NPASS Compound

Structure

NPC470517 OpenBabel07101719182D 98107 0 0 1 0 0 0 0 0999 V2000 -7.7221 -4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8641 -6.9352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4320 -6.9352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0694 4.3256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0786 4.3256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0694 -2.3441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0786 -2.3441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7160 0.9907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 -1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 -0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7221 -5.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8580 1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8580 -1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4320 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5740 0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5740 0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 2.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2900 -6.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 -3.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5801 0.9907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1480 -2.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5740 -4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4320 0.9907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8641 -5.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4320 -5.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 1.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1480 -5.9444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8580 -4.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7221 1.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1480 -1.9815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4320 -3.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7160 -0.9907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8580 0.4954 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4320 -0.9907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0060 -6.4398 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8580 -5.4491 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7221 2.4769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0060 -1.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8641 -5.9444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -5.9444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8641 2.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0060 -0.4954 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8641 -4.9537 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8580 -5.4491 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0060 2.4769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1480 -2.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2900 -4.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1480 -3.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1480 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4320 2.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4320 1.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0060 -5.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0060 -4.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8580 -4.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0060 1.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2900 -2.4769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2900 -0.4954 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5740 3.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5740 -1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7160 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8580 0.4954 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 2.5740 1.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2900 -7.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5740 -4.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5801 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5740 -5.4491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0060 -7.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 -5.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5801 2.9722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8641 -1.9815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7221 -6.4398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.9352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8641 3.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7221 -4.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7160 -5.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1480 2.9722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0060 -2.4769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2900 3.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2900 1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1480 -5.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0060 -3.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7160 -3.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4320 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2900 -5.4491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1480 -4.9537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8641 0.9907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2900 -1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4320 -2.9722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2900 -1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0060 -4.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1480 0.9907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 62 1 0 0 0 0 5 62 1 0 0 0 0 6 63 1 0 0 0 0 7 63 1 0 0 0 0 9 65 1 0 0 0 0 11 27 2 0 0 0 0 12 13 1 0 0 0 0 12 29 2 0 0 0 0 13 37 1 0 0 0 0 14 17 1 0 0 0 0 14 36 1 0 0 0 0 15 16 1 0 0 0 0 15 38 1 0 0 0 0 16 64 1 0 0 0 0 17 66 1 0 0 0 0 18 19 1 0 0 0 0 18 65 1 0 0 0 0 19 67 1 0 0 0 0 20 30 1 0 0 0 0 20 62 1 0 0 0 0 21 68 1 0 0 0 0 22 69 1 0 0 0 0 23 70 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 27 56 1 0 0 0 0 28 71 2 0 0 0 0 28 90 1 0 0 0 0 29 30 1 0 0 0 0 29 65 1 0 0 0 0 30 67 1 6 0 0 0 31 21 1 1 0 0 0 31 39 1 0 0 0 0 31 91 1 0 0 0 0 32 22 1 6 0 0 0 32 40 1 0 0 0 0 32 92 1 0 0 0 0 33 23 1 1 0 0 0 33 41 1 0 0 0 0 33 93 1 0 0 0 0 34 24 1 1 0 0 0 34 42 1 0 0 0 0 34 94 1 0 0 0 0 35 25 1 6 0 0 0 35 51 1 0 0 0 0 35 95 1 0 0 0 0 36 63 1 0 0 0 0 36 64 1 1 0 0 0 37 64 1 1 0 0 0 37 66 1 0 0 0 0 38 63 1 0 0 0 0 38 96 1 1 0 0 0 39 43 1 0 0 0 0 39 72 1 6 0 0 0 40 44 1 0 0 0 0 40 73 1 1 0 0 0 41 45 1 0 0 0 0 41 74 1 6 0 0 0 42 46 1 0 0 0 0 42 75 1 6 0 0 0 43 47 1 0 0 0 0 43 76 1 1 0 0 0 44 48 1 0 0 0 0 44 77 1 6 0 0 0 45 49 1 0 0 0 0 45 78 1 1 0 0 0 46 53 1 0 0 0 0 46 79 1 1 0 0 0 47 57 1 0 0 0 0 47 80 1 6 0 0 0 48 58 1 0 0 0 0 48 81 1 1 0 0 0 49 59 1 0 0 0 0 49 82 1 6 0 0 0 50 52 1 0 0 0 0 50 60 1 0 0 0 0 50 83 1 1 0 0 0 51 52 1 0 0 0 0 51 90 1 1 0 0 0 52 97 1 6 0 0 0 53 61 1 0 0 0 0 53 98 1 6 0 0 0 54 55 1 0 0 0 0 54 62 1 0 0 0 0 54 84 1 1 0 0 0 55 67 1 6 0 0 0 55 85 1 0 0 0 0 56 86 2 0 0 0 0 56 97 1 0 0 0 0 57 87 1 1 0 0 0 57 91 1 0 0 0 0 58 88 1 6 0 0 0 58 92 1 0 0 0 0 59 93 1 0 0 0 0 59 98 1 1 0 0 0 60 95 1 0 0 0 0 60 96 1 6 0 0 0 61 89 1 1 0 0 0 61 94 1 0 0 0 0 64 8 1 1 0 0 0 65 66 1 1 0 0 0 66 10 1 1 0 0 0 67 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1408.69
Volume:	1343.774
LogP:	1.833
LogD:	1.167
LogS:	-2.316
# Rotatable Bonds:	21
TPSA:	488.81
# H-Bond Aceptor:	31
# H-Bond Donor:	17
# Rings:	10
# Heavy Atoms:	31

