NPASS Compound

Natural Product: NPC258547

Natural Product ID	NPC258547
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	21-O-Angeloy-3Beta,16Alpha,22Alpha,24,28-Pentahydroxyolean-12-Ene
IUPAC Name	[(3R,4R,4aR,5R,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-4,5,10-trihydroxy-4a,9-bis(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl] (Z)-2-methylbut-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1095017
PubChem CID	46888299
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 98102 0 0 0 0 0 0 0 0999 V2000 9.5656 0.7367 -0.1623 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0737 -0.6013 0.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7898 -0.8287 0.3448 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3104 -2.2005 0.7339 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7691 0.1853 0.1285 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0789 1.3595 -0.1990 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4124 -0.0791 0.2686 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4042 0.9224 0.0551 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5680 0.5810 -1.1554 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3975 -0.2835 -0.8507 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9665 -1.7158 -0.7294 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9909 -2.6335 -0.4454 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6945 0.0526 0.4672 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1581 1.3921 0.8794 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6407 1.2093 1.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7899 0.2361 2.4097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0113 2.5969 1.8549 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2425 -0.1764 0.3374 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3152 -1.1164 1.0523 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7273 -1.5295 1.0896 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5509 -0.4595 0.4879 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0151 -0.7969 0.5362 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4051 -2.1443 0.1083 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4143 -0.6881 2.0133 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8710 -0.9443 2.2496 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7890 -0.5358 1.1674 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2214 0.4531 0.1855 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5368 1.8507 0.7811 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1037 0.4588 -1.0736 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1831 -0.7464 -1.7092 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7763 0.3559 -0.0803 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3455 0.5824 -1.5087 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9023 0.9995 -1.4236 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9732 -0.0232 -0.8042 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9044 -1.1209 -1.8439 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6135 0.6057 -0.5961 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8578 2.0194 -0.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2540 0.7157 -1.8184 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3441 -0.3144 -1.8976 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9937 -0.0874 -3.1351 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4247 -1.6271 0.5220 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2862 1.6876 -1.9611 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2589 1.5046 0.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6771 0.7453 -0.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1855 1.0689 -1.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7805 -1.3922 0.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1468 -2.7608 1.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4833 -2.0459 1.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8615 -2.7115 -0.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9646 1.8492 -0.2203 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2719 -0.0246 -1.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4506 -2.0133 -1.6759 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7557 -1.7467 0.0460 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1184 -3.0391 0.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1338 -0.6384 1.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6969 1.7972 1.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3079 2.1469 0.0733 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8112 0.1857 2.9608 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1882 -0.7453 2.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5014 0.6575 3.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8770 2.4413 2.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3390 3.2433 1.0286 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1911 2.9865 2.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3811 -1.6821 1.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7721 -2.5229 0.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9789 -1.7654 2.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4679 0.4409 1.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0812 -2.2012 -0.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9520 -2.7523 0.8971 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5587 -2.8119 -0.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2263 0.3882 2.2952 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8583 -1.3579 2.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1118 -0.4442 3.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0277 -2.0286 2.4636 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6804 -0.0489 1.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0020 1.9490 1.7273 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6236 1.9418 0.9848 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2259 2.6071 0.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8631 1.2608 -1.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1736 0.6851 -0.7616 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2060 -0.6499 -2.7046 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2865 1.2361 0.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8799 1.4901 -1.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5637 -0.2220 -2.1935 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9724 1.9227 -0.7666 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6079 1.2713 -2.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3007 -1.9855 -1.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6108 -0.7063 -2.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9057 -1.5537 -2.0571 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0275 2.5386 0.2774 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5867 2.1328 0.6832 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1101 2.6678 -1.0171 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2575 0.7600 -2.7763 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8110 1.7107 -1.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9613 -1.3477 -1.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3037 -0.2299 -3.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3787 -2.4363 1.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9723 1.8881 -2.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 13 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 27 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 6 34 36 1 0 36 37 1 1 36 38 1 0 38 39 1 0 39 40 1 0 26 41 1 0 9 42 1 0 15 8 1 0 36 18 1 0 39 10 1 0 34 21 1 0 31 22 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 4 47 1 0 4 48 1 0 4 49 1 0 8 50 1 6 9 51 1 6 11 52 1 0 11 53 1 0 12 54 1 0 13 55 1 1 14 56 1 0 14 57 1 0 16 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 17 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 21 67 1 1 23 68 1 0 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 26 75 1 1 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 29 80 1 0 30 81 1 0 31 82 1 1 32 83 1 0 32 84 1 0 33 85 1 0 33 86 1 0 35 87 1 0 35 88 1 0 35 89 1 0 37 90 1 0 37 91 1 0 37 92 1 0 38 93 1 0 38 94 1 0 39 95 1 6 40 96 1 0 41 97 1 0 42 98 1 0 M END

