NPASS Compound

Structure

CID110700 OpenBabel06191715462D 85 93 0 0 1 0 0 0 0 0999 V2000 5.9346 -1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6956 -4.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8806 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3701 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8478 2.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8806 1.1101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8478 -1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8478 -0.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9346 -2.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0868 -2.9368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5434 0.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5434 3.4263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 2.9368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5434 0.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5434 4.4053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8691 4.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3257 1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3701 1.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6956 -1.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6956 -3.9158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 0.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6956 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.8691 5.8737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1735 1.9579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3912 4.8947 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5434 1.4684 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8478 1.4684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8478 -1.4684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3912 2.9368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2390 -2.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0213 6.3632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1735 2.9368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3912 5.8737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2390 6.3632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1735 5.8737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0868 5.8737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7823 1.9579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7823 2.9368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9346 1.4684 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3257 3.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9346 3.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3912 -0.9789 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5434 -1.4684 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9346 0.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1735 4.8947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0868 4.8947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4779 2.9368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0868 2.9368 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3912 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 1.9579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3912 1.9579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8478 0.4895 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 1.6956 -0.9789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6956 4.8947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8596 1.1101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5434 -2.4474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -3.4263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.7169 6.3632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0213 1.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -2.4474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3912 -2.9368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0213 7.3421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0213 3.4263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5434 6.3632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2390 7.3421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3257 6.3632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9346 6.3632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6301 1.