NPASS Compound

Natural Product: NPC84013

Natural Product ID	NPC84013
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FFDULTAFAQRACT-UERZRVEUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	75368730
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 98103 0 0 0 0 0 0 0 0999 V2000 -3.2829 3.1703 0.2426 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9614 2.0811 -0.3511 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6284 0.7659 -0.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6416 0.5291 0.9189 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2569 -0.7610 1.3133 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9415 -1.7924 0.7102 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9399 -1.5505 -0.2217 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3130 -0.2672 -0.6049 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3183 -0.0579 -1.5395 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6752 0.0165 -1.1307 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3153 1.3016 -1.5053 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7887 1.2355 -1.6136 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4071 -0.1151 -1.7267 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5744 -1.1587 -1.0415 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1955 -2.5234 -1.1808 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3428 -2.8222 -2.5190 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3228 -1.1266 -1.6571 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6751 -0.1000 -1.1026 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1446 1.9183 -2.8101 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0229 2.2103 -0.4535 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5987 -2.6200 -0.8005 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2795 -3.9666 -0.4643 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2019 -0.9095 2.3243 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4788 -2.2255 2.3116 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0738 -2.7357 0.9805 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2858 -3.0165 0.9762 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8773 -2.3664 2.0127 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7914 -1.2595 1.5765 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4533 -0.4416 0.5096 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2625 0.5942 0.0946 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4447 0.8636 0.7224 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7975 0.0429 1.8044 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9822 -0.9914 2.2119 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 0.3521 2.4109 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4242 -0.4669 3.5148 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3141 1.9053 0.3418 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3363 1.5724 -0.6027 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4398 2.6898 -1.5942 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8392 3.2796 -1.5600 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8213 2.1236 -1.7779 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4952 1.0201 -0.8308 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7391 0.5117 -0.1704 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4394 -0.5704 0.6955 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5598 1.4672 0.1255 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7072 1.6695 -3.0835 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0947 3.7686 -0.2860 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1377 2.1707 -2.8522 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9253 1.4287 -0.9888 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7026 1.1694 -1.6570 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -1.8768 2.9706 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8143 -0.3669 3.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1940 0.0594 2.1966 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8837 4.1126 0.0811 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1730 3.0823 1.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3207 3.3684 -0.2756 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1005 1.3608 1.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6784 -2.8111 0.9981 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7075 -0.1057 -0.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8325 1.7626 -2.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2706 1.7945 -0.7703 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5160 -0.4143 -2.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4017 -0.9129 0.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1960 -2.5206 -0.6940 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5317 -3.2572 -0.6649 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2559 -3.2097 -2.6813 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6275 0.4316 -0.2690 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7066 2.7076 -2.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0966 1.7926 0.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9033 -4.6652 -1.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2125 -4.1245 -0.7535 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4215 -4.1770 0.6057 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6192 -0.7723 3.3501 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0148 -3.0252 2.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5551 -3.7377 0.7550 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4041 -2.0636 0.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4809 -3.1360 2.5787 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5312 -0.6389 0.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2847 -1.6206 3.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5752 -0.5727 4.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8161 -1.4355 3.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2127 0.1022 4.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1688 0.5717 -1.0237 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6722 3.4998 -1.4165 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9466 4.0366 -2.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8420 2.5437 -1.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0053 0.1442 -1.3395 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4553 0.0653 -0.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3018 1.2625 0.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2315 -1.1248 0.8816 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5234 0.7024 -3.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9335 3.4174 0.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2281 2.8935 -3.5422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6411 1.6995 -2.6271 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6048 0.0761 -1.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8826 1.4410 -0.9729 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8679 -2.3639 3.9650 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7845 0.1042 2.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4915 -0.1115 4.0880 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 0 13 18 1 0 12 19 1 0 11 20 1 0 7 21 1 0 21 22 1 0 5 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 31 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 30 48 1 0 48 49 1 0 27 50 1 0 50 51 1 0 51 52 1 0 8 3 1 0 17 10 1 0 52 23 1 0 50 24 1 0 33 28 1 0 44 37 1 0 1 53 1 0 1 54 1 0 1 55 1 0 4 56 1 0 6 57 1 0 10 58 1 1 11 59 1 6 12 60 1 1 13 61 1 6 14 62 1 1 15 63 1 0 15 64 1 0 16 65 1 0 18 66 1 0 19 67 1 0 20 68 1 0 22 69 1 0 22 70 1 0 22 71 1 0 23 72 1 1 24 73 1 1 25 74 1 0 25 75 1 0 27 76 1 1 29 77 1 0 33 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 37 82 1 6 38 83 1 1 39 84 1 6 40 85 1 1 41 86 1 6 42 87 1 0 42 88 1 0 43 89 1 0 45 90 1 0 46 91 1 0 47 92 1 0 49 93 1 0 49 94 1 0 49 95 1 0 50 96 1 1 51 97 1 0 51 98 1 0 M END

