0 0 0 36 58 1 0 0 0 0 37 61 1 0 0 0 0 37 63 1 0 0 0 0 38 62 1 0 0 0 0 38 64 1 0 0 0 0 39 59 1 0 0 0 0 39 70 1 0 0 0 0 40 60 1 0 0 0 0 40 69 1 0 0 0 0 41 65 1 0 0 0 0 41 67 1 0 0 0 0 42 66 1 0 0 0 0 42 68 1 0 0 0 0 44 2 1 1 0 0 0 44 72 1 0 0 0 0 45 3 1 1 0 0 0 45 73 1 0 0 0 0 46 76 1 0 0 0 0 47 5 1 1 0 0 0 47 91 1 0 0 0 0 48 6 1 1 0 0 0 48 92 1 0 0 0 0 49 7 1 6 0 0 0 49 65 1 0 0 0 0 49 69 1 0 0 0 0 50 8 1 6 0 0 0 50 66 1 0 0 0 0 50 70 1 0 0 0 0 51 9 1 1 0 0 0 51 67 1 0 0 0 0 51 74 1 0 0 0 0 52 10 1 1 0 0 0 52 68 1 0 0 0 0 52 75 1 0 0 0 0 53 11 1 1 0 0 0 53 72 1 0 0 0 0 54 12 1 1 0 0 0 54 73 1 0 0 0 0 55 77 1 1 0 0 0 56 78 1 1 0 0 0 57 19 1 1 0 0 0 57 93 1 0 0 0 0 58 20 1 1 0 0 0 58 94 1 0 0 0 0 59 21 1 6 0 0 0 59 93 1 0 0 0 0 60 22 1 6 0 0 0 60 94 1 0 0 0 0 61 30 1 6 0 0 0 61 91 1 0 0 0 0 62 31 1 6 0 0 0 62 92 1 0 0 0 0 63 87 1 1 0 0 0 64 88 1 1 0 0 0 65 79 1 6 0 0 0 66 80 1 6 0 0 0 67 81 1 6 0 0 0 68 82 1 6 0 0 0 69 89 1 1 0 0 0 70 90 1 1 0 0 0 71 83 2 0 0 0 0 71 95 1 0 0 0 0 72 84 1 6 0 0 0 73 85 1 6 0 0 0 74 53 1 6 0 0 0 74 95 1 0 0 0 0 75 54 1 6 0 0 0 75 96 1 0 0 0 0 76 86 2 0 0 0 0 76 96 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1362.92
Volume:	1437.618
LogP:	7.292
LogD:	4.332
LogS:	-5.392
# Rotatable Bonds:	16
TPSA:	288.28
# H-Bond Aceptor:	20
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.053
Synthetic Accessibility Score:	8.368
Fsp3:	0.842
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:	-5.161
MDCK Permeability:	0.0003474639670457691
Pgp-inhibitor:	1.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.812
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	70.20291900634766%
Volume Distribution (VD):	0.702
Pgp-substrate:	20.634458541870117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	4.222
Half-life (T1/2):	0.009

ADMET: Toxicity

hERG Blockers:	0.652
Human Hepatotoxicity (H-HT):	0.997
Drug-inuced Liver Injury (DILI):	0.306
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.979
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.658

Download Data

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

Natural Product: NPC159092

Natural Product ID:	NPC159092
*Common Name:**	Hurghadolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PBOKTYWXRURPFG-ZHYZYMJSSA-N
Standard InCHI:	InChI=1S/C76H130O20/c1-43-23-28-55(77)35-57-19-17-21-59(93-57)39-70(90-16)50(8)66(80)42-68(82)52(10)75(54(12)73(85)45(3)27-31-62-38-64(88-14)34-48(6)92-62)96-76(86)46(4)25-29-56(78)36-58-20-18-22-60(94-58)40-69(89-15)49(7)65(79)41-67(81)51(9)74(95-71(83)32-24-43)53(11)72(84)44(2)26-30-61-37-63(87-13)33-47(5)91-61/h17-20,23-25,32,44-45,47-70,72-75,77-82,84-85H,21-22,26-31,33-42H2,1-16H3/b32-24+,43-23+,46-25+/t44-,45-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63+,64+,65-,66-,67+,68+,69-,70-,72-,73-,74-,75-/m0/s1
SMILES:	C/C/1=CC[C@@H](C[C@@H]2C=CC[C@@H](C[C@@H]([C@@H](C)[C@H](C[C@H]([C@H](C)[C@@H]([C@@H](C)[C@H]([C@@H](C)CC[C@H]3C[C@@H](C[C@H](C)O3)OC)O)OC(=O)/C(=C/C[C@@H](C[C@@H]3C=CC[C@@H](C[C@@H]([C@@H](C)[C@H](C[C@H]([C@H](C)[C@@H]([C@@H](C)[C@H]([C@@H](C)CC[C@H]4C[C@@H](C[C@H](C)O4)OC)O)OC(=O)C=C1)O)O)OC)O3)O)/C)O)O)OC)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500428
