NPASS Compound

Natural Product: NPC93556

Natural Product ID	NPC93556
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QDKLRKZQSOQWJQ-AKAMJVKKSA-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:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 94 96 0 0 0 0 0 0 0 0999 V2000 6.8648 1.0391 3.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5094 0.3966 3.2612 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4248 1.0135 2.8259 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0416 0.5711 2.8726 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2701 0.6419 1.5775 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8899 0.2210 1.7368 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1046 0.1745 0.6813 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1718 -0.7169 -0.4632 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5318 -2.0933 -0.3512 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1776 -2.9563 -1.2875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1764 -4.3628 -1.4471 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6379 -5.3839 -1.2140 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0311 -5.2360 -0.7561 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1066 -6.7533 -1.4292 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0322 -1.9858 -0.4518 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6576 -2.9516 0.5792 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6140 -2.3485 -1.7680 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3919 -0.6149 0.0706 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7569 -0.4771 0.6876 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9001 -0.7701 -0.1993 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8004 0.1556 -0.5021 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9273 -0.1858 -1.3942 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6785 1.5288 0.0511 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3108 0.4576 -0.9525 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9455 0.4766 -2.0123 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3931 1.6245 -0.7039 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6442 1.5403 0.3663 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3547 2.5886 1.1808 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3666 2.7341 -1.6078 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2750 2.6299 -2.5620 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5449 3.8998 -1.6420 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6061 4.1689 -0.9729 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2621 5.4151 -1.0466 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7557 6.4250 -1.8141 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4053 6.1940 -2.5094 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0257 4.9793 -2.4229 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9636 7.2068 -3.3158 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3870 7.6611 -1.8998 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4370 -0.4241 1.2026 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5589 -0.6513 2.3423 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0862 0.3467 0.4309 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1330 -0.4869 0.3866 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8833 1.0457 -0.8988 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4960 -0.9244 3.9168 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 2.1120 2.8888 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3203 0.6036 2.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5089 0.8710 3.9853 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5982 2.0084 2.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9090 -0.4504 3.3044 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5105 1.2476 3.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1529 1.8364 1.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9123 -0.8282 2.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4050 0.7969 2.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1024 -0.3135 -1.4635 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2462 -1.0711 -0.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3242 -2.3856 0.7223 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1886 -2.4684 -2.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2733 -2.9505 -0.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1682 -4.6149 -1.7793 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0088 -4.6212 0.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7148 -4.8342 -1.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4167 -6.2230 -0.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7678 -7.5286 -0.9967 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8848 -6.8327 -0.9133 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1058 -6.9695 -2.5092 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9978 -3.8442 0.6998 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7104 -2.5112 1.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6008 -3.3688 0.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3371 -1.6674 -2.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1285 -3.3645 -1.7289 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8345 -2.4874 -2.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8893 -0.9312 1.6704 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8188 0.6400 0.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0588 -1.7485 -0.6305 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6610 0.6534 -1.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4373 -1.1299 -1.0865 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5236 -0.2978 -2.4194 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7113 1.5580 1.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7163 1.9601 -0.3519 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5217 2.1646 -0.3469 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9660 3.0143 1.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0769 3.4137 -0.4052 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1657 5.5788 -0.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9242 4.8631 -2.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8519 7.5740 -3.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9178 8.5061 -1.5926 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6826 -0.6276 -0.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4352 -1.0511 1.2398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8771 1.3999 -1.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2675 0.4161 -1.7467 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5641 1.9471 -0.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6207 -1.4858 3.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4660 -0.8422 5.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4001 -1.5287 3.6821 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 4 5 1 0 5 6 1 0 7 6 1 1 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 3 12 13 1 0 12 14 1 0 9 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 1 19 20 1 0 20 21 2 3 21 22 1 0 21 23 1 0 18 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 26 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 35 37 1 0 34 38 1 0 18 39 1 0 39 40 2 0 5 41 1 0 41 42 2 0 41 43 1 0 2 44 1 0 27 7 1 0 36 31 1 0 39 7 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 6 6 52 1 0 6 53 1 0 8 54 1 0 8 55 1 0 9 56 1 1 10 57 1 0 10 58 1 0 11 59 1 0 13 60 1 0 13 61 1 0 13 62 1 0 14 63 1 0 14 64 1 0 14 65 1 0 16 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 17 71 1 0 19 72 1 0 19 73 1 0 20 74 1 0 22 75 1 0 22 76 1 0 22 77 1 0 23 78 1 0 23 79 1 0 23 80 1 0 28 81 1 0 32 82 1 0 33 83 1 0 36 84 1 0 37 85 1 0 38 86 1 0 42 87 1 0 42 88 1 0 43 89 1 0 43 90 1 0 43 91 1 0 44 92 1 0 44 93 1 0 44 94 1 0 M END

