NPASS Compound

Natural Product: NPC248976

Natural Product ID	NPC248976
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LXBHENGHUHPUQC-YJCQZJKPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102588711
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 101106 0 0 0 0 0 0 0 0999 V2000 -1.5567 1.8724 5.0661 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2746 1.6148 3.7558 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1806 0.4481 3.8839 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7965 -0.7660 3.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3610 -0.5241 1.7055 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6854 -1.7287 1.1479 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2384 -1.9345 1.4649 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 -0.6733 1.3510 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9279 -0.3533 2.8264 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2932 0.3199 0.7704 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0654 0.8465 -0.3962 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1080 0.4940 -1.2313 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2365 0.2187 -0.2858 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5577 0.1366 -1.0318 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5875 -0.8494 -2.1294 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6663 1.5168 -1.7251 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0476 1.9941 -1.8756 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1310 0.9945 -1.7676 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0508 0.1509 -0.5082 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7517 -1.1353 -0.7716 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8598 0.8591 0.6024 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1903 0.9603 0.1152 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6537 0.1008 -0.0405 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4452 -0.9513 1.0353 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1023 -0.7572 1.7080 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9427 -0.8542 0.6929 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0511 -2.2517 0.1671 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3627 0.2342 -2.9131 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.7162 1.4749 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3870 1.6347 2.5884 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4281 2.5439 2.5647 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6557 -0.4368 0.9122 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7666 -0.5545 1.4687 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6441 -0.2237 -0.4549 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8517 -0.1417 -1.1968 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0222 1.1630 -1.9032 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0235 0.9802 -3.0230 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0115 -0.1337 -2.7250 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3293 -1.4020 -2.3197 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4928 -2.5202 -3.2963 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8622 -2.7401 -3.4636 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9533 -1.1680 -2.1403 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8391 0.3528 -1.6872 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4061 0.7937 -4.2499 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4354 2.1468 -1.0001 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2596 1.5181 5.8748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3789 2.9308 5.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6466 1.2562 5.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9503 2.5220 3.6321 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2458 0.6959 3.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2283 0.1362 4.9702 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0188 -1.3398 3.6893 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7307 -1.4080 3.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2288 -2.6245 1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8806 -1.7728 0.0342 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2038 -2.3831 2.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0770 -2.7540 0.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2845 -1.3173 3.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0116 -0.1838 3.4007 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5385 0.5151 2.9808 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7678 1.6076 -0.8225 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3599 1.3618 -1.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8732 -0.3300 -1.9334 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3530 1.1691 0.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7256 -0.3980 -3.1614 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5761 -1.2945 -2.2345 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3810 -1.6167 -2.0716 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1908 1.4525 -2.7485 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0800 2.2846 -1.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1643 2.5148 -2.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2662 2.8055 -1.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0918 1.5920 -1.6690 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8580 -0.9609 -0.5955 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4999 -1.9816 -0.1418 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7474 -1.4331 -1.8620 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4925 1.8980 0.6881 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8570 0.2907 1.5317 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6902 1.4272 0.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5003 1.0729 0.5405 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1800 -0.7021 1.8472 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6888 -1.9686 0.7512 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0626 -1.4789 2.5020 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1192 0.3254 2.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3721 -2.5579 -0.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0030 -2.9551 1.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0832 -2.4706 -0.2567 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9428 0.6080 -3.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1775 1.3293 0.7337 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2608 3.2641 3.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2381 2.5785 1.7160 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6991 -0.2730 -0.4879 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0651 1.5256 -2.3666 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6204 1.9164 -3.0826 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5876 -0.3098 -3.6381 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7173 -1.6996 -1.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9817 -2.3082 -4.2447 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0161 -3.4243 -2.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2784 -2.6460 -2.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5306 -0.2961 -1.4742 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0458 0.2887 -4.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9530 3.0081 -1.1527 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 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 18 28 1 0 10 29 1 0 29 30 1 0 30 31 2 0 5 32 1 6 32 33 2 0 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 30 2 1 0 42 35 1 0 29 5 1 0 26 8 1 0 26 13 1 0 23 14 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 6 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 9 58 1 0 9 59 1 0 9 60 1 0 11 61 1 0 12 62 1 0 12 63 1 0 13 64 1 1 15 65 1 0 15 66 1 0 15 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 18 72 1 1 20 73 1 0 20 74 1 0 20 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 23 79 1 1 24 80 1 0 24 81 1 0 25 82 1 0 25 83 1 0 27 84 1 0 27 85 1 0 27 86 1 0 28 87 1 0 29 88 1 6 31 89 1 0 31 90 1 0 35 91 1 1 36 92 1 6 37 93 1 6 38 94 1 6 39 95 1 1 40 96 1 0 40 97 1 0 41 98 1 0 43 99 1 0 44100 1 0 45101 1 0 M END

Standard InCHIKey	LXBHENGHUHPUQC-YJCQZJKPSA-N
Standard InCHI	InChI=1S/C36H56O9/c1-19-9-14-36(31(43)45-30-29(42)28(41)27(40)22(17-37)44-30)16-15-34(5)21(26(36)20(19)2)7-8-24-32(3)12-11-25(39)33(4,18-38)23(32)10-13-35(24,34)6/h7,19,22-30,37-42H,2,8-18H2,1,3-6H3/t19-,22-,23-,24-,25+,26+,27-,28+,29-,30+,32+,33+,34-,35-,36+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O)[C@@H]2C1=C)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	632.39	Volume:	651.076 ? Van der Waals volume.
Dense:	0.971	LogP:	2.699 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.023 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.473 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	34.0
TPSA:	156.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.202	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.582	Fsp³:	0.861
MCE-18:	124.955 ? 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:	0.84	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.092 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.165	Promiscuous compounds:	0.086