PubChem CID:	44566239
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	=	365.0	nM	PMID[496316]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	0.5	ug.mL-1	PMID[496316]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	31.3	ug.mL-1	PMID[496316]

☑ 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 NPC159092 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	189
0.1-0.2	994
0.2-0.3	3856
0.3-0.4	7700
0.4-0.5	15993
0.5-0.6	9148
0.6-0.7	4406
0.7-0.8	366
0.8-0.85	22
0.85-0.9	15
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	NPC109406
0.9655	High Similarity	NPC476084
0.9655	High Similarity	NPC476075
0.9341	High Similarity	NPC475332
0.8977	High Similarity	NPC199382
0.8721	High Similarity	NPC8538
0.8721	High Similarity	NPC184208
0.871	High Similarity	NPC300710
0.8617	High Similarity	NPC255410
0.8556	High Similarity	NPC316138
0.8556	High Similarity	NPC313658
0.8526	High Similarity	NPC120299
0.8506	High Similarity	NPC315731
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
0.8444	Intermediate Similarity	NPC186332
0.8444	Intermediate Similarity	NPC47220
0.8438	Intermediate Similarity	NPC475653
0.828	Intermediate Similarity	NPC177668
0.8182	Intermediate Similarity	NPC473596
0.8172	Intermediate Similarity	NPC133450
0.814	Intermediate Similarity	NPC469880
0.8132	Intermediate Similarity	NPC242233
0.8119	Intermediate Similarity	NPC315070
0.8085	Intermediate Similarity	NPC3952
0.8041	Intermediate Similarity	NPC173329
0.8041	Intermediate Similarity	NPC288350
0.8023	Intermediate Similarity	NPC285840
0.8023	Intermediate Similarity	NPC327041
0.8021	Intermediate Similarity	NPC159698
0.8021	Intermediate Similarity	NPC256368
0.8	Intermediate Similarity	NPC123908
0.8	Intermediate Similarity	NPC10080
0.7961	Intermediate Similarity	NPC193765
0.7917	Intermediate Similarity	NPC238090
0.7917	Intermediate Similarity	NPC472196
0.7917	Intermediate Similarity	NPC472195
0.7879	Intermediate Similarity	NPC203627
0.7841	Intermediate Similarity	NPC477203
0.7791	Intermediate Similarity	NPC329914
0.7791	Intermediate Similarity	NPC185186
0.7791	Intermediate Similarity	NPC327383
0.7788	Intermediate Similarity	NPC473807
0.7767	Intermediate Similarity	NPC476738
0.7767	Intermediate Similarity	NPC476740
0.7745	Intermediate Similarity	NPC474581
0.7745	Intermediate Similarity	NPC475367
0.7745	Intermediate Similarity	NPC473816
0.7742	Intermediate Similarity	NPC471494
0.7732	Intermediate Similarity	NPC476049
0.7727	Intermediate Similarity	NPC477202
0.7717	Intermediate Similarity	NPC44261
0.7717	Intermediate Similarity	NPC16488
0.766	Intermediate Similarity	NPC316426
0.766	Intermediate Similarity	NPC61527
0.766	Intermediate Similarity	NPC315395
0.7647	Intermediate Similarity	NPC201191
0.764	Intermediate Similarity	NPC315394
0.7629	Intermediate Similarity	NPC110072
0.7609	Intermediate Similarity	NPC477390
0.7609	Intermediate Similarity	NPC477385
0.7604	Intermediate Similarity	NPC285588
0.7586	Intermediate Similarity	NPC477085
0.7586	Intermediate Similarity	NPC329890
0.7582	Intermediate Similarity	NPC133226
0.7582	Intermediate Similarity	NPC470147
0.7579	Intermediate Similarity	NPC86005
