NPASS Compound

Natural Product: NPC118519

Natural Product ID	NPC118519
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta,6Beta,19Alpha-Trihydroxyurs-12-En-28-Oic Acid
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8R,8aR,10S,12aR,14bS)-1,8,10-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL517004
PubChem CID	10838721
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 83 87 0 0 0 0 0 0 0 0999 V2000 3.4242 -1.0402 -2.1517 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9096 -1.4587 -0.9370 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4303 -1.6625 -0.9368 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6329 -0.4341 -0.6150 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3524 0.2887 -1.9014 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2285 0.4130 0.4625 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6994 0.7052 0.2556 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3942 -0.6192 0.2371 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8518 -0.6224 0.4115 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2492 -1.8230 1.3003 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5988 -0.9568 -0.8968 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5069 0.5745 0.9705 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4122 1.1734 0.0502 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6398 1.6595 1.4981 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1757 1.3931 1.5362 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9569 1.6015 -0.8750 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3861 1.5517 0.8433 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0124 1.3948 0.4199 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6137 0.3142 -0.0112 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7207 -0.9021 -0.0636 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5855 -1.3724 1.3676 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3163 -1.9883 -0.8784 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7274 -2.2496 -0.5181 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6565 -1.0682 -0.5155 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0408 0.2773 -0.4285 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8567 1.3397 0.2544 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7909 2.6656 -0.5323 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4929 1.5398 1.5790 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3254 0.9968 0.2747 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6890 -0.3347 0.7838 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6301 -1.3520 0.6346 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0202 2.0244 1.1922 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4553 -1.1993 -1.7575 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6745 -1.3807 -1.7141 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8135 -1.1152 -2.9727 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2899 -1.7729 -2.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3773 -2.4750 -0.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1494 -2.0474 -1.9407 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1933 -2.5121 -0.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9885 -0.0938 -2.7545 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4260 1.3746 -1.8465 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6983 0.0868 -2.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2673 -0.2706 1.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9403 -1.1695 1.1231 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3127 -2.0605 1.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5588 -2.6546 1.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1723 -1.4236 2.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6841 -0.9842 -0.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5219 -0.1565 -1.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3699 -1.9641 -1.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2146 0.3059 1.8185 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4165 2.1581 0.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7683 2.6142 0.9047 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9223 1.9911 2.5446 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9603 0.7097 2.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6633 2.3673 1.6860 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8124 1.1890 -1.8851 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9758 2.0385 -0.8823 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2799 2.4785 -0.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7333 2.5453 0.4934 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3563 1.6688 1.9699 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6227 2.3114 0.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4523 -1.9903 1.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6061 -0.5130 2.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2903 -2.0346 1.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7513 -2.9311 -0.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2348 -1.8563 -1.9744 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7930 -2.8189 0.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0822 -3.0277 -1.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9904 0.6464 -1.5093 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7658 2.8764 -1.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0697 2.5907 -1.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6375 3.5317 0.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0678 0.7794 2.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6877 1.1287 -0.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6468 -0.6456 0.2668 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0016 -0.3296 1.8718 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1249 -2.3245 0.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0729 -1.5965 1.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3460 2.8525 0.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8559 1.5539 1.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2693 2.4407 1.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2951 -0.9202 -3.8514 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 6 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 9 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 7 16 1 6 6 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 1 20 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 1 26 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 24 33 1 6 33 34 2 0 33 35 1 0 8 2 1 0 25 19 1 0 20 4 1 0 31 24 1 0 15 7 1 0 1 36 1 0 2 37 1 1 3 38 1 0 3 39 1 0 5 40 1 0 5 41 1 0 5 42 1 0 6 43 1 1 8 44 1 1 10 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 1 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 25 70 1 6 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 6 30 76 1 0 30 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 35 83 1 0 M END

Standard InCHIKey	JPGOJQJBPLCRQP-HUVCIBQSSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-20-26(4)12-11-21(32)25(2,3)23(26)19(31)16-28(20,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20-,21+,22-,23+,26-,27-,28-,29-,30+/m1/s1
SMILES	O[C@@H]1C[C@]2(C)[C@@H]([C@@]3([C@@H]1C(C)(C)[C@@H](O)CC3)C)CC=C1[C@@]2(C)CC[C@@]2([C@H]1[C@](C)(O)[C@@H](CC2)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	2.365 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.407 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.013 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.382	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.089	Fsp³:	0.9
MCE-18:	110.772 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.59	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.208 ? 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:	0.296	Promiscuous compounds:	0.088

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.577	MDCK Permeability:	-5.147
Pgp-inhibitor:	0.0	Pgp-substrate:	0.562
PAMPA:	1.0 ? 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):	0.007
20% Bioavailability (F20%):	0.763	30% Bioavailability (F30%):	0.152
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.154	MRP1:	0.999
Plasma Protein Binding (PPB):	82.717%	Volume Distribution (VD):	-0.415
Fu:	14.324% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.896	BCRP inhibitor:	0.0
BSEP inhibitor:	0.408

