NPASS Compound

Natural Product: NPC470119

Natural Product ID	NPC470119
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MJNRBOGIPLCVIM-JLDAJYGSSA-N
IUPAC Name	n.a.
Synonyms	3-Deacetylsalannin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1774413
PubChem CID	54583361
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 82 87 0 0 0 0 0 0 0 0999 V2000 0.4148 -3.2549 -4.3631 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1585 -2.5325 -3.2052 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2241 -1.1779 -3.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5710 -0.6435 -4.1953 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0080 -0.2528 -2.0075 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1157 -0.6032 -0.5685 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0989 -1.2326 0.0453 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9471 -2.0650 -0.8614 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1213 -0.1878 0.5391 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8168 1.1272 0.1661 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6784 1.9563 -0.5584 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7784 1.4393 -0.8703 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3487 3.3149 -0.9341 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2225 4.0096 -1.6282 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5498 3.4827 -2.0605 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0635 3.9524 -0.5551 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3284 -0.1966 2.0313 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6191 -1.5749 2.6076 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6914 -2.6255 2.1056 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6874 -1.9082 1.2912 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4272 -2.8919 1.2116 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6313 -2.0403 0.9092 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4484 -1.1467 -0.2824 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1508 -1.8602 -1.4300 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4299 -0.0725 0.1666 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4080 0.7697 -0.0710 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0142 0.8843 -1.4517 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8093 1.5033 1.1303 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1497 0.8231 2.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0625 0.0585 1.6028 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8137 -1.1994 2.0269 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6779 2.9553 1.0865 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6352 3.8003 0.7698 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1073 5.0879 0.9155 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3463 5.0716 1.2931 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7220 3.8358 1.4060 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4583 -3.4327 2.4794 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6695 -3.0686 3.1861 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2873 -3.8707 1.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4019 -1.4530 3.9856 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1777 -2.7705 -5.0090 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 -4.2474 -4.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4926 -3.4767 -4.9520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 0.6120 -2.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9576 0.3126 -2.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1097 0.4263 -0.0539 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9629 -2.1738 -0.3557 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2316 -1.5113 -1.7743 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6338 -3.0503 -1.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1541 -0.3698 0.1244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9682 5.0475 -1.9130 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2235 3.2678 -1.2063 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0767 4.2547 -2.6602 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4495 2.6126 -2.7580 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7116 3.3732 0.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2538 4.9947 -0.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3791 3.8733 -1.4131 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2697 0.3870 2.2405 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5521 0.3567 2.6008 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7054 -1.8246 2.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3081 -1.1316 1.9977 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3164 -3.6518 0.4114 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5066 -2.7059 0.8052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2488 -1.9099 -1.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9024 -2.9359 -1.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1529 -1.3260 -2.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2820 0.7876 -2.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4667 1.9153 -1.5681 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8292 0.1809 -1.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9213 1.2584 1.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7608 1.6337 2.9535 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8234 0.1936 2.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1699 0.7481 1.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6635 3.4443 0.4714 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5168 5.9723 0.7368 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7232 3.5601 1.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0953 -3.9166 3.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4412 -2.2317 3.8753 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3123 -4.6658 2.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 -3.8373 1.3001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6191 -4.3706 0.8595 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0833 -1.8863 4.5265 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 13 16 1 0 9 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 2 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 28 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 21 37 1 0 37 38 1 0 19 39 1 6 18 40 1 0 23 6 1 0 30 25 1 0 36 32 2 0 20 7 1 0 31 22 1 0 38 19 1 0 1 41 1 0 1 42 1 0 1 43 1 0 5 44 1 0 5 45 1 0 6 46 1 1 8 47 1 0 8 48 1 0 8 49 1 0 9 50 1 6 14 51 1 0 15 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 1 20 61 1 1 21 62 1 6 22 63 1 6 24 64 1 0 24 65 1 0 24 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 1 29 71 1 0 29 72 1 0 30 73 1 6 33 74 1 0 34 75 1 0 36 76 1 0 38 77 1 0 38 78 1 0 39 79 1 0 39 80 1 0 39 81 1 0 40 82 1 0 M END

