NPASS Compound

Natural Product: NPC149388

Natural Product ID	NPC149388
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DNPBJHZABOJXGA-HPBGPLOVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44559123
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 85 89 0 0 0 0 0 0 0 0999 V2000 4.9445 -2.0439 -1.5114 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8765 -0.5342 -1.4050 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7102 -0.1053 -0.2456 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9606 -0.4579 1.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7715 0.4517 1.1028 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4753 1.7937 1.5041 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9189 0.1528 2.2753 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6552 -0.5956 2.1764 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0162 -0.5840 0.7546 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5500 -1.8864 0.2017 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.6342 0.1883 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8900 1.7212 0.1115 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5502 1.7722 0.5985 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1600 0.5108 0.1386 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6582 0.4667 0.1023 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3494 0.6595 1.3914 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1512 1.6272 -0.7854 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5347 1.4512 -1.3145 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9356 0.1399 -1.8299 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4425 -1.0097 -0.9831 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4561 -2.2293 -1.9261 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3652 -1.3120 0.1296 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0246 -0.7524 -0.6738 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3946 -2.0147 -0.2112 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8806 -1.8453 -0.1594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4712 -0.6733 0.7543 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9326 -1.0614 2.1130 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3280 0.0596 -1.8643 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0475 2.9576 0.1758 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2469 3.8955 1.1944 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0390 0.6956 -0.1968 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4638 -0.0082 -1.4057 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4009 0.9260 -2.6501 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3457 -2.5434 -0.6287 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5700 -2.3777 -2.3916 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9311 -2.4544 -1.7311 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4568 -0.1742 -2.3172 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9739 0.9612 -0.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6439 -0.7037 -0.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7115 -1.5242 0.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5935 -0.2399 1.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7634 2.3322 0.5920 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7066 2.4361 2.0202 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2693 1.6099 2.2236 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5912 -0.4171 2.9994 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7424 1.1086 2.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7970 -1.6291 2.5423 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9359 -0.1340 2.8858 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1727 -2.2216 -0.7403 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6281 -1.9999 0.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2320 -2.6511 0.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2952 2.6669 -0.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4775 1.8403 1.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8735 0.4329 -0.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6905 1.3105 2.0409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2725 1.3094 1.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7233 -0.2254 1.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4705 1.8155 -1.6086 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3032 2.5274 -0.1143 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6177 2.1892 -2.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3446 1.8055 -0.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6001 0.0250 -2.8938 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6681 -2.1656 -2.6809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4364 -2.1407 -2.4772 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5090 -3.1646 -1.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9892 -1.9866 0.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2684 -1.8353 -0.3116 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8184 -0.3761 0.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5443 -0.5655 -1.6947 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 -2.7407 -1.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8348 -2.5294 0.6283 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5358 -2.8153 0.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6214 -1.5824 -1.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0659 -0.2425 2.8391 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2035 -1.7687 2.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8669 -1.6847 2.1363 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7435 0.7263 -1.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6582 4.8084 0.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0158 3.6064 1.9169 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2955 4.2376 1.6483 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2673 1.7865 -0.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8186 -0.8315 -1.7783 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8621 1.8911 -2.3794 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3402 1.0420 -2.9541 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9816 0.4544 -3.4526 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 1 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 28 1 0 13 29 1 0 29 30 1 0 11 31 1 0 31 32 1 0 32 33 1 0 32 2 1 0 31 5 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 6 42 1 0 6 43 1 0 6 44 1 0 7 45 1 0 7 46 1 0 8 47 1 0 8 48 1 0 10 49 1 0 10 50 1 0 10 51 1 0 12 52 1 0 13 53 1 1 14 54 1 6 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 19 62 1 6 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 23 69 1 6 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 28 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 31 81 1 6 32 82 1 6 33 83 1 0 33 84 1 0 33 85 1 0 M END

Standard InCHIKey	DNPBJHZABOJXGA-HPBGPLOVSA-N
Standard InCHI	InChI=1S/C31H52O2/c1-19-10-13-28(5)16-17-30(7)21(25(28)20(19)2)18-22(33-9)26-29(6)14-12-24(32)27(3,4)23(29)11-15-31(26,30)8/h18-20,22-26,32H,10-17H2,1-9H3/t19-,20+,22-,23+,24+,25+,26-,28-,29+,30-,31-/m1/s1
SMILES	C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=C[C@H]([C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)OC)[C@@H]2[C@H]1C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.4	Volume:	516.894 ? Van der Waals volume.
Dense:	0.883	LogP:	5.469 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.319 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.869 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	29.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.411	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.981	Fsp³:	0.935
MCE-18:	101.333 ? 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:	0.832	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.26 ? 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:	0.372	Promiscuous compounds:	0.184

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.264	MDCK Permeability:	-4.889
Pgp-inhibitor:	0.977	Pgp-substrate:	0.127
PAMPA:	0.412 ? 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%):	0.627	30% Bioavailability (F30%):	0.188
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.981	MRP1:	0.861
Plasma Protein Binding (PPB):	90.473%	Volume Distribution (VD):	-0.207
Fu:	8.786% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.979
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.459
CYP2C19-inhibitor:	0.428	CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.008	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

16.013

Half-life (T1/2):

0.828

ADMET: Toxicity

hERG Blockers:	0.111	hERG Blockers (10um):	0.399
Human Hepatotoxicity (H-HT):	0.625	Drug-induced Liver Injury (DILI):	0.133
AMES Toxicity:	0.366	Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.686	Skin Sensitization:	0.963
Carcinogencity:	0.853	Eye Corrosion:	0.075
Eye Irritation:	0.87	Respiratory Toxicity:	0.768
Drug-induced Neurotoxicity:	0.098	Ototoxicity:	0.456
Hematotoxicity:	0.302	Drug-induced Nephrotoxicity:	0.44
Genotoxicity:	0.62	RPMI-8226 Immunitoxicity:	0.107
A549 Cytotoxicity:	0.191	Hek293 Cytotoxicity:	0.615
BCF:	2.78 ? 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:	4.407 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.07 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.02 ? 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
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0040-4039(99)00339-1]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10746886]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10757718]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[23252270]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2534610]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[535601]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8328267]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Phytochemistry, 2000, 53, 715-722.]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22423	Microtropis fokienensis	Species	Celastraceae	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

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

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 NPC149388 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	19154
0.1-0.2	26744
0.2-0.3	3406
0.3-0.4	459
0.4-0.5	80
0.5-0.6	10
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8136	Intermediate Similarity	NPC304285
0.6885	Remote Similarity	NPC292015
0.661	Remote Similarity	NPC27765
0.661	Remote Similarity	NPC122418
0.661	Remote Similarity	NPC491014
0.6349	Remote Similarity	NPC602872
0.5857	Remote Similarity	NPC91010
0.5672	Remote Similarity	NPC40552
0.5606	Remote Similarity	NPC95594
0.5493	Remote Similarity	NPC98874
0.5455	Remote Similarity	NPC40394
0.5362	Remote Similarity	NPC477579
0.5286	Remote Similarity	NPC272075
0.5152	Remote Similarity	NPC295131
0.5143	Remote Similarity	NPC479748
0.5075	Remote Similarity	NPC132478

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC149388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6928
0.1-0.2	2175
0.2-0.3	44
0.3-0.4	1
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