NPASS Compound

Natural Product: NPC589719

Natural Product ID	NPC589719
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	9,10,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-dodecaen-21-ol
IUPAC Name	9,10,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-dodecaen-21-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 91 0 0 0 0 0 0 0 0999 V2000 6.0031 -3.7460 -1.0570 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7493 -3.4131 -0.4452 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4524 -2.0827 -0.2123 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3627 -1.0814 -0.5665 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0496 0.2517 -0.3254 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8462 0.5676 0.2576 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9585 -0.4174 0.6035 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2536 -1.7657 0.3699 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3715 -2.7687 0.7099 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0243 -2.5402 0.9577 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1175 -2.5249 -0.0661 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2453 -2.2993 0.1467 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6157 -2.0926 1.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7195 -2.1032 2.4989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6120 -2.3286 2.2525 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5501 -2.3431 3.3151 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -2.3072 -0.9974 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5786 -1.9012 -0.7083 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8250 -0.5157 -0.2681 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7486 -0.1900 0.6955 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0093 1.1066 1.0663 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3434 2.1732 0.4774 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5538 3.4987 0.7979 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4504 3.9867 1.7463 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4098 1.8792 -0.4923 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7008 2.9244 -1.1287 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2294 3.5096 -2.3016 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1647 0.5722 -0.8460 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1870 0.3997 -1.8427 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9373 0.9658 -1.5380 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0159 1.0982 -2.5513 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2185 1.6487 -2.2861 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5465 2.0743 -1.0035 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6143 1.9362 -0.0008 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6144 1.3886 -0.2589 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8829 2.6612 -0.7125 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5477 2.0029 0.4849 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7848 2.7412 0.7070 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3293 2.3617 1.9658 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6957 2.6740 -0.3880 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0548 1.2707 -0.7043 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4989 -1.2460 1.3831 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6347 -2.4040 0.4237 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3240 -2.8776 0.0468 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4518 -4.1453 -0.6102 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0011 -3.5150 -2.1323 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1138 -4.8417 -0.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8398 -3.2796 -0.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3011 -1.3832 -1.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0090 -0.2436 1.0722 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4716 -2.6963 -1.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6842 -1.9213 1.6222 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0662 -1.9332 3.5209 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3123 -3.0163 3.3171 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6880 -1.7706 -1.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1965 -3.3843 -1.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1050 -1.9414 -1.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7472 1.3693 1.8363 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4897 3.9563 1.3876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2984 3.4644 2.7109 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2045 5.0812 1.8810 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5157 3.2782 -3.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3225 4.5905 -2.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1859 3.0104 -2.5688 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2300 0.7817 -3.5567 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9761 1.7746 -3.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8882 2.2754 0.9936 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 1.2969 0.5744 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4789 2.5732 -1.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7378 3.7110 -0.4654 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8993 2.1775 1.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7355 1.5550 2.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3614 1.9844 1.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4081 3.2236 2.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6225 3.2322 -0.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3575 3.2437 -1.2793 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9891 1.0258 -0.1145 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3778 1.1527 -1.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9676 -1.6515 2.2725 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5059 -0.9090 1.7232 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1832 -3.2613 0.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1620 -2.0357 -0.4787 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3190 -4.6717 -0.1168 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7081 -4.0943 -1.6721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5719 -4.8070 -0.3908 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 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 12 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 1 0 22 25 1 0 25 26 1 0 26 27 1 0 25 28 2 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 33 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 20 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 8 3 1 0 15 10 1 0 44 18 1 0 41 5 1 0 37 6 1 0 28 19 1 0 35 30 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 7 50 1 0 11 51 1 0 13 52 1 0 14 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 21 58 1 0 24 59 1 0 24 60 1 0 24 61 1 0 27 62 1 0 27 63 1 0 27 64 1 0 31 65 1 0 32 66 1 0 34 67 1 0 35 68 1 0 36 69 1 0 36 70 1 0 37 71 1 0 39 72 1 0 39 73 1 0 39 74 1 0 40 75 1 0 40 76 1 0 41 77 1 0 41 78 1 0 42 79 1 0 42 80 1 0 43 81 1 0 43 82 1 0 45 83 1 0 45 84 1 0 45 85 1 0 M END

