NPASS Compound

Natural Product: NPC473479

Natural Product ID	NPC473479
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Guttiferone B
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL442991
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

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 107109 0 0 0 0 0 0 0 0999 V2000 1.3184 -6.1841 0.0496 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1407 -5.7103 -0.7088 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1104 -4.4766 -1.1662 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2729 -3.5648 -0.9107 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7345 -2.3736 -0.1731 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1249 -2.8543 1.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7675 -3.2043 2.0771 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3879 -2.9177 1.1494 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0482 -1.8729 0.6827 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2912 -0.9353 -0.1868 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3630 -1.7312 -1.0138 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4287 -1.8810 -2.2125 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1417 0.0283 -0.9543 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9308 0.9657 -0.1404 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7130 2.2992 -0.2959 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4899 3.2637 0.5076 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3200 4.2267 -0.2618 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5055 5.0879 -1.1582 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7340 5.0501 -2.4628 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9099 5.9181 -3.3443 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7736 4.1838 -3.0736 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6973 2.7094 -1.2652 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3400 -0.1381 0.7421 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0462 0.0158 0.0892 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7586 -1.2781 0.0240 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6512 -1.6457 1.1456 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6097 -1.2752 -1.2570 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6832 1.1276 0.8538 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0205 1.5552 0.4605 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2722 2.8124 0.0353 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6550 3.1572 -0.3419 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2195 4.2825 0.4971 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6126 4.5954 0.0792 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6247 4.4903 0.9283 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3676 4.0543 2.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0006 4.8131 0.4684 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2060 3.8086 -0.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3747 -1.6871 1.0162 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0003 -4.1264 1.6327 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1738 -4.9772 2.2313 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3409 -4.5995 1.5953 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7841 -5.5333 2.5406 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0100 -6.1214 2.5053 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8826 -5.7892 1.4821 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5180 -4.8869 0.5231 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2523 -4.3165 0.6059 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4059 -4.5584 -0.5061 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1226 -6.4081 1.4815 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0119 -6.6044 -0.9629 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5165 -5.5818 0.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2164 -6.0520 -0.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1893 -7.2520 0.3303 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7490 -4.1265 -1.7223 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0316 -4.0542 -0.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6765 -3.3244 -1.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6309 0.4933 -1.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9242 -0.6343 -1.4550 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6853 0.7261 0.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7256 3.8731 1.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0996 2.7755 1.2916 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1720 3.7634 -0.7910 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7875 4.9301 0.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7342 5.7421 -0.7333 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5130 6.8128 -2.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0421 5.3511 -3.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5353 6.2131 -4.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7974 4.5792 -2.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7536 3.1476 -2.6887 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6009 4.1053 -4.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1244 2.6552 -2.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7204 2.1857 -1.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4200 3.7953 -1.1158 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7226 0.8968 0.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2759 -0.5616 1.7398 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8342 0.3616 -0.9519 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2993 -1.3224 2.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7651 -2.7782 1.0971 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7042 -1.3023 1.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2543 -2.1702 -1.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1559 -0.3267 -1.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9291 -1.3292 -2.1574 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7076 0.7996 1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9505 1.9929 0.8740 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8826 0.9130 0.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3572 2.3114 -0.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6558 3.5072 -1.3983 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1791 4.0877 1.5759 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6218 5.2121 0.3247 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7716 4.9145 -0.9504 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3273 4.0722 2.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7044 4.8067 2.8179 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9063 3.0504 2.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4430 5.5177 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9688 5.2511 -0.5365 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5793 3.8528 0.5064 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6348 3.9378 0.8929 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6496 4.7985 -0.2782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5221 3.5772 -0.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1322 -1.4721 0.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0913 -5.7776 3.3303 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2810 -6.8329 3.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0092 -3.6776 -0.2209 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1293 -5.2387 -0.7412 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1738 -7.4138 1.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9165 -6.0309 -1.2292 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7444 -7.3686 -1.7292 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1875 -7.1757 -0.0248 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 5 4 1 6 5 6 1 0 6 7 2 0 6 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 2 0 10 13 1 6 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 3 19 20 1 0 19 21 1 0 15 22 1 0 10 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 3 34 35 1 0 34 36 1 0 30 37 1 0 9 38 1 0 8 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 45 47 1 0 44 48 1 0 2 49 1 0 11 5 1 0 46 41 1 0 25 5 1 0 1 50 1 0 1 51 1 0 1 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 13 56 1 0 13 57 1 0 14 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 0 20 64 1 0 20 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 22 72 1 0 23 73 1 0 23 74 1 0 24 75 1 6 26 76 1 0 26 77 1 0 26 78 1 0 27 79 1 0 27 80 1 0 27 81 1 0 28 82 1 0 28 83 1 0 29 84 1 0 31 85 1 0 31 86 1 0 32 87 1 0 32 88 1 0 33 89 1 0 35 90 1 0 35 91 1 0 35 92 1 0 36 93 1 0 36 94 1 0 36 95 1 0 37 96 1 0 37 97 1 0 37 98 1 0 38 99 1 0 42100 1 0 43101 1 0 46102 1 0 47103 1 0 48104 1 0 49105 1 0 49106 1 0 49107 1 0 M END

