NPASS Compound

Natural Product: NPC156851

Natural Product ID	NPC156851
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UTUISHMYVAZILQ-NBJODKRESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	16109840
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 68 72 0 0 0 0 0 0 0 0999 V2000 -6.2558 1.6151 0.3711 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0542 2.2958 -0.8076 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8651 2.1326 -1.9044 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9072 1.2400 -1.7669 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1319 0.5500 -0.6152 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2726 0.7383 0.5075 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4888 -0.1036 1.6575 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6263 -0.6855 2.4162 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2041 -0.6495 2.2790 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4888 -1.2524 3.1873 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4191 -0.0838 1.3236 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0064 -0.1178 1.2805 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4724 1.2761 1.3809 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8567 1.8308 2.7634 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0567 1.1644 3.7189 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1717 1.4704 1.0975 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6656 0.8672 0.0016 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5764 -0.0447 -0.7767 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5046 -0.8540 0.0652 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9095 -2.0641 0.4101 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3114 0.7039 -1.6960 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5668 0.2157 0.2288 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7544 0.4102 -0.4050 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9677 1.2936 -1.4573 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2427 1.4000 -2.0236 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3097 0.6533 -1.5726 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5519 0.7809 -2.1515 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7436 1.5723 -3.0951 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5753 -0.0170 -1.6285 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3372 -0.8813 -0.5874 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3959 -1.7188 -0.0318 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1170 -2.5807 1.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1052 -3.3738 1.5676 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3993 -3.3725 1.0961 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6848 -2.5261 0.0420 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6778 -1.7146 -0.5025 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3823 -4.1810 1.6468 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1242 -0.9436 -0.0915 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1081 -0.2336 -0.5202 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8525 -0.3301 0.0278 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4694 2.2806 -3.0784 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5974 2.8516 -3.0492 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6199 1.8770 1.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2202 3.0070 -0.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5581 1.1118 -2.6488 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9405 -0.1436 -0.5063 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5994 -0.2346 1.8828 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0871 -1.2672 3.2558 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6806 -0.6765 2.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0860 1.9071 0.6698 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7682 2.9127 2.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9048 1.5541 2.9979 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5557 0.4473 4.1321 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4192 1.7113 -0.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9227 -0.7140 -1.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3968 -1.1155 -0.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1518 -2.7731 -0.2398 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7934 0.9040 -2.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1761 1.8879 -1.8395 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5370 0.0928 -2.0892 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1103 -2.5782 1.4000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9017 -4.0466 2.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6914 -2.5095 -0.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9352 -1.0719 -1.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1282 -4.5970 1.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7017 -1.0180 0.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2445 3.2682 -2.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2447 2.4505 -3.9142 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 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 0 17 22 1 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 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 30 38 1 0 38 39 1 0 39 40 2 0 25 41 1 0 3 42 1 0 6 1 1 0 19 12 1 0 40 23 1 0 39 26 1 0 36 31 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 7 47 1 0 8 48 1 0 12 49 1 1 13 50 1 6 14 51 1 0 14 52 1 0 15 53 1 0 17 54 1 6 18 55 1 6 19 56 1 6 20 57 1 0 21 58 1 0 24 59 1 0 29 60 1 0 32 61 1 0 33 62 1 0 35 63 1 0 36 64 1 0 37 65 1 0 40 66 1 0 41 67 1 0 42 68 1 0 M END

Standard InCHIKey	UTUISHMYVAZILQ-NBJODKRESA-N
Standard InCHI	InChI=1S/C30H26O12/c31-14-24-29(42-25(36)10-3-15-1-6-17(32)7-2-15)27(37)28(38)30(41-24)39-19-11-20(34)26-21(35)13-22(40-23(26)12-19)16-4-8-18(33)9-5-16/h1-13,24,27-34,37-38H,14H2/b10-3-/t24-,27-,28-,29-,30-/m1/s1
SMILES	c1cc(ccc1/C=CC(=O)O[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)Oc1cc(c2c(=O)cc(c3ccc(cc3)O)oc2c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.14	Volume:	555.862 ? Van der Waals volume.
Dense:	1.04	LogP:	1.615 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.647 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.399 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	196.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.138	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.127	Fsp³:	0.2
MCE-18:	101.611 ? 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:	0.849	Fluc inhibitor:	0.976 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.977 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.97 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.375	Promiscuous compounds:	0.569

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.198	MDCK Permeability:	-5.207
Pgp-inhibitor:	0.001	Pgp-substrate:	0.045
PAMPA:	0.997 ? 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):	0.375
20% Bioavailability (F20%):	0.963	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.079
Plasma Protein Binding (PPB):	87.832%	Volume Distribution (VD):	-0.028
Fu:	10.816% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.053
BSEP inhibitor:	0.226

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.955
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.979
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.009 ? 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):

3.428

Half-life (T1/2):