0.7579	Intermediate Similarity	NPC477959
0.7576	Intermediate Similarity	NPC272050
0.7573	Intermediate Similarity	NPC309398
0.7558	Intermediate Similarity	NPC476012
0.7553	Intermediate Similarity	NPC92633
0.7547	Intermediate Similarity	NPC133625
0.7528	Intermediate Similarity	NPC188860
0.7527	Intermediate Similarity	NPC185949
0.7527	Intermediate Similarity	NPC107498
0.7525	Intermediate Similarity	NPC308567
0.7525	Intermediate Similarity	NPC161855
0.7525	Intermediate Similarity	NPC65700
0.7525	Intermediate Similarity	NPC261377
0.7525	Intermediate Similarity	NPC255592
0.75	Intermediate Similarity	NPC473291
0.75	Intermediate Similarity	NPC477204
0.7475	Intermediate Similarity	NPC469491
0.7474	Intermediate Similarity	NPC311163
0.7474	Intermediate Similarity	NPC164393
0.7473	Intermediate Similarity	NPC180725
0.7473	Intermediate Similarity	NPC470148
0.7473	Intermediate Similarity	NPC470149
0.7471	Intermediate Similarity	NPC477087
0.7471	Intermediate Similarity	NPC477086
0.7471	Intermediate Similarity	NPC316185
0.7451	Intermediate Similarity	NPC475053
0.7447	Intermediate Similarity	NPC186155
0.7447	Intermediate Similarity	NPC78673
0.7447	Intermediate Similarity	NPC160517
0.7444	Intermediate Similarity	NPC474026
0.7444	Intermediate Similarity	NPC233071
0.7444	Intermediate Similarity	NPC84360
0.7444	Intermediate Similarity	NPC475711
0.7442	Intermediate Similarity	NPC101622
0.7423	Intermediate Similarity	NPC212598
0.74	Intermediate Similarity	NPC170204
0.7396	Intermediate Similarity	NPC118077
0.7396	Intermediate Similarity	NPC471055
0.7396	Intermediate Similarity	NPC471056
0.7396	Intermediate Similarity	NPC475186
0.7374	Intermediate Similarity	NPC162615
0.7374	Intermediate Similarity	NPC320552
0.7374	Intermediate Similarity	NPC205034
0.7374	Intermediate Similarity	NPC152778
0.7363	Intermediate Similarity	NPC248775
0.7358	Intermediate Similarity	NPC109376
0.7356	Intermediate Similarity	NPC476037
0.7356	Intermediate Similarity	NPC4299
0.7353	Intermediate Similarity	NPC83895
0.7353	Intermediate Similarity	NPC187761
0.7347	Intermediate Similarity	NPC313670
0.7347	Intermediate Similarity	NPC327253
0.7327	Intermediate Similarity	NPC16967
0.7327	Intermediate Similarity	NPC472995
0.7312	Intermediate Similarity	NPC112868
0.7303	Intermediate Similarity	NPC107654
0.7303	Intermediate Similarity	NPC315843
0.73	Intermediate Similarity	NPC294293
0.7292	Intermediate Similarity	NPC208473
0.7292	Intermediate Similarity	NPC477389
0.7292	Intermediate Similarity	NPC477387
0.7292	Intermediate Similarity	NPC122502
0.729	Intermediate Similarity	NPC475263
0.729	Intermediate Similarity	NPC224660
0.729	Intermediate Similarity	NPC470024
0.7283	Intermediate Similarity	NPC477088
0.7283	Intermediate Similarity	NPC471537
0.7282	Intermediate Similarity	NPC227865
0.7273	Intermediate Similarity	NPC477749
0.7264	Intermediate Similarity	NPC218158
0.7264	Intermediate Similarity	NPC93026
0.7264	Intermediate Similarity	NPC82251
0.7264	Intermediate Similarity	NPC29389
0.7264	Intermediate Similarity	NPC265502
0.7264	Intermediate Similarity	NPC469960
0.7264	Intermediate Similarity	NPC172867
0.7263	Intermediate Similarity	NPC266718
0.7255	Intermediate Similarity	NPC40812
