NPASS Compound

Natural Product: NPC605081

Natural Product ID	NPC605081
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KMOHJUXDKSMQOG-CPUVFPGGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL4167976
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 85 90 0 0 0 0 0 0 0 0999 V2000 0.1498 -2.0413 -0.7630 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4921 -2.1840 0.7004 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5778 -1.7611 1.4520 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9778 -0.4822 1.1692 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2616 -0.2405 1.7001 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3381 -0.6563 0.9092 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0072 -1.8283 1.1292 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6874 -2.7382 2.2178 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9067 -2.4987 3.2880 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6389 -3.4596 4.2693 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1884 -4.7042 4.1500 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9470 -5.6825 5.0996 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9940 -4.9917 3.0713 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2391 -4.0310 2.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0130 -2.1541 0.3028 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4340 -1.4702 -0.6969 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4728 -1.8582 -1.5111 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8703 -1.0737 -2.5662 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9089 -1.4479 -3.3914 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2072 0.1076 -2.7921 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1608 0.5304 -1.9984 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4909 1.7342 -2.2340 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7763 -0.2657 -0.9478 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7381 0.1550 -0.1658 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1158 1.2317 -0.3520 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0641 0.5351 1.6991 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2691 1.4551 0.8465 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2833 2.6635 0.2944 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2560 3.5184 1.1030 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7798 3.0846 -0.9645 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8304 4.2969 -1.4009 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4300 5.4750 -0.7316 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1841 6.4468 -1.5487 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5434 7.6858 -1.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3206 8.0543 0.1715 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7011 9.3265 0.5976 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2750 7.1537 1.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6485 5.8727 0.5569 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2823 -0.3198 2.1076 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3758 0.5338 2.3465 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6524 -1.2495 1.0029 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8252 -1.9907 1.2792 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9637 -1.9308 0.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7262 -1.1934 -0.5605 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1075 -2.7241 0.7500 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1717 -2.8515 0.0580 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4864 -2.2862 -1.2149 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6897 -1.9696 -2.2669 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2090 -1.3007 -3.3821 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5412 -0.9454 -3.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0505 -0.2888 -4.5485 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3750 -1.2543 -2.4070 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8606 -1.9052 -1.3221 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6576 -2.8309 -1.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9278 -2.1457 -0.9886 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4439 -1.0223 -1.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7357 -3.2323 0.9713 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0716 -0.4171 0.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4756 -1.5242 3.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0122 -3.2432 5.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2644 -5.5239 5.8480 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4130 -5.9904 3.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8746 -4.3072 1.2992 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9694 -2.8147 -1.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8725 -2.3391 -3.8935 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5438 0.7117 -3.6403 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9675 2.3885 -2.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3879 0.8081 2.7142 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1647 2.2554 -1.6614 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2557 4.4113 -2.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 6.2321 -2.6002 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0139 8.4009 -1.7778 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3413 9.6661 1.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4489 7.4531 2.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 5.3014 1.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0285 -0.8706 3.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0071 0.4515 1.5931 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8381 -0.6671 0.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0293 -3.2722 1.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9571 -3.5220 0.5537 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 -2.3019 -2.2853 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5496 -1.0568 -4.2114 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0043 0.0275 -4.5884 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4459 -0.9732 -2.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5392 -2.1346 -0.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 7 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 18 20 2 0 20 21 1 0 21 22 1 0 21 23 2 0 23 24 1 0 24 25 2 0 4 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 2 0 26 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 50 52 1 0 52 53 2 0 41 2 1 0 53 47 1 0 24 6 1 0 38 32 1 0 14 8 1 0 23 16 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 6 4 58 1 6 9 59 1 0 10 60 1 0 12 61 1 0 13 62 1 0 14 63 1 0 17 64 1 0 19 65 1 0 20 66 1 0 22 67 1 0 26 68 1 1 30 69 1 0 31 70 1 0 33 71 1 0 34 72 1 0 36 73 1 0 37 74 1 0 38 75 1 0 39 76 1 1 40 77 1 0 41 78 1 6 45 79 1 0 46 80 1 0 48 81 1 0 49 82 1 0 51 83 1 0 52 84 1 0 53 85 1 0 M END

Standard InCHIKey	KMOHJUXDKSMQOG-CPUVFPGGSA-N
Standard InCHI	InChI=1S/C39H32O14/c1-20-35(51-30(45)16-6-21-2-10-24(40)11-3-21)34(48)38(52-31(46)17-7-22-4-12-25(41)13-5-22)39(49-20)53-37-33(47)32-28(44)18-27(43)19-29(32)50-36(37)23-8-14-26(42)15-9-23/h2-20,34-35,38-44,48H,1H3/b16-6-,17-7-/t20-,34+,35-,38+,39-/m0/s1
SMILES	C[C@@H]1O[C@@H](Oc2c(-c3ccc(O)cc3)oc3cc(O)cc(O)c3c2=O)[C@H](OC(=O)/C=Cc2ccc(O)cc2)[C@H](O)[C@H]1OC(=O)/C=Cc1ccc(O)cc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	724.18	Volume:	707.368 ? Van der Waals volume.
Dense:	1.024	LogP:	3.926 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.265 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.505 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	40.0
TPSA:	222.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.515	Fsp³:	0.154
MCE-18:	122.444 ? 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:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.882 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.698 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.444	Promiscuous compounds:	0.715

