NPASS Compound

Natural Product: NPC262970

Natural Product ID	NPC262970
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZPBONBNZOMMCQS-FVSCCVIRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102150860
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 99104 0 0 0 0 0 0 0 0999 V2000 2.3913 -5.1646 2.1882 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3324 -4.9788 1.1483 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0173 -5.5912 1.5561 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8386 -5.5703 -0.1599 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4051 -4.5433 -1.1010 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4018 -3.5316 -1.5945 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9636 -2.1937 -1.8920 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8949 -1.2136 -2.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0360 -0.8515 -1.0249 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9905 -0.3158 -0.0208 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6609 0.7949 -0.6339 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 1.5222 0.0626 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8404 1.1201 1.2083 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2304 2.6058 -0.6518 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0925 3.4303 -0.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6113 3.4524 1.1613 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9767 3.8375 1.2508 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6355 4.0318 2.4276 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9613 3.8510 3.6185 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6405 3.4806 3.5406 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9735 3.2857 2.3409 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5721 4.0301 4.8464 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4867 -2.2160 -0.6670 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7650 -2.4113 -0.6057 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8344 -1.4408 -0.8538 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2558 -0.0955 -0.4733 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2989 0.9382 -0.3358 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3667 0.9850 -1.3664 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0240 0.6719 1.0008 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0830 1.6567 1.3046 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8722 3.0515 0.8211 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4893 3.3785 0.3884 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8094 4.0757 1.5912 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5289 4.4977 -0.6570 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6333 2.2657 -0.0522 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6940 2.5935 -1.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5987 1.5611 -1.0954 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0463 0.1353 -1.2995 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3105 0.0463 -2.8012 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8263 3.4315 -0.1577 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3991 -3.3686 -0.4426 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1560 -3.4727 0.8180 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7036 -4.0385 -2.8062 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5418 -4.1697 -2.7601 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3875 -4.3639 -3.9663 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -4.3020 2.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0213 -6.0695 1.9461 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9339 -5.2901 3.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6979 -4.8819 1.9760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4327 -6.1924 0.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2350 -6.3566 2.3501 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6481 -6.2969 0.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0455 -6.1319 -0.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6897 -5.1395 -2.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3640 -4.1069 -0.7677 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5681 -2.3162 -2.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7145 -1.8623 -1.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4048 -0.3121 -2.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2803 -1.7310 -3.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4836 0.0313 0.9255 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7732 -0.9554 0.3492 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9228 2.7638 -1.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4566 4.2104 -0.9115 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5256 3.9847 0.3328 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6789 4.3262 2.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0827 3.3305 4.4602 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 3.0751 2.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5762 3.9549 4.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1064 -3.4407 -0.3295 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1483 -1.4330 -1.9360 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7468 -1.6954 -0.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8466 -0.2478 0.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2454 0.1606 -2.0913 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4088 0.8387 -0.9699 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4112 1.9294 -1.9430 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2603 0.7231 1.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4443 -0.3330 1.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2533 1.6015 2.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0784 1.3135 0.8911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1644 3.7213 1.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0936 5.1424 1.6349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7168 3.9070 1.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1690 3.5024 2.4863 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5979 4.1495 -1.6803 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3163 5.2452 -0.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5643 5.0558 -0.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9339 2.0147 0.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1667 2.6819 -2.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2243 3.5651 -0.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1461 1.9125 -1.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2768 1.6846 -0.0173 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3896 0.4441 -3.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5912 -0.9468 -3.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1092 0.7425 -3.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1555 4.3352 -0.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1839 -4.3460 -0.5497 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7218 -2.9705 1.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2550 -3.2229 0.6771 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9603 -4.9669 -4.6437 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 1 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 19 22 1 0 9 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 6 31 40 1 0 23 41 1 0 41 42 1 0 6 43 1 6 43 44 2 0 43 45 1 0 42 2 1 0 41 6 1 0 38 9 1 0 21 16 1 0 38 26 1 0 35 27 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 10 60 1 0 10 61 1 0 14 62 1 0 15 63 1 0 17 64 1 0 18 65 1 0 20 66 1 0 21 67 1 0 22 68 1 0 24 69 1 0 25 70 1 0 25 71 1 0 26 72 1 1 28 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 30 79 1 0 31 80 1 1 33 81 1 0 33 82 1 0 33 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 1 36 88 1 0 36 89 1 0 37 90 1 0 37 91 1 0 39 92 1 0 39 93 1 0 39 94 1 0 40 95 1 0 41 96 1 1 42 97 1 0 42 98 1 0 45 99 1 0 M END

Standard InCHIKey	ZPBONBNZOMMCQS-FVSCCVIRSA-N
Standard InCHI	InChI=1S/C39H54O6/c1-34(2)19-20-38(33(43)44)21-22-39(24-45-32(42)14-9-25-7-10-26(40)11-8-25)27(28(38)23-34)12-13-30-36(5)17-16-31(41)35(3,4)29(36)15-18-37(30,39)6/h7-12,14,28-31,40-41H,13,15-24H2,1-6H3,(H,43,44)/b14-9-/t28-,29-,30+,31-,36-,37+,38-,39-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(COC(=O)/C=Cc4ccc(cc4)O)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.39	Volume:	666.047 ? Van der Waals volume.
Dense:	0.928	LogP:	4.645 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.92 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.46 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.175	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.9	Fsp³:	0.692
MCE-18:	162.273 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.992	Fluc inhibitor:	0.824 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.037 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.145	Promiscuous compounds:	0.058

