NPASS Compound

Natural Product: NPC47063

Natural Product ID	NPC47063
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oblonganoside J
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2253397
PubChem CID	16109699
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 109115 0 0 0 0 0 0 0 0999 V2000 9.6721 0.5111 -1.7791 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6645 -0.3174 -0.6577 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2163 -0.5663 -0.2902 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6235 -1.1773 -1.3833 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2429 -1.4060 -1.1712 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6284 -0.0047 -1.0025 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2948 0.5260 0.2530 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6453 0.6723 -0.0060 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6799 1.7800 0.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2333 1.5258 1.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4744 1.0409 -0.1862 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1847 -0.1639 -0.7707 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4222 -0.6670 -1.9630 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9955 -1.0020 -1.6739 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3020 -0.1577 -0.6851 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1634 0.5209 0.3233 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3511 1.5068 1.0802 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0032 1.0241 1.3799 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5213 -0.1404 0.9551 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3116 -1.0167 0.1253 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1248 -1.9055 1.0427 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4958 -1.9237 -0.7696 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9333 -1.5949 -0.8426 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6251 -1.4445 0.5164 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9340 -0.4377 1.3752 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0472 -0.6177 2.8410 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0512 0.3686 3.4604 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8079 -0.2370 3.4124 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3620 -1.9719 3.3310 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2797 -2.7801 2.4600 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -2.8123 1.0796 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1619 -2.8317 3.6683 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9985 -0.9999 0.1277 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9707 -1.7140 0.4124 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2346 0.1862 -0.5428 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5507 0.5558 -0.8840 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7370 0.6586 -2.2684 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1129 0.6287 -2.4841 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4416 0.5175 -3.9582 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9311 1.5924 -4.6641 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8015 1.8188 -1.9102 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0107 2.5962 -0.9154 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9687 1.8275 -0.1829 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3331 1.4982 1.1277 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4709 3.7684 -1.4909 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0735 1.4798 -1.3927 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4222 0.8817 -1.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3898 2.1861 -1.1276 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0380 0.7855 -2.1947 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6953 1.4692 -1.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0879 -1.3009 -0.9946 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2428 0.1084 0.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1400 -1.2690 0.5623 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0730 -1.9797 -0.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9011 -1.9061 -2.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1257 -0.2683 1.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1536 1.9596 1.7830 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8944 2.6819 0.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7109 2.3530 1.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1889 0.6650 1.7729 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0677 -0.9671 0.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9086 -1.6063 -2.3013 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4878 0.0311 -2.8313 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4459 -0.9022 -2.6589 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8878 -2.0869 -1.4199 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4627 -0.2687 1.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8481 1.7235 2.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2587 2.4954 0.5880 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6526 1.6674 2.0052 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5781 -2.8896 1.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0966 -2.2047 0.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2148 -1.5185 2.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1031 -1.9073 -1.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4124 -3.0067 -0.4571 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4477 -2.4955 -1.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2254 -0.7626 -1.4935 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4624 0.5417 1.1361 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0270 1.3381 2.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7883 0.5371 4.5258 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0697 -0.1001 3.4778 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8609 -0.3354 4.4121 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9176 -1.8612 4.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3129 -2.4420 2.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2178 -3.8339 2.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8150 -3.4237 0.9731 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4948 -3.3598 0.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3940 -3.4758 4.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9822 -3.5679 2.8304 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2685 -2.2212 3.8105 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2561 -0.2299 -0.5347 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5161 -0.3134 -2.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9818 -0.4007 -4.4067 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5356 0.3988 -4.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1830 1.4887 -5.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0339 2.5229 -2.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7401 2.9817 -0.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0597 2.4685 -0.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9828 2.1868 1.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2067 4.4516 -1.5812 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5594 2.3193 -1.1796 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8226 1.8900 -1.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3419 0.5842 -2.4734 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5974 0.9128 -1.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8248 2.9971 -0.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4385 2.5990 -1.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0713 1.9280 -2.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2447 1.0646 -2.8820 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8197 0.2614 -2.8227 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5802 1.7107 -1.8373 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 7 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 2 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 1 26 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 24 33 1 6 33 34 2 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 15 47 1 6 11 48 1 6 6 49 1 6 8 3 1 0 16 11 1 0 25 19 1 0 43 36 1 0 12 6 1 0 20 15 1 0 31 24 1 0 1 50 1 0 2 51 1 0 2 52 1 0 3 53 1 1 5 54 1 0 5 55 1 0 7 56 1 1 9 57 1 0 9 58 1 0 10 59 1 0 10 60 1 0 12 61 1 1 13 62 1 0 13 63 1 0 14 64 1 0 14 65 1 0 16 66 1 1 17 67 1 0 17 68 1 0 18 69 1 0 21 70 1 0 21 71 1 0 21 72 1 0 22 73 1 0 22 74 1 0 23 75 1 0 23 76 1 0 25 77 1 1 27 78 1 0 27 79 1 0 27 80 1 0 28 81 1 0 29 82 1 1 30 83 1 0 30 84 1 0 31 85 1 0 31 86 1 0 32 87 1 0 32 88 1 0 32 89 1 0 36 90 1 1 38 91 1 1 39 92 1 0 39 93 1 0 40 94 1 0 41 95 1 6 42 96 1 1 43 97 1 1 44 98 1 0 45 99 1 0 46100 1 0 47101 1 0 47102 1 0 47103 1 0 48104 1 0 48105 1 0 48106 1 0 49107 1 0 49108 1 0 49109 1 0 M END