MedChem Properties

QED Drug-Likeness Score:	0.026
Synthetic Accessibility Score:	7.823
Fsp3:	0.91
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:	-6.36
MDCK Permeability:	0.0005578119889833033
Pgp-inhibitor:	0.097
Pgp-substrate:	0.089
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	55.71855926513672%
Volume Distribution (VD):	-0.48
Pgp-substrate:	15.595250129699707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	-0.409
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.238
Human Hepatotoxicity (H-HT):	0.756
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.05
Carcinogencity:	0.003
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.125

Download Data

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

Natural Product: NPC470517

Natural Product ID:	NPC470517
*Common Name:**	Sorbifoliaside F
IUPAC Name:	[(2R,3R,4R,5R,6R)-2-[[(3S,4aR,6aR,6bS,8aR,9R,10R,12aS,14aR,14bR)-8a-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-9,10-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-acetyloxy-3-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:	sorbifoliaside F
Standard InCHIKey:	YQPIHQHVTWOTDZ-GFDWXXGQSA-N
Standard InCHI:	InChI=1S/C67H108O31/c1-11-27(2)56(86)97-52-50(83)60(95-35(51(52)90-28(3)71)25-88-58-48(81)44(77)40(73)32(22-69)92-58)96-38-15-16-64(8)36(63(38,6)7)14-17-66(10)37(64)13-12-29-30-20-62(4,5)54(84)55(85)67(30,19-18-65(29,66)9)26-89-61-53(98-59-49(82)45(78)41(74)33(23-70)93-59)46(79)42(75)34(94-61)24-87-57-47(80)43(76)39(72)31(21-68)91-57/h11-12,30-55,57-61,68-70,72-85H,13-26H2,1-10H3/b27-11-/t30-,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-,57+,58+,59-,60-,61+,64-,65+,66+,67-/m0/s1
SMILES:	CC=C(C)C(=O)OC1C(C(OC(C1OC(=O)C)COC2C(C(C(C(O2)CO)O)O)O)OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(C(C7O)O)(C)C)COC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2058432
PubChem CID:	66552845
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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]

☑ 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	10

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[568469]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	100000.0	nM	PMID[568469]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[568469]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[568469]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[568469]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[568469]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[568469]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	100000.0	nM	PMID[568469]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[568469]

