NPASS Compound

Structure

CID68767 OpenBabel06191715402D 95105 0 0 1 0 0 0 0 0999 V2000 -4.1532 -8.2422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3807 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8900 0.8498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8498 2.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3807 1.9626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8498 -1.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8498 -0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8498 1.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5495 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6997 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 -0.9813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5495 -1.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5495 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6997 2.9439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3482 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6485 3.4346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4298 -5.7207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1987 -6.2784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8900 1.1128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4835 -9.2058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6120 -7.4953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4072 -7.2944 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8498 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6997 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5495 3.4346 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1237 -6.4146 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8926 -6.9723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4984 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7987 2.9439 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5495 1.4720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8498 1.4720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8498 -1.4720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0715 -6.1606 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4984 -0.9813 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7987 1.9626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6485 -1.4720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6090 -6.0925 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7987 -0.9813 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9151 -5.3986 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6907 -8.1742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0990 1.9626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3551 -7.0404 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6386 -7.9202 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9489 1.4720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3255 -5.2127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0430 -8.9777 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3994 2.9439 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9968 -7.4803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9673 -5.6526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7987 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0990 2.9439 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6316 -4.5188 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2803 -8.3601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1917 -2.8771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6997 1.9626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3994 1.9626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8498 0.4907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.8659 -8.4432 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6997 -0.9813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1981 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4984 2.9439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8713 1.1128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.4527 -9.0523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5495 4.4159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8697 -7.3624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8404 -6.7184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8498 -2.4533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7654 -6.8545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3482 -1.4720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6485 1.4720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6485 -2.4533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5569 -5.8385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9489 -1.4720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1691 -4.4508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4367 -9.1221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2492 1.4720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9916 -9.9576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2438 -3.1310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8352 -8.2897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2508 -6.5324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6838 -4.7728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6320 -7.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7133 -6.6005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6485 0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9489 3.4346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0489 -7.7343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3325 -8.6141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9489 0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2734 -4.9587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2492 3.4346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8856 -3.5709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 57 1 0 0 0 0 3 57 1 0 0 0 0 6 60 1 0 0 0 0 8 9 1 0 0 0 0 8 25 2 0 0 0 0 9 33 1 0 0 0 0 10 11 1 0 0 0 0 10 32 1 0 0 0 0 11 60 1 0 0 0 0 12 13 1 0 0 0 0 12 57 1 0 0 0 0 13 63 1 0 0 0 0 14 26 1 0 0 0 0 14 57 1 0 0 0 0 15 27 1 0 0 0 0 15 58 1 0 0 0 0 16 34 1 0 0 0 0 16 61 1 0 0 0 0 17 64 1 0 0 0 0 18 65 1 0 0 0 0 19 28 1 0 0 0 0 19 85 1 0 0 0 0 20 29 1 0 0 0 0 20 84 1 0 0 0 0 21 59 1 0 0 0 0 21 66 1 0 0 0 0 22 62 1 0 0 0 0 22 67 1 0 0 0 0 23 62 1 0 0 0 0 23 86 1 0 0 0 0 24 1 1 1 0 0 0 24 44 1 0 0 0 0 24 87 1 0 0 0 0 25 26 1 0 0 0 0 25 61 1 0 0 0 0 26 63 1 1 0 0 0 27 49 1 0 0 0 0 27 68 1 6 0 0 0 28 35 1 0 0 0 0 28 69 1 6 0 0 0 29 45 1 0 0 0 0 29 70 1 6 0 0 0 30 17 1 6 0 0 0 30 36 1 0 0 0 0 30 88 1 0 0 0 0 31 18 1 6 0 0 0 31 37 1 0 0 0 0 31 89 1 0 0 0 0 32 58 1 6 0 0 0 32 59 1 0 0 0 0 33 58 1 6 0 0 0 33 60 1 0 0 0 0 34 63 1 1 0 0 0 34 71 1 0 0 0 0 35 47 1 0 0 0 0 35 72 1 6 0 0 0 36 38 1 0 0 0 0 36 73 1 1 0 0 0 37 46 1 0 0 0 0 37 74 1 1 0 0 0 38 40 1 0 0 0 0 38 75 1 6 0 0 0 39 41 1 0 0 0 0 39 44 1 0 0 0 0 39 76 1 1 0 0 0 40 52 1 0 0 0 0 40 77 1 1 0 0 0 41 51 1 0 0 0 0 41 78 1 1 0 0 0 42 45 1 0 0 0 0 42 50 1 0 0 0 0 42 79 1 6 0 0 0 43 46 1 0 0 0 0 43 53 1 0 0 0 0 43 80 1 1 0 0 0 44 90 1 6 0 0 0 45 91 1 1 0 0 0 46 92 1 6 0 0 0 47 54 1 0 0 0 0 47 93 1 1 0 0 0 48 55 1 0 0 0 0 48 62 1 6 0 0 0 48 81 1 0 0 0 0 49 59 1 6 0 0 0 49 94 1 0 0 0 0 50 84 1 0 0 0 0 50 90 1 1 0 0 0 51 87 1 0 0 0 0 51 93 1 6 0 0 0 52 88 1 0 0 0 0 52 92 1 6 0 0 0 53 89 1 0 0 0 0 53 94 1 6 0 0 0 54 85 1 0 0 0 0 54 95 1 6 0 0 0 55 86 1 0 0 0 0 55 91 1 1 0 0 0 56 82 2 0 0 0 0 56 95 1 0 0 0 0 58 4 1 6 0 0 0 59 5 1 6 0 0 0 60 61 1 1 0 0 0 61 7 1 1 0 0 0 62 83 1 6 0 0 0 63 56 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1370.64
Volume:	1280.097
LogP:	-0.011
LogD:	0.188
LogS:	-2.489
# Rotatable Bonds:	17
TPSA:	512.2
# H-Bond Aceptor:	32
# H-Bond Donor:	19
# Rings:	11
# Heavy Atoms:	32

MedChem Properties

QED Drug-Likeness Score:	0.039
Synthetic Accessibility Score:	7.879
Fsp3:	0.952
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:	-6.519
MDCK Permeability:	0.00036042064311914146
Pgp-inhibitor:	0.001
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.731
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	46.584510803222656%
Volume Distribution (VD):	-0.273
Pgp-substrate:	23.907522201538086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-0.715
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.476
Skin Sensitization:	0.069
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC68767

Natural Product ID:	NPC68767