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.049	MDCK Permeability:	-5.176
Pgp-inhibitor:	0.004	Pgp-substrate:	0.002
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%):	0.892	30% Bioavailability (F30%):	0.922
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.052
Plasma Protein Binding (PPB):	76.115%	Volume Distribution (VD):	-0.136
Fu:	20.165% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.994
BSEP inhibitor:	0.911

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.025	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.05
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.417
HLM stability:	0.003 ? 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):

1.788

Half-life (T1/2):

2.271

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.656	Drug-induced Liver Injury (DILI):	0.533
AMES Toxicity:	0.812	Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.056	Skin Sensitization:	1.0
Carcinogencity:	0.843	Eye Corrosion:	0.0
Eye Irritation:	0.016	Respiratory Toxicity:	0.1
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.969
Hematotoxicity:	0.706	Drug-induced Nephrotoxicity:	0.942
Genotoxicity:	0.228	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.953	Hek293 Cytotoxicity:	0.282
BCF:	1.424 ? 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:	3.879 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.599 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.812 ? 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

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 NPC248976 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	20971
0.1-0.2	23139
0.2-0.3	4519
0.3-0.4	975
0.4-0.5	170
0.5-0.6	62
0.6-0.7	15
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8354	Intermediate Similarity	NPC102914
0.8	Intermediate Similarity	NPC137917
0.7778	Intermediate Similarity	NPC7870
0.7778	Intermediate Similarity	NPC75747
0.7654	Intermediate Similarity	NPC37739
0.7531	Intermediate Similarity	NPC237503
0.6829	Remote Similarity	NPC191763
0.6786	Remote Similarity	NPC46388
0.6782	Remote Similarity	NPC220984
0.6778	Remote Similarity	NPC29069
0.6706	Remote Similarity	NPC190837
0.6667	Remote Similarity	NPC167383
0.6667	Remote Similarity	NPC110139
0.6667	Remote Similarity	NPC108709
0.6512	Remote Similarity	NPC116794
0.6477	Remote Similarity	NPC271138
0.6364	Remote Similarity	NPC68419
0.6067	Remote Similarity	NPC306746
0.6023	Remote Similarity	NPC605954
0.6	Remote Similarity	NPC310014
0.6	Remote Similarity	NPC269315
0.5957	Remote Similarity	NPC269095
0.5895	Remote Similarity	NPC78046
0.5842	Remote Similarity	NPC101744
0.5806	Remote Similarity	NPC256798
0.5789	Remote Similarity	NPC189884
0.5789	Remote Similarity	NPC138334
0.5686	Remote Similarity	NPC102439
0.5684	Remote Similarity	NPC47063
0.567	Remote Similarity	NPC179434
0.5652	Remote Similarity	NPC212968
0.5638	Remote Similarity	NPC128925
0.5625	Remote Similarity	NPC204458
0.5625	Remote Similarity	NPC90856
0.5545	Remote Similarity	NPC475171
0.5543	Remote Similarity	NPC199457
0.55	Remote Similarity	NPC473373
0.5484	Remote Similarity	NPC187056
0.5484	Remote Similarity	NPC606216
0.5484	Remote Similarity	NPC607023
0.5464	Remote Similarity	NPC214484
0.54	Remote Similarity	NPC235405
0.5354	Remote Similarity	NPC48499
0.5347	Remote Similarity	NPC58448
0.5347	Remote Similarity	NPC249848
0.5347	Remote Similarity	NPC107966
0.5319	Remote Similarity	NPC604133
0.5294	Remote Similarity	NPC295371
0.5294	Remote Similarity	NPC473884
0.5258	Remote Similarity	NPC209894
0.5248	Remote Similarity	NPC139894
0.5248	Remote Similarity	NPC475516
0.5243	Remote Similarity	NPC473343
0.5243	Remote Similarity	NPC469946
0.5238	Remote Similarity	NPC11551
0.5238	Remote Similarity	NPC473459
0.5213	Remote Similarity	NPC65590
0.5213	Remote Similarity	NPC125923
0.5196	Remote Similarity	NPC150400
0.5192	Remote Similarity	NPC75417
0.5146	Remote Similarity	NPC39211
0.5146	Remote Similarity	NPC157868
0.5143	Remote Similarity	NPC109588
0.5143	Remote Similarity	NPC104071
0.5143	Remote Similarity	NPC30735
0.5143	Remote Similarity	NPC160415
0.5143	Remote Similarity	NPC309714
0.5096	Remote Similarity	NPC161674
0.5094	Remote Similarity	NPC40775
0.5094	Remote Similarity	NPC480475
0.5093	Remote Similarity	NPC134835
0.5091	Remote Similarity	NPC480474
0.5051	Remote Similarity	NPC195132
0.5048	Remote Similarity	NPC192791
0.5048	Remote Similarity	NPC223301
0.5048	Remote Similarity	NPC242840
0.5048	Remote Similarity	NPC171544
0.5048	Remote Similarity	NPC112352
0.5047	Remote Similarity	NPC148417
0.5047	Remote Similarity	NPC68175
0.5047	Remote Similarity	NPC235438
0.5046	Remote Similarity	NPC281148
0.5046	Remote Similarity	NPC73318

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC248976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7467
0.1-0.2	1615
0.2-0.3	63
0.3-0.4	4
0.4-0.5	1
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