NPASS Compound

Structure

NPC476090 OpenBabel07101719172D 97107 0 0 1 0 0 0 0 0999 V2000 7.7221 3.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4381 4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4381 6.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5861 7.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7425 -1.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 2.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4403 1.2969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0121 1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7281 5.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7281 10.8981 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 -3.4320 4.9537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5740 6.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5693 -2.3613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8330 -3.0242 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 -1.7160 5.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3633 -1.3922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8580 4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8580 3.4676 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 2.5740 3.4676 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 1.7160 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1913 -1.0727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2060 -0.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8907 -2.7181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4320 1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1480 1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4381 1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0121 4.9537 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 16.3021 6.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8641 2.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4381 3.4676 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2961 5.9444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7281 7.9259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5365 -0.4737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7160 4.9537 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 3.4320 2.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4210 -1.0860 0.0000 C 0 0 0 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 10.2961 1.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0121 5.9444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 16.3021 7.4306 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8580 1.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8580 1.4861 0.0000 C 0 0 2 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 5.1480 2.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5801 1.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1541 4.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.1601 7.9259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 17.1601 8.9167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 16.3021 9.4120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0121 8.9167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8641 1.9815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2961 2.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1541 6.4398 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7281 8.9167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8701 9.4120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2150 -0.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4441 8.9167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0121 7.9259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7160 1.9815 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 -1.5943 -0.1676 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6848 -1.7490 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 17.1601 5.