NPASS Compound

Natural Product: NPC322546

Natural Product ID	NPC322546
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SIEHUSRDVBNRGT-GRBUMBGESA-N
IUPAC Name	n.a.
Synonyms	2',3'-Dihydrosalannin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1774400
PubChem CID	52952323
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 89 94 0 0 0 0 0 0 0 0999 V2000 0.2465 -1.7768 3.2926 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6616 -1.2804 2.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7316 -2.0893 0.9042 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3893 -3.3098 1.0806 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1688 -1.5908 -0.4084 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6794 -0.3011 -0.8696 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7765 -0.0536 -1.1032 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2999 -0.8169 -2.3034 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7393 -0.2532 0.0093 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9230 -1.5229 0.5144 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1351 -2.2341 0.4841 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0992 -1.5992 -0.0611 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3161 -3.5832 1.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0221 -3.7025 2.5034 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2726 -5.1768 2.8513 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7457 -4.0187 0.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6288 0.8552 1.0695 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2554 2.1334 0.4677 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0240 2.1915 -1.0335 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8020 1.4368 -1.2900 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2700 1.9700 -2.5562 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2145 1.5858 -2.4997 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4884 0.2121 -2.0284 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5685 -0.7548 -3.1981 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8878 0.4505 -1.4924 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1276 0.0734 -1.3608 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7096 -1.1686 -1.9215 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9183 1.0662 -0.5835 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1307 2.3452 -0.7271 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7169 1.8035 -0.8494 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9146 2.5033 -1.7215 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2415 0.6705 0.7796 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3387 0.2077 1.7121 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0375 -0.0515 2.8701 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2833 0.2369 2.6490 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4690 0.6675 1.4357 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4358 3.3377 -2.3419 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4443 3.5636 -1.4404 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2338 1.9673 -1.8375 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8557 3.2819 1.1403 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7588 4.0705 1.8464 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9676 3.6730 1.8361 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3657 5.2970 2.5713 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9057 -1.4216 4.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7636 -1.3895 3.5136 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3066 -2.8895 3.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3037 -1.4962 -0.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0439 -2.4404 -1.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9352 0.4378 -0.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2776 -1.2566 -2.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3804 -0.2484 -3.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6448 -1.7069 -2.4550 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7578 0.0500 -0.4586 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6664 -4.3461 0.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9206 -3.5659 2.6220 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6087 -3.0254 3.1231 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3749 -5.3074 2.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8675 -5.4341 3.8288 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8167 -5.7546 2.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8655 -5.1015 0.6910 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4629 -3.5198 1.4227 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0085 -3.6232 -0.2861 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2354 0.5267 1.9261 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6101 1.0350 1.3991 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3486 1.9945 0.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0697 1.8481 -0.5002 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7452 1.6306 -3.4730 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5778 1.6853 -3.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6888 -1.7982 -2.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5563 -0.4886 -3.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8207 -0.5203 -3.9619 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7374 -1.1724 -3.0306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7292 -1.3678 -1.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0972 -2.0258 -1.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8884 1.2635 -1.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2905 2.9490 0.1753 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4240 2.9417 -1.6141 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3424 1.7295 0.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2519 0.0569 1.5886 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6244 -0.4303 3.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3787 0.9797 0.9648 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2705 4.1874 -1.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9812 3.9661 -0.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4718 2.8835 -2.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1661 1.8351 -1.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1602 1.1648 -2.5897 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4757 6.1585 1.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3867 5.2250 3.0452 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1185 5.4658 3.3761 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 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 9 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 2 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 28 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 21 37 1 0 37 38 1 0 19 39 1 6 18 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 23 6 1 0 30 25 1 0 36 32 2 0 20 7 1 0 31 22 1 0 38 19 1 0 1 44 1 0 1 45 1 0 1 46 1 0 5 47 1 0 5 48 1 0 6 49 1 1 8 50 1 0 8 51 1 0 8 52 1 0 9 53 1 6 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 16 61 1 0 16 62 1 0 17 63 1 0 17 64 1 0 18 65 1 6 20 66 1 1 21 67 1 6 22 68 1 6 24 69 1 0 24 70 1 0 24 71 1 0 27 72 1 0 27 73 1 0 27 74 1 0 28 75 1 6 29 76 1 0 29 77 1 0 30 78 1 1 33 79 1 0 34 80 1 0 36 81 1 0 38 82 1 0 38 83 1 0 39 84 1 0 39 85 1 0 39 86 1 0 43 87 1 0 43 88 1 0 43 89 1 0 M END

