NPASS Compound

Natural Product: NPC215019

Natural Product ID	NPC215019
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BTVDGMUSPORWED-MMNRRLNTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21575645
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 75 80 0 0 0 0 0 0 0 0999 V2000 7.4342 1.1244 -0.0450 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2125 1.5411 0.1987 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0120 0.7330 0.1097 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0755 -0.5767 -0.2494 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8960 -1.3288 -0.3267 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6693 -0.7686 -0.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6298 0.5411 0.3105 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7887 1.2931 0.3900 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3621 0.8572 0.5297 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5661 -0.1672 0.3383 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9040 -0.1506 0.4982 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4691 -0.7950 1.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8615 -0.7795 1.6849 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6636 -0.1237 0.7773 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0552 0.5139 -0.2657 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6740 0.5199 -0.4351 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0195 -0.1292 0.9427 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9696 0.4803 0.1222 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9081 -0.6083 -0.4226 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8380 0.0788 -1.3848 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5866 1.1506 -0.6444 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7014 2.0095 0.2107 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6113 2.6843 1.2416 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1936 1.6381 1.9680 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7741 1.2748 0.9379 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2004 1.9708 -1.6121 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7769 -0.8218 -1.9068 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1933 -1.6389 -1.0167 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3697 -1.2172 -0.0291 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 -2.5635 -0.3432 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4800 -3.4702 0.6126 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0650 -4.7274 0.2122 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0698 -5.1226 -1.1086 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5081 -4.2235 -2.0712 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9193 -2.9752 -1.6671 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5374 -4.5614 -3.4225 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3767 -5.6415 1.1563 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9147 -2.6677 -0.6888 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6198 1.9480 0.0497 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5433 3.2633 0.4126 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6972 4.0522 0.5011 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9233 3.4981 0.2197 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0121 2.1733 -0.1470 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8593 1.3949 -0.2328 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0928 4.2352 0.2924 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5386 0.0645 -0.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0720 2.5805 0.4945 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9811 -1.1001 -0.4863 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7154 2.3336 0.6777 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8521 -1.3171 2.2814 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2453 -1.3164 2.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6054 1.0503 -1.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2127 1.0314 -1.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5929 1.0249 -0.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5114 -0.9428 0.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2013 0.5093 -2.2013 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3728 0.6875 -0.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2291 2.8335 -0.3638 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9631 3.2335 1.9802 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3699 3.3172 0.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4660 1.0928 2.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8034 2.8738 -1.5939 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6485 -0.6869 -1.4874 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5198 -1.9742 -0.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4762 -3.1730 1.6561 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2623 -6.1253 -1.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2626 -2.2691 -2.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3464 -4.9903 -3.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2368 -5.8352 1.9581 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5972 -2.9765 -1.3819 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6179 3.7683 0.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6565 5.0960 0.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9539 1.7071 -0.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8923 0.3455 -0.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1082 5.2394 0.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 1 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 14 17 1 0 17 18 1 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 22 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 10 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 32 37 1 0 5 38 1 0 1 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 42 45 1 0 8 3 1 0 16 11 1 0 25 18 1 0 35 30 1 0 44 39 1 0 29 6 1 0 1 46 1 0 2 47 1 0 4 48 1 0 8 49 1 0 12 50 1 0 13 51 1 0 15 52 1 0 16 53 1 0 18 54 1 6 19 55 1 1 20 56 1 6 21 57 1 1 22 58 1 6 23 59 1 0 23 60 1 0 24 61 1 0 26 62 1 0 27 63 1 0 28 64 1 0 31 65 1 0 33 66 1 0 35 67 1 0 36 68 1 0 37 69 1 0 38 70 1 0 40 71 1 0 41 72 1 0 43 73 1 0 44 74 1 0 45 75 1 0 M END

Standard InCHIKey	BTVDGMUSPORWED-MMNRRLNTSA-N
Standard InCHI	InChI=1S/C34H30O11/c35-16-27-30(40)31(41)32(42)34(45-27)43-24-9-5-19(6-10-24)33-28(20-13-22(37)15-23(38)14-20)29-25(39)11-18(12-26(29)44-33)2-1-17-3-7-21(36)8-4-17/h1-15,27,30-32,34-42H,16H2/b2-1+/t27-,30-,31+,32-,34-/m1/s1
SMILES	C(=Cc1cc(c2c(c1)oc(c1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)c2c1cc(cc(c1)O)O)O)/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	614.18	Volume:	605.063 ? Van der Waals volume.
Dense:	1.015	LogP:	3.371 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.28 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.21 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	35.0
TPSA:	193.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.124	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.254	Fsp³:	0.176
MCE-18:	117.0 ? 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:	0.952	Fluc inhibitor:	0.996 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.965 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.999 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.44	Promiscuous compounds:	0.242

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.267	MDCK Permeability:	-5.032
Pgp-inhibitor:	0.0	Pgp-substrate:	0.084
PAMPA:	0.961 ? 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):	0.004
20% Bioavailability (F20%):	0.776	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.053
Plasma Protein Binding (PPB):	89.232%	Volume Distribution (VD):	0.02
Fu:	11.802% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.316
BSEP inhibitor:	0.126

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.332	CYP2D6-substrate:	0.756
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.619
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.843 ? 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):

2.145

Half-life (T1/2):

3.654

ADMET: Toxicity

hERG Blockers:	0.129	hERG Blockers (10um):	0.424
Human Hepatotoxicity (H-HT):	0.786	Drug-induced Liver Injury (DILI):	0.897
AMES Toxicity:	0.861	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.51	Skin Sensitization:	0.99
Carcinogencity:	0.106	Eye Corrosion:	0.0
Eye Irritation:	0.591	Respiratory Toxicity:	0.029
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.764
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.507
Genotoxicity:	0.971	RPMI-8226 Immunitoxicity:	0.193
A549 Cytotoxicity:	0.939	Hek293 Cytotoxicity:	0.933
BCF:	1.255 ? 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:	4.397 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.588 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.242 ? 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
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[30413343]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783160]
NPO18427	Axinella agnata	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10064	Diospyros canaliculata	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5869	Anthocercis albicans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19091	Bacterium from	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16548	Chenopodium formosanum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10984	Euclea crispa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17900	Iotrochota birotulata	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11360	Tiliacora racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3096	Verbascum laxum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3096	Verbascum laxum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10064	Diospyros canaliculata	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18427	Axinella agnata	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11360	Tiliacora racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10984	Euclea crispa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5869	Anthocercis albicans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16548	Chenopodium formosanum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19091	Bacterium from	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17900	Iotrochota birotulata	Species	Iotrochotidae	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

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

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 NPC215019 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	20460
0.1-0.2	25639
0.2-0.3	2732
0.3-0.4	830
0.4-0.5	189
0.5-0.6	5
0.6-0.7	1
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	Natural Product ID
0.6375	Remote Similarity	NPC137100
0.5181	Remote Similarity	NPC26080
0.5181	Remote Similarity	NPC165686
0.5106	Remote Similarity	NPC143851
0.5053	Remote Similarity	NPC64305
0.5045	Remote Similarity	NPC470712

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC215019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4478
0.1-0.2	4610
0.2-0.3	51
0.3-0.4	10
0.4-0.5	1
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