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5740 3.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.0181 7.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.0181 9.4120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.3021 10.4028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1541 9.4120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9513 0.5460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3305 0.4954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 -1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9853 -0.1036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0060 0.4954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1541 1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8701 6.4398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8701 10.4028 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 8.5801 2.9722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2961 4.9537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8701 7.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2728 0.1892 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 15.4441 7.9259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7160 1.9815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7221 1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1541 3.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1541 7.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5861 9.4120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7 67 1 0 0 0 0 8 82 1 0 0 0 0 9 83 1 0 0 0 0 10 84 1 0 0 0 0 11 85 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 28 1 0 0 0 0 17 40 2 0 0 0 0 18 40 1 0 0 0 0 19 43 2 0 0 0 0 20 21 2 0 0 0 0 20 40 1 0 0 0 0 21 50 1 0 0 0 0 22 25 1 0 0 0 0 22 41 2 0 0 0 0 23 24 1 0 0 0 0 23 42 1 0 0 0 0 24 66 1 0 0 0 0 25 69 1 0 0 0 0 26 27 1 0 0 0 0 26 68 1 0 0 0 0 27 70 1 0 0 0 0 28 71 2 0 0 0 0 29 41 1 0 0 0 0 29 42 1 0 0 0 0 30 44 1 0 0 0 0 30 51 1 0 0 0 0 31 45 1 0 0 0 0 31 52 1 0 0 0 0 32 46 1 0 0 0 0 32 53 1 0 0 0 0 33 48 1 0 0 0 0 33 49 1 0 0 0 0 34 72 1 0 0 0 0 35 1 1 6 0 0 0 35 58 1 0 0 0 0 35 86 1 0 0 0 0 36 2 1 6 0 0 0 36 59 1 0 0 0 0 36 87 1 0 0 0 0 37 3 1 6 0 0 0 37 60 1 0 0 0 0 37 88 1 0 0 0 0 38 4 1 1 0 0 0 38 61 1 0 0 0 0 38 89 1 0 0 0 0 39 5 1 6 0 0 0 39 68 1 0 0 0 0 39 90 1 0 0 0 0 41 66 1 0 0 0 0 42 91 1 6 0 0 0 43 63 1 0 0 0 0 43 71 1 0 0 0 0 44 58 1 0 0 0 0 44 82 1 1 0 0 0 45 59 1 0 0 0 0 45 83 1 1 0 0 0 46 60 1 0 0 0 0 46 84 1 1 0 0 0 47 34 1 1 0 0 0 47 54 1 0 0 0 0 47 92 1 0 0 0 0 48 66 1 6 0 0 0 48 69 1 0 0 0 0 49 67 1 6 0 0 0 49 93 1 0 0 0 0 50 73 2 0 0 0 0 50 93 1 0 0 0 0 51 86 1 0 0 0 0 51 91 1 6 0 0 0 52 87 1 0 0 0 0 52 94 1 6 0 0 0 53 88 1 0 0 0 0 53 95 1 6 0 0 0 54 55 1 0 0 0 0 54 74 1 6 0 0 0 55 56 1 0 0 0 0 55 75 1 1 0 0 0 56 64 1 0 0 0 0 56 76 1 6 0 0 0 57 62 1 0 0 0 0 57 65 1 0 0 0 0 57 77 1 6 0 0 0 58 94 1 1 0 0 0 59 95 1 1 0 0 0 60 96 1 1 0 0 0 61 62 1 0 0 0 0 61 97 1 6 0 0 0 62 85 1 1 0 0 0 63 78 2 0 0 0 0 63 90 1 0 0 0 0 64 92 1 0 0 0 0 64 97 1 1 0 0 0 65 89 1 0 0 0 0 65 96 1 1 0 0 0 66 6 1 6 0 0 0 67 68 1 1 0 0 0 68 79 1 1 0 0 0 69 70 1 1 0 0 0 69 80 1 0 0 0 0 70 67 1 6 0 0 0 70 81 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1371.66
Volume:	1338.332
LogP:	3.561
LogD:	2.639
LogS:	-4.228
# Rotatable Bonds:	23
TPSA:	356.55
# H-Bond Aceptor:	27
# H-Bond Donor:	8
# Rings:	11
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	7.693
Fsp3:	0.757
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:	-6.103
MDCK Permeability:	0.0002273252757731825
Pgp-inhibitor:	0.003
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.199
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	60.23842239379883%
