NPASS Compound

Natural Product: NPC216940

Natural Product ID	NPC216940
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(23E)-Coumaroylhederagenin
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	(23E)-Coumaroylhederagenin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508035
PubChem CID	21599995
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 99104 0 0 0 0 0 0 0 0999 V2000 -7.7057 2.6377 -0.3948 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0992 1.7348 0.6616 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4597 2.3993 2.0029 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7579 0.3878 0.7005 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7322 -0.7090 1.0171 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7824 -0.6696 -0.1872 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9597 -1.9356 -0.2451 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6329 -1.6295 -0.8977 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8251 -0.8315 0.1406 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8746 -1.6233 1.3979 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5775 0.4592 0.1946 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9607 1.5492 0.6121 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5334 1.5448 1.0339 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7580 0.3554 0.5792 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6778 0.7323 0.1938 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7559 1.7332 -0.8823 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2461 1.3786 1.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5958 0.8504 1.8131 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4933 0.6400 0.6451 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8851 -0.4084 -0.2653 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2658 -0.2012 -1.6839 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5457 -1.7288 0.1795 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9502 -1.4921 -0.0345 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9084 -2.4435 0.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5276 -3.5419 0.6985 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3214 -2.1334 0.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6802 -0.9762 -0.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0366 -0.5563 -0.7527 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2686 0.7177 -1.2618 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5308 1.1887 -1.5530 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6400 0.3946 -1.3455 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4094 -0.8670 -0.8413 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1381 -1.3437 -0.5471 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9088 0.8717 -1.6396 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4242 -0.5549 0.0149 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7571 -1.5620 -0.8574 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6417 -1.8861 -0.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 -0.5696 -0.3601 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5172 -0.1703 -1.7820 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8129 1.8154 -0.0433 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0043 0.5982 -0.2153 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6163 1.7236 0.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7048 -0.7557 -1.3807 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6727 0.1745 -2.2155 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5614 -1.8036 -1.5742 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7181 2.3116 -0.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0116 2.7308 -1.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7969 3.6730 -0.0076 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5404 2.5162 2.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8646 3.2992 2.1817 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1219 1.6482 2.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1645 0.1610 -0.2901 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5488 0.3008 1.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2519 -1.6773 0.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1892 -0.5069 1.9420 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8895 -2.2961 0.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5040 -2.7472 -0.7898 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1461 -2.5630 -1.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8845 -0.9727 -1.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9846 -1.5585 2.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7052 -1.2253 2.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9708 -2.7370 1.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4677 2.5024 0.6697 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5496 1.6803 2.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0928 2.5137 0.6541 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5599 -0.2429 1.5274 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2546 2.1362 -1.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2736 1.4476 -1.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2683 2.6911 -0.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5989 1.2645 2.3404 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3605 2.4935 1.3256 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5820 -0.0749 2.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0916 1.6201 2.4751 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4871 0.3002 1.0687 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2036 -0.7814 -1.9434 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 -0.4914 -2.4337 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6003 0.8722 -1.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3172 -1.9739 1.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3220 -2.5526 -0.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0737 -2.8724 0.2185 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8670 -0.2650 -0.6732 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4041 1.3773 -1.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6507 2.1964 -1.9501 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2633 -1.4989 -0.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9878 -2.3452 -0.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6877 0.2440 -1.4689 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3922 -1.0254 1.0529 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3123 -2.5357 -0.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7717 -1.3772 -1.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5033 -2.2586 0.7003 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0796 -2.6567 -0.9534 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2063 0.7102 -1.9386 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6028 0.0610 -2.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9375 -1.0698 -2.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5300 2.3083 0.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0351 0.9459 -1.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1982 1.7428 1.6079 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3434 2.6931 0.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4478 -1.6298 -2.0546 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 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 31 34 1 0 20 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 6 19 40 1 0 11 41 1 0 41 42 1 0 6 43 1 6 43 44 2 0 43 45 1 0 42 2 1 0 41 6 1 0 38 9 1 0 38 14 1 0 35 15 1 0 33 28 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 10 60 1 0 10 61 1 0 10 62 1 0 12 63 1 0 13 64 1 0 13 65 1 0 14 66 1 1 16 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 18 72 1 0 18 73 1 0 19 74 1 1 21 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 26 80 1 0 27 81 1 0 29 82 1 0 30 83 1 0 32 84 1 0 33 85 1 0 34 86 1 0 35 87 1 1 36 88 1 0 36 89 1 0 37 90 1 0 37 91 1 0 39 92 1 0 39 93 1 0 39 94 1 0 40 95 1 0 41 96 1 6 42 97 1 0 42 98 1 0 45 99 1 0 M END

