NPASS Compound

Structure

CID22709 OpenBabel06191715352D 107119 0 0 1 0 0 0 0 0999 V2000 0.5828 -3.1165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2799 -2.7011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6043 -4.3722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5618 -4.3799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2692 -1.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7488 -2.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7307 -3.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4100 -3.5334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4333 -0.6240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9412 -2.0989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1053 -1.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5740 -3.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5974 -0.1324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1276 -2.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5119 -1.6798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1269 -1.6798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0171 -2.1791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4863 5.0501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0893 1.1669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0927 -4.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4556 1.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1371 4.0793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9087 -3.1085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4326 -1.6524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7341 -3.5939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3194 5.5222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.0970 2.1244 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9181 -4.9837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2810 0.7347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9625 3.5939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2580 -2.1378 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2538 -3.0552 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4256 -1.5938 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2311 -1.2062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9608 -1.9559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9335 -3.0687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.5672 -3.1218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3271 6.4797 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.9301 2.5965 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9104 -5.9411 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1141 1.2068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2503 -3.0953 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1601 6.9518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.9377 3.5540 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7358 -6.4265 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.5748 -2.1643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9855 6.4664 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.1124 4.0394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5689 -5.9544 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.6132 2.6231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7955 4.0660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9394 0.7214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.6209 3.5806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4173 -3.5674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9318 -0.2361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7495 -1.6790 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9778 5.5089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.2793 3.5673 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5765 -4.9969 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7802 2.1510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5919 -3.0820 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0987 -0.7082 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9472 -0.2084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5112 -2.