NPASS Compound

Natural Product: NPC228784

Natural Product ID	NPC228784
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Echinocystic Acid
IUPAC Name	(4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bR)-5,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	Echinocystic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL464557
PubChem CID	476486
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 82 86 0 0 0 0 0 0 0 0999 V2000 -4.8105 2.8691 -0.9695 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8283 1.4047 -1.3947 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5959 1.3762 -2.7247 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5827 0.5463 -0.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7959 0.1441 0.7765 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4958 -0.5097 0.3242 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7654 0.5212 -0.4617 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4350 0.9190 -1.7067 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3629 0.0534 -0.6324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8436 -0.3596 -1.7568 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5842 -0.8323 -1.9073 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3240 -0.3392 -0.7145 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8242 -0.5948 -0.7778 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1826 -2.0050 -0.9883 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3463 0.1747 -2.0005 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8389 0.1292 -2.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5979 0.1630 -0.8406 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8288 0.4606 0.3904 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5779 -0.2133 1.5536 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0318 1.9626 0.6881 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3877 0.0926 0.4081 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9565 -0.6556 1.6480 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4552 -0.6285 1.7978 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6720 -0.7190 0.5630 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1520 -2.1679 0.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5863 0.1397 0.6489 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2083 1.6248 0.7366 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4670 -0.1788 1.7864 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6855 -0.9779 1.5076 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5208 -0.8579 2.6442 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4151 -0.9832 -0.6655 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8768 -1.6607 -0.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4856 -1.8064 -1.6606 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7195 -2.6788 -0.0104 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7945 3.1667 -0.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5141 3.0864 -0.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0381 3.5488 -1.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0444 2.1086 -3.3776 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5070 0.3965 -3.1927 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6263 1.7155 -2.5318 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9864 -0.3450 -0.9623 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4613 1.1242 -0.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3755 -0.6373 1.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6225 0.9956 1.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7776 1.4470 0.2064 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3932 0.2226 -2.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8941 1.8797 -2.0487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4446 -0.3659 -2.6508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5568 -1.9074 -2.0724 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9401 -0.3318 -2.8438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2742 0.7933 -0.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4253 -2.5044 -1.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3283 -2.6249 -0.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1224 -2.1479 -1.6049 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9636 -0.3589 -2.9209 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9359 1.1864 -1.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1640 -0.7823 -2.6999 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1107 0.9763 -2.8151 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3920 0.9628 -0.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6799 -0.0962 1.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3916 0.3680 2.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3134 -1.2545 1.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9716 2.1493 1.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1325 2.3029 1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9576 2.4630 -0.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8335 1.0724 0.5052 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3999 -0.1117 2.5094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3302 -1.6825 1.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1549 0.2400 2.4220 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2307 -1.5008 2.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9704 -2.8773 0.2211 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7281 -2.2465 -0.1745 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1726 -2.4857 1.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0778 2.1458 1.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7212 1.8166 1.2568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1639 2.1092 -0.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9329 -0.7155 2.6284 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8241 0.7672 2.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5202 -2.0678 1.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1691 -1.5893 2.6646 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9839 -1.6947 -0.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3259 -3.1289 -0.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 17 31 1 0 6 32 1 6 32 33 2 0 32 34 1 0 8 2 1 0 26 9 1 0 29 6 1 0 24 12 1 0 21 13 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 7 45 1 1 8 46 1 0 8 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 6 14 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 17 59 1 6 19 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 20 65 1 0 21 66 1 1 22 67 1 0 22 68 1 0 23 69 1 0 23 70 1 0 25 71 1 0 25 72 1 0 25 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 28 77 1 0 28 78 1 0 29 79 1 6 30 80 1 0 31 81 1 0 34 82 1 0 M END

Standard InCHIKey	YKOPWPOFWMYZJZ-RQDPUMMDSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-25(2)14-15-30(24(33)34)19(16-25)18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-28(21,6)29(18,7)17-23(30)32/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,21-,22+,23-,27+,28-,29-,30-/m1/s1
SMILES	CC1(C)CC[C@]2([C@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.214 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.077 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.758 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.397	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.795	Fsp³:	0.9
MCE-18:	108.07 ? 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:	0.698	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.379	Promiscuous compounds:	0.08

