NPASS Compound

Natural Product: NPC118162

Natural Product ID	NPC118162
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gomisin C
IUPAC Name	n.a.
Synonyms	Gomisin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL404875
PubChem CID	151529
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 75 0 0 0 0 0 0 0 0999 V2000 0.7222 -3.3405 -0.4260 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0425 -2.5024 -1.6786 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2016 -2.5358 -2.5042 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4315 -2.2562 -1.7357 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3623 -3.2139 -1.9234 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5776 -3.1748 -1.2645 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8509 -2.1217 -0.3797 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9319 -1.1248 -0.1546 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7474 -1.2208 -0.8473 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0422 -0.0048 -0.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2632 0.2286 -0.0333 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 1.4820 0.3138 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3365 2.5103 0.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6396 2.2392 -0.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0119 0.9675 -0.5759 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2504 0.5799 -1.0530 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6041 0.6008 -2.4205 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5680 3.2595 -0.2863 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4231 3.6002 0.7970 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0021 3.8050 0.6003 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3151 4.0518 1.0466 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4467 -0.6841 0.0895 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6673 -1.2625 -1.2881 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4071 -0.1800 -2.3429 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0740 -1.4586 -1.3467 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5295 0.1573 0.4504 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2233 -0.0388 1.6406 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8211 -0.9993 2.3515 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3333 0.7886 2.0563 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7858 1.8395 1.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8594 2.6137 1.7312 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4617 2.3165 2.9303 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0234 1.2799 3.6922 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9535 0.5130 3.2514 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0728 -0.0532 0.7059 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6928 -0.0947 2.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1269 -2.2923 0.1637 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7652 -3.2684 -0.6391 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6902 -3.9889 -1.2608 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6324 -3.4164 0.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4923 -4.3835 -0.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1558 -2.9523 0.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7790 -3.1408 -2.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0897 -1.8394 -3.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3137 -3.5524 -2.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1186 -4.0160 -2.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6110 1.6633 0.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7039 0.7205 -3.0229 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1177 -0.3500 -2.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3366 1.4382 -2.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0028 2.6884 1.0810 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0864 4.4230 0.4607 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7992 3.9904 1.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5298 3.3345 1.8576 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0743 3.9068 0.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3292 5.0690 1.4881 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2799 -1.4432 0.8544 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9115 0.7721 -2.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3236 -0.0207 -2.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8429 -0.4685 -3.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3357 -1.7940 -2.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3318 2.0964 0.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1833 3.4271 1.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3037 2.9593 3.2259 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5016 1.0612 4.6216 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6557 -0.2970 3.9070 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9724 0.6946 2.2598 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3057 -1.0796 2.3668 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5757 0.1288 2.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4241 -3.9276 -0.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3119 -2.7091 -1.4520 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 14 18 1 0 18 19 1 0 13 20 1 0 20 21 1 0 11 22 1 0 22 23 1 0 23 24 1 0 23 25 1 1 22 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 8 35 1 0 35 36 1 0 7 37 1 0 37 38 1 0 38 39 1 0 23 2 1 0 34 29 1 0 9 4 1 0 15 10 1 0 39 6 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 6 3 44 1 0 3 45 1 0 5 46 1 0 12 47 1 0 17 48 1 0 17 49 1 0 17 50 1 0 19 51 1 0 19 52 1 0 19 53 1 0 21 54 1 0 21 55 1 0 21 56 1 0 22 57 1 1 24 58 1 0 24 59 1 0 24 60 1 0 25 61 1 0 30 62 1 0 31 63 1 0 32 64 1 0 33 65 1 0 34 66 1 0 36 67 1 0 36 68 1 0 36 69 1 0 38 70 1 0 38 71 1 0 M END

Standard InCHIKey	UFCGDBKFOKKVAC-DSASHONVSA-N
Standard InCHI	InChI=1S/C30H32O9/c1-16-12-18-13-21-25(38-15-37-21)26(35-5)22(18)23-19(14-20(33-3)24(34-4)27(23)36-6)28(30(16,2)32)39-29(31)17-10-8-7-9-11-17/h7-11,13-14,16,28,32H,12,15H2,1-6H3/t16-,28-,30-/m0/s1
SMILES	C[C@H]1Cc2cc3c(c(c2-c2c(cc(c(c2OC)OC)OC)[C@@H]([C@@]1(C)O)OC(=O)c1ccccc1)OC)OCO3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.2	Volume:	537.401 ? Van der Waals volume.
Dense:	0.998	LogP:	3.902 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.658 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.191 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	29.0
TPSA:	101.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.438	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.867	Fsp³:	0.367
MCE-18:	103.805 ? 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:	0.389	Fluc inhibitor:	0.241 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.457 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.669 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.049	Promiscuous compounds:	0.088

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.279	Pgp-substrate:	0.014
PAMPA:	0.212 ? 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%):	0.007	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.371