☑ 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 NPC470517 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	270
0.1-0.2	1784
0.2-0.3	4931
0.3-0.4	10220
0.4-0.5	11577
0.5-0.6	6951
0.6-0.7	4115
0.7-0.8	1793
0.8-0.85	520
0.85-0.9	434
0.9-0.95	97
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470911
1.0	High Similarity	NPC470915
0.9908	High Similarity	NPC470515
0.9464	High Similarity	NPC470914
0.931	High Similarity	NPC297950
0.9231	High Similarity	NPC470516
0.9204	High Similarity	NPC471548
0.9153	High Similarity	NPC112492
0.9153	High Similarity	NPC45606
0.9153	High Similarity	NPC220838
0.9153	High Similarity	NPC472270
0.9153	High Similarity	NPC472269
0.9153	High Similarity	NPC23020
0.9153	High Similarity	NPC472268
0.9115	High Similarity	NPC473405
0.9043	High Similarity	NPC135369
0.9018	High Similarity	NPC473159
0.9	High Similarity	NPC311178
0.9	High Similarity	NPC476780
0.9	High Similarity	NPC476775
0.9	High Similarity	NPC43589
0.9	High Similarity	NPC476774
0.9	High Similarity	NPC300655
0.9	High Similarity	NPC271610
0.9	High Similarity	NPC222951
0.8991	High Similarity	NPC281939
0.8947	High Similarity	NPC471547
0.8938	High Similarity	NPC100639
0.8938	High Similarity	NPC298034
0.8938	High Similarity	NPC309907
0.8938	High Similarity	NPC294453
0.8938	High Similarity	NPC65105
0.8938	High Similarity	NPC305981
0.8938	High Similarity	NPC4328
0.8938	High Similarity	NPC43550
0.8938	High Similarity	NPC236638
0.8938	High Similarity	NPC161717
0.8938	High Similarity	NPC476068
0.8938	High Similarity	NPC261506
0.8938	High Similarity	NPC473714
0.8938	High Similarity	NPC60557
0.8938	High Similarity	NPC224381
0.8938	High Similarity	NPC227551
0.8938	High Similarity	NPC475140
0.8938	High Similarity	NPC71065
0.8938	High Similarity	NPC67857
0.8938	High Similarity	NPC79643
0.8938	High Similarity	NPC293330
0.8938	High Similarity	NPC204414
0.8938	High Similarity	NPC119592
0.8938	High Similarity	NPC471550
0.8938	High Similarity	NPC250247
0.8938	High Similarity	NPC76972
0.8938	High Similarity	NPC123199
0.8938	High Similarity	NPC57484
0.8938	High Similarity	NPC475160
0.8938	High Similarity	NPC471385
0.8938	High Similarity	NPC54636
0.8938	High Similarity	NPC41061
0.8938	High Similarity	NPC202828
0.8938	High Similarity	NPC469782
0.8938	High Similarity	NPC70809
0.8926	High Similarity	NPC30279
0.8926	High Similarity	NPC196874
0.8926	High Similarity	NPC71391
0.8926	High Similarity	NPC178264
0.8926	High Similarity	NPC322904
0.8926	High Similarity	NPC277212
0.8926	High Similarity	NPC473918
0.8926	High Similarity	NPC475177
0.8926	High Similarity	NPC192765
0.8926	High Similarity	NPC233223
0.8926	High Similarity	NPC324933
0.8926	High Similarity	NPC319719
0.8926	High Similarity	NPC183816
0.8926	High Similarity	NPC475444
0.8926	High Similarity	NPC476776
0.8926	High Similarity	NPC46823
0.8926	High Similarity	NPC473679
0.8926	High Similarity	NPC312650
0.8917	High Similarity	NPC305793
0.8917	High Similarity	NPC280029
0.8917	High Similarity	NPC472267
0.8917	High Similarity	NPC252657
0.8917	High Similarity	NPC88311
0.8917	High Similarity	NPC47995
0.8917	High Similarity	NPC1314
0.8917	High Similarity	NPC82380
0.8917	High Similarity	NPC273878
0.8917	High Similarity	NPC269484
0.8917	High Similarity	NPC252289
0.8917	High Similarity	NPC11577
0.8917	High Similarity	NPC9470
0.8917	High Similarity	NPC107536
0.8917	High Similarity	NPC97918
0.8917	High Similarity	NPC141600