Standard InCHIKey	DGAIZFTYTKDOEN-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(42-4)36(37)43-5)13-15-39(2)29(35)17-23-8-11-30(40)31(18-23)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3
SMILES	COC1=CC2=C3C=C1OC1=CC(=CC=C1O)CC1C4=C(C=C(OC)C(OC)=C4OC4=CC=C(C=C4)CC3N(C)CC2)CCN1C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.29	Volume:	631.71 ? Van der Waals volume.
Dense:	0.963	LogP:	3.319 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.154 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.328 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	42.0
TPSA:	72.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	8.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.271	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.745	Fsp³:	0.351
MCE-18:	129.48 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.994	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.75 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.922 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.152

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.82	MDCK Permeability:	-4.765
Pgp-inhibitor:	0.344	Pgp-substrate:	0.272
PAMPA:	0.008 ? 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):	0.0
20% Bioavailability (F20%):	0.146	30% Bioavailability (F30%):	0.093
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979	MRP1:	0.994
Plasma Protein Binding (PPB):	72.888%	Volume Distribution (VD):	0.072
Fu:	26.445% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.125
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.831
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.947	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.226
CYP2B6-substrate:	0.989	CYP2C8-inhibitor:	0.0
HLM stability:	0.032 ? 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):

10.77

Half-life (T1/2):