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.063	MDCK Permeability:	-4.895
Pgp-inhibitor:	0.004	Pgp-substrate:	0.002
PAMPA:	0.984 ? 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):	0.002
20% Bioavailability (F20%):	0.98	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.004
Plasma Protein Binding (PPB):	94.358%	Volume Distribution (VD):	-0.007
Fu:	7.133% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.148
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.582 ? 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):

3.509

Half-life (T1/2):

2.784

ADMET: Toxicity

hERG Blockers:	0.383	hERG Blockers (10um):	0.809
Human Hepatotoxicity (H-HT):	0.643	Drug-induced Liver Injury (DILI):	0.083
AMES Toxicity:	0.46	Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.877	Skin Sensitization:	1.0
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.971	Respiratory Toxicity:	0.228
Drug-induced Neurotoxicity:	0.069	Ototoxicity:	0.109
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.054
Genotoxicity:	0.896	RPMI-8226 Immunitoxicity:	0.096
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.998
BCF:	0.996 ? 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:	4.361 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.988 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.844 ? 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
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1080/10412905.2001.9699624]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11912066]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12419922]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21188975]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30813368]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38695450]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38851735]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29515	Laurus nobilis	Species	Lauraceae	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
IC50	3
Inhibition	1

Activity Type	# Activity
Individual protein	2
Cell line	1
Single protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24914	Single protein	Cystathionine gamma-lyase	Homo sapiens	IC50	>	400000.0	nM	PMID[30108705]
NPT4717	Individual protein	Cystathionine beta-synthase	Homo sapiens	IC50	=	6200.0	nM	PMID[30108705]
NPT4717	Individual protein	Cystathionine beta-synthase	Homo sapiens	Inhibition	n.a.	n.a.	%	PMID[30108705]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	1500.0	nM	PMID[30108705]

