NPASS Compound

Natural Product: NPC473667

Natural Product ID	NPC473667
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Avadharidine
IUPAC Name	n.a.
Synonyms	Avadharidine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448609
PubChem CID	44566469
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid alkaloids

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 100106 0 0 0 0 0 0 0 0999 V2000 -2.7171 -3.1050 2.7971 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4148 -2.4742 3.1279 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8651 -1.6365 2.1000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3435 -1.0590 2.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8625 0.1442 1.7479 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8818 1.4074 2.5868 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4453 1.9318 3.0189 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5520 1.0412 2.6268 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4630 0.5238 1.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0794 0.4139 0.6064 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1762 -0.7107 -0.3720 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5988 -1.3196 -0.1603 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7948 -0.9876 1.2573 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4819 -0.6561 -1.1693 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8722 -1.1633 -1.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9651 -0.2635 -0.7958 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5626 1.1801 -0.6061 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8022 1.2957 0.7169 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3539 1.3091 0.3588 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3127 0.8309 -1.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5457 1.5380 -1.6449 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8517 1.0013 -2.8925 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8041 1.9867 -3.8500 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0535 -0.2564 -1.6781 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2454 -0.6087 -1.0586 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9185 -1.0000 -2.4308 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5585 -2.6763 -0.4650 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6325 -1.8044 -0.1877 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1455 -2.1641 -1.4584 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7352 1.7922 2.8555 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4576 1.3132 3.9396 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2851 -0.0933 1.3227 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0389 0.8042 0.6654 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6841 1.9499 0.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6599 2.4118 2.1018 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3927 2.6715 -0.1282 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9255 3.9186 0.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5581 4.6450 -0.8912 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6558 4.1182 -2.1564 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1243 2.8666 -2.4138 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4985 2.1616 -1.3841 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9898 0.8517 -1.6257 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9463 -0.2119 -1.4410 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1272 0.1159 -1.0929 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6055 -1.6413 -1.6403 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8834 -2.4590 -1.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8500 -2.0207 -2.5269 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5985 -1.1010 -3.3707 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1378 -2.6072 -2.6367 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5773 -2.4036 2.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9379 -3.9627 3.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8404 -3.5112 1.7991 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4783 -2.0258 4.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6720 -3.3202 3.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3892 -0.8567 3.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1391 -1.8734 2.3519 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5875 1.3004 3.4137 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2602 2.2589 1.9133 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6010 2.9798 2.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3899 2.0575 4.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6190 0.2477 3.4194 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1768 1.3713 0.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1426 -0.3486 -1.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8159 -1.0658 1.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8959 -2.0685 -0.5158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1663 -1.6126 -2.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3970 -0.5702 0.2030 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4285 1.8415 -0.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1490 2.2918 1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1333 0.4453 1.3184 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9855 2.3461 0.3538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4222 1.1921 -1.6116 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3334 2.6117 -1.6766 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0556 1.5065 -4.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8098 2.4510 -3.8570 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5707 2.7802 -3.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5361 0.0522 -0.2378 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0334 -0.5479 -1.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2185 -1.6890 -0.7473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4433 -1.6627 -2.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9729 -3.1473 0.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8182 -3.0437 -1.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7318 -1.3446 -1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3542 -2.4690 -2.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3493 1.9609 4.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8172 1.3412 4.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7367 0.2635 3.7255 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4402 -1.0877 0.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8619 -0.2427 2.3529 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8639 4.3515 1.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9705 5.6144 -0.6901 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1474 4.6699 -2.9688 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2086 2.4709 -3.4035 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0350 0.6379 -1.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2226 -1.7988 -2.6642 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9167 -2.0068 -0.8446 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3172 -2.1961 -0.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6049 -3.5191 -1.5837 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6015 -2.7671 -3.5732 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6821 -2.9057 -1.8020 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 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 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 16 24 1 0 24 25 1 0 14 26 1 0 12 27 1 0 11 28 1 0 28 29 1 0 8 30 1 0 30 31 1 0 5 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 45 46 1 0 46 47 1 0 47 48 2 0 47 49 1 0 13 3 1 0 10 5 1 0 13 9 1 0 19 9 1 0 20 14 1 0 21 17 1 0 41 36 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 0 2 54 1 0 4 55 1 0 4 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 0 10 62 1 0 11 63 1 0 13 64 1 0 15 65 1 0 15 66 1 0 16 67 1 0 17 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 20 72 1 0 21 73 1 0 23 74 1 0 23 75 1 0 23 76 1 0 25 77 1 0 25 78 1 0 25 79 1 0 26 80 1 0 27 81 1 0 29 82 1 0 29 83 1 0 29 84 1 0 31 85 1 0 31 86 1 0 31 87 1 0 32 88 1 0 32 89 1 0 37 90 1 0 38 91 1 0 39 92 1 0 40 93 1 0 42 94 1 0 45 95 1 0 45 96 1 0 46 97 1 0 46 98 1 0 49 99 1 0 49100 1 0 M END

