NPASS Compound

Natural Product: NPC22676

Natural Product ID	NPC22676
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3Z)-Coumaroylhederagenin
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-10-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-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	(3Z)-Coumaroylhederagenin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL450311
PubChem CID	21599996
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 4.0935 -2.3737 -1.9571 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7559 -1.8982 -1.8720 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8198 -0.7334 -0.8589 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7436 0.2784 -1.4215 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3192 -1.3473 0.3882 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0722 -0.4677 1.5881 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5686 -0.1775 1.7375 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0768 0.5807 0.4868 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4026 -0.2662 -0.6881 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7702 0.2394 -1.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7337 0.1266 -1.7219 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2031 1.0461 -0.5791 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4359 0.5781 0.6042 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9235 1.1434 1.8939 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3594 0.7275 1.9793 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1600 0.6408 0.9595 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6650 0.9608 -0.3868 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2346 0.0783 -1.4785 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4155 2.2956 -0.6825 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8990 2.0876 -0.5340 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3691 1.4349 0.7063 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5725 0.2644 1.2154 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9599 -1.0956 0.8498 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2862 -1.3462 0.2248 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0180 -0.1282 -0.2455 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8005 1.0686 0.6296 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2555 -2.0825 1.1688 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1311 -2.2776 -0.9574 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2610 2.5013 1.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2979 2.8553 2.3779 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0811 3.1020 2.1214 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8827 2.4277 -1.0780 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6845 1.9217 0.5959 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6984 -1.6149 0.3589 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2353 -2.8486 0.5584 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2998 -3.7505 0.7573 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5442 -3.3820 0.6128 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6581 -2.7748 0.4467 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8401 -1.3981 0.1454 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9893 -0.8038 0.7060 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3646 0.4824 0.4393 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6241 1.2689 -0.4044 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5064 0.7423 -0.9738 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1339 -0.5832 -0.6908 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0480 2.5710 -0.6413 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1441 -3.2002 -2.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5884 -1.4935 -2.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0594 -2.6758 -1.5783 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5151 0.6582 -0.7213 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3409 -0.2155 -2.2498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2258 1.0980 -1.9800 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7218 -2.2800 0.5662 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3389 -1.0671 2.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6544 0.4483 1.6178 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9891 -1.0708 1.9474 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5837 0.5736 2.5633 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8425 -1.2398 -0.4781 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1163 1.1801 -2.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9614 -0.5160 -2.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8519 -0.9296 -1.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1780 0.3306 -2.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6786 -0.5340 0.6719 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3802 0.7161 2.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 2.2418 1.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6973 0.4937 3.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3653 0.0324 -1.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1002 0.6618 -2.4149 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7837 -0.8894 -1.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2766 2.6193 -1.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1312 3.0864 -0.0026 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3116 3.1539 -0.4987 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3806 1.7231 -1.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7666 0.3056 2.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9389 -1.8082 1.7466 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1264 -1.5863 0.2574 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7530 0.1513 -1.2857 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1206 -0.3066 -0.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4559 1.8801 0.2673 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1535 0.8268 1.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2864 -1.9102 0.7892 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1252 -1.7416 2.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0560 -3.1620 1.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1348 -2.7463 -1.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3717 -3.0516 -0.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9457 -1.6949 -1.8957 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1050 3.9643 2.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1778 2.6107 -1.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3461 2.4783 -2.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1951 3.2493 -0.4359 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2462 2.3134 -0.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8689 2.6350 0.9344 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4125 2.0380 1.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5760 -4.5028 0.8361 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5666 -3.4474 0.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6203 -1.3634 1.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2563 0.9254 0.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9097 1.3476 -1.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2985 -0.9451 -1.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5099 3.1384 0.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 24 28 1 0 21 29 1 1 29 30 2 0 29 31 1 0 12 32 1 6 8 33 1 6 5 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 42 45 1 0 9 3 1 0 17 12 1 0 26 21 1 0 44 39 1 0 13 8 1 0 22 16 1 0 1 46 1 0 2 47 1 0 2 48 1 0 4 49 1 0 4 50 1 0 4 51 1 0 5 52 1 1 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 9 57 1 1 10 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 13 62 1 1 14 63 1 0 14 64 1 0 15 65 1 0 18 66 1 0 18 67 1 0 18 68 1 0 19 69 1 0 19 70 1 0 20 71 1 0 20 72 1 0 22 73 1 1 23 74 1 0 23 75 1 0 25 76 1 0 25 77 1 0 26 78 1 0 26 79 1 0 27 80 1 0 27 81 1 0 27 82 1 0 28 83 1 0 28 84 1 0 28 85 1 0 31 86 1 0 32 87 1 0 32 88 1 0 32 89 1 0 33 90 1 0 33 91 1 0 33 92 1 0 37 93 1 0 38 94 1 0 40 95 1 0 41 96 1 0 43 97 1 0 44 98 1 0 45 99 1 0 M END