Standard InCHIKey	APFPLZLTXJYXMM-WWQZRTGHSA-N
Standard InCHI	InChI=1S/C39H54O6/c1-34(2)19-21-39(33(43)44)22-20-37(5)27(28(39)23-34)12-13-30-35(3)17-16-31(41)36(4,29(35)15-18-38(30,37)6)24-45-32(42)14-9-25-7-10-26(40)11-8-25/h7-12,14,28-31,40-41H,13,15-24H2,1-6H3,(H,43,44)/b14-9+/t28-,29+,30+,31-,35-,36-,37+,38+,39-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(COC(=O)/C=C/c6ccc(cc6)O)[C@@H]5CC[C@@]34C)O)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.39	Volume:	666.047 ? Van der Waals volume.
Dense:	0.928	LogP:	4.508 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.783 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.407 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.175	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.911	Fsp³:	0.692
MCE-18:	162.273 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.978	Fluc inhibitor:	0.942 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.034 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.036 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.155	Promiscuous compounds:	0.038

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.641	MDCK Permeability:	-5.118
Pgp-inhibitor:	0.026	Pgp-substrate:	0.0
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):	0.0
20% Bioavailability (F20%):	0.846	30% Bioavailability (F30%):	0.123
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.516
Plasma Protein Binding (PPB):	97.369%	Volume Distribution (VD):	-0.46
Fu:	2.095% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.746	BCRP inhibitor:	0.006
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.491
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.963
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.924 ? 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):

3.159

Half-life (T1/2):

1.2

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.071
Human Hepatotoxicity (H-HT):	0.77	Drug-induced Liver Injury (DILI):	0.887
AMES Toxicity:	0.406	Rat Oral Acute Toxicity:	0.327
Maximum Recommended Daily Dose:	0.72	Skin Sensitization:	0.979
Carcinogencity:	0.911	Eye Corrosion:	0.0
Eye Irritation:	0.164	Respiratory Toxicity:	0.743
Drug-induced Neurotoxicity:	0.081	Ototoxicity:	0.625
Hematotoxicity:	0.389	Drug-induced Nephrotoxicity:	0.937
Genotoxicity:	0.95	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.287	Hek293 Cytotoxicity:	0.485
BCF:	1.009 ? 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:	4.346 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.763 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.268 ? 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
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738395]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	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	2

Activity Type	# Activity
Cell line	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
NPT91	Cell line	KB	Homo sapiens	IC50	=	1300.0	nM	PMID[14738395]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	2400.0	nM	PMID[14738395]