0.7248	Intermediate Similarity	NPC21713
0.7248	Intermediate Similarity	NPC297945
0.7248	Intermediate Similarity	NPC126897
0.7248	Intermediate Similarity	NPC475608
0.7241	Intermediate Similarity	NPC151481
0.7234	Intermediate Similarity	NPC224455
0.7228	Intermediate Similarity	NPC281134
0.7228	Intermediate Similarity	NPC469543
0.7222	Intermediate Similarity	NPC313668
0.7222	Intermediate Similarity	NPC315836
0.7216	Intermediate Similarity	NPC477386
0.7216	Intermediate Similarity	NPC477388
0.7212	Intermediate Similarity	NPC197447
0.7212	Intermediate Similarity	NPC169365
0.7212	Intermediate Similarity	NPC477717
0.72	Intermediate Similarity	NPC320089
0.72	Intermediate Similarity	NPC478036
0.72	Intermediate Similarity	NPC478037
0.7196	Intermediate Similarity	NPC473586
0.7196	Intermediate Similarity	NPC469959
0.7196	Intermediate Similarity	NPC469957
0.7196	Intermediate Similarity	NPC472263
0.7196	Intermediate Similarity	NPC108682
0.7188	Intermediate Similarity	NPC471223
0.7188	Intermediate Similarity	NPC67081
0.7184	Intermediate Similarity	NPC92275
0.7182	Intermediate Similarity	NPC241477
0.7172	Intermediate Similarity	NPC182136
0.7172	Intermediate Similarity	NPC310479
0.7172	Intermediate Similarity	NPC202886
0.7172	Intermediate Similarity	NPC475855
0.7172	Intermediate Similarity	NPC473448
0.717	Intermediate Similarity	NPC469869
0.7159	Intermediate Similarity	NPC469660
0.7158	Intermediate Similarity	NPC170377
0.7158	Intermediate Similarity	NPC263087
0.7158	Intermediate Similarity	NPC2379
0.7158	Intermediate Similarity	NPC106912
0.7158	Intermediate Similarity	NPC31019
0.7158	Intermediate Similarity	NPC27314
0.7158	Intermediate Similarity	NPC474809
0.7158	Intermediate Similarity	NPC116543
0.7157	Intermediate Similarity	NPC180722
0.7157	Intermediate Similarity	NPC195645
0.7157	Intermediate Similarity	NPC165332
0.7157	Intermediate Similarity	NPC472997

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 NPC159092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1098
0.2-0.3	3489
0.3-0.4	2855
0.4-0.5	1126
0.5-0.6	333
0.6-0.7	80
0.7-0.8	5
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
0.828	Intermediate Similarity	NPD7838	Discovery
0.8247	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6698	Approved
0.7708	Intermediate Similarity	NPD46	Approved
0.7273	Intermediate Similarity	NPD7983	Approved
0.7248	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7839	Suspended
0.703	Intermediate Similarity	NPD5778	Approved
0.703	Intermediate Similarity	NPD5779	Approved
0.6983	Remote Similarity	NPD8513	Phase 3
0.6972	Remote Similarity	NPD6686	Approved
0.6952	Remote Similarity	NPD6648	Approved
0.6931	Remote Similarity	NPD7637	Suspended
0.6907	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6101	Approved
0.69	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5344	Discontinued
0.6857	Remote Similarity	NPD7638	Approved
0.6838	Remote Similarity	NPD8517	Approved
0.6838	Remote Similarity	NPD8515	Approved
0.6838	Remote Similarity	NPD7503	Approved
0.6838	Remote Similarity	NPD8516	Approved
0.6792	Remote Similarity	NPD7639	Approved
0.6792	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD6411	Approved
