NPASS Compound

Natural Product: NPC126405

Natural Product ID	NPC126405
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Schisantherin B
IUPAC Name	n.a.
Synonyms	Schisantherin B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL490308
PubChem CID	6438572
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 71 74 0 0 0 0 0 0 0 0999 V2000 5.6104 -2.4784 -1.6552 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7692 -1.8671 -0.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8226 -1.1450 0.2467 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0810 -0.5773 1.5919 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5765 -0.9338 -0.4621 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3409 -1.4075 -1.6009 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5300 -0.1707 0.0884 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3131 0.0294 -0.6157 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1451 -0.5364 0.0881 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4393 -1.7931 0.5468 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4876 -2.5102 1.2643 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7449 -1.9744 1.5438 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0777 -0.7167 1.1043 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1277 -0.0359 0.3857 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8240 1.2008 0.0126 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4586 2.5472 0.0879 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2094 3.2234 0.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0087 2.3507 0.3532 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2086 3.2598 0.6072 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1299 1.5338 -0.8656 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4468 1.9390 -1.5574 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1565 1.7610 -1.8292 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4038 3.4583 -0.2977 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6437 3.0586 -0.7352 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9633 1.6942 -0.7971 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0462 0.7392 -0.4226 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2546 -0.6244 -0.4673 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9868 -1.4334 -1.5905 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2651 1.5811 -1.2692 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7585 2.8616 -1.6104 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7445 3.7604 -1.1663 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2767 -0.0864 1.3439 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5239 0.7118 2.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7090 -2.6647 2.2647 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6004 -3.4785 1.4964 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2017 -3.7740 1.7258 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0659 -4.3297 1.4510 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5234 -3.0608 -1.9250 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4808 -1.7395 -2.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7859 -3.2360 -1.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7210 -2.0334 0.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1565 -0.6125 2.2060 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8379 -1.1811 2.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4873 0.4503 1.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3918 -0.5031 -1.5852 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4214 -2.2249 0.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3040 3.5425 1.5399 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0954 4.1556 -0.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9869 1.6533 1.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1574 2.7731 0.4043 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2229 3.5686 1.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1332 4.1988 0.0310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5429 3.0405 -1.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4106 1.6138 -2.6394 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3042 1.4249 -1.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1374 0.9367 -2.4005 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1488 4.5229 -0.2501 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5958 -2.3397 -1.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9042 -1.6356 -1.6252 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1992 -0.7677 -2.4768 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6918 3.0050 -1.0309 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9550 2.9845 -2.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7188 0.6043 3.2443 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6673 1.7375 2.1677 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4590 0.3802 3.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9788 -3.9801 0.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2926 -2.7843 0.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1383 -4.1956 2.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0945 -5.3162 1.9704 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8763 -3.7148 1.8629 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1404 -4.4400 0.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 6 16 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 25 29 1 0 29 30 1 0 30 31 1 0 13 32 1 0 32 33 1 0 12 34 1 0 34 35 1 0 11 36 1 0 36 37 1 0 20 8 1 0 31 24 1 0 14 9 1 0 26 15 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 4 42 1 0 4 43 1 0 4 44 1 0 8 45 1 6 10 46 1 0 17 47 1 0 17 48 1 0 18 49 1 1 19 50 1 0 19 51 1 0 19 52 1 0 21 53 1 0 21 54 1 0 21 55 1 0 22 56 1 0 23 57 1 0 28 58 1 0 28 59 1 0 28 60 1 0 30 61 1 0 30 62 1 0 33 63 1 0 33 64 1 0 33 65 1 0 35 66 1 0 35 67 1 0 35 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 M END

Standard InCHIKey	BKGUPIVDQHHVMV-RZGKOBFOSA-N
Standard InCHI	InChI=1S/C28H34O9/c1-9-14(2)27(29)37-26-17-12-18(31-5)22(32-6)25(34-8)21(17)20-16(10-15(3)28(26,4)30)11-19-23(24(20)33-7)36-13-35-19/h9,11-12,15,26,30H,10,13H2,1-8H3/b14-9-/t15-,26-,28-/m0/s1
SMILES	C/C=C(/C)C(=O)O[C@H]1c2cc(c(c(c2-c2c(C[C@H](C)[C@]1(C)O)cc1c(c2OC)OCO1)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	514.22	Volume:	516.639 ? Van der Waals volume.
Dense:	0.995	LogP:	2.894 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.992 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.477 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	24.0
TPSA:	101.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.437	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.139	Fsp³:	0.464
MCE-18:	94.073 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.2	Fluc inhibitor:	0.233 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.435 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.434 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.115	Promiscuous compounds:	0.314