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.481	MDCK Permeability:	-5.092
Pgp-inhibitor:	0.0	Pgp-substrate:	0.037
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):	0.003
20% Bioavailability (F20%):	0.608	30% Bioavailability (F30%):	0.069
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.781	MRP1:	0.974
Plasma Protein Binding (PPB):	94.681%	Volume Distribution (VD):	-0.318
Fu:	6.162% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.923	BCRP inhibitor:	0.078
BSEP inhibitor:	0.214

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.02	CYP2C19-substrate:	0.408
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.471
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.464
HLM stability:	0.068 ? 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):

2.508

Half-life (T1/2):

1.209

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.061
Human Hepatotoxicity (H-HT):	0.709	Drug-induced Liver Injury (DILI):	0.426
AMES Toxicity:	0.384	Rat Oral Acute Toxicity:	0.536
Maximum Recommended Daily Dose:	0.501	Skin Sensitization:	0.928
Carcinogencity:	0.933	Eye Corrosion:	0.064
Eye Irritation:	0.651	Respiratory Toxicity:	0.92
Drug-induced Neurotoxicity:	0.052	Ototoxicity:	0.586
Hematotoxicity:	0.448	Drug-induced Nephrotoxicity:	0.895
Genotoxicity:	0.587	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.385	Hek293 Cytotoxicity:	0.258
BCF:	1.66 ? 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:	4.113 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.567 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.967 ? 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
NPO27443	Gymnocladus chinensis	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27443	Gymnocladus chinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7631	Gleditsia japonica	Species	Fabaceae	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
Kd	2
Inhibition	7
EC50	1
IC50	2
Activity	7

Activity Type	# Activity
Individual protein	3
Cell line	3
Organism	12
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2639	Individual protein	CD81 antigen	Homo sapiens	Kd	=	21.0	nM	PMID[23662817]
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	30.48	%	PMID[23571415]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	69.3	%	PMID[23571415]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell line	H9	Homo sapiens	IC50	=	74000.0	nM	PMID[7494144]
NPT380	Cell line	U-251	Homo sapiens	Activity	=	33.73	%	PMID[25442304]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	52.31	%	PMID[25442304]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	42000.0	nM	PMID[7494144]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	90.0	%	PMID[23662817]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	IC50	=	1400.0	nM	PMID[23662817]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	77.7	%	PMID[23662817]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	27.5	%	PMID[23662817]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	=	75.5	%	PMID[23644199]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	=	21.3	%	PMID[23644199]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	=	90.0	%	PMID[26318066]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Inhibition	=	9.0	%	PMID[23662817]
NPT2	Others	Unspecified	n.a.	Kd	=	24000.0	nM	PMID[23662817]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Inhibition	=	7.2	%	PMID[23662817]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	-0.1	%	PMID[23644199]

