NPASS Compound

Natural Product: NPC96580

Natural Product ID	NPC96580
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GZTXRAOZNVKIDQ-ZOGWWOATSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID: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 89 94 0 0 0 0 0 0 0 0999 V2000 -4.4802 -2.4488 1.7773 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0449 -1.0733 1.4794 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1867 -0.9024 2.5005 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7320 -1.1486 0.1419 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8814 0.1764 -0.5083 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4919 0.7304 -0.7893 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7843 -0.0057 -1.8656 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3977 0.5327 -2.0293 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5564 0.3061 -0.7588 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5700 -1.1868 -0.5585 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2565 1.0397 0.3115 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5767 1.8071 1.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1286 2.0321 1.1331 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5306 0.9860 0.2781 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0363 1.1152 0.2231 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5535 2.4325 -0.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4895 0.9312 1.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9683 0.7412 1.8118 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4146 -0.4120 0.9898 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0274 -0.2911 -0.4684 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8809 0.6684 -1.2235 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2962 -1.6832 -1.0625 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7802 -2.4919 -0.0429 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9112 -2.0175 0.5690 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1648 -2.1647 -0.2514 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1220 -2.8665 1.8307 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7545 -0.6968 1.0501 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5697 -0.0586 -0.5390 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0306 0.0344 -1.9503 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5368 -0.3052 -1.8137 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1629 0.7782 -1.0199 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2328 1.9876 -1.9063 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7651 0.9103 0.4885 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0642 0.0070 1.6234 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8102 2.0994 -1.3699 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5383 2.4291 -2.5388 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4437 3.0631 -0.5704 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5876 -2.3809 2.4602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2082 -3.0978 2.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1587 -2.9828 0.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3177 0.1843 2.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1128 -1.3676 2.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8224 -1.3009 3.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7732 -1.5765 0.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2303 -1.8441 -0.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4826 0.0716 -1.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3695 0.8717 0.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8312 -1.1048 -1.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3188 0.2506 -2.8303 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4732 1.6304 -2.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8895 0.0711 -2.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4267 -1.7002 -1.5180 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8557 -1.5669 0.1637 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5884 -1.5069 -0.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1325 2.3534 1.9434 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2057 1.9507 2.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1044 3.0739 0.8504 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3837 0.0185 0.8544 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9797 2.4535 -1.2413 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8381 3.2786 -0.1715 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4112 2.7840 0.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2288 1.8844 2.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9559 0.1166 2.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5660 1.6551 1.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1319 0.4493 2.8916 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8708 -1.3250 1.3702 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4313 0.8188 -2.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1490 1.5833 -0.6986 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8579 0.1385 -1.4319 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3807 -2.1507 -1.4431 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0315 -1.6586 -1.8647 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9301 -2.4105 -1.2914 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6615 -1.1522 -0.2801 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8824 -2.8935 0.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1803 -3.0780 2.3357 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8326 -2.2679 2.4644 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6807 -3.7757 1.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0767 -0.9725 -0.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1774 1.0032 -2.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4499 -0.7511 -2.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5445 -1.2862 -1.2842 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0732 -0.4724 -2.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7542 2.4399 -2.1294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8862 2.7813 -1.5528 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5930 1.6276 -2.9026 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0537 1.9494 0.8533 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0872 -0.4936 1.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3026 0.5721 2.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2307 4.0503 -0.6665 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 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 20 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 6 11 33 1 0 33 34 1 0 6 35 1 6 35 36 2 0 35 37 1 0 34 2 1 0 33 6 1 0 31 9 1 0 31 14 1 0 28 15 1 0 27 19 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 5 46 1 0 5 47 1 0 7 48 1 0 7 49 1 0 8 50 1 0 8 51 1 0 10 52 1 0 10 53 1 0 10 54 1 0 12 55 1 0 13 56 1 0 13 57 1 0 14 58 1 1 16 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 18 64 1 0 18 65 1 0 19 66 1 1 21 67 1 0 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 25 72 1 0 25 73 1 0 25 74 1 0 26 75 1 0 26 76 1 0 26 77 1 0 28 78 1 1 29 79 1 0 29 80 1 0 30 81 1 0 30 82 1 0 32 83 1 0 32 84 1 0 32 85 1 0 33 86 1 1 34 87 1 0 34 88 1 0 37 89 1 0 M END

Standard InCHIKey	GZTXRAOZNVKIDQ-ZOGWWOATSA-N
Standard InCHI	InChI=1S/C33H52O4/c1-27(2)15-17-33(26(34)35)18-16-31(7)21(22(33)19-27)9-10-24-29(5)13-12-25-30(6,20-36-28(3,4)37-25)23(29)11-14-32(24,31)8/h9,22-25H,10-20H2,1-8H3,(H,34,35)/t22-,23+,24+,25-,29-,30-,31+,32+,33-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H]6[C@@](C)(COC(C)(C)O6)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.39	Volume:	557.873 ? Van der Waals volume.
Dense:	0.918	LogP:	4.162 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.612 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.157 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	32.0
TPSA:	55.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.362	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.938	Fsp³:	0.909
MCE-18:	121.429 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.834	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.414	Promiscuous compounds:	0.093

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.259	MDCK Permeability:	-4.883
Pgp-inhibitor:	0.023	Pgp-substrate:	0.0
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):	0.0
20% Bioavailability (F20%):	0.179	30% Bioavailability (F30%):	0.003
50% Bioavailability (F50%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.907	MRP1:	0.94
Plasma Protein Binding (PPB):	96.662%	Volume Distribution (VD):	-0.313
Fu:	4.079% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.202	BCRP inhibitor:	0.044
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.951	CYP2C19-substrate:	0.224
CYP2C9-inhibitor:	0.127	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.142	CYP3A4-substrate:	0.014
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.053
HLM stability:	0.73 ? 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):