Standard InCHIKey	BCJLQRJLEJBGFM-DMMZMUBQSA-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(36(4,24-40)29(35)15-18-38(30,37)6)45-32(42)14-9-25-7-10-26(41)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	OC[C@]1(C)[C@H](CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C)OC(=O)/C=Cc1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.39	Volume:	666.047 ? Van der Waals volume.
Dense:	0.928	LogP:	5.225 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.189 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.59 ? 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:	4.908	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:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.985	Fluc inhibitor:	0.939 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.083 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.052 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.179	Promiscuous compounds:	0.06

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.687	MDCK Permeability:	-5.1
Pgp-inhibitor:	0.217	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):	0.001
20% Bioavailability (F20%):	0.877	30% Bioavailability (F30%):	0.133
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016	MRP1:	0.752
Plasma Protein Binding (PPB):	97.431%	Volume Distribution (VD):	-0.311
Fu:	2.005% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.272	BCRP inhibitor:	0.005
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.074	CYP2C19-substrate:	0.016
CYP2C9-inhibitor:	0.044	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.066	CYP3A4-substrate:	0.112
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.476 ? 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):

3.16

Half-life (T1/2):

1.045

ADMET: Toxicity

hERG Blockers:	0.084	hERG Blockers (10um):	0.112
Human Hepatotoxicity (H-HT):	0.752	Drug-induced Liver Injury (DILI):	0.227
AMES Toxicity:	0.169	Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.384	Skin Sensitization:	1.0
Carcinogencity:	0.297	Eye Corrosion:	0.005
Eye Irritation:	0.532	Respiratory Toxicity:	0.763
Drug-induced Neurotoxicity:	0.088	Ototoxicity:	0.417
Hematotoxicity:	0.059	Drug-induced Nephrotoxicity:	0.944
Genotoxicity:	0.261	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.699	Hek293 Cytotoxicity:	0.509
BCF:	1.033 ? 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:	4.439 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.839 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.334 ? 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	=	1200.0	nM	PMID[14738395]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	2100.0	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 NPC22676 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	7247
0.1-0.2	37127
0.2-0.3	4616
0.3-0.4	572
0.4-0.5	186
0.5-0.6	70
0.6-0.7	22
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	Natural Product ID
0.7978	Intermediate Similarity	NPC482052
0.7978	Intermediate Similarity	NPC605663
0.7527	Intermediate Similarity	NPC610795
0.7283	Intermediate Similarity	NPC198621
0.7283	Intermediate Similarity	NPC216940
0.7128	Intermediate Similarity	NPC132126
0.7021	Intermediate Similarity	NPC172311
0.6882	Remote Similarity	NPC171007
0.6882	Remote Similarity	NPC190849
0.6869	Remote Similarity	NPC601567
0.6869	Remote Similarity	NPC606631
