NPASS Compound

Natural Product: NPC204465

Natural Product ID	NPC204465
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DXDSZUXZQIKMRQ-GMZGOHOASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	13945472
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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 75 79 0 0 0 0 0 0 0 0999 V2000 -3.2370 2.2749 0.5868 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4745 1.4715 -0.4825 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5739 1.0448 -1.4681 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6525 0.2463 -0.8527 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1300 -0.8244 0.0585 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5227 -0.5227 1.5020 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6329 -1.0070 -0.0640 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8739 0.3008 0.1981 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4198 0.0618 -0.0911 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2155 -0.3909 -1.5440 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0701 -1.0529 0.7632 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5457 -1.3361 0.6276 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3736 -0.0776 0.6815 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4404 0.4052 2.1574 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7686 -0.4196 0.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3360 -1.4623 1.0851 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6561 -1.8229 0.8590 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4229 -1.1458 -0.0720 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8547 -0.1055 -0.7733 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5310 0.2363 -0.5291 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9303 1.3258 -1.2805 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6182 1.9340 -2.1196 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5204 1.6490 -0.9983 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7972 1.0098 -0.1063 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3423 1.3610 0.0677 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0595 2.1201 1.3083 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1026 2.1914 -1.1135 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5692 2.3532 -1.2515 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6168 0.6333 -1.7580 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6217 0.2554 -2.9483 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3274 1.7482 -1.3577 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7534 -1.5288 -0.2820 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2128 -2.8736 1.5741 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7637 -2.1243 -0.2707 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0652 -3.0798 -0.6224 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1487 -2.2944 -0.1911 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7576 -3.5316 -0.5039 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8461 3.3351 0.5517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9733 1.9244 1.6108 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3025 2.3414 0.4153 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0285 2.0265 -1.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1849 0.5854 -2.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4618 0.8570 -0.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2014 -0.2569 -1.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0901 -1.3416 1.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6430 -0.3398 2.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2122 0.3578 1.4960 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4010 -1.4028 -1.0528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3907 -1.7357 0.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9308 0.3955 1.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3583 -1.5080 -1.5904 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 -0.2217 -1.8077 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8495 0.1362 -2.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2555 -0.9297 1.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4243 -1.9914 0.3799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7647 -1.9317 -0.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8202 -1.9504 1.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4848 0.3642 2.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9950 1.3393 2.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1104 -0.3187 2.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7958 -2.0401 1.8358 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1574 2.4770 -1.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4748 1.5646 2.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9897 2.5179 1.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5143 3.0737 1.0675 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3821 3.1873 -0.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3551 1.7351 -2.0137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7744 2.3534 -2.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8326 3.4240 -0.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0660 2.1556 -1.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2620 -1.8292 0.5633 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3084 -3.7838 1.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4048 -4.3515 0.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5877 -3.8497 -1.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8538 -3.3912 -0.2883 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 1 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 19 29 1 0 29 30 2 0 29 31 1 0 18 32 1 0 17 33 1 0 5 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 28 2 1 0 8 2 1 0 25 9 1 0 24 13 1 0 20 15 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 6 45 1 0 6 46 1 0 6 47 1 0 7 48 1 0 7 49 1 0 8 50 1 1 10 51 1 0 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 12 56 1 0 12 57 1 0 14 58 1 0 14 59 1 0 14 60 1 0 16 61 1 0 23 62 1 0 26 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 31 70 1 0 32 71 1 0 33 72 1 0 37 73 1 0 37 74 1 0 37 75 1 0 M END

