NPASS Compound

Natural Product: NPC119866

Natural Product ID	NPC119866
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DHTPVCYNNWQRMN-LHRGPQAGSA-O
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15922818
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl glycosides [CHEMONTID:0002708] Anthocyanidin 3-O-p-coumaroyl glycosides [CHEMONTID:0002711] Anthocyanidin 3-O-6-p-coumaroyl 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 71 75 0 0 0 0 0 0 0 0999 V2000 9.0311 -1.0172 0.2844 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0871 -0.1878 0.0619 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9783 1.0007 -0.6175 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7408 1.3490 -1.0861 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6504 0.4963 -0.8596 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7246 -0.6938 -0.1848 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6660 -1.6260 0.0179 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4078 -1.5924 -0.0387 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4097 -0.6235 -0.3208 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1863 -1.0775 -0.2873 O 0 0 0 0 0 3 0 0 0 0 0 0 2.0625 -0.2992 -0.5338 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0350 -0.4345 0.5995 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5421 -1.8881 0.5407 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4034 -2.0469 1.6981 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9522 -0.7646 2.2165 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0645 0.3376 1.1996 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2673 0.2515 0.5396 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3444 1.0588 0.4401 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3020 2.2778 1.1404 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3864 3.1024 1.0463 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 2.6586 0.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5893 3.5052 0.1466 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6085 4.7173 0.8117 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5581 5.1585 1.5931 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4596 4.3288 1.6915 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4717 4.6874 2.3952 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7148 5.5501 0.7108 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4560 1.5178 -0.3816 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4168 0.6768 -0.3196 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4948 -0.5732 -1.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5456 -1.5503 -1.1052 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7090 -2.7241 -1.8450 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8558 -2.9538 -2.5713 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8305 -1.9829 -2.5384 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6546 -0.8296 -1.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9864 -2.2143 -3.2703 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0249 -4.1316 -3.3164 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7132 -3.6768 -1.8568 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0280 0.3544 0.2833 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2811 -0.3094 3.3549 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4051 -2.9918 1.4199 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6520 -2.6995 0.6983 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5233 0.6928 -0.6133 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0901 1.8043 -0.8119 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1299 -1.9517 0.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0818 -0.4459 0.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5995 2.2719 -1.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7167 0.8059 -1.2891 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0641 -2.6760 0.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9493 -2.6543 0.2123 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5647 -0.5856 -1.5070 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3639 0.7513 -0.6857 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5461 -0.2182 1.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0497 -2.0292 -0.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1892 -2.5083 2.5403 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0058 -0.9700 2.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9915 1.2846 1.7607 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4492 2.5579 1.7312 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4201 3.1577 -0.4710 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5861 6.1105 2.1084 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5427 5.3905 1.2863 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6238 -1.4588 -0.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4175 -0.0763 -1.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8994 -1.8897 -2.9646 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8237 -4.7137 -3.0272 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8675 -4.6083 -1.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0698 0.6438 3.3252 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1533 -3.5588 0.6531 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7509 -3.3230 -0.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1106 1.4057 0.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9763 2.6506 -1.3580 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 3 8 9 1 0 9 10 2 3 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 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 23 27 1 0 21 28 1 0 28 29 1 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 33 37 1 0 32 38 1 0 16 39 1 0 15 40 1 0 14 41 1 0 13 42 1 0 9 43 1 0 3 44 1 0 6 1 1 0 39 12 1 0 29 18 2 0 35 30 1 0 25 20 1 0 1 45 1 0 2 46 1 0 4 47 1 0 5 48 1 0 7 49 1 0 8 50 1 0 11 51 1 0 11 52 1 0 12 53 1 1 13 54 1 6 14 55 1 1 15 56 1 1 16 57 1 1 19 58 1 0 22 59 1 0 24 60 1 0 27 61 1 0 31 62 1 0 35 63 1 0 36 64 1 0 37 65 1 0 38 66 1 0 40 67 1 0 41 68 1 0 42 69 1 0 43 70 1 0 44 71 1 0 M CHG 1 10 1 M END

Standard InCHIKey	DHTPVCYNNWQRMN-LHRGPQAGSA-O
Standard InCHI	InChI=1S/C30H26O14/c31-15-4-1-13(2-5-15)3-6-24(36)41-12-23-26(38)27(39)28(40)30(44-23)43-22-11-17-18(33)9-16(32)10-21(17)42-29(22)14-7-19(34)25(37)20(35)8-14/h1-11,23,26-28,30,38-40H,12H2,(H5-,31,32,33,34,35,36,37)/p+1/t23-,26-,27+,28-,30-/m1/s1
SMILES	c1cc(ccc1C=CC(=[O+]C[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc3-c(cc(cc3=O)O)oc2c2cc(c(c(c2)O)O)O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[10395493]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11534769]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	fruit	n.a.	PMID[16417304]
NPO14284	Delphinium shawurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20351801]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[36557810]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[8988596]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3949	Ceramium rubrum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7713	Euplotes raikovi	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12982	Dysidea amblia	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6347	Iryanthera paraensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11912	Peltogyne porphyrocardia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10887	Pseudeurotium zonatum	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28601	Aspergillus falconensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15160	Gutierrezia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14043	Caulerpa serrulata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Bulb	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10191	Ormosia balansae	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15626	Alternaria japonica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13311	Agelas linnaei	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11128	Ratibida mexicana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11912	Peltogyne porphyrocardia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15253	Helichrysum graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6347	Iryanthera paraensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13160	Garcinia xipshuanbannaensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15160	Gutierrezia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4512	Fagraea gracilipes	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3244	Ascidia ahodori	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7713	Euplotes raikovi	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO965	Bleekeria vitiensis	Species	Plesiopidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14043	Caulerpa serrulata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10887	Pseudeurotium zonatum	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3949	Ceramium rubrum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12982	Dysidea amblia	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28601	Aspergillus falconensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9860.1	Pinus brutia var. eldarica	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14284	Delphinium shawurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12756	Roboastra tigris	Species	Polyceridae	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 NPC119866 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	22823
0.1-0.2	24978
0.2-0.3	1868
0.3-0.4	190
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC119866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4524
0.1-0.2	4600
0.2-0.3	25
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