2.421

ADMET: Toxicity

hERG Blockers:	0.906	hERG Blockers (10um):	0.888
Human Hepatotoxicity (H-HT):	0.284	Drug-induced Liver Injury (DILI):	0.001
AMES Toxicity:	0.656	Rat Oral Acute Toxicity:	0.603
Maximum Recommended Daily Dose:	0.929	Skin Sensitization:	0.952
Carcinogencity:	0.787	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.954
Drug-induced Neurotoxicity:	0.408	Ototoxicity:	0.879
Hematotoxicity:	0.029	Drug-induced Nephrotoxicity:	0.032
Genotoxicity:	0.137	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.237	Hek293 Cytotoxicity:	0.842
BCF:	1.782 ? 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:	4.36 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.013 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.126 ? 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
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[20593839]
NPO40796	Berberis brevissima	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32364734]
NPO40796	Berberis brevissima	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47356	Chondodendron platyphyllum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO52571	Isolona ghesquireina	Genus	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22739	Uvaria ovata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22739	Uvaria ovata	Species	Annonaceae	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 NPC589719 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	28554
0.1-0.2	19741
0.2-0.3	1297
0.3-0.4	125
0.4-0.5	30
0.5-0.6	40
0.6-0.7	34
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC223690
1.0	High Similarity	NPC9532
0.9429	High Similarity	NPC185639
0.9429	High Similarity	NPC251735
0.9429	High Similarity	NPC49075
0.9429	High Similarity	NPC599951
0.8312	Intermediate Similarity	NPC24260
0.7949	Intermediate Similarity	NPC212237
0.7922	Intermediate Similarity	NPC290005
0.7848	Intermediate Similarity	NPC611658
0.7792	Intermediate Similarity	NPC274716
0.7792	Intermediate Similarity	NPC167116
0.7792	Intermediate Similarity	NPC609821
0.7778	Intermediate Similarity	NPC76682
0.7778	Intermediate Similarity	NPC10908
0.7778	Intermediate Similarity	NPC63646
0.7778	Intermediate Similarity	NPC317145
0.7778	Intermediate Similarity	NPC198498
0.7778	Intermediate Similarity	NPC115284
0.7692	Intermediate Similarity	NPC181796
0.7692	Intermediate Similarity	NPC54654
0.7692	Intermediate Similarity	NPC7715
0.7692	Intermediate Similarity	NPC328155
0.7692	Intermediate Similarity	NPC222661
0.7692	Intermediate Similarity	NPC285931
0.7639	Intermediate Similarity	NPC256012
0.7639	Intermediate Similarity	NPC610965
0.7561	Intermediate Similarity	NPC480586
0.75	Intermediate Similarity	NPC480587
0.747	Intermediate Similarity	NPC206900
0.7465	Intermediate Similarity	NPC317272
0.7465	Intermediate Similarity	NPC268503
0.7432	Intermediate Similarity	NPC276890
0.7308	Intermediate Similarity	NPC239824
0.7143	Intermediate Similarity	NPC480590
0.7089	Intermediate Similarity	NPC311973
0.7059	Intermediate Similarity	NPC317439
0.6962	Remote Similarity	NPC608819
0.6951	Remote Similarity	NPC16357
0.6951	Remote Similarity	NPC302245
0.6835	Remote Similarity	NPC290582
0.6835	Remote Similarity	NPC217748
0.6835	Remote Similarity	NPC73492
0.6835	Remote Similarity	NPC182052
0.6835	Remote Similarity	NPC271013
0.6835	Remote Similarity	NPC299990
0.6835	Remote Similarity	NPC42663
0.6835	Remote Similarity	NPC15414
0.6818	Remote Similarity	NPC41122
0.6818	Remote Similarity	NPC318805
0.6795	Remote Similarity	NPC240841
0.6795	Remote Similarity	NPC610959
0.679	Remote Similarity	NPC254441
0.679	Remote Similarity	NPC116465
0.6786	Remote Similarity	NPC8836
0.675	Remote Similarity	NPC279228
0.6667	Remote Similarity	NPC227060
0.6623	Remote Similarity	NPC480592
0.6582	Remote Similarity	NPC12424
0.6582	Remote Similarity	NPC129518
0.6582	Remote Similarity	NPC251580
0.65	Remote Similarity	NPC603853
0.6489	Remote Similarity	NPC475654
0.6386	Remote Similarity	NPC601503
0.6301	Remote Similarity	NPC247639
0.6301	Remote Similarity	NPC25084
0.6265	Remote Similarity	NPC600054
0.6265	Remote Similarity	NPC601504
0.625	Remote Similarity	NPC603603
0.6118	Remote Similarity	NPC229373
0.6098	Remote Similarity	NPC480591
0.5909	Remote Similarity	NPC601489
0.5909	Remote Similarity	NPC604804
0.5851	Remote Similarity	NPC60295
0.5851	Remote Similarity	NPC191132
0.5843	Remote Similarity	NPC605743
0.5789	Remote Similarity	NPC175890
0.5789	Remote Similarity	NPC201508
0.5745	Remote Similarity	NPC85381
0.5732	Remote Similarity	NPC41376
0.573	Remote Similarity	NPC139783
0.573	Remote Similarity	NPC65312
0.573	Remote Similarity	NPC475479
0.573	Remote Similarity	NPC323537
0.573	Remote Similarity	NPC611798
0.5667	Remote Similarity	NPC485712
0.5667	Remote Similarity	NPC275680
0.5667	Remote Similarity	NPC22115
0.5618	Remote Similarity	NPC195538
0.5556	Remote Similarity	NPC243454
0.5543	Remote Similarity	NPC10871
0.5517	Remote Similarity	NPC286119
0.5479	Remote Similarity	NPC185838
0.5455	Remote Similarity	NPC104196
0.5432	Remote Similarity	NPC30779
0.5263	Remote Similarity	NPC135538
0.5263	Remote Similarity	NPC24233
0.5263	Remote Similarity	NPC82457
0.5258	Remote Similarity	NPC475597
0.5204	Remote Similarity	NPC234318
0.5169	Remote Similarity	NPC112248
0.5169	Remote Similarity	NPC600872
0.5139	Remote Similarity	NPC314682
0.5104	Remote Similarity	NPC11296
0.5104	Remote Similarity	NPC281581
0.5104	Remote Similarity	NPC254581
0.5104	Remote Similarity	NPC274661
0.5068	Remote Similarity	NPC213206
0.5068	Remote Similarity	NPC188163
0.5068	Remote Similarity	NPC328750
0.5052	Remote Similarity	NPC485711

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC589719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4701
0.1-0.2	4336
0.2-0.3	102
0.3-0.4	5
0.4-0.5	0
0.5-0.6	1
0.6-0.7	3
0.7-0.8	2
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
0.7778	Intermediate Similarity	NPD8099	Discontinued
0.7143	Intermediate Similarity	NPD8156	Discontinued
0.6556	Remote Similarity	NPD8053	Approved
0.642	Remote Similarity	NPD8095	Phase 1
0.6129	Remote Similarity	NPD8054	Phase 4
0.5068	Remote Similarity	NPD4664	Clinical (unspecified phase)

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