NPASS Compound

Natural Product: NPC95075

Natural Product ID	NPC95075
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(-)-Antofine
IUPAC Name	(13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
Synonyms	(-)-Antofine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL228286
PubChem CID	639288
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001906] Phenanthroindolizidines

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 52 56 0 0 0 0 0 0 0 0999 V2000 6.2853 0.8052 1.1742 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1175 0.3330 0.9193 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9275 -0.1111 0.6589 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6463 -1.4939 0.6166 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3682 -1.8977 0.3359 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3373 -0.9920 0.0912 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6254 0.3675 0.1352 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8931 0.8065 0.4130 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6201 1.3094 -0.1077 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9045 2.6590 -0.0667 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1293 3.5458 -0.3178 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0798 4.9156 -0.2941 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3392 5.4961 -0.0164 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4050 3.0978 -0.6006 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6492 1.7237 -0.6321 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6414 0.8322 -0.3866 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9516 -0.5267 -0.4351 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0667 -1.4240 -0.1897 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1344 -2.9100 -0.2056 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4925 -3.3020 -0.4083 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8795 -4.5148 0.2326 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4032 -4.4415 0.2896 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7405 -2.9918 -0.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4223 -2.3182 0.1739 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2622 -1.0857 -0.7298 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4488 3.9744 -0.8539 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7239 3.4393 -1.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2723 1.5513 2.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7106 1.3812 0.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0453 0.0098 1.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4418 -2.2059 0.8059 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1145 -2.9584 0.2909 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1874 1.8241 0.4636 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8648 3.0772 0.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8674 4.9966 0.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9668 5.3627 -0.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2812 6.5661 0.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6265 1.3416 -0.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5031 -3.3017 -1.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2099 -3.3484 0.7562 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6111 -5.4097 -0.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4290 -4.5752 1.2371 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8805 -5.1494 -0.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6827 -4.6433 1.3470 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0030 -2.9007 -1.1122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5173 -2.5993 0.6298 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1752 -2.1023 1.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1375 -0.4784 -0.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -1.5215 -1.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6446 2.8114 -2.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4814 4.2361 -1.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0121 2.7401 -0.3153 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 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 2 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 1 0 22 23 1 0 23 24 1 0 24 25 1 0 14 26 1 0 26 27 1 0 8 3 1 0 16 9 1 0 25 17 1 0 18 6 1 0 24 20 1 0 1 28 1 0 1 29 1 0 1 30 1 0 4 31 1 0 5 32 1 0 8 33 1 0 10 34 1 0 13 35 1 0 13 36 1 0 13 37 1 0 15 38 1 0 19 39 1 0 19 40 1 0 21 41 1 0 21 42 1 0 22 43 1 0 22 44 1 0 23 45 1 0 23 46 1 0 24 47 1 1 25 48 1 0 25 49 1 0 27 50 1 0 27 51 1 0 27 52 1 0 M END

Standard InCHIKey	NCVWJDISIZHFQS-CQSZACIVSA-N
Standard InCHI	InChI=1S/C23H25NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,10-12,14H,4-5,8-9,13H2,1-3H3/t14-/m1/s1
SMILES	COc1ccc2c(c1)c1cc(OC)c(cc1c1c2CN2CCC[C@@H]2C1)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	363.18	Volume:	382.494 ? Van der Waals volume.
Dense:	0.95	LogP:	3.927 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.37 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	25.0
TPSA:	30.93 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.639	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.868	Fsp³:	0.391
MCE-18:	87.75 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.853	Fluc inhibitor:	0.057 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.771 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.304 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.453

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.481	MDCK Permeability:	-4.687
Pgp-inhibitor:	0.894	Pgp-substrate:	0.907
PAMPA:	0.001 ? 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%):	0.014	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.57