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 NPC228784 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	22252
0.1-0.2	22996
0.2-0.3	3467
0.3-0.4	745
0.4-0.5	268
0.5-0.6	82
0.6-0.7	32
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324341
1.0	High Similarity	NPC601810
0.8308	Intermediate Similarity	NPC222047
0.7656	Intermediate Similarity	NPC480946
0.7656	Intermediate Similarity	NPC130577
0.7656	Intermediate Similarity	NPC142415
0.7656	Intermediate Similarity	NPC102683
0.7313	Intermediate Similarity	NPC29765
0.7206	Intermediate Similarity	NPC201657
0.7183	Intermediate Similarity	NPC601365
0.6866	Remote Similarity	NPC198664
0.6857	Remote Similarity	NPC471588
0.6582	Remote Similarity	NPC31839
0.6522	Remote Similarity	NPC270768
0.6522	Remote Similarity	NPC59263
0.6522	Remote Similarity	NPC182797
0.6522	Remote Similarity	NPC210106
0.6522	Remote Similarity	NPC52169
0.6522	Remote Similarity	NPC488562
0.6522	Remote Similarity	NPC606443
0.65	Remote Similarity	NPC242611
0.6438	Remote Similarity	NPC6255
0.6338	Remote Similarity	NPC298554
0.6286	Remote Similarity	NPC84319
0.6286	Remote Similarity	NPC52021
0.6286	Remote Similarity	NPC599947
0.6143	Remote Similarity	NPC187722
0.6118	Remote Similarity	NPC76999
0.6111	Remote Similarity	NPC202728
0.6111	Remote Similarity	NPC158059
0.6056	Remote Similarity	NPC51700
0.6056	Remote Similarity	NPC64872
0.6056	Remote Similarity	NPC171203
0.6056	Remote Similarity	NPC25906
0.6056	Remote Similarity	NPC88716
0.6056	Remote Similarity	NPC307426
0.6056	Remote Similarity	NPC98442
0.6056	Remote Similarity	NPC68160
0.6056	Remote Similarity	NPC242468
0.6056	Remote Similarity	NPC112866
0.6026	Remote Similarity	NPC603645
0.6	Remote Similarity	NPC477872
0.5921	Remote Similarity	NPC474727
0.589	Remote Similarity	NPC293564
0.5833	Remote Similarity	NPC7260
0.5833	Remote Similarity	NPC210037
0.5833	Remote Similarity	NPC282616
0.5833	Remote Similarity	NPC275809
0.5833	Remote Similarity	NPC120968
0.5833	Remote Similarity	NPC227467
0.5833	Remote Similarity	NPC273621
0.5778	Remote Similarity	NPC488516
0.5753	Remote Similarity	NPC231063
0.5753	Remote Similarity	NPC282395
0.5753	Remote Similarity	NPC110308
0.5735	Remote Similarity	NPC34177
0.5714	Remote Similarity	NPC480950
0.5714	Remote Similarity	NPC80843
0.5694	Remote Similarity	NPC274330
0.5667	Remote Similarity	NPC480424
0.5652	Remote Similarity	NPC253807
0.5652	Remote Similarity	NPC158662
0.5616	Remote Similarity	NPC121798
0.5616	Remote Similarity	NPC306541
0.5616	Remote Similarity	NPC234346
0.5541	Remote Similarity	NPC130278
0.5541	Remote Similarity	NPC158141
0.5522	Remote Similarity	NPC290598
0.5522	Remote Similarity	NPC30590
0.5507	Remote Similarity	NPC311078
0.5479	Remote Similarity	NPC610937
0.5429	Remote Similarity	NPC235341
0.5405	Remote Similarity	NPC290972
0.5405	Remote Similarity	NPC488519
0.5395	Remote Similarity	NPC91010
0.5361	Remote Similarity	NPC488515
0.5352	Remote Similarity	NPC604575
0.5333	Remote Similarity	NPC106112
0.5333	Remote Similarity	NPC261935
0.5333	Remote Similarity	NPC18872
0.5333	Remote Similarity	NPC290614
0.5333	Remote Similarity	NPC472149
0.5333	Remote Similarity	NPC481360
0.5325	Remote Similarity	NPC130520
0.5286	Remote Similarity	NPC101475
0.5263	Remote Similarity	NPC200752
0.5263	Remote Similarity	NPC136697
0.5253	Remote Similarity	NPC75318
0.5238	Remote Similarity	NPC204407
0.5227	Remote Similarity	NPC18982
0.5205	Remote Similarity	NPC246708
0.52	Remote Similarity	NPC229281
0.52	Remote Similarity	NPC195019
0.5195	Remote Similarity	NPC263393
0.5195	Remote Similarity	NPC191412
0.5195	Remote Similarity	NPC114159
0.5195	Remote Similarity	NPC6818
0.5176	Remote Similarity	NPC606107
0.5169	Remote Similarity	NPC475627
0.5165	Remote Similarity	NPC198621
0.5165	Remote Similarity	NPC216940
0.5165	Remote Similarity	NPC262970
0.5149	Remote Similarity	NPC475486
0.5143	Remote Similarity	NPC474989
0.5139	Remote Similarity	NPC159168
0.5135	Remote Similarity	NPC17733
0.5135	Remote Similarity	NPC470629
0.5132	Remote Similarity	NPC61543
0.5132	Remote Similarity	NPC293048
0.5132	Remote Similarity	NPC225585
0.5132	Remote Similarity	NPC470375
0.5132	Remote Similarity	NPC470376
0.5072	Remote Similarity	NPC27765
0.5072	Remote Similarity	NPC122418
0.5072	Remote Similarity	NPC491014
0.507	Remote Similarity	NPC132478
0.5068	Remote Similarity	NPC72638
0.5067	Remote Similarity	NPC2539
0.5065	Remote Similarity	NPC145667
0.5065	Remote Similarity	NPC120840
0.5063	Remote Similarity	NPC187933
0.5063	Remote Similarity	NPC116457
0.5049	Remote Similarity	NPC288205
0.5049	Remote Similarity	NPC51465

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC228784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6545
0.1-0.2	2544
0.2-0.3	56
0.3-0.4	2
0.4-0.5	3
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