NPASS Compound

Natural Product: NPC479354

Natural Product ID	NPC479354
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OZKVJTUNVRZNLD-QAXFLFCBSA-N
IUPAC Name	n.a.
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 107113 0 0 0 0 0 0 0 0999 V2000 -4.7961 -1.9044 0.7584 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0369 -0.6872 0.3240 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9420 0.3470 -0.3340 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0138 1.2672 -1.0942 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9576 1.7808 -0.1663 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4305 0.8044 0.8243 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4039 -0.0289 1.3760 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4302 -0.0091 0.3485 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2843 0.1570 1.0795 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1167 -1.0873 1.8461 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6133 -1.0674 1.9712 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2927 -1.2345 0.6293 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1553 -2.7232 0.2784 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6675 -0.3702 -0.4460 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6528 0.3496 -1.2944 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9229 -0.3459 -1.6216 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4151 -1.2940 -0.5465 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7268 -0.8517 0.7196 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4578 -1.3118 1.9354 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7667 -0.5282 1.9049 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5946 -0.8024 0.6790 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7301 -1.6882 1.1459 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0135 0.5085 0.1083 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3130 0.2792 -1.3538 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6170 -1.0132 -1.7032 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8665 -1.4725 -0.4491 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1535 -2.8525 -0.3504 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0561 1.2782 0.8140 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2032 2.6091 0.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5489 2.6215 -0.5268 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0110 3.2524 -1.5072 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3023 1.7466 0.2478 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4408 0.7528 0.7927 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8186 0.6831 0.2356 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4303 2.9071 0.5218 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6558 2.3533 -1.6537 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4917 2.3522 -3.0461 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9259 -0.2278 -1.0940 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1923 0.0326 -0.6294 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1163 0.6756 -1.6209 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4227 0.9699 -0.8811 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9756 -0.3514 -0.4130 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9175 -1.0332 0.4321 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3839 -2.3730 0.9195 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5453 -2.2662 1.6862 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7597 -1.2243 -0.3206 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0968 -0.1748 0.4038 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3551 1.5458 -1.7669 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6723 1.8693 -2.1345 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0476 -2.6451 1.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2569 -2.3470 -0.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4969 -1.7196 1.5713 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2959 -0.9806 -0.4479 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3814 0.9256 0.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5087 0.6300 -1.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0920 2.1355 -0.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0430 1.3962 1.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4627 0.9280 1.8859 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2984 -1.9648 1.3584 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2897 -1.0805 2.8934 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8924 -0.1245 2.4686 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9171 -1.9287 2.6020 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0111 -3.3086 0.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9764 -2.8797 -0.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2525 -3.1612 0.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9991 -1.0541 -1.0367 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1370 0.5725 -2.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8493 1.3805 -0.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8145 -0.8984 -2.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7117 0.4413 -1.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9241 -2.2793 -0.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7714 0.2748 0.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6098 -2.3880 2.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9168 -0.9675 2.8307 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3250 -0.7217 2.8545 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4696 0.5401 1.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2318 -2.5744 1.6619 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3100 -2.1357 0.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3356 -1.2507 1.9560 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0832 1.1561 0.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9883 1.1346 -1.9801 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4171 0.2239 -1.4781 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9503 -0.9381 -2.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4202 -1.7312 -1.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3366 -3.3888 -0.2233 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6912 1.5600 1.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0081 3.4801 0.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4703 2.6957 -0.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6265 -0.1786 0.2667 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7940 0.6116 1.8557 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5208 1.2763 0.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3893 1.4024 -0.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1404 3.7484 0.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0210 3.2411 -3.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 2.4103 -3.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8935 1.4070 -3.4228 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1979 0.6807 0.2950 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3881 -0.0310 -2.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2600 1.6020 0.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2534 -1.0083 -1.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7186 -0.3629 1.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6149 -2.8163 1.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6109 -3.0265 0.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2884 -1.8263 2.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0483 0.6861 0.9114 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5996 2.4566 -1.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7743 1.8779 -3.1314 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 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 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 23 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 14 34 1 0 5 35 1 0 4 36 1 0 36 37 1 0 3 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 7 2 1 0 34 9 1 0 46 39 1 0 18 12 1 0 26 21 1 0 33 28 1 0 26 17 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 6 3 54 1 1 4 55 1 6 5 56 1 6 6 57 1 1 9 58 1 1 10 59 1 0 10 60 1 0 11 61 1 0 11 62 1 0 13 63 1 0 13 64 1 0 13 65 1 0 14 66 1 6 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 17 71 1 6 18 72 1 6 19 73 1 0 19 74 1 0 20 75 1 0 20 76 1 0 22 77 1 0 22 78 1 0 22 79 1 0 23 80 1 6 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 27 85 1 0 28 86 1 1 29 87 1 0 29 88 1 0 33 89 1 0 33 90 1 0 34 91 1 0 34 92 1 0 35 93 1 0 37 94 1 0 37 95 1 0 37 96 1 0 39 97 1 1 40 98 1 6 41 99 1 1 42100 1 6 43101 1 1 44102 1 0 44103 1 0 45104 1 0 47105 1 0 48106 1 0 49107 1 0 M END

