NPASS Compound

Natural Product: NPC40552

Natural Product ID	NPC40552
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl Ursolate
IUPAC Name	methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
Synonyms	Methyl Ursolate; Ursolic Acid Methyl Ester
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL260673
PubChem CID	636516
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 84 88 0 0 0 0 0 0 0 0999 V2000 -5.2478 -3.3085 -0.2492 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6971 -2.1135 0.5047 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5028 -0.8970 0.2033 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8864 -0.2287 -0.9758 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5364 0.3937 -0.5795 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7548 0.7979 -1.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3754 0.3139 -1.9378 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5730 -0.1190 -0.7774 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0334 -1.5158 -1.0309 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3830 -0.2213 0.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8637 -0.0789 1.6993 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5525 0.1961 2.0131 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3135 0.1615 0.7304 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7659 0.5272 0.8478 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0825 1.9470 1.0211 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3012 -0.2980 2.0303 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7644 -0.1303 2.2039 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5573 0.0850 0.9714 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8903 -0.2466 -0.3145 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3212 -1.6784 -0.7006 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5991 0.6036 -1.3879 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4248 -0.1329 -0.3708 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8540 0.4789 -1.5866 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5358 1.1638 -1.4789 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5963 0.8086 -0.4285 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1001 2.0870 0.0722 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1154 1.3897 0.9475 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8607 -0.4886 0.4039 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2010 -1.9404 0.1923 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5164 -2.8799 1.1423 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9540 1.6512 0.1475 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6315 1.8288 1.3300 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7034 2.6347 -0.4808 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0815 3.7969 0.2135 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8872 -4.2162 0.2664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9547 -3.2473 -1.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3614 -3.2448 -0.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8255 -2.3418 1.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6069 -0.2075 1.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5265 -1.2240 -0.0766 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5454 0.5547 -1.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6804 -0.9822 -1.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3627 0.4634 -2.6775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8397 1.9236 -1.9317 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3978 -0.5360 -2.6925 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8627 1.1139 -2.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0700 -2.1976 -0.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9584 -1.4838 -1.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7018 -1.9974 -1.8128 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5251 -0.1686 2.5822 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7208 1.0843 2.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8931 -0.6660 2.6651 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3482 -0.9452 0.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2311 2.6437 1.1520 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6726 2.0831 1.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6796 2.4031 0.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7916 0.0098 2.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0550 -1.3425 1.8091 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9238 0.7543 2.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1309 -1.0037 2.8205 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4846 -0.5607 1.0733 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8881 -2.3597 0.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9631 -1.8198 -1.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4397 -1.6486 -0.6849 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4666 1.6707 -1.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6927 0.3574 -1.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3694 0.2328 -2.4035 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0051 -1.1896 -0.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6283 1.2045 -1.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8588 -0.3148 -2.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1394 1.1301 -2.5405 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7763 2.2721 -1.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1109 2.1923 1.1479 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1359 2.1684 -0.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4148 2.9945 -0.3650 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9982 1.4014 0.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3319 -0.2656 1.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0628 -2.2116 -0.8755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6411 -2.3978 1.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0821 -3.7038 0.5011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1725 -3.3144 1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5466 4.7042 -0.1764 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8903 3.6483 1.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1799 3.9928 0.1090 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 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 2 0 11 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 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 18 27 1 0 10 28 1 0 28 29 1 0 29 30 1 0 5 31 1 1 31 32 2 0 31 33 1 0 33 34 1 0 29 2 1 0 28 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 6 43 1 0 6 44 1 0 7 45 1 0 7 46 1 0 9 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 6 15 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 1 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 21 67 1 0 22 68 1 6 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 27 76 1 0 28 77 1 1 29 78 1 6 30 79 1 0 30 80 1 0 30 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 M END

Standard InCHIKey	YCBSMEKEDOHEQI-QHQGJMPNSA-N
Standard InCHI	InChI=1S/C31H50O3/c1-19-11-16-31(26(33)34-8)18-17-29(6)21(25(31)20(19)2)9-10-23-28(5)14-13-24(32)27(3,4)22(28)12-15-30(23,29)7/h9,19-20,22-25,32H,10-18H2,1-8H3/t19-,20+,22+,23-,24+,25+,28+,29-,30-,31+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@H]1C)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.38	Volume:	523.047 ? Van der Waals volume.
Dense:	0.899	LogP:	5.442 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.494 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.21 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.326	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.746	Fsp³:	0.903
MCE-18:	101.763 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.902	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.048 ? 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:	0.337	Promiscuous compounds:	0.164

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.515	MDCK Permeability:	-5.065
Pgp-inhibitor:	0.195	Pgp-substrate:	0.171
PAMPA:	0.926 ? 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%):	0.724	30% Bioavailability (F30%):	0.329
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925	MRP1:	0.754
Plasma Protein Binding (PPB):	95.817%	Volume Distribution (VD):	-0.008
Fu:	5.495% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.774
BSEP inhibitor:	0.962

