NPASS Compound

Natural Product: NPC85778

Natural Product ID	NPC85778
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZQSHCFZNMUPVTD-XNWPAUOFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 81 85 0 0 0 0 0 0 0 0999 V2000 -6.1205 2.1921 0.2565 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1897 1.2419 0.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6607 -0.0367 0.9734 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4163 -0.8695 1.1927 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7531 -0.9850 -0.1922 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9268 -2.2354 -0.2290 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5441 -2.0273 -0.7824 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8726 -0.8467 -0.1018 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8716 -1.1298 1.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6251 0.3744 -0.5479 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0911 1.5489 0.1999 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3564 1.7834 -0.2853 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1265 0.5630 0.0428 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6246 0.7017 -0.0929 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1094 1.1791 -1.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0138 1.8014 0.9112 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4704 1.8719 1.1739 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1615 0.5969 1.4569 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6879 -0.5678 0.6356 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5437 -0.6785 -0.5769 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9837 -1.8124 1.4946 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2212 -0.5704 0.3996 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8287 -1.7267 -0.4683 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3307 -1.9261 -0.3045 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5626 -0.6837 -0.6224 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6356 -0.5089 -2.1065 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5306 0.7711 1.1998 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1078 0.2580 -0.6546 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7913 1.4688 -0.0513 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8643 2.5774 -1.1163 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9573 -1.2833 -1.0740 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2786 -0.5082 -2.0106 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6842 -2.4234 -0.8189 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1466 2.0771 0.5575 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8167 3.1397 -0.1680 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1516 0.2319 1.9351 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4165 -0.5536 0.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7903 -0.3559 1.9196 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7334 -1.8841 1.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9669 -2.7354 0.7576 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3751 -3.0347 -0.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7085 -1.8830 -1.8692 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9770 -2.9658 -0.6224 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4167 -0.3970 1.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2390 -2.1715 1.6120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1439 -1.1663 1.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2441 0.5617 -1.6054 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5855 2.5182 0.0010 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0174 1.4542 1.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3959 2.1700 -1.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7111 2.6036 0.3861 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0155 0.4909 1.1709 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 1.5963 -1.2371 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5173 2.0865 -1.6797 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2219 0.4525 -2.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4400 1.7176 1.8350 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7368 2.7627 0.3831 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5892 2.5239 2.0909 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0480 2.4388 0.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0997 0.3718 2.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3761 -1.4331 -0.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0407 -0.9440 -1.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1011 0.2883 -0.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1464 -2.6885 0.8565 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9331 -1.6206 2.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1806 -1.9054 2.2252 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7385 -0.7698 1.4062 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3017 -2.6526 -0.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1304 -1.6540 -1.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0622 -2.6706 -1.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1115 -2.4322 0.6231 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2320 -0.8084 -2.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4696 -1.1279 -2.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8367 0.5563 -2.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7876 1.7223 1.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3991 0.3366 -1.7578 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2571 1.8292 0.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0349 2.4346 -1.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8960 3.5760 -0.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7855 2.4563 -1.7472 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5272 -2.6532 -1.3255 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 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 6 18 27 1 0 10 28 1 0 28 29 1 0 29 30 1 0 5 31 1 6 31 32 2 0 31 33 1 0 29 2 1 0 28 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 9 44 1 0 9 45 1 0 9 46 1 0 10 47 1 6 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 1 15 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 1 20 61 1 0 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 21 66 1 0 22 67 1 1 23 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 28 76 1 6 29 77 1 1 30 78 1 0 30 79 1 0 30 80 1 0 33 81 1 0 M END

Standard InCHIKey	ZQSHCFZNMUPVTD-XNWPAUOFSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24-,27-,28+,29+,30-/m0/s1
SMILES	C=C1CC[C@@]2(CC[C@]3(C)[C@H](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)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	505.751 ? Van der Waals volume.
Dense:	0.902	LogP:	3.879 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.297 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.907 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.414	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.896	Fsp³:	0.9
MCE-18:	104.0 ? 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:	0.846	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.395	Promiscuous compounds:	0.049

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.546	MDCK Permeability:	-5.117
Pgp-inhibitor:	0.005	Pgp-substrate:	0.049
PAMPA:	0.972 ? 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%):	0.807	30% Bioavailability (F30%):	0.182
50% Bioavailability (F50%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416	MRP1:	0.994
Plasma Protein Binding (PPB):	97.475%	Volume Distribution (VD):	-0.385
Fu:	3.097% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.858	BCRP inhibitor:	0.096
BSEP inhibitor:	0.815

