NPASS Compound

Natural Product: NPC234077

Natural Product ID	NPC234077
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asimilobin
IUPAC Name	(2S)-4-[(2R)-2-hydroxy-7-[(2R,5S)-5-[(2S,5S)-5-[(1S)-1-hydroxypentadecyl]oxolan-2-yl]oxolan-2-yl]heptyl]-2-methyl-2H-furan-5-one
Synonyms	Asimilobin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510067
PubChem CID	10257606
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 103105 0 0 0 0 0 0 0 0999 V2000 -13.3383 0.3060 -1.5796 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6972 -0.7923 -0.7734 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2564 -1.0236 -1.1578 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4024 0.2025 -0.9579 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3791 0.6749 0.4595 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8605 -0.2669 1.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5461 -0.8711 1.3981 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2942 -0.0306 1.4016 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0733 0.8178 0.2368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9233 1.7446 0.2519 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5250 1.3033 0.4365 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1880 0.8279 1.7782 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8010 0.3744 2.0583 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2008 -0.7633 1.3845 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0110 -0.8135 -0.0703 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1674 0.3054 -0.6307 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8840 -0.0343 -2.0850 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5898 0.2965 -2.1855 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0517 -0.0430 -0.7840 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0309 0.4596 0.0067 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3559 0.6910 -0.5572 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4248 -0.0160 -1.3629 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7738 -1.1547 -0.4025 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4607 -0.6073 0.9185 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7822 0.6075 0.7561 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5164 -0.5112 1.9555 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7043 0.3113 1.7020 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6327 -0.0290 0.6093 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2917 -1.3759 0.7543 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1928 -1.6870 -0.3812 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3374 -0.7345 -0.5998 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2509 -0.6357 0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3945 0.3027 0.3372 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6282 0.9805 -0.7603 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8446 1.7794 -0.5747 C 0 0 1 0 0 0 0 0 0 0 0 0 13.2897 1.5047 0.7137 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4490 0.6153 1.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5258 0.1344 2.4774 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9634 1.3027 -1.5198 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8988 0.4964 -1.0870 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1661 -1.9793 -0.2806 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2012 1.2987 -1.0838 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4440 0.1680 -1.6533 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9540 0.3955 -2.6023 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2462 -1.7337 -0.9881 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8341 -0.5712 0.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8468 -1.8617 -0.5968 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2331 -1.2796 -2.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3736 -0.0863 -1.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6943 1.0408 -1.6086 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9636 1.6756 0.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5027 0.8976 0.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6072 -1.1057 1.6711 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9166 0.3057 2.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4883 -1.5857 0.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3809 -1.5872 2.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2671 0.5404 2.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4629 -0.8304 1.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9585 1.4659 -0.0516 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9725 0.0847 -0.6556 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2006 2.5272 1.0618 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0103 2.4195 -0.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8850 2.2193 0.2359 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3375 0.5564 -0.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2645 1.8064 2.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9477 0.2138 2.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8014 0.1298 3.1795 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1051 1.2841 2.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1580 -0.9110 1.8442 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7135 -1.7120 1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8413 -1.0174 -0.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7426 1.2659 -0.6524 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5097 0.5063 -2.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0016 -1.1260 -2.2866 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7109 1.3727 -2.3614 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0614 -0.3378 -2.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1975 -1.1219 -0.6696 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2802 1.7472 -0.8643 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9975 -0.4227 -2.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2882 0.6387 -1.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7508 -1.5748 -0.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0417 -1.9693 -0.6885 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6555 -1.2822 1.3737 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0049 -0.0573 2.8679 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7477 -1.5469 2.3184 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3160 0.4139 2.6385 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3519 1.3733 1.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5057 0.7103 0.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3119 0.1387 -0.4161 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5050 -2.1471 0.8035 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8100 -1.4477 1.7487 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5954 -1.7046 -1.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6336 -2.6949 -0.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9406 -1.1826 -1.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7537 -0.3062 1.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7198 -1.6126 0.8028 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0384 0.9796 -1.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6643 2.8691 -0.7439 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7887 2.0182 -1.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6312 1.2570 -2.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2868 0.3128 -1.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3322 0.3069 -1.8760 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7307 -2.7927 -0.1588 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 7 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 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 35 39 1 0 31 40 1 0 15 41 1 0 20 16 1 0 25 21 1 0 37 33 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 8 57 1 0 8 58 1 0 9 59 1 0 9 60 1 0 10 61 1 0 10 62 1 0 11 63 1 0 11 64 1 0 12 65 1 0 12 66 1 0 13 67 1 0 13 68 1 0 14 69 1 0 14 70 1 0 15 71 1 6 16 72 1 6 17 73 1 0 17 74 1 0 18 75 1 0 18 76 1 0 19 77 1 6 21 78 1 6 22 79 1 0 22 80 1 0 23 81 1 0 23 82 1 0 24 83 1 1 26 84 1 0 26 85 1 0 27 86 1 0 27 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 29 91 1 0 30 92 1 0 30 93 1 0 31 94 1 6 32 95 1 0 32 96 1 0 34 97 1 0 35 98 1 1 39 99 1 0 39100 1 0 39101 1 0 40102 1 0 41103 1 0 M END

