NPASS Compound

Structure

NPC475121 OpenBabel07101718222D 97106 0 0 1 0 0 0 0 0999 V2000 1.6057 4.9418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7647 3.6547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0705 3.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2784 2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6113 -9.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2094 -5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6113 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8136 3.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5352 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0878 -5.1391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0878 -3.4071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4773 -8.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.2094 -4.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7453 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5878 -4.2731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.3434 -9.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.0754 -4.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7453 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.2094 -8.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.0754 -3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8793 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.2094 -7.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.2094 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0132 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5878 -2.5411 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0878 -3.4071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3434 -7.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.3434 -3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0132 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0878 -3.4071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 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 -9.6113 -10.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4158 1.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -6.0052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -4.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5878 -4.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3434 -10.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.9414 -4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6113 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.0754 -9.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.9414 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.0754 -7.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2094 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 -3.4071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -4.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3434 -6.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4773 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4773 -7.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3434 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 4 29 1 0 0 0 0 6 65 1 0 0 0 0 7 84 1 0 0 0 0 8 85 1 0 0 0 0 9 13 1 0 0 0 0 9 27 1 0 0 0 0 10 14 2 0 0 0 0 10 30 1 0 0 0 0 11 12 1 0 0 0 0 11 31 2 0 0 0 0 13 36 1 0 0 0 0 14 39 1 0 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 18 1 0 0 0 0 16 34 1 0 0 0 0 17 64 1 0 0 0 0 18 65 1 0 0 0 0 19 30 2 0 0 0 0 19 40 1 0 0 0 0 20 31 1 0 0 0 0 20 32 1 0 0 0 0 21 35 1 0 0 0 0 21 44 1 0 0 0 0 22 67 1 0 0 0 0 23 37 1 0 0 0 0 23 86 1 0 0 0 0 24 38 1 0 0 0 0 24 87 1 0 0 0 0 25 88 1 0 0 0 0 26 89 1 0 0 0 0 28 3 1 1 0 0 0 28 36 1 0 0 0 0 28 66 1 0 0 0 0 29 68 2 0 0 0 0 29 90 1 0 0 0 0 30 58 1 0 0 0 0 31 64 1 0 0 0 0 32 91 1 1 0 0 0 33 12 1 6 0 0 0 33 34 1 0 0 0 0 33 35 1 0 0 0 0 34 64 1 1 0 0 0 35 65 1 1 0 0 0 36 69 2 0 0 0 0 37 45 1 0 0 0 0 37 70 1 6 0 0 0 38 55 1 0 0 0 0 38 71 1 1 0 0 0 39 40 2 0 0 0 0 39 84 1 0 0 0 0 40 85 1 0 0 0 0 41 22 1 6 0 0 0 41 46 1 0 0 0 0 41 92 1 0 0 0 0 42 