NPASS Compound

Natural Product: NPC213629

Natural Product ID	NPC213629
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Segetalin A
IUPAC Name	(3S,9S,12S,15S,18S)-12-(1H-indol-3-ylmethyl)-9-methyl-3,15-di(propan-2-yl)-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosane-2,5,8,11,14,17-hexone
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL378333
PubChem CID	10483858
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

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 87 90 0 0 0 0 0 0 0 0999 V2000 2.0461 1.9452 0.7477 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0414 2.2927 -0.5921 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7490 1.7746 -1.4629 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7408 0.7450 -1.4946 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7247 1.0684 -0.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8763 0.1582 -0.2281 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3433 2.4268 -0.8484 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0723 -0.5530 -1.4431 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8904 -0.5994 -1.0290 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5597 -1.8130 -1.8073 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7756 -2.1865 -2.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2230 -3.3649 -1.5843 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9335 -3.8798 -0.9803 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8628 -3.0494 -1.6760 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5715 -3.1039 -1.0505 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2939 -2.8323 0.1659 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0029 -2.8974 0.7672 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9646 -1.8672 0.3586 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4859 -1.0932 1.2369 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4412 -0.0416 1.0040 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3962 0.9085 2.1428 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2922 2.1464 1.9625 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2005 2.9086 0.7822 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7922 3.3122 0.5284 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2784 3.0617 -0.6105 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0684 3.4072 -0.9567 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0893 3.9507 1.5467 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9784 4.2292 0.9491 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4803 0.3312 3.4166 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8538 -0.6228 0.8570 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8488 0.4390 0.6194 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7174 0.9265 1.5714 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4995 1.8897 1.0545 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1642 2.0521 -0.2320 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1416 1.1620 -0.5236 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6120 1.1204 -1.7747 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0973 1.9688 -2.7538 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1056 2.8506 -2.4775 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6368 2.8866 -1.2072 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3694 -1.6575 -0.9517 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1258 -2.9303 2.2977 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9549 -4.1790 2.6422 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2285 -3.1836 2.9314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4631 -3.4978 -1.8365 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0195 1.0104 1.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2235 0.8534 -2.5232 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2322 1.1860 0.5554 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5179 0.1768 -1.1330 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6285 -0.8760 -0.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5036 0.6030 0.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7149 2.9739 0.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2292 2.2346 -1.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6238 2.9981 -1.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5389 -1.4190 -2.5721 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5060 -2.6387 -3.4315 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6755 -4.1569 -2.2228 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9189 -3.0921 -0.7830 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8049 -4.9511 -1.2356 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8967 -3.7902 0.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8598 -3.4864 -2.7306 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4876 -3.8982 0.5371 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1985 0.4187 0.0284 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5620 2.3869 -0.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1805 3.6163 -2.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3695 4.3037 -0.3910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5728 4.6869 1.3723 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5294 4.9991 0.2918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0361 4.0496 0.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8345 4.5632 1.9953 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2221 0.9080 4.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8569 -1.3949 0.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1195 -1.1531 1.7919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7665 0.5846 2.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2566 2.4522 1.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8163 0.4185 -1.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6829 1.9443 -3.7546 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5005 3.5234 -3.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4364 3.5813 -0.9764 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3006 -0.7337 -1.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6345 -2.0376 2.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7087 -4.4068 3.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0168 -4.0308 2.4649 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5098 -5.0073 2.0545 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7500 -2.2914 3.2669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0795 -3.8110 3.8452 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8092 -3.8054 2.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2806 -4.1021 -1.4713 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 5 7 1 0 4 8 1 0 8 9 2 0 8 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 2 3 16 17 1 0 17 18 1 0 18 19 2 3 19 20 1 0 20 21 1 0 21 22 2 3 22 23 1 0 23 24 1 0 24 25 2 3 25 26 1 0 24 27 1 0 23 28 1 0 21 29 1 0 20 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 18 40 1 0 17 41 1 0 41 42 1 0 41 43 1 0 15 44 1 0 26 2 1 0 35 31 1 0 14 10 1 0 39 34 1 0 1 45 1 0 4 46 1 6 5 47 1 0 6 48 1 0 6 49 1 0 6 50 1 0 7 51 1 0 7 52 1 0 7 53 1 0 11 54 1 0 11 55 1 0 12 56 1 0 12 57 1 0 13 58 1 0 13 59 1 0 14 60 1 6 17 61 1 6 20 62 1 6 23 63 1 6 26 64 1 0 26 65 1 0 27 66 1 0 28 67 1 0 28 68 1 0 28 69 1 0 29 70 1 0 30 71 1 0 30 72 1 0 32 73 1 0 33 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 39 78 1 0 40 79 1 0 41 80 1 0 42 81 1 0 42 82 1 0 42 83 1 0 43 84 1 0 43 85 1 0 43 86 1 0 44 87 1 0 M END