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0897 -3.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2615 -2.0854 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5818 -2.0720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7458 -1.5803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3747 -1.0789 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7536 -0.6106 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6610 5.5355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2563 0.6948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2597 -4.9704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6226 0.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3040 3.6072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7264 -4.5514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5573 -2.6919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3925 -3.6072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5017 6.9651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.7554 2.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0774 -6.4132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1217 2.1643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0757 -3.5806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1678 7.9093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.7708 4.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7281 -7.3840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4079 -1.6922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8185 6.9385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.1200 4.9969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3942 -6.4398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4386 2.1377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5321 0.5368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9164 -2.1511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5996 -2.1245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1448 5.0368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2716 2.6098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7512 -4.5116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2733 -0.2228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9548 2.6364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0910 -1.6657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7588 -3.5541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8032 5.0235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7725 1.1935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4539 4.0527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4096 -4.5248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7571 -0.7215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 64 1 0 0 0 0 2 64 1 0 0 0 0 3 65 1 0 0 0 0 4 65 1 0 0 0 0 6 67 1 0 0 0 0 7 68 1 0 0 0 0 8 12 1 0 0 0 0 8 32 1 0 0 0 0 9 13 1 0 0 0 0 9 33 1 0 0 0 0 10 11 1 0 0 0 0 10 36 1 0 0 0 0 11 66 1 0 0 0 0 12 67 1 0 0 0 0 14 15 1 0 0 0 0 14 64 1 0 0 0 0 16 34 1 0 0 0 0 16 64 1 0 0 0 0 17 35 1 0 0 0 0 17 68 1 0 0 0 0 18 71 1 0 0 0 0 19 72 1 0 0 0 0 20 73 1 0 0 0 0 21 74 1 0 0 0 0 22 75 1 0 0 0 0 23 25 1 0 0 0 0 23 93 1 0 0 0 0 24 31 1 0 0 0 0 24 94 1 0 0 0 0 25 37 1 0 0 0 0 25 76 1 1 0 0 0 26 18 1 1 0 0 0 26 38 1 0 0 0 0 26 95 1 0 0 0 0 27 19 1 6 0 0 0 27 39 1 0 0 0 0 27 96 1 0 0 0 0 28 20 1 6 0 0 0 28 40 1 0 0 0 0 28 97 1 0 0 0 0 29 21 1 1 0 0 0 29 41 1 0 0 0 0 29 98 1 0 0 0 0 30 22 1 1 0 0 0 30 51 1 0 0 0 0 30 99 1 0 0 0 0 31 42 1 0 0 0 0 31100 1 1 0 0 0 32 65 1 0 0 0 0 32 66 1 1 0 0 0 33 66 1 1 0 0 0 33 67 1 0 0 0 0 34 69 1 1 0 0 0 34 70 1 0 0 0 0 35 69 1 6 0 0 0 35 77 1 0 0 0 0 36 65 1 0 0 0 0 36101 1 1 0 0 0 37 46 1 0 0 0 0 37 78 1 6 0 0 0 38 43 1 0 0 0 0 38 79 1 6 0 0 0 39 44 1 0 0 0 0 39 80 1 1 0 0 0 40 45 1 0 0 0 0 40 81 1 1 0 0 0 41 52 1 0 0 0 0 41 82 1 6 0 0 0 42 54 1 0 0 0 0 42 83 1 1 0 0 0 43 47 1 0 0 0 0 43 84 1 1 0 0 0 44 48 1 0 0 0 0 44 85 1 6 0 0 0 45 49 1 0 0 0 0 45 86 1 6 0 0 0 46 56 1 0 0 0 0 46 87 1 1 0 0 0 47 57 1 0 0 0 0 47 88 1 6 0 0 0 48 58 1 0 0 0 0 48 89 1 1 0 0 0 49 59 1 0 0 0 0 49 90 1 1 0 0 0 50 53 1 0 0 0 0 50 60 1 0 0 0 0 50 91 1 6 0 0 0 51 53 1 0 0 0 0 51102 1 6 0 0 0 52 55 1 0 0 0 0 52103 1 1 0 0 0 53104 1 1 0 0 0 54 61 1 0 0 0 0 54105 1 6 0 0 0 55 62 1 0 0 0 0 55106 1 6 0 0 0 56 93 1 0 0 0 0 56106 1 6 0 0 0 57 95 1 0 0 0 0 57102 1 1 0 0 0 58 96 1 0 0 0 0 58104 1 6 0 0 0 59 97 1 0 0 0 0 59105 1 6 0 0 0 60 99 1 0 0 0 0 60103 1 1 0 0 0 61 94 1 0 0 0 0 61101 1 1 0 0 0 62 98 1 0 0 0 0 62100 1 1 0 0 0 63 69 1 0 0 0 0 63 92 2 0 0 0 0 63107 1 0 0 0 0 66 5 1 1 0 0 0 67 68 1 6 0 0 0 68 70 1 6 0 0 0 69 15 1 6 0 0 0 70 13 1 6 0 0 0 70107 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1546.7
