NPASS Compound

Natural Product: NPC473283

Natural Product ID	NPC473283
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	13E-Globostellatic Acid B Methyl Ester
IUPAC Name	methyl (3E,3aS,5aR,6R,7R,9aR,9bS)-7-acetyloxy-3-[(3E,5E,8E)-10-hydroxy-7-methoxy-6,10-dimethylundeca-3,5,8-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalene-6-carboxylate
Synonyms	13E-Globostellatic Acid B Methyl Ester
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL392801
PubChem CID	44434368
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 91 93 0 0 0 0 0 0 0 0999 V2000 5.4874 3.8705 0.8290 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0036 2.6961 0.2824 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4549 1.5744 0.8882 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7545 0.7867 -0.1727 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4687 0.4978 -0.0866 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8782 -0.2803 -1.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6059 -0.6189 -1.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9536 -1.3822 -2.2275 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3604 -1.5896 -2.1189 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0941 -2.3542 -3.1281 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7378 -2.6173 -4.2781 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4014 -2.7575 -2.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6440 -1.4277 -1.8074 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3429 -1.1805 -1.0930 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0999 -2.0675 0.1016 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3193 0.2810 -0.7340 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7292 0.9101 -0.7822 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6368 -0.0811 -0.0935 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8921 -1.1930 -1.0989 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9170 -0.6627 -2.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5648 -2.3266 -0.4141 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9012 -1.9789 1.0438 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6713 -0.6633 1.0875 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8438 0.4894 0.5442 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3540 1.2332 1.8014 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6201 1.4366 -0.2336 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8181 1.2099 -0.5023 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0587 2.6077 -0.6952 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7915 3.5559 -1.4592 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0617 -0.4715 2.4266 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3863 -0.4452 2.8359 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2689 -0.5996 1.9706 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7192 -0.2386 4.2619 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6956 -1.9623 -3.4118 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5642 0.3392 -1.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5602 0.7723 1.4698 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7974 0.9960 1.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9557 0.2278 1.5904 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5533 -0.4983 0.5418 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9797 1.2379 2.0486 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5458 -0.7031 2.6916 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9282 4.7492 0.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6795 3.9196 1.9178 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3884 3.9129 0.6650 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7221 1.8872 1.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9228 0.8358 0.7589 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4984 -0.5784 -2.0022 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0468 -0.2886 -0.3253 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1439 -3.0741 -3.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1212 -3.5630 -1.7774 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5852 -0.6973 -2.6858 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9507 -2.6443 0.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2672 -2.8003 -0.0593 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6904 -1.3821 0.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0369 0.3741 0.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7031 0.8831 -1.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7404 1.8494 -0.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9923 1.1510 -1.8087 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0233 -0.5199 0.7412 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6714 -1.1958 -3.0726 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8118 0.4009 -2.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9452 -0.9962 -1.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0540 -3.2836 -0.4003 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5881 -2.5656 -0.8462 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6015 -2.7600 1.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0346 -2.0020 1.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5799 -0.7800 0.4748 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9505 2.2002 1.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1761 1.4137 2.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5231 0.6487 2.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3030 3.5831 -2.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8507 3.2150 -1.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8147 4.5448 -0.9704 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3496 -1.0616 4.6611 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2479 0.7365 4.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8223 -0.1804 4.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7670 -1.8913 -3.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3864 -3.0364 -3.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4488 -1.3393 -4.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5962 -0.7695 -1.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0893 0.6724 -2.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5587 0.7985 -1.3274 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3840 -0.0006 2.2368 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0493 1.7482 0.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0217 -0.4321 -0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5289 1.8305 2.8598 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9287 0.7839 2.3749 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1530 1.9223 1.1789 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4556 -1.2556 3.0153 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1548 -0.1374 3.5428 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8464 -1.4487 2.2975 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 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 23 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 8 34 1 0 4 35 1 0 3 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 38 40 1 0 38 41 1 0 14 9 1 0 24 18 1 0 19 13 1 0 1 42 1 0 1 43 1 0 1 44 1 0 3 45 1 0 5 46 1 0 6 47 1 0 7 48 1 0 12 49 1 0 12 50 1 0 13 51 1 6 15 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 1 20 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 23 67 1 6 25 68 1 0 25 69 1 0 25 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 33 74 1 0 33 75 1 0 33 76 1 0 34 77 1 0 34 78 1 0 34 79 1 0 35 80 1 0 35 81 1 0 35 82 1 0 36 83 1 0 37 84 1 0 39 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 41 89 1 0 41 90 1 0 41 91 1 0 M END