Standard InCHIKey	OOALYLWGJHIEKK-XFCMFZKPSA-N
Standard InCHI	InChI=1S/C38H60O11/c1-20-9-14-38(32(44)49-31-29(43)28(42)27(41)22(17-39)47-31)16-15-35(4)21(30(38)37(20,6)45)7-8-24-33(2)12-11-25-34(3,19-46-26(18-40)48-25)23(33)10-13-36(24,35)5/h7,20,22-31,39-43,45H,8-19H2,1-6H3/t20-,22-,23-,24-,25+,26-,27-,28+,29-,30-,31+,33+,34+,35-,36-,37-,38+/m1/s1
SMILES	OC[C@@H]1OC[C@@]2([C@@H](O1)CC[C@]1([C@H]2CC[C@@]2([C@@H]1CC=C1[C@@]2(C)CC[C@@]2([C@H]1[C@](C)(O)[C@@H](CC2)C)C(=O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	692.41	Volume:	697.328 ? Van der Waals volume.
Dense:	0.993	LogP:	1.637 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.192 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.928 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	38.0
TPSA:	175.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.189	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.781	Fsp³:	0.921
MCE-18:	142.466 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.841	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.04 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.125	Promiscuous compounds:	0.137

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.995	MDCK Permeability:	-5.206
Pgp-inhibitor:	0.0	Pgp-substrate:	0.048
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):	0.009
20% Bioavailability (F20%):	0.547	30% Bioavailability (F30%):	0.952
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.859	MRP1:	0.484
Plasma Protein Binding (PPB):	76.392%	Volume Distribution (VD):	-0.324
Fu:	18.251% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.936	BCRP inhibitor:	0.027
BSEP inhibitor:	0.142

ADMET: Metabolism

CYP1A2-inhibitor:	0.125	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.61	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.79	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.224	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.008
HLM stability:	0.017 ? 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):

0.89

Half-life (T1/2):

2.186

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.972	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.03	Skin Sensitization:	1.0
Carcinogencity:	0.916	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.2	Ototoxicity:	0.985
Hematotoxicity:	0.875	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.196
A549 Cytotoxicity:	0.972	Hek293 Cytotoxicity:	0.642
BCF:	1.327 ? 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:	3.702 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.427 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.524 ? 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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27642865]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235013]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409699]
NPO9182	Lychnophora passerina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25339	Trillium smallii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25649	Calliandra haematocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26345	Sideroxylon tomentosum	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25992	Lasallia papulosa	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25765	Dryopteris aemula	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26399	Crepidiastrum lanceolatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28950	Angelonia integerrima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9182	Lychnophora passerina	Species	Asteraceae	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
Inhibition	1

Activity Type	# Activity
Organism	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
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	28.1	%	PMID[17274628]