Standard InCHIKey	OZKVJTUNVRZNLD-QAXFLFCBSA-N
Standard InCHI	InChI=1S/C36H58O13/c1-17-30(49-32-28(41)27(40)26(39)24(15-37)48-32)31(44-4)29(42)33(46-17)47-20-7-10-34(2)19(14-20)5-6-23-22(34)8-11-35(3)21(9-12-36(23,35)43)18-13-25(38)45-16-18/h17-24,26-33,37,39-43H,5-16H2,1-4H3/t17-,18+,19+,20-,21+,22-,23+,24+,26+,27-,28+,29+,30-,31-,32-,33-,34-,35+,36-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)[C@@H]2CC(=O)OC2)C1)O)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	698.39	Volume:	682.953 ? Van der Waals volume.
Dense:	1.023	LogP:	0.977 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.64 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.966 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	38.0
TPSA:	193.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.163	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.631	Fsp³:	0.972
MCE-18:	133.718 ? 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:	0.705	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.248	Promiscuous compounds:	0.248

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.868	MDCK Permeability:	-5.138
Pgp-inhibitor:	0.005	Pgp-substrate:	0.712
PAMPA:	0.999 ? 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%):	0.023	30% Bioavailability (F30%):	0.09
50% Bioavailability (F50%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.278
Plasma Protein Binding (PPB):	69.394%	Volume Distribution (VD):	-0.588
Fu:	32.325% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.034
BSEP inhibitor:	0.207

ADMET: Metabolism

CYP1A2-inhibitor:	0.123	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.245	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.991	CYP3A4-substrate:	0.065
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.07 ? 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):

2.18

Half-life (T1/2):

3.148

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.027
Human Hepatotoxicity (H-HT):	0.614	Drug-induced Liver Injury (DILI):	0.915
AMES Toxicity:	0.937	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	1.0
Carcinogencity:	0.519	Eye Corrosion:	0.0
Eye Irritation:	0.016	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.993
Hematotoxicity:	0.76	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.284	RPMI-8226 Immunitoxicity:	0.137
A549 Cytotoxicity:	0.474	Hek293 Cytotoxicity:	0.218
BCF:	0.58 ? 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:	3.213 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.591 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.761 ? 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
NPO40948	Vallaris glabra	Species	n.a.	n.a.	Leaves	n.a.	n.a.	PMID[29072457]
NPO40948	Vallaris glabra	Species	n.a.	n.a.	Stems	n.a.	n.a.	PMID[31820973]

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	4

Activity Type	# Activity
Cell line	4

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
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[31820973]
NPT91	Cell line	KB	Homo sapiens	IC50	=	6600.0	nM	PMID[31820973]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	6200.0	nM	PMID[31820973]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	>	10000.0	nM	PMID[31820973]