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 NPC216940 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	7486
0.1-0.2	36709
0.2-0.3	4848
0.3-0.4	522
0.4-0.5	189
0.5-0.6	67
0.6-0.7	27
0.7-0.8	0
0.8-0.85	1
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	NPC198621
0.8182	Intermediate Similarity	NPC262970
0.7312	Intermediate Similarity	NPC605663
0.7283	Intermediate Similarity	NPC22676
0.7041	Intermediate Similarity	NPC206232
0.7041	Intermediate Similarity	NPC14515
0.6979	Remote Similarity	NPC479747
0.6979	Remote Similarity	NPC479746
0.6979	Remote Similarity	NPC482049
0.6979	Remote Similarity	NPC482050
0.6771	Remote Similarity	NPC54627
0.6771	Remote Similarity	NPC249817
0.6768	Remote Similarity	NPC479740
0.6768	Remote Similarity	NPC479741
0.6633	Remote Similarity	NPC475482
0.6632	Remote Similarity	NPC271494
0.6531	Remote Similarity	NPC132126
0.6526	Remote Similarity	NPC475627
0.6364	Remote Similarity	NPC606782
0.6311	Remote Similarity	NPC601567
0.6311	Remote Similarity	NPC606631
0.6289	Remote Similarity	NPC171007
0.6289	Remote Similarity	NPC190849
0.6265	Remote Similarity	NPC480946
0.6265	Remote Similarity	NPC130577
0.6265	Remote Similarity	NPC142415
0.6265	Remote Similarity	NPC102683
0.6238	Remote Similarity	NPC610795
0.6224	Remote Similarity	NPC488215
0.6047	Remote Similarity	NPC298554
0.6	Remote Similarity	NPC270768
0.6	Remote Similarity	NPC59263
0.6	Remote Similarity	NPC210106
0.5979	Remote Similarity	NPC43353
0.5941	Remote Similarity	NPC172311
0.5941	Remote Similarity	NPC482052
0.5889	Remote Similarity	NPC474727
0.5882	Remote Similarity	NPC304110
0.5882	Remote Similarity	NPC25491
0.5882	Remote Similarity	NPC27518
0.5882	Remote Similarity	NPC611516
0.5849	Remote Similarity	NPC310729
0.5849	Remote Similarity	NPC150310
0.5833	Remote Similarity	NPC53520
0.5825	Remote Similarity	NPC178093
0.5784	Remote Similarity	NPC479744
0.5769	Remote Similarity	NPC475311
0.5769	Remote Similarity	NPC324798
0.5769	Remote Similarity	NPC479742
0.5673	Remote Similarity	NPC479739
0.5619	Remote Similarity	NPC473773
0.5619	Remote Similarity	NPC475579
0.5506	Remote Similarity	NPC200752
0.5481	Remote Similarity	NPC488214
0.5455	Remote Similarity	NPC182797
0.5455	Remote Similarity	NPC52169
0.5455	Remote Similarity	NPC478270
0.5455	Remote Similarity	NPC488562
0.5455	Remote Similarity	NPC478271
0.5446	Remote Similarity	NPC18982
0.54	Remote Similarity	NPC139243
0.54	Remote Similarity	NPC116742
0.5393	Remote Similarity	NPC158141
0.5392	Remote Similarity	NPC477874
0.5341	Remote Similarity	NPC198664
0.534	Remote Similarity	NPC475457
0.5327	Remote Similarity	NPC482051
0.5281	Remote Similarity	NPC282616
0.5281	Remote Similarity	NPC275809
0.5281	Remote Similarity	NPC121798
0.5281	Remote Similarity	NPC64872
0.5281	Remote Similarity	NPC84319
0.5281	Remote Similarity	NPC25906
0.5281	Remote Similarity	NPC234346
0.5281	Remote Similarity	NPC52021
0.5281	Remote Similarity	NPC599947
0.5278	Remote Similarity	NPC479745
0.5275	Remote Similarity	NPC474963
0.5243	Remote Similarity	NPC266365
0.5229	Remote Similarity	NPC473680
0.5222	Remote Similarity	NPC231063
0.5222	Remote Similarity	NPC282395
0.5222	Remote Similarity	NPC130278
0.5222	Remote Similarity	NPC481360
0.5222	Remote Similarity	NPC110308
0.5165	Remote Similarity	NPC228784
0.5165	Remote Similarity	NPC324341
0.5165	Remote Similarity	NPC120840
0.5165	Remote Similarity	NPC601810
0.5111	Remote Similarity	NPC156981
0.51	Remote Similarity	NPC283849
0.51	Remote Similarity	NPC28198
0.51	Remote Similarity	NPC476123
0.5098	Remote Similarity	NPC100383
0.5089	Remote Similarity	NPC481234
0.5089	Remote Similarity	NPC118033
0.5089	Remote Similarity	NPC479431
0.5057	Remote Similarity	NPC604575
0.5055	Remote Similarity	NPC106112
0.5055	Remote Similarity	NPC261935

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC216940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3360
0.1-0.2	5674
0.2-0.3	112
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
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
0.6364	Remote Similarity	NPD8166	Discontinued

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