Standard InCHIKey	DXDSZUXZQIKMRQ-GMZGOHOASA-N
Standard InCHI	InChI=1S/C30H38O7/c1-26-7-8-27(2,25(36)37-6)15-20(26)30(5)12-10-28(3)16-13-18(32)23(33)22(24(34)35)21(16)17(31)14-19(28)29(30,4)11-9-26/h13-14,20,32-33H,7-12,15H2,1-6H3,(H,34,35)/t20-,26-,27-,28+,29-,30+/m1/s1
SMILES	C[C@@]12CC[C@](C)(C[C@H]2[C@]2(C)CC[C@@]3(C)c4cc(c(c(c4C(=O)C=C3[C@@]2(C)CC1)C(=O)O)O)O)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	510.26	Volume:	527.73 ? Van der Waals volume.
Dense:	0.967	LogP:	2.551 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.22 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.07 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	29.0
TPSA:	121.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.341	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.809	Fsp³:	0.633
MCE-18:	141.224 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.698	Fluc inhibitor:	0.545 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.5 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.235 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.192	Promiscuous compounds:	0.32

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.263	MDCK Permeability:	-4.815
Pgp-inhibitor:	0.021	Pgp-substrate:	0.003
PAMPA:	0.997 ? 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%):	0.756	30% Bioavailability (F30%):	0.337
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418	MRP1:	1.0
Plasma Protein Binding (PPB):	97.33%	Volume Distribution (VD):	-0.115
Fu:	2.176% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.082
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.095	CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.526
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.521 ? 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):

2.686

Half-life (T1/2):

1.344

ADMET: Toxicity

hERG Blockers:	0.166	hERG Blockers (10um):	0.186
Human Hepatotoxicity (H-HT):	0.808	Drug-induced Liver Injury (DILI):	0.932
AMES Toxicity:	0.249	Rat Oral Acute Toxicity:	0.589
Maximum Recommended Daily Dose:	0.477	Skin Sensitization:	0.947
Carcinogencity:	0.341	Eye Corrosion:	0.0
Eye Irritation:	0.524	Respiratory Toxicity:	0.865
Drug-induced Neurotoxicity:	0.259	Ototoxicity:	0.623
Hematotoxicity:	0.589	Drug-induced Nephrotoxicity:	0.858
Genotoxicity:	0.972	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.314	Hek293 Cytotoxicity:	0.168
BCF:	0.617 ? 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:	3.583 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.252 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.621 ? 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
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	Tanzania	n.a.	PMID[11430019]
NPO26894	Kokoona zeylanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678653]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[12027753]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502337]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16557460]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17960072]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	root	n.a.	PMID[17960072]
NPO25915	Sinularia dura	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18630962]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
NPO25915	Sinularia dura	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24128077]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26221771]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
NPO783	Pholiota squarrosa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15815	Macrophomina phaseolina	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26894	Kokoona zeylanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6076	Pentzia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26920	Liatris punctata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2642	Maytenus apurimacensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27299	Litsea gracilipes	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27299	Litsea gracilipes	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20434	Tolypocladium ophioglossoides	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15601	Pyrus x bretschneideri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27299	Litsea gracilipes	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6076	Pentzia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1358	Iris pallida	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3588	Crucianella maritima	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1019	Citrus hybr	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26920	Liatris punctata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27056	Sageretia thea	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27245	Lecanora glaucoma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2642	Maytenus apurimacensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27299	Litsea gracilipes	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3835	Reticulitermes flavipes	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5923	Bidens cernua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15769	Solidago chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26894	Kokoona zeylanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8278	Perenniporia ochroleuca	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15815	Macrophomina phaseolina	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25915	Sinularia dura	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24527	Plazia daphnoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25151	Euphorbia cheiradenia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15601	Pyrus x bretschneideri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20434	Tolypocladium ophioglossoides	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2309	Achillea micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO783	Pholiota squarrosa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6313	Phormidium sp	Species	Oscillatoriaceae	Bacteria	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 NPC204465 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	9980
0.1-0.2	38446
0.2-0.3	1413
0.3-0.4	10
0.4-0.5	5
0.5-0.6	3
0.6-0.7	1
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	Natural Product ID
0.7436	Intermediate Similarity	NPC10842
0.6883	Remote Similarity	NPC184935
0.5926	Remote Similarity	NPC476282
0.5506	Remote Similarity	NPC185617
0.5227	Remote Similarity	NPC606106

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC204465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3747
0.1-0.2	5363
0.2-0.3	40
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