Standard InCHIKey	ICSXGOKNISTZTO-GCCZPAPFSA-N
Standard InCHI	InChI=1S/C35H62O6/c1-3-4-5-6-7-8-9-10-11-12-13-17-20-31(37)32-23-24-34(41-32)33-22-21-30(40-33)19-16-14-15-18-29(36)26-28-25-27(2)39-35(28)38/h25,27,29-34,36-37H,3-24,26H2,1-2H3/t27-,29+,30+,31-,32-,33-,34-/m0/s1
SMILES	CCCCCCCCCCCCCC[C@@H]([C@@H]1CC[C@H](O1)[C@@H]1CC[C@H](O1)CCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.45	Volume:	635.715 ? Van der Waals volume.
Dense:	0.91	LogP:	6.087 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.256 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.442 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	16.0
TPSA:	85.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.094	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.549	Fsp³:	0.914
MCE-18:	40.836 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.892	Fluc inhibitor:	0.09 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.058 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.582	Promiscuous compounds:	0.342

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.114	MDCK Permeability:	-4.86
Pgp-inhibitor:	0.002	Pgp-substrate:	0.85
PAMPA:	0.01 ? 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):	0.003
20% Bioavailability (F20%):	0.926	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.963
Plasma Protein Binding (PPB):	97.948%	Volume Distribution (VD):	0.752
Fu:	2.316% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.928
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.819
BSEP inhibitor:	0.906

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.922	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.828
HLM stability:	0.001 ? 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):

5.382

Half-life (T1/2):

1.095

ADMET: Toxicity

hERG Blockers:	0.576	hERG Blockers (10um):	0.829
Human Hepatotoxicity (H-HT):	0.689	Drug-induced Liver Injury (DILI):	0.63
AMES Toxicity:	0.551	Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.91	Skin Sensitization:	1.0
Carcinogencity:	0.472	Eye Corrosion:	0.107
Eye Irritation:	0.867	Respiratory Toxicity:	0.921
Drug-induced Neurotoxicity:	0.142	Ototoxicity:	0.529
Hematotoxicity:	0.171	Drug-induced Nephrotoxicity:	0.833
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.132
A549 Cytotoxicity:	0.988	Hek293 Cytotoxicity:	0.451
BCF:	0.959 ? 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:	4.856 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.198 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.036 ? 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
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11087592]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15730242]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1593281]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30028612]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8676130]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946743]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7697	Asimina triloba	Species	Annonaceae	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
ED50	12

Activity Type	# Activity
Cell line	12

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	3.01	10'-2 ug/ml	PMID[20681570]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.14	ug ml-1	PMID[21060288]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	6.3	10'-2 ug/ml	PMID[9461654]
NPT376	Cell line	A498	Homo sapiens	ED50	=	2.26	10'-2 ug/ml	PMID[9461654]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	1.47	ug ml-1	PMID[22264149]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	1.04	10'-1 ug/ml	PMID[22264170]

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
-	Artemia	LC50	=	1.06	ug.mL-1	PMID[20681570]