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7823 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0868 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0213 4.4053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4779 1.9579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5434 -3.4263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2390 4.4053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2390 3.4263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2390 -1.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6301 3.4263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0868 1.9579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3257 4.4053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9346 4.4053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 24 1 0 0 0 0 3 53 1 0 0 0 0 4 53 1 0 0 0 0 7 56 1 0 0 0 0 9 10 2 0 0 0 0 10 34 1 0 0 0 0 11 12 1 0 0 0 0 11 25 2 0 0 0 0 12 31 1 0 0 0 0 13 16 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 33 1 0 0 0 0 15 54 1 0 0 0 0 16 56 1 0 0 0 0 17 26 1 0 0 0 0 17 53 1 0 0 0 0 18 32 1 0 0 0 0 18 57 1 0 0 0 0 19 59 1 0 0 0 0 20 27 1 0 0 0 0 20 76 1 0 0 0 0 21 28 1 0 0 0 0 21 77 1 0 0 0 0 22 55 1 0 0 0 0 22 60 2 0 0 0 0 23 61 1 0 0 0 0 24 62 2 0 0 0 0 24 78 1 0 0 0 0 25 26 1 0 0 0 0 25 57 1 0 0 0 0 26 58 1 6 0 0 0 27 35 1 0 0 0 0 27 63 1 1 0 0 0 28 36 1 0 0 0 0 28 64 1 6 0 0 0 29 19 1 1 0 0 0 29 37 1 0 0 0 0 29 79 1 0 0 0 0 30 54 1 0 0 0 0 30 55 1 0 0 0 0 31 54 1 1 0 0 0 31 56 1 0 0 0 0 32 58 1 6 0 0 0 32 65 1 0 0 0 0 33 55 1 1 0 0 0 33 80 1 0 0 0 0 34 66 2 0 0 0 0 34 81 1 0 0 0 0 35 39 1 0 0 0 0 35 67 1 6 0 0 0 36 44 1 0 0 0 0 36 68 1 6 0 0 0 37 38 1 0 0 0 0 37 69 1 1 0 0 0 38 40 1 0 0 0 0 38 70 1 1 0 0 0 39 49 1 0 0 0 0 39 71 1 1 0 0 0 40 50 1 0 0 0 0 40 72 1 6 0 0 0 41 42 1 0 0 0 0 41 43 1 0 0 0 0 41 73 1 1 0 0 0 42 45 1 0 0 0 0 42 82 1 6 0 0 0 43 48 1 6 0 0 0 43 83 1 0 0 0 0 44 51 1 0 0 0 0 44 84 1 1 0 0 0 45 52 1 0 0 0 0 45 85 1 1 0 0 0 46 47 1 0 0 0 0 46 53 1 0 0 0 0 46 81 1 1 0 0 0 47 58 1 6 0 0 0 47 78 1 0 0 0 0 48 74 2 0 0 0 0 48 75 1 0 0 0 0 49 76 1 0 0 0 0 49 84 1 6 0 0 0 50 79 1 0 0 0 0 50 85 1 1 0 0 0 51 77 1 0 0 0 0 51 82 1 6 0 0 0 52 80 1 6 0 0 0 52 83 1 0 0 0 0 54 5 1 1 0 0 0 55 6 1 1 0 0 0 56 57 1 6 0 0 0 57 8 1 6 0 0 0 58 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1216.55
Volume:	1156.233
LogP:	0.283
LogD:	0.468
LogS:	-2.667
# Rotatable Bonds:	17
TPSA:	423.57
# H-Bond Aceptor:	27
# H-Bond Donor:	13
# Rings:	9
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.027
Synthetic Accessibility Score:	7.373
Fsp3:	0.862
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.634
MDCK Permeability:	0.00042097020195797086
Pgp-inhibitor:	0.019
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.279
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	38.53343200683594%
Volume Distribution (VD):	0.196
Pgp-substrate:	24.7308292388916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	0.19
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.148
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.177
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.892

Download Data

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

Natural Product: NPC110700

Natural Product ID:	NPC110700
*Common Name:**	Theasaponin E1
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4S,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-acetyloxy-10-[(Z)-but-2-enoyl]oxy-4-formyl-8-hydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:	Theasaponin E1
Standard InCHIKey:	ZYXKWKYFPFVOAL-WUXQPFAESA-N
Standard InCHI:	InChI=1S/C58H88O27/c1-9-10-34(66)81-46-47(78-24(2)62)58(23-61)26(17-53(46,3)4)25-11-12-31-54(5)15-14-33(55(6,22-60)30(54)13-16-56(31,7)57(25,8)18-32(58)65)80-52-45(85-50-40(72)38(70)37(69)29(19-59)79-50)42(41(73)43(83-52)48(74)75)82-51-44(36(68)28(64)21-77-51)84-49-39(71)35(67)27(63)20-76-49/h9-11,22,26-33,35-47,49-52,59,61,63-65,67-73H,12-21,23H2,1-8H3,(H,74,75)/b10-9-/t26-,27+,28-,29+,30?,31+,32+,33-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+,46-,47-,49-,50-,51-,52+,54-,55-,56+,57+,58-/m0/s1