Standard InCHIKey	QDKLRKZQSOQWJQ-AKAMJVKKSA-N
Standard InCHI	InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-40,42H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37+,38-/m1/s1
SMILES	CC(=CC[C@H](C[C@]12C[C@H](CC=C(C)C)C(C)(C)[C@](CC=C(C)C)(C(=O)C(=C1O)C(=O)c1ccc(c(c1)O)O)C2=O)C(=C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.36	Volume:	663.875 ? Van der Waals volume.
Dense:	0.907	LogP:	6.176 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.74 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.766 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
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:	0.077	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.607	Fsp³:	0.5
MCE-18:	101.614 ? 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:	0.991	Fluc inhibitor:	0.11 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.09 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.435 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.636	Promiscuous compounds:	0.235

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.894	MDCK Permeability:	-4.726
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	0.989 ? 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%):	0.002	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.876

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028	MRP1:	0.991
Plasma Protein Binding (PPB):	93.689%	Volume Distribution (VD):	0.135
Fu:	7.279% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.752
OATP1B3 inhibitor:	0.089	BCRP inhibitor:	0.002
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.558
CYP2C19-inhibitor:	0.794	CYP2C19-substrate:	0.015
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.05	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.91
HLM stability:	0.988 ? 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):

6.422

Half-life (T1/2):

1.171

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.261
Human Hepatotoxicity (H-HT):	0.642	Drug-induced Liver Injury (DILI):	0.722
AMES Toxicity:	0.766	Rat Oral Acute Toxicity:	0.911
Maximum Recommended Daily Dose:	0.186	Skin Sensitization:	0.994
Carcinogencity:	0.468	Eye Corrosion:	0.0
Eye Irritation:	0.019	Respiratory Toxicity:	0.886
Drug-induced Neurotoxicity:	0.296	Ototoxicity:	0.958
Hematotoxicity:	0.629	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.934	Hek293 Cytotoxicity:	0.359
BCF:	1.838 ? 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:	5.499 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.716 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.495 ? 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
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4020(01)89039-6]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421754]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193024]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[15679329]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16441091]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[16562837]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125225]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318032]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[19961178]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	palau	n.a.	PMID[20078073]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078073]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	seeds and rinds	n.a.	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21028890]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21028890]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428459]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23830699]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27213234]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27548648]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29989811]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30346758]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32191460]
NPO4768	Lunaria annua	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39202882]
NPO6556	Garcinia intermedia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4768	Lunaria annua	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3858	Pimpinella magna	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1970	Rubus palmatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10493	Casearia thwaitesii	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3858	Pimpinella magna	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4768	Lunaria annua	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO104	Hymenodictyon floribundum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6556	Garcinia intermedia	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	14
EC50	2
MIC	1

