NPASS Compound

Natural Product: NPC290833

Natural Product ID	NPC290833
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,3S,4R,5R,7S,8S,9S13S,15R*)-3Beta,7Beta,8Alpha,9Alpha,15Beta-Pentaacetoxy-5Alpha-Benzoyloxyjatropha-6(17),11E-Dien-14-One
IUPAC Name	[(1S,2S,3aR,5S,6E,9S,10S,11S,13R,13aR)-1,3a,9,10,11-pentaacetyloxy-2,5,8,8-tetramethyl-12-methylidene-4-oxo-2,3,5,9,10,11,13,13a-octahydro-1H-cyclopenta[12]annulen-13-yl] benzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL526702
PubChem CID	10349753
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane 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 96 98 0 0 0 0 0 0 0 0999 V2000 -1.2776 -4.6412 -1.7088 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7611 -3.1713 -1.8898 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0305 -2.3860 -1.7341 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2862 -1.7005 -0.6473 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4827 -0.8966 -0.4007 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1041 -0.3065 -1.6358 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5249 -1.8913 0.1241 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3360 0.1078 0.7201 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0879 0.9577 0.6234 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0929 0.7622 1.6828 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0633 -0.1002 1.6190 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1970 -1.0948 2.5089 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1830 -0.0189 0.6395 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0042 -0.6307 -0.6821 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1049 -0.0577 -1.5980 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7928 -0.9495 -2.8496 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8678 -0.6214 -3.8413 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9709 -2.2824 -2.1591 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -2.0871 -0.7827 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1443 -2.9698 -0.7482 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0439 -3.5697 0.3300 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2548 -2.3907 0.2355 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7396 -3.6912 0.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2907 -4.5504 -0.3996 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7342 -4.0374 1.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3327 -0.5370 -1.1720 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5409 0.0982 -1.1449 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5751 1.2852 -1.5607 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7910 -0.5333 -0.6568 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5432 1.3736 0.4872 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7176 1.8747 1.0248 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5090 1.1206 1.6781 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1167 3.2682 0.8819 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2935 3.6974 1.4650 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7374 4.9984 1.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9775 5.9127 0.6639 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8095 5.4823 0.0861 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3604 4.1838 0.1775 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8158 0.3294 2.8959 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9606 1.0999 3.9986 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4599 2.2541 4.0198 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7064 0.5779 5.1694 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7598 1.4197 -0.6253 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9281 2.6145 -1.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4833 3.4913 -0.5426 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4895 2.8868 -2.5960 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4915 0.9637 0.4591 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4880 1.0568 1.4153 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3806 0.4060 2.4850 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6951 1.9282 1.1864 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4597 -5.3192 -1.9944 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1605 -4.7183 -2.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6016 -4.7282 -0.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3538 -3.1290 -2.8819 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7194 -2.4242 -2.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5612 -1.7385 0.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4988 -1.0923 -2.3131 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9969 0.2759 -1.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4031 0.2907 -2.2431 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5247 -1.4131 0.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5517 -2.7185 -0.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1436 -2.2804 1.0709 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4781 -0.3291 1.6630 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5822 1.9728 1.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7768 1.8199 2.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9994 -1.7929 2.5648 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5923 -1.2243 3.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1200 -0.4513 1.1030 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0280 -0.4692 -1.1677 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9917 0.9527 -1.9002 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7946 -0.7635 -3.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8202 -1.0937 -3.6125 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0010 0.4932 -3.8038 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5865 -0.8726 -4.8851 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5624 -3.0669 -2.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0628 -2.4492 -2.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4715 -5.0492 1.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7104 -4.1433 0.9412 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8016 -3.2725 2.2299 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2839 -1.0903 -1.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6059 -1.1751 0.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5071 0.2450 -0.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9097 3.0045 2.0249 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6699 5.2692 1.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3346 6.9447 0.5917 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2071 6.2010 -0.4741 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4478 3.8243 -0.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6133 0.0249 4.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0874 -0.1119 5.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9625 1.4301 5.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4683 2.4538 -2.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1634 2.2873 -3.2752 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5044 3.9554 -2.8693 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8524 2.0395 0.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6028 1.4550 1.6064 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5316 2.9410 1.6212 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 4 5 1 0 5 6 1 0 5 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 19 22 1 1 22 23 1 0 23 24 2 0 23 25 1 0 15 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 13 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 10 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 9 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 8 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 20 2 1 0 38 33 1 0 19 14 1 0 1 51 1 0 1 52 1 0 1 53 1 0 2 54 1 6 3 55 1 0 4 56 1 0 6 57 1 0 6 58 1 0 6 59 1 0 7 60 1 0 7 61 1 0 7 62 1 0 8 63 1 1 9 64 1 1 10 65 1 1 12 66 1 0 12 67 1 0 13 68 1 1 14 69 1 6 15 70 1 6 16 71 1 6 17 72 1 0 17 73 1 0 17 74 1 0 18 75 1 0 18 76 1 0 25 77 1 0 25 78 1 0 25 79 1 0 29 80 1 0 29 81 1 0 29 82 1 0 34 83 1 0 35 84 1 0 36 85 1 0 37 86 1 0 38 87 1 0 42 88 1 0 42 89 1 0 42 90 1 0 46 91 1 0 46 92 1 0 46 93 1 0 50 94 1 0 50 95 1 0 50 96 1 0 M END