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.036	MDCK Permeability:	-4.762
Pgp-inhibitor:	0.037	Pgp-substrate:	0.038
PAMPA:	0.423 ? 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%):	0.144	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.777

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.363	MRP1:	0.999
Plasma Protein Binding (PPB):	94.645%	Volume Distribution (VD):	0.23
Fu:	5.063% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.972
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.009
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.28	CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.036	CYP2D6-substrate:	0.99
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.101	CYP2C8-inhibitor:	0.284
HLM stability:	0.781 ? 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):

4.068

Half-life (T1/2):

1.03

ADMET: Toxicity

hERG Blockers:	0.136	hERG Blockers (10um):	0.526
Human Hepatotoxicity (H-HT):	0.685	Drug-induced Liver Injury (DILI):	0.794
AMES Toxicity:	0.652	Rat Oral Acute Toxicity:	0.554
Maximum Recommended Daily Dose:	0.867	Skin Sensitization:	0.961
Carcinogencity:	0.968	Eye Corrosion:	0.006
Eye Irritation:	0.359	Respiratory Toxicity:	0.733
Drug-induced Neurotoxicity:	0.826	Ototoxicity:	0.439
Hematotoxicity:	0.525	Drug-induced Nephrotoxicity:	0.878
Genotoxicity:	0.697	RPMI-8226 Immunitoxicity:	0.342
A549 Cytotoxicity:	0.654	Hek293 Cytotoxicity:	0.749
BCF:	1.679 ? 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:	3.921 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.66 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.718 ? 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
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	Stems	Luoji Mountain Village, Xichang County, Sicuan Province, China	2011-Sep	PMID[23738539]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34684838]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	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
EC50	2
IC50	1

Activity Type	# Activity
Cell line	1
Organism	2

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
NPT759	Cell line	H9	Homo sapiens	IC50	>	49000.0	nM	PMID[17190445]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40000.0	nM	PMID[17190445]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	22.1	ug.mL-1	PMID[21232955]

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 NPC126405 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	11334
0.1-0.2	35852
0.2-0.3	2390
0.3-0.4	164
0.4-0.5	57
0.5-0.6	29
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC53669
1.0	High Similarity	NPC77237
1.0	High Similarity	NPC297271
1.0	High Similarity	NPC16791
1.0	High Similarity	NPC217708
0.9661	High Similarity	NPC198461
0.8814	High Similarity	NPC295297
0.8154	Intermediate Similarity	NPC224472
0.7606	Intermediate Similarity	NPC485504
0.7463	Intermediate Similarity	NPC470916
0.7424	Intermediate Similarity	NPC308739
0.7324	Intermediate Similarity	NPC29727
0.6806	Remote Similarity	NPC83049
0.6806	Remote Similarity	NPC320471
0.6806	Remote Similarity	NPC118162
0.6716	Remote Similarity	NPC85141
0.6528	Remote Similarity	NPC79322
0.625	Remote Similarity	NPC53722
0.625	Remote Similarity	NPC201404
0.625	Remote Similarity	NPC290714
0.6212	Remote Similarity	NPC327352
0.6212	Remote Similarity	NPC198129
0.6212	Remote Similarity	NPC252281
0.6029	Remote Similarity	NPC322426
0.6029	Remote Similarity	NPC76415
0.6029	Remote Similarity	NPC218510
0.5921	Remote Similarity	NPC475592
0.589	Remote Similarity	NPC24562
0.5857	Remote Similarity	NPC316989
0.5616	Remote Similarity	NPC312763
0.5513	Remote Similarity	NPC476065
0.5507	Remote Similarity	NPC304821
0.5484	Remote Similarity	NPC145722
0.5484	Remote Similarity	NPC256776
0.5484	Remote Similarity	NPC185680
0.5443	Remote Similarity	NPC63061
0.5432	Remote Similarity	NPC348849
0.5432	Remote Similarity	NPC178195
0.5395	Remote Similarity	NPC473323
0.5385	Remote Similarity	NPC326144
0.5325	Remote Similarity	NPC477885
0.525	Remote Similarity	NPC475229
0.5238	Remote Similarity	NPC88557
0.5217	Remote Similarity	NPC318286
0.5161	Remote Similarity	NPC32189
0.5143	Remote Similarity	NPC137352
0.5143	Remote Similarity	NPC183083
0.5143	Remote Similarity	NPC485503
0.5132	Remote Similarity	NPC471154
0.5072	Remote Similarity	NPC327651
0.507	Remote Similarity	NPC321958
0.507	Remote Similarity	NPC230538
0.507	Remote Similarity	NPC229172
0.507	Remote Similarity	NPC103637
0.507	Remote Similarity	NPC36531

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC126405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3901
0.1-0.2	5158
0.2-0.3	88
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