25 1 6 0 0 0 42 47 1 0 0 0 0 42 93 1 0 0 0 0 43 26 1 6 0 0 0 43 48 1 0 0 0 0 43 94 1 0 0 0 0 44 66 1 1 0 0 0 44 95 1 0 0 0 0 45 56 1 0 0 0 0 45 72 1 1 0 0 0 46 49 1 0 0 0 0 46 73 1 1 0 0 0 47 50 1 0 0 0 0 47 74 1 1 0 0 0 48 51 1 0 0 0 0 48 75 1 1 0 0 0 49 52 1 0 0 0 0 49 76 1 6 0 0 0 50 53 1 0 0 0 0 50 77 1 6 0 0 0 51 54 1 0 0 0 0 51 78 1 6 0 0 0 52 59 1 0 0 0 0 52 79 1 1 0 0 0 53 60 1 0 0 0 0 53 80 1 1 0 0 0 54 61 1 0 0 0 0 54 81 1 1 0 0 0 55 57 1 0 0 0 0 55 97 1 1 0 0 0 56 62 1 0 0 0 0 56 96 1 6 0 0 0 57 63 1 0 0 0 0 57 90 1 6 0 0 0 58 82 2 0 0 0 0 58 96 1 0 0 0 0 59 88 1 6 0 0 0 59 92 1 0 0 0 0 60 89 1 6 0 0 0 60 93 1 0 0 0 0 61 91 1 6 0 0 0 61 94 1 0 0 0 0 62 86 1 0 0 0 0 62 97 1 1 0 0 0 63 87 1 0 0 0 0 63 95 1 1 0 0 0 64 5 1 1 0 0 0 65 66 1 6 0 0 0 66 83 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1388.62
Volume:	1318.569
LogP:	1.922
LogD:	0.806
LogS:	-2.859
# Rotatable Bonds:	25
TPSA:	463.65
# H-Bond Aceptor:	31
# H-Bond Donor:	14
# Rings:	10
# Heavy Atoms:	31

MedChem Properties

QED Drug-Likeness Score:	0.04
Synthetic Accessibility Score:	7.548
Fsp3:	0.833
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:	-6.246
MDCK Permeability:	0.0006070248200558126
Pgp-inhibitor:	0.05
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155
Plasma Protein Binding (PPB):	56.80497741699219%
Volume Distribution (VD):	-0.1
Pgp-substrate:	17.602487564086914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	0.271
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.642
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.098
Carcinogencity:	0.141
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.557

Download Data

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

Natural Product: NPC475121

Natural Product ID:	NPC475121
*Common Name:**	3Beta-[(O-Beta-D-Glucopyranosyl-(1->4)-O-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl)Oxy)]-17Alpha-Hydroxy-16Beta-[(O-(2-O-3,4-Dimethoxybenzoyl-Beta-D-Xylopyranosyl)-(1->3)-2-O-Acetyl-Alphal-Arabinopyranosyl)Oxy]Cholest-5-En-22-One
IUPAC Name:	[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-5-hydroxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-hydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] 3,4-dimethoxybenzoate
Synonyms:
Standard InCHIKey:	QJQIJQZEBUTRGW-YQEFZMCWSA-N
Standard InCHI:	InChI=1S/C66H100O31/c1-27(2)9-13-36(69)28(3)66(83)44(95-63-57(90-29(4)68)55(38(71)24-87-63)97-62-56(45(72)37(70)23-86-62)96-58(82)30-10-14-39(84-7)40(19-30)85-8)21-35-33-12-11-31-20-32(15-17-64(31,5)34(33)16-18-65(35,66)6)91-61-54(81)51(78)48(75)43(94-61)26-89-60-53(80)50(77)47(74)42(93-60)25-88-59-52(79)49(76)46(73)41(22-67)92-59/h10-11,14,19,27-28,32-35,37-38,41-57,59-63,67,70-81,83H,9,12-13,15-18,20-26H2,1-8H3/t28-,32+,33-,34+,35+,37-,38+,41-,42-,43-,44+,45+,46-,47-,48-,49+,50+,51+,52-,53-,54-,55+,56-,57-,59-,60-,61-,62+,63+,64+,65+,66-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC[C@H]3O[C@@H](O[C@H]4CC[C@]5(C(=CC[C@@H]6[C@@H]5CC[C@]5([C@H]6C[C@@H]([C@]5(O)[C@@H](C(=O)CCC(C)C)C)O[C@@H]5OC[C@@H]([C@@H]([C@H]5OC(=O)C)O[C@@H]5OC[C@H]([C@@H]([C@H]5OC(=O)c5ccc(c(c5)OC)OC)O)O)O)C)C4)C)[C@@H]([C@H]([C@@H]3O)O)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498837
PubChem CID:	44575967
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[12398536]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	n.a.	bulb	n.a.	PMID[12398536]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[15497941]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.73	ug.mL-1	PMID[510186]

☑ 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 NPC475121 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	431
0.1-0.2	1651
0.2-0.3	3118
0.3-0.4	6072
0.4-0.5	9522
0.5-0.6	9048
0.6-0.7	9390
0.7-0.8	3251
0.8-0.85	150
0.85-0.9	46
0.9-0.95	4
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476067
0.9942	High Similarity	NPC189704
0.9883	High Similarity	NPC299855
0.9883	High Similarity	NPC96194
0.9828	High Similarity	NPC475299