Standard InCHIKey	ZBALYAJAWGGUCX-RLNVAPDASA-N
Standard InCHI	InChI=1S/C36H51N3O10/c1-6-39-17-33(18-49-31(42)19-9-7-8-10-22(19)38-26(41)12-11-25(37)40)14-13-24(46-3)35-21-15-20-23(45-2)16-34(43,27(21)28(20)47-4)36(44,32(35)39)30(48-5)29(33)35/h7-10,20-21,23-24,27-30,32,43-44H,6,11-18H2,1-5H3,(H2,37,40)(H,38,41)/t20-,21-,23+,24+,27-,28+,29-,30+,32+,33+,34-,35+,36+/m1/s1
SMILES	CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7NC(=O)CCC(=O)N

Calculated Properties

Physi-Chem Properties

Molecular Weight:	685.36	Volume:	676.391 ? Van der Waals volume.
Dense:	1.013	LogP:	1.936 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.29 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.227 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	33.0
TPSA:	179.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	5.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.233	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.081	Fsp³:	0.75
MCE-18:	219.429 ? 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:	0.005	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.345 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.025

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.331	MDCK Permeability:	-5.049
Pgp-inhibitor:	0.0	Pgp-substrate:	0.708
PAMPA:	0.982 ? 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):	0.397
20% Bioavailability (F20%):	0.053	30% Bioavailability (F30%):	0.553
50% Bioavailability (F50%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122	MRP1:	0.997
Plasma Protein Binding (PPB):	84.611%	Volume Distribution (VD):	0.315
Fu:	17.666% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.022
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.0
BSEP inhibitor:	0.571

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.794	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.009	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.344	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.0
HLM stability:	0.019 ? 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):

8.72

Half-life (T1/2):

1.137

ADMET: Toxicity

hERG Blockers:	0.33	hERG Blockers (10um):	0.456
Human Hepatotoxicity (H-HT):	0.286	Drug-induced Liver Injury (DILI):	0.249
AMES Toxicity:	0.335	Rat Oral Acute Toxicity:	0.218
Maximum Recommended Daily Dose:	0.552	Skin Sensitization:	0.674
Carcinogencity:	0.072	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.57
Drug-induced Neurotoxicity:	0.872	Ototoxicity:	0.879
Hematotoxicity:	0.039	Drug-induced Nephrotoxicity:	0.049
Genotoxicity:	0.972	RPMI-8226 Immunitoxicity:	0.12
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.38
BCF:	0.473 ? 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:	3.773 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.741 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.534 ? 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
NPO33014	delphinium cashmirianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[541686]

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	6

Activity Type	# Activity
Organism	6

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
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	8.0	bpm	DrugMatrix in vitro pharmacology data
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	0.0	bpm	PMID[15679321]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	5.0	bpm	PMID[25237727]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-10.0	bpm	PMID[15679321]

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 NPC473667 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	14251
0.1-0.2	35063
0.2-0.3	486
0.3-0.4	23
0.4-0.5	8
0.5-0.6	18
0.6-0.7	6
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
0.7041	Intermediate Similarity	NPC223590
0.6606	Remote Similarity	NPC106593
0.6538	Remote Similarity	NPC473781
0.6415	Remote Similarity	NPC35390
0.6415	Remote Similarity	NPC611189
0.6182	Remote Similarity	NPC481816
0.6036	Remote Similarity	NPC470631
0.5982	Remote Similarity	NPC481815
0.5897	Remote Similarity	NPC605697
0.5847	Remote Similarity	NPC603798
0.5833	Remote Similarity	NPC476501
0.5678	Remote Similarity	NPC603869
0.5593	Remote Similarity	NPC602545
0.5556	Remote Similarity	NPC600720
0.5462	Remote Similarity	NPC599985
0.5372	Remote Similarity	NPC609143
0.5333	Remote Similarity	NPC610006
0.5328	Remote Similarity	NPC610425
0.5312	Remote Similarity	NPC474210
0.5208	Remote Similarity	NPC96080
0.5208	Remote Similarity	NPC99905
0.5208	Remote Similarity	NPC208118
0.5164	Remote Similarity	NPC605561
0.5164	Remote Similarity	NPC608036
0.5128	Remote Similarity	NPC475316

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2671
0.1-0.2	6430
0.2-0.3	49
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