Standard InCHIKey	FFDULTAFAQRACT-UERZRVEUSA-N
Standard InCHI	InChI=1S/C34H46O18/c1-43-17-5-13(6-18(44-2)31(17)51-33-27(41)25(39)23(37)21(9-35)49-33)29-15-11-48-30(16(15)12-47-29)14-7-19(45-3)32(20(8-14)46-4)52-34-28(42)26(40)24(38)22(10-36)50-34/h5-8,15-16,21-30,33-42H,9-12H2,1-4H3/t15-,16-,21+,22+,23+,24+,25-,26-,27+,28+,29-,30-,33-,34-/m0/s1
SMILES	COc1cc(cc(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC)[C@H]1[C@H]2CO[C@@H](c3cc(c(c(c3)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)OC)[C@H]2CO1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	742.27	Volume:	687.687 ? Van der Waals volume.
Dense:	1.079	LogP:	-1.273 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.419 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.981 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	33.0
TPSA:	254.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.119	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.139	Fsp³:	0.647
MCE-18:	142.857 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.481	Fluc inhibitor:	0.017 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.03 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.112	Promiscuous compounds:	0.054

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.847	MDCK Permeability:	-5.263
Pgp-inhibitor:	0.0	Pgp-substrate:	0.166
PAMPA:	0.931 ? 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):	0.314
20% Bioavailability (F20%):	0.037	30% Bioavailability (F30%):	0.928
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.526	MRP1:	0.026
Plasma Protein Binding (PPB):	74.128%	Volume Distribution (VD):	-0.271
Fu:	22.4% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.014
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.111	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.013
HLM stability:	0.003 ? 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):

1.289

Half-life (T1/2):

5.709

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.942	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.984	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.106	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.998
Hematotoxicity:	0.73	Drug-induced Nephrotoxicity:	0.966
Genotoxicity:	0.932	RPMI-8226 Immunitoxicity:	0.389
A549 Cytotoxicity:	0.471	Hek293 Cytotoxicity:	0.28
BCF:	0.792 ? 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:	3.259 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.73 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.824 ? 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
NPO41077	Xanthoceras sorbifolia Bunge	Strain	Sapindaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[27623545]

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	4
IC50	1

Activity Type	# Activity
Non-molecular	5

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	97.55	%	PMID[27623545]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	100.03	%	PMID[27623545]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[27623545]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	100.35	%	PMID[27623545]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	94.91	%	PMID[27623545]

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 NPC84013 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	20005
0.1-0.2	25936
0.2-0.3	2941
0.3-0.4	684
0.4-0.5	220
0.5-0.6	26
0.6-0.7	19
0.7-0.8	0
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC95392
1.0	High Similarity	NPC55715
1.0	High Similarity	NPC35877
0.8772	High Similarity	NPC216129
0.8772	High Similarity	NPC130449
0.8772	High Similarity	NPC248132
0.8197	Intermediate Similarity	NPC51328
0.8197	Intermediate Similarity	NPC55158
0.8	Intermediate Similarity	NPC486104
0.8	Intermediate Similarity	NPC486102
0.7759	Intermediate Similarity	NPC276753
0.7759	Intermediate Similarity	NPC205796
0.7627	Intermediate Similarity	NPC246947
0.7333	Intermediate Similarity	NPC486107
0.7273	Intermediate Similarity	NPC486100
0.7273	Intermediate Similarity	NPC486101
0.7077	Intermediate Similarity	NPC286235
0.6716	Remote Similarity	NPC38041
0.6716	Remote Similarity	NPC22150
0.6716	Remote Similarity	NPC279298
0.6667	Remote Similarity	NPC486099
0.662	Remote Similarity	NPC486098
0.6545	Remote Similarity	NPC299144
0.6429	Remote Similarity	NPC605526
0.6377	Remote Similarity	NPC486109
0.6377	Remote Similarity	NPC486108
0.6316	Remote Similarity	NPC69513
0.6286	Remote Similarity	NPC486105
0.6207	Remote Similarity	NPC48863
0.6207	Remote Similarity	NPC251981
0.6207	Remote Similarity	NPC13745
0.6167	Remote Similarity	NPC162093
0.6143	Remote Similarity	NPC486106
0.6102	Remote Similarity	NPC215833
0.6	Remote Similarity	NPC217854
0.6	Remote Similarity	NPC49074
0.5974	Remote Similarity	NPC486097
0.5806	Remote Similarity	NPC210478
0.5789	Remote Similarity	NPC152722
0.5781	Remote Similarity	NPC232673
0.5733	Remote Similarity	NPC186316
0.5694	Remote Similarity	NPC471063
0.5692	Remote Similarity	NPC470236
0.5658	Remote Similarity	NPC486103
0.5584	Remote Similarity	NPC478055
0.5536	Remote Similarity	NPC276195
0.549	Remote Similarity	NPC281864
0.549	Remote Similarity	NPC328682
0.549	Remote Similarity	NPC54321
0.5469	Remote Similarity	NPC479029
0.541	Remote Similarity	NPC95292
0.5325	Remote Similarity	NPC39657
0.5294	Remote Similarity	NPC479030
0.527	Remote Similarity	NPC199539
0.519	Remote Similarity	NPC185307
0.5161	Remote Similarity	NPC166040
0.5139	Remote Similarity	NPC606627
0.5091	Remote Similarity	NPC228907
0.5085	Remote Similarity	NPC153149
0.5082	Remote Similarity	NPC608788
0.5072	Remote Similarity	NPC470098
0.5072	Remote Similarity	NPC473266

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC84013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5303
0.1-0.2	3732
0.2-0.3	100
0.3-0.4	14
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