Volume Distribution (VD):	-0.009
Pgp-substrate:	14.580231666564941%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.205
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.426
CYP3A4-substrate:	0.867

ADMET: Excretion

Clearance (CL):	0.493
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.839
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.406
Rat Oral Acute Toxicity:	0.42
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.818
Carcinogencity:	0.187
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.496

Download Data

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

Natural Product: NPC476090

Natural Product ID:	NPC476090
*Common Name:**	[(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17R)-8,14,17-Trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5R,6R)-3-Hydroxy-4-Methoxy-6-Methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-10,13-Dimethyl-12-[(E)-3-Phenylprop-2-Enoyl]Oxy-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-17-Yl]Ethyl] Pyridine-2-Carboxylate
IUPAC Name:	[(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17R)-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] pyridine-2-carboxylate
Synonyms:
Standard InCHIKey:	RPFMXDKVDYAPIN-PEAUOBRLSA-N
Standard InCHI:	InChI=1S/C70H101NO26/c1-35-58(94-52-31-45(83-9)59(36(2)87-52)95-53-32-46(84-10)60(37(3)88-53)96-65-57(77)62(85-11)61(38(4)89-65)97-64-56(76)55(75)54(74)47(34-72)92-64)44(82-8)30-51(86-35)91-42-23-24-66(6)41(29-42)22-25-69(80)48(66)33-49(93-50(73)21-20-40-17-13-12-14-18-40)67(7)68(79,26-27-70(67,69)81)39(5)90-63(78)43-19-15-16-28-71-43/h12-22,28,35-39,42,44-49,51-62,64-65,72,74-77,79-81H,23-27,29-34H2,1-11H3/b21-20+/t35-,36-,37-,38-,39+,42+,44+,45+,46+,47-,48-,49-,51+,52+,53+,54-,55+,56-,57-,58-,59-,60-,61-,62-,64+,65+,66+,67-,68+,69+,70-/m1/s1
SMILES:	CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C(=CC[C@@]4([C@@H]3C[C@@H](OC(=O)/C=C/c3ccccc3)[C@]3([C@]4(O)CC[C@]3(O)[C@@H](OC(=O)c3ccccn3)C)C)O)C2)C)O[C@@H]([C@H]1O[C@H]1C[C@H](OC)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](OC)[C@@H]([C@H](O1)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525449
PubChem CID:	44575250
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32487	leptadenia pyrotechnica	Species	Apocynaceae	Eukaryota	whole plant	Dogon region, Mali	2002-Apr	PMID[16643040]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	1370.0	nM	PMID[531528]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	640.0	nM	PMID[531528]

☑ 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 NPC476090 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	405
0.1-0.2	1635
0.2-0.3	3941
0.3-0.4	12018
0.4-0.5	17674
0.5-0.6	5710
0.6-0.7	1086
0.7-0.8	142
0.8-0.85	83
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8451	Intermediate Similarity	NPC471190
0.8451	Intermediate Similarity	NPC471977
0.8451	Intermediate Similarity	NPC475644
0.8451	Intermediate Similarity	NPC470486
0.8421	Intermediate Similarity	NPC30456
0.8407	Intermediate Similarity	NPC122968
0.8407	Intermediate Similarity	NPC87152
0.8407	Intermediate Similarity	NPC475600
0.8407	Intermediate Similarity	NPC477787
0.8407	Intermediate Similarity	NPC476110
0.8407	Intermediate Similarity	NPC328186
0.8407	Intermediate Similarity	NPC228377
0.8407	Intermediate Similarity	NPC475631
0.8377	Intermediate Similarity	NPC475303
0.8377	Intermediate Similarity	NPC316841
0.8377	Intermediate Similarity	NPC475596
0.8363	Intermediate Similarity	NPC473506
0.8348	Intermediate Similarity	NPC327769
0.8319	Intermediate Similarity	NPC473850
0.8319	Intermediate Similarity	NPC475137
0.8319	Intermediate Similarity	NPC475498
0.8304	Intermediate Similarity	NPC237702
0.8297	Intermediate Similarity	NPC292416
0.8297	Intermediate Similarity	NPC473689