0.6701	Remote Similarity	NPC178093
0.6633	Remote Similarity	NPC324798
0.6633	Remote Similarity	NPC479742
0.6596	Remote Similarity	NPC477874
0.6559	Remote Similarity	NPC155192
0.6429	Remote Similarity	NPC304110
0.6429	Remote Similarity	NPC25491
0.6429	Remote Similarity	NPC27518
0.6429	Remote Similarity	NPC611516
0.6392	Remote Similarity	NPC262970
0.6364	Remote Similarity	NPC479739
0.6327	Remote Similarity	NPC479744
0.6289	Remote Similarity	NPC488215
0.619	Remote Similarity	NPC53520
0.6118	Remote Similarity	NPC120840
0.6078	Remote Similarity	NPC479745
0.6042	Remote Similarity	NPC43353
0.6	Remote Similarity	NPC488214
0.5979	Remote Similarity	NPC284807
0.5979	Remote Similarity	NPC473538
0.596	Remote Similarity	NPC477873
0.5957	Remote Similarity	NPC28198
0.5957	Remote Similarity	NPC476123
0.5938	Remote Similarity	NPC485587
0.5876	Remote Similarity	NPC173569
0.5851	Remote Similarity	NPC204407
0.5825	Remote Similarity	NPC482051
0.5758	Remote Similarity	NPC475627
0.5714	Remote Similarity	NPC479740
0.5714	Remote Similarity	NPC479741
0.5632	Remote Similarity	NPC158141
0.5631	Remote Similarity	NPC606782
0.5577	Remote Similarity	NPC479747
0.5577	Remote Similarity	NPC479746
0.5577	Remote Similarity	NPC482049
0.5577	Remote Similarity	NPC482050
0.5568	Remote Similarity	NPC200752
0.5556	Remote Similarity	NPC481234
0.5556	Remote Similarity	NPC118033
0.5556	Remote Similarity	NPC479431
0.5556	Remote Similarity	NPC248287
0.5556	Remote Similarity	NPC234548
0.5514	Remote Similarity	NPC206232
0.5514	Remote Similarity	NPC14515
0.5402	Remote Similarity	NPC480946
0.5402	Remote Similarity	NPC130577
0.5402	Remote Similarity	NPC142415
0.5402	Remote Similarity	NPC102683
0.54	Remote Similarity	NPC182249
0.54	Remote Similarity	NPC473591
0.5385	Remote Similarity	NPC296164
0.5385	Remote Similarity	NPC136877
0.5361	Remote Similarity	NPC478273
0.5341	Remote Similarity	NPC270768
0.5341	Remote Similarity	NPC59263
0.5341	Remote Similarity	NPC210106
0.534	Remote Similarity	NPC270667
0.5333	Remote Similarity	NPC174679
0.5333	Remote Similarity	NPC279554
0.5333	Remote Similarity	NPC59804
0.5326	Remote Similarity	NPC96580
0.5306	Remote Similarity	NPC283849
0.5306	Remote Similarity	NPC606107
0.53	Remote Similarity	NPC100383
0.5283	Remote Similarity	NPC475482
0.5281	Remote Similarity	NPC110308
0.525	Remote Similarity	NPC488211
0.5243	Remote Similarity	NPC485423
0.5238	Remote Similarity	NPC54627
0.5238	Remote Similarity	NPC12288
0.5238	Remote Similarity	NPC249817
0.5222	Remote Similarity	NPC298554
0.52	Remote Similarity	NPC286347
0.5196	Remote Similarity	NPC294112
0.5196	Remote Similarity	NPC485424
0.5179	Remote Similarity	NPC481235
0.5169	Remote Similarity	NPC156981
0.5161	Remote Similarity	NPC111466
0.5116	Remote Similarity	NPC604575
0.5111	Remote Similarity	NPC231063
0.5111	Remote Similarity	NPC282395
0.5111	Remote Similarity	NPC481360
0.5104	Remote Similarity	NPC86257
0.5096	Remote Similarity	NPC475472
0.5096	Remote Similarity	NPC469447
0.5096	Remote Similarity	NPC475611
0.5093	Remote Similarity	NPC475311
0.5048	Remote Similarity	NPC101863

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC22676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3526
0.1-0.2	5513
0.2-0.3	103
0.3-0.4	7
0.4-0.5	0
0.5-0.6	1
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
0.5631	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