NPASS Compound

Natural Product: NPC127026

Natural Product ID	NPC127026
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BILLVHCBRMUWHZ-SAIWUOSISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1076611
PubChem CID	10919621
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 93 98 0 0 0 0 0 0 0 0999 V2000 -3.3383 2.0156 -3.1220 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2849 0.9779 -2.9009 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6949 0.6053 -3.9812 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9518 0.4719 -1.8070 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1117 -0.4391 -1.1743 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0002 0.1791 -0.3501 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8209 -0.9073 0.2183 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0986 -1.8634 -0.9517 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1339 -0.6508 0.8228 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1895 -0.4557 2.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1078 -1.1922 3.0559 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6729 -2.3580 2.1627 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1349 -1.5992 1.2264 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2671 -2.2874 0.5610 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0749 -3.7579 0.2831 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8687 -1.5359 -0.5737 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1774 -1.0202 -0.2679 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3506 -1.4352 -0.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2567 -2.3850 -1.6692 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6650 -0.9061 -0.4869 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8369 0.1008 0.4177 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1169 0.6025 0.7197 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2312 0.0766 0.0984 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0265 -0.9262 -0.7997 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8014 -1.4019 -1.0838 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3006 -2.2809 1.5548 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7036 -0.4951 1.9172 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0892 -0.3026 3.1158 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1769 1.1587 3.3970 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9894 -0.6716 4.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1756 -3.4494 2.8058 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6413 -4.7002 2.9330 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7055 -4.8550 2.3613 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0596 -5.7411 3.6736 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8868 0.3078 0.1236 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0007 0.0385 -0.6325 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3015 -1.2250 -0.6895 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8426 0.9749 -1.3479 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7774 2.3308 -1.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5719 3.2201 -1.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4722 2.7063 -2.8684 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5635 1.3465 -3.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7758 0.4770 -2.2678 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6867 1.1505 -1.0600 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6475 2.5103 -0.7968 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0910 2.7519 0.2137 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3135 3.5623 -1.5119 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0168 3.3994 -2.6599 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6663 4.4550 -3.3102 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6094 5.7202 -2.7900 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8978 5.9198 -1.6150 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2651 4.8666 -0.9920 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7093 2.4260 -2.1434 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9095 2.8024 -3.7690 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1924 1.5563 -3.6790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5415 -0.8715 -2.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5477 0.7114 0.4499 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2915 -2.4486 -1.3040 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5445 -1.2271 -1.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9281 -2.5465 -0.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7553 -1.6049 0.6688 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3185 0.6081 2.6106 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1503 -0.8957 2.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4313 -1.5834 4.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5894 -2.7556 1.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0474 -4.1177 0.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6581 -3.9873 -0.6628 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5790 -4.4227 1.0467 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1021 -2.3336 -1.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9988 0.5608 0.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2680 1.4010 1.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2538 0.4228 0.2895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6624 -2.2162 -1.8086 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9399 -3.0185 1.4117 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5059 1.3382 4.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6727 1.7207 2.6253 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8748 1.6066 3.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7470 0.0692 4.5250 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3179 -0.7624 5.2000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4810 -1.6186 4.0352 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3249 -6.7686 3.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1604 -5.6758 3.4233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0428 -5.5423 4.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0809 2.7832 -0.5514 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4963 4.2965 -1.8565 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1100 3.3792 -3.4697 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2860 0.9870 -3.7213 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8949 -0.5796 -2.4155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0723 2.3963 -3.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2170 4.2949 -4.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1023 6.5887 -3.2552 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8770 6.9293 -1.2230 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7042 5.0139 -0.0732 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 6 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 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 14 26 1 1 13 27 1 1 27 28 1 0 28 29 1 0 28 30 1 0 12 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 9 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 6 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 16 5 1 0 25 20 1 0 43 38 1 0 52 47 1 0 13 7 1 0 28 11 1 0 1 53 1 0 1 54 1 0 1 55 1 0 5 56 1 6 6 57 1 1 8 58 1 0 8 59 1 0 8 60 1 0 9 61 1 1 10 62 1 0 10 63 1 0 11 64 1 1 12 65 1 6 15 66 1 0 15 67 1 0 15 68 1 0 16 69 1 6 21 70 1 0 22 71 1 0 23 72 1 0 25 73 1 0 26 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 34 81 1 0 34 82 1 0 34 83 1 0 39 84 1 0 40 85 1 0 41 86 1 0 42 87 1 0 43 88 1 0 48 89 1 0 49 90 1 0 50 91 1 0 51 92 1 0 52 93 1 0 M END