Volume:	1430.643
LogP:	-0.821
LogD:	0.072
LogS:	-2.216
# Rotatable Bonds:	19
TPSA:	580.35
# H-Bond Aceptor:	37
# H-Bond Donor:	21
# Rings:	13
# Heavy Atoms:	37

MedChem Properties

QED Drug-Likeness Score:	0.042
Synthetic Accessibility Score:	8.272
Fsp3:	0.986
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:	-6.606
MDCK Permeability:	0.000782820105087012
Pgp-inhibitor:	0.002
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.317
Plasma Protein Binding (PPB):	45.6816520690918%
Volume Distribution (VD):	-0.525
Pgp-substrate:	16.32896614074707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-1.478
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.322
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.792
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC22709

Natural Product ID:	NPC22709
*Common Name:**	Ardisianoside H
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WCJAQHZDGNSJBM-BNJUBNBQSA-N
Standard InCHI:	InChI=1S/C70H114O37/c1-64(2)14-15-69-34(16-64)70(107-63(69)92)13-9-33-66(5)11-10-36(65(3,4)32(66)8-12-67(33,6)68(70,7)17-35(69)77)101-61-54(105-59-49(90)45(86)40(81)28(20-73)97-59)42(83)31(24-94-61)100-62-55(106-56-46(87)37(78)25(76)23-93-56)52(41(82)29(21-74)98-62)103-60-50(91)53(104-58-48(89)44(85)39(80)27(19-72)96-58)51(30(22-75)99-60)102-57-47(88)43(84)38(79)26(18-71)95-57/h25-62,71-91H,8-24H2,1-7H3/t25-,26-,27-,28-,29-,30-,31+,32+,33-,34-,35-,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,46-,47-,48-,49-,50-,51-,52+,53-,54-,55-,56+,57+,58+,59+,60+,61+,62+,66+,67-,68+,69-,70+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CO[C@H]([C@@H]([C@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@]34[C@@]2(C)C[C@H]([C@@]2([C@H]4CC(C)(C)CC2)C(=O)O3)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL374043
PubChem CID:	16109782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	whole plants	Sendai, Miyagi Prefecture, Japan	2000-Sep	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17397219]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940450]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	28400.0	nM	PMID[531560]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	33400.0	nM	PMID[531560]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100000000.0	nM	PMID[531561]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000000.0	nM	PMID[531561]
NPT27	Others	Unspecified		IC50	=	8300.0	nM	PMID[531560]
NPT27	Others	Unspecified		IC50	>	100000000.0	nM	PMID[531561]

☑ 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 NPC22709 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	517
0.1-0.2	3748
0.2-0.3	8997
0.3-0.4	12711
0.4-0.5	7330
0.5-0.6	4508
0.6-0.7	2724
0.7-0.8	1546
0.8-0.85	471
0.85-0.9	101
0.9-0.95	33
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC207693
0.9604	High Similarity	NPC471430
0.9519	High Similarity	NPC157571
0.9515	High Similarity	NPC470622
0.9505	High Similarity	NPC273189
0.9505	High Similarity	NPC184805
0.9412	High Similarity	NPC126753
0.9406	High Similarity	NPC267637
0.934	High Similarity	NPC477465
0.9327	High Similarity	NPC471431
0.9208	High Similarity	NPC80640
0.92	High Similarity	NPC471426
0.92	High Similarity	NPC471428
0.92	High Similarity	NPC471427
0.9143	High Similarity	NPC66513
0.9135	High Similarity	NPC471626
0.9135	High Similarity	NPC262567
0.9135	High Similarity	NPC473688
0.9135	High Similarity	NPC231566
0.91	High Similarity	NPC471374
0.91	High Similarity	NPC209798
0.91	High Similarity	NPC471375
0.9048	High Similarity	NPC87393
0.9038	High Similarity	NPC40716
0.9038	High Similarity	NPC475630
0.9038	High Similarity	NPC475234
0.9038	High Similarity	NPC138219
0.9029	High Similarity	NPC469827