*Common Name:**	Polygalacin D2
IUPAC Name:	[(2S,3R,4S,5S)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:	Polygalacin D2
Standard InCHIKey:	DSHSDWSTXKYPEQ-DAANLMTCSA-N
Standard InCHI:	InChI=1S/C63H102O32/c1-24-44(90-50-42(79)45(29(70)20-84-50)91-55-48(81)62(83,22-67)23-86-55)39(76)41(78)51(87-24)93-47-35(72)28(69)19-85-54(47)95-56(82)63-13-12-57(2,3)14-26(63)25-8-9-33-58(4)15-27(68)49(59(5,21-66)32(58)10-11-60(33,6)61(25,7)16-34(63)71)94-53-43(80)46(37(74)31(18-65)89-53)92-52-40(77)38(75)36(73)30(17-64)88-52/h8,24,26-55,64-81,83H,9-23H2,1-7H3/t24-,26-,27-,28-,29+,30+,31+,32+,33+,34+,35-,36+,37+,38-,39-,40+,41+,42+,43+,44-,45-,46-,47+,48-,49-,50-,51-,52-,53-,54-,55-,58-,59-,60+,61+,62+,63+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1OC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC[C@@H]3[C@@]4(C)C[C@@H]([C@@H]([C@@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O[C@H]1[C@@H]([C@@](CO)(CO1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641866
PubChem CID:	53325781
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	root	n.a.	PMID[17851435]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20939516]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	root	n.a.	PMID[20939516]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO214	Platycodon grandiflorus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO214	Platycodon grandiflorus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO214	Platycodon grandiflorus	Species	Campanulaceae	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	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	3800.0	nM	PMID[503792]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3400.0	nM	PMID[503792]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2600.0	nM	PMID[503792]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5800.0	nM	PMID[503792]

☑ 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 NPC68767 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	263
0.1-0.2	1708
0.2-0.3	5265
0.3-0.4	11476
0.4-0.5	9960
0.5-0.6	6215
0.6-0.7	4291
0.7-0.8	2014
0.8-0.85	743
0.85-0.9	377
0.9-0.95	356
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC51099
1.0	High Similarity	NPC293031
1.0	High Similarity	NPC275225
0.991	High Similarity	NPC267694
0.991	High Similarity	NPC142151
0.991	High Similarity	NPC144644
0.991	High Similarity	NPC153673
0.991	High Similarity	NPC37860
0.991	High Similarity	NPC110385
0.982	High Similarity	NPC477464
0.982	High Similarity	NPC471577
0.9732	High Similarity	NPC473645
0.973	High Similarity	NPC475899
0.973	High Similarity	NPC237191
0.9646	High Similarity	NPC477463
0.9643	High Similarity	NPC207738
0.964	High Similarity	NPC85154
0.964	High Similarity	NPC470876
0.964	High Similarity	NPC8524
0.964	High Similarity	NPC286457
0.964	High Similarity	NPC475209
0.964	High Similarity	NPC123522
0.964	High Similarity	NPC69811
0.964	High Similarity	NPC473452
0.964	High Similarity	NPC475514
0.964	High Similarity	NPC33012
0.964	High Similarity	NPC220160
0.964	High Similarity	NPC102505
0.964	High Similarity	NPC191827
0.964	High Similarity	NPC309223
0.964	High Similarity	NPC104137
0.9558	High Similarity	NPC476991
0.9554	High Similarity	NPC105800
0.9554	High Similarity	NPC232237
0.955	High Similarity	NPC26626
0.955	High Similarity	NPC75287
0.955	High Similarity	NPC288205
0.955	High Similarity	NPC305267
0.955	High Similarity	NPC476992
0.955	High Similarity	NPC51465
0.9469	High Similarity	NPC51564
0.9469	High Similarity	NPC135849
0.9469	High Similarity	NPC25663
0.9469	High Similarity	NPC473386
0.9464	High Similarity	NPC300419
0.9464	High Similarity	NPC473824
0.9464	High Similarity	NPC475119
0.9464	High Similarity	NPC471580
0.9459	High Similarity	NPC224381
0.9459	High Similarity	NPC164389
0.9459	High Similarity	NPC305981
0.9459	High Similarity	NPC4328
0.9459	High Similarity	NPC67857
0.9459	High Similarity	NPC41061
0.9459	High Similarity	NPC236638
0.9459	High Similarity	NPC309907
0.9459	High Similarity	NPC469782
0.9459	High Similarity	NPC227551
0.9459	High Similarity	NPC471550
0.9459	High Similarity	NPC161717
0.9459	High Similarity	NPC119592
0.9459	High Similarity	NPC476068
0.9459	High Similarity	NPC43550
0.9459	High Similarity	NPC250247
