NPASS Compound

Natural Product: NPC472760

Natural Product ID	NPC472760
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VRNFFDMZKHRMEH-KNMGUQBGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3582007
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

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 93 96 0 0 0 0 0 0 0 0999 V2000 10.5806 -4.2618 1.6941 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4380 -3.2819 1.7463 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3602 -2.5448 0.4255 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2155 -1.5610 0.5426 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0767 -0.8190 -0.7742 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9394 0.1841 -0.7046 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6462 -0.4496 -0.3570 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1834 -1.4950 -1.3153 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9109 -2.0498 -0.8007 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0202 -3.1687 -0.1552 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6349 -1.4772 -0.9494 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2284 -0.4039 -1.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9096 0.6182 -2.2606 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2891 1.6899 -2.7889 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8937 1.8731 -2.6472 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2857 2.9848 -3.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1225 2.9993 -2.8744 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8432 3.9576 -3.2773 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7224 2.0172 -2.1647 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0959 1.9291 -1.8090 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6687 3.0074 -0.9963 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6012 2.8017 0.4865 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7299 1.3603 0.8298 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4604 0.6350 -0.2400 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5779 0.5733 -1.4703 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0024 1.1631 -2.7463 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3003 0.5836 -3.9871 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 1.5665 -3.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7059 -0.7786 0.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5164 -1.0891 1.2411 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3402 -0.1421 2.0442 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4525 0.8583 2.6844 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0969 1.0634 2.2311 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2899 -0.0174 2.8359 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9181 -0.4884 3.8857 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1773 0.2417 4.0511 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8456 0.3205 5.0803 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5095 -1.5860 4.8513 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1762 2.0234 3.0483 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5750 -2.5347 1.5880 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9029 -2.9725 1.4116 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3922 0.8549 0.7252 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5626 3.7381 1.1665 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3365 -5.1173 1.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4958 -3.7594 1.2702 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8050 -4.5932 2.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5128 -2.5898 2.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4722 -3.8390 1.8675 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1272 -3.2812 -0.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2955 -2.0499 0.1670 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3026 -2.1473 0.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3732 -0.8575 1.3756 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9808 -1.5046 -1.6262 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0100 -0.2337 -0.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2163 0.9500 0.0333 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8690 0.6188 -1.7195 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6510 -0.8859 0.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8952 0.3808 -0.2646 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9468 -2.3446 -1.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1447 -1.1789 -2.3551 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7854 -2.0977 -0.4531 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1223 -0.2166 -1.4163 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9769 0.5862 -2.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9158 2.3959 -3.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2429 1.1662 -2.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8208 3.6777 -3.7092 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6833 3.3267 -1.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0370 3.9335 -1.2005 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5820 3.1423 0.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4183 1.0458 -0.5235 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8701 -0.2611 -1.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0906 0.0880 -4.5793 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6177 -0.2512 -3.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7993 1.3586 -4.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9245 2.0408 -2.1762 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0232 0.7191 -3.4123 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3877 2.3293 -3.8441 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1579 -1.5396 -0.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9667 -0.7153 2.7581 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0328 0.3816 1.3624 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7288 1.9994 2.7996 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3419 -0.3574 2.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2064 -2.4131 4.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5154 -1.0829 5.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4682 -1.8679 4.6868 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7423 2.4172 3.8493 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1818 -2.7473 2.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9570 -3.0864 0.8571 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0756 -2.9936 0.4308 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8358 1.3131 1.4153 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3509 3.8434 2.2471 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3153 4.7730 0.7603 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6105 3.6023 0.9472 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 3 12 13 1 0 13 14 2 3 14 15 1 0 15 16 2 3 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 24 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 35 38 1 0 32 39 1 0 30 40 1 0 40 41 1 0 23 42 1 0 22 43 1 0 25 20 1 0 26 20 1 0 33 23 1 0 36 32 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 11 61 1 0 12 62 1 0 13 63 1 0 14 64 1 0 15 65 1 0 16 66 1 0 21 67 1 0 21 68 1 0 22 69 1 0 24 70 1 0 25 71 1 0 27 72 1 0 27 73 1 0 27 74 1 0 28 75 1 0 28 76 1 0 28 77 1 0 29 78 1 0 31 79 1 0 31 80 1 0 33 81 1 0 34 82 1 0 38 83 1 0 38 84 1 0 38 85 1 0 39 86 1 0 40 87 1 0 40 88 1 0 41 89 1 0 42 90 1 0 43 91 1 0 43 92 1 0 43 93 1 0 M END

Standard InCHIKey	VRNFFDMZKHRMEH-KNMGUQBGSA-N
Standard InCHI	InChI=1S/C36H50O7/c1-6-7-8-9-10-13-16-27(38)17-14-11-12-15-18-30(39)43-35-21-25(3)36(42)28(31(35)33(35,4)5)20-26(23-37)22-34(41)29(36)19-24(2)32(34)40/h11-12,14-15,17-20,25,28-29,31,37,41-42H,6-10,13,16,21-23H2,1-5H3/b12-11+,17-14+,18-15+/t25-,28+,29-,31-,34-,35+,36-/m1/s1
SMILES	CCCCCCCCC(=O)C=CC=CC=CC(=O)OC12CC(C3(C(C1C2(C)C)C=C(CC4(C3C=C(C4=O)C)O)CO)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.36	Volume:	637.426 ? Van der Waals volume.
Dense:	0.932	LogP:	5.73 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.527 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.596 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	24.0
TPSA:	121.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.085	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.219	Fsp³:	0.639
MCE-18:	77.186 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.667	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.102 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.272 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.265	Promiscuous compounds:	0.098