Standard InCHIKey	MJNRBOGIPLCVIM-JLDAJYGSSA-N
Standard InCHI	InChI=1S/C32H42O8/c1-8-16(2)29(35)40-23-13-22(33)30(4)15-38-26-27(30)31(23,5)21(12-24(34)36-7)32(6)25-17(3)19(18-9-10-37-14-18)11-20(25)39-28(26)32/h8-10,14,19-23,26-28,33H,11-13,15H2,1-7H3/b16-8-/t19-,20-,21-,22-,23+,26-,27+,28-,30-,31+,32-/m1/s1
SMILES	COC(=O)C[C@@H]1[C@@]2(C)[C@@H](OC(=O)/C(=CC)/C)C[C@H]([C@@]3([C@@H]2[C@H]([C@@H]2[C@@]1(C)C1=C(C)[C@@H](C[C@H]1O2)c1ccoc1)OC3)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	554.29	Volume:	565.192 ? Van der Waals volume.
Dense:	0.981	LogP:	2.798 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.087 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.401 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	104.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.317	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.538	Fsp³:	0.688
MCE-18:	144.259 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.95	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.025	Promiscuous compounds:	0.433

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.11	MDCK Permeability:	-4.806
Pgp-inhibitor:	0.221	Pgp-substrate:	0.879
PAMPA:	0.856 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.744	30% Bioavailability (F30%):	0.627
50% Bioavailability (F50%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095	MRP1:	0.998
Plasma Protein Binding (PPB):	93.545%	Volume Distribution (VD):	0.095
Fu:	7.776% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.612
OATP1B3 inhibitor:	0.296	BCRP inhibitor:	0.06
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	0.034	CYP1A2-substrate:	0.474
CYP2C19-inhibitor:	0.781	CYP2C19-substrate:	0.148
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.913
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.919
HLM stability:	0.969 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

11.778

Half-life (T1/2):

1.505

ADMET: Toxicity

hERG Blockers:	0.102	hERG Blockers (10um):	0.294
Human Hepatotoxicity (H-HT):	0.691	Drug-induced Liver Injury (DILI):	0.906
AMES Toxicity:	0.634	Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.993	Skin Sensitization:	0.933
Carcinogencity:	0.723	Eye Corrosion:	0.0
Eye Irritation:	0.287	Respiratory Toxicity:	0.894
Drug-induced Neurotoxicity:	0.356	Ototoxicity:	0.868
Hematotoxicity:	0.612	Drug-induced Nephrotoxicity:	0.975
Genotoxicity:	0.989	RPMI-8226 Immunitoxicity:	0.193
A549 Cytotoxicity:	0.201	Hek293 Cytotoxicity:	0.084
BCF:	0.731 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.686 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.715 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.89 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s12038-008-0027-6]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37151484]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4406	Azadirachta indica	Species	Meliaceae	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	Organism Name	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	5

Activity Type	# Activity
Cell line	3
Non-molecular	2

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	20000.0	nM	Open TG-GATES in vivo data: Hematology
NPT81	Cell line	A549	Homo sapiens	IC50	>	20000.0	nM	Open TG-GATES in vivo data: Hematology
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	Open TG-GATES in vivo data: Hematology
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[21381696]

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC470119 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	10326
0.1-0.2	37305
0.2-0.3	2075
0.3-0.4	114
0.4-0.5	12
0.5-0.6	13
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC214495
0.7907	Intermediate Similarity	NPC475226
0.7674	Intermediate Similarity	NPC308205
0.6667	Remote Similarity	NPC475066
0.6629	Remote Similarity	NPC29695
0.6517	Remote Similarity	NPC182427
0.6413	Remote Similarity	NPC322546
0.62	Remote Similarity	NPC475237
0.618	Remote Similarity	NPC291150
0.6122	Remote Similarity	NPC475641
0.6105	Remote Similarity	NPC488535
0.6061	Remote Similarity	NPC61967
0.59	Remote Similarity	NPC27541
0.587	Remote Similarity	NPC604850
0.58	Remote Similarity	NPC126984
0.5761	Remote Similarity	NPC5180
0.5699	Remote Similarity	NPC116717
0.5446	Remote Similarity	NPC118086
0.53	Remote Similarity	NPC62692
0.5243	Remote Similarity	NPC307781
0.5243	Remote Similarity	NPC472670
0.5243	Remote Similarity	NPC601577
0.52	Remote Similarity	NPC610307
0.5196	Remote Similarity	NPC608851
0.5096	Remote Similarity	NPC264690

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC470119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3723
0.1-0.2	5397
0.2-0.3	30
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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