4.354

Half-life (T1/2):

0.651

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.069
Human Hepatotoxicity (H-HT):	0.884	Drug-induced Liver Injury (DILI):	0.861
AMES Toxicity:	0.414	Rat Oral Acute Toxicity:	0.722
Maximum Recommended Daily Dose:	0.112	Skin Sensitization:	0.766
Carcinogencity:	0.988	Eye Corrosion:	0.021
Eye Irritation:	0.397	Respiratory Toxicity:	0.91
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.741
Hematotoxicity:	0.2	Drug-induced Nephrotoxicity:	0.531
Genotoxicity:	0.287	RPMI-8226 Immunitoxicity:	0.004
A549 Cytotoxicity:	0.025	Hek293 Cytotoxicity:	0.189
BCF:	2.071 ? 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:	4.452 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.694 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.24 ? 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
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	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	2
Ratio IC50	1
ED50	1

Activity Type	# Activity
Individual protein	2
Others	1
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual protein	Carboxylesterase 2	Homo sapiens	IC50	=	1900.0	nM	PMID[32951423]
NPT166	Individual protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	IC50	=	100.0	nM	PMID[32951423]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	30.0	n.a.	PMID[32951423]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	ED50	=	83.6	uM	PMID[37859723]

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 NPC96580 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	27488
0.1-0.2	19740
0.2-0.3	2027
0.3-0.4	338
0.4-0.5	183
0.5-0.6	65
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8028	Intermediate Similarity	NPC478836
0.6901	Remote Similarity	NPC120840
0.6377	Remote Similarity	NPC604575
0.625	Remote Similarity	NPC480946
0.625	Remote Similarity	NPC130577
0.625	Remote Similarity	NPC142415
0.625	Remote Similarity	NPC102683
0.6092	Remote Similarity	NPC475611
0.6081	Remote Similarity	NPC158141
0.6024	Remote Similarity	NPC283849
0.6024	Remote Similarity	NPC28198
0.6024	Remote Similarity	NPC476123
0.6	Remote Similarity	NPC200752
0.5974	Remote Similarity	NPC296164
0.5946	Remote Similarity	NPC270768
0.5946	Remote Similarity	NPC59263
0.5946	Remote Similarity	NPC210106
0.5921	Remote Similarity	NPC474963
0.5904	Remote Similarity	NPC204407
0.5875	Remote Similarity	NPC23241
0.5833	Remote Similarity	NPC606107
0.5814	Remote Similarity	NPC100383
0.5789	Remote Similarity	NPC298554
0.5769	Remote Similarity	NPC158347
0.5753	Remote Similarity	NPC280654
0.5733	Remote Similarity	NPC275809
0.5733	Remote Similarity	NPC84319
0.5733	Remote Similarity	NPC156981
0.5733	Remote Similarity	NPC52021
0.5733	Remote Similarity	NPC599947
0.5698	Remote Similarity	NPC286347
0.5682	Remote Similarity	NPC284807
0.5682	Remote Similarity	NPC473538
0.5658	Remote Similarity	NPC231063
0.5658	Remote Similarity	NPC282395
0.5658	Remote Similarity	NPC481360
0.5658	Remote Similarity	NPC110308
0.5625	Remote Similarity	NPC474727
0.5618	Remote Similarity	NPC191410
0.5584	Remote Similarity	NPC478841
0.5584	Remote Similarity	NPC488166
0.5526	Remote Similarity	NPC282616
0.5526	Remote Similarity	NPC37038
0.5506	Remote Similarity	NPC294112
0.5455	Remote Similarity	NPC106112
0.5455	Remote Similarity	NPC261935
0.5385	Remote Similarity	NPC475472
0.5376	Remote Similarity	NPC136877
0.5375	Remote Similarity	NPC488521
0.5326	Remote Similarity	NPC22676
0.5326	Remote Similarity	NPC270667
0.5326	Remote Similarity	NPC164194
0.5325	Remote Similarity	NPC182797
0.5325	Remote Similarity	NPC52169
0.5325	Remote Similarity	NPC488562
0.5319	Remote Similarity	NPC174679
0.5319	Remote Similarity	NPC279554
0.5319	Remote Similarity	NPC56713
0.5319	Remote Similarity	NPC59804
0.5301	Remote Similarity	NPC481362
0.5263	Remote Similarity	NPC127056
0.525	Remote Similarity	NPC608622
0.5213	Remote Similarity	NPC12288
0.5208	Remote Similarity	NPC6377
0.5208	Remote Similarity	NPC488561
0.5208	Remote Similarity	NPC208381
0.5208	Remote Similarity	NPC610795
0.5195	Remote Similarity	NPC198664
0.5158	Remote Similarity	NPC25605
0.5128	Remote Similarity	NPC121798
0.5128	Remote Similarity	NPC234346
0.5125	Remote Similarity	NPC485589
0.5104	Remote Similarity	NPC114441
0.5104	Remote Similarity	NPC109079
0.5102	Remote Similarity	NPC469945
0.506	Remote Similarity	NPC485588
0.5052	Remote Similarity	NPC472949
0.505	Remote Similarity	NPC73829

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC96580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6842
0.1-0.2	2287
0.2-0.3	13
0.3-0.4	7
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