0.6726	Remote Similarity	NPD6053	Discontinued
0.6723	Remote Similarity	NPD7830	Approved
0.6723	Remote Similarity	NPD7829	Approved
0.6633	Remote Similarity	NPD7154	Phase 3
0.6577	Remote Similarity	NPD7899	Clinical (unspecified phase)
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)
0.6489	Remote Similarity	NPD8039	Approved
0.6471	Remote Similarity	NPD8294	Approved
0.6471	Remote Similarity	NPD8377	Approved
0.6436	Remote Similarity	NPD4249	Approved
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)
0.6364	Remote Similarity	NPD5209	Approved
0.6356	Remote Similarity	NPD7115	Discovery
0.6337	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5363	Approved
0.6327	Remote Similarity	NPD4820	Approved
0.6327	Remote Similarity	NPD4819	Approved
0.6327	Remote Similarity	NPD4821	Approved
0.6327	Remote Similarity	NPD4822	Approved
0.6303	Remote Similarity	NPD7328	Approved
0.6303	Remote Similarity	NPD7327	Approved
0.63	Remote Similarity	NPD6695	Phase 3
0.63	Remote Similarity	NPD5362	Discontinued
0.629	Remote Similarity	NPD8448	Approved
0.6289	Remote Similarity	NPD4271	Approved
0.6289	Remote Similarity	NPD4268	Approved
0.6281	Remote Similarity	NPD8444	Approved
0.6262	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD7516	Approved
0.6238	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7632	Discontinued
0.6214	Remote Similarity	NPD7750	Discontinued
0.621	Remote Similarity	NPD8451	Approved
0.62	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7748	Approved
0.6167	Remote Similarity	NPD7641	Discontinued
0.6162	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7514	Phase 3
0.6162	Remote Similarity	NPD7332	Phase 2
0.6146	Remote Similarity	NPD8264	Approved
0.6142	Remote Similarity	NPD8390	Approved
0.6142	Remote Similarity	NPD8391	Approved
0.6142	Remote Similarity	NPD8392	Approved
0.6139	Remote Similarity	NPD5331	Approved
0.6139	Remote Similarity	NPD5332	Approved
0.6122	Remote Similarity	NPD7145	Approved
0.6111	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8133	Approved
0.61	Remote Similarity	NPD6902	Approved
0.61	Remote Similarity	NPD4790	Discontinued
0.6094	Remote Similarity	NPD7260	Phase 2
0.6087	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7505	Discontinued
0.608	Remote Similarity	NPD7507	Approved
0.608	Remote Similarity	NPD8273	Phase 1
0.6061	Remote Similarity	NPD6929	Approved
0.6058	Remote Similarity	NPD7524	Approved
0.6048	Remote Similarity	NPD8328	Phase 3
0.604	Remote Similarity	NPD6435	Approved
0.604	Remote Similarity	NPD4270	Approved
0.604	Remote Similarity	NPD4269	Approved
0.602	Remote Similarity	NPD4756	Discovery
0.602	Remote Similarity	NPD6925	Approved
0.602	Remote Similarity	NPD5776	Phase 2
0.602	Remote Similarity	NPD6932	Approved
0.6019	Remote Similarity	NPD5282	Discontinued
0.6019	Remote Similarity	NPD1694	Approved
0.6018	Remote Similarity	NPD6647	Phase 2
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD6931	Approved
0.5985	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7515	Phase 2
0.5962	Remote Similarity	NPD5786	Approved
0.596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.595	Remote Similarity	NPD7500	Approved
0.5943	Remote Similarity	NPD1695	Approved