SMILES:	C/C=CC(=O)O[C@H]1[C@H](OC(=O)C)[C@]2(CO)[C@H](O)C[C@@]3(C(=CC[C@H]4[C@@]3(C)CCC3[C@]4(C)CC[C@@H]([C@@]3(C)C=O)O[C@@H]3O[C@H](C(=O)O)[C@H]([C@@H]([C@H]3O[C@@H]3O[C@H](CO)[C@@H]([C@@H]([C@H]3O)O)O)O[C@@H]3OC[C@@H]([C@@H]([C@H]3O[C@@H]3OC[C@H]([C@@H]([C@H]3O)O)O)O)O)O)[C@@H]2CC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465965
PubChem CID:	44566563
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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8258	Camellia sinensis	Species	Theaceae	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
Others	9

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	578.5	mg/dl	PMID[500760]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	373.9	mg/dl	PMID[500760]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	342.3	mg/dl	PMID[500760]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	430.7	mg/dl	PMID[500760]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	312.2	mg/dl	PMID[500760]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	389.5	mg/dl	PMID[500760]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	233.9	mg/dl	PMID[500760]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	267.2	mg/dl	PMID[500760]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	294.9	mg/dl	PMID[500760]

☑ 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 NPC110700 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	313
0.1-0.2	1870
0.2-0.3	4820
0.3-0.4	8348
0.4-0.5	12118
0.5-0.6	8387
0.6-0.7	4396
0.7-0.8	1670
0.8-0.85	377
0.85-0.9	192
0.9-0.95	136
0.95-1	70

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279915
0.9919	High Similarity	NPC476778
0.9919	High Similarity	NPC476777
0.9837	High Similarity	NPC476779
0.9756	High Similarity	NPC477195
0.9756	High Similarity	NPC476776
0.9756	High Similarity	NPC312650
0.9677	High Similarity	NPC225791
0.9675	High Similarity	NPC476775
0.9675	High Similarity	NPC476774
0.9675	High Similarity	NPC271610
0.9675	High Similarity	NPC476780
0.9597	High Similarity	NPC46823
0.9597	High Similarity	NPC192765
0.9597	High Similarity	NPC30279
0.9597	High Similarity	NPC71391
0.9597	High Similarity	NPC473918
0.9597	High Similarity	NPC277212
0.9597	High Similarity	NPC178264
0.9593	High Similarity	NPC470518
0.9593	High Similarity	NPC252289
0.9593	High Similarity	NPC11577
0.9593	High Similarity	NPC141600
0.9593	High Similarity	NPC472267
0.9593	High Similarity	NPC82380
0.9593	High Similarity	NPC1314
0.9593	High Similarity	NPC97918
0.9593	High Similarity	NPC252657
0.9593	High Similarity	NPC273878
0.9593	High Similarity	NPC265841
0.9593	High Similarity	NPC107536
0.9593	High Similarity	NPC88311
0.9593	High Similarity	NPC115656
0.9593	High Similarity	NPC47995
0.9593	High Similarity	NPC477196
0.9593	High Similarity	NPC244296
0.9593	High Similarity	NPC9470
0.9593	High Similarity	NPC305793
0.9593	High Similarity	NPC269484
0.9593	High Similarity	NPC280029
0.9516	High Similarity	NPC477197
0.9512	High Similarity	NPC477191
0.9512	High Similarity	NPC477194
0.9512	High Similarity	NPC477193
0.9512	High Similarity	NPC477192
0.9435	High Similarity	NPC477079
0.9435	High Similarity	NPC477077
0.9435	High Similarity	NPC470912
0.9435	High Similarity	NPC470913
0.9435	High Similarity	NPC477076
0.936	High Similarity	NPC478155
0.936	High Similarity	NPC25998
0.9355	High Similarity	NPC475281
0.9355	High Similarity	NPC477075
0.9355	High Similarity	NPC477078
0.9355	High Similarity	NPC470475
0.9355	High Similarity	NPC329923
0.935	High Similarity	NPC284449
0.9286	High Similarity	NPC478154
0.9286	High Similarity	NPC478153
0.9286	High Similarity	NPC478152
0.9286	High Similarity	NPC478150
0.9274	High Similarity	NPC470516
0.9268	High Similarity	NPC160452
0.9213	High Similarity	NPC478151
0.9206	High Similarity	NPC476074
0.9206	High Similarity	NPC172374
0.9206	High Similarity	NPC45346
0.9206	High Similarity	NPC301639
0.9206	High Similarity	NPC329993
0.9206	High Similarity	NPC475377
0.9206	High Similarity	NPC262796
0.9206	High Similarity	NPC264566
0.9206	High Similarity	NPC475167
0.9206	High Similarity	NPC134914