0.9714	High Similarity	NPC473711
0.9657	High Similarity	NPC112708
0.96	High Similarity	NPC71385
0.96	High Similarity	NPC230670
0.9415	High Similarity	NPC195972
0.9096	High Similarity	NPC473776
0.9096	High Similarity	NPC473205
0.8701	High Similarity	NPC469773
0.8701	High Similarity	NPC469775
0.8701	High Similarity	NPC469772
0.8701	High Similarity	NPC469778
0.8701	High Similarity	NPC100925
0.8701	High Similarity	NPC469776
0.8701	High Similarity	NPC469777
0.8701	High Similarity	NPC32723
0.8701	High Similarity	NPC135334
0.8701	High Similarity	NPC295941
0.8701	High Similarity	NPC469774
0.8693	High Similarity	NPC21956
0.8686	High Similarity	NPC282551
0.8659	High Similarity	NPC475613
0.8613	High Similarity	NPC474936
0.8571	High Similarity	NPC100420
0.8547	High Similarity	NPC124828
0.8514	High Similarity	NPC206815
0.85	High Similarity	NPC475244
0.8492	Intermediate Similarity	NPC470685
0.8483	Intermediate Similarity	NPC202428
0.8483	Intermediate Similarity	NPC266545
0.8475	Intermediate Similarity	NPC477488
0.8475	Intermediate Similarity	NPC200726
0.8466	Intermediate Similarity	NPC109990
0.8444	Intermediate Similarity	NPC475197
0.8444	Intermediate Similarity	NPC473467
0.8436	Intermediate Similarity	NPC472803
0.8427	Intermediate Similarity	NPC286809
0.8427	Intermediate Similarity	NPC177362
0.8418	Intermediate Similarity	NPC318472
0.8415	Intermediate Similarity	NPC188217
0.8409	Intermediate Similarity	NPC476011
0.8409	Intermediate Similarity	NPC145847
0.8398	Intermediate Similarity	NPC469354
0.8389	Intermediate Similarity	NPC13989
0.8382	Intermediate Similarity	NPC476784
0.8371	Intermediate Similarity	NPC469419
0.8371	Intermediate Similarity	NPC301910
0.8371	Intermediate Similarity	NPC130730
0.8362	Intermediate Similarity	NPC327694
0.8362	Intermediate Similarity	NPC475198
0.8362	Intermediate Similarity	NPC475531
0.8362	Intermediate Similarity	NPC475175
0.8343	Intermediate Similarity	NPC179914
0.8324	Intermediate Similarity	NPC476364
0.8315	Intermediate Similarity	NPC102465
0.8306	Intermediate Similarity	NPC469418
0.8305	Intermediate Similarity	NPC473557
0.8305	Intermediate Similarity	NPC473468
0.8305	Intermediate Similarity	NPC477491
0.8305	Intermediate Similarity	NPC326278
0.8305	Intermediate Similarity	NPC246024
0.8305	Intermediate Similarity	NPC475567
0.8297	Intermediate Similarity	NPC469438
0.8286	Intermediate Similarity	NPC471878
0.827	Intermediate Similarity	NPC186746
0.827	Intermediate Similarity	NPC473883
0.8261	Intermediate Similarity	NPC473895
0.8256	Intermediate Similarity	NPC475379
0.8251	Intermediate Similarity	NPC469397
0.8251	Intermediate Similarity	NPC475054
0.8249	Intermediate Similarity	NPC477627
0.8242	Intermediate Similarity	NPC316539
0.8242	Intermediate Similarity	NPC471871
0.8232	Intermediate Similarity	NPC52598
0.8229	Intermediate Similarity	NPC131405
0.8212	Intermediate Similarity	NPC180586
0.8207	Intermediate Similarity	NPC475261
0.8192	Intermediate Similarity	NPC473797
0.8192	Intermediate Similarity	NPC475300
0.8192	Intermediate Similarity	NPC475437
0.8192	Intermediate Similarity	NPC473641
0.8192	Intermediate Similarity	NPC475464
0.8192	Intermediate Similarity	NPC208676
0.8192	Intermediate Similarity	NPC475505
0.8192	Intermediate Similarity	NPC130489
0.8192	Intermediate Similarity	NPC476337
0.8187	Intermediate Similarity	NPC477617
0.8187	Intermediate Similarity	NPC148185
0.8182	Intermediate Similarity	NPC187205
0.8182	Intermediate Similarity	NPC226759
0.8182	Intermediate Similarity	NPC268602
0.8177	Intermediate Similarity	NPC61791
0.8177	Intermediate Similarity	NPC471870
0.8171	Intermediate Similarity	NPC475484
0.8167	Intermediate Similarity	NPC477466
0.8167	Intermediate Similarity	NPC477473
0.8167	Intermediate Similarity	NPC477469
0.8167	Intermediate Similarity	NPC477471
0.8162	Intermediate Similarity	NPC108191
0.8162	Intermediate Similarity	NPC93685
0.8162	Intermediate Similarity	NPC275690
0.8162	Intermediate Similarity	NPC161609
0.8161	Intermediate Similarity	NPC137813