0.901	High Similarity	NPC51579
0.901	High Similarity	NPC80417
0.8952	High Similarity	NPC469826
0.8942	High Similarity	NPC158367
0.8942	High Similarity	NPC158051
0.8942	High Similarity	NPC119628
0.8879	High Similarity	NPC469824
0.88	High Similarity	NPC471424
0.88	High Similarity	NPC106701
0.88	High Similarity	NPC471425
0.88	High Similarity	NPC189575
0.88	High Similarity	NPC471429
0.88	High Similarity	NPC205129
0.87	High Similarity	NPC253611
0.87	High Similarity	NPC471373
0.87	High Similarity	NPC267238
0.87	High Similarity	NPC148593
0.87	High Similarity	NPC77717
0.8692	High Similarity	NPC469825
0.8649	High Similarity	NPC179429
0.86	High Similarity	NPC171741
0.86	High Similarity	NPC470623
0.86	High Similarity	NPC18724
0.86	High Similarity	NPC224003
0.86	High Similarity	NPC323231
0.8519	High Similarity	NPC228190
0.8519	High Similarity	NPC236753
0.8509	High Similarity	NPC293031
0.8509	High Similarity	NPC275225
0.8509	High Similarity	NPC68767
0.8509	High Similarity	NPC51099
0.8496	Intermediate Similarity	NPC207738
0.8421	Intermediate Similarity	NPC37860
0.8421	Intermediate Similarity	NPC473645
0.8421	Intermediate Similarity	NPC144644
0.8421	Intermediate Similarity	NPC110385
0.8421	Intermediate Similarity	NPC267694
0.8421	Intermediate Similarity	NPC142151
0.8421	Intermediate Similarity	NPC153673
0.8407	Intermediate Similarity	NPC232237
0.8407	Intermediate Similarity	NPC105800
0.8378	Intermediate Similarity	NPC146563
0.8349	Intermediate Similarity	NPC220836
0.8349	Intermediate Similarity	NPC273002
0.8349	Intermediate Similarity	NPC92297
0.8349	Intermediate Similarity	NPC94086
0.8349	Intermediate Similarity	NPC233433
0.8349	Intermediate Similarity	NPC473817
0.8333	Intermediate Similarity	NPC477464
0.8333	Intermediate Similarity	NPC471577
0.8333	Intermediate Similarity	NPC203974
0.8319	Intermediate Similarity	NPC475119
0.8319	Intermediate Similarity	NPC33012
0.8319	Intermediate Similarity	NPC286457
0.8319	Intermediate Similarity	NPC473824
0.8319	Intermediate Similarity	NPC473452
0.8319	Intermediate Similarity	NPC475514
0.8319	Intermediate Similarity	NPC85154
0.8319	Intermediate Similarity	NPC309223
0.8319	Intermediate Similarity	NPC69811
0.8319	Intermediate Similarity	NPC475209
0.8319	Intermediate Similarity	NPC102505
0.8319	Intermediate Similarity	NPC470876
0.8319	Intermediate Similarity	NPC8524
0.8319	Intermediate Similarity	NPC104137
0.8319	Intermediate Similarity	NPC220160
0.8319	Intermediate Similarity	NPC191827
0.8319	Intermediate Similarity	NPC123522
0.8302	Intermediate Similarity	NPC310031
0.8302	Intermediate Similarity	NPC80191
0.8261	Intermediate Similarity	NPC476991
0.8257	Intermediate Similarity	NPC92890
0.8257	Intermediate Similarity	NPC202898
0.8257	Intermediate Similarity	NPC475319
0.8246	Intermediate Similarity	NPC237191
0.8246	Intermediate Similarity	NPC475899
0.8246	Intermediate Similarity	NPC36831
0.823	Intermediate Similarity	NPC469823
0.823	Intermediate Similarity	NPC51465
0.823	Intermediate Similarity	NPC37134
0.823	Intermediate Similarity	NPC476992
0.823	Intermediate Similarity	NPC75287
0.823	Intermediate Similarity	NPC291903
0.823	Intermediate Similarity	NPC26626
0.823	Intermediate Similarity	NPC288205
0.823	Intermediate Similarity	NPC469820
0.823	Intermediate Similarity	NPC137414
0.823	Intermediate Similarity	NPC305267
0.822	Intermediate Similarity	NPC470218
0.8218	Intermediate Similarity	NPC50443
0.8218	Intermediate Similarity	NPC18536
0.8208	Intermediate Similarity	NPC477172
0.8198	Intermediate Similarity	NPC204392
0.8198	Intermediate Similarity	NPC1876
0.8198	Intermediate Similarity	NPC11035
0.8198	Intermediate Similarity	NPC275668
0.8198	Intermediate Similarity	NPC240734
0.8198	Intermediate Similarity	NPC91838
0.819	Intermediate Similarity	NPC470478
0.819	Intermediate Similarity	NPC477463
0.8174	Intermediate Similarity	NPC25663
0.8174	Intermediate Similarity	NPC51564
0.8174	Intermediate Similarity	NPC135849
0.8174	Intermediate Similarity	NPC473386
0.8173	Intermediate Similarity	NPC203434
0.8173	Intermediate Similarity	NPC238796
0.8173	Intermediate Similarity	NPC237071
0.8158	Intermediate Similarity	NPC68175
0.8158	Intermediate Similarity	NPC471580
0.8158	Intermediate Similarity	NPC148417
