NPASS Compound

Natural Product: NPC85454

Natural Product ID	NPC85454
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SRTGQBIWSBCVSM-XZQLKIIMSA-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 76 81 0 0 0 0 0 0 0 0999 V2000 7.9310 -0.0488 -0.1126 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5500 -0.0473 -0.6840 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9261 1.3223 -0.7510 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5498 1.2043 -1.3445 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7835 0.1845 -0.5720 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4634 -0.1852 -1.2700 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7883 -1.1179 -2.4136 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7992 -0.9029 -0.1545 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2981 -0.1573 1.0649 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0534 0.5313 1.5869 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0106 -0.4988 1.2826 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3848 -0.1128 1.5665 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1548 -1.3453 1.9342 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4612 -1.4994 1.2468 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2141 -0.1985 1.3608 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5576 -0.4201 0.6820 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3635 -0.3388 -0.7957 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0435 1.0952 -1.1318 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1994 1.8043 -0.1642 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4729 0.9952 0.8594 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3734 1.9397 2.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0294 0.7364 0.5081 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7549 0.3361 -0.8888 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2487 0.1852 -1.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3085 -0.8523 -0.1445 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1947 -2.2261 -0.5328 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9891 2.8119 0.4492 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5479 1.0801 -2.4552 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5986 -0.6991 -1.3886 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2575 0.7340 0.6180 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4427 -1.0000 -0.3599 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6737 -0.8892 0.2294 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1203 -1.0755 0.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7209 0.1026 -0.8623 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0634 0.6436 0.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5930 -0.5434 -1.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5904 1.9933 -1.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8512 1.6984 0.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0539 2.1881 -1.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6507 0.8936 -2.3941 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0122 0.7497 -1.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7201 -0.8584 -2.9296 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8693 -2.1381 -1.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9869 -1.1282 -3.1800 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1939 -1.9348 -0.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6979 -0.8613 1.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1294 0.7366 2.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8943 1.4908 1.0833 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2710 -1.4086 1.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3663 0.5322 2.4984 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3517 -1.4161 3.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5593 -2.2838 1.7236 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0611 -2.2530 1.8421 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4268 -1.9201 0.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4868 -0.1411 2.4599 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8596 -1.4644 0.9265 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3422 0.2371 1.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6372 -1.0627 -1.1596 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0528 1.5967 -1.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4307 2.4031 -0.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1668 1.3451 3.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4175 2.3241 2.2206 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6561 2.7415 1.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5060 1.7429 0.6019 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9714 1.2372 -1.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3159 -0.4799 -1.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0816 -0.0677 -2.1282 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1792 1.1825 -0.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1301 -3.0065 0.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3357 -2.4770 -1.4984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2631 -2.2507 -0.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4853 3.6288 0.6013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2198 0.1783 -2.7048 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3359 -0.5866 -0.7410 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1188 -1.9038 0.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5642 -0.4267 1.2184 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 19 27 1 0 18 28 1 0 17 29 1 0 9 30 1 0 5 31 1 1 31 32 1 0 32 2 1 0 30 5 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 6 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 6 41 1 6 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 1 9 46 1 1 10 47 1 0 10 48 1 0 11 49 1 1 12 50 1 1 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 1 16 56 1 0 16 57 1 0 17 58 1 6 18 59 1 6 19 60 1 6 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 6 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 28 73 1 0 29 74 1 0 32 75 1 0 32 76 1 0 M END

Standard InCHIKey	SRTGQBIWSBCVSM-XZQLKIIMSA-N
Standard InCHI	InChI=1S/C27H44O5/c1-14-7-10-27(31-13-14)15(2)22-21(32-27)12-19-17-6-5-16-11-20(28)23(29)24(30)26(16,4)18(17)8-9-25(19,22)3/h14-24,28-30H,5-13H2,1-4H3/t14-,15+,16-,17-,18-,19+,20-,21+,22+,23+,24-,25-,26+,27-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC[C@@H]6C[C@H]([C@@H]([C@H]([C@]6(C)[C@@H]5CC[C@@]34C)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	448.32	Volume:	468.16 ? Van der Waals volume.
Dense:	0.958	LogP:	4.468 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.195 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.263 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	30.0
TPSA:	79.15 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.526	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.559	Fsp³:	1.0
MCE-18:	146.37 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.715	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.053 ? 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:	0.202	Promiscuous compounds:	0.032