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.062	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.658	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.968	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.006
HLM stability:	0.023 ? 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):

4.285

Half-life (T1/2):

1.206

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.047
Human Hepatotoxicity (H-HT):	0.635	Drug-induced Liver Injury (DILI):	0.365
AMES Toxicity:	0.417	Rat Oral Acute Toxicity:	0.571
Maximum Recommended Daily Dose:	0.531	Skin Sensitization:	0.987
Carcinogencity:	0.891	Eye Corrosion:	0.006
Eye Irritation:	0.318	Respiratory Toxicity:	0.934
Drug-induced Neurotoxicity:	0.106	Ototoxicity:	0.75
Hematotoxicity:	0.53	Drug-induced Nephrotoxicity:	0.941
Genotoxicity:	0.95	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.558	Hek293 Cytotoxicity:	0.286
BCF:	0.504 ? 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:	3.172 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.701 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.974 ? 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
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1279126]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919590]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	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
Inhibition	1
Activity	4
TC50	1

Activity Type	# Activity
Individual protein	1
Cell line	1
Organism	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5212	Individual protein	Sentrin-specific protease 1	Homo sapiens	Inhibition	=	3.2	%	PMID[35500202]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell line	C8166	Homo sapiens	TC50	=	2.0	ug ml-1	PMID[20041704]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	0.0	%	PMID[17070063]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	1.0	%	PMID[20232858]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	Activity	=	100.0	%	PMID[21144756]
NPT338	Organism	Sindbis virus	Sindbis virus	Activity	=	100.0	%	PubChem BioAssay data set

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 NPC118519 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	23354
0.1-0.2	22722
0.2-0.3	3063
0.3-0.4	521
0.4-0.5	131
0.5-0.6	37
0.6-0.7	18
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8594	High Similarity	NPC137072
0.8	Intermediate Similarity	NPC202728
0.8	Intermediate Similarity	NPC158059
0.7463	Intermediate Similarity	NPC136697
0.7353	Intermediate Similarity	NPC191412
0.7353	Intermediate Similarity	NPC114159
0.7353	Intermediate Similarity	NPC6818
0.7164	Intermediate Similarity	NPC64872
0.7164	Intermediate Similarity	NPC25906
0.7143	Intermediate Similarity	NPC187933
0.6986	Remote Similarity	NPC327179
0.6857	Remote Similarity	NPC132824
0.6714	Remote Similarity	NPC259733
0.6714	Remote Similarity	NPC158371
0.6714	Remote Similarity	NPC207922
0.6667	Remote Similarity	NPC157113
0.6389	Remote Similarity	NPC35239
0.6389	Remote Similarity	NPC247139
0.6338	Remote Similarity	NPC73489
0.6301	Remote Similarity	NPC118964
0.6301	Remote Similarity	NPC62516
0.625	Remote Similarity	NPC256247
0.6111	Remote Similarity	NPC235053
0.6111	Remote Similarity	NPC130278
0.6104	Remote Similarity	NPC96693
0.6104	Remote Similarity	NPC54909
0.6081	Remote Similarity	NPC148964
0.6053	Remote Similarity	NPC603658
0.5972	Remote Similarity	NPC290972
0.5915	Remote Similarity	NPC43686
0.5897	Remote Similarity	NPC233012
0.5833	Remote Similarity	NPC187722
0.5789	Remote Similarity	NPC284865
0.5753	Remote Similarity	NPC51700
0.5753	Remote Similarity	NPC88716
0.5753	Remote Similarity	NPC68160
0.5616	Remote Similarity	NPC480946
0.5616	Remote Similarity	NPC130577
0.5616	Remote Similarity	NPC142415
0.5616	Remote Similarity	NPC102683
0.56	Remote Similarity	NPC293564
0.5584	Remote Similarity	NPC147232
0.5584	Remote Similarity	NPC116457
0.5541	Remote Similarity	NPC182797
0.5541	Remote Similarity	NPC52169
0.5541	Remote Similarity	NPC488562
0.5395	Remote Similarity	NPC305464
0.5395	Remote Similarity	NPC139570
0.5395	Remote Similarity	NPC19376
0.5395	Remote Similarity	NPC25848
0.5333	Remote Similarity	NPC229281
0.5301	Remote Similarity	NPC600756
0.5263	Remote Similarity	NPC61543
0.5263	Remote Similarity	NPC293048
0.5263	Remote Similarity	NPC225585
0.52	Remote Similarity	NPC274330
0.5195	Remote Similarity	NPC291028
0.519	Remote Similarity	NPC174663
0.5132	Remote Similarity	NPC270768
0.5132	Remote Similarity	NPC59263
0.5132	Remote Similarity	NPC307282
0.5132	Remote Similarity	NPC210106
0.5132	Remote Similarity	NPC121798
0.5132	Remote Similarity	NPC234346
0.5132	Remote Similarity	NPC606443

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC118519 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6612
0.1-0.2	2484
0.2-0.3	49
0.3-0.4	4
0.4-0.5	1
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