Standard InCHIKey	ZVFCKHLBNXUAAD-AVTDRASNSA-N
Standard InCHI	InChI=1S/C35H56O7/c1-9-20(2)29(41)42-28-27(40)35(19-37)22(16-30(28,3)4)21-10-11-24-31(5)14-13-25(38)32(6,18-36)23(31)12-15-33(24,7)34(21,8)17-26(35)39/h9-10,22-28,36-40H,11-19H2,1-8H3/b20-9-/t22-,23+,24+,25-,26+,27-,28-,31-,32+,33+,34+,35-/m0/s1
SMILES	C/C=C(/C)C(=O)O[C@H]1[C@@H]([C@@]2(CO)[C@@H](CC1(C)C)C1=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	588.4	Volume:	624.756 ? Van der Waals volume.
Dense:	0.942	LogP:	3.303 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.473 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.914 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	28.0
TPSA:	127.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.185	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.42	Fsp³:	0.857
MCE-18:	112.462 ? 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:	0.584	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.293	Promiscuous compounds:	0.239

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.599	MDCK Permeability:	-5.037
Pgp-inhibitor:	0.053	Pgp-substrate:	0.096
PAMPA:	0.981 ? 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%):	1.0	30% Bioavailability (F30%):	0.919
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1.0	MRP1:	0.872
Plasma Protein Binding (PPB):	86.187%	Volume Distribution (VD):	-0.031
Fu:	14.692% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.017	BCRP inhibitor:	0.79
BSEP inhibitor:	0.971

ADMET: Metabolism

CYP1A2-inhibitor:	0.155	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.082	CYP2C19-substrate:	0.311
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.755	CYP3A4-substrate:	0.29
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.387
HLM stability:	0.014 ? 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):

5.912

Half-life (T1/2):

1.348

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.125
Human Hepatotoxicity (H-HT):	0.551	Drug-induced Liver Injury (DILI):	0.326
AMES Toxicity:	0.752	Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.743	Skin Sensitization:	1.0
Carcinogencity:	0.993	Eye Corrosion:	0.001
Eye Irritation:	0.385	Respiratory Toxicity:	0.963
Drug-induced Neurotoxicity:	0.183	Ototoxicity:	0.511
Hematotoxicity:	0.793	Drug-induced Nephrotoxicity:	0.972
Genotoxicity:	0.975	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.917
BCF:	0.882 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.67 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.62 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.701 ? 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
NPO21201	Camellia oleifera	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21201	Camellia oleifera	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21201	Camellia oleifera	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21201	Camellia oleifera	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21201	Camellia oleifera	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21201	Camellia oleifera	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21201	Camellia oleifera	Species	Theaceae	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
GI50	4

Activity Type	# Activity
Individual protein	2
Cell line	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual protein	DNA topoisomerase II alpha	Homo sapiens	IC50	>	250000.0	nM	PMID[20371180]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	>	250000.0	nM	PMID[20371180]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell line	MRC5	Homo sapiens	GI50	=	18110.0	nM	PMID[20371180]
NPT461	Cell line	PANC-1	Homo sapiens	GI50	=	11860.0	nM	PMID[20371180]
NPT306	Cell line	PC-3	Homo sapiens	GI50	=	2230.0	nM	PMID[20371180]
NPT81	Cell line	A549	Homo sapiens	GI50	=	2450.0	nM	PMID[20371180]

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 NPC258547 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	19444
0.1-0.2	24622
0.2-0.3	4899
0.3-0.4	713
0.4-0.5	152
0.5-0.6	21
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8955	High Similarity	NPC283343
0.6623	Remote Similarity	NPC473160
0.6197	Remote Similarity	NPC253402
0.6146	Remote Similarity	NPC603832
0.5844	Remote Similarity	NPC164349
0.5728	Remote Similarity	NPC609119
0.5694	Remote Similarity	NPC311078
0.5679	Remote Similarity	NPC88349
0.5631	Remote Similarity	NPC472267
0.5631	Remote Similarity	NPC115656
0.5556	Remote Similarity	NPC475263
0.5556	Remote Similarity	NPC488518
0.5541	Remote Similarity	NPC159168
0.54	Remote Similarity	NPC611191
0.5357	Remote Similarity	NPC480921
0.5357	Remote Similarity	NPC480920
0.5333	Remote Similarity	NPC230295
0.5333	Remote Similarity	NPC98386
0.5309	Remote Similarity	NPC294360
0.5301	Remote Similarity	NPC273668
0.527	Remote Similarity	NPC196753
0.5256	Remote Similarity	NPC213412
0.52	Remote Similarity	NPC253807
0.52	Remote Similarity	NPC158662
0.5179	Remote Similarity	NPC476774

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC258547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7140
0.1-0.2	1959
0.2-0.3	49
0.3-0.4	0
0.4-0.5	1
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
0.5584	Remote Similarity	NPD7645	Phase 2

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