0.9459	High Similarity	NPC60557
0.9459	High Similarity	NPC65105
0.9459	High Similarity	NPC475486
0.9459	High Similarity	NPC76972
0.9459	High Similarity	NPC79643
0.9459	High Similarity	NPC71065
0.9459	High Similarity	NPC123199
0.9459	High Similarity	NPC473714
0.9459	High Similarity	NPC294453
0.9459	High Similarity	NPC475160
0.9459	High Similarity	NPC57484
0.9459	High Similarity	NPC54636
0.9459	High Similarity	NPC70809
0.9459	High Similarity	NPC475140
0.9459	High Similarity	NPC471385
0.9459	High Similarity	NPC204414
0.9459	High Similarity	NPC293330
0.9459	High Similarity	NPC298034
0.9459	High Similarity	NPC202828
0.9459	High Similarity	NPC100639
0.9459	High Similarity	NPC261506
0.9381	High Similarity	NPC473459
0.9381	High Similarity	NPC36831
0.9381	High Similarity	NPC470513
0.9381	High Similarity	NPC470514
0.9375	High Similarity	NPC291903
0.9375	High Similarity	NPC37134
0.9369	High Similarity	NPC473826
0.9369	High Similarity	NPC251263
0.9369	High Similarity	NPC96641
0.9369	High Similarity	NPC46665
0.9369	High Similarity	NPC241909
0.9369	High Similarity	NPC73318
0.9369	High Similarity	NPC295823
0.9369	High Similarity	NPC475467
0.9369	High Similarity	NPC238935
0.9369	High Similarity	NPC309714
0.9369	High Similarity	NPC323341
0.9369	High Similarity	NPC473343
0.9369	High Similarity	NPC133818
0.9369	High Similarity	NPC174720
0.9369	High Similarity	NPC166422
0.9369	High Similarity	NPC475208
0.9369	High Similarity	NPC114304
0.9369	High Similarity	NPC192600
0.9369	High Similarity	NPC155410
0.9369	High Similarity	NPC219180
0.9369	High Similarity	NPC475287
0.9369	High Similarity	NPC114287
0.9369	High Similarity	NPC151543
0.9369	High Similarity	NPC150400
0.9369	High Similarity	NPC134835
0.9369	High Similarity	NPC163183
0.9316	High Similarity	NPC470218
0.9292	High Similarity	NPC68175
0.9292	High Similarity	NPC110633
0.9292	High Similarity	NPC323359
0.9292	High Similarity	NPC148417
0.9292	High Similarity	NPC185466
0.9292	High Similarity	NPC136768
0.9279	High Similarity	NPC473383
0.9279	High Similarity	NPC102439
0.9279	High Similarity	NPC257468
0.9279	High Similarity	NPC104400
0.9279	High Similarity	NPC109079
0.9279	High Similarity	NPC10320
0.9279	High Similarity	NPC471383
0.9279	High Similarity	NPC48249
0.9279	High Similarity	NPC101744
0.9279	High Similarity	NPC79718
0.9279	High Similarity	NPC139894
0.9279	High Similarity	NPC473373
0.9279	High Similarity	NPC324875
0.9279	High Similarity	NPC475516
0.9279	High Similarity	NPC1046
0.9279	High Similarity	NPC104071
0.9279	High Similarity	NPC292677
0.9279	High Similarity	NPC276093
0.9279	High Similarity	NPC80843
0.9279	High Similarity	NPC469946
0.9279	High Similarity	NPC475504
0.9279	High Similarity	NPC139044
0.9231	High Similarity	NPC33068
0.9217	High Similarity	NPC268184
0.9204	High Similarity	NPC160415
0.9204	High Similarity	NPC161674
0.9204	High Similarity	NPC58448
0.9204	High Similarity	NPC471384
0.9196	High Similarity	NPC124296
0.9196	High Similarity	NPC258885
0.9189	High Similarity	NPC179434
0.9189	High Similarity	NPC31839
0.9189	High Similarity	NPC164419
0.9167	High Similarity	NPC43589
0.9167	High Similarity	NPC300655
0.9167	High Similarity	NPC311178
0.9167	High Similarity	NPC222951
0.9145	High Similarity	NPC235405
0.9145	High Similarity	NPC281148
0.9145	High Similarity	NPC258617
0.9145	High Similarity	NPC200049
0.9145	High Similarity	NPC302543
0.9145	High Similarity	NPC283417
0.9145	High Similarity	NPC257211
0.9145	High Similarity	NPC30735
0.9123	High Similarity	NPC471547
0.9099	High Similarity	NPC279554
0.9099	High Similarity	NPC75747
0.9099	High Similarity	NPC242611
0.9099	High Similarity	NPC270667
0.9099	High Similarity	NPC199457
0.9099	High Similarity	NPC127056
0.9099	High Similarity	NPC164194
0.9099	High Similarity	NPC102914
0.9099	High Similarity	NPC29069
0.9099	High Similarity	NPC59804
0.9099	High Similarity	NPC56713
0.9099	High Similarity	NPC136877
0.9099	High Similarity	NPC110139
0.9099	High Similarity	NPC108709
0.9099	High Similarity	NPC174679
0.9099	High Similarity	NPC7870
0.9099	High Similarity	NPC68419
0.9099	High Similarity	NPC474589
0.9099	High Similarity	NPC475296
0.9099	High Similarity	NPC90856
0.9091	High Similarity	NPC233223
0.9091	High Similarity	NPC475177
0.9091	High Similarity	NPC319719