0.8917	High Similarity	NPC470518
0.8917	High Similarity	NPC265841
0.8917	High Similarity	NPC244296
0.8917	High Similarity	NPC115656
0.8909	High Similarity	NPC475263
0.8899	High Similarity	NPC470512
0.8899	High Similarity	NPC173859
0.887	High Similarity	NPC237191
0.8852	High Similarity	NPC225791
0.885	High Similarity	NPC150400
0.885	High Similarity	NPC251263
0.885	High Similarity	NPC309714
0.885	High Similarity	NPC323341
0.885	High Similarity	NPC133818
0.885	High Similarity	NPC114304
0.885	High Similarity	NPC219180
0.885	High Similarity	NPC155410
0.885	High Similarity	NPC473826
0.885	High Similarity	NPC73318
0.885	High Similarity	NPC475287
0.885	High Similarity	NPC192600
0.885	High Similarity	NPC241909
0.885	High Similarity	NPC114287
0.885	High Similarity	NPC163183
0.885	High Similarity	NPC46665
0.885	High Similarity	NPC473343
0.885	High Similarity	NPC151543
0.885	High Similarity	NPC134835
0.885	High Similarity	NPC174720
0.885	High Similarity	NPC295823
0.885	High Similarity	NPC96641
0.885	High Similarity	NPC475467
0.885	High Similarity	NPC166422
0.8833	High Similarity	NPC477191
0.8833	High Similarity	NPC477192
0.8833	High Similarity	NPC477193
0.8833	High Similarity	NPC477194
0.8818	High Similarity	NPC473586
0.8807	High Similarity	NPC148603
0.8807	High Similarity	NPC203354
0.8807	High Similarity	NPC473127
0.8807	High Similarity	NPC110656
0.8807	High Similarity	NPC173583
0.8793	High Similarity	NPC477464
0.8793	High Similarity	NPC471577
0.8793	High Similarity	NPC473401
0.8783	High Similarity	NPC85154
0.8783	High Similarity	NPC69811
0.8783	High Similarity	NPC185466
0.8783	High Similarity	NPC104137
0.8783	High Similarity	NPC286457
0.8783	High Similarity	NPC148417
0.8783	High Similarity	NPC110633
0.8783	High Similarity	NPC473452
0.8783	High Similarity	NPC8524
0.8783	High Similarity	NPC475209
0.8783	High Similarity	NPC309223
0.8783	High Similarity	NPC475514
0.8783	High Similarity	NPC470876
0.8783	High Similarity	NPC33012
0.8783	High Similarity	NPC102505
0.8783	High Similarity	NPC123522
0.8783	High Similarity	NPC220160
0.8783	High Similarity	NPC191827
0.8783	High Similarity	NPC136768
0.878	High Similarity	NPC476777
0.878	High Similarity	NPC476778
0.8761	High Similarity	NPC104400
0.8761	High Similarity	NPC276093
0.8761	High Similarity	NPC473383
0.8761	High Similarity	NPC109079
0.8761	High Similarity	NPC79718
0.8761	High Similarity	NPC473373
0.8761	High Similarity	NPC471383
0.8761	High Similarity	NPC10320
0.8761	High Similarity	NPC475504
0.8761	High Similarity	NPC101744
0.8761	High Similarity	NPC257468
0.8761	High Similarity	NPC475516
0.8761	High Similarity	NPC102439
0.8761	High Similarity	NPC104071
0.8761	High Similarity	NPC292677
0.8761	High Similarity	NPC139894
0.8761	High Similarity	NPC469946
0.8761	High Similarity	NPC139044
0.8761	High Similarity	NPC324875
0.876	High Similarity	NPC477196
0.876	High Similarity	NPC477076
0.876	High Similarity	NPC477079
0.876	High Similarity	NPC470912
0.876	High Similarity	NPC470913
0.876	High Similarity	NPC477077
0.8739	High Similarity	NPC471090
0.8729	High Similarity	NPC74259
0.8729	High Similarity	NPC474423
0.8727	High Similarity	NPC88349
0.8718	High Similarity	NPC476127
0.8718	High Similarity	NPC268184
0.8718	High Similarity	NPC476150
0.8716	High Similarity	NPC473123
0.8716	High Similarity	NPC473124
0.8716	High Similarity	NPC123796
0.871	High Similarity	NPC279915
0.871	High Similarity	NPC110700

