NPASS Compound

Natural Product: NPC158663

Natural Product ID	NPC158663
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2Beta,3Beta,4Beta,Trihydroxycelarbico
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1076610
PubChem CID	46239957
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 82 86 0 0 0 0 0 0 0 0999 V2000 2.2176 -1.1673 -5.0077 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4757 -0.8794 -3.5528 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5449 -0.2742 -3.2868 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 -1.2619 -2.5692 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8625 -0.9718 -1.2145 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0065 -2.2456 -0.4369 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6726 -2.9494 -0.2602 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9140 -4.0934 0.6835 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4675 -2.0712 -0.0314 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4627 -2.4317 1.0065 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7317 -1.9260 0.2879 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6776 -0.4453 0.1134 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3805 0.1913 0.5118 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1244 -0.6086 0.3072 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6563 -0.6555 1.6451 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8296 -0.0079 -0.6727 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5275 1.0178 0.0878 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6555 2.3126 -0.3934 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1438 2.5223 -1.5041 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3545 3.3509 0.3767 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 3.0866 1.6052 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5670 4.0401 2.3450 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6839 5.3235 1.8388 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1292 5.5915 0.6049 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4589 4.6171 -0.1441 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3140 1.5504 0.1741 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3726 2.6019 1.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4792 2.2818 2.2409 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3222 4.0148 0.6933 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3308 4.9722 1.6871 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3022 6.3039 1.3767 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2635 6.7664 0.0762 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2553 5.7973 -0.9070 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2840 4.4512 -0.6127 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4103 -2.5074 -1.1000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6029 -3.9626 -1.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3839 -1.9527 -2.1262 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1702 -1.9856 -1.2637 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5577 -3.7304 1.4256 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6227 -4.1401 2.7408 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5921 -3.2530 3.6310 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7262 -5.5541 3.1864 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5344 -3.6323 -1.5158 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8426 -3.0841 -1.1787 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1708 -1.4150 -5.5295 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8046 -0.2745 -5.5007 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5664 -2.0462 -5.0735 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8380 -0.4442 -1.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5517 -2.0709 0.5055 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2055 -4.9405 0.5112 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0748 -3.8555 1.7224 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8993 -4.5505 0.3420 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4468 -1.7651 1.9216 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6452 -2.3330 0.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0193 -0.2095 -0.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5175 -0.0439 0.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4949 0.2472 1.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6292 -1.6144 2.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6365 -0.1907 1.5819 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0807 0.0305 2.3478 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3868 0.4445 -1.5753 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8224 2.0966 2.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0045 3.8344 3.3136 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1965 6.0562 2.4177 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2318 6.5952 0.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0631 4.9157 -1.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3612 4.6549 2.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 7.0799 2.1485 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2409 7.8220 -0.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2251 6.1552 -1.9420 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2834 3.7244 -1.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8195 -4.3638 -2.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8468 -4.6114 -0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5718 -4.1833 -0.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8679 -1.1411 -2.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3052 -1.6139 -1.6275 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5898 -2.7367 -2.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6714 -5.8969 3.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2251 -5.6243 4.1725 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1497 -6.2140 2.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1293 -3.0388 -2.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5661 -3.4807 -0.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 13 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 11 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 10 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 7 43 1 6 6 44 1 0 16 5 1 0 25 20 1 0 34 29 1 0 14 9 1 0 9 38 1 6 1 45 1 0 1 46 1 0 1 47 1 0 5 48 1 6 6 49 1 1 8 50 1 0 8 51 1 0 8 52 1 0 10 53 1 1 11 54 1 1 12 55 1 0 12 56 1 0 13 57 1 1 15 58 1 0 15 59 1 0 15 60 1 0 16 61 1 6 21 62 1 0 22 63 1 0 23 64 1 0 24 65 1 0 25 66 1 0 30 67 1 0 31 68 1 0 32 69 1 0 33 70 1 0 34 71 1 0 36 72 1 0 36 73 1 0 36 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 42 78 1 0 42 79 1 0 42 80 1 0 43 81 1 0 44 82 1 0 M END

Standard InCHIKey	VUXZIMAQBPJZQB-YIBJYTJTSA-N
Standard InCHI	InChI=1S/C33H38O11/c1-18(34)40-24-25(36)32(6,39)33-26(41-19(2)35)22(30(3,4)44-33)17-23(42-28(37)20-13-9-7-10-14-20)31(33,5)27(24)43-29(38)21-15-11-8-12-16-21/h7-16,22-27,36,39H,17H2,1-6H3/t22-,23+,24-,25+,26-,27+,31-,32+,33-/m1/s1
SMILES	CC(=O)O[C@@H]1[C@@H]([C@@](C)([C@@]23[C@@H]([C@@H](C[C@@H]([C@]2(C)[C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)C(C)(C)O3)OC(=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.24	Volume:	606.87 ? Van der Waals volume.
Dense:	1.006	LogP:	2.865 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.833 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.743 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.366	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.824	Fsp³:	0.515
MCE-18:	173.16 ? 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:	0.394	Fluc inhibitor:	0.034 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.038 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.117	Promiscuous compounds:	0.132

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.53	MDCK Permeability:	-4.835
Pgp-inhibitor:	1.0	Pgp-substrate:	0.702
PAMPA:	0.924 ? 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%):	0.119	30% Bioavailability (F30%):	0.55
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.999
Plasma Protein Binding (PPB):	79.631%	Volume Distribution (VD):	-0.429
Fu:	18.988% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.94	BCRP inhibitor:	0.032
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.442
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.975 ? 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):

