NPASS Compound

Natural Product: NPC294436

Natural Product ID	NPC294436
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RMPVPCOAQGDYKB-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	91387732
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

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 62 67 0 0 0 0 0 0 0 0999 V2000 0.2512 -4.2925 1.7231 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2999 -3.1086 0.9624 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7883 -2.2473 0.8124 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9982 -2.5063 1.4090 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1029 -1.6499 1.2696 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9065 -0.5338 0.5002 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9902 0.4592 0.3887 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2407 0.1939 0.8788 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2688 1.1235 0.6632 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0050 2.2707 -0.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7682 2.5522 -0.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7212 1.6276 -0.3124 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3756 2.0038 -0.7804 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4594 0.8789 -1.0145 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6842 -0.2713 -0.1063 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5866 -1.1327 0.0407 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6942 -0.8398 -0.6020 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6683 -0.0782 0.0719 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3238 0.3284 1.4241 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2318 1.3564 1.9693 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5338 1.5128 1.3316 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5058 2.2677 2.0106 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7376 2.4945 1.4396 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0508 2.0009 0.2134 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0810 1.2420 -0.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8582 1.0176 0.0975 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8767 0.1764 -0.5866 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0852 -0.3131 -1.8488 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1122 -1.0695 -2.5098 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9292 -1.3180 -1.8681 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0936 -2.0697 -2.4718 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1608 -2.5561 -3.7745 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2475 -0.1001 -2.5483 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6443 3.2444 2.1626 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0267 3.1860 -0.2402 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2692 -2.0123 1.9166 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3701 -4.1938 2.6456 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2609 -4.5913 2.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1621 -5.0877 1.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1389 -3.4039 2.0208 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4766 -0.6863 1.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2290 0.8611 1.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5265 3.4558 -1.0767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4646 2.6738 -1.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9291 2.6216 0.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5660 0.5546 -2.0853 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4150 1.2743 -0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2664 0.6830 1.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4175 -0.5745 2.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7002 2.3604 1.8578 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4182 1.2093 3.0822 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2691 2.6653 2.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0072 2.1618 -0.2615 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3535 0.8690 -1.4214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2832 -1.4518 -3.5032 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6891 -3.1652 -4.1396 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0834 -3.1947 -3.8002 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3502 -1.7354 -4.4951 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6748 -0.7576 -3.1855 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5963 2.9033 2.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0950 3.6775 -1.1230 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6259 -2.9661 1.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 28 33 1 0 23 34 1 0 10 35 1 0 5 36 1 0 16 3 1 0 30 17 1 0 15 6 1 0 27 18 1 0 12 7 1 0 26 21 1 0 1 37 1 0 1 38 1 0 1 39 1 0 4 40 1 0 8 41 1 0 9 42 1 0 11 43 1 0 13 44 1 0 13 45 1 0 14 46 1 0 14 47 1 0 19 48 1 0 19 49 1 0 20 50 1 0 20 51 1 0 22 52 1 0 24 53 1 0 25 54 1 0 29 55 1 0 32 56 1 0 32 57 1 0 32 58 1 0 33 59 1 0 34 60 1 0 35 61 1 0 36 62 1 0 M END

Standard InCHIKey	RMPVPCOAQGDYKB-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C30H26O6/c1-35-25-13-23(33)27-19-9-5-17(31)11-15(19)3-7-21(27)29(25)30-22-8-4-16-12-18(32)6-10-20(16)28(22)24(34)14-26(30)36-2/h5-6,9-14,31-34H,3-4,7-8H2,1-2H3
SMILES	COc1cc(c2-c3ccc(cc3CCc2c1c1c2CCc3cc(ccc3-c2c(cc1OC)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	482.17	Volume:	497.201 ? Van der Waals volume.
Dense:	0.97	LogP:	3.72 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.26 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.128 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	32.0
TPSA:	99.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.298	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.981	Fsp³:	0.2
MCE-18:	75.556 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.998	Fluc inhibitor:	0.646 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.717 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.611 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.283	Promiscuous compounds:	0.151