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 NPC234077 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	17623
0.1-0.2	29683
0.2-0.3	2229
0.3-0.4	93
0.4-0.5	13
0.5-0.6	23
0.6-0.7	76
0.7-0.8	0
0.8-0.85	12
0.85-0.9	19
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC169511
1.0	High Similarity	NPC287164
0.9412	High Similarity	NPC91067
0.875	High Similarity	NPC81045
0.875	High Similarity	NPC39754
0.875	High Similarity	NPC171135
0.875	High Similarity	NPC61257
0.875	High Similarity	NPC320569
0.875	High Similarity	NPC133730
0.875	High Similarity	NPC191929
0.875	High Similarity	NPC100454
0.875	High Similarity	NPC242364
0.875	High Similarity	NPC172821
0.875	High Similarity	NPC274446
0.875	High Similarity	NPC485251
0.875	High Similarity	NPC151403
0.875	High Similarity	NPC261952
0.875	High Similarity	NPC605171
0.8571	High Similarity	NPC93794
0.8571	High Similarity	NPC473504
0.8571	High Similarity	NPC81778
0.8571	High Similarity	NPC40066
0.8431	Intermediate Similarity	NPC20621
0.8431	Intermediate Similarity	NPC318963
0.8431	Intermediate Similarity	NPC602738
0.8431	Intermediate Similarity	NPC605101
0.8364	Intermediate Similarity	NPC473663
0.8364	Intermediate Similarity	NPC473723
0.8364	Intermediate Similarity	NPC475173
0.8269	Intermediate Similarity	NPC473478
0.8269	Intermediate Similarity	NPC473651
0.8269	Intermediate Similarity	NPC66346
0.8235	Intermediate Similarity	NPC42598
0.8113	Intermediate Similarity	NPC283085
0.7778	Intermediate Similarity	NPC231096
0.7778	Intermediate Similarity	NPC475581
0.7778	Intermediate Similarity	NPC62118
0.7778	Intermediate Similarity	NPC132496
0.7778	Intermediate Similarity	NPC107717
0.7778	Intermediate Similarity	NPC488252
0.7755	Intermediate Similarity	NPC606043
0.76	Intermediate Similarity	NPC107986
0.76	Intermediate Similarity	NPC223871
0.76	Intermediate Similarity	NPC231009
0.76	Intermediate Similarity	NPC103284
0.76	Intermediate Similarity	NPC110710
0.76	Intermediate Similarity	NPC1083
0.76	Intermediate Similarity	NPC82795
0.76	Intermediate Similarity	NPC286338
0.76	Intermediate Similarity	NPC603931
0.76	Intermediate Similarity	NPC604237
0.75	Intermediate Similarity	NPC239517
0.7455	Intermediate Similarity	NPC473995
0.7451	Intermediate Similarity	NPC488253
0.7451	Intermediate Similarity	NPC473669
0.7451	Intermediate Similarity	NPC488251
0.7368	Intermediate Similarity	NPC473520
0.7368	Intermediate Similarity	NPC480081
0.7308	Intermediate Similarity	NPC232555
0.7308	Intermediate Similarity	NPC171174
0.7308	Intermediate Similarity	NPC182383
0.7308	Intermediate Similarity	NPC114694
0.7308	Intermediate Similarity	NPC485248
0.7308	Intermediate Similarity	NPC142117
0.7308	Intermediate Similarity	NPC480249
0.7308	Intermediate Similarity	NPC485249
0.7308	Intermediate Similarity	NPC240695
0.717	Intermediate Similarity	NPC488632
0.717	Intermediate Similarity	NPC473649
0.717	Intermediate Similarity	NPC473156
0.717	Intermediate Similarity	NPC134865
0.717	Intermediate Similarity	NPC154097
0.717	Intermediate Similarity	NPC103523
0.717	Intermediate Similarity	NPC159750
0.717	Intermediate Similarity	NPC73248
0.717	Intermediate Similarity	NPC282815
0.717	Intermediate Similarity	NPC488627
0.717	Intermediate Similarity	NPC488631
0.717	Intermediate Similarity	NPC470401
0.717	Intermediate Similarity	NPC600956
0.717	Intermediate Similarity	NPC610454
0.7143	Intermediate Similarity	NPC606740
0.7143	Intermediate Similarity	NPC608614
0.7069	Intermediate Similarity	NPC488630
0.7069	Intermediate Similarity	NPC488625
0.7069	Intermediate Similarity	NPC488626
0.7037	Intermediate Similarity	NPC280621
0.7037	Intermediate Similarity	NPC473671
0.7037	Intermediate Similarity	NPC475268
0.7037	Intermediate Similarity	NPC470400
0.7037	Intermediate Similarity	NPC77871
0.7037	Intermediate Similarity	NPC48338
0.7037	Intermediate Similarity	NPC9678
0.7037	Intermediate Similarity	NPC319036
0.7037	Intermediate Similarity	NPC488628
0.7037	Intermediate Similarity	NPC604764