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 NPC479354 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	19640
0.1-0.2	25798
0.2-0.3	3420
0.3-0.4	789
0.4-0.5	125
0.5-0.6	45
0.6-0.7	24
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC479353
0.9286	High Similarity	NPC479357
0.7753	Intermediate Similarity	NPC486143
0.7753	Intermediate Similarity	NPC486142
0.7753	Intermediate Similarity	NPC486149
0.7634	Intermediate Similarity	NPC479358
0.7444	Intermediate Similarity	NPC231518
0.7444	Intermediate Similarity	NPC488944
0.7263	Intermediate Similarity	NPC486144
0.7263	Intermediate Similarity	NPC486145
0.7263	Intermediate Similarity	NPC486147
0.7263	Intermediate Similarity	NPC486148
0.7065	Intermediate Similarity	NPC488941
0.7065	Intermediate Similarity	NPC488940
0.6979	Remote Similarity	NPC479360
0.6979	Remote Similarity	NPC479359
0.6979	Remote Similarity	NPC488943
0.6979	Remote Similarity	NPC488942
0.6939	Remote Similarity	NPC120390
0.686	Remote Similarity	NPC479351
0.686	Remote Similarity	NPC479352
0.6809	Remote Similarity	NPC486135
0.6809	Remote Similarity	NPC486137
0.6737	Remote Similarity	NPC232785
0.6737	Remote Similarity	NPC486139
0.6667	Remote Similarity	NPC474423
0.6569	Remote Similarity	NPC488945
0.6569	Remote Similarity	NPC488946
0.6517	Remote Similarity	NPC5311
0.6489	Remote Similarity	NPC236973
0.64	Remote Similarity	NPC486136
0.6327	Remote Similarity	NPC486146
0.6275	Remote Similarity	NPC475419
0.6211	Remote Similarity	NPC30483
0.6211	Remote Similarity	NPC470897
0.6058	Remote Similarity	NPC486134
0.6058	Remote Similarity	NPC486141
0.602	Remote Similarity	NPC475629
0.5979	Remote Similarity	NPC292467
0.5979	Remote Similarity	NPC40749
0.5962	Remote Similarity	NPC74259
0.5918	Remote Similarity	NPC486130
0.5905	Remote Similarity	NPC474908
0.5859	Remote Similarity	NPC486127
0.5842	Remote Similarity	NPC488939
0.5825	Remote Similarity	NPC488938
0.5825	Remote Similarity	NPC488937
0.5769	Remote Similarity	NPC475590
0.5761	Remote Similarity	NPC99620
0.5686	Remote Similarity	NPC329986
0.5686	Remote Similarity	NPC140092
0.5657	Remote Similarity	NPC32177
0.5657	Remote Similarity	NPC469756
0.5657	Remote Similarity	NPC275901
0.5638	Remote Similarity	NPC77299
0.5638	Remote Similarity	NPC480906
0.56	Remote Similarity	NPC188234
0.5596	Remote Similarity	NPC488947
0.5579	Remote Similarity	NPC480914
0.5577	Remote Similarity	NPC486132
0.5577	Remote Similarity	NPC486131
0.5524	Remote Similarity	NPC486128
0.5481	Remote Similarity	NPC486138
0.5481	Remote Similarity	NPC276838
0.5446	Remote Similarity	NPC480910
0.5446	Remote Similarity	NPC240070
0.5446	Remote Similarity	NPC480909
0.5429	Remote Similarity	NPC475219
0.5354	Remote Similarity	NPC480907
0.534	Remote Similarity	NPC208193
0.5321	Remote Similarity	NPC486140
0.5321	Remote Similarity	NPC117445
0.5321	Remote Similarity	NPC308262
0.5273	Remote Similarity	NPC486133
0.5273	Remote Similarity	NPC486150
0.5258	Remote Similarity	NPC199428
0.5258	Remote Similarity	NPC109448
0.5258	Remote Similarity	NPC76572
0.5258	Remote Similarity	NPC310341
0.5258	Remote Similarity	NPC193382
0.5192	Remote Similarity	NPC125077
0.505	Remote Similarity	NPC72260
0.5043	Remote Similarity	NPC486152

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6723
0.1-0.2	2318
0.2-0.3	89
0.3-0.4	7
0.4-0.5	11
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7444	Intermediate Similarity	NPD8033	Approved
0.505	Remote Similarity	NPD8294	Phase 4

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