0.8156	Intermediate Similarity	NPC161151
0.8156	Intermediate Similarity	NPC120012
0.8142	Intermediate Similarity	NPC199357
0.8136	Intermediate Similarity	NPC68619
0.8136	Intermediate Similarity	NPC475536
0.8136	Intermediate Similarity	NPC165234
0.8132	Intermediate Similarity	NPC472129
0.8132	Intermediate Similarity	NPC43434
0.8129	Intermediate Similarity	NPC476359
0.8129	Intermediate Similarity	NPC476338
0.8128	Intermediate Similarity	NPC167045
0.8128	Intermediate Similarity	NPC114120
0.8122	Intermediate Similarity	NPC471860
0.8122	Intermediate Similarity	NPC471859
0.8118	Intermediate Similarity	NPC85316
0.8118	Intermediate Similarity	NPC197357
0.8118	Intermediate Similarity	NPC469371
0.8114	Intermediate Similarity	NPC478232
0.8111	Intermediate Similarity	NPC475738
0.8108	Intermediate Similarity	NPC120952
0.8105	Intermediate Similarity	NPC264302
0.8098	Intermediate Similarity	NPC223735
0.8098	Intermediate Similarity	NPC307754
0.8098	Intermediate Similarity	NPC294149
0.809	Intermediate Similarity	NPC150893
0.809	Intermediate Similarity	NPC295408
0.809	Intermediate Similarity	NPC329960
0.809	Intermediate Similarity	NPC138993
0.8087	Intermediate Similarity	NPC472638
0.8077	Intermediate Similarity	NPC658
0.8077	Intermediate Similarity	NPC197708
0.8077	Intermediate Similarity	NPC472133
0.8075	Intermediate Similarity	NPC199172
0.8075	Intermediate Similarity	NPC35924
0.8073	Intermediate Similarity	NPC470200
0.8073	Intermediate Similarity	NPC470194
0.8073	Intermediate Similarity	NPC470195
0.8073	Intermediate Similarity	NPC470193
0.8073	Intermediate Similarity	NPC316274
0.8073	Intermediate Similarity	NPC470197
0.8073	Intermediate Similarity	NPC470196
0.8073	Intermediate Similarity	NPC282474
0.8073	Intermediate Similarity	NPC470198
0.8068	Intermediate Similarity	NPC10205
0.8068	Intermediate Similarity	NPC131532
0.8066	Intermediate Similarity	NPC306475
0.8066	Intermediate Similarity	NPC476277
0.8065	Intermediate Similarity	NPC254588
0.8065	Intermediate Similarity	NPC195114
0.8057	Intermediate Similarity	NPC87403
0.8056	Intermediate Similarity	NPC100425
0.8054	Intermediate Similarity	NPC176246
0.8046	Intermediate Similarity	NPC289021
0.8046	Intermediate Similarity	NPC158546
0.8043	Intermediate Similarity	NPC477881
0.8042	Intermediate Similarity	NPC313063
0.8042	Intermediate Similarity	NPC286301
0.8034	Intermediate Similarity	NPC469384
0.8033	Intermediate Similarity	NPC52353
0.8033	Intermediate Similarity	NPC293004
0.8033	Intermediate Similarity	NPC194483
0.8032	Intermediate Similarity	NPC224557
0.8032	Intermediate Similarity	NPC292706
0.8032	Intermediate Similarity	NPC318119
0.8023	Intermediate Similarity	NPC471405
0.8023	Intermediate Similarity	NPC478248
0.8023	Intermediate Similarity	NPC10945
0.8022	Intermediate Similarity	NPC298847
0.8021	Intermediate Similarity	NPC476358
0.8021	Intermediate Similarity	NPC477860
0.8021	Intermediate Similarity	NPC170203
0.8021	Intermediate Similarity	NPC475161
0.8021	Intermediate Similarity	NPC102367
0.8011	Intermediate Similarity	NPC99216
0.8011	Intermediate Similarity	NPC472131
0.8011	Intermediate Similarity	NPC472387
0.8011	Intermediate Similarity	NPC260300
0.8011	Intermediate Similarity	NPC472130
0.8011	Intermediate Similarity	NPC267549
0.8011	Intermediate Similarity	NPC80360
0.8011	Intermediate Similarity	NPC477882
0.8011	Intermediate Similarity	NPC477880
0.8011	Intermediate Similarity	NPC469417
0.8011	Intermediate Similarity	NPC469420
0.8	Intermediate Similarity	NPC469456
0.8	Intermediate Similarity	NPC102028
0.8	Intermediate Similarity	NPC476335
0.8	Intermediate Similarity	NPC148273
0.8	Intermediate Similarity	NPC471873
0.8	Intermediate Similarity	NPC198199
0.8	Intermediate Similarity	NPC41009
0.8	Intermediate Similarity	NPC134905
0.8	Intermediate Similarity	NPC473630

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 NPC475121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	922
0.2-0.3	2001
0.3-0.4	2717
0.4-0.5	1949
0.5-0.6	886
0.6-0.7	260