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.249	MDCK Permeability:	-4.917
Pgp-inhibitor:	0.059	Pgp-substrate:	0.486
PAMPA:	0.49 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.98	30% Bioavailability (F30%):	0.869
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.724
Plasma Protein Binding (PPB):	91.958%	Volume Distribution (VD):	0.217
Fu:	11.389% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.57	BCRP inhibitor:	0.327
BSEP inhibitor:	0.875

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.572	CYP2C19-substrate:	0.289
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.212	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.989
HLM stability:	0.817 ? 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):

8.731

Half-life (T1/2):

1.705

ADMET: Toxicity

hERG Blockers:	0.138	hERG Blockers (10um):	0.431
Human Hepatotoxicity (H-HT):	0.424	Drug-induced Liver Injury (DILI):	0.358
AMES Toxicity:	0.292	Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.555	Skin Sensitization:	0.992
Carcinogencity:	0.555	Eye Corrosion:	0.024
Eye Irritation:	0.353	Respiratory Toxicity:	0.111
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.836
Hematotoxicity:	0.038	Drug-induced Nephrotoxicity:	0.73
Genotoxicity:	0.023	RPMI-8226 Immunitoxicity:	0.13
A549 Cytotoxicity:	0.18	Hek293 Cytotoxicity:	0.584
BCF:	2.24 ? 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:	3.657 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.571 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.269 ? 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
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11473431]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575945]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163582]
NPO26918	Taricha granulosa	Species	Salamandridae	Eukaryota	n.a.	n.a.	n.a.	PMID[32896120]
NPO17338	Solanum asperum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14627	Caloscypha fulgens	Species	Caloscyphaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22836	Alpinia mutica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22402	Lupinus mutabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16398	Nicotiana alata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12967	Reseda suffruticosa	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20565	Aplysina fulva	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23001	Halimium umbellatum	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17338	Solanum asperum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16398	Nicotiana alata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1463	Corethrodendron scoparium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22402	Lupinus mutabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22836	Alpinia mutica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23001	Halimium umbellatum	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18364	Genista lusitanica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12967	Reseda suffruticosa	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14902	Pteris marginata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19482	Tapinoma nigerrimum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20402	Ageratina gilbertii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14627	Caloscypha fulgens	Species	Caloscyphaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26918	Taricha granulosa	Species	Salamandridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23067	Shorea maranti	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20565	Aplysina fulva	Species	Aplysinidae	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 NPC85454 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	25073
0.1-0.2	23388
0.2-0.3	1182
0.3-0.4	98
0.4-0.5	74
0.5-0.6	32
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
0.7541	Intermediate Similarity	NPC227260
0.6984	Remote Similarity	NPC248944
0.6984	Remote Similarity	NPC7479
0.6984	Remote Similarity	NPC257296
0.6364	Remote Similarity	NPC273290
0.6364	Remote Similarity	NPC232044
0.6119	Remote Similarity	NPC296734
0.6061	Remote Similarity	NPC24556
0.5857	Remote Similarity	NPC305808
0.5857	Remote Similarity	NPC481427
0.5696	Remote Similarity	NPC473774
0.5696	Remote Similarity	NPC481418
0.5696	Remote Similarity	NPC481419
0.5696	Remote Similarity	NPC481417
0.5625	Remote Similarity	NPC24960
0.5616	Remote Similarity	NPC235126
0.5616	Remote Similarity	NPC242419
0.5541	Remote Similarity	NPC177818
0.5405	Remote Similarity	NPC52585
0.5405	Remote Similarity	NPC161035
0.5405	Remote Similarity	NPC170438
0.5316	Remote Similarity	NPC144790
0.5316	Remote Similarity	NPC149400
0.5316	Remote Similarity	NPC88962
0.5309	Remote Similarity	NPC481420
0.5309	Remote Similarity	NPC481421
0.5287	Remote Similarity	NPC206003
0.5287	Remote Similarity	NPC473610
0.525	Remote Similarity	NPC277715
0.5176	Remote Similarity	NPC297348
0.5176	Remote Similarity	NPC325828
0.5176	Remote Similarity	NPC249204
0.5176	Remote Similarity	NPC48339
0.5176	Remote Similarity	NPC177834
0.5176	Remote Similarity	NPC141769
0.5176	Remote Similarity	NPC477547
0.5132	Remote Similarity	NPC68630
0.5116	Remote Similarity	NPC294686
0.5116	Remote Similarity	NPC234352
0.5057	Remote Similarity	NPC477451

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7281
0.1-0.2	1791
0.2-0.3	72
0.3-0.4	2
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
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
0.6984	Remote Similarity	NPD6928	Phase 2
0.5185	Remote Similarity	NPD7991	Discontinued
0.5176	Remote Similarity	NPD8171	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