Activity Type	# Activity
Individual protein	8
Cell line	5
Organism	3
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	IC50	=	500.0	nM	PMID[29989811]
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	IC50	=	7000.0	nM	PMID[28505447]
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	IC50	=	7000.0	nM	PMID[30297119]
NPT1080	Individual protein	Histone acetyltransferase PCAF	Homo sapiens	IC50	=	5000.0	nM	PMID[30297119]
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	IC50	=	7000.0	nM	PMID[31910017]
NPT1044	Individual protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	101200.0	nM	PMID[31618025]
NPT322	Individual protein	DNA topoisomerase II beta	Homo sapiens	IC50	=	101200.0	nM	PMID[31618025]
NPT956	Individual protein	Prostaglandin E synthase	Homo sapiens	IC50	=	300.0	nM	PMID[29329790]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	3460.0	nM	PMID[33325699]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	2870.0	nM	PMID[33325699]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	2860.0	nM	PMID[33325699]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	2130.0	nM	PMID[33325699]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	2430.0	nM	PMID[33325699]
NPT20	Organism	Candida albicans	Candida albicans	EC50	=	30000.0	nM	PMID[28051303]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	7.0	ug.mL-1	PMID[32791400]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	EC50	=	1800.0	nM	PMID[31585276]
NPT2	Others	Unspecified	n.a.	IC50	=	0.04305	ug.mL-1	PMID[31255927]

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 NPC93556 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	7480
0.1-0.2	40665
0.2-0.3	1587
0.3-0.4	42
0.4-0.5	21
0.5-0.6	21
0.6-0.7	14
0.7-0.8	0
0.8-0.85	2
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46242
1.0	High Similarity	NPC91887
0.8939	High Similarity	NPC469857
0.8939	High Similarity	NPC245760
0.8676	High Similarity	NPC471971
0.8676	High Similarity	NPC471972
0.8676	High Similarity	NPC469855
0.8636	High Similarity	NPC297797
0.8571	High Similarity	NPC149773
0.8551	High Similarity	NPC469856
0.8529	High Similarity	NPC294330
0.8429	Intermediate Similarity	NPC471970
0.8406	Intermediate Similarity	NPC469854
0.7778	Intermediate Similarity	NPC237441
0.7639	Intermediate Similarity	NPC603871
0.7606	Intermediate Similarity	NPC165191
0.7606	Intermediate Similarity	NPC30846
0.7606	Intermediate Similarity	NPC177501
0.7465	Intermediate Similarity	NPC114333
0.7465	Intermediate Similarity	NPC28592
0.7465	Intermediate Similarity	NPC51531
0.7361	Intermediate Similarity	NPC473479
0.7361	Intermediate Similarity	NPC50615
0.7361	Intermediate Similarity	NPC141650
0.7042	Intermediate Similarity	NPC289358
0.7042	Intermediate Similarity	NPC4289
0.7042	Intermediate Similarity	NPC42384
0.7027	Intermediate Similarity	NPC479151
0.6667	Remote Similarity	NPC479148
0.6618	Remote Similarity	NPC259400
0.6618	Remote Similarity	NPC130591
0.6618	Remote Similarity	NPC234637
0.6538	Remote Similarity	NPC479146
0.6494	Remote Similarity	NPC5014
0.6429	Remote Similarity	NPC611064
0.6389	Remote Similarity	NPC473779
0.6364	Remote Similarity	NPC23667
0.6364	Remote Similarity	NPC157284
0.6184	Remote Similarity	NPC473527
0.6154	Remote Similarity	NPC482621
0.6098	Remote Similarity	NPC482617
0.6098	Remote Similarity	NPC482616
0.5976	Remote Similarity	NPC482618
0.5974	Remote Similarity	NPC198803
0.5443	Remote Similarity	NPC479147
0.5422	Remote Similarity	NPC264229
0.5422	Remote Similarity	NPC25736
0.5422	Remote Similarity	NPC46549
0.5422	Remote Similarity	NPC606601
0.5395	Remote Similarity	NPC474715
0.5375	Remote Similarity	NPC48949
0.5244	Remote Similarity	NPC8493
0.5244	Remote Similarity	NPC469375
0.5244	Remote Similarity	NPC110855
0.5244	Remote Similarity	NPC144247
0.519	Remote Similarity	NPC600618
0.5176	Remote Similarity	NPC294679
0.5176	Remote Similarity	NPC145301
0.5176	Remote Similarity	NPC302044
0.5176	Remote Similarity	NPC600911
0.5119	Remote Similarity	NPC482619
0.5116	Remote Similarity	NPC231479
0.5059	Remote Similarity	NPC7464

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC93556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3481
0.1-0.2	5620
0.2-0.3	49
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