Standard InCHIKey	OGBLTDAGYQWRIK-XKLZQMNUSA-N
Standard InCHI	InChI=1S/C43H58O6/c1-27(2)13-11-15-30(7)17-19-33-26-42(23-22-31(8)16-12-14-28(3)4)38(47)36(37(46)32-18-20-34(44)35(45)25-32)39(48)43(40(42)49,41(33,9)10)24-21-29(5)6/h13-14,17-18,20-22,25,33,44-45,47H,11-12,15-16,19,23-24,26H2,1-10H3/b30-17+,31-22+/t33-,42-,43+/m1/s1
SMILES	CC(=CC[C@]12C(=O)C(=C([C@@](C1=O)(C/C=C(/CCC=C(C)C)C)C[C@H](C2(C)C)C/C=C(/CCC=C(C)C)C)O)C(=O)c1ccc(c(c1)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	670.42	Volume:	747.718 ? Van der Waals volume.
Dense:	0.897	LogP:	8.837 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.902 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.28 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	24.0
TPSA:	111.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.06	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.522	Fsp³:	0.512
MCE-18:	100.923 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.999	Fluc inhibitor:	0.125 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.056 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.486 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.632	Promiscuous compounds:	0.218

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.835	MDCK Permeability:	-4.699
Pgp-inhibitor:	0.208	Pgp-substrate:	0.0
PAMPA:	0.673 ? 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%):	0.001	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.867

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.991
Plasma Protein Binding (PPB):	93.24%	Volume Distribution (VD):	0.079
Fu:	7.229% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.364	BCRP inhibitor:	0.0
BSEP inhibitor:	0.199

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.372	CYP2C19-substrate:	0.015
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.988
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	1.0 ? 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):

5.633

Half-life (T1/2):

1.152

ADMET: Toxicity

hERG Blockers:	0.061	hERG Blockers (10um):	0.389
Human Hepatotoxicity (H-HT):	0.855	Drug-induced Liver Injury (DILI):	0.533
AMES Toxicity:	0.075	Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.402	Skin Sensitization:	0.995
Carcinogencity:	0.159	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.988
Drug-induced Neurotoxicity:	0.422	Ototoxicity:	0.985
Hematotoxicity:	0.572	Drug-induced Nephrotoxicity:	0.982
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.963	Hek293 Cytotoxicity:	0.384
BCF:	1.98 ? 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:	6.194 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.57 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	8.748 ? 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
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724839]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113969]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	leaves	Bobai, Guangxi Province, China	2005-Dec	PMID[24679044]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	Barks	n.a.	n.a.	PMID[24754786]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	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	1

Activity Type	# Activity
Others	1

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
NPT2	Others	Unspecified	n.a.	IC50	=	53000.0	nM	PMID[24411199]

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 NPC473479 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	7876
0.1-0.2	39474
0.2-0.3	2368
0.3-0.4	61
0.4-0.5	30
0.5-0.6	7
0.6-0.7	17
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC50615
1.0	High Similarity	NPC141650
0.9844	High Similarity	NPC114333
0.9844	High Similarity	NPC28592
0.9692	High Similarity	NPC165191
0.9692	High Similarity	NPC177501
0.9538	High Similarity	NPC51531
0.8462	Intermediate Similarity	NPC149773
0.8429	Intermediate Similarity	NPC23667
0.8429	Intermediate Similarity	NPC157284
0.831	Intermediate Similarity	NPC5014
0.7534	Intermediate Similarity	NPC30846
0.7465	Intermediate Similarity	NPC289358
0.7465	Intermediate Similarity	NPC4289
0.7465	Intermediate Similarity	NPC42384
0.7361	Intermediate Similarity	NPC46242
0.7361	Intermediate Similarity	NPC91887
0.7361	Intermediate Similarity	NPC93556
0.7308	Intermediate Similarity	NPC482617
0.7308	Intermediate Similarity	NPC482616
0.7297	Intermediate Similarity	NPC469857
0.7297	Intermediate Similarity	NPC245760
0.726	Intermediate Similarity	NPC297797
0.7237	Intermediate Similarity	NPC25736
0.6962	Remote Similarity	NPC482618
0.6883	Remote Similarity	NPC471971
0.6883	Remote Similarity	NPC471972
0.6883	Remote Similarity	NPC469855
0.6571	Remote Similarity	NPC259400
0.6571	Remote Similarity	NPC130591
0.6571	Remote Similarity	NPC234637
0.6538	Remote Similarity	NPC482621
0.6375	Remote Similarity	NPC469856
0.6364	Remote Similarity	NPC198803
0.6329	Remote Similarity	NPC294330
0.6329	Remote Similarity	NPC479151
0.6296	Remote Similarity	NPC471970
0.625	Remote Similarity	NPC469854
0.625	Remote Similarity	NPC603871
0.6203	Remote Similarity	NPC479148
0.6118	Remote Similarity	NPC482620
0.5976	Remote Similarity	NPC237441
0.5946	Remote Similarity	NPC611064
0.5921	Remote Similarity	NPC473779
0.575	Remote Similarity	NPC48949
0.5714	Remote Similarity	NPC479146
0.5556	Remote Similarity	NPC473527
0.5116	Remote Similarity	NPC482619

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473479 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3797
0.1-0.2	5294
0.2-0.3	59
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