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.976	MDCK Permeability:	-4.71
Pgp-inhibitor:	0.001	Pgp-substrate:	0.034
PAMPA:	0.837 ? 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):	0.721
20% Bioavailability (F20%):	0.922	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.987
Plasma Protein Binding (PPB):	96.692%	Volume Distribution (VD):	0.379
Fu:	4.019% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.598
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.92

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.652
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.995	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.497	CYP3A4-substrate:	0.258
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.63 ? 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):

3.778

Half-life (T1/2):

1.067

ADMET: Toxicity

hERG Blockers:	0.285	hERG Blockers (10um):	0.543
Human Hepatotoxicity (H-HT):	0.568	Drug-induced Liver Injury (DILI):	0.249
AMES Toxicity:	0.475	Rat Oral Acute Toxicity:	0.529
Maximum Recommended Daily Dose:	0.672	Skin Sensitization:	0.669
Carcinogencity:	0.312	Eye Corrosion:	0.0
Eye Irritation:	0.067	Respiratory Toxicity:	0.921
Drug-induced Neurotoxicity:	0.32	Ototoxicity:	0.775
Hematotoxicity:	0.237	Drug-induced Nephrotoxicity:	0.45
Genotoxicity:	0.051	RPMI-8226 Immunitoxicity:	0.16
A549 Cytotoxicity:	0.419	Hek293 Cytotoxicity:	0.464
BCF:	1.738 ? 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:	4.893 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.771 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.908 ? 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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
EC50	5
Inhibition	3
Ratio CC50/EC50	4
CC50	2

Activity Type	# Activity
Cell line	5
Organism	4
Non-molecular	1
Others	4

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
NPT393	Cell line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[17844994]
NPT83	Cell line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[17844994]
NPT306	Cell line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[16793266]
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	=	13000.0	nM	DrugMatrix in vivo data: Biochemistry
NPT25	Cell line	MT4	Homo sapiens	CC50	=	13000.0	nM	PMID[20805391]
NPT856	Organism	Semliki forest virus	Semliki forest virus	EC50	>	168000.0	nM	PMID[22264149]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	18.0	nM	PMID[25316316]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	2200.0	nM	PMID[25946116]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	43.0	nM	PubChem BioAssay data set
NPT338	Organism	Sindbis virus	Sindbis virus	EC50	=	11000.0	nM	PMID[16563751]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	299.0	n.a.	PMID[18698821]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	1431.0	n.a.	PMID[17181158]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	5.9	n.a.	PMID[17685651]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	1.2	n.a.	DOI[10.6019/CHEMBL1201861]

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 NPC472760 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	15712
0.1-0.2	33195
0.2-0.3	808
0.3-0.4	61
0.4-0.5	33
0.5-0.6	33
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8182	Intermediate Similarity	NPC180640
0.7123	Intermediate Similarity	NPC485736
0.7123	Intermediate Similarity	NPC277477
0.7123	Intermediate Similarity	NPC479003
0.7123	Intermediate Similarity	NPC485735
0.6857	Remote Similarity	NPC153036
0.6711	Remote Similarity	NPC482454
0.6667	Remote Similarity	NPC158523
0.6667	Remote Similarity	NPC485732
0.6486	Remote Similarity	NPC71889
0.6486	Remote Similarity	NPC475937
0.6395	Remote Similarity	NPC185876
0.6395	Remote Similarity	NPC19336
0.6049	Remote Similarity	NPC477091
0.5823	Remote Similarity	NPC485733
0.5814	Remote Similarity	NPC153651
0.561	Remote Similarity	NPC17138
0.561	Remote Similarity	NPC101825
0.561	Remote Similarity	NPC170212
0.561	Remote Similarity	NPC215643
0.561	Remote Similarity	NPC265499
0.5542	Remote Similarity	NPC221511
0.5526	Remote Similarity	NPC91189
0.5476	Remote Similarity	NPC485731
0.5402	Remote Similarity	NPC145238
0.5385	Remote Similarity	NPC96739
0.5349	Remote Similarity	NPC151216
0.5349	Remote Similarity	NPC89227
0.5333	Remote Similarity	NPC482199
0.5333	Remote Similarity	NPC482197
0.5326	Remote Similarity	NPC479001
0.5326	Remote Similarity	NPC479002
0.5287	Remote Similarity	NPC484333
0.5287	Remote Similarity	NPC479000
0.5238	Remote Similarity	NPC275696
0.5238	Remote Similarity	NPC255081
0.5222	Remote Similarity	NPC236999
0.5217	Remote Similarity	NPC482198
0.5185	Remote Similarity	NPC174471
0.5176	Remote Similarity	NPC474872
0.5176	Remote Similarity	NPC5991
0.5176	Remote Similarity	NPC196500
0.5176	Remote Similarity	NPC471108
0.5176	Remote Similarity	NPC5989
0.5172	Remote Similarity	NPC478999
0.506	Remote Similarity	NPC474871
0.506	Remote Similarity	NPC260786

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6439
0.1-0.2	2688
0.2-0.3	23
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