0.7-0.8	50
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
0.8547	High Similarity	NPD7685	Pre-registration
0.8162	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD8312	Approved
0.7957	Intermediate Similarity	NPD8313	Approved
0.7935	Intermediate Similarity	NPD7074	Phase 3
0.7923	Intermediate Similarity	NPD7799	Discontinued
0.7853	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD8127	Discontinued
0.7842	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7472	Approved
0.7826	Intermediate Similarity	NPD7228	Approved
0.7807	Intermediate Similarity	NPD7808	Phase 3
0.7784	Intermediate Similarity	NPD7054	Approved
0.7754	Intermediate Similarity	NPD7240	Approved
0.774	Intermediate Similarity	NPD7028	Phase 2
0.766	Intermediate Similarity	NPD7251	Discontinued
0.7644	Intermediate Similarity	NPD8434	Phase 2
0.7634	Intermediate Similarity	NPD3818	Discontinued
0.7606	Intermediate Similarity	NPD6797	Phase 2
0.7556	Intermediate Similarity	NPD37	Approved
0.7554	Intermediate Similarity	NPD7199	Phase 2
0.7527	Intermediate Similarity	NPD4966	Approved
0.7527	Intermediate Similarity	NPD4967	Phase 2
0.7527	Intermediate Similarity	NPD4965	Approved
0.7526	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6273	Approved
0.7514	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7473	Discontinued
0.7486	Intermediate Similarity	NPD7458	Discontinued
0.7472	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD8151	Discontinued
0.7446	Intermediate Similarity	NPD6234	Discontinued
0.7433	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6166	Phase 2
0.7433	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD5494	Approved
0.7401	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7783	Phase 2
0.7376	Intermediate Similarity	NPD7497	Discontinued
0.7376	Intermediate Similarity	NPD7435	Discontinued
0.7371	Intermediate Similarity	NPD8150	Discontinued
0.7345	Intermediate Similarity	NPD7236	Approved
0.734	Intermediate Similarity	NPD8319	Approved
0.734	Intermediate Similarity	NPD8320	Phase 1
0.7337	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4628	Phase 3
0.733	Intermediate Similarity	NPD8166	Discontinued
0.7326	Intermediate Similarity	NPD6232	Discontinued
0.7322	Intermediate Similarity	NPD7819	Suspended
0.7322	Intermediate Similarity	NPD5761	Phase 2
0.7322	Intermediate Similarity	NPD5760	Phase 2
0.7292	Intermediate Similarity	NPD6559	Discontinued
0.7291	Intermediate Similarity	NPD7697	Approved
0.7291	Intermediate Similarity	NPD7696	Phase 3
0.7291	Intermediate Similarity	NPD7698	Approved
0.7257	Intermediate Similarity	NPD7266	Discontinued
0.7246	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7874	Approved
0.7238	Intermediate Similarity	NPD7239	Suspended
0.7233	Intermediate Similarity	NPD7701	Phase 2
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6780	Approved
0.7228	Intermediate Similarity	NPD6777	Approved
0.7189	Intermediate Similarity	NPD3817	Phase 2
0.7174	Intermediate Similarity	NPD1934	Approved
0.7173	Intermediate Similarity	NPD3751	Discontinued
0.7171	Intermediate Similarity	NPD7871	Phase 2
0.7171	Intermediate Similarity	NPD7870	Phase 2
0.7163	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4380	Phase 2
0.7135	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7700	Phase 2
0.7129	Intermediate Similarity	NPD7699	Phase 2
0.7129	Intermediate Similarity	NPD7801	Approved
0.7122	Intermediate Similarity	NPD7680	Approved
0.7113	Intermediate Similarity	NPD6764	Approved
0.7113	Intermediate Similarity	NPD6765	Approved
0.7113	Intermediate Similarity	NPD8368	Discontinued
0.7112	Intermediate Similarity	NPD7075	Discontinued
0.7094	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD8407	Phase 2
0.7079	Intermediate Similarity	NPD6674	Discontinued
0.7073	Intermediate Similarity	NPD6823	Phase 2
0.7072	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3787	Discontinued
0.7043	Intermediate Similarity	NPD1465	Phase 2
0.7005	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD6959	Discontinued