0.9091	High Similarity	NPC322904
0.9091	High Similarity	NPC324933
0.9091	High Similarity	NPC183816
0.9091	High Similarity	NPC475444
0.9091	High Similarity	NPC473679
0.9091	High Similarity	NPC196874
0.9068	High Similarity	NPC23275

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 NPC68767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1986
0.2-0.3	4017
0.3-0.4	1904
0.4-0.5	525
0.5-0.6	294
0.6-0.7	151
0.7-0.8	34
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD8328	Phase 3
0.8475	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8376	Intermediate Similarity	NPD8133	Approved
0.8348	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD8515	Approved
0.8049	Intermediate Similarity	NPD8517	Approved
0.8049	Intermediate Similarity	NPD8516	Approved
0.7903	Intermediate Similarity	NPD8513	Phase 3
0.7823	Intermediate Similarity	NPD8377	Approved
0.7823	Intermediate Similarity	NPD8294	Approved
0.7812	Intermediate Similarity	NPD7736	Approved
0.776	Intermediate Similarity	NPD8296	Approved
0.776	Intermediate Similarity	NPD8380	Approved
0.776	Intermediate Similarity	NPD8378	Approved
0.776	Intermediate Similarity	NPD8335	Approved
0.776	Intermediate Similarity	NPD8379	Approved
0.7752	Intermediate Similarity	NPD7319	Approved
0.7712	Intermediate Similarity	NPD6412	Phase 2
0.7656	Intermediate Similarity	NPD7507	Approved
0.7647	Intermediate Similarity	NPD6686	Approved
0.7619	Intermediate Similarity	NPD8033	Approved
0.7597	Intermediate Similarity	NPD8293	Discontinued
0.746	Intermediate Similarity	NPD7516	Approved
0.7459	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD6370	Approved
0.7381	Intermediate Similarity	NPD7327	Approved
0.7381	Intermediate Similarity	NPD7328	Approved
0.7368	Intermediate Similarity	NPD7748	Approved
0.7328	Intermediate Similarity	NPD7902	Approved
0.7308	Intermediate Similarity	NPD7492	Approved
0.7266	Intermediate Similarity	NPD6054	Approved
0.7266	Intermediate Similarity	NPD6059	Approved
0.7252	Intermediate Similarity	NPD6616	Approved
0.725	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7503	Approved
0.7197	Intermediate Similarity	NPD7078	Approved
0.7193	Intermediate Similarity	NPD7515	Phase 2
0.7132	Intermediate Similarity	NPD6319	Approved
0.7077	Intermediate Similarity	NPD6016	Approved
0.7077	Intermediate Similarity	NPD6015	Approved
0.7073	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7900	Approved
0.7023	Intermediate Similarity	NPD5988	Approved
0.7016	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8297	Approved
0.6984	Remote Similarity	NPD6882	Approved
0.694	Remote Similarity	NPD8074	Phase 3
0.6899	Remote Similarity	NPD6009	Approved
0.6899	Remote Similarity	NPD7115	Discovery
0.6897	Remote Similarity	NPD8034	Phase 2
0.6897	Remote Similarity	NPD8035	Phase 2
0.6842	Remote Similarity	NPD6067	Discontinued
0.6838	Remote Similarity	NPD8171	Discontinued
0.6833	Remote Similarity	NPD7638	Approved
0.6825	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4632	Approved
0.6777	Remote Similarity	NPD7639	Approved
0.6777	Remote Similarity	NPD7640	Approved
0.6774	Remote Similarity	NPD7128	Approved
0.6774	Remote Similarity	NPD5739	Approved
0.6774	Remote Similarity	NPD6675	Approved
0.6774	Remote Similarity	NPD6402	Approved
0.6765	Remote Similarity	NPD6033	Approved
0.6746	Remote Similarity	NPD6372	Approved
0.6746	Remote Similarity	NPD6373	Approved
0.6695	Remote Similarity	NPD6399	Phase 3
0.6694	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6643	Remote Similarity	NPD8450	Suspended
0.6641	Remote Similarity	NPD8130	Phase 1
0.6641	Remote Similarity	NPD6649	Approved
0.6641	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD6411	Approved
0.6587	Remote Similarity	NPD5697	Approved
0.6587	Remote Similarity	NPD5701	Approved
0.6587	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7645	Phase 2
0.6571	Remote Similarity	NPD8449	Approved
0.6567	Remote Similarity	NPD6921	Approved
0.6562	Remote Similarity	NPD7290	Approved
0.6562	Remote Similarity	NPD7102	Approved
0.6562	Remote Similarity	NPD4634	Approved
0.6562	Remote Similarity	NPD6883	Approved
0.6512	Remote Similarity	NPD6869	Approved
0.6512	Remote Similarity	NPD6847	Approved
0.6512	Remote Similarity	NPD6617	Approved
0.6508	Remote Similarity	NPD6008	Approved