0.7037	Intermediate Similarity	NPC605867
0.7018	Intermediate Similarity	NPC488623
0.7018	Intermediate Similarity	NPC488624
0.7018	Intermediate Similarity	NPC488629
0.6923	Remote Similarity	NPC25764
0.6923	Remote Similarity	NPC235809
0.6923	Remote Similarity	NPC39279
0.6923	Remote Similarity	NPC39167
0.6923	Remote Similarity	NPC292809
0.6923	Remote Similarity	NPC202055
0.6923	Remote Similarity	NPC606804
0.6923	Remote Similarity	NPC607425
0.6923	Remote Similarity	NPC608574
0.6909	Remote Similarity	NPC178215
0.6909	Remote Similarity	NPC473687
0.6909	Remote Similarity	NPC204686
0.6909	Remote Similarity	NPC219498
0.6909	Remote Similarity	NPC308412
0.6909	Remote Similarity	NPC134885
0.6909	Remote Similarity	NPC488247
0.6909	Remote Similarity	NPC132940
0.6909	Remote Similarity	NPC210218
0.6909	Remote Similarity	NPC488248
0.6885	Remote Similarity	NPC482766
0.6885	Remote Similarity	NPC279267
0.6852	Remote Similarity	NPC47937
0.6842	Remote Similarity	NPC258068
0.6842	Remote Similarity	NPC476583
0.6786	Remote Similarity	NPC20533
0.6786	Remote Similarity	NPC488250
0.6727	Remote Similarity	NPC241360
0.6727	Remote Similarity	NPC293136
0.6724	Remote Similarity	NPC233551
0.6724	Remote Similarity	NPC40376
0.6724	Remote Similarity	NPC21208
0.6667	Remote Similarity	NPC473707
0.6667	Remote Similarity	NPC69082
0.6667	Remote Similarity	NPC488249
0.6607	Remote Similarity	NPC65930
0.6552	Remote Similarity	NPC120398
0.6552	Remote Similarity	NPC130359
0.6552	Remote Similarity	NPC14901
0.6552	Remote Similarity	NPC471567
0.6545	Remote Similarity	NPC477011
0.6545	Remote Similarity	NPC600524
0.6545	Remote Similarity	NPC608355
0.6538	Remote Similarity	NPC112685
0.6531	Remote Similarity	NPC608138
0.6491	Remote Similarity	NPC134807
0.6441	Remote Similarity	NPC89001
0.6429	Remote Similarity	NPC219652
0.6429	Remote Similarity	NPC473840
0.6429	Remote Similarity	NPC480079
0.6296	Remote Similarity	NPC100921
0.6296	Remote Similarity	NPC475159
0.6296	Remote Similarity	NPC131002
0.6296	Remote Similarity	NPC473780
0.6296	Remote Similarity	NPC477018
0.6296	Remote Similarity	NPC604521
0.6207	Remote Similarity	NPC329615
0.6207	Remote Similarity	NPC485250
0.6207	Remote Similarity	NPC605396
0.6167	Remote Similarity	NPC477014
0.6167	Remote Similarity	NPC477013
0.614	Remote Similarity	NPC25703
0.6102	Remote Similarity	NPC20339
0.6071	Remote Similarity	NPC156804
0.6038	Remote Similarity	NPC73310
0.6038	Remote Similarity	NPC473529
0.6038	Remote Similarity	NPC180363
0.6038	Remote Similarity	NPC94875
0.6038	Remote Similarity	NPC11332
0.6038	Remote Similarity	NPC145914
0.6038	Remote Similarity	NPC601174
0.6038	Remote Similarity	NPC601403
0.6038	Remote Similarity	NPC603568
0.6038	Remote Similarity	NPC604330
0.6038	Remote Similarity	NPC608300
0.6038	Remote Similarity	NPC611200
0.6038	Remote Similarity	NPC611571
0.5965	Remote Similarity	NPC163093
0.5902	Remote Similarity	NPC480082
0.5873	Remote Similarity	NPC253801
0.5833	Remote Similarity	NPC480076
0.5833	Remote Similarity	NPC480077
0.5714	Remote Similarity	NPC329829
0.5714	Remote Similarity	NPC473791
0.569	Remote Similarity	NPC480078
0.569	Remote Similarity	NPC480071
0.5667	Remote Similarity	NPC309211
0.5667	Remote Similarity	NPC329838
0.5667	Remote Similarity	NPC480075
0.5667	Remote Similarity	NPC477010
0.5645	Remote Similarity	NPC320458
0.5625	Remote Similarity	NPC473905
0.5606	Remote Similarity	NPC477017
0.5606	Remote Similarity	NPC477016
0.5469	Remote Similarity	NPC322529
0.5424	Remote Similarity	NPC488246
0.5424	Remote Similarity	NPC144415
0.5424	Remote Similarity	NPC480080
0.5424	Remote Similarity	NPC607439
0.5424	Remote Similarity	NPC608157

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC234077 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6626
0.1-0.2	2474
0.2-0.3	50
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
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
		NPD

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