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.917	MDCK Permeability:	-4.79
Pgp-inhibitor:	0.025	Pgp-substrate:	0.28
PAMPA:	0.074 ? 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):	0.006
20% Bioavailability (F20%):	0.638	30% Bioavailability (F30%):	0.683
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019	MRP1:	0.648
Plasma Protein Binding (PPB):	94.925%	Volume Distribution (VD):	0.58
Fu:	6.88% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.597
BSEP inhibitor:	0.701

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.994
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.997	CYP2D6-substrate:	0.961
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	0.993
CYP2B6-substrate:	0.772	CYP2C8-inhibitor:	1.0
HLM stability:	0.989 ? 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):

2.277

Half-life (T1/2):

2.186

ADMET: Toxicity

hERG Blockers:	0.485	hERG Blockers (10um):	0.739
Human Hepatotoxicity (H-HT):	0.802	Drug-induced Liver Injury (DILI):	0.214
AMES Toxicity:	0.887	Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.981	Skin Sensitization:	0.959
Carcinogencity:	0.913	Eye Corrosion:	0.0
Eye Irritation:	0.152	Respiratory Toxicity:	0.992
Drug-induced Neurotoxicity:	0.537	Ototoxicity:	0.869
Hematotoxicity:	0.356	Drug-induced Nephrotoxicity:	0.385
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.099
A549 Cytotoxicity:	0.915	Hek293 Cytotoxicity:	0.953
BCF:	1.731 ? 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:	5.372 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.888 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.689 ? 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
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425112]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15686910]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	Fibrous Roots	n.a.	n.a.	PMID[25760525]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31415170]
NPO11893	Telesto riisei	Species	Telestidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7857405]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14620	Sedum alfredi	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO445	Desmarestia aculeata	Species	Desmarestiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26125	Pseudomonas corrugata	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13086	Streptomyces carzinostaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3644	Climacoptera lanata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8734	Centaurea pabotii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11893	Telesto riisei	Species	Telestidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26125	Pseudomonas corrugata	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13086	Streptomyces carzinostaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14620	Sedum alfredi	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12919	Clibadium glabrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13913	Ravensara aromatica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6224	Grindelia boliviana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12597	Eria barbata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7186	Hypogymnia enteromorpha	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14509	Stevia seleriana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13511	Monopteryx inpae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO445	Desmarestia aculeata	Species	Desmarestiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16226	Prinsepia utilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
MIC	9
EC50	1

Activity Type	# Activity
Cell line	1
No target	1
Non-molecular	6
Others	6

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
NPT34	Cell line	BV-2	Mus musculus	IC50	=	39400.0	nM	PMID[31415170]
NPT28833	No target	No relevant target	n.a.	EC50	=	7700.0	nM	PMID[29280630]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[27310249]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	MIC	>	400000.0	nM	PMID[27310249]
NPT610	Others	Molecular identity unknown	n.a.	MIC	>	400000.0	nM	PMID[27310249]

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 NPC294436 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	27859
0.1-0.2	18620
0.2-0.3	3244
0.3-0.4	91
0.4-0.5	18
0.5-0.6	12
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8636	High Similarity	NPC258780
0.8039	Intermediate Similarity	NPC58963
0.7451	Intermediate Similarity	NPC478417
0.7308	Intermediate Similarity	NPC191462
0.717	Intermediate Similarity	NPC31342
0.7018	Intermediate Similarity	NPC206158
0.6889	Remote Similarity	NPC228503
0.6809	Remote Similarity	NPC138248
0.678	Remote Similarity	NPC274472
0.6552	Remote Similarity	NPC478412
0.64	Remote Similarity	NPC478416
0.6154	Remote Similarity	NPC220688
0.6032	Remote Similarity	NPC478413
0.5862	Remote Similarity	NPC212048
0.58	Remote Similarity	NPC69029
0.5738	Remote Similarity	NPC480632
0.5672	Remote Similarity	NPC206525
0.56	Remote Similarity	NPC108198
0.5588	Remote Similarity	NPC472648
0.5517	Remote Similarity	NPC282508
0.5385	Remote Similarity	NPC200557
0.5319	Remote Similarity	NPC142588
0.5254	Remote Similarity	NPC105620
0.5192	Remote Similarity	NPC105718
0.5098	Remote Similarity	NPC125649

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC294436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5426
0.1-0.2	3648
0.2-0.3	75
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