0.9206	High Similarity	NPC478064
0.9206	High Similarity	NPC478065
0.9206	High Similarity	NPC173435
0.92	High Similarity	NPC470476
0.9194	High Similarity	NPC475368
0.9187	High Similarity	NPC2370
0.9187	High Similarity	NPC44716
0.9187	High Similarity	NPC257211
0.9113	High Similarity	NPC471963
0.9113	High Similarity	NPC33068
0.9113	High Similarity	NPC247315
0.9113	High Similarity	NPC471962
0.9106	High Similarity	NPC80986
0.9106	High Similarity	NPC213952
0.9106	High Similarity	NPC187290
0.9106	High Similarity	NPC4749
0.9106	High Similarity	NPC475591
0.9106	High Similarity	NPC236870
0.9106	High Similarity	NPC10607
0.9106	High Similarity	NPC21691
0.9055	High Similarity	NPC300655
0.9055	High Similarity	NPC222951
0.9055	High Similarity	NPC311178
0.9055	High Similarity	NPC43589
0.9048	High Similarity	NPC472269
0.9048	High Similarity	NPC23020
0.9048	High Similarity	NPC472268
0.9048	High Similarity	NPC112492
0.9048	High Similarity	NPC472270
0.9032	High Similarity	NPC471961
0.9032	High Similarity	NPC202666
0.9032	High Similarity	NPC200049
0.9032	High Similarity	NPC302543
0.9032	High Similarity	NPC283417
0.9032	High Similarity	NPC14617
0.9032	High Similarity	NPC471964
0.9032	High Similarity	NPC258617
0.9032	High Similarity	NPC262199
0.9024	High Similarity	NPC31193
0.9024	High Similarity	NPC301449
0.9024	High Similarity	NPC222580
0.9024	High Similarity	NPC114484
0.9024	High Similarity	NPC171544
0.9024	High Similarity	NPC62725
0.9024	High Similarity	NPC223301
0.9024	High Similarity	NPC104372
0.9024	High Similarity	NPC22956
0.9024	High Similarity	NPC187618
0.9024	High Similarity	NPC297263
0.9024	High Similarity	NPC86222
0.9024	High Similarity	NPC242840
0.9024	High Similarity	NPC159309
0.9024	High Similarity	NPC31838
0.9024	High Similarity	NPC302887
0.9024	High Similarity	NPC64715
0.9024	High Similarity	NPC11242
0.8984	High Similarity	NPC475177
0.8984	High Similarity	NPC233223
0.8984	High Similarity	NPC322904
0.8984	High Similarity	NPC319719
0.8984	High Similarity	NPC183816
0.8984	High Similarity	NPC324933
0.8984	High Similarity	NPC473679
0.8984	High Similarity	NPC475444
0.8984	High Similarity	NPC196874
0.896	High Similarity	NPC23275
0.8952	High Similarity	NPC131469
0.8952	High Similarity	NPC313110
0.8952	High Similarity	NPC471965
0.8952	High Similarity	NPC162574
0.8943	High Similarity	NPC294112
0.8943	High Similarity	NPC236657
0.8943	High Similarity	NPC118440
0.8898	High Similarity	NPC220838
0.8898	High Similarity	NPC45606
0.8889	High Similarity	NPC297950
0.8889	High Similarity	NPC285091
0.8889	High Similarity	NPC470218
0.8889	High Similarity	NPC181066
0.8889	High Similarity	NPC469947
0.888	High Similarity	NPC30735
0.888	High Similarity	NPC235405
0.888	High Similarity	NPC281148
0.8862	High Similarity	NPC214484
0.8862	High Similarity	NPC11551
0.8862	High Similarity	NPC208381
0.8862	High Similarity	NPC6377
0.8862	High Similarity	NPC475171
0.8862	High Similarity	NPC157868
0.8862	High Similarity	NPC180550
0.8862	High Similarity	NPC192791
0.8862	High Similarity	NPC472949
0.8862	High Similarity	NPC114441
0.8862	High Similarity	NPC39211
0.8862	High Similarity	NPC469945
0.8862	High Similarity	NPC309780
0.8862	High Similarity	NPC473884
0.8862	High Similarity	NPC35405
0.8855	High Similarity	NPC190065
0.8855	High Similarity	NPC141215
0.8855	High Similarity	NPC471089
0.881	High Similarity	NPC470477
0.88	High Similarity	NPC107966
0.88	High Similarity	NPC235438
0.88	High Similarity	NPC40775
0.88	High Similarity	NPC249848
0.8788	High Similarity	NPC295885
0.8788	High Similarity	NPC140045
0.8788	High Similarity	NPC596
0.878	High Similarity	NPC470515
0.878	High Similarity	NPC286347
0.878	High Similarity	NPC471548
0.878	High Similarity	NPC473459
0.8779	High Similarity	NPC262813
0.873	High Similarity	NPC478066
0.872	High Similarity	NPC75417
0.8712	High Similarity	NPC251998
0.871	High Similarity	NPC470517
0.871	High Similarity	NPC470915
0.871	High Similarity	NPC473401
0.871	High Similarity	NPC473386
0.871	High Similarity	NPC470911
0.8699	High Similarity	NPC473824
0.8699	High Similarity	NPC323359
0.8699	High Similarity	NPC475119