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.563	MDCK Permeability:	-5.085
Pgp-inhibitor:	0.003	Pgp-substrate:	0.001
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.968	30% Bioavailability (F30%):	0.366
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023	MRP1:	0.739
Plasma Protein Binding (PPB):	97.844%	Volume Distribution (VD):	-0.393
Fu:	1.41% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.001
BSEP inhibitor:	0.955

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.189	CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.039	CYP3A4-substrate:	0.759
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.125 ? 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):

1.603

Half-life (T1/2):

1.58

ADMET: Toxicity

hERG Blockers:	0.115	hERG Blockers (10um):	0.131
Human Hepatotoxicity (H-HT):	0.699	Drug-induced Liver Injury (DILI):	0.17
AMES Toxicity:	0.336	Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.759	Skin Sensitization:	0.997
Carcinogencity:	0.506	Eye Corrosion:	0.0
Eye Irritation:	0.208	Respiratory Toxicity:	0.855
Drug-induced Neurotoxicity:	0.143	Ototoxicity:	0.585
Hematotoxicity:	0.072	Drug-induced Nephrotoxicity:	0.893
Genotoxicity:	0.761	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.731	Hek293 Cytotoxicity:	0.631
BCF:	1.116 ? 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:	4.451 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.789 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.329 ? 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
NPO12611	Lonicera korolkovii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520235]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1254564]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855442]
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192236]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26195800]
NPO40948	Vallaris glabra	Species	n.a.	n.a.	Leaves	n.a.	n.a.	PMID[29072457]
NPO40948	Vallaris glabra	Species	n.a.	n.a.	Stems	n.a.	n.a.	PMID[31820973]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8626242]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12611	Lonicera korolkovii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3376	Eriostemon brucei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10807	Melanothamnus somalensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7106	Talaromyces helicus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3376	Eriostemon brucei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18675	Pteris aquilina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11305	Garcinia cantleyana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12611	Lonicera korolkovii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10967	Parmelia gigas	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6430	Cercosporina kikuchii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10807	Melanothamnus somalensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11827	Zerynthia polyxena	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2644	Portulaca pilosa	Species	Portulacaceae	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
Cell line	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
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	600.0	nM	PMID[31820973]

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 NPC262970 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	7345
0.1-0.2	36736
0.2-0.3	5017
0.3-0.4	561
0.4-0.5	129
0.5-0.6	54
0.6-0.7	7
0.7-0.8	1
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8556	High Similarity	NPC206232
0.8556	High Similarity	NPC14515
0.8182	Intermediate Similarity	NPC198621
0.8182	Intermediate Similarity	NPC216940
0.809	Intermediate Similarity	NPC54627
0.809	Intermediate Similarity	NPC249817
0.734	Intermediate Similarity	NPC475482
0.7234	Intermediate Similarity	NPC606782
0.7065	Intermediate Similarity	NPC475627
0.697	Remote Similarity	NPC310729
0.697	Remote Similarity	NPC150310
0.6765	Remote Similarity	NPC53520
0.6429	Remote Similarity	NPC605663
0.6392	Remote Similarity	NPC22676
0.6238	Remote Similarity	NPC475311
0.62	Remote Similarity	NPC132126
0.598	Remote Similarity	NPC479747
0.598	Remote Similarity	NPC479746
0.598	Remote Similarity	NPC482049
0.598	Remote Similarity	NPC482050
0.5918	Remote Similarity	NPC18982
0.59	Remote Similarity	NPC488215
0.5882	Remote Similarity	NPC480946
0.5882	Remote Similarity	NPC130577
0.5882	Remote Similarity	NPC142415
0.5882	Remote Similarity	NPC102683
0.5882	Remote Similarity	NPC198664
0.581	Remote Similarity	NPC479740
0.581	Remote Similarity	NPC479741
0.58	Remote Similarity	NPC475457
0.5644	Remote Similarity	NPC271494
0.5556	Remote Similarity	NPC601567
0.5556	Remote Similarity	NPC606631
0.549	Remote Similarity	NPC171007
0.549	Remote Similarity	NPC190849
0.5472	Remote Similarity	NPC610795
0.5376	Remote Similarity	NPC474727
0.537	Remote Similarity	NPC473680
0.5333	Remote Similarity	NPC172311
0.5333	Remote Similarity	NPC479744
0.5333	Remote Similarity	NPC482052
0.5283	Remote Similarity	NPC304110
0.5283	Remote Similarity	NPC25491
0.5283	Remote Similarity	NPC27518
0.5283	Remote Similarity	NPC611516
0.5234	Remote Similarity	NPC479739
0.5234	Remote Similarity	NPC178093
0.5196	Remote Similarity	NPC43353
0.5185	Remote Similarity	NPC473773
0.5185	Remote Similarity	NPC475579
0.5185	Remote Similarity	NPC324798
0.5185	Remote Similarity	NPC479742
0.5165	Remote Similarity	NPC228784
0.5165	Remote Similarity	NPC324341
0.5165	Remote Similarity	NPC298554
0.5165	Remote Similarity	NPC29765
0.5165	Remote Similarity	NPC601810
0.5149	Remote Similarity	NPC478270
0.5149	Remote Similarity	NPC478271
0.5138	Remote Similarity	NPC475454
0.5138	Remote Similarity	NPC473579
0.5111	Remote Similarity	NPC270768
0.5111	Remote Similarity	NPC59263
0.5111	Remote Similarity	NPC182797
0.5111	Remote Similarity	NPC210106
0.5111	Remote Similarity	NPC52169
0.5111	Remote Similarity	NPC488562
0.5048	Remote Similarity	NPC486700
0.5048	Remote Similarity	NPC275312
0.5047	Remote Similarity	NPC488214

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC262970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3177
0.1-0.2	5845
0.2-0.3	124
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7234	Intermediate Similarity	NPD8166	Discontinued

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