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 NPC605081 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	11948
0.1-0.2	33512
0.2-0.3	3539
0.3-0.4	538
0.4-0.5	161
0.5-0.6	97
0.6-0.7	31
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221288
1.0	High Similarity	NPC194836
1.0	High Similarity	NPC91493
0.9186	High Similarity	NPC483767
0.9186	High Similarity	NPC483769
0.9186	High Similarity	NPC483768
0.9186	High Similarity	NPC483766
0.8864	High Similarity	NPC483765
0.8	Intermediate Similarity	NPC101399
0.8	Intermediate Similarity	NPC217822
0.8	Intermediate Similarity	NPC11847
0.8	Intermediate Similarity	NPC198938
0.7889	Intermediate Similarity	NPC104883
0.7889	Intermediate Similarity	NPC488679
0.7857	Intermediate Similarity	NPC259957
0.7553	Intermediate Similarity	NPC218161
0.7196	Intermediate Similarity	NPC231787
0.7053	Intermediate Similarity	NPC205824
0.6909	Remote Similarity	NPC30011
0.6832	Remote Similarity	NPC470712
0.6768	Remote Similarity	NPC478277
0.6768	Remote Similarity	NPC96605
0.6768	Remote Similarity	NPC280642
0.6768	Remote Similarity	NPC478276
0.6768	Remote Similarity	NPC478275
0.6768	Remote Similarity	NPC92815
0.6762	Remote Similarity	NPC162394
0.6667	Remote Similarity	NPC484158
0.6538	Remote Similarity	NPC470718
0.6465	Remote Similarity	NPC85751
0.6465	Remote Similarity	NPC19240
0.646	Remote Similarity	NPC72554
0.6444	Remote Similarity	NPC216496
0.6374	Remote Similarity	NPC48093
0.6304	Remote Similarity	NPC224530
0.6296	Remote Similarity	NPC156785
0.6292	Remote Similarity	NPC104677
0.6262	Remote Similarity	NPC474093
0.6262	Remote Similarity	NPC104910
0.6239	Remote Similarity	NPC97817
0.6207	Remote Similarity	NPC249560
0.6196	Remote Similarity	NPC159579
0.6176	Remote Similarity	NPC223426
0.6147	Remote Similarity	NPC474522
0.614	Remote Similarity	NPC275977
0.6055	Remote Similarity	NPC470713
0.6038	Remote Similarity	NPC164704
0.6036	Remote Similarity	NPC241781
0.6	Remote Similarity	NPC477628
0.5962	Remote Similarity	NPC214621
0.5962	Remote Similarity	NPC34267
0.5957	Remote Similarity	NPC85707
0.5851	Remote Similarity	NPC129217
0.5794	Remote Similarity	NPC477895
0.5769	Remote Similarity	NPC260504
0.5769	Remote Similarity	NPC89809
0.5743	Remote Similarity	NPC470125
0.5741	Remote Similarity	NPC217520
0.5741	Remote Similarity	NPC470715
0.5739	Remote Similarity	NPC25946
0.5714	Remote Similarity	NPC487502
0.567	Remote Similarity	NPC476215
0.566	Remote Similarity	NPC81042
0.5588	Remote Similarity	NPC61904
0.5588	Remote Similarity	NPC472992
0.5577	Remote Similarity	NPC472991
0.5556	Remote Similarity	NPC33083
0.5534	Remote Similarity	NPC297503
0.551	Remote Similarity	NPC170052
0.551	Remote Similarity	NPC135846
0.549	Remote Similarity	NPC35167
0.5484	Remote Similarity	NPC111929
0.5484	Remote Similarity	NPC320283
0.5484	Remote Similarity	NPC41121
0.5481	Remote Similarity	NPC139060
0.5462	Remote Similarity	NPC473554
0.5446	Remote Similarity	NPC163242
0.5446	Remote Similarity	NPC272068
0.5439	Remote Similarity	NPC470717
0.5435	Remote Similarity	NPC288084
0.5429	Remote Similarity	NPC603079
0.5424	Remote Similarity	NPC21359
0.5424	Remote Similarity	NPC460984
0.5392	Remote Similarity	NPC304741
0.5391	Remote Similarity	NPC470720
0.5385	Remote Similarity	NPC12013
0.5385	Remote Similarity	NPC11432
0.5385	Remote Similarity	NPC477613
0.5377	Remote Similarity	NPC188815
0.536	Remote Similarity	NPC475179
0.5347	Remote Similarity	NPC139320
0.534	Remote Similarity	NPC129264
0.5327	Remote Similarity	NPC36138
0.5326	Remote Similarity	NPC54802
0.5326	Remote Similarity	NPC197304
0.53	Remote Similarity	NPC95866
0.5294	Remote Similarity	NPC470405
0.5288	Remote Similarity	NPC253521
0.5288	Remote Similarity	NPC113836
0.5263	Remote Similarity	NPC488734
0.5263	Remote Similarity	NPC77672
0.5263	Remote Similarity	NPC133671
0.5263	Remote Similarity	NPC135391
0.5263	Remote Similarity	NPC78263
0.5263	Remote Similarity	NPC250069
0.5263	Remote Similarity	NPC488735
0.5263	Remote Similarity	NPC488739
0.5263	Remote Similarity	NPC488732
0.5263	Remote Similarity	NPC488738
0.5253	Remote Similarity	NPC209023
0.5234	Remote Similarity	NPC89127
0.5221	Remote Similarity	NPC139571
0.5221	Remote Similarity	NPC470716
0.5214	Remote Similarity	NPC488737
0.5204	Remote Similarity	NPC182121
0.5204	Remote Similarity	NPC175107
0.5192	Remote Similarity	NPC144097
0.5185	Remote Similarity	NPC221342
0.5185	Remote Similarity	NPC476470
0.5155	Remote Similarity	NPC52550
0.5149	Remote Similarity	NPC254855
0.5149	Remote Similarity	NPC94610
0.514	Remote Similarity	NPC97119
0.5138	Remote Similarity	NPC602448
0.5118	Remote Similarity	NPC487501
0.5104	Remote Similarity	NPC127546
0.5104	Remote Similarity	NPC57625
0.5104	Remote Similarity	NPC173637
0.5104	Remote Similarity	NPC317489
0.5104	Remote Similarity	NPC223424
0.5104	Remote Similarity	NPC600591
0.5096	Remote Similarity	NPC473862
0.5096	Remote Similarity	NPC155877
0.5094	Remote Similarity	NPC75574
0.5093	Remote Similarity	NPC477629
0.5053	Remote Similarity	NPC67037
0.5053	Remote Similarity	NPC255615
0.5049	Remote Similarity	NPC258044
0.5049	Remote Similarity	NPC217387
0.5048	Remote Similarity	NPC255157
0.5048	Remote Similarity	NPC259896
0.5047	Remote Similarity	NPC122467
0.5046	Remote Similarity	NPC292929
0.5043	Remote Similarity	NPC488740
0.5043	Remote Similarity	NPC488736
0.5043	Remote Similarity	NPC488733

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3874
0.1-0.2	5212
0.2-0.3	57
0.3-0.4	6
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