ADMET: Metabolism

CYP1A2-inhibitor:	0.732	CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.928	CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.025	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.095	CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.954	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.939
HLM stability:	0.799 ? 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):

9.42

Half-life (T1/2):

0.379

ADMET: Toxicity

hERG Blockers:	0.083	hERG Blockers (10um):	0.177
Human Hepatotoxicity (H-HT):	0.582	Drug-induced Liver Injury (DILI):	0.373
AMES Toxicity:	0.369	Rat Oral Acute Toxicity:	0.433
Maximum Recommended Daily Dose:	0.58	Skin Sensitization:	0.869
Carcinogencity:	0.909	Eye Corrosion:	0.04
Eye Irritation:	0.641	Respiratory Toxicity:	0.945
Drug-induced Neurotoxicity:	0.033	Ototoxicity:	0.446
Hematotoxicity:	0.56	Drug-induced Nephrotoxicity:	0.7
Genotoxicity:	0.558	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.658	Hek293 Cytotoxicity:	0.481
BCF:	2.488 ? 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:	4.395 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.386 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.11 ? 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
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	DOI[10.1016/j.tetlet.2016.12.029]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np50070a005]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO16699	Agave utahensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19645463]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	leaves	Botanical Garden of Innsbruck, Austria	n.a.	PMID[20100662]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21070010]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21070010]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21923134]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24066589]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38732062]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO14757	Acacia acuminata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16207	Acacia glaucescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16699	Agave utahensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO642	Artemisia bigelovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15300	Bipolaris zeicola	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15984	Blainvillea rhomboidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11453	Centaurea cadmea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7720	Cyathocline purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13047	Epipolasis kushimotoensis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11633	Kelletia kelletii	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8606	Mallotus repandus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11429	Matricaria parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14435	Mnium hornum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13938	Plantago alpina	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12218	Pulicaria wightiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16102	Senecio chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12393	Xanthoparmelia subincerta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4754	Yucca flexilis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11487	Senecio madagascariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6284	Frasera caroliniensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13295	Teucrium nuchense	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28189	Metzgeria pubescens	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16699	Agave utahensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14253	Bothriocline longipes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11429	Matricaria parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14435	Mnium hornum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7720	Cyathocline purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13653	Sorbus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12393	Xanthoparmelia subincerta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16102	Senecio chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15984	Blainvillea rhomboidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13938	Plantago alpina	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11003	Euphorbia sancta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11453	Centaurea cadmea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4754	Yucca flexilis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO642	Artemisia bigelovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15300	Bipolaris zeicola	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO191	Amaranthus hybr	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12739	Pseudoscleropodium purum	Species	Brachytheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11633	Kelletia kelletii	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11814	Asphodeline tenuior	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6284	Frasera caroliniensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14757	Acacia acuminata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11985	Glycyrrhiza triphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11487	Senecio madagascariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16207	Acacia glaucescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13047	Epipolasis kushimotoensis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13164	Iris hoogiana	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8606	Mallotus repandus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12218	Pulicaria wightiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15620	Kingiella taenialis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25618	Eriobotrya japonica	Species	Rosaceae	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	22
Ki	1
Inhibition	1
GI	7
EC50	3

Activity Type	# Activity
Individual protein	4
Cell line	23
Non-molecular	7

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1547	Individual protein	Cathepsin D	Homo sapiens	IC50	=	4.45	ug.mL-1	DOI[10.1007/s00044-012-0397-z]
NPT1218	Individual protein	Carbonic anhydrase II	Bos taurus	Ki	>	10000.0	nM	PMID[25147151]
NPT5212	Individual protein	Sentrin-specific protease 1	Homo sapiens	Inhibition	=	7.3	%	PMID[34688014]
NPT4886	Individual protein	Ubiquitin carboxyl-terminal hydrolase 7	Homo sapiens	IC50	>	50000.0	nM	PMID[32092586]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell line	PANC-1	Homo sapiens	IC50	=	11750.0	nM	PMID[18359628]
NPT81	Cell line	A549	Homo sapiens	IC50	=	191000.0	nM	PMID[15730243]
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	=	96100.0	nM	PMID[15730243]
NPT2297	Cell line	ASPC1	Homo sapiens	IC50	=	17700.0	nM	PMID[22959527]
NPT744	Cell line	IMR-32	Homo sapiens	GI	=	11.0	%	DOI[10.1007/s00044-012-0106-y]
NPT81	Cell line	A549	Homo sapiens	GI	=	20.0	%	DOI[10.1007/s00044-012-0106-y]
NPT165	Cell line	HeLa	Homo sapiens	GI	=	2.0	%	DOI[10.1007/s00044-012-0106-y]
NPT2245	Cell line	SiHa	Homo sapiens	GI	=	21.0	%	DOI[10.1007/s00044-012-0106-y]
NPT323	Cell line	SW-620	Homo sapiens	GI	=	0.0	%	DOI[10.1007/s00044-012-0106-y]
NPT407	Cell line	COLO 205	Homo sapiens	GI	=	0.0	%	DOI[10.1007/s00044-012-0106-y]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI	<	5.0	%	DOI[10.1007/s00044-012-0397-z]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	22200.0	nM	PMID[24361521]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	25400.0	nM	PMID[24361521]
NPT81	Cell line	A549	Homo sapiens	IC50	=	20200.0	nM	PMID[24361521]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	15300.0	nM	PMID[24361521]
NPT1215	Cell line	8505C	Homo sapiens	IC50	=	20600.0	nM	PMID[24361521]
NPT139	Cell line	HT-29	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	20000.0	nM	PMID[34688014]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	8950.0	nM	PMID[18359628]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	6130.0	nM	PMID[18359628]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	10580.0	nM	PMID[18359628]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	105000.0	nM	PMID[15730243]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	37130.0	nM	PMID[19758808]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	17700.0	nM	PMID[24361521]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[26177446]