Standard InCHIKey	QIHQIMPZPQVOJO-ZWZVHUMJSA-N
Standard InCHI	InChI=1S/C34H50O7/c1-21(25(39-9)14-17-31(4,5)38)12-11-13-22(2)29-24(36)20-27-32(6)19-16-28(41-23(3)35)34(8,30(37)40-10)26(32)15-18-33(27,29)7/h11-14,17,25-28,38H,15-16,18-20H2,1-10H3/b13-11+,17-14+,21-12+,29-22-/t25?,26-,27+,28-,32+,33+,34-/m1/s1
SMILES	COC(/C(=C/C=C/C(=C1/C(=O)C[C@@H]2[C@]1(C)CC[C@@H]1[C@]2(C)CC[C@H]([C@]1(C)C(=O)OC)OC(=O)C)/C)/C)/C=C/C(O)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	570.36	Volume:	614.027 ? Van der Waals volume.
Dense:	0.929	LogP:	3.239 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.149 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.462 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	22.0
TPSA:	99.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.164	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.276	Fsp³:	0.676
MCE-18:	73.965 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.591	Fluc inhibitor:	0.039 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.058 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.012 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.436	Promiscuous compounds:	0.25

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.073	MDCK Permeability:	-4.821
Pgp-inhibitor:	0.967	Pgp-substrate:	0.052
PAMPA:	0.017 ? 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):	0.0
20% Bioavailability (F20%):	0.012	30% Bioavailability (F30%):	0.044
50% Bioavailability (F50%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.989
Plasma Protein Binding (PPB):	88.081%	Volume Distribution (VD):	-0.294
Fu:	9.734% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.314
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.487	CYP1A2-substrate:	0.668
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.232
CYP2C9-inhibitor:	0.02	CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.479
CYP2B6-substrate:	0.01	CYP2C8-inhibitor:	0.999
HLM stability:	0.908 ? 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):

7.709

Half-life (T1/2):

0.444

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.131
Human Hepatotoxicity (H-HT):	0.673	Drug-induced Liver Injury (DILI):	0.525
AMES Toxicity:	0.448	Rat Oral Acute Toxicity:	0.492
Maximum Recommended Daily Dose:	0.529	Skin Sensitization:	0.967
Carcinogencity:	0.87	Eye Corrosion:	0.0
Eye Irritation:	0.051	Respiratory Toxicity:	0.476
Drug-induced Neurotoxicity:	0.122	Ototoxicity:	0.708
Hematotoxicity:	0.607	Drug-induced Nephrotoxicity:	0.814
Genotoxicity:	0.926	RPMI-8226 Immunitoxicity:	0.079
A549 Cytotoxicity:	0.125	Hek293 Cytotoxicity:	0.409
BCF:	1.133 ? 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:	4.11 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.84 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.205 ? 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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	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	4
Ratio IC50	3

Activity Type	# Activity
Cell line	5
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
NPT737	Cell line	HUVEC	Homo sapiens	IC50	=	1100.0	nM	PMID[15921431]
NPT111	Cell line	K562	Homo sapiens	IC50	=	9300.0	nM	PMID[22372956]
NPT737	Cell line	HUVEC	Homo sapiens	Ratio IC50	=	6.0	n.a.	PMID[12398531]
NPT111	Cell line	K562	Homo sapiens	Ratio IC50	=	9.0	n.a.	PMID[12398531]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	6500.0	nM	PMID[17524651]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	6000.0	nM	PMID[17524651]

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 NPC473283 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	17750
0.1-0.2	27212
0.2-0.3	4747
0.3-0.4	87
0.4-0.5	33
0.5-0.6	16
0.6-0.7	4
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	NPC475526
0.7794	Intermediate Similarity	NPC473482
0.7538	Intermediate Similarity	NPC151725
0.7313	Intermediate Similarity	NPC473435
0.7313	Intermediate Similarity	NPC473280
0.7313	Intermediate Similarity	NPC471078
0.7286	Intermediate Similarity	NPC473284
0.7101	Intermediate Similarity	NPC106425
0.7101	Intermediate Similarity	NPC122324
0.6818	Remote Similarity	NPC2049
0.6711	Remote Similarity	NPC329345
0.6061	Remote Similarity	NPC161638
0.6061	Remote Similarity	NPC80335
0.5789	Remote Similarity	NPC155332
0.5789	Remote Similarity	NPC114540
0.5658	Remote Similarity	NPC266955
0.5616	Remote Similarity	NPC474842
0.5616	Remote Similarity	NPC475965
0.5616	Remote Similarity	NPC604299
0.5526	Remote Similarity	NPC605871
0.5513	Remote Similarity	NPC115899
0.5455	Remote Similarity	NPC110937
0.5256	Remote Similarity	NPC10064
0.5256	Remote Similarity	NPC170221
0.5181	Remote Similarity	NPC318363
0.5128	Remote Similarity	NPC6206
0.5065	Remote Similarity	NPC471153
0.5057	Remote Similarity	NPC473617
0.5057	Remote Similarity	NPC473828

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6325
0.1-0.2	2751
0.2-0.3	74
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