NPASS Compound

Structure

NPC99847 OpenBabel06302215332D 75 82 0 0 1 0 0 0 0 0999 V2000 0.5023 -3.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4533 -3.8193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1965 -3.1501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6613 -4.7974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9181 -5.4665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1260 -6.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0771 -6.7537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3829 -7.1138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5682 -6.8048 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7761 -5.8267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7271 -5.5176 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9351 -4.5395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9840 -4.8485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1919 -3.8704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -2.8922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3509 -2.5832 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0940 -3.2523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8861 -4.2305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6293 -4.8996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4213 -5.8778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4703 -6.1868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2624 -7.1649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8502 -7.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2624 -8.7829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3113 -8.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3168 -8.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2710 -7.7694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0899 -9.4920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3113 -7.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3168 -7.3694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9046 -9.3875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0055 -6.4958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2134 -6.8559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1032 -1.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6123 -5.1064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 4 5 2 3 0 0 0 4 75 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 9 8 1 1 0 0 0 9 10 1 0 0 0 0 9 29 1 0 0 0 0 11 10 1 1 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 13 1 1 0 0 0 12 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 16 34 1 1 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 33 1 1 0 0 0 22 29 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 25 31 1 1 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 29 30 1 1 0 0 0 35 34 1 1 0 0 0 35 36 1 0 0 0 0 35 41 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 37 73 1 6 0 0 0 38 39 1 0 0 0 0 38 42 1 6 0 0 0 39 40 1 1 0 0 0 39 41 1 0 0 0 0 43 42 1 1 0 0 0 43 44 1 0 0 0 0 43 49 1 0 0 0 0 44 45 1 0 0 0 0 45 46 1 0 0 0 0 45 71 1 6 0 0 0 46 47 1 0 0 0 0 46 50 1 6 0 0 0 47 48 1 6 0 0 0 47 49 1 0 0 0 0 51 50 1 6 0 0 0 51 52 1 0 0 0 0 51 57 1 0 0 0 0 52 53 1 0 0 0 0 53 54 1 0 0 0 0 53 69 1 1 0 0 0 54 55 1 0 0 0 0 54 58 1 1 0 0 0 55 56 1 6 0 0 0 55 57 1 0 0 0 0 59 58 1 6 0 0 0 59 60 1 0 0 0 0 59 65 1 0 0 0 0 60 61 1 0 0 0 0 61 62 1 0 0 0 0 61 67 1 6 0 0 0 62 63 1 0 0 0 0 62 66 1 6 0 0 0 63 64 1 1 0 0 0 63 65 1 0 0 0 0 67 68 1 0 0 0 0 69 70 1 0 0 0 0 71 72 1 0 0 0 0 73 74 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1066.61
Volume:	1065.148
LogP:	4.416
LogD:	3.427
LogS:	-5.137
# Rotatable Bonds:	17
TPSA:	235.05
# H-Bond Aceptor:	19
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	6.968
Fsp3:	0.893
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.15
MDCK Permeability:	0.00023657383280806243
Pgp-inhibitor:	0.165
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	76.81512451171875%
Volume Distribution (VD):	0.514
Pgp-substrate:	9.668985366821289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.55
CYP3A4-substrate:	0.95

ADMET: Excretion

Clearance (CL):	2.512
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.887
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.414
AMES Toxicity:	0.367
Rat Oral Acute Toxicity:	0.703
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.846
Carcinogencity:	0.906
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC99847

Natural Product ID:	NPC99847
*Common Name:**	YUDOHRCAEPBFBO-KXNNMBJLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YUDOHRCAEPBFBO-KXNNMBJLSA-N
Standard InCHI:	InChI=1S/C56H90O19/c1-28(2)29(3)21-43(58)72-42-27-41-52(9)17-16-36(22-35(52)15-18-55(41,61)56(62)20-19-54(60,34(8)57)53(42,56)10)71-44-24-38(64-12)49(31(5)68-44)74-46-26-40(66-14)51(33(7)70-46)75-47-25-39(65-13)50(32(6)69-47)73-45-23-37(63-11)48(59)30(4)67-45/h15,21,28,30-33,36-42,44-51,59-62H,16-20,22-27H2,1-14H3/t30-,31+,32+,33-,36-,37+,38-,39-,40-,41+,42+,44-,45-,46-,47-,48-,49+,50+,51+,52-,53+,54+,55-,56+/m0/s1
SMILES:	CC(C)C(=CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@@H](CC3=CC[C@]2([C@]2(CC[C@@](C(=O)C)([C@@]12C)O)O)O)O[C@H]1C[C@@H]([C@@H]([C@@H](C)O1)O[C@H]1C[C@@H]([C@@H]([C@H](C)O1)O[C@H]1C[C@@H]([C@@H]([C@@H](C)O1)O[C@H]1C[C@H]([C@H]([C@H](C)O1)O)OC)OC)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	123327196
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
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)80275-7]
NPO8809	Cynanchum wilfordii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217732]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16644212]
NPO280	Dysidea chlorea	Species	Dysideidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[16872148]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24054487]
NPO55	Croton urucurana	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354204]
NPO55	Croton urucurana	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354204]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24412339]
NPO55	Croton urucurana	Species	Euphorbiaceae	Eukaryota	Latex	n.a.	n.a.	PMID[26561866]
NPO8809	Cynanchum wilfordii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26716755]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5745	Randia formosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8809	Cynanchum wilfordii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23643	Thalictrum aquilegiifolium	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7220	Artemisia latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8942	Hedysarum coronarium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5745	Randia formosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3834	Periplaneta americana	Species	Blattoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5486	Helicoon richonis	Species	Orbiliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1017	Dendrobium gibsonii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO280	Dysidea chlorea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6312	Picea engelmannii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8276	Harpullia ramiflora	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8809	Cynanchum wilfordii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4983	Bromelia pinguin	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13333	Paenibacillus thiaminolyticus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28100	Jacobaea othonnae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2641	Marsupella aquatica	Species	Gymnomitriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8531	Centaurea ferox	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6086	Axinella polypoides	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO55	Croton urucurana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8407	Polyporus fomentarius	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4010	Flemingia philippinensis	Species	Fabaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC99847 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	342
0.1-0.2	1899
0.2-0.3	5141
0.3-0.4	8637
0.4-0.5	11353
0.5-0.6	7547
0.6-0.7	4737
0.7-0.8	1940
0.8-0.85	756
0.85-0.9	300
0.9-0.95	35
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID

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 NPC99847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	2067
0.2-0.3	3927
0.3-0.4	1827
0.4-0.5	534
0.5-0.6	288
0.6-0.7	127
0.7-0.8	57
0.8-0.85	7
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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