6.496

Half-life (T1/2):

0.684

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.342
Human Hepatotoxicity (H-HT):	0.105	Drug-induced Liver Injury (DILI):	0.543
AMES Toxicity:	0.234	Rat Oral Acute Toxicity:	0.312
Maximum Recommended Daily Dose:	0.415	Skin Sensitization:	0.991
Carcinogencity:	0.447	Eye Corrosion:	0.002
Eye Irritation:	0.529	Respiratory Toxicity:	0.195
Drug-induced Neurotoxicity:	0.092	Ototoxicity:	0.43
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.727
Genotoxicity:	0.74	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.029	Hek293 Cytotoxicity:	0.114
BCF:	0.584 ? 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:	3.597 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.244 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.64 ? 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
NPO3859	Maytenus magellanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11741484]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16643052]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	Roots; Stems; Tubers	n.a.	n.a.	PMID[16872143]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[18452334]
NPO8299	Sorocea muriculata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[18847244]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36060112]
NPO25504	Streptomyces rutgersensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7948	Galium sinaicum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3599	Rheum maximowiczii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13443	Doris montereyensis	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3439	Streptomyces koyangensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3599	Rheum maximowiczii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3599	Rheum maximowiczii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21651	Cheilocostus speciosus	Species	Costaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4827	Glycyrrhiza macedonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6325	Senecio nebrodensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5157	Penstemon nitidus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13443	Doris montereyensis	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3021	Arcicella aquatica	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21651	Cheilocostus speciosus	Species	Costaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO787	Lentinus degener	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8419	Lepechinia glomerata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3859	Maytenus magellanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1521	Curcuma oligantha	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7948	Galium sinaicum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5329	Aspilia bishoplecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25504	Streptomyces rutgersensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO473	Artemisia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2479	Dorstenia drakena	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3439	Streptomyces koyangensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3599	Rheum maximowiczii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2887	Ottonia ovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5501	Pulicaria angustifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8299	Sorocea muriculata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3107	Bupleurum falcatum	Species	Apiaceae	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
Activity	8
FR50	4

Activity Type	# Activity
Cell line	1
Organism	7
Others	4

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[20146433]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	FR50	=	0.44	n.a.	DOI[10.1016/S0305-1978(97)00035-5]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	FR50	=	0.24	n.a.	DOI[10.1016/0305-1978(92)90042-C]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[20146433]
NPT2	Others	Unspecified	n.a.	Activity	=	33.2	%	PMID[20146433]
NPT2	Others	Unspecified	n.a.	Activity	=	77.5	%	PMID[20146433]
NPT2	Others	Unspecified	n.a.	Activity	=	98.6	%	PMID[20146433]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.0	%	PMID[20146433]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	53.3	%	PMID[20146433]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	90.0	%	PMID[20146433]

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 NPC158663 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	12106
0.1-0.2	34816
0.2-0.3	2282
0.3-0.4	456
0.4-0.5	140
0.5-0.6	39
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9344	High Similarity	NPC270590
0.7917	Intermediate Similarity	NPC184817
0.6957	Remote Similarity	NPC483883
0.6957	Remote Similarity	NPC151585
0.625	Remote Similarity	NPC127026
0.625	Remote Similarity	NPC483890
0.6053	Remote Similarity	NPC70716
0.6053	Remote Similarity	NPC97667
0.5897	Remote Similarity	NPC479042
0.5867	Remote Similarity	NPC171207
0.5775	Remote Similarity	NPC473081
0.5775	Remote Similarity	NPC195647
0.5732	Remote Similarity	NPC188865
0.5732	Remote Similarity	NPC56953
0.5641	Remote Similarity	NPC95265
0.5634	Remote Similarity	NPC474608
0.561	Remote Similarity	NPC483865
0.5556	Remote Similarity	NPC200592
0.5556	Remote Similarity	NPC270498
0.5556	Remote Similarity	NPC610542
0.5541	Remote Similarity	NPC483879
0.5526	Remote Similarity	NPC471101
0.5476	Remote Similarity	NPC483870
0.5467	Remote Similarity	NPC281717
0.5467	Remote Similarity	NPC163087
0.5467	Remote Similarity	NPC483886
0.5443	Remote Similarity	NPC96903
0.5422	Remote Similarity	NPC174982
0.5417	Remote Similarity	NPC283375
0.5402	Remote Similarity	NPC479045
0.5395	Remote Similarity	NPC163719
0.5395	Remote Similarity	NPC95810
0.5325	Remote Similarity	NPC27377
0.5256	Remote Similarity	NPC473673
0.525	Remote Similarity	NPC127720
0.5205	Remote Similarity	NPC183122
0.5195	Remote Similarity	NPC291599
0.519	Remote Similarity	NPC41481
0.519	Remote Similarity	NPC92293
0.5161	Remote Similarity	NPC483880
0.5161	Remote Similarity	NPC156941
0.5132	Remote Similarity	NPC483862
0.5128	Remote Similarity	NPC139067
0.5128	Remote Similarity	NPC43241
0.5128	Remote Similarity	NPC472572
0.5125	Remote Similarity	NPC57628
0.5125	Remote Similarity	NPC266265

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3785
0.1-0.2	5176
0.2-0.3	188
0.3-0.4	1
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