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 NPC47063 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	20484
0.1-0.2	24226
0.2-0.3	4004
0.3-0.4	896
0.4-0.5	160
0.5-0.6	67
0.6-0.7	6
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
0.7614	Intermediate Similarity	NPC204458
0.7614	Intermediate Similarity	NPC189884
0.7614	Intermediate Similarity	NPC269095
0.7614	Intermediate Similarity	NPC138334
0.759	Intermediate Similarity	NPC46388
0.7412	Intermediate Similarity	NPC37739
0.7204	Intermediate Similarity	NPC58448
0.7126	Intermediate Similarity	NPC310014
0.7126	Intermediate Similarity	NPC269315
0.7045	Intermediate Similarity	NPC271138
0.6907	Remote Similarity	NPC160415
0.6804	Remote Similarity	NPC75417
0.6768	Remote Similarity	NPC68175
0.6075	Remote Similarity	NPC36831
0.6	Remote Similarity	NPC128925
0.6	Remote Similarity	NPC256798
0.5934	Remote Similarity	NPC167383
0.5889	Remote Similarity	NPC191763
0.5859	Remote Similarity	NPC48499
0.5816	Remote Similarity	NPC90856
0.5816	Remote Similarity	NPC214484
0.5806	Remote Similarity	NPC237503
0.5758	Remote Similarity	NPC78046
0.5743	Remote Similarity	NPC475516
0.5631	Remote Similarity	NPC295371
0.5631	Remote Similarity	NPC39211
0.5625	Remote Similarity	NPC110139
0.5625	Remote Similarity	NPC108709
0.5588	Remote Similarity	NPC235405
0.5577	Remote Similarity	NPC469946
0.5534	Remote Similarity	NPC473373
0.5534	Remote Similarity	NPC249848
0.5534	Remote Similarity	NPC107966
0.5532	Remote Similarity	NPC605954
0.5524	Remote Similarity	NPC112352
0.5521	Remote Similarity	NPC7870
0.5521	Remote Similarity	NPC137917
0.5521	Remote Similarity	NPC75747
0.5481	Remote Similarity	NPC473884
0.5481	Remote Similarity	NPC157868
0.5474	Remote Similarity	NPC116794
0.5464	Remote Similarity	NPC102914
0.5455	Remote Similarity	NPC209894
0.5446	Remote Similarity	NPC29069
0.5429	Remote Similarity	NPC161674
0.5429	Remote Similarity	NPC475171
0.5421	Remote Similarity	NPC46665
0.5392	Remote Similarity	NPC179434
0.5377	Remote Similarity	NPC192791
0.5377	Remote Similarity	NPC223301
0.5377	Remote Similarity	NPC242840
0.5377	Remote Similarity	NPC171544
0.537	Remote Similarity	NPC63159
0.537	Remote Similarity	NPC235438
0.5361	Remote Similarity	NPC68419
0.5327	Remote Similarity	NPC30735
0.5327	Remote Similarity	NPC309714
0.5321	Remote Similarity	NPC222580
0.5321	Remote Similarity	NPC297263
0.5278	Remote Similarity	NPC40775
0.5278	Remote Similarity	NPC10607
0.5278	Remote Similarity	NPC251768
0.5278	Remote Similarity	NPC159309
0.5278	Remote Similarity	NPC480475
0.5278	Remote Similarity	NPC86222
0.5253	Remote Similarity	NPC220984
0.5229	Remote Similarity	NPC148417
0.5229	Remote Similarity	NPC475591
0.5229	Remote Similarity	NPC236870
0.5225	Remote Similarity	NPC104372
0.5179	Remote Similarity	NPC301449
0.5179	Remote Similarity	NPC601290
0.5143	Remote Similarity	NPC139894
0.5138	Remote Similarity	NPC11551
0.5133	Remote Similarity	NPC80986
0.5094	Remote Similarity	NPC150400
0.5089	Remote Similarity	NPC281148
0.5089	Remote Similarity	NPC114484
0.5088	Remote Similarity	NPC31838
0.5088	Remote Similarity	NPC481078
0.5088	Remote Similarity	NPC187290
0.5086	Remote Similarity	NPC268184
0.5045	Remote Similarity	NPC31193

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC47063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7214
0.1-0.2	1877
0.2-0.3	56
0.3-0.4	3
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