Standard InCHIKey	YVUZOKYOUUCVBV-WJTDBPPMSA-N
Standard InCHI	InChI=1S/C31H43N7O6/c1-16(2)25-30(43)35-22(13-19-14-32-21-10-7-6-9-20(19)21)28(41)34-18(5)27(40)33-15-24(39)36-26(17(3)4)31(44)38-12-8-11-23(38)29(42)37-25/h6-7,9-10,14,16-18,22-23,25-26,32H,8,11-13,15H2,1-5H3,(H,33,40)(H,34,41)(H,35,43)(H,36,39)(H,37,42)/t18-,22-,23-,25-,26-/m0/s1
SMILES	OC1=N[C@@H](C(C)C)C(=O)N2CCC[C@H]2C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=NC1)O)C)O)Cc1c[nH]c2c1cccc2)O)C(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	609.33	Volume:	613.86 ? Van der Waals volume.
Dense:	0.993	LogP:	0.359 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.216 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.266 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	199.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.298	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.639	Fsp³:	0.548
MCE-18:	97.875 ? 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:	0.352	Fluc inhibitor:	0.023 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.172 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.863 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.154

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.006	MDCK Permeability:	-5.239
Pgp-inhibitor:	1.0	Pgp-substrate:	0.998
PAMPA:	0.127 ? 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):	0.944
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.855
Plasma Protein Binding (PPB):	54.338%	Volume Distribution (VD):	-0.111
Fu:	45.065% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.002
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.951	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.63	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.007 ? 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):

0.704

Half-life (T1/2):

1.628

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.016	Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.912	Skin Sensitization:	1.0
Carcinogencity:	0.746	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.978
Drug-induced Neurotoxicity:	0.646	Ototoxicity:	0.998
Hematotoxicity:	0.592	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.309 ? 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:	3.203 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.869 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.902 ? 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
NPO40525	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[9157189]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40525	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6752	Melandryum firmum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	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
Activity	1

Activity Type	# Activity
Organism	1

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
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	54.4	mg	PMID[9157189]

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 NPC213629 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	28152
0.1-0.2	19908
0.2-0.3	1310
0.3-0.4	368
0.4-0.5	82
0.5-0.6	26
0.6-0.7	8
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
0.7528	Intermediate Similarity	NPC171317
0.7179	Intermediate Similarity	NPC160105
0.701	Intermediate Similarity	NPC155143
0.6421	Remote Similarity	NPC293917
0.6354	Remote Similarity	NPC483341
0.6296	Remote Similarity	NPC17059
0.6186	Remote Similarity	NPC107077
0.617	Remote Similarity	NPC489625
0.6139	Remote Similarity	NPC54420
0.6126	Remote Similarity	NPC69843
0.6019	Remote Similarity	NPC284549
0.5941	Remote Similarity	NPC31385
0.5893	Remote Similarity	NPC483985
0.5865	Remote Similarity	NPC479075
0.5842	Remote Similarity	NPC223791
0.5769	Remote Similarity	NPC279918
0.573	Remote Similarity	NPC255447
0.5714	Remote Similarity	NPC282231
0.5714	Remote Similarity	NPC314603
0.5701	Remote Similarity	NPC479073
0.5648	Remote Similarity	NPC479076
0.5586	Remote Similarity	NPC480300
0.5524	Remote Similarity	NPC110602
0.5524	Remote Similarity	NPC479071
0.5463	Remote Similarity	NPC479065
0.5315	Remote Similarity	NPC479066
0.5278	Remote Similarity	NPC162860
0.5268	Remote Similarity	NPC75726
0.5263	Remote Similarity	NPC59269
0.5263	Remote Similarity	NPC34779
0.521	Remote Similarity	NPC479574
0.52	Remote Similarity	NPC487596
0.5181	Remote Similarity	NPC49954
0.5126	Remote Similarity	NPC325976
0.5126	Remote Similarity	NPC326363
0.5091	Remote Similarity	NPC482001
0.5057	Remote Similarity	NPC228835

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC213629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3311
0.1-0.2	5534
0.2-0.3	240
0.3-0.4	47
0.4-0.5	17
0.5-0.6	0
0.6-0.7	1
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
0.6421	Remote Similarity	NPD7621	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