NPASS Compound

Natural Product: NPC473300

Natural Product ID	NPC473300
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ADDGUHVEJPNWQZ-PSDZGDCNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL398922
PubChem CID	44445496
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 108113 0 0 0 0 0 0 0 0999 V2000 10.4724 4.4577 -0.8147 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2070 3.8847 -1.3080 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4632 3.1829 -0.4805 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8922 2.9677 0.9419 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2208 2.6138 -0.9241 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8592 2.8105 -2.1288 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3873 1.8459 -0.0761 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1597 1.3058 -0.5779 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2914 -0.1807 -0.5964 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8273 -0.8923 0.4607 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9491 -2.2632 0.4500 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5175 -2.9458 -0.6618 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9691 -2.2912 -1.7585 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8755 -0.9184 -1.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9615 1.7329 0.2428 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6817 1.2696 -0.3083 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3332 1.6375 -1.4765 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7833 0.4429 0.3389 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5875 -0.0028 -0.1305 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6516 0.5049 0.6449 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5919 -0.6162 0.7204 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0286 -0.6293 0.8893 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8179 -1.4024 -0.1601 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6201 -2.8482 -0.3376 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3578 -3.1436 -1.6740 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7884 -2.8174 -1.6726 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2517 -1.7272 -0.8166 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1950 -0.8883 -0.1382 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0442 -0.9581 1.0846 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7543 -2.0102 0.4539 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3148 0.4188 -0.6986 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0699 0.7826 -1.9842 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6880 -0.0967 -2.7981 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2475 2.2066 -2.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2287 -4.4928 -2.0012 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3531 -3.4966 -0.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5714 -4.6861 -0.7331 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8028 -3.4166 -0.6090 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3424 -2.2770 0.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5014 -1.4758 -0.4584 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3610 -2.0564 -1.5011 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8254 -1.7147 1.4389 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6116 -2.7134 2.2076 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2827 -1.3077 2.3273 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2722 -4.5644 0.0301 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4116 -3.7450 0.6296 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3763 0.7619 0.7083 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9466 1.5277 1.7063 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1915 0.9965 2.8191 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2441 2.9221 1.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9171 3.5931 0.2891 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2336 4.9129 0.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9100 5.6090 1.0426 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2520 4.9782 2.2006 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9315 3.6426 2.4216 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6261 -0.8432 -0.7407 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1590 1.2614 1.5587 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1965 3.6331 -0.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9178 5.1462 -1.5872 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3038 5.0048 0.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8697 4.0195 -2.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3628 3.6563 1.6173 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9901 3.0835 0.9619 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6684 1.9280 1.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6717 1.6838 0.8992 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0070 1.6381 -1.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1584 -0.3300 1.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3652 -2.8290 1.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6067 -4.0166 -0.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6257 -2.8395 -2.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4456 -0.3722 -2.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9510 2.8409 0.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4964 0.4758 -1.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3937 1.0644 1.5358 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1620 1.3062 -0.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3998 -0.8074 1.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4202 -0.9805 -1.1406 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8154 -2.5729 -2.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0483 -2.5590 -2.7495 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4576 -3.7187 -1.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0638 -1.1045 -1.3135 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7945 -0.1178 1.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6187 -1.1597 2.0491 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8201 2.7545 -1.7164 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2955 2.7118 -2.6434 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8864 2.1731 -3.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7211 -4.6010 -2.8531 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6122 -3.5431 -1.6596 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0108 -1.2429 -1.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8150 -2.3916 -2.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0606 -2.8276 -1.1339 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6113 -3.7468 1.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1100 -2.9882 3.2032 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6029 -2.4538 2.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2147 -1.9176 3.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2937 -1.5763 2.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1283 -0.2900 2.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5914 -4.3806 0.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6034 -3.2158 1.5703 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2565 -4.2557 0.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7273 -4.5915 0.9513 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3734 3.0452 -0.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9655 5.4162 -0.8363 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1607 6.6366 0.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7853 5.4980 2.9878 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2017 3.1486 3.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6923 -0.0018 -1.2020 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5749 1.7191 2.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 8 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 25 35 1 0 24 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 39 40 2 0 40 41 1 0 39 42 1 0 42 43 1 0 42 44 1 0 38 45 1 0 24 46 1 0 22 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 21 56 1 0 15 57 1 0 14 9 1 0 40 19 1 0 42 21 1 0 28 23 1 0 30 27 1 0 55 50 1 0 1 58 1 0 1 59 1 0 1 60 1 0 2 61 1 0 4 62 1 0 4 63 1 0 4 64 1 0 7 65 1 0 8 66 1 0 10 67 1 0 11 68 1 0 12 69 1 0 13 70 1 0 14 71 1 0 15 72 1 0 19 73 1 0 20 74 1 0 20 75 1 0 22 76 1 0 23 77 1 0 25 78 1 0 26 79 1 0 26 80 1 0 27 81 1 0 29 82 1 0 29 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 0 38 88 1 0 41 89 1 0 41 90 1 0 41 91 1 0 43 92 1 0 43 93 1 0 43 94 1 0 44 95 1 0 44 96 1 0 44 97 1 0 45 98 1 0 46 99 1 0 46100 1 0 46101 1 0 51102 1 0 52103 1 0 53104 1 0 54105 1 0 55106 1 0 56107 1 0 57108 1 0 M END