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.777	CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.802	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.682
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.091
HLM stability:	0.012 ? 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):

4.742

Half-life (T1/2):

0.689

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.051
Human Hepatotoxicity (H-HT):	0.576	Drug-induced Liver Injury (DILI):	0.545
AMES Toxicity:	0.316	Rat Oral Acute Toxicity:	0.409
Maximum Recommended Daily Dose:	0.403	Skin Sensitization:	0.967
Carcinogencity:	0.847	Eye Corrosion:	0.238
Eye Irritation:	0.842	Respiratory Toxicity:	0.923
Drug-induced Neurotoxicity:	0.09	Ototoxicity:	0.599
Hematotoxicity:	0.494	Drug-induced Nephrotoxicity:	0.886
Genotoxicity:	0.578	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.263	Hek293 Cytotoxicity:	0.172
BCF:	1.349 ? 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:	3.762 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.217 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.693 ? 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
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499313]
NPO24232	Boehmeria pannosa	Species	Urticaceae	Eukaryota	roots	n.a.	n.a.	PMID[16872154]
NPO26529	Hypericum oblongifolium	Species	Hypericaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16880649]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26315	Trikentrion flabelliforme	Species	Raspailiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26529	Hypericum oblongifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4308	Pericome caudata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25943	Cirsium carolinianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26529	Hypericum oblongifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25812	Dipentodon sinicus	Species	Dipentodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24232	Boehmeria pannosa	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3170	Piper lanceifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4308	Pericome caudata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26315	Trikentrion flabelliforme	Species	Raspailiidae	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 NPC85778 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	20312
0.1-0.2	23994
0.2-0.3	4520
0.3-0.4	780
0.4-0.5	198
0.5-0.6	37
0.6-0.7	8
0.7-0.8	1
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
0.7667	Intermediate Similarity	NPC264317
0.7667	Intermediate Similarity	NPC294438
0.7302	Intermediate Similarity	NPC18064
0.7302	Intermediate Similarity	NPC16377
0.7097	Intermediate Similarity	NPC30583
0.6984	Remote Similarity	NPC476071
0.6774	Remote Similarity	NPC472608
0.6515	Remote Similarity	NPC151191
0.6462	Remote Similarity	NPC488164
0.6462	Remote Similarity	NPC264005
0.6087	Remote Similarity	NPC488165
0.6056	Remote Similarity	NPC481311
0.6029	Remote Similarity	NPC2783
0.597	Remote Similarity	NPC474686
0.5735	Remote Similarity	NPC488506
0.5735	Remote Similarity	NPC220498
0.5714	Remote Similarity	NPC301226
0.5507	Remote Similarity	NPC181225
0.5507	Remote Similarity	NPC213832
0.5429	Remote Similarity	NPC271974
0.5429	Remote Similarity	NPC474512
0.5429	Remote Similarity	NPC247312
0.5429	Remote Similarity	NPC201655
0.5373	Remote Similarity	NPC298168
0.5373	Remote Similarity	NPC143133
0.5352	Remote Similarity	NPC4309
0.5312	Remote Similarity	NPC185536
0.5303	Remote Similarity	NPC211009
0.5286	Remote Similarity	NPC30322
0.5231	Remote Similarity	NPC91573
0.5224	Remote Similarity	NPC68828
0.5205	Remote Similarity	NPC160506
0.52	Remote Similarity	NPC127689
0.5156	Remote Similarity	NPC192638
0.5156	Remote Similarity	NPC212733
0.5156	Remote Similarity	NPC25511
0.5156	Remote Similarity	NPC600137
0.5152	Remote Similarity	NPC237460
0.5143	Remote Similarity	NPC80590
0.5135	Remote Similarity	NPC478841
0.5135	Remote Similarity	NPC488166
0.5082	Remote Similarity	NPC232112
0.507	Remote Similarity	NPC24772
0.507	Remote Similarity	NPC211162
0.507	Remote Similarity	NPC183374
0.507	Remote Similarity	NPC291373
0.5068	Remote Similarity	NPC269360
0.5068	Remote Similarity	NPC475061
0.5068	Remote Similarity	NPC601275
0.5062	Remote Similarity	NPC486709

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5785
0.1-0.2	3230
0.2-0.3	123
0.3-0.4	8
0.4-0.5	2
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7667	Intermediate Similarity	NPD7520	Phase 1
0.5205	Remote Similarity	NPD8035	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