NPASS Compound

Natural Product: NPC95428

Natural Product ID	NPC95428
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ODSSDTBFHAYYMD-TXMWGPFBSA-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 86 90 0 0 0 0 0 0 0 0999 V2000 -6.6733 -0.6574 1.8003 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3673 -0.5934 1.7084 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5951 -1.7634 2.3096 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5474 0.4803 1.0978 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4196 1.5159 0.4603 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3229 1.2788 -1.0589 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8319 0.9768 -1.1465 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1067 2.2464 -1.0995 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4422 0.2156 -2.3744 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9842 -0.1534 -2.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6542 -0.9455 -1.0058 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1843 -2.3430 -1.3568 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3328 -0.4691 0.2511 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6268 0.5061 1.0898 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2180 0.8127 0.8297 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3909 0.3412 -0.4502 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9003 0.3899 -0.3524 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4675 0.5835 -1.7081 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3048 1.6653 0.4177 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8007 1.7779 0.4960 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5938 0.5655 0.2713 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9259 -0.7558 0.5995 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6448 -1.7911 -0.2303 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3674 -1.0574 2.0513 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4599 -0.7296 0.4885 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7920 -2.0454 0.3180 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2719 -1.8972 0.3072 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1438 -1.0076 -0.8208 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3811 -1.5799 -2.0953 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8098 0.6816 1.0289 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0641 0.7360 0.4817 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1478 0.6792 -0.7858 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3150 0.8540 1.2351 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7119 -0.0048 -0.0370 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1031 -1.5482 2.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4061 0.0324 1.4571 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4260 -2.5481 1.5748 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2427 -2.2313 3.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7096 -1.4104 2.8657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9475 0.8938 1.9434 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0900 2.5563 0.6992 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4798 1.4896 0.6834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6003 2.1917 -1.5816 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9028 0.3858 -1.3115 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3815 2.7812 -2.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4130 2.9837 -0.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9922 2.1846 -1.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5407 0.8699 -3.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0809 -0.6699 -2.5115 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3919 0.7203 -2.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8353 -0.8114 -3.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2354 -2.4921 -1.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1878 -2.5123 -2.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6280 -3.1654 -0.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4462 -1.4306 0.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2036 1.4844 1.0801 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8052 0.2226 2.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0295 1.9326 0.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3569 0.4740 1.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1609 1.1322 -1.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1062 -0.1826 -2.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6466 0.7564 -2.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0622 1.5423 -1.8403 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9174 1.7070 1.4277 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8431 2.4993 -0.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1008 2.2568 1.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0949 2.5489 -0.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9631 0.5370 -0.7969 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6479 -2.0146 0.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9557 -1.4023 -1.2395 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1506 -2.7528 -0.3060 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4847 -0.0915 2.6110 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5861 -1.6308 2.5799 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3341 -1.5579 2.0793 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1245 -0.4317 1.5420 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9861 -2.6447 1.2647 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1301 -2.7013 -0.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0264 -1.4719 1.3116 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1009 -2.9143 0.3119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1713 -2.5613 -2.2312 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4249 -1.8532 -2.1415 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1584 -1.0173 -3.0129 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1871 0.4794 0.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2671 0.2544 2.1872 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5011 1.9310 1.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2883 -0.9123 -0.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 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 1 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 13 34 1 0 34 4 1 0 34 7 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 1 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 10 50 1 0 10 51 1 0 12 52 1 0 12 53 1 0 12 54 1 0 13 55 1 1 14 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 6 18 61 1 0 18 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 20 66 1 0 20 67 1 0 21 68 1 6 23 69 1 0 23 70 1 0 23 71 1 0 24 72 1 0 24 73 1 0 24 74 1 0 25 75 1 1 26 76 1 0 26 77 1 0 27 78 1 0 27 79 1 0 29 80 1 0 29 81 1 0 29 82 1 0 33 83 1 0 33 84 1 0 33 85 1 0 34 86 1 6 M END

Standard InCHIKey	ODSSDTBFHAYYMD-TXMWGPFBSA-N
Standard InCHI	InChI=1S/C32H52O2/c1-20(2)22-12-15-29(6)18-19-31(8)23(27(22)29)10-11-25-30(7)16-14-26(34-21(3)33)28(4,5)24(30)13-17-32(25,31)9/h22-27H,1,10-19H2,2-9H3/t22-,23-,24-,25-,26+,27+,29+,30-,31+,32+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@@H](CC[C@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)C)[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.4	Volume:	531.553 ? Van der Waals volume.
Dense:	0.881	LogP:	5.965 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.306 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.253 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.299	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.692	Fsp³:	0.906
MCE-18:	102.164 ? 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:	0.981	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.666	Promiscuous compounds:	0.352