0.8296	Intermediate Similarity	NPC294579
0.8296	Intermediate Similarity	NPC144779
0.8274	Intermediate Similarity	NPC250807
0.8274	Intermediate Similarity	NPC57797
0.8274	Intermediate Similarity	NPC471980
0.8274	Intermediate Similarity	NPC76565
0.8268	Intermediate Similarity	NPC475406
0.8261	Intermediate Similarity	NPC320324
0.8261	Intermediate Similarity	NPC244839
0.8261	Intermediate Similarity	NPC319880
0.8259	Intermediate Similarity	NPC301368
0.8259	Intermediate Similarity	NPC84815
0.8251	Intermediate Similarity	NPC475408
0.8251	Intermediate Similarity	NPC6981
0.8251	Intermediate Similarity	NPC471014
0.8248	Intermediate Similarity	NPC37473
0.8238	Intermediate Similarity	NPC477902
0.8233	Intermediate Similarity	NPC38959
0.8233	Intermediate Similarity	NPC327904
0.823	Intermediate Similarity	NPC127720
0.823	Intermediate Similarity	NPC477788
0.823	Intermediate Similarity	NPC127026
0.8214	Intermediate Similarity	NPC62367
0.821	Intermediate Similarity	NPC475362
0.8206	Intermediate Similarity	NPC470306
0.8178	Intermediate Similarity	NPC216428
0.817	Intermediate Similarity	NPC471016
0.8166	Intermediate Similarity	NPC211920
0.8166	Intermediate Similarity	NPC124029
0.8166	Intermediate Similarity	NPC146824
0.8158	Intermediate Similarity	NPC328154
0.8125	Intermediate Similarity	NPC42678
0.8125	Intermediate Similarity	NPC477907
0.8125	Intermediate Similarity	NPC477909
0.8112	Intermediate Similarity	NPC170751
0.8106	Intermediate Similarity	NPC477912
0.8097	Intermediate Similarity	NPC472555
0.808	Intermediate Similarity	NPC4421
0.8072	Intermediate Similarity	NPC472553
0.806	Intermediate Similarity	NPC477906
0.8053	Intermediate Similarity	NPC75600
0.8053	Intermediate Similarity	NPC473089
0.8053	Intermediate Similarity	NPC6576
0.8053	Intermediate Similarity	NPC473115
0.8053	Intermediate Similarity	NPC212768
0.8053	Intermediate Similarity	NPC158020
0.8051	Intermediate Similarity	NPC253482
0.8026	Intermediate Similarity	NPC477903
0.8025	Intermediate Similarity	NPC475648
0.8009	Intermediate Similarity	NPC477908
0.8009	Intermediate Similarity	NPC206343
0.7991	Intermediate Similarity	NPC477911
0.7991	Intermediate Similarity	NPC476467
0.7983	Intermediate Similarity	NPC96801
0.7983	Intermediate Similarity	NPC150698
0.7965	Intermediate Similarity	NPC148860
0.7965	Intermediate Similarity	NPC477910
0.7957	Intermediate Similarity	NPC35208
0.7957	Intermediate Similarity	NPC475426
0.7937	Intermediate Similarity	NPC48042
0.7937	Intermediate Similarity	NPC304179
0.7937	Intermediate Similarity	NPC472550
0.793	Intermediate Similarity	NPC162812
0.7922	Intermediate Similarity	NPC477900
0.7922	Intermediate Similarity	NPC477899
0.792	Intermediate Similarity	NPC319128
0.7913	Intermediate Similarity	NPC235364
0.7892	Intermediate Similarity	NPC63041
0.7854	Intermediate Similarity	NPC14116
0.7854	Intermediate Similarity	NPC475601
0.7854	Intermediate Similarity	NPC285411
0.7845	Intermediate Similarity	NPC26881
0.7841	Intermediate Similarity	NPC264674
0.7841	Intermediate Similarity	NPC228331
0.7826	Intermediate Similarity	NPC477901
0.7821	Intermediate Similarity	NPC311196
0.7821	Intermediate Similarity	NPC134384
0.7797	Intermediate Similarity	NPC469748
0.7787	Intermediate Similarity	NPC91125
0.7768	Intermediate Similarity	NPC475835
0.7753	Intermediate Similarity	NPC280473
0.7753	Intermediate Similarity	NPC323551
0.7729	Intermediate Similarity	NPC30570
0.7719	Intermediate Similarity	NPC51008
0.7719	Intermediate Similarity	NPC41724
0.7692	Intermediate Similarity	NPC233727
0.7689	Intermediate Similarity	NPC238278
0.7675	Intermediate Similarity	NPC292517
0.7655	Intermediate Similarity	NPC470280
0.7647	Intermediate Similarity	NPC213143
0.7642	Intermediate Similarity	NPC165837
0.7578	Intermediate Similarity	NPC470279
0.752	Intermediate Similarity	NPC85879
