NPASS Compound

Natural Product: NPC605573

Natural Product ID	NPC605573
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WPPPFZJNKLMYBW-FAEUQDRCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL75533
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 87 91 0 0 0 0 0 0 0 0999 V2000 -1.2557 -5.4212 -0.0754 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8325 -4.2252 0.5832 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9164 -4.3533 1.2075 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2393 -2.9986 0.5399 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7428 -1.8200 1.1493 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7793 -1.2375 2.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4521 0.2186 1.8808 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1846 0.7282 3.1856 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6223 0.3332 0.9271 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8917 -0.9797 0.3465 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9325 -1.7985 0.6341 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7320 -1.3845 1.5122 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2142 -3.0861 0.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4933 -3.6636 -0.9831 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8374 -4.9158 -1.4874 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9159 -5.6083 -0.9718 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6446 -5.0545 0.0393 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2815 -3.8067 0.5241 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9646 1.4033 -0.0311 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4270 1.8568 0.0513 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1381 1.5717 1.2139 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9408 2.0091 2.4815 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7890 1.6049 3.6470 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0035 2.7968 2.7227 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9604 3.1270 -0.4285 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1085 2.3788 -0.8545 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1094 1.5128 -1.2738 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2300 1.9345 -2.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8704 2.3807 -2.2233 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4827 3.5680 -2.8335 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2353 2.3736 -0.7857 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4210 3.8648 -0.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2119 2.3370 -1.0688 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5329 3.0447 -2.2629 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9903 1.0580 -1.1424 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3539 1.5024 -1.3167 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0141 1.2798 -2.4822 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4341 1.7215 -2.7243 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4592 0.6857 -3.4247 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9306 0.4394 0.1610 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0109 -0.8767 -0.0204 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3587 -1.4780 -1.3251 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7974 0.8224 1.5805 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8254 2.2433 1.9844 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9779 0.2341 2.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2624 -5.6085 0.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9131 -6.2873 -0.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0420 -5.1128 -1.1409 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6872 -2.1747 1.6163 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1300 -1.8640 2.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0835 -1.4197 3.2017 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4378 0.0910 3.6398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5245 0.3491 1.6399 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6509 -3.1367 -1.4043 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2858 -5.3831 -2.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2147 -6.5854 -1.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4964 -5.5833 0.4582 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9236 -3.4348 1.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0971 0.6358 -0.9399 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5462 2.4009 3.7622 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1587 1.5603 4.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2166 0.5979 3.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3809 3.8540 0.3353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6901 3.6780 -1.2863 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4592 0.4794 -1.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8041 2.6989 -3.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3195 1.0565 -3.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2304 1.6076 -2.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1585 3.9664 -3.3999 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5530 4.5342 -1.2100 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5924 4.2590 0.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9988 3.9973 0.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8156 2.9787 -0.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5347 2.4872 -3.0547 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6814 0.5644 -2.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6036 2.6037 -2.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1534 0.9420 -2.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5949 1.9523 -3.7966 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6664 -1.3506 -2.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3508 -2.6154 -1.1782 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4487 -1.3366 -1.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8935 2.1862 3.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9278 2.8330 1.8793 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7909 2.7574 1.7669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7715 -0.1285 1.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6270 1.0371 2.8250 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7827 -0.4100 3.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 9 19 1 0 19 20 1 0 20 21 1 1 21 22 1 0 22 23 1 0 22 24 2 0 20 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 37 39 2 0 35 40 1 0 40 41 2 0 41 42 1 0 40 43 1 0 43 44 1 0 43 45 1 0 41 5 1 0 43 7 1 0 18 13 1 0 31 19 1 0 27 20 1 0 1 46 1 0 1 47 1 0 1 48 1 0 5 49 1 1 6 50 1 0 6 51 1 0 8 52 1 0 9 53 1 1 14 54 1 0 15 55 1 0 16 56 1 0 17 57 1 0 18 58 1 0 19 59 1 6 23 60 1 0 23 61 1 0 23 62 1 0 25 63 1 0 25 64 1 0 27 65 1 1 28 66 1 0 28 67 1 0 29 68 1 6 30 69 1 0 32 70 1 0 32 71 1 0 32 72 1 0 33 73 1 1 34 74 1 0 35 75 1 6 38 76 1 0 38 77 1 0 38 78 1 0 42 79 1 0 42 80 1 0 42 81 1 0 44 82 1 0 44 83 1 0 44 84 1 0 45 85 1 0 45 86 1 0 45 87 1 0 M END

Standard InCHIKey	WPPPFZJNKLMYBW-FAEUQDRCSA-N
Standard InCHI	InChI=1S/C33H42O12/c1-16-21(42-17(2)34)14-33(40)28(44-29(39)20-11-9-8-10-12-20)26-31(7,22(37)13-23-32(26,15-41-23)45-19(4)36)27(38)25(43-18(3)35)24(16)30(33,5)6/h8-12,21-23,25-28,37-38,40H,13-15H2,1-7H3/t21-,22-,23+,25+,26-,27-,28-,31+,32-,33+/m0/s1
SMILES	CC(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)[C@@H](O)[C@H](OC(C)=O)C(=C1C)C2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	630.27	Volume:	620.933 ? Van der Waals volume.
Dense:	1.015	LogP:	1.8 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.224 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.669 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	175.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.246	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.659	Fsp³:	0.636
MCE-18:	144.259 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.61	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.052	Promiscuous compounds:	0.279