3.131

ADMET: Toxicity

hERG Blockers:	0.107	hERG Blockers (10um):	0.327
Human Hepatotoxicity (H-HT):	0.766	Drug-induced Liver Injury (DILI):	0.874
AMES Toxicity:	0.909	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.359	Skin Sensitization:	1.0
Carcinogencity:	0.115	Eye Corrosion:	0.0
Eye Irritation:	0.613	Respiratory Toxicity:	0.069
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.497
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	0.451
Genotoxicity:	0.952	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.969	Hek293 Cytotoxicity:	0.966
BCF:	0.807 ? 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:	3.646 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.646 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.218 ? 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
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711344]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19025748]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245240]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22351977]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO19826	Helicoverpa armigera	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2012	Turnera diffusa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26103	Streptomyces bobili	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2495	Agave xylonacantha	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6766	Antiphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9567	Enicosanthum cupulare	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10991	Maackia tashiroi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9136	Pseudocyclosorus subochthodes	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2012	Turnera diffusa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2495	Agave xylonacantha	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19826	Helicoverpa armigera	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26103	Streptomyces bobili	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6766	Antiphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9567	Enicosanthum cupulare	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10991	Maackia tashiroi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9136	Pseudocyclosorus subochthodes	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	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 NPC156851 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	15095
0.1-0.2	29926
0.2-0.3	3748
0.3-0.4	793
0.4-0.5	221
0.5-0.6	52
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8427	Intermediate Similarity	NPC484301
0.7582	Intermediate Similarity	NPC210961
0.7312	Intermediate Similarity	NPC270675
0.7312	Intermediate Similarity	NPC195685
0.6907	Remote Similarity	NPC472994
0.6634	Remote Similarity	NPC472993
0.6634	Remote Similarity	NPC473278
0.6552	Remote Similarity	NPC39360
0.6552	Remote Similarity	NPC29763
0.6552	Remote Similarity	NPC210003
0.6517	Remote Similarity	NPC27942
0.625	Remote Similarity	NPC331652
0.625	Remote Similarity	NPC164704
0.6238	Remote Similarity	NPC179862
0.6061	Remote Similarity	NPC477628
0.604	Remote Similarity	NPC80068
0.604	Remote Similarity	NPC188815
0.6	Remote Similarity	NPC139060
0.596	Remote Similarity	NPC472992
0.5943	Remote Similarity	NPC470715
0.5909	Remote Similarity	NPC471030
0.5842	Remote Similarity	NPC104883
0.5842	Remote Similarity	NPC488679
0.5833	Remote Similarity	NPC470716
0.5789	Remote Similarity	NPC199172
0.5761	Remote Similarity	NPC95090
0.5761	Remote Similarity	NPC27408
0.5761	Remote Similarity	NPC189142
0.5761	Remote Similarity	NPC77660
0.5728	Remote Similarity	NPC477629
0.5699	Remote Similarity	NPC181712
0.5684	Remote Similarity	NPC601144
0.5673	Remote Similarity	NPC298171
0.5657	Remote Similarity	NPC44931
0.5644	Remote Similarity	NPC64051
0.5625	Remote Similarity	NPC311830
0.5625	Remote Similarity	NPC470717
0.5575	Remote Similarity	NPC470720
0.5567	Remote Similarity	NPC190003
0.5524	Remote Similarity	NPC101636
0.5524	Remote Similarity	NPC260504
0.5524	Remote Similarity	NPC89809
0.5521	Remote Similarity	NPC22832
0.5521	Remote Similarity	NPC243930
0.5484	Remote Similarity	NPC261866
0.5484	Remote Similarity	NPC19709
0.5481	Remote Similarity	NPC472991
0.5446	Remote Similarity	NPC65003
0.5413	Remote Similarity	NPC480796
0.5392	Remote Similarity	NPC122809
0.5361	Remote Similarity	NPC80188
0.5306	Remote Similarity	NPC220169
0.5258	Remote Similarity	NPC282169
0.521	Remote Similarity	NPC35924
0.5189	Remote Similarity	NPC488089
0.5181	Remote Similarity	NPC234133
0.5175	Remote Similarity	NPC295625
0.5164	Remote Similarity	NPC223860
0.5152	Remote Similarity	NPC607707
0.5104	Remote Similarity	NPC93337
0.5104	Remote Similarity	NPC297987
0.5104	Remote Similarity	NPC146792
0.5104	Remote Similarity	NPC323593
0.5104	Remote Similarity	NPC203500
0.5094	Remote Similarity	NPC229409
0.5086	Remote Similarity	NPC470719
0.5053	Remote Similarity	NPC473043
0.5052	Remote Similarity	NPC105025
0.5052	Remote Similarity	NPC610763
0.5047	Remote Similarity	NPC205824

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC156851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4203
0.1-0.2	4857
0.2-0.3	78
0.3-0.4	11
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