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 NPC110700 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	2062
0.2-0.3	3767
0.3-0.4	1947
0.4-0.5	658
0.5-0.6	266
0.6-0.7	118
0.7-0.8	30
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD8328	Phase 3
0.8548	High Similarity	NPD8295	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD7319	Approved
0.803	Intermediate Similarity	NPD7507	Approved
0.8	Intermediate Similarity	NPD8516	Approved
0.8	Intermediate Similarity	NPD8515	Approved
0.8	Intermediate Similarity	NPD8517	Approved
0.791	Intermediate Similarity	NPD7736	Approved
0.7863	Intermediate Similarity	NPD8513	Phase 3
0.776	Intermediate Similarity	NPD6686	Approved
0.7734	Intermediate Similarity	NPD8133	Approved
0.7698	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD8294	Approved
0.7652	Intermediate Similarity	NPD8377	Approved
0.7594	Intermediate Similarity	NPD8378	Approved
0.7594	Intermediate Similarity	NPD8380	Approved
0.7594	Intermediate Similarity	NPD8296	Approved
0.7594	Intermediate Similarity	NPD8335	Approved
0.7594	Intermediate Similarity	NPD8379	Approved
0.7537	Intermediate Similarity	NPD6370	Approved
0.748	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD8033	Approved
0.7445	Intermediate Similarity	NPD8293	Discontinued
0.7426	Intermediate Similarity	NPD7492	Approved
0.7388	Intermediate Similarity	NPD6054	Approved
0.7388	Intermediate Similarity	NPD6319	Approved
0.7372	Intermediate Similarity	NPD6616	Approved
0.7333	Intermediate Similarity	NPD7503	Approved
0.7319	Intermediate Similarity	NPD7078	Approved
0.7313	Intermediate Similarity	NPD7516	Approved
0.7308	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD8297	Approved
0.7252	Intermediate Similarity	NPD6882	Approved
0.7239	Intermediate Similarity	NPD7327	Approved
0.7239	Intermediate Similarity	NPD7328	Approved
0.7206	Intermediate Similarity	NPD6015	Approved
0.7206	Intermediate Similarity	NPD6016	Approved
0.7164	Intermediate Similarity	NPD7115	Discovery
0.7164	Intermediate Similarity	NPD6009	Approved
0.7153	Intermediate Similarity	NPD5988	Approved
0.7132	Intermediate Similarity	NPD6059	Approved
0.7132	Intermediate Similarity	NPD6412	Phase 2
0.7045	Intermediate Similarity	NPD6649	Approved
0.7045	Intermediate Similarity	NPD6650	Approved
0.704	Intermediate Similarity	NPD7902	Approved
0.6957	Remote Similarity	NPD6921	Approved
0.695	Remote Similarity	NPD8074	Phase 3
0.6947	Remote Similarity	NPD6899	Approved
0.6947	Remote Similarity	NPD6881	Approved
0.694	Remote Similarity	NPD4632	Approved
0.6935	Remote Similarity	NPD7748	Approved
0.6917	Remote Similarity	NPD8130	Phase 1
0.6894	Remote Similarity	NPD6372	Approved
0.6894	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6373	Approved
0.687	Remote Similarity	NPD5697	Approved
0.685	Remote Similarity	NPD7638	Approved
0.685	Remote Similarity	NPD4225	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7900	Approved
0.6797	Remote Similarity	NPD7640	Approved
0.6797	Remote Similarity	NPD7639	Approved
0.6794	Remote Similarity	NPD5739	Approved
0.6794	Remote Similarity	NPD6675	Approved
0.6794	Remote Similarity	NPD7128	Approved
0.6794	Remote Similarity	NPD6402	Approved
0.6791	Remote Similarity	NPD6617	Approved
0.6791	Remote Similarity	NPD6847	Approved
0.6791	Remote Similarity	NPD6869	Approved
0.6774	Remote Similarity	NPD7515	Phase 2
0.6767	Remote Similarity	NPD6014	Approved
0.6767	Remote Similarity	NPD6013	Approved
0.6767	Remote Similarity	NPD6012	Approved
0.6738	Remote Similarity	NPD7604	Phase 2
0.6716	Remote Similarity	NPD4634	Approved
0.6714	Remote Similarity	NPD5983	Phase 2
0.6713	Remote Similarity	NPD8448	Approved
0.6692	Remote Similarity	NPD7320	Approved
0.6692	Remote Similarity	NPD6011	Approved
0.669	Remote Similarity	NPD8392	Approved
0.669	Remote Similarity	NPD8391	Approved
0.669	Remote Similarity	NPD8390	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6644	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD8451	Approved
0.6643	Remote Similarity	NPD6336	Discontinued
0.662	Remote Similarity	NPD7830	Approved
0.662	Remote Similarity	NPD7829	Approved
0.6617	Remote Similarity	NPD5701	Approved
0.6617	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7799	Discontinued
0.6531	Remote Similarity	NPD7260	Phase 2