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 NPC40552 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	18624
0.1-0.2	25626
0.2-0.3	4516
0.3-0.4	837
0.4-0.5	175
0.5-0.6	50
0.6-0.7	7
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
0.7869	Intermediate Similarity	NPC307335
0.7869	Intermediate Similarity	NPC74855
0.7679	Intermediate Similarity	NPC27765
0.7679	Intermediate Similarity	NPC122418
0.7679	Intermediate Similarity	NPC491014
0.7627	Intermediate Similarity	NPC95594
0.7541	Intermediate Similarity	NPC477579
0.7167	Intermediate Similarity	NPC40394
0.7143	Intermediate Similarity	NPC272075
0.7097	Intermediate Similarity	NPC246708
0.7097	Intermediate Similarity	NPC606009
0.6984	Remote Similarity	NPC127855
0.6721	Remote Similarity	NPC132478
0.6714	Remote Similarity	NPC171208
0.65	Remote Similarity	NPC120098
0.625	Remote Similarity	NPC470588
0.6061	Remote Similarity	NPC610552
0.6029	Remote Similarity	NPC488519
0.5968	Remote Similarity	NPC290598
0.5968	Remote Similarity	NPC30590
0.5857	Remote Similarity	NPC49776
0.5857	Remote Similarity	NPC63118
0.5857	Remote Similarity	NPC474436
0.5846	Remote Similarity	NPC235341
0.5846	Remote Similarity	NPC291379
0.5758	Remote Similarity	NPC602872
0.5652	Remote Similarity	NPC610937
0.5634	Remote Similarity	NPC98874
0.5606	Remote Similarity	NPC290495
0.5571	Remote Similarity	NPC51700
0.5571	Remote Similarity	NPC259788
0.5571	Remote Similarity	NPC88716
0.5571	Remote Similarity	NPC255589
0.5571	Remote Similarity	NPC68160
0.5571	Remote Similarity	NPC195019
0.5556	Remote Similarity	NPC110139
0.5556	Remote Similarity	NPC108709
0.5542	Remote Similarity	NPC477292
0.5493	Remote Similarity	NPC18872
0.5493	Remote Similarity	NPC290614
0.5455	Remote Similarity	NPC191763
0.5455	Remote Similarity	NPC101475
0.5443	Remote Similarity	NPC46388
0.5429	Remote Similarity	NPC86372
0.5429	Remote Similarity	NPC136313
0.5385	Remote Similarity	NPC82477
0.5352	Remote Similarity	NPC171203
0.5352	Remote Similarity	NPC307426
0.5352	Remote Similarity	NPC98442
0.5352	Remote Similarity	NPC242468
0.5316	Remote Similarity	NPC167383
0.5286	Remote Similarity	NPC479748
0.5217	Remote Similarity	NPC234617
0.5211	Remote Similarity	NPC214756
0.5211	Remote Similarity	NPC304285
0.5211	Remote Similarity	NPC329943
0.5205	Remote Similarity	NPC164349
0.5161	Remote Similarity	NPC101744
0.5143	Remote Similarity	NPC48756
0.5139	Remote Similarity	NPC7260
0.5139	Remote Similarity	NPC210037
0.5139	Remote Similarity	NPC120968
0.5139	Remote Similarity	NPC227467
0.5139	Remote Similarity	NPC273621
0.5139	Remote Similarity	NPC112866
0.5114	Remote Similarity	NPC179434
0.5072	Remote Similarity	NPC292015
0.507	Remote Similarity	NPC477872

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC40552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7003
0.1-0.2	2080
0.2-0.3	62
0.3-0.4	3
0.4-0.5	2
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