0.752	Intermediate Similarity	NPC53255
0.752	Intermediate Similarity	NPC326930
0.752	Intermediate Similarity	NPC475301
0.75	Intermediate Similarity	NPC476516
0.749	Intermediate Similarity	NPC13603
0.7489	Intermediate Similarity	NPC309498
0.748	Intermediate Similarity	NPC328928
0.7455	Intermediate Similarity	NPC160127
0.7455	Intermediate Similarity	NPC50997
0.7449	Intermediate Similarity	NPC475533
0.7446	Intermediate Similarity	NPC111732
0.7436	Intermediate Similarity	NPC187494
0.7436	Intermediate Similarity	NPC319556
0.7425	Intermediate Similarity	NPC193361
0.7425	Intermediate Similarity	NPC62844
0.7419	Intermediate Similarity	NPC324619
0.7419	Intermediate Similarity	NPC475315
0.7412	Intermediate Similarity	NPC471978
0.7403	Intermediate Similarity	NPC470189
0.7403	Intermediate Similarity	NPC40919
0.7402	Intermediate Similarity	NPC473833
0.7391	Intermediate Similarity	NPC472752
0.7368	Intermediate Similarity	NPC289086
0.735	Intermediate Similarity	NPC207531
0.7348	Intermediate Similarity	NPC470190
0.7341	Intermediate Similarity	NPC471015
0.7339	Intermediate Similarity	NPC471013
0.7339	Intermediate Similarity	NPC148896
0.7339	Intermediate Similarity	NPC180668
0.7304	Intermediate Similarity	NPC156044
0.7297	Intermediate Similarity	NPC127647
0.7284	Intermediate Similarity	NPC471004
0.7269	Intermediate Similarity	NPC476517
0.7259	Intermediate Similarity	NPC471979
0.724	Intermediate Similarity	NPC328798
0.7222	Intermediate Similarity	NPC10904
0.7217	Intermediate Similarity	NPC25442
0.7217	Intermediate Similarity	NPC12944
0.7215	Intermediate Similarity	NPC141385
0.7207	Intermediate Similarity	NPC182814
0.7193	Intermediate Similarity	NPC79223
0.7176	Intermediate Similarity	NPC478045
0.7156	Intermediate Similarity	NPC103230
0.7149	Intermediate Similarity	NPC318020
0.7149	Intermediate Similarity	NPC123395
0.7126	Intermediate Similarity	NPC183537
0.7119	Intermediate Similarity	NPC317752
0.7105	Intermediate Similarity	NPC324245
0.7105	Intermediate Similarity	NPC320748
0.7104	Intermediate Similarity	NPC207851
0.7089	Intermediate Similarity	NPC274842
0.7087	Intermediate Similarity	NPC328559
0.7087	Intermediate Similarity	NPC32451
0.7085	Intermediate Similarity	NPC325775
0.7083	Intermediate Similarity	NPC140311
0.708	Intermediate Similarity	NPC210296
0.7076	Intermediate Similarity	NPC318299
0.707	Intermediate Similarity	NPC131273
0.707	Intermediate Similarity	NPC473441
0.7069	Intermediate Similarity	NPC477043
0.7063	Intermediate Similarity	NPC124313
0.7059	Intermediate Similarity	NPC325093
0.7059	Intermediate Similarity	NPC77878
0.7056	Intermediate Similarity	NPC108342
0.7056	Intermediate Similarity	NPC57453
0.7046	Intermediate Similarity	NPC306644
0.7046	Intermediate Similarity	NPC236424
0.7031	Intermediate Similarity	NPC477044
0.7031	Intermediate Similarity	NPC477041
0.7031	Intermediate Similarity	NPC59033
0.7028	Intermediate Similarity	NPC189903
0.7028	Intermediate Similarity	NPC182907
0.7018	Intermediate Similarity	NPC109922
0.7008	Intermediate Similarity	NPC472762
0.7005	Intermediate Similarity	NPC475198
0.7005	Intermediate Similarity	NPC475531
0.7005	Intermediate Similarity	NPC475175
0.7	Intermediate Similarity	NPC477045
0.6988	Remote Similarity	NPC476514
0.6987	Remote Similarity	NPC329024
0.6984	Remote Similarity	NPC84164
0.6984	Remote Similarity	NPC207283
0.6974	Remote Similarity	NPC135950

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 NPC476090 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	564
0.2-0.3	743
0.3-0.4	2244
0.4-0.5	3470
0.5-0.6	1651
0.6-0.7	230
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.834	Intermediate Similarity	NPD8468	Phase 2
0.7319	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD8326	Phase 3
0.7319	Intermediate Similarity	NPD8325	Phase 3