Standard InCHIKey	ADDGUHVEJPNWQZ-PSDZGDCNSA-N
Standard InCHI	InChI=1S/C43H51NO13/c1-8-22(2)37(50)44-31(25-15-11-9-12-16-25)33(48)39(52)55-27-20-43(53)36(56-38(51)26-17-13-10-14-18-26)34-41(7,35(49)32(47)30(23(27)3)40(43,5)6)28(46)19-29-42(34,21-54-29)57-24(4)45/h8-18,27-29,31-34,36,46-48,53H,19-21H2,1-7H3,(H,44,50)/b22-8-/t27-,28+,29+,31-,32+,33+,34-,36-,41+,42-,43+/m0/s1
SMILES	CC=C(C)C(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)O)C)OC(=O)C6=CC=CC=C6)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	789.34	Volume:	791.941 ? Van der Waals volume.
Dense:	0.997	LogP:	2.45 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.649 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.243 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	38.0
TPSA:	215.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.107	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.008	Fsp³:	0.512
MCE-18:	163.2 ? 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:	0.458	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.107 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.483 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.011	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982	MDCK Permeability:	-4.591
Pgp-inhibitor:	0.013	Pgp-substrate:	0.982
PAMPA:	1.0 ? 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):	0.445
20% Bioavailability (F20%):	0.978	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	94.642%	Volume Distribution (VD):	0.18
Fu:	4.459% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.828
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.0
BSEP inhibitor:	0.595

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.024	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.951 ? 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):

2.652

Half-life (T1/2):

2.859

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.278
Human Hepatotoxicity (H-HT):	0.677	Drug-induced Liver Injury (DILI):	0.962
AMES Toxicity:	0.67	Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.942	Skin Sensitization:	0.1
Carcinogencity:	0.076	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.989	Ototoxicity:	0.994
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	0.968
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.261
A549 Cytotoxicity:	0.063	Hek293 Cytotoxicity:	0.941
BCF:	0.554 ? 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:	3.489 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.38 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.446 ? 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
NPO32766	luteibacter sp.	Species	Rhodanobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[18001087]

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	5

Activity Type	# Activity
Cell line	5

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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	2230.0	nM	PMID[9051909]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	3530.0	nM	PMID[1955884]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	790.0	nM	PMID[11473426]
NPT81	Cell line	A549	Homo sapiens	IC50	=	3240.0	nM	Open TG-GATES in vivo data: Organ Weight
NPT179	Cell line	A2780	Homo sapiens	IC50	=	350.0	nM	PMID[10891117]

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 NPC473300 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	10015
0.1-0.2	37383
0.2-0.3	2263
0.3-0.4	128
0.4-0.5	17
0.5-0.6	30
0.6-0.7	10
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8925	High Similarity	NPC317882
0.76	Intermediate Similarity	NPC453583
0.7426	Intermediate Similarity	NPC473400
0.7383	Intermediate Similarity	NPC472392
0.7184	Intermediate Similarity	NPC471754
0.7184	Intermediate Similarity	NPC479183
0.7184	Intermediate Similarity	NPC479181
0.7157	Intermediate Similarity	NPC321072
0.7157	Intermediate Similarity	NPC215892
0.7157	Intermediate Similarity	NPC242662
0.7157	Intermediate Similarity	NPC102167
0.7157	Intermediate Similarity	NPC488127
0.6923	Remote Similarity	NPC603171
0.6667	Remote Similarity	NPC471606
0.6389	Remote Similarity	NPC33372
0.6389	Remote Similarity	NPC67246
0.633	Remote Similarity	NPC478329
0.6316	Remote Similarity	NPC229545
0.6316	Remote Similarity	NPC248265
0.6316	Remote Similarity	NPC134685
0.6036	Remote Similarity	NPC487360
0.6	Remote Similarity	NPC473558
0.5962	Remote Similarity	NPC603140
0.5946	Remote Similarity	NPC324251
0.5946	Remote Similarity	NPC206211
0.5929	Remote Similarity	NPC275170
0.5909	Remote Similarity	NPC478328
0.5893	Remote Similarity	NPC479182
0.5893	Remote Similarity	NPC479180
0.5893	Remote Similarity	NPC471629
0.5893	Remote Similarity	NPC306001
0.5856	Remote Similarity	NPC471623
0.5856	Remote Similarity	NPC208553
0.5856	Remote Similarity	NPC181964
0.5856	Remote Similarity	NPC307628
0.5856	Remote Similarity	NPC191193
0.5826	Remote Similarity	NPC487361
0.5758	Remote Similarity	NPC605573
0.5739	Remote Similarity	NPC486061
0.5739	Remote Similarity	NPC486060
0.5676	Remote Similarity	NPC36607
0.5487	Remote Similarity	NPC327699
0.5447	Remote Similarity	NPC472375
0.5392	Remote Similarity	NPC11588
0.5347	Remote Similarity	NPC197037
0.5289	Remote Similarity	NPC289383
0.5285	Remote Similarity	NPC479186
0.5243	Remote Similarity	NPC155329
0.5243	Remote Similarity	NPC114357
0.5196	Remote Similarity	NPC91730
0.5196	Remote Similarity	NPC609501
0.5043	Remote Similarity	NPC453588

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3155
0.1-0.2	5847
0.2-0.3	135
0.3-0.4	0
0.4-0.5	3
0.5-0.6	8
0.6-0.7	0
0.7-0.8	2
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
0.7157	Intermediate Similarity	NPD8360	Approved
0.7157	Intermediate Similarity	NPD8361	Phase 4
0.5856	Remote Similarity	NPD8485	Phase 4
0.547	Remote Similarity	NPD8434	Phase 2
0.5455	Remote Similarity	NPD8404	Phase 2
0.5259	Remote Similarity	NPD8368	Phase 2
0.5254	Remote Similarity	NPD8486	Phase 1
0.5217	Remote Similarity	NPD8424	Phase 3
0.5118	Remote Similarity	NPD8462	Phase 2
0.5043	Remote Similarity	NPD8435	Phase 4

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