0.8158	Intermediate Similarity	NPC300419
0.8158	Intermediate Similarity	NPC110633
0.8158	Intermediate Similarity	NPC136768
0.8142	Intermediate Similarity	NPC76972
0.8142	Intermediate Similarity	NPC298034
0.8142	Intermediate Similarity	NPC54395
0.8142	Intermediate Similarity	NPC294453
0.8142	Intermediate Similarity	NPC471550
0.8142	Intermediate Similarity	NPC41061
0.8142	Intermediate Similarity	NPC227551
0.8142	Intermediate Similarity	NPC65105
0.8142	Intermediate Similarity	NPC79193
0.8142	Intermediate Similarity	NPC204414
0.8142	Intermediate Similarity	NPC476068
0.8142	Intermediate Similarity	NPC293330
0.8142	Intermediate Similarity	NPC4328
0.8142	Intermediate Similarity	NPC236638
0.8142	Intermediate Similarity	NPC469782
0.8142	Intermediate Similarity	NPC123199
0.8142	Intermediate Similarity	NPC475486
0.8142	Intermediate Similarity	NPC60557
0.8142	Intermediate Similarity	NPC475160
0.8142	Intermediate Similarity	NPC475140
0.8142	Intermediate Similarity	NPC71065
0.8142	Intermediate Similarity	NPC305981
0.8142	Intermediate Similarity	NPC309907
0.8142	Intermediate Similarity	NPC119592
0.8142	Intermediate Similarity	NPC161717
0.8142	Intermediate Similarity	NPC70809
0.8142	Intermediate Similarity	NPC469821
0.8142	Intermediate Similarity	NPC43550
0.8142	Intermediate Similarity	NPC164389
0.8142	Intermediate Similarity	NPC250247
0.8142	Intermediate Similarity	NPC79643
0.8142	Intermediate Similarity	NPC57484
0.8142	Intermediate Similarity	NPC471385
0.8142	Intermediate Similarity	NPC473714
0.8142	Intermediate Similarity	NPC224381
0.8142	Intermediate Similarity	NPC54636
0.8142	Intermediate Similarity	NPC100639
0.8142	Intermediate Similarity	NPC261506
0.8142	Intermediate Similarity	NPC67857
0.8142	Intermediate Similarity	NPC202828
0.8125	Intermediate Similarity	NPC477489
0.8125	Intermediate Similarity	NPC477492
0.8113	Intermediate Similarity	NPC20028
0.8103	Intermediate Similarity	NPC268184
0.8099	Intermediate Similarity	NPC300655
0.8099	Intermediate Similarity	NPC311178
0.8099	Intermediate Similarity	NPC222951
0.8099	Intermediate Similarity	NPC43589
0.8095	Intermediate Similarity	NPC472273
0.8095	Intermediate Similarity	NPC470591
0.8087	Intermediate Similarity	NPC469822
0.8087	Intermediate Similarity	NPC470513
0.8087	Intermediate Similarity	NPC473459
0.8087	Intermediate Similarity	NPC470514
0.8077	Intermediate Similarity	NPC94582
0.8077	Intermediate Similarity	NPC57964
0.8073	Intermediate Similarity	NPC215408
0.807	Intermediate Similarity	NPC58448
0.807	Intermediate Similarity	NPC160415

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 NPC22709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	558
0.1-0.2	3759
0.2-0.3	3225
0.3-0.4	890
0.4-0.5	400
0.5-0.6	222
0.6-0.7	69
0.7-0.8	24
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7982	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8133	Approved
0.7845	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD8328	Phase 3
0.7547	Intermediate Similarity	NPD8171	Discontinued
0.7544	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3669	Approved
0.7019	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8517	Approved
0.7016	Intermediate Similarity	NPD8515	Approved
0.7016	Intermediate Similarity	NPD8516	Approved
0.688	Remote Similarity	NPD8513	Phase 3
0.6864	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD1780	Approved
0.6827	Remote Similarity	NPD1779	Approved
0.68	Remote Similarity	NPD8294	Approved
0.68	Remote Similarity	NPD8377	Approved
0.6769	Remote Similarity	NPD7319	Approved
0.6748	Remote Similarity	NPD6940	Discontinued
0.6746	Remote Similarity	NPD8296	Approved
0.6746	Remote Similarity	NPD8380	Approved
0.6746	Remote Similarity	NPD8335	Approved
0.6746	Remote Similarity	NPD8379	Approved
0.6746	Remote Similarity	NPD8378	Approved
0.6699	Remote Similarity	NPD6114	Approved
0.6699	Remote Similarity	NPD6697	Approved
0.6699	Remote Similarity	NPD6115	Approved
0.6699	Remote Similarity	NPD6118	Approved
0.6692	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6614	Remote Similarity	NPD8033	Approved
0.6602	Remote Similarity	NPD6116	Phase 1
0.6583	Remote Similarity	NPD6686	Approved
0.6557	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD8035	Phase 2