0.7253	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8063	Discontinued
0.6996	Remote Similarity	NPD7396	Approved
0.6939	Remote Similarity	NPD8289	Discontinued
0.6905	Remote Similarity	NPD7886	Phase 2
0.6905	Remote Similarity	NPD7885	Phase 2
0.6904	Remote Similarity	NPD3794	Approved
0.6904	Remote Similarity	NPD3795	Approved
0.6903	Remote Similarity	NPD7234	Approved
0.6903	Remote Similarity	NPD7233	Approved
0.6875	Remote Similarity	NPD7707	Approved
0.6855	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6635	Approved
0.6792	Remote Similarity	NPD7069	Discontinued
0.6786	Remote Similarity	NPD5891	Approved
0.6771	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.676	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7010	Phase 3
0.6735	Remote Similarity	NPD8479	Phase 2
0.6721	Remote Similarity	NPD7395	Discontinued
0.6708	Remote Similarity	NPD3394	Approved
0.6708	Remote Similarity	NPD3393	Approved
0.6708	Remote Similarity	NPD3389	Approved
0.6693	Remote Similarity	NPD8409	Suspended
0.6681	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD8370	Discontinued
0.6667	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4528	Approved
0.6638	Remote Similarity	NPD4526	Approved
0.6638	Remote Similarity	NPD4529	Approved
0.662	Remote Similarity	NPD6026	Approved
0.6613	Remote Similarity	NPD8356	Approved
0.6599	Remote Similarity	NPD3280	Approved
0.659	Remote Similarity	NPD2582	Approved
0.659	Remote Similarity	NPD2581	Approved
0.6585	Remote Similarity	NPD6568	Discontinued
0.6578	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6298	Discontinued
0.6565	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7187	Phase 2
0.6555	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7708	Approved
0.6553	Remote Similarity	NPD8485	Approved
0.6538	Remote Similarity	NPD4427	Phase 2
0.6534	Remote Similarity	NPD5640	Discontinued
0.6529	Remote Similarity	NPD6529	Discontinued
0.6527	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1483	Discontinued
0.6525	Remote Similarity	NPD8412	Phase 1
0.6516	Remote Similarity	NPD5866	Approved
0.6515	Remote Similarity	NPD5429	Discontinued
0.6509	Remote Similarity	NPD6281	Approved
0.6509	Remote Similarity	NPD8360	Approved
0.6509	Remote Similarity	NPD8361	Approved
0.6509	Remote Similarity	NPD8435	Approved
0.6508	Remote Similarity	NPD8430	Approved
0.6496	Remote Similarity	NPD7688	Phase 1
0.6492	Remote Similarity	NPD7404	Approved
0.649	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4989	Phase 2
0.6475	Remote Similarity	NPD5475	Discontinued
0.6473	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7957	Phase 1
0.6463	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7803	Approved
0.6452	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5512	Phase 3
0.6439	Remote Similarity	NPD5482	Discontinued
0.6432	Remote Similarity	NPD4122	Approved
0.6432	Remote Similarity	NPD32	Approved
0.6432	Remote Similarity	NPD4034	Approved
0.6432	Remote Similarity	NPD4033	Approved
0.6432	Remote Similarity	NPD4039	Approved
0.6432	Remote Similarity	NPD4035	Approved
0.6432	Remote Similarity	NPD8114	Approved
0.6432	Remote Similarity	NPD8115	Approved
0.6432	Remote Similarity	NPD4037	Approved
0.6432	Remote Similarity	NPD4038	Approved
0.6432	Remote Similarity	NPD4036	Approved
0.6432	Remote Similarity	NPD31	Approved
0.6429	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7417	Discontinued
0.6422	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8021	Approved
0.6422	Remote Similarity	NPD8020	Approved
0.642	Remote Similarity	NPD2509	Approved
0.642	Remote Similarity	NPD2510	Approved
0.6419	Remote Similarity	NPD3178	Discontinued
0.6418	Remote Similarity	NPD7169	Suspended
0.6411	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4417	Approved
0.6407	Remote Similarity	NPD4889	Approved