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 NPC470517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	1984
0.2-0.3	3874
0.3-0.4	2075
0.4-0.5	593
0.5-0.6	268
0.6-0.7	73
0.7-0.8	19
0.8-0.85	6
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD8377	Approved
0.8559	High Similarity	NPD8294	Approved
0.8487	Intermediate Similarity	NPD8335	Approved
0.8487	Intermediate Similarity	NPD8380	Approved
0.8487	Intermediate Similarity	NPD8379	Approved
0.8487	Intermediate Similarity	NPD8378	Approved
0.8487	Intermediate Similarity	NPD8296	Approved
0.8333	Intermediate Similarity	NPD8033	Approved
0.8197	Intermediate Similarity	NPD8328	Phase 3
0.8167	Intermediate Similarity	NPD7516	Approved
0.8087	Intermediate Similarity	NPD6686	Approved
0.8083	Intermediate Similarity	NPD7327	Approved
0.8083	Intermediate Similarity	NPD7328	Approved
0.8051	Intermediate Similarity	NPD8133	Approved
0.8033	Intermediate Similarity	NPD7503	Approved
0.7863	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7507	Approved
0.7705	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7319	Approved
0.746	Intermediate Similarity	NPD8516	Approved
0.746	Intermediate Similarity	NPD8515	Approved
0.746	Intermediate Similarity	NPD8517	Approved
0.7395	Intermediate Similarity	NPD6412	Phase 2
0.7391	Intermediate Similarity	NPD7638	Approved
0.7328	Intermediate Similarity	NPD7640	Approved
0.7328	Intermediate Similarity	NPD7639	Approved
0.7323	Intermediate Similarity	NPD8513	Phase 3
0.7193	Intermediate Similarity	NPD7748	Approved
0.7155	Intermediate Similarity	NPD7902	Approved
0.7154	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7736	Approved
0.7094	Intermediate Similarity	NPD4225	Approved
0.7018	Intermediate Similarity	NPD7515	Phase 2
0.6975	Remote Similarity	NPD5344	Discontinued
0.6949	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7900	Approved
0.6897	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7625	Phase 1
0.6875	Remote Similarity	NPD7115	Discovery
0.6791	Remote Similarity	NPD8293	Discontinued
0.6783	Remote Similarity	NPD7838	Discovery
0.6777	Remote Similarity	NPD7632	Discontinued
0.6742	Remote Similarity	NPD6370	Approved
0.6697	Remote Similarity	NPD7645	Phase 2
0.6694	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8297	Approved
0.6693	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD8171	Discontinued
0.6642	Remote Similarity	NPD7492	Approved
0.664	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6698	Approved
0.6638	Remote Similarity	NPD46	Approved
0.6615	Remote Similarity	NPD6009	Approved
0.6612	Remote Similarity	NPD6648	Approved
0.6593	Remote Similarity	NPD6616	Approved
0.6591	Remote Similarity	NPD6054	Approved
0.6591	Remote Similarity	NPD6319	Approved
0.6544	Remote Similarity	NPD7078	Approved
0.6532	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4632	Approved
0.65	Remote Similarity	NPD8450	Suspended
0.6466	Remote Similarity	NPD6059	Approved
0.6444	Remote Similarity	NPD6067	Discontinued
0.6429	Remote Similarity	NPD8449	Approved
0.6423	Remote Similarity	NPD8074	Phase 3
0.6418	Remote Similarity	NPD6016	Approved
0.6418	Remote Similarity	NPD6015	Approved
0.6404	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6881	Approved
0.6378	Remote Similarity	NPD6899	Approved
0.637	Remote Similarity	NPD5988	Approved
0.6357	Remote Similarity	NPD6649	Approved
0.6357	Remote Similarity	NPD6650	Approved
0.6357	Remote Similarity	NPD8130	Phase 1
0.6349	Remote Similarity	NPD7128	Approved
0.6349	Remote Similarity	NPD6675	Approved
0.6349	Remote Similarity	NPD6402	Approved
0.6349	Remote Similarity	NPD5739	Approved
0.6328	Remote Similarity	NPD6372	Approved
0.6328	Remote Similarity	NPD6373	Approved
0.6303	Remote Similarity	NPD8034	Phase 2
0.6303	Remote Similarity	NPD8035	Phase 2
0.6299	Remote Similarity	NPD5697	Approved
0.6279	Remote Similarity	NPD7102	Approved
0.6279	Remote Similarity	NPD7290	Approved
0.6279	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD7320	Approved
0.6231	Remote Similarity	NPD6847	Approved
0.6231	Remote Similarity	NPD6617	Approved
0.6231	Remote Similarity	NPD6869	Approved
0.6204	Remote Similarity	NPD7830	Approved