0.6484	Remote Similarity	NPD6013	Approved
0.6484	Remote Similarity	NPD6012	Approved
0.6484	Remote Similarity	NPD6014	Approved
0.6475	Remote Similarity	NPD6083	Phase 2
0.6475	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD7604	Phase 2
0.6444	Remote Similarity	NPD5983	Phase 2
0.6441	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6101	Approved
0.6406	Remote Similarity	NPD6011	Approved
0.6391	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6336	Discontinued
0.6356	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4755	Approved
0.6333	Remote Similarity	NPD7625	Phase 1
0.6333	Remote Similarity	NPD7983	Approved
0.6325	Remote Similarity	NPD3618	Phase 1
0.6312	Remote Similarity	NPD5956	Approved
0.6303	Remote Similarity	NPD5328	Approved
0.6293	Remote Similarity	NPD4786	Approved
0.6286	Remote Similarity	NPD8336	Approved
0.6286	Remote Similarity	NPD8337	Approved
0.6281	Remote Similarity	NPD5778	Approved
0.6281	Remote Similarity	NPD5779	Approved
0.6281	Remote Similarity	NPD4202	Approved
0.6271	Remote Similarity	NPD3573	Approved
0.627	Remote Similarity	NPD7632	Discontinued
0.6261	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD46	Approved
0.625	Remote Similarity	NPD6698	Approved
0.624	Remote Similarity	NPD5285	Approved
0.624	Remote Similarity	NPD4696	Approved
0.624	Remote Similarity	NPD5286	Approved
0.624	Remote Similarity	NPD4700	Approved
0.6228	Remote Similarity	NPD7525	Registered
0.6224	Remote Similarity	NPD8338	Approved
0.6214	Remote Similarity	NPD8448	Approved
0.6207	Remote Similarity	NPD3669	Approved
0.6207	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6079	Approved
0.6197	Remote Similarity	NPD8392	Approved
0.6197	Remote Similarity	NPD8390	Approved
0.6197	Remote Similarity	NPD8391	Approved
0.6194	Remote Similarity	NPD6274	Approved
0.6194	Remote Similarity	NPD6940	Discontinued
0.6187	Remote Similarity	NPD8341	Approved
0.6187	Remote Similarity	NPD8340	Approved
0.6187	Remote Similarity	NPD8342	Approved
0.6187	Remote Similarity	NPD8299	Approved
0.6186	Remote Similarity	NPD7334	Approved
0.6186	Remote Similarity	NPD7146	Approved
0.6186	Remote Similarity	NPD6409	Approved
0.6186	Remote Similarity	NPD5330	Approved
0.6186	Remote Similarity	NPD6684	Approved
0.6186	Remote Similarity	NPD7521	Approved
0.6179	Remote Similarity	NPD5695	Phase 3
0.6179	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7100	Approved
0.6176	Remote Similarity	NPD7101	Approved
0.616	Remote Similarity	NPD5696	Approved
0.616	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD8080	Discontinued
0.6143	Remote Similarity	NPD8451	Approved
0.6142	Remote Similarity	NPD5225	Approved
0.6142	Remote Similarity	NPD5226	Approved
0.6142	Remote Similarity	NPD5224	Approved
0.6142	Remote Similarity	NPD4633	Approved
0.6142	Remote Similarity	NPD5211	Phase 2
0.6124	Remote Similarity	NPD4768	Approved
0.6124	Remote Similarity	NPD4767	Approved
0.6103	Remote Similarity	NPD6335	Approved
0.6098	Remote Similarity	NPD5282	Discontinued
0.6094	Remote Similarity	NPD5174	Approved
0.6094	Remote Similarity	NPD5175	Approved
0.6087	Remote Similarity	NPD6909	Approved
0.6087	Remote Similarity	NPD6908	Approved
0.6083	Remote Similarity	NPD6903	Approved
0.6083	Remote Similarity	NPD5737	Approved
0.6083	Remote Similarity	NPD6672	Approved
0.6066	Remote Similarity	NPD7637	Suspended
0.6063	Remote Similarity	NPD5223	Approved
0.6063	Remote Similarity	NPD5344	Discontinued
0.6061	Remote Similarity	NPD6371	Approved
0.6053	Remote Similarity	NPD6114	Approved
0.6053	Remote Similarity	NPD6115	Approved
0.6053	Remote Similarity	NPD6697	Approved
0.6053	Remote Similarity	NPD6118	Approved
0.605	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7799	Discontinued
0.6047	Remote Similarity	NPD5141	Approved
0.6034	Remote Similarity	NPD1779	Approved
0.6034	Remote Similarity	NPD1780	Approved
0.6033	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD4753	Phase 2
0.6031	Remote Similarity	NPD4729	Approved
0.6031	Remote Similarity	NPD4730	Approved
0.6029	Remote Similarity	NPD6317	Approved
0.6017	Remote Similarity	NPD3666	Approved
0.6017	Remote Similarity	NPD3665	Phase 1
0.6017	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD7524	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