0.651	Remote Similarity	NPD8415	Approved
0.6503	Remote Similarity	NPD7642	Approved
0.6493	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD8340	Approved
0.6458	Remote Similarity	NPD8341	Approved
0.6458	Remote Similarity	NPD8299	Approved
0.6458	Remote Similarity	NPD8342	Approved
0.6454	Remote Similarity	NPD7101	Approved
0.6454	Remote Similarity	NPD7100	Approved
0.6439	Remote Similarity	NPD5211	Phase 2
0.6434	Remote Similarity	NPD4697	Phase 3
0.6429	Remote Similarity	NPD46	Approved
0.6429	Remote Similarity	NPD6698	Approved
0.6423	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD8368	Discontinued
0.6412	Remote Similarity	NPD4696	Approved
0.6412	Remote Similarity	NPD5285	Approved
0.6412	Remote Similarity	NPD5286	Approved
0.6383	Remote Similarity	NPD6335	Approved
0.6378	Remote Similarity	NPD6411	Approved
0.6378	Remote Similarity	NPD7983	Approved
0.6364	Remote Similarity	NPD5344	Discontinued
0.6357	Remote Similarity	NPD6274	Approved
0.6357	Remote Similarity	NPD6868	Approved
0.6343	Remote Similarity	NPD5141	Approved
0.6328	Remote Similarity	NPD5778	Approved
0.6328	Remote Similarity	NPD5779	Approved
0.632	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD5226	Approved
0.6316	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD5224	Approved
0.6316	Remote Similarity	NPD4633	Approved
0.6316	Remote Similarity	NPD7632	Discontinued
0.6312	Remote Similarity	NPD6317	Approved
0.6308	Remote Similarity	NPD5222	Approved
0.6308	Remote Similarity	NPD5221	Approved
0.6308	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD8407	Phase 2
0.6276	Remote Similarity	NPD6067	Discontinued
0.6269	Remote Similarity	NPD5174	Approved
0.6269	Remote Similarity	NPD5175	Approved
0.6268	Remote Similarity	NPD6314	Approved
0.6268	Remote Similarity	NPD6313	Approved
0.6268	Remote Similarity	NPD7641	Discontinued
0.6266	Remote Similarity	NPD7625	Phase 1
0.626	Remote Similarity	NPD6083	Phase 2
0.626	Remote Similarity	NPD6084	Phase 2
0.626	Remote Similarity	NPD4755	Approved
0.626	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD8444	Approved
0.625	Remote Similarity	NPD6079	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8034	Phase 2
0.6243	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD5956	Approved
0.6241	Remote Similarity	NPD5223	Approved
0.6232	Remote Similarity	NPD6371	Approved
0.622	Remote Similarity	NPD6101	Approved
0.622	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8080	Discontinued
0.6204	Remote Similarity	NPD4730	Approved
0.6204	Remote Similarity	NPD4729	Approved
0.6188	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6008	Approved
0.6172	Remote Similarity	NPD7838	Discovery
0.6167	Remote Similarity	NPD8435	Approved
0.6165	Remote Similarity	NPD4700	Approved
0.6159	Remote Similarity	NPD6845	Suspended
0.6159	Remote Similarity	NPD8338	Approved
0.6143	Remote Similarity	NPD6053	Discontinued
0.6138	Remote Similarity	NPD6909	Approved
0.6138	Remote Similarity	NPD6908	Approved
0.6138	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD5248	Approved
0.6115	Remote Similarity	NPD5249	Phase 3
0.6115	Remote Similarity	NPD5247	Approved
0.6115	Remote Similarity	NPD5251	Approved
0.6115	Remote Similarity	NPD5250	Approved
0.6107	Remote Similarity	NPD8337	Approved
0.6107	Remote Similarity	NPD8336	Approved
0.6107	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5328	Approved
0.609	Remote Similarity	NPD5696	Approved
0.6085	Remote Similarity	NPD8320	Phase 1
0.6085	Remote Similarity	NPD8319	Approved
0.6077	Remote Similarity	NPD8361	Approved
0.6077	Remote Similarity	NPD6399	Phase 3
0.6077	Remote Similarity	NPD8360	Approved
0.6067	Remote Similarity	NPD8312	Approved
0.6067	Remote Similarity	NPD8313	Approved
0.6065	Remote Similarity	NPD6334	Approved
0.6065	Remote Similarity	NPD6333	Approved
0.6061	Remote Similarity	NPD7839	Suspended
0.6058	Remote Similarity	NPD4768	Approved
0.6058	Remote Similarity	NPD4767	Approved
0.6056	Remote Similarity	NPD8434	Phase 2
0.6056	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD6648	Approved
0.6032	Remote Similarity	NPD1694	Approved
0.6027	Remote Similarity	NPD8274	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