Standard InCHIKey	CCEJPZNXXDEIOF-YXHNETSESA-N
Standard InCHI	InChI=1S/C37H46O13/c1-19-16-17-36(9,10)34(48-25(7)41)32(47-24(6)40)31(46-23(5)39)21(3)30(49-35(44)27-14-12-11-13-15-27)28-29(45-22(4)38)20(2)18-37(28,33(19)43)50-26(8)42/h11-17,19-20,28-32,34H,3,18H2,1-2,4-10H3/b17-16+/t19-,20-,28+,29-,30-,31-,32+,34+,37+/m0/s1
SMILES	C[C@H]1/C=C/C(C)(C)[C@@H]([C@@H]([C@H](C(=C)[C@@H]([C@H]2[C@H]([C@@H](C)C[C@@]2(C1=O)OC(=O)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	698.29	Volume:	705.474 ? Van der Waals volume.
Dense:	0.99	LogP:	2.762 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.02 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.736 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	30.0
TPSA:	174.87 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.225	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.694	Fsp³:	0.541
MCE-18:	108.351 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.712	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.318	Promiscuous compounds:	0.118

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.178	MDCK Permeability:	-4.72
Pgp-inhibitor:	1.0	Pgp-substrate:	0.043
PAMPA:	0.025 ? 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):	0.001
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	95.079%	Volume Distribution (VD):	-0.326
Fu:	4.992% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.002
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

4.593

Half-life (T1/2):

0.522

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.091
Human Hepatotoxicity (H-HT):	0.42	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.743	Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.071	Skin Sensitization:	0.991
Carcinogencity:	0.614	Eye Corrosion:	0.001
Eye Irritation:	0.127	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.224	Ototoxicity:	0.293
Hematotoxicity:	0.664	Drug-induced Nephrotoxicity:	0.864
Genotoxicity:	0.996	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.376	Hek293 Cytotoxicity:	0.348
BCF:	0.661 ? 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:	3.678 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.597 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.177 ? 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
NPO18344	Euphorbia mongolica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880317]
NPO33056	euphorbia squamosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25437914]
NPO33056	euphorbia squamosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18344	Euphorbia mongolica	Species	Euphorbiaceae	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
Flu intensity	2
Ratio	2

Activity Type	# Activity
Individual protein	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	33.71	n.a.	PMID[12880317]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	354.21	n.a.	PMID[12880317]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	2.79	n.a.	PMID[16643052]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	29.29	n.a.	PMID[23691978]

In vitro activity

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

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 NPC290833 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	13193
0.1-0.2	34227
0.2-0.3	1910
0.3-0.4	418
0.4-0.5	52
0.5-0.6	27
0.6-0.7	18
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC482249
0.8857	High Similarity	NPC265459
0.8857	High Similarity	NPC475262
0.8857	High Similarity	NPC482265
0.8333	Intermediate Similarity	NPC482304
0.7703	Intermediate Similarity	NPC482314
0.75	Intermediate Similarity	NPC482251
0.7375	Intermediate Similarity	NPC482250
0.7317	Intermediate Similarity	NPC482258
0.7105	Intermediate Similarity	NPC482307
0.7051	Intermediate Similarity	NPC482254
0.7013	Intermediate Similarity	NPC86772
0.6962	Remote Similarity	NPC482268
0.6875	Remote Similarity	NPC482263
0.6835	Remote Similarity	NPC482248
0.6795	Remote Similarity	NPC482300
0.675	Remote Similarity	NPC482301
0.675	Remote Similarity	NPC482269
0.6709	Remote Similarity	NPC194769
0.6709	Remote Similarity	NPC482270
0.6667	Remote Similarity	NPC482252
0.6625	Remote Similarity	NPC285221
0.6582	Remote Similarity	NPC482315
0.6543	Remote Similarity	NPC475660
0.6543	Remote Similarity	NPC482267
0.65	Remote Similarity	NPC82467
0.6296	Remote Similarity	NPC482247
0.6265	Remote Similarity	NPC482255
0.625	Remote Similarity	NPC482308
0.6173	Remote Similarity	NPC482266
0.5952	Remote Similarity	NPC482310
0.5952	Remote Similarity	NPC482302
0.5934	Remote Similarity	NPC482261
0.5889	Remote Similarity	NPC187494
0.5814	Remote Similarity	NPC482201
0.5765	Remote Similarity	NPC472247
0.5765	Remote Similarity	NPC482359
0.5765	Remote Similarity	NPC482272
0.5761	Remote Similarity	NPC482262
0.5591	Remote Similarity	NPC482260
0.5529	Remote Similarity	NPC482231
0.5476	Remote Similarity	NPC482360
0.5395	Remote Similarity	NPC105725
0.5376	Remote Similarity	NPC482259
0.5333	Remote Similarity	NPC317191
0.5301	Remote Similarity	NPC196683
0.5294	Remote Similarity	NPC228674
0.5275	Remote Similarity	NPC482155
0.5275	Remote Similarity	NPC470190
0.5256	Remote Similarity	NPC482404
0.5222	Remote Similarity	NPC170668
0.5217	Remote Similarity	NPC482204
0.5172	Remote Similarity	NPC272523
0.5165	Remote Similarity	NPC482202
0.5161	Remote Similarity	NPC482154
0.5057	Remote Similarity	NPC276652
0.5056	Remote Similarity	NPC205389

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC290833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3938
0.1-0.2	5100
0.2-0.3	111
0.3-0.4	1
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