0.698	Remote Similarity	NPD6534	Approved
0.698	Remote Similarity	NPD6535	Approved
0.6973	Remote Similarity	NPD6599	Discontinued
0.6971	Remote Similarity	NPD7999	Approved
0.697	Remote Similarity	NPD6784	Approved
0.697	Remote Similarity	NPD6785	Approved
0.6968	Remote Similarity	NPD3882	Suspended
0.6959	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD2801	Approved
0.6948	Remote Similarity	NPD7930	Approved
0.6944	Remote Similarity	NPD4110	Phase 3
0.6944	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7411	Suspended
0.6919	Remote Similarity	NPD3226	Approved
0.6914	Remote Similarity	NPD4140	Approved
0.6914	Remote Similarity	NPD3620	Phase 2
0.6914	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6801	Discontinued
0.6895	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7097	Phase 1
0.6891	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8404	Phase 2
0.6878	Remote Similarity	NPD7058	Phase 2
0.6878	Remote Similarity	NPD7057	Phase 3
0.6875	Remote Similarity	NPD5735	Approved
0.6872	Remote Similarity	NPD5762	Approved
0.6872	Remote Similarity	NPD5763	Approved
0.6866	Remote Similarity	NPD8435	Approved
0.6866	Remote Similarity	NPD8360	Approved
0.6866	Remote Similarity	NPD8361	Approved
0.6857	Remote Similarity	NPD8032	Phase 2
0.6825	Remote Similarity	NPD5402	Approved
0.6796	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD2533	Approved
0.6793	Remote Similarity	NPD2532	Approved
0.6793	Remote Similarity	NPD2534	Approved
0.6778	Remote Similarity	NPD2346	Discontinued
0.6774	Remote Similarity	NPD1653	Approved
0.6766	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6212	Phase 3
0.6765	Remote Similarity	NPD6213	Phase 3
0.6761	Remote Similarity	NPD6663	Approved
0.6758	Remote Similarity	NPD7003	Approved
0.6758	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6385	Approved
0.6755	Remote Similarity	NPD6386	Approved
0.6754	Remote Similarity	NPD3749	Approved
0.675	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6799	Approved
0.6738	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5353	Approved
0.6731	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5736	Approved
0.6723	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7768	Phase 2
0.6685	Remote Similarity	NPD230	Phase 1
0.6685	Remote Similarity	NPD1933	Approved
0.6682	Remote Similarity	NPD8059	Phase 3
0.6682	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6649	Remote Similarity	NPD5977	Approved
0.6649	Remote Similarity	NPD1511	Approved
0.6649	Remote Similarity	NPD5978	Approved
0.6648	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6653	Approved
0.6634	Remote Similarity	NPD7296	Approved
0.6632	Remote Similarity	NPD919	Approved
0.6631	Remote Similarity	NPD5403	Approved
0.663	Remote Similarity	NPD2935	Discontinued
0.6613	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5401	Approved
0.661	Remote Similarity	NPD3764	Approved
0.6606	Remote Similarity	NPD7907	Approved
0.6603	Remote Similarity	NPD8285	Discontinued
0.6592	Remote Similarity	NPD6355	Discontinued
0.6592	Remote Similarity	NPD447	Suspended
0.6587	Remote Similarity	NPD8485	Approved
0.6582	Remote Similarity	NPD5242	Approved
0.6582	Remote Similarity	NPD3926	Phase 2
0.6578	Remote Similarity	NPD1512	Approved
0.6576	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD3750	Approved
0.6575	Remote Similarity	NPD7033	Discontinued
0.6557	Remote Similarity	NPD1549	Phase 2
0.6556	Remote Similarity	NPD6353	Approved
0.6555	Remote Similarity	NPD4420	Approved
0.6554	Remote Similarity	NPD7095	Approved
0.6554	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7584	Approved
0.6538	Remote Similarity	NPD2438	Suspended
0.6538	Remote Similarity	NPD6099	Approved
0.6538	Remote Similarity	NPD2796	Approved
0.6538	Remote Similarity	NPD6100	Approved
0.6534	Remote Similarity	NPD9494	Approved
0.6531	Remote Similarity	NPD7315	Approved
0.6524	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7422	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data