0.5941	Remote Similarity	NPD5369	Approved
0.594	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.594	Remote Similarity	NPD5124	Phase 1
0.5938	Remote Similarity	NPD7319	Approved
0.5932	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7642	Approved
0.5913	Remote Similarity	NPD4211	Phase 1
0.5897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8297	Approved
0.5856	Remote Similarity	NPD6084	Phase 2
0.5856	Remote Similarity	NPD6083	Phase 2
0.5847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4252	Approved
0.5842	Remote Similarity	NPD5368	Approved
0.5833	Remote Similarity	NPD7087	Discontinued
0.5825	Remote Similarity	NPD6110	Phase 1
0.5812	Remote Similarity	NPD6881	Approved
0.5812	Remote Similarity	NPD6899	Approved
0.581	Remote Similarity	NPD6422	Discontinued
0.58	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8130	Phase 1
0.5798	Remote Similarity	NPD6649	Approved
0.5798	Remote Similarity	NPD6650	Approved
0.5794	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6051	Approved
0.5784	Remote Similarity	NPD6898	Phase 1
0.578	Remote Similarity	NPD6399	Phase 3
0.5776	Remote Similarity	NPD5048	Discontinued
0.5773	Remote Similarity	NPD4732	Discontinued
0.5766	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6882	Approved
0.5743	Remote Similarity	NPD6683	Phase 2
0.5729	Remote Similarity	NPD7144	Approved
0.5729	Remote Similarity	NPD7143	Approved
0.5727	Remote Similarity	NPD7900	Approved
0.5727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5697	Approved
0.5726	Remote Similarity	NPD6685	Approved
0.5725	Remote Similarity	NPD7266	Discontinued
0.5714	Remote Similarity	NPD6893	Approved
0.5714	Remote Similarity	NPD4193	Approved
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD4194	Approved
0.5714	Remote Similarity	NPD6926	Approved
0.5714	Remote Similarity	NPD4192	Approved
0.5714	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD6924	Approved
0.5714	Remote Similarity	NPD4191	Approved
0.5701	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.569	Remote Similarity	NPD5909	Discontinued
0.5688	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD6845	Suspended
0.568	Remote Similarity	NPD6319	Approved
0.5678	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5695	Phase 3
0.567	Remote Similarity	NPD7152	Approved
0.567	Remote Similarity	NPD7151	Approved
0.567	Remote Similarity	NPD7150	Approved
0.5667	Remote Similarity	NPD6617	Approved
0.5667	Remote Similarity	NPD6869	Approved
0.5667	Remote Similarity	NPD6847	Approved
0.566	Remote Similarity	NPD5330	Approved
0.566	Remote Similarity	NPD7521	Approved
0.566	Remote Similarity	NPD7146	Approved
0.566	Remote Similarity	NPD5279	Phase 3
0.566	Remote Similarity	NPD7334	Approved
0.566	Remote Similarity	NPD6684	Approved
0.566	Remote Similarity	NPD6409	Approved
0.5648	Remote Similarity	NPD5370	Suspended
0.5641	Remote Similarity	NPD7128	Approved
0.5641	Remote Similarity	NPD6675	Approved
0.5641	Remote Similarity	NPD5739	Approved
0.5641	Remote Similarity	NPD6640	Phase 3
0.5641	Remote Similarity	NPD6402	Approved
0.563	Remote Similarity	NPD6372	Approved
0.563	Remote Similarity	NPD6014	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