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202	MRP1:	0.92
Plasma Protein Binding (PPB):	81.655%	Volume Distribution (VD):	0.167
Fu:	14.332% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.998
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.78
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.993	CYP3A4-substrate:	0.584
CYP2B6-substrate:	0.999	CYP2C8-inhibitor:	0.003
HLM stability:	0.915 ? 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):

8.488

Half-life (T1/2):

1.168

ADMET: Toxicity

hERG Blockers:	0.827	hERG Blockers (10um):	0.749
Human Hepatotoxicity (H-HT):	0.804	Drug-induced Liver Injury (DILI):	0.701
AMES Toxicity:	0.755	Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.977	Skin Sensitization:	0.558
Carcinogencity:	0.795	Eye Corrosion:	0.0
Eye Irritation:	0.117	Respiratory Toxicity:	0.995
Drug-induced Neurotoxicity:	0.975	Ototoxicity:	0.739
Hematotoxicity:	0.562	Drug-induced Nephrotoxicity:	0.92
Genotoxicity:	0.839	RPMI-8226 Immunitoxicity:	0.292
A549 Cytotoxicity:	0.477	Hek293 Cytotoxicity:	0.802
BCF:	2.141 ? 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:	4.447 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.023 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.342 ? 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
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087617]
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	roots	n.a.	n.a.	PMID[14738392]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24897106]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18056	Silene rubicunda	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24694	Vincetoxicum pycnostelma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24981	Dimetia capitellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24694	Vincetoxicum pycnostelma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17803	Parmelia omphalodes	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24981	Dimetia capitellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14290	Bryonia cretica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18515	Uncaria pilosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18788	Isertia hypoleuca	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18056	Silene rubicunda	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8035	Tylophora tanakae	Species	Apocynaceae	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	10
IC50	40
Inhibition	14
GI50	8
Ratio	1
GI	1

Activity Type	# Activity
Cell line	36
Individual protein	1
Non-molecular	8
Organism	21
Others	8