Standard InCHIKey	BILLVHCBRMUWHZ-SAIWUOSISA-N
Standard InCHI	InChI=1S/C39H41NO12/c1-22(41)47-29-31(50-34(44)25-16-11-8-12-17-25)37(5)28(49-33(43)24-14-9-7-10-15-24)20-27-30(48-23(2)42)39(37,52-36(27,3)4)38(6,46)32(29)51-35(45)26-18-13-19-40-21-26/h7-19,21,27-32,46H,20H2,1-6H3/t27-,28+,29+,30-,31+,32+,37-,38+,39-/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H]([C@@]2(C)[C@H](C[C@@H]3[C@H]([C@@]2([C@](C)([C@H]1OC(=O)c1cccnc1)O)OC3(C)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	715.26	Volume:	711.33 ? Van der Waals volume.
Dense:	1.006	LogP:	2.983 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.933 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.946 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	37.0
TPSA:	173.85 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.259	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.98	Fsp³:	0.436
MCE-18:	193.286 ? 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:	0.31	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.254 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.029	Promiscuous compounds:	0.028

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.473	MDCK Permeability:	-5.003
Pgp-inhibitor:	1.0	Pgp-substrate:	0.349
PAMPA:	0.606 ? 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%):	0.035	30% Bioavailability (F30%):	0.481
50% Bioavailability (F50%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	1.0
Plasma Protein Binding (PPB):	81.196%	Volume Distribution (VD):	-0.488
Fu:	16.897% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.955	BCRP inhibitor:	0.061
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.254
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.222	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.985 ? 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):

5.816

Half-life (T1/2):

0.504

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.336
Human Hepatotoxicity (H-HT):	0.1	Drug-induced Liver Injury (DILI):	0.811
AMES Toxicity:	0.142	Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.321	Skin Sensitization:	0.989
Carcinogencity:	0.546	Eye Corrosion:	0.0
Eye Irritation:	0.305	Respiratory Toxicity:	0.063
Drug-induced Neurotoxicity:	0.16	Ototoxicity:	0.281
Hematotoxicity:	0.035	Drug-induced Nephrotoxicity:	0.794
Genotoxicity:	0.784	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.048	Hek293 Cytotoxicity:	0.119
BCF:	0.786 ? 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:	3.7 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.01 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.665 ? 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	5

Activity Type	# Activity
Cell line	1
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]
NPT2	Others	Unspecified	n.a.	Activity	=	7.5	%	PMID[20146433]
NPT2	Others	Unspecified	n.a.	Activity	=	36.6	%	PMID[20146433]
NPT2	Others	Unspecified	n.a.	Activity	=	87.6	%	PMID[20146433]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[20146433]

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 NPC127026 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	15321
0.1-0.2	32316
0.2-0.3	1618
0.3-0.4	386
0.4-0.5	170
0.5-0.6	27
0.6-0.7	13
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC483890
0.8214	Intermediate Similarity	NPC483880
0.8214	Intermediate Similarity	NPC156941
0.6951	Remote Similarity	NPC483889
0.675	Remote Similarity	NPC127720
0.6667	Remote Similarity	NPC483881
0.6395	Remote Similarity	NPC188865
0.6395	Remote Similarity	NPC56953
0.6279	Remote Similarity	NPC610927
0.625	Remote Similarity	NPC158663
0.6222	Remote Similarity	NPC483885
0.6207	Remote Similarity	NPC301368
0.6207	Remote Similarity	NPC84815
0.6129	Remote Similarity	NPC483891
0.6044	Remote Similarity	NPC479045
0.6	Remote Similarity	NPC609309
0.5909	Remote Similarity	NPC611111
0.5854	Remote Similarity	NPC270590
0.5778	Remote Similarity	NPC75600
0.5778	Remote Similarity	NPC483884
0.5625	Remote Similarity	NPC471980
0.5604	Remote Similarity	NPC483870
0.5604	Remote Similarity	NPC483871
0.5568	Remote Similarity	NPC483887
0.5568	Remote Similarity	NPC158020
0.5532	Remote Similarity	NPC176413
0.5532	Remote Similarity	NPC294512
0.5333	Remote Similarity	NPC212768
0.5233	Remote Similarity	NPC171207
0.5227	Remote Similarity	NPC70716
0.5227	Remote Similarity	NPC97667
0.5176	Remote Similarity	NPC483883
0.5176	Remote Similarity	NPC151585
0.5165	Remote Similarity	NPC276735
0.5165	Remote Similarity	NPC479049
0.5165	Remote Similarity	NPC4421
0.5165	Remote Similarity	NPC608007
0.5161	Remote Similarity	NPC184817
0.5119	Remote Similarity	NPC152440
0.5119	Remote Similarity	NPC483882
0.5119	Remote Similarity	NPC483888
0.5111	Remote Similarity	NPC479042
0.5054	Remote Similarity	NPC479048

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC127026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3515
0.1-0.2	5479
0.2-0.3	153
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