0.6407	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD7426	Phase 1
0.6397	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD7956	Approved
0.6394	Remote Similarity	NPD7955	Approved
0.6392	Remote Similarity	NPD5022	Discontinued
0.6387	Remote Similarity	NPD7778	Approved
0.6387	Remote Similarity	NPD53	Approved
0.6387	Remote Similarity	NPD7777	Approved
0.6383	Remote Similarity	NPD6569	Phase 2
0.6381	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.636	Remote Similarity	NPD8123	Approved
0.636	Remote Similarity	NPD6642	Approved
0.636	Remote Similarity	NPD6641	Approved
0.636	Remote Similarity	NPD8122	Approved
0.636	Remote Similarity	NPD6974	Phase 3
0.6352	Remote Similarity	NPD7191	Phase 2
0.635	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7967	Discontinued
0.6345	Remote Similarity	NPD5003	Discontinued
0.6341	Remote Similarity	NPD7470	Discontinued
0.6337	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5255	Approved
0.6331	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5088	Discontinued
0.6316	Remote Similarity	NPD8101	Phase 3
0.6316	Remote Similarity	NPD3816	Phase 1
0.6316	Remote Similarity	NPD3815	Phase 1
0.6314	Remote Similarity	NPD4376	Phase 3
0.6314	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD4086	Phase 1
0.6314	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4301	Approved
0.6307	Remote Similarity	NPD7727	Phase 2
0.6303	Remote Similarity	NPD6550	Discontinued
0.6301	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3947	Discontinued
0.6295	Remote Similarity	NPD6770	Approved
0.6293	Remote Similarity	NPD7482	Phase 2
0.6293	Remote Similarity	NPD1096	Discontinued
0.6293	Remote Similarity	NPD7483	Phase 2
0.6288	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6361	Phase 2
0.6286	Remote Similarity	NPD7467	Discontinued
0.6282	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3263	Phase 3
0.6269	Remote Similarity	NPD7853	Phase 2
0.6266	Remote Similarity	NPD8407	Phase 2
0.6264	Remote Similarity	NPD8375	Approved
0.6261	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.626	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD5805	Approved
0.6245	Remote Similarity	NPD7562	Approved
0.6235	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD3477	Phase 2
0.6234	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6987	Phase 1
0.623	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD3321	Discontinued
0.6228	Remote Similarity	NPD2077	Approved
0.6228	Remote Similarity	NPD2076	Approved
0.622	Remote Similarity	NPD6995	Phase 1
0.6218	Remote Similarity	NPD5450	Discontinued
0.6217	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD820	Phase 3
0.6215	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD6791	Phase 2
0.621	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD8364	Approved
0.6209	Remote Similarity	NPD8363	Approved
0.6208	Remote Similarity	NPD7859	Phase 2
0.6207	Remote Similarity	NPD3006	Discontinued
0.6207	Remote Similarity	NPD8368	Discontinued
0.6207	Remote Similarity	NPD8408	Discontinued
0.6206	Remote Similarity	NPD7180	Phase 3
0.6206	Remote Similarity	NPD1996	Discontinued
0.6206	Remote Similarity	NPD5850	Phase 3
0.6204	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD8100	Phase 3
0.6202	Remote Similarity	NPD8374	Phase 3
0.6198	Remote Similarity	NPD6479	Discontinued
0.6198	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD6241	Phase 1
0.6196	Remote Similarity	NPD7673	Phase 3
0.6192	Remote Similarity	NPD6494	Phase 2
0.6192	Remote Similarity	NPD7944	Discontinued
0.6192	Remote Similarity	NPD4602	Approved
0.619	Remote Similarity	NPD7878	Phase 2
0.619	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD7994	Phase 2
0.618	Remote Similarity	NPD7962	Phase 2

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