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152	MDCK Permeability:	-4.928
Pgp-inhibitor:	1.0	Pgp-substrate:	0.0
PAMPA:	0.002 ? 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%):	0.031	30% Bioavailability (F30%):	0.143
50% Bioavailability (F50%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027	MRP1:	0.221
Plasma Protein Binding (PPB):	95.819%	Volume Distribution (VD):	0.178
Fu:	4.831% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.392
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.994	CYP1A2-substrate:	0.268
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.025	CYP2C9-substrate:	0.412
CYP2D6-inhibitor:	0.115	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.835	CYP2C8-inhibitor:	1.0
HLM stability:	0.872 ? 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):

11.783

Half-life (T1/2):

0.334

ADMET: Toxicity

hERG Blockers:	0.084	hERG Blockers (10um):	0.342
Human Hepatotoxicity (H-HT):	0.539	Drug-induced Liver Injury (DILI):	0.533
AMES Toxicity:	0.245	Rat Oral Acute Toxicity:	0.258
Maximum Recommended Daily Dose:	0.418	Skin Sensitization:	0.92
Carcinogencity:	0.918	Eye Corrosion:	0.638
Eye Irritation:	0.876	Respiratory Toxicity:	0.721
Drug-induced Neurotoxicity:	0.043	Ototoxicity:	0.333
Hematotoxicity:	0.57	Drug-induced Nephrotoxicity:	0.55
Genotoxicity:	0.122	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.349	Hek293 Cytotoxicity:	0.461
BCF:	3.256 ? 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:	5.467 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.064 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.628 ? 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
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075788]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18321057]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19099222]
NPO13162	Glycosmis petelotii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24949913]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724086]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31550154]
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463095]
NPO12346	Daphnandra apatela	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10762	Brasilia sickii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5896	Crinum laurentii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10762	Brasilia sickii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9211	Margyricarpus setosus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5896	Crinum laurentii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12346	Daphnandra apatela	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12829	Ocotea acutifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15995	Moesziomyces rugulosus	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26146	Ruilopezia lindenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13162	Glycosmis petelotii	Species	Rutaceae	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 NPC95428 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	24461
0.1-0.2	21370
0.2-0.3	3542
0.3-0.4	336
0.4-0.5	93
0.5-0.6	34
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC305835
0.8519	High Similarity	NPC611062
0.7679	Intermediate Similarity	NPC98270
0.7636	Intermediate Similarity	NPC84868
0.7544	Intermediate Similarity	NPC5280
0.7541	Intermediate Similarity	NPC475416
0.7414	Intermediate Similarity	NPC304194
0.7414	Intermediate Similarity	NPC473742
0.7188	Intermediate Similarity	NPC239362
0.6949	Remote Similarity	NPC481227
0.6833	Remote Similarity	NPC261616
0.6721	Remote Similarity	NPC168231
0.6667	Remote Similarity	NPC474092
0.6452	Remote Similarity	NPC471901
0.625	Remote Similarity	NPC473690
0.614	Remote Similarity	NPC43300
0.6094	Remote Similarity	NPC4309
0.5968	Remote Similarity	NPC61107
0.5965	Remote Similarity	NPC192638
0.5965	Remote Similarity	NPC25511
0.5965	Remote Similarity	NPC600137
0.5833	Remote Similarity	NPC475509
0.5833	Remote Similarity	NPC488509
0.5781	Remote Similarity	NPC303863
0.5738	Remote Similarity	NPC302280
0.5606	Remote Similarity	NPC180204
0.5484	Remote Similarity	NPC269396
0.5441	Remote Similarity	NPC160506
0.541	Remote Similarity	NPC293803
0.5385	Remote Similarity	NPC488508
0.5333	Remote Similarity	NPC102708
0.5323	Remote Similarity	NPC159497
0.5303	Remote Similarity	NPC31031
0.5263	Remote Similarity	NPC473612
0.5254	Remote Similarity	NPC35652
0.5231	Remote Similarity	NPC190940
0.5231	Remote Similarity	NPC488510
0.5211	Remote Similarity	NPC471902
0.519	Remote Similarity	NPC148404
0.519	Remote Similarity	NPC35212
0.5167	Remote Similarity	NPC80297
0.5167	Remote Similarity	NPC475727
0.5167	Remote Similarity	NPC116119
0.5161	Remote Similarity	NPC248830
0.5161	Remote Similarity	NPC212241
0.5156	Remote Similarity	NPC132386
0.5156	Remote Similarity	NPC103754
0.5132	Remote Similarity	NPC473844
0.5077	Remote Similarity	NPC12774
0.5075	Remote Similarity	NPC607755
0.507	Remote Similarity	NPC287118

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC95428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7057
0.1-0.2	2048
0.2-0.3	38
0.3-0.4	5
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
0.5441	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