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	37.9	%	PMID[23294831]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	IC50	=	8.0	nM	PMID[17585747]
NPT91	Cell line	KB	Homo sapiens	IC50	=	13.0	nM	PMID[17585747]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	9.0	nM	PMID[17585747]
NPT133	Cell line	ZR-75-1	Homo sapiens	IC50	=	8.0	nM	PMID[17585747]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	9.9	nM	PMID[17049857]
NPT453	Cell line	HT-1080	Homo sapiens	IC50	=	9.6	nM	PMID[17049857]
NPT81	Cell line	A549	Homo sapiens	IC50	=	10.4	nM	PMID[17049857]
NPT461	Cell line	PANC-1	Homo sapiens	GI50	=	2.2	nM	PMID[18077159]
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	=	5.2	nM	PMID[18077159]
NPT91	Cell line	KB	Homo sapiens	IC50	=	36.0	nM	PMID[22823514]
NPT81	Cell line	A549	Homo sapiens	IC50	=	22.0	nM	PMID[22823514]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	25.0	nM	PMID[22823514]
NPT81	Cell line	A549	Homo sapiens	GI50	=	22.0	nM	PMID[21668000]
NPT90	Cell line	DU-145	Homo sapiens	GI50	=	25.0	nM	PMID[21668000]
NPT91	Cell line	KB	Homo sapiens	GI50	=	36.0	nM	PMID[21668000]
NPT81	Cell line	A549	Homo sapiens	GI50	=	10.0	nM	PMID[22417638]
NPT116	Cell line	HL-60	Homo sapiens	GI50	<	1.0	nM	PMID[22417638]
NPT81	Cell line	A549	Homo sapiens	IC50	=	18.0	nM	PMID[23294831]
NPT81	Cell line	A549	Homo sapiens	IC50	=	11.0	nM	PMID[23294831]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	8.0	nM	PMID[23294831]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	13.0	nM	PMID[23294831]
NPT2548	Cell line	SNU-638	Homo sapiens	IC50	=	10.0	nM	PMID[23294831]
NPT1086	Cell line	SK-HEP1	Homo sapiens	IC50	=	8.0	nM	PMID[23294831]
NPT81	Cell line	A549	Homo sapiens	IC50	=	10.0	nM	PMID[25499434]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	12.34	nM	PMID[26393416]
NPT308	Cell line	CAKI-1	Homo sapiens	IC50	=	6.23	nM	PMID[26393416]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	6.04	nM	PMID[26393416]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	6.03	nM	PMID[26393416]
NPT81	Cell line	A549	Homo sapiens	IC50	=	8.52	nM	PMID[26393416]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	12.0	nM	PMID[28431881]
NPT81	Cell line	A549	Homo sapiens	IC50	=	20000.0	nM	PMID[35033884]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	9.0	nM	PMID[17585747]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	4.9	nM	PMID[18077159]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	16.0	nM	PMID[12350151]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	14.0	nM	PMID[12350151]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	25.0	nM	PMID[22823514]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	6.32	nM	PMID[26393416]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	10.38	nM	PMID[26393416]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	65.0	%	PMID[17822295]
NPT2	Others	Unspecified	n.a.	IC50	=	7.3	nM	PMID[18077159]
NPT2	Others	Unspecified	n.a.	IC50	=	167.0	nM	PMID[18077159]
NPT2	Others	Unspecified	n.a.	IC50	=	135.0	nM	PMID[18077159]
NPT2	Others	Unspecified	n.a.	IC50	=	24.0	nM	PMID[18077159]
NPT2	Others	Unspecified	n.a.	Ratio	=	1.5	n.a.	PMID[18077159]
NPT2	Others	Unspecified	n.a.	Activity	=	34.0	n.a.	PMID[18077159]
NPT2	Others	Unspecified	n.a.	Activity	=	28.0	n.a.	PMID[18077159]
NPT2	Others	Unspecified	n.a.	Activity	=	4.9	n.a.	PMID[18077159]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	63.0	%	PMID[22662864]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	GI	=	63.0	%	PMID[22880628]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	20.4	%	PMID[23035814]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	45.5	%	PMID[23035814]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	19.4	%	PMID[23035814]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	46.0	%	PMID[23035814]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	15.3	%	PMID[23035814]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	42.7	%	PMID[23035814]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	27.4	%	PMID[23035814]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	52.8	%	PMID[23035814]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	29.2	%	PMID[16190646]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	14.0	%	PMID[16190646]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	33.4	%	PMID[23320928]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	62.5	%	PMID[23320928]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	29.4	%	PMID[23320928]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	58.0	%	PMID[23320928]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	32.3	%	PMID[23320928]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	55.7	%	PMID[23320928]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.4	%	PMID[23320928]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	65.8	%	PMID[23320928]

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 NPC95075 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	31866
0.1-0.2	17537
0.2-0.3	429
0.3-0.4	6
0.4-0.5	1
0.5-0.6	5
0.6-0.7	3
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC90844
1.0	High Similarity	NPC253883
0.9245	High Similarity	NPC219162
0.9245	High Similarity	NPC605089
0.8947	High Similarity	NPC76079
0.8269	Intermediate Similarity	NPC130941
0.8269	Intermediate Similarity	NPC605913
0.8246	Intermediate Similarity	NPC92541
0.7797	Intermediate Similarity	NPC603531
0.75	Intermediate Similarity	NPC244112
0.7302	Intermediate Similarity	NPC487714
0.6935	Remote Similarity	NPC186063
0.6349	Remote Similarity	NPC150879
0.6094	Remote Similarity	NPC233650
0.5909	Remote Similarity	NPC169743
0.5606	Remote Similarity	NPC487715
0.5429	Remote Similarity	NPC487711
0.5429	Remote Similarity	NPC487712
0.5429	Remote Similarity	NPC487713

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC95075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4762
0.1-0.2	4207
0.2-0.3	180
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