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.437	MRP1:	0.999
Plasma Protein Binding (PPB):	97.198%	Volume Distribution (VD):	0.037
Fu:	2.381% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.021
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.798	CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.525
CYP2C9-inhibitor:	0.031	CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.988
HLM stability:	0.767 ? 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):

3.172

Half-life (T1/2):

0.991

ADMET: Toxicity

hERG Blockers:	0.26	hERG Blockers (10um):	0.768
Human Hepatotoxicity (H-HT):	0.275	Drug-induced Liver Injury (DILI):	0.885
AMES Toxicity:	0.378	Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.717	Skin Sensitization:	0.878
Carcinogencity:	0.954	Eye Corrosion:	0.0
Eye Irritation:	0.319	Respiratory Toxicity:	0.57
Drug-induced Neurotoxicity:	0.901	Ototoxicity:	0.345
Hematotoxicity:	0.159	Drug-induced Nephrotoxicity:	0.832
Genotoxicity:	0.406	RPMI-8226 Immunitoxicity:	0.26
A549 Cytotoxicity:	0.602	Hek293 Cytotoxicity:	0.816
BCF:	1.57 ? 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:	4.135 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.944 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.897 ? 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
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350139]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
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]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8946749]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8584	Schisandra arisanensis	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]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	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]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	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]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14102	Kadsura interior	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]
NPO8584	Schisandra arisanensis	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
Ki	1
Kinact	1
IC50	7
Activity	5
Inhibition	1
GI50	6

Activity Type	# Activity
Individual protein	2
Cell line	11
Others	5
Non-molecular	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	399.0	nM	PMID[16248836]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Kinact	=	0.092	min-1	PMID[16248836]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	56400.0	nM	PMID[18063366]
NPT1086	Cell line	SK-HEP1	Homo sapiens	IC50	=	70400.0	nM	PMID[18063366]
NPT2548	Cell line	SNU-638	Homo sapiens	IC50	=	44700.0	nM	PMID[18063366]
NPT396	Cell line	T47D	Homo sapiens	IC50	=	51200.0	nM	PMID[18063366]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	>	100000.0	nM	PMID[18063366]
NPT111	Cell line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[18063366]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[12350139]
NPT2245	Cell line	SiHa	Homo sapiens	GI50	=	14700.0	nM	DOI[10.1039/C6MD00097E]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	=	2800.0	nM	DOI[10.1039/C6MD00097E]
NPT81	Cell line	A549	Homo sapiens	GI50	=	74900.0	nM	DOI[10.1039/C6MD00097E]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	>	100000.0	nM	DOI[10.1039/C6MD00097E]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	3600.0	nM	DOI[10.1039/C6MD00097E]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	13300.0	nM	DOI[10.1039/C6MD00097E]
NPT2	Others	Unspecified	n.a.	Activity	=	19.7	%	PMID[12350139]
NPT2	Others	Unspecified	n.a.	Activity	=	60.2	%	PMID[12350139]
NPT2	Others	Unspecified	n.a.	Activity	=	87.4	%	PMID[12350139]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[12350139]
NPT2	Others	Unspecified	n.a.	Inhibition	=	-139.0	%	PMID[23265871]

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 NPC118162 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	16641
0.1-0.2	29990
0.2-0.3	2983
0.3-0.4	138
0.4-0.5	69
0.5-0.6	18
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC83049
1.0	High Similarity	NPC320471
0.9677	High Similarity	NPC79322
0.7703	Intermediate Similarity	NPC88557
0.7571	Intermediate Similarity	NPC42797
0.6857	Remote Similarity	NPC191352
0.6849	Remote Similarity	NPC280778
0.6806	Remote Similarity	NPC126405
0.6806	Remote Similarity	NPC53669
0.6806	Remote Similarity	NPC77237
0.6806	Remote Similarity	NPC297271
0.6806	Remote Similarity	NPC224472
0.6806	Remote Similarity	NPC16791
0.6806	Remote Similarity	NPC217708
0.6575	Remote Similarity	NPC258322
0.6528	Remote Similarity	NPC198461
0.6364	Remote Similarity	NPC29727
0.6111	Remote Similarity	NPC319749
0.5833	Remote Similarity	NPC295297
0.5735	Remote Similarity	NPC53722
0.5735	Remote Similarity	NPC201404
0.5735	Remote Similarity	NPC290714
0.5732	Remote Similarity	NPC311912
0.5732	Remote Similarity	NPC477880
0.5465	Remote Similarity	NPC477882
0.5432	Remote Similarity	NPC475229
0.5366	Remote Similarity	NPC477884
0.5342	Remote Similarity	NPC76415
0.5342	Remote Similarity	NPC218510
0.5278	Remote Similarity	NPC304821
0.527	Remote Similarity	NPC328122
0.5238	Remote Similarity	NPC485504
0.5231	Remote Similarity	NPC145722
0.5231	Remote Similarity	NPC256776
0.5231	Remote Similarity	NPC185680
0.506	Remote Similarity	NPC483405

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC118162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3148
0.1-0.2	5837
0.2-0.3	163
0.3-0.4	2
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