0.6518	Remote Similarity	NPD8034	Phase 2
0.6508	Remote Similarity	NPD7327	Approved
0.6508	Remote Similarity	NPD7328	Approved
0.6505	Remote Similarity	NPD6117	Approved
0.65	Remote Similarity	NPD6412	Phase 2
0.6489	Remote Similarity	NPD8293	Discontinued
0.6476	Remote Similarity	NPD7329	Approved
0.6457	Remote Similarity	NPD7516	Approved
0.6441	Remote Similarity	NPD8084	Approved
0.6441	Remote Similarity	NPD8086	Approved
0.6441	Remote Similarity	NPD8138	Approved
0.6441	Remote Similarity	NPD8082	Approved
0.6441	Remote Similarity	NPD8083	Approved
0.6441	Remote Similarity	NPD8085	Approved
0.6441	Remote Similarity	NPD8139	Approved
0.6417	Remote Similarity	NPD8393	Approved
0.6415	Remote Similarity	NPD6928	Phase 2
0.6387	Remote Similarity	NPD8275	Approved
0.6387	Remote Similarity	NPD8276	Approved
0.6357	Remote Similarity	NPD6921	Approved
0.6356	Remote Similarity	NPD1700	Approved
0.6333	Remote Similarity	NPD8081	Approved
0.6311	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1810	Approved
0.6311	Remote Similarity	NPD1811	Approved
0.6308	Remote Similarity	NPD6370	Approved
0.626	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7902	Approved
0.6212	Remote Similarity	NPD7492	Approved
0.621	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD6616	Approved
0.6154	Remote Similarity	NPD6059	Approved
0.6154	Remote Similarity	NPD6054	Approved
0.6126	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7748	Approved
0.6119	Remote Similarity	NPD7078	Approved
0.6107	Remote Similarity	NPD7503	Approved
0.6098	Remote Similarity	NPD8140	Approved
0.6098	Remote Similarity	NPD8307	Discontinued
0.6095	Remote Similarity	NPD3703	Phase 2
0.6031	Remote Similarity	NPD6319	Approved
0.6019	Remote Similarity	NPD2686	Approved
0.6019	Remote Similarity	NPD2687	Approved
0.6019	Remote Similarity	NPD2254	Approved
0.6	Remote Similarity	NPD8306	Approved
0.6	Remote Similarity	NPD8305	Approved
0.6	Remote Similarity	NPD8074	Phase 3
0.5985	Remote Similarity	NPD6015	Approved
0.5985	Remote Similarity	NPD6016	Approved
0.5983	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7900	Approved
0.5968	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD8087	Discontinued
0.5948	Remote Similarity	NPD7515	Phase 2
0.5943	Remote Similarity	NPD3702	Approved
0.594	Remote Similarity	NPD5988	Approved
0.5923	Remote Similarity	NPD7115	Discovery
0.5922	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6882	Approved
0.5859	Remote Similarity	NPD8297	Approved
0.581	Remote Similarity	NPD5777	Approved
0.5802	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6009	Approved
0.5798	Remote Similarity	NPD7991	Discontinued
0.5789	Remote Similarity	NPD8347	Approved
0.5789	Remote Similarity	NPD8345	Approved
0.5789	Remote Similarity	NPD8346	Approved
0.5785	Remote Similarity	NPD4225	Approved
0.5785	Remote Similarity	NPD7638	Approved
0.578	Remote Similarity	NPD4802	Phase 2
0.578	Remote Similarity	NPD4238	Approved
0.5778	Remote Similarity	NPD6067	Discontinued
0.5755	Remote Similarity	NPD3181	Approved
0.5748	Remote Similarity	NPD6373	Approved
0.5748	Remote Similarity	NPD6372	Approved
0.5738	Remote Similarity	NPD7639	Approved
0.5738	Remote Similarity	NPD8418	Phase 2
0.5738	Remote Similarity	NPD7640	Approved
0.5725	Remote Similarity	NPD6033	Approved
0.5714	Remote Similarity	NPD4245	Approved
0.5714	Remote Similarity	NPD4244	Approved
0.5692	Remote Similarity	NPD4632	Approved
0.5673	Remote Similarity	NPD5360	Phase 3
0.5673	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6081	Approved
0.5659	Remote Similarity	NPD6649	Approved
0.5659	Remote Similarity	NPD6650	Approved
0.5645	Remote Similarity	NPD8301	Approved
0.5645	Remote Similarity	NPD8300	Approved
0.5645	Remote Similarity	NPD7632	Discontinued
0.5635	Remote Similarity	NPD6675	Approved
0.5635	Remote Similarity	NPD5739	Approved
0.5635	Remote Similarity	NPD7128	Approved
0.5635	Remote Similarity	NPD6402	Approved
0.5634	Remote Similarity	NPD8450	Suspended
0.5631	Remote Similarity	NPD4224	Phase 2
0.563	Remote Similarity	NPD6399	Phase 3
0.563	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD3698	Phase 2
0.56	Remote Similarity	NPD6123	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