0.6204	Remote Similarity	NPD7604	Phase 2
0.6204	Remote Similarity	NPD7829	Approved
0.6202	Remote Similarity	NPD6014	Approved
0.6202	Remote Similarity	NPD6013	Approved
0.6202	Remote Similarity	NPD6012	Approved
0.6176	Remote Similarity	NPD5983	Phase 2
0.6176	Remote Similarity	NPD6921	Approved
0.6172	Remote Similarity	NPD5701	Approved
0.6124	Remote Similarity	NPD6011	Approved
0.6116	Remote Similarity	NPD6399	Phase 3
0.6115	Remote Similarity	NPD6336	Discontinued
0.6102	Remote Similarity	NPD3573	Approved
0.6087	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6053	Discontinued
0.6053	Remote Similarity	NPD7525	Registered
0.605	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6083	Phase 2
0.6048	Remote Similarity	NPD6084	Phase 2
0.6047	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD3669	Approved
0.6033	Remote Similarity	NPD6079	Approved
0.6031	Remote Similarity	NPD6371	Approved
0.6031	Remote Similarity	NPD4634	Approved
0.6028	Remote Similarity	NPD6033	Approved
0.6017	Remote Similarity	NPD3618	Phase 1
0.6014	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD7266	Discontinued
0.5985	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5211	Phase 2
0.5969	Remote Similarity	NPD6008	Approved
0.5966	Remote Similarity	NPD7524	Approved
0.5957	Remote Similarity	NPD8448	Approved
0.5952	Remote Similarity	NPD5285	Approved
0.5952	Remote Similarity	NPD4696	Approved
0.5952	Remote Similarity	NPD5286	Approved
0.5944	Remote Similarity	NPD8390	Approved
0.5944	Remote Similarity	NPD8392	Approved
0.5944	Remote Similarity	NPD8391	Approved
0.5932	Remote Similarity	NPD1694	Approved
0.5928	Remote Similarity	NPD7799	Discontinued
0.5926	Remote Similarity	NPD6274	Approved
0.592	Remote Similarity	NPD4755	Approved
0.5915	Remote Similarity	NPD8336	Approved
0.5915	Remote Similarity	NPD8337	Approved
0.5912	Remote Similarity	NPD7100	Approved
0.5912	Remote Similarity	NPD7101	Approved
0.5902	Remote Similarity	NPD7637	Suspended
0.5902	Remote Similarity	NPD7983	Approved
0.5902	Remote Similarity	NPD6411	Approved
0.5891	Remote Similarity	NPD5141	Approved
0.5887	Remote Similarity	NPD8451	Approved
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD6684	Approved
0.5868	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8338	Approved
0.5859	Remote Similarity	NPD5226	Approved
0.5859	Remote Similarity	NPD4633	Approved
0.5859	Remote Similarity	NPD5224	Approved
0.5859	Remote Similarity	NPD5225	Approved
0.5854	Remote Similarity	NPD5778	Approved
0.5854	Remote Similarity	NPD4202	Approved
0.5854	Remote Similarity	NPD5779	Approved
0.585	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.584	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.584	Remote Similarity	NPD5221	Approved
0.584	Remote Similarity	NPD5222	Approved
0.5839	Remote Similarity	NPD6335	Approved
0.5839	Remote Similarity	NPD8455	Phase 2
0.5827	Remote Similarity	NPD8444	Approved
0.5827	Remote Similarity	NPD4700	Approved
0.5814	Remote Similarity	NPD5174	Approved
0.5814	Remote Similarity	NPD5175	Approved
0.5814	Remote Similarity	NPD8312	Approved
0.5814	Remote Similarity	NPD8313	Approved
0.5811	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD6868	Approved
0.5794	Remote Similarity	NPD5173	Approved
0.5785	Remote Similarity	NPD6672	Approved
0.5785	Remote Similarity	NPD5737	Approved
0.5785	Remote Similarity	NPD6903	Approved
0.5782	Remote Similarity	NPD8415	Approved
0.5781	Remote Similarity	NPD5223	Approved
0.5781	Remote Similarity	NPD4159	Approved
0.5766	Remote Similarity	NPD6317	Approved
0.576	Remote Similarity	NPD5695	Phase 3
0.5758	Remote Similarity	NPD4729	Approved
0.5758	Remote Similarity	NPD4730	Approved
0.5753	Remote Similarity	NPD6845	Suspended
0.5748	Remote Similarity	NPD5696	Approved
0.5745	Remote Similarity	NPD7642	Approved
0.574	Remote Similarity	NPD7228	Approved
0.5738	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6101	Approved
0.5725	Remote Similarity	NPD7641	Discontinued
0.5725	Remote Similarity	NPD4768	Approved
0.5725	Remote Similarity	NPD6313	Approved
0.5725	Remote Similarity	NPD6314	Approved
0.5725	Remote Similarity	NPD4767	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