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.77	MDCK Permeability:	-5.22
Pgp-inhibitor:	1.0	Pgp-substrate:	1.0
PAMPA:	0.998 ? 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):	0.04
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	83.82%	Volume Distribution (VD):	-0.046
Fu:	15.613% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.946	BCRP inhibitor:	0.004
BSEP inhibitor:	0.979

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.52 ? 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):

7.9

Half-life (T1/2):

1.67

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.099
Human Hepatotoxicity (H-HT):	0.506	Drug-induced Liver Injury (DILI):	0.963
AMES Toxicity:	0.986	Rat Oral Acute Toxicity:	0.504
Maximum Recommended Daily Dose:	0.789	Skin Sensitization:	1.0
Carcinogencity:	0.794	Eye Corrosion:	0.0
Eye Irritation:	0.068	Respiratory Toxicity:	0.049
Drug-induced Neurotoxicity:	0.784	Ototoxicity:	0.665
Hematotoxicity:	0.727	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.308
A549 Cytotoxicity:	0.887	Hek293 Cytotoxicity:	0.434
BCF:	0.409 ? 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:	3.157 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.756 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.779 ? 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
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plantsci.2006.08.002]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(00)00306-X]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(01)00432-0]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np990201k]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	Needles	n.a.	n.a.	PMID[11325226]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955887]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2878063]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7130988]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	bark	n.a.	n.a.	PMID[7623034]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27064	Taxus brevifolia	Species	Taxaceae	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

Activity Type	# Activity
Cell line	2

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
NPT168	Cell line	P388	Mus musculus	IC50	=	52480746.02	nM	DOI[10.1016/S0960-894X(97)00439-3]
NPT168	Cell line	P388	Mus musculus	IC50	=	20.0	ug.mL-1	DOI[10.1021/np50089a022]

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 NPC605573 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	8660
0.1-0.2	37767
0.2-0.3	2896
0.3-0.4	456
0.4-0.5	24
0.5-0.6	42
0.6-0.7	10
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
0.7922	Intermediate Similarity	NPC217918
0.764	Intermediate Similarity	NPC327699
0.6629	Remote Similarity	NPC603140
0.631	Remote Similarity	NPC609501
0.6267	Remote Similarity	NPC79303
0.6163	Remote Similarity	NPC155329
0.6163	Remote Similarity	NPC114357
0.6082	Remote Similarity	NPC36607
0.6023	Remote Similarity	NPC259144
0.6023	Remote Similarity	NPC219419
0.6	Remote Similarity	NPC471629
0.6	Remote Similarity	NPC306001
0.596	Remote Similarity	NPC471623
0.596	Remote Similarity	NPC208553
0.596	Remote Similarity	NPC181964
0.596	Remote Similarity	NPC307628
0.596	Remote Similarity	NPC473400
0.596	Remote Similarity	NPC603171
0.593	Remote Similarity	NPC197037
0.593	Remote Similarity	NPC229545
0.593	Remote Similarity	NPC248265
0.593	Remote Similarity	NPC134685
0.59	Remote Similarity	NPC33372
0.59	Remote Similarity	NPC67246
0.59	Remote Similarity	NPC324251
0.59	Remote Similarity	NPC206211
0.5842	Remote Similarity	NPC487360
0.5842	Remote Similarity	NPC479182
0.5842	Remote Similarity	NPC479180
0.5795	Remote Similarity	NPC11588
0.5758	Remote Similarity	NPC473300
0.5747	Remote Similarity	NPC91730
0.5743	Remote Similarity	NPC471754
0.5728	Remote Similarity	NPC471606
0.5728	Remote Similarity	NPC275170
0.57	Remote Similarity	NPC321072
0.57	Remote Similarity	NPC215892
0.57	Remote Similarity	NPC242662
0.57	Remote Similarity	NPC102167
0.57	Remote Similarity	NPC488127
0.5673	Remote Similarity	NPC486061
0.5673	Remote Similarity	NPC486060
0.5644	Remote Similarity	NPC453583
0.5644	Remote Similarity	NPC317882
0.5644	Remote Similarity	NPC191193
0.5619	Remote Similarity	NPC487361
0.5588	Remote Similarity	NPC479183
0.5588	Remote Similarity	NPC479181
0.5534	Remote Similarity	NPC478329
0.5444	Remote Similarity	NPC473632
0.5392	Remote Similarity	NPC473490
0.5192	Remote Similarity	NPC473558
0.5111	Remote Similarity	NPC38696
0.5096	Remote Similarity	NPC478328

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605573 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3262
0.1-0.2	5686
0.2-0.3	189
0.3-0.4	0
0.4-0.5	3
0.5-0.6	10
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
0.596	Remote Similarity	NPD8485	Phase 4
0.57	Remote Similarity	NPD8360	Approved
0.57	Remote Similarity	NPD8361	Phase 4
0.5437	Remote Similarity	NPD8368	Phase 2
0.5392	Remote Similarity	NPD8424	Phase 3
0.534	Remote Similarity	NPD8435	Phase 4
0.5283	Remote Similarity	NPD8486	Phase 1
0.5185	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.513	Remote Similarity	NPD8462	Phase 2
0.5093	Remote Similarity	NPD8434	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