Standard InCHIKey	SIEHUSRDVBNRGT-GRBUMBGESA-N
Standard InCHI	InChI=1S/C34H46O9/c1-9-17(2)31(37)43-25-14-24(41-19(4)35)32(5)16-40-28-29(32)33(25,6)23(13-26(36)38-8)34(7)27-18(3)21(20-10-11-39-15-20)12-22(27)42-30(28)34/h10-11,15,17,21-25,28-30H,9,12-14,16H2,1-8H3/t17?,21-,22-,23-,24-,25+,28-,29+,30-,32-,33+,34-/m1/s1
SMILES	COC(=O)C[C@@H]1[C@@]2(C)[C@@H](OC(=O)C(CC)C)C[C@H]([C@@]3([C@@H]2[C@H]([C@@H]2[C@@]1(C)C1=C(C)[C@@H](C[C@H]1O2)c1ccoc1)OC3)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	598.31	Volume:	608.574 ? Van der Waals volume.
Dense:	0.983	LogP:	3.021 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.063 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.45 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	110.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.232	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.537	Fsp³:	0.735
MCE-18:	145.932 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.963	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.106	Promiscuous compounds:	0.312

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.012	MDCK Permeability:	-4.74
Pgp-inhibitor:	0.99	Pgp-substrate:	0.813
PAMPA:	0.211 ? 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):	0.001
20% Bioavailability (F20%):	0.452	30% Bioavailability (F30%):	0.719
50% Bioavailability (F50%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	0.999
Plasma Protein Binding (PPB):	81.046%	Volume Distribution (VD):	-0.198
Fu:	17.489% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.776
OATP1B3 inhibitor:	0.31	BCRP inhibitor:	0.048
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.652	CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.991	CYP2C19-substrate:	0.177
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.525	CYP3A4-substrate:	0.961
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.978
HLM stability:	0.995 ? 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):

9.408

Half-life (T1/2):

0.713

ADMET: Toxicity

hERG Blockers:	0.135	hERG Blockers (10um):	0.325
Human Hepatotoxicity (H-HT):	0.74	Drug-induced Liver Injury (DILI):	0.95
AMES Toxicity:	0.558	Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.984	Skin Sensitization:	0.946
Carcinogencity:	0.72	Eye Corrosion:	0.0
Eye Irritation:	0.141	Respiratory Toxicity:	0.791
Drug-induced Neurotoxicity:	0.537	Ototoxicity:	0.803
Hematotoxicity:	0.727	Drug-induced Nephrotoxicity:	0.978
Genotoxicity:	0.984	RPMI-8226 Immunitoxicity:	0.157
A549 Cytotoxicity:	0.291	Hek293 Cytotoxicity:	0.074
BCF:	0.814 ? 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:	3.82 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.898 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.197 ? 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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s12038-008-0027-6]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37151484]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4406	Azadirachta indica	Species	Meliaceae	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	5

Activity Type	# Activity
Cell line	3
Non-molecular	2

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	17100.0	nM	PMID[21381696]
NPT81	Cell line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[21381696]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[21381696]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[21381696]

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 NPC322546 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	14510
0.1-0.2	33939
0.2-0.3	1283
0.3-0.4	83
0.4-0.5	13
0.5-0.6	16
0.6-0.7	6
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8395	Intermediate Similarity	NPC308205
0.7931	Intermediate Similarity	NPC61967
0.7654	Intermediate Similarity	NPC604850
0.7442	Intermediate Similarity	NPC488535
0.7349	Intermediate Similarity	NPC182427
0.7262	Intermediate Similarity	NPC29695
0.7045	Intermediate Similarity	NPC62692
0.6596	Remote Similarity	NPC27541
0.6489	Remote Similarity	NPC126984
0.6413	Remote Similarity	NPC214495
0.6413	Remote Similarity	NPC470119
0.6207	Remote Similarity	NPC291150
0.6067	Remote Similarity	NPC116717
0.5955	Remote Similarity	NPC5180
0.5895	Remote Similarity	NPC475226
0.5816	Remote Similarity	NPC475641
0.5761	Remote Similarity	NPC469847
0.5743	Remote Similarity	NPC475237
0.5638	Remote Similarity	NPC475066
0.5604	Remote Similarity	NPC601664
0.5455	Remote Similarity	NPC118086
0.5417	Remote Similarity	NPC469848
0.5204	Remote Similarity	NPC610307
0.52	Remote Similarity	NPC608851
0.5169	Remote Similarity	NPC470120
0.5161	Remote Similarity	NPC470118
0.5098	Remote Similarity	NPC307781
0.5098	Remote Similarity	NPC472670
0.5098	Remote Similarity	NPC601577

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC322546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4153
0.1-0.2	4971
0.2-0.3	26
0.3-0.4	0
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